Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
  • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
  • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/37—Esters of carboxylic acids
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
  • A61L9/00—Disinfection, sterilisation or deodorisation of air
  • A61L9/01—Deodorant compositions
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q13/00—Formulations or additives for perfume preparations
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
  • C11B9/00—Essential oils; Perfumes
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
  • C11B9/00—Essential oils; Perfumes
  • C11B9/0007—Aliphatic compounds
  • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
  • C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof

Definitions

• the present invention relates to an isobutyric acid ester compound having an alkenoyloxy group at the ⁇ -position, a fragrance composition, and use as a fragrance.
• isobutyric acid ester compounds are used as fragrances.
• methyl isobutyrate has a sweet apricot-like fruity aroma
• propyl isobutyrate has a heavy pineapple-like aroma
• butyl isobutyrate has a fresh apple- and banana-like fruity aroma
• isobutyrate has a sweet apricot-like fruity aroma.
• Isoamyl butyrate is described as having a sweet apricot and pineapple-like odor.
• Patent Document 1 discloses that an isobutyric acid ester compound having a butyryloxy group or a pivaloyloxy group at the ⁇ -position has a mint-like odor or a damascone-like odor and can be used as a raw material for perfumes and mixed perfumes.
• Patent Documents 2 and 3 disclose that isobutyric acid esters having an acryloyloxy group or a methacryloyloxy group at the ⁇ -position can be used as raw materials for resists. It is disclosed that it can be used as a raw material for molding materials such as lenses, and Patent Document 5 discloses that it can be used as a raw material for pressure-sensitive adhesives. There is no description of the composition, nor of its use as a perfume.
• Isobutyric acid ester compounds include compounds used as fragrances as described above.
• perfumes are used in various fields such as fragrance products, detergents, miscellaneous goods, pharmaceuticals, and foods. Therefore, the present invention contains an isobutyric acid ester compound, which is useful as a fragrance, as an active ingredient because it has a complex fragrance of a floral fragrance and other fragrances, and in addition to the above fragrance, the strength and diffusibility of the fragrance.
• the present inventors have synthesized various compounds and extensively studied their odors. found to do. Furthermore, the present inventors have found that the above problems can be solved by using a specific isobutyric acid ester compound having an alkenoyloxy group at the ⁇ -position and using it as a perfume. That is, the present invention is as follows.
• a fragrance composition containing a compound represented by the following formula (1) as an active ingredient (In formula (1), R 1 is a linear or branched olefinic unsaturated hydrocarbon group having 2 to 4 carbon atoms, and R 2 is a linear, branched or It is a cyclic alkyl group.)
• R 1 is a linear or branched olefinic unsaturated hydrocarbon group having 2 to 4 carbon atoms
• R 2 is a linear, branched or It is a cyclic alkyl group.
• R 1 is a linear or branched olefinic unsaturated hydrocarbon group having 3 to 4 carbon atoms.
• R 1 is an isopropenyl group.
• ⁇ 4> The fragrance composition according to any one of ⁇ 1> to ⁇ 3> above, wherein R 2 in formula (1) is a branched alkyl group having 3 to 4 carbon atoms.
• R 2 in formula (1) is a branched alkyl group having 3 to 4 carbon atoms.
• R 2 is an isopropyl group or a secondary butyl group.
• R 6> The fragrance composition according to any one of ⁇ 1> to ⁇ 5> above, wherein R 2 in formula (1) is an isopropyl group.
• R 1 is an isopropenyl group and R 2 is an isopropyl group
• R 1 is an isopropenyl group and R 2 is a secondary butyl group
• R 1 is a 1-propenyl group and R 2 is an isopropyl group
• R 1 is 1-propenyl group and R 2 is secondary butyl group
• R 1 is 1-butenyl group and R 2 is isopropyl group
• R 1 is 1-methyl-1-propenyl group and R 2 is isopropyl group
• R 1 is a 2-methyl-1-propenyl group and R 2 is an isopropyl group.
