Esters of cyclohexane and / or cyclohexene as fragrances

Abstract

The present invention proposes the use of at least one compound of formula I as a fragrance. [Chemical 1] TIFF2025524083000018.tif72162

Description

Technical Field

[0001] The present invention relates to the use of cyclohexane and / or cyclohexene esters as fragrances. Furthermore, the present invention relates to fragrance compositions, their use, and methods for imparting, modifying and / or enhancing specific fragrance notes.

Background Art

[0002] In the perfume industry, there is always a demand for the creation of new fragrances. However, the creation of new fragrances and fragrance compositions involves many challenges. For example, in order to meet specific market needs and provide products that match specific profiles required by customers, it is necessary to select specific compositions of a small number of fragrances from a virtually infinite number of possible structures known from the prior art. Suitable fragrances exhibit very beneficial properties, but when combined with other fragrances, they may exhibit unfavorable odor aspects due to being unpleasant, making it difficult or even impossible to use them for specific purposes.

[0003] The second important issue relates to the need to provide fragrance compositions that not only match specific odor profiles but also have so-called second beneficial properties. In fact, many fragrance compositions known in the market have not only serious drawbacks in use such as poor solubility and low stability to storage, but also have not been successful in subjective issues such as richness and charisma. Furthermore, many of the known fragrance compositions require high dosages to obtain the desired odor results. Another requirement for today's fragrances is high biodegradability and dermatological and toxicological safety. Therefore, there is a particular need to provide fragrances that have a great effect on other fragrances even in small amounts, rather change the impression of unpleasant odors into positive ones, and / or enhance the impression of pleasant odors.

Summary of the Invention

Problems to be Solved by the Invention

[0004] Accordingly, the underlying problem of the present invention was to provide a novel fragrance having the ability to enhance the positive and beneficial fragrance aspects of other fragrances and / or (simultaneously) reduce, suppress and / or mask the unwanted and unpleasant fragrance aspects. In particular, said novel fragrance should also have the feature of improving the stability, solubility and overall performance of other fragrances and reducing the required dosage. Finally, it is required that the fragrance composition itself has excellent biodegradability and is harmless to humans and the environment.

Means for Solving the Problem

[0005] This problem is solved by using at least one compound of formula I

[0006]

Chemical formula

[0007] The compounds of formula I used according to the present invention may exist in the form of any stereoisomer or as a mixture of any stereoisomers.

[0008] What has been said herein about the compounds of formula I, in particular the advantages described herein, apply also to mixtures of stereoisomers of the compounds of formula I used or employed according to the present invention or to mixtures of different compounds of formula I.

[0009] The said compounds of formula I have very unique olfactory properties, clearly different from and even overriding those of known odoriferous substances. The suitability of the said compounds of formula I as fragrances was not previously known. Thus, it is particularly surprising that in a field that has already been well studied, a fragrance having valuable and interesting complex olfactory properties has been found.

[0010] As described above, the suitability of the compounds of formula I as fragrances is not known. Similarly, while an exact description of the odor is not available, according to the inventors, the compounds of formula I have, inter alia, a cinnamon-like odor, a marzipan-like odor, a fruity odor, a valerate-like odor, a sweet odor, an apple-like odor, a pear-like odor, a pineapple-like odor, a strawberry-like odor, a green odor and / or a castoreum-like odor.

[0011] As a result, the inventors have made the surprising discovery that the compounds of formula I are suitable as fragrances and, in small amounts, produce a special effect in combination with other fragrances.

[0012] For the sake of clarity, the expression "the dotted line represents a carbon-carbon single bond or a carbon-carbon double bond" or a similar expression represents the ordinary meaning understood by those skilled in the art, i.e., the entire bond (solid and dotted line) between the carbon atoms connected by said dotted line is a single bond or a double bond.

[0013] In a preferred embodiment according to the invention, R represents ethyl, butyl or cyclopentyl. In a further preferred embodiment according to the invention, R represents ethyl, butyl or cyclopentyl and the dotted line represents a carbon-carbon single bond. In a further preferred embodiment according to the invention, R represents ethyl, butyl or cyclopentyl and the dotted line represents a carbon-carbon double bond.

[0014] Preferably, the compound of formula I is ethyl cyclohexene-1-carboxylate and has the structure according to formula II,

[0015]

Chemical formula

[0016] Preferably, ethyl cyclohexene-1-carboxylate has the following odor notes: cinnamon note, marzipan note, chlorine note and / or benzophenone note.

[0017] More preferably, the compound of formula I is butyl cyclohexene carboxylate and has the structure according to formula III,

[0018]

Chemical formula

[0019] Preferably, butyl cyclohexene carboxylate has the following odor notes: fruity note, valerianate note, sweet note, cinnamon note, castoreum note, apple note, pear note and / or pineapple note.

[0020] More preferably, the compound of formula I is cyclopentyl cyclohexanecarboxylate and has the structure according to formula IV,

[0021]

Chemical formula

[0022] Preferably, cyclopentyl cyclohexanecarboxylate has the following odor notes: fruity note, pineapple note, green note and / or strawberry note.

[0023] More preferably, the compound of formula I is selected from the group consisting of ethyl cyclohexene-1-carboxylate, butyl cyclohexene carboxylate, cyclopentyl cyclohexanecarboxylate or a mixture thereof.

[0024] In a preferred embodiment according to the invention, at least one compound of formula I is used in a fragrance composition to obtain at least one of the following fragrance notes: cinnamon note, marzipan note, fruity note, valerianate note, sweet note, apple note, pear note, pineapple note, strawberry note, green note and / or castoreum note. Even more preferred is to use at least one compound of formula I to impart, modify and / or enhance the fragrance notes of a fragrance composition to make it more fruity, more juicy, softer, clearer, fresher, sweeter and / or more floral. However, among the compounds of formula I, there are some that, like ethyl cyclohexene-1-carboxylate for example, not only do not have a fruity note, a juicy note or a floral note, and / or have few pleasant odor notes, which is particularly surprising in light of the above description of the odor.

