Novel aldehyde compound

Abstract

Provided are: 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.　The compound is represented by formula (I). [In formula (I), R represents an alkyl group having 1 to 5 carbon atoms.]

Description

New aldehyde compounds

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

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

[0003] Japanese Patent Laid-Open No. 61-268643 (Patent Document 1) discloses cis (or trans)-1-[1' (or 2' or 3')-formylpropoxy]-4-tert-butylcyclohexane and a fragrance composition containing the same. Patent Document 1 states that this fragrance composition has a green, aldehydic, citrus-like scent.

[0004]

[0005] Japanese Patent Laid-Open No. 5-339188 (Patent Document 2) discloses 2-(2-t-butylcyclohexyloxy)-1-butanol and a fragrance composition containing the same. Patent Document 2 states that this fragrance composition has a woody, amber-like fragrance with excellent lingering fragrance.

[0006]

[0007] The present invention is a compound represented by formula (I).

[0008] [In the formula (I), R is an alkyl group having 1 to 5 carbon atoms] Detailed Description of the Invention

[0009] The present invention aims to provide novel compounds with a woody aroma and fragrance compositions thereof. This woody aroma is a minty and camphor-like aroma with slight earthy and floral-lily-like aspects. This woody aroma also has a honey-like sweetness.

[0010] The present inventors have discovered a novel aldehyde compound with a woody aroma, and have completed the present invention. This woody aroma is minty and camphor-like, with slight earthy and floral-lily-like aspects. This woody aroma also has a honey-like sweetness.

[0011] The present invention is a compound represented by formula (I).

[0012]

[0013] [In the formula (I), R is an alkyl group having 1 to 5 carbon atoms]

[0014] The present invention also relates to a fragrance composition containing a compound represented by formula (I). Furthermore, the present invention also relates to a method of using a compound represented by formula (I) as a fragrance component.

[0015] The compound of formula (I) of the present invention has a woody odor. This woody odor is a minty and camphor-like odor with slight earthy and floral-lily-like aspects. This woody odor also has a honey-like sweetness.

[0016] As described above, the present invention is a compound represented by formula (I).

[0017]

[0018] [In the formula (I), R is an alkyl group having 1 to 5 carbon atoms.]

[0019] In the present specification, examples of an alkyl group having from 1 to 5 carbon atoms include a linear or branched alkyl group such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a sec-butyl group, a t-butyl group, an n-pentyl group, an i-pentyl group, a sec-pentyl group, a t-pentyl group, and a 2-methylbutyl group. An alkyl group having from 1 to 5 carbon atoms is preferably an alkyl group having from 1 to 4 carbon atoms, more preferably an alkyl group having from 3 to 4 carbon atoms, and more preferably a t-butyl group.

[0020] In the formula (I), from the viewpoint of imparting a woody fragrance with slight earthy and floral-lily-like aspects, mint and camphor-like, and honey-like sweetness, 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.

[0021] The compound represented by the formula (I) can be produced, for example, by the following method.

[0022]

[0023] In formula (I) and formula (III), R is an alkyl group having 1 to 5 carbon atoms.

[0024] The production method of the present invention includes a step of oxidizing a compound of formula (III) to obtain a compound of formula (I). This step involves, for example, subjecting the compound of formula (III) to oxidation using an oxidizing agent (e.g., Dess-Martine periodinane, etc.), Swern oxidation, PCC oxidation, TPAP (Ray-Griffiths) oxidation, TEMPO oxidation, or oxidation using MnO to obtain a compound of formula (I). The obtained compound of formula (I) can be separated and purified by distillation or column chromatography.

[0025] The present invention also relates to a fragrance composition containing a compound represented by formula (I).

[0026]

[0027] [In the formula (I), R is an alkyl group having 1 to 5 carbon atoms.]

[0028] Fragrance compositions containing the compound represented by formula (I) can impart a woody fragrance with slight earthy and floral-lily-like aspects, minty and camphor-like notes, and a honeyed sweetness, making them highly compatible with a variety of other fragrances and enabling the creation of distinctive fragrance effects by blending them together. 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.

[0029] In a fragrance composition containing a compound represented by formula (I), from the viewpoint of imparting a woody fragrance with slight earthy and floral-lily-like aspects, mint and camphor-like, and honey-like sweetness (hereinafter simply referred to as the viewpoint of imparting a woody fragrance with mint and camphor-like, and honey-like sweetness), R in formula (I) is preferably an alkyl group having from 1 to 4 carbon atoms, more preferably an alkyl group having from 3 to 4 carbon atoms, and even more preferably a t-butyl group.

[0030] The content of the compound of formula (I) in the fragrance composition is preferably 0.05% by mass or more, more preferably 0.5% by mass or more, even more preferably 1% by mass or more, and preferably 30% by mass or less, more preferably 20% by mass or less, and even more preferably 10% by mass or less, from the viewpoint of imparting a mint- and camphor-like, honey-like sweet, and woody fragrance; from the above viewpoints, 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.

