1-alkoxyethyl-3-isobutylbenzene and 1-carboxyethyl-3-isobutylbenzene as fragrance ingredients

Abstract

The present invention relates to the use of a compound of formula (I) to impart a fragrance effect to a composition. The present invention also relates to a method of imparting the fragrance effect. The present invention also includes a composition of a compound of formula (I). The present invention also relates to a compound of formula (I').

Description

Invention Field

[0001] This invention relates to the use of compounds of formula (I) to impart an aromatic effect to compositions. The invention also relates to a method for imparting this aromatic effect. The invention further relates to compositions comprising a compound of formula (I) and at least one aromatic chemical, and compositions comprising a compound of formula (I) and at least one other component selected from aromatic chemicals, surfactants, oil components, antioxidants, deodorizing agents, and solvents. The invention also relates to compounds of formula (I'). Background of the Invention

[0003] Aromatic chemicals, especially fragrances, are of great interest in cosmetic, cleaning, and laundry compositions. Most natural fragrances are expensive, their availability is often limited, and their content and purity tend to vary due to fluctuations in environmental conditions. Therefore, to circumvent these disadvantages, it is of great interest to develop synthetic substances that possess sensory properties similar to more expensive natural fragrances or that have novel and interesting sensory characteristics.

[0004] Despite the existence of a large number of aromatic chemicals, there is a continuous need for new components capable of meeting the numerous properties desired in a highly diverse range of applications. These primarily include sensory properties, i.e., compounds should possess favorable aroma (olfactory) or taste properties. Furthermore, aromatic chemicals should also possess additional positive secondary properties, such as efficient preparation methods, the potential to provide better sensory properties due to synergistic effects with other aromatic chemicals, greater stability over a wide compositional range, and greater extensibility and / or better persistence under certain application conditions.

[0005] There is a growing demand for aromatic chemicals that can impart fragrance effects to compositions, particularly floral and / or marine and / or greenish scents. This property is of particular interest for compositions such as body care compositions, hygiene products, cleaning compositions, textile detergent compositions, and fragrance dispenser compositions. Of particular interest are aromatic chemicals that can impart one or more special aromatic effects to a composition, thereby providing the composition with rich and interesting sensory properties, especially olfactory properties. Furthermore, with regard to aromatic chemicals that can impart fragrance effects, durability and fragrance longevity are of particular interest in achieving a lasting fragrance effect in the composition and on surfaces treated with the composition.

[0006] However, because even small changes in chemical structure can cause significant changes in sensory properties such as odor and fragrance, the search for substances possessing certain sensory properties, such as a particular odor, is extremely difficult. Therefore, in most cases, the search for new aromatic chemicals is difficult and laborious, with no guarantee that a substance with the desired odor and / or fragrance will ultimately be found.

[0007] The object of this invention is to provide new aromatic chemicals. These should preferably have pleasant sensory properties.

[0008] The purpose of this invention is to provide an aromatic chemical that can impart an aromatic effect to a composition, preferably a carrot, chocolate, herbal, waxy, woody, citrus, lily of the valley, aquatic, soapy, floral, grapefruit-like, sweet, or musty aroma, or any combination of two or more of the above aromas.

[0009] Another object of the present invention is to provide aromatic chemicals that can impart a lasting fragrance effect to compositions and surfaces treated with such compositions, such as skin and / or textiles, preferably a carrot or chocolate or herbal or waxy or woody or citrus or lily of the valley or aquatic or soapy or floral or grapefruit-like or sweet or musty fragrance effect, or any combination of two or more of the above fragrances, and are stable in a wide variety of compositions. Invention Overview

[0011] The discovery of compound (I) is remarkable; it imparts aromatic effects to the composition, particularly carrot, chocolate, herbal, waxy, woody, citrus, lily of the valley, aquatic, soapy, floral, grapefruit-like, sweet, or musty aromas. This aromatic effect is stable across a wide range of compositions and thus provides the composition with rich and interesting aromatic properties.

[0012] Therefore, one aspect of the present invention relates to the use of at least one compound of formula (I) or its salt or its stereoisomer to impart an aromatic effect to a composition:

[0013]

[0014] in

[0015] X is selected from -OR, -O(C=O)-R and =O;

[0016] R is selected from -H, linear or branched unsubstituted -C1-C5 alkyl and unsubstituted -C3-C5 cycloalkyl.

[0017] Another aspect of the present invention provides a method for imparting an aromatic effect to a composition, comprising at least the step of adding at least one compound of formula (I) or a salt thereof or a stereoisomer thereof to the composition:

[0018]

[0019] in

[0020] X is selected from -OR, -O(C=O)-R and =O;

[0021] R is selected from -H, linear or branched unsubstituted -C1-C5 alkyl and unsubstituted -C3-C5 cycloalkyl.

[0022] In another aspect, the present invention provides a composition comprising at least one compound of formula (I) or a salt thereof or a stereoisomer thereof:

[0023]

[0024] in

[0025] X is selected from -OR, -O(C=O)-R and =O;

[0026] R is selected from -H, linear or branched unsubstituted -C1-C5 alkyl and unsubstituted -C3-C5 cycloalkyl;

[0027] as well as

[0028] (i) at least one aromatic chemical different from formula (I), or

[0029] (ii) at least one non-aromatic chemical carrier, or

[0030] (iii)(i) and (ii) both.

[0031] In another aspect, the present invention provides a compound of formula (I') or a salt thereof or a stereoisomer thereof:

[0032]

[0033] in

[0034] X is selected from -OR a and -O(C=O)-R b ;

[0035] R a Selected from linear or branched unsubstituted C2-C5 alkyl and unsubstituted C3-C5 cycloalkyl;

[0036] R b Selected from linear or branched unsubstituted C1-C5 alkyl and unsubstituted C3-C5 cycloalkyl.

[0037] Another aspect of the invention relates to a mixture comprising at least one compound of formula (II) or a salt thereof or a stereoisomer thereof:

[0038]

[0039] in

[0040] Y is selected from -O-R1, -O(C=O)-R1 and =O;

[0041] R1 is selected from linear or branched unsubstituted C1-C5 alkyl and unsubstituted C3-C5 cycloalkyl; and at least one compound of formula (I) or a salt thereof or a stereoisomer thereof:

[0042]

[0043] in

[0044] X is selected from -OR, -O(C=O)-R and =O;

[0045] R is selected from -H, linear or branched unsubstituted -C1-C5 alkyl and unsubstituted -C3-C5 cycloalkyl.

[0046] Another aspect of the present invention relates to the use of mixtures comprising at least one compound of formula (I) and at least one compound of formula (II) to impart an aromatic effect.

[0047] Another aspect of the invention relates to a composition comprising a mixture of at least one compound of formula (I) and at least one compound of formula (II) and its use in imparting an aromatic effect. Invention Details

[0049] The following detailed description is merely exemplary and is not intended to limit the invention or its application and uses. Furthermore, it is not intended to be bound by any theory set forth in the foregoing technical field, background, overview, or the following detailed description.

[0050] The terms “comprising,” “including,” and “consisting of” as used herein are synonyms with “including” or “containing,” and are either inclusive or open-ended and do not exclude additional unreferenced members, elements, or method steps. It should be understood that the terms “comprising,” “including,” and “consisting of” as used herein include the term “composed of.”

[0051] Furthermore, the terms “(a)”, “(b)”, “(c)”, “(d)”, etc., used in the specification and claims are used to distinguish similar elements and are not necessarily used to describe a sequential or chronological order. It should be understood that such terms are interchangeable where appropriate and embodiments of the subject matter described herein can be operated in orders other than those described or shown herein. In cases where the terms “(A)”, “(B)”, and “(C)” or “AA), BB) and CC)” or “(a)”, “(b)”, “(c)”, “(d)”, “(i)”, “(ii)”, etc., relate to steps of a method, use, or analysis, there is no temporal or time interval coherence between the steps; that is, these steps may be performed simultaneously or there may be time intervals of seconds, minutes, hours, days, weeks, months, or even years between these steps, unless otherwise specified in this application as described in the context.

[0052] The different aspects of the subject matter are defined in more detail in the following paragraphs. These aspects, as thus defined, may be combined with any one or more other aspects unless explicitly stated otherwise. Specifically, any feature shown as preferred or advantageous may be combined with any one or more other features shown as preferred or advantageous.

[0053] Throughout this specification, references to "an embodiment," "an embodiment," or "a preferred embodiment" mean that the specific feature, structure, or characteristic described for that embodiment is included in at least one embodiment of the invention. Therefore, the phrases "in an embodiment," "in a particular embodiment," or "in a preferred embodiment," appearing in various places throughout the specification, do not necessarily all refer to the same embodiment, but may. Furthermore, these features, structures, or characteristics can be combined in any suitable manner in one or more embodiments, as will be apparent to those skilled in the art from this disclosure. Moreover, although some embodiments described herein include some, but not others, features included in other embodiments, combinations of features from different embodiments are intended to be within the scope of the subject matter and form different embodiments, as will be understood by those skilled in the art. For example, in the appended claims, any claimed embodiment can be used in any combination.

[0054] Furthermore, the ranges defined throughout this specification also include end values; that is, the range of 1-10 implies that both 1 and 10 are included within this range. For the avoidance of doubt, any equivalent should be authorized to the applicant in accordance with applicable law.

[0055] definition

[0056] In the context of this invention, the term "aromatic gas" refers to sensory properties and includes odor and / or fragrance.

[0057] The term "aromatic chemicals" refers to substances used to achieve sensory or perceptual effects (which are used interchangeably herein) and includes their use in achieving olfactory and / or aroma effects. The term "olfactory effect" refers to an odor effect that does not elicit any positive or negative judgment, while the terms "aroma effect," "fragrance effect," or "aromatic effect" (which are used interchangeably herein) relate to an overall pleasant odor effect. Therefore, "fragrance" or "aroma" refers to aromatic chemicals that primarily result in a pleasant odor effect. Fragrance leads to taste effects.

[0058] As used herein, the term "aromatic composition" refers to a composition that produces an aroma. The term aromatic composition includes "odor composition" and / or "fragrance composition." An odor composition is a composition that primarily produces an odor effect, and a fragrance composition is a composition that primarily produces a taste effect.

[0059] The term odor composition includes "fragrance composition" or "aroma composition" (which are used interchangeably in this document), which primarily results in an overall pleasant odor effect.

