2,3,6-TRIMETHYLCYCLOHEXANOL AS AN ODORBING AND / OR AROMATING SUBSTANCE
Patent Information
- Application Number
- DE502017016824
- Authority / Receiving Office
- DE · DE
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2017-03-21
- Filing Date
- 2017-11-27
- Publication Date
- 2025-05-22
- Estimated Expiration
- 2037-11-27
AI Technical Summary
The perfume and aroma industry faces a need for new smell and aroma substances that can generate interesting notes beyond primary fragrance/taste notes, expanding the possibilities for perfumers and flavorists with original olfactory properties, particularly in harmonious combinations with floral and fruity substances.
Utilization of 2,3,6-trimethylcyclohexanol as a smell and aroma compound to convey, modify, and reinforce odor and flavor notes such as green, woody, animal, earthy, fruity, floral, and leather notes, offering complex and original sensory profiles.
The use of 2,3,6-trimethylcyclohexanol provides a complex and diverse smell and taste impression, enhancing the stability and naturalness of aroma compositions, and offering a booster effect to intensify fragrance mixtures while maintaining biodegradability.
Description
[0001] The present invention primarily relates to the use of 2,3,6-trimethylcyclohexanol, i.e., a compound of formula (I) as described herein, as a fragrance and / or flavoring agent for imparting, modifying, and / or enhancing one or more odor and / or flavor notes as described herein. The invention also relates to novel fragrance and / or flavoring compositions comprising the compound of formula (I) as described herein, perfumed and / or flavored articles comprising the compound of formula (I) as described herein, and various methods for imparting, modifying, and / or enhancing certain odor and / or flavor notes.
[0002] Further aspects and preferred embodiments of the present invention will become apparent from the following explanations, the attached examples and in particular the attached patent claims.
[0003] Despite a multitude of existing fragrances and / or aromas, there is still a general need for new fragrances and / or aromas in the perfume and aroma industry. For example, there is a need for fragrances and / or aromas that are capable of creating additional interesting notes (in fragrance and / or aroma compositions) in addition to a primary fragrance / flavor note, and that, with their novel or original olfactory properties, expand the options available to perfumers and flavorists. There is particular interest in fragrances with notes that are capable of harmoniously combining with floral and / or fruity fragrances. The preferred approach is to layer the different olfactory aspects and notes to create an overall complex olfactory impression.
[0004] For the creation of novel compositions, there is a constant demand for fragrances and / or aromas with special sensory properties that are suitable for serving as the basis for the composition of novel perfumes or aromas with complex sensory characteristics. Preferred fragrances and / or aromas should, in addition to a specific note, exhibit additional notes and aspects that lend them character and complexity.
[0005] The search for suitable substances, which led to the present invention, was complicated by the following facts: The mechanisms of olfactory perception are not sufficiently known; the relationships between the specific olfactory perception on the one hand and the chemical structure of the corresponding odorant on the other hand have not been sufficiently researched; often even minor changes in the structural composition of a known odorant cause significant changes in the sensory properties and impair its tolerance to the human organism.
[0006] The primary task was now to find fragrances and / or flavorings that have an interesting, preferably complex, and original sensory profile and are suitable as fragrances for use in, for example, perfumery or as flavorings for flavoring, for example, edible preparations.
[0007] Within the scope of the present invention, substances were particularly sought which have or can convey, modify and / or intensify one, several or all of the notes green, woody, animalic, earthy, amber, fruity, floral and leather notes.
[0008] The sought-after substances should enable the production of novel fragrance and / or flavor compositions with distinctive odor and / or flavor notes and aspects. Advantageous would be those substances that are particularly suitable for combination with other fragrances or flavors that exhibit woody, animalic, earthy, and amber notes.
[0009] In addition, the fragrances and / or flavorings fulfilling this primary task should preferably have additional positive secondary properties beyond their primary, namely olfactory or taste-related, properties, such as high stability under certain application conditions, high yield, good adhesion, high substantivity or odor and / or taste-enhancing properties (so-called booster or enhancer effect), and / or in combination with other fragrances and / or flavorings, round off their naturalness, freshness, fullness, (radiance) power and / or charisma, so that sensory remarkable effects can be achieved.
[0010] DE 2317000 by Wilkinson Sword Ltd. relates to ingestible, topical, and other compositions with a physiological cooling effect on the skin and mucous membranes of the body, particularly the mucous membranes of the nose and respiratory tract. 2,3,6-Trimethylcyclohexanol is not disclosed in DE 2317000.
[0011] DE 3003518 concerns the use of 1-ethyl-2,2,6-trimethyl-cyclohexanol as a perfume and aroma ingredient.
[0012] JP S50 22548B discloses a process for producing 2,3,6-trimethylcyclohexanol starting from 2,3,6-trimethylphenol. The odor properties of the substances or mixtures used or obtained are not mentioned.
[0013] According to the invention, the primary object is achieved by using the compound of formula (I) (2,3,6-trimethylcyclohexanol, CAS No. 58210-03-0) as a fragrance and / or flavoring substance for imparting, modifying and / or enhancing one or more odor and / or flavor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalic, sweet, earthy, amber, fatty, metallic, balsamic, leather note and chlorine note, preferably one or more of the odor and / or flavor notes selected from the group consisting of the notes green, woody, animalic, earthy, amber, fruity, floral, leather note and chlorine note.
[0014] The compound of formula (I) to be used according to the invention can exist as any stereoisomer and thus also in any optically active form. Within the scope of the present invention, any mixtures of stereoisomers of the compound of formula (I) can also be used, for example a diastereomer mixture, enantiomer mixture, or a racemate. That is, the term "compound of formula (I)" in this text also includes any mixtures of different stereoisomers of the compound of formula (I).
[0015] What has been said herein for a compound of formula (I), in particular the advantages described herein, also apply to a mixture of stereoisomers of the compound of formula (I) to be used or employed according to the invention (see above).
[0016] The compound of formula (I) possesses unique olfactory properties that clearly distinguish and even surpass known fragrances and / or aromas. The suitability of the compound of formula (I) as a fragrance and / or aroma substance was previously unknown. It is therefore particularly surprising that, in this already well-researched field, a fragrance and / or aroma substance with valuable, interesting, and complex olfactory properties could be discovered.
[0017] The use according to the invention preferably relates to a use for imparting, modifying and / or enhancing one or more odor and / or taste notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalic, sweet, earthy, amber, fatty, metallic, balsamic and leather note, preferably one or more of the odor and / or taste notes selected from the group consisting of the notes green, woody, animalic, earthy, amber, fruity, floral and leather note.
[0018] A preferred embodiment relates to the use of the compound of formula (I) for imparting one, two or more olfactory and / or taste notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, sweet, earthy, fatty, metallic and balsamic.
[0019] A further preferred embodiment relates to the use of the compound of formula (I) for imparting a green and / or fruity, preferably a green and fruity, preferably a pineapple-like, odor and / or taste note and additionally one, two or more odor and / or taste notes selected from the group consisting of the notes herbaceous, fresh, floral, woody, sweet, earthy, fatty, metallic and balsamic.
[0020] The fact that the compound of formula (I) to be used according to the invention may impart a very complex and diverse olfactory and taste impression, which can otherwise usually only be achieved by mixtures of several components (such as essential oils or spice mixtures), is particularly surprising.
[0021] In addition to the primary, namely olfactory and gustatory, properties, the compound of formula (I) also has positive secondary properties, in particular good adhesion and high substantivity compared to fragrances with similar olfactory properties, as well as high stability in certain media and preparations and high yield, and is also biodegradable.
[0022] The compound of formula (I) to be used according to the invention exhibits high, exceptional stability, particularly in largely neutral, but especially in alkaline and / or oxidizing media. These properties in particular make the compound of formula (I) eminently suitable for use as a fragrance and / or flavoring agent, particularly when used in perfumed or flavored articles (preparations) that have a pH of 5.5 or greater, preferably greater than or equal to 6, preferably greater than 7, more preferably greater than 7.5, and particularly preferably greater than 8; furthermore, in oxidizing preparations that preferably have a pH of greater than or equal to 7, preferably in oxidizing preparations with a pH of greater than or equal to 8. The pH values stated refer in each case to values measured at 25°C.
[0023] The compound of formula (I) to be used according to the invention can advantageously enhance the intensity of an odoriferous or aromatic substance mixture (odoriferous and / or aromatic substance composition) and round off the overall odor and / or flavor of the mixture and can be used to impart more fullness, freshness, (radiant) power, radiance, shine, roundness, harmony and / or naturalness to an odoriferous and / or aromatic substance composition.
[0024] Furthermore, the compound of formula (I) is suitable as an agent for increasing the substantivity and / or retention of an odoriferous and / or aromatic substance mixture and / or as a fixative.
[0025] If inadvertently a discrepancy should occur in this text between the chemical name and the structural formula shown of the compound of formula (I), the structural formula shown shall prevail.
[0026] Advantageously, the compound of formula (I) to be used according to the invention also exhibits sensory properties of the ocimene type and has a chloro-skatole note.
[0027] Due to the chlorine-skatole note, the compound of formula (I) is suitable, among other things, as a signaling substance in antibacterial applications.
[0028] A further preferred embodiment therefore relates to the use of the compound of formula (I) for imparting, modifying and / or enhancing the odor and / or taste note of chlorine.
[0029] In many countries, a chlorine-like odor or taste note, in particular an olfactory note, is associated with the impression of cleanliness, hygiene and antibacterial properties. The use according to the invention is particularly advantageous for this reason, since it can convey, modify and / or intensify a chlorine note without chlorine actually having to be added to the fragrance and / or aroma compositions according to the invention or to perfumed and / or flavored articles (as described further below) containing the compound of the formula (I), or more advantageously, these can have a much lower actual chlorine content, which without the odor enhancement by the compound of the formula (I) would under certain circumstances not be detectable by the senses. This chlorine signaling effect of the compound of the formula (I), i.e. conveying the impression that a fragrance and / or aroma composition according to the invention orA perfumed and / or flavored article according to the invention (as described below) is or has a particularly clean, hygienic and / or antibacterial effect due to its sensorially perceptible chlorine note, is particularly popular with many consumers and can be used particularly advantageously in oral care products, such as mouthwashes and dental care products, and surface cleaners, such as toilet cleaners and all-purpose cleaners.
[0030] The compound of formula (I) is already known from the literature (see, for example, WO2010122178, WO2014198602, WO2010097479, EP2389922, EP50229, and US20110294876). However, its sensory properties and suitability as a fragrance and / or flavoring agent are not described in the prior art.
[0031] The compound of formula (I) to be used according to the invention can be prepared using conventional reactions and processes. For example, the corresponding phenol (CAS No. 2416-94-6) or a corresponding ketone (e.g., CAS No. 20030-30-2) can be hydrogenated to the compound of formula (I) using appropriate catalysts and under appropriate conditions (the starting materials used for this purpose are commercially available):
[0032] Preparation of the compound of formula (I) from the corresponding phenol (above) or a corresponding ketone (below) by hydrogenation
[0033] The compound of formula (I) to be used according to the invention is usually used in a sensorially effective amount within the scope of the inventive use, i.e. in a total amount in which it exerts a sensory effect. The compound of formula (I) to be used according to the invention is preferably used together with other fragrances and / or flavorings. Such fragrance and / or flavoring compositions can be prepared in the usual way, for example by simply mixing or homogenizing the components. These further fragrances and / or flavorings can be any desired other fragrances and / or flavorings (preferred combinations are set out below).
