Perfume composition

Abstract

To provide a new perfume composition.SOLUTION: The perfume composition comprises a compound represented by general formula (I) and a compound represented by general formula (II), where 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 from 0.10:99.90 to 4.00:96.00 inclusive. [In formulas (I) and (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.]SELECTED DRAWING: None

Description

Technical Field

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

Background Art

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

[0003] Patent Document 1 discloses that α-alkylcyclohexyloxy ketones have a soft woody aroma reminiscent of natural flowers and fruits, and that their aroma characteristics can be changed to be extremely close to natural ones by adding them to compounded fragrances.

[0004]

Chemical formula

[0005] Patent Document 2 discloses that α-(alkylcyclohexyloxy)-β-alcohols have a woody and amber-like aroma.

[0006]

Chemical formula

Prior Art Documents

Patent Documents

[0007]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0008] The present invention focuses on α-alkylcyclohexyl oxiketones, which have not been conventionally noted, and aims to provide a new perfume composition.

[0009] The present inventors have surprisingly found that in a perfume composition containing α-alkylcyclohexyl oxiketones and α-(alkylcyclohexyloxy)-β-alkanols, when the perfume composition contains a specific ratio of α-alkylcyclohexyl oxiketones, a perfume composition excellent in balance is obtained, which imparts an orris-like sweetness and volume of fragrance to amber-like and woody scents. Based on this finding, the perfume composition of the present invention has been completed.

[0010] The present invention is a perfume composition containing a compound represented by the general formula (I) and a compound represented by the general formula (II), wherein the mass ratio of the compound represented by the formula (I) to the compound represented by the formula (II) [compound represented by the formula (I): compound represented by the formula (II)] is 0.10:99.90 or more and 4.00:96.00 or less.

[0011]

Chemical formula

[0012] [In the above formulas (I) and (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. ]

[0013] Further, the present invention is a composition comprising a compound represented by the general formula (I) and a compound represented by the general formula (II), A method of using, as a fragrance component, a composition in which the mass ratio of the compound represented by the formula (I) to the compound represented by the formula (II) [compound represented by the formula (I): compound represented by the formula (II)] is 0.10:99.90 or more and 4.00:96.00 or less.

[0014]

Chemical formula

[0015] [In the above formulas (I) and (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.]

Advantages of the Invention

[0016] The composition of the present invention contains specific ratios of α-alkylcyclohexyloxyketones and has the effect of being excellent in balance, imparting an orris-like sweetness and volume to the amber-like and woody scents, and is useful as a fragrance composition.

Modes for Carrying Out the Invention

[0017] As described above, the present invention is a fragrance composition containing a compound represented by the general formula (I) and a compound represented by the general formula (II), which is a fragrance composition in which the mass ratio of the compound represented by the formula (I) to the compound represented by the formula (II) [compound represented by the formula (I): compound represented by the formula (II)] is 0.10:99.90 or more and 4.00:96.00 or less.

[0018]

Chemical formula

[0019] [In the above formulas (I) and (II), R 1 and R 3 are, independently of each other, an alkyl group having 1 to 5 carbon atoms, R 2 and R 4 are, independently of each other, a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.]

[0020] In the fragrance composition, the content of the compound of the formula (II) is preferably 96.00% by mass or more, more preferably 97.00% by mass or more, still more preferably 98.0% by mass or more, preferably 99.90% by mass or less, more preferably 99.80% by mass or less, still more preferably 99.75% by mass or less, from the viewpoint of imparting orris-like sweetness and volume, imparting persistence to the fragrance, and obtaining a well-balanced fragrance composition. From the above viewpoints, it 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, still more preferably 98.00% by mass or more and 99.75% by mass or less.

[0021] The mass ratio of the compound represented by the formula (I) to the compound represented by the formula (II) [compound represented by the formula (I): compound represented by the formula (II)] is 0.10:99.90 or more, preferably 0.20:99.80 or more, more preferably 0.25:99.75 or more, from the viewpoint of imparting orris-like sweetness and volume, imparting persistence to the fragrance, and obtaining a well-balanced fragrance composition. It is 4.00:96.00 or less, preferably 3.00:97:00 or less, 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.

[0022] The mass ratio of the compound represented by the formula (I) to the compound represented by the formula (II) [compound represented by the formula (I): compound represented by the 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, more preferably 0.25:99.75 or more and 2.00:98:00 or less, from the above viewpoints.

[0023] Furthermore, the mass ratio of the compound represented by the formula (I) to the compound represented by the formula (II) [compound represented by the formula (I): compound represented by the formula (II)] being 0.10:99.90 or more means that the mass ratio of the compound represented by the formula (I) / compound represented by the formula (II) is 0.10 / 99.90 or more, and the mass ratio of the compound represented by the formula (I) to the compound represented by the formula (II) [compound represented by the formula (I): compound represented by the formula (II)] being 4.00:96.00 or less means that the mass ratio of the compound represented by the formula (I) / compound represented by the formula (II) is 4.00 / 96.00 or less.

