Fragrance composition

Abstract

This fragrance composition comprises a compound represented by general formula (I) and a compound represented by general formula (II), wherein the mass ratio [compound represented by formula (I):compound represented by formula (II)] of the compound represented by formula (I) to the compound represented by formula (II) is 0.10:99.90 to 4.00:96.00. [In formula (I) and formula (II), R1 and R3 are each independently a C1-C5 alkyl group and R2 and R4 are each independently a hydrogen atom or a C1-C4 alkyl group.]

Description

fragrance composition

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

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

[0003] Japanese Patent Laid-Open No. 8-27056 (Patent Document 1) discloses that α-alkylcyclohexyloxy ketones have a soft, woody odor reminiscent of natural flowers and fruits, and that adding them to a blended fragrance can change the fragrance characteristics to one that is extremely close to natural.

[0004]

[0005] Japanese Patent Laid-Open No. 4-217937 (Patent Document 2) discloses that α-(alkylcyclohexyloxy)-β-alkanols have woody and ambery odors.

[0006]

[0007] The present invention relates to a fragrance composition comprising a compound represented by general formula (I) and a compound represented by general formula (II), wherein the mass ratio of the compound represented by formula (I) to the compound represented by formula (II) [compound represented by formula (I):compound represented by formula (II)] is 0.10:99.90 or more and 4.00:96.00 or less.

[0008]

[0009] [In the formula (I) and the formula (II), R 1 and R 3 are each independently an alkyl group having 1 to 5 carbon atoms, 2 and R 4 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Detailed Description of the Invention

[0010] The present invention focuses on α-alkylcyclohexyloxy ketones, which have not received much attention in the past, and aims to provide a new fragrance composition.

[0011] The present inventors have surprisingly found that, in a fragrance composition comprising an α-alkylcyclohexyloxy ketone and an α-(alkylcyclohexyloxy)-β-alkanol, when the α-alkylcyclohexyloxy ketone is contained in a specific ratio, a fragrance composition having an excellent balance of an ambery and woody scent with the sweetness and fullness of an orris scent can be obtained. Based on this finding, the fragrance composition of the present invention has been completed.

[0012] The present invention relates to a fragrance composition comprising a compound represented by general formula (I) and a compound represented by general formula (II), wherein the mass ratio of the compound represented by formula (I) to the compound represented by formula (II) [compound represented by formula (I):compound represented by formula (II)] is 0.10:99.90 or more and 4.00:96.00 or less.

[0013]

[0014] [In the formula (I) and the formula (II), R 1 and R 3 are each independently an alkyl group having 1 to 5 carbon atoms, 2 and R 4 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0015] The present invention also relates to a method for using, as a fragrance component, a composition comprising a compound represented by general formula (I) and a compound represented by general formula (II), wherein the mass ratio of the compound represented by formula (I) to the compound represented by formula (II) [compound represented by formula (I):compound represented by formula (II)] is 0.10:99.90 or more and 4.00:96.00 or less.

[0016]

[0017] [In the formula (I) and the formula (II), R 1 and R 3 are each independently an alkyl group having 1 to 5 carbon atoms, 2 and R 4are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0018] The composition of the present invention contains α-alkylcyclohexyloxy ketones in a specific ratio, and exhibits the effect of achieving an excellent balance of an amber-like and woody scent with the sweetness and fullness of an orris-like scent, making it useful as a fragrance composition.

[0019] As described above, the present invention is a fragrance composition comprising a compound represented by general formula (I) and a compound represented by general formula (II), wherein the mass ratio of the compound represented by formula (I) to the compound represented by formula (II) [compound represented by formula (I):compound represented by formula (II)] is 0.10:99.90 or more and 4.00:96.00 or less.