[0034] A further aspect of the present invention therefore relates to a fragrance and / or aroma composition comprising or consisting of the compound of formula (I) and one, two, three, four, five, six, seven, eight, nine, ten or more further fragrance and / or flavoring substance(s), wherein the weight ratio of the total amount of compound of formula (I) to the total amount of further fragrance and / or flavoring substance(s) is in the range from 1:1000 to 1:0.1, preferably from 1:1000 to 1:0.5, and wherein the total amount of compound of formula (I) is contained in the fragrance and / or flavoring composition in an amount sufficient to produce one or more fragrance and / or flavor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalic, sweet, earthy, amber, greasy, metallic, balsamic, leather note and chlorine note, preferably at least one of the fragrance and / or flavor notes selected from the group consisting of the notes green, woody, animalic, earthy, amber, fruity, floral, leather note and chlorine note,to impart and / or intensify and / or modify one or more odor and / or taste notes of one or more of the other odor and / or flavor substances of the odor and / or flavor composition in the direction of one or more of these odor and / or taste notes.
[0035] It is preferred if the total amount of compound of formula (I), based on the total weight of the fragrance and / or aroma composition, is in the range from 0.0001 to 90% by weight, preferably 0.05 to 80% by weight, 0.1 to 70% by weight, 0.25 to 50% by weight, 0.5 to 40% by weight or 0.75 to 25% by weight.
[0036] If the compound of formula (I) is primarily used to impart more freshness, radiance, roundness, harmony and / or naturalness to a fragrance and / or aroma composition and / or to enhance certain notes (already present due to other fragrances and / or aromas), the total amount of the compound of formula (I) can also be selected to be comparatively low and, for example, preferably in the range of 0.01 to 5 wt.%, more preferably in the range of 0.1 to 2 wt.%, based on the total amount of the fragrance and / or aroma composition. If a comparatively low concentration is selected within the preferred concentration ranges, depending on the other components of the respective composition, the inherent odor and / or flavor notes stated herein may not yet be imparted in individual cases.Thus, depending on the desired effect of the compound of formula (I), the skilled person can select a suitable amount of compound of formula (I) for the particular application.
[0037] Due to its olfactory properties, the compound of formula (I) is ideally suited for use in fragrance and / or aroma compositions according to the invention. The compound of formula (I) can advantageously be combined with a variety of other fragrances or aromas and used in numerous different products and articles.
[0038] Preferably, for a fragrance and / or aroma composition according to the invention, the total amount of compound of formula (I) is present in the fragrance and / or aroma composition in a sensorially effective amount, preferably in an amount sufficient to impart and / or intensify one or more odor and / or taste notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalic, sweet, earthy, amber, fatty, metallic, balsamic and leather note, preferably at least one of the odor and / or taste notes selected from the group consisting of the notes green, woody, animalic, earthy, amber, fruity, floral and leather note, preferably consisting of green and fruity, more preferably a leather note, and / or to impart and / or intensify one or more odor and / or taste notes of one or moreof the further odoriferous and / or aromatic substance(s) of the odoriferous and / or aromatic substance composition in the direction of one or more of these odor and / or flavor notes.
[0039] It is particularly preferred if (i) the or one, several or all of the further fragrance and / or aroma substances (likewise) impart, modify and / or intensify one or more odor and / or taste notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalic, sweet, earthy, amber, fatty, metallic, balsamic and leather note, preferably one or more of the odor and / or taste notes selected from the group consisting of the notes green, woody, animalic, earthy, amber, fruity, floral and leather note, particularly preferably selected from the group consisting of the notes fruity and floral, or (ii) the or one, several or all of the further fragrance and / or aroma substances impart, modify and / or intensify one or more other odor and / or taste notes than those mentioned in (i). It is further preferred if
[0040] (i) the or one, several or all of the further fragrance and / or aroma substances (likewise) impart, modify and / or intensify one or more odor and / or taste notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalic, sweet, earthy, amber, fatty, metallic, balsamic, leather note and chlorine note, preferably one or more of the odor and / or taste notes selected from the group consisting of the notes green, woody, animalic, earthy, amber, fruity, floral, leather note and chlorine note, particularly preferably selected from the group consisting of the notes fruity, floral and chlorine note, or (ii) the or one, several or all of the further fragrance and / or aroma substances impart, modify and / or intensify one or more other odor and / or taste notes than those mentioned in (i).
[0041] Examples of fragrances and / or flavorings which can be advantageously combined with the compound of formula (I) within the scope of the present invention can be found, for example, in S. Arctander, Perfume and Flavor Materials, Vol. I and II, Montclair, NJ 1969, self-published, or K. Bauer et al., Common Fragrance and Flavor Materials, 4th Edition, Wiley-VCH, Weinheim 2001.
[0042] In detail: extracts from natural raw materials such as essential oils, concretes, absolutes, resins, resinoids, balsams, tinctures such as Ambergris tincture; Amyris oil; Angelica seed oil; Angelica root oil; Anise oil; Valerian oil; Basil oil; Tree moss absolute; Bay oil; Mugwort oil; Benzoeresin; Bergamot oil; Beeswax absolute; Birch tar oil; Bitter almond oil; Savory oil; Bucco leaf oil; Cabreuva oil; Cade oil; Calmus oil; Camphor oil; Cananga oil; Cardamom oil; Cascarilla oil; Cassia oil; Cassia absolute; Castoreum absolute; Cedar leaf oil; Cedarwood oil; Cistus oil; Citronella oil; Lemon oil; Copaiva balsam; Copaiva balsam oil; Coriander oil; Costus root oil; Cumin oil; Cypress oil; Davana oil; Dill herb oil; Dill seed oil; Eau de brouts absolute; Oakmoss absolute; Elemi oil; Tarragon oil; Eucalyptus citriodora oil; Eucalyptus oil; Fennel oil; Pine needle oil; Galbanum oil; Galbanum resin; Geranium oil; Grapefruit oil; Guaiac wood oil; Gurjun balsam; Gurjun 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; Cascarilla oil; Pine needle oil; Spearmint oil; Caraway oil; Labdanum oil;Labdanum absolute; Labdanum resin; Lavandin absolute; Lavandin oil; Lavender absolute; Lavender oil; Lemongrass oil; Lovage oil; Distilled lime oil; Pressed lime oil; Linaloe oil; Litsea cubeba oil; Bay leaf oil; Mace oil; Marjoram oil; Mandarin oil; Massoirie bark oil; Mimosa absolute; Musk seed oil; Musk tincture; Clary sage oil; Nutmeg oil; Myrrh absolute; Myrrh oil; Myrtle oil; Clove leaf oil; Clove flower oil; Neroli oil; Olibanum absolute; Olibanum oil; Opopanax oil; Orange blossom absolute; Orange oil; Origanum oil; Palmarosa oil; Patchouli oil; Perilla oil; Peru balsam oil; Parsley leaf oil; Parsley seed oil; Petitgrain oil; peppermint oil; pepper oil; allspice oil; pine oil; poly oil; rose absolute; rosewood oil; rose oil; rosemary oil; Dalmatian sage oil; sage oil Spanish; sandalwood oil; celery seed oil; spiclave oil; star anise oil; styrax oil; marigold oil; pine needle oil; tea tree oil; turpentine oil; thyme oil; tolu balm; Tonka absolute; tuberose absolute; vanilla extract; violet leaf absolute; verbena oil;Vetiver oil; juniper berry oil; wine yeast oil; wormwood oil; wintergreen oil; ylang oil; hyssop oil; civet absolute; cinnamon leaf oil; cinnamon bark oil and fractions thereof or ingredients isolated therefrom; individual fragrance substances from the group of hydrocarbons, such as 3-carene; α-pinene; β-pinene; α-terpinene; γ-terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E,Z)-1,3,5-undecatriene; styrene; diphenylmethane; aliphatic alcohols such as hexanol; octanol; 3-octanol; 2,6-dimethylheptanol; 2-methyl-2-heptanol; 2-Methyl-2-octanol; (E)-2-hexenol; 1-octen-3-ol; 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-methoxyoctan-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol; the aliphatic aldehydes and their acetals such as hexanal; heptanal; octanal; nonanal; decanal; undecanal; dodecanal; 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-undecadienal; Heptanal diethyl acetal; 1,1-Dimethoxy-2,2,5-trimethyl-4-hexene; Citronellyloxyacetaldehyde; 1-(1-Methoxypropoxy)-(E / Z)-3-hexene; the 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; aliphatic sulfur-containing compounds such as 3-methylthiohexanol; 3-methylthiohexyl acetate; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthiohexyl acetate; 1-menthene-8-thiol; aliphatic nitriles such as 2-nonenonitrile; 2-undecenonitrile; 2-tridecenonitrile; 3,12-tridecadienonitrile; 3,7-dimethyl-2,6-octadienonitrile; 3,7-dimethyl-6-octenonitrile; the esters of aliphatic carboxylic acids such as (E)- and (Z)-3-hexenylformate; ethyl acetoacetate; isoamyl acetate;3,5,5-Trimethylhexylacetat; 3-Methyl-2-butenylacetat; (E)-2-Hexenylacetat; (E)- und (Z)-3-Hexenylacetat; Octylacetat; 3-Octylacetat; 1-Octen-3-ylacetat; Ethylbutyrat; Butylbutyrat; Isoamylbutyrat; Hexylbutyrat; (E)- und (Z)-3-Hexenyl-isobutyrat; Hexylcrotonat; Ethylisovalerianat; Ethyl-2-methylpentanoat; Ethylhexanoat; Allylhexanoat; Ethylheptanoat; Allylheptanoat; Ethyloctanoat; Ethyl-(E,Z)-2,4-decadienoat; Methyl-2-octinat; Methyl-2-noninat; Allyl-2-isoamyloxyacetat; Methyl-3,7-dimethyl-2,6-octadien-oat;4-Methyl-2-pentyl-crotonat; der acyclischen Terpenalkohole wie z. B. Geraniol; Nerol; Lavadulol; Nerolidol; Farnesol; Tetrahydrolinalool; Tetrahydrogeraniol; 2,6-Dimethyl-7-octen-2-ol; 2,6-Dimethyloctan-2-ol; 2-Methyl-6-methylen-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-1-ol;as well as their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates; of the acyclic terpene aldehydes and ketones such as citronellal; 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal; geranylacetone; as well as the dimethyl and diethyl acetals of geranial, neral; of the cyclic terpene alcohols such as menthol; isopulegol; alpha-terpineol; terpinenol-4; menthan-8-ol; menthan-1-ol; menthan-7-ol; borneol; isoborneol; linalool oxide; nopol; cedrol; ambrinol; vetiverol; guajol; as well as their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates; of the cyclic terpene aldehydes and ketones such as menthone; isomenthone; 8-mercaptomenthan-3-one; carvone; camphor; fenchone; alpha-ionone; beta-ionone; alpha-n-methylionone; beta-n-methylionone; alpha-isomethylionone; beta-isomethylionone; alpha-iron; beta-damascenone;1-(2,4,4-Trimethyl-2-cyclohexen-1-yl)-2-buten-1-on; 1,3,4,6,7,8a-Hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methano-naphthalen-8(5H)-on;2-Methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal; Nootkaton; Dihydronootkaton; 4,6,8-Megastigmatrien-3-on; alpha-Sinensal; beta-Sinensal; acetyliertes Cedernholzöl (Methylcedrylketon); der cyclischen Alkohole wie z.B. 4-tert.-Butylcyclohexanol; 3,3,5-Trimethylcyclohexanol; 3-Isocamphylcyclohexanol; 2,6,9-Trimethyl-Z2,Z5,E9-cyclododecatrien-1-ol; 2-Isobutyl-4-methyltetrahydro-2H-pyran-4-ol; der cycloaliphatischen Alkohole wie z.B. alpha,3,3-Trimethylcyclohexylmethanol;1-(4-Isopropylcyclohexyl)ethanol; 2-Methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)butanol; 2-Methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-buten-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-(2,2,6-Trimethylcyclohexyl)pentan-3-ol;1-(2,2,6-Trimethylcyclohexyl)hexan-3-ol; der cyclischen und cycloaliphatischen Ether wie z.B. Cineol; Cedrylmethylether; Cyclododecylmethylether;1,1-Dimethoxycyclododecan; (Ethoxymethoxy)cyclo-dodecan; alpha-Cedrenepoxid; 3a,6,6,9a-Tetramethyldodecahydro-naphtho[2,1-b]furan; 3a-Ethyl-6,6,9a-trimethyldodecahydronaphtho[2,1b]furan; 1,5,9-Tri-methyl-13-oxabicyclo[10.1.0]trideca-4,8-dien; Rosenoxid; 2-(2,4-Dimethyl-3-cyclohexen-1-yl)-5-methyl-5-(1-methylpropyl)-1,3-dioxan; der cyclischen und makrocyclischen Ketone wie z.B. 4-tert.-Butylcyclohexanon; 2,2,5-Trimethyl-5-pentylcyclopentanon; 2-Heptylcyclopentanon; 2-Pentyl-cyclopentanon; 2-Hydroxy-3-methyl-2-cyclopenten-1-on; 3-Methyl-cis-2-penten-1-yl-2-cyclopenten-1-on; 3-Methyl-2-pentyl-2-cyclopenten-1-on; 3-Methyl-4-cyclopentadecenon; 3-Methyl-5-cyclopentadecenon; 3-Methylcyclopenta-decanon; 4-(1-Ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanon; 4-tert.-Pentylcyclo-hexanon; 5-Cyclohexadecen-1-on;6,7-Dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanon; 8-Cyclohexadecen-1-on; 9-Cycloheptadecen-1-on; Cyclopentadecanon; Cyclohexadecanon; der cycloaliphatischen Aldehyde wie z.B. 2-Methyl-4-(2,2,6-trimethyl-cyclohexen-1-yl)-2-butenal; 4-(4-Hydroxy-4-methylpentyl)-3-cyclohexencarbaldehyd; 4-(4-Methyl-3-penten-1-yl)-3-cyclohexencarbaldehyd; der cycloaliphatischen Ketone wie z. B. 1-(3,3-Dimethylcyclohexyl)-4-penten-1-on; 2,2-Dimethyl-1-(2,4-dimethyl-3-cyclohexen-1-yl)-1-propanon; 1-(5,5-Dimethyl-1-cyclohexen-1-yl)-4-penten-1-on; 2,3,8,8-Tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphtalenylmethylketon; Methyl-2,6,10-trimethyl-2,5,9-cyclododecatrienylketon; tert.-Butyl-(2,4-dimethyl-3-cyclohexen-1-yl)keton; der Ester cyclischer Alkohole wie z.B. 2-tert-Butylcyclohexylacetat; 4-tert-Butylcyclohexylacetat; 2-tert-Pentylcyclohexylacetat; 4-tert-Pentyl-cyclo-hexyl-acetat; 3,3,5-Trimethylcyclohexylacetat; Decahydro-2-naphthylacetat;2-Cyclo-pentylcyclopentylcrotonat;3-pentyltetrahydro-2H-pyran-4-yl acetate; decahydro-2,5,5,8a-tetramethyl-2-naphthyl acetate; 4,7-methano-3a,4,5,6,7,7a-hexahydro-5, or 6-indenyl acetate; 4,7-methano-3a,4,5,6,7,7a-hexahydro-5, or 6-indenyl propionate; 4,7-methano-3a,4,5,6,7,7a-hexahydro-5, or 6-indenyl isobutyrate; 4,7-methanooctahydro-5, or 6-indenyl acetate; the esters of cycloaliphatic alcohols such as 1-cyclohexyl ethyl crotonate; the esters of cycloaliphatic carboxylic acids such as e.g. B. Allyl-3-cyclohexylpropionate; allylcyclohexyloxyacetate; cis- and trans-methyldihydrojasmonate; cis- and trans-methyl jasmonate; Methyl 2-hexyl-3-oxocyclopentane carboxylate; Ethyl 2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate; Ethyl 2,3,6,6-tetramethyl-2-cyclohexene carboxylate; Ethyl 2-methyl-1,3-dioxolane-2-acetate; the araliphatic alcohols such as benzyl alcohol; 1-phenylethyl alcohol; 3-phenylpropanol; 2-phenylpropanol; 2-phenoxyethanol; 2,2-dimethyl-3-phenylpropanol; 2,2-Dimethyl-3-(3-methylphenyl)propanol; 1,1-dimethyl-2-phenylethyl alcohol;1,1-Dimethyl-3-phenylpropanol; 1-Ethyl-1-methyl-3-phenyl-propanol; 2-Methyl-5-phenylpentanol; 3-Methyl-5-phenylpentanol; 3-Phenyl-2-propen-1-ol; 4-Methoxybenzylalkohol; 1-(4-Isopropylphenyl)ethanol; der Ester von araliphatischen Alkoholen und aliphatischen Carbonsäuren wie z.B. Benzylacetat; Benzylpropionat; Benzylisobutyrat; Benzylisovalerianat; 2-Phenylethylacetat; 2-Phenylethylpropionat; 2-Phenylethylisobutyrat; 2-Phenylethylisovalerianat; 1-Phenylethylacetat; alpha-Trichlormethylbenzylacetat; alpha,alpha-Dimethylphenylethylacetat; alpha,alpha-Dimethylphenylethylbutyrat; Cinnamylacetat; 2-Phenoxyethylisobutyrat; 4-Methoxybenzylacetat; der araliphatischen Ether wie z.B. 2-Phenylethylmethylether; 2-Phenylethyl-isoamylether; 2-Phenylethyl-1-ethoxyethylether; Phenylacetaldehyddimethylacetal; Phenylacetaldehyddiethylacetal; Hydratropaaldehyddimethylacetal; Phenylacetaldehydglycerinacetal; 2,4,6-Trimethyl-4-phenyl-1,3-dioxan; 4,4a,5,9b-Tetra-hydroindeno[1,2-d]-m-dioxin;4,4a,5,9b-Tetrahydro-2,4-dimethylindeno[1,2-d]-m-dioxin; der aromatischen und araliphatischen Aldehyde wie z. B. Benzaldehyd; Phenylacetaldehyd; 3-Phenylpropanal; Hydratropaaldehyd; 4-Methylbenzaldehyd; 4-Methylphenylacetaldehyd; 3-(4-Ethylphenyl)-2,2-dimethylpropanal; 2-Methyl-3-(4-isopropylphenyl)propanal; 2-Methyl-3-(4-isobutylphenyl)propanal; 3-(4-tert.-Butylphenyl)propanal; Zimtaldehyd; alpha-Butylzimtaldehyd; alpha-Hexylzimtaldehyd; 3-Methyl-5-phenylpentanal; 4-Methoxybenzaldehyd; 4-Hydroxy-3-methoxybenz-aldehyd; 4-Hydroxy-3-ethoxybenzaldehyd; 3,4-Methylendioxybenzaldehyd; 3,4-Dimethoxybenzaldehyd; 2-Methyl-3-(4-methoxyphenyl)propanal; 2-Methyl-3-(4-methylendioxyphenyl)propanal; der aromatischen und araliphatischen Ketone wie z.B. Acetophenon; 4-Methylacetophenon; 4-Methoxyacetophenon; 4-tert.-Butyl-2,6-dimethylaceto-phenon; 4-Phenyl-2-butanon; 4-(4-Hydroxyphenyl)-2-butanon; 1-(2-Naphtha-lenyl)ethanon;2-Benzofuranylethanon;(3-Methyl-2-benzofuranyl)ethanon; Benzophenon;1,1,2,3,3,6-Hexamethyl-5-indanyl methyl ketone; 6-tert-butyl-1,1-dimethyl-4-indanyl methyl 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-aceto-naphthone; of aromatic and araliphatic carboxylic acids and their esters such as benzoic acid; phenylacetic acid; methyl benzoate; ethyl benzoate; hexyl benzoate; benzyl benzoate; methyl phenyl acetate; ethyl phenyl acetate; geranyl phenyl acetate; phenylethyl phenyl acetate; methyl cinnamate; ethyl cinnamate; benzyl cinnamate; phenylethyl cinnamate; Cinnamyl cinnamate; allyl phenoxyacetate; methyl 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; 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-pentensäurenitril; 3-Methyl-5-phenylpentan-säurenitril; Methylanthranilat; Methy-N-methylanthranilat; Schiff'sche Basen von Methylanthranilat mit 7-Hydroxy-3,7-dimethyloctanal, 2-Methyl-3-(4-tert.-butyl-phenyl)propanal oder 2,4-Dimethyl-3-cyclohexencarbaldehyd; 6-Isopropyl-chinolin; 6-Isobutylchinolin; 6-sec.-Butylchinolin;2-(3-Phenylpropyl)pyridin; Indol; Skatol; 2-Methoxy-3-isopropylpyrazin; 2-Isobutyl-3-methoxypyrazin; der Phenole, Phenylether und Phenylester wie z.B. Estragol; Anethol; Eugenylmethylether; Isoeugenol; Isoeugenylmethylether; Thymol; Carvacrol; Diphenylether; beta-Naphthylmethylether; beta-Naphthylethylether; beta-Naphthylisobutylether; 1,4-Dimethoxybenzol; Eugenylacetat; 2-Methoxy-4-methylphenol; 2-Ethoxy-5-(1-propenyl)phenol; p-Kresylphenylacetat; der heterocyclischen Verbindungen wie z.B. 2,5-Dimethyl-4-hydroxy-2H-furan-3-on; 2-Ethyl-4-hydroxy-5-methyl-2H-furan-3-on; 3-Hydroxy-2-methyl-4H-pyran-4-on; 2-Ethyl-3-hydroxy-4H-pyran-4-on;the lactones such as 1,4-octanolide; 3-methyl-1,4-octanolide; 1,4-nonanolide; 1,4-decanolide; 8-decene-1,4-olide; 1,4-undecanolide; 1,4-dodecanolide; 1,5-decanolide; 1,5-dodecanolide; 4-methyl-1,4-decanolide; 1,15-pentadecanolide; 1,16-Hexadeca-nolide; 9-hexadecene-1,16-olide; 10-oxa-1,16-hexadecanolide; 11-oxa-1,16-hexa-decanolide; 12-oxa-1,16-hexadecanolide; ethylene 1,12-dodecanedioate; ethylene 1,13-tridecanedioate; 2,3-dihydrocoumarin; Octahydrocoumarin. ;
[0043] According to a preferred embodiment of the fragrance and / or aroma composition according to the invention, the compound of formula (I) to be used according to the invention is preferably combined with one or more, particularly preferably with two, three, four, five or more, floral and / or fruity further fragrance and / or aroma substances.
