Ethyl 2-cyclooctylacetate as a fragrance

Abstract

The use of ethyl 2-cyclooctylacetate as a fragrance is proposed.

Description

Technical Field

[0001] The present invention relates to the use of ethyl 2-cyclooctylacetate as a fragrance. The present invention also relates to fragrance compositions, their use, and methods for imparting, modifying and / or enhancing certain fragrance notes.

Background Art

[0002] In the fragrance industry, there is always a demand for the development of new fragrances. However, the development of new fragrances and fragrance compositions involves many challenges. For example, in order to meet specific market requirements and provide products that match specific profiles desired by customers, it is necessary to select specific compositions of several fragrances from a virtually infinite number of possible structures known in the prior art. Suitable fragrances exhibit very beneficial properties. However, when combined with other fragrances, they may produce unpleasant and thus harmful odor characteristics, making them difficult or impossible to use for specific purposes.

[0003] The second important issue relates to the requirement to provide fragrance compositions that not only match a specific aromatic profile but also have so-called secondarily beneficial properties. In fact, many fragrance compositions known in the market have not only serious drawbacks in use, such as low solubility and storage stability, but also deficiencies in subjective issues such as richness and charisma. Also, many known fragrance compositions require high dosages to obtain the desired aromatic results. Another requirement for fragrances today is high biodegradability, as well as dermatological and toxicological safety. Thus, there is a particular need to provide fragrances that, even in small amounts, have a large impact on other fragrances, change unpleasant aromatic impressions into positive ones, and / or enhance pleasant aromatic impressions.

Summary of the Invention

Problems to be Solved by the Invention

[0004] Accordingly, an object of the present invention is to provide a new fragrance having the ability to enhance the positive and beneficial aromatic properties of other fragrances and / or (simultaneously) the ability to reduce, suppress and / or mask undesirable unpleasant aromatic properties. In particular, the new fragrance should also be characterized by improving the stability, solubility and overall performance of other fragrances and reducing the required amount. Finally, the fragrance composition itself must have excellent biodegradability and be harmless to the human body and the environment.

Means for Solving the Problems

[0005] This is solved by the use of ethyl 2-cyclooctylacetate as a fragrance.

Embodiments for Carrying Out the Invention

[0006] Ethyl 2-cyclooctylacetate used in the present invention may exist in the form of any stereoisomer or as a mixture of any stereoisomers.

[0007] What has been described herein about ethyl 2-cyclooctylacetate, in particular, the advantages described herein also apply to mixtures of stereoisomers of ethyl 2-cyclooctylacetate used or employed according to the present invention.

[0008] Ethyl 2-cyclooctylacetate is very unique and has olfactory properties that are clearly different from and superior to known aromatic substances. The compatibility of ethyl 2-cyclooctylacetate as a fragrance has not been known so far. Therefore, it is particularly surprising that a fragrance having valuable, interesting and complex olfactory properties has been discovered in a field that has already been well studied.

[0009] Ethyl 2-cyclooctylacetate has the following structural formula and preferably has the following unique Cas number: 80246-71-5. TIFF2025518220000001.tif34147

[0010] As described above, its suitability as a fragrance is not known. Similarly, there is no exact fragrance description. However, according to the inventors, ethyl 2-cyclooctylacetate has a fruity, floral, somewhat orange-like fragrance.

[0011] As a result, the inventors have surprisingly found that ethyl 2-cyclooctylacetate is suitable as a fragrance and exhibits a specific effect when combined in small amounts with a compound having a pleasant odor different from ethyl 2-cyclooctylacetate.

[0012] In a preferred embodiment of the present invention, ethyl 2-cyclooctylacetate is used to enhance one or more pleasant olfactory impressions of one or more compounds having a pleasant odor. Here, one or more of the said compounds are different from ethyl 2-cyclooctylacetate. Preferably, one or more pleasant olfactory impressions of one or more compounds having a pleasant odor are selected from enhancing and / or improving fruity notes. This means that ethyl 2-cyclooctylacetate preferably enhances or improves the fruity notes of compounds having a pleasant odor.

[0013] As used herein, the singular forms "a", "an", and "the" include plural referents unless the context clearly dictates otherwise. For example, the term "compound" or "at least one compound" can include a plurality of compounds (including mixtures thereof). Also, the plural form includes singular referents unless the context clearly dictates otherwise. For example, "one or more compounds having a pleasant odor" also encompasses embodiments having only one compound having a pleasant odor.

[0014] The fact that ethyl 2-cyclooctylacetate used according to the present invention can give a very complex and diverse overall sensory impression, which can usually only be achieved by a mixture of a plurality of components (such as essential oils or spice mixtures), is particularly surprising.

[0015] Ethyl 2-cyclooctylacetate, in addition to its main properties, namely olfactory properties, further has favorable secondary properties, in particular, higher persistence compared to fragrances having similar olfactory properties, as well as high stability and high extensibility in specific media and compositions, and also has biodegradability.

[0016] Ethyl 2-cyclooctylacetate has also been found to function excellently as a so-called booster (amplifier, enhancer). Preferably, ethyl 2-cyclooctylacetate is used as a booster for one or more pleasant olfactory impressions of one or more pleasant-smelling compounds. In other words, the use of ethyl 2-cyclooctylacetate in combination with other pleasant-smelling compounds enhances their pleasant-smelling aromatic notes.

[0017] Furthermore, ethyl 2-cyclooctylacetate used according to the present invention can enhance the strength of the fragrance composition and can soften the overall aroma of the mixture. Accordingly, the compounds described herein can be used to impart a higher degree of fruitiness and / or enhanced fruity notes to other compounds, particularly to pleasant-smelling compounds having one or more pleasant olfactory impressions. Also, ethyl 2-cyclooctylacetate is suitable as an agent for enhancing the persistence and / or retention power of a constant composition.

