Novel aldehyde compound

Abstract

To provide: a novel compound having a slightly earthy and floral muguet-like aspect, mint- and camphor-like notes, a honey-like sweetness, and a woody fragrance; and a perfume composition.SOLUTION: The compound is represented by formula (I). [In formula (I), R represents a C1-5 alkyl group.]SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a compound represented by the general formula (I) and a perfume composition containing the compound.

Background Art

[0002] Aldehyde compounds are known to exhibit useful activities in pharmaceuticals, perfumes, and agricultural chemicals.

[0003] Patent Document 1 discloses cis (or trans)-1-[1'(or 2' or 3')-formylpropoxy]-4-tert-butylcyclohexane and a perfume composition containing the same. It is described in Patent Document 1 that this perfume composition has a green, aldehyde-like, citrus-like scent.

[0004]

Chemical Formula

[0005] Patent Document 2 discloses 2-(2-t-butylcyclohexyloxy)-1-butanol and a perfume composition containing the same. It is described in Patent Document 2 that this perfume composition has a woody, amber-like aroma with excellent residual fragrance properties.

[0006]

Chemical Formula

Prior Art Documents

Patent Documents

[0007]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0008] An object of the present invention is to provide a novel compound having a woody fragrance and a perfume composition containing the same. This woody fragrance is a mint and camphor-like fragrance with slightly earthy and floral-muguet-like aspects. This woody fragrance further has a honey-like sweetness.

Means for Solving the Problems

[0009] The present inventors have found a novel aldehyde compound having a woody fragrance and completed the present invention. This woody fragrance is a mint and camphor-like fragrance with slightly earthy and floral-muguet-like aspects. This woody fragrance further has a honey-like sweetness.

[0010] The present invention is a compound represented by formula (I).

[0011]

Chemical Formula

[0012] [In the above formula (I), R is an alkyl group having 1 to 5 carbon atoms]

[0013] Further, the present invention is a perfume composition containing the compound represented by formula (I). Furthermore, the present invention is a method of using the compound represented by formula (I) as a fragrance component.

Effects of the Invention

[0014] The compound represented by formula (I) of the present invention has a woody fragrance. This woody fragrance is a mint and camphor-like fragrance with slightly earthy and floral-muguet-like aspects. This woody fragrance further has a honey-like sweetness.

Modes for Carrying Out the Invention

[0015] As described above, the present invention is a compound represented by formula (I).

[0016]

Chem.

[0017] [In the formula (I), R is an alkyl group having 1 to 5 carbon atoms.]

[0018] In the present specification, the alkyl group having 1 to 5 carbon atoms includes, for example, linear or branched alkyl groups such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, t-butyl group, n-pentyl group, i-pentyl group, sec-pentyl group, t-pentyl group, 2-methylbutyl group, etc. The alkyl group having 1 to 5 carbon atoms is preferably an alkyl group having 1 to 4 carbon atoms, more preferably an alkyl group having 3 to 4 carbon atoms, and even more preferably a t-butyl group.

[0019] In the formula (I), from the viewpoint of imparting a mint and camphor-like, honey-like sweetness, and a woody aroma with a slightly earthy and floral-muguet-like side, R is preferably an alkyl group having 1 to 4 carbon atoms, more preferably an alkyl group having 3 to 4 carbon atoms, and even more preferably a t-butyl group.

[0020] The compound represented by the formula (I) can be produced, for example, by the following method.

[0021]

Chem.

[0022] In the formula (I) and the formula (III), R is an alkyl group having 1 to 5 carbon atoms.

[0023] The production method of the present invention includes a step of obtaining a compound of formula (I) by oxidizing a compound of formula (III). The step may be, for example, oxidation of the compound of formula (III) with an oxidizing agent (e.g., Dess-Martine periodinane, etc.), Swern oxidation, PCC oxidation, TPAP (Ray-Griffiths) oxidation, TEMPO oxidation, or MnO 2 The compound of formula (I) is obtained by oxidation using the following reaction product. The compound of formula (I) obtained can be separated and purified by distillation or column chromatography.

[0024] The present invention also relates to a fragrance composition comprising a compound represented by formula (I).

[0025] [ka]

[0026] [In the formula (I), R is an alkyl group having 1 to 5 carbon atoms.

[0027] The fragrance composition containing the compound represented by formula (I) can impart a woody fragrance with slight earthy and floral-lily-like aspects, minty and camphor-like, honey-like sweetness, and excellent compatibility with various other fragrances, and can create a distinctive fragrance effect by blending. Specifically, the fragrance composition can impart a natural feel to alcohol-based fragrance compounds. That is, the compound represented by formula (I) can impart the complexity of natural fragrance compositions to alcohol-based fragrance compounds that are not naturally derived fragrance compositions such as extracts.

[0028] In a fragrance composition containing a compound represented by the formula (I), from the viewpoint of imparting a mint and camphor-like, and a woody aroma with a honey-like sweetness, with a slightly earthy and floral-muguet-like aspect (hereinafter, simply referred to as the viewpoint of imparting a mint and camphor-like, and a woody aroma with a honey-like sweetness), in the formula (I), R is preferably an alkyl group having 1 to 4 carbon atoms, more preferably an alkyl group having 3 to 4 carbon atoms, and even more preferably a t-butyl group.

[0029] In the fragrance composition, from the viewpoint of imparting a mint and camphor-like, and a woody aroma with a honey-like sweetness, the content of the compound of the formula (I) is preferably 0.05% by mass or more, more preferably 0.5% by mass or more, even more preferably 1% by mass or more, preferably 30% by mass or less, more preferably 20% by mass or less, and even more preferably 10% by mass or less. From the above viewpoint, it is preferably 0.05% by mass or more and 30% by mass or less, more preferably 0.5% by mass or more and 20% by mass or less, and even more preferably 1% by mass or more and 10% by mass or less.

[0030] The fragrance composition preferably further contains an alcohol having 8 to 14 carbon atoms. By further containing an alcohol having 8 to 14 carbon atoms, the naturalness of the fragrance composition containing this is enhanced, and a complexity similar to that of a natural fragrance composition is produced. As a result, from the viewpoint of making the scent of a mixture of the fragrance composition further containing an alcohol having 8 to 14 carbon atoms and a compounded fragrance closer to a natural scent, the alcohol having 8 to 14 carbon atoms is preferably a monoalcohol (monool), and an alcohol-based fragrance compound is preferred. An alcohol-based fragrance compound means a compound used for the purpose of imparting a scent and having a hydroxyl group.

