Odor and colorant stable compositions
By using ammonoid amino acid compounds in food, cosmetics or pharmaceutical preparations with aromatics or fragrance/flavor compositions, the existing antioxidant toxicity and stability problems are solved, and the efficient stability and antioxidant effects on aromatics or fragrance/flavor agents are achieved.
Patent Information
- Application Number
- CN202380054708.2
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-08-04
- Filing Date
- 2023-08-07
- Publication Date
- 2025-04-01
AI Technical Summary
Commonly used antioxidants such as BHT in existing food, cosmetics or pharmaceutical preparations have toxicity problems and are difficult to effectively stabilize the fragrance or fragrance/flavor composition, resulting in their prone to degradation, discoloration and adverse odor under the action of light and heat.
Animycinoid amino acid compounds are used to mix with aromatic or fragrance/flavor compositions, or in combination with antioxidants, to stabilize these compounds and prevent their degradation of the effects of oxygen, temperature and light.
By using mycocytosin-like amino acid compounds, the stability of aromatics or fragrance/flavors can be significantly improved, their degradation and discoloration under light and heat can be reduced, and the production of adverse odors can be avoided, while providing synergistic stability and antioxidant effects.
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Figure FDA0005300367320000011 
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Abstract
Description
Technical Field
[0001] The present invention relates to a food, cosmetic or pharmaceutical preparation or a home care product, which contains an aromatic or fragrance / flavor compound and an effective amount of a certain mycosporin-like amino acid compound or consists of these compounds. In addition, the present invention relates to the use of such mycosporin-like amino acid compounds for stabilizing aromatic or fragrance / flavor compounds in food, cosmetic or pharmaceutical preparations or home care products. In addition, the present invention relates to the use of such mycosporin-like amino acid compounds for promoting the antioxidant effect of antioxidants in food, cosmetic or pharmaceutical preparations or home care products. Finally, the present invention relates to a method for stabilizing aromatic or fragrance / flavor compounds in food, cosmetic or pharmaceutical preparations or home care products, the method comprising mixing at least one of the mycosporin-like amino acid compounds with an aromatic or fragrance / flavor compound in the food, cosmetic or pharmaceutical preparation or home care product, or to a method for promoting the antioxidant effect in a food, cosmetic or pharmaceutical preparation or home care product, the method comprising mixing at least one of the mycosporin-like amino acid compounds with an antioxidant in the food, cosmetic or pharmaceutical preparation or home care product. Background Art
[0002] Foods, cosmetic compositions (such as fragrance compositions), pharmaceutical compositions or household care products (such as cleaning compositions) are extremely sensitive to oxidation by light and heat. For example, in cleaning compositions, oxidation induces rancidity, discoloration and odor deviation. Fragrances and colorants are often used to mask the unpleasant and typical odor and / or color of oxidized compounds obtained thereby.
[0003] However, those frequently used additives, such as fragrances and colorants, also suffer from instability issues, which result in strong odors and color deviations over time, especially when exposed to oxidizing agents, such as air, UV, light, and heat.
[0004] For this reason, antioxidants are usually used in foods, cosmetics or pharmaceutical preparations or home care products to protect fatty acids, fragrances, flavors / flavors and colorants from oxidation. Based on the same principle, fragrance compositions are also very susceptible to oxidation and show strong deviations in color and odor. The most widely used antioxidant for odor or colorant protection in foods, cosmetics (such as fragrance compositions) or pharmaceutical preparations or home care products (such as cleaning compositions) on the market is butylated hydroxytoluene, also known as butylated hydroxytoluene (BHT).
[0005] BHT is a lipophilic organic compound that is chemically a derivative of phenol. Industrially, BHT is prepared by the reaction of p-cresol (4-methylphenol) with isobutylene (2-methylpropylene) catalyzed by sulfuric acid. Alternatively, BHT is prepared from 2,6-di-tert-butylphenol by hydroxymethylation or aminomethylation followed by hydrogenolysis.
[0006] However, the toxicity of BHT is also known. Currently, the link between BHT and cancer risk and asthma is being discussed. In addition, there are in vitro indications for endocrine disruption. In addition, BHT is suspected of triggering allergy-like symptoms. Allergic skin reactions have been reported especially when BHT is used in cosmetics.
[0007] Therefore, there is a need for food, cosmetic or pharmaceutical preparations or home care products, especially fragrance or aroma / flavor compositions, which have antioxidant stability.
[0008] Furthermore, there is a need for new substances which protect fragrances or aromas / flavors in food, cosmetic or pharmaceutical preparations or household care products against degradation, in particular oxidation.
[0009] Furthermore, there is a constant interest on the market to improve the potential and efficacy spectrum of antioxidants by achieving a higher performance of antioxidants with the same amount, or vice versa, by achieving the same performance with a lower amount of antioxidants, so that the total content of antioxidants in ready-to-use formulations can be reduced.
[0010] It was therefore an object of the present invention to provide a food, cosmetic or pharmaceutical preparation or a household care product which overcomes the disadvantages of the prior art.
[0011] In particular, it is an object of the present invention to provide an efficient and cost-effective BHT replacement capable of protecting fragrance or aroma / flavor compositions from degradation, odor and / or color deviation.
[0012] Finally, it was an object of the present invention to provide a process for stabilizing fragrance or flavor components in food, cosmetic or pharmaceutical preparations or household care products.
[0013] The object is solved by the subject matter of the present invention by using a mycosporin-like amino acid compound as defined herein for stabilizing foods, cosmetics (especially fragrance compositions) or pharmaceutical preparations or household care products (especially cleaning compositions).
[0014] Surprisingly, it has been found that mycosporin-like amino acid compounds as defined herein stabilize fragrances or aromas / flavors in foods, cosmetics or pharmaceutical preparations or home care products, preferably in fragrances or aromas / flavor compositions. Stabilization in the sense of the present invention is to be understood as a stabilization by which fragrances or aromas / flavors, in particular fragrances or aromas / flavor compositions, in foods, cosmetics or pharmaceutical preparations or home care products are protected from degradation caused by oxygen, temperature and / or light. Thus, the use of mycosporin-like amino acid compounds protects the formulation from degradation, odor changes (i.e., malodor formation) and / or discoloration.
[0015] In addition, the concomitant combined use of at least one mycosporin-like amino acid compound as defined herein with well-known antioxidants produces a synergistic stabilizing effect against degradation caused by oxygen, temperature and / or light. The use of such combinations in food, cosmetic or pharmaceutical preparations or household care products then produces stable formulations with no or only slight odor and / or color deviations. Summary of the invention
[0016] In order to solve the above problems, the present invention provides a food, cosmetic or pharmaceutical preparation or household care product in the first aspect, which comprises or consists of the following items
[0017] (a) at least one fragrance or flavor compound; and
[0018] (a) at least one mycosporine-like amino acid compound,
[0019] It is represented by the general formula (V)
[0020]
[0021] as defined herein, or a tautomer or salt thereof;
[0022] or
[0023] Represented by the general formula (VI)
[0024]
[0025]
[0026] as defined herein, or a tautomer or salt thereof;
[0027] or any mixture of the foregoing compounds.
[0028] In a second aspect, the present invention provides the use of at least one mycosporin-like amino acid compound or a mixture thereof as defined herein for stabilizing fragrance or flavor compounds in food, cosmetic or pharmaceutical formulations or home care products.
[0029] Finally, the present invention relates in a further aspect to a method for stabilizing fragrance or flavor compounds using an effective amount of at least one mycosporin-like amino acid compound or a mixture thereof and thereby reducing or inhibiting fragrance or flavor degradation in a food, cosmetic or pharmaceutical preparation or household care product.
[0030] The present invention is specifically described in the appended claims. However, the present invention itself and its preferred variations, other objects and advantages are also apparent from the following detailed description in conjunction with the appended embodiments and drawings. DETAILED DESCRIPTION
[0031] In the context of the present invention, the following general meanings apply:
[0032] As used herein, the singular forms "a", "an", and "the" include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to "a cosmetic formulation" also includes a plurality of cosmetic formulations.
[0033] The terms “comprising”, “including” and “containing” should be understood as open terms, and mean that the components mentioned after the terms are essential but not “limited to”, and other components may be added and still be encompassed by the present invention.
[0034] The term "consisting of" as used in accordance with the present invention means that the total amount of components (a) and (b) adds up to 100 wt. %, based on the total weight of the food, cosmetic or pharmaceutical preparation or household care product, and indicates that the subject matter is closed and may include only the limitations explicitly recited.
[0035] Unless the context indicates otherwise, whenever "comprising" is mentioned, it is intended to encompass both meanings as alternatives, ie, the meaning may be "including" or "consisting of."
[0036] The terms "or" or "and / or" are used as function words to indicate that two words or phrases are to be taken together or separately.
[0037] The term "optionally" means that the subsequently described compound may but need not be present in the composition, and that the description includes variations in which the compound is included and variations in which the compound is not present.
[0038] The endpoints of all ranges directed to the same component or property are inclusive and independently combinable.
[0039] The term "compound" or "compound of the present invention" refers to all compounds covered by the structural formula (V) and / or formula (VI) and / or formula (VII) and / or formula (XIII) and / or formula (IX) and / or formula (X) and / or formula (A) and their subformulae disclosed herein, and includes each subgenus and all specific compounds whose structures are within the formulae disclosed herein.
[0040] Compounds can be identified by their chemical structure and / or chemical name. When there is a conflict between the chemical structure and the chemical name, the chemical structure determines the identity of the compound.
[0041] The term "at least one ... compound" means that the food, cosmetic or pharmaceutical preparation or household care product according to the invention (hereinafter also referred to as "composition") may contain any one of the subsequently described individual compounds or a mixture of two, three, four, five, six or even more different subsequently described compounds.
[0042] The term "effective amount of a compound" means an amount of the compound sufficient to achieve the desired effect or improvement.
[0043] With respect to fragrances / flavors or aroma compounds, an effective amount is the amount that imparts a perceptible odor or flavor in a fragrance or fragrance / flavor composition or in a ready-to-use product. When applied to a combination of fragrances / flavors or aroma substances, the term refers to the total amount of the combination of fragrances / flavors or aroma substances that produces the flavor or odor.
[0044] With respect to mycosporin-like amino acid compounds, an effective amount is that amount necessary to stabilize the aroma or fragrance / flavor compound and protect the composition from degradation.
[0045] The term "synergistic effect" is the effect achieved when two different chemical substances or biological structures interact so that the cumulative total effect is greater than the sum of the individual effects of either of them. In the present invention, the synergistic effect relates to a synergistic stabilizing or antioxidant effect.
[0046] In the context of the present invention, the term "food" is any substance or preparation consumed in order to provide nutritional support to an organism. Food is typically of plant, animal or fungal origin and contains essential nutrients such as carbohydrates, fats, proteins, vitamins or minerals. The substance or preparation is ingested by an organism and assimilated by the cells of the organism to provide energy, sustain life or stimulate growth. The term "food" also encompasses food for animals.
[0047] In the context of the present invention, the term "cosmetic or pharmaceutical preparation" is a composition intended for cosmetic or pharmaceutical purposes. The term "cosmetic or pharmaceutical preparation" also covers sunscreen products, i.e. photoprotective external products for the skin comprising UV-filter compounds which absorb or reflect some of the sun's ultraviolet (UV) radiation and thus help prevent sunburn and, most importantly, skin cancer.
[0048] The term "sunscreen composition" or "sunscreen" or "skin care product", also known as "sun cream", "sunscreen milk" or "sunscreen lotion", refers to any external product that reflects and / or absorbs a certain portion of the UV radiation and thus helps to prevent sunburn and, most importantly, skin cancer. Therefore, the term "sunscreen composition" is to be understood as including not only sunscreen compositions, but also any cosmetic composition that provides UV protection. According to the present invention, the sunscreen composition may contain one or more active agents, such as organic UV-filters, and other ingredients or additives, such as emulsifiers, emollients, viscosity regulators, stabilizers, preservatives or fragrances. Sunscreens come in the form of lotions, sprays, gels, foams (such as expanding foam lotions or whipping lotions), sticks, powders and other external products. UV-absorbing compounds are used not only in sunscreens, but also in other personal care products (such as lipsticks, shampoos, hair sprays, shower gels, soaps and insect repellents).
[0049] In the context of the present invention, the term "home care products" are necessities used in the home for daily care and cleaning purposes. They are used to maintain hygiene and a good atmosphere in the home. Home care products typically include laundry detergents (powders, liquids and tablets), fabric care agents, dishwashing detergents (liquids and tablets), hard floor and surface cleaners, glass cleaners, carpet cleaners, oven cleaners, air fresheners, disinfectants, stain removers, car wash products. These products are typically manufactured in the form of liquids, powders, sprays, granules, etc.
[0050] According to the invention, the main object of the invention is solved by a food, a cosmetic (especially a dermatological cosmetic) or a pharmaceutical preparation or a home care product (also called a formulation or a composition) comprising or consisting of:
[0051] (a) at least one aroma or fragrance / flavor compound;
[0052] (b) at least one mycosporine-like amino acid compound,
[0053] It is represented by the general formula (V)
[0054]
[0055] in
[0056] -Z is selected from the group consisting of: O-R2' or amide';
[0057] -R1' is selected from the group consisting of: CH 2 , unsubstituted or substituted CH(alkyl), unsubstituted or substituted C(alkyl) 2 , unsubstituted or substituted CH(cycloalkyl), unsubstituted or substituted CH(aryl), unsubstituted or substituted CH(heterocycloalkyl), unsubstituted or substituted CH(heteroaryl), CR7'R8', C=O, halogen, O, S, SO, SO 2 , NH, unsubstituted or substituted N(alkyl), unsubstituted or substituted N(alkenyl), unsubstituted or substituted N(alkynyl), unsubstituted or substituted N(alkoxy), unsubstituted or substituted N(alkylthio), unsubstituted or substituted N(cycloalkyl), unsubstituted or substituted N(aryl), unsubstituted or substituted N(heterocycloalkyl), and unsubstituted or substituted N(heteroaryl), and unsubstituted or substituted C-spiro;
[0058] -R2' is selected from the group consisting of H, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted alkoxy, unsubstituted or substituted alkylthio, unsubstituted or substituted cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted heteroaryl;
[0059] -amide' is selected from the group consisting of: NH 2 , unsubstituted or substituted NH(alkyl), unsubstituted or substituted NH(alkenyl), unsubstituted or substituted NH(alkynyl), unsubstituted or substituted NH(alkoxy), unsubstituted or substituted NH(alkylthio), unsubstituted or substituted NH(cycloalkyl), unsubstituted or substituted NH(aryl), unsubstituted or substituted NH(heterocycloalkyl), unsubstituted or substituted NH(heteroaryl), and unsubstituted or substituted NR9'R10', unsubstituted or substituted -N(O-alkyl)(alkyl)
[0060] (Weinreb amide), -N(OH)(H)(hydroxamic acid), and unsubstituted or substituted -N(OH)(alkyl)(alkylated hydroxamic acid);
[0061] -R3' is selected from the group consisting of H, OH, halogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted alkoxy, unsubstituted or substituted alkylthio, unsubstituted or substituted alkanoyl / acyl RC(=O)-, -CH 2 -OH, -R-CH 2 -OH, -C(=O)-OY, -R-
[0062] C(═O)—OY, unsubstituted or substituted cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted heteroaryl, SO, SO 2 NH 2 , unsubstituted or substituted NH(alkyl), unsubstituted or substituted NH(cycloalkyl), unsubstituted or substituted NH(aryl), unsubstituted or substituted NH(heterocycloalkyl), unsubstituted or substituted NH(heteroaryl), unsubstituted or substituted NR9'R10' and unsubstituted or substituted C-spiro;
[0063] - the substituents R4', R5' and R6', which may be the same or different, are independently selected from the group consisting of H, OH, halogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted alkoxy, unsubstituted or substituted alkylthio, unsubstituted or substituted alkanoyl / acyl R-
[0064] C(=O)-, -CH 2 -OH, -R-CH 2 -OH, -C(=O)-OY, -RC(=O)-O-
[0065] Y, unsubstituted or substituted cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted heteroaryl, SO, SO 2 、-
[0066] S(=O) 2 OH, sulfonyl, NH 2 , unsubstituted or substituted NH(alkyl), unsubstituted or substituted NH(alkenyl), unsubstituted or substituted NH(alkynyl), unsubstituted or substituted NH(alkoxy), unsubstituted or substituted NH(alkylthio), unsubstituted or substituted NH(cycloalkyl), unsubstituted or substituted NH(aryl), unsubstituted or substituted NH(heterocycloalkyl), and unsubstituted or substituted NH(heteroaryl), unsubstituted or substituted NR9'R10', and unsubstituted or substituted C-spiro;
[0067] - R7' and R8', which may be the same or different, are independently selected from the group consisting of:
[0068] H, OH, halogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted alkoxy, unsubstituted or substituted alkylthio, unsubstituted or substituted alkanoyl / acyl RC(═O)-, —CH 2 -
[0069] OH, -R-CH 2-OH, -C(=O)-OY, -RC(=O)-OY, unsubstituted or substituted cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted heteroaryl, SO, SO 2 NH 2 , unsubstituted or substituted NH(alkyl), unsubstituted or substituted NH(alkenyl), unsubstituted or substituted NH(alkynyl), unsubstituted or substituted NH(alkoxy), unsubstituted or substituted NH(alkylthio), unsubstituted or substituted NH(cycloalkyl), unsubstituted or substituted NH(aryl), unsubstituted or substituted NH(heterocycloalkyl), unsubstituted or substituted NH(heteroaryl), and unsubstituted or substituted NR9'R10';
[0070] - R9' and R10', which may be identical or different, are independently selected from the group consisting of H, OH, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted alkoxy, unsubstituted or substituted alkylthio, unsubstituted or substituted alkanoyl / acyl RC(=O)-, unsubstituted or substituted cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heterocycloalkyl and unsubstituted or substituted heteroaryl;
[0071] -Y is selected from the group consisting of: H and unsubstituted or substituted alkyl; and -R is unsubstituted or substituted alkyl;
[0072] or a tautomer or stereoisomer or salt of the aforementioned compound;
[0073] Or represented by general formula (VI)
[0074]
[0075] in
[0076] -R1" is selected from the group consisting of: CH 2 , unsubstituted or substituted CH(alkyl), unsubstituted or substituted C(alkyl) 2 , unsubstituted or substituted CH(cycloalkyl), unsubstituted or substituted CH(aryl), unsubstituted or substituted CH(heterocycloalkyl), unsubstituted or substituted CH(heteroaryl), CR7'R8', C=O, halogen, O, S, SO, SO 2 , NH, unsubstituted or substituted N(alkyl), unsubstituted or substituted N(alkenyl), unsubstituted or substituted N(alkynyl), unsubstituted or substituted N(alkoxy), unsubstituted or substituted N(alkylthio), unsubstituted or substituted N(cycloalkyl), unsubstituted or substituted N(aryl), unsubstituted or substituted N(heterocycloalkyl), unsubstituted or substituted N(heteroaryl), and unsubstituted or substituted C-spiro;
[0077] -R2" is selected from the group consisting of H, OH, halogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted alkoxy, unsubstituted or substituted alkylthio, unsubstituted or substituted alkanoyl / acyl RC(=O)-, -CH 2 -OH, -R-CH 2 -OH, -C(=O)-OY, -
[0078] C(=O)-amide", unsubstituted or substituted cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted heteroaryl, SO, SO 2 NH 2 , unsubstituted or substituted NH(alkyl), unsubstituted or substituted NH(alkenyl), unsubstituted or substituted NH(alkynyl), unsubstituted or substituted NH(alkoxy), unsubstituted or substituted NH(alkylthio), unsubstituted or substituted NH(cycloalkyl), unsubstituted or substituted NH(aryl), unsubstituted or substituted NH(heterocycloalkyl), unsubstituted or substituted NH(heteroaryl), unsubstituted or substituted NR9"R10" and unsubstituted or substituted C-spiro;
[0079] -X Select the group consisting of: CH 2 , unsubstituted or substituted CH(alkyl), unsubstituted or substituted CH(alkenyl), unsubstituted or substituted CH(alkynyl), unsubstituted or substituted CH(alkoxy), unsubstituted or substituted CH(alkylthio), unsubstituted or substituted CH(cycloalkyl), unsubstituted or substituted CH(aryl), unsubstituted or substituted CH(heterocycloalkyl), unsubstituted or substituted CH(heteroaryl), -
[0080] CR7”R8”, C=O, O, S, SO, SO 2 , NH, unsubstituted or substituted N(alkyl), unsubstituted or substituted N(alkenyl), unsubstituted or substituted N(alkynyl), unsubstituted or substituted N(alkoxy), unsubstituted or substituted N(alkylthio), unsubstituted or substituted N(cycloalkyl), unsubstituted or substituted N(aryl), unsubstituted or substituted N(heterocycloalkyl), unsubstituted or substituted N(heteroaryl), and unsubstituted or substituted C-spiro;
[0081] - the substituents R4", R5" and R6", which may be the same or different, are independently selected from the group consisting of H, OH, halogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted alkoxy, unsubstituted or substituted alkylthio, unsubstituted or substituted alkanoyl / acyl R-
[0082] C(=O)-, -CH2 -OH, -R-CH 2 -OH, -C(=O)-OY, -RC(=O)-O-
[0083] Y, unsubstituted or substituted cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted heteroaryl, SO, SO 2 、-
[0084] S(=O) 2 OH, sulfonyl, NH 2 , unsubstituted or substituted NH(alkyl), unsubstituted or substituted NH(alkenyl), unsubstituted or substituted NH(alkynyl), unsubstituted or substituted NH(alkoxy), unsubstituted or substituted NH(alkylthio), unsubstituted or substituted NH(cycloalkyl), unsubstituted or substituted NH(aryl), unsubstituted or substituted NH(heterocycloalkyl), and unsubstituted or substituted NH(heteroaryl), unsubstituted or substituted NR9"R10", and unsubstituted or substituted C-spiro;
[0085] - R7" and R8", which may be the same or different, are independently selected from the group consisting of H, OH, halogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted alkoxy, unsubstituted or substituted alkylthio, unsubstituted or substituted alkanoyl / acyl RC(=O)-, -CH 2 -
[0086] OH, -R-CH 2 -OH, -C(=O)-OY, -RC(=O)-OY, unsubstituted or substituted cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted heteroaryl, SO, SO 2 NH 2 , unsubstituted or substituted NH(alkyl), unsubstituted or substituted NH(alkenyl), unsubstituted or substituted NH(alkynyl), unsubstituted or substituted NH(alkoxy), unsubstituted or substituted NH(alkylthio), unsubstituted or substituted NH(cycloalkyl), unsubstituted or substituted NH(aryl), unsubstituted or substituted NH(heterocycloalkyl), unsubstituted or substituted NH(heteroaryl), and unsubstituted or substituted NR9"R10";
[0087] -amide" is selected from the group consisting of: NH 2, unsubstituted or substituted NH(alkyl), unsubstituted or substituted NH(alkenyl), unsubstituted or substituted NH(alkynyl), unsubstituted or substituted NH(alkoxy), unsubstituted or substituted NH(alkylthio), unsubstituted or substituted NH(cycloalkyl), unsubstituted or substituted NH(aryl), unsubstituted or substituted NH(heterocycloalkyl), unsubstituted or substituted NH(heteroaryl), unsubstituted or substituted NR9"R10", unsubstituted or substituted -N(O-alkyl)(alkyl)
[0088] (Weinreb amide), -N(OH)(H)(hydroxamic acid), and unsubstituted or substituted -N(OH)(alkyl)(alkylated hydroxamic acid);
[0089] - R9" and R10", which may be identical or different, are independently selected from the group consisting of H, OH, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted alkoxy, unsubstituted or substituted alkylthio, unsubstituted or substituted alkanoyl / acyl RC(=O)-, unsubstituted or substituted cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heterocycloalkyl and unsubstituted or substituted heteroaryl;
[0090] -Y is selected from the group consisting of H and unsubstituted or substituted alkyl; and
[0091] -R is unsubstituted or substituted alkyl;
[0092] or a tautomer or stereoisomer or salt of the aforementioned compound;
[0093] or any mixture of the foregoing compounds; and
[0094] (c) optionally at least one antioxidant.
[0095] Component (a) of the food, cosmetic or pharmaceutical preparation or home care product according to the first aspect of the invention relates to fragrance or fragrance / flavor compounds or substances, which are usually used in food, cosmetic preparations, especially skin care, hair care or body care, or in pharmaceutical preparations or home care products.
[0096] In the context of the present invention, a fragrance is generally a chemical compound or a class of two or more different chemical compounds that imparts an odor or smell.
[0097] In the context of the present invention, a fragrance / flavoring agent is generally a chemical compound or a class of two or more different chemical compounds that imparts flavor and / or taste.
[0098] Fragrances / flavors affect both taste and smell, whereas fragrances affect only the sense of smell.
[0099] Additionally, in the context of the present invention, the terms "fragrance" or "flavoring agent" are used interchangeably and have equivalent meanings.
[0100] Aroma or fragrance / flavoring compound (a) can be selected from synthetic flavoring liquids and / or oils derived from plant leaves, flowers, fruits, etc., and combinations thereof. Representative aroma or fragrance / flavoring liquids include artificial, natural or synthetic fruit flavors, such as eucalyptus, lemon, orange, banana, grape, lime, apricot and grapefruit oils, and fruit essences, including apple, strawberry, cherry, orange, pineapple, etc.; flavors derived from beans and nuts, such as coffee, cocoa, cola, peanuts, almonds, etc.; and flavors derived from roots, such as licorice or ginger.
[0101] Food, cosmetics or pharmaceutical preparations or home care products according to the present invention include one or more aromatics and / or perfume oils. Suitable perfume oils are mixtures of natural and / or synthetic perfumes. Natural perfumes include flowers (lily, lavender, rose, jasmine, orange blossom, ylang-ylang), stems and leaves (geranium, patchouli, bitter orange), fruits (fennel, coriander, caraway, juniper), peels (bergamot, lemon, orange), roots (nutmeg, angelica, celery, cardamom, ginger, iris, calamus), timber (pine, sandalwood, guaiac, fir, yellow sandalwood), herbs and grasses (tarragon, lemongrass, sage, thyme), needles and branches (spruce, fir, pine, dwarf pine), resins and balsams (galbanum, elemi, benzoin, myrrh, frankincense, windproof) extracts. Animal raw materials, such as civet and castoreum, can also be used. Typical synthetic fragrance compounds are products of ester, ether, aldehyde, ketone alcohol and hydrocarbon types. Examples of ester-type fragrance compounds are benzyl acetate, phenoxyethyl isobutyrate, p-tert-butyl cyclohexyl acetate, linalyl acetate, dimethylbenzyl methyl acetate, phenylethyl acetate, linalyl benzoate, benzyl formate, glycine ethyl methyl phenyl ester, allyl cyclohexyl propionate, styroyl propionate and benzyl salicylate. Ethers include, for example, benzyl ethyl ether, and aldehydes include, for example, straight chain alkanals containing 8 to 18 carbon atoms, citral, citronellal, camphor acyloxy acetaldehyde, cyclamen aldehyde, hydroxycitronellal, lily aldehyde and lily aldehyde. Examples of suitable ketones are ionone, β-isomethyl ionone and methyl cedryl ketone. Suitable alcohols are anethole, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol. Hydrocarbons mainly include terpenes and balsams.
[0102] However, preference is given to using mixtures of different fragrance compounds which together produce a pleasant fragrance. Other suitable fragrance oils are relatively low-volatile essential oils which are used primarily as flavor components. Examples are sage oil, clove oil, melissa oil, peppermint oil, cinnamon leaf oil, linden flower oil, juniper berry oil, vetiver oil, frankincense oil, galbanum oil and labdanum oil.
[0103] Advantageously suitable fragrances (a) are listed, for example, in S. Arctander, Perfume and Flavor Materials, Volume I and Volume II, Montclair, NJ 1969, private publication, and / or in H. Surburg, J. Panten, Common Fragrance and Flavor Materials, 6th edition, Wiley-VCH, Weinheim 2016. The following list contains examples of known odorous substances that are advantageously suitable for use in the present invention:
[0104] - extracts of natural raw materials, such as essential oils, concretes, absolutes, resins, balsams, tinctures, such as, for example: ambergris tincture; tantalum oil; angelica seed oil; angelica root oil; anise oil; valerian oil; basil oil; moss absolute; laurel oil; artemisia annua oil; benzoin resin; bergamot oil; dihydromyrcenol; lilial; lyral; citronellol; phenylethyl alcohol; hexyl cinnamaldehyde; geraniol;
[0105] benzyl acetone; linalool; ethoxymethoxycycloundecane; ambroxan; indole; methyl dihydrojasmonate; sandelice; citrus oil; tangerine oil; orange oil; galbanum; cyclovertal; lavender oil; clary sage oil; damascena; bourbon geranium oil; cyclohexyl salicylate; methyl cedryl ketone (Vertofix Coeur); ambroxan;
[0106] Fixolide NP; synthetic oakmoss; gamma-methylionone (iraldein gamma); phenylacetic acid; geranyl acetate; benzyl acetate; rose oxide; romillat; irotyl, floramat; beeswax absolute; birch tar; bitter almond oil; savory oil; buchu leaf oil; Brazilian sandalwood oil; juniper oil; calamus oil; camphor oil; cananga oil; cardamom oil; quinoa oil; cinnamon oil; acacia absolute; castoreum absolute cedar leaf oil; cedarwood oil; rockrose oil; citronella oil; lemon oil; copaiba balsam; copaiba balsam oil; coriander oil; cassia root oil; cumin oil; cypress oil; davana oil; dill oil; dill seed oil; eau de brouts absolute; oakmoss absolute; elemi oil; tarragon oil; lemon eucalyptus oil; eucalyptus oil; fennel oil; pine needle oil; galbanum oil; galbanum resin; geranium oil; grapefruit oil; guaiac wood oil; guyun balsam; guyun balsam oil; helichrysum absolute; helichrysum oil; ginger oil; orris root absolute; orris root oil; jasmine absolute; calamus oil; blue chamomile oil; Roman chamomile oil; carrot seed oil; quinoa oil; pine needle oil; spearmint oil; caraway oil; labdanum oil; labdanum absolute; labdanum resin; lavender absolute; labdanum Lavender oil; lavender absolute; lavender oil; lemongrass oil; lovage oil; distilled lime oil; pressed lime oil; agarwood oil; litsea cubeba oil; bay leaf oil; nutmeg oil; marjoram oil; tangerine oil; cassia bark oil; mimosa absolute; ambrette oil; musk tincture; muscadine sage oil; nutmeg oil; myrrh absolute; myrrh oil; myrtle oil; clove leaf oil; clove bud oil; neroli oil; frankincense absolute; frankincense oil; red myrrh oil; neroli absolute; orange oil; oregano oil; palmarosa oil; patchouli oil; basil oil ; Peruvian balsam oil; parsley leaf oil; parsley seed oil; orange leaf oil; mint oil; pepper oil; allspice oil; pine oil; lip mint oil; rose absolute; rosewood oil; rose oil; rosemary oil; Dalmatian sage oil; Spanish sage oil; sandalwood oil; celery seed oil; spike lavender oil; star anise oil; styrax oil; marigold oil; fir oil; tea tree oil; turpentine oil; thyme oil; tolu balsam; tonka oil; tuberose absolute; vanilla extract; violet leaf absolute; verbena oil; vetiver oil; juniper berry oil ; Connaught oil; Artemisia oil; Wintergreen oil; Ylang-ylang oil; Hyssop oil; Civet absolute; Cinnamon leaf oil; Cinnamon bark oil and fractions thereof or components isolated therefrom; Individual aromatic substances from the group comprising: hydrocarbons, such as, for example: 3-carene; α-pinene; β-pinene; α-terpene; γ-terpene; p-cymene; Bisabolene; Camphene; Caryophyllene; Cedrene; Farnesene; Limonene; Longifolene; Myrcene; Ocimene; Valerenene; (E,Z)-1,3,5-undecatriene; Styrene; Diphenylmethane;
[0107] aliphatic alcohols, such as, for example: hexanol; octanol; 3-octanol; 2,6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E)-2-hexenol; (E)- and (Z)-3-hexenol; 1-octen-3-ol; a mixture of 3,4,5,6,6-pentamethyl-3,4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methyleneheptan-2-ol; (E,Z)-2,6-nonadienol; 3,7-dimethyl-7-methoxyoctenol;
[0108] -2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol;
[0109] - aliphatic aldehydes and acetals thereof, such as, for example: hexanal; heptanal; octanal; nonanal; decanal; undecanal; dodecanal; tridecanal; 2-methyloctanal; 2-methylnonanal; (E)-2-hexenal;
[0110] (Z)-4-heptenal; 2,6-dimethyl-5-heptenal; 10-undecenal; (E)-4-decenal; 2-dodecenal; 2,6,10-trimethyl-9-undecenal; 2,6,10-trimethyl-5,9-undecadienal; heptaldehyde diethyl acetal; 1,1-dimethoxy-2,2,5-trimethyl-4-hexene; citronellyloxyacetaldehyde; 1-(1-methoxypropoxy)-(E / Z)-3-hexene;
[0111] - aliphatic ketones and their oximes, such as, for example: 2-heptanone; 2-octanone; 3-octanone; 2-nonanone; 5-methyl-3-heptanone; 5-methyl-3-heptanone oxime; 2,4,4,7-tetramethyl-6-octen-3-one; 6-methyl-5-hepten-2-one;
[0112] - aliphatic sulfur-containing compounds, such as, for example: 3-methylmercapto-hexanol; 3-methylmercaptohexyl acetate;
[0113] 3-Mercaptohexanol; 3-Mercaptohexyl acetate; 3-Mercaptohexyl butyrate; 3-Acetylmercaptohexyl acetate; 1-Menthene-8-thiol;
[0114] - aliphatic nitriles, such as, for example: 2-nonenoic acid nitrile; 2-undecenoic acid nitrile; 2-tridecenoic acid nitrile; 3,12-tridecadienoic acid nitrile; 3,7-dimethyl-2,6-octadienoic acid nitrile; 3,7-dimethyl-6-octenoic acid nitrile;
[0115] - Esters of aliphatic carboxylic acids, such as, for example: (E)- and (Z)-3-hexenyl formate; ethyl acetoacetate; isoamyl acetate; hexyl acetate; 3,5,5-trimethylhexyl acetate; 3-methyl-2-butenyl acetate; (E)-2-hexenyl acetate; (E)- and (Z)-3-hexenyl acetate; octyl acetate; 3-octyl acetate; 1-octen-3-yl acetate; ethyl butyrate; butyl butyrate; isoamyl butyrate; hexyl butyrate Esters; (E)- and (Z)-3-hexene-isobutyrate; hexyl crotonate; ethyl isovalerate; ethyl 2-methylpentanoate; ethyl hexanoate; allyl hexanoate; ethyl heptanoate; allyl heptanoate; ethyl octanoate; ethyl (E,Z)-2,4-decadienoate; methyl 2-octanoate; methyl 2-nonanoate; allyl 2-isopentyloxyacetate; methyl 3,7-dimethyl-2,6-octadienoate; 4-methyl-2-pentyl-crotonate;
[0116] acyclic terpene alcohols, such as, for example: citronellol; geraniol; nerol; linalool; lavandinol; nerolidol; farnesol; tetrahydrolinalool; tetrahydrogeraniol; 2,6-dimethyl-7-octen-2-ol; 2,6-dimethyloctan-2-ol; 2-methyl-6-methylene-7-octen-2-ol; 2,6-dimethyl-5,7-octadien-2-ol; 2,6-dimethyl-3,5-octadien-2-ol; 3,7-dimethyl-4,6-octadien-3-ol; 3,7-dimethyl-1,5,7-octatrien-3-ol; 2,6-dimethyl-2,5,7-octatrien-2-ol
[0117] -1-ol; and its formate acetate, propionate, isobutyrate, butyrate, isovalerate, valerate, caproate, crotonate, tiglate and 3-methyl-2-butenoate;
[0118] - acyclic terpene aldehydes and ketones, such as, for example: geranial; neral; citronellal; 7-hydroxy-3,7-dimethyloctanal; 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal; geranylacetone; and the dimethyl acetal and diethyl acetal of geranial; neral; 7-hydroxy-3,7-dimethyloctanal;
[0119] - Cyclic terpene alcohols, such as, for example: menthol; isopulegol; α-terpineol; terpinenol
[0120] -4; menthane-8-ol; menthane-1-ol; menthane-7-ol; borneol; isoborneol; linalool oxide; nopol; cedrol; ambroxol; vetiverol; guaiacol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, valerates, caproates, crotonates, tiglic acid esters and 3-methyl-2-butenoate esters;
[0121] - Cyclic terpene aldehydes and ketones, such as, for example: menthone; isomenthone; 8-mercaptomenth-3-one; carvone; camphor; fenchone; methylionone; methylionone; methyl-n-methylionone; methyl-n-methylionone; methyl-isomethylionone; ethyl-isomethylionone; α-irone; methyl-damascone; ethyl-damascone; ethyl-damascone; butyl-damascone; propyl-damascone; 1-(2,4,4-trimethyl-2-cyclohexane); Hexen-1-yl)-2-buten-1-one; 1,3,4,6,7,8a-hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methylenenaphthalene-8(5H)one; 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal; oleic acid ketone; dihydroleic acid ketone; 4,6,8-megatrien-3-one; methyl cedaraldehyde; ethyl cedaraldehyde; acetylated cedarwood oil (methyl cedarwood ketone);
[0122] - cyclic alcohols, such as, for example: 4-tert-butylcyclohexanol; 3,3,5-trimethylcyclohexanol; 3-isobornylcyclohexanol; 2,6,9-trimethyl-Z2,Z5,E9-cyclododecatrien-1-ol; 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol; cycloaliphatic alcohols, such as, for example: α-3,3-trimethylcyclohexylmethanol; 1-(4-isopropylcyclohexyl)ethanol; 2-methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)butan-ol; 2-methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-buten-1-ol; 2-ethyl
[0123] -4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-butene-1-ol; 3-methyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-pentan-2-ol; 3-methyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol; 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol; 1-
[0124] (2,2,6-trimethylcyclohexyl)pentan-3-ol; 1-(2,2,6-trimethylcyclohexyl)hexan-3-ol;
[0125] - cyclic and cycloaliphatic ethers, such as, for example: eucalyptol; methyl cedarwood ether; cyclododecyl methyl ether; 1,1-dimethoxycyclododecane; (ethoxymethoxy)cyclododecane; α-cedarwood oxide; 3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan; 3a-ethyl-6,6,9a-trimethyldodecahydronaphtho[2,1-b]furan; 1,5,9-trimethyl-13-oxabicyclo[10.1,0]trideca-4,8-diene; rose oxide; 2-(2,4-dimethyl-3-cyclohexen-1-yl)-5-methyl-5-(1-methylpropyl)-1,3-dioxane;
[0126] - cyclic and macrocyclic ketones, such as, for example: 4-tert-butylcyclohexanone; 2,2,5-trimethyl-5-pentylcyclopentanone; 2-pentylcyclopentanone; 2-pentylcyclo-pentanone; 2-hydroxy-3-methyl-2-cyclopenten-1-one; 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one; 3-methyl-2-pentyl-2-cyclopenten-1-one; 3-methyl-4-cyclopentadecenone ; 3-methyl-5-cyclopentadecenone; 3-methylcyclopentadecanone; 4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone; 4-tert-pentylcyclohexanone; 5-cyclohexadecene-1-one; 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone; 8-cyclohexadecene-1-one; 9-cycloheptadecene-1-one; cyclopentadecanone; cyclohexadecanone;
[0127] - cycloaliphatic aldehydes, such as, for example: 2,4-dimethyl-3-cyclohexenecarboxaldehyde; 2-methyl-4-(2,2,6-trimethyl-cyclohexen-1-yl)-2-butenal; 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarboxaldehyde; 4-(4-methyl-3-penten-1-yl)-3-cyclo-hexenecarboxaldehyde;
[0128] - Cycloaliphatic ketones such as, for example: 1-(3,3-dimethyl-cyclohexyl)-4-penten-1-one; 2,2-dimethyl-1-(2,4-dimethyl-3-cyclohexen-1-yl)-1-propanone; 1-(5,5-dimethyl-1-cyclohexene
[0129] -1-yl)-4-penten-1-one; 2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthylmethyl ketone; methyl-2,6,10-trimethyl-2,5,9-cyclododecatrienyl ketone; tert-butyl-(2,4-dimethyl-3-cyclohexen-1-yl) ketone;
[0130] - esters of cyclic alcohols, such as, for example: 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-amylcyclohexyl acetate; 4-tert-amylcyclohexyl acetate; 3,3,5-trimethylcyclohexyl acetate; decahydro-2-naphthyl acetate; 2-cyclopentylcyclopentyl crotonate; 3-pentyltetrahydro-2H-pyran-4-yl acetate; decahydro-2,5,5,8a-tetramethyl -2-naphthyl ester; 4,7-methylene-3a,4,5,6,7,7a-hexahydro-5- or 6-indenyl acetate; 4,7-methylene-3a,4,5,6,7,7a-hexahydro-5- or 6-indenyl propionate; 4,7-methylene-3a,4,5,6,7,7a-hexahydro-5- or 6-indenyl butyrate; 4,7-methyleneoctahydro-5- or 6-indenyl acetate;
[0131] - esters of cycloaliphatic alcohols, such as, for example: 1-cyclohexylethyl crotonate;
[0132] - esters of cycloaliphatic carboxylic acids, such as, for example: allyl 3-cyclohexylpropionate; allyl cyclohexyloxyacetate; cis- and trans-methyl dihydrojasmonate; cis- and trans-methyl jasmonate; methyl 2-hexyl-3-oxocyclopentanecarboxylate; ethyl 2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate; ethyl 2,3,6,6-tetramethyl-2-cyclohexenecarboxylate; ethyl 2-methyl-1,3-dioxolane-2-acetate;
[0133] - aromatic aliphatic alcohols, such as, for example: benzyl alcohol; 1-phenylethanol; 2-phenylethanol; 3-phenylpropanol; 2-phenylpropanol; 2-phenoxyethanol; 2,2-dimethyl-3-phenylpropanol; 2,2-dimethyl-3-(3-methylphenyl)propanol; 1,1-dimethyl-2-phenylethanol; 1,1-dimethyl-3-phenylpropanol; 1-ethyl-1-methyl-3-phenylpropanol; 2-methyl-5-phenylpentanol; 3-methyl-5-phenylpentanol; 3-phenyl-2-propen-1-ol; 4-methoxybenzyl alcohol; 1-(4-isopropylphenyl)ethanol;
[0134] - Esters of aromatic aliphatic alcohols and aliphatic carboxylic acids, such as, for example: benzyl acetate; benzyl propionate; benzyl isobutyrate; benzyl isovalerate; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-phenylethyl isobutyrate; 2-phenylethyl isovalerate; 1-phenylethyl acetate; α-trichloromethylbenzyl acetate; α,α-dimethylphenylethyl acetate; α,α-dimethylphenyl-ethyl butyrate; cinnamyl acetate; 2-phenoxyethyl isobutyrate; 4-methoxybenzyl acetate;
[0135] - aromatic aliphatic ethers, such as, for example: 2-phenylethyl methyl ether; 2-phenylethyl isopentyl ether;
[0136] 2-Phenylethyl 1-ethoxyethyl ether; phenylacetaldehyde dimethyl acetal; phenylacetaldehyde diethyl acetal; hydrogenated atroaldehyde dimethyl acetal; phenylacetaldehyde glycerol acetal; 2,4,6-trimethyl-4-phenyl-1,3-dioxane; 4,4a,5,9b-tetrahydroindeno[1,2-d]-m-dioxin; 4,4a,5,9b-tetrahydro-2,4-dimethylindeno[1,2-d]-m-dioxin;
[0137] - aromatic and aromatic aliphatic aldehydes, such as, for example: benzaldehyde; phenylacetaldehyde; 3-phenylpropionaldehyde; hydroataldehyde; 4-methylbenzaldehyde; 4-methylphenylacetaldehyde; 3-(4-ethylphenyl)-2,2-dimethylpropionaldehyde; 2-methyl-3-(4-isopropylphenyl)propionaldehyde; 2-methyl-3-(4-tert-butylphenyl)propionaldehyde;
[0138] 2-methyl-3-(4-isobutylphenyl)propanal; 3-(4-tert-butylphenyl)propanal; cinnamaldehyde; α-butylcinnamaldehyde; α-amylcinnamaldehyde; α-hexylcinnamaldehyde; 3-methyl-5-phenylpentanal;
[0139] 4-Methoxybenzaldehyde; 4-hydroxy-3-methoxybenzaldehyde; 4-hydroxy-3-ethoxybenzaldehyde; 3,4-methylenedioxybenzaldehyde; 3,4-dimethoxybenzaldehyde; 2-methyl-3-(4-methoxyphenyl)propanal; 2-methyl-3-(4-methylenedioxyphenyl)propanal;
[0140] - aromatic and araliphatic ketones, such as, for example: acetophenone; 4-methyl-acetophenone; 4-methoxyacetophenone; 4-tert-butyl-2,6-dimethylacetophenone; 4-phenyl-2-butanone; 4-(4-hydroxyphenyl)-2-butanone; 1-(2-naphthyl)ethanone; 2-benzofuranethanone; (3-methyl-2-benzofuranyl)ethanone; benzophenone; 1,1,2,3,3,6-hexamethyl-5-indanylmethyl ketone; 6-tert-butyl-1,1-dimethyl-4-indanylmethyl ketone; 1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-5-indenyl]ethanone; 5',6',7',8'-tetrahydro-3',5',5',6',8',8'-hexamethyl-2-naphthylacetophenone;
[0141] - aromatic and araliphatic carboxylic acids and esters thereof, such as, for example: benzoic acid; phenylacetic acid; methyl benzoate; ethyl benzoate; hexyl benzoate; benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geranyl phenylacetate; phenylethyl phenylacetate; methyl cinnamate; ethyl cinnamate; benzyl cinnamate; phenylethyl cinnamate; cinnamyl cinnamate; allyl phenoxyacetate; methyl salicylate; isopentyl salicylate; hexyl salicylate; cyclohexyl salicylate; cis-3-hexenyl salicylate; benzyl salicylate; phenylethyl salicylate; methyl 2,4-dihydroxy-3,6-dimethylbenzoate; ethyl 3-phenylglycidate; ethyl 3-methyl-3-phenylglycidate;
[0142] - nitrogen-containing aromatic compounds, such as, for example: 2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert-butylacetophenone; cinnamonitrile; 3-methyl-5-phenyl-2-pentenoic acid nitrile; 3-methyl-5-phenylvaleric acid nitrile; methyl anthranilate; methyl N-methyl anthranilate; Schiff bases of methyl anthranilate with 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3-(4-tert-butylphenyl)propanal or 2,4-dimethyl-3-cyclohexenecarboxaldehyde 6-isopropylquinoline; 6-isobutylquinoline; 6-sec-butylquinoline; 2-(3-phenylpropyl)pyridine; indole; skatole; 2-methoxy-3-isopropylpyrazine; 2-isobutyl-3-methoxypyrazine;
[0143] - phenols, phenyl ethers and phenyl esters, such as, for example: estragole; anethole; eugenol; eugenol methyl ether; isoeugenol; isoeugenol methyl ether; thymol; carvacrol; diphenyl ether;
[0144] β-Naphthyl methyl ether; β-Naphthyl ethyl ether; β-Naphthyl isobutyl ether; 1,4-Dimethoxybenzene; Eugenyl acetate; 2-Methoxy-4-methylphenol; 2-Ethoxy-5-(1-propenyl)phenol; P-cresyl phenylacetate;
[0145] - heterocyclic compounds, such as, for example: 2,5-dimethyl-4-hydroxy-2H-furan-3-one; 2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one; 3-hydroxy-2-methyl-4H-pyran-4-one; 2-ethyl-3-hydroxy-4H-pyran-4-one;
[0146] - lactones, such as, for example: 1,4-octanolactone; 3-methyl-1,4-octanolactone; 1,4-nonanolactone;
[0147] 1,4-decanolide; 8-decene-1,4-lactone; 1,4-undecalactone; 1,4-dodecalactone; 1,5-decanolide; 1,5-dodecalactone; 4-methyl-1,4-decanolide; 1,15-pentadecalactone; cis- and trans-11-pentadecaene-1,15-lactone; cis- and trans-12-pentadecaene-1,15-lactone;
[0148] 1,16-hexadecene lactone; 9-hexadecene-1,16-lactone; 10-oxa-1,16-hexadecene lactone;
[0149] 11-Oxa-1,16-hexadecanolide; 12-Oxa-1,16-hexadecanolide; 1,12-dodecanoic acid ethylene ester; 1,13-tridecanedioic acid ethylene ester; coumarin; 2,3-dihydrocoumarin; octahydrocoumarin; and any mixture of the above aromatic substances.
