Cyclohexane and / or cyclohexene esters as fragrances

Abstract

The use of at least one compound of formula I # imgabs0 # as perfume is proposed.

Description

Field of the Invention

[0001] The present invention relates to the use of cyclohexanes and / or cyclohexenyl esters as fragrances. Furthermore, the present invention relates to fragrance compositions, their use and methods for imparting, modifying and / or enhancing certain fragrance notes. Background of the Invention

[0002] As far as the perfume industry is concerned, there is a permanent need for new perfume creations. However, the creation of new fragrances or fragrance compositions involves many challenges. For example, it is necessary to select a specific composition of several fragrances from an almost infinite number of possible structures known from the prior art in order to meet specific needs of the market and to provide a product that matches the specific characteristics desired by the customer. Suitable fragrances exhibit very beneficial properties, but in combination with other fragrances may produce unpleasant and therefore harmful odors, making them difficult or even impossible to use for a specific purpose.

[0003] A second important problem relates to the need to provide fragrance compositions which are not only consistent with a specific odor profile but also have so-called secondary beneficial properties. In fact, many fragrance compositions known on the market have significant disadvantages in use, such as poor solubility and storage stability, but also have deficiencies in subjective issues such as richness, charm, etc. In addition, many known fragrance compositions require high dosages to achieve the desired odor result. Another requirement currently placed on fragrances is high biodegradability as well as dermatological and toxicological safety. Therefore, there is a particularly high need to provide fragrances which, even in small doses, have a large impact on other fragrances and transform rather unpleasant odor impressions into positive odor impressions and / or enhance pleasant odor impressions.

[0004] The problem underlying the present invention is therefore to provide a new fragrance which is able to enhance the positive and beneficial odor aspects of other fragrances and / or (at the same time) reduce, inhibit and / or mask the undesirable unpleasant odor aspects. In particular, the new fragrance should also have the characteristics of improving the stability, solubility and overall performance of other fragrances, as well as reducing the required dosage. Finally, the fragrance composition itself should have excellent biodegradability and be harmless to humans and the environment. Summary of the invention

[0005] This is accomplished by using at least one compound of formula I As a spice to solve, R represents ethyl, propyl, butyl or cyclopentyl, and Dashed lines represent carbon-carbon single bonds or carbon-carbon double bonds.

[0006] The compounds of the formula I used according to the invention may be present in any stereoisomeric form or in any mixture of stereoisomers.

[0007] What has been said herein for the compounds of the formula I, in particular the advantages stated herein, also applies to mixtures of stereoisomers of the compounds of the formula I or mixtures of different compounds of the formula I used or to be employed according to the invention.

[0008] The compounds of formula I have very unique olfactory properties, which are clearly different from and also exceed the olfactory properties of known odorous substances. The suitability of the compounds of formula I as fragrances was previously unknown. It is therefore particularly surprising that in an area that has been well studied, a valuable, interesting and complex olfactory fragrance can be found.

[0009] As mentioned above, the suitability of the compounds of formula I as fragrances is unclear. Likewise, no precise odor description is available, however, according to the inventors, the compounds of formula I smell particularly like cinnamon, almond sugar, fruity, valeric acid, sweet, apple, pear, pineapple, strawberry, green and / or castoreum.

[0010] Therefore, the inventors surprisingly found that the compounds of formula I are suitable as fragrances and can produce special effects in combination with other fragrances at small doses.

[0011] For the sake of clarity, the expression "the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond" or similar expressions refers to the normal meaning understood by those skilled in the art, that is, the entire bond (solid line and dashed line) between the carbon atoms connected by the dashed line is a single bond or a double bond.

[0012] In a preferred embodiment according to the present invention, R represents ethyl, butyl or cyclopentyl. In another preferred embodiment according to the present invention, R represents ethyl, butyl or cyclopentyl and the dotted line represents a carbon-carbon single bond. In another preferred embodiment according to the present invention, R represents ethyl, butyl or cyclopentyl and the dotted line represents a carbon-carbon double bond.

[0013] Preferably, the compound of formula I is ethyl cyclohexene-1-carboxylate having the structure of formula II and / or molecular weight 154.1.

[0014] Preferably, ethyl cyclohexene-1-carboxylate has the following odor notes: cinnamon, almond sugar, chlorine and / or benzophenone.

[0015] Further preferably, the compound of formula I is butyl cyclohexenecarboxylate, which has the structure of formula III and / or molecular weight 184.14.

[0016] Preferably, butyl cyclohexenecarboxylate has the following odor notes: fruity, valeric, sweet, cinnamon, castoreum, apple, pear and / or pineapple.

[0017] Further preferably, the compound of formula I is cyclopentyl cyclohexanecarboxylate having a structure of formula IV and / or molecular weight 196.15.

[0018] Preferably, cyclopentyl cyclohexanecarboxylate has the following odor notes: fruity, pineapple, green and / or strawberry.

[0019] Further preferably, the compound of formula I is selected from the group consisting of ethyl cyclohexene-1-carboxylate, butyl cyclohexenecarboxylate, cyclopentyl cyclohexanecarboxylate or a mixture thereof.

[0020] In a preferred embodiment according to the invention, at least one compound of formula I is used in a perfume composition to obtain at least one of the following notes: cinnamon, almond, fruity, valeric, sweet, apple, pear, pineapple, strawberry, green and / or castoreum. It is further preferred to use at least one compound of formula I to impart, improve and / or enhance the perfume composition to make it more fruity, juicy, softer, sharper, fresher, sweeter and / or more floral. However, in view of the above odor description, this is particularly surprising, because some compounds of formula I do not have any fruity, juicy or floral notes and / or even less pleasant odor notes, such as ethyl cyclohexene-1-carboxylate.