[0020]

[0021] [In the formula (I) and the formula (II), R 1 and R 3 are each independently an alkyl group having 1 to 5 carbon atoms, 2 and R 4 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0022] In the fragrance composition, from the viewpoints of imparting orris-like sweetness and volume, imparting fragrance longevity, and providing a well-balanced fragrance composition, the content of the compound of formula (II) is preferably 96.00% by mass or more, more preferably 97.00% by mass or more, even more preferably 98.0% by mass or more, preferably 99.90% by mass or less, more preferably 99.80% by mass or less, and even more preferably 99.75% by mass or less; from the above viewpoints, the content is preferably 96.00% by mass or more and 99.90% by mass or less, more preferably 97.00% by mass or more and 99.80% by mass or less, and even more preferably 98.00% by mass or more and 99.75% by mass or less.

[0023] The mass ratio of the compound represented by formula (I) to the compound represented by formula (II) [compound represented by formula (I):compound represented by formula (II)] is 0.10:99.90 or more, preferably 0.20:99.80 or more, and more preferably 0.25:99.75 or more, from the viewpoint of imparting orris-like sweetness and volume, imparting long-lasting fragrance, and obtaining a well-balanced fragrance composition; and is 4.00:96.00 or less, preferably 3.00:97:00 or less, and more preferably 2.00:98:00 or less, from the viewpoint of enhancing amber-like and woody fragrances, imparting volume, and obtaining a well-balanced fragrance composition.

[0024] From the above-mentioned viewpoints, the mass ratio of the compound represented by formula (I) to the compound represented by formula (II) [compound represented by formula (I):compound represented by formula (II)] is 0.10:99.90 or more and 4.00:96.00 or less, preferably 0.20:99.80 or more and 3.00:97:00 or less, and more preferably 0.25:99.75 or more and 2.00:98:00 or less.

[0025] The mass ratio of the compound represented by formula (I) to the compound represented by formula (II) [compound represented by formula (I):compound represented by formula (II)] being 0.10:99.90 or more means that the mass ratio of the compound represented by formula (I) / compound represented by formula (II) is 0.10 / 99.90 or more, and the mass ratio of the compound represented by formula (I) to the compound represented by formula (II) [compound represented by formula (I):compound represented by formula (II)] being 4.00:96.00 or less means that the mass ratio of the compound represented by formula (I) / compound represented by formula (II) is 4.00 / 96.00 or less.

[0026] In this specification, R 1 and R 3Among these, examples of the alkyl group having 1 to 5 carbon atoms include linear or branched alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, t-butyl, n-pentyl, i-pentyl, sec-pentyl, t-pentyl, and 2-methylbutyl. 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 more preferably a t-butyl group.

[0027] In this specification, R 2 and R 4 Among these, examples of the alkyl group having from 1 to 4 carbon atoms include linear or branched alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, and t-butyl. The alkyl group having from 1 to 4 carbon atoms is preferably an alkyl group having from 1 to 3 carbon atoms, more preferably an alkyl group having from 2 to 3 carbon atoms, and more preferably an ethyl group, in order to ensure that the fragrance composition of the present invention has an excellent balance of an amber-like and woody scent with an orris-like sweetness and fullness of scent.

[0028] In the formula (I), in order to provide the fragrance composition of the present invention with an excellent balance of amber-like and woody scents with orris-like sweetness and fragrant volume, R 1 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 formula (I), in order to provide the fragrance composition of the present invention with an excellent balance of amber-like and woody scents with orris-like sweetness and fragrant volume, R 2 is preferably an alkyl group having 1 to 3 carbon atoms, more preferably an alkyl group having 2 to 3 carbon atoms, and even more preferably an ethyl group.

[0030] As the compound represented by formula (I), for example, the following R shown in Table 1 can be used in order to provide the fragrance composition of the present invention with an excellent balance of amber-like and woody scents with orris-like sweetness and fragrant volume. 1 and R 2 A compound having a combination of R 1 is a t-butyl group, and R 2 However, an ethyl group is more preferred.

[0031]

[0032] As the compound represented by formula (I), for example, the following compounds are preferred, because they enable the fragrance composition of the present invention to have an excellent balance of amber-like and woody scents with orris-like sweetness and fragrant volume.

[0033]

[0034] The compound represented by formula (I) may be a mixture of the following cis- and trans-isomers, or may be any one of them.