[0031] Examples of the alcohol having 8 to 14 carbon atoms include bacdanol (2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol), cinnamic alcohol, citronellol, geraniol, phenethyl alcohol, dihydromyrcenol, sandal mysol core (2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol), amber core (1-(2-t-butylcyclohexyloxy)-2-butanol), linalool, myrcenol, nerol, tetrahydrolinalool, tetrahydrogeraniol, hydroxycitronellol, terpineol, isopulegol, nopol, thymol, eugenol, 3-methyl-5-phenylpentanol, etc. By further containing an alcohol having 8 to 14 carbon atoms, the natural feeling of the perfume composition containing this is enhanced, and a complexity similar to that of a natural perfume composition is generated. As a result, from the viewpoint of making the scent of the mixture of the perfume composition further containing an alcohol having 8 to 14 carbon atoms and the compounded perfume closer to a natural scent, one or more selected from the group consisting of bacdanol, sandal mysol core, and amber core are preferable.

[0032]

Chemical formula

[0033] The mass ratio of the compound represented by formula (I) to an alcohol having 8 to 14 carbon atoms [compound represented by formula (I) / alcohol having 8 to 14 carbon atoms] is preferably 0.001 or more, more preferably 0.01 or more, still more preferably 0.05 or more, even more preferably 0.07 or more, from the viewpoint of enhancing the natural feeling of the perfume composition containing the same by further containing an alcohol having 8 to 14 carbon atoms and creating a complexity like that of a natural perfume composition, and as a result, making the scent of the mixture of the perfume composition further containing an alcohol having 8 to 14 carbon atoms and a compounded perfume closer to a natural scent. From the viewpoint of imparting the fragrance tone of the original alcohol having 8 to 14 carbon atoms, it is preferably 20 or less, more preferably 10 or less, still more preferably 5 or less, even more preferably 1 or less. From these viewpoints, it is preferably from 0.001 to 20, more preferably from 0.01 to 10, still more preferably from 0.05 to 5, even more preferably from 0.07 to 1.

[0034] Further, in the perfume composition containing the compound represented by formula (I), the content of the alcohol having 8 to 14 carbon atoms is preferably 1% by mass or more, more preferably 5% by mass or more, still more preferably 10% by mass or more, from the viewpoint of enhancing the natural feeling and creating a complexity like that of a natural perfume composition. From the same viewpoint, it is preferably 90% by mass or less, more preferably 70% by mass or less, still more preferably 50% by mass or less, and preferably from 1% by mass to 90% by mass, more preferably from 5% by mass to 70% by mass, still more preferably from 10% by mass to 50% by mass.

[0035] When a plurality of types of alcohols having 8 to 14 carbon atoms are contained, the total of their masses is the "mass of the alcohol having 8 to 14 carbon atoms".

[0036] It is preferable that the alcohol having 8 to 14 carbon atoms contains a compound represented by formula (II).

[0037]

Chemical formula

[0038] In the formula (II), R 1 and R 2 are each independently a hydrogen atom or a methyl group, R 3 is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, or a t-butyl group, R 4 is a methyl group or an ethyl group, R 5 is a hydroxy group or a hydroxymethyl group, X is -CH 2 - or -O-, n is 1 or 2, The dashed lines are each independently a single bond or a double bond.

[0039] The alcohol having 8 to 14 carbon atoms or the compound represented by the formula (II) further contains an alcohol having 8 to 14 carbon atoms, thereby enhancing the natural feeling of the perfume composition containing this, and causing a complexity like that of a natural perfume composition. As a result, from the viewpoint of making the scent of the mixture of the perfume composition further containing an alcohol having 8 to 14 carbon atoms and a compounded perfume closer to a natural scent, one or more selected from bacdanol (2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol), sandal mysol core (2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol), and amber core (1-(2-t-butylcyclohexyloxy)-2-butanol) are preferable.

[0040] The perfume composition of the present invention containing the compound represented by the formula (I) and the alcohol having 8 to 14 carbon atoms preferably further contains one or more of alcohol, phenol, ester, carbonate, aldehyde, ketone, acetal, ether, lactone, nitrile, and amine other than the compound represented by the formula (I) and the alcohol having 8 to 14 carbon atoms.

[0041] In this specification, the "type" of each fragrance means a single compound or a mixture of two or more compounds.

[0042] Examples of alcohols include aliphatic alcohols, terpene alcohols, aromatic alcohols, and other alcohols. Among these, aliphatic alcohols are preferred.

[0043] Examples of terpene alcohols include linalool, ethyl linalool, hydroxycitronellol, nerol, terpineol, α-terpineol, dihydromyrcenol, farnesol, nerolidol, cedrol, menthol, borneol, etc.

[0044] Examples of aromatic alcohols include phenylethyl alcohol, benzyl alcohol, dimethylbenzyl carbinol, phenylethyldimethyl carbinol, phenylhexanol, etc.

[0045] Examples of aliphatic alcohols include cis-3-hexenol, 1-(2,2,6-trimethylcyclohexyl)-3-hexanol, Magnol (trade name of Kao Corporation, a mixture mainly composed of ethyl norbornylcyclohexanol), Undecabeltol (trade name of Givaudan, 4-methyl-3-decen-5-ol), isobornyl cyclohexanol, Terpyrosa (trade name of Kao Corporation, 3,6-dimethyl-2-heptanol), etc.

[0046] Examples of other alcohols include glycols such as dipropylene glycol, Florosa (trade name of Givaudan, chemical name: 4-methyl-2-(2-methylpropyl)tetrahydro-2H-4-pyranol), maltol, ethyl maltol, etc.

[0047] Examples of hydrocarbons include limonene, α-pinene, β-pinene, terpinene, cedrene, longifolene, valencene, etc.

[0048] Examples of phenols include guaiacol, eugenol, dihydroeugenol, isoeugenol, thymol, p-cresol, vanillin, ethyl vanillin, and the like.