[0021] The fact that the compounds of the formula I used according to the invention can impart very complex and varied overall sensory impressions, which can usually only be achieved by mixtures of several components (eg essential oils or fragrance mixtures) is particularly surprising.

[0022] Besides their main, olfactory properties, the compounds of the formula I additionally have positive secondary properties, in particular high substantivity compared with fragrances having similar olfactory properties, high stability in certain media and formulations, high extensibility and are also biodegradable.

[0023] With regard to the preferred use for imparting, modifying and / or intensifying perfume notes, it is also recognized that the compounds of formula I can act very well as so-called enhancers (amplifiers; intensifiers).

[0024] In addition, the compounds of formula I used according to the present invention can enhance the intensity of the fragrance mixture (fragrance composition) and make the overall smell of the mixture mellow. Therefore, the compounds described herein can be used to give the fragrance composition more fullness, freshness, (diffusion) intensity, diffusivity, mellowness, harmony, naturalness and / or less greasy feeling, in particular, the compounds can be used to give the fragrance composition softer, clearer and / or fresher.

[0025] Furthermore, the compounds of the formula I are suitable as agents for increasing the substantivity and / or retention of fragrance compositions.

[0026] The compounds of formula I can be used in a variety of products; they can be used as single fragrances, but they can be combined with other fragrances in different, different proportions to form fragrance mixtures, and can also produce novel and original fragrance compositions. Therefore, one aspect of the present invention also relates to fragrance mixtures and possible other ingredients (solvents, etc.), which contain at least one compound of formula I, 4-cyclohexylbutan-2-one.

[0027] The fragrance composition according to the invention comprises at least one compound of formula I in R represents ethyl, propyl, butyl or cyclopentyl, and Dashed lines represent carbon-carbon single bonds or carbon-carbon double bonds, and at least one other flavorant.

[0028] In a preferred embodiment, the compound of formula I is selected from the group consisting of ethyl cyclohexene-1-carboxylate, butyl cyclohexenecarboxylate, cyclopentyl cyclohexanecarboxylate or mixtures thereof.

[0029] Preferably, the fragrance composition according to the present invention comprises at least one compound of formula I and two or more other fragrances or consists thereof. More preferably, the fragrance composition according to the present invention comprises at least one compound of formula I and three or more other fragrances or consists thereof. Most preferably, the fragrance composition according to the present invention comprises at least one compound of formula I and four or more other fragrances or consists thereof.

[0030] Preferably, the fragrance composition according to the present invention comprises ethyl cyclohexene-1-carboxylate and two or more other fragrances or consists thereof. More preferably, the fragrance composition according to the present invention comprises ethyl cyclohexene-1-carboxylate and three or more other fragrances or consists thereof. Most preferably, the fragrance composition according to the present invention comprises ethyl cyclohexene-1-carboxylate and four or more other fragrances or consists thereof.

[0031] Preferably, the fragrance composition according to the present invention comprises butyl cyclohexenecarboxylate and two or more other fragrances or consists thereof. More preferably, the fragrance composition according to the present invention comprises butyl cyclohexenecarboxylate and three or more other fragrances or consists thereof. Most preferably, the fragrance composition according to the present invention comprises butyl cyclohexenecarboxylate and four or more other fragrances or consists thereof.

[0032] Preferably, the fragrance composition according to the present invention comprises cyclopentyl cyclohexanecarboxylate and two or more other fragrances or consists thereof. More preferably, the fragrance composition according to the present invention comprises cyclopentyl cyclohexanecarboxylate and three or more other fragrances or consists thereof. Most preferably, the fragrance composition according to the present invention comprises cyclopentyl cyclohexanecarboxylate and four or more other fragrances or consists thereof.

[0033] The compounds of the formula I according to the invention are generally used in an organoleptically effective amount, ie in such total amount that they produce a sensory effect.

[0034] Preferably, the weight ratio of at least one compound of formula I to the total amount of other fragrances is in the range of 1:100 to 1:10. More preferably, the weight ratio of at least one compound of formula I to the total amount of other fragrances is in the range of 1:85 to 1:15.

[0035] In this context, preference is given to a total amount of at least one compound of the formula I in the range from 0.0001 to 99.9% by weight, preferably from 0.001 to 99.5% by weight, particularly preferably from 0.01 to 99% by weight, from 0.01 to 90% by weight, from 0.01 to 50% by weight, from 0.01 to 20% by weight, from 0.01 to 10% by weight and particularly preferably from 0.01 to 5% by weight, in particular from 0.05 to 2.0% by weight, in each case based on the total weight of the composition.

[0036] In a preferred embodiment according to the invention, the compound of formula I is contained in the flavor composition in an organoleptically effective amount, which is sufficient to modify an existing flavor to make it fruitier, juicier, softer, sharper, fresher, sweeter and / or more floral.

[0037] Examples of fragrances which can advantageously be combined with 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, NJ 1969, self-published, or K. Bauer ei a / ., Common Fragrance and Flavor Materials, 4th Edition, Wiley-VCH, Weinheim 2001.