[0035]

[0036] In the formula (II), R is preferably 0.01 to 0.10, in order to provide the fragrance composition of the present invention with an excellent balance of amber-like and woody scents with orris-like sweetness and fragrant volume. 3 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.

[0037] In the formula (II), R is preferably 0.01 to 0.10, in order to provide the fragrance composition of the present invention with an excellent balance of amber-like and woody scents with orris-like sweetness and fragrant volume. 4 is preferably an alkyl group having 1 to 3 carbon atoms, more preferably an alkyl group having 2 to 3 carbon atoms, and even more preferably an ethyl group.

[0038] As the compound represented by formula (II), for example, the following R shown in Table 2 may be used in order to provide the fragrance composition of the present invention with an excellent balance of amber-like and woody scents with orris-like sweetness and fragrant volume. 3and R 4 A compound having a combination of R 3 is a t-butyl group, and R 4 However, an ethyl group is more preferred.

[0039]

[0040] As the compound represented by formula (II), for example, the following compounds are preferred, because they enable the fragrance composition of the present invention to have an excellent balance of amber-like and woody scents with orris-like sweetness and fragrant volume.

[0041]

[0042] The compound represented by formula (II) may be a mixture of the following cis- and trans-isomers, or may be any one of them.

[0043]

[0044] In the fragrance composition of the present invention, in order to obtain a fragrance composition having an excellent balance of amber-like and woody scents with orris-like sweetness and fragrant volume, R 1 and R 3 is preferably a t-butyl group.

[0045] In the fragrance composition of the present invention, in order to obtain a fragrance composition having an excellent balance of amber-like and woody scents with orris-like sweetness and fragrant volume, R 2 and R 4 is preferably a methyl group or an ethyl group.

[0046] In the fragrance composition of the present invention, in order to obtain a fragrance composition having an excellent balance of amber-like and woody scents with orris-like sweetness and fragrant volume, R 1 and R 3 is a t-butyl group, and R 2 and R 4 is more preferably a methyl group or an ethyl group.

[0047] In the fragrance composition of the present invention, examples of the combination of the compound represented by formula (I) and the compound represented by formula (II) include a combination of one or more selected from the group consisting of combinations I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, I-10, I-11, I-12, I-13, I-14, I-15, and I-16 shown in Table 1 and one or more selected from the group consisting of combinations II-1, II-2, II-3, II-4, II-5, II-6, II-7, II-8, II-9, II-10, II-11, II-12, II-13, II-14, II-15, and II-16 shown in Table 2. The combination of the compound represented by formula (I) and the compound represented by formula (II) makes the fragrance composition of the present invention well-balanced, imparting an amber-like and woody scent with orris-like sweetness and fragrant volume, and therefore the combination I-16 and the combination II-16 are more preferred. 1 is a t-butyl group, R 2 is an ethyl group, R 3 is a t-butyl group, R 4 An ethyl group is preferred.

[0048] The compound represented by the formula (I) can be produced, for example, by the method described in JP-A-8-27056.

[0049] The compound represented by the formula (I) can also be produced, for example, by the following method.

[0050]

[0051] In the formula (I) and formula (III), R 1 is an alkyl group having 1 to 5 carbon atoms, 2 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0052] The method includes a step of oxidizing a compound of formula (III) to obtain a compound of formula (I). In the step, for example, the compound of formula (III) is oxidized using an oxidizing agent (e.g., Dess-Martine periodinane) to obtain a compound of formula (I). The obtained compound of formula (I) can be separated and purified by distillation or column chromatography.

[0053] The compound represented by the formula (II) can be produced, for example, by the method described in JP-A-4-217937.

[0054] In order to achieve an excellent balance of amber-like and woody scents with orris-like sweetness and fragrant volume, the fragrance composition of the present invention preferably further contains, in addition to the compound represented by formula (I) and the compound represented by formula (II), one or more of alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, and nitriles.

[0055] As used herein, each fragrance "class" refers to a single compound or a mixture of two or more compounds.

[0056] Examples of alcohols include aliphatic alcohols, terpene alcohols, aromatic alcohols, and other alcohols, among which aliphatic alcohols are preferred.

