α-Hydroxyisobutyric acid ester compound and fragrance composition

Abstract

This fragrance composition contains a compound represented by formula (1) as an active ingredient. (In formula (1), R1 is a C7-20 chain hydrocarbon group, can be linear or branched, and can be a saturated group or an unsaturated group. If unsaturated, the group can have one or more carbon-carbon double bonds or carbon-carbon triple bonds.)

Description

[Technical field]

[0001] The present invention relates to an α-hydroxyisobutyric acid ester compound and a fragrance composition. [Background technology]

[0002] It is known that isobutyric acid esters include compounds useful as flavorings. For example, Non-Patent Document 1 describes that various isobutyric acid esters are mainly used as flavors, and specifically, it describes that methyl isobutyrate is sweet apricot-like, propyl isobutyrate is heavy pineapple-like, butyl isobutyrate is fresh apple and banana-like, and isoamyl isobutyrate is sweet apricot and pineapple-like, all of which are flavor materials with a fruity aroma. Furthermore, Patent Document 1 discloses that linear or branched alkyl esters of α-alkoxyisobutyric acid having 4 to 12 carbon atoms are useful as isobutyric acid esters having a bond to oxygen at the α-position, and describes that normal hexyl α-ethoxyisobutyrate has a lavender-like odor.

[0003] There are many known substances that are α-hydroxyisobutyric acid esters of chain higher alcohols having 7 or more carbon atoms, and for example, Patent Document 2 discloses that alkyl esters of α-hydroxyisobutyric acid having 8 to 20 carbon atoms are useful as lubricating oils and resin additives, and can be synthesized from acetone cyanohydrin and the corresponding alcohol in the presence of hydrochloric acid. Specifically, 2-ethylhexyl ester, a mixture of decyl ester and dodecyl ester, and a mixture of hexadecyl ester, octadecyl ester and eicosa ester of α-hydroxyisobutyric acid are disclosed.

[0004] In addition, Non-Patent Document 2 discloses that octyl α-hydroxyisobutyrate can be selectively synthesized by reacting α-hydroxyisobutyric acid with octyl alcohol in the presence of a special catalyst. Non-Patent Document 3 discloses that nonanyl α-hydroxyisobutyrate can be synthesized from α-hydroxyisobutyric acid and nonanyl alcohol in the presence of an acid catalyst. Patent Document 3 discloses that decyl α-hydroxyisobutyrate is useful as a raw material for surfactants. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] U.S. Pat. No. 3,368,943 [Patent Document 2] Czechoslovak Patent No. 240,718 [Patent Document 3] U.S. Patent No. 5,260,051 [Non-patent literature]

[0006] [Non-Patent Document 1] "Synthetic Fragrances: Chemistry and Product Knowledge, Revised and Expanded Edition," Chemical Daily, 2016, pp. 580-582 [Non-Patent Document 2] Organic Letters (2005), 7(22), 5047-5050. [Non-Patent Document 3] Zhurnal Organicheskoi Khimii (1971), 7(9), 1875-8. Summary of the Invention [Problem to be solved by the invention]

[0007] The problem to be solved by the present invention is to provide an α-hydroxyisobutyric acid ester compound that is useful as a fragrance and a blended fragrance material. Another problem to be solved by the present invention is to provide a fragrance composition containing the α-hydroxyisobutyric acid ester compound as an active ingredient, and use of the compound as a fragrance. [Means for solving the problem]

[0008] The present inventors synthesized various compounds and conducted extensive research into their odors, and found that specific ester compounds of α-hydroxyisobutyric acid are useful as fragrances and blended fragrance materials. That is, the present invention is as follows.

[0009] <1> A fragrance composition comprising a compound represented by formula (1) as an active ingredient. [ka] (In formula (1), R 1 represents a chain hydrocarbon group having 7 to 20 carbon atoms, which may be linear or branched, and may be a saturated or unsaturated group. If it is an unsaturated group, it may have one or more carbon-carbon double bonds or carbon-carbon triple bonds. <2> In formula (1), R 1 is a straight-chain hydrocarbon group, <1> The fragrance composition according to claim 1. <3> In formula (1), R 1 is a branched hydrocarbon group, <1> The fragrance composition according to claim 1. <4> In formula (1), R 1 has at least one quaternary carbon atom, <3> The fragrance composition according to claim 1. <5> In formula (1), R 1 is a hydrocarbon group having a carbon-carbon unsaturated bond, <1> The fragrance composition according to claim 1. <6> In formula (1), R 1 is a hydrocarbon group having one or more carbon-carbon double bonds, <5> The fragrance composition according to claim 1. <7> In formula (1), R1 is a branched hydrocarbon group, <5> or <6> The fragrance composition according to claim 1. <8> A compound represented by formula (2). [ka] (In formula (2), R 2 is a saturated branched chain hydrocarbon group having 7 to 20 carbon atoms, except for the 2-ethylhexyl group. <9> In formula (2), R 2 has at least one quaternary carbon atom, <8> The compound according to claim 1, <10> A compound represented by formula (3). [ka] (In formula (3), R 3 represents an unsaturated chain hydrocarbon group having 7 to 20 carbon atoms. <11> In formula (3), R 3 is a hydrocarbon group having at least one carbon-carbon double bond. <10> The compound according to claim 1, <12> In formula (3), R 3 is a branched hydrocarbon group, <10> or <11> The compound according to claim 1, Effect of the Invention

[0010] According to the present invention, it is possible to provide an α-hydroxyisobutyric acid ester compound that is useful as a fragrance or blended fragrance material. Furthermore, according to the present invention, it is possible to provide a fragrance composition containing an α-hydroxyisobutyric acid ester compound as an active ingredient. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0011] [Fragrance composition and use] The fragrance composition of the present invention contains a compound represented by the following formula (1) as an active ingredient. Although there have been reports on α-hydroxyisobutyric acid ester compounds, there has been no description in the prior art of the unique scent of α-hydroxyisobutyric acid esters.

[0012] The present invention will be described in detail below. <Compound represented by formula (1)> The compound used in the fragrance composition of the present invention is represented by the following formula (1). [ka] (In formula (1), R 1 represents a chain hydrocarbon group having 7 to 20 carbon atoms, which may be linear or branched, and may be a saturated or unsaturated group. If it is an unsaturated group, it may have one or more carbon-carbon double bonds or carbon-carbon triple bonds.