[0024] In the present specification, R 1 and R 3 Among them, the alkyl group having 1 to 5 carbon atoms refers to, for example, linear or branched alkyl groups such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, t-butyl group, n-pentyl group, i-pentyl group, sec-pentyl group, t-pentyl group, 2-methylbutyl group and the like. 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 still more preferably a t-butyl group.

[0025] In the present specification, R 2 and R 4 Among them, the alkyl group having 1 to 4 carbon atoms refers to, for example, linear or branched alkyl groups such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, t-butyl group and the like. The alkyl group having 1 to 4 carbon atoms is preferably an alkyl group having 1 to 3 carbon atoms, more preferably an alkyl group having 2 to 3 carbon atoms, and still more preferably an ethyl group in order to make the perfume composition of the present invention excellent in balance by imparting orris-like sweetness and volume of fragrance to amber-like and woody scents.

[0026] In the formula (I), in order for the perfume composition of the present invention to have an excellent balance in imparting orris-like sweetness and volume of fragrance to amber-like and woody fragrances, 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.

[0027] In the formula (I), in order for the perfume composition of the present invention to have an excellent balance in imparting orris-like sweetness and volume of fragrance to amber-like and woody fragrances, 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.

[0028] As the compound represented by the formula (I), for example, in order for the perfume composition of the present invention to have an excellent balance in imparting orris-like sweetness and volume of fragrance to amber-like and woody fragrances, the following R shown in Table 1 1 and R 2 compounds in combination are preferred, and it is even more preferred that R 1 is a t-butyl group and R 2 is an ethyl group.

[0029] [Table 1]

[0030] As the compound represented by the formula (I), for example, in order for the perfume composition of the present invention to have an excellent balance in imparting orris-like sweetness and volume of fragrance to amber-like and woody fragrances, the following compounds are preferred.

[0031] [Chemical formula]

[0032] The compound represented by the formula (I) may be a mixture of the following cis-isomer and trans-isomer, or may be any one of them.

[0033] [Chemical formula]

[0034] In the above formula (II), in order for the perfume composition of the present invention to have an excellent balance in imparting orris-like sweetness and volume of fragrance to amber-like and woody fragrances, R 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.

[0035] In the above formula (II), in order for the perfume composition of the present invention to have an excellent balance in imparting orris-like sweetness and volume of fragrance to amber-like and woody fragrances, R 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.

[0036] As the compound represented by the formula (II), for example, in order for the perfume composition of the present invention to have an excellent balance in imparting orris-like sweetness and volume of fragrance to amber-like and woody fragrances, the following R shown in Table 2 3 and R 4 in the combination of compounds are preferred, and R 3 is a t-butyl group, and R 4 is an ethyl group is even more preferred.

[0037] [Table 2]

[0038] As the compound represented by the formula (II), for example, in order for the perfume composition of the present invention to have an excellent balance in imparting orris-like sweetness and volume of fragrance to amber-like and woody fragrances, the following compounds are preferred.

[0039] [Chemical formula]

[0040] The compound represented by formula (II) may be a mixture of the following cis and trans isomers, or may be either one of them.

[0041]

Chemical formula

[0042] In the perfume composition of the present invention, in order for the perfume composition of the present invention to have an excellent balance in imparting orris-like sweetness and volume of fragrance to amber-like and woody fragrances, R 1 and R 3 are preferably t-butyl groups.

[0043] In the perfume composition of the present invention, in order for the perfume composition of the present invention to have an excellent balance in imparting orris-like sweetness and volume of fragrance to amber-like and woody fragrances, R 2 and R 4 are preferably methyl groups or ethyl groups.

[0044] In the perfume composition of the present invention, in order for the perfume composition of the present invention to have an excellent balance in imparting orris-like sweetness and volume of fragrance to amber-like and woody fragrances, R 1 and R 3 is a t-butyl group, and R 2 and R 4 are more preferably methyl groups or ethyl groups.

[0045] In the perfume composition of the present invention, the combination of the compound represented by the formula (I) and the compound represented by the formula (II) is, for example, 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 described 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 described in Table 2. The combination of the compound represented by the formula (I) and the compound represented by the formula (II) is preferably a combination of combination I-16 and combination II-16 so that the perfume composition of the present invention has an excellent balance in imparting an amber-like and woody scent with an orris-like sweetness and scent volume. That is, R 1 is a t-butyl group, R 2 is an ethyl group, R 3 is a t-butyl group, R 4 is an ethyl group is preferred.

[0046] The compound represented by the formula (I) can be produced, for example, by the method described in JP-A-8-27056.

[0047] The compound represented by the formula (I) can also be produced, for example, by the following method.

[0048]

Chemical formula

[0049] In the above formula (I) and formula (III), R 1 is an alkyl group having 1 to 5 carbon atoms, R 2 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0050] The method includes a step of obtaining a compound of formula (I) by oxidizing a compound of formula (III). For example, this step can be carried out by oxidizing the compound of formula (III) with an oxidizing agent (such as Dess-Martin periodinane), to obtain the compound of formula (I). The obtained compound of formula (I) can be separated and purified by distillation or column chromatography.