• R 1 is a linear or branched olefinic unsaturated hydrocarbon group having 2 to 4 carbon atoms
• R 2 is a linear, branched or It is a cyclic alkyl group.
• R 3 is a linear or branched olefinic unsaturated hydrocarbon group having 3 to 4 carbon atoms
• R 4 is a linear, branched or branched hydrocarbon group having 1 to 6 carbon atoms.
• R 4 is a branched alkyl group having 3 to 4 carbon atoms.
• R 4 is an isopropyl group or a secondary butyl group.
• R 4 is an isopropyl group.
• the present invention since it has a complex scent of a floral scent and other scents, it contains an isobutyric acid ester compound that is useful as a fragrance as an active ingredient, and in addition to the above scent, the strength and diffusibility of the scent. It is possible to provide a fragrance composition to which is added. Further, it is possible to provide an isobutyric acid ester compound having a complex fragrance of floral fragrance and other fragrances, and its use as a fragrance.
• the perfume composition of the present invention contains a compound represented by the following formula (1) as an active ingredient.
• BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail below.
• ⁇ Compound Represented by Formula (1)> A compound represented by the following formula (1) is contained as an active ingredient in the perfume composition of the present invention.
• R 1 is a linear or branched olefinic unsaturated hydrocarbon group having 2 to 4 carbon atoms
• R 2 is a linear, branched or It is a cyclic alkyl group.
• the compound represented by the above formula (1) has a complex scent of a floral scent and other scents, and in addition to the above scent, can impart strength and diffusibility of the scent to the perfume composition.
• the compound represented by the above formula (1) has a floral scent, and in addition, depending on the difference in R 1 or R 2 , green tone, rose tone, herbal tone, woody tone, balsamic tone, fruity tone, etc. It also exhibits odor.
• R 1 is a linear or branched olefinic unsaturated hydrocarbon group having 2 to 4 carbon atoms, preferably a linear or branched olefinic unsaturated hydrocarbon group having 3 to 4 carbon atoms. It is a saturated hydrocarbon group, more preferably a linear or branched olefinic unsaturated hydrocarbon group having 3 carbon atoms. R 1 may have an internal carbon-carbon double bond, a terminal carbon-carbon double bond, or both. When R 1 has one or more carbon-carbon double bonds, the compound represented by formula (1) includes any one of the resulting stereoisomers or a mixture in any proportion. .
• R 1 examples include vinyl, 1-propenyl, 2-propenyl (allyl), isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1- propenyl group, 1-methyl-2-propenyl group, 1-methylidene-propyl group, 2-methyl-1-propenyl group, and 2-methylidene-propyl group, preferably 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 1-methyl-1-propenyl group or 2-methyl-1-propenyl group, more preferably 1-propenyl group, isopropenyl group, 1-butenyl group, 1-methyl -1-propenyl group or 2-methyl-1-propenyl group, more preferably isopropenyl group.
• R 1 is an isopropenyl group.
• R 1 is a 1-propenyl group.
• R 1 is a 1-butenyl group.
• R 1 is a 1-methyl-1-propenyl group.
• R 1 is a 2-methyl-1-propenyl group.
• R 2 is a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms, preferably a linear or branched alkyl group having 3 to 4 carbon atoms.
• the compound represented by formula (1) includes any one of the resulting optical isomers or a mixture in any ratio.
• R 2 examples include methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group (2-methylpropyl group), secondary butyl group (1-methylpropyl group) and tertiary butyl group.
• R 2 is an isopropyl group.
• R 2 is a secondary butyl group.
• R 1 is a linear or branched olefinic unsaturated hydrocarbon group having 3 to 4 carbon atoms
• R 2 is a C 3 to 4 is a linear or branched alkyl group
• R 1 is a linear or branched olefinically unsaturated hydrocarbon group having 3 carbon atoms
• R 2 is a linear or branched chain having 3 to 4 carbon atoms.
• a combination of a chain or branched alkyl group is more preferable
• R 1 is a linear or branched olefinically unsaturated hydrocarbon group having 3 carbon atoms
• R 2 is a branched chain having 3 to 4 carbon atoms.