[0013] In formula (1), R 1 is a chain hydrocarbon group having 7 to 20 carbon atoms, and preferably a chain hydrocarbon group having 7 to 15 carbon atoms. R 1 When is a saturated chain hydrocarbon group, it is preferably a saturated branched chain hydrocarbon group having 7 to 20 carbon atoms, and more preferably a saturated branched chain hydrocarbon group having 7 to 10 carbon atoms. R 1 When is an unsaturated chain hydrocarbon group, it is preferably an unsaturated chain hydrocarbon group having 7 to 20 carbon atoms, and more preferably an unsaturated chain hydrocarbon group having 8 to 15 carbon atoms. In formula (1), R 1Specific examples of the aryl groups include normal heptyl group, heptan-2-yl group, heptan-3-yl group, 2-methylhexyl group, 2-ethylpentyl group, 2,4-dimethylpentyl group, 2,2-dimethylpentyl group, 2,4-dimethylpentan-3-yl group, 5-methylhexan-2-yl group, normal octyl group, octan-2-yl group, octan-3-yl group, 2-ethylhexyl group, 2-ethyl-4-methylpentyl group, 2,2-dimethylhexyl group, 2,2,4-trimethylpentyl group, 4,4-dimethylhexan-2-yl group, 3,4-dimethyl Hexan-2-yl group, 6-methylheptan-2-yl group, 5-methylheptan-4-yl group, 5-methylheptan-3-yl group, n-nonyl group, nonan-2-yl group, nonan-3-yl group, 7-methyloctyl group, 6-methyloctane-2-yl group, 2,6-dimethylheptyl group, 2,6-dimethylheptane-4-yl group, 3,5,5-trimethylhexyl group, n-decyl group, 8-methylnonyl group, 3-propylheptyl group, 3,7-dimethyloctyl group, 2-ethyl-5-methylheptyl group, 4,7-dimethyloctane-3-yl group, 2 ,3,5-trimethylheptyl group, 2,5,6-trimethylheptyl group, 3,5,5-trimethylheptyl group, n-undecyl group, undecane-2-yl group, n-dodecyl group, 4,8-dimethyldecyl group, 5,9-dimethyldecyl group, 3,4,5,6,6-pentamethylheptane-2-yl group, 11-methyldodecyl group, 6,10-dimethylundecane-2-yl group, 3,7,9-trimethyldecyl group, n-tetradecyl group, 2,6,10-trimethylundecanyl group, 3,7,11-trimethyldodecadecyl group, n-hexadecyl group, normal octadecyl group, 6,10,14-trimethylpentadecan-2-yl group, normal eicosyl group, 3,7,11,15-tetramethylhexadecyl group, 1-octen-3-yl group, 1-nonen-3-yl group, 6-methyl-5-hepten-2-yl group, 5-methyl-2-hepten-4-yl group, 4,4-dimethyl-5-hexen-2-yl group, 6-nonenyl group, 2,6-nonadienyl group, 3,6-nonadienyl group, 2,6-dimethyl-5-heptenyl group, 9-decenyl group, 3,7-dimethyl-6-octenyl group, 3,7-dimethyl-2,6-Octadienyl group, 2-isopropenyl-5-methyl-4-hexenyl group, 2-isopropyl-5-methyl-2-hexenyl group, 4,7-dimethyl-6-octen-3-yl group, 2,5,6-trimethyl-4-heptenyl group, 3,5,5-trimethyl-2,6-heptadienyl group, 9-undecenyl group, 10-undecenyl group, 4-methyl-3-decen-5-yl group , 4,8-dimethyl-4,9-decadienyl group, 5,9-dimethyl-4,8-decadienyl group, 3,5,6,6-tetramethyl-4-methyleneheptan-2-yl group, 6,10-dimethyl-5,9-undecadien-2-yl group, 3,7,9-trimethyl-2,6-decadienyl group, 2,6,10-trimethyl-9-undecenyl group, 2,6,10-trimethyl-5,9 -undecadienyl group, (E)-3,7,11-trimethyl-6,10-dodecadienyl group, (Z)-3,7,11-trimethyl-6,10-dodecadienyl group, (2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl group, (2E,6Z)-3,7,11-trimethyl-2,6,10-dodecatrienyl group, (2Z,6Z)-3,7,11-trimethyl-2,6,10-dodecatrienyl group, Examples of the methyl-2,6,10-dodecatrienyl group include a (2Z,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl group, a 6,10,14-trimethyl-5,9,13-pentadecatrien-2-yl group, an (E)-3,7,11,15-tetramethyl-2-hexadecenyl group, and a (Z)-3,7,11,15-tetramethyl-2-hexadecenyl group.

[0014] R 1 When the group has one or more carbon-carbon double bonds, the compounds of formula (1) include any one or mixture of the resulting stereoisomers in any ratio. 1 When the group has one or more asymmetric carbon atoms, the compound represented by formula (1) includes any one or a mixture of the resulting optical isomers in any ratio.

[0015] The compound represented by the above formula (1) is useful as a fragrance or blended fragrance material, and has a floral odor. In addition, depending on the alkyl group (R) in the ester moiety, it can also exhibit woody, fruity, spicy, green, or other odors. Preferably, R 1 The group is a saturated straight chain hydrocarbon group. Preferably, R 1 The group is a saturated branched hydrocarbon group. Preferably, R 1 The group is a saturated branched hydrocarbon group having at least one quaternary carbon atom. Preferably, R 1 The group is a hydrocarbon group having a carbon-carbon unsaturated bond. Preferably, R 1 The group is a branched hydrocarbon group having a carbon-carbon unsaturated bond. Preferably, R 1 The group is a hydrocarbon group having one or more carbon-carbon double bonds. Preferably, R 1 The group is a branched hydrocarbon group having one or more carbon-carbon double bonds. Particularly preferably, R 1 The group is a 5-methylhexan-2-yl group. Particularly preferably, R 1 The group is a normal octyl group. Particularly preferably, R 1 The group is an octan-3-yl group. Particularly preferably, R 1 The group is a 6-methylheptan-2-yl group. Particularly preferably, R 1 The group is a 2-ethylhexyl group. Particularly preferably, R 1 The group is a 3,5,5-trimethylhexyl group. Particularly preferably, R 1 The group is a 3,7-dimethyloctyl group. Particularly preferably, R 1 The group is a 1-octen-3-yl group. Particularly preferably, R1 The group is a 3,7-dimethyl-6-octenyl group. Particularly preferably, R 1 The group is a (2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl group. Particularly preferably, R 1 The group is a (2E,6Z)-3,7,11-trimethyl-2,6,10-dodecatrienyl group. Particularly preferably, R 1 The group is a (2Z,6Z)-3,7,11-trimethyl-2,6,10-dodecatrienyl group. Particularly preferably, R 1 The group is a (2Z,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl group.