[0150] Alternatively, the food, cosmetic or pharmaceutical preparation or home care product according to the first aspect of the present invention comprises at least one fragrance / flavor compound (a) selected from the group consisting of acetophenone, allyl hexanoate, methylionone, ethylionone, anisaldehyde, anisyl acetate, anisyl formate, anethole, benzaldehyde, benzothiazole, benzyl acetate, benzyl alcohol, benzyl benzoate, ethylionone, butyl butyrate, butyl hexanoate, butylidenephthalide, carvone, camphene, caryophyllene, eucalyptol, cinnamyl acetate, citral, citronellol, citronellal, citronellyl acetate, cyclohexyl acetate, cymene, damascone, decalactone, dihydrocoumarin, dimethyl o-aminobenzoate, dimethyl o-aminobenzoate, dodecalactone , ethoxyethyl acetate, ethyl butyric acid, ethyl butyrate, ethyl decanoate, ethyl hexanoate, ethyl crotonate, soy sauce ketone, ethyl guaiacol, ethyl isobutyrate, ethyl isovalerate, ethyl lactate, ethyl methyl butyrate, ethyl propionate, eucalyptol, eugenol, ethyl heptanoate, 4-(p-hydroxyphenyl)-2-butanone, γ-decalactone, geraniol, geranyl acetate, geranyl acetate, citrullaldehyde, methyl dihydrojasmonate (e.g. methyl dihydrojasmonate (R)), jasmonaldehyde, 2-heptanone, 3-heptanone, 4-heptanone, trans-2-heptenal, cis-4-heptenal, trans-2-hexenal, cis-3-hexenol, trans-2-hexenoic acid, trans-3-hexenoic acid, cis-2-hexenyl acetate, cis- 3-Hexenyl hexanoate, cis-3-hexenyl hexanoate, trans-2-hexenyl hexanoate, cis-3-hexenyl formate, cis-2-hexyl acetate, cis-3-hexyl acetate, trans-2-hexyl acetate, cis-3-hexyl formate, p-hydroxybenzyl acetone, isoamyl alcohol, isoamyl isovalerate, isobutyl butyrate, isobutyraldehyde, isoeugenol methyl ether, isopropylmethylthiazole, lauric acid, citric acid, linalool, linalool oxide, linalyl acetate, menthol, menthofuran, methyl o-aminobenzoate, methyl butanol, methylbutyric acid, 2-methylbutyl acetate, methyl hexanoate, methyl cinnamate, 5-methylfurfural, 3,2,2-methylcyclopentenolone, 6,5,2-methylheptenone, methyl dihydrojasmonate, jasmonic acid Methyl ester, methyl 2-methylbutyrate, 2-methyl-2-pentenoyl oleic acid, methyl thiobutyrate, 3,1-methylthiohexanol, 3-methylthiohexanol acetate, nerol, neryl acetate, trans, trans-2,4-nonadienal, 2,4-nonadienol, 2,6-nonadienol, 2,4-nonadienol, nootkatone, butyl octanoic acid, propyl octanoic acid, 2-octanol, 3-octanol, 1,3-octenol, 1-octyl acetate, 3-octyl acetate, palmitic acid, paraaldehyde, phellandrene, pentanedione, phenylethyl acetate, phenylethyl alcohol, phenylethyl isovalerate, piperonal, propionaldehyde, propyl butyrate, long leaf mintone, pulegol, sweet orange aldehyde, thiothiazole, terpenes, terpineol, terpinene, 8,3-thiomenthone, 4,4,2-thiomethylpentyl ketone, thymol, butyl undecalactone, γ undecalactone, valeric acid, vanillin, acetoin, ethyl vanillin, ethyl vanillyl isobutyrate (= 3-ethoxy-4-isobutyryloxybenzaldehyde), 2,5-dimethyl-4-hydroxy-3(2H)-furanone and its derivatives (preferably cyclohomofuranone (= 2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone), homofuranone (= 2-ethyl-5-methyl-4-hydroxy-3(2H)-furanone and 5-ethyl-2-methyl-4-hydroxy-3(2H)-furanone), maltol and maltol derivatives (preferably ethyl maltol), coumarin 1-Hydroxy-2-(or 5-methyl-2-cyclopentenone), 1-Hydroxy-4-(5-methyl-2-cyclopentenone), 1-Hydroxy-4-(5-methyl-2-cyclopentenone), 1-Hydroxy-4-(5-methyl-2-cyclopentenone), 1-Hydroxy-4-(5-methyl-2-cyclopentenone), 1-Hydroxy-4-(5-methyl-2-cyclopentenone), 1-Hydroxy-4-(5-methyl-2-cyclopentenone), 1-Hydroxy-4-(5-methyl-2-cyclopentenone), 1-Hydroxy-4-(5-methyl-2-cyclopentenone), 1-Hydroxy-4-(5-methyl-2-cyclopentenone, ... 3-phenylglycidyl acid ethyl ester, 2-trans-4-cis-decadienoic acid ethyl ester, 4-(p-hydroxyphenyl)-2-butanone, 1,1-dimethoxy-2,2,5-trimethyl-4-hexane, 2,6-dimethyl-5-heptene-1-al and phenylacetaldehyde, 2-methyl-3-(methylthio)furan, 2-methyl-3-furanthiol, bis(2-methyl-3-furanyl) disulfide, furfurylthiol, methylthiopropionaldehyde, 2-acetyl-2-thiazoline, 3-mercapto-2-pentanone, 2,5-dimethyl-3-furanthiol, 2,4,5-trimethylthiazole, 2-acetylthiazole, 2,4-dimethyl-5-ethylthiazole, 2- Acetyl-1-pyrroline, 2-methyl-3-ethylpyrazine, 2-ethyl-3,5-dimethylpyrazine, 2-ethyl-3,6-dimethylpyrazine, 2,3-diethyl-5-methylpyrazine, 3-isopropyl-2-methoxypyrazine, 3-isobutyl-2-methoxypyrazine, 2-acetylpyrazine, 2-pentylpyridine, (E,E)-2,4-decadienal, (E,E)-2,4-nonadienal, (E)-2-octenal, (E)-2-nonenal, 2-undecenal, 12-methyltridecenal, 1-penten-3-one, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, guaiacol, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, 3-hydroxy-4-methyl-5-ethyl-2(5H)-furanone, cinnamaldehyde, cinnamyl alcohol, methyl salicylate, isopulegol, sugar alcohols (e.g., erythritol, threitol, arabitol, ribitol, xylitol, sorbitol, mannitol, dulcitol, lactitol); proteins (e.g., miraculin, monellin, thaumatin, curculin, brazilian melaleuca); sugar substitutes / bulk sweeteners (e.g., Magap, sodium cyclamate, acesulfame potassium, neohesperidin dihydrochalcone, saccharin sodium salt), aspartame, super aspartame, neotame, alitame, sucralose, steviosides, rebaudiosides, lugdarme, carrelame, sucrononate, sucrooctate, monatin, phenylodulcine; SUESS-TASTING amino acids (e.g. glycine, D-leucine, D-threonine, D-asparagine, D-phenylalanine, D-tryptophan, L-proline); SUESS-TASTING low molecular weight substances (e.g. hernanduxin, dihydrochalcone glycosides, glycyrrhizin, glycyrrhizic acid, its derivatives and salts, liquorice (Glycyrrhizza glabra ssp.) extract, sweet oregano (Lipia dulcis extract, Momordica charantia sp. extract), plant extracts (e.g. Momordica grosvenori [Luo Han Guo] and mogrosides obtained therefrom, sweet hydrangea or stevia (e.g. Stevia rebaudiana) extracts or steviosides obtained therefrom), and any mixtures of the above-mentioned flavoring / flavoring substances.
[0151] The above-mentioned fragrances (a) are used in food, cosmetic or pharmaceutical preparations or home care products alone or in the form of a mixture of one, two, three, four or even more fragrances.
[0152] According to the present invention, the food, cosmetic or pharmaceutical preparation or household care product comprises at least one fragrance or fragrance / flavor compound, preferably two, three, four, five, six, seven, eight or more fragrance or fragrance / flavor compounds. Preferably, the fragrance or fragrance / flavor is a fragrance composition comprising a mixture of multiple fragrance compounds or a fragrance / flavor composition comprising a mixture of multiple fragrance / flavor compounds.
[0153] Therefore, in the context of the present invention, the term "fragrance" similarly encompasses a "fragrance composition" and the term "aroma / flavor" similarly encompasses a "aroma / flavor composition".
[0154] The above-mentioned aromatic or fragrance / flavor substances can also be used in encapsulated form. Suitable coating materials here are, for example, starch, including its degradation products and chemically or physically produced derivatives (especially dextrins and maltodextrins), gelatin, gum arabic, agar, gum ghatti, gellan gum, modified and unmodified cellulose, pullulan, curdlan, carrageenan, alginic acid, alginates, pectin, inulin, xanthan gum and mixtures of two or more of these substances.
[0155] Due to their chemical structure and functionality, the abovementioned fragrance or aroma / flavor substances are susceptible to oxidation, temperature and / or light and are susceptible to degradation, which leads to odor changes, i.e. malodor formation, and / or discoloration in the formulations according to the invention.
[0156] Component (b) in the food, cosmetic or pharmaceutical preparation or home care product according to the first aspect of the present invention is at least one mycosporin-like amino acid compound represented by the general formula (V):
[0157]
[0158] As defined herein;
[0159] or
[0160] Represented by the general formula (VI)
[0161]
[0162] As defined herein.
[0163] Mycosporin-like amino acids (MAAs) are minor secondary metabolites produced by organisms living in environments with a lot of sunlight, usually marine environments. MAAs are imine derivatives of mycosporins and contain an amino-cyclohexene-imine ring linked to an amino acid, amino alcohol or amino group. It is known that the compounds exhibit solar radiation absorption properties or UV protection properties. These compounds are capable of electron delocalization. In addition, the compounds exhibit antioxidant properties.
[0164] Unless otherwise indicated, in the context of the present invention, in particular for the definition of mycosporin-like amino acid compounds represented by any general formula, the following general meanings apply:
[0165] According to the present invention, the term "halogen" residue / moiety or group refers to F, Cl, Br or I alone or as part of another substituent.
[0166] According to the present invention, the term "alkyl" alone or as part of another substituent refers to a saturated or mono- or poly-unsaturated straight or branched chain monovalent hydrocarbon radical obtained by removing a hydrogen atom from a single carbon atom of the corresponding parent alkane.
[0167] In a preferred variation, the term "alkyl" also includes any alkyl moiety in the radical derived therefrom, such as alkoxy, alkylthio, alkylsulfonyl saturated straight or branched chain hydrocarbon radicals having 1 to 10, 1 to 8, 1 to 6 or 1 to 4 carbon atoms.
[0168] If the alkyl group is further bonded to another atom, it becomes an alkylene group or alkylene. In other words, the term "alkylene" also refers to a divalent straight or branched chain alkyl group. For example, -CH 2 CH 3 is ethyl, and -CH 2 CH 2 - is ethylene.
[0169] The term "alkylene" alone or as part of another substituent refers to a saturated straight or branched chain divalent hydrocarbon radical derived by the removal of two hydrogen atoms from a single carbon atom or from two different carbon atoms of a starting alkane.
[0170] In a preferred variant according to the invention, the straight-chain or branched alkyl or alkylene group contains 1 to 10 carbon atoms. In other still more preferred variants, the straight-chain or branched alkyl or alkylene group contains 1 to 6 carbon atoms.
[0171] More preferred according to the present invention are saturated straight chain or branched C1-C6 alkyl groups or saturated straight chain or branched C1-C6 alkylene groups.
[0172] Most preferred are straight-chain or branched alkyl or alkylene groups having 1 to 4 carbon atoms.
[0173] Preferred alkyl groups / moieties or alkyl groups include, but are not limited to, C1-C6 alkyl groups including methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl.
[0174] In a preferred variation, the alkyl group / moiety is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, more preferably from the group consisting of methyl and ethyl.
[0175] The alkyl or alkylene groups as defined above may be further substituted.
[0176] The term "alkyl" or "alkylene" also includes radicals or groups having any degree of saturation, i.e., groups having only single carbon-carbon bonds ("alkyl" or "alkylene"), groups having one or more double carbon-carbon bonds ("alkenyl"), groups having one or more triple carbon-carbon bonds ("alkynyl"), and groups having mixtures of single, double and / or triple carbon-carbon bonds.
[0177] According to the present invention, the term "alkenyl", alone or as part of another substituent, refers to an unsaturated straight or branched monovalent hydrocarbon radical having at least one carbon-carbon double bond (C=C double bond). The group may be in a cis or trans conformation around the double bond. Therefore, the term "alkenyl" also includes the corresponding cis / trans isomers.
[0178] In a preferred variant according to the invention, the straight-chain or branched alkenyl group contains 2 to 10 carbon atoms. In a further preferred variant, the straight-chain or branched alkenyl group contains 2 to 6 carbon atoms.
[0179] In a still further preferred variant, the straight-chain or branched alkenyl group contains 2 to 4 carbon atoms.
[0180] Preferred according to the invention are mono- or di-unsaturated straight-chain or branched C1-C6 alkenyl groups.
[0181] Typical alkenyl groups or alkenyl groups include, but are not limited to, vinyl; propenyl, such as prop-1-en-1-yl, prop-1-en-2-yl, prop-2-en-1-yl (allyl), prop-2-en-2-yl, cycloprop-1-en-1-yl, cycloprop-2-en-1-yl; butenyl, such as but-1-en-1-yl, but-1-en-2-yl, 2-methyl-prop-1-en-1-yl, but-2-en-1-yl, but-2-en-2-yl, buta-1,3-dien-1-yl, buta-1,3-dien-2-yl, and the like.
[0182] Alkenyl groups as defined above may be further substituted.
[0183] According to the present invention, the term "alkynyl" alone or as part of another substituent refers to an unsaturated straight or branched monovalent hydrocarbon radical having at least one carbon-carbon triple bond (C≡C triple bond).
[0184] In preferred variants according to the invention, the straight-chain or branched alkynyl group contains 2 to 10 carbon atoms. In other preferred variants, the alkynyl group contains 2 to 6 carbon atoms. In further preferred variants, the alkynyl group contains 2 to 4 carbon atoms.
[0185] Most preferred according to the invention are mono- or di-unsaturated straight-chain or branched C1-C6 alkynyl groups.
[0186] Typical alkynyl groups / moieties or alkynyl groups include, but are not limited to, ethynyl; propynyl such as prop-1-yn-1-yl, prop-2-yn-1-yl, etc.; butynyl such as but-1-yn-1-yl, but-1-yn-3-yl, but-3-yn-1-yl, etc.
[0187] Alkynyl groups as defined above may be further substituted. Alkyl or alkylene groups as defined above may be further substituted.
[0188] According to the present invention, the term "alkoxy" alone or as part of another substituent refers to a straight or branched chain radical of the formula -OR, wherein R is alkyl or substituted alkyl as defined herein.
[0189] In preferred variants according to the invention, the straight-chain or branched alkoxy group contains 2 to 10 carbon atoms. In other preferred variants, the straight-chain or branched alkoxy group contains 2 to 6 carbon atoms. In further preferred variants, the straight-chain or branched alkoxy group contains 2 to 4 carbon atoms.
[0190] Most preferred according to the present invention is a straight-chain or branched C1-C6 alkoxy group.
[0191] Typical alkoxy groups / moieties or alkoxy groups include C1-C6 alkoxy groups including C1-C4 alkoxy groups such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy; and pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy , 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy.
[0192] In a preferred variant, the alkoxy group or alkoxy group is selected from the group consisting of methoxy (-O-ethyl), ethoxy (-O-ethyl), propoxy (-O-propyl) and butoxy (-O-butyl), more preferably from the group consisting of methoxy (-O-methyl) and ethoxy (-O-ethyl).
[0193] The alkoxy or alkylene groups as defined above may be further substituted.
[0194] According to the present invention, the term "alkylthio" or "thioalkoxy" alone or as part of another substituent refers to a radical of formula -SR, wherein R is alkyl or substituted alkyl as defined herein.
[0195] According to the present invention, the term "alkyl" or "alkylene" also includes heteroalkyl groups or heteroalkyl. The term "heteroalkyl" by itself or as part of another substituent refers to an alkyl group in which one or more of the carbon atoms are independently replaced by the same or another heteroatom or by the same or another heteroatom group. Typical heteroatoms or heteroatom groups that can replace carbon atoms include, but are not limited to, -O-, -S-, -N-, -Si-, -NH-, -S(O)-, -S(O) 2 -、-S(O)NH-、-S(O) 2 The heteroatom or heteroatom group may be located at any interior position of the alkyl group.
[0196] Typical heteroatom groups that may be included in these groups include, but are not limited to, -O-, -S-, -OO-, -SS-, -OS-, -NRR-, =NN=, -N=N-, -N=N-NRR, -PR-, -P(O) 2 -、-POR-、-OP(O) 2 -、-SO-、-SO 2 -、-SR 2 OR-, etc., wherein R is independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, or substituted heteroarylalkyl, as defined herein.
[0197] The alkyl or alkylene groups as defined above may be further substituted.
[0198] According to the present invention, the term "acyl" or "alkanoyl", alone or as part of another substituent, refers to the group RC(=O)-, wherein R is hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted aryl, arylalkyl, unsubstituted or substituted arylalkyl, unsubstituted or substituted heteroalkyl, unsubstituted or substituted heteroarylalkyl, as defined herein.
[0199] Representative examples include, but are not limited to, formyl, acetyl, propionyl, butyryl, valeryl, benzoyl, cyclohexylcarbonyl, cyclohexylmethylcarbonyl, benzylcarbonyl, and the like.
[0200] According to the present invention, the term "cycloalkyl" alone or as part of another substituent refers to a saturated or mono- or polyunsaturated non-aromatic cyclic monovalent hydrocarbon radical, in which the carbon atoms are ring-linked and which has no heteroatoms.
[0201] The carbocycle may exist as a monocyclic compound having only a single ring, or as a polycyclic compound having two or more rings.
[0202] In a preferred variation, the term "cycloalkyl" includes a three-membered to ten-membered monocyclic cycloalkyl group or cycloalkyl, or a nine-membered to twelve-membered polycyclic cycloalkyl group or cycloalkyl. In other still more preferred variations, the cycloalkyl moiety comprises a five-membered, six-membered or seven-membered monocyclic cycloalkyl moiety, or a nine-membered to twelve-membered bicyclic cycloalkyl moiety.
[0203] In a preferred embodiment according to the present invention, the cycloalkyl group contains 3 to 20 carbon atoms. In an even more preferred embodiment, the cycloalkyl group contains 6 to 15 carbon atoms. In a most preferred embodiment, the cycloalkyl group contains 6 to 10 carbon atoms. Most preferred is a monocyclic C3-C7 cycloalkyl group.
[0204] Typical cycloalkyl groups or cycloalkyl groups include, but are not limited to, saturated carbocyclic groups having 3 to 20 carbon atoms, such as C3-C12 carbocyclic groups including cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl and cyclododecyl; cyclopentyl, cyclohexyl, cycloheptyl and cyclopropyl-methyl, cyclopropyl-ethyl, cyclobutyl-methyl, cyclobutyl-ethyl, cyclopentyl-methyl, cyclopentyl-ethyl, cyclohexyl-methyl, or C3- C7 carbocyclic group, which includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopropyl-methyl, cyclopropyl-ethyl, cyclobutyl-methyl, cyclopentyl-ethyl, cyclohexyl-methyl, cyclobut-1-en-1-yl, cyclobut-1-en-3-yl, 3-dien-1-yl and the like.
[0205] Preferred polycyclic cycloalkyl groups or cycloalkyl groups according to the present invention include, but are not limited to, naphthyl, indenyl, and the like.
[0206] According to the invention, the term "cycloalkyl" also includes cycloalkenyl, i.e. an unsaturated cyclic hydrocarbon radical containing a C=C double bond between two carbon atoms of the ring molecule. In a broader sense, cycloalkenyl is a compound with one, two or more double bonds, wherein the number of possible (mostly conjugated) double bonds in the molecule depends on the ring size.
[0207] Typical cycloalkenyl groups include, but are not limited to, cyclopropenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, and the like.
[0208] According to the invention, the term "cycloalkyl" also includes cycloalkynyl groups containing a cyclic hydrocarbon radical, ie an unsaturated -C≡C- triple bond between two carbon atoms of the ring molecule, which triple bond depends on the ring size due to ring strain.
[0209] Typical cycloalkynyl groups include cyclooctene.
[0210] The cycloalkyl, cycloalkenyl or cycloalkynyl moieties or groups as defined above may be further substituted.
[0211] According to the present invention, the term "aryl", alone or as part of another substituent, refers to a monovalent aromatic hydrocarbon radical derived by removing a hydrogen atom from a single carbon atom of an aromatic ring SY-stem.
[0212] In a preferred variation, the term "aryl" includes a three- to ten-membered monocyclic aryl group or aryl, or a nine- to twelve-membered polycyclic aryl group or aryl. In other still more preferred variations, carboaryl includes a five-, six- or seven-membered monocyclic carboaryl, or a nine- to twelve-membered bicyclic carboaryl.
[0213] In a preferred embodiment according to the invention, the aryl group comprises 3 to 20 carbon atoms. In a preferred variant, the aryl moiety comprises 6 to 15 ring atoms. In an even more preferred embodiment, the aryl group comprises 6 to 10 carbon atoms.
[0214] Most preferred according to the present invention is a monocyclic C3-C10 aryl group. Most preferred is a monocyclic C3-C7 aryl group.
[0215] Typical aryl groups include, but are not limited to, benzene, phenyl, biphenyl, naphthyl (such as 1- or 2-naphthyl), tetrahydronaphthyl, fluorenyl, indenyl, and phenanthrenyl. Typical carboaryl moieties also include, but are not limited to, groups derived from aceanthrylene, acenaphthylene, acephenanthrylene, anthracene, azulene, benzene, chrysene, hexabenzophenone, fluoranthene, fluorene, hexacene, hexaphene, hexalene, as-indacene, s-indacene, indane, indene, naphthalene, octacene ... taphene), octalene, ovalene, pentane-2,4-diene, pentacene, cyclopentadiene, pentaphene, perylene, phenalene, phenanthrene, picene, pleiadene, pyrene, pyranthrene, rubicene, triphenylene, trinaphthalene, etc.
[0216] Preferred aromatic polycyclic aryl groups or aryl groups according to the present invention include, but are not limited to, naphthalene, biphenyl and the like.
[0217] The aryl moieties or groups as defined above may be further substituted.
[0218] According to the present invention, the term "arylalkyl" refers to an acyclic alkyl group, either alone or as part of another substituent, in which one of the hydrogen atoms attached to a carbon atom (usually a terminal or sp carbon atom) is replaced by an aryl group as defined herein. In other words, arylalkyl can also be considered to be an alkyl group substituted with an aryl group. Typical arylalkyl groups include, but are not limited to, benzyl, 2-phenylethane-1-yl, 2-phenylethene-1-yl, naphthylmethyl, 2-naphthylethane-1-yl, 2-naphthylethene-1-yl, naphthylbenzyl, 2-naphthylphenylethane-1-yl, etc.
[0219] The term "heteroarylalkyl" alone or as part of another substituent refers to a cyclic alkyl group in which one of the hydrogen atoms attached to the carbon atom is replaced by a heteroaryl group. In a preferred embodiment according to the present invention, the heteroarylalkyl group is a 6- to 20-membered heteroarylalkyl group, for example, the alkyl, alkenyl or alkynyl group of the heteroarylalkyl group is a C1-C6 alkyl group and the heteroaryl group is a 5- to 15-membered heteroaryl group. In other embodiments, the heteroarylalkyl group is a 6- to 13-membered heteroarylalkyl group, for example, the alkyl, alkenyl or alkynyl group is a C1-C3 alkyl group and the heteroaryl group is a 5- to 10-membered heteroaryl group.
[0220] According to the present invention, the term "heterocycloalkyl" alone or as part of another substituent refers to a saturated or mono- or poly-unsaturated non-aromatic cyclic monovalent hydrocarbon radical in which one or more carbon atoms are independently replaced by the same or different heteroatoms. Typical heteroatoms replacing carbon atoms include, but are not limited to, N, P, O, S, Si, etc. Typical heterocycloalkyls include, but are not limited to, groups derived from epoxides, aziridines, thiopyrans, imidazolidines, morpholines, piperazines, piperidines, pyrazolidines, pyrrolidinones, quinuclidines, etc.
[0221] In a preferred embodiment according to the invention, the heterocycloalkyl moiety or group comprises 3 to 20 ring atoms. In a preferred variant, the heterocycloalkyl moiety comprises 6 to 15 ring atoms. In an even more preferred embodiment, the heterocycloalkyl moiety comprises 6 to 10 carbon atoms.
[0222] The heterocycloalkyl moiety may exist as a monocyclic compound having only a single ring, or as a polycyclic compound having two or more rings such as a bicyclic, tricyclic, or spirocyclic ring.
[0223] Preferably, the term "heterocycloalkyl" includes three- to seven-membered saturated or mono- or polyunsaturated heterocycloalkyl moieties containing one, two, three or four heteroatoms selected from the group consisting of O, N and S. These heteroatoms may occupy any position in the heterocycloalkyl ring.
[0224] In a preferred variation, the term "heterocycloalkyl" includes a three-membered to ten-membered monocyclic heterocycloalkyl, or a nine-membered to twelve-membered polycyclic heterocycloalkyl. In other still more preferred variations, the heterocycloalkyl moiety comprises a five-membered, six-membered or seven-membered monocyclic heterocycloalkyl moiety, or a nine-membered to twelve-membered bicyclic heterocycloalkyl moiety.
[0225] Most preferred according to the invention are monocyclic heterocycloalkyl groups containing 3 to 12 carbon atoms.Most preferred are monocyclic heterocycloalkyl groups having 5 to 7 ring atoms.
[0226] Typical heterocycloalkyl moieties include, but are not limited to, five-membered or six-membered saturated or monounsaturated heterocycloalkyl groups containing one or two nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms as ring members, including 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-ox ... oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 1-piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxane-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl and the like.
[0227] The heterocycloalkyl moieties or groups as defined above may be further substituted.
[0228] According to the present invention, the term "heteroaryl" by itself or as part of another substituent refers to a monovalent heteroaromatic group obtained by removing a hydrogen atom from a single atom of a heteroaromatic ring SY-stem. Typical heteroaryl groups or heteroaryls include, but are not limited to, those derived from acridine, β-carboline, chroman, chromium, cinnoline, furan, imidazole, indazole, indole, indoline, indolizine, isobenzofuran, isochromium, isoindole, isoindolin, isoquinoline, isothiazole, isoxazole, naphthyridine, oxadiazole, oxazole, bethridine, phenanthridine, phenanthroline, phenazine, phthalazine, pteridine, purine, pyran, pyrazine, pyrazole, pyridazine, pyridine, pyrimidine, pyrrole, thiazole, thiophene, triazole, xanthene, etc.
[0229] The heteroaryl moiety may exist as a monocyclic compound having only a single ring, or as a polycyclic compound having two or more rings.
[0230] In a preferred variation, the term "heteroaryl" includes a three- to ten-membered monocyclic heteroaryl, or a nine- to twelve-membered polycyclic heteroaryl. In other still more preferred variations, the heteroaryl moiety comprises a five-, six- or seven-membered monocyclic heteroaryl moiety, or a nine- to twelve-membered bicyclic heteroaryl moiety.
[0231] Preferably, the term "heteroaryl" includes three- to seven-membered monocyclic heteroaryl groups containing one, two, three or four heteroatoms selected from the group consisting of O, N and S. These heteroatoms may occupy any position in the heteroaryl ring.
[0232] In a preferred embodiment according to the invention, the heteroaryl moiety or group contains 3 to 20 ring atoms. In an even more preferred variant, the heteroaryl moiety contains 6 to 15 ring atoms. In a most preferred embodiment, the heteroaryl contains 6 to 10 ring atoms. Most preferred according to the invention is a monocyclic C3 -C7 heteroaryl.
[0233] Particularly preferred heteroaryl moieties or heteroaryl groups include, but are not limited to, those derived from furan, thiophene, pyrrole, benzothiophene, benzofuran, benzimidazole, indole, pyridine, pyrazole, quinoline, imidazole, oxazole, isoxazole and pyrazine.
[0234] Five-membered aromatic heteroaryl groups which contain, in addition to carbon atoms, one, two or three nitrogen atoms or one or two nitrogen atoms and one sulfur or oxygen atom as ring atoms include 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl and 1,3,4-triazol-2-yl.
[0235] Five-membered aromatic heteroaryl groups containing one, two, three or four nitrogen atoms as ring atoms include 1-, 2- or 3-pyrrolyl, 1-, 3- or 4-pyrazolyl, 1-, 2- or 4-imidazolyl, 1,2,3-[1H]-triazol-1-yl, 1,2,3-[2H]-triazol-2-yl, 1,2,3-[1H]-triazol-4-yl, 1,2,3-[1H]-triazol-5-yl, 1,2,3-[2H]-triazol-6-yl, 1,2,3-[2H]-triazol-7-yl, 1,2,3-[2H]-triazol-8-yl, 1,2,3-[2H]-triazol-9-yl, 1,2,3-[2H]-triazol-10-yl, 1,2,3-[2H]-triazol-20-yl, 1,2,3-[1H]-triazol-40-yl, 1,2,3-[1H]-triazol-50-yl, 1,2,3-[2H]-triazol-60-yl, 1,2,3-[2H]-triazol-70-yl, 1,2,3-[2H]-triazol-80-yl, 1,2,3-[2H]-triazol-90-yl, 1,2,3-[2H]-triazol-100-yl, 1,2,3-[2H]-triazol-20-yl, 1,2,3-[1H]-triazol-40-yl, 1,2,3-[1H]-triazol-50-yl, 1,2,3-[2H]-triazol-20-yl, 1,2, ]-triazol-4-yl, 1,2,4-[1H]-triazol-1-yl, 1,2,4-[1H]-triazol-3-yl, 1,2,4-[1H]-triazol-5-yl, 1,2,4-[4H]-triazol-4-yl, 1,2,4-[4H]-triazol-3-yl, [1H]-tetrazole-1-yl, [1H]-tetrazole-5-yl, [2H]-tetrazole-2-yl, [2H]-tetrazole-5-yl, and the like.
[0236] Five-membered aromatic heteroaryl groups containing as ring atoms a heteroatom selected from oxygen or sulfur and optionally one, two or three nitrogen atoms include 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 3- or 4-isoxazolyl, 3- or 4-isothiazolyl, 2-, 4- or 5-oxazolyl, 2-, 4- or 5-thiazolyl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,3,4-oxadiazol-2-yl.
[0237] Six-membered heteroaryl groups which contain, in addition to carbon atoms, one or two or one, two or three nitrogen atoms as ring atoms include, for example, 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,2,4-triazin-3-yl; 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl and 1,3,5-triazin-2-yl.
[0238] The heteroaryl moieties or groups as defined above may be further substituted.
[0239] In the context of the present application, the term "C-spiro" means a compound having at least two molecular rings with only one common atom. The simplest spiro compound is bicyclic (having only two rings) or has a bicyclic moiety as part of a larger ring system, in either case, the two rings are connected by a defined single common atom. A common atom connected to the participating rings distinguishes spiro compounds from other bicyclic structures: from isolated ring compounds (such as biphenyl) without connecting atoms, from condensed ring compounds (such as decalin) with two rings connected by two adjacent atoms, and from bridged ring compounds (such as norbornane) with two rings connected by two non-adjacent atoms. Spiro compounds can be completely carbocyclic (all carbon) or heterocyclic (with one or more non-carbon atoms, such as N, O and S). The common atom connecting two (or sometimes three) rings is referred to as a spiral atom. Preferably, the spiral atom is a carbon atom. More preferably, C-spiro compounds mean a compound of a complete carbocyclic (all carbon).
[0240] In the context of the present invention, the term "substituted" means that one or more hydrogen atoms of the free radical or group are independently replaced by the same or different substituents. In addition, the term "substituted" particularly provides one or more, i.e. two, three, four, five, six or even more substitutions commonly used in the art. However, it is generally known that substituents should be selected so that they do not have an adverse effect on the useful properties of the compound or its function.
[0241] In the context of the present invention, suitable substituents preferably include halogen, perfluoroalkyl, perfluoroalkoxy, alkyl, alkenyl, alkynyl, hydroxy, oxo, mercapto, alkylthio, alkoxy, aryl or heteroaryl, aryloxy or heteroaryloxy, arylalkyl or heteroarylalkyl, arylalkoxy or heteroarylalkoxy, amino, alkyl and dialkylamino, carbamoyl, alkylcarbonyl, carboxyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, arylcarbonyl, aryloxycarbonyl, alkylsulfonyl, arylsulfonyl, cycloalkyl, cyano, C1-C6 alkylthio, arylthiol, nitro, keto, acyl, borate or boroyl, phosphate or phosphonyl, sulfamoyl, sulfonyl, sulfinyl and combinations thereof.
[0242] Substituents or substituent groups for substituting saturated carbon atoms in the radicals or free radicals shown more preferably include, but are not limited to, halogen, hydroxy, alkyl, alkenyl, alkynyl, alkoxy, -NH 2 , amino (primary, secondary or tertiary), nitro, thiol, thioether, imine, cyano, amido, phosphono, phosphine, carboxyl, thiocarbonyl, sulfonyl, sulfonamide, ketone, aldehyde, ester, acetyl, acetoxy, carbamoyl, oxygen (O); haloalkyl (e.g., trifluoromethyl); aminoacyl and aminoalkyl; carbocyclic cycloalkyl, which can be a monocyclic or fused or non-fused polycyclic (e.g., cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl); or heterocycloalkyl, which can be a monocyclic or fused or non-fused polycyclic (e.g., pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl or thiazinyl); carbocyclic or heterocyclic, monocyclic or fused or non-fused polycyclic aromatic (e.g., phenyl, naphthyl, pyrrolyl, indolyl, furanyl, thienyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, benzimidazolyl, benzothienyl or benzofuranyl); -CO 2 CH 3 、-CONH 2 、-OCH 2 CONH 2 ;-SO 2 NH 2 、-OCHF 2 , -CF 3 、-OCF 3 .