[0038] Particularly mentioned are: extracts of natural raw materials such as essential oils, extracts, absolutes, resins, balsams, salves, tinctures, etc. Ambergris tincture, sandalwood oil, angelica seed oil, angelica root oil, fennel oil, valerian oil, basil oil, tree moss absolute, bay leaf oil, wormwood oil, benzoin resin, bergamot oil, beeswax absolute, birch tar, bitter almond oil, savory oil, buchu leaf oil, Brazilian sandalwood oil, juniper oil, calamus oil, camphor oil, ylang-ylang oil, cardamom oil, quinoa oil, cinnamon oil, acacia absolute, castoreum absolute, cedar leaf oil, cedarwood oil, labdanum oil, citronella oil, lemon oil, copaiba balsam, copaiba balsam oil, coriander oil, costus root oil, cumin oil, cedar oil, davana oil, dill grass oil, dill seed oil, Eau de brouts-Absolue, Oakmoss Absolute, Elemi Oil, Tarragon Oil, Lemon Eucalyptus Oil, Eucalyptus Oil, Fennel Oil, Fir Needle Oil, Ginger Oil, Guaiac Wood Oil, Guar Balsam, Guar Balsam Oil, Helichrysum Absolute, Helichrysum Oil, Ginger Oil, Orris Root Absolute, Orris Root Oil, Jasmine Absolute, Calamus Oil, Blue Chamomile Oil, Roman Chamomile Oil, Carrot Seed Oil, Quinoa Oil, Pine Needle Oil, Peppermint Oil, Caraway Oil, Cistus Oil, Cistus Absolute, Cistus Resin, Lavender Absolute, Lavender Oil, Lavender Absolute, Lavender Oil, Lemongrass Oil, Angelica Oil, Distilled Lime Oil, Pressed Lime Oil, Agarwood Oil, Litsea Cubeba Oil, Bay Leaf Oil, Nutmeg Oil, Oregano Oil, Citrus Oil, Massoir Bark oil, Mimosa Absolute, Ambrette Seed Oil, Ambrette Tincture, Sage Oil, Nutmeg Oil, Myrrh Absolute, Myrrh Oil, Myrtle Oil, Clove Leaf Oil, Clove Flower Oil, Neroli Oil, Frankincense Absolute, Frankincense Oil, Oopso Oil, Neroli Absolute, Orange Oil, Oregano Oil, Palmarosa Oil, Patchouli Oil, Perilla Seed Oil, Peruvian Balsam Oil, Parsley Leaf Oil, Parsley Seed Oil, Petitgrain Oil, Peppermint Oil, Chili Oil, Allspice Oil, Pine Oil, Poleyoil, Rose Absolute, Rosewood Oil, Rose Oil, Rosemary Oil, Dalmatian sage oil, Spanish sage oil, sandalwood oil, rapeseed oil, spike lavender oil, star anise oil, benzoin oil, marigold oil, cedar needle oil, tea tree oil, turpentine oil, thyme oil, tolu balsam, tonka bean absolute, tuberose absolute, vanilla extract, violet leaf absolute, verbena oil, vetiver oil, juniper oil, grapeseed oil, wormwood oil, wintergreen oil, ylang-ylang oil, hyssop oil, civet absolute, cinnamon leaf oil, cinnamon bark oil, and fractions thereof or contents separated therefrom;