[0016] In the present invention, examples of the compound represented by formula (1) include compounds represented by any of the following formulas (1-1) to (1-86). The compound represented by formula (1) is preferably a compound represented by any of the following formulas (1-9), (1-13), (1-14), (1-18), (1-33), (1-56), (1-57), and (1-84).

[0017] [ka]

[0018] [ka]

[0019] [ka]

[0020] [ka]

[0021] [ka]

[0022] [ka]

[0023] [ka]

[0024] [ka]

[0025] [ka]

[0026] [ka]

[0027] [ka]

[0028] Exemplary compounds containing a double bond represented by a crossed double line represent both the trans (E) and cis (Z) stereoisomers resulting from the double bond.

[0029] The compound represented by formula (1) is useful as a fragrance since it has an excellent fragrance by itself as described below. Generally, fragrances are rarely used as single items, but are often used as blended fragrances (fragrance compositions) in which multiple fragrances are blended according to a purpose. The compound represented by formula (1) is useful as a fragrance (also called a "blended fragrance material") to be blended in a blended fragrance (fragrance composition), and the fragrance composition of the present invention contains the compound represented by formula (1) as an active ingredient. As a fragrance, the compound represented by the above formula (1) may be used alone or in combination of two or more kinds. In addition, the compound represented by formula (1) does not exclude the inclusion of small amounts of impurities, by-products, contaminants, etc., within the scope that does not impair the effects of the present invention.

[0030] The compound represented by formula (1) has a floral odor as well as a woody, fruity, spicy, green, or other odor, and is also excellent in diffusibility. The compound represented by formula (1) may be used alone as a fragrance to impart an odor to various cosmetics, health and hygienic materials, medicines, daily necessities, foods, and the like, or the compound represented by formula (1) may be mixed with other blended fragrance materials, etc. to prepare a fragrance composition (blended fragrance) described below, which is then blended into various products to impart an odor. Among these, from the viewpoint of obtaining a desired odor, it is preferable to blend the compound represented by formula (1) as a blended fragrance material into a fragrance composition to prepare a fragrance composition containing the compound represented by formula (1) as an active ingredient, and blend the fragrance composition into a product to impart an odor.

[0031] <Fragrance composition> The fragrance composition (blended fragrance) of the present invention contains a compound represented by formula (1) as an active ingredient. There are no particular limitations on the composition as long as it contains at least one type of compound represented by formula (1), and it may contain two or more types of compounds represented by formula (1). The fragrance composition of the present invention may contain the compound represented by formula (1) as an active ingredient, and other ingredients are not particularly limited, but it is preferable that the fragrance composition further contains other blended fragrance materials (hereinafter also referred to as "conventional fragrances"). It should be noted that a "fragrance composition (blended fragrance)" is a composition that imparts a fragrance when added to various cosmetics, pharmaceuticals, foods, beverages, etc., or a composition that can be used as such in perfumes, etc., and may contain additives such as solvents as necessary in addition to conventional fragrances. The amount of the compound represented by formula (1) to be blended varies depending on the type of compound, the type and intensity of the desired fragrance, etc., but the amount of the compound represented by formula (1) in the fragrance composition is preferably 0.001 mass% or more, more preferably 0.01 mass% or more, even more preferably 0.1 mass% or more, and is preferably 90 mass% or less, more preferably 70 mass% or less, even more preferably 50 mass% or less.

[0032] The conventional fragrance is not particularly limited as long as it is a conventionally known fragrance component, and a wide range of fragrances can be used. For example, the following can be selected and used alone or in any mixture of two or more kinds in any ratio: For example, hydrocarbons such as limonene, α-pinene, β-pinene, terpinene, cedrene, longifolene, and valencene; linalool, citronellol, geraniol, nerol, terpineol, dihydromyrcenol, ethyl linalool, farnesol, nerolidol, cis-3-hexenol, cedrol, menthol, borneol, β-phenylethyl alcohol, benzyl alcohol, phenylhexanol, 2,2,6-trimethylcyclohexyl-3-hexanol, 1-(2-t-butylcyclohexyloxy)-2-butanol, 4- Alcohols such as isopropylcyclohexanemethanol, 4-t-butylcyclohexanol, 4-methyl-2-(2-methylpropyl)tetrahydro-2H-pyran-4-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, isocamphylcyclohexanol, and 3,7-dimethyl-7-methoxyoctan-2-ol; phenols such as eugenol, thymol, and vanillin;Linalyl formate, citronellyl formate, geranyl formate, n-hexyl acetate, cis-3-hexenyl acetate, linalyl acetate, citronellyl acetate, geranyl acetate, neryl acetate, terpinyl acetate, nopyr acetate, bornyl acetate, isobornyl acetate, ot-butylcyclohexyl acetate, pt-butylcyclohexyl acetate, tricyclodecenyl acetate, benzyl acetate, styraryl acetate, cinnamyl acetate, dimethyl benzyl acetate, Dimethylbenzylcarbinyl acetate, 3-pentyltetrahydropyran-4-yl acetate, citronellyl propionate, tricyclodecenyl propionate, allyl cyclohexyl propionate, ethyl 2-cyclohexyl propionate, benzyl propionate, citronellyl butyrate, dimethylbenzylcarbinyl n-butyrate, tricyclodecenyl isobutyrate, methyl 2-nonenoate, methyl benzoate, benzyl benzoate, methyl cinnamate, methyl salicylate, n-hexyl salicylate esters such as cis-3-hexenyl salicylate, geranyl tiglate, cis-3-hexenyl tiglate, methyl jasmonate, methyl dihydrojasmonate, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, ethyl methylphenylglycidate, methyl anthranilate, and flutate; n-octanal, n-decanal, n-dodecanal, 2-methylundecanal, 10-undecenal, citronellal, citral, hydroxycitronellal, dimethyltetrahydrobenzaldehyde, and the like. aldehydes such as cinnamic aldehyde, 4(3)-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde, 2-cyclohexylpropanal, p-butyl-α-methylhydrocinnamic aldehyde, p-isopropyl-α-methylhydrocinnamic aldehyde, p-ethyl-α,α-dimethylhydrocinnamic aldehyde, α-amylcinnamic aldehyde, α-hexylcinnamic aldehyde, piperonal, and α-methyl-3,4-methylenedioxyhydrocinnamic aldehyde;Methylheptenone, 4-methylene-3,5,6,6-tetramethyl-2-heptanone, amylcyclopentanone, 3-methyl-2-(cis-2-penten-1-yl)-2-cyclopenten-1-one, methylcyclopentenolone, rose ketone, gamma-methylionone, alpha-ionone, carvone, menthone, camphor, nootkatone, benzylacetone, anisylacetone, methyl beta-naphthyl ketone, 2,5-dimethyl-4-hydroxy-3(2H)-furanone Ketones such as maltol, 7-acetyl-1,2,3,4,5,6,7,8-octahydro-1,1,6,7-tetramethylnaphthalene, muscone, civetone, cyclopentadecanone, and cyclohexadecenone; acetals and ketals such as acetaldehyde ethyl phenylpropyl acetal, citral diethyl acetal, phenylacetaldehyde glycerin acetal, and ethyl acetoacetate ethylene glycol ketals; anethole, β-naphthalene, Ethers such as butyl methyl ether, β-naphthyl ethyl ether, limonene oxide, rose oxide, 1,8-cineole, racemic or optically active dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan; nitriles such as citronellyl nitrile; γ-nonalactone, γ-undecalactone, σ-decalactone, γ-jasmolactone, coumarin, cyclopentadecanolide, cyclohexadecanolide, ambrette, ethyl lactones such as ambrosialate and 11-oxahexadecanolide; natural essential oils and extracts such as orange, lemon, bergamot, mandarin, peppermint, spearmint, lavender, chamomile, rosemary, eucalyptus, sage, basil, rose, geranium, jasmine, ylang-ylang, anise, clove, ginger, nutmeg, cardamom, cedar, cypress, sandalwood, vetiver, patchouli, labdanum, and other fragrance substances such as synthetic fragrances;