[0057] Examples of terpene alcohols include linalool, ethyl linalool, citronellol, hydroxycitronellol, geraniol, tetrahydrogeraniol, nerol, terpineol, α-terpineol, dihydromyrcenol, farnesol, nerolidol, cedrol, menthol, and borneol.

[0058] Examples of aromatic alcohols include phenylethyl alcohol, benzyl alcohol, dimethylbenzylcarbinol, phenylethyldimethylcarbinol, and phenylhexanol.

[0059] Examples of aliphatic alcohols include cis-3-hexenol, 1-(2,2,6-trimethylcyclohexyl)-3-hexanol, Sandalmysole Core (trade name, manufactured by Kao Corporation, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol), 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).

[0060] Other alcohols include glycols such as dipropylene glycol, Florosa (manufactured by Givaudan, chemical name: 4-methyl-2-(2-methylpropyl)tetrahydro-2H-4-pyranol), maltol, and ethyl maltol.

[0061] Examples of hydrocarbons include limonene, α-pinene, β-pinene, terpinene, cedrene, longifolene, and valencene.

[0062] Examples of phenols include guaiacol, eugenol, dihydroeugenol, isoeugenol, thymol, para-cresol, vanillin, and ethyl vanillin.

[0063] Examples of esters include aliphatic carboxylic acid esters, aromatic carboxylic acid esters, and other carboxylic acid esters.

[0064] 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.

[0065] Examples of formic acid esters include linalyl formate, citronellyl formate, and geranyl formate.

[0066] 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.

[0067] 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.

[0068] Examples of butyric acid esters include citronellyl butyrate, dimethylbenzylcarbinyl n-butyrate, isoamyl n-butyrate, and n-amyl n-butyrate; examples of isobutyric acid esters include tricyclodecenyl isobutyrate and phenoxyethyl isobutyrate.

[0069] 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.

[0070] Examples of heptanoic acid esters include methylheptanoate and allylheptanoate.

[0071] Examples of nonenoic acid esters include methyl 2-nonenoate, ethyl 2-nonenoate, and ethyl 3-nonenoate.

[0072] Examples of benzoic acid esters include methyl benzoate, benzyl benzoate, and 3,6-dimethyl benzoate.

[0073] Examples of cinnamic acid esters include methyl cinnamate and benzyl cinnamate.

[0074] Examples of salicylate esters include methyl salicylate, n-hexyl salicylate, cis-3-hexenyl salicylate, cyclohexyl salicylate, and benzyl salicylate (benzyl salicylate).

[0075] Furthermore, examples of brassylic acid esters include ethylene brassylate.

[0076] Examples of tiglic acid esters include geranyl tiglate, 1-hexyl tiglate, and cis-3-hexenyl tiglate.

[0077] 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).

[0078] Examples of glycidic acid esters include methyl 2,4-dihydroxy-ethylmethylphenylglycidate and 4-methylphenylethylglycidate.

[0079] Examples of anthranilate esters include methyl anthranilate, ethyl anthranilate, and dimethyl anthranilate.

[0080] Examples of glycolic acid esters include allyl cyclohexyl glycolate.

[0081] 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.

[0082] Examples of carbonates include Lifarome (trade name, manufactured by IFF, cis-3-hexenylmethyl carbonate), Jasmacliclat (trade name, manufactured by Kao Corporation, methyl cyclooctyl carbonate), and Floramat (trade name, manufactured by Kao Corporation, ethyl 2-t-butylcyclohexyl carbonate).

[0083] 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), and Polenal II (trade name, manufactured by Kao Corporation). 2-Cyclohexylpropanal), Lilial (Givaudan: p-tert-butyl-α-methylhydrocinnamic aldehyde), p-isopropyl-α-methylhydrocinnamic aldehyde, Floralozone (IFF: 3-(o-(and p-)ethylphenyl)-2,2-dimethylpropionaldehyde), α-amyl cinnamic aldehyde, α-hexyl cinnamic aldehyde, Heliotropin (Takasago International Corporation: 3,4-methylenedioxybenzaldehyde), Helional (IFF: alpha-methyl-1,3-benzodioxole-5-propanal), Canthoxal (IFF: 2-methyl-3-(paramethoxyphenyl)propanal), Aldehyde C-6 (Kao Corporation) Examples include n-hexanal (trade name).