[0049] Examples of esters include aliphatic carboxylic acid esters, aromatic carboxylic acid esters, and other carboxylic acid esters.

[0050] Examples of the aliphatic carboxylic acids that form aliphatic carboxylic acid esters include linear and branched carboxylic acids having 1 to 18 carbon atoms. Among them, carboxylic acids having 1 to 6 carbon atoms such as formic acid, acetic acid, and propionic acid are preferred, and acetic acid is more preferred. Examples of the aromatic carboxylic acids that form aromatic carboxylic acid esters include benzoic acid, anisic acid, phenylacetic acid, cinnamic acid, salicylic acid, anthranilic acid, and the like. Examples of the alcohols that form aliphatic and aromatic esters include linear and branched aliphatic alcohols having 1 to 5 carbon atoms and the above-mentioned perfume component alcohols.

[0051] Examples of formates include linalyl formate, citronellyl formate, geranyl formate, and the like.

[0052] Examples of acetate esters include ethyl acetate, isoamyl acetate (isopentyl acetate), benzyl acetate, hexyl acetate, phenyl acetate, p-cresyl acetate, cis-3-hexenyl acetate, linalyl acetate, citronellyl acetate, geranyl acetate, neryl acetate, terpinyl acetate, nopyl acetate, bornyl acetate, isobornyl acetate, acetyl eugenol, acetyl iso eugenol, o-tert-butyl cyclohexyl acetate, p-tert-butyl cyclohexyl acetate, tricyclodecenyl acetate, phenylethyl acetate, styrallyl acetate, cinnamyl acetate, dimethyl benzyl carbinyl acetate, 3-pentyltetrahydropyran-4-yl acetate, prenyl acetate, geranyl acetate, methyl phenyl carbinyl acetate, etc.; examples of phenylacetate esters include phenylethyl phenylacetate, p-cresyl phenylacetate, etc.

[0053] Examples of propionate esters include ethyl propionate, citronellyl propionate, tricyclodecenyl propionate, benzyl propionate, styrallyl propionate, helvetolide (trade name of Firmenich, 2-[1-(3,3-dimethylcyclohexyl)ethoxy]-2-methylpropyl) propionate, etc.

[0054] Examples of butyrate esters include citronellyl butyrate, dimethyl benzyl carbinyl n-butyrate, isoamyl n-butyrate, n-amyl n-butyrate, etc.; examples of isobutyrate esters include tricyclodecenyl isobutyrate, phenoxyethyl isobutyrate, etc.

[0055] Examples of valerate esters include methyl valerate, ethyl valerate, butyl valerate, amyl valerate, benzyl valerate, phenylethyl valerate, etc.; examples of hexanoate esters include methyl hexanoate, ethyl hexanoate, allyl hexanoate, linalyl hexanoate, citronellyl hexanoate, etc.

[0056] Examples of heptanoic acid esters include methyl heptanoate, allyl heptanoate, etc.

[0057] Examples of nonenoic acid esters include methyl 2-nonenoate, ethyl 2-nonenoate, ethyl 3-nonenoate, etc.

[0058] Examples of benzoic acid esters include methyl benzoate, benzyl benzoate, 3,6-dimethylbenzoate, etc.

[0059] Examples of cinnamic acid esters include methyl cinnamate, benzyl cinnamate, etc.

[0060] Examples of salicylic acid esters include methyl salicylate, n-hexyl salicylate, cis-3-hexenyl salicylate, cyclohexyl salicylate, benzyl salicylate (benzyl salicylate), etc.

[0061] Furthermore, examples of brassidic acid esters include ethylene brassilate, etc.

[0062] Examples of tiglic acid esters include geranyl tiglate, 1-hexyl tiglate, cis-3-hexenyl tiglate, etc.

[0063] Examples of jasmonic acid esters include methyl jasmonate, etc.; examples of dihydrojasmonic acid esters include MDJ (trade name of Kao Corporation, methyl dihydrojasmonate, methyl (2-pentyl-3-oxocyclopentyl) acetate), etc.

[0064] Examples of glycidic acid esters include methyl 2,4-dihydroxy-ethylmethylphenyl glycidate, 4-methylphenyl ethyl glycidate, etc.

[0065] Examples of anthranilic acid esters include methyl anthranilate, ethyl anthranilate, dimethyl anthranilate, and the like.

[0066] Examples of glycolic acid esters include allyl cyclohexyl glycolate and the like.

[0067] Furthermore, examples of other esters include ethyl safuranate (trade name, manufactured by Givaudan, ethyl dihydrocyclogeranate), poalenate (trade name, manufactured by Kao Corporation, ethyl-2-cyclohexylpropionate), flutetate (trade name, manufactured by Kao Corporation, ethyl tricyclo[5.2.1.0 2.6 decane-2-carboxylate), ethyl acetoacetate, fructone (trade name, manufactured by IFF, ethyl 2-(2-methyl-1,3-dioxolan-2-yl)acetate), manzanate (trade name, manufactured by Givaudan, ethyl 2-methylpentanoate), ethyl 2-methylbutyrate, allyl cyclohexylpropionate, allyl-2-pentyloxy glycolate, and the like.

[0068] Examples of carbonates include rifarome (trade name, manufactured by IFF, cis-3-hexenyl methyl carbonate), jasmasyclat (trade name, manufactured by Kao Corporation, methyl-cyclooctyl carbonate), floramat (trade name, manufactured by Kao Corporation, ethyl-2-t-butylcyclohexyl carbonate), and the like.