[0018] The "pleasant-smelling compound" in the present invention is generally understood to be a substance that evokes one or more pleasant aromatic impressions, which are primary or secondary / dependent olfactory notes. The terms "pleasant-smelling compound" and "fragrance" are used interchangeably herein.

[0019] Preferably, one or more pleasant-smelling compounds different from the above-mentioned ethyl 2-cyclooctylacetate are selected from the group consisting of fragrances having a molar mass in the range of 150 g / mol to 285 g / mol, particularly alcohols, aldehydes, ketones, ethers, esters, and carboxylates having a molar mass in the range of 150 g / mol to 285 g / mol.

[0020] More preferably, the one or more pleasant smell compounds are γ-undecalactone, γ-nonalactone, 6,6-dimethoxy-2,5,5-trimethylhex-2-ene, (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxol, (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan, 1-methoxy-4-[(E)-prop-1-enyl]benzene, 4-methoxybenzaldehyde, cyclohexadec-2-en-1-one, benzenecarbaldehyde benzyl acetate, 7-methyl-2,4-dihydro-3H-1,5-benzodioxepin-3-one, cis-6-nonenal, 3-(4-methoxyphenyl)-2-methylpropanal, 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone, cedrol methyl ether, (1S,2R,5S,7R,8R)-2,6,6,8-tetramethyltricyclo[5.3.1.01,5]undecan-8-ol, (3R)-3,7-dimethyloct-6-ene, citronellyl acetate, 2H-chromen-2-one, damascenone, γ-decalactone, di(octyl) hexanedioate, ethylene brassylate, (6E)-3,7-dimethylnona-1,6-dien-3-ol, 2-ethyl-3-hydroxy-4H-pyran-4-one, 3-(o-ethylphenyl)-2,2-dimethylpropionaldehyde and 3-(p-ethylphenyl)-2,2-dimethylpropionaldehyde, 3-(3-propan-2-ylphenyl)butanal, 4-methyl-2-(2-methylpropyl)oxan-4-ol, (3S)-3,6-dimethyl-3H-1-benzofuran-2-one, 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]isochromene, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, 2H-1,3-benzodioxole-5-carbaldehyde, 3a,4,5,6,7,7a-hexahydro-4,Selected from the group consisting of 7-methanoylnaphthalen-6-yl acetate, (3Z)-hex-3-en-1-ol, cis-3-hexen-1-yl acetate, cis-3-hexenyl salicylate, hexyl acetate, 1H-indole, 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl)ethenone, 1-(2,6,6-trimethyl-1-cyclohex-2-enyl)penta-1-en-3-one N,3,7-dimethyloct-1,6-dien-3-ol, 3,7-dimethyloct-1,6-dien-3-yl acetate, 3-hydroxy-2-methyl-4H-pyran-4-one, ethyl 2-methylpentanoate, methyl 2-aminobenzoate, methyl oct-2-ynoate, diethyl (E / Z)-2-methylbut-2-enedioate, 3-methyl-5-phenylpentan-1-ol, (E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, (E)-2-ethyl-4-(2,2,3-trimethyl-1-cyclopent-3-enyl)but-2-en-1-ol, styrallyl acetate, 3,7-dimethyloctan-3-ol, 2-methyl-2-sulfanylpentan-1-ol, (E)-4-methyldec-3-en-5-ol.,

[0021] In a preferred embodiment of the present invention, the ratio of the total mass of the pleasant-smelling compounds to the total mass of ethyl 2-cyclooctylacetate is in the range of 1:10 to 1:1000, more preferably 1:25 to 1:50.

[0022] Ethyl 2-cyclooctylacetate can be used in various products. It can be used as a single fragrance, but it can also be particularly advantageously combined with other pleasant-smelling compounds, especially fragrances in different proportions, to form a fragrance mixture and can also create new and innovative fragrance compositions. Preferably, the amount of ethyl 2-cyclooctylacetate in the fragrance composition is not sufficient to generate a characteristic aroma, especially a fruity and / or floral-like aroma. That is, ethyl 2-cyclooctylacetate, when used according to the present invention, has the advantage of exerting its effect at a concentration so low that its own characteristic aroma is not at all or at least hardly perceptible. Thereby, a particularly advantageous fragrance composition or product having any fragrance directionality can be manufactured.

[0023] Accordingly, one embodiment of the present invention also relates to a fragrance mixture and possible further components (such as solvents), which contain ethyl 2-cyclooctylacetate.

[0024] The fragrance composition of the present invention contains, or consists of, ethyl 2-cyclooctylacetate and at least one further pleasant-smelling compound different from ethyl 2-cyclooctylacetate. Preferably, the fragrance composition of the present invention contains, or consists of, ethyl 2-cyclooctylacetate and two or more pleasant-smelling compounds different from ethyl 2-cyclooctylacetate. More preferably, the fragrance composition of the present invention contains, or consists of, ethyl 2-cyclooctylacetate and three or more further pleasant-smelling compounds different from ethyl 2-cyclooctylacetate. Most preferably, the fragrance composition of the present invention contains, or consists of, ethyl 2-cyclooctylacetate and four or more further pleasant-smelling compounds different from ethyl 2-cyclooctylacetate.

[0025] Ethyl 2-cyclooctylacetate of the present invention is usually used in a functionally effective amount, that is, in the total amount in which it exerts a functional effect.