[0084] 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, manufactured by Symrise, 1-(2,4,4-trimethyl-2-cyclohexyl)-trans-2-butanone), damascenone, and Dynascone (trade name, manufactured by Firmenich). Trade name: 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one), irone, cashmeran (manufactured by IFF, trade name: 1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-4H-inden-4-one), Iso-E Super (manufactured by IFF, trade name: 1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-ethan-1-one), chalon (manufactured by Firmenich, trade name: 7-methyl-3,4-dihydro-2H-benzodioxepin-3-one), carvone, menthone, acetylcedrene, isolongifolanon, nootkatone, benzylacetone, raspberry ketone, benzophenone, tonalide (manufactured by PFW, trade name: Examples of such an isomer include 6-acetyl-1,1,2,4,4,7-hexamethyltetrahydronaphthalene (manufactured by Firmenich, trade name: 3-methyl-5-cyclopentadecen-1-one), civetone, Globanone (manufactured by Symrise, trade name: 8-cyclohexadecenone), methyl nonyl ketone, cis-jasmone, para-amylcyclohexanone (4-pentylcyclohexanone), and Tonalide (manufactured by PFW Aroma Chemicals, trade name: 1-(3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one).Among these, ionone, damascenone, Iso-E-Super, and γ-methylionone are preferred from the viewpoint of emphasizing floral sweetness when blended with the fragrance composition of the present invention.

[0085] 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 Co., Ltd., 2,4,6-trimethyl-4-phenyl-1,3-dioxane), and Magnolan (trade name, manufactured by Symrise Co., Ltd., 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxane).

[0086] 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 methylisoeugenol.

[0087] Examples of carboxylic acids include benzoic acid, phenylacetic acid, cinnamic acid, hydrocinnamic acid, butyric acid, and 2-hexenoic acid.

[0088] 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.

[0089] Examples of nitriles include tridecene-2-nitrile, geranyl nitrile, citronellyl nitrile, and dodecane nitrile.

[0090] In addition, the fragrance composition of the present invention preferably further contains natural essential oils or natural extracts to achieve an excellent balance of amber-like and woody scents with orris-like sweetness and fragrant volume.

[0091] 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.

[0092] The total content of the compound represented by formula (I) and the compound represented by formula (II) in the fragrance composition of the present invention can be appropriately selected depending on the type of blended fragrance, the type and intensity of the desired fragrance, and the like. From the viewpoint of imparting a well-balanced fragrance that combines amber-like and woody fragrances with orris-like sweetness and fragrant volume, the total content of the compound represented by formula (I) and the compound represented by formula (II) in the fragrance composition of the present invention is preferably 0.0001% by mass or more, more preferably 0.001% by mass or more, even more preferably 0.1% by mass or more, still more preferably 1% by mass or more, and preferably 99.99% by mass or less, more preferably 80% by mass or less, even more preferably 60% by mass or less, still more preferably 50% by mass or less, and is preferably 0.0001% by mass or more and 99.99% by mass or less, more preferably 0.001% by mass or more and 80% by mass or less, even more preferably 0.1% by mass or more and 60% by mass or less, and still more preferably 1% by mass or more and 50% by mass or less.

[0093] 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.

[0094] 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.

[0095] 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.

[0096] 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.

[0097] Examples of body cleanser compositions include skin cleanser compositions, hair cleanser compositions, and soap compositions, with skin cleanser compositions being preferred.

[0098] Examples of hard surface cleaner compositions include all-purpose cleaners and dishwashing detergent compositions.

[0099] The fabric treatment composition of the present invention is preferably a softener composition.

[0100] The cosmetic products other than the cleanser composition of the present invention are preferably perfumes, emulsions, lotions, and sunscreens, and more preferably perfumes.

[0101] 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.

[0102] 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.