[0243] According to the present invention, the substituents used to replace a particular group may in turn be further substituted, usually by one or more identical or different groups selected from the various groups noted above and defined in detail above. In the case of substituted combinations (such as substituted arylalkyl), either the aryl or alkyl may be substituted, or both the aryl and alkyl may be substituted by one or more substituents.
[0244] In a preferred variant, Z in general formula (V) is -O-R2' or amide'.
[0245] In a further preferred variant, R1' in the general formula (V) is CH 2 .
[0246] In a further preferred variant, R1' in the general formula (V) is C(alkyl) 2 .
[0247] In a further preferred variant, R1′ in the general formula (V) is O.
[0248] In a further preferred variant, R1′ in the general formula (V) is S.
[0249] In a further preferred variant, R1' in the general formula (V) is SO.
[0250] In a further preferred variant, R1' in the general formula (V) is SO 2 .
[0251] In a further preferred variant, R1' in the general formula (V) is NH.
[0252] In a further preferred variant, R1' in the general formula (V) is N(alkyl).
[0253] Most preferably, R1' in formula (V) is CH 2 or C(alkyl) 2 .
[0254] In a preferred variant, R2' in general formula (V) is H.
[0255] In a further preferred variant, R2' in the general formula (V) is methyl.
[0256] In a further preferred variant, R2' in the general formula (V) is ethyl.
[0257] In a further preferred variant, R2' in the general formula (V) is propyl.
[0258] In a further preferred variant, R2' in the general formula (V) is isopropyl.
[0259] In a further preferred variant, R2′ in the general formula (V) is butyl.
[0260] In a further preferred variant, R2′ in the general formula (V) is isobutyl.
[0261] In a further preferred variant, R2′ in the general formula (V) is tert-butyl.
[0262] In a further preferred variant, R2' in the general formula (V) is
[0263] In a further preferred variant, R2' in the general formula (V) is
[0264] In a preferred variation, R2' in the general formula (V) is (2-ethyl-hexyl).
[0265] In a further preferred variant, R2' in general formula (V) is phenyl.
[0266] Most preferably, R2' in general formula (V) is H or ethyl or isopropyl or 2-ethylhexyl or phenyl.
[0267] In a preferred variant, the amide ' in the general formula (V) is NH 2 .
[0268] In a further preferred variant, amide' in the general formula (V) is NH(alkyl), wherein alkyl is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl.
[0269] In a further preferred variant, the amide in the general formula (V) is N(alkyl) 2 , wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl.
[0270] In a further preferred variant, the amide' in the general formula (V) is -N(O-alkyl)(alkyl)(Weinreb amide), wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl.
[0271] In a further preferred variant, the amide' in general formula (V) is -N(OH)(H)(hydroxamic acid).
[0272] Most preferably, the amide in formula (V) is NH 2 、N(Methyl) 2 or N(ethyl) 2 or -N(O-alkyl)(alkyl)(Weinreb amide), wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, or -N(OH)(H)(hydroxamic acid).
[0273] In a preferred variant, R3' in formula (V) is H.
[0274] In a further preferred variant, R3' in the general formula (V) is methyl.
[0275] In a further preferred variant, R3' in the general formula (V) is ethyl.
[0276] In a further preferred variant, R3' in the general formula (V) is -O-methyl.
[0277] In a further preferred variant, R3' in the general formula (V) is -C(=O)-OH.
[0278] In a further preferred variant, R3' in the general formula (V) is -C(=O)-CH 3 .
[0279] In a further preferred variant, R3' in the general formula (V) is -C(=O)-C 3 H 7 .
[0280] In a further preferred variant, R3' in general formula (V) is -C(=O)-O-methyl.
[0281] Most preferably, R3' in formula (V) is H or methyl or -O-methyl.
[0282] In a preferred variation according to the first aspect of the present invention, the mycosporin-like amino acid compound (b) of general formula (V) is an acid compound or an ester compound represented by general formula (VII):
[0283]
[0284] wherein R1′, R2′, R3′, R4′, R5′ and R6′ have the same meanings as defined herein for Formula (V).
[0285] In a preferred variant according to the first aspect of the present invention, the mycosporin-like amino acid compound (b) of general formula (V) is an acid compound represented by general formula (VII-acid):
[0286]
[0287] wherein R1′, R3′, R4′, R5′ and R6′ have the same meanings as defined herein for Formula (V).
[0288] Such mycosporin-like amino acid compounds are particularly light-stable and temperature-stable compounds and show stability in pH solutions or in different emulsion types and do not degrade.
[0289] In particular, the mycosporin-like amino acid compounds have better pH stability in a wider pH range, whereas their respective ester compounds are hydrolyzed and thus unstable in alkaline solutions above pH 9.
[0290] In addition, the mycosporin-like amino acid compounds are also more soluble in water than the corresponding ester compounds. Due to their better solubility in water, the mycosporin-like amino acid compounds can be incorporated into the aqueous phase of the emulsion at a higher concentration, thereby producing an improved antioxidant boosting effect in food, cosmetic or pharmaceutical preparations or home care products.
[0291] In a preferred variant according to the first aspect of the present invention, the mycosporin-like amino acid compound (b) of general formula (V) is an ester compound represented by general formula (VII-ester):
[0292]
[0293] wherein R1′, R3′, R4′, R5′ and R6′ have the same meanings as defined herein for Formula (V).
[0294] Preferably, the alkyl residue in the general formula (VII-ester) is methyl or ethyl or propyl or isopropyl or butyl or isobutyl or tert-butyl. Most preferably, the alkyl residue in the general formula (VII-ester) is methyl. Such ester compounds are particularly stable.
[0295] In an alternative preferred variant according to the first aspect of the present invention, the mycosporin-like amino acid compound (b) of general formula (V) is an amide compound represented by general formula (VIII):
[0296]
[0297] wherein R1′, Amide′, R3′, R4′, R5′ and R6′ have the same meanings as defined herein for Formula (V).
[0298] In a more preferred variant according to the first aspect of the present invention, the mycosporin-like amino acid compound (b) of general formula (V) is an amide compound represented by general formula (VIII-amide):
[0299]
[0300] wherein R1′, R3′, R4′, R5′ and R6′ have the same meanings as defined herein for formula (V), and R11′ and R12′ are independently selected from the group consisting of H, OH and alkyl.
[0301] In a preferred variant according to the first aspect of the invention, in the general formula (VIII-amide), R11′ and / or R12′ is H.
[0302] In a further preferred variant, R11′ alkyl and R12′ alkyl in the general formula (VIII-amide) are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl.
[0303] Preferably, R11′ and / or R12′ in the general formula (VIII-amide) are each H or are each methyl.
[0304] In a still more preferred variation, the mycosporin-like amino acid compound (b) of general formula (V) is a Weinreb amide compound represented by the general formula (VIII-Weinreb amide):
[0305]
[0306] wherein R1′, R3′, R4′, R5′ and R6′ have the same meanings as defined herein for Formula (V).
[0307] In a preferred variant, the alkyl residue in the general formula (VIII-Weinreb amide) is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, more preferably, the alkyl residue is methyl.
[0308] Alternatively, in a still more preferred variation, the mycosporin-like amino acid compound (b) of general formula (V) is a hydroxamic acid compound represented by the general formula (VIII-hydroxamic acid derivative):
[0309]
[0310] wherein R1′, R3′, R4′, R5′ and R6′ have the same meanings as defined herein for Formula (V).
[0311] Alternatively, in a further preferred variant, the mycosporin-like amino acid compound (b) of general formula (V) is an alkylated hydroxamic acid compound represented by the general formula (VIII-alkylated hydroxamic acid derivative):
[0312]
[0313] wherein R1′, R3′, R4′, R5′ and R6′ have the same meanings as defined herein for Formula (V).
[0314] In a preferred variant, the alkyl residue in the general formula (VIII - alkylated hydroxamic acid derivative) is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, more preferably, the alkyl group is methyl.
[0315] In an alternative preferred variant, the mycosporin-like amino acid compound (b) is represented by the general formula (A):
[0316]
[0317] wherein R1′, R3′, R4′, R5′ and R6′ have the same meanings as defined herein for Formula (V).
[0318] In the present invention, the same preferred variants as defined herein for the mycosporin-like amino acid compounds according to general formula (V) apply analogously to the mycosporin-like amino acid compounds according to general formula (VII) or (VIII) and variants thereof or general formula (A).
[0319] In a further preferred variant, R1″ in the general formula (VI) is CH 2 .
[0320] In a further preferred variant, R1″ in the general formula (VI) is C(alkyl) 2 .
[0321] In a further preferred variant, R1″ in the general formula (VI) is O.
[0322] In a further preferred variant, R1″ in the general formula (VI) is S.
[0323] In a further preferred variant, R1″ in the general formula (VI) is SO.
[0324] In a further preferred variant, R1″ in the general formula (VI) is SO 2 .
[0325] In a further preferred variant, R1″ in the general formula (VI) is NH.
[0326] In a further preferred variant, R1″ in the general formula (VI) is N(alkyl).
[0327] Most preferably, R1" in the general formula (VI) is CH 2 or C(alkyl) 2 .
[0328] In a preferred variant, R2" in the general formula (VI) is -CH 2 -OH.
[0329] In a further preferred variant, R2″ in the general formula (VI) is —C(═O)—OY.
[0330] In a further preferred variant, R2" in the general formula (VI) is -C(=O)-amide".
[0331] Most preferably, R2" in the general formula (VI) is -C(=O)-OY or -C(=O)-amide".
[0332] In a further preferred variant, X in the general formula (VI) is CH 2 .
[0333] In a further preferred variant, X in the general formula (VI) is C═O.
[0334] In a further preferred variant, X in the general formula (VI) is O.
[0335] In a further preferred variant, X in the general formula (VI) is S.
[0336] In a further preferred variant, X in the general formula (VI) is SO.
[0337] In a further preferred variant, X in the general formula (VI) is SO 2 .
[0338] In a further preferred variant, X in the general formula (VI) is NH.
[0339] In a further preferred variant, X in the general formula (VI) is N(alkyl), wherein alkyl is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl.
[0340] Most preferably, X in formula (VI) is S, SO or SO 2 .
[0341] In a preferred variant, Y in formula (VI) is H.
[0342] In a further preferred variant, Y in the general formula (VI) is methyl.
[0343] In a further preferred variant, Y in the general formula (VI) is ethyl.
[0344] In a further preferred variant, Y in the general formula (VI) is propyl.
[0345] In a further preferred variant, Y in the general formula (VI) is isopropyl.
[0346] In a further preferred variant, Y in the general formula (VI) is butyl.
[0347] In a further preferred variant, Y in the general formula (VI) is isobutyl.
[0348] In a further preferred variant, Y in the general formula (VI) is tert-butyl.
[0349] In a further preferred variant, Y in the general formula (VI) is
[0350] In a further preferred variant, Y in the general formula (VI) is
[0351] In a preferred variant, Y in formula (VI) is (2-ethyl-hexyl).
[0352] In a further preferred variant, Y in the general formula (VI) is phenyl.
[0353] Most preferably, Y in formula (VI) is H or ethyl or isopropyl or 2-ethylhexyl or phenyl.
[0354] In a preferred variant, the amide in the general formula (VI) is NH2 .
[0355] In a further preferred variant, the "amide" in the general formula (VI) is NH(alkyl), wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl.
[0356] In a further preferred variant, the "amide" in the general formula (VI) is N(alkyl) 2 , wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl.
[0357] In a further preferred variant, the "amide" in the general formula (VI) is -N(O-alkyl)(alkyl)(Weinreb amide), wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl.
[0358] In a further preferred variant, the "amide" in general formula (V) is -N(OH)(H)(hydroxamic acid).
[0359] Most preferably, the amide in formula (V) is NH 2 、N(Methyl) 2 or N(ethyl)2 or -N(O-alkyl)(alkyl)(Weinreb amide), wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, or -N(OH)(H)(hydroxamic acid).
[0360] In a more preferred variant according to the first aspect of the present invention, the mycosporin-like amino acid compound (b) is an alcohol compound represented by the general formula (IX-alcohol):
[0361]
[0362] wherein R1", X, R4", R5" and R6" have the same meanings as defined herein for Formula (VI).
[0363] Alternatively, in a more preferred variant according to the first aspect of the present invention, the mycosporin-like amino acid compound (b) of general formula (VI) is an acid compound represented by general formula (IX-acid):
[0364]
[0365] wherein R1", X, R4", R5" and R6" have the same meanings as defined herein for Formula (VI).
[0366] Alternatively, in a more preferred variant according to the first aspect of the present invention, the mycosporin-like amino acid compound (b) of the general formula (VI) is an ester compound represented by the general formula (VII-ester):
[0367]
[0368] wherein R1", X, R4", R5" and R6" have the same meanings as defined herein for Formula (VI).
[0369] Preferably, the alkyl residue in the general formula (VII-ester) is methyl or ethyl or propyl or isopropyl or butyl or isobutyl or tert-butyl, more preferably, the alkyl residue is methyl.
[0370] In an alternative more preferred variant according to the first aspect of the present invention, the mycosporin-like amino acid compound (b) of general formula (VI) is an amide compound represented by general formula (X):
[0371]
[0372] wherein R1", amide", R4", R5" and R6" have the same meanings as defined herein for formula (VI).
[0373] In an alternative more preferred variant according to the first aspect of the present invention, the mycosporin-like amino acid compound (b) of general formula (VI) is an amide compound represented by the general formula (X-amide):
[0374]
[0375] wherein R1″, X, R4″, R5″ and R6″ have the same meanings as defined above for general formula (VI), and R11″ and R12″ are independently selected from the group consisting of H, OH and alkyl. In a preferred variant according to the first aspect of the invention, in the general formula (X-amide), R11″ and R12″ are H.
[0376] Preferably, R11" alkyl and / or R12" alkyl in the general formula (X-amide) is methyl or ethyl or propyl or isopropyl or butyl or isobutyl or butyl.
[0377] Preferably, R11′ and / or R12′ in the general formula (X-amide) are each H or are each methyl.
[0378] In a still more preferred variation, the mycosporin-like amino acid compound (b) of formula (VI) is a Weinreb amide compound represented by the general formula (X-Weinreb amide):
[0379]
[0380] wherein R1", X, R4", R5" and R6" have the same meanings as defined herein for Formula (VI).
[0381] In a preferred variant, the alkyl residue in the general formula (X-Weinreb amide) is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, more preferably, the alkyl residue is methyl.
[0382] Alternatively, in a still more preferred variation, the mycosporin-like amino acid compound (b) of general formula (VI) is a hydroxamic acid compound represented by the general formula (X-hydroxamic acid derivative):
[0383]
[0384] wherein R1", X, R4", R5" and R6" have the same meanings as defined herein for Formula (VI).
[0385] Alternatively, in a further preferred variant, the mycosporin-like amino acid compound (b) of general formula (VI) is an alkylated hydroxamic acid compound represented by the general formula (VIII - alkylated hydroxamic acid derivative):
[0386]
[0387] wherein R1", X, R4", R5" and R6" have the same meanings as defined herein for Formula (VI).
[0388] In a preferred variation, the alkyl residue in the formula (X-alkylated hydroxamic acid derivative) is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and butyl, more preferably, the alkyl residue is methyl.
[0389] In the present invention, the same preferred variants as defined herein for the mycosporin-like amino acid compounds according to general formula (VI) apply analogously to the mycosporin-like amino acid compounds according to general formula (IX) or (X) and variants thereof.
[0390] In the following and throughout the specification, the term "according to the general formula YZ and variants thereof" includes any subformula of said general formula as disclosed herein. Thus, variants of the general formula (V) and (VI) as defined herein include formula (VII), formula (VIII), formula (IX) and formula (X) as defined herein. Variants of the general formula (VII) and (VIII) as defined herein include subformula (VII-acid), subformula (VII-ester), subformula (VIII-amide), subformula (VIII-Weinreb amide), subformula (VIII-hydroxamic acid derivative) and subformula (VIII-alkylated hydroxamic acid derivative) as defined herein. Variants of the general formula (IX) and (X) as defined herein include formula (IX-acid), formula (IX-ester), formula (X-amide), formula (X-Weinreb amide), formula (X-hydroxamic acid derivative) and formula (X-alkylated hydroxamic acid derivative) as defined herein.
[0391] In a further preferred variant, in the general formula (VI), (IX), (X) and variants thereof, X is selected from the group consisting of: CH 2 , unsubstituted or substituted CH(alkyl), unsubstituted or substituted C(alkyl) 2 , unsubstituted or substituted CH(alkenyl), unsubstituted or substituted CH(alkynyl), unsubstituted or substituted CH(alkoxy), unsubstituted or substituted CH(alkylthio), unsubstituted or substituted CH(cycloalkyl), unsubstituted or substituted CH(aryl), unsubstituted or substituted CH(heterocycloalkyl), unsubstituted or substituted CH(heteroaryl), -CR7"R8", C=O, S, SO, SO 2 , NH, unsubstituted or substituted N(alkyl), unsubstituted or substituted N(alkenyl), unsubstituted or substituted N(alkynyl), unsubstituted or substituted N(alkoxy), unsubstituted or substituted N(alkylthio), unsubstituted or substituted N(cycloalkyl), unsubstituted or substituted N(aryl), unsubstituted or substituted N(heterocycloalkyl), unsubstituted or substituted N(heteroaryl), and unsubstituted or substituted C-spiro.
[0392] In further preferred variants according to the first aspect of the present invention, the mycosporin-like amino acid compound is a compound according to general formula (V), wherein
[0393] -Z is -O-R2' or amide'; and / or
[0394] -R1' is selected from the group consisting of: CH 2 、C(alkyl) 2 , O, S, SO, SO 2 , NH and N(alkyl); and / or
[0395] -R2' is selected from the group consisting of: H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl,
[0396] (2-ethyl-hexyl) and phenyl; or
[0397] -amide' is selected from the group consisting of: NH 2 、NH(alkyl), N(alkyl) 2 , -N(O-alkyl)(alkyl)(Weinreb amide) and -N(OH)(H)(hydroxamic acid); and / or
[0398] -R3' is selected from the group consisting of: H, methyl, ethyl, -O-methyl, -C(=O)-
[0399] OH, -C(=O)-CH 3 , -C(=O)-C 3 H 7 and -C(=O)-O-methyl; and / or
[0400] - the substituents R4', R5' and R6' have the same meanings as defined for formula (V);
[0401] - wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl.
[0402] In another preferred variant according to the first aspect of the present invention, the mycosporin-like amino acid compound is a compound according to general formula (VII) or (VIII), wherein
[0403] -R1' is selected from the group consisting of: CH 2 、C(alkyl) 2 , O, S, SO, SO 2 , NH and N(alkyl); and / or
[0404] -R2' is selected from the group consisting of: H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, (2-ethyl-hexyl) and phenyl; or
[0406] -amide' is selected from the group consisting of: NH 2 、NH(alkyl), N(alkyl) 2 , -N(O-alkyl)(alkyl)(Weinreb amide) and -N(OH)(H)(hydroxamic acid); and / or
[0407] -R3' is selected from the group consisting of: H, methyl, ethyl, -O-methyl, -C(=O)-
[0408] OH, -C(=O)-CH 3 , -C(=O)-C 3 H 7 and -C(=O)-O-methyl; and / or
[0409] - the substituents R4', R5' and R6' have the same meanings as defined for formula (V);
[0410] - wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl.
[0411] In another preferred variant according to the first aspect of the present invention, the mycosporin-like amino acid compound is a compound according to general formula (VI), wherein
[0412] -R1" is selected from the group consisting of: CH 2 、C(alkyl) 2 , O, S, SO, SO 2 , NH and N(alkyl); and / or
[0413] -R2" is selected from the group consisting of: -CH 2 -OH, -C(=O)-OY and -C(=O)-amide
[0414] "; and / or
[0415] -X Select the group consisting of: CH 2 、C=O、O、S、SO、SO 2 , NH and N(alkyl); and / or
[0416] -Y is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, (2-ethyl-hexyl) and phenyl; and / or
[0418] -amide" is selected from the group consisting of: NH 2 、NH(alkyl), N(alkyl) 2 , -N(O-alkyl)(alkyl)(Weinreb amide) and -N(OH)(H)(hydroxamic acid); and / or
[0419] - the substituents R4", R5" and R6" have the same meanings as defined for formula (VI);
[0420] - wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl.
[0421] In further preferred variants according to the first aspect of the present invention, the mycosporin-like amino acid compound is a compound according to general formula (V), wherein
[0422] -Z is -O-R2' or amide'; and / or
[0423] -R1' is selected from the group consisting of: CH 2 and C(methyl) 2 ; and / or
[0424] -R2' is selected from the group consisting of: H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, (2-ethyl-hexyl) and phenyl; or
[0426] -amide' is selected from the group consisting of: NH 2 、NH(alkyl), N(alkyl) 2 , -N(O-alkyl)(alkyl)(Weinreb amide) and -N(OH)(H)(hydroxamic acid); and / or
[0427] -R3' is selected from the group consisting of: H, methyl, ethyl, -O-methyl, -C(=O)-
[0428] OH, -C(=O)-CH 3 , -C(=O)-C 3 H 7 and -C(=O)-O-methyl; and / or
[0429] - the substituents R4', R5' and R6' have the same meanings as defined for formula (V);
[0430] - wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl.
[0431] In another preferred variant according to the first aspect of the present invention, the mycosporin-like amino acid compound is a compound according to general formula (VII) or (VIII), wherein
[0432] -R1' is selected from the group consisting of: CH 2 and C(methyl) 2 ; and / or
[0433] -R2' is selected from the group consisting of: H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, (2-ethyl-hexyl) and phenyl; or
[0435] -amide' is selected from the group consisting of: NH 2 、NH(alkyl), N(alkyl) 2 , -N(O-alkyl)(alkyl)(Weinreb amide) and -N(OH)(H)(hydroxamic acid); and / or
[0436] -R3' is selected from the group consisting of: H, methyl, ethyl, -O-methyl, -C(=O)-
[0437] OH, -C(=O)-CH 3 , -C(=O)-C 3 H 7 and -C(=O)-O-methyl; and / or
[0438] - the substituents R4', R5' and R6' have the same meanings as defined for formula (V);
[0439] - wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl.
[0440] In another preferred variant according to the first aspect of the present invention, the mycosporin-like amino acid compound is a compound according to general formula (VI), wherein
[0441] -R1" is selected from the group consisting of: CH 2 and C(methyl) 2 ; and / or
[0442] -R2" is selected from the group consisting of: -CH 2 -OH, -C(=O)-OY and -C(=O)-amide
[0443] "; and / or
[0444] -X Select the group consisting of: CH 2 、C=O、O、S、SO、SO 2 , NH and N(alkyl); and / or
[0445] -Y is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, (2-ethyl-hexyl) and phenyl; and / or
[0447] -amide" is selected from the group consisting of: NH 2 、NH(alkyl), N(alkyl)2 , -N(O-alkyl)(alkyl)(Weinreb amide) and -N(OH)(H)(hydroxamic acid); and / or
[0448] - the substituents R4", R5" and R6" have the same meanings as defined for formula (VI);
[0449] - wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl.
[0450] In a still more preferred variant according to the invention, the food, cosmetic or pharmaceutical preparation or household care product comprises at least one mycosporin-like amino acid compound selected from the group consisting of the following compounds I-1 to I-128 according to the general formula (V) and compounds II-1 to II-192 according to the general formula (VI):
[0451] Table 1 :
[0452]
[0453]
[0454]
[0455]
[0456]
[0457]
[0458]
[0459]
[0460] or a tautomer or stereoisomer or salt of the aforementioned compound, or any mixture of the aforementioned compounds.
[0461] In the mycosporin-like amino acid compounds of Table 1, the phenyl ring may be unsubstituted or substituted. The substituents R4', R5', R6', R4", R5", R6", amide', Y, amide" and alkyl have the same meanings as defined above for the mycosporin-like amino acid compounds according to general formula (V) or (VI).
[0462] Particularly preferred are those mycosporin-like amino acid compounds wherein in the general formula (V), R1' is CH 2 or C(methyl) 2 , or wherein in the general formula (VI), R1' is CH 2 or C(methyl)2 :
[0463] Table 2 :
[0464]
[0465]
[0466]
[0467] or a tautomer or stereoisomer or salt of the aforementioned compound, or any mixture of the aforementioned compounds.
[0468] In the mycosporin-like amino acid compounds of Table 2, the phenyl ring may be unsubstituted or substituted. The substituents R4', R5', R6', R4", R5", R6", amide', Y, amide" and alkyl have the same meanings as defined above for the mycosporin-like amino acid compounds according to general formula (V) or (VI).
[0469] Preferably, in the mycosporin-like amino acid compounds of general formula (V) or general formula (VI) specified in Table 1 and Table 2
[0470] -R2' is selected from the group consisting of: H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, (2-ethylhexyl) and phenyl;
[0472] -amide' is selected from the group consisting of: NH 2 、NH(alkyl), N(alkyl) 2 , -N(O-alkyl)(alkyl)(Weinreb amide), and -N(OH)(H)(hydroxamic acid);
[0473] -Y is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, (2-ethylhexyl) and phenyl;
[0475] -amide" is selected from the group consisting of: NH 2 、NH(alkyl), N(alkyl) 2 , -N(O-alkyl)(alkyl)(Weinreb amide), and -N(OH)(H)(hydroxamic acid); and
[0476] - Alkyl is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl.
[0477] In the most preferred variants according to the first aspect of the present invention, the mycosporin-like amino acid compound is a compound according to formula (V) and its variants or formula (VI) and its variants, wherein R1′ or R1″ is CH 2 Such mycosporin-like amino acid compounds have particularly good water solubility.
[0478] In a further preferred variant according to the first aspect of the present invention, the mycosporin-like amino acid compound is a compound according to the general formula (VI), (IX), (X) and variants thereof, wherein X is selected from S, SO and SO 2 Composed of groups.
[0479] In still more preferred variations according to the first aspect of the invention, the mycosporin-like amino acid compound is a compound according to general formula (VI), (IX), (X) and variations thereof, wherein X is S. However, the S atom in said compound is easily oxidized.
[0480] In the most preferred variants according to the first aspect of the present invention, the mycosporin-like amino acid compound is a compound according to the general formula (VI), (IX), (X) and variants thereof, wherein X is SO or SO 2 Such mycosporin-like amino acid compounds are particularly stable due to their oxidation state.
[0481] In a further preferred variant according to the invention, in the general formulae (V) to (X) and their variants, n is 1.
[0482] In a more preferred variant according to the first aspect of the invention, the mycosporin-like amino acid compound is a compound according to general formula (V), wherein
[0483] -Z is -O-R2' or amide'; and / or
[0484] -R1' is CH 2 or C(methyl) 2 ; and / or
[0485] - R2' is H or ethyl or isopropyl or 2-ethylhexyl or phenyl; or
[0486] -Amide' is NH 2 or N(methyl) 2 or N(ethyl) 2 or -N(O-alkyl)(alkyl)(Weinreb amide) or -N(OH)(H)(hydroxamic acid); and / or
[0487] -R3' is H or -O-methyl or -C(=O)-OH or -C(=O)-CH 3 or -C(=O)-O-methyl; and
[0488] and / or
[0489] - the substituents R4', R5' and R6' have the same meanings as defined for formula (V);
[0490] - wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl.
[0491] In a more preferred variant according to the first aspect of the invention, the mycosporin-like amino acid compound is a compound according to general formula (VII) or (VIII), wherein
[0492] -R1' is CH 2 or C(methyl) 2 ; and / or
[0493] - R2' is H or ethyl or isopropyl or 2-ethylhexyl or phenyl; or
[0494] -Amide' is NH 2 or N(methyl) 2 or N(ethyl) 2 or -N(O-alkyl)(alkyl)(Weinreb amide) or -N(OH)(H)(hydroxamic acid); and / or
[0495] -R3' is H or -O-methyl or -C(=O)-OH or -C(=O)-CH 3 or -C(=O)-O-methyl; and
[0496] and / or
[0497] - the substituents R4', R5' and R6' have the same meanings as defined for formula (V);
[0498] - wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl.
[0499] In a more preferred variant according to the first aspect of the invention, the mycosporin-like amino acid compound is a compound according to general formula (VI), wherein
[0500] -R1" is CH 2 or C(methyl) 2 ; and / or
[0501] -R2" is -C(=O)-OY or -C(=O)-amide"; and / or
[0502] -X is S, SO or SO 2 ; and / or
[0503] -Y is optionally H or ethyl or isopropyl or 2-ethylhexyl or phenyl; or
[0504] -amide" is NH 2 or N(methyl) 2 or N(ethyl) 2 or -N(O-alkyl)(alkyl)(Weinreb amide) or -N(OH)(H)(hydroxamic acid); and / or
[0505] - the substituents R4", R5" and R6" have the same meanings as defined for formula (VI);
[0506] - wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and butyl.
[0507] The phenyl ring in the mycosporin-like amino acid compounds according to general formula (V) to (X) and variations thereof may be unsubstituted or substituted.
[0508] In a preferred variant, the phenyl ring in the mycosporin-like amino acid compounds according to general formulae (V) to (X) and their variants is unsubstituted, i.e., the substituents R4′, R5′ and R6′ on the phenyl ring in general formula (V) are H; or the substituents R4″, R5″ and R6″ on the phenyl ring in general formula (VI) are H.
[0509] In a further preferred variant, the phenyl ring in the mycosporin-like amino acid compounds according to the general formulae (V) to (X) and variants thereof is substituted.
[0510] Most preferably, the phenyl ring in the mycosporin-like amino acid compound according to formula (V), (VII), (VIII) and variants thereof is unsubstituted, i.e., the substituents R4', R5' and R6' are each H. Alternatively, most preferably, the phenyl ring in the mycosporin-like amino acid compound according to formula (VI), (IX), (X) and variants thereof is unsubstituted, i.e., the substituents R4", R5" and R6" are each H. The compounds have improved water solubility.
[0511] Preferably, the phenyl ring in the mycosporin-like amino acid compounds according to general formula (V) to (X) and variants thereof is mono-, di- or tri-substituted.
[0512] In still more preferred variants according to the first aspect of the invention, the mycosporin-like amino acid is a compound according to the general formula (V), (VII), (VIII) and variants thereof, wherein the substituents R4', R5' and R6', which may be identical or different, are independently selected from the group consisting of: H; OH; alkyl, preferably methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl; alkoxy, preferably O-methyl, O-ethyl or O-butyl; -S(=O)2 OH; and sulfonyl.
[0513] Still more preferably, the substituents R4', R5' and R6', which may be the same or different, in the general formula (V), (VII), (VIII) and their variants are independently selected from the group consisting of: H, OH, methyl, O-methyl, -S(=O) 2 OH and sulfonyl.
[0514] Alternatively, the mycosporin-like amino acid compound is a compound according to the general formula (VI), (IX), (X) and variants thereof, wherein the substituents R4", R5" and R6" which may be the same or different are independently selected from the group consisting of: H; OH; alkyl, preferably methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl; alkoxy, preferably O-methyl, O-ethyl or O-butyl; -S(=O) 2 OH; and sulfonyl.
[0515] Still more preferably, the substituents R4", R5" and R6" in the general formula (VI), (IX), (X) and their variants, which may be the same or different, are independently selected from the group consisting of: H, OH, methyl, O-methyl, -S(=O) 2 OH and sulfonyl.