[0025] The fact that the compounds of formula I used according to the invention can give a very complex and varied overall sensory impression is particularly surprising, such an impression usually being achievable only by a mixture of multiple components (such as a mixture of essential oils and spices).

[0026] In addition to their primary, i.e., olfactory, properties, the compounds of formula I also have positive secondary properties, in particular high substantivity compared to fragrances with similar olfactory properties, as well as high stability, high spreadability and biodegradability in certain media and preparations.

[0027] In connection with their preferred use for imparting, modifying and / or enhancing fragrance notes, it is also recognized that the compounds of formula I can perform an excellent function as so-called boosters (amplifiers; enhancers).

[0028] Furthermore, the compounds of formula I used according to the present invention can enhance the strength of a perfume mixture (perfume composition) and round off the overall odor of said mixture. Accordingly, the compounds described herein can be used to add fullness, freshness, (diffusive) power, radiance, roundness, harmony, naturalness to a perfume composition and / or reduce greasiness, and in particular, said compounds can be used to impart more softness, more transparency and / or more freshness to a perfume composition.

[0029] Furthermore, said compounds of formula I are suitable as agents for enhancing the substantivity and / or retention of a perfume composition.

[0030] The compounds of formula I can be used in various products and can be used as a single perfume, but particularly advantageously, they can be combined in different ratios with other perfumes to form a perfume mixture and can also create new and original perfume compositions. Accordingly, one aspect of the present invention also relates to a perfume mixture containing at least one compound 4-cyclohexylbutan-2-one of formula I and optionally further constituents (such as solvents).

[0031] The perfume composition according to the present invention has formula I

[0032]

Chemical formula

[0033] In a preferred embodiment, the compound of formula I is selected from the group consisting of ethyl cyclohexene-1-carboxylate, butyl cyclohexene carboxylate, cyclopentyl cyclohexanecarboxylate, or mixtures thereof.

[0034] Preferably, the flavor composition according to the present invention comprises or consists of at least one compound of formula I and two or three or more additional flavors. More preferably, the flavor composition according to the present invention comprises or consists of at least one compound of formula I and three or four or more additional flavors. Most preferably, the flavor composition according to the present invention comprises or consists of at least one compound of formula I and four or five or more additional flavors.

[0035] Preferably, the flavor composition according to the present invention comprises or consists of ethyl cyclohexene-1-carboxylate and two or three or more additional flavors. More preferably, the flavor composition according to the present invention comprises or consists of ethyl cyclohexene-1-carboxylate and three or four or more additional flavors. Most preferably, the flavor composition according to the present invention comprises or consists of ethyl cyclohexene-1-carboxylate and four or five or more additional flavors.

[0036] Preferably, the flavor composition according to the present invention comprises or consists of butyl cyclohexene carboxylate and two or three or more additional flavors. More preferably, the flavor composition according to the present invention comprises or consists of butyl cyclohexene carboxylate and three or four or more additional flavors. Most preferably, the flavor composition according to the present invention comprises or consists of butyl cyclohexene carboxylate and four or five or more additional flavors.

[0037] Preferably, the perfume composition according to the present invention comprises or consists of cyclopentyl cyclohexanecarboxylate and two or more additional perfumes. More preferably, the perfume composition according to the present invention comprises or consists of cyclopentyl cyclohexanecarboxylate and three or more additional perfumes. Most preferably, the perfume composition according to the present invention comprises or consists of cyclopentyl cyclohexanecarboxylate and four or more additional perfumes.

[0038] The compound of formula I according to the present invention is usually used in a functionally effective amount, i.e., the total amount that exerts a functional effect.

[0039] Preferably, the weight ratio of the at least one compound of formula I to the total amount of other perfumes is in the range of 1:100 to 1:10. More preferably, the weight ratio of the at least one compound of formula I to the total amount of other perfumes is in the range of 1:85 to 1:15.

[0040] In this context, the total amount of the at least one compound of formula I is, in each case, 0.0001 to 99.9% by weight, preferably 0.001 to 99.5% by weight, particularly preferably 0.01 to 99% by weight, 0.01 to 90% by weight, 0.01 to 50% by weight, 0.01 to 20% by weight, 0.01 to 10% by weight, particularly preferably 0.01 to 5% by weight, especially 0.05 to 2.0% by weight, based on the total weight of the composition.

[0041] In a preferred embodiment according to the present invention, the compound of formula I is contained in the perfume composition in a functionally effective amount sufficient to modify an existing perfume and make it more fruity, more juicy, softer, clearer, fresher, sweeter and / or more floral.

[0042] Examples of fragrances which can advantageously be combined with the compounds of formula I in the context of the present invention can be found, for example, in S. Arctander, Perfume and Flavor Materials, Vol. I and II, Montclair, N. J. 1969, self - published, or K. Bauer et al., Common Fragrance and Flavor Materials, 4th Edition, Wiley - VCH, Weinheim 2001.