[0103] The perfume of the present invention may contain a solvent, water, etc. in addition to the fragrance composition of the present invention.

[0104] The present invention also relates to a method for using, as a fragrance component, a composition comprising a compound represented by general formula (I) and a compound represented by general formula (II), wherein the mass ratio of the compound represented by formula (I) to the compound represented by formula (II) [compound represented by formula (I):compound represented by formula (II)] is 0.10:99.90 or more and 4.00:96.00 or less.

[0105] The preferred mass ratio of the compound represented by formula (I) to the compound represented by formula (II) in the method [compound represented by formula (I):compound represented by formula (II)] is as described above.

[0106]

[0107] [In the formula (I) and the formula (II), R 1 and R 3 are each independently an alkyl group having 1 to 5 carbon atoms, 2 and R 4 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 1 , R 2 , R 3 , R 4 The preferred groups are as described above.

[0108] A specific example of a method for using the composition of the present invention as a fragrance component is a method for using the composition 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 and a hair detergent 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.

[0109] In the method of using the composition, the composition 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 in the cleanser composition, cosmetic, or fabric softener composition. By using the composition in this amount, the fragrance material can impart a new impression of an excellent balance of an amber-like and woody scent with the sweetness and fullness of an orris-like scent.

[0110] In the method of use, the composition may be used in combination 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 method of use, the composition may be used in combination with other fragrances, 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.

[0111] The present invention includes the following aspects: <1> A fragrance composition comprising a compound represented by general formula (I) and a compound represented by general formula (II), wherein the mass ratio of the compound represented by formula (I) to the compound represented by formula (II) [compound represented by formula (I):compound represented by formula (II)] is 0.10:99.90 or more and 4.00:96.00 or less.

[0112]

[0113] [In the formula (I) and the formula (II), R 1 and R 3 are each independently an alkyl group having 1 to 5 carbon atoms, 2 and R 4 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0114] <2> R 1 and R 3 is a t-butyl group.

[0115] <3> R2 and R 4 is a methyl group or an ethyl group.

[0116] <4> R 1 and R 3 is a t-butyl group, and R 2 and R 4 <1> <3> The fragrance composition according to any one of <1> to <3>, wherein is an ethyl group.

[0117] <5> The fragrance composition according to any one of <1> to <4>, wherein the mass ratio of the compound represented by formula (I) to the compound represented by formula (II) [compound represented by formula (I):compound represented by formula (II)] is 0.20:99.80 or more and 3.00:97:00 or less.

[0118] <6> The fragrance composition according to any one of <1> to <5>, wherein the mass ratio of the compound represented by formula (I) to the compound represented by formula (II) [compound represented by formula (I):compound represented by formula (II)] is 0.25:99.75 or more and 2.00:98:00 or less.

[0119] <7> The fragrance composition according to any one of <1> to <6>, wherein the total content of the compound represented by formula (I) and the compound represented by formula (II) in the fragrance composition is 0.0001% by mass or more and 99.99% by mass or less.

[0120] <8> The fragrance composition according to any one of <1> to <7>, wherein the total content of the compound represented by formula (I) and the compound represented by formula (II) in the fragrance composition is 0.001% by mass or more and 80% by mass or less.

[0121] <9> The fragrance composition according to any one of <1> to <8>, wherein the total content of the compound represented by formula (I) and the compound represented by formula (II) in the fragrance composition is more preferably 0.1% by mass or more and 60% by mass or less.

[0122] <10> The fragrance composition according to any one of <1> to <9>, wherein the total content of the compound represented by formula (I) and the compound represented by formula (II) in the fragrance composition is 1% by mass or more and 50% by mass or less.

[0123] <11> The fragrance composition according to any one of <1> to <10>, further comprising at least one of alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, and nitriles, other than the compound represented by formula (I) and the compound represented by formula (II).

[0124] <12> The fragrance composition according to any one of <1> to <11>, further comprising a natural essential oil or a natural extract other than the compound represented by formula (I) and the compound represented by formula (II). <13> A cosmetic comprising the fragrance composition according to any one of <1> to <12>.