[0051] The compound represented by the formula (II) can be produced, for example, by the method described in JP-A-4-217937.

[0052] In addition, in order to make the perfume composition of the present invention excellent in balance by imparting orris-like sweetness and scent volume to amber-like and woody scents, it preferably further contains one or more of alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, and nitriles, other than the compound represented by the formula (I) and the compound represented by the formula (II).

[0053] In this specification, the "category" of each perfume means a single compound or a mixture of two or more compounds.

[0054] Examples of alcohols include aliphatic alcohols, terpene alcohols, aromatic alcohols, and other alcohols. Among these, aliphatic alcohols are preferred.

[0055] Examples of terpene alcohols include linalool, ethyl linalool, citronellol, hydroxycitronellol, geraniol, tetrahydrogeraniol, nerol, terpineol, α-terpineol, dihydromyrcenol, farnesol, nerolidol, cedrol, menthol, borneol, etc.

[0056] Examples of aromatic alcohols include phenylethyl alcohol, benzyl alcohol, dimethylbenzyl carbinol, phenylethyldimethyl carbinol, phenylhexanol, and the like.

[0057] Examples of aliphatic alcohols include cis-3-hexenol, 1-(2,2,6-trimethylcyclohexyl)-3-hexanol, Sandal Mysore 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), Undecabeltol (trade name, manufactured by Givaudan, 4-methyl-3-decen-5-ol), isobornylcyclohexanol, Terpyrosa (trade name, manufactured by Kao Corporation, 3,6-dimethyl-2-heptanol), and the like.

[0058] Examples of other alcohols include glycols such as dipropylene glycol, Florosa (chemical name: 4-methyl-2-(2-methylpropyl)tetrahydro-2H-4-pyranol, manufactured by Givaudan), maltol, ethylmaltol, and the like.

[0059] Examples of hydrocarbons include limonene, α-pinene, β-pinene, terpinene, cedrene, longifolene, valencene, and the like.

[0060] Examples of phenols include guaiacol, eugenol, dihydroeugenol, isoeugenol, thymol, p-cresol, vanillin, ethylvanillin, and the like.

[0061] Examples of esters include aliphatic carboxylic acid esters, aromatic carboxylic acid esters, and other carboxylic acid esters.

[0062] Examples of aliphatic carboxylic acids that form aliphatic carboxylic acid esters include linear and branched carboxylic acids having 1 to 18 carbon atoms. Among them, carboxylic acids having 1 to 6 carbon atoms such as formic acid, acetic acid, and propionic acid are preferred, and acetic acid is more preferred. Examples of aromatic carboxylic acids that form aromatic carboxylic acid esters include benzoic acid, anisic acid, phenylacetic acid, cinnamic acid, salicylic acid, anthranilic acid, and the like. Examples of alcohols that form aliphatic and aromatic esters include linear and branched aliphatic alcohols having 1 to 5 carbon atoms and the above-mentioned perfume ingredient alcohols.

[0063] Examples of formic acid esters include linalyl formate, citronellyl formate, geranyl formate, and the like.

[0064] Examples of acetic acid esters include ethyl acetate, isoamyl acetate (isopentyl acetate), benzyl acetate, hexyl acetate, phenyl acetate, p-cresyl acetate, cis-3-hexenyl acetate, linalyl acetate, citronellyl acetate, geranyl acetate, neryl acetate, terpinyl acetate, nopyl acetate, bornyl acetate, isobornyl acetate, acetyl eugenol, acetyl iso-eugenol, o-tert-butylcyclohexyl 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, etc.; examples of phenylacetic acid esters include phenylethyl phenylacetate, p-cresyl phenylacetate, and the like.

[0065] Examples of propionate esters include ethyl propionate, citronellyl propionate, tricyclodecenyl propionate, benzyl propionate, styrallyl propionate, herberid (trade name, manufactured by Firmenich, 2-[1-(3,3-dimethylcyclohexyl)ethoxy]-2-methylpropyl) propionate, and the like.

[0066] Examples of butyrate esters include citronellyl butyrate, dimethylbenzylcarbinyl n-butyrate, isoamyl n-butyrate, n-amyl n-butyrate, and the like; examples of isobutyrate esters include tricyclodecenyl isobutyrate, phenoxyethyl isobutyrate, and the like.

[0067] Examples of valerate esters include methyl valerate, ethyl valerate, butyl valerate, amyl valerate, benzyl valerate, phenylethyl valerate, and the like; examples of hexanoate esters include methyl hexanoate, ethyl hexanoate, allyl hexanoate, linalyl hexanoate, citronellyl hexanoate, and the like.

[0068] Examples of heptanoate esters include methyl heptanoate, allyl heptanoate, and the like.

[0069] Examples of nonenoate esters include methyl 2-nonenoate, ethyl 2-nonenoate, ethyl 3-nonenoate, and the like.