[0026] Preferably, the weight ratio of ethyl 2-cyclooctylacetate to the total amount of compounds having a pleasant odor different from ethyl 2-cyclooctylacetate is in the range of 1:10 to 1:1000, preferably 1:25 to 1:50.

[0027] In a preferred embodiment of the present invention, ethyl 2-cyclooctylacetate is contained in the perfume composition in a functionally effective amount sufficient to enhance one or more pleasant olfactory impressions of one or more compounds having a pleasant odor different from ethyl 2-cyclooctylacetate, in particular to enhance or improve the fruity olfactory note of one or more compounds having a pleasant odor different from ethyl 2-cyclooctylacetate.

[0028] Examples of compounds having a pleasant odor, in particular perfumes, that can be advantageously combined with ethyl 2-cyclooctylacetate in the present invention can be found, for example, in S. Arctander, Perfume and Flavor Materials, Volumes I and II, Montclair, N.J. 1969, self-published, or K. Bauer et al., Common Fragrance and Flavor Materials, Fourth Edition, Wiley-VCH, Weinheim 2001.

[0029] Particularly, the following can be mentioned: extracts from natural raw materials such as essential oils, concretes, absolutes, resins, resinoids, balsams, tinctures, for example, Ambergris tincture; Amyris oil; Angelica seed oil; Angelica root oil, Anise oil; Valerian oil; Basil oil; Tree moss absolute; Bay oil; Mugwort oil; Benzoin resinoid; Bergamot oil; Beeswax absolute; Birch tar oil; Bitter almond oil; Celery seed oil; Buchu leaf oil; Cubeb oil; Cajeput oil; Calamus oil; Camphor oil; Cananga oil; Cardamom oil; Cassia oil; Cascarilla oil; Cassia 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; Hinoki oil; Davana oil; Dill herb oil; Dill seed oil; Bouquet 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 oil; Guaiacwood oil; Gurjun balsam; Gurjun balsam oil; Helichrysum absolute; Helichrysum oil; Ginger oil; Iris root absolute; Iris root oil; Jasmine absolute; Canna 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; Ravintsara absolute; Ravintsara oil; Lavender absolute; Lavender oil; Lemongrass oil; Rabdane oil; Distilled lime oil; Expressed lime oil; Linaloe oil; Litsea cubeba 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; Myrtle oil; Clove leaf oil; Clove flower oil; Neroli oil; Olibanum absolute; Olibanum oil; Opopanax oil; Orange blossom absolute; Orange oil; Oregano oil; Palmarosa oil; Patchouli oil; Perilla oil; Petitgrain oil; Parsley leaf oil; Parsley seed oil; Petitgrain bigarade oil; Peppermint oil; Pepper oil; Allspice oil; Pine oil; Boleyn 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; perilla oil; chamomile 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; wild chrysanthemum oil; wintergreen oil; ylang-ylang oil; hyssop oil; civet absolute; cinnamon leaf oil; cinnamon bark oil, and fractions thereof or components isolated therefrom;

[0030] Each aroma substance from the following group: Hydrocarbons, such as 3-carene; α-pinene; β-pinene; a-terpinene; γ-terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E,Z)-1,3,5-undecatriene; styrene; diphenylmethane; Aliphatic alcohols, such as hexanol; octanol; 3-octanol; 2,6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E)-2-hexenol; 1-octen-3-ol; mixture of 3,4,5,6,6-pentamethyl-3 / 4-hepten-2-ol and 3,5,6,6-tetramethyl-4-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;

[0031] Aliphatic aldehydes and their acetals, such as hexanal; heptanal; octanal; nonanal; decanal; undecanal; dodecanal; 2-methyloctanal; 2-methylnonanal; (E)-2-hexenal; (Z)-4-heptenal; 2,6-dimethyl-5-heptenal; 10-undecenal; (E)-4-decenal; 2-dodecenal; 2,6,10-trimethyl-9-undecenal; 2,6,10-trimethyl-5,9-undecadienal; heptanal diethyl acetal; 1,1-dimethoxy-2,2,5-trimethyl-4-hexene; citronellyloxyacetaldehyde; 1-(1-methoxypropoxy)-(E / Z)-3-hexene; 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;

[0032] 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; Esters of aliphatic carboxylic acids, for example, (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-dimethyl-2,6-octadienoate; 4-methyl-2-pentyl crotonate;

[0033] Acyclic terpene alcohols, for example, 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-dimethylocta-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, isovalerianates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates; Non-cyclic terpene aldehydes and ketones, such as citronellal; 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal; geranylacetone; and dimethyl and diethyl acetals of geranial and neral; 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; ambrinol; vetiverol; guaiol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerianates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates;

[0034] 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-isomethyliorone; 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-methanonaphthalene-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 cedrol oil (methyl cedryl ketone); 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; alicyclic 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;

[0035] cyclic and alicyclic 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[2,1b]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; Cyclic and macrocyclic ketones, 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-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; Alicyclic aldehydes, for example, 2-methyl-4-(2,2,6-trimethylcyclohexen-1-yl)-2-butenal; 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarbaldehyde; 4-(4-methyl-3-penten-1-yl)-3-cyclohexenecarbaldehyde;

[0036] Alicyclic 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-naphthalenyl methyl ketone; methyl 2,6,10-trimethyl-2,5,9-cyclododecatrienyl ketone; 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-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 or 6-indenyl acetate; 4,7-methano-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl propionate; 4,7-methano-3a,4,5,6,7,7a-hexahydro-5 or 6-indenyl isobutyrate; 4,7-methanooctahydro-5 or 6-indenyl acetate; Esters of alicyclic alcohols, such as 1-cyclohexylethyl crotonate; Esters of alicyclic 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;