[0039] A single flavoring agent selected from hydrocarbons, such as 3-carene, α-pinene, β-pinene, α-terpinene, γ-terpinene, p-cymene, bisabolol, camphene, caryophyllene, cedrene, farnesene, limonene, longifolene, myrcene, ocimene, valencene, (E,Z)-1,3,5-undecatriene; styrene; diphenylmethane; Fatty 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, a mixture of 3,4,5,6,6-pentamethyl-3 / 4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methyleneheptan-2-ol, (E,Z)-2,6-nonadienol, 3,7-dimethyl-7-methoxyoctan-2-ol, 9-decenol, 10-undecenol, 4-methyl-3-decenyl-5-ol; 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; 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-nonenoic acid nitrile, 2-undecenoic acid nitrile, 2-tridecenoic acid nitrile, 3,12-tridecadienoic acid nitrile, 3,7-dimethyl-2,6-octadienoic acid nitrile, 3,7-dimethyl-6-octenoic acid nitrile; Aliphatic carboxylic acid esters, such as (E) and (Z)-3-hexenyl formate, ethyl acetoacetate, isoamyl acetate, 3,5,5-trimethyl-hexyl acetate, 3-methyl-2-butenyl acetate, (E)-2-hexenyl acetate, (E) and (Z)-3-hexenyl acetate, octyl acetate, 3-octyl acetate, 1-octen-3-acetate, ethyl butyrate, butyl butyrate, isoamyl butyrate, hexyl butyrate, isobutyl butyrate Acid (E) and (Z)-3-hexenyl esters, 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-octenoate, methyl 2-nonenoate, allyl 2-isopentyloxyacetate, methyl 3,7-dimethyl-2,6-octadienoate; 4-methyl-2-pentyl crotonate; Acyclic terpene alcohols, such as geraniol, nerol, lavadulol, 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-di Methyl-4,6-octadien-3-ol, 3,7-dimethyloct-6-en-1-ol, (2E)-3,7-dimethyloct-2,6-dien-1-ol, 3,7-dimethyl-1,5,7-octatrien-3-ol, 2,6-dimethyl-2,5,7-octatrien-1-ol, and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, valerates, hexanoates, crotonates, Tiglinates and 3-methyl-2-butenoates; Acyclic terpene aldehydes and ketones, such as citronellal, 7-methoxy-3,7-dimethyloctanal, 2,6,10-trimethyl-9-undecenal, geranylacetone, and the dimethyl and diethyl acetals of geranial and neral; Cyclic terpene alcohols such as menthol, isopulegol, α-terpineol, terpineol-4, menthan-8-ol, menthan-1-ol, menthan-7-ol, bornyl alcohol, isobornyl alcohol, linalool oxide, nopol, cedrol, ambroxanol, vetivol, guaiacol, and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, valerates, hexanoates, crotonates, Tiglinate, 3-methyl-2-butenoate; Cyclic terpene aldehydes and ketones, such as menthone, isomenthone, 8-mercaptomenthan-3-one, carvone, camphor, fenchone, α-ionone, β-ionone, α-n-methylionone, β-n-methylionone; α-isomethylionone, β-isomethylionone, α-irone, 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-methylenenaphthylamine-8(5H) -ketone, 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal, nootkatone, dihydronootkatone, 4,6,8-megatrien-3-one, α-auricularial, β-auricularial, acetyl cedar oil (methyl cedar ketone); cyclic alcohols, such as, for example: 4-tert-butyl cyclohexanol, 3,3,5-trimethyl-cyclohexanol, 3-isobornyl cyclohexanol, 2,6,9-trimethyl-(Z2,Z5,E9)-cyclododecatrien-1-ol, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol; 4-cyclohexylbutan-2-ol; 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; Cyclic and alicyclic ethers, for example: eucalyptol, methyl cedar ether, cyclododecyl methyl ether, 1,1-dimethoxycyclododecane, (ethoxymethoxy)cyclododecane, α-epoxycedrene, 3a,6,6,9a-tetramethyldodecahydronaphthol[2,1-b]furan, 3a-ethyl-6,6,9a-trimethyldodecahydronaphthol[2,1-b]furan, 1,5,9-trimethyl-13-oxabicyclo[10.1.0]-tridecyl-4,8-diene, rose oxide, 2-(2,4-dimethyl-3-cyclohexen-1-yl)-5-methyl-5-(1-methylpropyl)-1,3-dioxane; Cyclic ketones and macrocyclic ketones, such as, for example: 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-cyclohexadecene-1-one, 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone, 8-cyclohexadecene-1-one, 9-cycloheptadecene-1-one, cyclopentadecanone, cyclohexadecanone; Cyclic aliphatic aldehydes, such as 2-methyl-4-(2,2,6-trimethyl-cyclohexen-1-yl)-2-butenal, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarboxaldehyde, 4-(4-methyl-3-penten-1-yl)-3-cyclohexenecarboxaldehyde; Cycloaliphatic ketones, for example: 1-(3,3-dimethylcyclohexyl)-4-penten-1-one, 2,2-dimethyl-1-(2,4-dimethyl-3-cyclohexen-1-yl)-1-propanone, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one, 2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthylmethyl ketone, methyl-2,6,10-trimethyl-2,5,9-cyclododecantrienone, tert-butyl-(2,4-dimethyl-3-cyclohexen-1-yl) ketone; Esters of cyclic alcohols, such as 2-tert-butylcyclohexyl acetate, 4-tert-butylcyclohexyl acetate, 2-tert-amylcyclohexyl acetate, 4-tert-amylcyclohexyl acetate, 3,3,5-trimethylcyclohexyl acetate, decahydro-2-naphthyl acetate, 2-cyclopentyl cyclopentyl crotonate, 3-pentyl-tetrahydro-2H-pyran-4 acetate, decahydro-2,5,5,8a-tetramethyl-2-naphthyl acetate, 4,7-formyloxy-3a,4,5,6,7,7a-hexahydro-5- or -6-indenyl acetate, 4,7-formyloxy-3a,4,5,6,7,7a-hexahydro-5- or -6-indenyl propionate, 4,7-formyloxy-3a,4,5,6,7,7a-hexahydro-5- or -6-indenyl isobutyrate, 4,7-formyloxy-3a,4,5,6,7,7a-hexahydro-5- or -6-indenyl acetate, Esters of cycloaliphatic alcohols, for example 1-cyclohexylethyl crotonate; Cycloaliphatic carboxylic acid esters, for example allyl 3-cyclohexylpropionate, allyl cyclohexyloxyacetate, methyl cis- and trans-dihydrojasmonate, methyl cis- and trans-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-dioxolanecarboxylate; Aromatic aliphatic alcohols, such as benzyl alcohol, 2-phenylethanol, 1-phenylethanol, 3-phenylpropanol, 2-phenylpropanol, 2-phenoxyethanol, 2,2-dimethyl-3-phenylpropanol, 2,2-dimethyl-3-(3-methylphenyl)propanol, 1,1-dimethyl-2-phenylethanol, 1,1-dimethyl-3-phenylpropanol, 1-ethyl-1-methyl-3-phenylpropanol, 2-methyl-5-phenylpentanol, 3-methyl-5-phenylpentanol, 3-phenyl-2-propen-1-ol, 4-methoxybenzyl alcohol, 1-(4-isopropylphenyl)ethanol; Esters of aromatic aliphatic alcohols and aliphatic carboxylic acids, for example benzyl acetate, benzyl propionate, benzyl isobutyrate, benzyl isovalerate, 2-phenylethyl acetate, 2-phenylethyl propionate, 2-phenylethyl isobutyrate, 2-phenylethyl isovalerate, 1-phenylethyl acetate, α-trichloromethylbenzyl acetate, α,α-dimethylphenyl ethyl acetate, α,α-dimethylphenyl ethyl butyrate, cinnamyl acetate, 2-phenoxyethyl isobutyrate, 4-methoxybenzyl acetate; Aromatic ethers, such as 2-phenylethyl methyl ether, 2-phenylethyl isopentyl ether, 2-phenylethyl-1-ethoxyethyl ether, phenylacetaldehyde dimethyl acetal, phenylacetaldehyde diethyl acetal, hydratropaaldehyde dimethyl acetal, phenylacetaldehyde glycerol acetal, 2,4,6-trimethyl-4-phenyl-1,3-dioxane, 4,4a,5,9b-tetrahydroindene-[1,2-d]-m-dioxine, 4,4a,5,9b-tetrahydro-2,4-dimethylindene[1,2-d]-m-dioxine; Aromatic and araliphatic aldehydes such as, for example: benzaldehyde, phenylacetaldehyde, 3-phenylpropanal, Hydratropaaldehyd, 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-butylphenyl)propanal, cinnamaldehyde, α-butylcinnamaldehyde, α-hexylcinnamaldehyde, 3-methyl-5-phenylvaleraldehyde, 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-tert-butylphenyl)propanal, methylenedioxyphenyl) propionaldehyde; aromatic and aromatic aliphatic ketones, such as acetophenone, 4-methyl-acetophenone, 4-methoxyacetophenone, 4-tert-butyl-2,6-dimethylacetophenone, 4-phenyl-2-butanone, 4-(4-hydroxyphenyl)-2-butanone, 1-(2-naphthyl)ethanone, 2-benzofuranethanone, 3-methyl-2-benzofuranyl)ethanone, benzophenone, 1,1, 2,3,6-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-indanyl]ethanone; 5',6',7',8'-tetrahydro-3',5',5',6',8',8'-hexamethyl-2-naphthone; Aromatic and araliphatic carboxylic acids and their esters, for example benzoic acid, phenylacetic acid, methyl benzoate, ethyl benzoate, hexyl benzoate, benzyl benzoate, methylphenyl acetate, ethylphenyl acetate, geranylphenyl acetate, 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, phenylethyl salicylate, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, ethyl 3-phenylglycidate, ethyl 3-methyl-3-phenylglycidate; 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; Lactones, such as 1,4-octanolactone, 3-methyl-1,4-octanolactone, 1,4-nonanolactone, 1,4-decanolactone, 8-decene-1,4-lactone, 1,4-undecalactone, 1,4-dodecalactone, 1,5-decanolactone, 1,5-dodecalactone, 4-methyl-1,4-decanolactone, 1,15-pentadecalactone, 1,16-hexadecanolactone, 9-hexadecene-1,16-lactone, 10-oxo-1,16-hexadecanolactone, 11-oxo-1,16-hexadecanolactone, 12-oxo-1,16-hexadecanolactone, vinyl-1,12-dodecyl-dialactone, vinyl-1,13-tridecyl-dialactone, 2,3-dihydrocoumarin, octahydrocoumarin.