[0060] The general hedonistic expression "favorable sensory properties" or "favorable sensory performance" describes the pleasantness and simplicity of the sensory effects conveyed by aromatic chemicals. "Pleasant" and "simple" are terms familiar to those skilled in the art, such as perfumers. Pleasantness generally refers to a spontaneously generated, positively perceived pleasant sensory effect. However, "pleasant" is not necessarily synonymous with "sweet." "Pleasant" can also refer to the scent of musk or sandalwood oil. "Simple" generally refers to a spontaneously generated sensory effect that produces a repetitive, identical reminder of certain things to the same test group. For example, a substance can have a scent that spontaneously evokes the smell of an "apple": the scent is simply an "apple" scent. If this apple scent is very pleasant because it evokes, for example, the scent of a fully ripe, sweet apple, then the scent is called "pleasant." However, the scent of a tart apple can also be simple. If both of these reactions occur when smelling the substance—and thus, in this example, it is a pleasant and simple apple scent—then the substance has particularly favorable sensory properties.

[0061] The expressions “combination of…”, “in combination with…”, or “in combination with…” used herein refer to compositions, methods, or uses of two compounds, taking into account the fact that the two compounds do not need to be used as a physical mixture of the compounds, but can be used separately (e.g., added). When the compounds are used separately, they can be used sequentially (i.e., one after another) or simultaneously (i.e., substantially at the same time) in any order (e.g., added).

[0062] The terms “enhancement” or “synergistic effect” are used herein to describe the effect of enhancing and / or modifying the aroma of an aromatic chemical or composition. The term “enhancement” includes improving the pleasantness and / or simplicity of the aroma and / or improving its intensity. The term “modification” includes altering the aromatic properties.

[0063] Intensity can be determined by a threshold. The odor threshold is when the odor effect is just perceptible to a representative test group, but the concentration of the substance in the relevant gas space is no longer required.

[0064] When applications requiring top-tasting aromas are desired, synergistic effects are particularly needed in fragrance compositions, such as in deodorants, air fresheners, or in the taste zones of chewing gum, where the aroma needs to be delivered particularly quickly and concentratedly.

[0065] The terms “in this invention” and “the purpose of this invention” are used synonymously throughout the invention.

[0066] The terms “compound” and “substance” are used synonymously throughout the invention.

[0067] The term "aroma persistence" describes the evaporation behavior of aromatic chemicals over time. Aroma persistence can be determined, for example, by applying the aromatic chemical to a test strip and then evaluating the odor effect of the test strip by smell. For aromatic chemicals with high aroma persistence, the duration for which the group can still identify the aromatic effect is long afterward.

[0068] The term "fastness" describes the interaction of aromatic chemicals with surfaces, such as skin or textiles, especially after subsequent treatment of that surface, such as washing. Fastness can be determined, for example, by washing textiles with a textile detergent composition containing the aromatic chemical and then evaluating the textiles by smell immediately after washing (wet textiles) and by evaluating dry textiles after long-term storage.

[0069] The term "stability" describes the behavior of aromatic chemicals when exposed to oxygen, light, and / or other substances. Aromatic chemicals with high stability retain their aromatic properties over long periods of time, preferably in a wide variety of compositions and under a variety of storage conditions.

[0070] In order to impart a lasting fragrance effect to the composition or the surface treated with the composition, the fragrance chemical in the composition should preferably have high fragrance persistence, robustness and stability.

[0071] Uses and methods

[0072] One embodiment of the present invention relates to the use of at least one compound of formula (I) or a salt thereof or a stereoisomer thereof to impart an aromatic effect to a composition:

[0073]

[0074] in

[0075] X is selected from -OR, -O(C=O)-R and =O;

[0076] R is selected from -H, linear or branched unsubstituted -C1-C5 alkyl and unsubstituted -C3-C5 cycloalkyl.

[0077] One embodiment of the present invention relates to a method for imparting an aromatic effect to a composition, comprising at least the step of adding at least one compound of formula (I) or a salt thereof or a stereoisomer thereof to the composition:

[0078]

[0079] in

[0080] X is selected from -OR, -O(C=O)-R and =O;

[0081] R is selected from -H, linear or branched unsubstituted -C1-C5 alkyl and unsubstituted -C3-C5 cycloalkyl.

[0082] In one implementation, X is selected from -OR, -O(C=O)-R, and =O;

[0083] In the preferred embodiment, X is OR.

[0084] In another preferred embodiment, X is -O(C=O)-R.

[0085] In a preferred embodiment, R is selected from -H, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)(C2H5), -CH2CH(CH3)2, -CH2CH2CH2CH3, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -CH(CH3)CH2CH3, cyclopropyl, and cyclobutyl.

[0086] In a more preferred embodiment, R is -CH2CH3.

[0087] In yet another preferred embodiment, the composition is selected from fragrance compositions, body care compositions, hygiene products, cleaning compositions, textile detergent compositions, fragrance dispenser compositions, food, food supplements, pharmaceutical compositions, and crop protection compositions.

[0088] In one embodiment, the effect is a carrot scent. In one embodiment, the effect is a chocolate scent. In one embodiment, the effect is an herbal scent. In one embodiment, the effect is a waxy scent. In one embodiment, the effect is a woody scent. In one embodiment, the effect is a citrus scent. In one embodiment, the effect is an aquatic scent. In one embodiment, the effect is a musty scent. In one embodiment, the effect is a soapy scent. In one embodiment, the effect is a floral scent. In one embodiment, the effect is a lily of the valley scent. In one embodiment, the effect is a grapefruit-like scent. In one embodiment, the effect is a sweet scent. In one embodiment, the compound may have more than one aromatic effect.

[0089] In a preferred embodiment, the compound of formula (I) or its salts or stereoisomers are present in an amount ranging from ≥0.01 wt% to ≤70.0 wt%, more preferably from ≥0.05 wt% to ≤60.0 wt%, and particularly from ≥0.1 wt% to ≤50.0 wt%, based on the total weight of the composition. In yet another preferred embodiment, the compound of formula (I) or its salts or stereoisomers are present in an amount ranging from 0.05 to 10 wt%, more preferably from 0.1 to 5 wt%, still more preferably from 0.2 to 3 wt%, and most preferably from 20 to 70 wt%, particularly from 25 to 50 wt%, based on the total weight of the composition.

[0090] Composition

[0091] One embodiment of the present invention relates to a composition comprising at least one compound of formula (I) or a salt thereof or a stereoisomer thereof:

[0092]

[0093] in

[0094] X is selected from -OR, -O(C=O)-R and =O;

[0095] R is selected from -H, linear or branched unsubstituted -C1-C5 alkyl and unsubstituted -C3-C5 cycloalkyl;

[0096] as well as

[0097] (i) at least one aromatic chemical different from formula (I), or

[0098] (ii) at least one non-aromatic chemical carrier, or

[0099] (iii)(i) and (ii) both.

[0100] In one implementation, X is selected from -OR, -O(C=O)-R, and =O.

[0101] In the preferred embodiment, X is OR.

[0102] In another preferred embodiment, X is -O(C=O)-R.

[0103] In a preferred embodiment, R is selected from -H, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)(C2H5), -CH2CH(CH3)2, -CH2CH2CH2CH3, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -CH(CH3)CH2CH3, cyclopropyl, and cyclobutyl.

[0104] In another preferred embodiment, the at least one aromatic chemical (i) is selected from geraniol acetate, α-hexylcinnamaldehyde, 2-phenoxyethyl isobutyrate, dihydrogeraniol, methyl dihydrojasmonate, 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopentadien[g]benzopyran, tetrahydrolinalool, ethyllinalool, benzyl salicylate, 2-methyl-3-(4-tert-butylphenyl)propanal, cinnamyl alcohol, 4,7-methylene-3a,4,5,6,7,7a-hexahydro-5-indenyl acetate and / or 4,7-methylene-3a,4,5,6,7,7a-hexahydro-6-indenyl acetate, citronellol. Citronellol acetate, tetrahydrogeraniol, vanillin, linaloyl acetate, styrax acetate, octahydro-2,3,8,8-tetramethyl-2-naphthyl ethyl ketone and / or 2-acetyl-1,2,3,4,6,7,8-octahydro-2,3,8,8-tetramethylnaphthalene, hexyl salicylate, 4-tert-butylcyclohexyl acetate, 2-tert-butylcyclohexyl acetate, α-ionone, n-α-methylionone, α-isomethylionone, coumarin, terpineol acetate, 2-phenylethanol, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarboxaldehyde, α-pentylcinnamaldehyde, ethylene brassinate, (E) and / or (Z)-3-methylcyclopentadecano-5 -enone, 15-pentadecano-11-enolactone and / or 15-pentadecano-12-enolactone, 15-cyclopentadecanolactone, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthyl)acetone, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, cis-3-hexenyl acetate, trans-3-hexenyl acetate, trans-2 / cis-6-nonadienol, 2,4-dimethyl-3-cyclohexenaldehyde, 2,4,4,7-tetramethyloct-6-en-3-one, 2,6- Dimethyl-5-hepten-1-aldehyde, Borneol, 3-(3-isopropylphenyl)butanal, 2-methyl-3-(3,4-methylenedioxyphenyl)propanal, 3-(4-ethylphenyl)-2,2-dimethylpropanal, 7-methyl-2H-1,5-benzodioxane-hepten-3(4H)-one, 3,3,5-trimethylcyclohexyl acetate, 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydronaphthyl-2-phenol, 3-(4-tert-butylphenyl)propanal, ethyl 2-methylvalerate, ethoxymethoxycyclododecane, 2,4-dimethyl-4,4a,5,9b-tetrahydroinden[1,2-d][1,3]di Alkenes, (2-tert-butylcyclohexyl) acetate and 3-[5,5,6-trimethylbicyclo[2.2.1]hept-2-yl]cyclohexane-1-ol.

[0105] In yet another preferred embodiment, the at least one aromatic chemical (i) is selected from methyl benzoate, benzyl acetate, geraniol acetate, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol, linalool, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol and methyl benzoate.

[0106] In yet another preferred embodiment, the at least one aromatic chemical (i) is selected from ethyl vanillin, vanillin, 2,5-dimethyl-4-hydroxy-2H-furan-3-one (furanone) or 3-hydroxy-2-methyl-4H-pyran-4-one (maltol).