• R 1 is a linear or branched olefinically unsaturated hydrocarbon group having 3 carbon atoms and R 2 is a branched alkyl group having 3 carbon atoms is more preferable. Even more preferred. Specifically, R 1 is one selected from the group consisting of a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 1-methyl-1-propenyl group, and a 2-methyl-1-propenyl group. , R 2 is one selected from the group consisting of an isopropyl group and a secondary butyl group. The compound represented by the above formula (1) is Particularly preferably, R 1 is isopropenyl and R 2 is isopropyl.
• R 1 is isopropenyl and R 2 is secondary butyl.
• R 1 is 1-propenyl and R 2 is isopropyl.
• R 1 is a 1-propenyl group and R 2 is a secondary butyl group.
• R 1 is 1-butenyl and R 2 is isopropyl.
• R 1 is 1-methyl-1-propenyl and R 2 is isopropyl.
• R 1 is 2-methyl-1-propenyl and R 2 is isopropyl.
• R 1 is an isopropenyl group and R 2 is an isopropyl group
• R 1 is an isopropenyl group and R 2 is a secondary butyl group
• R 1 is a 1-propenyl group and R 2 is an isopropyl group
• R 1 is a 1-propenyl group and R 2 is a secondary butyl group
• R 1 is a 1-butenyl group and R 2 is an isopropyl group
• R 1 is a 1-methyl-1-propenyl group and R 2 is an isopropyl group
• R 1 is A compound having a 2-methyl-1-propenyl group and R 2 being an isopropyl group is particularly preferably contained as an active ingredient in the perfume composition of the present invention.
• compounds represented by any of the following formulas (1-1) to (1-96) are exemplified as compounds represented by formula (1).
• preferred compounds are the following formulas (1-12), (1-16), (1-28), (1-32), (1-36), (1-60), (1-84) It is a compound represented by any one of
• the compound represented by the formula (1) has a complex scent of a floral scent and other scents
• a complex fragrance of a floral fragrance and other fragrances can be imparted.
• the compound represented by formula (1) can impart strength and diffusibility of fragrance to the fragrance composition.
• the compound represented by the above formula (1) has a floral scent, and in addition, depending on the difference in R 1 or R 2 , green tone, rose tone, herbal tone, woody tone, balsamic tone, fruity tone, etc.
• a fragrance composition containing the compound represented by the formula (1) as an active ingredient is a fragrance composition to which, in addition to the fragrance described above, the strength and diffusibility of the fragrance are imparted.
• the "active ingredient" in the fragrance composition refers to a component that changes the fragrance of the fragrance composition, particularly a component that changes the fragrance of the fragrance composition to a preferable fragrance tone, and has the property of improving the fragrance of the fragrance composition. It refers to a component having
• the content of the compound represented by the formula (1) in the fragrance composition may be changed as appropriate depending on the type of the compound and the type and intensity of the desired fragrance, but the content of the compound represented by the formula (1)
• the content is preferably 0.001% by mass or more, more preferably 0.01% by mass or more, and still more preferably 0.1% by mass or more in the fragrance composition. Also, it is preferably 90% by mass or less, more preferably 70% by mass or less, and even more preferably 50% by mass or less.
• the perfume composition of the present invention contains the compound represented by formula (1) as an active ingredient. There is no particular limitation as long as at least one compound represented by formula (1) is contained, and two or more compounds represented by formula (1) may be contained.
• the perfume composition of the present invention may contain the compound represented by the formula (1) as an active ingredient, and the other components are not particularly limited, but the perfume other than the compound represented by the formula (1) is preferably further contained.
• the "fragrance composition” is a composition that imparts fragrance by adding it to various cosmetics, pharmaceuticals, foods, beverages, etc., or a composition that is used as a perfume or the like by itself.
• additives such as solvents may be contained as necessary.