[0033] The fragrance composition may also contain, as components other than the blended fragrance materials, surfactants such as polyoxyethylene lauryl sulfate ether; solvents such as dipropylene glycol, diethyl phthalate, ethylene glycol, propylene glycol, methyl myristate, and triethyl citrate; antioxidants; colorants, etc.

[0034] The compound represented by formula (1) has a floral odor as well as a woody, fruity, spicy, green, or other odor. When combined with a conventional fragrance, the compound can impart a natural woody, fruity, spicy, or green odor as well as a floral odor. Therefore, the compound is useful for imparting an odor to various cosmetics, health and hygienic materials, medicines, daily necessities, foods, and the like by adding the compound to them.

[0035] Examples of products to which a fragrance composition containing a compound represented by formula (1) can be added in order to impart a fragrance and improve the fragrance of a compound to be blended include various products such as cosmetics, health and hygiene materials, miscellaneous goods, beverages, foods, quasi-drugs, and pharmaceuticals, and examples of such products include fragrance products such as perfumes and colognes; shampoos, rinses, hair tonics, hair creams, mousses, gels, pomades, sprays, and other hair cosmetics; lotions, beauty serums, creams, milky lotions, packs, foundations, It can be used as a fragrance component in skin cosmetics such as face powder, lipstick, and various types of make-up; dishwashing detergents, laundry detergents, softeners, disinfectant detergents, deodorizing detergents, room fresheners, furniture care, glass cleaners, furniture cleaners, floor cleaners, disinfectants, insecticides, bleaches, germicides, repellents, and other various health and hygiene detergents; toothpaste, mouthwash, bath additives, antiperspirant products, perm solution, and other quasi-drugs; miscellaneous goods such as toilet paper and tissue paper; pharmaceuticals, etc.; and foods, etc.

[0036] The blending amount of the fragrance composition in the above-mentioned product is not particularly limited, and can be selected from a wide range depending on the type, properties, and sensory effect of the product to be scented, etc. For example, it is 0.00001% by mass or more, preferably 0.0001% by mass or more, and more preferably 0.001% by mass or more, and in the case of fragrances such as perfume, it may be 100% by mass, but is preferably 80% by mass or less, more preferably 60% by mass or less, and even more preferably 40% by mass or less.

[0037] [Compound represented by formula (2)] The compound of the present invention is represented by formula (2). Hereinafter, the compound represented by formula (2) is also referred to as "the branched isobutyric acid ester of the present invention." [ka] (In formula (2), R 2 represents a saturated branched chain hydrocarbon group having 7 to 20 carbon atoms, excluding the 2-ethylhexyl group.

[0038] Although there have been reports on α-hydroxyisobutyric acid ester compounds, there has been no description in the prior art of α-hydroxyisobutyric acid esters of saturated branched hydrocarbon groups having 7 to 20 carbon atoms, except for the 2-ethylhexyl group.

[0039] In formula (2), R 2 is a saturated branched chain hydrocarbon group having 7 to 20 carbon atoms, and preferably a saturated branched chain hydrocarbon group having 7 to 10 carbon atoms. In formula (2), R 2Specific examples of the alkyl group include a 2-methylhexyl group, a 2-ethylpentyl group, a 2,4-dimethylpentyl group, a 2,2-dimethylpentyl group, a 2,4-dimethylpentan-3-yl group, a 5-methylhexan-2-yl group, a 2-ethyl-4-methylpentyl group, a 2,2-dimethylhexyl group, a 2,2,4-trimethylpentyl group, a 4,4-dimethylhexan-2-yl group, a 3,4-dimethylhexan-2-yl group, a 6-methylheptan-2-yl group, a 5-methylheptan-4-yl group, a 5-methylheptan-3-yl group, a 7-methyloctyl group, a 6-methyloctan-2-yl group, and a 2,6-dimethylheptyl group. , 2,6-dimethylheptan-4-yl group, 3,5,5-trimethylhexyl group, 8-methylnonyl group, 3-propylheptyl group, 3,7-dimethyloctyl group, 2-ethyl-5-methylheptyl group, 4,7-dimethyloctane-3-yl group, 2,3,5-trimethylheptyl group, 2,5,6-trimethylheptyl group, 3,5,5-trimethylheptyl group, 4,8-dimethyldecyl group, 5,9-dimethyldecyl group, 3,4,5,6,6-pentamethylheptan-2-yl group, 11-methyldodecyl group, 6,10-dimethylundecan-2-yl group, and 3,7,9-trimethyldecyl group.