[0516] In the general formulae (V) to (X) and their variants, the following substitution patterns are particularly preferred:
[0517] R4′=H and R5′=H and R6′=H; or
[0518] R4'=H and R5'=H and R6'=OH; or
[0519] R4'=H and R5'=H and R6'=methyl; or
[0520] R4′=H and R5′=H and R6′=O-methyl; or
[0521] R4'=H and R5'=H and R6'=-S(=O) 2 OH; or
[0522] R4'=H and R5'=H and R6'=sulfonyl; or
[0523] R4'=H and R5'=OH and R6'=H; or
[0524] R4'=H and R5'=OH and R6'=OH; or
[0525] R4'=H and R5'=OH and R6'=methyl; or
[0526] R4'=H and R5'=OH and R6'=O-methyl; or
[0527] R4'=H and R5'=OH and R6'=-S(=O) 2 OH; or
[0528] R4'=H and R5'=OH and R6'=sulfonyl; or
[0529] R4'=H and R5'=methyl and R6'=H; or
[0530] R4'=H and R5'=methyl and R6'=OH; or
[0531] R4'=H and R5'=methyl and R6'=methyl; or
[0532] R4'=H and R5'=methyl and R6'=O-methyl; or
[0533] R4'=H and R5'=methyl and R6'=-S(=O) 2 OH; or
[0534] R4'=H and R5'=methyl and R6'=sulfonyl; or
[0535] R4′=H and R5′=O-methyl and R6′=H; or
[0536] R4'=H and R5'=O-methyl and R6'=OH; or
[0537] R4'=H and R5'=O-methyl and R6'=methyl; or
[0538] R4′=H and R5′=O-methyl and R6′=O-methyl; or
[0539] R4'=H and R5'=O-methyl and R6'=-S(=O) 2 OH; or
[0540] R4'=H and R5'=O-methyl and R6'=sulfonyl; or
[0541] R4'=H and R5'=-S(=O) 2 OH and R6′=H; or
[0542] R4'=H and R5'=-S(=O) 2 OH and R6′=OH; or
[0543] R4'=H and R5'=-S(=O) 2 OH and R6' = methyl; or
[0544] R4'=H and R5'=-S(=O) 2 OH and R6'=O-methyl; or
[0545] R4'=H and R5'=-S(=O) 2 OH and R6'=-S(=O) 2 OH; or
[0546] R4'=H and R5'=-S(=O) 2 OH and R6' = sulfonyl; or
[0547] R4'=H and R5'=sulfonyl and R6'=H; or
[0548] R4'=H and R5'=sulfonyl and R6'=OH; or
[0549] R4'=H and R5'=sulfonyl and R6'=methyl; or
[0550] R4'=H and R5'=sulfonyl and R6'=O-methyl; or
[0551] R4'=H and R5'=sulfonyl and R6'=-S(=O) 2 OH; or
[0552] R4'=H and R5'=sulfonyl and R6'=sulfonyl; or
[0553] R4′=OH and R5′=H and R6′=H; or
[0554] R4'=OH and R5'=H and R6'=OH; or
[0555] R4'=OH and R5'=H and R6'=methyl; or
[0556] R4'=OH and R5'=H and R6'=O-methyl; or
[0557] R4'=OH and R5'=H and R6'=-S(=O) 2 OH; or
[0558] R4'=OH and R5'=H and R6'=sulfonyl; or
[0559] R4′=OH and R5′=OH and R6′=H; or
[0560] R4′=OH and R5′=OH and R6′=OH; or
[0561] R4'=OH and R5'=OH and R6'=methyl; or
[0562] R4′=OH and R5′=OH and R6′=O-methyl; or
[0563] R4'=OH and R5'=OH and R6'=-S(=O) 2 OH; or
[0564] R4'=OH and R5'=OH and R6'=sulfonyl; or
[0565] R4'=OH and R5'=methyl and R6'=H; or
[0566] R4'=OH and R5'=methyl and R6'=OH; or
[0567] R4'=OH and R5'=methyl and R6'=methyl; or
[0568] R4'=OH and R5'=methyl and R6'=O-methyl; or
[0569] R4'=OH and R5'=methyl and R6'=-S(=O) 2 OH; or
[0570] R4'=OH and R5'=methyl and R6'=sulfonyl; or
[0571] R4'=OH and R5'=O-methyl and R6'=H; or
[0572] R4'=OH and R5'=O-methyl and R6'=OH; or
[0573] R4'=OH and R5'=O-methyl and R6'=methyl; or
[0574] R4'=OH and R5'=O-methyl and R6'=O-methyl; or
[0575] R4'=OH and R5'=O-methyl and R6'=-S(=O) 2 OH; or
[0576] R4'=OH and R5'=O-methyl and R6'=sulfonyl; or
[0577] R4'=OH and R5'=-S(=O) 2 OH and R6′=H; or
[0578] R4'=OH and R5'=-S(=O) 2 OH and R6′=OH; or
[0579] R4'=OH and R5'=-S(=O) 2 OH and R6' = methyl; or
[0580] R4'=OH and R5'=-S(=O) 2 OH and R6'=O-methyl; or
[0581] R4'=OH and R5'=-S(=O) 2 OH and R6'=-S(=O) 2 OH; or
[0582] R4'=OH and R5'=-S(=O) 2 OH and R6' = sulfonyl; or
[0583] R4'=OH and R5'=sulfonyl and R6'=H; or
[0584] R4'=OH and R5'=sulfonyl and R6'=OH; or
[0585] R4'=OH and R5'=sulfonyl and R6'=methyl; or
[0586] R4'=OH and R5'=sulfonyl and R6'=O-methyl; or
[0587] R4'=OH and R5'=sulfonyl and R6'=-S(=O) 2 OH; or
[0588] R4'=OH and R5'=sulfonyl and R6'=sulfonyl; or
[0589] R4'=methyl and R5'=H and R6'=H; or
[0590] R4'=methyl and R5'=H and R6'=OH; or
[0591] R4'=methyl and R5'=H and R6'=methyl; or
[0592] R4'=methyl and R5'=H and R6'=O-methyl; or
[0593] R4'=methyl and R5'=H and R6'=-S(=O) 2 OH; or
[0594] R4'=methyl and R5'=H and R6'=sulfonyl; or
[0595] R4'=methyl and R5'=OH and R6'=H; or
[0596] R4'=methyl and R5'=OH and R6'=OH; or
[0597] R4'=methyl and R5'=OH and R6'=methyl; or
[0598] R4'=methyl and R5'=OH and R6'=O-methyl; or
[0599] R4'=methyl and R5'=OH and R6'=-S(=O) 2 OH; or
[0600] R4'=methyl and R5'=OH and R6'=sulfonyl; or
[0601] R4'=methyl and R5'=methyl and R6'=H; or
[0602] R4'=methyl and R5'=methyl and R6'=OH; or
[0603] R4'=methyl and R5'=methyl and R6'=methyl; or
[0604] R4'=methyl and R5'=methyl and R6'=O-methyl; or
[0605] R4'=methyl and R5'=methyl and R6'=-S(=O) 2 OH; or
[0606] R4'=methyl and R5'=methyl and R6'=sulfonyl; or
[0607] R4'=methyl and R5'=O-methyl and R6'=H; or
[0608] R4'=methyl and R5'=O-methyl and R6'=OH; or
[0609] R4'=methyl and R5'=O-methyl and R6'=methyl; or
[0610] R4'=methyl and R5'=O-methyl and R6'=O-methyl; or
[0611] R4'=methyl and R5'=O-methyl and R6'=-S(=O) 2 OH; or
[0612] R4'=methyl and R5'=O-methyl and R6'=sulfonyl; or
[0613] R4'=methyl and R5'=-S(=O) 2 OH and R6′=H; or
[0614] R4'=methyl and R5'=-S(=O) 2 OH and R6′=OH; or
[0615] R4'=methyl and R5'=-S(=O) 2 OH and R6' = methyl; or
[0616] R4'=methyl and R5'=-S(=O) 2 OH and R6'=O-methyl; or
[0617] R4'=methyl and R5'=-S(=O) 2 OH and R6'=-S(=O) 2 OH; or
[0618] R4'=methyl and R5'=-S(=O) 2 OH and R6' = sulfonyl; or
[0619] R4'=methyl and R5'=sulfonyl and R6'=H; or
[0620] R4'=methyl and R5'=sulfonyl and R6'=OH; or
[0621] R4'=methyl and R5'=sulfonyl and R6'=methyl; or
[0622] R4'=methyl and R5'=sulfonyl and R6'=O-methyl; or
[0623] R4'=methyl and R5'=sulfonyl and R6'=-S(=O) 2 OH; or
[0624] R4'=methyl and R5'=sulfonyl and R6'=sulfonyl; or
[0625] R4'=O-methyl and R5'=H and R6'=H; or
[0626] R4'=O-methyl and R5'=H and R6'=OH; or
[0627] R4'=O-methyl and R5'=H and R6'=methyl; or
[0628] R4'=O-methyl and R5'=H and R6'=O-methyl; or
[0629] R4'=O-methyl and R5'=H and R6'=-S(=O) 2 OH; or
[0630] R4'=O-methyl and R5'=H and R6'=sulfonyl; or
[0631] R4'=O-methyl and R5'=OH and R6'=H; or
[0632] R4'=O-methyl and R5'=OH and R6'=OH; or
[0633] R4'=O-methyl and R5'=OH and R6'=methyl; or
[0634] R4'=O-methyl and R5'=OH and R6'=O-methyl; or
[0635] R4'=O-methyl and R5'=OH and R6'=-S(=O) 2 OH; or
[0636] R4'=O-methyl and R5'=OH and R6'=sulfonyl; or
[0637] R4'=O-methyl and R5'=methyl and R6'=H; or
[0638] R4'=O-methyl and R5'=methyl and R6'=OH; or
[0639] R4'=O-methyl and R5'=methyl and R6'=methyl; or
[0640] R4'=O-methyl and R5'=methyl and R6'=O-methyl; or
[0641] R4'=O-methyl and R5'=methyl and R6'=-S(=O) 2 OH; or
[0642] R4'=O-methyl and R5'=methyl and R6'=sulfonyl; or
[0643] R4'=O-methyl and R5'=O-methyl and R6'=H; or
[0644] R4'=O-methyl and R5'=O-methyl and R6'=OH; or
[0645] R4'=O-methyl and R5'=O-methyl and R6'=methyl; or
[0646] R4'=O-methyl and R5'=O-methyl and R6'=O-methyl; or
[0647] R4'=O-methyl and R5'=O-methyl and R6'=-S(=O) 2 OH; or
[0648] R4'=O-methyl and R5'=O-methyl and R6'=sulfonyl; or
[0649] R4'=O-methyl and R5'=-S(=O) 2 OH and R6′=H; or
[0650] R4'=O-methyl and R5'=-S(=O) 2OH and R6′=OH; or
[0651] R4'=O-methyl and R5'=-S(=O) 2 OH and R6' = methyl; or
[0652] R4'=O-methyl and R5'=-S(=O) 2 OH and R6'=O-methyl; or
[0653] R4'=O-methyl and R5'=-S(=O) 2 OH and R6'=-S(=O) 2 OH; or
[0654] R4'=O-methyl and R5'=-S(=O) 2 OH and R6' = sulfonyl; or
[0655] R4'=O-methyl and R5'=sulfonyl and R6'=H; or
[0656] R4'=O-methyl and R5'=sulfonyl and R6'=OH; or
[0657] R4'=O-methyl and R5'=sulfonyl and R6'=methyl; or
[0658] R4'=O-methyl and R5'=sulfonyl and R6'=O-methyl; or
[0659] R4'=O-methyl and R5'=sulfonyl and R6'=-S(=O) 2 OH; or
[0660] R4'=O-methyl and R5'=sulfonyl and R6'=sulfonyl; or
[0661] R4'=-S(=O) 2 OH and R5′=H and R6′=H; or
[0662] R4'=-S(=O) 2 OH and R5′=H and R6′=OH; or
[0663] R4'=-S(=O) 2 OH and R5'=H and R6'=methyl; or
[0664] R4'=-S(=O) 2 OH and R5′=H and R6′=O-methyl; or
[0665] R4'=-S(=O) 2 OH and R5'=H and R6'=-S(=O) 2OH; or
[0666] R4'=-S(=O) 2 OH and R5'=H and R6'=sulfonyl; or
[0667] R4'=-S(=O) 2 OH and R5′=OH and R6′=H; or
[0668] R4'=-S(=O) 2 OH and R5′=OH and R6′=OH; or
[0669] R4'=-S(=O) 2 OH and R5'=OH and R6'=methyl; or
[0670] R4'=-S(=O) 2 OH and R5′=OH and R6′=O-methyl; or
[0671] R4'=-S(=O) 2 OH and R5'=OH and R6'=-S(=O) 2 OH; or
[0672] R4'=-S(=O) 2 OH and R5'=OH and R6'=sulfonyl; or
[0673] R4'=-S(=O) 2 OH and R5'=methyl and R6'=H; or
[0674] R4'=-S(=O) 2 OH and R5'=methyl and R6'=OH; or
[0675] R4'=-S(=O) 2 OH and R5'=methyl and R6'=methyl; or
[0676] R4'=-S(=O) 2 OH and R5'=methyl and R6'=O-methyl; or
[0677] R4'=-S(=O) 2 OH and R5'=methyl and R6'=-S(=O) 2 OH; or
[0678] R4'=-S(=O) 2 OH and R5'=methyl and R6'=sulfonyl; or
[0679] R4'=-S(=O) 2 OH and R5'=O-methyl and R6'=H; or
[0680] R4'=-S(=O) 2 OH and R5'=O-methyl and R6'=OH; or
[0681] R4'=-S(=O) 2 OH and R5'=O-methyl and R6'=methyl; or
[0682] R4'=-S(=O) 2 OH and R5′=O-methyl and R6′=O-methyl; or
[0683] R4'=-S(=O) 2 OH and R5'=O-methyl and R6'=-S(=O) 2 OH; or
[0684] R4'=-S(=O) 2 OH and R5'=O-methyl and R6'=sulfonyl; or
[0685] R4'=-S(=O) 2 OH and R5'=-S(=O) 2 OH= and R6′=H; or
[0686] R4'=-S(=O) 2 OH and R5'=-S(=O) 2 OH and R6'=OH; or
[0687] R4'=-S(=O) 2 OH and R5'=-S(=O) 2 OH and R6' = methyl; or
[0688] R4'=-S(=O) 2 OH and R5'=-S(=O) 2 OH and R6'=O-methyl; or
[0689] R4'=-S(=O) 2 OH and R5'=sulfonyl and R6'=H; or
[0690] R4'=-S(=O) 2 OH and R5'=sulfonyl and R6'=OH; or
[0691] R4'=-S(=O) 2 OH and R5'=sulfonyl and R6'=methyl; or
[0692] R4'=-S(=O) 2 OH and R5'=sulfonyl and R6'=O-methyl; or
[0693] R4'=sulfonyl and R5'=H and R6'=H; or
[0694] R4'=sulfonyl and R5'=H and R6'=OH; or
[0695] R4'=sulfonyl and R5'=H and R6'=methyl; or
[0696] R4'=sulfonyl and R5'=H and R6'=O-methyl; or
[0697] R4'=sulfonyl and R5'=H and R6'=-S(=O) 2 OH; or
[0698] R4'=sulfonyl and R5'=H and R6'=sulfonyl; or
[0699] R4'=sulfonyl and R5'=OH and R6'=H; or
[0700] R4'=sulfonyl and R5'=OH and R6'=OH; or
[0701] R4'=sulfonyl and R5'=OH and R6'=methyl; or
[0702] R4'=sulfonyl and R5'=OH and R6'=O-methyl; or
[0703] R4'=sulfonyl and R5'=OH and R6'=-S(=O) 2 OH; or
[0704] R4'=sulfonyl and R5'=OH and R6'=sulfonyl; or
[0705] R4'=sulfonyl and R5'=methyl and R6'=H; or
[0706] R4'=sulfonyl and R5'=methyl and R6'=OH; or
[0707] R4'=sulfonyl and R5'=methyl and R6'=methyl; or
[0708] R4'=sulfonyl and R5'=methyl and R6'=O-methyl; or
[0709] R4'=sulfonyl and R5'=methyl and R6'=-S(=O) 2 OH; or
[0710] R4'=sulfonyl and R5'=methyl and R6'=sulfonyl; or
[0711] R4'=sulfonyl and R5'=O-methyl and R6'=H; or
[0712] R4'=sulfonyl and R5'=O-methyl and R6'=OH; or
[0713] R4'=sulfonyl and R5'=O-methyl and R6'=methyl; or
[0714] R4'=sulfonyl and R5'=O-methyl and R6'=O-methyl; or
[0715] R4'=sulfonyl and R5'=O-methyl and R6'=-S(=O) 2 OH; or
[0716] R4'=sulfonyl and R5'=O-methyl and R6'=sulfonyl; or
[0717] R4'=sulfonyl and R5'=-S(=O) 2 OH and R6′=H; or
[0718] R4'=sulfonyl and R5'=-S(=O) 2 OH and R6′=OH; or
[0719] R4'=sulfonyl and R5'=-S(=O) 2 OH and R6' = methyl; or
[0720] R4'=sulfonyl and R5'=-S(=O) 2 OH and R6'=O-methyl; or
[0721] R4'=sulfonyl and R5'=sulfonyl and R6'=H; or
[0722] R4'=sulfonyl and R5'=sulfonyl and R6'=OH; or
[0723] R4'=sulfonyl and R5'=sulfonyl and R6'=methyl; or
[0724] R4'=sulfonyl and R5'=sulfonyl and R6'=O-methyl; or
[0725] R4"=H and R5"=H and R6"=H; or
[0726] R4"=H and R5"=H and R6"=OH; or
[0727] R4"=H and R5"=H and R6"=methyl; or
[0728] R4"=H and R5"=H and R6"=O-methyl; or
[0729] R4"=H and R5"=H and R6"=-S(=O) 2 OH; or
[0730] R4"=H and R5"=H and R6"=sulfonyl; or
[0731] R4"=H and R5"=OH and R6"=H; or
[0732] R4"=H and R5"=OH and R6"=OH; or
[0733] R4" = H and R5" = OH and R6" = methyl; or
[0734] R4"=H and R5"=OH and R6"=O-methyl; or
[0735] R4"=H and R5"=OH and R6"=-S(=O) 2 OH; or
[0736] R4"=H and R5"=OH and R6"=sulfonyl; or
[0737] R4"=H and R5"=methyl and R6"=H; or
[0738] R4"=H and R5"=methyl and R6"=OH; or
[0739] R4"=H and R5"=methyl and R6"=methyl; or
[0740] R4"=H and R5"=methyl and R6"=O-methyl; or
[0741] R4"=H and R5"=methyl and R6"=-S(=O) 2 OH; or
[0742] R4" = H and R5" = methyl and R6" = sulfonyl; or
[0743] R4"=H and R5"=O-methyl and R6"=H; or
[0744] R4"=H and R5"=O-methyl and R6"=OH; or
[0745] R4" = H and R5" = O-methyl and R6" = methyl; or
[0746] R4″=H and R5″=O-methyl and R6″=O-methyl; or
[0747] R4"=H and R5"=O-methyl and R6"=-S(=O) 2 OH; or
[0748] R4" = H and R5" = O-methyl and R6" = sulfonyl; or
[0749] R4"=H and R5"=-S(=O) 2 OH and R6″=H; or
[0750] R4"=H and R5"=-S(=O) 2 OH and R6″=OH; or
[0751] R4"=H and R5"=-S(=O) 2 OH and R6″=methyl; or
[0752] R4"=H and R5"=-S(=O) 2 OH and R6″=O-methyl; or
[0753] R4"=H and R5"=-S(=O) 2 OH and R6"=-S(=O) 2 OH; or
[0754] R4"=H and R5"=-S(=O) 2 OH and R6″=sulfonyl; or
[0755] R4"=H and R5"=sulfonyl and R6"=H; or
[0756] R4"=H and R5"=sulfonyl and R6"=OH; or
[0757] R4" = H and R5" = sulfonyl and R6" = methyl; or
[0758] R4" = H and R5" = sulfonyl and R6" = O-methyl; or
[0759] R4"=H and R5"=sulfonyl and R6"=-S(=O) 2 OH; or
[0760] R4"=H and R5"=sulfonyl and R6"=sulfonyl; or
[0761] R4"=OH and R5"=H and R6"=H; or
[0762] R4"=OH and R5"=H and R6"=OH; or
[0763] R4"=OH and R5"=H and R6"=methyl; or
[0764] R4"=OH and R5"=H and R6"=O-methyl; or
[0765] R4"=OH and R5"=H and R6"=-S(=O) 2 OH; or
[0766] R4"=OH and R5"=H and R6"=sulfonyl; or
[0767] R4"=OH and R5"=OH and R6"=H; or
[0768] R4″=OH and R5″=OH and R6″=OH; or
[0769] R4"=OH and R5"=OH and R6"=methyl; or
[0770] R4"=OH and R5"=OH and R6"=O-methyl; or
[0771] R4"=OH and R5"=OH and R6"=-S(=O) 2 OH; or
[0772] R4"=OH and R5"=OH and R6"=sulfonyl; or
[0773] R4"=OH and R5"=methyl and R6"=H; or
[0774] R4"=OH and R5"=methyl and R6"=OH; or
[0775] R4" = OH and R5" = methyl and R6" = methyl; or
[0776] R4" = OH and R5" = methyl and R6" = O-methyl; or
[0777] R4"=OH and R5"=methyl and R6"=-S(=O) 2 OH; or
[0778] R4" = OH and R5" = methyl and R6" = sulfonyl; or
[0779] R4"=OH and R5"=O-methyl and R6"=H; or
[0780] R4"=OH and R5"=O-methyl and R6"=OH; or
[0781] R4" = OH and R5" = O-methyl and R6" = methyl; or
[0782] R4″=OH and R5″=O-methyl and R6″=O-methyl; or
[0783] R4"=OH and R5"=O-methyl and R6"=-S(=O) 2 OH; or
[0784] R4" = OH and R5" = O-methyl and R6" = sulfonyl; or
[0785] R4"=OH and R5"=-S(=O) 2 OH and R6″=H; or
[0786] R4"=OH and R5"=-S(=O) 2 OH and R6″=OH; or
[0787] R4"=OH and R5"=-S(=O) 2 OH and R6″=methyl; or
[0788] R4"=OH and R5"=-S(=O) 2 OH and R6″=O-methyl; or
[0789] R4"=OH and R5"=-S(=O) 2 OH and R6"=-S(=O) 2 OH; or
[0790] R4"=OH and R5"=-S(=O) 2 OH and R6″=sulfonyl; or
[0791] R4"=OH and R5"=sulfonyl and R6"=H; or
[0792] R4"=OH and R5"=sulfonyl and R6"=OH; or
[0793] R4" = OH and R5" = sulfonyl and R6" = methyl; or
[0794] R4" = OH and R5" = sulfonyl and R6" = O-methyl; or
[0795] R4"=OH and R5"=sulfonyl and R6"=-S(=O) 2 OH; or
[0796] R4"=OH and R5"=sulfonyl and R6"=sulfonyl; or
[0797] R4"=methyl and R5"=H and R6"=H; or
[0798] R4" = methyl and R5" = H and R6" = OH; or
[0799] R4" = methyl and R5" = H and R6" = methyl; or
[0800] R4" = methyl and R5" = H and R6" = O-methyl; or
[0801] R4"=methyl and R5"=H and R6"=-S(=O) 2 OH; or
[0802] R4" = methyl and R5" = H and R6" = sulfonyl; or
[0803] R4"=methyl and R5"=OH and R6"=H; or
[0804] R4"=methyl and R5"=OH and R6"=OH; or
[0805] R4" = methyl and R5" = OH and R6" = methyl; or
[0806] R4" = methyl and R5" = OH and R6" = O-methyl; or
[0807] R4"=methyl and R5"=OH and R6"=-S(=O) 2 OH; or
[0808] R4" = methyl and R5" = OH and R6" = sulfonyl; or
[0809] R4" = methyl and R5" = methyl and R6" = H; or
[0810] R4" = methyl and R5" = methyl and R6" = OH; or
[0811] R4" = methyl and R5" = methyl and R6" = methyl; or
[0812] R4" = methyl and R5" = methyl and R6" = O-methyl; or
[0813] R4"=methyl and R5"=methyl and R6"=-S(=O) 2 OH; or
[0814] R4" = methyl and R5" = methyl and R6" = sulfonyl; or
[0815] R4" = methyl and R5" = O-methyl and R6" = H; or
[0816] R4" = methyl and R5" = O-methyl and R6" = OH; or
[0817] R4" = methyl and R5" = O-methyl and R6" = methyl; or
[0818] R4" = methyl and R5" = O-methyl and R6" = O-methyl; or
[0819] R4" = methyl and R5" = O-methyl and R6" = -S(=O)2 OH; or
[0820] R4" = methyl and R5" = O-methyl and R6" = sulfonyl; or
[0821] R4"=methyl and R5"=-S(=O) 2 OH and R6″=H; or
[0822] R4"=methyl and R5"=-S(=O) 2 OH and R6″=OH; or
[0823] R4"=methyl and R5"=-S(=O) 2 OH and R6″=methyl; or
[0824] R4"=methyl and R5"=-S(=O) 2 OH and R6″=O-methyl; or
[0825] R4"=methyl and R5"=-S(=O) 2 OH and R6"=-S(=O) 2 OH; or
[0826] R4"=methyl and R5"=-S(=O) 2 OH and R6″=sulfonyl; or
[0827] R4" = methyl and R5" = sulfonyl and R6" = H; or
[0828] R4" = methyl and R5" = sulfonyl and R6" = OH; or
[0829] R4" = methyl and R5" = sulfonyl and R6" = methyl; or
[0830] R4" = methyl and R5" = sulfonyl and R6" = O-methyl; or
[0831] R4" = methyl and R5" = sulfonyl and R6" = -S(=O) 2 OH; or
[0832] R4" = methyl and R5" = sulfonyl and R6" = sulfonyl; or
[0833] R4"=O-methyl and R5"=H and R6"=H; or
[0834] R4" = O-methyl and R5" = H and R6" = OH; or
[0835] R4" = O-methyl and R5" = H and R6" = methyl; or
[0836] R4" = O-methyl and R5" = H and R6" = O-methyl; or
[0837] R4"=O-methyl and R5"=H and R6"=-S(=O) 2 OH; or
[0838] R4" = O-methyl and R5" = H and R6" = sulfonyl; or
[0839] R4" = O-methyl and R5" = OH and R6" = H; or
[0840] R4"=O-methyl and R5"=OH and R6"=OH; or
[0841] R4" = O-methyl and R5" = OH and R6" = methyl; or
[0842] R4" = O-methyl and R5" = OH and R6" = O-methyl; or
[0843] R4"=O-methyl and R5"=OH and R6"=-S(=O) 2 OH; or
[0844] R4" = O-methyl and R5" = OH and R6" = sulfonyl; or
[0845] R4" = O-methyl and R5" = methyl and R6" = H; or
[0846] R4" = O-methyl and R5" = methyl and R6" = OH; or
[0847] R4" = O-methyl and R5" = methyl and R6" = methyl; or
[0848] R4" = O-methyl and R5" = methyl and R6" = O-methyl; or
[0849] R4"=O-methyl and R5"=methyl and R6"=-S(=O) 2 OH; or
[0850] R4" = O-methyl and R5" = methyl and R6" = sulfonyl; or
[0851] R4" = O-methyl and R5" = O-methyl and R6" = H; or
[0852] R4" = O-methyl and R5" = O-methyl and R6" = OH; or
[0853] R4" = O-methyl and R5" = O-methyl and R6" = methyl; or
[0854] R4" = O-methyl and R5" = O-methyl and R6" = O-methyl; or
[0855] R4"=O-methyl and R5"=O-methyl and R6"=-S(=O) 2 OH; or
[0856] R4" = O-methyl and R5" = O-methyl and R6" = sulfonyl; or
[0857] R4"=O-methyl and R5"=-S(=O) 2 OH and R6″=H; or
[0858] R4"=O-methyl and R5"=-S(=O) 2 OH and R6″=OH; or
[0859] R4"=O-methyl and R5"=-S(=O) 2 OH and R6″=methyl; or
[0860] R4"=O-methyl and R5"=-S(=O) 2 OH and R6″=O-methyl; or
[0861] R4" = O-methyl and R5" = -S(=O) 2 OH and R6"=-S(=O) 2 OH; or
[0862] R4"=O-methyl and R5"=-S(=O) 2 OH and R6″=sulfonyl; or
[0863] R4" = O-methyl and R5" = sulfonyl and R6" = H; or
[0864] R4" = O-methyl and R5" = sulfonyl and R6" = OH; or
[0865] R4" = O-methyl and R5" = sulfonyl and R6" = methyl; or
[0866] R4" = O-methyl and R5" = sulfonyl and R6" = O-methyl; or
[0867] R4" = O-methyl and R5" = sulfonyl and R6" = -S(=O) 2 OH; or
[0868] R4" = O-methyl and R5" = sulfonyl and R6" = sulfonyl; or
[0869] R4"=-S(=O) 2 OH and R5″=H and R6″=H; or
[0870] R4"=-S(=O) 2 OH and R5″=H and R6″=OH; or
[0871] R4"=-S(=O) 2 OH and R5″=H and R6″=methyl; or
[0872] R4"=-S(=O) 2 OH and R5″=H and R6″=O-methyl; or
[0873] R4"=-S(=O) 2 OH and R5"=H and R6"=-S(=O) 2 OH; or
[0874] R4"=-S(=O) 2 OH and R5″=H and R6″=sulfonyl; or
[0875] R4"=-S(=O) 2 OH and R5″=OH and R6″=H; or
[0876] R4"=-S(=O) 2 OH and R5″=OH and R6″=OH; or
[0877] R4"=-S(=O) 2 OH and R5″=OH and R6″=methyl; or
[0878] R4"=-S(=O) 2 OH and R5″=OH and R6″=O-methyl; or
[0879] R4"=-S(=O) 2 OH and R5"=OH and R6"=-S(=O) 2 OH; or
[0880] R4"=-S(=O) 2 OH and R5″=OH and R6″=sulfonyl; or
[0881] R4"=-S(=O) 2 OH and R5″=methyl and R6″=H; or
[0882] R4"=-S(=O) 2 OH and R5″=methyl and R6″=OH; or
[0883] R4"=-S(=O) 2 OH and R5″=methyl and R6″=methyl; or
[0884] R4"=-S(=O) 2 OH and R5″=methyl and R6″=O-methyl; or
[0885] R4"=-S(=O) 2 OH and R5"=methyl and R6"=-S(=O) 2 OH; or
[0886] R4"=-S(=O) 2 OH and R5″=methyl and R6″=sulfonyl; or
[0887] R4"=-S(=O) 2 OH and R5″=O-methyl and R6″=H; or
[0888] R4"=-S(=O) 2 OH and R5″=O-methyl and R6″=OH; or
[0889] R4"=-S(=O) 2 OH and R5″=O-methyl and R6″=methyl; or
[0890] R4"=-S(=O) 2 OH and R5″=O-methyl and R6″=O-methyl; or
[0891] R4"=-S(=O) 2 OH and R5"=O-methyl and R6"=-S(=O) 2 OH; or
[0892] R4"=-S(=O) 2 OH and R5″=O-methyl and R6″=sulfonyl; or
[0893] R4"=-S(=O) 2 OH and R5"=-S(=O) 2 OH= and R6″=H; or
[0894] R4"=-S(=O) 2 OH and R5"=-S(=O) 2 OH and R6″=OH; or
[0895] R4"=-S(=O) 2 OH and R5"=-S(=O) 2 OH and R6" = methyl; or
[0896] R4"=-S(=O) 2 OH and R5"=-S(=O) 2OH and R6″=O-methyl; or
[0897] R4"=-S(=O) 2 OH and R5"=sulfonyl and R6"=H; or
[0898] R4"=-S(=O) 2 OH and R5″=sulfonyl and R6″=OH; or
[0899] R4"=-S(=O) 2 OH and R5″=sulfonyl and R6″=methyl; or
[0900] R4"=-S(=O) 2 OH and R5″=sulfonyl and R6″=O-methyl; or
[0901] R4"=sulfonyl and R5"=H and R6"=H; or
[0902] R4"=sulfonyl and R5"=H and R6"=OH; or
[0903] R4" = sulfonyl and R5" = H and R6" = methyl; or
[0904] R4" = sulfonyl and R5" = H and R6" = O-methyl; or
[0905] R4"=sulfonyl and R5"=H and R6"=-S(=O) 2 OH; or
[0906] R4" = sulfonyl and R5" = H and R6" = sulfonyl; or
[0907] R4"=sulfonyl and R5"=OH and R6"=H; or
[0908] R4"=sulfonyl and R5"=OH and R6"=OH; or
[0909] R4" = sulfonyl and R5" = OH and R6" = methyl; or
[0910] R4" = sulfonyl and R5" = OH and R6" = O-methyl; or
[0911] R4"=sulfonyl and R5"=OH and R6"=-S(=O) 2 OH; or
[0912] R4" = sulfonyl and R5" = OH and R6" = sulfonyl; or
[0913] R4" = sulfonyl and R5" = methyl and R6" = H; or
[0914] R4" = sulfonyl and R5" = methyl and R6" = OH; or
[0915] R4" = sulfonyl and R5" = methyl and R6" = methyl; or
[0916] R4" = sulfonyl and R5" = methyl and R6" = O-methyl; or
[0917] R4"=sulfonyl, R5"=methyl, R6"=-S(=O) 2 OH; or
[0918] R4" = sulfonyl and R5" = methyl and R6" = sulfonyl; or
[0919] R4" = sulfonyl and R5" = O-methyl and R6" = H; or
[0920] R4" = sulfonyl and R5" = O-methyl and R6" = OH; or
[0921] R4" = sulfonyl and R5" = O-methyl and R6" = methyl; or
[0922] R4" = sulfonyl and R5" = O-methyl and R6" = O-methyl; or
[0923] R4"=sulfonyl and R5"=O-methyl and R6"=-S(=O) 2 OH; or
[0924] R4" = sulfonyl and R5" = O-methyl and R6" = sulfonyl; or
[0925] R4"=sulfonyl and R5"=-S(=O) 2 OH and R6″=H; or
[0926] R4"=sulfonyl and R5"=-S(=O) 2 OH and R6″=OH; or
[0927] R4"=sulfonyl and R5"=-S(=O) 2 OH and R6″=methyl; or
[0928] R4"=sulfonyl and R5"=-S(=O) 2 OH and R6″=O-methyl; or
[0929] R4"=sulfonyl and R5"=sulfonyl and R6"=H; or
[0930] R4"=sulfonyl and R5"=sulfonyl and R6"=OH; or
[0931] R4" = sulfonyl and R5" = sulfonyl and R6" = methyl; or
[0932] R4" = sulfonyl and R5" = sulfonyl and R6" = O-methyl.
[0933] In the general formulae (V), (VI), (VII), (VIII), (IX), (X) and variants thereof, the substituted phenyl ring bonded to the imino functional group is preferably selected from the group consisting of:
[0934]
[0935] The dotted line indicates the binding site to the cyclohexene imine ring.
[0936] In still more preferred variants according to the first aspect of the invention, in the general formula (V), (VII), (VIII) and variants thereof, the substituents R4', R5' and R6', which may be identical or different, are independently selected from the group consisting of: H; OH; alkyl, preferably methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl; alkoxy, preferably O-methyl, O-ethyl or O-butyl; -S(=O) 2 OH; and sulfonyl; provided that, if the substituted phenyl ring is monosubstituted, the substituent is located in the ortho or meta position but not in the para position to the imino function of the general formulae (V), (VII) and (VIII).
[0937] Alternatively, in still more preferred variants according to the first aspect of the present invention, in the general formula (VI), (IX), (X) and variants thereof, the substituents R4", R5" and R6" which may be identical or different are independently selected from the group consisting of: H; OH; alkyl, preferably methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl; alkoxy, preferably O-methyl, O-ethyl or O-butyl; -S(=O) 2 OH; and sulfonyl; provided that, if the substituted phenyl ring is monosubstituted, the substituent is located in the ortho or meta position but not in the para position to the imino function of the general formulae (VI), (IX) and (X).
[0938] Still more preferably according to the first aspect of the present invention, the food, cosmetic or pharmaceutical preparation or household care product comprises at least one mycosporin-like amino acid compound selected from the group consisting of:
[0939] Table 3 :
[0940]
[0941]
[0942]
[0943]
[0944]
[0945] or a tautomer or stereoisomer or salt of the aforementioned compound, or any mixture of the aforementioned compounds.
[0946] Among the above-mentioned mycosporin-like amino acid compounds, compounds MAA-1 and MAA-13 are particularly preferred because they have a significant stabilizing effect. Most preferred are acid compounds MAA-20, MAA-21, MAA-22, MAA-23, MAA-24, MAA-24, MAA-26, MAA-27, MAA-28, MAA-29, MAA-30, MAA-31 and amide compounds MAA-32, MAA-33, MAA-34, MAA-35, MAA-36, MAA-37, MAA-38 and MAA-39. The compounds having acid functional groups or amide functional groups are light-stable and temperature-stable, and show stability in pH solutions or in oil-in-water emulsions, and do not degrade compared to the corresponding ester analogs. Particularly preferred are the acid compounds MAA-20, MAA-21, MAA-22, MAA-23, MAA-24, MAA-24, MAA-26, MAA-27, MAA-28, MAA-29, MAA-30 and MAA-31 due to their stability and their enhanced solubility in water.
[0947] In particular, the mycosporin-like amino acid compounds MAA-20, MAA-21, MAA-22, MAA-23, MAA-24, MAA-24, MAA-26, MAA-27, MAA-28, MAA-29, MAA-30 and MAA-31 have better stability over a wider pH range, compared to their respective ester compounds which hydrolyze and are therefore unstable in alkaline solutions / formulations above pH 9.
[0948] Since the mycosporin-like amino acid compounds are more soluble in water, they can be incorporated into the aqueous phase of formulations at higher concentrations than the corresponding ester analogs, thereby producing better antioxidant enhancement or promotion effects in food, cosmetic or pharmaceutical preparations or home care products.
[0949] Still more preferably according to the first aspect of the present invention, the food, cosmetic or pharmaceutical preparation or household care product comprises at least one mycosporin-like amino acid compound selected from the group consisting of:
[0950] MAA-A:
[0951]
[0952] MAA-B:
[0953] as well as
[0954] MAA-C:
[0955]
[0956] or a tautomer or stereoisomer or salt of the aforementioned compound, or any mixture of the aforementioned compounds, wherein the alkyl group is preferably methyl or ethyl or propyl or isopropyl or butyl or isobutyl or tert-butyl, most preferably methyl.
[0957] The mycosporin-like amino acid compounds according to the invention and as defined herein are used as sole substances or in a mixture with one, two or more different mycosporin-like amino acid compounds as defined herein.
[0958] Particularly preferred are mixtures of two mycosporin-like amino acid compounds according to the invention and as defined herein. Such mixtures show particularly enhanced stabilizing and antioxidant boosting effects, as demonstrated in the following examples.
[0959] The food, cosmetic or pharmaceutical composition or household care product according to the first aspect of the present invention is also characterized in that it does not contain one or more of the following mycosporin-like amino acid compounds:
[0960] Compound 1:
[0961]
[0962] Compound 2:
[0963]
[0964] Compound 3:
[0965]
[0966] Compound 4:
[0967]
[0968] Compound 5:
[0969]
[0970] Compound 6:
[0971]
[0972] Compound 7:
[0973]
[0974] Compound 8:
[0975]
[0976] As described herein, various mycosporin amino acid compounds (b) contain one or more chiral centers and may therefore exist as racemic mixtures of enantiomers, mixtures of diastereomers, or enantiomers or optically pure compounds. It should also be noted that the compounds of the present invention include E and Z isomers or mixtures thereof, as well as cis and trans isomers or mixtures thereof.
[0977] Therefore, the chemical structures of the mycosporin-like amino acid compounds according to general formula (V) to (X) and variations thereof and the compounds explicitly disclosed herein include all possible enantiomers and diastereomers or stereoisomers thereof.
[0978] In certain embodiments, the mycosporin-like amino acid compound (b) of the present invention is isolated as an E or Z isomer. In other embodiments, the compound of the present invention is a mixture of E and Z isomers.
[0979] Alternatively, stereoisomerically pure compounds are used in food, cosmetics or pharmaceutical preparations or household care products according to the present invention. As used herein, and unless otherwise indicated, the term "stereoisomerically pure" means that one stereoisomer of a compound is substantially free of other stereoisomers of the compound, or a geometric isomer (e.g., about double bonds) is substantially free of other geometric isomers. For example, the stereoisomerically pure compound of the present invention with a chiral center will be substantially free of the opposite enantiomer of the compound. The stereoisomerically pure compound of the present invention with two chiral centers or its composition will be substantially free of other diastereomers of the compound. The stereoisomerically pure compound of the present invention or its composition with a double bond capable of E / Z isomerization will be substantially free of one of E / Z isomers.
[0980] A typical stereomerically pure compound contains greater than about 80% by weight of one stereoisomer or E / Z isomer of the compound and less than about 20% by weight of other stereoisomers or E / Z isomers of the compound, more preferably greater than about 90% by weight of one stereoisomer or E / Z isomer of the compound and less than about 10% by weight of other stereoisomers or E / Z isomers of the compound, even more preferably greater than about 95% by weight of one stereoisomer or E / Z isomer of the compound and less than about 5% by weight of other stereoisomers or E / Z isomers of the compound, and most preferably greater than about 97% by weight of one stereoisomer or E / Z isomer of the compound and less than about 3% by weight of other stereoisomers or E / Z isomers of the compound.
[0981] As used herein, and unless otherwise indicated, the term "stereoisomerically enriched" means a compound of the invention, or composition thereof, which contains greater than about 60% by weight of one stereoisomer or E / Z isomer of a compound of the invention, preferably greater than about 70% by weight, more preferably greater than about 80% by weight of one stereoisomer or E / Z isomer of a compound of the invention.
[0982] Therefore, it should be noted that, unless otherwise stated, the terms mycosporin-like amino acid compounds according to general formula (V) to (X) and variations thereof, as well as the individual mycosporin-like amino acid compounds specified herein, should be interpreted as covering racemic mixtures of enantiomers, mixtures of diastereomers or enantiomerically or optically pure compounds.
[0983] Due to their aminocyclohexene imine structure and their electron delocalization capabilities, the mycosporin-like amino acid compounds according to general formulae (V) to (X) and variants thereof are in equilibrium with their tautomeric structures, wherein the hydrogen of the amino group changes its position with the double bond of the cyclohexene ring.
[0984] Tautomerism is defined as each of two or more isomers of a compound that exist together in equilibrium and readily interchange by migration of atoms or groups within the molecule. A tautomerically pure or enriched system will readily interchange to an equilibrium state over time.
[0985] The tautomers of the general formula (V) are represented by the general formula (V-tau):
[0986]
[0987] The tautomers of the general formula (VI) are represented by the general formula (VI-tau):
[0988]
[0989] The above principles of tautomerism and redispersion explained based on the mycosporin-like amino acid compounds according to general formula (V) and (VI) are equally applicable to any mycosporin-like amino acid compound defined by general formula (VII), (VIII), (IX), (X) and variants thereof, or to any individual mycosporin-like amino acid compound specified herein.
[0990] Therefore, hereinafter and throughout the specification, references to a mycosporin-like amino acid compound represented by any one of the general formulae (V) to (X) and variations thereof, or to an individual mycosporin-like amino acid compound specified herein, also encompass tautomeric isomers thereof.
[0991] According to a first aspect of the invention, the mycosporin-like amino acid compounds according to the general formula (V) to (X) and their variants as well as the individual mycosporin-like amino acid compounds specified herein are used in neutral (i.e. uncharged) form or in the form of their salts with inorganic or organic acids (such as acid addition salts).
[0992] In the context of the present invention, the term "salt" refers to a salt of a compound that has the desired effect or pharmacological activity of the parent compound. Such salts include:
[0993] (1) Acid addition salts with inorganic acids, or with organic acids (preferably monovalent or polyvalent carboxylic acids)
[0994] an acid addition salt; or
[0995] (2) Salts formed when an acidic proton present in the starting compound is replaced by a metal ion (eg, an alkali metal ion, an alkaline earth metal ion, or an aluminum ion); or coordinated with an organic base.
[0996] Of these salts, acid addition salts are again particularly preferred, since the mycosporin-like amino acid compounds according to the general formulae (V) to (X) and variants thereof or the mycosporin-like amino acid compounds specified herein contain a protonatable N atom.
[0997] The inorganic acid which forms an acid addition salt with the mycosporin-like amino acid compound used according to the invention is preferably selected from the group consisting of hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, etc. Particularly preferred are hydrochlorides, sulfates or phosphates.
[0998] Even more preferred are acid addition salts with organic mono- or poly-carboxylic acids. Further preferred are acid addition salts with organic mono- or poly-carboxylic acids, wherein the carboxylic acid is selected from saturated or mono- or poly-unsaturated C1-C30 monocarboxylic acids, saturated or mono- or poly-unsaturated C3-10 di- or tri-carboxylic acids. The carboxylic acids may be mono- or poly-substituted by hydroxyl groups, preferably α-hydroxycarboxylic acids, wherein the hydroxyl group is located on a carbon atom adjacent to the carboxyl group. Many representative substances occur naturally as so-called fruit acids. Preferred α-hydroxycarboxylic acids are malic acid, citric acid, 2-hydroxy-4-methylmercaptobutyric acid, glycolic acid, isocitric acid, mandelic acid, lactic acid, tartronic acid or tartaric acid.
[0999] The organic acid that forms an acid addition salt with the mycosporin-like amino acid compound used according to the present invention is preferably selected from the group consisting of amino acids, acetic acid, trifluoroacetic acid, propionic acid, hexanoic acid, cyclopentanepropionic acid, glycolic acid, pyruvic acid, lactic acid, malonic acid, oxalic acid, succinic acid, malic acid, maleic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, 3-(4-hydroxybenzoyl)benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, 1,2-ethanedisulfonic acid, 2-hydroxyethanesulfonic acid, benzenesulfonic acid, 4-chlorobenzenesulfonic acid, 2-naphthalenesulfonic acid, 4-toluenesulfonic acid, camphorsulfonic acid, 4-methylbicyclo[2.2.2]-oct-2-ene-1-carboxylic acid, glucoheptonic acid, 3-phenylpropionic acid, trimethylacetic acid, tert-butylacetic acid, lauryl sulfuric acid, gluconic acid, glutamic acid, hydroxynaphthoic acid, salicylic acid, stearic acid, muconic acid, 4-hydroxybutyric acid, etc.
[1000] Suitable anionic counterions are specifically chloride, bromide, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C1- to C4-alkanoic acids, preferably formate, acetate, trifluoroacetate, propionate and butyrate, in addition there are lactate, gluconate, and the anions of polyacids such as succinate, oxalate, maleate, fumarate, malate, tartrate and citrate, in addition there are sulfonate anions, such as benzenesulfonate (benzenesulfonate), toluenesulfonate (toluenesulfonate), naphthenesulfonate (naphthalene-2-sulfonate), methanesulfonate (mesylate), ethanesulfonate (ethanesulfonate) and ethanedisulfonate. They can be formed by the acid reaction of the compound with basic functional groups according to the present invention with the corresponding anions. Preferred salts of the compounds of formula (I) to (III) and the individual mycosporin-like amino acid compounds specified herein are the hydrochloride salts.
[1001] The metal ion for salt formation which replaces the acidic protons present in the starting compound is selected from the group consisting of alkali metal ions (preferably Na+, K+ or Li+), alkaline earth metal ions (preferably Ca++ or Mg++), aluminum+++ or NH4+.
[1002] The coordinating organic base used for salt formation is selected from the group consisting of ethanolamine, diethanolamine, triethanolamine, N-methylglucamine, triethylamine and the like.
[1003] In the following description and claims, unless otherwise stated, the term mycosporin-like amino acid compound includes both the neutral, uncharged form of the compound / molecule and also the salt form of the compound.
[1004] The salt form of mycosporin-like amino acid compounds results in lower logP OW , thus making the compound more hydrophilic, which results in better water solubility. In particular, cationic salts of mycosporin-like amino acid compounds support the emulsification process in emulsions due to their surface reducing activity, i.e. co-emulsifying properties. In addition, cationic salt forms of mycosporin-like amino acid compounds show excellent substantivity behavior on skin and hair and other inanimate surfaces: most conditioning actives are cationic; the conditioning effect results in a softer skin feel, which makes the final product more acceptable to consumers. In addition, mycosporin-like amino acid compounds in cationic salt form exhibit antimicrobial activity.
[1005] Surprisingly, the addition of mycosporin-like amino acid compounds to fragrances or flavors / flavor compounds in food, cosmetic or pharmaceutical preparations or home care products results in an improvement in the stability of the fragrances or flavors / flavors. In the presence of mycosporin-like amino acid compounds, the fragrances or flavors / flavor compounds are not subject to degradation caused by oxygen, temperature and / or light. Thus, the use of mycosporin-like amino acid compounds prevents the formulation from degradation, odor change (i.e., malodor formation) and / or discoloration, as demonstrated in the following examples.
[1006] Due to the significant stabilizing effect as described above, the combined use of at least one aroma or fragrance / flavor compound (a) and at least one mycosporin-like amino acid compound (b) is suitable for improving the storage stability and extending the shelf life of food, cosmetic or pharmaceutical preparations or household care products.
[1007] The food, cosmetic or pharmaceutical preparation or household care product according to the invention optionally contains at least one antioxidant (c). Optionally means that the antioxidant (c) is not mandatory in the food, cosmetic or pharmaceutical preparation or household care product according to the invention, but can be advantageously incorporated.
[1008] The term "antioxidant" as used in this application refers to a substance or composition that significantly delays, prevents or even inhibits oxidation. Antioxidants react with free radicals, thereby reducing them to stable, non-reactive products. Oxidation is a chemical reaction that produces a free radical chain reaction that produces highly reactive peroxides and hydroperoxides. These peroxides and hydroperoxides then react with substrates present in cosmetic compositions or foods, which can produce decomposition products, such as carboxylic acids, aldehydes and ketones, etc., which change the organoleptic properties of the product and cause the composition to degrade.
[1009] Antioxidants play an important physiological role as free radical scavengers. In organisms, antioxidants inactivate biologically important reactive free radicals or other reactive oxygen species (ROS), excessive reactive free radicals or other reactive oxygen species can lead to oxidative stress. In a biological context, reactive oxygen species (ROS) are formed as natural byproducts of the normal metabolism of oxygen and have important roles in cell signaling and homeostasis. However, ROS levels can increase significantly during environmental stress (e.g., UV or heat exposure).
[1010] The above-mentioned oxidative processes or the above-mentioned biochemical reactions caused by oxidative stress and excess reactive oxygen species (ROS) in the preparations according to the invention can be downregulated when antioxidants are used.