[0107] Compounds of formula (I) can be combined with other aromatic chemicals to obtain compositions of the present invention, for example, which can be found in S. Arctander, Perfume and Flavor Chemicals, Volumes I and II, Montclair, NJ, 1969, self-published by the authors, or in K. Bauer, D. Garbe and H. Surburg, Common Fragrance and Flavor Materials, 4th edition, Wiley-VCH, Weinheim 2001. Specifically, it may be mentioned that:

[0108] Extracts from natural ingredients, such as essential oils, gels, absolutes, resins, aromatic resins, balms, and tinctures like ambergris tincture; sage oil; angelica seed oil; angelica root oil; fennel oil; valerian oil; basil oil; tree moss absolute; laurel oil; artemisia oil; benzoin resin; bergamot oil; beeswax absolute; birch tar; bitter almond oil; peppermint oil; bucco leaf oil; calomel oil; juniper oil; calamus oil; camphor oil; ylang-ylang oil; cardamom oil; calomel oil; cinnamon oil; cinnamon absolute; castoreum absolute; cedarwood leaf oil; cedarwood oil; osmanthus flower oil; lemongrass oil; coumarin oil; coumarin balsam; coumarin balsam oil; coriander oil; costus root oil; cumin oil; cypress oil; artemisia oil; dill oil; dill seed oil; Eau de Brouts absolute; Oakmoss absolute; Elemi oil; Tarragon oil; Lemon eucalyptus oil; Eucalyptus oil; Fennel oil; Spruce needle oil; Geffen oil; Geffen resin; Geranium oil; Grapefruit oil; Guaiac oil; Ancient rue resin; Ancient rue resin oil; Immortelle absolute; Immortelle oil; Ginger oil; Orris root absolute; Orris root oil; Jasmine absolute; Sweet flag oil; Blue chamomile oil; Roman chamomile oil; Carrot seed oil; Carrageenan oil; Pine needle oil; Spearmint oil; Artemisia Rockrose oil; Rockrose absolute; Rockrose resin; Mixed lavender absolute; Mixed lavender oil; Lavender absolute; Lavender oil; Lemongrass oil; Angelica dahurica oil; Distilled white lemon oil; Pressed white lemon oil; Linalool oil; Litsea cubeba oil; Bay leaf oil; Nutmeg oil; Oregano oil; Orange oil; Cinnamon bark oil; Mimosa absolute; Ambrette oil; Musk tincture; Sage oil; Nutmeg oil; Myrrh absolute; Myrrh oil; Myrtle oil; clove leaf oil; clove flower oil; neroli oil; frankincense absolute; frankincense oil; parsnip root oil; neroli absolute; orange oil; oregano oil; palmarosa oil; patchouli oil; perilla seed oil; Peruvian balsam oil; parsley leaf oil; parsley seed oil; orange leaf oil; peppermint oil; Sichuan pepper oil; allspice oil; pine oil; peppermint oil; rose absolute; rosewood oil; rose oil; rosemary oil; Dalmatian sage oil; Spanish sage oil; Sandalwood oil; celery seed oil; lavender seed oil; anise oil; styrax oil; marigold oil; cedar needle oil; tea tree oil; turpentine oil; thyme oil; turmeric balsam; lavender bean absolute oil; tuberose absolute oil; vanilla oil; violet leaf absolute oil; verbena oil; vetiver oil; juniper seed oil; lees oil; wormwood oil; wintergreen oil; hyacinth oil; civet absolute oil; cinnamon leaf oil; cinnamon bark oil, and their fractions or components separated therefrom;

[0109] Individual fragrances selected from hydrocarbons, such as 3-carene; α-pinene; β-pinene; α-terpinene; γ-terpinene; p-isopropylbenzylmethane; bisabolene; pinene; caryophyllene; cedrene; farnesene; limonene; longleafene; myrcene; ocimene; hesperene; (E,Z)-1,3,5-undecanetriene; styrene; diphenylmethane;

[0110] Aliphatic alcohols, such as 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; mixtures of 3,4,5,6,6-pentamethyl-3 / 4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methylenehepten-2-ol; (E,Z)-2,6-nonadienol; 3,7-dimethyl-7-methoxyoct-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol;

[0111] Aliphatic aldehydes and their acetals, such as hexanal; heptanal; octanal; nonanal; decanal; undecanal; dodecanal; tridecanal; 2-methyloctanal; 2-methylnonanal; (E)-2-hexenal; (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-undecenal. Dienal; heptanal diethanol; 1,1-dimethoxy-2,2,5-trimethyl-4-hexene; citronelloloxyacetaldehyde; (E / Z)-1-(1-methoxypropoxy)hex-3-ene; aliphatic ketones and their oximes, such as 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 3-methylthiohexanol; 3-methylthiohexyl acetate; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthiohexyl acetate; 1-menthol-8-thiol;

[0113] Aliphatic nitriles, such as 2-nonenonitrile; 2-undecenonitrile; 2-tetadecaenonitrile; 3,12-tetadecadienonitrile; 3,7-dimethyl-2,6-octadienonitrile; 3,7-dimethyl-6-octenonitrile;

[0114] Esters of aliphatic carboxylic acids, such as (E)- and (Z)-3-hexenyl formate; ethyl acetoacetate; isopentyl 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; isopentyl butyrate; butyl... Hexyl crotonate; (E)- and (Z)-3-hexenyl isobutyrate; hexyl crotonate; ethyl isovalerate; ethyl 2-methylvalerate; ethyl hexanoate; allyl hexanoate; ethyl heptaate; allyl heptaate; ethyl octanoate; (E,Z)-2,4-decadienoate; methyl 2-octynoate; methyl 2-nonynoate; allyl 2-isopentoxyacetate; methyl 3,7-dimethyl-2,6-octadienoate; 4-methyl-2-pentyl crotonate;

[0115] Acyclic terpene alcohols, such as geraniol; nerol; linalool; lavenderol; nerolidol; farnesol; tetrahydrolinalool; 2,6-dimethyl-7-octen-2-ol; 2,6-dimethyloct-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-octtrien-3-ol; 2,6-dimethyl-2,5,7-octtrien-1-ol; and their formates, acetates, propions, isobutyrates, butyrates, isovalerates, valerates, hexanoates, crotonates, tigrinates and 3-methyl-2-butenoates;

[0116] Acyclic terpenoid aldehydes and ketones, such as geranialdehyde; neraldehyde; citronellol; 7-hydroxy-3,7-dimethyloctanal; 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal; geraniol acetone, and diethanol and diethanol condensations of geranialdehyde, neraldehyde, and 7-hydroxy-3,7-dimethyloctanal; cyclic terpenoid alcohols, such as menthol; isopreneol; α-terpineol; terpine-4-ol; menthane-8-ol; menthane-1-ol; menthane-7-ol; borneol; isoborneol; linalool oxide; nobutol; cedrol; ambergris octahydronaphthol; vetiverol; guaiacol; and their formate, acetate, propionate, isobutyrate, butyrate, isovalerate, valerate, hexanoate, crotonate, tigrinate and 3-methyl-2-butenoate;

[0117] Cyclic terpenoid aldehydes and ketones, such as menthone; isomenthone; 8-mercaptomenthane-3-one; carvone; camphor; anisone; α-ionone; β-ionone; α-n-methylionone; β-n-methylionone; α-isomethylionone; β-isomethylionone; α-irisone; α-trakone; β-trakone; β-trakone; δ-trakone; γ-trakone; 1-(2,4,4-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one; 1,3,4,6,7,8a-hexahydro-1,1,5,5-tetramethyl-2 H-2,4a-methylenenaphthalene-8(5H)-one; 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal; nocacolone; dihydronocacolone; 4,6,8-macrostigmatrien-3-one; α-sweet orange aldehyde; β-sweet orange aldehyde; acetylated cedarwood oil (methyl cedarwood ketone); cyclic alcohols, such as 4-tert-butylcyclohexanol; 3,3,5-trimethylcyclohexanol; 3-isobenzylcyclohexanol; 2,6,9-trimethyl-Z2,Z5,E9-cyclododecanetrien-1-ol; 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol;

[0118] Alicyclic alcohols, such as α-3,3-trimethylcyclohexylethanol; 1-(4-isopropylcyclohexyl)ethanol; 2-methyl-4-(2,2,3-trimethyl-3-cyclopentan-1-yl)butanol; 2-methyl-4-(2,2,3-trimethyl-3-cyclopentan-1-yl)-2-buten-1-ol; 2-ethyl-4-(2,2,3-trimethyl-3-cyclopentan-1-yl)-2-buten-1-ol; 3-methyl-5- -(2,2,3-trimethyl-3-cyclopentan-1-yl)pentan-2-ol; 3-methyl-5-(2,2,3-trimethyl-3-cyclopentan-1-yl)-4-penten-2-ol; 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopentan-1-yl)-4-penten-2-ol; 1-(2,2,6-trimethylcyclohexyl)pentan-3-ol; 1-(2,2,6-trimethylcyclohexyl)hexyl-3-ol;

[0119] Cyclic and alicyclic ethers, such as eucalyptol; methyl cedarwood ether; cyclododecyl methyl ether; 1,1-dimethoxycyclododecane; (ethoxymethoxy)cyclododecane; α-cedrene epoxide; 3a,6,6,9a-tetramethyldodecanonaphtho[2,1-b]furan; 3a-ethyl-6,6,9a-trimethyldodecanonaphtho[2,1-b]furan; 1,5,9-trimethyl-13-oxabicyclo[10.1.0]tetane-4,8-diene; rose ether; 2-(2,4-dimethyl-3-cyclohexen-1-yl)-5-methyl-5-(1-methylpropyl)-1,3-di alkyl;

[0120] Cyclic and macrocyclic ketones, such as 4-tert-butylcyclohexanone; 2,2,5-trimethyl-5-pentylcyclopentanone; 2-heptylcyclopentanone; 2-pentylcyclopentanone; 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-cyclopentadecanone; 3-methyl-5-cyclopentadecanone; 3-methylcyclopentadecanone Alkane; 4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone; 4-tert-amylcyclohexanone; 5-cyclohexadecene-1-one; 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-2,3-dihydro-1-indanone; 8-cyclohexadecene-1-one; 7-cyclohexadecene-1-one; (7 / 8)-cyclohexadecene-1-one; 9-cycloheptadecene-1-one; cyclopentadecanone; cyclohexadecanecanone;

[0121] Alicyclic aldehydes, such as 2,4-dimethyl-3-cyclohexenaldehyde; 2-methyl-4-(2,2,6-trimethylcyclohexen-1-yl)-2-butenaldehyde; 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenaldehyde; 4-(4-methyl-3-penten-1-yl)-3-cyclohexenaldehyde;

[0122] Alicyclic ketones, such as 1-(3,3-dimethylcyclohexyl)-4-penten-1-one; 2,2-dimethyl-1-(2,4-dimethyl-3-cyclohexen-1-yl)-1-propanone; 1-(5,5-dimethyl-1-cyclohexen-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-cyclododecathitryl ketone; tert-butyl(2,4-dimethyl-3-cyclohexen-1-yl) ketone;

[0123] Esters of cyclic alcohols, such as 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert-pentylcyclohexyl 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 acetate. 4,7-methylene-3a,4,5,6,7,7a-hexahydro-5 or 6-indanyl acetate; 4,7-methylene-3a,4,5,6,7,7a-hexahydro-5 or 6-indanyl propionate; 4,7-methylene-3a,4,5,6,7,7a-hexahydro-5 or 6-indanyl isobutyrate; 4,7-methylene-octahydro-5 or 6-indanyl acetate;