[0043] Specifically, the following may be mentioned: extracts from natural raw materials such as essential oils, concretes, absolutes, resins, resinoids, balsams, tinctures. Further particulars are as follows. Ambergris tincture; Amyris oil; Angelica seed oil; Angelica root oil; Anise oil; Valerian oil; Basil oil; Tree moss absolute; Bay oil; Mugwort oil; Benzoin resin; Bergamot oil; Beeswax absolute; Birch tar oil; Bitter almond oil; Savory oil; Broccoli leaf oil; Cabreuva oil; cade oil; Calamus oil; Camphor oil; Cananga oil; Cardamom oil; Cassia oil; Cascarilla oil; Cinnamon oil; Cinnamon absolute; Castoreum absolute; Cider leaf oil; Cider wood oil; Cistus oil; Citronella oil; Citron oil; Copaiba balsam; Copaiba balsam oil; Coriander oil; Costus root oil; Cumin oil; Cypress oil; Davana oil; Dill herb oil; Dill seed oil; Oudh brot absolute; Oak moss absolute; Elemi oil; Tarragon oil; Eucalyptus citriodora oil; Eucalyptus oil; Fennel oil; Spruce needle oil; Galbanum oil; Galbanum resin; Geranium oil; Grapefruit peel oil; Guyac wood oil; Gurjun balsam; Gurjun balsam oil; Helichrysum absolute; Helichrysum oil; Ginger oil; Iris root absolute; Iris root oil; Jasmine absolute; Calamus oil; Chamomile oil blue; Chamomile oil roman; 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; Labège oil; Lime oil distilled; Lime oil pressed; Linaloe oil; Rittéa acube oil; Bay leaf oil; Mace oil; Marjoram oil; Mandarin oil; Massoia bark oil; Mimosa absolute; Musk grain oil; Musk tincture; Muscat sage oil; Nutmeg oil; Myrrh absolute; Myrrh oil; Martol oil; Clove leaf oil; Clove flower oil; Neroli oil; Olibanum absolute; Olibanum oil; Opopanax oil; Orange flower absolute; Orange oil; Oregano oil; Palmarosa oil; Patchouli oil; Egoima oil;Peruvian balsam oil; parsley leaf oil; parsley seed oil; ptych grain oil; peppermint oil; pepper oil; allspice oil; pine oil; poly oil; rose absolute; rosewood oil; rose oil; rosemary oil; sage oil Dalmatian; sage oil Spanish; sandalwood oil; celery seed oil; spicy lavender oil; star anise oil; styrax oil; tagetes oil; fir needle oil; tea tree oil; turpentine oil; thyme oil; tolu balsam; tonka absolute; tuberose absolute; vanilla extract; violet leaf absolute; verbena oil; vetiver oil; juniper berry oil; wine yeast oil; mugwort oil; wintergreen oil; ylang-ylang oil; hyssop oil; civet absolute; cinnamon leaf oil; cinnamon bark oil and their fractions, or components separated therefrom;