• perfumes other than the compound represented by formula (1) contained in the perfume composition of the present invention include perfumes other than the compound represented by formula (1), surfactants, solvents, antioxidants and colorants, etc., and at least one selected from the group consisting of perfumes other than the compound represented by formula (1), surfactants, solvents, antioxidants and colorants, represented by formula (1) At least one selected from the group consisting of a perfume other than the compound described above and a solvent is more preferable.
• a fragrance other than the compound represented by formula (1) the fragrance can be adjusted according to the intended product.
• containing a solvent it becomes easy to dissolve and impregnate the target product, and the intensity and persistence of the fragrance can be adjusted.
• Perfume other than the compound represented by formula (1) is not particularly limited as long as it is a conventionally known perfume component, and a wide range of perfumes can be used. can be selected and used in a mixing ratio of
• Flavors other than the compound represented by formula (1) include hydrocarbons, alcohols, phenols, esters, aldehydes, ketones, acetals, ketals, ethers, nitriles, lactones, natural Essential oils, natural extracts and the like can be mentioned.
• Hydrocarbons include limonene, ⁇ -pinene, ⁇ -pinene, terpinene, cedrene, longifolene, valencene and the like.
• Alcohols include linalool, citronellol, geraniol, nerol, terpineol, dihydromyrcenol, ethyllinalool, farnesol, nerolidol, cis-3-hexenol, cedrol, menthol, borneol, ⁇ -phenylethyl alcohol, benzyl alcohol, phenyl Hexanol, 2,2,6-trimethylcyclohexyl-3-hexanol, 1-(2-t-butylcyclohexyloxy)-2-butanol, 4-isopropylcyclohexanemethanol, 4-t-butylcyclohexanol, 4-methyl-2 -(2-methylpropyl)tetrahydro
• Phenols include eugenol, thymol, vanillin and the like.
• Esters include linalyl formate, citronellyl formate, geranyl formate, n-hexyl acetate, cis-3-hexenyl acetate, linalyl acetate, citronellyl acetate, geranyl acetate, neryl acetate, terpinyl acetate, nopil Acetate, bornyl acetate, isobornyl acetate, ot-butyl cyclohexyl acetate, pt-butyl cyclohexyl acetate, tricyclodecenyl acetate, benzyl acetate, styraryl acetate, cinnamyl acetate, dimethylbenzyl carbyl acetate , 3-pentyl tetrahydropyran-4-yl acetate, citr
• Aldehydes include n-octanal, n-decanal, n-dodecanal, 2-methylundecanal, 10-undecenal, citronellal, citral, hydroxycitronellal, dimethyltetrahydrobenzaldehyde, 4(3)-(4-hydroxy- 4-methylpentyl)-3-cyclohexene-1-carbaldehyde, 2-cyclohexylpropanal, pt-butyl- ⁇ -methylhydrocinnamic aldehyde, p-isopropyl- ⁇ -methylhydrocinnamic aldehyde, p-ethyl - ⁇ , ⁇ -dimethylhydrocinnamic aldehyde, ⁇ -amyl cinnamic aldehyde, ⁇ -hexyl cinnamic aldehyde, piperonal, ⁇ -methyl-3,4-methylenedioxyhydrocin
• Ketones include methylheptenone, 4-methylene-3,5,6,6-tetramethyl-2-heptanone, amylcyclopentanone, 3-methyl-2-(cis-2-penten-1-yl)-2 -Cyclopenten-1-one, methylcyclopentenolone, roseketone, ⁇ -methylionone, ⁇ -ionone, carvone, menthone, camphor, nootkatone, benzylacetone, anisylacetone, methyl ⁇ -naphthylketone, 2,5-dimethyl -4-hydroxy-3(2H)-furanone, maltol, 7-acetyl-1,2,3,4,5,6,7,8-octahydro-1,1,6,7-tetramethylnaphthalene, muscone, civetone, cyclopentadecanone, cyclohexadecenone and the like.
• Acetals and ketals include acetaldehyde ethyl phenyl propyl acetal, citral diethyl acetal, phenyl acetaldehyde glycerin acetal, ethyl acetoacetate ethylene glycol ketal and the like.