[0124] Esters of alicyclic alcohols, such as 1-cyclohexylethyl crotonate;

[0125] Esters of alicyclic carboxylic acids, such as allyl 3-cyclohexylpropionate; allyl cyclohexyloxyacetate; methyl cis- and trans-dihydrojasmonic acid; methyl cis- and trans-jasmonic acid; 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-ethyl acetate;

[0126] Aromatic aliphatic alcohols, such as 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;

[0127] Esters of aryl aliphatic alcohols and aliphatic carboxylic acids, such as benzyl acetate; benzyl propionate; benzyl isobutyrate; benzyl isovalerate; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-phenylethyl isovalerate; 1-phenylethyl acetate; α-trichloromethylbenzyl acetate; α,α-dimethylphenylethyl acetate; α,α-dimethylphenylethyl butyrate; cinnamyl acetate; 2-phenoxyethyl isovalerate; 4-methoxybenzyl acetate;

[0128] Aryl aliphatic ethers, such as 2-phenylethylmethyl ether; 2-phenylethyl isopentyl ether; 2-phenylethyl 1-ethoxyethyl ether; phenylacetaldehyde dimethyl acetal; phenylacetaldehyde diethanol acetal; solanal dimethyl acetal; phenylacetaldehyde glycerol acetal; 2,4,6-trimethyl-4-phenyl-1,3-diphenylacetal. Alkane; 4,4a,5,9b-tetrahydroindenzo[1,2-d]-m-di Alkene; 4,4a,5,9b-tetrahydro-2,4-dimethylindo[1,2-d]-m-di Alkenes; aromatic and arylaliphatic aldehydes, such as benzaldehyde; phenylacetaldehyde; 3-phenylpropanal; solanal; 4-methylbenzaldehyde; 4-methylphenylacetaldehyde; 3-(4-ethylphenyl)-2,2-dimethylpropanal; 2-methyl-3-(4-isopropylphenyl)propanal; 2-methyl-3-(4-tert-butylphenyl)propanal; 2-methyl-3-(4-isobutylphenyl)propanal; 3-(4-tert-butylphenyl)propanal; Cinnamaldehyde; α-Butylcinnamaldehyde; α-Pentylcinnamaldehyde; α-Hexylcinnamaldehyde; 3-Methyl-5-phenylpentanal; 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;

[0129] Aromatic and arylita-ketones, such as acetophenone; 4-methylacetophenone; 4-methoxyacetophenone; 4-tert-butyl-2,6-dimethylacetophenone; 4-phenyl-2-butanone; 4-(4-hydroxyphenyl)-2-butanone; 1-(2-naphthyl)acetophenone; 2-benzofuranylacetophenone; (3-methyl-2-benzofuranyl)acetophenone; benzophenone; 1,1,2,3,3,6-hexamethylene 5-2,3-dihydroindenemethyl ketone; 6-tert-butyl-1,1-dimethyl-4-2,3-dihydroindenemethyl ketone; 1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-5-indene] ethyl ketone; 5',6',7',8'-tetrahydro-3',5',5',6',8',8'-hexamethyl-2-naphthyl ethyl ketone;

[0130] Aromatic and aryl aliphatic carboxylic acids and their esters, such as benzoic acid; phenylacetic acid; methyl benzoate; ethyl benzoate; hexyl benzoate; benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geraniol phenylacetate; phenylethyl phenylacetate; methyl cinnamate; ethyl cinnamate; benzyl cinnamate; phenylethyl cinnamate; cinnamate; allyl phenoxyacetate; methyl salicylate; isoamyl 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;

[0131] Nitrogen-containing aromatic compounds, such as 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-pentenonitrile; 3-methyl-5-phenylpentenonitrile; methyl anthranilate; 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;

[0132] Phenolic compounds, phenyl ethers, and phenyl esters, such as artemisia argyi; anethole; eugenol; eugenol methyl ether; isoeugenol; isoeugenol methyl ether; thymol; carvacrol; diphenyl ether; β-naphthylmethyl ether; β-naphthylethyl ether; β-naphthyl isobutyl ether; 1,4-dimethoxybenzene; eugenol acetate; 2-methoxy-4-methylphenol; 2-ethoxy-5-(1-propenyl)phenol; p-cresol phenylacetate;

[0133] Heterocyclic compounds, such as 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;

[0134] Lactones, such as 1,4-octyl lactone; 3-methyl-1,4-octyl lactone; 1,4-nonyl lactone; 1,4-decyl lactone; 8-decen-1,4-lactone; 1,4-undecane lactone; 1,4-dodecane lactone; 1,5-decyl lactone; 1,5-dodecane lactone; 4-methyl-1,4-decyl lactone; 1,15-pentadecanyl lactone; cis- and trans-11-pentadecanene-1,15-lactone; cis- and Trans-12-pentadecane-1,15-lactone; 1,16-hexadecanelactone; 9-hexadececane-1,16-lactone; 10-oxa-1,16-hexadecanelactone; 11-oxa-1,16-hexadecanelactone; 12-oxa-1,16-hexadecanelactone; ethylene 1,12-dodecanoic acid; ethylene 1,13-tridecanoic acid; coumarin; 2,3-dihydrocoumarin; octahydrocoumarin.

[0135] The aromatic chemicals (i) used in the composition are obtained from known commercial sources and are sourced from Germany.

[0136] In a preferred embodiment, the at least one non-aromatic chemical carrier (ii) is selected from surfactants, oil components, antioxidants, deodorizing agents, and solvents.

[0137] In the context of this invention, "solvent" is used to dilute the compound of formula (I) to be used according to the invention and / or any other component of the composition without having its own aroma.

[0138] The amount of solvent chosen depends on the composition.

[0139] In yet another preferred embodiment, the solvent is selected from ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1,2-butanediol, dipropylene glycol, triethyl citrate, isopropyl myristate, and any mixture of two or more of the above solvents.

[0140] In yet another preferred embodiment, the solvent is present in the composition in an amount of 0.01-99.0% by weight, more preferably 0.05-95.0% by weight, still more preferably 0.1-80.0% by weight, most preferably 0.1-70.0% by weight, and particularly 0.1-60.0% by weight, based on the total weight of the composition.

[0141] In yet another preferred embodiment of the invention, the composition comprises 0.05-10% by weight, more preferably 0.1-5% by weight, and still more preferably 0.2-3% by weight of all solvents based on the total weight of the composition. In yet another preferred embodiment of the invention, the composition comprises 20-70% by weight, more preferably 25-50% by weight of all solvents based on the total weight of the composition.

[0142] One embodiment of the present invention relates to a composition comprising a compound of formula (I) and at least one oil component.

[0143] In a preferred embodiment, all oil components are present in an amount of 0.1-80% by weight, more preferably 0.5-70% by weight, still more preferably 1-60% by weight, even more preferably 1-50% by weight, particularly 1-40% by weight, and even more particularly 5-25% by weight, specifically 5-15% by weight, based on the total weight of the composition.

[0144] The oil component may be selected, for example, from guerbert alcohols based on fatty alcohols containing 6-18, preferably 8-10, carbon atoms, as well as other additional esters, such as myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl benzyl acid, myristyl erucic acid, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl benzyl acid, cetyl erucic acid, stearyl myristate, stearyl palmitate, stearyl stearate, stearyl isostearate, stearyl oleate, stearyl benzyl acid, stearyl erucic acid, and myristyl myristate. Isostearyl palmitate, isostearyl stearate, isostearyl stearate, isostearyl oleate, isostearyl benzyl acid, isostearyl oleate, oleyl palmitate, oleyl stearate, isostearyl isostearyl oleate, oleyl benzyl acid, oleyl erucic acid, oleyl myristate Betaine esters, betaine palmitate ester, betaine stearate ester, betaine isostearate ester, betaine oleate ester, betaine acid ester, betaine erucic acid ester, myristate betaine ester, betaine palmitate ester, betaine stearate ester, betaine isostearate ester, betaine oleate ester, betaine acid ester, and betaine erucic acid ester. Also suitable is C. 18 -C 38 Alkyl hydroxycarboxylic acids and linear or branched C6-C 22 Esters of fatty alcohols, especially dioctyl malate, are esters of linear and / or branched fatty acids with polyols (e.g., propylene glycol, dimer glycols, or trimer glycols), based on C6-C. 10 fatty acid triglycerides, based on C6-C 18 A liquid mixture of monoglycerides, diglycerides, and triglycerides of fatty acids, C6-C 22 Esters of fatty alcohols and / or guerbert alcohols with aromatic carboxylic acids, more specifically benzoic acid; esters of dicarboxylic acids with polyols containing 2-10 carbon atoms and 2-6 hydroxyl groups; vegetable oils; branched primary alcohols; substituted cyclohexanes; linear or branched C6-C... 22 Fatty alcohol carbonates, such as dioctyl carbonate ( CC), based on a fatty alcohol of guerbert alcohol carbonate having 6-18, preferably 8-10 carbon atoms, benzoic acid with linear and / or branched C6-C 22 Esters of alcohols (e.g.) TN), linear or branched, symmetrical or asymmetrical dialkyl ethers containing 6-22 carbon atoms per alkyl group, such as dioctyl ether (TN). OE), epoxidized fatty acids, esters of polyols, and ring-opening products of hydrocarbons, or mixtures thereof.

[0145] It should be understood that antioxidants can inhibit or prevent unwanted changes in the composition to be protected caused by oxygen effects and other oxidation processes. The effect of antioxidants in most cases lies in their function as free radical scavengers of free radicals that arise during auto-oxidation.