[1011] The food, cosmetic or pharmaceutical composition or home care product according to the first aspect of the present invention comprises at least one antioxidant selected from the group consisting of: dimethylmethoxychromanol at very low tolerated doses, arbutin, amino acids (e.g. arginine, lysine, glycine, histidine, tyrosine, tryptophan) and their derivatives (e.g. acetylcysteine), tert-butylhydroquinone, caffeic acid, chlorogenic acid, imidazoles (e.g. urocanic acid) and their derivatives, kojic acid, peptides such as D,L-carnosine, D-carnosine, L-carnosine and its derivatives (e.g., anserine), hydroxyphenylpropionamide benzoic acid (dihydroavenathramide D), diethylhexyl syringylidenemalonate, phenethylresorcinol, gallic acid and its derivatives, quercetin, hydroxyacetophenone, rosmarinic acid, carotenoids, carotenes (e.g., α-carotene, β-carotene, lycopene), phytoene, phytoene and its derivatives, lipoic acid and its derivatives (e.g., dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (e.g., thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleoyl, γ-linoleoyl, cholesterol and glyceride) and their salts, dilauryl thiodipropionate, pentaerythritol tetra-di-tert-butyl hydroxyhydrocinnamate, distearyl thiodipropionate, thiodipropionic acid and its derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and sulfenimide compounds (e.g. buthionine sulfenimide, lactobacilli (fermentation products, filtrates, lysates), homocysteine sulfenimide, butyl sulfone, pentathionine sulfenimide, hexathionine sulfenimide, heptathionine sulfenimide), and also (metal) chelates mixture (e.g., α-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin, α-hydroxy acids (e.g., citric acid, lactic acid, malic acid), humic acid, bile acid, bile extract, bilirubin, biliverdin, hinokitiol, EDTA, EGTA, trisodium dicarboxymethylalanine, MGDA (methylglycine diacetic acid), GLDA (glutamic acid diacetic acid)) and their derivatives, unsaturated fatty acids and their derivatives (e.g., γ-linolenic acid, linoleic acid, oleic acid), folic acid and its derivatives, ubiquinone and ubiquinol and their derivatives, triethyl citrate, vitamin C and its derivatives (e.g., ascorbyl palmitate, magnesium ascorbyl phosphate, ethyl ascorbate esters), tocopherol and its derivatives (e.g. α-tocopherol, β-tocopherol, γ-tocopherol, δ-tocopherol, tocopheryl acetate), panthenol, vitamin A and its derivatives (vitamin A palmitate, hydroxypinacolone retinoate) and coniferyl benzoate of benzoic acid resin, rutinic acid and its derivatives, ferulic acid and its derivatives, butylated hydroxytoluene, butylated hydroxyanisole, hydroxymethoxyphenyldecanoate, dehydroguaiac acid, nordihydroguaiac acid, allantoin, tropolone, trihydroxybutyrophenone, uric acid and its derivatives, mannose and its derivatives, hydroxyacetophenone (o / p), zinc and its derivatives (e.g. ZnO, ZnSO, 4), β-aspartyl arginine, selenium and its derivatives (e.g., methionine selenium), grape (Vitis Vinifera, Grape) seed extract, oat extract, chicory (Cichorium intubybus, chicory) leaf extract, alpine edelweiss (Leon-topodium Alpinum) extract, green tea extract, curculigo sweet protein, ginger (Zingiber Officinalis, Ginger) root extract, silymarin, stilbenes and their derivatives (e.g., stilbene oxide, trans-stilbene oxide) and derivatives of the antioxidants, such as salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids, and mixtures of two or more of the antioxidants.
[1012] In a preferred variant, the antioxidant of the cosmetic or pharmaceutical composition or home care product of the invention is selected from the group consisting of dimethylmethoxychromanol, hydroxyacetophenone, ascorbic acid and its salts, hydroxymethoxyphenyldecanoate, β-aspartylarginine, uric acid, urea, hydroxypinacolone retinoic acid ester, vitamin A and vitamin A derivatives, butylhydroxytoluene (BHT), butylhydroxyanisole (BHA), hydroxyphenylpropionamidobenzoic acid, ascorbyl palmitate, Ascorbyl phosphate and its salts, carnosine, rutin, tocopherol, tocopheryl acetate, ubiquinone-10, dilauryl thiodipropionate, pentaerythrityl tetra-di-tert-butyl hydroxyhydrocinnamate, triethyl citrate, diethylhexyl syringylidenemalonate, lactobacillus (fermentation product, filtrate, lysate), hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), green tea extract, ginger root extract, tropolone, allantoin, and a mixture of two or more of the above antioxidants.
[1013] In a particularly preferred variant, the antioxidant of the cosmetic or pharmaceutical composition according to the invention is tocopherol or tocopherol acetate. Also preferred is dimethylmethoxychromanol.
[1014] Still more preferred among the above antioxidants are antioxidants selected from the group consisting of hydroxyacetophenone, hydroxymethoxyphenyldecanone, and hydroxyphenylpropionamide benzoic acid (dihydroavenathramide D).
[1015] The above antioxidants may be used as a single component or in admixture with one or more additional antioxidants as described above.
[1016] Surprisingly, it has been found that by adding a mycosporin-like amino acid compound (b) as defined herein to a food, cosmetic or pharmaceutical preparation or home care product according to the present invention comprising an antioxidant, the antioxidant efficacy of the antioxidant (c) can be significantly improved. Preferably, the combination of mycosporin-like amino acid compound (b) and antioxidant (c) produces a synergistic stabilizing effect against oxidative degradation. The use of such a combination in a food, cosmetic or pharmaceutical preparation or home care product then produces a stable formulation with no malodor and / or color deviation or only slight malodor and / or color deviation. The improved antioxidant effect then produces a formulation with improved storage stability and extended shelf life.
[1017] Thus, in a preferred advantageous variant, the food, cosmetic or pharmaceutical composition or the household care product according to the first aspect of the invention comprises one of the following combinations of components (b) and (c):
[1018] ■ One or more of the following antioxidants: dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or ascorbic acid and its salts, and / or hydroxymethoxyphenyldecanoate, and / or β-aspartyl arginine, and / or uric acid, and / or urea, and / or hydroxypinacolone retinoate, and / or vitamin A and vitamin A derivatives, and / or butylated hydroxytoluene (BHT), and / or butylated hydroxyanisole (BHA), and / or hydroxyphenylpropionamidobenzoic acid, and / or ascorbyl palmitate, and / or ascorbyl phosphate and its salts, and / or carnosine, and and / or rutin, and / or tocopherol, and / or tocopherol acetate, and / or ubiquinone-10, and / or dilauryl thiodipropionate, and / or pentaerythritol tetra-di-tert-butyl hydroxyhydrocinnamate, and / or triethyl citrate, and / or diethylhexyl syringylidenemalonate, and / or lactobacillus (fermentation product, filtrate, lysate), and / or hydroxyphenylpropionamide benzoic acid (dihydroavenathramide D), and / or green tea extract, and / or ginger root extract, and / or tropolone, and / or allantoin, in combination with a mycosporin-like amino acid compound of formula (V); or
[1019] ■ One or more of the following antioxidants: dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or ascorbic acid and its salts, and / or hydroxymethoxyphenyldecanoate, and / or β-aspartyl arginine, and / or uric acid, and / or urea, and / or hydroxypinacolone retinoic acid ester, and / or vitamin A and vitamin A derivatives, and / or butylhydroxytoluene (BHT), and / or butylhydroxyanisole (BHA), and / or hydroxyphenylpropionamide Benzoic acid, and / or ascorbyl palmitate, and / or ascorbyl phosphate and its salts, and / or carnosine, and / or rutin, and / or tocopherol, and / or tocopherol acetate, and / or ubiquinone-10, and / or dilauryl thiodipropionate, and / or pentaerythritol tetra-di-tert-butyl hydroxyhydrocinnamate, and / or triethyl citrate, and / or diethylhexyl syringylidenemalonate, and / or lactobacillus (fermentation product, filtrate, lysate), and / or
[1020] Or hydroxyphenylpropionamide benzoic acid (dihydroavenathramide D), and / or green tea extract, and / or ginger root extract, and / or tropolone, and / or allantoin, in combination with the mycosporin-like amino acid compound of formula (VI).
[1021] The above antioxidant / mycosporine-like amino acid compound combination showed significant synergistic antioxidant efficacy against oxidative degradation and was significantly superior to the corresponding compound alone (at the same concentration).
[1022] The most preferred antioxidant / mycosporine-like amino acid compound combination in the food, cosmetic or pharmaceutical preparation or household care product according to the first aspect of the present invention is:
[1023] ■ one or more of the following antioxidants: tocopherol and / or tocopherol acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenathramide D), in combination with a mycosporin-like amino acid compound of formula (V); or
[1024] ■ one or more of the following antioxidants: tocopherol and / or tocopherol acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenathramide D), in combination with a mycosporin-like amino acid compound of formula (VI); or
[1025] ■ one or more of the following antioxidants: tocopherol and / or tocopherol acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-1; or
[1026] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-2; or
[1027] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-3; or
[1028] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-4; or
[1029] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-5; or
[1030] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-6; or
[1031] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-7; or
[1032] ■■ One or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-8; or
[1033] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-9; or
[1034] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-11; or
[1035] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-12; or
[1036] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-13; or
[1037] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-14; or
[1038] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-16; or
[1039] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-17; or
[1040] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-20; or
[1041] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-21; or
[1042] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-22; or
[1043] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-23; or
[1044] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-24; or
[1045] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-25; or
[1046] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-26; or
[1047] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-27; or
[1048] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-28; or
[1049] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-29; or
[1050] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-30; or
[1051] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-31; or
[1052] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-32; or
[1053] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-33; or
[1054] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-34; or
[1055] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-35; or
[1056] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-36; or
[1057] ■ one or more of the following antioxidants: tocopherol and / or tocopherol acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-37; or
[1058] ■ one or more of the following antioxidants: tocopherol and / or tocopheryl acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanoate, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-38; or
[1059] ■ One or more of the following antioxidants: tocopherol and / or tocopherol acetate, and / or dimethylmethoxychromanol, and / or hydroxyacetophenone, and / or hydroxymethoxyphenyldecanone, and / or hydroxyphenylpropionamide benzoic acid (dihydroavenanthramide D), in combination with MAA-39.
[1060] For the above combinations, a synergistic stabilization effect against oxidative degradation as well as an antioxidant promoting effect can be observed.
[1061] A synergistic antioxidant boosting effect was also observed for the mycosporin-like amino acid compounds MAA-A, MAA-B, and MAA-C when combined with any of the above antioxidants.
[1062] Based on the gross weight of food, cosmetics or pharmaceutical preparations or home care products, at least one fragrance or fragrance / flavor compound (a) is present in food, cosmetics or pharmaceutical preparations or home care products in an amount of 0.01 % by weight to 40.0 % by weight. In a preferred variant, based on the gross weight of food, cosmetics or pharmaceutical preparations or home care products, food, cosmetics or pharmaceutical preparations or home care products comprise fragrance or fragrance / flavor compounds in an amount of 0.02 % by weight to 35.0 % by weight. In a particularly preferred variant, based on the gross weight of a composition or final food, cosmetics or pharmaceutical preparations or home care products, fragrance or fragrance / flavor compounds are advantageously used in food, cosmetics or pharmaceutical preparations or home care products in an amount of 0.03 % by weight to 30.0 % by weight. In a most preferred variant, based on the gross weight of a composition or final food, cosmetics or pharmaceutical preparations or home care products, fragrance or fragrance / flavor compounds are advantageously used in food, cosmetics or pharmaceutical preparations or home care products in an amount of 0.04 % by weight to 25.0 % by weight.
[1063] For a mixture of fragrances, the above amounts relate to the total content of fragrances in the mixture, i.e., the amount is the sum of the contents of all fragrances in the mixture. Alternatively, for a mixture of fragrances / flavors, the above amounts relate to the total content of fragrances in the mixture, i.e., the amount is the sum of the contents of all fragrances / flavors in the mixture.
[1064] Based on the total weight of the final formulation, at least one mycosporin-like amino acid compound (b) is present in food, cosmetics or pharmaceutical preparations or home care products in an amount of 0.001% by weight to 15.0% by weight. In a preferred variant, based on the total weight of the final formulation, food, cosmetics or pharmaceutical preparations or home care products contain at least one mycosporin-like amino acid compound (b) in an amount of 0.01% by weight to 10.0% by weight. In a more preferred variant, based on the total weight of the final formulation, at least one mycosporin-like amino acid compound (b) is advantageously used in food, cosmetics or pharmaceutical preparations or home care products in an amount of 0.05% by weight to 7.5% by weight. In a most preferred variant, based on the total weight of the final formulation, at least one mycosporin-like amino acid compound is advantageously used in food, cosmetics or pharmaceutical preparations or home care products in an amount of 0.1% by weight to 5.0% by weight.
[1065] For a mixture of mycosporin-like amino acid compounds (b), the above amounts relate to the total content of mycosporin-like amino acid compounds in the mixture, ie the amount is the sum of the contents of all mycosporin-like amino acid compounds (b) in the mixture.
[1066] According to the first aspect of the invention, optionally at least one antioxidant (c) is present in the food, cosmetic or pharmaceutical preparation or home care product in an amount of 0.0001% to 10.0% by weight, based on the total weight of the final formulation. In a preferred variant, the food, cosmetic or pharmaceutical preparation or home care product comprises an antioxidant (c) in an amount of 0.0005% to 8.0% by weight, based on the total weight of the final formulation. In a most preferred variant, antioxidant (c) is advantageously used in the food, cosmetic or pharmaceutical preparation or home care product in an amount of 0.001% to 6.0% by weight, based on the total weight of the final formulation.
[1067] For a mixture of antioxidants (c), the above amounts relate to the total content of antioxidants in the mixture, ie the amount is the sum of the contents of all antioxidants (c) in the mixture.
[1068] Advantageously, the food, cosmetic or pharmaceutical preparation or household care product according to the first aspect of the invention comprises:
[1069] (ii) 0.01% to 40.0% by weight of at least one aroma or fragrance / flavor compound;
[1070] (iii) 0.001% to 15.0% by weight of at least one mycosporine-like amino acid compound as defined herein; and
[1071] (iv) optionally 0.0001 wt % to 10.0 wt % of at least one antioxidant;
[1072] Based on total weight of final formulation.
[1073] In a preferred variant, the cosmetic or pharmaceutical preparation according to the first aspect of the invention comprises:
[1074] (v) 0.04% to 25.0% by weight of at least one aroma or fragrance / flavor;
[1075] (vi) 0.1% to 5.0% by weight of at least one mycosporine-like amino acid compound as defined herein; and
[1076] (vii) optionally 0.001 wt % to 6.0 wt % of at least one antioxidant;
[1077] Based on total weight of final formulation.
[1078] In the context of the present invention, it is also possible and in some cases advantageous to combine the food, cosmetic or pharmaceutical preparations or household care products according to the first aspect of the invention with other customary active substances, auxiliaries or additives customary for sun protection products, cosmetic or pharmaceutical compositions or household care products (as further described below) to obtain ready-to-use preparations or formulations.
[1079] Other active agents and / or adjuvants and / or additives or auxiliaries are, for example, abrasives, anti-acne agents, anti-skin aging agents, anti-cellulite agents, anti-dandruff agents, anti-inflammatory agents, irritation preventers, irritation inhibitors, antioxidants, alkanediols, astringents, odor absorbers, antiperspirants, bactericides, antistatic agents, antimicrobial agents, binders, buffers, carrier materials, oil components, chelating agents, cell stimulants, cleaning agents, depilatories, surfactants, deodorants, antiperspirants, softeners, emulsifiers, enzymes, enzyme inhibitors, Essential oils, fibers, film formers, water resistance improvers, color fixatives, foam formers, foam stabilizers, defoamers, foam boosters, gelling agents, gel formers, hair care agents, hair fixatives, hair straighteners, moisturizers, moisturizing substances, water-retaining substances, whitening agents, strengthening agents, detergents, optical brighteners, impregnants, antifouling agents, dyes, friction reducers, lubricants, moisturizing creams, ointments, sunscreens, plasticizers, covering agents, polishes, preservatives, glossing agents, green and synthetic polymers, powders, proteins, added Lipid agents, abrasives, silicones, skin soothing agents, skin cleansers, skin care agents, skin healing agents, skin lightening agents, skin protectants, skin softeners, hair promoters, cooling agents, skin cooling agents, warming agents, skin warming agents, stabilizers, surfactants, antimicrobial agents, detergents / surfactants, fabric conditioners, suspending agents, skin tanning agents, active substances that regulate skin or hair pigmentation, matrix metalloproteinase inhibitors, skin moisturizers, glycosaminoglycan stimulators, TRPV1 antagonists, exfoliating dissolving agents, anti-cellulite or fat-enhancing agents, hair growth activators or inhibitors, thickeners, rheological additives, vitamins, oils, waxes, pearlescent waxes, fats, phospholipids, saturated fatty acids, mono- or polyunsaturated fatty acids, alpha-hydroxy acids, polyhydroxy fatty acids, liquefiers, dyes, color protection agents, pigments, anti-corrosion agents, fragrance or perfume oils, fragrances, flavoring substances, odor substances, polyols, electrolytes, organic solvents, and mixtures of two or more of the above substances, as further described below.
[1080] The above-mentioned cosmetic or pharmaceutical excipients and / or active substances and / or additives and / or auxiliary carriers, oil components, rheological additives, hydrotropes, solubilizers, powders, film formers, water resistance improvers, skin moisturizing and / or moisturizing substances, demulcent substances, physiological cooling agents, alkanediols, antioxidants, anti-skin aging agents, matrix metalloproteinase inhibitors (MMPI), anti-inflammatory agents, TRPV1 antagonists, emulsifiers, antimicrobial agents, preservatives, antibacterial or antifungal active substances, chelating agents, surfactants, fragrances / fragrances or perfume oils and any mixtures of two or more of the aforementioned substances are particularly preferred in the preparation of food, cosmetic and pharmaceutical preparations (such as sunscreen products) or home care products.
[1081] Carrier :Compositions according to the present invention may comprise a mixture of carriers or different carriers. The most common acceptable carrier is water. Acceptable carriers other than water include glycerol, C1-4 alcohols, organic solvents, fatty alcohols, fatty ethers, fatty esters, polyols, ethylene glycol, vegetable oils, mineral oils, liposomes, lamellar lipid materials, water or mixtures thereof. Non-limiting examples of organic solvents include monohydric alcohols and polyols, such as ethanol, isopropanol, propanol, benzyl alcohol and phenylethyl alcohol, or ethylene glycol or glycol ethers, such as monomethyl ether, monoethyl ether and monobutyl ether of ethylene glycol, propylene glycol or its ethers, such as monomethyl ether of propylene glycol, butylene glycol, hexylene glycol, dipropylene glycol and alkyl ether of diethylene glycol, such as monoethyl ether or monobutyl ether of diethylene glycol. Other suitable examples of organic solvents are ethylene glycol, propylene glycol, butylene glycol, hexylene glycol, propylene glycol and glycerol. Organic solvents can be volatile or non-volatile compounds. The total amount of carrier in the composition may vary but is typically from 40% to 90% by weight based on the total weight of the composition.
[1082] The product or preparation of the present invention may include at least one water-soluble or organic solvent. The non-limiting example of organic solvent includes monohydric alcohol and polyhydric alcohol, such as ethanol, isopropanol, propanol, benzyl alcohol and phenylethyl alcohol, or ethylene glycol or glycol ether, such as monomethyl ether, monoethyl ether and monobutyl ether of ethylene glycol, propylene glycol or its ether, such as monomethyl ether of propylene glycol, butylene glycol, hexylene glycol, dipropylene glycol and alkyl ether of diethylene glycol, such as monoethyl ether or monobutyl ether of diethylene glycol. Other suitable examples of organic solvent are ethylene glycol, propylene glycol, butylene glycol, hexylene glycol, propylene glycol and glycerine. The organic solvent can be volatile or non-volatile compound.
[1083] Additional non-limiting examples of water-soluble solvents include alkanols (polyols such as ethylene glycol and polyols) such as glycerol, 1,2,6-hexanetriol, trimethylolpropane, ethylene glycol, propylene glycol, diethylene glycol, butylene glycol, hexylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, dipropylene glycol, 1,3-butylene glycol, 2,3-butylene glycol, 1,4-butylene glycol, 3-methyl-1,3-butylene glycol, 1,5-pentanediol, tetraethylene glycol, 1,6- 1,2-octanediol, 1,2-decanediol and 4-methyl-1,2-pentanediol; alkyl alcohols having 1 to 4 carbon atoms, such as ethanol, methanol, 1,2-hexanediol, 2-methyl-2,4-pentanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, 1,2-decanediol and 4-methyl-1,2-pentanediol; alkyl alcohols having 1 to 4 carbon atoms, such as ethanol, methanol ... ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, ethylene glycol monoisopropyl ether, diethylene glycol monoisopropyl ether, ethylene glycol mono-n-butyl ether, ethylene glycol mono-tert-butyl ether, diethylene glycol mono-tert-butyl ether, 1-methyl-1-methoxybutanol, propylene glycol monomethyl ether, propylene glycol mono ethyl ether, propylene glycol mono-tert-butyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-isopropyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether and dipropylene glycol mono-isopropyl ether; 2-pyrrolidone, N-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, formamide, acetamide, dimethyl sulfoxide, sorbitol, sorbitan, acetin, diacetin, triacetin, sulfolane and any mixture thereof. The total amount of water-soluble or organic solvent in the composition according to the present invention can vary, but is generally 0.1% to 50% by weight based on the total weight of the composition.
[1084] Solubilizer: The product or formulation of the present invention may include at least one solubilizer. A solubilizer is a compound that aids in dissolving the components of the composition. A particularly useful but non-limiting example of a solubilizer is a hydrotrope. Hydrotropes (or hydrotropes) are a diverse class of typically water-soluble compounds that may be characterized by an amphiphilic molecular structure and the ability to significantly increase the solubility of poorly soluble organic molecules in water. Non-limiting examples of hydrotropes include sodium 1,3-benzenedisulfonate, sodium benzoate, sodium 4-picolinate, sodium salicylate, sodium benzenesulfonate, caffeine, sodium p-toluenesulfonate, sodium butyl monoglycol sulfate, 4-aminobenzoic acid HCl, sodium cumenesulfonate, N,N-diethylnicotinamide, N-picolyl nicotinamide, N-allyl nicotinamide, 2-methacryloyloxyethyl phosphorylcholine, resorcinol, butyl urea, pyrogallol, N-picolyl methyl acetamide 3.5, procaine HCl, proline HCl, nicotinamide, pyridine, 3-picolyl amine, sodium ibuprofen, sodium xylenesulfonate, ethyl carbamate, pyridoxal hydrochloride, sodium benzoate, 2-pyrrolidone, ethyl urea, N,N-dimethylacetamide, N-methylacetamide and isoniazid, and any mixtures thereof. In some cases, particularly useful hydrotropes include nicotinamide (nicotinamide), caffeine, sodium PCA, sodium salicylate, urea and dihydroxyethyl urea, in particular nicotinamide (nicotinamide) and / or caffeine. Combinations of two or more, three or more, or four or more hydrotropes may also be used in the composition according to the invention. The total amount of solubilizer in the composition of the invention may vary, but is typically in an amount of 0.01% to 20% by weight based on the total weight of the composition.
[1085] In addition, hydrotropes (e.g. ethanol, isopropanol or polyols) can be used to improve the flow behavior. Suitable polyols preferably contain 2 to 15 carbon atoms and at least two hydroxyl groups. The polyols may contain other functional groups, more particularly amino groups, or may be modified with nitrogen. Typical examples are
[1086] -glycerin;
[1087] - alkylene glycols having an average molecular weight of 100 to 1000 Daltons, such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butanediol, hexanediol and polyethylene glycol;
[1088] - technical oligoglycerol mixtures having a degree of self-condensation of from 1.5 to 10, such as, for example, technical diglycerol mixtures having a diglycerol content of from 40 to 50% by weight;
[1089] - methylol compounds, such as, in particular, trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;
[1090] - lower alkyl glucosides, especially those containing 1 to 8 carbon atoms in the alkyl group, for example methyl and butyl glucoside;
[1091] - sugar alcohols containing 5 to 12 carbon atoms, such as sorbitol or mannitol,
[1092] - sugars containing 5 to 12 carbon atoms, such as glucose or sucrose;
[1093] - amino sugars, such as glucosamine; and
[1094] - diolamines, such as diethanolamine or 2-aminopropane-1,3-diol.
[1095] Oil component : The product or formulation according to the present invention may comprise at least one oil phase or at least one oil component, wax, starch, tragacanth, cellulose derivatives, polyethylene glycol, silicone, bentonite, silicon dioxide, talc and zinc oxide or any mixture thereof. Powders include carriers such as lactose, talc, silicon dioxide, aluminum hydroxide, calcium silicate and polyamide powders or any mixture thereof. Solutions and emulsions include carriers such as solvents such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, propylene glycol, etc., or any mixture thereof. However, formulations based entirely on water are also possible. Oil, oil-in-water and water-in-oil emulsions, etc. are preferred.
[1096] Possibly suitable oily phases or oily components in the products or preparations according to the invention are, for example, vegetable oils, hydrocarbons, fatty alcohols, fatty acid esters or mixtures of two or more of the aforementioned oily components.
[1097] The oil phase or oil component in the product or preparation according to the invention is preferably a vegetable oil, even more preferably a liquid vegetable oil. It can also advantageously be a mixture of two or more vegetable oil components, especially a liquid vegetable oil mixture.
[1098] Plant oil or vegetable oil is an oil extracted from seeds, or less commonly, from other parts of the fruit. Similar to animal fats, vegetable oils are mixtures of triglycerides. Soybean oil, rapeseed oil, and cocoa butter are examples of vegetable oils from seeds. Olive oil, palm oil, and rice bran oil are examples of oils from other parts of the fruit. In common use, vegetable oil can refer specifically to plant fats that are liquid at room temperature or at a skin temperature of 35°C to 37°C. Vegetable oils are usually edible.
[1099] The term "vegetable oil" also includes unsaturated vegetable oils. Unsaturated oils or vegetable oils can be converted to oils with higher melting points by partial or complete "hydrogenation". The hydrogenation process involves "spraying" the oil with hydrogen at high temperature and pressure in the presence of a catalyst (usually a powdered nickel compound). When each carbon-carbon double bond is chemically reduced to a single bond, the two hydrogen atoms each form a single bond with two carbon atoms. The elimination of double bonds by adding hydrogen atoms is called saturation; as the degree of saturation increases, the oil progresses towards complete hydrogenation. The oil can be hydrogenated to increase resistance to rancidity (oxidation) or to change its physical properties. As the degree of saturation increases, the viscosity and melting point of the oil increase.
[1100] In a preferred variant, the vegetable oil is selected from the group consisting of: Persea Gratissima (Avocado Oil), Abies Alba Seed Oil, Acacia Victoriae Seed Oil, Actinidia Chinensis (Kiwifruit) Seed Oil, Amaranthus Hypochondriacus Seed Oil, Arachis Hypogaea (Peanut) Oil, Astrophicum Murumuru Seed Butter, Astrophicum Tucuma Seed Butter, Astrophicum Seed Oil, Astrophicum Vulgare Fruit Oil, Astrophicum Kernel Oil, Avena Sativa (Oat) Kernel Oil, Brassica Alba Seed Oil, Brassica Campestris (Rapeseed) Seed Oil, Butyrospermum Parkii (Shea) Butter, Shea Butter, Calendula Officinalis Seed Oil, Calophyllum Inophyllum Seed Oil, Calophyllum Tacamahaca Seed Oil, Camellia Oleifera Seed Oil, Camellia Reticulata Seed Oil, Camellia Sinensis Seed Oil, Canola Oil, Safflower Seed Oil, Chlorella Vulgaris Oil, Watermelon Seed Oil, Citrullus Lanatus, Lime Seed Oil, Orange Seed Oil, Grapefruit Seed Oil, Coconut Oil, Nucifera (Coconut) Seed Oil, Coconut Seed Butter, Coffee (Coffea Arabica, Coffee) Seed Oil, Chlorella Oil (biotech), Corylus Americana (Hazelnut) Seed Oil, Corylus Avellana (Hazelnut) Seed Oil, Cucumis Melo (Melon) Seed Oil, Cucumis Sativus,Cucumber Seed Oil, Cucurbita Pepo (Pumpkin) Seed Oil, Elaeis Guineensis (Palm) Oil, Palm (Palm) Fruit Oil, Glycine Soja (Soybean) Oil, GosSY-pium Herbaceum (Cotton) Seed Oil, GosSY-pium Hirsutum (Cotton) Seed Oil, Helianthus Annuus (Sunflower) Seed Oil, Macadamia Integrifolia Seed Oil, Macadamia Ternifolia Seed Oil, Mango (Mangifera Indica) Seed Butter, Mango Seed Oil, Melissa Officinalis Seed Oil, Microalgae Oil, Moringa Oleifera Seed Oil, Moringa Peregrina Seed Oil, Oenothera Biennis (Evening Primrose) Primrose Oil, Olea Europaea (Olive) Fruit Oil, Olus Oil, Orbignya Oleifera Seed Oil, Orbignya Speciosa Kernel Oil, Oryza Sativa (Rice) Bran / Germ Oil, Rice Bran Oil, Rice Germ Oil, Rice Lipids, Rice Seed Oil, Passiflora Edulis Seed Oil, Avocado Butter, Avocado Oil, Sweet Almond (Prunus Amygdalus Dulcis) Oil, Apricot (Prunus Armeniaca) Kernel Oil, Peach (Prunus Persica) Kernel Oil, Pomegranate (Punica Granatum) Seed Oil, Apple (Pyrus Malus) Seed Oil, Ricinoleic Acid / Caproic Acid / Caprylic / Capric Acid Triglycerides, Ricinus Communis (Ricinus Communis, Castor) Seed Oil, Rosa Canina Fruit Oil, Rosa Moschata Seed Oil, Rubus Idaeus, Raspberry Seed Oil, Sesame (Sesamum Indicum, Sesame) Seed Butter, Soybean Glycerides, Cocoa (Theobroma Cacao, Cocoa) Seed Butter, Theobroma Grandiflorum Seed Butter, Triticum Vulgare,Wheat bran lipid, wheat germ oil, grape (Vitis Vinifera, Grape) seed oil, corn (Zea Mays, Corn) germ oil and corn oil.
[1101] The abovementioned vegetable oils are the most common natural lipid components used as base substances for the production of cosmetic or pharmaceutical preparations.
[1102] Hydrocarbons (mineral oils) are organic compounds composed entirely of hydrogen and carbon. As defined by IUPAC nomenclature or organic chemistry, hydrocarbons are classified as:
[1103] 1. Saturated hydrocarbons are the simplest type of hydrocarbons. They are composed entirely of single bonds and are saturated with hydrogen. The chemical formula for acyclic saturated hydrocarbons (i.e., alkanes) is C n H 2n+2 The most general form of saturated hydrocarbons is C n H 2n+2(1-r) , where r is the number of rings. Those with exactly one ring are cycloalkanes. Saturated hydrocarbons are the basis of petroleum fuels and exist as straight-chain or branched species.
[1104] 2. Unsaturated hydrocarbons have one or more double or triple bonds between carbon atoms. Those with double bonds are called alkenes. Those with one double bond have the formula C n H 2n (Assuming a non-cyclic structure). Those containing a triple bond are called alkynes. Those with one triple bond have the formula C n H 2n-2 .
[1105] 3. Aromatic hydrocarbons, also called arenes, are hydrocarbons having at least one aromatic ring.
[1106] Hydrocarbons can be liquids (such as hexane and benzene), waxes or low melting point solids (such as paraffin and naphthalene) in particular. The term "aliphatic" refers to non-aromatic hydrocarbons. Saturated aliphatic hydrocarbons are sometimes referred to as "paraffins". Mineral oils and waxes are mainly a mixture of saturated hydrocarbons consisting of straight, branched and ring structures with carbon chain lengths greater than C14. Mineral oils and waxes are chemicals prepared from naturally occurring crude oil. They are mainly composed of mineral oil saturated hydrocarbons (MOSH) and mineral oil aromatic hydrocarbons (MOAH). For decades, hydrocarbons have been used in skin and lip care beauty products because of their excellent skin tolerance, high protection and cleaning properties, and a wide range of viscosity options. Compared with vegetable oils, mineral oils are non-allergenic because they are highly stable and not easily oxidized or rancid.
[1107] Fatty alcohols (or long-chain alcohols) are typically high molecular weight, straight-chain primary alcohols, but can range from as few as 4 to 6 carbons to as many as 22 to 26 carbons (derived from natural fats and oils). The exact chain length varies depending on the source. Some commercially important fatty alcohols are lauryl alcohol, stearyl alcohol, and oleyl alcohol. They are colorless oily liquids (for smaller carbon numbers) or waxy solids, but impure samples may be yellow. Fatty alcohols typically have an even number of carbon atoms and a single alcohol group (-OH) attached to the terminal carbon. Some are unsaturated, and some are branched. Most fatty alcohols are found in nature in the form of waxes, which are esters of fatty acids and fatty alcohols. The traditional sources of fatty alcohols are mostly various vegetable oils, and these vegetable oils are still large-scale raw materials. Alcohols are obtained from triglycerides (triglycerides of fatty acids), which form the bulk of the oil. The process involves transesterification of triglycerides to obtain methyl esters, which are then hydrogenated to obtain fatty alcohols. Fatty alcohols are also prepared from petrochemical sources. In the Ziegler process, ethylene is oligomerized using triethylaluminum, followed by air oxidation. Alternatively, ethylene can be oligomerized to obtain a mixture of olefins, which is hydroformylated, a process that yields odd-numbered aldehydes, which are subsequently hydrogenated. Fatty alcohols are primarily used in the production of detergents and surfactants. They are also a component of cosmetic solvents. They are used in cosmetics as co-emulsifiers, emollients, and thickeners.
[1108] In a preferred variant, the fatty alcohol is selected from the group consisting of phenyl propanol, dimethylphenyl butanol, hexyldecanol, octyldodecanol, octyldodecanol, tridecanol, isostearyl alcohol, phenyl isohexanol, phenyl propanol, trimethylphenyl propanol, isopentanol, isostearyl alcohol and isotridecanol. In a more preferred variant, the fatty alcohol is selected from the group consisting of hexyldecanol, octyldodecanol, phenylpropanol, isopentanol and a mixture of two or more of the above fatty alcohols. The fatty alcohol can be used as a single component or in a mixture with one or more of the above-mentioned other different fatty alcohols.
[1109] Fatty acid esters are a class of esters produced by the combination of fatty acids and alcohols. When the alcohol component is glycerol, the fatty acid esters produced can be monoglycerides, diglycerides or triglycerides. Fatty acid esters have a conditioning effect that softens the skin to produce a smooth feel. They are also added to cosmetics to dissolve highly polar active ingredients and UV absorbers. Esters of straight-chain fatty acids and lower alcohols are effective for dissolving slightly soluble ingredients and are used to make the oil have a soft touch during application. Isostearic acid and other liquid oils with branched fatty acids and unsaturated fatty acids are commonly used as emollients. Esters of higher fatty acids and higher alcohols with relatively high melting points are added to skin creams to adjust the touch when applied.
[1110] Oils and Emollients: In addition to the oil phase or oil component as defined above, the product or preparation according to the present invention preferably includes one or more oil bodies or emollients. Emollients are greasy or oily substances that help to smooth and soften the skin and can also reduce the roughness, chapped or irritated skin. In particular, in sunscreen products, emollients offset the known viscosity of some UV filters and keep crystalline and oil-soluble organic and inorganic UV-filters in a dissolved state and prevent them from recrystallizing. In addition, emollients act as wetting agents for inorganic UV-filters to make them evenly dispersed in the formulation. Suitable oil bodies as a component for forming O / W emulsions are, for example, Guerbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10, carbon atoms, esters of linear C5-C22 fatty acids with linear or branched C5-C22 fatty alcohols, or esters of branched C1-C13 carboxylic acids with linear or branched C6-C22 fatty alcohols, such as, for example, myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, myristyl stearate, palmitostearate, stearyl stearate, isostearyl oleate, fatty stearate, oleic stearate, behenic stearate, erucic stearate, myristic isostearate, palmitic isostearate, stearic isostearate, isostearic isostearate, oleic isostearate, behenic isostearate, oleic isostearate, myristic oleate, palmitic oleate, stearic oleate, isostearic oleate, oleic oleate, behenic oleate, erucic oleate, myristic behenate, palmitic behenate, stearic behenate, isostearic behenate, oleic behenate, behenic oleate, erucic oleate, myristic behenate, palmitic behenate, stearic behenate, isostearic behenate, oleic behenate, behenic behenate, erucic erucate, myristic sinapin, sinapin palmitic, sinapin stearate, sinapin isostearate, sinapin oleate, sinapin behenate and sinapin erucate. Also suitable are esters of linear C6-C22 fatty acids with branched alcohols, in particular 2-ethylhexanol, esters of C18-C38 alkylhydroxycarboxylic acids with linear or branched C6-C22 fatty alcohols, in particular dioctyl malate, esters of linear and / or branched fatty acids with polyols (such as, for example, propylene glycol, dimer or trimer) and / or Guerbet alcohols, triglycerides based on C6-C10 fatty acids, liquid mono- / di- / triglyceride mixtures based on C6-C18 fatty acids, esters of C6-C22 fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, in particular benzoic acid, esters of C2-C12 dicarboxylic acids with linear or branched alcohols having 1 to 22 carbon atoms or polyols having 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched primary alcohols, substituted cyclohexanes, linear and branched C6-C22 fatty alcohol carbonates such as, for example, dicaprylyl carbonate ( CC), Guerbet carbonates based on fatty alcohols having 6 to 18, preferably 8 to 10, carbon atoms, having linear and / or branched C 6 -C 22 Benzoate esters of alcohol (e.g. TN), a linear or branched, symmetrical or asymmetrical dialkyl ether having 6 to 22 carbon atoms in each alkyl group, such as, for example, dioctyl ether ( OE), ring-opening products of epoxidized fatty acid esters with polyols, silicone oils (cyclomethicone, siloxane methicone grade, etc.) and / or aliphatic or cycloalkane such as, for example, squalane, squalene or dialkylcyclohexanes, and any mixtures thereof.
[1111] powder : The composition as defined herein may optionally include a powder. The optional powder provides a smoother and softer formulation on the skin. Representative powders include talc, mica, magnesium carbonate, calcium carbonate, magnesium silicate, magnesium aluminum silicate, silicon dioxide, titanium dioxide, zinc oxide, red iron oxide, yellow iron oxide, black iron oxide, polyethylene powder, methacrylate powder, polystyrene powder, silk powder. Preferred solid powder materials that can be a component of the composition according to the invention are hydrocolloids, such as starch, degraded starch, chemically or physically modified starch, dextrin, (powdered) maltodextrin (preferably with a dextrose equivalent value of 5 to 25, preferably 10 to 20), lactose, silicon dioxide, glucose, modified cellulose, gum arabic, gum ghatti, traganth, gum karaya, carrageenan, pullulan, curdlan, xanthan gum, gellan gum, guar flour, carob flour, alginates, agar, pectin, inulin and mixtures of two or more of these solids, in particular maltodextrin (preferably with a dextrose equivalent value of 15 to 20), lactose, silicon dioxide and / or glucose.
[1112] Rheology Modifiers : The food, cosmetic or pharmaceutical preparation or household care product according to the present invention advantageously comprises one or more thickeners and / or rheology modifiers. The rheology modifier is present in an amount to prevent the composition from dripping or pooling significantly after being applied to the skin or surface. Preferably, the rheology modifier is a carbomer. In some embodiments, the rheology modifier is selected from stearic acid, palmitic acid, stearyl alcohol, cetyl alcohol, behenyl alcohol, stearic acid, palmitic acid, stearyl alcohol polyglycol ether having an average of about 1 to about 21 ethylene oxide units, cetyl alcohol polyglycol ether having an average of about 1 to about 5 ethylene oxide units, and mixtures thereof.
[1113] Other examples of rheology modifiers include thickeners or gelling agents, including materials that can increase the viscosity of the composition. Thickeners include those thickeners that can increase the viscosity of the composition without substantially changing the efficacy of the active ingredient in the formulation. Thickeners can also increase the stability of the formulation of the present application. In some aspects of the present application, thickeners include hydrogenated polyisobutylene or trihydroxystearin, or a mixture of the two. Other non-limiting examples of other thickeners that can be used in the context of the present application include carboxylic acid polymers, cross-linked polyacrylate polymers, polyacrylamide polymers, polysaccharides and gums. Examples of carboxylic acid polymers include cross-linked compounds containing one or more monomers derived from acrylic acid, substituted acrylic acid, and salts and esters of these acrylic acid and substituted acrylic acid, wherein the cross-linking agent contains two or more carbon-carbon double bonds and is derived from polyols (see CTFA International Cosmetic Ingredient Dictionary, Fourth Edition, 1991, Page 12 and Page 80). Examples of commercially available carboxylic acid polymers include carbomers, which are homopolymers of acrylic acid crosslinked with allyl ethers of sucrose or pentaerythritol (e.g., Carbopol from BF Goodrich). TM 900 Series). Non-limiting examples of cross-linked polyacrylate polymers include cationic and nonionic polymers.
[1114] Non-limiting examples of polyacrylamide polymers (including nonionic polyacrylamide polymers, including substituted branched or unbranched polymers) include polyacrylamide, isoparaffin and laureth-7, multi-block copolymers of acrylamide and substituted acrylamides with acrylic acid and substituted acrylic acid.
[1115] Non-limiting examples of polysaccharides include cellulose, carboxymethyl hydroxyethyl cellulose, cellulose acetate propionate carboxylate, hydroxyethyl cellulose, hydroxyethyl ethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose, methyl hydroxyethyl cellulose, microcrystalline cellulose, sodium cellulose sulfate and mixtures thereof. Another example is an alkyl-substituted cellulose, in which the hydroxyl groups of the cellulose polymer are hydroxyalkylated (preferably hydroxyethylated or hydroxypropylated) to form a hydroxyalkylated cellulose, which is then further modified by an ether bond with a C10-C30 straight or branched alkyl. Typically, these polymers are ethers of C10-C30 straight or branched alcohols and hydroxyalkyl cellulose. Other useful polysaccharides include scleroglucan, which comprises a straight chain of (1 to 3) connected glucose units, with (1 to 6) connected glucose per three units.