[0031] The fragrance composition preferably further contains an alcohol having from 8 to 14 carbon atoms. By further containing an alcohol having from 8 to 14 carbon atoms, the natural feel of the fragrance composition containing it is enhanced and a complexity similar to that of a natural fragrance composition is created, thereby making the scent of a mixture of the fragrance composition further containing an alcohol having from 8 to 14 carbon atoms and the blended fragrance more natural-looking. From this viewpoint, the alcohol having from 8 to 14 carbon atoms is preferably a monoalcohol (monool), and is preferably an alcohol-based fragrance compound. The alcohol-based fragrance compound means a compound used for imparting fragrance and having a hydroxyl group.

[0032] 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, sandalmysole 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, tetraisopropyl methyl ... Examples of the alcohol include hydrogeraniol, hydroxycitronellol, terpineol, isopulegol, nopol, thymol, eugenol, and 3-methyl-5-phenylpentanol. By further containing an alcohol having from 8 to 14 carbon atoms, the natural feel of the fragrance composition containing it is enhanced and complexity like that of a natural fragrance composition is created, and as a result, the scent of the mixture of the fragrance composition further containing an alcohol having from 8 to 14 carbon atoms and the blended fragrance is made to be closer to natural scents. From this viewpoint, one or more selected from the group consisting of bacdanol, sandalmysole core, and amber core are preferred.

[0033]

[0034] The mass ratio of the compound represented by formula (I) to the alcohol having from 8 to 14 carbon atoms [compound represented by formula (I) / alcohol having from 8 to 14 carbon atoms] is preferably 0.001 or more, more preferably 0.01 or more, even more preferably 0.05 or more, and still more preferably 0.07 or more, from the viewpoint that the natural feel of the fragrance composition containing the alcohol having from 8 to 14 carbon atoms is enhanced by further containing the alcohol and that complexity like that of a natural fragrance composition is imparted thereto, and as a result, the scent of a mixture of the fragrance composition further containing the alcohol having from 8 to 14 carbon atoms and the blended fragrance is made to be more natural-looking; and from the viewpoint of imparting the scent note of the original alcohol having from 8 to 14 carbon atoms, the mass ratio is preferably 20 or less, more preferably 10 or less, even more preferably 5 or less, and still more preferably 1 or less. From these viewpoints, it is preferably 0.001 or more and 20 or less, more preferably 0.01 or more and 10 or less, even more preferably 0.05 or more and 5 or less, and still more preferably 0.07 or more and 1 or less.

[0035] Furthermore, in the fragrance composition containing the compound represented by formula (I), the content of the alcohol having from 8 to 14 carbon atoms is preferably 1% by mass or more, more preferably 5% by mass or more, and even more preferably 10% by mass or more, from the viewpoint of enhancing a natural feeling and generating complexity like that of a natural fragrance composition, and from the same viewpoint, it is preferably 90% by mass or less, more preferably 70% by mass or less, and even more preferably 50% by mass or less, and is preferably 1% by mass or more and 90% by mass or less, more preferably 5% by mass or more and 70% by mass or less, and even more preferably 10% by mass or more and 50% by mass or less.

[0036] When multiple types of alcohols having 8 to 14 carbon atoms are contained, the total mass of the alcohols is the "mass of the alcohols having 8 to 14 carbon atoms."

[0037] The alcohol having 8 to 14 carbon atoms preferably includes a compound represented by formula (II).

[0038]

[0039] In the formula (II), R 1 and R 2are each independently a hydrogen atom or a methyl group, 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, and each dashed line is independently a single bond or a double bond.

[0040] The alcohol having from 8 to 14 carbon atoms or the compound represented by formula (II) is preferably one or more selected from bacdanol (2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol), sandalmysole 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), from the viewpoint that further containing an alcohol having from 8 to 14 carbon atoms enhances the natural feel of a fragrance composition containing it and creates complexity like that of a natural fragrance composition, thereby making the scent of a mixture of a fragrance composition further containing an alcohol having from 8 to 14 carbon atoms and a blended fragrance more natural-looking.

[0041] The fragrance composition of the present invention, which contains the compound represented by formula (I) and the alcohol having from 8 to 14 carbon atoms, preferably further contains, in addition to the compound represented by formula (I) and the alcohol having from 8 to 14 carbon atoms, one or more of alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, nitriles, and amines.

[0042] As used herein, each fragrance "class" refers to a single compound or a mixture of two or more compounds.

[0043] Examples of alcohols include aliphatic alcohols, terpene alcohols, aromatic alcohols, and other alcohols, among which aliphatic alcohols are preferred.

[0044] Examples of terpene alcohols include linalool, ethyl linalool, hydroxycitronellol, nerol, terpineol, α-terpineol, dihydromyrcenol, farnesol, nerolidol, cedrol, menthol, and borneol.

[0045] Examples of aromatic alcohols include phenylethyl alcohol, benzyl alcohol, dimethylbenzylcarbinol, phenylethyldimethylcarbinol, and phenylhexanol.