[0040] In a preferred embodiment according to the present invention, at least one other fragrance is selected from the group consisting of: AGRUMEX LC, C10 aldehyde, C11 aldehyde undecane aldehyde, C12 aldehyde laurin, C12 aldehyde MNA, C11 aldehyde MOA PURE, allyl cyclohexanepropionate, allyl heptanoate, ambroxol 10% IPM, anise aldehyde resin, watermelon ketone 10%, carvone L, coumarin, cyclodomol acetate (CYCLODUMOL ACETATE), 2,6-dimethyl-7-octen-2-ol (dihydromyrcenol), dynasty ketone 1% DPG, 10% DPG, sea breeze aldehyde, anthocyanin, BM / PYRANOL, FURAMINTON / TONKALACTONE TM 1% DPG, Methyl-3-oxo-2-pentyl-1-cyclopentyl acetate (HEDION), piperonal / PIPERONAL, hexyl acetate, hexyl salicylate, isoamyl acetate, KRAUSE peppermint oil 65% AMERIK., LINOLAL, magnolol, melonal, methyl naphthyl ketone beta crystals, NEROLIONE 0.1% DPG, 2-phenylethanol (phenylethanol), TIMBERSILK, isohexenyl cyclohexenyl carboxaldehyde (vertomugal), ethyl acetoacetate, C14 aldehyde, C18 aldehyde, allyl hexanoate, benzaldehyde DD, citral FF, citronellol 950, citronellol acetate EXTRA, Italian citronellol, citronella oil terpenes, cyclamen aldehyde, damascenone, δ-damascenone, γ-decanoate, ethyl butyrate, ethyl maltol, ethyl 2-methylbutyrate, neryl acetate, piperonal / PIPERONAL, HERBAFLORAT, cis-3-hexenol, cis-3-hexenyl acetate, β-ionone, ISO ESUPER, isoborneol, isopropylmethylthiazole-2,4 10% DPG, JASMAPRUNAT, linalool, pyrethrin, γ-octalactone, styroyl acetate, NX, Thiol Menthone-8,3 10% DPG, Methyldecenol, Vanillin, Ligustrum lucidum, Allyl Isoamyl Acetate, α-Amyl Cinnamal, Benzyl Acetate, Dimethyl Benzyl Butyrate, γ-Dodecanoate, Glycol Brazilic Acid, Ethyl Linalool, Ethyl Vanillin, FLOROPAL, Tricyclodecenyl propionate, α-hexylcinnamaldehyde, isoamyl acetate, isoamyl butyrate, JASMAPRUNAT, SUPRA, methyl anthranilate, methyl cinnamate, lyrachaline alcohol, Amyl acetate, ROMANDOLIDE.