[1116] Non-limiting examples of gums that can be used with the compositions of the present invention include gum arabic, agar, algin, alginic acid, ammonium alginate, pullulan, calcium alginate, calcium carrageenan, carnitine, carrageenan, dextrin, gelatin, gellan gum, guar gum, guar hydroxypropyltrimonium chloride, hectorite, hyaluronic acid, hydrated silica, hydroxypropyl chitosan, hydroxypropyl guar gum, karaya gum, kelp, locust bean gum, natto gum, potassium alginate, potassium carrageenan, propylene glycol alginate, sclerotium gum, sodium carboxymethyldextrin, sodium carrageenan, tragacanth gum, xanthan gum, and mixtures thereof. In one embodiment, the thickener is an extract of Irish moss (Chondrus crispus) (carrageenan).
[1117] Silicone : In order to give the skin a silky, spreadable and luxurious texture and make the skin look and feel smoother, and in addition to improve processability (defoaming), the food, cosmetic or pharmaceutical preparation or home care product according to the present invention preferably includes one or more silicones or silicone derivatives. The total amount of silicone compounds in the composition according to the present invention can vary, but is generally 0.1% to 35.0% by weight based on the total weight of the composition.
[1118] Dryness Conditioner :The food, cosmetic or pharmaceutical preparation or home care product according to the present invention is preferably combined with a dry feeling regulator. A dry feeling regulator is an agent that, when incorporated into an emulsion, imparts a "dry feeling" to the skin when the emulsion dries. Dry feeling regulators can also reduce the migration of sunscreens on the skin. Dry feeling regulators may include starch, talc, kaolin, chalk, zinc oxide, hydroxyapatite (such as Tinomax CC), silicone oil, inorganic salts (such as barium sulfate and sodium chloride), C6-C12 alcohols (such as octanol); sulfonated oils; surface-treated silica, precipitated silica, pyrogenic silica (such as silica available from Degussa Inc., New York, New York, USA) ) or mixtures thereof; polydimethylsiloxane, a mixture of methylated linear siloxane polymers, available from Dow Corning, Maryland, Michigan, USA under the trade name DC200 fluid. One or more dry feel modifiers may optionally be included in the sunscreen in an amount of 0.01 wt % to 20 wt %, more preferably 0.1 wt % to 10.0 wt %.
[1119] Mitigating substancesThe sunscreen products or cosmetic or pharmaceutical preparations according to the invention may also advantageously contain one or more demulcent substances, wherein any demulcent substances suitable or customary in cosmetic or pharmaceutical applications may be used, such as alpha-bisabolol, azulene, guaiac, 18-beta-glycyrrhetinic acid, allantoin, aloe vera juice or gel, extracts of Hamamelis virginiana (witch hazel), Echinacea species, Centella asiatica, chamomile, Arnica montana, Glycyrrhiza species, algae, seaweed and Calendula officinalis, and plant oils such as sweet almond oil, lanolin, olive oil and panthenol, laureth-9, trideceth-9 and 4-tert-butylcyclohexanol.
[1120] Physiological cooling agent : The food, cosmetic or pharmaceutical preparation or household care product according to the invention can be combined with one or more physiological coolants in a particularly advantageous manner. The use of coolants can relieve itching. Preferred individual coolants for use within the scope of the present invention are listed below. A person skilled in the art can add many other coolants to this list; the listed coolants can also be used in combination with one another, and these coolants are preferably selected from the following list: menthol and menthol derivatives (e.g. L-menthol, D-menthol, racemic menthol, isomenthol, neoisomenthol), menthyl ethers (e.g. (1-menthoxy)-1,2-propanediol, (L-menthoxy)-2-methyl-1,2-propanediol, l-menthyl-methyl ether), menthone glycerol acetal, menthone glycerol ketal or a mixture of the two, menthyl esters (e.g. menthyl formate, menthyl acetate, menthyl isobutyrate, menthyl hydroxyisobutyrate, menthyl lactate, L-menthyl methyl ether ...one glycerol acetal, menthone glycerol ketal or a mixture of the two, menthyl esters (e.g. menthyl formate, menthyl acetate, menthyl isobutyrate, menthyl hydroxyisobutyrate, menthyl lactate, L-menthyl methyl ether, menthyl methyl ether, menthone glycerol acetal, menthone glycerol ketal or a mixture of the two, menthyl esters (e.g. menthyl formate, menthyl acetate, menthyl isobuty Menthyl-L-lactate, L-menthyl-D-lactate, menthyl-(2-methoxy-)acetate, menthyl-(2-methoxyethoxy)acetate, menthyl pyroglutamate), menthyl carbonates (e.g. menthyl propylene glycol carbonate, menthyl ethylene glycol carbonate, menthyl glycerol carbonate or mixtures thereof), half esters of menthol with dicarboxylic acids or their derivatives (e.g. monomenthyl succinate, monomenthyl glutarate, monomenthyl malonate, O-menthyl succinate-N,N-(dimethyl)amide, O-menthyl succinate amide), menthanecarboxylic acid amides (in this case preferably menthanecarboxylic acid-N-acetamide [WS3] or N-(menthyl) succinate-N-acetamide [WS4] or N-(menthyl) succinate-N-acetamide [WS5] or N-(menthyl) succinate-N-acetamide [WS6] or N-(menthyl) succinate-N-acetamide [WS7] or N-(menthyl) succinate-N-acetamide [WS8] or N-(menthyl) succinate-N-acetamide [WS9] or N-(menthyl) succinate-N-acetamide [WS3] αWS5], menthanecarboxylic acid-N-(4-cyanophenyl)amide or menthanecarboxylic acid-N-(-4-cyanomethylphenyl)amide, menthanecarboxylic acid-N-(alkoxyalkyl)amide), menthone and menthone derivatives (e.g. L-menthone glycerol ketal), 2,3-dimethyl-2-(2-propyl)-butyric acid derivatives (e.g. 2,3-dimethyl-2-(2-propyl)-butyric acid-N-methylamide [WS23]), isopulegol or its esters (1-(-)-isopulegol, 1-(-)-isopulegol acetate), menthane derivatives (e.g. p-menthane-3,8-diol), cubebol or synthetic or natural mixtures containing cubebol, pyrrolidone derivatives of cycloalkyldione derivatives (e.g. 3-methyl-2(1-pyrrolidinyl)-2-cyclopenten-1-one) or tetrahydropyrimidin-2-one (e.g. WO 2004 / 026840), other carboxamides (e.g., N-(2-(pyridin-2-yl)ethyl)-3-p-menthanecarboxamide or related compounds), (1R,2S,5R)-N-(4-methoxyphenyl)-5-methyl-2-(1-isopropyl)cyclohexanecarboxamide [WS12], oxalates, and [(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]2-(ethylamino)-2-oxo-acetate (X Cooling). Preferred cooling agents due to their particular synergistic effects are l-menthol, d-menthol, racemic menthol, menthone glycerol acetal (trade names: MGA), menthyl lactate (preferably l-menthyl lactate, especially l-menthyl lactate (trade name: ML)), substituted menthyl-3-carboxamides (such as menthyl-3-carboxylic acid N-ethylamide), 2-isopropyl-N-2,3-trimethylbutyramide, substituted cyclohexanecarboxamides, 3-menthoxypropane-1,2-diol, 2-hydroxyethyl menthyl carbonate, 2-hydroxypropyl menthyl carbonate and isopulegol. Particularly preferred cooling agents are l-menthol, racemic menthol, menthone glycerol acetal (trade name: MGA), menthyl lactate (preferably l-menthyl lactate, especially l-menthyl lactate (trade name: ML)), 3-menthoxypropane-1,2-diol, 2-hydroxyethyl menthyl carbonate and 2-hydroxypropyl menthyl carbonate. Very particularly preferred cooling agents are l-menthol, menthone glycerol acetal (trade name: MGA) and menthyl lactate (preferably l-menthyl lactate, especially l-menthyl lactate (trade name: ML)).
[1121] Alkanediol: In a further preferred variant, the food, cosmetic or pharmaceutical preparation or household care product according to the invention comprises one or more linear alkanediols having a carbon chain of 5 to 12 carbon atoms. Preferably, the one or more linear alkanediols are selected from the group consisting of 1,2-alkanediol, 2,3-alkanediol, 3,4-alkanediol and 1,3-alkanediol, more preferably from the group consisting of 2,3-alkanediol and 1,3-alkanediol. Most preferably, the linear alkanediol is selected from the group consisting of 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, 1,2-nonanediol, 1,2-decanediol, 1,2-undecanediol, 1,2-dodecanediol, 2,3-pentanediol, 2,3-hexanediol, 2,3-heptanediol, 2,3-octanediol, 2,3-nonanediol, 2,3-decanediol, 2,3-undecanediol and 2,3-dodecanediol.
[1122] Initial observations by the inventors surprisingly showed that compositions according to the invention comprising one or more linear alkanediols having a carbon chain of 5 to 12 carbon atoms, preferably as defined herein, show particularly advantageous emulsifying properties. In particular, it was surprisingly found that one or more of said linear alkanediols (if not themselves an emulsion) support the formation of water or oil droplets having a particularly small average size in the emulsion or (if themselves an emulsion) contain water or oil droplets having a particularly small average size.
[1123] In addition, it has been found that the presence of an alkanediol, in particular 1,2-alkanediol or 2,3-alkanediol, improves the solubility of an oil component, such as one or more oil bodies or waxes, in a food, cosmetic or pharmaceutical preparation or a home care product according to the invention. Preferably, the one or more oil bodies or waxes are selected from the group consisting of natural fats and oils, fatty alcohols and alcohols, glycerides and their derivatives, esters, ethers, siloxanes and silanes, waxes and cycloalkanes, preferably from the group consisting of squalene, dialkylcyclohexanes, tetradecane, isohexadecane, dodecane, docosane, paraffin and mineral oils, and are further described below.
[1124] The combination of one or more of the alkanediols mentioned with 4-hydroxyacetophenone (generally in an amount of 0.1 to 2% by weight, more preferably 0.1 to 1% by weight) even increases the solubility of the oil component in a synergistic manner.
[1125] Preferably, the composition comprises 0.01% to 10% by weight, more preferably 0.1% to 5% by weight, still more preferably 0.3% to 3% by weight, most preferably 0.5% to 1% by weight of said linear alkanediol having a carbon chain of 5 to 12 carbon atoms as defined herein, based on the total weight of the composition.
[1126] Emulsifier : In addition, the food, cosmetic or pharmaceutical preparation or household care product according to the invention may advantageously contain one or more emulsifiers. Emulsifiers include amphoteric, anionic, cationic or nonionic emulsifiers, which are used alone or in the form of a mixture. The emulsifier is selected in an appropriate manner depending on the emulsion to be obtained. Preferred examples include:
[1127] - Add 2 mol to 30 mol of ethylene oxide and / or 0 mol to 5 mol of propylene oxide to the linear C 8-22 Fatty alcohol, C 12-22 Products of fatty acids and alkylphenols containing 8 to 15 carbon atoms in the alkyl group;
[1128] - C of the product of adding 1 mol to 30 mol of ethylene oxide to glycerol 12 / 18 Fatty acid monoesters and diesters;
[1129] - mono- and di-glycerides, mono- and di-sorbitan esters and ethylene oxide addition products thereof of saturated and unsaturated fatty acids containing from 6 to 22 carbon atoms;
[1130] - products of the addition of 15 to 60 mol of ethylene oxide onto castor oil and / or hydrogenated castor oil;
[1131] - polyol esters, and in particular polyglycerol esters, such as, for example, polyglycerol polyricinoleate, polyglycerol poly-12-hydroxystearate or polyglycerol dimethyl isostearate. Mixtures of compounds from several of these classes are also suitable;
[1132] - products of the addition of 2 to 15 mol of ethylene oxide onto castor oil and / or hydrogenated castor oil;
[1133] - Based on straight chain, branched, unsaturated or saturated C 6 / 22 Fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerol, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (e.g. sorbitol), alkyl glucosides (e.g. methyl glucoside, butyl glucoside, lauryl glucoside) and polyglucosides (e.g. cellulose);
[1134] - mono-, di- and tri-alkyl phosphates and mono-, di- and / or tri-PEG-alkyl phosphates and their salts;
[1135] -Wool wax alcohol;
[1136] - polysiloxane / polyalkyl polyether copolymers and corresponding derivatives;
[1137] - pentaerythritol, fatty acids, citric acid and fatty alcohols and / or C6-22 Mixed esters of fatty acids, methyl glucose and polyols, preferably glycerol or polyglycerol,
[1138] - polyalkylene glycol, and
[1139] -Glyceryl carbonate.
[1140] Products of the addition of ethylene oxide and / or propylene oxide to fatty alcohols, fatty acids, alkylphenols, glycerol monoesters and diesters and sorbitan monoesters and diesters of fatty acids or to castor oil are known products which are commercially available. They are homologous mixtures whose average degree of alkoxylation corresponds to the ratio between the amount of ethylene oxide and / or propylene oxide and the amount of substrate subjected to the addition reaction. The C of the addition products of ethylene oxide onto glycerol is 12 / 18 Fatty acid monoesters and diesters are known as lipid layer enhancers for cosmetic formulations. Preferred emulsifiers are described in more detail below:
[1141] Partial glycerides: Typical examples of suitable partial glycerides are hydroxystearic acid monoglyceride, hydroxystearic acid diglyceride, isostearic acid monoglyceride, isostearic acid diglyceride, oleic acid monoglyceride, oleic acid diglyceride, ricinoleic acid monoglyceride, ricinoleic acid diglyceride, linoleic acid monoglyceride, linoleic acid diglyceride, linolenic acid monoglyceride, linolenic acid diglyceride, erucic acid monoglyceride, erucic acid diglyceride, tartaric acid monoglyceride, tartaric acid diglyceride, citric acid monoglyceride, citric acid diglyceride, malic acid monoglyceride, malic acid diglyceride and technical mixtures thereof, which may still contain small amounts of triglycerides from the production process. Also suitable are products of the addition of 1 to 30 mol and preferably 5 to 10 mol of ethylene oxide to the abovementioned partial glycerides.
[1142] Sorbitan esters: Suitable sorbitan esters are sorbitan monoisostearate, sorbitan sesquiisostearate, sorbitan diisostearate, sorbitan triisostearate, sorbitan monooleate, sorbitan sesquioleate, sorbitan dioleate, sorbitan trioleate, sorbitan monoerucate, sorbitan hemierucate, sorbitan glycerol dierucate, sorbitan monoricinoleate, sorbitan sesquiricinoleate, sorbitan diricinoleate, sorbitan triricinoleate, sorbitan monooleate, sorbitan sesquioleate, sorbitan dioleate, sorbitan trioleate, sorbitan monoerucate, sorbitan hemierucate, sorbitan glycerol dierucate, sorbitan monoricinoleate, sorbitan sesquiricinoleate, sorbitan diricinoleate, sorbitan triricinoleate, sorbitan monooleate, sorbitan sesquioleate, sorbitan dioleate, sorbitan trioleate, sorbitan monooleate, sorbitan sesquioleate, sorbitan dioleate, sorbitan trioleate, sorbitan monooleate, sorbitan Sugar alcohol monohydroxystearate, sorbitan sesquihydroxystearate, sorbitan dihydroxystearate, sorbitan trihydroxystearate, sorbitan monotartrate, sorbitan sesquitartrate, sorbitan ditartrate, sorbitan tritartrate, sorbitan monocitrate, sorbitan sesquicitrate, sorbitan dicitrate, sorbitan tricitrate, sorbitan monomaleate, sorbitan sesquimaleate, sorbitan dimaleate, sorbitan trimalate and technical mixtures thereof. Also suitable are products of the addition of 1 to 30 mol and preferably 5 to 10 mol of ethylene oxide to the abovementioned sorbitan esters.
[1143] Polyglycerol esters: A typical example of a suitable polyglycerol ester is polyglyceryl-2 dipolyhydroxystearate ( PGPH), Polyglyceryl-3 Diisostearate ( TGI), polyglyceryl-4 isostearate ( GI 34), Polyglyceryl-3 Oleate, Polyglyceryl-3 Diisostearate ( PDI), polyglyceryl-3 methyl glucose distearate (Tego 450), Polyglyceryl-3 Beeswax (Cera )、Polyglyceryl-4 Caprate (Polyglyceryl Caprate T2010 / 90), Polyglyceryl-3 Cetyl Ether ( NL), Polyglyceryl-3 Distearate ( GS 32) and polyglyceryl polyricinoleate ( WOL 1403), polyglyceryl dimethyl ether isostearate and mixtures thereof. Other examples of suitable polyol esters are monoesters, diesters and triesters of trimethylolpropane or pentaerythritol with lauric acid, coconut fatty acid, tallow fatty acid, palmitic acid, stearic acid, oleic acid, behenic acid, etc., optionally reacted with 1 mol to 30 mol of ethylene oxide.
[1144] Anionic emulsifiers: Typical anionic emulsifiers are aliphatic C12-C22 fatty acids, such as palmitic acid, stearic acid or behenic acid, and C12-C22 dicarboxylic acids, such as azelaic acid or sebacic acid, for example potassium cetyl phosphate, and hydrogenated palm glycerides (Emulsiphos / Emulsiphos F).
[1145] Amphoteric emulsifiers: Other suitable emulsifiers are amphoteric or zwitterionic surfactants. Zwitterionic surfactants are surface-active compounds which contain at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule. Particularly suitable zwitterionic surfactants are so-called betaines, such as N-alkyl-N,N-dimethylammonium glycinates, for example cocoalkyldimethylammonium glycinates; N-acylaminopropyl-N,N-dimethylammonium glycinates, for example cocoacylaminopropyldimethylammonium glycinates; and 2-alkyl-3-carboxymethyl-3-hydroxyethylimidazoles containing 8 to 18 carbon atoms in the alkyl or acyl radical and cocoacylaminoethylhydroxyethylcarboxymethylglycinates. The fatty acid amide derivatives known under the CTFA name cocoacylaminopropyl betaine are particularly preferred. Amphoteric surfactants are also suitable emulsifiers. Amphoteric surfactants are compounds which contain in the molecule, except for C 8 / 18 In addition to the alkyl or acyl group, it also contains at least one free amino group and at least one -COOH- or -SO 3 H-group and can form internal salts. Examples of suitable amphoteric surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkyl-amidopropyl glycine, N-alkyltaurine, N-alkylsarcosine, 2-alkyl-aminopropionic acid and alkylaminoacetic acid containing about 8 to 18 carbon atoms in the alkyl group. Particularly preferred amphoteric surfactants are N-cocoyl-alkylamino-propionic esters, cocoylaminoethylaminopropionic esters and C12 / 18 acylsarcosine.
[1146] Anti-aging active ingredients : The composition according to the invention is preferably combined with one or more anti-aging active substances. In the context of the present invention, anti-aging agents or bioactivities are, for example, antioxidants, matrix metalloproteinase inhibitors (MMPIs), skin moisturizers, glycosaminoglycan stimulators, anti-inflammatory agents, TRPV1 antagonists and plant extracts.
[1147] Matrix metalloproteinase inhibitors (MMPIs)The composition according to the invention is preferably combined with one or more inhibitors of matrix metalloproteinases, in particular those inhibitors which inhibit the enzymatic cleavage of collagen by matrix metalloproteinases, selected from the group consisting of ursolic acid, retinyl palmitate, propyl gallate, antijuvenile hormone, 6-hydroxy-7-methoxy-2,2-dimethyl-1(2H)-benzopyran, 3,4-dihydro-6-hydroxy-7-methoxy-2,2-dimethyl-1(2H)-benzopyran, benzamidine hydrochloride, cysteine protease inhibitor N-ethylmaleimide ε-amino-n-hexanoic acid of imine and serine protease inhibitors: phenylmethylsulfonyl fluoride, collhibin (Pentapharm; INCI: hydrolyzed rice protein), oenotherol (Solliance; INCI: propylene glycol, water, evening primrose root extract, ellagic acid and ellagitannins, e.g. from pomegranate), hinokitiol phosphate, EDTA, MGDA (trisodium dicarboxymethyl alanine), galardin, EquiStat (Collaborative Group; apple fruit extract, soybean seed extract, ursolic acid, soy isoflavones and soy protein), sage extract, MDI (Atrium; INCI: glycosaminoglycans), fermiskin (Silab / Mawi; INCI: water and shiitake extract), actimp 1.9.3 (Expanscience / Rahn; INCI: hydrolyzed lupine protein), lipobelle soy aglycone (Mibelle; INCI: alcohol, polysorbate 80, lecithin and soy isoflavones), extracts from green and black tea and further plant extracts, proteins or glycoproteins from soybeans, hydrolyzed proteins from rice, pea or lupine, plant extracts inhibiting MMP, preferably extracts from shiitake, leaf extracts from the family Rosaceae, subfamily Rosoideae, in particular extracts from blackberry leaves, such as SymMatrix (Symrise, INCI: maltodextrin, blackberry (Rubus Fruticosus, Blackberry) leaf extract). Preferred actives are selected from the group consisting of retinyl palmitate, ursolic acid, leaf extracts from the family Rosaceae, subfamily Rosoidea, genistein and daidzein.
[1148] Skin moisturizers and / or humectants : The composition according to the invention advantageously comprises one or more skin moisturizing and / or humectant substances. Preferred skin moisturizing and / or humectant substances are selected from the group consisting of: alkanediols or alkanetriols containing 3 to 12 carbon atoms, preferably C 3 -C 10 -Alkanediol and C 3 -C 10More preferably, the skin moisturizer is selected from the group consisting of glycerol, 1,2-propylene glycol, 1,2-butylene glycol, 1,3-butylene glycol, 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol and 1,2-decanediol. Further skin moisturizing and / or humectant substances include sodium lactate, urea, urea derivatives, alcohols, glycerol, glycols (such as propylene glycol, hexylene glycol), collagen, elastin or hyaluronic acid, diacyl adipate, petrolatum, urocanic acid, lecithin, panthenol, phytantriol, lycopene, (pseudo)ceramides, glycosphingolipids, cholesterol, phytosterols, chitosan, chondroitin sulfate, lanolin, lanolin esters, amino acids, α-hydroxy acids (such as citric acid, lactic acid, malic acid) and derivatives thereof, monosaccharides, disaccharides and oligosaccharides (such as glucose, galactose, fructose, mannose, fructose and lactose), polysaccharides (such as R-glucans, in particular 1,3-1,4-β-glucan from oats), α-hydroxy fatty acids, triterpene acids (such as betulinic acid or ursolic acid) and algae extracts.
[1149] Glycosaminoglycan stimulators: Preferred compositions according to the invention comprise one or more substances stimulating the synthesis of glycosaminoglycans selected from the group consisting of: hyaluronic acid and its derivatives or salts, Subliskin (Sederma, INCI: Sinorhizobium meliloti ferment filtrate, cetyl hydroxyethylcellulose, lecithin), Hyalufix (BASF, INCI: water, butylene glycol, Alpinia galanga leaf extract, xanthan gum, caprylic / capric triglyceride), Stimulhyal (Soliance, INCI: calcium ketogluconate), Syn-Glycan (DSM, INCI: tetradecylaminobutyryl valinamidobutyric acid urea trifluoroacetate, glycerol, magnesium chloride), Kalpariane (Biotech Marine), DC Upregulex (Distinctive Cosmetic Ingredients, INCI: water, butylene glycol, phospholipids, hydrolyzed sericin), glucosamine, N-acetylglucosamine, retinoic acid (preferably retinol and vitamin A), burdock fruit extract, loquat extract, genkwain, N-methyl-L-serine, (-)-α-bisabolol or synthetic α-bisabolol, such as, for example, Dragosantol and Dragosantol 100 from Symrise, oat glucan, echinacea extract, and soy protein hydrolyzate. Preferred active substances are selected from the group consisting of hyaluronic acid and its derivatives or salts, retinol and its derivatives, (-)-α-bisabolol or synthetic α-bisabolol, such as, for example, Dragosantol and Dragosantol 100 from Symrise, oat glucan, Echinacea extract, Rhizobium meliloti ferment filtrate, calcium ketogluconate, calcium ketogluconate, Alpinia galanga leaf extract and tetradecylaminobutyryl valinamidobutyric acid urea trifluoroacetate.
[1150] Anti-inflammatory agents : The composition according to the invention is preferably combined with an anti-inflammatory and / or redness and / or itch relieving ingredient, in particular a steroidal substance of the corticosteroid type selected from the group consisting of: hydrocortisone, dexamethasone, dexamethasone phosphate, methylprednisolone or cortisone, which are advantageously used as anti-inflammatory active ingredients or active ingredients for relieving redness and itch, the list of which can be expanded by adding other steroidal anti-inflammatory agents. Non-steroidal anti-inflammatory drugs can also be used. More specifically:
[1151] (i) steroidal anti-inflammatory substances of the corticosteroid type, in particular hydrocortisone, hydrocortisone derivatives (such as hydrocortisone 17-butyrate), dexamethasone, dexamethasone phosphate, methylprednisolone or cortisone,
[1152] (ii) nonsteroidal anti-inflammatory substances, in particular oxicams such as piroxicam or tenoxicam; salicylates such as aspirin, disalcid, solprin or fendosal; acetic acid derivatives such as diclofenac, fenclofenac, indomethacin, sulindac, tolmetin or clindanac; fenamates such as mefenamic acid, meclofenamic acid, flufenamic acid or niflumic acid; propionic acid derivatives such as ibuprofen, naproxen or benoxaprofen; pyrazoles such as phenylbutazone, oxybutazone, febrazone or azapropazone,
[1153] (iii) natural or naturally occurring anti-inflammatory substances or substances which reduce redness and / or itching, in particular extracts or fractions thereof from chamomile, aloe, myrobalan, madder, willow, epilobium, oats, calendula, arnica, St John's wort, honeysuckle, rosemary, passionflower, witch hazel, ginger or echinacea, or the single active compounds thereof,
[1154] (iv) histamine receptor antagonists, serine protease inhibitors (e.g., serine protease inhibitors from soybean extract), TRPV1 antagonists (e.g., 4-tert-butylcyclohexanol), NK1 antagonists (e.g., aprepitant, hydroxyphenylpropionamide benzoic acid), and TRPV3 antagonists.
[1155] Examples that may be cited here are oxicams, such as piroxicam or tenoxicam; salicylates, such as aspirin, disalicylate, solprin or fendosal; acetic acid derivatives, such as diclofenac, fenclofenac, indomethacin, sulindac, tolmetin or clindanac; fenamates, such as mefenamic acid, meclofenamic acid, flufenamic acid or niflumic acid; propionic acid derivatives, such as ibuprofen, naproxen or benoxaprofen; or pyrazoles, such as phenylbutazone, oxybutazone, feprazone or azapropazone. Anthranilic acid derivatives are preferred antipruritic ingredients in the composition of the present invention.
[1156] Also useful are mixtures of natural or naturally occurring anti-inflammatory substances or substances which reduce redness and / or itching, in particular extracts or fractions from chamomile, aloe, myrobalan, madder, willow, willowherb, oats, calendula, arnica, St. John's wort, honeysuckle, rosemary, passion flower, witch hazel, ginger or echinacea; selected from the group consisting of extracts or fractions from chamomile, aloe, oats, calendula, arnica, honeysuckle, rosemary, witch hazel, ginger or echinacea, and / or pure substances, preferably alpha-bisabolol, apigenin, apigenin-7-glucoside, gingerols, shogaols , gingerdiols, dehydrogingerdiones, paradols, natural or naturally occurring avenanthramides, preferably tranilast, avenanthramide A, avenanthramide B, avenanthramide C, non-natural or non-naturally occurring avenanthramides, preferably dihydroavenanthramide D, dihydroavenanthramide E, avenanthramide D, avenanthramide E, avenanthramide F, boswellic acid, phytosterols, glycyrrhizin, glabridin and licoricechalcone A; selected from the group consisting of α-bisabolol, natural avenanthramides, non-natural avenanthramides, preferably dihydroavenanthramide D (such as WO 2004 047833A1), boswellic acid, phytosterols, glycyrrhizin and licoricechalcone A, and / or allantoin, panthenol, lanolin, (pseudo)ceramides [preferably ceramide 2, hydroxypropyl bispalmitamide MEA, hexadecyloxypropyl glyceryl methoxypropyl myristamide, N-(1-hexadecyl)-4-hydroxy-L-proline (1-hexadecyl) ester, hydroxyethyl palmityloxyhydroxypropyl palmitamide], glycosphingolipids, phytosterols, chitosan, mannose, lactose and β-glucans, in particular 1,3->1,4-β-glucans from oats.
[1157] TRPV1 antagonists : Preferred compositions according to the invention comprise one or more TRPV1 antagonists. Suitable compounds that reduce skin nerve hypersensitivity based on their action as TRPV1 antagonists include, for example, trans-4-tert-butylcyclohexanol, or compounds that indirectly modulate TRPV1 through activation of μ-receptors, such as acetyl tetrapeptide-15, are preferred.
[1158] Antimicrobial Agents:The food, cosmetic or pharmaceutical preparation or household care product according to the present invention can be advantageously combined with an antimicrobial agent that acts primarily against microorganisms (especially bacteria, yeasts and / or fungi) and includes one or more antimicrobial agents such as capryloylhydroxamic acid, o-cymene-5-ol, isopropylparaben, capryloylglycine, phenylpropanol, tropolone, PCA cocoyl arginine ethyl ester, 2-methyl 5-cyclohexylpentanol, phenoxyethanol, disodium EDTA, methylparaben and its salts, sodium benzoate, benzyl alcohol. , potassium sorbate, benzyl salicylate, propylparaben, sodium methylparaben, methylchloroisothiazolinone, methylisothiazolinone, ethylhexylglycerin, butylparaben, ethylparaben, sodium propylparaben, DMDM hydantoin, dehydroacetic acid, salicylic acid, chlorphenesin, isobutylparaben, sodium ethylparaben, diazolidinyl urea, diazolidinyl urea, farnesol, bisabolol, caprylic acid glyceryl, sodium phytate or phytic acid, sodium levulinate or levulinic acid and its esters and / or ketones, chlorhexidine, lauric acid glyceryl, anisic acid and its salts, chlorhexidine digluconate, TEA-salicylate, phenethyl alcohol, glyceryl caprate, sorbitan caprylate, tetrasodium glutamate diacetate, trisodium ethylenediamine disuccinate, hydroxyethoxyphenyl butanone, hydroxyethoxyphenyl butanol, itaconic acid, hydroxymethyloctopirox, propylene glycol caprylate, climbazole, undecylenyl glycine, thymol, 4-hydroxyacetophenone, lactic acid, sodium lactate, trisodium dicarboxymethyl alanine, raspberry ketone, sesquioctanoate, 3-hydroxypropyl benzoate, 3-hydroxypropyl anisic acid Esters, 3-hydroxypropyl 2-hydroxybenzoate, 1,3-propylene glycol, 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, 1,2-nonanediol, 1,2-decanediol, 1,2-undecanediol, 1,2-dodecanediol, 2,3-pentanediol, 2,3-hexanediol, 2,3-heptanediol, 2,3-octanediol, 2,3-nonanediol, 2,3-decanediol, 2,3-undecanediol, 2,3-dodecanediol, and any mixture thereof.
[1159] Preferably, the food, cosmetic or pharmaceutical preparation or household care product according to the invention comprises one or more antimicrobial agents selected from the group consisting of 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, 1,2-nonanediol, 1,2-decanediol, 1,2-undecanediol, 1,2-dodecanediol, 2,3-pentanediol, 2,3-hexanediol, 2,3-heptanediol, 2,3-octanediol, 2,3-nonanediol, 2,3-decanediol, 2,3-undecanediol, 2,3-dodecanediol, 2-benzylheptanol, 2-hydroxyacetophenone, 2-methyl 5-cyclohexylpentanol, 3-hydroxypropyl 2-hydroxybenzoate, 4-hydroxyacetophenone and any mixtures thereof. More preferably, the food, cosmetic or pharmaceutical preparation or the home care product according to the invention comprises one or more antimicrobial agents selected from the group consisting of 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, 1,2-nonanediol, 1,2-decanediol, 1,2-undecanediol, 1,2-dodecanediol, 1,2-tridecanediol, 4-hydroxyacetophenone and any mixture thereof.
[1160] In order to further enhance the antimicrobial efficacy, the food, cosmetic or pharmaceutical preparation or household care product as defined herein is advantageously combined with at least one additional antimicrobial agent different from the above-mentioned antimicrobial agent. The combination with additional antimicrobial agents provides reliable protection against microbial degradation and deterioration of the preparation, particularly during storage. In addition, other different antimicrobial agents provide reliable protection for other microorganisms as described above, and these other microorganisms are for example Corynebacterium, Anaerococcus, Finegoldia, Moraxella, Porphyromonas, Fusobacterium, Malassezia, Peptoniphilus, Streptococcus, Lactobacillus, Gardnerella, Fannyhessea, Epidermophyton, Trichophyton, Cutibacterium. Therefore, the combination with other different antimicrobial agents allows the antimicrobial protection for the microorganisms of different groups, and therefore allows the microorganisms of a wider range.In the context of the present invention, the further different antimicrobial agents are preferably selected from the group consisting of 2-benzylheptanol, alkyl (C 12-22) trimethylammonium bromides and chlorides, ascorbic acid and its salts, benzalkonium bromide, benzalkonium chloride, benzalkonium saccharinate, benzethonium chloride, benzoic acid, camphor, cetylpyridinium chloride, chlorhexidine diacetate, chlorhexidine dihydrochloride, chlorocresol, chloroxylenol, cyclohexylglycerol, dimethylphenylbutanol, dimethylphenylpropanol, ethanol, lauroylarginine ethyl ester HCl, lauroylarginine ethyl ester laurate, eucalyptol, gluconic acid and its salts, glycerol, hexamidine, hexamidine diisethionate. diisethionate), hexylglycerin, iodopropynyl butylcarbamate, jasmol, lauryl alcohol, levulinic acid and its esters and / or ketals, mannitol, menthol, methyl salicylate, octenidine HCl, polyarginine, polyglyceryl-10 laurate, polyglyceryl-2 caprate, polyglyceryl-3 caprylate, polylysine, salvia officinalis (sage) oil, silver chloride, silver citrate, sodium caproyl lactylate, sodium caproyl / lauroyl lactylate, sodium lauroyl lactylate, sorbic acid, sorbitol, plankton extract, triclocarban, triclosan, triethyl citrate, xylose sesquioctanoate, zinc citrate, zinc pyrithione, zinc ricinoleate, and any mixture thereof.
[1161] The abovementioned antimicrobial agents are used in food, cosmetic or pharmaceutical preparations or household care products as a single component or preferably in a mixture with two or more of the abovementioned additional antimicrobial agents.
[1162] The antimicrobial agent is present in the food, cosmetic or pharmaceutical preparation or home care product in an amount of 0.01 to 25.0 wt%, preferably 0.02 to 15.0 wt%, most preferably 0.05 to 6.0 wt%, based on the total weight of the final formulation.
[1163] Advantageously, the at least one antimicrobial alkanediol is present in the food, cosmetic or pharmaceutical preparation or household care product in an amount of 0.1% to 5% by weight, based on the total weight of the final formulation, and / or 4-hydroxyacetophenone is present in the food, cosmetic or pharmaceutical preparation or household care product in an amount of 0.01% to 2% by weight, based on the total weight of the final formulation.
[1164] preservativeFor preservation purposes, the composition according to the invention preferably comprises one or more preservatives. Suitable and advantageous preservatives are, for example, benzoic acid, sodium benzoate, ammonium benzoate, butyl benzoate, calcium benzoate, MEA benzoate, isobutyl benzoate, isopropyl benzoate, magnesium benzoate, tetrabutyl benzoate, methyl benzoate, phenyl benzoate, potassium benzoate, propyl benzoate, propionic acid, ammonium propionate, calcium propionate, magnesium propionate, potassium propionate, sodium propionate, salicylic acid, calcium salicylate, magnesium salicylate, salicylate, sodium salicylate, TEA salicylate, sorbic acid, calcium sorbate, sodium sorbate, potassium sorbate, o-phenylphenol, sodium sulfite, ammonium bisulfite, potassium bisulfite, potassium hydrogen ... sulfite), sodium bisulfite, sodium metabisulfite, potassium metabisulfite, chlorobutanol, 4-hydroxybenzoic acid, methylparaben, ethylparaben potassium, potassiumparaben, methylparaben sodium, ethylparaben sodium, ethylparaben, sodiumparaben, methylparaben potassium, calciumparaben, butylparaben, propylparaben, propylparaben sodium, butylparaben sodium, butylparaben potassium, propylparaben potassium, dehydroacetic acid, de Sodium hydroacetate, formic acid, sodium formate, dibromohexamidine isethionate, thimerosal, phenylmercuric acetate, phenylmercuric benzoate, undecylenic acid, potassium undecylenate, sodium undecylenate, calcium undecylenate, MEA undecylenate, TEA undecylenate, hexetidine, 5-bromo-5-nitro-1,3-dioxane, 2-bromo-2-nitropropane-1,3-diol, dichlorobenzyl alcohol, triclocarban, para-chloromecresol, triclosan, Chloroxylenol, imidazolidinyl urea, polyaminopropyl; biguanide, phenoxyethanol, methenamine, climbazole, DMDM hydantoin, benzyl alcohol, 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2-pyridone, piroctone olamine, bromochlorfen, o-cymene-5-ol, methylchloroisothiazolinone and methylisothiazolinone, chlorhexidine, chlorhexidine diacetate, chlorhexidine digluconate, chlorhexidine dihydrochloride, phenoxyisopropyl alcohol, behenyltrimethylammonium chloride (1), cetrimonium bromide, cetrimonium chloride (2), lauryltrimethylammonium bromide, lauryltrimethylammonium chloride, stearyltrimethylammonium bromide, stearyltrimethylammonium chloride (2), dimethyloxazoline, diazolidinyl urea, hexamidine, hexamidine dihydroxyethyl sulfonate, hexamidine dihydroxybenzoate (hexamidine diparaben), hexamidine paraben, glutaraldehyde, 7-ethylbicyclooxazoline, chlorphenesin, sodium hydroxymethylglycinate, silver chloride, benzethonium chloride, benzalkonium chloride, benzalkonium bromide, benzalkonium saccharinate, formaldehyde benzyl alcohol hemiacetal, iodopropynyl butylcarbamate, methylisothiazolinone, citric acid, silver citrate, hydroxyethoxyphenyl butyric acid (HEPB), and any mixture thereof.
[1165] Antibacterial or antifungal active substances In addition to the antimicrobial agents described therein, antibacterial or antifungal active substances can also be used particularly advantageously in the compositions according to the invention, wherein any antibacterial or antifungal active substances suitable or customary in cosmetic or pharmaceutical, in particular dermatological applications can be used. In addition to a large class of conventional antibiotics, other products that are advantageous here include those products related to cosmetics, such as, in particular, triclosan, climbazole, octoxyglycerol, (1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)-pyridone 2-aminoethanol salt), chitosan, farnesol, monolaurin, or a combination of the substances.
[1166] UV-Filters : The composition as defined herein is advantageously combined with at least one primary sun protection factor and / or with at least one secondary sun protection factor in order to increase the SPF, ie to obtain a high SPF and to cover a wide UVA and UVB range.
[1167] The compositions according to the invention advantageously contain at least one UVA filter and / or at least one further UVB filter and / or broadband filter and / or at least one inorganic pigment, preferably at least one UVA filter and at least one UVB filter, for their use in protecting against UV radiation.
[1168] For example, at least one primary UV-filter may be one or more organic UV-filters and / or one or more inorganic UV-filters. Non-limiting examples of UV-filters include:
[1169] (i) Sparingly soluble UV filters (no significant solubility in water or oil), such as methylenebis-benzotriazolyltetramethylbutylphenol, terphenyltriazine, ketone, 1,1'-(1,4-piperazinediyl)bis[1-[2-[4-(diethylamino)-2-hydroxybenzoyl-]phenyl];
[1170] (ii) oil-soluble organic UV-filters (at least partially soluble in oil or organic solvents), such as bis-ethylhexyloxyphenol methoxyphenyl triazine, butyl methoxydibenzoylmethane (BMBM), oxybenzone, sulisobenzone, diethylhexyl butamido triazone (DBT), drometrizole trisiloxane, ethylhexyl methoxycinnamate (EHMC), ethylhexyl salicylate (EHS), ethylhexyl triazone (EHT), homosalate, isopentyl p-methoxycinnamate, 4-methylbenzylidene camphor, octocrylene (OCR), polysilicone-15 and diethylaminohydroxybenzoyl hexyl benzoate (DHHB);
[1171] (iii) inorganic UV-filters, such as titanium and zinc oxides, iron oxide, zirconium oxide and cerium oxide; and
[1172] (iv) water-soluble UV-filters such as phenylbenzimidazole sulfonic acid (PBSA), sulisophenone-sodium salt, benzalkonium camphorsulfonic acid, camphorbenzalkonium chloride methosulfate, cinoxate, disodium phenyldibenzylimidazole tetrasulfonate, terephthalylidene dicamphorsulfonic acid, PABA and PEG-25PAB; and any mixtures thereof.