[0046] Examples of aliphatic alcohols include cis-3-hexenol, 1-(2,2,6-trimethylcyclohexyl)-3-hexanol, Magnol (trade name, manufactured by Kao Corporation; a mixture mainly composed of ethylnorbornylcyclohexanol), Undecavertol (trade name, manufactured by Givaudan; 4-methyl-3-decen-5-ol), isobornylcyclohexanol, and Terpirosa (trade name, manufactured by Kao Corporation; 3,6-dimethyl-2-heptanol).

[0047] 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, and ethyl maltol.

[0048] Examples of hydrocarbons include limonene, α-pinene, β-pinene, terpinene, cedrene, longifolene, and valencene.

[0049] Examples of phenols include guaiacol, eugenol, dihydroeugenol, isoeugenol, thymol, para-cresol, vanillin, and ethyl vanillin.

[0050] Examples of esters include aliphatic carboxylic acid esters, aromatic carboxylic acid esters, and other carboxylic acid esters.

[0051] Examples of aliphatic carboxylic acids that form aliphatic carboxylic acid esters include linear and branched carboxylic acids having 1 to 18 carbon atoms, of which carboxylic acids having 1 to 6 carbon atoms such as formic acid, acetic acid, and propionic acid are preferred, with acetic acid being more preferred. Examples of aromatic carboxylic acids that form aromatic carboxylic acid esters include benzoic acid, anisic acid, phenylacetic acid, cinnamic acid, salicylic acid, and anthranilic acid. Examples of alcohols that form aliphatic and aromatic esters include linear and branched aliphatic alcohols having 1 to 5 carbon atoms and the fragrance component alcohols described above.

[0052] Examples of formic acid esters include linalyl formate, citronellyl formate, and geranyl formate.

[0053] 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, nopyr acetate, bornyl acetate, isobornyl acetate, acetyleugenol, acetylisoeugenol, o-tert-butylcyclohexane, hexyl acetate, p-tert-butylcyclohexyl acetate, tricyclodecenyl acetate, phenylethyl acetate, styrallyl acetate, cinnamyl acetate, dimethylbenzylcarbinyl acetate, 3-pentyltetrahydropyran-4-yl acetate, prenyl acetate, geranyl acetate, methylphenylcarbinyl acetate, and the like; phenylacetic acid esters include phenylethyl phenyl acetate and p-cresyl phenyl acetate.

[0054] Examples of propionate esters include ethyl propionate, citronellyl propionate, tricyclodecenyl propionate, benzyl propionate, styrallyl propionate, and Helbetolide (trade name, manufactured by Firmenich GmbH, 2-[1-(3,3-dimethylcyclohexyl)ethoxy]-2-methylpropyl) propionate.

[0055] Examples of butyric acid esters include citronellyl butyrate, dimethylbenzylcarbinyl n-butyrate, isoamyl n-butyrate, n-amyl n-butyrate, and the like; examples of isobutyric acid esters include tricyclodecenyl isobutyrate, phenoxyethyl isobutyrate, and the like.

[0056] Examples of valeric acid esters include methyl valerate, ethyl valerate, butyl valerate, amyl valerate, benzyl valerate, and phenylethyl valerate; and examples of hexanoic acid esters include methyl hexanoate, ethyl hexanoate, allyl hexanoate, linalyl hexanoate, and citronellyl hexanoate.

[0057] Examples of heptanoic acid esters include methylheptanoate and allylheptanoate.

[0058] Examples of nonenoic acid esters include methyl 2-nonenoate, ethyl 2-nonenoate, and ethyl 3-nonenoate.

[0059] Examples of benzoic acid esters include methyl benzoate, benzyl benzoate, and 3,6-dimethyl benzoate.

[0060] Examples of cinnamic acid esters include methyl cinnamate and benzyl cinnamate.

[0061] Examples of salicylate esters include methyl salicylate, n-hexyl salicylate, cis-3-hexenyl salicylate, cyclohexyl salicylate, and benzyl salicylate (benzyl salicylate).

[0062] Furthermore, examples of brassylic acid esters include ethylene brassylate.

[0063] Examples of tiglic acid esters include geranyl tiglate, 1-hexyl tiglate, and cis-3-hexenyl tiglate.

[0064] Examples of jasmonates include methyl jasmonate, and examples of dihydrojasmonates include MDJ (trade name, manufactured by Kao Corporation, methyl dihydrojasmonate, methyl (2-pentyl-3-oxocyclopentyl) acetate).

[0065] Examples of glycidic acid esters include methyl 2,4-dihydroxy-ethylmethylphenylglycidate and 4-methylphenylethylglycidate.

[0066] Examples of anthranilate esters include methyl anthranilate, ethyl anthranilate, and dimethyl anthranilate.

[0067] Examples of glycolic acid esters include allyl cyclohexyl glycolate.

[0068] Further examples of other esters include ethyl safranate (trade name, manufactured by Givaudan, ethyl dihydrocyclogeranate), poarenate (trade name, manufactured by Kao Corporation, ethyl-2-cyclohexylpropionate), and fultate (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, and allyl-2-pentyloxyglycolate.