[0037] Aromatic aliphatic alcohols, for example, 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;

[0038] 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-dimethylphenylethyl acetate; α,α-dimethylphenylethyl butyrate; cinnamyl acetate; 2-phenoxyethyl isobutyrate; 4-methoxybenzyl acetate;

[0039] 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; aromatic and 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-butylphenyl)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;

[0040] 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',5',6',8',8'-hexamethyl-2-acetonaphthone;

[0041] 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; phenylethyl salicylate; methyl 2,4-dihydroxy-3,6-dimethylbenzoate; ethyl 3-phenylglycidate; ethyl 3-methyl-3-phenylglycidate;

[0042] 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;

[0043] Lactones, for example, 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-hexadecene-1,16-olide; 10-oxa-1,16-hexadecanolide; 11-oxa-1,16-hexadecanolide; 12-oxa-1,16-hexadecanolide; ethylene-1,12-dodecadioate; ethylene-1,13-tridecanedioate; 2,3-dihydrocoumarin; octahydrocoumarin.

[0044] In another preferred embodiment of the present invention, preferably, ethyl 2-cyclooctylacetate is combined with one or more, particularly preferably 2, 3, 4, 5 or more, pleasant-smelling compounds.

[0045] Correspondingly, the present invention also relates to a perfume composition comprising one, two, three, four, five or more other perfumes that convey woody and / or gurmar-type aromatic notes.

[0046] Ethyl 2-cyclooctylacetate used according to the present invention advantageously (at least partially) achieves an enhancement of the aroma of the olfactory impression of a pleasant smell.

[0047] Preferably, at least one pleasant-smelling compound different from ethyl 2-cyclooctylacetate described above is selected from perfumes having a molar mass in the range of 150 g / mol to 285 g / mol, particularly from the group consisting of alcohols, aldehydes, ketones, ethers, esters and carboxylates having a molar mass in the range of 150 g / mol to 285 g / mol.

[0048] In another preferred embodiment of the present invention, the at least one pleasant-smelling compound is γ-undecalactone, γ-nonalactone, 6,6-dimethoxy-2,5,5-trimethylhex-2-ene, (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazulenol(5,6-d)-1,3-dioxole, (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan, 1-methoxy-4-[(E)-prop-1-enyl]benzene, 4-methoxybenzaldehyde, cyclohexadec-2-en-1-one, benzenecarbaldehyde benzyl acetate, 7-methyl-2,4-dihydro-3H-1,5-benzodioxepin-3-one, cis-6-nonenal, 3-(4-methoxyphenyl)-2-methylpropanal, 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone, cedrol methyl ether, (1S,2R,5S,7R,8R)-2,6,6,8-tetramethyltricyclo[5.3.1.01,5]undecan-8-ol, (3R)-3,7-dimethyloct-6-ene, citronellyl acetate, 2H-chromen-2-one, damascenone, γ-decalactone, di(octyl) hexanedioate, ethylenebrassylate, (6E)-3,7-dimethylnona-1,6-dien-3-ol, 2-ethyl-3-hydroxy-4H-pyran-4-one, 3-(o-ethylphenyl)-2,2-dimethylpropionaldehyde and 3-(p-ethylphenyl)-2,2-dimethylpropionaldehyde, 3-(3-propan-2-ylphenyl)butanal, 4-methyl-2-(2-methylpropyl)oxan-4-ol, (3S)-3,6-dimethyl-3H-1-benzofuran-2-one, 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]isochromene, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, 2H-1,3-benzodioxole-5-carbaldehyde, 3a,4,5,6,7,7a-hexahydro-4,Selected from the group consisting of 7-methanoinden-6-yl acetate, (3Z)-hex-3-en-1-ol, cis-3-hexen-1-yl acetate, cis-3-hexenyl salicylate, hexyl acetate, 1H-indole, 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl)ethenone, 1-(2,6,6-trimethyl-1-cyclohex-2-enyl)pent-1-en-3-one N, 3,7-dimethyloct-1,6-dien-3-ol, 3,7-dimethyloct-1,6-dien-3-yl acetate, 3-hydroxy-2-methyl-4H-pyran-4-one, ethyl 2-methylpentanoate, methyl 2-aminobenzoate, methyl oct-2-inoate, diethyl (E / Z)-2-methylbut-2-enedioate, 3-methyl-5-phenylpentan-1-ol, (E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, (E)-2-ethyl-4-(2,2,3-trimethyl-1-cyclopent-3-enyl)but-2-en-1-ol, styrallyl acetate, 3,7-dimethyloctan-3-ol, 2-methyl-2-sulfanylpentan-1-ol, (E)-4-methyldec-3-en-5-ol.,

[0049] Preferably, ethyl 2-cyclooctylacetate is combined with one or more of these preferably pleasant-smelling compounds, particularly preferably 2, 3, 4, 5 or more thereof.

[0050] The perfume composition containing ethyl 2-cyclooctylacetate is advantageously used in fragrances in the form of a liquid that is undiluted or diluted with a solvent. Suitable solvents for this 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.

[0051] In addition, the fragrance composition of the present invention can be adsorbed on a carrier, which ensures both excellent dispersion of the fragrance in the product and controlled release during use. Such carriers can be porous inorganic materials such as light sulfate, silica gel, zeolite, gypsum, 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 resulting combination of the composition of the present invention and the carrier substance is also understood as the fragrance composition of the present invention.

[0052] The fragrance composition of the present invention can also be microencapsulated and spray-dried as an inclusion complex or an extruded product, and in this form, it can also be added to, for example, a scented product.