[0044] Individual odoriferous 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; Individual odoriferous substances from the group of 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-methylenheptan-2-ol; (E,Z)-2,6-nonadienol; 3,7-dimethyl-7-methoxyoctan-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol; Individual odor substances from the group of 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-methoxy-propoxy)-(E / Z)-3-hexene; Individual odor substances from the group of 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; Individual odor substances from the group of 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; Individual odor substances from the group of aliphatic nitriles, such as 2-nonenoic acid nitrile; 2-undecenoic acid nitrile; 2-tridecenoic acid nitrile; 3,12-tridecadienoic acid nitrile; 3,7-dimethyl-2,6-octadecadienoic acid nitrile; 3,7-dimethyl-6-octenoic acid nitrile; Individual odor substances from the group of esters of aliphatic carboxylic acids, such as (E)- and (Z)-3-hexenyl formate; ethyl acetoacetate; isoamyl acetate; 3,5,5-trimethylhexyl acetate; 3-methyl-2-butenyl acetate; (E)-2-hexenyl acetate; (E)- and (Z)-3-hexenyl acetate; octyl acetate; 3-octyl acetate; 1-octen-3-yl acetate; ethyl butyrate; butyl butyrate; isoamyl butyrate; hexyl butyrate; (E)- and (Z)-3-hexenyl isobutyrate; hexyl crotonate; ethyl isovalerate; ethyl 2-methylpentanoate; ethyl hexanoate; allyl hexanoate; ethyl heptanoate; allyl heptanoate; ethyl octanoate; ethyl (E,Z)-2,4-decadienoate; methyl 2-octynoate; methyl 2-nonynoate; allyl 2-isoamyloxyacetate; methyl 1,3,7-trimethyl-2,6-octadiene-oate; 4-methyl-2-pentyl crotonate; Individual odor substances from the group of acyclic terpene alcohols, such as geraniol; nerol; lavandulol; nerolidol; farnesol; tetrahydrolinalool; tetrahydrogeraniol; 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol; 2,6-dimethyl-7-octen-2-ol; 2,6-dimethyloctan-2-ol; 2-methyl-6-methylene-7-octen-2-ol; 2,6-dimethyl-5,7-octadien-2-ol; 2,6-dimethyl-3,5-octadien-2-ol; 3,7-dimethyl-4,6-octadien-3-ol; 3,7-dimethyloct-6-en-1-ol; (2E)-3,7-dimethylocta-2,6-dien-1-ol; 3,7-dimethyl-1,5,7-octatriene-3-ol; 2,6-dimethyl-2,5J-octatriene-1-ol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoate; Individual odor substances from the group of acyclic terpene aldehydes and ketones, such as citronellal; 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal; geranyl acetone; geranial, dimethyl acetal and diethyl acetal of neral, Individual odor substances from the group of cyclic terpene alcohols, such as menthol; isopulegol; α-terpineol; terpinolene-4; menthan-8-ol; menthan-1-ol; menthan-7-ol; borneol; isoborneol; linalool oxide; nopol; cedrol; ambroxol; vetiverol; guaiol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates, 3-methyl-2-butenoate; Individual odor substances from the group of cyclic terpene aldehydes and ketones, such as menthone; isomenthone; 8-mercaptomenthan-3-one; carvone; camphor; fenchone; α-ionone; β-ionone; α-n-methyliorone; β-n-methyliorone; α-isomethyliorone; β-isomethyl-ionone; α-iron; β-damascenone; 1-(2,4,4-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one; 1,3,4,6,7,8a-hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methano-naphthalen-8(5H)-one; 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal; nootkatone; dihydronootkatone; 4,6,8-megastigmatrien-3-one; α-sinensal; β-sinensal; acetylated cedarwood oil (methyl cedryl ketone); Individual odor substances from the group of cyclic alcohols, such as 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; 4-cyclohexylbutan-2-ol; Individual odor substances from the group of cycloaliphatic alcohols, such as α,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; Individual odor substances from the group of cyclic and cycloaliphatic ethers, such as cineole; cedryl methyl ether; cyclododecyl methyl ether; 1,1-dimethoxycyclododecane; (ethoxymethoxy)cyclododecane; α-cedrene epoxide; 3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan; 3a-ethyl-6,6,9a-trimethyldodecahydronaphtho[2,1-b]furan; 1,5,9-trimethyl-13-oxabicyclo[10.1.0]trideca-4,8-diene; rose oxide; 2-(2,4-dimethyl-3-cyclohexen-1-yl)-5-methyl-5-(1-methylpropyl)-1,3-dioxane; Individual odor substances from the group of cyclic and macrocyclic ketones, such as 4-tert-butylcyclohexanone; 2,2,5-trimethyl-5-pentylcyclopentanone; 2-heptylcyclopentanone; 2-pentylcyclopentanone; 2-hydroxy-3-methyl-2-cyclopenten-1-one; 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one; 3-methyl-2-pentyl-2-cyclopenten-1-one; 3-methyl-4-cyclopentadecenone; 3-methyl-5-cyclopentadecenone; 3-methylcyclopentadecanone; 4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone; 4-tert-pentylcyclohexanone; 5-cyclohexadecen-1-one; 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone; 8-cyclohexadecen-1-one; 9-cycloheptadecen-1-one; cyclopentadecanone; cyclohexadecanone; Individual odor substances from the group of cycloaliphatic aldehydes, such as 2-methyl-4-(2,2,6-trimethyl-cyclohexen-1-yl)-2-butenal; 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarbaldehyde; 4-(4-methyl-3-penten-1-yl)-3-cyclohexenecarbaldehyde; Individual odor substances from the group of cycloaliphatic ketones, such as 1-(3,3-dimethylcyclohexyl)-4-penten-1-one; 2,2-dimethyl-1-(2,4-dimethyl-3-cyclohexen-1-yl)-1-propanone; 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one; 2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthalenyl methyl ketone; methyl 2,6,10-trimethyl-2,5,9-cyclododecatrienyl ketone; tert-butyl-(2,4-dimethyl-3-cyclohexen-1-yl) ketone; Individual odor substances from the group of esters of cyclic alcohols, such as 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert-pentylcyclohexyl acetate; 3,3,5-trimethylcyclohexyl acetate; decahydro-2-naphthyl acetate; 2-cyclopentylcyclopentyl crotonate; 3-pentyltetrahydro-2H-pyran-4-yl acetate; decahydro-2,5,5,8a-tetramethyl-2-naphthyl acetate; 4,7-methano-3a,4,5,6,7,7a-hexahydro-5, resp. 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; Individual odor substances from the group of esters of cycloaliphatic alcohols, such as 1-cyclohexylethyl crotonate; Individual odor substances from the group of esters of cycloaliphatic carboxylic acids, such as allyl 3-cyclohexylpropionate; allyl cyclohexyloxyacetate; cis and trans-methyl dihydrojasmonate; cis and trans-methyl jasmonate; methyl 2-hexyl-3-oxocyclopentanecarboxylate; ethyl 2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate; ethyl 2,3,6,6-tetramethyl-2-cyclohexenecarboxylate; ethyl 2-methyl-1,3-dioxolane-2-acetate; Individual odor substances from the group of aromatic aliphatic alcohols, such as benzyl alcohol; 2-phenylethanol; 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-phenylpropanol; 2-methyl-5-phenylpentanol; 3-methyl-5-phenylpentanol; 3-phenyl-2-propen-1-ol; 4-methoxybenzyl alcohol; 1-(4-isopropylphenyl)ethanol; Individual odor substances from the group of esters of aromatic aliphatic alcohols and aliphatic carboxylic acids, such as benzyl acetate; benzyl propionate; benzyl isobutyrate; benzyl isovalerate; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-phenylethyl isobutyrate; 2-phenylethyl isovalerate; 1-phenylethyl acetate; α-trichloromethylbenzyl acetate; α,α-dimethylphenylethyl acetate; α,α-dimethylphenylethyl butyrate; cinnamyl acetate; 2-phenoxyethyl isobutyrate; 4-methoxybenzyl acetate; Individual odor substances from the group of aromatic aliphatic ethers, such as 2-phenylethyl methyl ether; 2-phenylethyl isoamyl ether; 2-phenylethyl 1-ethoxyethyl ether; phenylacetaldehyde dimethyl acetal; phenylacetaldehyde diethyl acetal; hydratropaldehyde dimethyl acetal; phenylacetaldehyde glycerol acetal; 2,4,6-trimethyl-4-phenyl-1,3-dioxane; 4,4a,5,9b-tetrahydroindeno[1,2-d]-m-dioxin; 4,4a,5,9b-tetrahydro-2,4-dimethylindeno[1,2-d]-m-dioxin; and individual odor substances from the group of aromatic aliphatic aldehydes, such as benzaldehyde; phenylacetaldehyde; 3-phenylpropanal; hydratropaldehyde; 4-methylbenzaldehyde; 4-methylphenylacetaldehyde; 3-(4-ethylphenyl)-2,2-dimethylpropanal; 2-methyl-3-(4-isopropylphenyl)propanal; 2-methyl-3-(4-isobutylphenyl)propanal; 3-(4-tert-butyl-phenyl)propanal; cinnamaldehyde; α-butylcinnamaldehyde; α-hexylcinnamaldehyde; 3-methyl-5-phenylpentanal; 4-methoxybenzaldehyde; 4-hydroxy-3-methoxybenzaldehyde; 4-hydroxy-3-ethoxybenzaldehyde; 3,4-methylenedioxybenzaldehyde; 3,4-dimethoxybenzaldehyde; 2-methyl-3-(4-methoxyphenyl)propanal; 2-methyl-3-(4-methylenedioxyphenyl)propanal; Individual odor substances from the group of aromatic and araliphatic ketones, such as acetophenone; 4-methylacetophenone; 4-methoxyacetophenone; 4-tert-butyl-2,6-dimethylacetophenone; 4-phenyl-2-butanone; 4-(4-hydroxyphenyl)-2-butanone; 1-(2-naphthalenyl)ethanone; 2-benzofuranylethanone; (3-methyl-2-benzofuranylethanone); benzophenone; 1,1,2,3,6-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´,6´,8´,8´-hexamethyl-2-acetonaphthone; Individual odor substances from the group of aromatic and araliphatic carboxylic acids and their esters, such as benzoic acid; phenylacetic acid; methyl benzoate; ethyl benzoate; hexyl benzoate; benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geranyl phenylacetate; phenylethyl phenylacetate; methyl cinnamate; ethyl cinnamate; benzyl cinnamate; phenylethyl cinnamate; cinnamyl cinnamate; allyl phenoxyacetate; methyl salicylate; hexyl salicylate; cyclohexyl salicylate; cis-3-hexenyl salicylate; benzyl salicylate; phenyl ethyl salicylate; methyl 2,4-dihydroxy-3,6-dimethylbenzoate; ethyl 3-phenylglycidate; ethyl 3-methyl-3-phenylglycidate; Individual odor substances from the group of heterocyclic compounds, such as 2,5-dimethyl-4-hydroxy-2H-furan-3-one; 2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one; 3-hydroxy-2-methyl-4H-pyran-4-one; 2-ethyl-3-hydroxy-4H-pyran-4-one; Individual odor substances from the group of lactones, such as 1,4-octanolide; 3-methyl-1,4-octanolide; 1,4-nonanolide; 1,4-decanolide; 8-decen-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-hexadecanolide; 9-hexadecen-1,16-olide; 10-oxa-1,16-hexadecanolide; 11-oxa-1,16-hexadecanolide; 12-oxa-1,16-hexadecanolide; ethylene-1,12-dodecanedioate; ethylene-1,13-tridecanedioate; 2,3-dihydrocoumarin; octahydrocoumarin.