[0069] Examples of carbonates include Lifarome (trade name, manufactured by IFF, cis-3-hexenylmethyl carbonate), Jasmaclat (trade name, manufactured by Kao Corporation, methyl cyclooctyl carbonate), and Floramat (trade name, manufactured by Kao Corporation, ethyl 2-t-butylcyclohexyl carbonate).

[0070] Examples of aldehydes include n-octanal, n-nonanal, n-decanal, n-dodecanal, 2-methylundecanal, 10-undecenal, citronellal, citral, hydroxycitronellal, Triplal (trade name, manufactured by IFF, 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde), Cyclovertal (trade name, manufactured by Kao Corporation, dimethyl-3-cyclohexenyl-1-carboxaldehyde), benzaldehyde, phenylacetaldehyde, phenylpropylaldehyde, cinnamic aldehyde, dimethyltetrahydrobenzaldehyde, bourgeonal (trade name, manufactured by Givaudan, 3-(4-tert-butylphenyl)propanal), Lyral (trade name, manufactured by IFF, hydroxymylac aldehyde), Polenal II (trade name, manufactured by Kao Corporation, 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde), and methylpropional (trade name, manufactured by Kao Corporation, 2,4-dimethyl-3-cyclohexenyl-1-carboxaldehyde). -cyclohexylpropanal), Lilial (trade name of Givaudan, p-tert-butyl-α-methylhydrocinnamic aldehyde), p-isopropyl-α-methylhydrocinnamic aldehyde, Floralozone (trade name of IFF, 3-(o-(and p-)ethylphenyl)-2,2-dimethylpropionaldehyde), α-amyl cinnamic aldehyde, α-hexyl cinnamic aldehyde, Heliotropin (trade name of Takasago International Corporation, 3,4-methylenedioxybenzaldehyde), Helional (trade name of IFF, alpha-methyl-1,3-benzodioxole-5-propanal), Canthoxal (trade name of IFF, 2-methyl-3-(paramethoxyphenyl)propanal), Aldehyde C-6 (trade name of Kao Corporation, n-hexanal), and the like.

[0071] Examples of ketones include methylheptenone, dimethyloctenone, 3-octanone, hexylcyclopentanone, dihydrojasmone, Beloutone (trade name, manufactured by Firmenich, 2,2,5-trimethyl-5-pentylcyclopentanone), Nectaryl (trade name, manufactured by Givaudan, 2-(2-(4-methyl-3-cyclohexen-1-yl)propyl)cyclopentanone), ionone, β-ionone, methylionone, methylionone-G, γ-methylionone, damascone, α -damascone, β-damascone, δ-damascone, isodamascone (trade name of Symrise, 1-(2,4,4-trimethyl-2-cyclohexyl)-trans-2-butanone), damascenone, dynascone (trade name of Firmenich, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one), irone, cashmeran (trade name of IFF, 1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-4H-indole), 4-one), Iso-E Super (trade name of IFF Co., Ltd., 1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-ethan-1-one), Karone (trade name of Firmenich Co., Ltd., 7-methyl-3,4-dihydro-2H-benzodioxepin-3-one), carvone, menthone, acetylcedrene, isolongifolanon, nootkatone, benzylacetone, raspberry ketone, benzophenone, tonalide (PFW Examples of suitable aromatic compounds include 6-acetyl-1,1,2,4,4,7-hexamethyltetrahydronaphthalene (a product of Firmenich), β-methyl naphthyl ketone, ethyl maltol, camphor, muscone, muscenone (3-methyl-5-cyclopentadecen-1-one, a product of Firmenich), civetone, Globanone (8-cyclohexadecenone, a product of Symrise), methyl nonyl ketone, cis-jasmone, and para-amylcyclohexanone (4-pentylcyclohexanone). Among these, ionone, damascenone, Iso-E-Super, and γ-methylionone are preferred from the viewpoint of emphasizing floral sweetness by blending with other fragrances.

[0072] Examples of acetals include acetaldehyde ethyl phenylpropyl acetal, citral diethyl acetal, phenylacetaldehyde glyceryl acetal, ethyl acetoacetate ethylene glycol acetal, Voisinbren Forte (trade name, manufactured by Kao Corporation, ethoxymethyl cyclododecyl ether), Troenan (trade name, manufactured by Kao Corporation, 5-methyl-5-propyl-2-(1-methylbutyl)-1,3-dioxane), Floropearl (trade name, manufactured by Symrise, 2,4,6-trimethyl-4-phenyl-1,3-dioxane), and Magnolan (trade name, manufactured by Symrise, 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxane).

[0073] 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, rosefuran, ambroxan (trade name, manufactured by Kao Corporation; [3aR-(3aα,5aβ,9aα,9bβ)]dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan), Herbaveil (trade name, manufactured by Kao Corporation; 3,3,5-trimethylcyclohexyl ethyl ether), Galaxolide (trade name, manufactured by IFF; hexamethylhexahydrocyclopentabenzopyran), phenylacetaldehyde dimethyl acetal, and methyl isoeugenol.