[0053] If necessary, the properties of the composition thus modified can be further optimized by "coating" with a suitable material for the purpose of more precisely releasing the fragrance. For this purpose, waxy plastics such as polyvinyl alcohol are preferably used. The resulting product corresponds to the article according to the present invention.

[0054] Preferably, the amount of ethyl 2-cyclooctylacetate ranges from 0.001 to 50% by weight based on the total weight of the fragrance composition. More preferably, the amount of ethyl 2-cyclooctylacetate ranges from 0.01 to 10% by weight based on the total weight of the fragrance composition. More preferably, the amount of ethyl 2-cyclooctylacetate ranges from 0.01 to 1% by weight based on the total weight of the fragrance composition. More preferably, the amount of ethyl 2-cyclooctylacetate ranges from 0.01 to 0.1% by weight based on the total weight of the fragrance composition.

[0055] The fragrance composition of the present invention can be advantageously used in a concentrated form, a solution form, or a modified form as described above for the production of the fragrance products of the present invention, such as, for example, B. fragrance extracts, eau de parfum, eau de toilette, aftershave, eau de cologne, pre-shave products, splash cologne, fragrance refreshment towels, acidic, alkaline and neutral detergents (e.g., floor detergents, window glass detergents, dishwashing detergents, bathroom and sanitary detergents, abrasive milks, solid and liquid toilet detergents, powder and foam carpet detergents, etc.), fabric fresheners, ironing aids, liquid detergents, powder detergents, bleaches, soaking agents and stain removers, etc. as pre-washing agents for laundry, fabric softeners, laundry soaps, laundry tablets, disinfectants, air fresheners, aerosol sprays, furniture polishes, floor waxes, shoe creams, etc. in the form applied on a liquid, gel or solid carrier, and personal care products, such as, for example, solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams, bath oils, water-in-oil, oil-in-water, water-in-oil-in-water cosmetic emulsions (e.g., skin creams and lotions, face creams and lotions, sunscreens and lotions, after-sun creams and lotions, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, aftershave creams and lotions, sunburn creams and lotions), hair care products (e.g., hair sprays, hair gels, hair setting lotions, hair conditioners, long-term and semi-permanent hair dyes, hair styling agents such as cold waves and hair straighteners, hair lotions, hair creams and lotions), underarm sprays, roll-ons, deodorant sticks, deodorant creams, etc. as deodorants and antiperspirants, decorative cosmetics such as eye shadows, nail polishes, lipsticks, mascaras, etc., and candles, lamp oils, incense sticks, insecticides, repellents and fuels, etc.

[0056] Of course, the fragrance composition of the present invention may be included in a cosmetic composition or a household composition.

[0057] Another embodiment of the present invention is an aromatic product containing the above perfume composition in a sensory effective amount, wherein the amount of the perfume composition calculated based on the total weight of the aromatic product is preferably in the range of 0.01 to 10% by weight, more preferably 0.1 to 5% by weight, and most preferably 0.25 to 3% by weight.

[0058] In a preferred embodiment, the aromatic product is selected from cosmetics, hygiene products and / or household products. Another preferred embodiment described above is also applicable to the aromatic product of the present invention.

[0059] Preferably, the aromatic product is preferably selected from the group consisting of detergents and cleaning agents, satellite or care products in the fields of body and hair care, cosmetics and household products, preferably perfume extracts, eau de parfum, eau de toilette, aftershave lotion, eau de cologne, pre-shave products, splash cologne, aromatic refresh tissues, acidic, alkaline or neutral cleaning agents, fabric fresheners, ironing aids, liquid detergents, powder detergents, pre-wash treatments, fabric softeners, cleaning 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, sunburn creams and lotions, hair care products, hair care products, decorative cosmetics, candles, lamp oils, incense sticks, insecticides, repellents and fuels. Most preferably, the aromatic product is selected from alcoholic perfumes, personal hygiene products, or cleaning or care products used at home.

[0060] Further, for the aromatic product of the present invention, it is preferably contained ethyl 2-cyclooctylacetate in a sensory effective amount sufficient for the consumer to have one or more olfactory characteristics selected from the group consisting of a higher degree of fruitiness and / or enhanced fruity notes.

[0061] The above additives, auxiliaries and / or active substances are preferably not substances that emit an aroma. These can be, for example, preservatives, antibacterial agents, chelating agents, detergents, emulsifiers, fats, etc., and in principle all substances used as additives, auxiliaries and / or active ingredients in cosmetics, particularly fragrance compositions, as well as household compositions.

[0062] Another embodiment of the present invention is a method for enhancing the olfactory impression of one or more pleasant-smelling notes of one or more pleasant-smelling compounds, particularly a method for enhancing and / or improving the fruity note of one or more pleasant-smelling compounds, wherein said compound is different from ethyl 2-cyclooctylacetate, said method comprising or consisting of the step of mixing a pleasant-smelling compound with ethyl 2-cyclooctylacetate, relating to a method wherein the amount of ethyl 2-cyclooctylacetate is an amount sufficient to enhance and / or improve the fruity note of one or more pleasant-smelling compounds.

[0063] Preferably, the weight ratio of ethyl 2-cyclooctylacetate to the total amount of a pleasant-smelling compound different from ethyl 2-cyclooctylacetate is in the range of 1:5000 to 1:1000, more preferably 1:3000 to 1:2000.