[0040] R 2 When the group has an asymmetric carbon, the compound represented by formula (2) includes any one or a mixture of the optical isomers thus generated in any ratio.

[0041] Preferably, R 2 The group is a saturated branched hydrocarbon group. Preferably, R 2 The group is a saturated branched hydrocarbon group having at least one quaternary carbon atom. Particularly preferably, R 2 The group is a 5-methylhexan-2-yl group. Particularly preferably, R 2 The group is a 6-methylheptan-2-yl group. Particularly preferably, R 2 The group is a 3,5,5-trimethylhexyl group. Particularly preferably, R 2 The group is a 3,7-dimethyloctyl group. Examples of the branched isobutyric acid ester of the present invention include compounds represented by any of the following formulas (2-1) to (2-33).

[0042] [ka]

[0043] [ka]

[0044] [ka]

[0045] [ka]

[0046] [ka]

[0047] As shown in the example, the branched isobutyric acid ester of the present invention is an α-hydroxyisobutyric acid ester (excluding 2-ethylhexyl group) of a saturated branched hydrocarbon group having 7 to 20 carbon atoms. In addition, the branched isobutyric acid ester of the present invention preferably includes one having at least one or more quaternary carbon atoms.

[0048] The branched isobutyric acid ester of the present invention is a compound represented by formula (1), 1 Thus, the branched isobutyric acid ester of the present invention is useful as a fragrance by itself, and is also useful as an active ingredient in a fragrance composition.

[0049] [Compound represented by formula (3)] The compound of the present invention is represented by formula (3). Hereinafter, the compound represented by formula (3) is also referred to as "the unsaturated isobutyric acid ester of the present invention." [ka] (In formula (3), R 3 represents an unsaturated chain hydrocarbon group having 7 to 20 carbon atoms.)

[0050] Although there have been reports on α-hydroxyisobutyric acid ester compounds, there has been no description in the prior art of α-hydroxyisobutyric acid esters of unsaturated hydrocarbon groups having 7 to 20 carbon atoms.

[0051] In formula (3), R 3 is an unsaturated chain hydrocarbon group having 7 to 20 carbon atoms, and preferably an unsaturated chain hydrocarbon group having 8 to 15 carbon atoms. In formula (3), R 3Specific examples of the alkyl group include 1-octen-3-yl group, 1-nonen-3-yl group, 6-methyl-5-hepten-2-yl group, 5-methyl-2-hepten-4-yl group, 4,4-dimethyl-5-hexen-2-yl group, 6-nonenyl group, 2,6-nonadienyl group, 3,6-nonadienyl group, 2,6-dimethyl-5-heptenyl group, 9-decenyl group, 3,7-dimethyl-6-octenyl group, 3,7-dimethyl-2,6-octadienyl group, 2-isopropenyl-5-methyl-4-hexenyl group, and the like. xenyl group, 2-isopropyl-5-methyl-2-hexenyl group, 4,7-dimethyl-6-octen-3-yl group, 2,5,6-trimethyl-4-heptenyl group, 3,5,5-trimethyl-2,6-heptadienyl group, 9-undecenyl group, 10-undecenyl group, 4-methyl-3-decen-5-yl group, 4,8-dimethyl-4,9-decadienyl group, 5,9-dimethyl-4,8-decadienyl group, 3,5,6,6-tetramethyl-4-methyleneheptan-2-yl group, 6 ,10-dimethyl-5,9-undecadien-2-yl group, 3,7,9-trimethyl-2,6-decadienyl group, 2,6,10-trimethyl-9-undecenyl group, 2,6,10-trimethyl-5,9-undecadienyl group, (E)-3,7,11-trimethyl-6,10-dodecadienyl group, (Z)-3,7,11-trimethyl-6,10-dodecadienyl group, (2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl group, (2E,6Z)-3,7 ,11-trimethyl-2,6,10-dodecatrienyl group, (2Z,6Z)-3,7,11-trimethyl-2,6,10-dodecatrienyl group, (2Z,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl group, 6,10,14-trimethyl-5,9,13-pentadecatrien-2-yl group, (E)-3,7,11,15-tetramethyl-2-hexadecenyl group, and (Z)-3,7,11,15-tetramethyl-2-hexadecenyl group.

[0052] R 3 When the group has one or more carbon-carbon double bonds, the compounds of formula (3) include any one or a mixture of the resulting stereoisomers in any ratio. 3When the group has an asymmetric carbon, the compound represented by formula (3) includes any one or a mixture of the optical isomers thus generated in any ratio.

[0053] Preferably, R 3 The group is a hydrocarbon group having a carbon-carbon unsaturated bond. Preferably, R 3 The group is a branched hydrocarbon group having a carbon-carbon unsaturated bond. Preferably, R 3 The group is a hydrocarbon group having one or more carbon-carbon double bonds. Preferably, R 3 The group is a branched hydrocarbon group having one or more carbon-carbon double bonds. Particularly preferably, R 3 The group is a 3,7-dimethyl-6-octenyl group. Particularly preferably, R 3 The group is a (2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl group. Particularly preferably, R 3 The group is a (2E,6Z)-3,7,11-trimethyl-2,6,10-dodecatrienyl group. Particularly preferably, R 3 The group is a (2Z,6Z)-3,7,11-trimethyl-2,6,10-dodecatrienyl group. Particularly preferably, R 3 The group is a (2Z,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl group. Examples of the unsaturated isobutyric acid ester of the present invention include compounds represented by any of the following formulas (3-1) to (3-27).

[0054] [ka]

[0055] [ka]

[0056] [ka]

[0057] [ka]

[0058] As illustrated, the unsaturated isobutyric acid ester of the present invention is an α-hydroxyisobutyric acid ester of an unsaturated hydrocarbon group having 7 to 20 carbon atoms. The unsaturated isobutyric acid ester of the present invention preferably includes one having at least one carbon-carbon double bond. In the illustrated compounds, those containing a double bond represented by a crossed double line indicate both the trans form (E form) and the cis form (Z form) of the stereoisomers generated by the double bond. The unsaturated isobutyric acid ester of the present invention preferably includes one having a branched hydrocarbon group.