[0074] Examples of carboxylic acids include benzoic acid, phenylacetic acid, cinnamic acid, hydrocinnamic acid, butyric acid, and 2-hexenoic acid.

[0075] 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, and butylidenephthalide.

[0076] Examples of nitriles include tridecene-2-nitrile, geranyl nitrile, citronellyl nitrile, and dodecane nitrile.

[0077] Examples of amines include indole, skatole, 6-methylquinoline, 6-isopropylquinoline, and isobutylquinoline.

[0078] Examples of Schiff bases include aurantiol and ligantral.

[0079] It is also preferable that the fragrance composition of the present invention, which contains the compound represented by formula (I) and the alcohol having 8 to 14 carbon atoms, further contains a natural essential oil or a natural extract.

[0080] Examples of natural essential oils and natural extracts include oils, concretes, absolutes, resinoids, oleoresins, tinctures, infusions, and balsams of natural products such as orange, lemon, lime, bergamot, vanilla, mandarin, peppermint, spearmint, lavender, galbanum, chamomile, rosemary, eucalyptus, sage, basil, rose, rock rose, geranium, jasmine, ylang-ylang, anise, clove, ginger, nutmeg, cardamom, cedar, cypress, vetiver, patchouli, hay, lemongrass, labdanum, grapefruit, elemi oil, and bergamot oil.

[0081] In the fragrance composition of the present invention, the total content of other components other than the compound represented by formula (I) and the alcohol having from 8 to 14 carbon atoms can be appropriately selected depending on the type of blended fragrance, the type and intensity of the desired fragrance, etc., but is preferably 1% by mass or more, more preferably 5% by mass or more, even more preferably 10% by mass or more, and preferably 99% by mass or less, more preferably 80% by mass or less, even more preferably 70% by mass or less, in a composition containing the fragrance composition of the present invention.

[0082] The fragrance composition of the present invention can be combined with an oil that does not have an odor of its own as a base. Such an oil allows the fragrance components to be mixed uniformly, making it easy to incorporate into products and to impart a fragrance of appropriate intensity. Examples of such oils 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 ethers and sorbitan fatty acid esters.

[0083] Among these, from the viewpoint of improving the solubility of all fragrance components, polyhydric alcohols and esters are preferred as the oil, and dipropylene glycol and isopropyl myristate are more preferred. The content of such oil in the fragrance composition is preferably 0.01% by mass or more, more preferably 1% by mass or more, even more preferably 5% by mass or more, and preferably 95% by mass or less, more preferably 90% by mass or less, even more preferably 80% by mass or less.

[0084] The present invention also provides a cleanser composition containing the fragrance composition of the present invention, a cosmetic composition containing the fragrance composition of the present invention, and a fabric treatment composition containing the fragrance composition of the present invention.

[0085] The detergent composition of the present invention is preferably a body detergent composition, a clothing detergent composition, or a hard surface detergent composition, more preferably a body detergent composition or a clothing detergent composition, and even more preferably a clothing detergent composition.

[0086] Examples of body cleanser compositions include skin cleanser compositions, hair cleanser compositions, and soap compositions, with skin cleanser compositions being preferred.

[0087] Examples of hard surface cleaner compositions include all-purpose cleaners and dishwashing detergent compositions.

[0088] The fabric treatment composition of the present invention is preferably a softener composition.

[0089] The cosmetic products other than the cleanser composition of the present invention are preferably perfumes, emulsions, lotions, and sunscreens, and more preferably perfumes.

[0090] The cleanser composition of the present invention preferably contains an anionic surfactant in addition to the fragrance composition of the present invention, and may further contain a nonionic surfactant, a pH adjuster, a viscosity adjuster, a solvent, an oil, a preservative, water, etc.

[0091] The fiber treatment composition of the present invention preferably contains a cationic surfactant in addition to the fragrance composition of the present invention, and may further contain a pH adjuster, a solvent, an oil, a preservative, water, etc.

[0092] The perfume of the present invention may contain a solvent, water, etc. in addition to the fragrance composition of the present invention.

[0093] The compound represented by formula (I) has a woody odor. This woody odor is a minty and camphor-like odor with slight earthy and floral-lily-like aspects. This woody odor also has a honey-like sweetness. Furthermore, a composition comprising the compound represented by formula (I) and an alcohol having from 8 to 14 carbon atoms can give a new impression of naturalness to the alcohol having from 8 to 14 carbon atoms.

[0094] Therefore, the present invention relates to a method for using a compound represented by formula (I) of the present invention or a composition comprising a compound represented by formula (I) and an alcohol having 8 to 14 carbon atoms as a fragrance component, specifically, a method for using the compound as a fragrance component in a fragrance composition, a detergent composition, a cosmetic, or a fabric treatment composition. The detergent composition is preferably a body detergent composition, a clothing detergent composition, or a hard surface detergent composition, more preferably a body detergent composition or a clothing detergent composition, and even more preferably a clothing detergent composition. 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 preferred. Examples of the hard surface detergent composition include an all-purpose cleaner and a dishwashing detergent composition. The cosmetic is preferably a perfume. The fabric treatment composition is preferably a fabric softener composition.