• Ethers include anethole, ⁇ -naphthylmethyl ether, ⁇ -naphthylethyl ether, limonene oxide, rose oxide, 1,8-cineol, racemic or optically active dodecahydro-3a,6,6,9a-tetramethylnaphtho [2,1-b]furan and the like.
• Nitriles include citronellyl nitrile and the like.
• Lactones include ⁇ -nonalactone, ⁇ -undecalactone, ⁇ -decalactone, ⁇ -jasmolactone, coumarin, cyclopentadecanolide, cyclohexadecanolide, ambrettolide, ethylene brassylate, 11-oxa hexadecanolide and the like.
• Natural essential oils and extracts include orange, lemon, bergamot, mandarin, peppermint, spearmint, lavender, chamomile, rosemary, eucalyptus, sage, basil, rose, geranium, jasmine, ylang ylang, anise, clove, ginger and nutmeg. , cardamom, cedar, cypress, sandalwood, vetiver, patchouli, labdanum, and the like.
• Solvents include dipropylene glycol, diethyl phthalate, ethylene glycol, propylene glycol, methyl myristate, triethyl citrate and the like.
• Surfactants include polyoxyethylene lauryl sulfate ether and the like.
• a fragrance composition containing the compound represented by formula (1) as an active ingredient can be used as a fragrance ingredient for various products.
• Products in which the fragrance composition can be used include, for example, fragrance products such as perfumes and colognes; shampoos, conditioners, hair tonics, hair creams, mousses, gels, pomades, sprays and other hair cosmetics; Skin cosmetics such as water, beauty essence, cream, milky lotion, mask, foundation, face powder, lipstick, and various types of make-up; dishwashing detergent, laundry detergent, softeners, disinfectant detergent, deodorant detergent, indoor Air Fresheners, Furniture Care, Glass Cleaners, Furniture Cleaners, Floor Cleaners, Disinfectants, Insecticides, Bleachers, Disinfectants, Repellents, and Other Hygiene Detergents; Toothpastes, Mouthwashes, Bath Salts, Antiperspirant Products , quasi-drugs such as perm solution; miscellaneous goods such as toilet paper and tissue paper; medicines, etc.;
• the amount of the fragrance composition to be blended in the above product is not particularly limited, and the amount of the fragrance composition to be blended can be selected according to the type, properties and sensory effects of the product to be scented.
• the amount of the fragrance composition in the product is preferably 0.00001% by mass or more, more preferably 0.0001% by mass or more, and even more preferably 0.001% by mass or more. Also, it is preferably 80% by mass or less, more preferably 60% by mass or less, and even more preferably 40% by mass or less.
• the blending amount of the fragrance composition in the product may be 80% by mass or more, or may be 100% by mass.
• a compound represented by the following formula (1) can be used as a perfume.
• the present invention also provides the use of compounds of formula (1) as fragrances.
• R 1 is a linear or branched olefinic unsaturated hydrocarbon group having 2 to 4 carbon atoms
• R 2 is a linear, branched or It is a cyclic alkyl group.
• the compound represented by the above formula (1) has a complex scent of floral scent and other scents, it can be used as a perfume.
• the compound represented by the above formula (1) has a floral scent, and in addition, depending on the difference in R 1 or R 2 , green tone, rose tone, herbal tone, woody tone, balsamic tone, fruity tone, etc. It can also be used as a fragrance because it also exhibits an odor at the same time.
• the compound represented by formula (1) that can be used as a perfume is the same as the compound described in the section ⁇ Compound represented by formula (1)> in [Perfume composition], and has a preferred structure are also the same. Specifically, it is as follows.
• R 1 is a linear or branched olefinic unsaturated hydrocarbon group having 2 to 4 carbon atoms, preferably a linear or branched olefinic unsaturated hydrocarbon group having 3 to 4 carbon atoms. It is a saturated hydrocarbon group, more preferably a linear or branched olefinic unsaturated hydrocarbon group having 3 carbon atoms. R 1 may have an internal carbon-carbon double bond, a terminal carbon-carbon double bond, or both. When R 1 has one or more carbon-carbon double bonds, the compound represented by formula (1) includes any one of the resulting stereoisomers or a mixture in any proportion. .