[0064] In a preferred embodiment of the present invention, one or more pleasant-smelling compounds are γ-undecalactone, γ-nonalactone, 6,6-dimethoxy-2,5,5-trimethylhex-2-ene, (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazulenol(5,6-d)-1,3-dioxole, (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan, 1-methoxy-4-[(E)-prop-1-enyl]benzene, 4-methoxybenzaldehyde, cyclohexadec-2-en-1-one, benzenecarbaldehyde benzyl acetate, 7-methyl-2,4-dihydro-3H-1,5-benzodioxepin-3-one, cis-6-nonenal, 3-(4-methoxyphenyl)-2-methylpropanal, 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone, cedrol methyl ether, (1S,2R,5S,7R,8R)-2,6,6,8-tetramethyltricyclo[5.3.1.01,5]undecan-8-ol, (3R)-3,7-dimethyloct-6-ene, citronellyl acetate, 2H-chromen-2-one, damascenone, γ-decalactone, di(octyl) hexanedioate, ethylene brassylate, (6E)-3,7-dimethylnona-1,6-dien-3-ol, 2-ethyl-3-hydroxy-4H-pyran-4-one, 3-(o-ethylphenyl)-2,2-dimethylpropionaldehyde and 3-(p-ethylphenyl)-2,2-dimethylpropionaldehyde, 3-(3-propan-2-ylphenyl)butanal, 4-methyl-2-(2-methylpropyl)oxan-4-ol, (3S)-3,6-dimethyl-3H-1-benzofuran-2-one, 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]isochromene, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, 2H-1,3-benzodioxole-5-carbaldehyde, 3a,4,5,6,7,7a-hexahydro-4,Selected from the group consisting of 7-methanoinden-6-yl acetate, (3Z)-hex-3-en-1-ol, cis-3-hexen-1-yl acetate, cis-3-hexenyl salicylate, hexyl acetate, 1H-indole, 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl)ethenone, 1-(2,6,6-trimethyl-1-cyclohex-2-enyl)pent-1-en-3-one N,3,7-dimethyloct-1,6-dien-3-ol, 3,7-dimethyloct-1,6-dien-3-yl acetate, 3-hydroxy-2-methyl-4H-pyran-4-one, ethyl 2-methylpentanoate, methyl 2-aminobenzoate, methyl oct-2-ynoate, diethyl (E / Z)-2-methylbut-2-enedioate, 3-methyl-5-phenylpentan-1-ol, (E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, (E)-2-ethyl-4-(2,2,3-trimethyl-1-cyclopent-3-enyl)but-2-en-1-ol, styrallyl acetate, 3,7-dimethyloctan-3-ol, 2-methyl-2-sulfanylpentan-1-ol, (E)-4-methyldec-3-en-5-ol.,

[0065] Preferably, ethyl 2-cyclooctylacetate is combined with one or more, particularly preferably 2, 3, 4, 5 or more of these pleasant-smelling compounds, especially in combination with a fragrance.,

[0066] The further preferred embodiments mentioned above are also applicable to the method of the present invention.,

[0067] The present invention will be further characterized based on the following examples. Unless otherwise specified, all amounts are shown in weight percent.,

Examples

[0068] Examples Example 1: Synthesis of ethyl 2-cyclooctylacetate 69 g (0.63 mol) of cyclooctene, 2500 g (15.6 mol) of diethyl malonate, and 26 g (0.18 mol) of di-tert-butyl peroxide were introduced into a 5 L autoclave, and heated under 5 bar of N 2 2. The mixture was stirred at 155 - 160 °C for 1 hour. The pressure rose to 11 bar. It was rapidly cooled to RT and evaporated on a rotary evaporator (bath temperature: 78 - 85 °C, vacuum: 4 mbar). The residue was fractionally distilled on a distillation bridge without a column. The product was distilled at a maximum temperature of 65 - 116 °C and a vacuum of 0.4 mbar. 116 g of diethyl 2-cyclooctylpropanedioate with a GC content of 84.9% was obtained. Diethyl 2-cyclooctylpropanedioate has the structure of Formula II. TIFF2025518220000002.tif40145 1 1H NMR: (400 MHz, CDCl3) δ 4.23 - 4.14 (m, 4H), 3.23 (dd, J = 8.9, 1.5 Hz, 1H), 2.42 - 2.31 (m, 1H), 1.76 - 1.34 (m, 14H), 1.30 - 1.24 (m, 6H) m / z: 41 (6), 55 (8), 69 (7), 88 (10), 105 (5), 115 (17), 133 (29), 160 (100), 197 (1), 225 (7)

[0069] 84.9% diethyl 2-cyclooctylpropanedioate of 111 g (0.35 mol) was introduced into a 250 mL stirrer equipped with a contact thermometer, a 10 cm Vigreux column, a distillation bridge, a dropping funnel, and a heating hood, and heated to 200 °C. At this temperature, 23 mL of water was added dropwise over 90 minutes while removing the distillate simultaneously. The residue (68 g) was distilled using a distillation bridge without a column. The crude product was distilled at a maximum temperature of 76 - 119 °C and a vacuum of 1 mbar. 60 g of the crude product was obtained. GC analysis showed that ethyl 2-cyclooctylacetate was 79.5% and unsaturated compounds were 16.6%. The crude product was hydrogenated in a 0.5 L autoclave using 100 mL of ethanol and 2 g of palladium on activated carbon (wet, 5% Pd) at a hydrogen pressure of 20 bar and 100 °C for 7 hours. The mixture was filtered, evaporated, and then distilled using a Kugelrohr at 70 - 95 °C under a vacuum of 0.6 mbar. 51 g of ethyl 2-cyclooctylacetate represented by Formula I with a GC content of 95.9% was obtained. 1 H NMR: (400 MHz, CDCl3) δ 4.12 (q, J = 7.1 Hz, 2H), 2.20 (d, J = 7.3 Hz, 2H), 2.13 - 2.01 (m, 1H), 1.73 - 1.63 (m, 2H), 1.61 - 1.41 (m, 10H), 1.39 - 1.29 (m, 2H), 1.25 (t, J = 7.1 Hz, 3H) m / z: 41 (18), 55 (20), 61 (23), 70 (24), 88 (100), 95 (2), 111 (6), 127 (3), 153 (7), 198 (2)