[0070] Examples of benzoate esters include methyl benzoate, benzyl benzoate, 3,6-dimethylbenzoate, and the like.

[0071] Examples of cinnamate esters include methyl cinnamate, benzyl cinnamate, and the like.

[0072] Examples of salicylate esters include methyl salicylate, n-hexyl salicylate, cis-3-hexenyl salicylate, cyclohexyl salicylate, benzyl salicylate (benzyl salicylate), and the like.

[0073] Furthermore, examples of the brassylate include ethylene brassylate.

[0074] Examples of the tiglate include geranyl tiglate, 1-hexyl tiglate, cis-3-hexenyl tiglate, etc.

[0075] Examples of the jasmonate include methyl jasmonate, etc.; examples of the dihydrojasmonate include MDJ (trade name, manufactured by Kao Corporation, methyl dihydrojasmonate, methyl (2-pentyl-3-oxocyclopentyl) acetate), etc.

[0076] Examples of the glycidate include methyl 2,4-dihydroxy-ethylmethylphenyl glycidate, 4-methylphenyl ethyl glycidate, etc.

[0077] Examples of the anthranilate include methyl anthranilate, ethyl anthranilate, dimethyl anthranilate, etc.

[0078] Examples of the glycolate include allyl cyclohexyl glycolate, etc.

[0079] Furthermore, examples of other esters include ethyl safuranate (trade name, manufactured by Dubodan, ethyl dihydrocyclogeranate), poarenate (trade name, manufactured by Kao Corporation, ethyl-2-cyclohexylpropionate), flutate (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 Dubodan, ethyl 2-methylpentanoate), ethyl 2-methylbutyrate, allyl cyclohexylpropionate, allyl-2-pentyloxy glycolate, etc.

[0080] Examples of carbonates include Refarm (trade name, manufactured by IFF, cis-3-hexenyl methyl carbonate), Jasmatclat (trade name, manufactured by Kao Corporation, methyl-cyclooctyl carbonate), Floramat (trade name, manufactured by Kao Corporation, ethyl-2-t-butylcyclohexyl carbonate), and the like.

[0081] 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-carboxyaldehyde), Cyclobertal (trade name, manufactured by Kao Corporation, dimethyl-3-cyclohexenyl-1-carboxyaldehyde), benzaldehyde, phenylacetaldehyde, phenylpropylaldehyde, cinnamic aldehyde, dimethyltetrahydrobenzaldehyde, Bourgeonal (trade name, manufactured by Givaudan, 3-(4-tert-butylphenyl)propanal), Lyrall (trade name, manufactured by IFF, hydroxymyrac aldehyde), Pollenal II (trade name, manufactured by Kao Corporation, 2-cyclohexylpropanal), Lilial (trade name, manufactured by Givaudan, p-tert-butyl-α-methylhydrocinnamic aldehyde), p-isopropyl-α-methylhydrocinnamic aldehyde, Floralozone (trade name, manufactured by IFF, 3-(o-(and p-)ethylphenyl)-2,2-dimethylpropionaldehyde), α-amylcinnamic aldehyde, α-hexylcinnamic aldehyde, Heliotropin (trade name, manufactured by Takasago International Corporation, 3,4-methylenedioxybenzaldehyde), Helional (trade name, manufactured by IFF, alpha-methyl-1,3-benzodioxole-5-propanal), Cantoxal (trade name, manufactured by IFF, 2-methyl-3-(paramethoxyphenyl)propanal), Aldehyde C-6 (trade name, manufactured by Kao Corporation, n-hexanal), and the like.

[0082] Examples of ketones include methyl heptenone, dimethyl octenone, 3-octanone, hexyl cyclopentanone, dihydro jasmon, Beloutone (trade name, 2,2,5-trimethyl-5-pentyl cyclopentanone manufactured by Firmenich), Nectaryl (trade name, 2-(2-(4-methyl-3-cyclohexen-1-yl)propyl) cyclopentanone manufactured by Givaudan), ionone, β-ionone, methyl ionone, methyl ionone-G, γ-methyl ionone, damascone, α-damascone, β-damascone, δ-damascone, isodamascone (trade name, 1-(2,4,4-trimethyl-2-cyclohexyl)-trans-2-butanone manufactured by Symrise), damasconone, Dynascone (trade name, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one manufactured by Firmenich), iron, Cashmeran (trade name, 1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-4H-indene-4-one manufactured by IFF), Iso-E-Super (trade name, 1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-ethan-1-one manufactured by IFF), Calone (trade name, 7-methyl-3,4-dihydro-2H-benzodioxepin-3-one manufactured by Firmenich), Carvone, menthone, acetyl cedrene, isolongifolanone, nutkatone, benzyl acetone, raspberry ketone, benzophenone, Tonalid (trade name, 6-acetyl-1,1,2,4,4,7-hexamethyl tetrahydronaphthalene manufactured by PFW), β-methyl naphthyl ketone, ethyl maltol, camphor, muscone, Muscenone (trade name, 3-methyl-5-cyclopentadecen-1-one manufactured by Firmenich), Civetone, Globanone (trade name, 8-cyclohexadecenone manufactured by Symrise), methyl nonyl ketone, cis-jasmon, para-amyl cyclohexanone (4-pentyl cyclohexanone), Tonaride (trade name, 1-(3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one manufactured by PFW Aromachemicals), and the like.Among them, from the viewpoint of emphasizing floral sweetness by blending with the perfume composition of the present invention, ionone, damascon, iso-E-super, or γ-methyl ionone is preferable.