[0044] Accordingly, the present invention also relates to a fragrance and / or aroma composition comprising one, two, three, four, five or more (further) fragrances and / or aromas that impart a floral and / or fruity odor and / or flavor note.
[0045] The compound of formula (I) to be used according to the invention advantageously achieves (at least partially) an olfactory and / or taste enhancement of the floral and / or fruity note(s).
[0046] Floral fragrances and / or aromas with which the compound of formula (I) to be used according to the invention (in particular in fragrance and / or aroma compositions according to the invention) can be advantageously combined are preferably selected from the group consisting of: hydroxycitronellal, methoxycitronellal, cyclamenaldehyde [2-methyl-3-(4-isopropylphenyl)propanal], 1-(4-isopropylcyclohexyl)ethanol (Mugetanol ®< ), 4-tert-butyl-α-methyldihydrocinnamaldehyde (Lilial ®< ), cis-hexahydrocuminyl alcohol (Mayol ®< ), 3-[4-(1,1-dimethylethyl)phenyl]propanal (Bourgeonal ®< ), 2,2-dimethyl-3-(3-methylphenyl)propanol (Majantol ®< ), 3-Methyl-3-(3-methylbenzyl)-butan-2-ol, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol (Florosa ®< ), 2-methyl-3-(3,4-methylenedioxyphenyl)propanal (Heliofolal ®< ), 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarbaldehyde (Lyral ®< ), 4-(Octahydro-4,7-methano-5H-indene-5-ylidene-butanal (Dupical ®< ), vernaldehyde,4-(4-Methyl-3-penten-1-yl)-3-cyclohexencarbaldehyd (Vertomugal ®< ), Octahydro-5-(4-methoxybutyliden)-4,7-methano-1H-inden (Mugoflor ®< ), 2,6-Dimethyl-2-heptanol (Freesiol ®< ), 1-Ethyl-1-methyl-3-phenylpropanol (Phemec ®< ), 2,2-Dimethyl-3-phenyl-1-propanol (Muguet alcohol), Profarnesol, Dihydrofarnesol, Farnesol, Nerolidol, Hydroxycitronellaldimethylacetal, Hexylbenzoat, Geraniol, Nerol, Linalool, Tetrahydrogeraniol, Tetrahydrolinalool, Ethyllinalool, Geranyltiglinat, Phenethylalkohol (2-Phenylethylalkohol), Citronellol, Rosenoxid, 2-Methyl-5-phenylpentanol (Rosaphen), 3-Methyl-5-phenylpentanol (Phenoxanol), Methyldihydrojasmonat (Hedion ®< , Hedione ®< high cis), 2-Heptylcyclopentanon (Projasmon P), cis-Jasmon, Dihydrojasmon, Zimtalkohol (3-Phenyl-2-propen-1-ol), Dihydrozimtalkohol (3-Phenylpropanol), 2-Methyl-4-phenyl-1,3-dioxolan (Jacinthaflor ®< ) und Dihydromyrcenol (2,6-Dimethyl-7-octen-2-ol).,
[0047] Fruity fragrances and / or flavorings with which the compound of formula (I) to be used according to the invention can be advantageously combined, and which are therefore particularly preferred (further) fragrances and / or flavorings of a fragrance and / or flavoring composition according to the invention, are preferably selected from the group consisting of: 2-methylbutyric acid ethyl ester, 4-(p-hydroxyphenyl)-2-butanone, ethyl 3-methyl-3-phenylglycidate, butyric acid isoamyl ester, acetate acid isoamyl ester, acetate acid n-butyl ester, butyric acid ethyl ester, 3-methylbutyric acid ethyl ester, n-hexanoic acid ethyl ester, n-hexanoic acid allyl ester, ethyl 2-trans-4-cis-decadienoate, 1,1-dimethoxy-2,2,5-trimethyl-4-hexane, 2,6-dimethyl-5-hepten-1-al, gamma-undecalactone, gamma-nonalactone, hexanal, 3Z-hexenal, n-decanal, n-dodecanal, citral, vanillin, ethylvanillin, maltol, ethylmaltol and mixtures thereof.
[0048] Fragrance and / or aroma compositions according to the invention containing the compound of formula (I) can be in liquid form, undiluted or diluted with a solvent, or are advantageously used for perfuming or aromatization. Preferred solvents for this purpose are ethanol, isopropanol, diethylene glycol monoethyl ether, glycerin, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, triacetin, and diacetin.
[0049] Furthermore, fragrance and / or aroma compositions according to the invention can be adsorbed onto a carrier, which ensures both a fine distribution of the fragrance and / or aroma substances in the product and a controlled release during application. Such carriers can be porous inorganic materials such as light sulfate, silica gels, zeolites, gypsum, clays, clay granules, aerated concrete, etc., or organic materials such as wood, cellulose-based materials, sugar, dextrins (e.g., maltodextrin), or plastics such as PVC, polyvinyl acetates, or polyurethanes. The combination of the composition according to the invention and the carrier is also to be understood as a fragrance and / or aroma composition according to the invention or can be present as an article according to the invention (as described further below).
[0050] Fragrance and / or aroma compositions or articles according to the invention (as described further below) may also be microencapsulated, spray-dried, in the form of inclusion complexes or extrusion products and - in the case of a fragrance and / or aroma composition - added in this form, for example, to an article to be perfumed or flavored (as described further below).
[0051] If necessary, the properties of the compositions or articles modified in this way can be further optimized by coating them with suitable materials for more targeted fragrance release. Wax-like plastics such as polyvinyl alcohol are preferably used for this purpose. The resulting products, in turn, represent articles according to the invention.
[0052] Microencapsulation can be achieved, for example, by the so-called coacervation process using capsule materials such as polyurethane-like substances or soft gelatin.
[0053] Spray-dried products are preferably produced by spray-drying an emulsion or dispersion containing the fragrance and / or flavoring composition, whereby modified starches, proteins, dextrin and vegetable gums can be used as carriers.
[0054] Inclusion complexes can be prepared, for example, by introducing dispersions of the fragrance and / or aroma composition and cyclodextrins or urea derivatives into a suitable solvent, e.g. water.
[0055] Extrusion products can be obtained, for example, by melting the fragrance and / or aroma compositions with a suitable waxy substance and by extrusion with subsequent solidification, optionally in a suitable solvent, e.g. isopropanol.
[0056] A further aspect of the present invention relates to the use of an odoriferous and / or flavoring composition according to the invention for imparting, modifying and / or enhancing one or more odor and / or flavor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalic, sweet, earthy, amber, fatty, metallic, balsamic, leather note and chlorine note, preferably at least one of the odor and / or flavor notes selected from the group consisting of the notes green, woody, animalic, earthy, amber, fruity, floral, leather note and chlorine note.
[0057] For preferred embodiments, what has been said above in connection with a use according to the invention or a fragrance and / or aroma composition according to the invention applies accordingly.
[0058] Fragrance and / or aroma compositions according to the invention can advantageously be used in concentrated form, in solutions or in the modified form described above for the production of perfumed and / or aromatized articles according to the invention (as described further below) such as perfume extracts, eau de parfums, eau de toilettes, aftershaves, eau de colognes, pre-shave products, splash colognes and perfumed refreshing wipes as well as the perfuming of acidic, alkaline and neutral cleaning agents, such asFloor cleaners, window glass cleaners, dishwashing detergents, bathroom and sanitary cleaners, scouring cream, solid and liquid toilet cleaners, powder and foam carpet cleaners, fabric fresheners, ironing aids, liquid detergents, powder detergents, laundry pre-treatment agents such as bleaching agents, soaking agents and stain removers, fabric softeners, laundry soaps, washing tablets, disinfectants, surface disinfectants as well as air fresheners in liquid, gel or solid carrier form, aerosol sprays, waxes and polishes such as furniture polishes, floor waxes, shoe polishes and personal care products such as solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams, bath oils, cosmetic emulsions of the oil-in-water, water-in-oil and water-in-oil-in-water type such asSkin creams and lotions, face creams and lotions, sun protection creams and lotions, after-sun creams and lotions, hand creams and lotions, foot creams and lotions, hair removal creams and lotions, after-shave creams and lotions, tanning creams and lotions, hair care products such as hair sprays, hair gels, firming hair lotions, hair conditioners, permanent and semi-permanent hair dyes, hair styling products such as cold waves and hair straighteners, hair tonics, hair creams and lotions, deodorants and antiperspirants such as underarm sprays, roll-ons, deodorant sticks, deodorant creams, decorative cosmetic products such as eye shadow, nail polish, make-up, lipsticks, mascara as well as candles, lamp oils, incense sticks, insecticides, repellents and fuels.
[0059] A further aspect of the present invention relates to a method for imparting, enhancing and / or modifying one or more odor and / or flavor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalic, sweet, earthy, amber, fatty, metallic, balsamic, leather note and chlorine note, preferably for imparting, enhancing and / or modifying one or more odor and / or flavor notes selected from the group consisting of the notes green, woody, animalic, earthy, amber, fruity, floral, leather note and chlorine note, comprising or consisting of the following steps: (a) Providing (a.1) the compound of formula (I) and (a.2) one, two, three, four, five, six, seven, eight, nine, ten or more further fragrance and / or aroma substance(s) with one or more odor and / or taste notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalic, sweet, earthy, amber, fatty, metallic, balsamic, leather note and chlorine note, preferably with one or more odor and / or taste notes selected from the group consisting of the notes green, woody, animalic, earthy, amber, fruity, floral, leather note and chlorine note, (b) adding the compound of formula (I) (a.1) to the further fragrance and / or aroma substance(s) (a.2), in an amount sufficient to impart, enhance and / or modify one or more olfactory and / or flavor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalic, sweet, earthy, amber, fatty, metallic, balsamic, leather note and chlorine note, preferably in an amount sufficient to impart, modify and / or enhance one or more olfactory and / or flavor notes selected from the group consisting of the notes green, woody, animalic, earthy, amber, fruity, floral, leather note and chlorine note.
[0060] In connection with the process described herein or the use for imparting, modifying and / or enhancing an odor and / or flavor note, there is also the finding that the compound of formula (I) can function excellently as a so-called booster (amplifier, enhancer).
[0061] A preferred embodiment accordingly relates to a method according to the invention for modifying and / or enhancing (boosting) a smell and / or taste, in particular with one, several or all of the notes floral, fruity and / or woody, comprising or consisting of the following steps: (a) Providing (a.1) the compound of formula (I) and (a.2) one or more further fragrances and / or aromas having one or more of the odor and / or taste notes selected from the group consisting of floral, fruity and / or woody, (b) adding the compound of formula (I) (a.1) to the further fragrances and / or aromas (a.2) in a sensorially effective amount, preferably in an amount sufficient to sensorially modify and / or enhance the odor and / or taste impression of the further fragrances and / or aromas (a.2).