[0069] Examples of aldehydes include n-octanal, n-nonanal, n-decanal, n-dodecanal, 2-methylundecanal, 10-undecenal, citronellal, citral, hydroxycitronellal, triplal (trade name of IFF, 2,4-dimethyl-3-cyclohexene-1-carboxyaldehyde), cyclovertal (trade name of Kao Corporation, dimethyl-3-cyclohexenyl-1-carboxyaldehyde), benzaldehyde, phenylacetaldehyde, phenylpropylaldehyde, cinnamic aldehyde, dimethyltetrahydrobenzaldehyde, bourgeonal (trade name of Givaudan, 3-(4-tert-butylphenyl)propanal), lilial (trade name of IFF, hydroxymyrac aldehyde), polanal II (trade name of Kao Corporation, 2-cyclohexylpropanal), lilyal (trade name of Givaudan, p-tert-butyl-α-methylhydrocinnamic aldehyde), p-isopropyl-α-methylhydrocinnamic aldehyde, florarozone (trade name of IFF, 3-(o-(and p-)ethylphenyl)-2,2-dimethylpropionaldehyde), α-amylcinnamic aldehyde, α-hexylcinnamic aldehyde, heliotropin (trade name of Takasago Perfumery Co., Ltd., 3,4-methylenedioxybenzaldehyde), helional (trade name of IFF, alpha-methyl-1,3-benzodioxole-5-propanal), cantoxal (trade name of IFF, 2-methyl-3-(paramethoxyphenyl)propanal), aldehyde C-6 (trade name of Kao Corporation, n-hexanal), and the like.

[0070] Examples of ketones include methyl heptenone, dimethyl octenone, 3-octanone, hexyl cyclopentanone, dihydrojasmon, Beloutone (trade name of Firmenich, 2,2,5-trimethyl-5-pentylcyclopentanone), Nectaryl (trade name of Givaudan, 2-(2-(4-methyl-3-cyclohexen-1-yl)propyl)cyclopentanone), ionone, β-ionone, methyl ionone, methyl ionone-G, γ-methyl ionone, damascone, α-damascone, β-damascone, δ-damascone, isodamascone (trade name of Symrise, 1-(2,4,4-trimethyl-2-cyclohexyl)-trans-2-butanone), damasconone, Dynascone (trade name of Firmenich, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one), iron, Cashmeran (trade name of IFF, 1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-4H-inden-4-one), Iso-E-Super (trade name of IFF, 1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-ethan-1-one), Calone (trade name of Firmenich, 7-methyl-3,4-dihydro-2H-benzodioxepin-3-one), Carvone, menthone, acetyl cedrene, isolongifolanone, nutkatone, benzyl acetone, raspberry ketone, benzophenone, tonalide (trade name of PFW, 6-acetyl-1,1,2,4,4,7-hexamethyltetrahydronaphthalene), β-methyl naphthyl ketone, ethyl maltol, camphor, muscone, muscenone (product of Firmenich, 3-methyl-5-cyclopentadecen-1-one), civetone, Globanone (trade name of Symrise, 8-cyclohexadecenone), methyl nonyl ketone, cis-jasmon, para-amyl cyclohexanone (4-pentylcyclohexanone), etc. Among them, from the viewpoint of emphasizing floral sweetness when blended with other fragrances, ionone, damasconone, Iso-E-Super, or γ-methyl ionone is preferred.

[0071] Examples of acetals include acetaldehyde ethyl phenyl propyl acetal, citral diethyl acetal, phenylacetaldehyde glyceryl acetal, ethyl acetoacetate ethylene glycol acetal, Boazambrene forte (trade name of Kao Corporation, ethoxymethyl cyclododecyl ether), Troenan (trade name of Kao Corporation, 5-methyl-5-propyl-2-(1-methylbutyl)-1,3-dioxane), Floropal (trade name of Shimrise Co., Ltd., 2,4,6-trimethyl-4-phenyl-1,3-dioxane), Magnolan (trade name of Shimrise Co., Ltd., 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxane), and the like.

[0072] Examples of ethers include cedryl methyl ether, estragole, anethole, β-naphthyl methyl ether, β-naphthyl ethyl ether, limonene oxide, rose oxide, nerol oxide, 1,8-cineole, rose furan, Ambroxan (trade name of Kao Corporation, [3aR-(3aα,5aβ,9aα,9bβ)]dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan), Herbavert (trade name of Kao Corporation, 3,3,5-trimethylcyclohexyl ethyl ether), Galaxolide (trade name of IFF, hexamethyl hexahydrocyclopenta benzopyran), phenylacetaldehyde dimethyl acetal, methyl isoeugenol, and the like.

[0073] Examples of carboxylic acids include benzoic acid, phenylacetic acid, cinnamic acid, hydrocinnamic acid, butyric acid, 2-hexenoic acid, and the like.

[0074] Examples of lactones include ambrettolide, γ-decalactone, δ-decalactone, γ-valerolactone, γ-nonalactone, γ-undecalactone, δ-hexalactone, γ-jasmolactone, whiskey lactone, coumarin, cyclopentadecanolide, cyclohexadecanolide, 11-oxahexadecanolide, butyrylidenephthalide, and the like.

[0075] Examples of the nitriles include tridecene-2-nitrile, geranyl nitrile, citronellyl nitrile, dodecane nitrile and the like.

[0076] Examples of the amines include indole, skatole, 6-methylquinoline, 6-isopropylquinoline, isobutylquinoline and the like.

[0077] Examples of the Schiff bases include aurantiol, ligandral and the like.

[0078] Moreover, it is also preferable that the perfume composition of the present invention containing the compound represented by the formula (I) and the alcohol having 8 to 14 carbon atoms further contains natural essential oils and natural extracts.

[0079] Examples of the natural essential oils and natural extracts include oils, concretes, absolutes, resinoids, oleoresins, tinctures, infusions, balsams and the like of natural products such as orange, lemon, lime, bergamot, vanilla, mandarin, peppermint, spearmint, lavender, galbanum, camomile, rosemary, eucalyptus, sage, basil, rose, rockrose, geranium, jasmine, ylang-ylang, anise, clove, ginger, nutmeg, cardamom, cedar, hinoki, vetiver, patchouli, hay, lemongrass, labdanum, grapefruit, elemi oil, bergamot oil and the like.

[0080] In the perfume composition of the present invention, the total content of other components other than the compound represented by the formula (I) and the alcohol having 8 to 14 carbon atoms can be appropriately selected depending on the type of the compounded perfume, the type of the intended fragrance and the strength of the fragrance, etc. However, in the composition containing the perfume composition of the present invention, it is preferably 1% by mass or more, more preferably 5% by mass or more, still more preferably 10% by mass or more, and preferably 99% by mass or less, more preferably 80% by mass or less, still more preferably 70% by mass or less.