[1173] Many different organic compounds can act as UV filters. They are divided into several structural types:
[1174] (3) Benzophenone
[1175] a. Benzophenone-3 (BP3)
[1176] b. Benzophenone-4 (BP4)
[1177] (4) Salicylate
[1178] a. Homosalate (HMS)
[1179] b. 2-Ethylhexyl salicylate (EHS)
[1180] (5) p-Aminobenzoic acid and its derivatives
[1181] a. Ethylhexyl dimethyl PABA (OD-PABA)
[1182] b.4-para-aminobenzoic acid (PABA)
[1183] (6) Benzimidazole derivatives
[1184] a. Phenylbenzimidazole sulfonic acid (PMDSA)
[1185] b. Disodium phenyl dibenzimidazole tetrasulfonate (disodium bis disulfonate)
[1186] (7) Triazine
[1187] a. Ethylhexyl triazone (OT)
[1188] b. Diethylhexyl butyramido triazone (DBT)
[1189] c. Bis-ethylhexyloxyphenol methoxyphenyl triazine (EMT)
[1190] (8) Benzotriazole
[1191] a. Dromtriazole trisiloxane (DRT)
[1192] b. Methylene bis-benzotriazolyl tetramethylbutylphenol (MBP, biscotrizole)
[1193] (9) Dibenzoylmethane derivatives
[1194] a.4-tert-Butyl-4'-methoxydibenzoylmethane (BM-DBM, avobenzone)
[1195] (10) Cinnamate
[1196] a. Ethylhexyl methoxycinnamate (OMC)
[1197] b. Isoamyl methoxycinnamate (IMC, amitraz)
[1198] (11) Camphor derivatives
[1199] a. Camphor terephthalate sulfonic acid (PDSA)
[1200] b.3-Benzalcamphor (3BC)
[1201] c. Benzylidene camphorsulfonic acid (BCSA)
[1202] d.4-Methylbenzylidene camphor (4-MBC)
[1203] e. Polyacrylamide methylbenzylidene camphor (PBC)
[1204] (12) Camphor benzalkonium chloride methylsulfate (CBM)
[1205] According to the invention, the at least one inorganic UV filter is selected from the group consisting of titanium dioxide (TiO 2 ) (amorphous or crystalline in the form of rutile and / or anatase), zinc oxide (ZnO), iron oxide (Fe 2 O 3 ), zirconium oxide (ZrO 2 ), silicon dioxide (SiO 2 ), manganese oxide (such as MnO), aluminum oxide (Al 2 O 3 ), cerium oxide (Ce 2 O 3 ), barium carbonate (BaCO 3 ), calcium carbonate (CaCO 3 ) and mixtures thereof.
[1206] Preferably, the at least one inorganic UV-filter is titanium dioxide, zinc oxide and mixtures thereof, more preferably, the at least one inorganic UV-filter is titanium dioxide and / or zinc oxide, and most preferably, the at least one inorganic UV-filter is zinc oxide. ZnO has a broad UVA / UVB absorption curve, while TiO 2 Provides better UVB protection.
[1207] According to another variant, the at least one inorganic UV filter has a weight median particle size d 50 In the form of particles ranging from 1 nm to 1000 nm, preferably from 3 nm to 800 nm, more preferably from 5 nm to 600 nm, and most preferably from 10 nm to 400 nm.
[1208] Inorganic UV filters also encompass nanopigments of untreated or treated metal oxides (average size of the primary particles: generally 1 nm to 100 nm, preferably 3 nm to 90 nm, more preferably 5 nm to 80 nm, and most preferably 10 nm to 70 nm), such as, for example, titanium dioxide (TiO 2 ) (amorphous or crystalline in the form of rutile and / or anatase), zinc oxide (ZnO), iron oxide (Fe 2 O 3 ), zirconium oxide (ZrO 2 ), silicon dioxide (SiO 2 ), manganese oxide (such as MnO), aluminum oxide (Al 2 O 3 ), cerium oxide (Ce 2 O 3 ), barium carbonate (BaCO 3 ), calcium carbonate (CaCO 3 ) and their mixtures.
[1209] Treated nanopigments and non-nanopigments are pigments that have been subjected to one or more surface treatments of chemical, electrical, mechanochemical and / or mechanical properties with compounds such as amino acids, beeswax, fatty acids, fatty acid esters, fatty alcohols, anionic surfactants, lecithin, sodium, potassium, zinc, iron or aluminum salts of fatty acids, metal (titanium or aluminum) alkoxides, polyethylene, silicones, proteins (collagen or elastin), alkanolamines, silica, metal oxides, sodium hexametaphosphate, alumina or glycerol, hydrated silica, stearic acid, jojoba esters or glutamic acid derivatives.
[1210] The treated nanopigments and non-nanopigments may more particularly be titanium oxide treated with silica and alumina, alumina and aluminum stearate, alumina and aluminum laurate, aluminum hydroxide, iron oxide and iron stearate, silica, alumina and silicone, sodium hexametaphosphate, octyl trimethoxy silane, alumina and stearic acid, alumina and glycerol, or alumina and silicone or polyhydroxystearic acid, hydrated silica, jojoba esters, stearoyl glutamic acid, glutamic acid and derivatives, trimethoxy caprylyl silane, glycerol, polydimethylsiloxane, hydrogenated polydimethylsiloxane, simethicone or a combination thereof. Other titanium oxide nanopigments treated with silicone are preferably TiO treated with octyl trimethyl silane. 2 , preferably, the average size of its basic particles is 25nm to 40nm; TiO treated with polydimethylsiloxane 2 , preferably, the average size of its basic particles is 21 nm; or TiO treated with polydimethylhydrogensiloxane 2 , preferably, the average size of its primary particles is 25 nm.
[1211] Coated zinc oxide nanopigments and zinc oxide non-nanopigments are, for example, ZnO coated with polymethylhydrogensiloxane; ZnO dispersions in cyclomethicone / oxyethylated polydimethylsiloxane containing 30% or 80% nano or non-nano zinc oxide coated with silica and polymethylhydrogensiloxane; ZnO coated with perfluoroalkyl phosphate and perfluoroalkylethyl-based copolymers as dispersions in cyclopentasiloxane; ZnO coated with dimethoxydiphenylsilane triethoxyoctylsilane crosspolymer; ZnO coated with glutamic acid; ZnO coated with octyltriethoxysilane; ZnO coated with polydimethylsiloxane; ZnO coated with silicone grafted acrylic dispersed in cyclomethicone ZnO coated with triethoxycaprylylsilane; ZnO coated with polyhydroxystearic acid; ZnO treated with alumina dispersed in a mixture of ethylhexyl methoxycinnamate / PVP-hexadecene / polymethicone copolymer; ZnO coated with silica and polymethylsilsesquioxane; ZnO dispersed in a hydroxystearic acid condensate; or ZnO coated with a mixture of stearoyl glutamate, jojoba esters, polyhydroxystearic acid, isopropyl titanium triisostearate, hydrogenated olive oil stearyl esters, cetearyl nonanoate, beeswax, polydimethicone, dimethoxydiphenylsilane triethoxycaprylylsilane crosspolymer, octyl triethoxysilane, glutamic acid and sodium stearoyl lactylate.
[1212] Preference is also given to particulate UV filters or inorganic pigments which may optionally be hydrophobized, such as iron oxides (Fe 2 O 3 ), zirconium oxide (ZrO 2), silicon oxide (SiO 2 ), manganese oxides (such as MnO), aluminum oxides (Al 2 O 3 ), cerium oxide (such as Ce 2 O 3 ), barium carbonate oxide (BaCO 3 ), calcium carbonate oxide (CaCO 3 ) or a mixture thereof.
[1213] The at least one essential organic and / or inorganic UV-filter is selected from the group consisting of camphor benzalkonium chloride methosulfate, homosalate, benzophenone-3, phenylbenzimidazole sulfonic acid, terephthalylidene dicamphor sulfonic acid, butyl methoxydibenzoylmethane, benzal camphor sulfonic acid, octocrylene, polyacrylamidomethyl benzalkonium camphor, ethylhexyl methoxycinnamate, PEG-25 PABA, isoamyl p-methoxycinnamate, ethylhexyl triazone, drometrizole trisiloxane, diethylhexyl butamido triazone, 4-methylbenzylidene camphor, ethylhexyl salicylate, ethylhexyl dimethyl PABA, benzophenone-4, benzophenone-5, methylene bis-benzotriazolyl tetramethylbutylphenol (nano), disodium phenyl dibenzimidazole tetrasulfonate, bis-ethylhexyloxyphenol methoxyphenyl triazine, polysilicone-15, titanium dioxide, titanium dioxide (nano), diethylamino hydroxybenzoyl hexyl benzoate, terphenyl triazine (nano), zinc oxide, zinc oxide (nano), phenylene bis-diphenyl triazine, methoxypropylaminocyclohexenylethyleneoxyethyl cyanoacetate, bis-(diethylaminohydroxybenzoyl) piperazine, TEA salicylate, benzophenone-8, PABA, ethylhexyl dimethyl PABA, menthyl anthranilate, and any mixture thereof.
[1214] The abovementioned essential organic or inorganic UV filters are used in the compositions according to the invention as individual components or preferably in the form of a mixture with two, three, four or more of the abovementioned UV filters.
[1215] In order to optimize the SPF, i.e. to obtain a high SPF of 6 to 100, preferably 6 to 70, and to cover a wide UVA and UVB range, these compositions contain at least two, more preferably at least three, most preferably at least four or even more different primary organic and / or inorganic UV-filters, i.e. in particular organic UV-filters and / or inorganic pigments (UV filter pigments). The combination of different kinds of effective sunscreen UV-filters (such as UVA filters, UVB, broadband filters, inorganic pigments) provides reliable protection against different UV rays in the wavelength range of 290 nm to 400 nm.
[1216] Advantageously, the amount of main organic and / or inorganic sunscreen substances (UV filters) in the compositions according to the invention is advantageously from 0.01% to 80.0% by weight, preferably from 0.1% to 75.0% by weight, most preferably from 0.5% to 70.0% by weight, based on the total weight of the ready-to-use formulation.
[1217] Besides the abovementioned primary organic and / or inorganic sunscreen UV-filters, secondary sunscreen ingredients of the antioxidant type can also advantageously be used in the compositions according to the invention in order to further optimize the UV protection.
[1218] Secondary sunscreen ingredients of the antioxidant type interrupt the chain of photochemical reactions that are initiated when UV rays penetrate the skin.
[1219] Typical examples of secondary sunscreen ingredients are amino acids (e.g. arginine, lysine, glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (e.g. urocanic acid) and their derivatives, peptides such as D,L-carnosine, D-carnosine, L-carnosine and their derivatives (e.g. anserine), carotenoids, carotenes (e.g. alpha-carotene, beta-carotene, lycopene) and their derivatives, chlorogenic acid and its derivatives, lipoic acid and its derivatives (e.g. dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (e.g. thioredoxin). , glutathione, cysteine, cystine, cystamine and glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, α-linoleyl, cholesterol and their glycerides) and their salts, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and its derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and sulfenyl imide compounds (e.g., buthionine sulfenyl imide, homocysteine sulfenyl imide, butyl sulfone, pentathionine sulfenyl imide, hexathionine sulfenyl imide and heptathionine sulfenyl imide) imines), also (metal) chelators (e.g. α-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), α-hydroxy acids (e.g. citric acid, lactic acid, malic acid), humic acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives), unsaturated fatty acids and their derivatives (e.g. linoleic acid, oleic acid), folic acid and its derivatives, ubiquinone and ubiquinol and their derivatives, vitamin C and its derivatives (e.g. ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl acetate), tocopherol and its derivatives (e.g. vitamin C benzoic acid resin, rutinic acid and its derivatives, glucosyl rutin, ferulic acid, furfurylidene glucitol, carnosine, butylated hydroxytoluene, butylated hydroxyanisole, dehydroguaiac acid, nordihydroguaiac acid, trihydroxybutyrophenone, uric acid and its derivatives, mannose and its derivatives, superoxide dismutase, sinapic acid, sinapoyl ... 4 ), selenium and its derivatives (e.g. methionine selenium), stilbenes and their derivatives (e.g. stilbene oxide, trans-stilbene oxide) and derivatives of these active substances (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) suitable for the purposes of the present invention.
[1220] The group of secondary sunscreen ingredients also encompasses plant extracts which have antioxidant and general photoprotective properties and interrupt the chain of photochemical reactions initiated when UV rays penetrate the skin and thus effectively prevent skin aging. The plant extract with UV protection properties is selected from the group consisting of lignin / cellulose, lignin, hydrolyzed lignin, propolis and green propolis, galangal extract, macroalgae and microalgae (Porphyra, red algae (Porphyra Umbilicalis), Palmaria palmata, Saccharina latissimi, Corallina pilulifera, Eckloina cava, Sargassumsagamianum, Porphyra rosengurttii, Sargassumsiliquastrum, Thalassiosira weissflogii, green microalgae (e.g. Interfilum and Klebsormidium), seaweeds (e.g. Padina australis, Eucheuma cottonii), Pongamia Glabra Seed Oil, Karanja Oil (Millettia pinnata), Rhatania Extrakt (Kramerialappacea), Lichens, Soybean, Caper (Capparis spinosa), Bamboo, Green Coffee Oil, Buriti Oil (Mauritia flexuosa), Black Sea Cucumber (Holothuria atra), Cyanobacteria, Fernblock (Polypodium leucotomos), Green Tea, Black Tea (Camellia sinensis), Aloe Vera, Walnut, Borage Oil, Evening Primrose Oil, Avocado Oil, Tea Tree Oil, Red Clover (Trifolium pratenseL.), soybean(Glycine max L.), Caper buds (Capper candidum), Almonds, Flame of the forest (Spathodea campanulata), Milk thistle (Silybum marianum L.), Cashew shells, Grapes, Red oranges, Pomegranates (Punica granatu), Bilberry (Vaccinium myrtillus L.), Bog blueberry (Vaccinium uliginosum L.), Strawberry (Fragariaananassa), Foti (Polygonum multiflorum Thunb), Turmeric (Curcumalonga L.), Ginseng (Panax ginseng), English ivy (Hedera helix), Broccoli (Brassica oleracea var italica), Tamarind (Tamarindus indica), indica), Opuntia ficus-indica, coffee, basil (Basil, Ocimum basilicum, Linn.), pomegranate seed oil (Punica granatum), wheat germ oil (Triticum vulgare), black currant seed oil (Ribes nigrum), sesame oil (Sesamumindicum), carrot root (Daucuscarotasativa), raspberry seed oil (Rubus idaeus), Sri Lankan traditional medicinal plants (Aporosalindleyana (Euphorbiaceae), Atalantia ceylanica (Rutaceae), Hibiscus furcatus (Malvaceae), Olaxzeylanica (Olacaceae), snakeroot (Ophiorrhiza mungos) (Rubiaceae), Argyreia populifolia (Convolvulaceae), Ipomoea mauritiana (Convolvulaceae), Lasia spinosa (Araceae), Leucas zeylanica (Lamiaceae), Plectranthus zeylanicus (Lamiaceae) and traditional Brazilian medicinal plants (D. gardneriana seeds, L. microphylla leaves, Amburana cearensis, Aspidosperma cuspa, Aspidosperma pyrifolium, Croton sonderianus, Curatella americana, Dimophandra gardneriana, Lippia microphylla, Luehea paniculata, Sidagalheirensis and any mixture thereof.
[1221] Preferably, the plant extract having UV protective properties is selected from the group consisting of lignin / cellulose, lignin, hydrolyzed lignin, galangal extract, Porphyra, red algae (Porphyra umbilicus), green microalgae (e.g. Entotrichum and Creatum), seaweeds (e.g. Padilla, Eucheuma), Pongamia glabrous seed oil, Karanja oil (Sophora japonica), Latany extract (Arctium lappa), soy, bamboo, Bridgeberry oil (Pendulum flexuosa), cyanobacteria, Phenoxylum bungeana (Polypodium album), green tea, black tea (Camellia sinensis), evening primrose oil, cashew nut shell, pomegranate and any mixture thereof.
[1222] Advantageously, the amount of secondary sunscreen substances in the cosmetic or pharmaceutical preparations or household care products according to the invention is 0.005 to 5.0 wt.-%, preferably 0.01 to 4.0 wt.-%, most preferably 0.05 to 3.0 wt.-%, based on the total weight of the ready-to-use formulation.
[1223] Film former : The food, cosmetic or pharmaceutical preparation (especially sunscreen product) or home care product according to the invention may advantageously include one or more film formers or film forming agents. A film former is a hydrophobic material which imparts water resistance and film-forming properties to the sunscreen product, cosmetic or pharmaceutical preparation or home care product. Standard film formers are preferably chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone / vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid and its salts and similar compounds. Preferred film formers for improving the water resistance of the composition are selected from the group consisting of polyamide-8 (such as Oleocraft LP 20PA (MV)), polyamide-3 (such as Oleocraft MP 32PA (MV)), trimethylpentanediol / adipic acid / glycerin crosspolymer (such as WetFilm), octyldodecyl citrate crosspolymer (such as CosmoSurf CE 100), polyglyceryl-3 methylglucose distearate (such as TegoCare 450), C28-52 olefin / undecenoic acid copolymer (such as Performa V6112), hydrolyzed jojoba esters, jojoba esters, water (such as Floraester Jojoba K100), cyclopentasiloxane acrylate / dimethicone copolymer (such as KP545), acrylates / beheneth-25 methacrylate copolymer (such as Volarest), styrene / acrylates copolymer (such as Dermacryl E polymer), polyurethane (such as Baycusan C1001), polyurethane-2 and polymethyl methacrylate (such as Hybridur 875 polymer), acrylates / octylacrylamide copolymer (such as Dermacryl 2.0 polymer), beeswax (Cera Alba) (and) sodium stearoyl lactylate (such as SymEffect Sun), pullulan, xanthan gum, hydrogenated palm oil, sugar cane extract (SymEffect TM UV), microcrystalline cellulose (and) Sphingomonas ferment extract (and) cellulose gum (such as PemuPur TM START polymers), gum arabic and xanthan gum (such as SOLAGUM TMAX), microcrystalline cellulose (and) cellulose gum (such as Natpure CellgumPlus), sodium stearoyl glutamate (such as HS-11P), hydrogenated polycyclopentadiene (and) caprylic / capric triglyceride (such as 5400CCT), Glyceryl Hydrogenated Rosinate (and) Caprylic / Capric Triglyceride (and) Tocopherol (such as NATURAL 2063-CCT), galactoarabinan (such as A200), C26-28 alkyl dimethicone (such as Wacker CDM 3526VP), Caprylyl Methicone (such as Silsoft 034), Stearyl Dimethicone (and) Octadecene (such as Dowsil 2503 Cosmetic Wax), VP / Hexadecene Copolymer (such as Antaron TM V 216), triacontanyl PVP (such as Antaron TM WP-660), caprylylglycerol / sebacic acid copolymer (such as LexFilm TM Sun Natural MB), poly C10-30 alkyl acrylate (such as TegoSP 13 Sun Up), microcrystalline cellulose (such as Sunspheres TM BIO SPF booster) and any mixture thereof. The above film forming agents are used in sunscreens, cosmetics or pharmaceutical preparations or home care products as a single component or preferably in a mixture with two or more of the above additional film forming agents. The film forming agent is used in an effective amount that allows the final formulation to remain on the skin or surface after exposure to circulating water for at least 40 minutes, preferably 80 minutes. The film forming agent is present in the food, cosmetic or pharmaceutical preparation or home care product in an amount of 0.01% to 10.0% by weight, preferably 0.05% to 8.0% by weight, based on the total weight of the final formulation.
[1224] Water resistance improver:Food, cosmetic or pharmaceutical preparation (especially sunscreen product) or household care product according to the present invention can advantageously include one or more agents for improving water resistance. The agent for improving water resistance is a hydrophobic material that imparts emulsion film formation and water resistance characteristics. Typical suitable water resistance improvers include copolymers derived from octadecene-1 and maleic anhydride polymerization. Preferred water resistance improvers are polyanhydride resins. Another preferred water resistance improver is a copolymer of vinyl pyrrolidone and eicosene monomers. The water resistance improver is used in an effective amount that allows the final formulation to remain on the skin or surface after being exposed to circulating water for at least 40 minutes, preferably 80 minutes. Based on the gross weight of the final formulation, one or more water resistance improvers can be optionally included in the final formulation in an amount of 0.01% to 10.0% by weight, preferably 0.05% to 8.0% by weight, more preferably 0.1% to 5.0% by weight.
[1225] Stripping solvent : The cosmetic or pharmaceutical composition according to the invention preferably contains one or more exfoliating solubilizing agents. The expression "exfoliating solubilizing agent" is understood to mean any compound capable of:
[1226] - acting directly on exfoliation by promoting exfoliation, such as beta-hydroxy acids, in particular salicylic acid and its derivatives (including 5-n-octanoylsalicylic acid); alpha-hydroxy acids, such as glycolic acid, citric acid, lactic acid, tartaric acid, malic acid or mandelic acid; urea; gentisic acid; oligofructose; cinnamic acid; extracts of Sophora japonica; resveratrol and some derivatives of jasmonic acid;
[1227] - or enzymes involved in the exfoliation or degradation of corneodesmosomes, glycosidases, stratum corneum chymotrypsin (SCCE) or other proteases (trypsin, chymotrypsin-like). Agents that may be mentioned are chelating inorganic salts: EDTA; N-acyl-N,N',N'-ethylenediaminetriacetic acid; aminosulfonic acid compounds, and in particular (N-2-hydroxyethylpiperazine-N-2-ethane)sulfonic acid (HEPES); derivatives of 2-oxothiazolidine-4-carboxylic acid (procysteine); derivatives of α-amino acids of the glycine type (such as described in EP-0 852949 and sodium methylglycine diacetate sold under the trade name TRILON M by the company BASF); honey; sugar derivatives, such as O-octanoyl-6-D-maltose, N-acetylglucosamine; chestnut extracts (such as those sold under the name TRILON by the company SILAB); Rosa roxburghii extracts (such as those sold under the name phytosphingosine sold by Degussa (Phytosphingosine grafted with salicylic acid).
[1228] The peeling dissolving agent suitable for the present invention may be chosen in particular from the group consisting of: sulfonic acid, calcium chelating agent, alpha-hydroxy acid (such as glycolic acid, citric acid, lactic acid, tartaric acid, malic acid or mandelic acid); ascorbic acid and its derivatives (such as ascorbyl glucoside and magnesium ascorbyl phosphate); niacinamide; urea; (N-2-hydroxyethylpiperazine-N-2-ethane) sulfonic acid (HEPES), beta-hydroxy acid (such as salicylic acid and its derivatives), retinoic acid (such as retinol and its esters, retinal, retinoic acid and its derivatives), chestnut or prickly pear extract (especially chestnut or prickly pear extract sold by SILAB); reducing compounds (such as cysteine or cysteine precursors). Also useful peeling dissolving agents are nicotinic acid and its esters and niacinamide, also known as vitamin B3 or vitamin PP, and ascorbic acid and its precursors.
[1229] Anti-dandruff substances In addition, the composition according to the present invention can also be advantageously used in combination with one or more anti-dandruff substances, including triclosan, climbazole, octoxyglycerol, (1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)-pyridone 2-aminoethanol salt), chitosan, farnesol, glyceryl monolaurate, propylene glycol monocaprylate or a combination of the substances, which are particularly useful for combating dandruff.
[1230] Other suitable antidandruff agents are piroctone olamine (1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2-(1H)-pyridone monoethanolamine salt), (Climbazole), (4-acetyl-1-{4-[2-(2,4-dichlorophenyl)r-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolane-c-4-ylmethoxyphenyl}-piperazine, ketoconazole, neoconazole, selenium disulfide, colloidal sulfur, sulfur polyethylene glycol sorbitan monooleate, sulfur ricinoleyl polyethoxylate, sulfur tar distillate, salicylic acid (or in combination with hexachlorophene), undecylenic acid, monoethanolamide sulfosuccinic acid sodium salt, UD (protein-undecylenic acid condensate), zinc pyrithione, aluminum pyrithione, and magnesium pyrithione / magnesium bipyrithione-sulfate.
[1231] Metal ChelatorsCombinations with one or more (metal) chelators can also be advantageously used in the compositions according to the invention, wherein any metal chelator suitable or conventional in cosmetic or pharmaceutical applications can be used. Preferred (metal) chelators include alpha-hydroxy fatty acids, phytic acid, lactoferrin, alpha-hydroxy acids, such as, in particular, gluconic acid, glyceric acid, glycolic acid, isocitric acid, citric acid, lactic acid, malic acid, mandelic acid, tartaric acid, and humic acid, bile acid, bile extract, bilirubin, biliverdin or EDTA, EGTA, MGDA (trisodium dicarboxymethylalanine) and their derivatives. The use of one or more chelators improves the stability of the compositions according to the invention.
[1232] Surfactants:The composition according to the present invention preferably comprises one or more anionic and / or amphoteric or zwitterionic surfactants. Typical examples include: almond amidopropylamine oxide, almond amidopropyl betaine, aminopropyl lauryl glutamine, ammonium C12-15 alkyl sulfate, ammonium C12-16 alkyl sulfate, ammonium capryl sulfate, ammonium monococoglyceryl sulfate, ammonium coconut sulfate, ammonium cocoyl isethionate, ammonium cocoyl sarcosinate, ammonium C12-15 alkylene sulfate, ammonium C9-10 perfluoroalkylsulfonate, ammonium dinonyl sulfosuccinate, ammonium dodecylbenzenesulfonate, ammonium isostearate, ammonium laureth-6 carboxylate, ammonium laureth-8 carboxylate, ammonium laureth sulfate, ammonium laureth-5 sulfate, ammonium laureth-7 sulfate, ammonium laureth-9 sulfate, ammonium laureth-10 sulfate, ammonium laureth-11 sulfate, ammonium laureth-12 sulfate, ammonium laureth-13 sulfate, ammonium laureth-14 sulfate, ammonium laureth-15 sulfate, ammonium laureth-16 sulfate, ammonium laureth-17 sulfate, ammonium laureth-18 sulfate, ammonium laureth-19 sulfate, ammonium laureth-20 sulfate, ammonium laureth-21 sulfate, ammonium laureth-23 sulfate, ammonium laureth-24 sulfate, ammonium laureth-25 sulfate, ammonium laureth-27 sulfate, ammonium laureth-28 sulfate, ammonium laureth-29 sulfate, ammonium laureth-30 sulfate, ammonium laureth-31 sulfate, ammonium laureth-32 sulfate, ammonium laureth-33 sulfate, ammonium laureth- Ammonium ether-12 sulfate, ammonium lauroyl sarcosinate, ammonium lauryl sulfate, ammonium lauryl sulfosuccinate, ammonium myristyl sulfate, ammonium myristyl sulfate, ammonium nonylphenol polyether-4 sulfate, ammonium nonylphenol polyether-30 sulfate, ammonium oleate, ammonium palm kernel alcohol sulfate, ammonium stearate, ammonium tall oil acid, isostearyl hydrolyzed collagen AMPD salt, rosin (acyl) hydrolyzed collagen AMPD salt, isostearyl hydrolyzed collagen AMP salt, isostearyl hydrolyzed keratin AMP salt, isostearyl hydrolyzed soy protein AMP salt, isostearyl hydrolyzed wheat protein AMP salt, wild apricot oleamidopropyl betaine, arachidic acid, hexyldecyl phosphate arginine salt, avocado oleamidopropyl betaine, avocado oil glyceryl polyether -8 Esters, Babassu Seed Acid, Babassu Amidopropylamine Oxide, Babassu Amidopropyl Betaine, Beeswax Acid, Behenamidopropyl Betaine, Behenamine Oxide, Beheneth-25, Beheneth-30 Behenic Acid, Behenyl Betaine, Bis-Butyl Dimethicone Polyglyceryl-3, Butylphenol Eth-5 Carboxylic Acid, Butylphenol Eth-19 Carboxylic Acid, Butyl Dimethyl (Hydroxypropyl Butyl Glucoside) Ammonium Chloride, Butyl Dimethyl (Hydroxypropyl Lauryl Glucoside) Ammonium Chloride, Butyl Glucoside, Butyl Glucoside Decanoate, Butyl Glucoside Hydroxypropyltrimonium Chloride, Butyl Caprylate, C18-36 Acid, C20-40 Acid, C30-50 Acid, C16-22 Acid Amide MEA, Deca Calcium dialkylbenzene sulfonate, calcium lauroyl taurate, C9-16 alkane / cycloalkane, C10-14 alkylbenzene sulfonic acid, C12-14 alkyl di(aminoethyl)glycine HCL, C9-15 alcohol phosphate, Candida / glucose / rapeseed methyl ester fermentation product, canola amidopropyl betaine, capric acid, caproic acid, caproyl ethyl glucoside, capryl / caprylamidopropyl betaine, capryleth-4 carboxylic acid, capryleth-6 carboxylic acid, capryleth-9 carboxylic acid, caprylic acid, capryloyl collagen amino acids, capryloyl glycine, capryloyl hydrolyzed collagen, capryloyl hydrolyzed keratin, capryloyl keratin amino acids, capryloyl silk amino acids, capryl / decyl glucoside, capryl / decyl wheat bran / straw glycosides, capryl glucoside,Caprylyl Glyceryl Ether, Caprylyl Pyrrolidone, Carnitine, Ceteareth-20, Ceteareth-23, Ceteareth-24, Ceteareth-25, Ceteareth-27, Ceteareth-28, Ceteareth-29, Ceteareth-30, Ceteareth-33, Ceteareth-34, Ceteareth-40, Ceteareth-50, Ceteareth-55, Ceteareth-60, Ceteareth-80, Ceteareth-100, Ceteareth-25 Carboxylic Acid, Ceteareth-2 Phosphate, Ceteareth-4 Phosphate, Ceteareth-5 Phosphate, Diceteareth-10 Phosphate, Ceteth-20, Ceteth-23, Ceteth-24, Ceteth-25, Ceteth-30, Ceteth-40, Ceteth-45, Ceteth-150, Ceteth-8 Phosphate, Ceteth-10 Phosphate, Ceteth-20 Phosphate, Ceteth-22, Ceteth-24, Ceteth-25, Ceteth-30, Cetyl Betaine, Chrysanthemum Sinense flower extract, C12-14 hydroxyalkyl hydroxyethyl beta-alanine, C12-14 hydroxyalkyl hydroxyethyl sarcosine, cocamidoethyl betaine, cocamidopropylamine oxide, cocamidopropyl betainamide MEA chloride, cocamidopropyl betaine, cocamidopropyl hydroxysultaine, cocamine oxide, cocoaminobutyric acid, cocoaminopropionic acid, cocoeth-7 carboxylic acid, coceth-4 glucoside, cocoamphopropionic acid, cocobetainamidoamphopropionate, cocobetaine, cocodimonium hydroxypropyl hydrolyzed rice protein, cocodimonium hydroxypropyl hydrolyzed soy protein, cocodimonium hydroxypropyl hydrolyzed wheat protein, coco-glucoside, coco-glucoside hydroxypropyltrimonium chloride, coco-hydroxysultaine, cocomorpholine oxide, cocoic acid, coco Glyceryl Polyether-8 Esters, Cocoyl / Oleamidopropyl Betaine, Cocoyl-Sultaine, Coco / Sunflower Oil Amidopropyl Betaine, Cocoyl Choline Methyl Sulfate, Cocoyl Glutamate, Cocoyl Hydrolyzed Collagen, Cocoyl Hydrolyzed Keratin, Cocoyl Hydrolyzed Oat Protein, Cocoyl Hydrolyzed Rice Protein, Cocoyl Hydrolyzed Silk, Cocoyl Hydrolyzed Soy Protein, Cocoyl Hydrolyzed Wheat Protein, Cocoyl Sarcosine, corn oil acid, cottonseed oil acid, cottonseed oil glyceryl polyether-8 esters, C10-16 polyether-1, C10-16 polyether-2, C11-13 polyether-6, C11-13 polyether-9, C11-13 polyether-10, C11-15 polyether-30, C11-15 polyether-40, C12-13 polyether-1,C12-13 pareth-23, C12-14 pareth-5, C12-14 pareth-9, C13-15 pareth-21, C14-15 pareth-8, C20-22 pareth-30, C20-40 pareth-40, C20-40 pareth-95, C22-24 pareth-33, C30-50 pareth-40, C9-11 pareth-6 carboxylic acid, C9-11 pareth-8 carboxylic acid, C C11-15 pareth-7 carboxylic acid, C12-13 pareth-5 carboxylic acid, C12-13 pareth-7 carboxylic acid, C12-13 pareth-8 carboxylic acid, C12-13 pareth-12 carboxylic acid, C12-15 pareth-7 carboxylic acid, C12-15 pareth-8 carboxylic acid, C12-15 pareth-12 carboxylic acid, C14-15 pareth-8 carboxylic acid, C6-10 pareth-4 phosphate, C12-13 pareth-2 phosphate, C 12-13 Pareth-10 Phosphate, C12-15 Pareth-6 Phosphate, C12-15 Pareth-8 Phosphate, C12-15 Pareth-10 Phosphate, C12-16 Pareth-6 Phosphate, C4-18 Perfluoroalkyl Ethyl Mercaptopropyl Trimethylammonium Chloride, Cocoamidopropyl Betaine, C12-13 Alcohol Sulfate DEA, C12-15 Alcohol Sulfate DEA, Ceteareth-2 Phosphate DEA, Cetyl Alcohol Sulfate DEA , DEA cocoamphodipropionate, DEA C12-13 alkane polyether-3 sulfate, DEA cyclopentyl oleate, DEA dodecylbenzene sulfonate, DEA isostearate, DEA laureth sulfate, DEA lauryl sulfate, DEA linoleate, DEA myristyl methyl sulfonate, DEA myristyl ether sulfate, DEA myristate, DEA myristyl sulfate, DEA oleth-5 phosphate, DEA oleth-20 phosphate, DEA PG-oleate, Deceth-7 Carboxylic Acid, Deceth-7 Glucoside, Deceth-9 Phosphate, Decylamine Oxide, Decyl Betaine, Undecyl Glucoside, Decyltetradeceth-30, Decyltetradeceth-7 Oxide, Diammonium Laureth-MEA Sulfosuccinate, Diammonium Laureth Sulfosuccinate, Diammonium Oleamido PEG-2 Sulfosuccinate, Dibutoxymethane, Di-CI 2-15 Pareth-2 Phosphate, Di-CI 2-15 Pareth-4 Phosphate, Di-CI 2-15 Pareth-6 Phosphate, Di-C12-15 Pareth-8 Phosphate, Di-CI 2-15 Alkyl Polyether-10 Phosphate, Butyl Dodecyl Tetracarboxylate, Diethylamine Laureth Sulfate, Diethylhexyl Sodium Sulfosuccinate, Dihydroxyethyl C8-10 Alkoxypropylamine Oxide,Dihydroxyethyl C9-11 alkoxypropylamine oxide, dihydroxyethyl C12-15 alkoxypropylamine oxide, dihydroxyethyl cocoamine oxide, dihydroxyethyl laurylamine oxide, dihydroxyethyl stearamine oxide, dihydroxyethyl tallowamine oxide, dimethicone PEG-7 phosphate, dimethicone PEG-10 phosphate, dimethicone PEG / PPG-7 / 4 phosphate, dimethicone PEG / PPG-12 / 4 phosphate, dimethicone / polyglyceryl-3 crosspolymer, dimethicone propyl PG-betaine, dimyristyl phosphate, dioleamide ethyl Hydroxyethyl methyl ammonium methyl sulfate, hydrogenated coconut acid DIPA salt, lanolin acid DIPA salt, myristic acid DIPA salt, capryloyl glutamate dipotassium, lauryl sulfosuccinate dipotassium, undecylenyl glutamate dipotassium, babassu oleamido MEA-sulfosuccinate disodium, capryloylamphodiacetate disodium, capryloylamphodipropionate disodium, capryloylamphodiacetate disodium, capryloylamphodipropionate disodium, capryloyl glutamate disodium, cetearyl alcohol sulfosuccinate disodium, cetyl phenyl ether disulfonate disodium, cetyl alcohol sulfosuccinate disodium, cocamide MEA-sulfosuccinate disodium, cocamide MIPA Disodium PEG-4 Sulfosuccinate, Disodium Cocoamido MIPA-Sulfosuccinate, Disodium Cocoamido PEG-3 Sulfosuccinate, Disodium Cocoeth-3 Sulfosuccinate, Disodium Cocoamphocarboxyethyl Hydroxypropyl Sulfonate, Disodium Cocoamphodiacetate, Disodium Cocoamphodipropionate, Disodium Coco-Glucoside Sulfosuccinate, Disodium Coco-Sulfosuccinate, Coco Disodium butyl gluceth-10 sulfosuccinate, disodium cocoyl glutamate, disodium C12-14 pareth-1 sulfosuccinate, disodium C12-14 pareth-2 sulfosuccinate, disodium C12-15 pareth sulfosuccinate, disodium C12-14 sec-pareth-3 sulfosuccinate, disodium C12-14 sec-pareth-5 sulfosuccinate, C12-14 sec-pareth-6 sulfosuccinate Disodium 2-14 sec-Pareth-7 Sulfosuccinate, Disodium C12-14 sec-Pareth-9 Sulfosuccinate, Disodium C12-14 sec-Pareth-12 Sulfosuccinate, Disodium Deceth-5 Sulfosuccinate, Disodium Deceth-6 Sulfosuccinate, Disodium Decyl Phenyl Ether Disulfonate, Disodium Dihydroxyethyl Sulfosuccinyl Undecylenate, Disodium Cocoyl Ethylenediamine PEG-15 Disulfate Disodium ester, disodium hydrogenated cottonseed oil glycerides sulfosuccinate, disodium hydrogenated tallow glutamate, disodium hydroxydecyl sorbitan citrate, disodium isodecyl sulfosuccinate, disodium isostearamide MEA sulfosuccinate, disodium isostearamide MIPA-sulfosuccinate, disodium isostearylamphodiacetate, disodium isostearylamphodipropionate, disodium isostearyl sulfosuccinate, disodium lanolin alcohol ether-5 sulfosuccinate,Disodium lauramido MEA-sulfosuccinate, disodium lauramido MIPA glycol sulfosuccinate, disodium lauramido PEG-2 sulfosuccinate, disodium lauramido PEG-5 sulfosuccinate, disodium laureth-5 carboxyamphodiacetate, disodium laureth-7 citrate, disodium laureth sulfosuccinate, disodium laureth-6 sulfosuccinate, disodium laureth-9 sulfosuccinate, disodium laureth-12 sulfosuccinate, disodium laurimidobishydroxypropyl sulfonate, disodium laurimidodiacetate, disodium laurimidodipropionate, disodium laurimidodipropionate tocopheryl phosphate, disodium lauroamphodiacetate, disodium lauroamphodipropionate , Disodium N-lauroyl Aspartate, Disodium Lauroyl Glutamate, Disodium Lauryl Phenyl Ether Disulfonate, Diammonium Lauryl Sulfosuccinate, Disodium Myristamide MEA-Sulfosuccinate, Disodium Nonylphenol Polyether-10 Sulfosuccinate, Disodium Oleamide MEA Sulfosuccinate, Disodium Oleamide MIPA Sulfosuccinate, Disodium Oleamide PEG-2 Sulfosuccinate, Disodium Oleoamphodipropionate, Disodium Oleth-3 Sulfosuccinate, Disodium Oleth-3 Sulfosuccinate, Disodium Oleth Phosphate, Disodium Oleth Sulfosuccinate, Disodium Palmitamide PEG-2 Sulfosuccinate, Disodium Palmitamide PEG-2 Sulfosuccinate, Disodium Palmitamide PEG-2 Sulfosuccinate, Disodium PEG-4 Cocoamide MIPA-Sulfosuccinate, PEG-12 Polydimethicone Disodium sulfosuccinate, PEG-8 palmitic acid glyceryl sulfosuccinate, PPG-2-isodecyl polyether-7 carboxyamphodiacetate, disodium ricinoleamide MEA sulfosuccinate, disodium sitosterol polyether-14 sulfosuccinate, disodium soybean oleylamphodiacetate, disodium stearamide MEA-sulfosuccinate, disodium stearimidodipropionate, disodium stearoylamphodiacetate, disodium stearoyl glutamate, disodium sulfosuccinic acid monoacyl stearylamine, disodium stearyl alcohol sulfosuccinate, disodium 2-sulfolaurate, disodium 2-sulfopalmitate, disodium tallowamide MEA sulfosuccinate, disodium tallow amphodiacetate, tallowiminodipropionate Disodium Glutamate, Disodium Monoacyl Tallowamine Sulfosuccinate, Disodium Tridecyl Sulfosuccinate, Disodium Undecylenamide MEA Sulfosuccinate, Disodium Undecylenamide PEG-2 Sulfosuccinate, Disodium Undecylenyl Glutamate, Disodium Monowheatgerm Oily MEA Sulfosuccinate, Disodium Monowheatgerm Oily Amphoteric Acid, Disodium Cocoamide Diacetate TEA, Oleoyl PEG-2 Sulfosuccinate TEA, Palmitoyl Aspartate TEA, Tridecyl Sulfosuccinate Sodium, Dodecylbenzenesulfonic Acid, Erucamidopropyl Hydroxysulfobetaine, Ethylhexyl Ether-3 Carboxylic Acid, Ethyl PEG-15 Cocoamine Sulfate, Caprylyl Glyceryl Ether, Hexyl Decanoate,Hydrogenated Coconut Acid, Hydrogenated Lanolin Alcohol Polyether-25, Hydrogenated Menhaden Oil Fatty Acid, Hydrogenated Palmitoleic Acid, Hydrogenated Palm Kernel Oil Amine Oxide, Hydrogenated Tallow Acid, Hydrogenated Tallow Amine Oxide, Hydrogenated Tallow Betaine, Hydrogenated Tallow Alcohol Polyether-25, Hydrogenated Tallowyl Glutamic Acid, Hydrogenated Candida Extract, Hydroxycetyl Alcohol Polyether-60, Hydroxyethyl Acetoxymethyl Ammonium PG-Dimethicone, Hydroxyethyl Butylamine Laureth Sulfate, Hydroxyethyl Carboxymethyl Cocamidopropylamine, Hydroxyethyl Hydroxypropyl C12-15 Alkoxypropylamine Oxide, Hydroxylauryl / Hydroxymyristyl Betaine, Hydroxystearic Acid, Amidohydroxysuccinimide C10-40 Ethylhexyl Isoalkanoate, Amidohydroxysuccinimide C21-22 Ethylhexyl Isoalkanoate, Hydroxy Sultaine, IPDI / PEG-15 soybean amine oxide copolymer, IPDI / PEG-15 soybean amine ethanol methyl sulfate copolymer, IPDI / PEG-15 soybean glycine ester copolymer, Isoceteth-30, Isolaureth-4 phosphate, Isopolyglyceryl-3 polydimethylsiloxane, Isopolyglyceryl-3 polydimethylsiloxane, Isopropylamine lanolinate, Isopropylamine dodecylbenzenesulfonate, Isostearamidopropylamine oxide, Isostearamidopropyl betaine, Isostearamidopropyl morpholine oxide, Isosteareth-8, Isosteareth-16, Isosteareth-22, Isosteareth-25, Isosteareth-50, Isostearic acid, Isostearyl hydrolyzed collagen , Jojoba Oil PEG-150 Esters, Jojoba Wax PEG-80 Esters, Jojoba Wax PEG-120 Esters, Lanolin Alcohol Polyether-20, Lanolin Alcohol Polyether-25, Lanolin Alcohol Polyether-40, Lanolin Alcohol Polyether-50, Lanolin Alcohol Polyether-60, Lanolin Alcohol Polyether-75, Lanolin Acid, Lauramidopropylamine Oxide, Lauramidopropyl Betaine, Lauramidopropyl Hydroxysulfobetaine, Lauramine Oxide, Lauryl Aminopropionic Acid, Lauryl Dimethyl Hydroxypropyl Decyl Glucoside Ammonium Chloride, Lauryl Dimethyl Lauryl Glucoside Hydroxypropyl Ammonium Chloride, Laureth-16, Laureth-20, Laureth-21, Laureth-23, Laureth-25, Laureth-30, Laureth-38, Laureth-40, Laureth-3 Carboxylic Acid, Laureth-4 Carboxylic Acid, Laureth-5 Carboxylic Acid, Laureth-6 Carboxylic Acid, Laureth-8 Carboxylic Acid, Laureth-10 Carboxylic Acid, Laureth-11 Carboxylic Acid, Laureth-12 Carboxylic Acid, Laureth-13 Carboxylic Acid, Laureth-14 Carboxylic Acid, Laureth-17 Carboxylic Acid, Laureth-6 Citrate, Laureth-7 Citrate, Laureth-1 Phosphate, Laureth-2 Phosphate, Laureth-3 Phosphate, Laureth-4 Phosphate, Laureth-7 Phosphate, Laureth-8 Phosphate, Laureth-7 Tartrate, Lauric Acid, Lauryl Imidodipropylene Glycol,Lauriminodipropionic acid, lauroylamphodipropionic acid, lauroyl-β-aminopropionic acid, lauroyl collagen amino acids, lauroyl ethyltrimonium methylsulfate, lauroyl hydrolyzed collagen, lauroyl hydrolyzed elastin, lauroyl methylglucamide, lauroyl sarcosine, laur...