• R 1 examples include vinyl, 1-propenyl, 2-propenyl (allyl), isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1- propenyl group, 1-methyl-2-propenyl group, 1-methylidene-propyl group, 2-methyl-1-propenyl group and 2-methylidene-propyl group, preferably 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 1-methyl-1-propenyl group or 2-methyl-1-propenyl group, more preferably 1-propenyl group, isopropenyl group, 1-butenyl group, 1-methyl -1-propenyl group or 2-methyl-1-propenyl group, more preferably isopropenyl group.
• R 1 is an isopropenyl group.
• R 1 is a 1-propenyl group.
• R 1 is a 1-butenyl group.
• R 1 is a 1-methyl-1-propenyl group.
• R 1 is a 2-methyl-1-propenyl group.
• R 2 is a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms, preferably a linear or branched alkyl group having 3 to 4 carbon atoms.
• the compound represented by formula (1) includes any one of the resulting optical isomers or a mixture in any ratio.
• R 2 examples include methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group (2-methylpropyl group), secondary butyl group (1-methylpropyl group) and tertiary butyl group.
• R 2 is an isopropyl group.
• R 2 is a secondary butyl group.
• R 1 is a linear or branched olefinic unsaturated hydrocarbon group having 3 to 4 carbon atoms
• R 2 is a C 3 to 4 is a linear or branched alkyl group
• R 1 is a linear or branched olefinically unsaturated hydrocarbon group having 3 carbon atoms
• R 2 is a linear or branched chain having 3 to 4 carbon atoms.
• a combination of a chain or branched alkyl group is more preferable
• R 1 is a linear or branched olefinically unsaturated hydrocarbon group having 3 carbon atoms
• R 2 is a branched chain having 3 to 4 carbon atoms.
• R 1 is a linear or branched olefinically unsaturated hydrocarbon group having 3 carbon atoms and R 2 is a branched alkyl group having 3 carbon atoms is more preferable. Even more preferred. Specifically, R 1 is one selected from the group consisting of a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 1-methyl-1-propenyl group, and a 2-methyl-1-propenyl group. , R 2 is one selected from the group consisting of an isopropyl group and a secondary butyl group. The compound represented by the above formula (1) is Particularly preferably, R 1 is isopropenyl and R 2 is isopropyl.
• R 1 is isopropenyl and R 2 is secondary butyl.
• R 1 is 1-propenyl and R 2 is isopropyl.
• R 1 is a 1-propenyl group and R 2 is a secondary butyl group.
• R 1 is 1-butenyl and R 2 is isopropyl.
• R 1 is 1-methyl-1-propenyl and R 2 is isopropyl.
• R 1 is 2-methyl-1-propenyl and R 2 is isopropyl.
• R 1 is an isopropenyl group and R 2 is an isopropyl group
• R 1 is an isopropenyl group and R 2 is a secondary butyl group
• R 1 is a 1-propenyl group and R 2 is an isopropyl group
• R 1 is a 1-propenyl group and R 2 is a secondary butyl group
• R 1 is a 1-butenyl group and R 2 is an isopropyl group
• R 1 is a 1-methyl-1-propenyl group and R 2 is an isopropyl group
• R 1 is Compounds in which 2-methyl-1-propenyl and R 2 are isopropyl are particularly preferably used as fragrances.
• R 3 is a linear or branched olefinic unsaturated hydrocarbon group having 3 to 4 carbon atoms
• R 4 is a linear, branched or branched hydrocarbon group having 1 to 6 carbon atoms.
• the compound represented by the formula (2) is useful as a fragrance because it has a complex fragrance of floral fragrance and other fragrances.
• the compound represented by the above formula (2) has a floral fragrance, and in addition, green tone, rose tone, herbal tone, woody tone, balsamic tone, fruity tone, etc. depending on the difference in R 3 or R 4 . It is useful as a fragrance because it also exhibits an odor at the same time.