[0081] The fragrance composition of the present invention can be combined, as a base, with an oil agent that has no odor by itself. Such an oil agent can uniformly mix fragrance components, facilitate blending into products, and easily impart a fragrance of appropriate intensity. Examples of the oil agent include polyhydric alcohols such as ethylene glycol, propylene glycol, butylene glycol, and dipropylene glycol; esters such as isopropyl myristate, dibutyl adipate, and diethyl sebacate; hydrocarbons such as liquid paraffin and squalane; and surfactants such as polyoxyethylene alkyl ether and sorbitan fatty acid ester.

[0082] Among these, from the viewpoint of improving the solubility of all fragrance components, polyhydric alcohols and esters are preferable as the oil agent, and dipropylene glycol and isopropyl myristate are more preferable. The content of such an oil agent in the fragrance composition is preferably 0.01% by mass or more, more preferably 1% by mass or more, still more preferably 5% by mass or more, and preferably 95% by mass or less, more preferably 90% by mass or less, still more preferably 80% by mass or less.

[0083] The present invention also provides a detergent composition containing the fragrance composition of the present invention, a cosmetic containing the fragrance composition of the present invention, and a fiber treatment composition containing the fragrance composition of the present invention.

[0084] As the detergent composition of the present invention, a body detergent composition, a laundry detergent composition, and a hard surface detergent composition are preferable, a body detergent composition and a laundry detergent composition are more preferable, and a laundry detergent composition is still more preferable.

[0085] Examples of the body detergent composition include a skin detergent composition, a hair detergent composition, and a soap composition, and a skin detergent composition is preferable.

[0086] Examples of the hard surface detergent composition include an all-purpose cleaner and a dishwashing detergent composition.

[0087] As the fiber treatment composition of the present invention, a softening agent composition is preferred.

[0088] As cosmetics other than the detergent composition of the present invention, perfume, emulsion, lotion, sunscreen are preferred, and perfume is more preferred.

[0089] In the detergent composition of the present invention, in addition to the perfume composition of the present invention, it is preferably contained an anionic surfactant, and further a nonionic surfactant, a pH adjuster, a viscosity adjuster, a solvent, an oil agent, a preservative, water and the like can be blended.

[0090] In the fiber treatment composition of the present invention, in addition to the perfume composition of the present invention, it is preferably contained a cationic surfactant, and further a pH adjuster, a solvent, an oil agent, a preservative, water and the like can be blended.

[0091] In the perfume of the present invention, in addition to the perfume composition of the present invention, a solvent, water and the like can be contained.

[0092] The compound represented by the formula (I) has a woody aroma. This woody aroma is a mint and camphor-like aroma with a slightly earthy and floral-muguet-like aspect. This woody aroma is further an aroma with a honey-like sweetness. Furthermore, a composition comprising the compound represented by the formula (I) and an alcohol having 8 to 14 carbon atoms can give a new impression that a natural feeling is imparted to the alcohol having 8 to 14 carbon atoms.

[0093] Accordingly, the present invention relates to a method of using a compound represented by the formula (I) of the present invention or a composition comprising a compound represented by the formula (I) and an alcohol having 8 to 14 carbon atoms as a fragrance component, specifically, a method of using it as a fragrance component in a fragrance composition, a detergent composition, a cosmetic or a fiber treatment composition. As the detergent composition, a body detergent composition, a laundry detergent composition, or a hard surface detergent composition is preferable, a body detergent composition or a laundry detergent composition is more preferable, and a laundry detergent composition is even more preferable. Examples of the body detergent composition include a skin detergent composition, a hair detergent composition, and a soap composition, and a skin detergent composition is preferable. Examples of the hard surface detergent composition include an all-purpose cleaner and a dishwashing detergent composition. As the cosmetic, a perfume is preferable. As the fiber treatment composition, a softener composition is preferable.

[0094] In the method of use, the compound represented by the formula (I) of the present invention or the composition comprising a compound represented by the formula (I) and an alcohol having 8 to 14 carbon atoms is preferably used in a content of 0.0001% by mass or more, more preferably 0.001% by mass or more, and preferably 30% by mass or less, more preferably 20% by mass or less, still more preferably 10% by mass or less, 1% by mass or less, and more preferably 0.1% by mass or less, based on the detergent composition, the cosmetic or the softener composition. By using in this amount, when formulating this fragrance composition as a fragrance material with other components, a new impression can be imparted that a woody fragrance is imparted.

[0095] In the method of use, the fragrance composition of the present invention may be combined with an oil agent that has no odor by itself. The oil agent is the same as that described in the fragrance composition. Further, in the method of use, as other fragrances, other commonly used fragrance components and compounded fragrances having a desired composition may be included. Such other fragrances are the same as those described in the fragrance composition.

[0096] The present invention includes the following aspects. <1> A compound represented by formula (I).

[0097] [Chemical formula]

[0098] [In the above formula (I), R is an alkyl group having 1 to 5 carbon atoms]

[0099] <2> The flavoring agent according to <1>, wherein R is a t-butyl group.

[0100] <3> A flavor composition containing the compound according to <1> or <2>.

[0101] <4> The flavor composition according to any one of <1> to <3>, wherein the content of the compound of formula (I) in the flavor composition is 0.05% by mass or more and 30% by mass or less.

[0102] <5> The flavor composition according to any one of <1> to <4>, wherein the content of the compound of formula (I) in the flavor composition is 0.5% by mass or more and 20% by mass or less.

[0103] <6> The flavor composition according to any one of <1> to <5>, wherein the content of the compound of formula (I) in the flavor composition is 1% by mass or more and 10% by mass or less.

[0104] <7> The flavor composition according to any one of <3> to <6>, further comprising an alcohol having 8 to 14 carbon atoms.

[0105] <8> The flavor composition according to <7>, wherein the alcohol having 8 to 14 carbon atoms is an alcoholic perfume compound.

[0106] <9> The flavor composition according to <7> or <8>, wherein the alcohol having 8 to 14 carbon atoms is a monoalcohol.

[0107] <10>An alcohol having 8 to 14 carbon atoms is a perfume composition according to any one of <7> to <9>, which is selected from the group consisting of bacdanol (2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol), cinnamic alcohol, citronellol, geraniol, phenethyl alcohol, dihydromyrcenol, sandal mysol core (2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol), amber core (1-(2-t-butylcyclohexyloxy)-2-butanol), linalool, myrcenol, nerol, tetrahydrolinalool, tetrahydrogeraniol, hydroxycitronellol, terpineol, isopulegol, nopol, thymol, eugenol, and 3-methyl-5-phenylpentanol.