[0146] In a preferred embodiment, the antioxidant is selected from:

[0147] • Amino acids (such as glycine, alanine, arginine, serine, threonine, histidine, tyrosine, tryptophan) and their derivatives,

[0148] • Imidazoles (e.g., uric acid) and their derivatives,

[0149] • Peptides, such as D,L-carnosine, D-carnosine, L-carnosine (=β-alanyl-L-histidine) and their derivatives,

[0150] • Carotenoids, carotenoids (e.g., α-carotene, β-carotene, lycopene, lutein) or their derivatives,

[0151] Chlorogenic acid and its derivatives

[0152] • Lipoic acid and its derivatives (e.g., dihydrolipoic acid),

[0153] • Glucosamine, propylthiouracil, and other thiols (such as thioreductin, glutathione, cysteine, cystine, cystamine and its glycosyl, N-acetyl, methyl, ethyl, propyl, pentyl, butyl, as well as lauryl, palmitoyl, oleyl, γ-linolenic acid, cholesterol, and glyceryl esters) and their salts,

[0154] • Dilauryl thiodipropionate, distearate thiodipropionate, thiodipropionic acid and its derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts),

[0155] • Sulfonium imine compounds (e.g., butyryl sulfonium imines, homocysteine ​​sulfonium imines, butyryl sulfones, penta-, hex-, and heptyl sulfonium imines),

[0156] • (Metal) chelating agents (e.g., α-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin),

[0157] • Alpha-hydroxy acids (e.g., citric acid, lactic acid, malic acid),

[0158] • Humic acid, bile acids, bile extract, bilirubin, biliverdin, Bordeaux alkaloid (an alkaloid derived from the Bordeaux tree (Peumus boldus), Bordeaux extract),

[0159] ·EDTA, EGTA and their derivatives,

[0160] • Unsaturated fatty acids and their derivatives (e.g., gamma-linolenic acid, linoleic acid, oleic acid),

[0161] Folic acid and its derivatives

[0162] ubiquinone and ubiquinol and their derivatives,

[0163] • Vitamin C and its salts (e.g., ascorbate palmitate, magnesium ascorbate phosphate, ascorbate acetate),

[0164] • Tocopherols and halogenated compounds (e.g., vitamin E acetate),

[0165] • Vitamin A and its salts (such as vitamin A palmitate),

[0166] Benzoin gum, rutin and its derivatives, coniferyl benzoate, α-saccharyl rutin, ferulic acid, furfuryl glucosyl alcohol,

[0167] • Butylated hydroxytoluene (BHT) and butylated hydroxyanisole (BHA)

[0168] • Nordihydroguaiacol, Nordihydroguaiacol, Trihydroxyphenylbutanone, Uric acid and its derivatives, Mannose and its derivatives,

[0169] Superoxide dismutase

[0170] Zinc and its derivatives (e.g., ZnO, ZnSO4),

[0171] • Selenium and its derivatives (such as selenomethionine), and

[0172] · Classes and their derivatives (e.g., oxides) trans-oxidation )

[0173] • A mixture of two or more of the above.

[0174] In a preferred embodiment, the antioxidant is selected from pentaerythritol tetra-di-tert-butylhydroxyhydrocinnamate, nordihydroguaiaric acid, ferulic acid, resveratrol, propyl gallate, butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), ascorbyl palmitate, tocopherol, and mixtures of two or more of the above.

[0175] In yet another preferred embodiment, the composition of the present invention may contain the antioxidant in an amount of 0.001-25% by weight, preferably 0.005-10% by weight, more preferably 0.01-8% by weight, still more preferably 0.025-7% by weight, and even more preferably 0.05-5% by weight, based on the total weight of the composition.

[0176] Deodorant compositions (deodorants and antiperspirants) counteract, mask, or eliminate body odor. Body odor is formed through the action of skin bacteria during apocrine sweating, which leads to the formation of unpleasant-smelling degradation products.

[0177] Therefore, one embodiment of the present invention relates to a composition comprising a compound of formula (I) and at least one deodorizing agent. In a preferred embodiment, the deodorizing agent is selected from antiperspirants, esterase inhibitors, and antibacterial agents.

[0178] Suitable antiperspirants are selected from salts of aluminum, zirconium, or zinc. Examples include aluminum chloride, hydrated aluminum chloride, hydrated aluminum dichloride, hydrated sesquichloride, and their complexes, such as complexes with 1,2-propanediol; aluminum hydroxyallantoin; aluminum chloride tartrate; hydrated aluminum trichloride zirconium; hydrated aluminum tetrachloride zirconium; hydrated aluminum pentachloride zirconium, and their complexes, such as complexes with amino acids like glycine. Hydrated aluminum chloride, hydrated aluminum tetrachloride zirconium, hydrated aluminum pentachloride zirconium, and their complexes are preferred.

[0179] In a preferred embodiment, the antiperspirant is selected from aluminum chloride, hydrated aluminum chloride, hydrated aluminum dichloride, hydrated sesquichloride, aluminum allantoin, aluminum chloride tartrate, hydrated aluminum trichloride, hydrated aluminum tetrachloride, hydrated aluminum pentachloride, and mixtures of two or more of the above.

[0180] When sweating occurs in the armpit area, bacteria form extracellular enzymes—esterases, primarily proteases and / or lipases—that break down esters present in sweat beads, releasing odor in the process. Suitable esterase inhibitors are, for example, trialkyl citrates, such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate, and especially triethyl citrate. Esterase inhibitors suppress enzyme activity and thus reduce odor formation. Free acids may be released by the cleavage of citrate esters and lower the skin's pH to a level where the enzyme is inactivated by acylation. Other esterase inhibitors are sterol sulfates or phosphates, such as lanosterol, cholesterol, campesterol, stigmasterol, and sitosterol sulfates or phosphates; dicarboxylic acids and their esters, such as glutaric acid, monoethyl glutaric acid, diethyl glutaric acid, adipic acid, monoethyl adipic acid, diethyl adipic acid, malonic acid, and diethyl malonate; hydroxycarboxylic acids and their esters, such as citric acid, malic acid, tartaric acid, or diethyl tartaric acid; and zinc glycinate.

[0181] In a preferred embodiment, the esterase inhibitor is selected from trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate, triethyl citrate, lanosterol, cholesterol, campesterol, stigmasterol, sitosterol sulfate, sitosterol phosphate, glutaric acid, monoethyl glutarate, diethyl glutarate, adipic acid, monoethyl adipic acid, diethyl adipic acid, malonic acid, diethyl malonate, citric acid, malic acid, tartaric acid, diethyl tartarate, zinc glycinate, and mixtures of two or more of the above.

[0182] The composition of the present invention contains, based on the total weight of the composition, 0.01-20% by weight, preferably 0.1-10% by weight, and more specifically 0.5-5% by weight of the esterase inhibitor.

[0183] The term "antimicrobial agent" as used in this article includes substances that have bactericidal and / or bacteriostatic properties. These substances typically act on Gram-positive bacteria, such as 4-hydroxybenzoic acid and its salts and esters, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)urea, 2,4,4'-trichloro-2'-hydroxydiphenyl ether (triclosan), 4-chloro-3,5-dimethylphenol, 2,2'-methylenedi(6-bromo-4-chlorophenol), 3-methyl-4-(1-methylethyl)phenol, 2-benzyl-4-chlorophenol, 3-(4-chlorophenoxy)-1,2-propanediol, 3-iodo-2-propynyl butyl carbamate, chlorhexidine, 3,4,4'-trichloroaniline (TTC), phenoxyethanol, glyceryl monodecanoate, glyceryl monooctanoate, glyceryl monolaurate (GML), diglyceryl monodecanoate (DMC), and N-alkyl amides of salicylic acid such as N-octyl salicylate or N-decyl salicylate.

[0184] In a preferred embodiment, the antibacterial agent is selected from chitosan, phenoxyethanol, 5-chloro-2-(2,4-dichlorophenoxy)phenol, 4-hydroxybenzoic acid and its salts and esters, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)urea, 2,4,4'-trichloro-2'-hydroxydiphenyl ether (triclosan), 4-chloro-3,5-dimethylphenol, 2,2'-methylenebis(6-bromo-4-chlorophenol), 3-methyl-4-( 1-Methylethyl)phenol, 2-benzyl-4-chlorophenol, 3-(4-chlorophenoxy)-1,2-propanediol, 3-iodo-2-propynyl butyl carbamate, chlorhexidine, 3,4,4'-trichloroaniline (TTC), phenoxyethanol, glyceryl monodecanoate, glyceryl monooctanoate, glyceryl monolaurate (GML), diglyceryl monodecanoate (DMC), N-alkylamide of salicylic acid, and mixtures of two or more of the above.

[0185] The composition of the present invention contains the antibacterial agent in a range of 0.01-5% by weight, preferably 0.1-2% by weight, based on the total weight of the composition.

[0186] In a preferred embodiment, the composition preferably comprises a surfactant. Due to the characteristic aroma properties of the compound of formula (I) and its robustness, aroma persistence, and stability, it can be used particularly to impart a scent, preferably a fragrance effect, to compositions containing surfactants, such as detergents (especially laundry care products and general detergents). It is preferably used to impart a lasting floral and / or marine and / or green and / or sweet and / or rubbery and / or nutty and / or woody and / or gray and / or root-like and / or lemony aroma effect to compositions containing surfactants.

[0187] In a preferred embodiment, the surfactant is selected from anionic, nonionic, cationic, amphoteric, zwitterionic surfactants, and mixtures of two or more of the above. In yet another preferred embodiment, the surfactant is anionic.

[0188] Therefore, the compositions of the present invention preferably contain at least one surfactant. The surfactant may be selected from anionic, nonionic, cationic, and / or amphoteric or zwitterionic surfactants. Compositions containing surfactants, such as shower gels, foam baths, shampoos, etc., preferably contain at least one anionic surfactant.

[0189] The compositions of the present invention typically contain surfactants in an amount of 0-40% by weight, preferably 0-20% by weight, more preferably 0.1-15% by weight, and particularly 0.1-10% by weight, based on the total weight of the composition. Typical examples of nonionic surfactants are fatty alcohol polyethylene glycol ethers, alkylphenol polyethylene glycol ethers, fatty acid polyethylene glycol esters, fatty acid amide polyethylene glycol ethers, fatty amine polyethylene glycol ethers, alkoxylated triglycerides, mixed ethers and mixed formaldehydes, optionally partially oxidized alkyl (alkenyl) oligosaccharides or glucuronic acid derivatives, fatty acid N-alkyl glucamides, hydrolyzed proteins (especially wheat-based plant products), polyol fatty acid esters, glycol esters, dehydrated sorbitan esters, polysorbates, and amine oxides. If the nonionic surfactants contain polyethylene glycol ether groups, they can have a conventional homologue distribution, but they preferably have a narrow range of homologue distributions.

[0190] Amphoteric surfactants are surface-active compounds containing at least one quaternary ammonium group and at least one COO(-) or SO3(-) group in their molecules. Particularly suitable amphoteric surfactants are so-called betaines, such as N-alkyl-N,N-dimethylglycinine ammonium containing 8-18 carbon atoms in the alkyl or acyl group, for example, cocoalkyldimethylglycinine ammonium; N-acylaminopropyl-N,N-dimethylglycinine ammonium, for example, cocoylaminopropyldimethylglycinine ammonium; and 2-alkyl-3-carboxymethyl-3-hydroxyethylimidazoline derivatives, as well as cocoylaminoethylhydroxyethylcarboxymethylglycinate salts. Fatty acid amide derivatives known as cocamidopropyl betaine under the name CTFA are particularly preferred.