[0045] In a preferred embodiment according to the present invention, the at least one additional fragrance is Agrumex LC, Aldehyde C10, Aldehyde C11 undecanal, Aldehyde C12 laurin, Aldehyde C12 MNA, Aldehyde C11 MOA pure, allyl cyclohexylpropionate, allyl heptylate, Ambroxide 10% IPM, anisaldehyde pure, Calone 10%, Carboxylic L, coumarin, cyclodumol acetate, 2,6-dimethyl-7-octen-2-ol (dihydromyrcenol), DYNASCONE® 1% DPG, FARENAL® 10% DPG, Florazon, FLORHYDRAL® , Florosa BM / Pyranol, FRUCTATE®, Furaminton / Tonkalactone™ 1% DPG, GLOBALIDE®, methyl 3-oxo-2-pentyl-1-cyclopentylacetate (HEDION®), heliotropin / piperonal, hexyl acetate, hexyl salicylate, isoamyl acetate, Spirit Mint Oil (KRAUSEMINZOEL) 65% from the United States, LEAFOVERT®, linolal, MAGNOLAN®, MELONAL®, methyl naphthyl ketone beta crystal, neroliol 0.Selected from the group consisting of 1% DPG, 2-phenylethanol (phenylethyl alcohol), Timber Silk, VERTOMUGAL (registered trademark), ethyl acetoacetate, aldehyde C14 SOG, aldehyde C18 SOG, allyl caproate, benzaldehyde DD, citral FF, citronellol 950, citronellyl acetate extra, lemon oil from Italy, lemon oil terpene, cyclamen aldehyde, damasconone, damascone delta, decalactone gamma, ethyl butyrate, ethyl maltol, ethyl-2-methylbutyrate (ethyl methyl butyrate-2), geranyl acetate pure, heliotropin / piperonal, HERBAFLORAT (registered trademark), cis-3-hexenol, cis-3-hexenyl acetate, ionone beta, ISO E SUPER (registered trademark), isoborneol, isopropylmethylthiazole-2,4 10% DPG, jasmaplurnut, linalool, MANZANATE (registered trademark), octalactone gamma, styrallyl acetate, SYMFRESH (registered trademark) NX, thiomenthanone-8,3 10% DPG, undecabeltol, vanillin, vertocitral (VERTOCITRAL), allylamyl glycolate, alpha-amylcinnamaldehyde, benzyl acetate, dimethylbenzylcarbinyl butyrate (dimethylbenzylcarbinyl butyrate), dodecalactone gamma, ethylene brassylate, ethyl linalool, ethyl vanillin, floropal, FRAMBINON (registered trademark), herbyl propionate, alpha-hexylcinnamaldehyde, isoamyl acetate, isoamyl butyrate, jasmaplurnut (JASMAPRUNAT), MACROLIDE (registered trademark) supra, methyl anthranilate (METHYLANTHRANILAT), methyl cinnamate, mugetanol, PHENIRAT (registered trademark), prenyl acetate and ROMANDOLIDE (registered trademark).

[0046] Preferably, at least one compound of formula I is combined with one or two or more, particularly preferably two, three, four, five or six or more of their preferred other fragrances.

[0047] A perfume composition (= fragrance mixture) containing at least one compound of formula I is advantageously used in liquid form, undiluted or diluted with a solvent, for perfume making. Suitable solvents are, for example, ethanol, isopropanol, diethylene glycol monoethyl ether, glycerin, propylene glycol, 1,2 - butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, etc.

[0048] Furthermore, the perfume composition according to the invention can be adsorbed on a carrier which ensures both a fine distribution of the perfume in the product and a controlled release during use. Such carriers can be porous inorganic materials such as light sulfate, silica gel, zeolite, plaster, clay, clay granules, cellular concrete, or organic materials such as wood, cellulose - based substances, sugar, dextrin (e.g., maltodextrin) or plastics such as PVC, polyvinyl acetate or polyurethane. The combination obtained from the composition according to the invention and the carrier substance is also understood as a perfume composition according to the invention.

[0049] The perfume composition according to the invention can also be microencapsulated, spray - dried, used as an inclusion complex or as an extruded product and added in this form, for example, to the product to be perfumed.

[0050] If necessary, the properties of the composition thus modified can be further optimized, from the point of view of a more targeted release of the perfume, by means of a so - called "coating" with a suitable material. For this purpose, waxy plastics such as polyvinyl alcohol are preferably used. As a result, the product thus obtained becomes an article according to the invention.