[0108] <11>A perfume composition according to any one of <7> to <10>, wherein the alcohol having 8 to 14 carbon atoms is one or more selected from the group consisting of bacdanol, sandal mysol core, and amber core.

[0109] <12>A perfume composition according to <7>, wherein the alcohol having 8 to 14 carbon atoms contains a compound represented by the formula (II).

[0110]

Chemical formula

[0111] [In the formula (II), R 1 and R 2 are each independently a hydrogen atom or a methyl group, R 3 is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, or a t-butyl group, R 4 is a methyl group or an ethyl group, R 5 is a hydroxy group or a hydroxymethyl group, X is -CH2 -or -O-, n is 1 or 2, The dashed lines are each independently a single bond or a double bond.]

[0112] <13> The alcohol having 8 to 14 carbon atoms is one or more selected from the group consisting of 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, and 1-(2-t-butylcyclohexyloxy)-2-butanol, and is the perfume composition according to any one of <7> to <10>.

[0113] <14> The mass ratio of the compound represented by formula (I) to the alcohol having 8 to 14 carbon atoms [compound represented by formula (I) / alcohol having 8 to 14 carbon atoms] is 0.001 or more and 20 or less, and is the perfume composition according to any one of <7> to <13>.

[0114] <15> The mass ratio of the compound represented by formula (I) to the alcohol having 8 to 14 carbon atoms [compound represented by formula (I) / alcohol having 8 to 14 carbon atoms] is 0.01 or more and 10 or less, and is the perfume composition according to any one of <7> to <14>.

[0115] <16> The mass ratio of the compound represented by formula (I) to the alcohol having 8 to 14 carbon atoms [compound represented by formula (I) / alcohol having 8 to 14 carbon atoms] is 0.05 or more and 5 or less, and is the perfume composition according to any one of <7> to <15>.

[0116] <17> The mass ratio of the compound represented by formula (I) to the alcohol having 8 to 14 carbon atoms [compound represented by formula (I) / alcohol having 8 to 14 carbon atoms] is 0.07 or more and 1 or less, and is the perfume composition according to any one of <7> to <16>.

[0117] <18> In the perfume composition, other than the compound represented by the formula (I) and the alcohol having 8 to 14 carbon atoms, preferably further containing one or more of alcohol, phenol, ester, carbonate, aldehyde, ketone, acetal, ether, lactone, nitrile, and amine, the perfume composition according to any one of <7> to <17>.

[0118] <19> Other than the compound represented by the formula (I) and the alcohol having 8 to 14 carbon atoms, the total content of other components, preferably the total content of alcohol, phenol, ester, carbonate, aldehyde, ketone, acetal, ether, lactone, nitrile, and amine is 1% by mass or more and 99% by mass or less, the perfume composition according to any one of <7> to <18>.

[0119] <20> Other than the compound represented by the formula (I) and the alcohol having 8 to 14 carbon atoms, the total content of other components, preferably the total content of alcohol, phenol, ester, carbonate, aldehyde, ketone, acetal, ether, lactone, nitrile, and amine is 5% by mass or more and 80% by mass or less, the perfume composition according to any one of <7> to <19>.

[0120] <21> Other than the compound represented by the formula (I) and the alcohol having 8 to 14 carbon atoms, the total content of other components, preferably the total content of alcohol, phenol, ester, carbonate, aldehyde, ketone, acetal, ether, lactone, nitrile, and amine is 10% by mass or more and 70% by mass or less, the perfume composition according to any one of <7> to <20>.

[0121] <22> In the perfume composition, other than the compound represented by the formula (I) and the alcohol having 8 to 14 carbon atoms, preferably further containing a natural essential oil or a natural extract, the perfume composition according to any one of <7> to <17>.

[0122] <23> A cosmetic containing the fragrance composition described in any one of <3> to <22>.

[0123] <24> A detergent composition containing the fragrance composition described in any one of <3> to <22>.

[0124] <25> A fiber treatment agent composition containing the fragrance composition described in any one of <3> to <22>.

[0125] <26> A method of using the compound described in <1> or <2> as a fragrance component.

[0126] <27> A method of using a composition composed of the compound described in <1> or <2> and an alcohol having 8 to 14 carbon atoms as a fragrance component.

[0127] <28> A method for producing the compound described in <1>, wherein the compound of formula (I) is obtained by oxidizing the compound of formula (III).

[0128]

Chemical formula

[0129] [In the above formulas (I) and (III), R is an alkyl group having 1 to 5 carbon atoms]

[0130] In the following examples, “%” is “% by mass” unless otherwise specified. Also, the mass of the catalyst is the mass in the dry state.

[0131] <Gas chromatograph apparatus and analysis conditions> GC apparatus: 7890B manufactured by Agilent Technologies, hydrogen flame ionization detector

[0132] Column: When analyzing the yield, DB-1 (capillary column, 100% dimethylpolysiloxane, inner diameter 0.25 mm, length 30 m, film thickness 0.25 μm, manufactured by Agilent Technologies) was used.

[0133] When analyzing the cis and trans isomers, DB-WAX (capillary column, polyethylene glycol, inner diameter 0.25 mm, length 30 m, film thickness 0.25 μm, manufactured by Agilent Technologies) was used.

[0134] Carrier gas: He, 1.5 mL / min Injection conditions: 300 °C, split ratio 100 / 1 Injection volume: 1 μL Detection conditions: FID method, 300 °C Column temperature conditions: Starting from 80 °C, the temperature was raised to 300 °C at a rate of 10 °C / min. Then, it was held at 300 °C for 10 minutes.