[0083] Examples of acetals include acetaldehyde ethyl phenyl propyl acetal, citral diethyl acetal, phenylacetaldehyde glyceryl acetal, ethyl acetoacetate ethylene glycol acetal, Boazambrene 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), Floropal (trade name, manufactured by Symrise, 2,4,6-trimethyl-4-phenyl-1,3-dioxane), Magnolan (trade name, manufactured by Symrise, 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxane), and the like.

[0084] Examples of ethers include cedryl methyl ether, estragole, anethole, β-naphthyl methyl ether, β-naphthyl ethyl ether, limonene oxide, rose oxide, nerol oxide, 1,8-cineole, rose furan, Ambroxan (trade name, manufactured by Kao Corporation, [3aR-(3aα,5aβ,9aα,9bβ)]dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan), Herbavert (trade name, manufactured by Kao Corporation, 3,3,5-trimethylcyclohexyl ethyl ether), Galaxolide (trade name, manufactured by IFF, hexamethyl hexahydrocyclopentabenzopyran), phenylacetaldehyde dimethyl acetal, methyl isoeugenol, and the like.

[0085] Examples of carboxylic acids include benzoic acid, phenylacetic acid, cinnamic acid, hydrocinnamic acid, butyric acid, 2-hexenoic acid, and the like.

[0086] Examples of lactones include ambuletide, γ-decalactone, δ-decalactone, γ-valerolactone, γ-nonalactone, γ-undecalactone, δ-hexalactone, γ-jasmolactone, whisky lactone, coumarin, cyclopentadecanolide, cyclohexadecanolide, 11-oxahexadecanolide, butyrylidenephthalide, and the like.

[0087] Examples of nitriles include tridecene-2-nitrile, geranyl nitrile, citronellyl nitrile, dodecanenitrile, and the like.

[0088] In addition, in order to make the fragrance composition of the present invention excellent in balance by imparting orris-like sweetness and fragrance volume to amber-like and woody scents, it is also preferable to further contain natural essential oils and natural extracts.

[0089] Examples of natural essential oils and natural extracts include oils, concretes, absolutes, resinoids, oleoresins, tinctures, infusions, balsams, etc. of natural products such as orange, lemon, lime, bergamot, vanilla, mandarin, peppermint, spearmint, lavender, galbanum, chamomile, rosemary, eucalyptus, sage, basil, rose, rockrose, geranium, jasmine, ylang-ylang, anise, clove, ginger, nutmeg, cardamom, cedar, hinoki, vetiver, patchouli, hay, lemongrass, labdanum, grapefruit, elemi oil, bergamot oil, and the like.

[0090] In the perfume composition of the present invention, the total content of the compound represented by the formula (I) and the compound represented by the formula (II) can be appropriately selected depending on the type of compounded perfume, the type of target aroma, the strength of the aroma, etc. However, from the viewpoint of imparting an excellent aroma with a balance of orris-like sweetness and aroma volume to amber-like and woody scents, in the composition containing the perfume composition of the present invention, it is preferably 0.0001% by mass or more, more preferably 0.001% by mass or more, still more preferably 0.1% by mass or more, even more preferably 1% by mass or more, and preferably 99.99% by mass or less, more preferably 80% by mass or less, still more preferably 60% by mass or less, even more preferably 50% by mass or less, and 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, still more preferably 0.1% by mass or more and 60% by mass or less, even more preferably 1% by mass or more and 50% by mass or less.

[0091] The perfume composition of the present invention can be combined, as a base, with an oil agent that itself has no odor. Such an oil agent can uniformly mix the perfume components, make it easy to blend into the product, and easily impart an appropriate intensity of aroma. Examples of the oil agent include polyhydric alcohols such as ethylene glycol, propylene glycol, butylene glycol, and dipropylene glycol, esters such as isopropyl myristate, dibutyl adipate, and diethyl sebacate, hydrocarbons such as liquid paraffin and squalane, and surfactants such as polyoxyethylene alkyl ether and sorbitan fatty acid ester.

[0092] Among these, from the viewpoint of improving the solubility of all perfume components, polyhydric alcohols and esters are preferred as the oil agent, and dipropylene glycol and isopropyl myristate are more preferred. The content of such an oil agent in the perfume composition is preferably 0.01% by mass or more, more preferably 1% by mass or more, still more preferably 5% by mass or more, and preferably 95% by mass or less, more preferably 90% by mass or less, still more preferably 80% by mass or less.