[0062] A further aspect of the present invention relates to a perfumed and / or flavored article comprising or consisting of (i) a fragrance and / or aroma composition according to the invention (as described herein), or the compound of formula (I) and one, two, three, four, five, six, seven, eight, nine, ten or more further fragrance and / or flavoring substance(s), wherein the weight ratio of the total amount of compound of formula (I) to the total amount of further fragrance and / or flavoring substance(s) is in the range from 1:1000 to 1:0.1, preferably from 1:1000 to 1:0.5, and (ii) one or more further constituent(s), preferably at least one or more, preferably one, two, three, four, five or more, additive(s), auxiliary(s) and / or active(s), and wherein the article is selected from the group consisting of washing and cleaning agents, hygiene or care products, preferably in the field of body, hair and oral care, cosmetics and household, preferably from the group consisting of surface cleaners, toilet cleaners, all-purpose cleaners, mouthwashes, toothpastes, tooth gels, toothpastes, tooth powders, dental care chewing gums, perfume extracts, eau de parfums, eau de toilettes, aftershaves, eau de colognes, pre-shave products, splash colognes, perfumed refreshing wipes, acidic, alkaline or neutral cleaning agents, textile fresheners, ironing aids, liquid detergents, powdered detergents, laundry pretreatment agents, fabric softeners, washing soaps, washing tablets, disinfectants, surface disinfectants, air fresheners, aerosol sprays, waxes and polishes, body care products, hand creams and lotions, foot creams and lotions, depilatory creams and -lotions,Aftershave creams and lotions, tanning creams and lotions, hair care products, deodorants, antiperspirants, decorative cosmetic products, candles, lamp oils, incense sticks, insecticides, repellents and fuels.
[0063] For preferred embodiments, what has been said above in connection with a use according to the invention, a fragrance and / or aroma composition according to the invention or a method according to the invention applies accordingly.
[0064] Preferably, an article according to the invention is selected from the group consisting of washing and cleaning agents, hygiene or care products in the field of body and hair care, cosmetics and household, preferably from the group consisting of perfume extracts, eau de parfums, eau de toilettes, aftershaves, eau de colognes, pre-shave products, splash colognes, perfumed refreshing wipes, acidic, alkaline or neutral cleaning agents, textile fresheners, ironing aids, liquid washing agents, powdered washing agents, laundry pretreatment agents, fabric softeners, washing soaps, washing tablets, disinfectants, surface disinfectants, air fresheners, aerosol sprays, waxes and polishes, body care products, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, after-shave creams and lotions, tanning creams and lotions, hair care products, deodorants, antiperspirants, products of decorative cosmetics,Candles, lamp oils, incense sticks, insecticides, repellents and fuels.
[0065] Furthermore, for a perfumed and / or flavored article according to the invention, that component (i) is contained in a sensorially effective amount, preferably in an amount sufficient for a consumer to perceive one or more odor and / or taste notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalic, sweet, earthy, amber, fatty, metallic, balsamic and leather note, preferably one or more odor and / or taste notes selected from the group consisting of the notes green, woody, animalic, earthy, amber, fruity, floral and leather note, and / or that one, two, three, four, five, six, seven, eight, nine, ten or more of the further odoriferous and / or aromatic substances in component (i) impart, modify and / or enhance a green, woody, animalic, earthy, amber, fruity, floral and / or leathery odor and / or taste.
[0066] Particularly preferred for a perfumed and / or flavored article according to the invention, that component (i) is contained in a sensorially effective amount, preferably in an amount sufficient for a consumer to perceive one or more odor and / or taste notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalic, sweet, earthy, amber, fatty, metallic, balsamic, leather note and chlorine note, preferably one or more odor and / or taste notes selected from the group consisting of the notes green, woody, animalic, earthy, amber, fruity, floral, leather note and chlorine note, and / or that one, two, three, four, five, six, seven, eight, nine, ten or more of the further odor and / or flavor substances in component (i) impart, modify and / or intensify a green, woody, animalic, earthy, amber, fruity, floral, leathery and / or chlorine-like odor and / or taste.
[0067] It is also preferred if the perfumed and / or flavored article contains a total amount of compound of formula (I), based on the total weight of the article, in the range from 0.00001 to 10% by weight, preferably 0.0001 to 5% by weight, particularly preferably 0.001 to 2% by weight, further preferably 0.005 to 1% by weight.
[0068] The additives, auxiliaries and / or active ingredients described above are preferably not fragrances and / or flavorings and, if included, are preferably selected from the group consisting of: Preservatives, preferably those mentioned in US 2006 / 0089413, abrasives, anti-acne agents and sebum-reducing agents, preferably those mentioned in WO 2008 / 046791, anti-aging agents, preferably those mentioned in WO 2005 / 123101, antibacterial agents, anti-cellulite agents, anti-dandruff agents, preferably those mentioned in WO 2008 / 046795, anti-inflammatory agents, anti-irritant agents, anti-irritants (anti-inflammatory, anti-irritant and anti-irritant agents), preferably those mentioned in WO 2007 / 042472 and US 2006 / 0089413, antimicrobial agents, preferably those mentioned in WO 2005 / 123101, antioxidants, preferably those mentioned in WO 2005 / 123101, Astringents, antiseptic agents, antistatic agents, binders, buffers, carrier materials, preferably those mentioned in WO 2005 / 123101, chelating agents, preferably those mentioned in WO 2005 / 123101, cell stimulants, cleaning agents, care agents, depilatory agents,surfactants, deodorants and antiperspirants, preferably those mentioned in WO 2005 / 123101, plasticizers, emulsifiers, preferably those mentioned in WO 2005 / 123101, enzymes, essential oils, preferably those mentioned in US 2008 / 0070825, insect repellents, preferably those mentioned in WO 2005 / 123101, fibers, film formers, (other) fixatives, foam formers, foam stabilizers, substances for preventing foaming, foam boosters, fungicides, gelling agents and gel-forming agents, preferably those mentioned in WO 2005 / 123101, hair care products, hair shaping products, hair straightening products, moisture regulators (moisturizing, moisturizing and / or humectant-retaining substances), preferably those mentioned in WO 2005 / 123101, Osmolytes, preferably those mentioned in WO 2005 / 123101, compatible solutes, preferably those mentioned in WO 01 / 76572 and WO 02 / 15686, bleaching agents, strengthening agents, stain-removing agents, optically brightening agents,Impregnating agents, dirt-repellent agents, friction-reducing agents, lubricants, moisturizing creams, ointments, opacifying agents, plasticizing agents, covering agents, polishes, glossing agents, polymers, preferably those mentioned in WO 2008 / 046676, powders, proteins and protein hydrolysates, preferably those mentioned in WO 2005 / 123101 and WO 2008 / 046676, refatting agents, abrasives, skin-soothing agents, skin-cleansing agents, skin-care agents, skin-healing agents (skin repair agents), preferably containing cholesterol and / or fatty acids and / or ceramides and / or pseudoceramides, preferably those mentioned in WO 2006 / 053912, skin-lightening agents, preferably those mentioned in WO 2007 / 110415, skin-protecting agents, skin-softening agents, skin-cooling agents, preferably the skin-warming agents mentioned in WO 2005 / 123101, preferably the stabilizers, UV-absorbing agents and UV filters mentioned in WO 2005 / 123101,preferably those mentioned in WO 2005 / 123101, benzylidene-betadicarbonyl compounds, preferably those mentioned in WO 2005 / 107692, alpha-benzoylcinnamonitriles, preferably those mentioned in WO 2006 / 015954, AhR receptor antagonists, preferably those mentioned in WO 2007 / 128723 and WO 2007 / 060256, detergents, fabric softeners, suspending agents, skin tanning agents, preferably those mentioned in WO 2006 / 045760, thickeners, vitamins, preferably those mentioned in WO 2005 / 123101, fatty oils, waxes and fats, preferably those mentioned in WO 2005 / 123101, phospholipids, preferably those mentioned in WO 2005 / 123101, fatty acids (saturated fatty acids, mono- or polyunsaturated fatty acids, α-hydroxy acids, polyhydroxy fatty acids), preferably those mentioned in WO 2005 / 123101, dyes and color-protecting agents and pigments, preferably those mentioned in WO 2005 / 123101, anticorrosives, alcohols and polyols, preferably those mentioned in WO 2005 / 123101, surfactants,preferably those mentioned in WO 2005 / 123101, animal extracts, yeast extracts, extracts of algae or microalgae, electrolytes, liquefiers, organic solvents, preferably those mentioned in WO 2005 / 123101, hair growth modulating agents (hair growth promoting or hair growth inhibiting), preferably those mentioned in EP 2168570 and EP 2193785 or silicones and silicone derivatives, preferably those mentioned in WO 2008 / 046676, preferably from the group consisting of preservatives, inorganic salts, chelating agents, surfactants, skin and / or hair care agents, enzymes, emulsifiers, fats, fatty oils, waxes, fatty alcohols, silicones, silicone derivatives and water.
[0069] The perfumed and / or flavored article according to the invention, as described above, is, according to a preferred embodiment, a preparation (according to the invention) serving for oral care.
[0070] Preparations intended for food or pleasure include, for example, baked goods (e.g. bread, biscuits, cakes, other pastries), sweets (e.g. chocolates, chocolate bar products, other bar products, fruit gums, hard and soft caramels, chewing gum), alcoholic or non-alcoholic beverages (e.g. coffee, tea, wine, wine-based beverages, beer, beer-based beverages, liqueurs, schnapps, brandies, fruit-based lemonades, isotonic drinks, soft drinks, nectars, fruit and vegetable juices, fruit or vegetable juice preparations), instant beverages (e.g. instant cocoa drinks, instant tea drinks, instant coffee drinks), meat products (e.g. ham, fresh sausage or raw sausage preparations, seasoned or marinated fresh or cured meat products), eggs or egg products (dried egg, egg white, egg yolk), cereal products (e.g. breakfast cereals, Muesli bars, pre-cooked rice products), dairy products (e.g.Milk drinks, milk ice cream, yogurt, kefir, cream cheese, soft cheese, hard cheese, dried milk powder, whey, butter, buttermilk, partially or fully hydrolyzed products containing milk protein), products made from soy protein or other soybean fractions (e.g. soy milk and products made from it, preparations containing soy lecithin, fermented products such as tofu or tempeh or products made from them, soy sauces), fruit preparations (e.g. jams, fruit ice cream, fruit sauces, fruit fillings), vegetable preparations (e.g. ketchup, sauces, dried vegetables, frozen vegetables, pre-cooked vegetables, pickled vegetables, canned vegetables), snacks (e.g. baked or fried potato chips or potato dough products, bread dough products, corn- or peanut-based extrudates), fat- and oil-based products or emulsions thereof (e.g. mayonnaise, tartar sauce, dressings, seasonings), other ready meals and soups (e.g.Dry soups, instant soups, pre-cooked soups), spices, seasoning mixes and, in particular, seasonings, which are used, for example, in the snack sector.
[0071] Preparations according to the invention can be in the form of semi-finished products or seasoning mixtures.
[0072] Preparations described herein can be used, in particular, as semi-finished products for the manufacture of further preparations for nutrition or enjoyment, particularly in spray-dried form. Preparations described herein can also be in the form of capsules, tablets (uncoated and coated tablets, e.g., enteric-coated tablets), coated tablets, granules, pellets, solid mixtures, dispersions in liquid phases, as emulsions, as powders, as solutions, as pastes, or as other swallowable or chewable preparations as food supplements.