[0125] <14> A cleanser composition containing the fragrance composition according to any one of <1> to <12>.

[0126] <15> A fabric treatment composition containing the fragrance composition according to any one of <1> to <12>.

[0127] <16> A method for using, as a fragrance component, a composition comprising a compound represented by general formula (I) and a compound represented by general formula (II), wherein the mass ratio of the compound represented by formula (I) to the compound represented by formula (II) [compound represented by formula (I):compound represented by formula (II)] is 0.10:99.90 or more and 4.00:96.00 or less.

[0128]

[0129] [In the formula (I) and the formula (II), R 1 and R 3 are each independently an alkyl group having 1 to 5 carbon atoms, 2 and R 4 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0130] In the following examples, "%" means "% by mass" unless otherwise specified. The mass of the catalyst is the mass in a dry state.

[0131] <Gas Chromatography Apparatus and Analysis Conditions> GC apparatus: 7890B manufactured by Agilent Technologies, Inc., 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 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 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.

[0135] [Production Example 1] Production of 1-(2-t-butylphenyloxy)-2-butanol (3)

[0136]

[0137] 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 to room temperature (25°C), 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.

[0138] [Production Example 2] Production of 1-(2-t-butylcyclohexyloxy)-2-butanol (4)

[0139]

[0140] 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.

[0141] After completion of the reaction, the catalyst was filtered off and the filtrate was distilled to obtain 1-(2-t-butylcyclohexyloxy)-2-butanol (4) with a purity of 100% and a yield of 70%. The product was analyzed by gas chromatography, and the mass ratio of cis to trans was found to be cis:trans=57:43.

[0142]

[0143] [Production Example 3] Production of 1-(2-t-butylcyclohexyloxy)butan-2-one (5)

[0144]

[0145] 1-(2-t-butylcyclohexyloxy)-2-butanol (4) (2 g) obtained in Preparation Example 2 was dissolved in dichloromethane (35.0 mL), and Dess-Martine periodinane (4.5 g) was added at 0°C. After 10 minutes, the cooling bath was removed, and the reaction mixture was warmed to room temperature (25°C) and stirred for 30 minutes. The reaction was quenched by adding saturated aqueous sodium thiosulfate solution as a post-treatment. The mixture was extracted with diethyl ether, dried over sodium sulfate, and filtered. The solvent was then evaporated to obtain 1-(2-t-butylcyclohexyloxy)butan-2-one (5). The obtained crude product was purified by silica gel column chromatography to obtain 1-(2-t-butylcyclohexyloxy)butan-2-one (5) with a purity of 100% and a yield of 92%.

[0146] Example 1 9.981 g of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) obtained in Production Example 3 was added to 19 mg of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) obtained in Production Example 3, and the mixture was mixed to obtain a fragrance composition (GC composition ratio of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) / 1-(2-t-butylcyclohexyloxy)-2-butanol (4) in the mixture = 0.19 / 99.81).

[0147] Example 2 9.979 g of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) (cis / trans mass ratio = 57:43) obtained in Production Example 2 was added to 21 mg of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) obtained in Production Example 3 and mixed to obtain a fragrance composition (GC composition ratio of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) / 1-(2-t-butylcyclohexyloxy)-2-butanol (4) in the mixture = 0.21 / 99.79).

[0148] Example 3 9.971 g of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) obtained in Production Example 3 was added to 29 mg of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) obtained in Production Example 3, and the mixture was mixed to obtain a fragrance composition (GC composition ratio of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) / 1-(2-t-butylcyclohexyloxy)-2-butanol (4) in the mixture = 0.29 / 99.71).

[0149] Example 4 9.888 g of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) obtained in Production Example 3 was added to 0.112 g of the 1-(2-t-butylcyclohexyloxy)butanol (4) obtained in Production Example 2 and mixed to obtain a fragrance composition (GC composition ratio of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) / 1-(2-t-butylcyclohexyloxy)-2-butanol (4) in the mixture = 1.12 / 98.88).