[0070] Example 2: Flavor composition Table 1: Examples of the flavor compositions of the present invention Dipropylene glycol 50 AGRUMEX LC 20 Aldehyde C14 SOG 5 Aldehyde C18 SOG. 1 AMAROCIT (registered trademark) 1 AMBROCENIDE (Registered Trademark) 10 DPG 3 AMBROXIDE 10% IPM 0.5 Anethole SUPRA 21.5 CELSIUS 10% DPG 5 Anisaldehyde REIN 5 AURELIONE (Registered Trademark) 2 Benzaldehyde DD 2 Benzyl Acetate 10 CALONE FF 10% IPM 0.5 CANTALOOP (Registered Trademark)1% DPG 5 CANTHOXAL (Registered Trademark) 3 Cashmeran 5 CEDERNHOLZOEL SUPER REKT. 2 CEDRAMBER 2 CEDROL CRIST.NAT. 2 Citronellol 950 5 Citronellyl Acetate EXTRA 2 Coumarin 2 Damascenone 10% IPM 5 Decalactone γ 2 Dioctyl Adipate 50 Ethylene Brassylate 60 Ethyl Linalool 10 Ethyl Maltol 10 FLORAZON 0.5 FLORHYDRAL 10% DPG 2 FLOROSA BM / Pyranol 40 FURAMINTON / TONKALACTONE (Trademark)1% IPM 2 GALAXOLID PURE 82 Hedione 260 Helotropin / Piperonal 10 HERBAFLORAT 100 Hexenol CIS-3 2 Hexenyl Acetate CIS-3 1 Hexenyl Salicylate CIS-3 10 Hexyl acetate 5 Indole FF 0.5 ISO E SUPER 150 ISORALDEIN 70 10 Linalool 15 Linalyl acetate 4 Maltol 1 Mandarino Noel ENTF. 1 Manzanate 2 Methyl anthranilate 2 Methyl heptin carbonate 1% IPM 5 PEARADISE 10% DPG 2 Phenoxanol 8 Polysantol 1 SANDRANOL (registered trademark) 20 Styryl acetate 5 Tetrahydrolinalool (Fass) 20 TROPICOL 0.1% IPM 1% IPM 10 Undecabeltol 9

[0071] According to the expert panel, after the addition of 0.5% ethyl 2-cyclooctylacetate, the composition has a more fruity aromatic note.

Claims

1. Use of ethyl 2-cyclooctylacetate as a fragrance.

2. Use of ethyl 2-cyclooctylacetate according to claim 1 for enhancing one or more pleasant olfactory impressions of one or more compounds with a pleasant odor, wherein said compound is different from ethyl 2-cyclooctylacetate.

3. The use according to claim 2, wherein the one or more pleasant olfactory impressions are selected from enhancing and / or improving a fruity olfactory note.

4. The one or more compounds with a pleasant odor different from the above-mentioned ethyl 2-cyclooctylacetate are fragrances having a molar mass in the range of 150 g / mol to 285 g / mol, in particular alcohols, aldehydes, ketones, ethers, esters and carboxylates having a molar mass in the range of 150 g / mol to 285 g / mol, and are selected from the group consisting of the use according to any one of claims 1 to 3.

5. The above-mentioned one or more pleasant-smelling compounds are γ-undecalactone, γ-nonalactone, 6,6-dimethoxy-2,5,5-trimethylhex-2-ene, (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxol, (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan, 1-methoxy-4-[(E)-prop-1-enyl]benzene, 4-methoxybenzaldehyde, cyclohexadec-2-en-1-one, benzenecarbaldehyde benzyl acetate, 7-methyl-2,4-dihydro-3H-1,5-benzodioxepin-3-one, cis-6-nonenal, 3-(4-methoxyphenyl)-2-methylpropanal, 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone, cedrol methyl ether, (1S,2R,5S,7R,8R)-2,6,6,8-tetramethyltricyclo[5.3.1.01,5]undecan-8-ol, (3R)-3,7-dimethyloct-6-ene, citronellyl acetate, 2H-chromen-2-one, damascenone, γ-decalactone, di(octyl) hexanedioate, ethylene brassylate, (6E)-3,7-dimethylnona-1,6-dien-3-ol, 2-ethyl-3-hydroxy-4H-pyran-4-one, 3-(o-ethylphenyl)-2,2-dimethylpropionaldehyde and 3-(p-ethylphenyl)-2,2-dimethylpropionaldehyde, 3-(3-propan-2-ylphenyl)butanal, 4-methyl-2-(2-methylpropyl)oxan-4-ol, (3S)-3,6-dimethyl-3H-1-benzofuran-2-one, 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]isochromene, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, 2H-1,3-benzodioxole-5-carbaldehyde, 3a,4,5,6,7,7a-hexahydro-4,Use according to any one of claims 1 to 4, selected from the group consisting of 7-methanoylnaphthalen-6-yl acetate, (3Z)-hex-3-en-1-ol, cis-3-hexen-1-yl acetate, cis-3-hexenyl salicylate, hexyl acetate, 1H-indole, 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl)ethenone, 1-(2,6,6-trimethyl-1-cyclohex-2-enyl)penta-1-en-3-one N, 3,7-dimethylocta-1,6-dien-3-ol, 3,7-dimethylocta-1,6-dien-3-yl acetate, 3-hydroxy-2-methyl-4H-pyran-4-one, ethyl 2-methylpentanoate, methyl 2-aminobenzoate, methyl oct-2-ynoate, diethyl (E / Z)-2-methylbut-2-enedioate, 3-methyl-5-phenylpentan-1-ol, (E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, (E)-2-ethyl-4-(2,2,3-trimethyl-1-cyclopent-3-enyl)but-2-en-1-ol, styrallyl acetate, 3,7-dimethyloctan-3-ol, 2-methyl-2-sulfanylpentan-1-ol, (E)-4-methyldec-3-en-5-ol.,