Claims
1. A food, cosmetic or pharmaceutical preparation or household care product comprising or consisting of: (a) at least one aroma or fragrance / flavor compound; (b) at least one mycosporine-like amino acid compound, It is represented by the general formula (V) in -Z is selected from the group consisting of: O-R2' or amide'; -R1' is selected from the group consisting of CH2, unsubstituted or substituted CH(alkyl), unsubstituted or substituted C(alkyl), unsubstituted or substituted CH(cycloalkyl), unsubstituted or substituted CH(aryl), unsubstituted or substituted CH(heterocycloalkyl), unsubstituted or substituted CH(heteroaryl), CR7'R8', C=O, halogen, O, S, SO, SO2, NH, unsubstituted or substituted N(alkyl), unsubstituted or substituted N(alkenyl), unsubstituted or substituted N(alkynyl), unsubstituted or substituted N(alkoxy), unsubstituted or substituted N(alkylthio), unsubstituted or substituted N(cycloalkyl), unsubstituted or substituted N(aryl), unsubstituted or substituted N(heterocycloalkyl) and unsubstituted or substituted N(heteroaryl) and unsubstituted or substituted C-spiro; -R2' is selected from the group consisting of H, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted alkoxy, unsubstituted or substituted alkylthio, unsubstituted or substituted cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted heteroaryl; -amide' is selected from the group consisting of NH2, unsubstituted or substituted NH(alkyl), unsubstituted or substituted NH(alkenyl), unsubstituted or substituted NH(alkynyl), unsubstituted or substituted NH(alkoxy), unsubstituted or substituted NH(alkylthio), unsubstituted or substituted NH(cycloalkyl), unsubstituted or substituted NH(aryl), unsubstituted or substituted NH(heterocycloalkyl), unsubstituted or substituted NH(heteroaryl), and unsubstituted or substituted NR9'R10', unsubstituted or substituted -N(O-alkyl)(alkyl)(Weinreb amide), -N(OH)(H)(hydroxamic acid), and unsubstituted or substituted -N(OH)(alkyl)(alkylated hydroxamic acid); -R3' is selected from the group consisting of H, OH, halogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted alkoxy, unsubstituted or substituted alkylthio, unsubstituted or substituted alkanoyl / acyl RC(=O)-, -CH2-OH, -R-CH2-OH, -C(=O)-OY, -RC(=O)-OY, unsubstituted or substituted cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted heteroaryl, SO, SO2, NH2, unsubstituted or substituted NH(alkyl), unsubstituted or substituted NH(cycloalkyl), unsubstituted or substituted NH(aryl), unsubstituted or substituted NH(heterocycloalkyl), unsubstituted or substituted NH(heteroaryl), unsubstituted or substituted NR9'R10' and unsubstituted or substituted C-spiro; - the substituents R4', R5' and R6' which may be the same or different are independently selected from the group consisting of H, OH, halogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted alkoxy, unsubstituted or substituted alkylthio, unsubstituted or substituted alkanoyl / acyl RC(=O)-, -CH2-OH, -R-CH2-OH, -C(=O)-OY, -RC(=O)-OY, unsubstituted or substituted cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heterocycloalkyl, unsubstituted unsubstituted or substituted heteroaryl, SO, SO2, -S(=O)2OH, sulfonyl, NH2, unsubstituted or substituted NH(alkyl), unsubstituted or substituted NH(alkenyl), unsubstituted or substituted NH(alkynyl), unsubstituted or substituted NH(alkoxy), unsubstituted or substituted NH(alkylthio), unsubstituted or substituted NH(cycloalkyl), unsubstituted or substituted NH(aryl), unsubstituted or substituted NH(heterocycloalkyl) and unsubstituted or substituted NH(heteroaryl), unsubstituted or substituted NR9'R10' and unsubstituted or substituted C-spiro; - R7' and R8', which may be the same or different, are independently selected from the group consisting of H, OH, halogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted alkoxy, unsubstituted or substituted alkylthio, unsubstituted or substituted alkanoyl / acyl RC(=O)-, -CH2-OH, -R-CH2-OH, -C(=O)-OY, -RC(=O)-OY, unsubstituted or substituted cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted heteroaryl, SO, SO2, NH2, unsubstituted or substituted NH(alkyl), unsubstituted or substituted NH(alkenyl), unsubstituted or substituted NH(alkynyl), unsubstituted or substituted NH(alkoxy), unsubstituted or substituted NH(alkylthio), unsubstituted or substituted NH(cycloalkyl), unsubstituted or substituted NH(aryl), unsubstituted or substituted NH(heterocycloalkyl), unsubstituted or substituted NH(heteroaryl), and unsubstituted or substituted NR9'R10'; - R9' and R10', which may be identical or different, are independently selected from the group consisting of H, OH, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted alkoxy, unsubstituted or substituted alkylthio, unsubstituted or substituted alkanoyl / acyl RC(=O)-, unsubstituted or substituted cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heterocycloalkyl and unsubstituted or substituted heteroaryl; -Y is selected from the group consisting of H and unsubstituted or substituted alkyl; and -R is unsubstituted or substituted alkyl; or a tautomer or stereoisomer or salt of the aforementioned compound; Or represented by general formula (VI) in -R1" is selected from the group consisting of CH2, unsubstituted or substituted CH(alkyl), unsubstituted or substituted C(alkyl), unsubstituted or substituted CH(cycloalkyl), unsubstituted or substituted CH(aryl), unsubstituted or substituted CH(heterocycloalkyl), unsubstituted or substituted CH(heteroaryl), CR7'R8', C=O, halogen, O, S, SO, SO2, NH, unsubstituted or substituted N(alkyl), unsubstituted or substituted N(alkenyl), unsubstituted or substituted N(alkynyl), unsubstituted or substituted N(alkoxy), unsubstituted or substituted N(alkylthio), unsubstituted or substituted N(cycloalkyl), unsubstituted or substituted N(aryl), unsubstituted or substituted N(heterocycloalkyl), unsubstituted or substituted N(heteroaryl), and unsubstituted or substituted C-spiro; -R2" is selected from the group consisting of H, OH, halogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted alkoxy, unsubstituted or substituted alkylthio, unsubstituted or substituted alkanoyl / acyl RC(=O)-, -CH2-OH, -R-CH2-OH, -C(=O)-OY, -C(=O)-amide", unsubstituted or substituted cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted heteroaryl, SO, SO2, NH2, unsubstituted or substituted NH(alkyl), unsubstituted or substituted NH(alkenyl), unsubstituted or substituted NH(alkynyl), unsubstituted or substituted NH(alkoxy), unsubstituted or substituted NH(alkylthio), unsubstituted or substituted NH(cycloalkyl), unsubstituted or substituted NH(aryl), unsubstituted or substituted NH(heterocycloalkyl), unsubstituted or substituted NH(heteroaryl), unsubstituted or substituted NR9"R10", and unsubstituted or substituted C-spiro; -X is selected from the group consisting of CH2, unsubstituted or substituted CH(alkyl), unsubstituted or substituted CH(alkenyl), unsubstituted or substituted CH(alkynyl), unsubstituted or substituted CH(alkoxy), unsubstituted or substituted CH(alkylthio), unsubstituted or substituted CH(cycloalkyl), unsubstituted or substituted CH(aryl), unsubstituted or substituted CH(heterocycloalkyl), unsubstituted or substituted CH(heteroaryl), -CR7"R8", C=O, O, S, SO, SO2, NH, unsubstituted or substituted N(alkyl), unsubstituted or substituted N(alkenyl), unsubstituted or substituted N(alkynyl), unsubstituted or substituted N(alkoxy), unsubstituted or substituted N(alkylthio), unsubstituted or substituted N(cycloalkyl), unsubstituted or substituted N(aryl), unsubstituted or substituted N(heterocycloalkyl), unsubstituted or substituted N(heteroaryl), and unsubstituted or substituted C-spiro; - the substituents R4", R5" and R6", which may be the same or different, are independently selected from the group consisting of H, OH, halogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted alkoxy, unsubstituted or substituted alkylthio, unsubstituted or substituted alkanoyl / acyl RC(=O)-, -CH2-OH, -R-CH2-OH, -C(=O)-OY, -RC(=O)-OY, unsubstituted or substituted cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heterocycloalkyl, unsubstituted unsubstituted or substituted heteroaryl, SO, SO2, -S(=O)2OH, sulfonyl, NH2, unsubstituted or substituted NH(alkyl), unsubstituted or substituted NH(alkenyl), unsubstituted or substituted NH(alkynyl), unsubstituted or substituted NH(alkoxy), unsubstituted or substituted NH(alkylthio), unsubstituted or substituted NH(cycloalkyl), unsubstituted or substituted NH(aryl), unsubstituted or substituted NH(heterocycloalkyl) and unsubstituted or substituted NH(heteroaryl), unsubstituted or substituted NR9"R10" and unsubstituted or substituted C-spiro; - R7" and R8", which may be the same or different, are independently selected from the group consisting of H, OH, halogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted alkoxy, unsubstituted or substituted alkylthio, unsubstituted or substituted alkanoyl / acyl RC(=O)-, -CH2-OH, -R-CH2-OH, -C(=O)-OY, -RC(=O)-OY, unsubstituted or substituted cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted heteroaryl, SO, SO2, NH2, unsubstituted or substituted NH(alkyl), unsubstituted or substituted NH(alkenyl), unsubstituted or substituted NH(alkynyl), unsubstituted or substituted NH(alkoxy), unsubstituted or substituted NH(alkylthio), unsubstituted or substituted NH(cycloalkyl), unsubstituted or substituted NH(aryl), unsubstituted or substituted NH(heterocycloalkyl), unsubstituted or substituted NH(heteroaryl), and unsubstituted or substituted NR9"R10"; -amide" is selected from the group consisting of NH2, unsubstituted or substituted NH(alkyl), unsubstituted or substituted NH(alkenyl), unsubstituted or substituted NH(alkynyl), unsubstituted or substituted NH(alkoxy), unsubstituted or substituted NH(alkylthio), unsubstituted or substituted NH(cycloalkyl), unsubstituted or substituted NH(aryl), unsubstituted or substituted NH(heterocycloalkyl), unsubstituted or substituted NH(heteroaryl), unsubstituted or substituted NR9"R10", unsubstituted or substituted -N(O-alkyl)(alkyl)(Weinreb amide), -N(OH)(H)(hydroxamic acid), and unsubstituted or substituted -N(OH)(alkyl)(alkylated hydroxamic acid); - R9" and R10", which may be identical or different, are independently selected from the group consisting of H, OH, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted alkoxy, unsubstituted or substituted alkylthio, unsubstituted or substituted alkanoyl / acyl RC(=O)-, unsubstituted or substituted cycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heterocycloalkyl and unsubstituted or substituted heteroaryl; -Y is selected from the group consisting of H and unsubstituted or substituted alkyl; and -R is unsubstituted or substituted alkyl; or a tautomer or stereoisomer or salt of the aforementioned compound; or any mixture of the foregoing compounds; and (c) optionally at least one antioxidant; The following compounds are disclaimed / excluded: Compound 1: Compound 2: Compound 3: Compound 4: Compound 5: Compound 6: Compound 7: as well as Compound 8:
2. The food, cosmetic or pharmaceutical preparation or household care product according to claim 1, The mycosporin-like amino acid compound (b) is represented by the general formula (VII): wherein R1′, R2′, R3′, R4′, R5′ and R6′ have the same meanings as defined for formula (V); Or represented by general formula (VIII) wherein R1′, Amide′, R3′, R4′, R5′ and R6′ have the same meanings as defined for formula (V).
3. The food, cosmetic or pharmaceutical preparation or home care product according to claim 1 or claim 2, wherein in the general formula (VI), X is selected from the group consisting of: CH2, unsubstituted or substituted CH(alkyl), unsubstituted or substituted C(alkyl), unsubstituted or substituted CH(alkenyl), unsubstituted or substituted CH(alkynyl), unsubstituted or substituted CH(alkoxy), unsubstituted or substituted CH(alkylthio), unsubstituted or substituted CH(cycloalkyl), unsubstituted or substituted CH(aryl), unsubstituted or substituted unsubstituted or substituted CH(heterocycloalkyl), unsubstituted or substituted CH(heteroaryl), -CR7"R8", C=O, S, SO, SO2, NH, unsubstituted or substituted N(alkyl), unsubstituted or substituted N(alkenyl), unsubstituted or substituted N(alkynyl), unsubstituted or substituted N(alkoxy), unsubstituted or substituted N(alkylthio), unsubstituted or substituted N(cycloalkyl), unsubstituted or substituted N(aryl), unsubstituted or substituted N(heterocycloalkyl), unsubstituted or substituted N(heteroaryl) and unsubstituted or substituted C-spiro.
4. The food, cosmetic, pharmaceutical preparation or household care product according to any one of claims 1 to 3, wherein in the general formula (V) -Z is -O-R2' or amide'; and / or - R1' is selected from the group consisting of CH2, C(alkyl)2, O, S, SO, SO2, NH and N(alkyl); and / or -R2' is selected from the group consisting of: H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, (2-ethylhexyl) and phenyl; or -amide' is selected from the group consisting of: NH2, NH(alkyl) and N(alkyl)2, -N(O-alkyl)(alkyl)(Weinreb amide) and -N(OH)(H)(hydroxamic acid); and / or -R3' is selected from the group consisting of: H, methyl, ethyl, -O-methyl, -C(=O)-OH, -C(=O)-CH3, -C(=O)-C3H7 and -C(=O)-O-methyl; and / or - the substituents R4', R5' and R6' have the same meanings as defined for formula (V); - wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl; or wherein in the general formula (VII) or (VIII) - R1' is selected from the group consisting of CH2, C(alkyl)2, O, S, SO, SO2, NH and N(alkyl); and / or -R2' is selected from the group consisting of: H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, (2-ethylhexyl) and phenyl; or -amide' is selected from the group consisting of: NH2, NH(alkyl) and N(alkyl)2, -N(O-alkyl)(alkyl)(Weinreb amide) and -N(OH)(H)(hydroxamic acid); and / or -R3' is selected from the group consisting of: H, methyl, ethyl, -O-methyl, -C(=O)-OH, -C(=O)-CH3, -C(=O)-C3H7 and -C(=O)-O-methyl; and / or - the substituents R4', R5' and R6' have the same meanings as defined for formulae (VII) and (VIII); - wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl; Or wherein in the general formula (VI) -R1" is selected from the group consisting of CH2, C(alkyl)2, O, S, SO, SO2, NH and N(alkyl); and / or -R2" is selected from the group consisting of: -CH2-OH, -C(=O)-OY and -C(=O)-amide"; and / or -X is selected from the group consisting of CH2, C=O, O, S, SO, SO2, NH and N(alkyl); and / or -Y is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, (2-ethylhexyl) and phenyl; and / or -amide" is selected from the group consisting of: NH2, NH(alkyl) and N(alkyl)2, -N(O-alkyl)(alkyl)(Weinreb amide) and -N(OH)(H)(hydroxamic acid); and / or - the substituents R4", R5" and R6" have the same meanings as defined for formula (VI); - wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl.
5. The food, cosmetic, pharmaceutical preparation or household care product according to any one of claims 1 to 4, wherein in the general formula (V) -Z is -O-R2' or amide'; and / or - R1' is selected from the group consisting of: CH2 and C(methyl)2; and / or -R2' is selected from the group consisting of: H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, (2-ethylhexyl) and phenyl; or -amide' is selected from the group consisting of: NH2, NH(alkyl) and N(alkyl)2, -N(O-alkyl)(alkyl)(Weinreb amide) and -N(OH)(H)(hydroxamic acid); and / or -R3' is selected from the group consisting of: H, methyl, ethyl, -O-methyl, -C(=O)-OH, -C(=O)-CH3, -C(=O)-C3H7 and -C(=O)-O-methyl; and / or - the substituents R4', R5' and R6' have the same meanings as defined for formula (V); - wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl; or wherein in the general formula (VII) or (VIII) -R1' is selected from the group consisting of: CH2 and C(methyl)2; -R2' is selected from the group consisting of: H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, (2-ethylhexyl) and phenyl; or -amide' is selected from the group consisting of: NH2, NH(alkyl) and N(alkyl)2, -N(O-alkyl)(alkyl)(Weinreb amide) and -N(OH)(H)(hydroxamic acid); and / or -R3' is selected from the group consisting of: H, methyl, ethyl, -O-methyl, -C(=O)-OH, -C(=O)-CH3, -C(=O)-C3H7 and -C(=O)-O-methyl; and / or - the substituents R4', R5' and R6' have the same meanings as defined for formulae (VII) and (VIII); - wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl; and / or Or wherein in the general formula (VI) -R1" is selected from the group consisting of: CH2 and C(methyl)2; and / or -R2" is selected from the group consisting of: -CH2-OH, -C(=O)-OY and -C(=O)-amide"; and / or -X is selected from the group consisting of CH2, C=O, O, S, SO, SO2, NH and N(alkyl); and / or -Y is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, (2-ethylhexyl) and phenyl; and / or -amide" is selected from the group consisting of: NH2, NH(alkyl) and N(alkyl)2, -N(O-alkyl)(alkyl)(Weinreb amide) and -N(OH)(H)(hydroxamic acid); and / or - the substituents R4", R5" and R6" have the same meanings as defined for formula (VI); - wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl.
6. The food, cosmetic, pharmaceutical preparation or home care product according to any one of claims 1 to 5, wherein the mycosporin-like amino acid compound (b) is selected from the group consisting of the following compounds I-1 to I-128 according to the general formula (V) and compounds II-1 to II-192 according to the general formula (VI): wherein in the above-mentioned mycosporin-like amino acid compound, the phenyl ring may be unsubstituted or substituted, and R4′, R5′, R6′, R4″, R5″, R6″, amide′, Y, amide″ and alkyl have the same meanings as defined in any one of the preceding claims, or a tautomer or stereoisomer or salt of the aforementioned compound; or wherein the mycosporin-like amino acid is selected from the group consisting of MAA-A MAA-B as well as MAA-C wherein alkyl is methyl or ethyl or propyl or isopropyl or butyl or isobutyl or tert-butyl, preferably methyl, or a tautomer or stereoisomer or salt of the aforementioned compound; or any mixture of the foregoing compounds.
7. The food, cosmetic or pharmaceutical preparation or household care product according to any one of claims 1 to 6, wherein in the general formulae (VI), (IX) and (X), X is S, SO or SO2, and / or wherein in the general formulae (V) to (X), n=1.
8. The food, cosmetic or pharmaceutical preparation or household care product according to any one of claims 1 to 7, wherein in the general formulae (V), (VII) and (VIII), the substituents R4', R5' and R6', which may be the same or different, are independently selected from the group consisting of: H; OH; alkyl, preferably methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl; alkoxy, preferably O-methyl, O-ethyl or O-butyl; -S(=O)2OH; and sulfonyl; or In the general formulae (VI), (IX) and (X), the substituents R4", R5" and R6", which may be the same or different, are independently selected from the group consisting of: H; OH; alkyl, preferably methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl; alkoxy, preferably O-methyl, O-ethyl or O-butyl; -S(=O)2OH; and sulfonyl.
9. The food, cosmetic or pharmaceutical preparation or home care product according to any one of claims 1 to 8, wherein in the general formulae (V) to (X), the substituted phenyl group bonded to the imino functional group is selected from the group consisting of: The dotted lines indicate the binding sites.
10. The food, cosmetic or pharmaceutical preparation or household care product according to any one of claims 1 to 9, wherein in the general formulae (V), (VII) and (VIII), the substituents R4', R5', R6', which may be identical or different, are independently selected from the group consisting of: H; OH; alkyl, preferably methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl; and alkoxy, preferably O-methyl, O-ethyl or O-butyl; -S(=O)2OH; and sulfonyl; provided that, if the substituted phenyl ring is monosubstituted, the substituents are located at the amino functional group ortho or meta; or wherein in the general formulae (VI), (IX) and (X), the substituents R4", R5" and R6", which may be the same or different, are independently selected from the group consisting of: H; OH; alkyl, preferably methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl; alkoxy, preferably O-methyl, O-ethyl or O-butyl; -S(=O)2OH; and sulfonyl; provided that, if the substituted phenyl ring is monosubstituted, the substituent is located in the ortho or meta position, but not in the para position, of the imino functional group of the general formulae (VI), (IX) and (X).
11. The food, cosmetic, pharmaceutical preparation or household care product according to any one of claims 1 to 10, wherein the mycosporin-like amino acid compound (b) is selected from the group consisting of or a tautomer or stereoisomer or salt of the aforementioned compound; or any mixture of the foregoing compounds.
12. The food, cosmetic or pharmaceutical preparation or household care product according to any one of claims 1 to 11, wherein the at least one fragrance compound (a) is selected from the group consisting of - extracts from natural raw materials such as essential oils, extracts, absolutes, resins, balsams, tinctures; - aliphatic alcohols; - aliphatic aldehydes and their acetals; - aliphatic ketones and their oximes; - aliphatic sulfur compounds; - aliphatic nitriles; - Esters of aliphatic carboxylic acids; - acyclic terpene alcohols; - acyclic terpene aldehydes and ketones; - cyclic terpene alcohols; - Cyclic terpene aldehydes and ketones; - Cyclic alcohols; - cyclic and cycloaliphatic ethers; - Cyclic and macrocyclic ketones; - cycloaliphatic aldehydes; - cycloaliphatic ketones; - Esters of cyclic alcohols; - esters of cycloaliphatic alcohols; - esters of cycloaliphatic carboxylic acids; - aromatic aliphatic alcohols; - Esters of aromatic aliphatic alcohols and aliphatic carboxylic acids; - aromatic aliphatic ethers; - aromatic and araliphatic aldehydes; - aromatic and araliphatic ketones; - aromatic and araliphatic carboxylic acids and their esters; - nitrogen-containing aromatic compounds; - phenol, phenyl ethers and phenyl esters; - heterocyclic compounds; - lactones; and any mixture of the above-mentioned aromatic substances; Or wherein the at least one fragrance / flavor compound (a) is selected from the group consisting of acetophenone, allyl hexanoate, methylionone, ethylionone, anisaldehyde, anisyl acetate, anisyl formate, anethole, benzaldehyde, benzothiazole, benzyl acetate, benzyl alcohol, benzyl benzoate, ethylionone, butyl butyrate, butyl hexanoate, butylidenephthalide, carvone, camphene, caryophyllene, eucalyptol, cinnamyl acetate, citral, citronellol, citronellal, citronellyl acetate, cyclohexyl acetate, cymene, damascone, decanoic acid, dihydrocoumarin, dimethyl o-aminobenzoate, dimethyl o-aminobenzoate, dodecalactone, ethoxyethyl acetate, ethylbutyric acid, ethyl butyrate, ethyl decanoate , ethyl hexanoate, ethyl crotonate, soy sauce ketone, ethyl guaiacol, ethyl isobutyrate, ethyl isovalerate, ethyl lactate, ethyl methylbutyrate, ethyl propionate, eucalyptol, eugenol, ethyl heptanoate, 4-(p-hydroxyphenyl)-2-butanone, γ-decalactone, geraniol, geranyl acetate, geranyl acetate, citrullaldehyde, methyl dihydrojasmonate (e.g. methyl dihydrojasmonate (R)), jasmonaldehyde, 2-heptanone, 3-heptanone, 4-heptanone, trans-2-heptenal, cis-4-heptenal, trans-2-hexenal, cis-3-hexenol, trans-2-hexenoic acid, trans-3-hexenoic acid, cis-2-hexenyl acetate, cis-3-hexenyl acetate, cis-3-hexenyl hexanoate , trans-2-hexenyl hexanoate, cis-3-hexenyl formate, cis-2-hexyl acetate, cis-3-hexyl acetate, trans-2-hexyl acetate, cis-3-hexyl formate, p-hydroxybenzyl acetone, isoamyl alcohol, isoamyl isovalerate, isobutyl butyrate, isobutyraldehyde, isoeugenol methyl ether, isopropyl methylthiazole, lauric acid, citric acid, linalool, linalool oxide, linalyl acetate, menthol, menthofuran, methyl o-aminobenzoate, methyl butanol, methylbutyric acid, 2-methylbutyl acetate, methyl hexanoate, methyl cinnamate, 5-methylfurfural, 3,2,2-methylcyclopentenolone, 6,5,2-methylheptenone, methyl dihydrojasmonate, methyl jasmonate, 2-methylbutyric acid Methyl ester, 2-methyl-2-pentenoic acid, methyl thiobutyrate, 3,1-methylthiohexanol, 3-methylthiohexanol acetate, nerol, neryl acetate, trans, trans-2,4-nonadienal, 2,4-nonadienol, 2,6-nonadienol, 2,4-nonadienol, nootkatone, butyl octanoic acid, propyl octanoic acid, 2-octanol, 3-octanol, 1,3-octenol, 1-octyl acetate, 3-octyl acetate, palmitic acid, trimeraldehyde, phellandrene, pentanedione, phenylethyl acetate, phenylethyl alcohol, phenylethyl isovalerate, piperonal, propionaldehyde, propyl butyrate, long leaf mintone, pulegol, sweet orange aldehyde, thiothiazole, terpenes, terpineol, terpinene, 8,3-thiomenthone, 4,4,2-thiomethylpentyl ketone, thymol, butyl undecalactone, γ undecalactone, valeric acid, vanillin, acetoin, ethyl vanillin, ethyl vanillyl isobutyrate (= 3-ethoxy-4-isobutyryloxybenzaldehyde), 2,5-dimethyl-4-hydroxy-3(2H)-furanone and its derivatives (preferably cyclohomofuranone (= 2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone), homofuranone (= 2-ethyl-5-methyl-4-hydroxy-3(2H)-furanone and 5-ethyl-2-methyl-4-hydroxy-3(2H)-furanone), maltol and maltol derivatives (preferably ethyl maltol), coumarin 1-Hydroxy-2-(or 5-methyl-2-cyclopentenone), 1-Hydroxy-4-(5-methyl-2-cyclopentenone), 1-Hydroxy-4-(5-methyl-2-cyclopentenone), 1-Hydroxy-4-(5-methyl-2-cyclopentenone), 1-Hydroxy-4-(5-methyl-2-cyclopentenone), 1-Hydroxy-4-(5-methyl-2-cyclopentenone), 1-Hydroxy-4-(5-methyl-2-cyclopentenone), 1-Hydroxy-4-(5-methyl-2-cyclopentenone), 1-Hydroxy-4-(5-methyl-2-cyclopentenone), 1-Hydroxy-4-(5-methyl-2-cyclopentenone, ... 3-phenylglycidyl acid ethyl ester, 2-trans-4-cis-decadienoic acid ethyl ester, 4-(p-hydroxyphenyl)-2-butanone, 1,1-dimethoxy-2,2,5-trimethyl-4-hexane, 2,6-dimethyl-5-heptene-1-al and phenylacetaldehyde, 2-methyl-3-(methylthio)furan, 2-methyl-3-furanthiol, bis(2-methyl-3-furanyl) disulfide, furfurylthiol, methylthiopropionaldehyde, 2-acetyl-2-thiazoline, 3-mercapto-2-pentanone, 2,5-dimethyl-3-furanthiol, 2,4,5-trimethylthiazole, 2-acetylthiazole, 2,4-dimethyl-5-ethylthiazole, 2- Acetyl-1-pyrroline, 2-methyl-3-ethylpyrazine, 2-ethyl-3,5-dimethylpyrazine, 2-ethyl-3,6-dimethylpyrazine, 2,3-diethyl-5-methylpyrazine, 3-isopropyl-2-methoxypyrazine, 3-isobutyl-2-methoxypyrazine, 2-acetylpyrazine, 2-pentylpyridine, (E,E)-2,4-decadienal, (E,E)-2,4-nonadienal, (E)-2-octenal, (E)-2-nonenal, 2-undecenal, 12-methyltridecanal, 1-penten-3-one, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, guaiacol, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, 3-hydroxy-4-methyl-5-ethyl-2(5H)-furanone, cinnamaldehyde, cinnamyl alcohol, methyl salicylate, isopulegol, sugar alcohols (e.g., erythritol, threitol, arabitol, ribitol, xylitol, sorbitol, mannitol, dulcitol, lactitol); proteins (e.g., miraculin, monellin, thaumatin, curculigo sweet protein, brazilian sweet protein); sugar substitutes / bulk sweeteners (e.g., Magapol, sodium cyclamate, acesulfame potassium, neohesperidin dihydrochalcone, saccharin sodium salt, aspartame, super aspartame, neotame, alitame, sucralose, stevioside, rebaudioside, guanidineacetic acid, carrel, suronate, suronate , monatin, phenylodulcine); SUESS-TASTING amino acids (e.g. glycine, D-leucine, D-threonine, D-asparagine, D-phenylalanine, D-tryptophan, L-proline); SUESS-TASTING low molecular weight substances (e.g. hernandusine, dihydrochalcone glycosides, glycyrrhizic saponins, glycyrrhizic acid, its derivatives and salts, glycyrrhizin (licorice) extract, sweet oregano extract, bitter melon extract), plant extracts (e.g. monk fruit and mogrosides obtained therefrom, sweet hydrangea or stevia (e.g. stevia) extract or steviol glycosides obtained therefrom, and any mixtures of the above flavor / flavor substances.
13. The food, cosmetic or pharmaceutical preparation or home care product according to any one of claims 1 to 12, wherein the at least one antioxidant (c) is selected from the group consisting of: dimethylmethoxychromanol at very low tolerated doses, arbutin, amino acids (e.g. arginine, lysine, glycine, histidine, tyrosine, tryptophan) and their derivatives (e.g. acetylcysteine), tert-butylhydroquinone, caffeic acid, chlorogenic acid, imidazoles (e.g. urocanic acid) and their derivatives, kojic acid, peptides such as D,L-carnosine, D-carnosine, L-carnosine and their derivatives (e.g. anserine), hydroxyphenylpropionamidobenzoic acid (dihydroavenanthramide D), diethylhexyl syringylidenemalonate, phenethylresorcinol, gallic acid and its derivatives, quercetin, hydroxyacetophenone, rosmarinic acid, carotenoids, carotenes (e.g. α-carotene, β-carotene, lycopene) ), phytoene, phytoene and its derivatives, lipoic acid and its derivatives (e.g. dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (e.g. thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleoyl, γ-linoleoyl, cholesterol and glycerides) and their salts, dilauryl thiodipropionate , pentaerythritol tetra-di-tert-butyl hydroxyhydrocinnamate, distearyl thiodipropionate, thiodipropionic acid and its derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and sulfenimide compounds (e.g., buthionine sulfenimide, lactobacillus (fermentation products, filtrates, lysates), homocysteine sulfenimide, butyl sulfone, pentathionine sulfenimide, hexathionine sulfenimide, heptathionine sulfenimide),and (metal) chelators (e.g. α-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin, α-hydroxy acids (e.g. citric acid, lactic acid, malic acid), humic acid, bile acid, bile extract, bilirubin, biliverdin, hinokitiol, EDTA, EGTA, trisodium dicarboxymethylalanine, MGDA (methylglycine diacetic acid), GLDA (glutamic acid diacetic acid)) and derivatives thereof, unsaturated fatty acids and derivatives thereof (e.g. γ-linolenic acid, linoleic acid, oleic acid), folic acid and derivatives thereof, ubiquinone and ubiquinol and derivatives thereof, triethyl citrate, vitamin C and derivatives thereof (e.g. ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl acetate), tocopherol and derivatives thereof (e.g. α-tocopherol, β-tocopherol, γ-tocopherol, δ-tocopherol, tocopheryl acetate), panthenol, vitamin A and derivatives thereof (vitamin A palmitate, hydroxypinacolone retinoic acid ester) and Coniferyl benzoate of benzoic acid resin, rutinic acid and its derivatives, ferulic acid and its derivatives, butylated hydroxytoluene, butylated hydroxyanisole, hydroxymethoxyphenyl decanone, dehydroguaiac resin acid, nordihydroguaiac acid, allantoin, tropolone, trihydroxybutyrophenone, uric acid and its derivatives, mannose and its derivatives, hydroxyacetophenone (o / p), zinc and its derivatives (e.g. ZnO, ZnSO4), β-aspartyl arginine, selenium and its derivatives (e.g. methionine selenium), grape seed extract, oat extract, chicory leaf extract, alpine edelweiss extract, green tea extract, curculigo sweet protein, ginger root extract, silymarin, stilbenes and their derivatives (e.g. stilbene oxide, trans-stilbene oxide) and derivatives of the antioxidants, such as salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids, and mixtures of two or more of the antioxidants. , 14. The food, cosmetic or pharmaceutical preparation or household care product according to any one of claims 1 to 13, comprising the at least one fragrance or aroma / flavor compound (a) or a mixture thereof in an amount of 0.01 to 40.0 wt.-%, more preferably in an amount of 0.02 to 35.0 wt.-%, still more preferably in an amount of 0.03 to 30.0 wt.-%, most preferably in an amount of 0.04 to 25.0 wt.-%, based on the total weight of the composition or product.
15. The food, cosmetic or pharmaceutical preparation or household care product according to any one of claims 1 to 14, comprising the mycosporin-like amino acid compound (b) or a mixture thereof in an amount of 0.001 to 15.0 wt. %, particularly 0.01 to 10.0 wt. %, more particularly 0.05 to 7.5 wt. %, most particularly 0.1 to 5.0 wt. %, based on the total weight of the composition or product.
16. The food, cosmetic or pharmaceutical preparation or household care product according to any one of claims 1 to 15, comprising the antioxidant (c) or a mixture thereof in an amount of 0.0001 to 10.0 wt. %, particularly 0.0005 to 8.0 wt. %, more particularly 0.001 to 6.0 wt. %, based on the total weight of the composition or product.
17. The food, cosmetic or pharmaceutical preparation or household care product according to any one of claims 1 to 16, further comprising at least one 1,2-alkanediol or one 2,3-alkanediol having 5 to 12 carbon atoms, wherein the 1,2-alkanediol is preferably selected from the group consisting of 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, 1,2-nonanediol, 1,2-decanediol, 1,2-undecanediol, 1,2-dodecanediol, and wherein the 2,3-alkanediol is preferably selected from the group consisting of 2,3-pentanediol, 2,3-hexanediol, 2,3-heptanediol, 2,3-octanediol, 2,3-nonanediol, 2,3-decanediol, 2,3-undecanediol, 2,3-dodecanediol and any mixtures thereof.
18. The food, cosmetic or pharmaceutical preparation or household care product according to any one of claims 1 to 17, further comprising one or more antimicrobial agents, preferably wherein the antimicrobial agent is selected from the group consisting of 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, 1,2-nonanediol, 1,2-decanediol, 1,2-undecanediol, 1,2-dodecanediol, 2,3-pentanediol, 2,3-hexanediol, 2,3-heptanediol, 2,3-octanediol, 2,3-nonanediol, 2,3-decanediol, 2,3-undecanediol, 2,3-dodecanediol, 2-benzylheptanol, 2-hydroxyacetophenone, 2-methyl 5-cyclohexylpentanol, 3-hydroxypropyl 2-hydroxybenzoate, 4-hydroxyacetophenone and any mixture thereof.
19. The food, cosmetic or pharmaceutical preparation or home care product according to any one of claims 1 to 18, further comprising at least one excipient and / or active substance selected from the group consisting of anti-skin aging agents, emulsifiers, preservatives, UV-filters, silicones, chelating agents, surfactants, green and synthetic polymers, skin cooling agents, rheological additives, oils, carriers and hydrotropes, fragrances or perfume oils, and any mixture of two or more of the aforementioned substances.
20. The food, cosmetic or pharmaceutical preparation or household care product according to any one of claims 1 to 19, which is in the form of (i) dispersions, preferably wherein the cosmetic or pharmaceutical preparation is in the form of an emulsion, in particular an O / W emulsion, a W / O emulsion, a multiple emulsion, an aqueous dispersion gel, a balm, a water-in-oil (W / O / W) or an oil-in-water (O / W / O) multiple emulsion, a PIT emulsion, a Pickering emulsion, a microemulsion, a liquid, a lotion, a suspension, a milk, an ointment, a paste, a gel, a cream-based, an oil-based or a liposome-based formulation or an aerosol, in particular foams and sprays, including all types of silicone-based emulsions; (ii) liquid surfactant formulations; (iii) solid surfactant formulations; (iv) anhydrous preparations; or (v) Aqueous solutions or water / alcohol solutions, in particular water / ethanol solutions, or water / glycol solutions, or alcohol / glycol solutions, in particular ethanol / glycol solutions.
21. The food, cosmetic or pharmaceutical preparation or home care product according to any one of claims 1 to 20, which is used as a food, cosmetic for personal care, in particular for skin care, skin protection, sun protection, scalp protection, scalp care, hair care, nail care, as a medicament for animal care or for home care; preferably wherein the preparation is a fragrance composition or a fragrance / flavor composition.
22. Use of a mycosporin-like amino acid compound or a mixture thereof according to any one of claims 1 to 11 for stabilizing an aroma or fragrance / flavor compound, preferably an aroma or fragrance / flavor compound as defined in claim 12; and / or for promoting the antioxidant effect of an antioxidant, preferably an antioxidant as defined in claim 13.
23. A method for stabilizing an aroma or fragrance / flavor compound, the method comprising the step of mixing an effective amount of at least one mycosporin-like amino acid compound as defined in any one of claims 1 to 11 or a mixture thereof with an aroma or fragrance / flavor compound, preferably an aroma or fragrance / flavor compound as defined in claim 12; and / or a method for promoting the antioxidant effect of an antioxidant, the method comprising the step of mixing an effective amount of at least one mycosporin-like amino acid compound as defined in any one of claims 1 to 11 or a mixture thereof with an antioxidant, preferably an antioxidant as defined in claim 13.
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