[0073] Preparations according to the invention for oral care are in particular oral and / or dental care products such as toothpastes, tooth gels, tooth powders, mouthwashes, chewing gums and other oral care products.
[0074] Other conventional active ingredients, base substances, auxiliaries, and additives for oral care preparations according to the invention can be contained in amounts of 5 to 99.9999 wt.%, preferably 10 to 80 wt.%, based on the total weight of the preparation. Furthermore, the preparations can contain water in an amount of up to 99.9 wt.%, preferably 5 to 80 wt.%, based on the total weight of the preparation.
[0075] Preparations according to the invention (as examples of articles according to the invention) are produced according to a preferred embodiment by incorporating compounds as a substance, as a solution (e.g. in ethanol, water or 1,2-propylene glycol) or in the form of a mixture with a solid or liquid carrier (e.g. maltodextrin, starch, silica gel), other flavorings or flavoring substances and optionally further auxiliaries and / or stabilizers (e.g. natural or artificial polysaccharides and / or plant gums such as modified starches or gum arabic) into a base preparation used for oral care. Advantageously, preparations according to the invention present as a solution and / or suspension or emulsion can also be converted into a solid preparation according to the invention (preferably a semi-finished product) by spray drying.
[0076] The spray-dried solid preparations according to the invention (as a further example of articles according to the invention) are particularly well suited as semi-finished products for the production of further preparations according to the invention. The spray-dried solid preparations according to the invention preferably contain 50 to 95% by weight of carriers, in particular maltodextrin and / or starch, and 5 to 40% by weight of excipients, preferably natural or artificial polysaccharides and / or plant gums such as modified starches or gum arabic.
[0077] According to a further preferred embodiment, for the production of preparations according to the invention, the compound of formula (I) and optionally other constituents of the preparation according to the invention are first incorporated into emulsions, in liposomes, e.g. starting from phosphatidylcholine, in microspheres, in nanospheres or also in capsules, granules or extrudates made from a matrix suitable for food and beverages, e.g. from starch, starch derivatives (e.g. modified starch), cellulose or cellulose derivatives (e.g. hydroxypropyl cellulose), other polysaccharides (e.g. dextrin, alginate, curdlan, carageenan, chitin, chitosan, pullulan), natural fats, natural waxes (e.g. beeswax, carnauba wax), from proteins, e.g. gelatin or other natural products (e.g. shellac).Depending on the matrix, the products can be obtained by spray drying, spray granulation, melt granulation, coacervation, coagulation, extrusion, melt extrusion, emulsion processes, coating, or other suitable encapsulation processes, and optionally a suitable combination of the aforementioned processes. In another preferred production process for a preparation according to the invention, compounds are first complexed with one or more complexing agents, for example with cyclodextrins or cyclodextrin derivatives, preferably α- or β-cyclodextrin, and used in this complexed form.
[0078] Particularly preferred is a preparation according to the invention in which the matrix is selected such that the compound of formula (I) is released from the matrix with a delay, thus achieving a long-lasting effect. A fat, wax, polysaccharide, or protein matrix is particularly preferred in this regard.
[0079] As further ingredients for preparations described herein for nutrition or enjoyment, common basic, auxiliary and additive substances for food or beverages can be used, e.g. water, mixtures of fresh or processed, vegetable or animal basic or raw materials (e.g. raw, fried, dried, fermented, smoked and / or cooked meat, bones, cartilage, fish, vegetables, fruits, herbs, nuts, vegetable or fruit juices or pastes or mixtures thereof), digestible or indigestible carbohydrates (e.g. sucrose, maltose, fructose, glucose, dextrins, amylose, amylopectin, inulin, xylans, cellulose, tagatose), sugar alcohols (e.g. sorbitol, erythritol), natural or hydrogenated fats (e.g. tallow, lard, palm fat, coconut fat, hydrogenated vegetable fat), oils (e.g. sunflower oil, peanut oil, corn oil, olive oil, fish oil, soybean oil, sesame oil), fatty acids or their salts (e.g.Potassium stearate), proteinogenic or non-proteinogenic amino acids and related compounds (e.g. γ-aminobutyric acid, taurine), peptides (e.g. glutathione), native or processed proteins (e.g. gelatin), enzymes (e.g. peptidases), nucleic acids, nucleotides, taste correctors for unpleasant taste impressions, other taste modulators for other, generally not unpleasant taste impressions, other taste modulating substances (e.g. inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), emulsifiers (e.g. lecithins, diacylglycerols, gum arabic), stabilizers (e.g. carageenan, alginate), preservatives (e.g. benzoic acid, sorbic acid), antioxidants (e.g. tocopherol, ascorbic acid), chelators (e.g. citric acid), organic or inorganic acidifiers (e.g. malic acid, acetic acid, citric acid, tartaric acid, phosphoric acid), bitter substances (e.g.Quinine, caffeine, limonin, amarogentin, humolone, lupolone, catechins, tannins), mineral salts (e.g. sodium chloride, potassium chloride, magnesium chloride, sodium phosphates), substances that prevent enzymatic browning (e.g. sulfite, ascorbic acid), essential oils, plant extracts, natural or synthetic dyes or color pigments (e.g. carotenoids, flavonoids, anthocyanins, chlorophyll and their derivatives), spices, trigeminal active substances or plant extracts containing such trigeminal active substances, synthetic, natural or nature-identical flavorings or fragrances and odor correctors.
[0080] Dental care products (preparations according to the invention serving as a basis for oral care) generally comprise an abrasive system (grinding or polishing agents), such as silicic acids, calcium carbonates, calcium phosphates, aluminum oxides and / or hydroxyapatites, surface-active substances such as sodium lauryl sulfate, sodium lauryl sarcosinate and / or cocamidopropyl betaine, humectants such as glycerol and / or sorbitol, thickeners such as carboxymethylcellulose, polyethylene glycols, carrageenan and / or Laponite ®< , sweeteners such as saccharin, taste correctors for unpleasant taste impressions, taste correctors for other, generally not unpleasant taste impressions, taste modulating substances (e.g. inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), cooling agents such as menthol, Menthol derivatives (e.g.L-menthol, L-menthyl lactate, L-menthyl alkyl carbonates, menthone ketals, menthane carboxylic acid amides), 2,2,2-trialkylacetic acid amides (e.g. 2,2-diisopropylpropionic acid methylamide), icilin and icilin derivatives, stabilizers and active ingredients such as sodium fluoride, sodium monofluorophosphate, tin difluoride, quaternary ammonium fluorides, zinc citrate, zinc sulfate, tin pyrophosphate, tin dichloride, mixtures of various pyrophosphates, triclosan, cetylpyridinium chloride, aluminum lactate, potassium citrate, potassium nitrate, potassium chloride, strontium chloride, hydrogen peroxide, flavors and / or sodium bicarbonate or odor correctors.
[0081] Chewing gums (as a further example of preparations according to the invention serving for oral care) generally comprise a chewing gum base, ie a chewing mass which becomes plastic when chewed, various types of sugar, sugar substitutes, other sweet-tasting substances, sugar alcohols, taste correctors for unpleasant taste impressions, other taste modulators for further, generally not unpleasant taste impressions, taste modulating substances (e.g. inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), humectants, thickeners, emulsifiers, flavourings and stabilisers or odour correctors.
[0082] A further aspect of the present invention relates to a method for perfuming and / or flavoring an article, comprising or consisting of the following steps: (a) Providing (a.1) a fragrance and / or flavor composition (as described herein), or (a.2) the compound of formula (I) and optionally one, two, three, four, five, six, seven, eight, nine, ten or more further fragrance and / or flavoring substance(s), wherein the weight ratio of the total amount of compound of formula (I) to the total amount of further fragrance and / or flavoring substance(s) is in the range from 1:1000 to 1:0.1, preferably from 1:1000 to 1:0.5, and (b) adding the fragrance and / or flavoring substance composition (a.1) or the compound / fragrances (a.2) to the article to be perfumed and / or flavored, in an amount sufficient to impart, enhance and / or modify one or more olfactory and / or flavor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalic, sweet, earthy, amber, fatty, metallic, balsamic, leather note and chlorine note, preferably one or more of the olfactory and / or flavor notes selected from the group consisting of the notes green, woody, animalic, earthy, amber, fruity, floral, leather note and chlorine note.
[0083] Furthermore, the present invention relates to a method for perfuming hair, skin, textile fibers, surfaces and / or room air comprising or consisting of the following steps: (a) Providing (a.1) a fragrance and / or aroma composition (as described herein), preferably containing a surfactant or a surfactant mixture, or (a.2) the compound of formula (I) and optionally one, two, three, four, five, six, seven, eight, nine, ten or more further fragrance and / or aroma substance(s), wherein the weight ratio of the total amount of compound of the formula (I) to the total amount of further fragrance and / or aroma substance(s) is in the range from 1:1000 to 1:0.1, preferably from 1:1000 to 1:0.5, and additionally preferably a surfactant or a surfactant mixture, or (a.3) an article according to the invention (as described herein), preferably containing a surfactant or a surfactant mixture, and (b) applying or introducing the fragrance and / or aroma substance composition (a.1) or the compound / fragrances (a.2) or the article (a.3) onto the hair or skin or fibers or surface orinto the room air to be perfumed in an amount sufficient for the consumer to perceive one or more odor and / or taste notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalic, sweet, earthy, amber, fatty, metallic, balsamic, leather note and chlorine note, preferably at least one of the odor and / or taste notes selected from the group consisting of the notes green, woody, animalic, earthy, amber, fruity, floral, leather note and chlorine note.
[0084] For preferred embodiments of the methods described herein, what has been said in connection with uses according to the invention or fragrance and / or aroma compositions according to the invention or articles according to the invention applies accordingly.
[0085] Furthermore, what is stated in the context of an embodiment of the present invention described herein also applies to other embodiments described herein. Accordingly, the embodiments described herein can be combined with one another in any way—as long as it is reasonable for a person skilled in the art.