6. The use according to any one of claims 1 to 5, wherein the ratio of the total mass of the compound with a pleasant odor to the total mass of ethyl 2-cyclooctylacetate is in the range of 1:10 to 1:1000.

7. A fragrance composition comprising ethyl 2-cyclooctylacetate and at least one further compound with a pleasant odor different from ethyl 2-cyclooctylacetate, or consisting of these.

8. The fragrance composition according to claim 7, wherein the weight ratio of ethyl 2-cyclooctylacetate to the total amount of compounds with a pleasant odor different from ethyl 2-cyclooctylacetate is in the range of 1:10 to 1:1000.

9. The amount of ethyl 2-cyclooctylacetate is an amount sufficient to enhance one or more pleasant olfactory impressions of one or more compounds with a pleasant odor different from ethyl 2-cyclooctylacetate, in particular to enhance or improve the fruity olfactory note of one or more compounds with a pleasant odor, of the fragrance composition according to claim 7 and / or 8.

10. The amount of ethyl 2-cyclooctylacetate is in the range of 0.001 to 50% by weight based on the total weight of the fragrance composition, of the fragrance composition according to any one of claims 7 to 9.

11. The amount of ethyl 2-cyclooctylacetate is in the range of 0.01 to 10% by weight based on the total weight of the fragrance composition, of the fragrance composition according to any one of claims 7 to 9.

12. At least one pleasant-smelling compound is γ-undecalactone, γ-nonalactone, 6,6-dimethoxy-2,5,5-trimethylhex-2-ene, (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole, (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan, 1-methoxy-4-[(E)-prop-1-enyl]benzene, 4-methoxybenzaldehyde, cyclohexadec-2-en-1-one, benzenecarbaldehyde benzyl acetate, 7-methyl-2,4-dihydro-3H-1,5-benzodioxepin-3-one, cis-6-nonenal, 3-(4-methoxyphenyl)-2-methylpropanal, 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone, cedrol methyl ether, (1S,2R,5S,7R,8R)-2,6,6,8-tetramethyltricyclo[5.3.1.01,5]undecan-8-ol, (3R)-3,7-dimethyloct-6-ene, citronellyl acetate, 2H-chromen-2-one, damascenone, γ-decalactone, di(octyl) hexanedioate, ethylene brassylate, (6E)-3,7-dimethylnona-1,6-dien-3-ol, 2-ethyl-3-hydroxy-4H-pyran-4-one, 3-(o-ethylphenyl)-2,2-dimethylpropionaldehyde and 3-(p-ethylphenyl)-2,2-dimethylpropionaldehyde, 3-(3-propan-2-ylphenyl)butanal, 4-methyl-2-(2-methylpropyl)oxan-4-ol, (3S)-3,6-dimethyl-3H-1-benzofuran-2-one, 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]isochromene, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, 2H-1,3-benzodioxole-5-carbaldehyde, 3a,4,5,6,7,7a-hexahydro-4,The perfume composition according to any one of claims 7 to 11, selected from the group consisting of 7-methanoylnaphthalen-6-yl acetate, (3Z)-hex-3-en-1-ol, cis-3-hexen-1-yl acetate, cis-3-hexenyl salicylate, hexyl acetate, 1H-indole, 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl)ethenone, 1-(2,6,6-trimethyl-1-cyclohex-2-enyl)penta-1-en-3-one N, 3,7-dimethylocta-1,6-dien-3-ol, 3,7-dimethylocta-1,6-dien-3-yl acetate, 3-hydroxy-2-methyl-4H-pyran-4-one, ethyl 2-methylpentanoate, methyl 2-aminobenzoate, methyl oct-2-inoate, diethyl (E / Z)-2-methylbut-2-enedioate, 3-methyl-5-phenylpentan-1-ol, (E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, (E)-2-ethyl-4-(2,2,3-trimethyl-1-cyclopent-3-enyl)but-2-en-1-ol, styrallyl acetate, 3,7-dimethyloctan-3-ol, 2-methyl-2-sulfanylpentan-1-ol, (E)-4-methyldec-3-en-5-ol.,

13. An aromatic product comprising the perfume composition according to any one of claims 7 to 12 in an effective amount, wherein the amount of the perfume composition calculated based on the total amount of the product is preferably in the range of 0.01 to 10% by weight, more preferably 0.1 to 5% by weight, and most preferably 0.25 to 3% by weight.

14. The aromatic product according to claim 13, selected from cosmetics, hygiene products and / or household products.

15. A method for enhancing one or more pleasant olfactory impressions of one or more pleasant odor compounds, in particular a method for enhancing and / or improving the fruity floral note of one or more pleasant odor compounds, wherein the compound is different from ethyl 2-cyclooctylacetate, the method comprising or consisting of the step of mixing a pleasant odor compound with ethyl 2-cyclooctylacetate, wherein the amount of ethyl 2-cyclooctylacetate is an amount sufficient to enhance and / or improve the fruity note of one or more pleasant odor compounds.

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