[0059] The unsaturated isobutyric acid ester of the present invention is a compound represented by formula (1), 1 Therefore, the unsaturated isobutyric acid ester of the present invention is useful as a fragrance by itself, and is also useful as an active ingredient in a fragrance composition.

[0060] [Method for producing the compound represented by formula (1)] The method for producing the compound represented by formula (1) is not particularly limited, and may be appropriately selected from conventionally known methods.

[0061] For example, α-hydroxyisobutyric acid ester can be produced by the Grignard reaction of pyruvate ester with methyl magnesium halide. The reaction formula for this reaction is shown in the following formula (4). [ka] In formula (4), R is R in formula (1). 1 It represents a chain-like hydrocarbon group similar to that shown in the figure. X represents a halogen element such as chlorine, bromine, or iodine.

[0062] In addition, α-hydroxyisobutyric acid esters can be produced by esterifying α-hydroxyisobutyric acid with an alcohol in the presence of a catalyst. The reaction formula for this reaction is shown in the following formula (5). [ka] In formula (5), R is R in formula (1). 1 It indicates a chain-like hydrocarbon group similar to that shown in FIG.

[0063] In addition, the desired α-hydroxyisobutyric acid ester can be produced by transesterification of another type of α-hydroxyisobutyric acid ester with an alcohol in the presence of a catalyst. The reaction formula for this reaction is shown in the following formula (6). [ka] In formula (6), R is R in formula (1). 1 R' is not particularly limited as long as it is a group different from R.

[0064] The catalyst, reaction method, reaction conditions, and reaction apparatus used in these reactions are not particularly limited and may be any conventionally known catalyst, reaction method, reaction conditions, and reaction apparatus. The method for purifying the obtained compound of formula (1) is also not particularly limited and may be any conventionally known purification method. EXAMPLES

[0065] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0066] The reaction results were evaluated according to the following formula. Reaction yield (%) = [(number of moles of ester produced in the reaction mixture) / (number of moles of raw material ester in the feed mixture)] x 100%

[0067] <Gas Chromatography Analysis (GC Analysis)> Apparatus: "GC-2010" (manufactured by Shimadzu Corporation, product name) Detector: FID Column: "DB-1" (J&W capillary column, product name) (0.25 mm φ × 60 m × 0.25 μm)

[0068] <NMR Spectrum Analysis> The identification of the ester was 1 performed by 1H-NMR measurement and 13 13C-NMR measurement. The measurement conditions are shown below. Apparatus: "ECA500" (manufactured by JEOL Ltd., product name) 1 [[1H-NMR]] Nucleus: 1 1H Measurement frequency: 500 MHz Measurement sample: 5% CDCl 3 solution 13 [[13C-NMR]] Nucleus: 13 13C Measurement frequency: 125 MHz Measurement sample: 5% CDCl 3 solution

[0069] <Gas Chromatography-Mass Spectrometry Analysis (GC-MS Analysis)> The identification of the compound was also performed by specifying the molecular weight through GC-MS measurement (chemical ionization method [CI+], high-resolution mass spectrometry [millimas]). The measurement conditions are shown below. GC apparatus: "Agilent 7890A" (manufactured by Agilent Technologies, product name) GC measurement conditions Column: "DB-1" (J&W capillary column, product name) (0.25 mm φ × 30 m × 0.25 μm) MS apparatus: "JMS-T100GCV" (manufactured by JEOL Ltd., product name) MS measurement conditions, chemical ionization method Detector conditions: 200 eV, 300 μA Detector voltage: 2300 V ​​GC interface temperature: 210℃ Ionization chamber temperature: 250℃ Reagent gas: Isobutane The exact mass values ​​of the fragments detected in a protonated state by chemical ionization and the chemical formulas assigned based on the values ​​are shown. Those obtained by chemical ionization are indicated as [CI].

[0070] In addition, molecular weights of some samples were measured by combining field ionization [FI] and high-resolution mass spectrometry [millimass]. Except for the conditions below, the analytical equipment and conditions were the same as those for the chemical ionization method, but the reagent gas isobutane was not used. Ionization chamber temperature: 50℃ Counter electrode voltage: -10000V The exact mass values ​​obtained by field ionization were not protonated, and the chemical formula assigned by the protonation method is shown. The values ​​obtained by field ionization are indicated as [FI].

[0071] <Product isolation by chromatographic method> The following materials were used for chromatographic product isolation: Filler: "Wakogel C-200" (product name, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) Developing solvent: ethyl acetate-hexane

[0072] <Example 1: Synthesis of 3,5,5-trimethylhexyl α-hydroxyisobutyrate> A 300 ml glass flask equipped with a distillation tube was charged with 40.0 g of methyl α-hydroxyisobutyrate (manufactured by Mitsubishi Gas Chemical Co., Ltd.), 58.6 g of 3,5,5-trimethylhexanol (manufactured by Tokyo Chemical Industry Co., Ltd.), and 0.55 g of sodium methoxide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.). The transesterification reaction was carried out while heating and refluxing under normal pressure, and the reaction was carried out for 8 hours while the produced methanol was removed from the system. As a result, 3,5,5-trimethylhexyl α-hydroxyisobutyrate was obtained with a reaction yield of 95% by the reaction of the following formula (7). After adding water to the reaction system to deactivate the catalyst, reduced pressure distillation was carried out to obtain 50.8 g of 3,5,5-trimethylhexyl α-hydroxyisobutyrate (purity by GC analysis (hereinafter also referred to as GC purity): 98.9%) as a fraction at 3 hPa and 94 ° C. The results of NMR spectrum analysis and GC-MS analysis of the obtained isobutyrate ester are shown below.