[0051] A further aspect of the invention relates to the use of a perfume composition for modifying an existing perfume to make it more fruity, more juicy, softer, clearer, fresher, sweeter and / or more floral. The above - mentioned preferred embodiments are also applicable to the use of the perfume composition.

[0052] The perfume composition according to the present invention can advantageously be used in concentrated form, in solution, or in the improved form described above, for the manufacture of perfumed articles according to the present invention. Specific examples of said articles include B. perfume extracts, eau de parfum, eau de toilette, aftershave, eau de cologne, pre-shave products, splash cologne and aromatic refreshment towels, as well as acidic, alkaline and neutral detergents, such as floor cleaners, window glass cleaners, dishwashing detergents, bathroom and sanitary cleaners, abrasive emulsions, solid and liquid toilet cleaners, powder and foam carpet cleaners, fabric perfumes, ironing aids, liquid detergents, powder detergents, fragrance imparting agents, pre-washing treatment agents, such as bleaching agents, soaking agents, stain removers, softening finishes, laundry soaps, laundry tablets, as well as bactericidal perfumes, aerosol sprays, waxes and polishes, such as furniture polishes, floor waxes, shoe creams, in the form applied to liquid, gel-like or solid carriers, and personal care products such as solid and liquid soaps, shower gels, shampoos, beard soaps, beard foams, bath oils, water-in-oil, oil-in-water and water-in-oil-in-water cosmetic emulsions, such as skin creams and skin lotions, face creams and face lotions, sunscreens and sun lotions, aftersun creams and aftersun lotions, hand creams and hand lotions, foot creams and foot lotions, depilatory creams and depilatory lotions, aftershave creams and aftershave lotions, sunburn creams and sunburn lotions, hair care products, such as hair sprays, hair gels, hair setting lotions, hair conditioners, permanent hair dyes, semi-permanent hair dyes, hair forming agents, such as cold wave agents, hair straightening agents, hair lotions, hair creams, hair lotions, deodorants and antiperspirants, such as underarm sprays, roll-ons, deodorant sticks, deodorant creams, decorative cosmetics, such as eye shadows, nail polishes, lipsticks, mascaras, as well as products such as candles, lamp oils, incense sticks, insecticides, repellents, fuels, etc.

[0053] Of course, the perfume composition according to the present invention can also be included in cosmetic compositions and household compositions.

[0054] Another aspect of the present invention relates to a method of modifying an existing perfume to make it more fruity, more juicy, softer, clearer, fresher, sweeter and / or more floral. The method comprises the following steps: (a) preparing at least one compound of formula I

[0055] [Chemical formula] wherein R represents ethyl, propyl, butyl or cyclopentyl; and the dotted line represents a carbon-carbon single bond or a carbon-carbon double bond; and (b) preparing at least one additional perfume, (c) adding said at least one compound of formula (I) to said at least one additional perfume in a functionally effective amount sufficient to modify the existing perfume to make it more fruity, more juicy, softer, clearer, fresher, sweeter and / or more floral. comprises or consists of the above steps.

[0056] Preferably, the weight ratio of said at least one compound of formula I to the total amount of other perfumes is in the range of 1:100 to 1:10. More preferably, the weight ratio of said at least one compound of formula I to the total amount of other perfumes is in the range of 1:85 to 1:15.

[0057] In this context, in each case, based on the total weight of the composition, it is preferred that the total amount of the at least one compound of formula I is in the range of 0.0001 to 99.9% by weight, preferably 0.001 to 99.5% by weight, particularly preferably 0.01 to 99% by weight, 0.01 to 90% by weight, 0.01 to 50% by weight, 0.01 to 20% by weight, 0.01 to 10% by weight, particularly preferably 0.01 to 5% by weight, especially preferably in the range of 0.05 to 2.0% by weight.

[0058] In a preferred embodiment according to the present invention, the at least one additional fragrance is Agrumex LC, Aldehyde C10, Aldehyde C11 undecanal, Aldehyde C12 laurin, Aldehyde C12 MNA, Aldehyde C11 MOA pure, allyl cyclohexylpropionate, allyl heptylate, Ambroxide 10% IPM, anisaldehyde pure, Calone 10%, Carboxylic L, Coumarin, cyclodumol acetate, 2,6-dimethyl-7-octen-2-ol (dihydromyrcenol), DYNASCONE® 1% DPG, FARENAL® 10% DPG, Florazon, FLORHYDRAL® , Florosa BM / Pyranol, FRUCTATE® , Furaminton / Tonkalactone™ 1% DPG, GLOBALIDE® , methyl 3-oxo-2-pentyl-1-cyclopentylacetate (HEDION®), heliotropin / piperonal, hexyl acetate, hexyl salicylate, isoamyl acetate, Spirit Mint Oil (KRAUSEMINZOEL) 65% from the USA, LEAFOVERT® , Linolal, MAGNOLAN® , MELONAL® , beta-crystalline methyl naphthyl ketone, Neralion 0.Selected from the group consisting of 1% DPG, 2-phenylethanol (phenylethyl alcohol), Timber Silk, VERTOMUGAL (registered trademark), ethyl acetoacetate, aldehyde C14 SOG, aldehyde C18 SOG, allyl caproate, benzaldehyde DD, citral FF, citronellol 950, citronellyl acetate extra, lemon oil from Italy, lemon oil terpene, cyclamen aldehyde, damasconone, damascone delta, decalactone gamma, ethyl butyrate, ethyl maltol, ethyl methyl butyrate-2 (ethyl methyl butyrate-2), geranyl acetate pure, heliotropin / piperonal, HERBAFLORAT (registered trademark), cis-3-hexenol, cis-3-hexenyl acetate, ionone beta, ISO E SUPER (registered trademark), isoborneol, isopropylmethylthiazole-2,4 10% DPG, jasmaplurnut, linalool, MANZANATE (registered trademark), octalactone gamma, styryl acetate, SYMFRESH (registered trademark) NX, thiomenthanone-8,3 10% DPG, undecabeltol, vanillin, vertocitral (VERTOCITRAL), allyl amyl glycolate, alpha-amyl cinnamaldehyde, benzyl acetate, dimethylbenzylcarbinyl butyrate (dimethylbenzylcarbinyl butyrate), dodecalactone gamma, ethylene brassylate, ethyl linalool, ethyl vanillin, floropal, FRAMBINON (registered trademark), herbyl propionate, alpha-hexyl cinnamaldehyde, isoamyl acetate, isoamyl butyrate, jasmaplurnut (JASMAPRUNAT), MACROLIDE (registered trademark) supra, methyl anthranilate (METHYLANTHRANILAT), methyl cinnamate, mugetanol, PHENIRAT (registered trademark), prenyl acetate and ROMANDOLIDE (registered trademark).