[0093] The present invention also provides a detergent composition containing the perfume composition of the present invention, a cosmetic containing the perfume composition of the present invention, and a fiber treatment composition containing the perfume composition of the present invention.

[0094] As the detergent composition of the present invention, a body detergent composition, a fabric detergent composition, and a hard surface detergent composition are preferable, a body detergent composition and a fabric detergent composition are more preferable, and a fabric detergent composition is even more preferable.

[0095] Examples of the body detergent composition include a skin detergent composition, a hair detergent composition, and a soap composition, and a skin detergent composition is preferable.

[0096] Examples of the hard surface detergent composition include an all-purpose cleaner and a dishwashing detergent composition.

[0097] As the fiber treatment composition of the present invention, a softener composition is preferable.

[0098] As the cosmetic excluding the detergent composition of the present invention, perfume, emulsion, lotion, and sunscreen are preferable, and perfume is more preferable.

[0099] The detergent composition of the present invention preferably contains an anionic surfactant in addition to the perfume composition of the present invention, and further, a nonionic surfactant, a pH adjuster, a viscosity adjuster, a solvent, an oil agent, a preservative, water, etc. can be blended.

[0100] The fiber treatment composition of the present invention preferably contains a cationic surfactant in addition to the perfume composition of the present invention, and further, a pH adjuster, a solvent, an oil agent, a preservative, water, etc. can be blended.

[0101] The perfume of the present invention can contain a solvent, water, etc. in addition to the perfume composition of the present invention.

[0102] Further, the present invention is a composition comprising a compound represented by the general formula (I) and a compound represented by the general formula (II), A method of using, as a flavoring component, a composition in which the mass ratio of the compound represented by the formula (I) to the compound represented by the formula (II) [compound represented by the formula (I): compound represented by the formula (II)] is 0.10:99.90 or more and 4.00:96.00 or less.

[0103] The preferred mass ratio of the compound represented by the formula (I) to the compound represented by the formula (II) [compound represented by the formula (I): compound represented by the formula (II)] in the above method is as described above.

[0104]

Chemical formula

[0105] [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.] R 1 、R 2 、R 3 、R 4 The preferred groups of are as described above.

[0106] As a method of using the above composition of the present invention as a fragrance component, specifically, it is a method of using it as a fragrance component of a fragrance composition, a detergent composition, a cosmetic or a fiber treatment composition. As the detergent composition, a body detergent composition, a laundry detergent composition, and a hard surface detergent composition are preferable, a body detergent composition and a laundry detergent composition are more preferable, and a laundry detergent composition is even more preferable. Examples of the body detergent composition include a skin detergent composition and a hair detergent composition, and a skin detergent composition is preferable. Examples of the hard surface detergent composition include an all-purpose cleaner and a dishwashing detergent composition. As the cosmetic, perfume is preferable. As the fiber treatment composition, a softener composition is preferable.

[0107] In the above method of use, the composition is preferably used in a detergent composition, a cosmetic or a softener composition in an amount of 0.0001% by mass or more, more preferably 0.001% by mass or more, and preferably 30% by mass or less, more preferably 20% by mass or less, still more preferably 10% by mass or less, 1% by mass or less, and more preferably 0.1% by mass or less. By using in this amount, as a fragrance material, it is possible to impart a new impression of excellent balance with amber-like and woody scents, with orris-like sweetness and scent volume.

[0108] In the above method of use, the composition may be used in combination with an oil agent that itself has no odor. The oil agent is the same as that described in the fragrance composition. Also, in the above method of use, the composition may be used in combination with other commonly used fragrance components and compounded fragrances of a desired composition as other fragrances. Such other fragrances are the same as those described in the fragrance composition.

[0109] The present invention includes the following aspects. <1> A fragrance composition comprising a compound represented by the general formula (I) and a compound represented by the general formula (II), A perfume composition in which the mass ratio of the compound represented by the formula (I) to the compound represented by the formula (II) [compound represented by the formula (I): compound represented by the formula (II)] is 0.10:99.90 or more and 4.00:96.00 or less.

[0110] [Chemical formula]

[0111] [In the formulas (I) and (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.]

[0112] <2> The perfume composition according to <1>, wherein R 1 and R 3 are t-butyl groups.

[0113] <3> The perfume composition according to <1> or <2>, wherein R 2 and R 4 are a methyl group or an ethyl group.

[0114] <4> The perfume composition according to any one of <1> to <3>, wherein R 1 and R 3 are t-butyl groups, and R 2 and R 4 are ethyl groups.

[0115] <5> The perfume composition according to any one of <1> to <4>, wherein the mass ratio of the compound represented by the formula (I) to the compound represented by the formula (II) [compound represented by the formula (I): compound represented by the formula (II)] is 0.20:99.80 or more and 3.00:97.00 or less.

[0116] <6> The mass ratio of the compound represented by the formula (I) to the compound represented by the formula (II) [compound represented by the formula (I): compound represented by the formula (II)] in the perfume composition is 0.25:99.75 or more and 2.00:98.00 or less, and the perfume composition according to any one of <1> to <5>.