[0041] Preferably, at least one compound of the formula I is combined with one or more, particularly preferably with two, three, four, five or more of those preferred further fragrances.

[0042] The perfume oil compositions (= perfume mixtures) containing at least one compound of the formula I are advantageously used for perfuming in liquid form, undiluted or diluted with a solvent. Suitable solvents for this are, for example: ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, etc.

[0043] Furthermore, the fragrance composition according to the invention can be adsorbed on a carrier, which ensures a fine distribution of the fragrance in the product and a controlled release during use. Such a carrier can be a porous inorganic material, such as light sulfate, silica gel, zeolite, gypsum, clay, clay particles, aerated concrete, etc., or an organic material, such as wood, cellulose-based substances, sugars, dextrins (such as maltodextrin) or plastics such as PVC, polyvinyl acetate or polyurethane. The resulting combination of the composition according to the invention and the carrier substance is also to be understood as a fragrance composition according to the invention.

[0044] The fragrance composition according to the invention can also be microencapsulated, spray-dried, as an inclusion complex or as an extruded product and added in this form, for example, to the product to be perfumed.

[0045] If desired, the properties of the composition modified in this way can be further optimized by so-called "coating" with suitable materials for a more targeted release of the fragrance, for which purpose waxy plastics such as polyvinyl alcohol are preferably used. The resulting product in turn represents the preparation according to the invention.

[0046] Another aspect of the invention relates to the use of a flavor composition for improving an existing flavor to improve an existing flavor to make it fruitier, juicier, softer, sharper, fresher, sweeter and / or more floral. The preferred embodiments listed above also apply to the use of the flavor composition.

[0047] The perfume compositions according to the invention can advantageously be used in the form of concentrates, solutions or in the modified forms described above for the production of perfumed articles according to the invention, such as, for example, perfume extracts, perfume concentrates, eau de toilette, shaving waters, colognes, pre-shave products, cologne pomades and perfumed wet wipes, for the perfuming of acidic, alkaline and neutral cleaners, such as floor cleaners, glass cleaners, dishwashing detergents, bathroom and sanitary cleaners, scrubbing creams, solid and liquid toilet cleaners, carpet cleaners in powder and foam form, textile refreshers, ironing aids, liquid washing compositions, powdered washing compositions, laundry pretreatment preparations such as bleaches, soaking agents and stain removers, fabric softeners, washing soaps, laundry tablets, disinfectants, air fresheners in liquid form, gel form or in the form of an application to a solid carrier, aerosol sprays, waxes and polishes, such as furniture polish, floor wax, shoe cream 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 as skin creams and lotions, face creams and lotions, sunscreen creams and lotions, after-sun repair creams and lotions, hand creams and lotions, foot creams and lotions, hair removal creams and lotions, aftershave creams and lotions, suntan creams and lotions, hair care products such as hair sprays, hair gels, styling creams, conditioners, permanent and semi-permanent hair colorants, hair styling products such as cold wave and hair straightening products, hair nourishers, hair creams and shampoos, deodorants and antiperspirants such as underarm sprays, roll-ons, deodorant sticks, deodorant creams, decorative cosmetics such as eye shadows, nail polishes, lipsticks, mascaras and candles, lamp oils, insecticides, insect repellents and propellants.

[0048] Of course, the fragrance composition according to the present invention may also be contained in a cosmetic composition or a household composition.

[0049] Another aspect of the present invention relates to a method for improving an existing flavor to make it fruitier, juicier, milder, sharper, fresher, sweeter and / or more floral, Include or consist of the following steps: (a) providing at least one compound of formula I in R represents ethyl, propyl, butyl or cyclopentyl; and Dashed lines represent carbon-carbon single bonds or carbon-carbon double bonds; and (b) providing at least one other flavorant, (c) adding at least one compound of formula (I) to at least one other flavor in an organoleptically effective amount sufficient to modify the existing flavor to make it fruitier, juicier, softer, sharper, fresher, sweeter and / or more floral.

[0050] Preferably, the weight ratio of at least one compound of formula I to the total amount of other fragrances is in the range of 1:100 to 1:10. More preferably, the weight ratio of at least one compound of formula I to the total amount of other fragrances is in the range of 1:85 to 1:15.

[0051] In this context, preference is given to a total amount of at least one compound of the formula I in the range from 0.0001 to 99.9% by weight, preferably from 0.001 to 99.5% by weight, particularly preferably from 0.01 to 99% by weight, from 0.01 to 90% by weight, from 0.01 to 50% by weight, from 0.01 to 20% by weight, from 0.01 to 10% by weight and particularly preferably from 0.01 to 5% by weight, in particular from 0.05 to 2.0% by weight, in each case based on the total weight of the composition.