[0095] In the above-mentioned method of use, the compound represented by formula (I) of the present invention or the composition comprising the compound represented by formula (I) and an alcohol having from 8 to 14 carbon atoms is used in an amount of preferably 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, even more preferably 10% by mass or less, 1% by mass or less, and more preferably 0.1% by mass or less, based on the cleanser composition, cosmetic, or fabric softener composition. By using this amount, when this fragrance composition is formulated as a fragrance material with other ingredients, it is possible to impart a new impression of a woody fragrance.

[0096] In the above-mentioned method of use, the fragrance composition of the present invention may be combined with an oil that does not have an odor by itself. The oil is the same as that described for the fragrance composition. In addition, in the above-mentioned method of use, other fragrances may be included, such as other commonly used fragrance ingredients or blended fragrances of a desired composition. Such other fragrances are the same as those described for the fragrance composition.

[0097] The present invention includes the following aspects: <1> A compound represented by formula (I).

[0098]

[0099] [In the formula (I), R is an alkyl group having 1 to 5 carbon atoms]

[0100] <2> The fragrance according to <1>, wherein R is a t-butyl group.

[0101] <3> A fragrance composition containing the compound according to <1> or <2>.

[0102] <4> The fragrance composition according to any one of <1> to <3>, wherein the content of the compound of formula (I) in the fragrance composition is 0.05% by mass or more and 30% by mass or less.

[0103] <5> The fragrance composition according to any one of <1> to <4>, wherein the content of the compound of formula (I) in the fragrance composition is 0.5% by mass or more and 20% by mass or less.

[0104] <6> The fragrance composition according to any one of <1> to <5>, wherein the content of the compound of formula (I) in the fragrance composition is 1% by mass or more and 10% by mass or less.

[0105] <7> The fragrance composition according to any one of <3> to <6>, further comprising an alcohol having from 8 to 14 carbon atoms.

[0106] <8> The fragrance composition according to <7>, wherein the alcohol having 8 to 14 carbon atoms is an alcohol-based fragrance compound.

[0107] <9> The fragrance composition according to <7> or <8>, wherein the alcohol having 8 to 14 carbon atoms is a monoalcohol.

[0108] <10> The fragrance composition according to any one of <7> to <9>, wherein the alcohol having 8 to 14 carbon atoms 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, sandalmysole 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.

[0109] <11> The fragrance 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, sandalmysole core, and amber core.

[0110] <12> The fragrance composition according to <7>, wherein the alcohol having 8 to 14 carbon atoms includes a compound represented by formula (II).

[0111]

[0112] [wherein in the formula (II), R1 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— or —O—, n is 1 or 2, and each dashed line is independently a single bond or a double bond.

[0113] <13> The fragrance composition according to any one of <7> to <10>, wherein the alcohol having from 8 to 14 carbon atoms is at least one 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.

[0114] <14> The fragrance composition according to any one of <7> to <13>, wherein the mass ratio of the compound represented by formula (I) to the alcohol having from 8 to 14 carbon atoms [compound represented by formula (I) / alcohol having from 8 to 14 carbon atoms] is from 0.001 to 20.

[0115] <15> The fragrance composition according to any one of <7> to <14>, wherein the mass ratio of the compound represented by formula (I) to the alcohol having from 8 to 14 carbon atoms [compound represented by formula (I) / alcohol having from 8 to 14 carbon atoms] is from 0.01 to 10.

[0116] <16> The fragrance composition according to any one of <7> to <15>, wherein the mass ratio of the compound represented by formula (I) to the alcohol having from 8 to 14 carbon atoms [compound represented by formula (I) / alcohol having from 8 to 14 carbon atoms] is from 0.05 to 5.

[0117] <17> The fragrance composition according to any one of <7> to <16>, wherein the mass ratio of the compound represented by formula (I) to the alcohol having from 8 to 14 carbon atoms [compound represented by formula (I) / alcohol having from 8 to 14 carbon atoms] is from 0.07 to 1.

[0118] <18> The fragrance composition according to any one of <7> to <17>, further comprising, other than the compound represented by formula (I) and the alcohol having from 8 to 14 carbon atoms, preferably one or more of alcohol, phenol, ester, carbonate, aldehyde, ketone, acetal, ether, lactone, nitrile, and amine.

[0119] <19> The fragrance composition according to any one of <7> to <18>, wherein the total content of other components other than the compound represented by formula (I) and the alcohol having from 8 to 14 carbon atoms, preferably the total content of alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, nitriles, and amines, is from 1% by mass to 99% by mass.

[0120] <20> The fragrance composition according to any one of <7> to <19>, wherein the total content of other components other than the compound represented by formula (I) and the alcohol having from 8 to 14 carbon atoms, preferably the total content of alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, nitriles, and amines, is from 5% by mass to 80% by mass.