[0135] [Production Example 1] Production of 1-(2-t-butylphenyloxy)-2-butanol

[0136] [Chemical formula]

[0137] To a 1-liter round-bottom flask equipped with a Dimroth condenser and a dropping funnel, under a nitrogen stream, 2-t-butylphenol (1) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., 350 g) and 35 g of a 48% aqueous sodium hydroxide solution (manufactured by Kanto Chemical Co., Inc.) were added and heated to 80 °C. To this, 1,2-butylene oxide (2) (manufactured by Tokyo Chemical Industry Co., Ltd., 176 g) was added dropwise over about 2 hours, and then stirred at 80 °C for 5 hours. After cooling the reaction mixture, the lower-layer aqueous sodium hydroxide solution was separated from the organic layer, and the organic layer was distilled to obtain 1-(2-t-butylphenyloxy)-2-butanol (3) in a yield of 96%.

[0138] [Production Example 2] Production of a mixture of 1-(2-t-butylcyclohexyloxy)-2-butanol (4) and 2-(2-t-butylcyclohexyloxy)-1-butanol (5)

[0139] [Chemistry]

[0140] Into a 500 ml autoclave were added 250 g of 1-(2-t-butylphenyloxy)-2-butanol (3) obtained in Production Example 1, 4.75 g of a palladium catalyst supported on activated carbon (manufactured by N.E. Chemcat Corporation, trade name: S type, 50% water-containing product, palladium supported amount 2%), and 0.25 g of a ruthenium catalyst supported on activated carbon (manufactured by N.E. Chemcat Corporation, 50% water-containing product, ruthenium supported amount 5%), and the reaction was carried out at a hydrogen pressure of 2.0 MPa and 190 °C for 6 hours.

[0141] After completion of the reaction, the catalyst was filtered and the filtrate was distilled to obtain a mixture of 1-(2-t-butylcyclohexyloxy)-2-butanol (4) and 2-(2-t-butylcyclohexyloxy)-1-butanol (5) in a yield of 25%. As a result of analyzing the product by gas chromatography, the mass ratio of 1-(2-t-butylcyclohexyloxy)-2-butanol (4) to 2-(2-t-butylcyclohexyloxy)-1-butanol (5) was (4):(5) = 75:25.

[0142] [Example 1] Production of 2-(2-t-butylcyclohexyloxy)-butanal (6)

[0143] [Chemistry]

[0144] 158 g of a mixture of 1-(2-t-butylcyclohexyloxy)-2-butanol (4) and 2-(2-t-butylcyclohexyloxy)-1-butanol (5) obtained in Production Example 2 was rectified using a 20-tray rectification column at a reflux ratio of 20 to obtain a mixture of 1-(2-t-butylcyclohexyloxy)-2-butanol (4) and 2-(2-t-butylcyclohexyloxy)-1-butanol (5) with a mass ratio of compound (4) to compound (5) of 31:69 in a yield of 50%.

[0145] 1 g of the obtained mixture of 1-(2-t-butylcyclohexyloxy)-2-butanol (4) and 2-(2-(t-butylcyclohexyloxy)-1-butanol (5) (the mass ratio of compound (4) to compound (5) is 31:69)) was dissolved in dichloromethane (43.8 mL), and Dess-Martin periodinane (2.2 g) was added at 0 °C. After 10 minutes, the cooling bath was removed, the reaction mixture was warmed to room temperature, and stirred for 30 minutes to carry out the reaction.

[0146] As a post-treatment, an aqueous sodium thiosulfate solution was added to the reaction mixture to stop the reaction. The reaction mixture was extracted with diethyl ether, the organic phase was dried over sodium sulfate, the sodium sulfate was filtered off, and then the solvent was distilled off from the obtained filtrate to obtain a mixture of 2-(2-t-butylcyclohexyloxy)butanal (6) and 1-(2-t-butylcyclohexyloxy)butan-2-one (7).

[0147] An aqueous sodium bisulfite solution (100 mL) was added to the resulting mixture of 2-(2-t-butylcyclohexyloxy)butanal (6) and 1-(2-t-butylcyclohexyloxy)butan-2-one (7), and the resulting aqueous solution was stirred at room temperature (25 °C) for 30 minutes. After the reaction mixture was extracted with hexane (50 mL), a 1 mol / L sodium hydroxide solution was slowly added dropwise to the separated aqueous phase until the pH reached 10. After stirring the aqueous phase at room temperature (25 °C) for 12 hours, it was extracted with diethyl ether (100 mL), the organic phase was dried over sodium sulfate, the sodium sulfate was filtered off, and the solvent was distilled off under reduced pressure from the organic phase to obtain a crude product. The obtained crude product was purified by silica gel column chromatography to obtain 2-(2-t-butylcyclohexyloxy)butanal (6) in a yield of 77%.

[0148] 2-(2-t-Butylcyclohexyloxy)butanal (6) (diastereomer mixture) 1 H-NMR (400 MHz, CDCl 3 ): δ = 9.75 (s, 0.5H), 9.68 (s, 0.5H), 3.96 (m, 1H), 3.60 (m, 1H), 3.25 (m, 1H), 2.06~1.56 (m, 9H), 1.56~1.19 (m, 4H), 1.03 (s, 9H) 13 C-NMR (100 MHz, CDCl 3 ): δ = 205.73, 204.82, 84.34, 82.50, 81.50, 79.74, 52.02, 51.51, 33.27, 31.10, 29.35, 29.28, 28.66, 28.56, 28.47, 26.56, 26.48, 25.82, 25.79, 24.44, 24.31, 24.22, 24.11, 9.22 IR (neat): 2931, 2862, 1731, 1078, 1013 cm -1

[0149] [Functional evaluation] The odor of 2-(2-t-butylcyclohexyloxy)butanal (6) obtained in Example 1 and its effects in a compounded fragrance were evaluated by three professional panelists. The evaluation was carried out using odor test strips (made of large-sized Western paper, 150 mm × 7 mm). The tip of the odor test strip was scented with 2-(2-t-butylcyclohexyloxy)butanal (6) of Example 1, and the evaluation was conducted indoors. The sensory evaluation was carried out from the perspective of the characteristics of the odor. The description was also made regarding the overall quality and characteristics of the scent felt by the three professional panelists in the sensory evaluation.

[0150] [Evaluation of Example 1] [Odor Evaluation of 2-(2-t-butylcyclohexyloxy)butanal (6)] It was confirmed that 2-(2-t-butylcyclohexyloxy)butanal (6) of Example 1 has a mint and camphor-like scent with a slightly earthy and floral-muguet-like aspect, and a woody aroma with a honey-like sweetness.