[0191] Amphoteric surfactants are also suitable, especially as co-surfactants. Amphoteric surfactants are those other than C8-C... 18 Surfactant compounds containing at least one free amino group and at least one -COOH or -SO3H group in the alkyl or acyl group and capable of forming an inner salt. Examples of suitable amphoteric surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkylaminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkylsarcosine, 2-alkylaminopropionic acid, and alkylaminoacetic acid, which contain about 8-18 carbon atoms in the alkyl group. Particularly preferred amphoteric surfactants are N-cocoalkylaminopropionate, cocoylaminoethyl aminopropionate, and acylsarcosine.

[0192] Anionic surfactants are characterized by water-soluble anionic groups, such as carboxyl, sulfate, sulfonate, or phosphate groups, and lipophilic groups. A large number of dermatologically safe anionic surfactants are known to professionals from relevant textbooks and are commercially available. These are especially those containing linear C... 12 -C 18 Alkyl sulfates, alkyl ether sulfates, alkyl ether carboxylates, acyl hydroxyethanesulfonates, acyl sarcosinates, acyl taurines, and sulfosuccinates and acyl glutamates in the form of their alkali metal, ammonium, or alkanol ammonium salts.

[0193] Particularly suitable cationic surfactants are quaternary ammonium compounds, preferably ammonium halides, and more particularly ammonium chloride and ammonium bromide, such as alkyltrimethylammonium chloride, dialkyldimethylammonium chloride, and trialkylmethylammonium chloride, for example cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearate dimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride, and tricetylated methylammonium chloride. In addition, readily biodegradable quaternary ester compounds, such as methyldialkylammonium sulfate and methylhydroxyalkyldialkoxyalkylammonium sulfate sold under the name Stepantexe, and... The corresponding products in this series are used as cationic surfactants. "Quaternary ammonium esters" should generally be understood as quaternized triethanolamine ester salts of fatty acids. They can provide compositions with special softening properties. They are known substances prepared by relevant methods of organic chemistry. Other cationic surfactants suitable for the uses of this invention are quaternized hydrolyzed proteins.

[0194] One embodiment of the present invention relates to a composition selected from perfume compositions, body care compositions, hygiene products, cleaning compositions, textile detergent compositions, fragrance dispenser compositions, food, food supplements, pharmaceutical compositions, and crop protection compositions.

[0195] The composition is preferably an aromatic chemical composition, and more preferably a fragrance composition.

[0196] Suitable compositions include, for example, fragrance compositions, body care compositions (including cosmetic compositions and oral and dental hygiene products), hygiene products, cleaning compositions (including dishwashing compositions), textile detergent compositions, fragrance dispenser compositions, food, food supplements, pharmaceutical compositions, and crop protection compositions.

[0197] Perfume compositions may be selected from premium perfumes, air fresheners in liquid, gel, or solid carrier form, sprays, scented cleansers, candles, and aromatherapy oils such as lamp oil or massage oil.

[0198] Examples of high-end perfumes include fragrance extracts, eau de toilette, cologne, solid perfumes, and fragrance essences.

[0199] Body care compositions include cosmetic compositions and oral and dental hygiene products, and may be selected from aftershave, pre-shave products, spray cologne, solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving creams, bath oils, oil-in-water, oil-in-water or water-in-oil-in-water cosmetic emulsions, such as skin creams and lotions, face creams and moisturizers, sunscreens and sunblocks, after-sun creams and after-sun lotions, hand creams and hand lotions, foot creams and foot lotions, depilatory creams and depilatory liquids, aftershave creams and aftershave lotions, tanning creams and tanning lotions, and hair care products. Products such as hairspray, hair gel, styling lotion, conditioner, shampoo, long-lasting and short-lasting hair dyes, hair styling compositions such as cold-setting curlers and hair smoothing compositions, styling lotions, hair creams and hair lotions, deodorants and antiperspirants such as underarm sprays, roll-on deodorants, deodorant sticks and deodorant creams, decorative cosmetic products such as eyeliner, eyeshadow, nail polish, beauty products, lipsticks and mascara, and oral and dental hygiene products such as toothpaste, dental floss, mouthwash, oral rinsing, dental foam, dental gel and dental strips.

[0200] Hygiene products can be selected from incense sticks, insecticides, insect repellents, sprays, rust removers, scented and refreshing wipes, armpit pads, baby diapers, sanitary napkins, toilet paper, cosmetic wipes, handkerchiefs, dishwashing liquid, and deodorants.

[0201] Cleaning compositions, such as solid surface cleaners, may be selected from scented acidic, alkaline, and neutral cleaners, such as floor cleaners, window cleaners, dishwashing compositions for both hand and machine washing, bathroom and hygiene cleaners, scrub milks, solid and liquid toilet cleaners, powder and foam carpet cleaners, waxes and polishes such as furniture polish, floor wax, shoe cream, disinfectants, surface disinfectants and hygiene cleaners, brake disc cleaners, pipe cleaners, limescale removers, grill and oven cleaners, algae and moss removers, mold removers, and camouflage removers.

[0202] Textile detergent compositions may be selected from liquid detergents, powder detergents, laundry pretreatment agents such as bleach, soaking agents and stain removers, fabric softeners, laundry soaps, and laundry sheets.

[0203] Food refers to raw, cooked or processed edible substances, ice, beverages or ingredients intended for or intended for human consumption in whole or in part, or chewing gum, soft candy, jelly and preserves.

[0204] Food supplements are intended-use products containing dietary components intended to further enhance the nutritional value of a diet. These dietary components can be one or any combination of the following substances: vitamins, minerals, herbal or other plant-based substances, amino acids, dietary substances intended to supplement the diet by increasing total dietary intake, concentrates, metabolites, components, or extracts. Food supplements are available in many forms such as tablets, capsules, softgels, sac-like tablets, liquids, or powders.

[0205] Pharmaceutical compositions include compositions intended for the diagnosis, cure, relief, treatment or prevention of disease, and articles (non-food) intended to affect the structure or any function of a human or other animal body.

[0206] Crop protection compositions include compositions intended to manage diseases, weeds, and other pests (both vertebrates and invertebrates) that damage crops and forestry plants.

[0207] In a preferred embodiment, the composition further comprises at least one adjuvant selected from the following: preservatives, abrasives, acne-reducing agents, anti-skin aging agents, anti-cellulite agents, anti-dandruff agents, anti-inflammatory agents, anti-irritant agents, irritation-reducing agents, astringents, antiperspirants, bactericides, antistatic agents, adhesives, buffers, carrier materials, chelating agents, cell stimulants, conditioning agents, depilatory agents, emulsifiers, enzymes, essential oils, fibers, film-forming agents, fixatives, foam-forming agents, foam stabilizers, anti-foaming substances, foaming agents, fungicides, gelling agents, gelling agents, hair care agents, styling agents, hair smoothing agents, hydrating agents, moisturizing substances, wetting substances, bleaching agents, reinforcing agents, detergents, fluorescent whitening agents, impregnating agents. Antifouling agents, friction reducers, lubricants, moisturizing creams, ointments, sunscreens, plasticizers, opacifiers, polishing agents, luminescent agents, polymers, powders, proteins, fatliquoring agents, stripping agents, polysiloxanes, skin soothing agents, cleansing agents, skin care agents, skin healing agents, skin whitening agents, skin protectants, skin softeners, coolants, skin coolants, heat absorbers, skin warming agents, stabilizers, UV absorbers, UV filters, fabric softeners, suspending agents, skin tanning agents, thickeners, vitamins, waxes, fats, phospholipids, saturated fatty acids, mono- or polyunsaturated fatty acids, α-hydroxy acids, polyhydroxy fatty acids, liquefying agents, dyes, color protectants, pigments, corrosion inhibitors, polyols, electrolytes, and polysiloxane derivatives.

[0208] mixture

[0209] One embodiment of the present invention relates to a mixture comprising at least one compound of formula (II) or a salt thereof or a stereoisomer thereof:

[0210]

[0211] in

[0212] Y is selected from -O-R1, -O(C=O)-R1 and =O;

[0213] R1 is selected from linear or branched unsubstituted C1-C5 alkyl and unsubstituted C3-C5 cycloalkyl; and at least one compound of formula (I) or a salt thereof or a stereoisomer thereof:

[0214]

[0215] in

[0216] X is selected from -OR, -O(C=O)-R and =O;

[0217] R is selected from -H, linear or branched unsubstituted -C1-C5 alkyl and unsubstituted -C3-C5 cycloalkyl.

[0218] In a preferred embodiment of the invention, the mixture comprises a compound of formula (I) wherein R is selected from -H, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)(C2H5), -CH2CH(CH3)2, -CH2CH2CH2CH3, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)CH2CH3, cyclopropyl, and cyclobutyl.

[0219] In another preferred embodiment of the invention, the mixture comprises a compound of formula (II) wherein R1 is selected from -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)(C2H5), -CH2CH(CH3)2, -CH2CH2CH2CH3, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)CH2CH3 and cyclopropyl.

[0220] In another embodiment of the invention, a mixture according to the above embodiment is used to impart an aromatic effect to the composition.

[0221] In another embodiment of the invention, the weight ratio of the compound of formula (I) to the compound of formula (II) is in the range of 99.9:0.1-0.1:99.9, preferably 90:10-10:90, and more preferably 80:20-20:80.

[0222] In another embodiment of the invention, the mixture according to the above embodiments provides an aromatic effect that evokes citrus, violet, lily of the valley, sweet, and waxy notes.

[0223] In one embodiment of the invention, a mixture of compounds of formula (I) and formula (II) is particularly preferred due to the nostalgic aromatic effect they impart.

[0224] In another embodiment of the invention, the composition comprises:

[0225] (i) the mixture according to any of the above embodiments, and

[0226] (ii) at least one aromatic chemical that is different from formula (I) and formula (II), or

[0227] (iii) at least one non-aromatic chemical carrier, or

[0228] (iv)(ii) and (iii) both.

[0229] compound

[0230] One embodiment of the present invention relates to a compound of formula (I') or a salt thereof or a stereoisomer thereof:

[0231]

[0232] in

[0233] X is selected from -OR a and -O(C=O)-R b ;

[0234] R a Selected from linear or branched unsubstituted C2-C5 alkyl and unsubstituted C3-C5 cycloalkyl;

[0235] R b Selected from linear or branched unsubstituted C1-C5 alkyl and unsubstituted C3-C5 cycloalkyl.

[0236] In the preferred embodiment, X is -OR a .

[0237] In another preferred embodiment, X is -O(C=O)-R b .

[0238] In the preferred embodiment, R a Selected from -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)(C2H5), -CH2CH(CH3)2, -CH2CH2CH2CH3, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)CH2CH3, cyclopropyl and cyclobutyl.

[0239] In the preferred embodiment, R b Selected from -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)(C2H5), -CH2CH(CH3)2, -CH2CH2CH2CH3, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)CH2CH3, cyclopropyl and cyclobutyl.