[0052] In a preferred embodiment according to the present invention, at least one other fragrance is selected from the group consisting of AGRUMEX LC, C10 aldehyde, C11 aldehyde undecanal, C12 aldehyde laurin, C12 aldehyde MNA, C11 aldehyde MOA PURE, allyl cyclohexanepropionate, allyl heptanoate, ambroxol 10% IPM, anise aldehyde resin, watermelon ketone 10%, carvone L, coumarin, cyclodomol acetate, 2,6-dimethyl-7-octen-2-ol (dihydromyrcenol), dynasty ketone 1% DPG, 10% DPG, sea breeze aldehyde, anthocyanin, BM / PYRANOL, FURAMINTON / TONKALACTONE TM 1% DPG, Methyl-3-oxo-2-pentyl-1-cyclopentyl acetate (HEDION), piperonal / PIPERONAL, hexyl acetate, hexyl salicylate, isoamyl acetate, KRAUSE peppermint oil 65% AMERIK., LINOLAL, magnolol, melonal, methyl naphthyl ketone beta crystals, NEROLIONE 0.1% DPG, 2-phenylethanol (phenylethanol), TIMBERSILK, isohexenyl cyclohexenyl carboxaldehyde (vertomugal), ethyl acetoacetate, C14 aldehyde, C18 aldehyde, allyl hexanoate, benzaldehyde DD, citral FF, citronellol 950, citronellol acetate EXTRA, Italian citronellol, citronella oil terpenes, cyclamen aldehyde, damascenone, δ-damascenone, γ-decanoate, ethyl butyrate, ethyl maltol, ethyl 2-methylbutyrate, neryl acetate, piperonal / PIPERONAL, HERBAFLORAT, cis-3-hexenol, cis-3-hexenyl acetate, β-ionone, ISO E SUPER, isoborneol, isopropylmethylthiazole-2,410% DPG, JASMAPRUNAT, linalool, pyrethrin, γ-octalactone, styroyl acetate, NX, Thiol Menthone-8,3 10% DPG, Methyldecenol, Vanillin, Ligustrum lucidum, Allyl Isoamyl Acetate, α-Amyl Cinnamal, Benzyl Acetate, Dimethyl Benzyl Butyrate, γ-Dodecanoate, Glycol Brazilic Acid, Ethyl Linalool, Ethyl Vanillin, FLOROPAL, Tricyclodecenyl propionate, α-hexylcinnamaldehyde, isoamyl acetate, isoamyl butyrate, JASMAPRUNAT, SUPRA, methyl anthranilate, methyl cinnamate, lyrachaline alcohol, Amyl acetate, ROMANDOLIDE.

[0053] Preferably, at least one compound of the formula I is combined with one or more, particularly preferably with two, three, four, five or more of those preferred further fragrances.

[0054] Further preferably, the compound of formula I is selected from the group consisting of ethyl cyclohexene-1-carboxylate, butyl cyclohexenecarboxylate, cyclopentyl cyclohexanecarboxylate or a mixture thereof.

[0055] The other preferred embodiments listed above are also applicable to the method of the present invention.

[0056] Another aspect of the invention relates to a perfuming product comprising at least one compound of formula I in R represents ethyl, propyl, butyl or cyclopentyl; and Dashed lines represent carbon-carbon single bonds or carbon-carbon double bonds; and Two or more other flavors and optionally other ingredients, characterized in that the product comprises at least one compound of formula (I) in an amount that modifies the olfactory properties of the two or more other flavors to make them fruitier, juicier, softer, sharper, fresher, sweeter and / or more floral.

[0057] In a preferred embodiment, the perfumed product is selected from cosmetics, hygiene products and / or household products.The further preferred embodiments listed above also apply to the perfumed product according to the invention.

[0058] Preferably, the perfumed household item is selected from the group consisting of detergents and cleaning agents, hygiene or care products, preferably in the field of body and hair care, cosmetics and household, preferably selected from perfume extracts, perfumes, eau de toilette, aftershave lotions, colognes, pre-shave products, cologne pomades, perfumed refreshing tissues, acidic, alkaline or neutral detergents, textile fresheners, ironing aids, liquid detergents, powder detergents, laundry pretreaters, fabric softeners, washing tablets, disinfectants, surface disinfectants, air fresheners, aerosol sprays, waxes and polishes, personal care products, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, aftershave creams and lotions, suntan creams and lotions, hair care products, hair care products, decorative cosmetic products, candles, lamp oils, incense, insecticides, insect repellents and fuels. Most preferably, the perfumed product is selected from alcohol fragrances, personal hygiene products or household cleaning or care products.

[0059] Furthermore, it is preferred for the perfumed product according to the invention that the content of at least one compound of formula II is sufficient to provide the consumer with one or more olfactory properties selected from the group consisting of: fruitier, juicier, softer, sharper, fresher, sweeter and / or more floral.

[0060] It is also preferred that the total amount of compounds of formula I is in the range from 0.00001 to 10 wt.-%, preferably 0.0001 to 5 wt.-%, particularly preferably 0.001 to 2 wt.-%, more preferably 0.5 to 2 wt.-%, based on the total weight of the perfumed product.

[0061] The above-mentioned additives, auxiliary agents and / or active substances are preferably not odorous substances. These can be, for example, preservatives, antimicrobial agents, chelating agents, detergents, emulsifiers, fats, etc., and in principle can be all substances used as additives, auxiliary agents and / or active ingredients in cosmetics, especially perfume compositions and household products.

[0062] The further preferred embodiments listed above also apply to the perfumed product according to the invention.

[0063] Next, the present invention will be further described based on examples.