[0150] Example 5 0.97 g of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) obtained in Production Example 3 was added to 30 mg of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) obtained in Production Example 3, and the mixture was mixed to obtain a fragrance composition (GC composition ratio of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) / 1-(2-t-butylcyclohexyloxy)-2-butanol (4) in the mixture = 3.00 / 97.00).

[0151] Comparative Example 1 0.9515 g of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) obtained in Production Example 3 was added to 48.5 mg of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) obtained in Production Example 3, and the mixture was mixed to obtain a fragrance composition (GC composition ratio of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) / 1-(2-t-butylcyclohexyloxy)-2-butanol (4) in the mixture = 4.85 / 95.15).

[0152] [Sensory Evaluation] The odors of the fragrance compositions obtained in Examples 1 to 5 and Comparative Example 1 were evaluated by three expert panelists. The evaluation was performed using odor test paper (manufactured by Daimonji Paper, 150 mm x 7 mm). Each of Examples 1 to 5 and Comparative Example 1, which have different isomer ratios, was applied to the tip of the odor test paper, and the evaluation was performed indoors. The sensory evaluation was performed from the perspective of odor characteristics and intensity. The odor characteristics and intensity were relatively rated on a 5-point scale, with higher values ​​being preferred. Regarding lingering odor, the length of time the odor lasted was confirmed, and the elapsed time and odor intensity at that time were relatively rated on a 10-point scale, with higher values ​​being preferred. The overall quality and characteristics of the odor perceived by the three expert panelists during the sensory evaluation were also described. The results are shown in Tables 3 and 4.

[0153] From the viewpoint of scent characteristics and intensity, the fragrances were ranked according to the following criteria as an overall evaluation of their usefulness as fragrance ingredients: A: Extremely interesting and highly valuable as fragrance ingredients B: Sufficient value as fragrance ingredients C: Almost sufficient value as fragrance ingredients D: Slightly less valuable as fragrance ingredients

[0154]

[0155] [Evaluation Results] As shown in Tables 3 and 4, the fragrance composition of the present invention is an excellently balanced fragrance composition that has an inherent amber-like and woody (and camphor-like) scent combined with the sweetness and volume of orris.

Claims

1. A fragrance composition comprising a compound represented by general formula (I) and a compound represented by general formula (II), wherein the mass ratio of the compound represented by formula (I) to the compound represented by formula (II) [compound represented by formula (I): compound represented by formula (II)] is 0.10:99.90 or more and 4.00:96.00 or less. [In the above formula (I) and formula (II), R 1 and R 3 are each independently an alkyl group having 1 to 5 carbon atoms; R 2 and R 4 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

2. R 1 and R 3 The fragrance composition according to claim 1, wherein is a t-butyl group.

3. R 2 and R 4 The fragrance composition according to claim 1 or 2, wherein is a methyl group or an ethyl group.

4. R 1 and R 3 is a t-butyl group, R 2 and R 4 The fragrance composition according to any one of claims 1 to 3, wherein is an ethyl group.

5. The fragrance composition according to any one of claims 1 to 4, wherein the mass ratio of the compound represented by formula (I) to the compound represented by formula (II) [compound represented by formula (I):compound represented by formula (II)] is 0.25:99.75 or more and 2.00:98:00 or less.

6. The fragrance composition according to any one of claims 1 to 5, further comprising at least one of alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, and nitriles other than the compound represented by formula (I) and the compound represented by formula (II).

7. A cosmetic comprising the fragrance composition according to any one of claims 1 to 6.

8. A cleaning composition comprising the fragrance composition according to any one of claims 1 to 6.

9. A fabric treatment composition comprising the fragrance composition according to any one of claims 1 to 6.

10. A method for using a composition comprising a compound represented by general formula (I) and a compound represented by general formula (II), in which the mass ratio of the compound represented by formula (I) to the compound represented by formula (II) [compound represented by formula (I): compound represented by formula (II)] is 0.10:99.90 or more and 4.00:96.00 or less, as a fragrance component. [In the above formula (I) and formula (II), R 1 and R 3 are each independently an alkyl group having 1 to 5 carbon atoms; R 2 and R 4 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

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