[0151] [Example 2: Blending Example 1] A composition (Example 2) was prepared by adding 50 parts by mass of 2-(2-t-butylcyclohexyloxy)butanal (6) obtained in Example 1 to 950 parts by mass of a compounded fragrance having a floral-rose fragrance tone with the composition shown in Table 1 below, or a composition (Comparative Example 1) was prepared by adding 50 parts by mass of propylene glycol, and a sensory evaluation was carried out.

[0152] In Table 1, the alcohols having 8 or more and 14 or less carbon atoms are budanol, cinnamic alcohol, citronellol, geraniol, and phenethyl alcohol. In Example 2, the total amount of these alcohols having 8 or more and 14 or less carbon atoms is 41.5% by mass, and the amount of the compound of formula (I) (2-(2-t-butylcyclohexyloxy)butanal (6)) is 5% by mass. Also, the mass ratio of the compound represented by formula (I) to the alcohol having 8 or more and 14 or less carbon atoms [compound represented by formula (I) / alcohol having 8 or more and 14 or less carbon atoms] was 0.12.

[0153] [Table 1]

[0154] In Table 1, * represents an alcohol having 8 to 14 carbon atoms. 1) Bacdanol: Trade name of IFF, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl) 2) Florosa: Trade name of Givaudan, 4-methyl-2-(2-methylpropyl)tetrahydro-2H-4-pyranol 3) Heliotropin: Trade name of Takasago Perfumery Co., Ltd., 3,4-methylenedioxybenzaldehyde 4) Iso-E-Super: Trade name of IFF, 1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)ethan-1-one 5) MDJ: Trade name of Kao Corporation, methyl (2-pentyl-3-oxocyclopentyl)acetate

[0155] [Table 2]

[0156] As a result of the sensory evaluation by three professional panelists, it was found that the fragrance composition of Example 2, compared with the fragrance composition of Comparative Example 1, harmonizes with the overall fragrance of the compounded fragrance and enhances the natural feeling, making the fragrance of the compounded fragrance closer to a natural fragrance.

[0157] [Example 3: Blending Example 2] A composition (Example 3) in which 50 parts by mass of 2-(2-t-butylcyclohexyloxy)butanal (6) obtained in Example 1 was added to 920 parts by mass of a floral-oriental fragrance compound having the composition shown in Table 3 below, and a composition (Comparative Example 2) in which 50 parts by mass of dipropylene glycol was added were each prepared, and a sensory evaluation was carried out.

[0158] In Table 3, the alcohols having 8 to 14 carbon atoms are dihydromyrcenol, sandalmysore core, and amber core. In Example 3, the total amount of these alcohols having 8 to 14 carbon atoms is 12.9% by mass, and the compound of formula (I) (2-(2-t-butylcyclohexyloxy)butanal (6)) is 5% by mass. Further, the mass ratio of the compound represented by formula (I) to the alcohol having 8 to 14 carbon atoms [compound represented by formula (I) / alcohol having 8 to 14 carbon atoms] was 0.38.

[0159]

Table 3

[0160] In Table 3, * indicates an alcohol having 8 to 14 carbon atoms. 5) MDJ: Trade name of Kao Corporation, methyl-(2-pentyl-3-oxocyclopentyl)acetate 6) Sandalmysore core: Trade name of Kao Corporation, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol 7) Tonalid: Trade name of PFW Aromachemicals, 1-(3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one

[0161]

Table 4

[0162] As a result of the sensory evaluation by three professional panelists, it was found that the fragrance composition of Example 3 was harmonious with the fragrance of the compounded fragrance as compared with the fragrance composition of Comparative Example 2, and emphasized the sweetness of the fragrance of the floral-oriental compounded fragrance.

[0163] The compound represented by formula (I) of the present invention and the fragrance composition containing the compound represented by formula (I) have a woody aroma. This woody aroma is a mint and camphor-like aroma with a slightly earthy and floral-muguet-like aspect. This woody aroma is further an aroma with a honey-like sweetness.

Claims

1. A compound represented by formula (I). 【Chemical Formula 15】 [In the above formula (I), R is an alkyl group having 1 to 5 carbon atoms]

2. The compound according to claim 1, wherein R is a t-butyl group.

3. A perfume composition comprising the compound according to claim 1 or 2.

4. The perfume composition according to claim 3, further comprising an alcohol having 8 to 14 carbon atoms.

5. The perfume composition according to claim 4, wherein the alcohol having 8 to 14 carbon atoms comprises a compound represented by formula (II). 【Chemical 16】 [In the above formula (II), R 1 and R 2 are each independently a hydrogen atom or a methyl group, R 3 is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, or a t-butyl group, R 4 is a methyl group or an ethyl group, R 5 is a hydroxy group or a hydroxymethyl group, X is -CH 2 - or -O- and n is 1 or 2, The dashed lines are each independently a single bond or a double bond.]

6. The perfume composition according to claim 4 or 5, wherein the alcohol having 8 to 14 carbon atoms is one or more selected from the group consisting of 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, and 1-(2-t-butylcyclohexyloxy)-2-butanol.

7. The perfume composition according to any one of claims 4 to 6, wherein the mass ratio of the compound represented by formula (I) to the alcohol having 8 to 14 carbon atoms [compound represented by formula (I) / alcohol having 8 to 14 carbon atoms] is 0.001 or more and 20 or less.

8. The perfume composition according to any one of claims 4 to 7, which further comprises one or more of alcohol, phenol, ester, carbonate, aldehyde, ketone, acetal, ether, lactone, nitrile, and amine, other than the compound represented by formula (I) and the alcohol having 8 to 14 carbon atoms.

9. A cosmetic comprising the perfume composition according to any one of claims 3 to 8.

10. A detergent composition comprising the perfume composition according to any one of claims 3 to 8.

11. A fiber treatment agent composition comprising the perfume composition according to any one of claims 3 to 8.

12. A method of using the compound according to claim 1 or 2 as a fragrance component.

13. A method for producing the compound according to claim 1, wherein the compound of formula (III) is oxidized to obtain the compound of formula (I). 【Chemical 17】 [In the above formulas (I) and (III), R is an alkyl group having 1 to 5 carbon atoms]

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