[0064] Example 1: Synthesis of ethyl cyclohexene-1-carboxylate

[0065] 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 was distilled. After the reaction was complete, the organic layer was washed to neutrality and evaporated in a rotary evaporator to give a crude product, which was then distilled by bulb-to-bulb distillation to give the title compound with Wt=2.5 g, Y=66.6%. 2.5g cyclohexene-1-carboxylic acid produces 1.1g, y = 98% 1 H NMR(400MHz, CDCl3)δ6.98(tt,J=3.8,1.8Hz,1H),4.18(q,J=7.1Hz,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=7.1Hz,3H). 13 C NMR (101MHz, CDCl3) δ167.71,139.44,130.50,60.17,25.76,24.14,22.11,21.50,14.31. Smell: Cinnamon, Almond Sugar, Chlorine, Benzophenone

[0066] Example 2: Synthesis of Butyl Cyclohexenecarboxylate

[0067] A mixture of cyclohexanecarboxylic acid (400.0 g, 3.1 mol), 1-butanol (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 was distilled out. After the reaction was complete, the organic layer was washed to neutrality and evaporated in a rotary evaporator to give a crude product (571.0 g), which was subsequently distilled by short-path distillation (bulb-to-bulb distillation) to give butyl cyclohexenecarboxylate with wt=467.0 g, Y=98%. 1H NMR (400MHz, CDCl3) δ4.06 (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=7.5,6.6Hz,2H),1.51–1.35(m,2H),1.38(h,J=7.5Hz,2H),1.34–1.17(m,3H),0.93(t,J=7.4Hz,3H). 13C NMR (101MHz, CDCl3) δ176.26,63.97,43.32,30.76,29.08,29.08,25.82,25.50,25.50,19.18,13.74. MS:184,168,129,111,83,55,41,29. Aroma: Fruity, Valeric, Sweet, Cinnamon, Castoreum, Apple, Pear, Pineapple

[0068] Example 3: Synthesis of Cyclopentyl Cyclohexanecarboxylate

[0069] 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 was distilled. After the reaction was complete, the organic layer was washed to neutrality and evaporated in a rotary evaporator to give a crude product (629.3 g), which was subsequently distilled by short-path distillation (bulb-to-bulb distillation) to give wt=551.6 g, Y=97% cyclopentyl cyclohexanecarboxylate. 1H NMR(400MHz, CDCl3)δ5.15(tt,J=5.7,2.7Hz,1H),2.23(tt,J=11.2,3.6Hz,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). 13C NMR (101MHz, CDCl3) δ175.98,76.51,43.35,32.71,32.71,29.01,29.01,25.83,25.47,25.47,23.77,23.77. MS:196,168,152,129,111,83,69,55,41,29 Smell: Fruity, pineapple, green, strawberry

[0070] Example 4: Spice Mixture

[0071] Table 1: Spice mixture More fruity, juicy and Citrus, watery pineapple, softer and floral notes

[0072] Table 2: Spice Mixture

[0073] According to the panel, the fragrance blend without cyclopentyl cyclohexanecarboxylate smelled fruity with mango, peach, pineapple and citrus. The addition of cyclopentyl cyclohexanecarboxylate to the fragrance blend made the fragrance blend sharper, fresher and juicier.

[0074] Table 3: Spice Mixture 3

[0075] According to the expert panel, the fragrance blend without cyclopentyl cyclohexanecarboxylate smelled fruity and like apples. Adding a small amount (40 parts) of cyclopentyl cyclohexanecarboxylate to the fragrance blend made the fragrance blend more fruity and produced an additional orange effect. Adding a larger amount (60 parts) of cyclopentyl cyclohexanecarboxylate to the fragrance blend made the fragrance blend more fruity with an additional sweetness.

Claims

1. At least one compound of formula I As a spice, R represents ethyl, propyl, butyl or cyclopentyl, and Dashed lines represent carbon-carbon single bonds or carbon-carbon double bonds.

2. The method 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 perfume composition to obtain at least one of the following notes: cinnamon, almond, fruity, valeric, sweet, apple, pear, pineapple, strawberry, green and / or castoreum, 7. Use according to claims 1 to 5 for imparting, improving and / or enhancing a fragrance composition to make it fruitier, juicier, softer, sharper, fresher, sweeter and / or more floral.

8. A fragrance composition comprising at least one compound of formula I in R represents ethyl, propyl, butyl or cyclopentyl; and Dashed lines represent carbon-carbon single bonds or carbon-carbon double bonds; and at least one other flavoring, or consisting thereof.

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

10.

10. The flavor composition according to claim 9, wherein the weight ratio of at least one compound of formula I to the total amount of other flavors is in the range of 1:85 to 1:15 11. The fragrance composition according to claims 8 to 10, wherein the total amount of 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. A flavor composition according to at least one of claims 8 to 11, wherein at least one compound of formula (I) is added to the flavor composition in an organoleptically effective amount sufficient to modify the existing flavor to make it fruitier, juicier, softer, sharper, fresher, sweeter and / or more floral.

13. Use of a flavor composition according to at least one of claims 8 to 11 for modifying an existing flavor to make it fruitier, juicier, softer, sharper, fresher, sweeter and / or more floral.

14. A method for improving an existing flavor to make it fruitier, juicier, pineappleier, milder and / or more floral, Include or consist of the following steps: (a) providing at least one compound of formula I in R represents ethyl, propyl, butyl or cyclopentyl; and Dashed lines represent carbon-carbon single bonds or carbon-carbon double bonds; and (b) providing at least one other flavorant, (c) adding at least one compound of formula (I) to at least one other flavor in an organoleptically effective amount sufficient to modify the existing flavor to make it fruitier, juicier, softer, sharper, fresher, sweeter and / or more floral.

15. Perfumed products comprising at least one compound of formula I in R represents ethyl, propyl, butyl or cyclopentyl; and Dashed lines represent carbon-carbon single bonds or carbon-carbon double bonds; and Two or more other spices and optionally other ingredients, characterized in that The product comprises at least one compound of formula (I) in an amount which modifies the olfactory properties of two or more other flavorants to make them fruitier, juicier, softer, sharper, fresher, sweeter and / or more floral.

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