[0073] [α-Hydroxyisobutyric acid 3,5,5-trimethylhexyl] 1 H NMR (500 MHz, CDCl 3 ) δ0.90 (9H, s), 0.96 (3H, d, J = 6.5 Hz), 1.10 (1H, dd, J = 14.0, 6.0Hz), 1.23 (1H, dd, J = 14.0, 4.0), 1.43 (3H, s), 1.43 (3H, s), 1.50 (1H, m), 1.61 (1H, dtd, J = 13.0, 6.5, 4.0 Hz), 1.68 (1H, dq, J = 13.0, 6.5Hz), 3.18 (1H, s), 4.20 (2H, t, J = 6.5Hz) 13 C NMR (125 MHz, CDCl 3 ) δ22.60, 26.20, 27.33, 30.03, 31.20, 37.86, 51.04, 64.49, 72.06, 177.74 Exact.Mass [CI] 231.19733 (C 13 H 26 O 3 , parent peak), 127.15036 (C9 H 18 )

[0074] [ka]

[0075] <Examples 2 to 10: Synthesis of various α-hydroxyisobutyric acid esters> Using the same reaction apparatus as in Example 1, an appropriate amount of methyl α-hydroxyisobutyrate (manufactured by Mitsubishi Gas Chemical Co., Ltd.) and various alcohols (normal octanol, 3,7-dimethyloctanol, 3,7-dimethyl-6-octenol, 2-ethylhexanol, 3-octanol, 1-octen-3-ol, 6-methylhept-2-ol, 5-methylhex-2-ol, 3,7,11-trimethyl-2,6,10-dodecatrienol) were subjected to an ester exchange reaction under suitable reaction conditions while heating in the presence of a suitable catalyst such as titanium tetraalkoxide and / or sodium alkoxide, and in some cases in the presence of a solvent such as hexane or toluene. The ester exchange reaction was completed while the methanol produced by the reaction was removed from the system by distillation or azeotropy with the reaction solvent under reaction conditions, and the following α-hydroxyisobutyric acid esters were obtained by separation by distillation or column chromatography in the same manner as in Example 1. The GC purity of the obtained isobutyric acid ester is shown below, and in the case of new compounds, the NMR spectrum analysis and GC-MS analysis are also shown.

[0076] [α-Hydroxyisobutyric acid n-octyl] GC purity:99.9%

[0077] [α-Hydroxyisobutyric acid 3,7-dimethyloctyl] GC purity: 99.5% 1 H NMR (500 MHz, CDCl 3) δ0.87 (6H, d, J = 6.5Hz), 0.91 (3H, d, J = 6.5Hz), 1.12 - 1.16 (3H, m), 1.22 - 1.33 (3H, m), 1.42 (6H, s), 1.43 - 1.54 (3H, m), 1.70 (1H, dq, J = 12.5, 6.5Hz), 3.11 (1H, s), 4.17 - 4.25 (2H, m) 13 C NMR (125 MHz, CDCl 3 ) δ19.64, 22.72, 22.81, 24.75, 27.32, 28.07, 29.94, 35.55, 37.19, 39.28, 64.56, 72.08, 177.75 Exact.Mass [CI] 245.21163 (C 14 H 28 O 3 , parent peak), 141.16420 (C 10 H 20 )

[0078] [α-Hydroxyisobutyric acid 3,7-dimethyl-6-octenyl] GC purity: 98.4% 1 H NMR (500 MHz, CDCl 3 ) δ0.93 (3H, d, J = 6.5Hz), 1.20 (1H, dddd, J = 13.5, 9.0, 7.5, 6.0), 1.35 (1H, dddd, J = 13.5, 9.0, 6.5, 5.5), 1.42, (6H, s), 1.48 (1H, m), 1.56 (1H, m), 1.60 (3H, s), 1.68 (3H, s) 1.71 (1H, m), 1.92 - 2.05 (2H, m), 3.11 (1H, s), 4.17 - 4.25 (2H, m), 5.08 (1H, tt, J = 7.0Hz, 1.5Hz) 13 C NMR (125 MHz, CDCl 3) δ17.78, 19.51, 25.47, 25.84, 27.30, 29.46, 35.49, 37.00, 64.46, 72.07, 124.53, 131.62, 177.73 Exact.Mass [CI] 243.19691 (C 14 H 26 O 3 , parent peak), 139.14897 (C 10 H 18 )

[0079] [2-Ethylhexyl α-hydroxyisobutyrate] GC purity: 99.8%

[0080] [α-Hydroxyisobutyric acid oct-3-yl] GC purity: 99.8% 1 H NMR (500 MHz, CDCl 3 ) δ0.87-0.91 (6H, m), 1.26-1.30 (6H, m), 1.43(s, 3H), 1.43(s, 3H), 1.56-1.62 (4H, m), 3.20 (1H, s), 4.88 (1H, qn, J = 6.5Hz) 13 C NMR (125 MHz, CDCl 3 ) δ9.47, 13.93, 22.48, 24.84, 26.94, 27.17, 27.19, 31.57, 33.51, 71.94, 77.32, 177.47 Exact.Mass [CI] 217.18252 (C 12 H 24 O 3 , parent peak), 105.05765 (C 4 H 8 O 3 )

[0081] [α-Hydroxyisobutyric acid 1-octen-3-yl] GC purity: 99.8% 1 H NMR (500 MHz, CDCl3 ) δ0.89 (3H, t, J = 6.5 Hz), 1.25 - 1.35 (6H, m), 1.44 (3H, s), 1.45 (3H, s), 1.58 - 1.69 (2H, m), 3.14 (1H, s), 5.19 (1H, dt, J = 10.5, 1.0 Hz), 5.25 (1H, dt, J = 17.0, 1.0 Hz), 5.28 (1H, qt, J = 6.5, 1.0 Hz), 5.79 (1H, ddd, J = 17.0, 10.5, 6.5) 13 C NMR (125 MHz, CDCl 3 ) δ14.07, 22.60, 24.76, 27.28, 31.56, 34.21, 72.09, 76.44, 117.07, 136.12, 177.03 Exact.Mass [CI] 215.16762 (C 12 H 22 O 3 , parent peak), 111.11767 (C 8 H 14 )

[0082] [(6 - methylheptan - 2 - yl) α - hydroxyisobutyrate] GC purity: 99.9% 1 H NMR (500 MHz, CDCl 3 ) δ0.86 (6H, d, J = 6.0Hz), 1.14 - 1.20 (2H, m), 1.24 (3H, d, J = 6.0Hz), 1.26 - 1.35 (2H, m), 1.41 (3H, s), 1.42 (3H, s), 1.46 - 1.55 (2H, m), 1.59 (1H, m), 3.17 (1H, s), 4.96 (1H, sext, J = 6.5 Hz) 13 C NMR (125 MHz, CDCl 3) δ19.82, 22.42, 22.47, 23.00, 27.06, 27.08, 27.75, 35.95, 38.53, 71.81, 72.71, 177.18 Exact.Mass [CI] 217.18164 (C 12 H 24 O 3 , parent peak), 113.13416 (C 8 H 16 )