[0059] Preferably, said at least one compound of formula I is combined with one or two or more, particularly preferably two, three, four, five or six or more of their preferred other fragrances.

[0060] More preferably, the compound of formula I is selected from the group consisting of ethyl cyclohexene-1-carboxylate, butyl cyclohexene carboxylate, cyclopentyl cyclohexanecarboxylate, or mixtures thereof.

[0061] The more preferred embodiments listed above are also applicable to the method of the present invention.

[0062] A further aspect of the present invention is at least one compound of formula I, and

[0063]

Chemical formula

[0064] In a preferred embodiment, the perfumed product is selected from cosmetics, hygiene products and / or household products. The further preferred embodiments listed above are also applicable to the perfumed product of the present invention.

[0065] Preferably, the perfumed household products are hereinafter selected from the group consisting of detergents and cleaning agents, hygiene products or care products, preferably body care and hair care, cosmetics and household products, preferably perfume extracts, eau de parfum, eau de toilette, aftershave lotion, eau de cologne, preshave products, splash cologne, scented refreshment tissues, acidic, alkaline or neutral cleaning agents, fabric perfumes, ironing aids, liquid detergents, powder detergents, pre-washing treatments, fabric softeners, cleaning tablets, disinfectants, surface disinfectants, perfumes, aerosol sprays, waxes and polishes, personal care products, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, aftershave creams and lotions, sun creams and lotions, hair care products, hair care products, decorative cosmetics products, candles, lamp oils, incense sticks, insecticides, repellents and fuels. Most preferably, the perfumed products are selected from alcoholic perfumes, personal hygiene products, cleaning or care products for household use.

[0066] Furthermore, with respect to the perfumed products according to the invention, it is preferred that at least one compound of formula Il is contained in a sensory effective amount sufficient for the consumer to perceive one or more olfactory characteristics selected from the group consisting of more fruity, more juicy, softer, clearer, fresher, sweeter and / or more floral.

[0067] It is also preferred that the total amount of the compound of formula I 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 0.5 to 2% by weight, based on the total weight of the perfumed product.

[0068] The above-mentioned additives, auxiliaries and / or active substances are preferably not odoriferous substances. These are, for example, preservatives, antibacterial agents, chelating agents, detergents, emulsifiers, fats and oils, etc., and in principle can be all substances used as additives, auxiliaries and / or active ingredients in cosmetics, especially fragrance compositions, and household compositions.

[0069] The more preferred embodiments listed above are also applicable to the scented products of the present invention.

[0070] In the following, the present invention will be further characterized based on examples.

Examples

[0071] Example 1: Synthesis of Ethyl Cyclohexene-1-carboxylate

[0072] A mixture of cyclohexene-1-carboxylic acid (2.5 g, 19.2 mmol), ethanol (5.6 mL) and p-toluenesulfonic acid (0.4 g) in toluene (10 mL) was refluxed in a Dean-Stark apparatus until no more water evaporated. After completion of the reaction, the organic layer was washed until neutral and evaporated on a rotary evaporator to obtain a crude product, and then the title compound with Wt = 2.5 g and Y = 66.6% was obtained by bulb-to-bulb distillation. The following 1.1 g, y = 98% of the title compound was obtained from 2.5 g of cyclohexene-1-carboxylic acid. 1 H NMR (400 MHz, CDCl3) δ 6.98 (tt, J = 3.8, 1.8 Hz, 1H), 4.18 (q, J = 7.1 Hz, 2H), 2.29 - 2.22 (m, 2H), 2.22 - 2.14 (m, 2H), 1.70 - 1.60 (m, 2H), 1.65 - 1.56 (m, 2H), 1.29 (t, J = 7.1 Hz, 3H). 1313C NMR (101 MHz, CDCl3) δ 167.71, 139.44, 130.50, 60.17, 25.76, 24.14, 22.11, 21.50, 14.31. In the case of: Cinnamon, marzipan, chlorine, benzophenone

[0073] Example 2: Synthesis of butyl cyclohexene carboxylate

[0074] A mixture of cyclohexene carboxylic acid (400.0 g, 3.1 mol), butan-1-ol (418.4 g, 5.6 mol) and p-toluenesulfonic acid (2.5 g) in toluene (600 mL) was refluxed in a Dean-Stark apparatus until no more water evaporated. After completion of the reaction, the organic layer was washed until neutral and evaporated on a rotary evaporator to obtain a crude product (571.0 g), which was then subjected to bulb-to-bulb distillation to obtain 467.0 g of butyl cyclohexene carboxylate with a yield of 98%. 1 1H NMR (400 MHz, CDCl3) δ 4.06 (t, J = 6.6 Hz, 2H), 2.28 (tt, J = 11.3, 3.6 Hz, 1H), 1.95 - 1.84 (m, 2H), 1.80 - 1.69 (m, 2H), 1.69 - 1.62 (m, 1H), 1.60 (p, J = 7.5, 6.6 Hz, 2H), 1.51 - 1.35 (m, 2H), 1.38 (h, J = 7.5 Hz, 2H), 1.34 - 1.17 (m, 3H), 0.93 (t, J = 7.4 Hz, 3H). 13 13C NMR (101 MHz, CDCl3) δ 176.26, 63.97, 43.32, 30.76, 29.08, 29.08, 25.82, 25.50, 25.50, 19.18, 13.74. MS: 184, 168, 129, 111, 83, 55, 41, 29. Odor: Fruity, valerian ester, sweet, cinnamon, castoreum, apple, pear, pineapple