[0086] The invention is explained in more detail below using examples. Unless otherwise stated, all data refer to weight. Abbreviations used: DPG = dipropylene glycol, TEC = triethyl citrate Example 1: Preparation of 2,3,6-trimethylcyclohexanol (compound of formula (I)
[0087] In a 250 ml autoclave, 138 g of 2,5,6-trimethylcyclohex-2-en-1-one in 50 g of isopropanol are hydrogenated with 2 g of Raney nickel at 10 bar and 120°C for 6 h. After cooling, the catalyst is filtered off and the mixture is concentrated. The crude product (141 g) is fractionally distilled under vacuum on a 30 cm Vigreux column. Yield: 138 g (97.2% of theory) Bp: 95°-98°C / 2 mbar MS: m / z (%) = 142(1-12), 124(20-57), 109(50-85), 95(56-98), 85(96-100), 71(62-100), 55(53-80), 41(48-77) Example 2: Perfume composition (fragrance composition)
[0088] IRIS SAFFIAN Total in g (18 parts): 1.000,00 ALDEHYDE C14 SOG 5 ALLYLIONONE 4 AMBROCENIDE ®< 10 DPG 10% DPG 10 AMYRIS OIL 100 CEDARWOOD OIL 200 ELEMI RESIN 70% IN BB 275 Guajyl acetate 5 IONONE ALPHA 80 IRALDEIN GAMMA 80 IRISNITRIL 1% DPG 25 CARROT SEED OIL 5 MADRANOL ®< 100 MYRRH ABSOLUTE 10 NONADIENOL-2.6 1% DPG 10 PATCHOULI OIL REMOVED 5 PERUBALSAM OEL ED 3 TABANON 10% DPG 3 VERTOFIX 80
[0089] According to the perfumers, this perfume composition becomes more rounded and harmonious with the addition of 3% by weight of a compound of formula (I) (e.g., product from Example 1, 1% solution in DPG), adding a leathery note and enhancing the woody and floral aspects. The combination or use according to the invention gives the composition its own character and unites the different olfactory elements. Example 3: Perfume composition (fragrance composition)
[0090] CRISTAL CHEAP Total in g (39 parts): 1.000,00 ALDEHYDE C14 SOG. 3 BASIL OIL COMORES TYPE E 0,5 BENZYL SALICYLATE 45 CEDRYL ACETATE 5 CITRAL FF 2 CITRONE RCO 60 CITRONELLOL 950 12 CITRORANGE BASE COLIPA 2 DIHYDROJASMON 4 DIHYDROMYRCENOL 10 DIPROPYLENE GLYCOL 201,5 EVERNYL 2 FARENAL ®< 0,5 GALBANUM OIL 1 GALBASCONE 10% DPG 9 GERANIOL SUPRA 5 PURE GERANYL ACETATE 3 HEDION 280 HELIONAL 25 HERBAFLORAT 5 HEXYL CINNAMALTADEHYDE ALPHA 45 INDOLENE 50 CASTOR OIL 10% DPG 10 ISORALDEIN 70 40 JASMIN 61 TYPE BASE 10 JASMOPYRAN 4 LAVENDER OIL MT. BLANC 40 / 42% 2 LILIAL 35 LINALOOL 30 LINALYL ACETATE 25 MACROLIDE ®< SUPRA 3 MYSORANE ®< BASE 20 NEOFOLIONE 10% DPG 2,5 ORANGE OIL FLORIDA TYPE VALENZIA 25 Patchouli Light 2 PHENYLETHYL ALCOHOL 20 SANDRANOL ®< 5 Vetiverylia Base 5 YLANG MC TYPE BASE 40 ZIBETH ABO394E 10% DPG 1
[0091] According to the perfumers, this perfume composition is revitalized by the addition of 1% by weight of a compound of formula (I) (e.g., the product from Example 1, a 1% solution in DPG). The fruity and floral impression is significantly enhanced. The composition appears more harmonious, adding a natural note. The product from Example 1 (i.e., the isomer mixture of the compound of formula (I)) lends the composition its own character through its inherent odor as well as its modifying and enhancing effect (booster effect), and unites the different olfactory elements. Example 4: Perfume composition (fragrance composition)
[0092] MAGIC Total in g (30 parts): 1.000,00 ALDEHYDE C14 SOG 5 AMBERWOOD ®< F 15 AMBROCENIDE ®< 10 DPG 10% DPG 15 BENZYL ACETATE 10 BENZYL SALICYLATE 95 BERGAMOT IDENTOIL ®< COLOURLESS 25 Cashmere 5 CEDARWOOD OIL CHIN. 20 DAMASCONE DELTA 10% DPG 10 DIPROPYLENE GLYCOL 195 ELEMIOEL 5 ETHYLVANILLIN 5 FRAMBINONE ®< 15 Geraniol 60 10 GLOBALIDE ®< 120 HEDION 65 HELIONAL 10 IONON BETA 20 ISO E SUPER 95 JASMINE ABS. BASE 25 LILIAL 95 METHYL BENZOATE 10% DPG 5 ORANGE OIL 15 REAL PATCHOULI OIL 25 PHENYLETHYL ALCOHOL 35 ROSE OXIDE HIGH CIS 10% DPG 5 VANILLIN 10 YSAMBER ®< K 35 ZIBETH ABO394E 10% DPG 5 CINNAMON ALCOHOL 5
[0093] According to perfumers, the perfume composition gains radiance through the addition of 1% by weight of a compound of formula (I) (e.g., the product from Example 1, a 1% solution in DPG). The impression of a delicate leather note is significantly enhanced. The composition appears softer, with a natural note added. The product from Example 1 (i.e., the isomer mixture of the compound of formula (I)) lends the composition its own character through its inherent odor as well as its modifying and enhancing effect (booster effect), and unites the various olfactory elements. Example 5: Shampoo
[0094] The product to be used according to the invention from Example 1 (ie the isomer mixture of the compound of formula (I)) was incorporated in a dosage of 0.5 wt.% into a shampoo base of the following composition: Sodium lauryl ether sulfate (e.g. Texapon NSO, Cognis Deutschland GmbH) 12% Cocamidopropyl betaine (e.g. Dehyton K, Cognis Deutschland GmbH) 2% Sodium chloride 1,4% Citric acid 1,3% Phenoxyethanol, methyl, ethyl, butyl and propyl paraben 0,5% Water 82,8%
[0095] The pH of the shampoo base was approximately 6. From this, 100 mL of a 20 wt% aqueous shampoo solution was prepared. Two strands of hair were washed together in this shampoo solution for 2 minutes and then rinsed under lukewarm running water for 20 seconds. One strand of hair was wrapped wet in aluminum foil, and the second strand was dried with a hairdryer. Both strands were assessed for odor by a panel.
[0096] Odor description of both hair strands: Strongly woody, animalic, earthy with an amber note. Example 6: Fabric softener
[0097] The perfume composition from Example 2 (after adding 1% by weight of a 1% solution of the product from Example 1 in DPG) was incorporated in a dosage of 0.5% by weight into a fabric softener base with the following composition: Quarternary ammonium methosulfate (esterquat), approx. 90% (e.g. Rewoquat WE 18, Witco Surfactants GmbH) 5,5% Alkyldimethylbenzylammonium chloride, approx. 50% (e.g. Preventol R50, Bayer AG) 0,2% Color solution, approx. 1% 0,3% Water 94,0%
[0098] The pH of the fabric softener base was in the range of 2 to 3. Two cloth rags were rinsed with 370 g of a 1% aqueous fabric softener solution based on the fabric softener base containing 0.5% w / w of the perfume composition from Example 2 in a line test machine using the fabric softener program for 30 minutes at 20°C. The rags were wrung out and then spun for 20 seconds. One rag was shrink-wrapped while wet, and the other was hung up to dry. Both rags were then evaluated for odor by a panel.
[0099] Odor description of both cloth rags: Rounded and harmonious in smell, with a fine leather note. Example 7: Washing powder
[0100] The perfume oil composition from Example 3 (after adding 1% by weight of a 1% solution of the product from Example 1 in DPG) was incorporated at a dosage of 0.4% by weight into a washing powder base of the following recipe: Linear Na alkyl benzene sulfonate 8,8 % Ethoxylated fatty alcohol C12-18 (7 EO) 4,7 % Na soap 3,2 % Defoamer DOW CORNING 2-4248S POWDERED ANTIFOAM, silicone oil on zeolite as carrier material 3,9 % Zeolite 4A 28,3 % Na carbonate 11,6 % Na salt of a copolymer of acrylic and maleic acid (Sokalan CP5) 2,4 % Na silicate 3,0 % Carboxymethylcellulose 1,2 % Dequest 2066 ([[(Phosphonomethyl)imino]bis[(ethylenenitrilo)bis(methylene)]]tetrakisphosphonic acid, sodium salt) 2,8 % Optical brightener 0,2 % Na sulfate 6,5 % Protease 0,4 % Sodium perborate tetrahydrate 22,0 % TAED 1,0 %
[0101] Two cloth rags were washed with 370 g of a 1% aqueous washing powder solution based on the washing powder base containing 0.4% by weight of the perfume oil composition from Example 3 (the pH of the washing powder solution is clearly in the alkaline range) in a Linetest washing machine on the main wash cycle for 45 minutes at 60°C. The rags were first rinsed with cold water for 5 minutes, wrung out, and then spun for 20 seconds. One rag was shrink-wrapped while wet, and the other was hung up to dry. Both rags were then assessed for odor by a panel.
[0102] Odor description of both cloth rags: Fruity and floral, harmonious, with a natural woody note. Example 8: Toothpaste
[0103] Toothpaste composition comprising a fragrance and aroma composition with wintergreen character Example 8.1 (comparison example):
[0104] By mixing 17 % by weight Peppermint oil Mentha arvensis, rectified 17,5 % by weight Peppermint oil Mentha piperita type Willamette 25 % by weight Methyl salicylate 40 % by weight I-Menthol 0,5 % by weight Menthanecarboxylic acid N-(4-methoxyphenyl)amide A fragrance and flavoring composition for toothpaste compositions with wintergreen character was produced. Example 8.2:
[0105] By mixing 17 % by weight Peppermint oil Mentha arvensis, rectified 17,5 % by weight Peppermint oil Mentha piperita type Willamette 25 % by weight Methyl salicylate 40 % by weight I-Menthol 0,3 % by weight Menthanecarboxylic acid N-(4-methoxyphenyl)amide 0,2 % by weight Product from Example 1 (compound of formula (I)) A fragrance and flavor composition according to the invention was prepared with a proportion of 0.2 wt.% of the compound of formula (I) for toothpaste compositions with wintergreen character.
[0106] The fragrance and flavor compositions according to Example 8.1 (for a comparative toothpaste composition) and Example 8.2 (for a toothpaste composition according to the invention) were each incorporated into a respective standard silica-based toothpaste composition at a concentration of 1.2 wt.%, based on the total mass of the resulting toothpaste.
[0107] The resulting toothpastes were tested by a sensory-trained panel of experts under practical conditions. The sensory evaluation for the toothpaste containing a fragrance and flavor composition according to Example 8.2 revealed a distinct, fresh, peppermint wintergreen note with a very strong and distinct, very long-lasting, cooling sensation and a slight chlorine note, which conveys the antibacterial effectiveness of the toothpaste. The chlorine note was not perceptible in the comparison toothpaste composition 8.1. Example 9: Mouthwash
[0108] Mouthwash or mouthwash concentrate comprising a fragrance and aroma composition with eucalyptus character Example 9.1 (comparison example):
[0109] By mixing 10 % by weight Anethole 17,5 % by weight Eucalyptus oil (70-75% 1,8-cineole) 17,5 % by weight 1,8-Cineole (Eucalyptol) 54,4 % by weight I -Menthol 0,6 % by weight Menthanecarboxylic acid N-(4-methoxyphenyl)amide A fragrance and flavor composition was produced for use in mouthwashes or mouthwash concentrates. Example 9.2:
[0110] By mixing 10 % by weight Anethole 17,5 % by weight Eucalyptus oil (70-75% 1,8-cineole) 17,5 % by weight 1,8-Cineole (Eucalyptol) 54,4 % by weight I -Menthol 0,3 % by weight Menthanecarboxylic acid N-(4-methoxyphenyl)amide 0,3 % by weight Product from Example 1 (compound of formula (I)) A fragrance and flavoring composition containing 0.2% by weight of the compound of formula (I) was prepared for use in mouthwashes or mouthwash concentrates.