[0240] Implementation Plan

[0241] Further examples of embodiments of this disclosure are provided below, but it is not intended to limit this disclosure to the specific embodiments listed below.

[0242] 1. Use of at least one compound of formula (I) or its salt or its stereoisomer to impart an aromatic effect to a composition:

[0243]

[0244] in

[0245] X is selected from -OR, -O(C=O)-R and =O;

[0246] R is selected from -H, linear or branched unsubstituted -C1-C5 alkyl and unsubstituted -C3-C5 cycloalkyl.

[0247] 2. A method for imparting an aromatic effect to a composition, comprising at least the step of adding at least one compound of formula (I) or a salt thereof or a stereoisomer thereof to the composition:

[0248]

[0249] in

[0250] X is selected from -OR, -O(C=O)-R and =O;

[0251] R is selected from -H, linear or branched unsubstituted -C1-C5 alkyl and unsubstituted -C3-C5 cycloalkyl.

[0252] 3. According to the purpose or method of implementation scheme 1 or 2, where X is -OR.

[0253] 4. According to the purpose or method of implementation scheme 1 or 2, where X is -O(C=O)-R.

[0254] 5. The use or method according to any of the foregoing embodiments, wherein R is selected from -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)(C2H5), -CH2CH(CH3)2, -CH2CH2CH2CH3, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -CH(CH3)CH2CH3, cyclopropyl and cyclobutyl.

[0255] 6. The use or method according to any of the foregoing embodiments, wherein the composition is selected from perfume compositions, body care compositions, hygiene products, cleaning compositions, textile detergent compositions, fragrance dispenser compositions, food, food supplements, pharmaceutical compositions, or crop protection compositions.

[0256] 7. The use or method according to any of the foregoing embodiments, wherein the effect is selected from carrot, chocolate, herbal, waxy, woody, citrus, lily of the valley, aquatic, soapy, floral, grapefruit-like, sweet, and musty notes.

[0257] 8. The use or method according to any of the foregoing embodiments, wherein the compound of formula (I) or its salt or stereoisomer is present in an amount ranging from ≥0.01% by weight to ≤70.0% by weight based on the total weight of the composition.

[0258] 9. A composition comprising at least one compound of formula (I) or a salt thereof or a stereoisomer thereof:

[0259]

[0260] in

[0261] X is selected from -OR, -O(C=O)-R and =O;

[0262] R is selected from -H, linear or branched unsubstituted -C1-C5 alkyl and unsubstituted -C3-C5 cycloalkyl;

[0263] as well as

[0264] (i) at least one aromatic chemical different from formula (I), or

[0265] (ii) at least one non-aromatic chemical carrier, or

[0266] (iii)(i) and (ii) both.

[0267] 10. The composition according to embodiment 9, wherein X is -OR.

[0268] 11. The composition according to embodiment 9, wherein X is -O(C=O)-R.

[0269] 12. The composition according to any one of embodiments 9-11, wherein R is selected from -H, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)(C2H5), -CH2CH(CH3)2, -CH2CH2CH2CH3, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)CH2CH3, cyclopropyl and cyclobutyl.

[0270] 13. The composition according to any one of embodiments 9-12, wherein the at least one non-aromatic chemical carrier (ii) is selected from surfactants, oil components, antioxidants, deodorizing agents, solvents, and mixtures of two or more of the above.

[0271] 14. A composition according to any one of embodiments 9-13, wherein the composition is selected from perfume compositions, body care compositions, hygiene products, cleaning compositions, textile detergent compositions, fragrance dispenser compositions, food, food supplements, pharmaceutical compositions or crop protection compositions.

[0272] 15. Compounds of formula (I') or their salts or stereoisomers:

[0273]

[0274] in

[0275] X is selected from -OR a and -O(C=O)-R b ;

[0276] R a Selected from linear or branched unsubstituted C2-C5 alkyl and unsubstituted C3-C5 cycloalkyl;

[0277] R b Selected from linear or branched unsubstituted C1-C5 alkyl and unsubstituted C3-C5 cycloalkyl.

[0278] 16. The compound according to embodiment 15, wherein X is -OR a .

[0279] 17. The compound according to embodiment 15, wherein X is -O(C=O)-R b .

[0280] 18. A compound according to any one of embodiments 15-17 above, wherein R a Selected from -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)(C2H5), -CH2CH(CH3)2, -CH2CH2CH2CH3, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)CH2CH3, cyclopropyl and cyclobutyl.

[0281] 19. A compound according to any one of embodiments 15-17 above, wherein R b Selected from -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)(C2H5), -CH2CH(CH3)2, -CH2CH2CH2CH3, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)CH2CH3, cyclopropyl and cyclobutyl.

[0282] 20. A mixture comprising at least one compound of formula (II) or a salt thereof or a stereoisomer thereof:

[0283]

[0284] in

[0285] Y is selected from -O-R1, -O(C=O)-R1 and =O;

[0286] R1 is selected from linear or branched unsubstituted C1-C5 alkyl and unsubstituted C3-C5 cycloalkyl; and at least one compound of formula (I) or a salt thereof or a stereoisomer thereof:

[0287]

[0288] in

[0289] X is selected from -OR, -O(C=O)-R and =O;

[0290] R is selected from -H, linear or branched unsubstituted -C1-C5 alkyl and unsubstituted -C3-C5 cycloalkyl.

[0291] 21. The mixture according to embodiment 20, wherein R1 is selected from -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)(C2H5), -CH2CH(CH3)2, -CH2CH2CH2CH3, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)CH2CH3 and cyclopropyl.

[0292] 22. The mixture according to embodiment 20, wherein R is selected from -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)(C2H5), -CH2CH(CH3)2, -CH2CH2CH2CH3, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)CH2CH3, cyclopropyl and cyclobutyl.

[0293] 23. Use of a mixture according to any one of embodiments 20-22 to impart an aromatic effect to the composition.

[0294] 24. A composition comprising:

[0295] (i) a mixture according to any one of embodiments 20-22, and

[0296] (ii) at least one aromatic chemical that is different from formula (I) and formula (II), or

[0297] (iii) at least one non-aromatic chemical carrier, or

[0298] (iv)(i) and (ii) both. Example

[0299] The present invention is described in detail by the following non-limiting working embodiments. More specifically, the test methods described below are part of the general disclosure of this application and are not limited to the specific working embodiments.

[0300] Analysis method:

[0301] Characterization by 13 The C-NMR was performed. 13 C-NMR spectra were measured on a Bruker DPX-500 spectrophotometer.

[0302] Product purity determination:

[0303] The purity of the product was determined by gas chromatography (area %).

[0304] GC system: Agilent 6890N;

[0305] GC column: DB-WAX: 30m (length), 0.32mm (inner diameter), 0.25 micrometers (film thickness);

[0306] Temperature program: from 50°C to 200°C at 5° / min, held at 200°C for 17 min, total run time: 47 minutes.

[0307] Example 1:

[0308] Step 1: Synthesis of acetophenone derivative 1: Preparation of 1-(3-isobutylphenyl)acetophenone

[0309]

[0310] In a reaction vessel, 2-isobutyl-6-methyl-1,3,6,2-boronate diethanolamine ester-4,8-dione (=(2-methylpropyl)boronate MIDA ester, 100%, 20 g, 0.94 mol, 1.1 eq) and 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloromethane dichloride complex (PdCl2(ddpf)*CH2Cl2, 100%, 6.98 g, 0.008 mol, 0.1 eq), tetrahydrofuran (85 mL), 3'-bromoacetophenone (100%, 17 g, 0.85 mol, 1 eq.), and water (17 mL) were added. The mixture was stirred at room temperature for 5 minutes. Then, over 5 minutes, potassium carbonate (70.82 g, 0.512 mol, 6 eq) was added to the mixture, followed by tetrahydrofuran (30 mL). The reaction mixture was stirred at 65 °C for 32 hours, then allowed to reach room temperature. 100 mL of tert-butyl methyl ether and 150 mL of water were added to the reaction mixture, and the mixture was stirred for another 25 minutes. The phases were separated, and the aqueous phase was extracted twice more with tert-butyl methyl ether (100 mL each time). The combined organic phases were dried over sodium sulfate and filtered. The organic solvent was removed under reduced pressure to give 20 g of the desired crude product. After column chromatography (cyclohexane:ethyl acetate), 6.9 g of 1-(3-isobutylphenyl)ethyl ketone was obtained as a clear liquid.

[0311] After purification, the purity was 99.7 GC area at a total yield of 55%.

[0312] 1 ¹H-NMR (500MHz, chloroform-d) δ 7.78 (dt, J = 7.0, 1.8 Hz, 1H), 7.75 (s, 1H), 7.42–7.33 (m, 2H), 2.61 (s, 3H), 2.54 (d, J = 7.2 Hz, 2H), 1.95–1.9 (m, 1H), 0.91 (d, J = 6.6, Hz, 6H).

[0313] 13 C-NMR (126MHz, CDCl3) δ198.55, 142.21, 137.02, 133.98, 128.78, 128.30, 125.96, 45.19, 30.22, 26.73, 22.29, 22.28.

[0314] Step 2: Synthesis of the corresponding alcohol: Preparation of 1-(3-isobutylphenyl)ethanol

[0315]

[0316] In a reaction vessel, 1-(3-isobutylphenyl)ethyl ketone (99.7 GC area%, 6 g, 34 mmol, 1 eq) obtained in step 1 was stirred at room temperature. Sodium borohydride (1.42 g, 37.5 mmol, 1.1 eq) was added dropwise over 5 minutes. The reaction mixture was stirred at room temperature for 2 hours. Water (15 mL) and ethyl acetate (30 mL) were added to the reaction mixture. The solvent was removed under reduced pressure, resulting in phase separation from the solid residue. Water (20 mL) and ethyl acetate (15 mL) were added to the solid residue. The phases were separated, and the aqueous phase was extracted twice with ethyl acetate (15 mL each time). The combined organic phases were dried over sodium sulfate and filtered to remove the organic solvent under reduced pressure, yielding 5.8 g of the desired product as a clear liquid.

[0317] The purity was 98.4 GC area% (0.33 GC area% of the raw material) at a total yield of 94%.

[0318] 13 C-NMR (126MHz, CDCl3) δ145.59, 141.97, 128.27, 128.20, 126.14, 122.68, 70.46, 45.44, 30.23, 25.14, 22.40, 22.38.