[0117] <7> In the perfume composition, the total content of the compound represented by the formula (I) and the compound represented by the formula (II) is 0.0001% by mass or more and 99.99% by mass or less, and the perfume composition according to any one of <1> to <6>.

[0118] <8> In the perfume composition, the total content of the compound represented by the formula (I) and the compound represented by the formula (II) is 0.001% by mass or more and 80% by mass or less, and the perfume composition according to any one of <1> to <7>.

[0119] <9> In the perfume composition, the total content of the compound represented by the formula (I) and the compound represented by the formula (II) is more preferably 0.1% by mass or more and 60% by mass or less, and the perfume composition according to any one of <1> to <8>.

[0120] <10> In the perfume composition, the total content of the compound represented by the formula (I) and the compound represented by the formula (II) is 1% by mass or more and 50% by mass or less, and the perfume composition according to any one of <1> to <9>.

[0121] <11> In addition to the compound represented by the formula (I) and the compound represented by the formula (II), the perfume composition according to any one of <1> to <10> further contains one or more of alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, and nitriles.

[0122] <12> In addition to the compound represented by the formula (I) and the compound represented by the formula (II), the perfume composition according to any one of <1> to <11> further contains a natural essential oil or a natural extract. <13> A cosmetic containing the perfume composition according to any one of <1> to <12>.

[0123] <14> A detergent composition containing the perfume composition according to any one of <1> to <12>.

[0124] <15> A fiber treatment agent composition containing the perfume composition according to any one of <1> to <12>.

[0125] <16> A composition comprising a compound represented by the general formula (I) and a compound represented by the general formula (II), A method of using, as a fragrance component, a composition in which the mass ratio of the compound represented by the formula (I) to the compound represented by the formula (II) [compound represented by the formula (I): compound represented by the formula (II)] is 0.10:99.90 or more and 4.00:96.00 or less.

[0126]

Chemical formula

[0127] [In the above formulas (I) and (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.]

[0128] In the following examples, “%” is “mass %” unless otherwise specified. Also, the mass of the catalyst is the mass in the dry state.

[0129] <Gas chromatography apparatus and analysis conditions> GC apparatus: 7890B manufactured by Agilent Technologies, hydrogen flame ionization detector

[0130] 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, Inc.) was used.

[0131] When analyzing the cis and trans isomers, DB-WAX (capillary column, polyethylene glycol, inner diameter 0.25 mm, length 30 m, film thickness 0.25 μm, manufactured by Agilent Technologies, Inc.) was used.

[0132] Carrier gas: He, 1.5 mL / min Injection conditions: 300 °C, split ratio 100 / 1 Injection volume: 1 μL Detection conditions: FID method, 300 °C Column temperature conditions: Starting from 80 °C, the temperature was raised to 300 °C at a rate of 10 °C / min. Then, it was held at 300 °C for 10 minutes.

[0133] [Production Example 1] Production of 1-(2-t-butylphenyloxy)-2-butanol (3)

[0134] [Chemical formula]

[0135] To a 1 L round-bottom flask equipped with a Dimroth condenser and a dropping funnel, under a nitrogen stream, 2-t-butylphenol (1) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., 350 g) and 35 g of a 48% aqueous sodium hydroxide solution (manufactured by Kanto Chemical Co., Inc.) were added and heated to 80 °C. To this, 1,2-butylene oxide (2) (manufactured by Tokyo Chemical Industry Co., Ltd., 176 g) was added dropwise over about 2 hours, and then stirred at 80 °C for 5 hours. After cooling the reaction mixture to room temperature (25 °C), the lower-layer aqueous sodium hydroxide solution was separated from the organic layer, and the organic layer was distilled to obtain 1-(2-t-butylphenyloxy)-2-butanol (3) with a yield of 96%.

[0136] [Production Example 2] Production of 1-(2-t-butylcyclohexyloxy)-2-butanol (4)

[0137]

Chem.

[0138] Into a 500 ml autoclave, 1-(2-t-butylphenyloxy)-2-butanol (3) (250 g) obtained in Production Example 1, activated carbon supported palladium catalyst (manufactured by N.E. Chemcat Corporation, trade name: S type, 50% water-containing product, palladium loading 2%, 4.75 g), and activated carbon supported ruthenium catalyst (manufactured by N.E. Chemcat Corporation, 50% water-containing product, ruthenium loading 5%, 0.25 g) were added, and the reaction was carried out at a hydrogen pressure of 2.0 MPa and 190 °C for 6 hours.

[0139] After completion of the reaction, the catalyst was filtered and the filtrate was distilled to obtain 1-(2-t-butylcyclohexyloxy)-2-butanol (4) with a yield of 70% and a purity of 100%. As a result of analyzing the product by gas chromatography, the mass ratio of cis to trans was cis:trans = 57:43.

[0140]

Chem.

[0141] [Production Example 3] Production of 1-(2-t-butylcyclohexyloxy)butan-2-one (5)

[0142]

Chem.