[0111] The fragrance and flavor compositions according to Example 9.1 (for a comparison mouthwash or a comparison mouthwash concentrate) and Example 9.2 (for a mouthwash according to the invention or a mouthwash concentrate according to the invention) were each incorporated into a ready-to-use mouthwash at a concentration of 0.45 wt.% and into a ready-to-use mouthwash concentrate at a concentration of 3 wt.%, based on the total mass of the resulting mouthwash or the resulting mouthwash concentrate.
[0112] The resulting mouthwashes and mouthwash concentrates were tested by a sensory-trained panel of experts under practical conditions. The sensory evaluation for the mouthwash / mouthwash concentrate containing an odor and flavor composition according to Example 9.2 revealed a strong, pleasantly fresh eucalyptus note with a very long-lasting sensation of freshness, which persisted for well over 30 minutes after use of the mouthwash / mouthwash concentrate. In addition, a chlorine note was clearly perceptible, conveying an impression of hygiene and antibacterial effectiveness. In contrast, the mouthwash / mouthwash concentrate containing an odor and flavor composition according to Example 9.1 exhibited no perceptible chlorine note. Example 10: All-purpose cleaner
[0113] material Manufacturer Chemical name function % by weight Deionized water Water solvent 59,6 Mergal K9N Troy Chemie, Seelze 5-Chloro-2-methyl-3-(2H)-isothiazolone and 2-methyl-3-(2H)-isothiazolone Preservatives 0,1 Trisodium citrate dihydrate Different Tri Sodium Citrate Dihydrate Complexing agents 3,0 Zetesol NL-2 Zschimmer & Schwarz, Germany Fatty alcohol C12-14-sulfate, sodium Anionic surfactant 30,0 Imbentin C / 125 / 055 Dr. W. Kolb AG Chem. Fatty alcohol C12-C15, 8EO Non-ionic surfactant 5,0 Ethanol 96% Different Ethanol solvent 2,0 Perfume composition from example 3 Symrise Perfume (Fragrance) 0,3
[0114] At a dosage of 0.3 wt.% of the perfume composition from Example 3 in the all-purpose cleaner, the following result is obtained: Adding 1 wt.% of a 1% solution of the product from Example 1 in DPG (based on the total weight of the perfume composition from Example 3) to the all-purpose cleaner significantly enhances the impression of fruitiness and florality. Furthermore, after adding the compound of formula (I), a subtle chloro-skatole note can be perceived, conveying the impression of cleanliness and hygiene.
Claims
1. Use of a compound of formula (I), as fragrance and / or flavoring for imparting, modifying and / or enhancing one or more scent and / or flavor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalistic, sweet, earthy, ambery, fatty, metallic, balsamic, leather note and chlorine note, preferably one or more of the scent and / or flavor notes selected from the group consisting of the notes green, woody, animalistic, earthy, ambery, fruity, floral, leather note and chlorine note.
2. Fragrance and / or flavoring composition comprising or consisting of a compound of formula (I) and one, two, three, four, five, six, seven, eight, nine, ten or more further fragrance(s) and / or flavoring(s), wherein the weight ratio of the total amount of compound of formula (I) to the total amount of further fragrance(s) and / or flavoring(s) is in the range of 1 : 1000 to 1 : 0.1, preferably 1 : 1000 to 1 : 0.5, and wherein the total amount of the compound of formula (I) in the fragrance and / or flavoring composition is contained in an amount sufficient to impart and / or enhance one or more scent and / or flavor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalistic, sweet, earthy, ambery, fatty, metallic, balsamic, leather note and chlorine note, preferably at least one of the scent and / or flavor notes selected from the group consisting of the notes green, woody, animalistic, earthy, ambery, fruity, floral, leather note and chlorine note, and / or to modify one or more scent and / or flavor notes of a or the further fragrance(s) and / or flavoring(s) of the fragrance and / or flavoring composition in the direction of one or more of said scent and / or flavor notes.
3. Fragrance and / or flavoring composition according to claim 2, wherein the total amount of the compound of formula (I), based on the total weight of the fragrance and / or flavoring composition, is in the range of 0.0001 to 90% by weight.
4. Fragrance and / or flavoring composition according to one of the claims 2 or 3, wherein (i) the or one, several or all of the further fragrances and / or flavorings (also) impart, modify and / or enhance one or more scent and / or flavor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalistic, sweet, earthy, ambery, fatty, metallic, balsamic, leather note and chlorine note, preferably one or more of the scent and / or flavor notes selected from the group consisting of the notes green, woody, animalistic, earthy, ambery, fruity, floral, leather note and chlorine note, particularly preferably selected from the group consisting of the notes fruity, floral and chlorine note, or wherein (ii) the or one, several or all of the further fragrances and / or flavorings impart, modify and / or enhance one or more scent and / or flavor notes other than those mentioned in (i).
5. Use of a fragrance and / or flavoring composition according to one of claims 2 to 4 for imparting, modifying and / or enhancing one or more scent and / or flavor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalistic, sweet, earthy, ambery, fatty, metallic, balsamic, leather note and chlorine note, preferably at least one of the scent and / or flavor notes selected from the group consisting of the notes green, woody, animalistic, earthy, ambery, fruity, floral, leather note and chlorine note.
6. Method for imparting, enhancing and / or modifying one or more scent and / or flavor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalistic, sweet, earthy, ambery, fatty, metallic, balsamic, leather note and chlorine note, preferably for imparting, enhancing and / or modifying one or more scent and / or flavor notes selected from the group consisting of the notes green, woody, animalistic, earthy, ambery, fruity, floral, leather note and chlorine note, comprising or consisting of the following steps: (a) Providing (a.1) the compound of formula (I) and (a.2) one, two, three, four, five, six, seven, eight, nine, ten or more further fragrance(s) and / or flavoring(s) with one or more scent and / or flavor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalistic, sweet, earthy, ambery, fatty, metallic, balsamic, leather note and chlorine note, preferably with one or more scent and / or flavor notes selected from the group consisting of the notes green, woody, animalistic, earthy, ambery, fruity, floral, leather note and chlorine note, (b) adding the compound of formula (I) (a.1) to the further fragrance(s) and / or flavoring(s) (a.2), in an amount sufficient to impart, enhance and / or modify one or more scent and / or flavor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalistic, sweet, earthy, ambery, fatty, metallic, balsamic, leather note and chlorine note, preferably in an amount sufficient to impart, modify and / or enhance one or more scent and / or flavor notes selected from the group consisting of the notes green, woody, animalistic, earthy, ambery, fruity, floral, leather note and chlorine note.
7. Perfumed and / or flavored article, comprising or consisting of (i) a fragrance and / or flavoring composition according to any of the claims 2 to 4, or the compound of formula (I) and one, two, three, four, five, six, seven, eight, nine, ten or more further fragrance(s) and / or flavoring(s), wherein the weight ratio of the total amount of the compound of formula (I) to the total amount of further fragrance(s) and / or flavoring(s) is in the range of 1 : 1000 to 1 : 0.1, preferably 1 : 1000 to 1 : 0.5, and (ii) one or more further component(s), preferably at least one or several, preferably one, two, three, four, five or more, additive(s), excipient(s) and / or active substance(s), and wherein the article is selected from the group consisting of laundry and cleaning detergents, hygiene or care products, preferably in the field of body, hair and oral care, cosmetics and household, preferably from the group consisting of surface cleaners, WC cleaners, all-purpose cleaners, mouthwashes, toothpastes, tooth gels, dentifrices, tooth powders, tooth care chewing gums, perfume extracts, eau de parfums, eau de toilettes, shaving lotions, eau de colognes, pre-shave products, splash colognes, perfumed refreshing wipes, acidic, alkaline or neutral detergents, textile fresheners, ironing aids, liquid laundry detergents, powdery laundry detergents, laundry pretreatment agents, fabric softeners, washing soaps, washing tablets, disinfectants, surface disinfectants, air fresheners, aerosol sprays, waxes and polishes, body care products, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, after-shave creams and lotions, tanning creams and lotions, hair care products, deodorants, antiperspirants, decorative cosmetic products, candles, lamp oils, incense sticks, insecticides, repellents and fuels.
8. Perfumed and / or flavored article according to claim 7, wherein component (i) is contained in an amount sufficient for a consumer to perceive one or more scent and / or flavor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalistic, sweet, earthy, ambery, fatty, metallic, balsamic, leather note and chlorine note, preferably one or more scent and / or flavor notes selected from the group consisting of the notes green, woody, animalistic, earthy, ambery, fruity, floral, leather note and chlorine note.
9. Perfumed and / or flavored article according to any of the claims 7 or 8, wherein the total amount of the compound of formula (I), based on the total weight of the article, is in the range of 0.00001 to 10% by weight, preferably 0.0001 to 5% by weight, particularly preferably 0.001 to 2% by weight, more preferably 0.005 to 1% by weight.
10. Method for perfuming and / or flavoring an article, comprising or consisting of the steps of: (a) Providing (a.1) a fragrance and / or flavoring composition according to any of the claims 2 to 4, or (a.2) the compound of formula (I) and optionally one, two, three, four, five, six, seven, eight, nine, ten or more further fragrance(s) and / or flavoring(s), wherein the weight ratio of the total amount of the compound of formula (I) to the total amount of further fragrance(s) and / or flavoring(s) is in the range from 1 : 1000 to 1 : 0.1, preferably from 1 : 1000 to 1 : 0.5, and (b) adding the fragrance and / or flavoring composition (a.1) or the compound / fragrances (a.2) to the article to be perfumed and / or flavored, in an amount sufficient to impart, enhance and / or modify one or more scent and / or flavor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalistic, sweet, earthy, ambery, fatty, metallic, balsamic, leather note and chlorine note, preferably one or more of the scent and / or flavor notes selected from the group consisting of the notes green, woody, animalistic, earthy, ambery, fruity, floral, leather note and chlorine note.
11. Method for perfuming hair, skin, textile fibers, surfaces and / or room air comprising or consisting of the following steps: (a) Providing (a.1) a fragrance and / or flavoring composition according to any of the claims 2 to 4, preferably containing a surfactant or a surfactant mixture, or (a.2) the compound of formula (I) and optionally one, two, three, four, five, six, seven, eight, nine, ten or more further fragrance(s) and / or flavoring(s), wherein the weight ratio of the total amount of the compound of formula (I) to the total amount of further fragrance(s) and / or flavoring(s) is in the range from 1 : 1000 to 1 : 0.1, preferably from 1 : 1000 to 1 : 0.5, and preferably additionally a surfactant or a surfactant mixture, or (a.3) an article according to any of the claims 7 to 9, preferably containing a surfactant or a surfactant mixture, and (b) applying or incorporating the fragrance and / or flavoring composition (a.1) or the compound / fragrances (a.2) or the article (a.3) to the hair or skin or fibers or surface to be perfumed, or into the room air to be perfumed in an amount sufficient for the consumer to perceive one or more scent and / or flavor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, animalistic, sweet, earthy, ambery, fatty, metallic, balsamic, leather note and chlorine note, preferably at least one of the scent and / or flavor notes selected from the group consisting of the notes green, woody, animalistic, earthy, ambery, fruity, floral, leather note and chlorine note.