[0319] 1 ¹H-NMR (500 MHz, chloroform-d) δ 7.27–7.22 (m., 1H), 7.18 (d, J = 7.7 Hz, 1H), 7.15 (s, 1H), 7.05 (d, J = 7.5 Hz, 1H), 4.86 (q, J = 6.5 Hz, 1H), 2.47 (d, J = 7.2 Hz, 2H), 1.92–1.80 (m, 1H), 1.48 (d, J = 6.5 Hz, 3H), 0.90 (d, J = 6.7 Hz, 6H). Step 3: Synthesis of the corresponding ether: Preparation of 1-(1-ethoxyethyl)-3-isobutylbenzene (R = Et)

[0320]

[0321] Anhydrous ethanol (3.05 g, 66.2 mmol, 3 eq.) and 1-(3-isobutylphenyl)ethanol (98.4 GC area%, 4 g, 22 mmol, 1 eq.) obtained in step 2 were mixed in a reaction vessel. Methanesulfonic acid (149 mg, 1.55 mmol, 0.07 eq.) was added, and the mixture was refluxed (78 °C). After reflux for 23.5 h, the reaction mixture was cooled to room temperature, and 2 g of saturated NaHCO3 solution was added. The solvent was further removed under reduced pressure (180–90 mbar) and at 60 °C, and the two phases were separated. The upper organic phase was subjected to silica gel column chromatography and eluted with cyclohexane:ethyl acetate to give 0.6 g of the desired crude product with a purity of 98.9 GC area%.

[0322] 13 C-NMR (176MHz, CDCl3) δ143.93, 141.79, 128.11, 128.07, 126.85, 123.50, 77.82, 63.83, 45.45, 30.25, 24.29, 22.39, 22.35, 15.42.

[0323] 1 H-NMR (700MHz, chloroform-d) δ7.27-7.21 (m, 1H), 7.12 (d, J=7.6Hz, 1H), 7.09 (s, 1H), 7.04 (d, J=7.5Hz, 1H), 4.37 (q, J=6.5Hz, 1H), 3.35 (q, J=7 .0Hz, 2H), 2.48 (d, J=7.2Hz, 2H), 1.85 (d, J=13.5, 6.8Hz, 1H), 1.43 (d, J=6.6Hz, 3H), 1.18 (t, J=7.0Hz, 3H), 0.90 (dd, J=6.7, 2.2Hz, 6H).

[0324] Example 2

[0325] Replacing anhydrous ethanol with anhydrous methanol in step 3 results in the formation of 1-(1-methoxyethyl)-3-isobutylbenzene.

[0326] Example 3

[0327] In step 3, replacing anhydrous ethanol with anhydrous isopropanol results in the formation of 1-(1-propoxyethyl)-3-isobutylbenzene.

[0328] Table 1—Aromatic effects of compounds or mixtures of formula (I)

[0329]

[0330] Compound A = any compound or mixture according to Table 1

[0331] Advantageous spice composition

[0332] Compound A as described above was formulated in the compositions according to Tables 2 and 3. The amounts given in Tables 2 and 3 are in grams by weight.

[0333] Table 2: Fragrance Compositions 1A and 1B

[0334]

[0335]

[0336] Table 3: Fragrance Compositions 2A and 2B

[0337]

[0338]

[0339] The compositions according to Tables 2 and 3, namely 1A, 1B, 2A, and 2B, may be included in a variety of compositions selected from deodorant pump sprays, cleansing conditioners, facial cleansing gels, foam bath concentrates, hair gels, self-foaming shower gels, spray sunscreen lotions, spray sun protection lotions, moisturizing gels, two-phase oil foam baths, shampoos, shower gels, hydroalcohol AP / deodorant pump sprays, aerosols, hydroalcohol AP / roll-on deodorants, "get-out-of-bed" hair gels, styling creams, baby shampoos for sensitive skin, body washes for sensitive skin, shine-enhancing shampoos for sensitive scalps, deodorant sticks, baby wipes, aftershave balms, face creams, daily face creams, facial cleansers, colognes, sunscreens SPF50+, spray washes, hand dishwashing detergents - standard, hand dishwashing detergents - concentrate, hygienic cleaners - concentrate, general-purpose cleaners, antibacterial fabric softeners, detergent compositions, powder detergent compositions, and liquid detergent compositions.

[0340] Those skilled in the art are likely well aware of the various generic formulations of the above-mentioned products.

[0341] Compositions 1A, 1B, 2A, and 2B can be formulated, for example, with the specific formulation disclosed in Table 1-D13, IPCOM000258614D, on pages 6-46 of IP.com entitled “Novel Aromatic Chemicals”, wherein “fragrance composition 1A” is replaced by the same amount of composition 1A, 1B, 2A, or 2B.

Claims

1. Use of at least one compound of formula (I) or its salt or its stereoisomer to impart an aromatic effect to a composition: in X is selected from -OR, -O(C=O)-R and =O; R is selected from -H, linear or branched unsubstituted -C1-C5 alkyl and unsubstituted -C3-C5 cycloalkyl.

2. The use according to claim 1, wherein X is -OR.

3. The use according to claim 1, wherein X is -O(C=O)-R.

4. The use according to any one of claims 1-3, wherein R is selected from -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)(C2H5), -CH2CH(CH3)2, -CH2CH2CH2CH3, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -CH(CH3)CH2CH3, cyclopropyl and cyclobutyl.

5. The use according to any one of claims 1-3, wherein the composition is selected from perfume compositions, body care compositions, hygiene products, cleaning compositions, fragrance dispenser compositions, food, food supplements, pharmaceutical compositions, or crop protection compositions.

6. The use according to claim 5, wherein the composition is selected from textile detergent compositions.

7. The use according to any one of claims 1-3, wherein the aromatic effect is selected from carrot, chocolate, herbal, waxy, woody, citrus, aquatic, soapy, floral, grapefruit-like, sweet, and musty notes.

8. The use according to claim 7, wherein the aromatic effect is selected from lily of the valley fragrance.

9. Use according to any one of claims 1-3, wherein the compound of formula (I) or its salt or stereoisomer is present in an amount ranging from ≥0.01% by weight to ≤70.0% by weight based on the total weight of the composition.

10. A method for imparting an aromatic effect to a composition, comprising at least the step of adding at least one compound of formula (I) or a salt thereof or a stereoisomer thereof to the composition: in X is selected from -OR, -O(C=O)-R and =O; R is selected from -H, linear or branched unsubstituted -C1-C5 alkyl and unsubstituted -C3-C5 cycloalkyl.

11. The method of claim 10, wherein X is -OR.

12. The method of claim 10, wherein X is -O(C=O)-R.

13. The method according to any one of claims 10-12, wherein R is selected from -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)(C2H5), -CH2CH(CH3)2, -CH2CH2CH2CH3, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -CH(CH3)CH2CH3, cyclopropyl, and cyclobutyl.

14. The method according to any one of claims 10-12, wherein the composition is selected from perfume compositions, body care compositions, hygiene products, cleaning compositions, fragrance dispenser compositions, food, food supplements, pharmaceutical compositions, or crop protection compositions.

15. The method of claim 14, wherein the composition is selected from textile detergent compositions.

16. The method according to any one of claims 10-12, wherein the aromatic effect is selected from carrot, chocolate, herbal, waxy, woody, citrus, aquatic, soapy, floral, grapefruit-like, sweet, and musty notes.

17. The method of claim 16, wherein the aromatic effect is selected from the lily of the valley fragrance family.

18. The method according to any one of claims 10-12, wherein the compound of formula (I) or its salt or stereoisomer is present in an amount ranging from ≥0.01% by weight to ≤70.0% by weight based on the total weight of the composition.

19. A composition comprising at least one compound of formula (I) or a salt thereof or a stereoisomer thereof: in X is selected from -OR, -O(C=O)-R and =O; R is selected from -H, linear or branched unsubstituted -C1-C5 alkyl and unsubstituted -C3-C5 cycloalkyl; and (i) at least one aromatic chemical different from formula (I), or (ii) at least one non-aromatic chemical carrier, or (iii)(i) and (ii) both.

20. The composition of claim 19, wherein X is -OR.

21. The composition according to claim 19, wherein X is -O(C=O)-R.

22. The composition according to any one of claims 19-21, wherein R is selected from -H, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)(C2H5), -CH2CH(CH3)2, -CH2CH2CH2CH3, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)CH2CH3, cyclopropyl, and cyclobutyl.

23. The composition according to any one of claims 19-21, wherein the at least one non-aromatic chemical carrier (ii) is selected from surfactants, oil components, antioxidants, deodorizing agents, solvents, and mixtures of two or more of the above.

24. The composition according to any one of claims 19-21, wherein the composition is selected from perfume compositions, body care compositions, hygiene products, cleaning compositions, fragrance dispenser compositions, food, food supplements, pharmaceutical compositions or crop protection compositions.

25. Compound of formula (I') or its salt or its stereoisomer: in X is selected from -OR a and -O(C=O)-R b ; R a Selected from linear or branched unsubstituted C2-C5 alkyl and unsubstituted C3-C5 cycloalkyl; R b Selected from linear or branched unsubstituted C1-C5 alkyl and unsubstituted C3-C5 cycloalkyl.

26. The compound of claim 25, wherein X is -OR a .

27. The compound of claim 25, wherein X is -O(C=O)-R b .

28. The compound according to any one of claims 25-27, wherein R a Selected from -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)(C2H5), -CH2CH(CH3)2, -CH2CH2CH2CH3, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)CH2CH3, cyclopropyl and cyclobutyl.

29. The compound according to any one of claims 25-27, wherein R b Selected from -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)(C2H5), -CH2CH(CH3)2, -CH2CH2CH2CH3, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)CH2CH3, cyclopropyl and cyclobutyl.

30. A mixture comprising at least one compound of formula (II) or a salt thereof or a stereoisomer thereof: in Y is selected from -O-R1, -O(C=O)-R1 and =O; R1 is selected from linear or branched unsubstituted C1-C5 alkyl and unsubstituted C3-C5 cycloalkyl; and at least one compound of formula (I) or a salt thereof or a stereoisomer thereof: in X is selected from -OR, -O(C=O)-R and =O; R is selected from -H, linear or branched unsubstituted -C1-C5 alkyl and unsubstituted -C3-C5 cycloalkyl.

31. The mixture according to claim 30, wherein R1 is selected from -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)(C2H5), -CH2CH(CH3)2, -CH2CH2CH2CH3, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)CH2CH3 and cyclopropyl.

32. The mixture according to claim 30, wherein R is selected from -H, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH(CH3)(C2H5), -CH2CH(CH3)2, -CH2CH2CH2CH3, -CH(CH3)2, -CH2CH(CH3)2, -CH(CH3)CH2CH3, cyclopropyl and cyclobutyl.

33. Use of the mixture according to any one of claims 30-32 to impart an aromatic effect to the composition.

34. A composition comprising: (i) a mixture according to any one of claims 30-32, and (ii) at least one aromatic chemical that is different from formula (I) and formula (II), or (iii) at least one non-aromatic chemical carrier, or (iv)(i) and (ii) both.

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