[0143] 1-(2-t-Butylcyclohexyloxy)-2-butanol (4) (2 g) obtained in Production Example 2 was dissolved in dichloromethane (35.0 mL), and Dess-Martin periodinane (4.5 g) was added at 0 °C. After 10 minutes, the cooling bath was removed, the reaction mixture was warmed to room temperature (25 °C), and stirred for 30 minutes to conduct the reaction. As a post-treatment, a saturated aqueous sodium thiosulfate solution was added to stop the reaction. The mixture was extracted with diethyl ether, dried over sodium sulfate, filtered, and then the solvent was distilled off 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%.

[0144] [Example 1] To 19 mg of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) obtained in Production Example 3, 9.981 g of 1-(2-t-butylcyclohexyloxy)-2-butanol (4) obtained in Production Example 2 was added and mixed to obtain a flavor 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).

[0145] [Example 2] To 21 mg of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) obtained in Production Example 3, 9.979 g of 1-(2-t-butylcyclohexyloxy)-2-butanol (4) (cis / trans mass ratio = 57:43) obtained in Production Example 2 was added and mixed to obtain a flavor 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).

[0146] [Example 3] To 29 mg of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) obtained in Production Example 3, 9.971 g of (1-(2-t-butylcyclohexyloxy)-2-butanol (4) obtained in Production Example 2 was added 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 = 0.29 / 99.71).

[0147] [Example 4] To 0.112 g of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) obtained in Production Example 3, 9.888 g of (1-(2-t-butylcyclohexyloxy)-2-butanol (4) obtained in Production Example 2 was added 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).

[0148] [Example 5] To 30 mg of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) obtained in Production Example 3, 0.97 g of (1-(2-t-butylcyclohexyloxy)-2-butanol (4) obtained in Production Example 2 was added 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 = 3.00 / 97.00).

[0149] [Comparative Example 1] To 48.5 mg of 1-(2-t-butylcyclohexyloxy)butan-2-one (5) obtained in Production Example 3, 0.9515 g of (1-(2-t-butylcyclohexyloxy)-2-butanol (4) obtained in Production Example 2 was added 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 = 4.85 / 95.15).

[0150] [Sensory Evaluation] The odors of the fragrance compositions obtained in Examples 1 to 5 and Comparative Example 1 were evaluated by three professional panelists. The evaluation was carried out using odor test strips (made of large-sized Japanese paper, 150 mm × 7 mm). Examples 1 to 5 and Comparative Example 1 with different isomer ratios were each perfumed at the tip of the odor test strip and evaluated indoors. The sensory evaluation was carried out from the viewpoints of the characteristics and intensity of the odor. The characteristics and intensity of the odor were relatively evaluated on a five-point scale, and the larger the numerical value, the more preferable. Regarding the residual fragrance, it was confirmed how many hours the fragrance lasted, and the elapsed time and the odor intensity at that time were relatively evaluated on a ten-point scale, and the larger the numerical value, the more preferable. Also, the quality and characteristics of the overall scent felt by the three professional panelists in the sensory evaluation were described. The results obtained are shown in Tables 3 and 4.

[0151] From the viewpoints of the characteristics and intensity of the odor, a ranking was made according to the following criteria as a comprehensive evaluation of the usefulness of the fragrance as a fragrance material. A: Extremely interesting and highly valuable as a fragrance material B: Sufficiently valuable as a fragrance material C: Almost sufficiently valuable as a fragrance material D: Somewhat low value as a fragrance material [Table 3]

[0152] [Table 4]

[0153] [Evaluation result] As shown in Tables 3 and 4, the perfume composition of the present invention is an excellent perfume composition with an excellent balance that imparts orris-like sweetness and volume to the original amber-like and wood-like (and camphor-like) scents.

Claims

1. A fragrance composition comprising a compound represented by the general formula (I) and a compound represented by the general formula (II), wherein the mass ratio of the compound represented by the formula (I) to the compound represented by the formula (II) [compound represented by the formula (I): compound represented by the formula (II)] is 0.10:99.90 or more and 4.00:96.00 or less. 【Chemical 18】 [In the above formulas (I) and (II), R 1 and R 3 are each independently an alkyl group having 1 to 5 carbon atoms, R 2 and R 4 are, independently of each other, a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.]

2. R 1 and R 3 is a t-butyl group, the perfume composition according to claim 1.

3. R 2 and R 4 is a methyl group or an ethyl group, and the perfume composition according to claim 1 or 2.

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

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

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

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

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

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

10. A composition comprising a compound represented by the general formula (I) and a compound represented by the general formula (II), wherein the mass ratio of the compound represented by the formula (I) to the compound represented by the formula (II) [compound represented by the formula (I): compound represented by the formula (II)] is 0.10:99.90 or more and 4.00:96.00 or less, and the method of using the composition as a flavoring ingredient. 【Chemical Formula 19】 [In the above formulas (I) and (II), R 1 and R 3 are, independently of each other, an alkyl group having 1 to 5 carbon atoms, R 2 and R 4 are, independently of each other, a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.]

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