[0083] [α-Hydroxyisobutyric acid 5-methylhex-2-yl] GC purity: 99.7% 1 H NMR (500 MHz, CDCl 3 ) δ0.88 (3H, d, J = 6.5Hz), 0.88 (3H, d, J = 6.5Hz), 1.16-1.22 (2H, m), 1.24 (3H, d, J = 6.0Hz), 1.41 (3H, s), 1.42 (3H, s), 1.50-1.54 (2H, m), 1.60 (1H, m) 3.16 (1H, s) 4.94 (1H, sext J = 6.5 Hz) 13 C NMR (125 MHz, CDCl 3 ) δ19.83, 22.43, 22.53, 27.09, 27.12, 27.78, 33.57, 34.34, 71.85, 73.03, 177.22 Exact.Mass [CI] 203.16554 (C 11 H 22 O 3 , parent peak), 105.05609 (C 4 H 8 O 3 )

[0084] [α-Hydroxyisobutyric acid 3,7,11-trimethyl-2,6,10-dodecatrienyl] GC purity: 98.2% (total value of four isomers) The farnesol used as the raw material is a mixture of four isomers resulting from two double bonds, with a composition ratio of 54.0% (2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol, 42.1% (2E,6Z)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol, and 3.9% as the total of the remaining (2Z,6Z)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol and (2Z,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol. The α-hydroxyisobutyric acid esters of farnesol obtained through the reaction and purification process were 59.8% esters derived from (2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol, 37.9% esters derived from (2E,6Z)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol, and the remaining esters derived from (2Z,6Z)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol and (2Z,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol, totaling 2.3%. The two isomers with low abundance were not identified. The individual GC-MS analyses are shown below.

[0085] Esters derived from (2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol; Exact.Mass [FI] 308.23700 (C 19 H 32 O 3 , parent peak),

[0086] Esters derived from (2E,6Z)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol; Exact.Mass [FI] 308.23884 (C 19 H 32 O 3 , parent peak), 204.18909 (C 15 H 24 )

[0087] Esters derived from (2Z,6Z)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol and (2Z,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol (unspecified); Exact.Mass [FI] 308.23680 (C 19 H 32 O 3 , parent peak), 204.19123 (C 15 H 24 ) Exact.Mass [FI] 308.23547 (C 19 H 32 O 3 , parent peak), 204.20633 (C 15 H 24 )

[0088] The various α-hydroxyisobutyric acid esters obtained by the above-mentioned methods were subjected to an odor evaluation by a perfumer, and the results are shown in Table 1.

[0089] [Table 1]

[0090] Example 11: Fragrance composition with a fresh, forest-like scent A fragrance composition was prepared by adding 100 parts by mass of the 3,5,5-trimethylhexyl α-hydroxyisobutyrate obtained in Example 1 to 900 parts by mass of a fragrance composition having the composition shown in Table 2. According to an odor evaluation by a perfumer, a soft floral feeling could be imparted by adding 3,5,5-trimethylhexyl α-hydroxyisobutyrate of Example 1 to the odor composition having the composition shown in Table 2, and a odor composition with a fresher forest-like scent was obtained. The odor of this odor composition is considered to be suitable for adding fragrance to men's air fresheners and bath additives.

[0091] [Table 2]

[0092] Example 12: Citrus fruity type fragrance composition A fragrance composition was prepared by adding 100 parts by mass of 6-methylhept-2-yl α-hydroxyisobutyrate obtained in Example 8 to 900 parts by mass of a fragrance composition having the composition shown in Table 3. According to an odor evaluation by a perfumer, the addition of 6-methylhept-2-yl α-hydroxyisobutyrate of Example 8 to the fragrance composition having the composition shown in Table 3 made the citrus-like top note softer and gave the body a sense of transparency. As a result, a more cohesive citrus-fruity fragrance composition was obtained that was imparted with a woody floral odor. The odor of this fragrance composition is considered to be suitable for adding fragrance to hair care products such as shampoos, air fresheners, etc.

[0093] [Table 3] [Industrial Applicability]

[0094] The α-hydroxyisobutyric acid ester compound of the present invention has an excellent fragrance and is expected to be used as a fragrance itself. In addition, by using the compound as a blended fragrance ingredient, a fragrance composition with an excellent fragrance can be obtained, and by blending the compound in various products, the desired fragrance-imparting properties can be exhibited.

Claims

1. A fragrance composition comprising a compound represented by formula (1) as an active ingredient. 【Chemistry 1】 (In formula (1), R 1 represents a chain hydrocarbon group having 7 to 20 carbon atoms, which may be linear or branched, and may be a saturated or unsaturated group. If it is an unsaturated group, it may have one or more carbon-carbon double bonds or carbon-carbon triple bonds.

2. In formula (1), R 1 The fragrance composition according to claim 1 , wherein is a linear hydrocarbon group.

3. In formula (1), R 1 The fragrance composition according to claim 1 , wherein is a branched hydrocarbon group.

4. In formula (1), R 1 The fragrance composition according to claim 3, wherein said aromatic compound has at least one quaternary carbon atom.

5. In formula (1), R 1 The fragrance composition according to claim 1, wherein is a hydrocarbon group having a carbon-carbon unsaturated bond.

6. In formula (1), R 1 The fragrance composition according to claim 5, wherein is a hydrocarbon group having one or more carbon-carbon double bonds.

7. In formula (1), R 1 The fragrance composition according to claim 5 or 6, wherein is a branched hydrocarbon group.

8. A compound represented by formula (2). 【Chemistry 2】 (In formula (2), R 2 is an unsubstituted, saturated, branched, chain-like hydrocarbon group having 7 to 20 carbon atoms, except for 2-ethylhexyl and t-octyl groups.

9. In formula (2), R 2 The compound of claim 8, wherein has at least one quaternary carbon atom.

10. A compound represented by formula (3). 【Chemistry 3】 (In formula (3), R 3 represents an unsaturated chain hydrocarbon group having 7 to 20 carbon atoms.)

11. In formula (3), R 3 The compound according to claim 10, wherein is a hydrocarbon group having at least one carbon-carbon double bond.

12. In formula (3), R 3 The compound according to claim 10 or 11, wherein is a branched hydrocarbon group.

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