[0121] <21> The fragrance composition according to any one of <7> to <20>, wherein the total content of other components other than the compound represented by formula (I) and the alcohol having from 8 to 14 carbon atoms, preferably the total content of alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, nitriles, and amines, is from 10% by mass to 70% by mass.

[0122] <22> The fragrance composition according to any one of <7> to <17>, further comprising a component other than the compound represented by formula (I) and the alcohol having from 8 to 14 carbon atoms, preferably a natural essential oil or a natural extract.

[0123] <23> A cosmetic comprising the fragrance composition according to any one of <3> to <22>.

[0124] <24> A cleanser composition containing the fragrance composition according to any one of <3> to <22>.

[0125] <25> A fabric treatment composition containing the fragrance composition according to any one of <3> to <22>.

[0126] <26> A method of using the compound according to <1> or <2> as a fragrance component.

[0127] <27> A method for using a composition comprising the compound according to <1> or <2> and an alcohol having 8 to 14 carbon atoms as a fragrance component.

[0128] <28> A method for producing the compound according to <1>, wherein the compound of formula (I) is obtained by oxidizing the compound of formula (III).

[0129]

[0130] [In the formulas (I) and (III), R is an alkyl group having 1 to 5 carbon atoms]

[0131] In the following examples, "%" means "% by mass" unless otherwise specified. The mass of the catalyst is the mass in a dry state.

[0132] <Gas Chromatography Apparatus and Analysis Conditions> GC apparatus: 7890B manufactured by Agilent Technologies, Inc., hydrogen flame ionization detector

[0133] 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.

[0134] When analyzing 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.

[0135] Carrier gas: He, 1.5 mL / min Injection conditions: 300°C, split ratio 100 / 1 Injection amount: 1 μL Detection conditions: FID method, 300°C Column temperature conditions: Starting from 80°C, the column was heated to 300°C at a rate of 10°C / min, and then held at 300°C for 10 minutes.

[0136] [Production Example 1] Production of 1-(2-t-butylphenyloxy)-2-butanol

[0137]

[0138] A 1-liter round-bottom flask equipped with a Dimroth tube and a dropping funnel was charged with 2-t-butylphenol (1) (350 g, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and 35 g of 48% aqueous sodium hydroxide solution (manufactured by Kanto Chemical Co., Ltd.) under a nitrogen stream, and the mixture was heated to 80°C. 1,2-butylene oxide (2) (176 g, manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise to the mixture over approximately 2 hours, followed by stirring at 80°C for 5 hours. After cooling the reaction mixture, the lower layer of 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 96% yield.

[0139] [Production Example 2] Production of a mixture of 1-(2-t-butylcyclohexyloxy)-2-butanol (4) and 2-(2-t-butylcyclohexyloxy)-1-butanol (5)

[0140]

[0141] 250 g of 1-(2-t-butylphenyloxy)-2-butanol (3) obtained in Production Example 1, an activated carbon-supported palladium catalyst (manufactured by N.E. Chemcat Corporation, trade name: S-Type, 50% water content, palladium loading of 2%, 4.75 g), and an activated carbon-supported ruthenium catalyst (manufactured by N.E. Chemcat Corporation, 50% water content, ruthenium loading of 5%, 0.25 g) were placed in a 500 ml autoclave, and the reaction was carried out at 190°C under a hydrogen pressure of 2.0 MPa for 6 hours.

[0142] 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%. The product was analyzed by gas chromatography, and the mass ratio of 1-(2-t-butylcyclohexyloxy)-2-butanol (4) to 2-(2-t-butylcyclohexyloxy)-1-butanol (5) was (4):(5)=75:25.

[0143] Example 1: Preparation of 2-(2-t-butylcyclohexyloxy)-butanal (6)

[0144]

[0145] 158 g of the 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-plate rectification column at a reflux ratio of 20, thereby obtaining a mixture of 1-(2-t-butylcyclohexyloxy)-2-butanol (4) and 2-(2-t-butylcyclohexyloxy)-1-butanol (5) in a mass ratio of compound (4) to compound (5) of 31:69 in a 50% yield.

[0146] The obtained mixture (1 g) 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) was 31:69) was dissolved in dichloromethane (43.8 mL), and Dess-Martine periodinane (2.2 g) was added at 0°C. After 10 minutes, the cooling bath was removed, and the reaction mixture was warmed to room temperature and stirred for 30 minutes to carry out the reaction.

[0147] As a post-treatment, a saturated aqueous solution of sodium thiosulfate was added to the reaction mixture to terminate the reaction. The reaction mixture was extracted with diethyl ether, the organic phase was dried over sodium sulfate, and the sodium sulfate was filtered off. The solvent was then 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).

[0148] Aqueous sodium hydrogen sulfite solution (100 mL) was added to a mixture of the obtained 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. The reaction mixture was extracted with hexane (50 mL), and then 1 mol / L sodium hydroxide solution was slowly added dropwise to the separated aqueous phase until the pH reached 10. The aqueous phase was stirred at room temperature (25°C) for 12 hours, then extracted with diethyl ether (100 mL), and the organic phase was dried over sodium sulfate. The sodium sulfate was filtered, and the solvent was then 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 77% yield.