[0075] Example 3: Synthesis of cyclopentyl cyclohexanecarboxylate

[0076] A mixture of cyclohexanecarboxylic acid (400.0 g, 3.1 mol), cyclopentanol (304.0 g, 3.5 mol) and p-toluenesulfonic acid (4.0 g) in toluene (800 mL) was refluxed in a Dean-Stark apparatus until no more water evaporated. After completion of the reaction, the organic layer was washed until neutral and evaporated on a rotary evaporator to obtain a crude product (629.3 g), and then cyclopentyl cyclohexanecarboxylate with wt = 551.6 g and Y = 97% was obtained by bulb-to-bulb distillation. 1 H NMR (400 MHz, CDCl3) δ 5.15 (tt, J = 5.7, 2.7 Hz, 1H), 2.23 (tt, J = 11.2, 3.6 Hz, 1H), 1.92 - 1.77 (m, 4H), 1.77 - 1.72 (m, 2H), 1.72 - 1.65 (m, 2H), 1.65 - 1.50 (m, 5H), 1.49 - 1.35 (m, 2H), 1.33 - 1.22 (m, 2H), 1.27 - 1.14 (m, 1H). 13 C NMR (101 MHz, CDCl3) δ 175.98, 76.51, 43.35, 32.71, 32.71, 29.01, 29.01, 25.83, 25.47, 25.47, 23.77, 23.77. MS: 196, 168, 152, 129, 111, 83, 69, 55, 41, 29 Odor: Fruity, pineapple, green, strawberry

[0077] Example 4: Flavor mixture

[0078] [Table 1-1]

[0079] [Table 1-2]

[0080] [Table 2-1]

[0081]

Table 2-2

[0082] According to the expert panel, a fragrance mixture without cyclopentyl cyclohexanecarboxylate has a fruity smell of mango, peach, pineapple and citrus. When cyclopentyl cyclohexanecarboxylate is added to the fragrance mixture, the fragrance mixture becomes clearer, fresher and juicier.

[0083]

Table 3

[0084] According to the expert panel, a fragrance mixture without cyclopentyl cyclohexanecarboxylate has a fruity smell like that of an apple. When a small amount (40 parts) of cyclopentyl cyclohexanecarboxylate is added to the fragrance mixture, the fragrance mixture becomes more fruity and is further imparted with the effect of orange. When a larger amount (60 parts) of cyclopentyl cyclohexanecarboxylate is added, the fruitiness of the fragrance mixture becomes even stronger and a sweet note is added.

Claims

1. Use as a fragrance of at least one compound of Formula I, wherein 【Chemical 1】 R represents ethyl, propyl, butyl or cyclopentyl; and the dotted line represents a carbon-carbon single bond or a carbon-carbon double bond.

2. The use according to claim 1, wherein R represents ethyl, butyl or cyclopentyl.

3. The use according to claim 1 and / or 2, wherein the compound of Formula I is ethyl cyclohexene-1-carboxylate.

4. The use according to claim 1 and / or 2, wherein the compound of Formula I is butyl cyclohexenecarboxylate.

5. The use according to claim 1 and / or 2, wherein the compound of Formula I is cyclopentyl cyclohexanecarboxylate.

6. Use according to claims 1 to 5 in a fragrance composition for obtaining at least one of the following fragrance notes: cinnamon note, marzipan note, fruity note, valerian ester note, sweet note, apple note, pear note, pineapple note, strawberry note, green note and / or castoreum note.

7. Use according to claims 1 to 6 for imparting, modifying and / or enhancing a fragrance composition to make it more fruity, more juicy, softer, clearer, fresher, sweeter and / or more floral.

8. A fragrance composition comprising at least one compound of Formula I wherein 【Chemical 2】 R represents ethyl, propyl, butyl or cyclopentyl; and the dotted line represents a carbon-carbon single bond or a carbon-carbon double bond; and at least one further fragrance.

9. The fragrance composition according to claim 8, wherein the weight ratio of the at least one compound of Formula I to the total amount of the other fragrances is in the range of 1:100 to 1:

10.

10. The fragrance composition according to claim 9, wherein the weight ratio of the at least one compound of Formula I to the total amount of the other fragrances is in the range of 1:85 to 1:

15.

11. The fragrance composition according to claims 8 to 10, wherein the amount of the at least one compound of Formula I is in the range of 0.01 to 10% by weight based on the total weight of the fragrance composition.

12. [[ID= ​ ​ The olfactory composition according to at least one of claims 8 to 11, wherein said at least one compound of formula I is contained in said olfactory composition in a functionally effective amount sufficient to modify an existing olfactory to make it more fruity, more juicy, more soft, more clear, more fresh, more sweet and / or more floral.

13. Use of the olfactory composition according to any one of claims 8 to 12 for modifying an existing olfactory to make it more fruity, more juicy, more soft, more clear, more fresh, more sweet and / or more floral.

14. A method for modifying an existing olfactory to make it more fruity, more juicy, more pineapple, more soft and / or more floral, said method comprising: The following steps: (a) preparing at least one compound of formula I 【Chemical 3】 wherein R represents ethyl, propyl, butyl or cyclopentyl; and the dotted line represents a carbon-carbon single bond or a carbon-carbon double bond, and (b) preparing at least one additional olfactory, (c) adding said at least one compound of formula (I) to said at least one additional olfactory in a functionally effective amount sufficient to modify the existing olfactory to make it more fruity, more juicy, more soft, more clear, more fresh, more sweet and / or more floral A method comprising or consisting of said steps.

15. An olfactory product comprising at least one compound of formula I and 【Chemical Formula 4】 wherein R represents ethyl, propyl, butyl or cyclopentyl; and the dotted line represents a carbon-carbon single bond or a carbon-carbon double bond, two or more other olfactorics and optionally other components, characterized in that said product contains said at least one compound of formula (I) in an amount sufficient to modify the olfactory properties of said two or more other olfactorics to make said olfactory properties more fruity, more juicy, more soft, more clear, more fresh, more sweet and / or more floral.

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