[0149] 2-(2-t-Butylcyclohexyloxy)butanal (6) (diastereomeric mixture) 1 H-NMR (400MHz, CDCl3): 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 (100MHz, CDCl3): 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, 1013cm -1

[0150] [Sensory Evaluation] The odor of 2-(2-t-butylcyclohexyloxy)butanal (6) obtained in Example 1 and its effect in a blended fragrance were evaluated by three expert panelists. The evaluation was carried out using odor test paper (manufactured by Daimonji Paper, 150 mm x 7 mm), with 2-(2-t-butylcyclohexyloxy)butanal (6) from Example 1 applied to the tip of the odor test paper, and the evaluation was carried out indoors. The sensory evaluation was carried out from the perspective of odor characteristics. The overall quality and characteristics of the odor perceived by the three expert panelists in the sensory evaluation were also described.

[0151] [Evaluation of Example 1] [Odor Evaluation of 2-(2-t-butylcyclohexyloxy)butanal (6)] 2-(2-t-butylcyclohexyloxy)butanal (6) of Example 1 was confirmed to have a woody odor with slight earthy and floral-lily-like aspects, mint and camphor-like, and honey-like sweetness.

[0152] 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 the blended fragrance with a floral rose scent having the composition shown in Table 1 below, and a composition (Comparative Example 1) was prepared by adding 50 parts by mass of propylene glycol, and a sensory evaluation was carried out.

[0153] In Table 1, the alcohols having 8 to 14 carbon atoms are bagdanol, cinnamic alcohol, citronellol, geraniol, and phenethyl alcohol. In Example 2, the total amount of these alcohols having 8 to 14 carbon atoms was 41.5% by mass, and the amount of the compound of formula (I) (2-(2-t-butylcyclohexyloxy)butanal (6)) was 5% by mass. 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 0.12.

[0154]

[0155] In Table 1, * denotes alcohols 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 International Corporation, 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

[0156]

[0157] As a result of sensory evaluation by three expert panelists, it was found that the fragrance composition of Example 2, compared to the fragrance composition of Comparative Example 1, harmonizes with the overall scent of the blended fragrance and enhances the natural feeling, thereby making the scent of the blended fragrance more natural.

[0158] Example 3: Blending Example 2 A composition (Example 3) was prepared by adding 80 parts by mass of 2-(2-t-butylcyclohexyloxy)butanal (6) obtained in Example 1 to 920 parts by mass of the blended fragrance with a floral-oriental scent having the composition shown in Table 3 below, and a composition (Comparative Example 2) was prepared by adding 80 parts by mass of dipropylene glycol, and sensory evaluations were carried out.

[0159] In Table 3, the alcohols having 8 to 14 carbon atoms are dihydromyrcenol, sandalmysole core, and amber core. In Example 3, the total amount of these alcohols having 8 to 14 carbon atoms was 12.9% by mass, and the compound of formula (I) (2-(2-t-butylcyclohexyloxy)butanal (6)) was 5% by mass. 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.

[0160]

[0161] 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) Sandal Mysore Core: Trade name of Kao Corporation, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol 7) Tonalide: Trade name of PFW Aroma Chemicals, 1-(3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one

[0162]

[0163] As a result of sensory evaluation by three expert panelists, it was found that the fragrance composition of Example 3 harmonizes with the scent of the blended fragrance and emphasizes the sweetness of the floral-oriental blended fragrance, compared to the fragrance composition of Comparative Example 2.

[0164] The compound represented by formula (I) of the present invention and the fragrance composition containing the compound represented by formula (I) have a woody odor. This woody odor is a minty and camphor-like odor with slight earthy and floral-lily-like aspects. This woody odor also has a honey-like sweetness.

Claims

1. A compound represented by formula (I). [In the formula (I), R is an alkyl group having 1 to 5 carbon atoms] 2. The compound of claim 1, wherein R is a t-butyl group.

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

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

5. The fragrance composition according to claim 4, wherein the alcohol having 8 to 14 carbon atoms comprises a compound represented by formula (II). [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 -CH2- or -O-, n is 1 or 2, and each dashed line is independently a single bond or a double bond.

6. The fragrance composition according to claim 4 or 5, wherein the alcohol having 8 to 14 carbon atoms is at least one 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 fragrance 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 fragrance composition according to any one of claims 4 to 7, further comprising, other than the compound represented by formula (I) and the alcohol having from 8 to 14 carbon atoms, one or more of alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, nitriles, and amines.

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

10. A cleaning composition comprising the fragrance composition according to any one of claims 3 to 8.

11. A fabric treatment composition comprising the fragrance 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 ingredient.

13. A method for producing the compound of claim 1, comprising oxidizing a compound of formula (III) to obtain a compound of formula (I). In the formulas (I) and (III), R is an alkyl group having 1 to 5 carbon atoms.

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