• R 3 is a linear or branched olefinic unsaturated hydrocarbon group with 3 to 4 carbon atoms excluding an isopropenyl group, more preferably a linear or branched chain with 3 carbon atoms. is an olefinically unsaturated hydrocarbon group.
• R 3 may have an internal carbon-carbon double bond, a terminal carbon-carbon double bond, or both.
• the compound represented by formula (2) includes any one of the resulting stereoisomers or a mixture in any proportion. .
• R 3 examples include 1-propenyl group, 2-propenyl group (allyl group), 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-1-propenyl group, 1-methyl- 2-propenyl group, 1-methylidene-propyl group, 2-methyl-1-propenyl group, and 2-methylidene-propyl group, preferably 1-propenyl group, 1-butenyl group, 1-methyl-1- It is a propenyl group or a 2-methyl-1-propenyl group.
• R 3 is a 1-propenyl group.
• R 3 is a 1-butenyl group.
• R 3 is a 1-methyl-1-propenyl group.
• R 3 is a 2-methyl-1-propenyl group.
• R 4 is a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms, preferably a linear or branched alkyl group having 3 to 4 carbon atoms.
• the compound represented by formula (2) includes any one of the resulting optical isomers or a mixture in any ratio.
• R 4 examples include methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group (2-methylpropyl group), secondary butyl group (1-methylpropyl group) and tertiary butyl group.
• R4 is an isopropyl group.
• R4 is a secondary butyl group.
• R 3 is a linear or branched olefinic unsaturated hydrocarbon group having 3 to 4 carbon atoms
• R 4 is a C 3 to 4 is a linear or branched alkyl group
• R 3 is a linear or branched olefinically unsaturated hydrocarbon group having 3 carbon atoms
• R 4 is a linear or branched alkyl group having 3 to 4 carbon atoms.
• a combination of a chain or branched alkyl group is more preferable
• R 3 is a linear or branched olefinically unsaturated hydrocarbon group having 3 carbon atoms
• R 4 is a branched chain having 3 to 4 carbon atoms.
• R 3 is a linear or branched olefinically unsaturated hydrocarbon group having 3 carbon atoms and R 4 is a branched alkyl group having 3 carbon atoms is more preferable. Even more preferred. Specifically, R 3 is one selected from the group consisting of a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 1-methyl-1-propenyl group, and a 2-methyl-1-propenyl group. , R 4 is one selected from the group consisting of an isopropyl group and a secondary butyl group. The compound represented by the above formula (2) is Particularly preferably, R 3 is 1-propenyl and R 4 is isopropyl.
• R 3 is a 1-propenyl group and R 4 is a secondary butyl group. Particularly preferably, R 3 is 1-butenyl and R 4 is isopropyl. Particularly preferably, R 3 is 1-methyl-1-propenyl and R 4 is isopropyl. Particularly preferably, R 3 is 2-methyl-1-propenyl and R 4 is isopropyl.
• compounds represented by formula (2) are exemplified by compounds represented by any of the following formulas (2-1) to (2-80).
• preferred compounds are compounds represented by any one of the following formulas (2-4), (2-8), (2-20), (2-44) and (2-68).
• the compound represented by formula (2) is useful as a fragrance because it has a complex fragrance of floral fragrance and other fragrances.
• the compound represented by the formula (2) has a floral scent, and in addition, green tone, rose tone, herbal tone, woody tone, balsamic tone, fruity tone, etc. depending on the difference in R 3 or R 4 .
• it is useful as a perfume.
• the compound represented by Formula (2) can be used as an aromatic component for various products.
• Products in which the compound represented by formula (2) can be used as an aromatic component include fragrance products such as perfumes and colognes; shampoos, rinses, hair tonics, hair creams, mousses, gels and pomades.
• skin cosmetics such as lotions, serums, creams, milky lotions, packs, foundations, powders, lipsticks, and various types of make-up
• dishwashing detergents laundry detergents, softeners, disinfectants Detergents, deodorant detergents, room air fresheners, furniture care, glass cleaners, furniture cleaners, floor cleaners, disinfectants, insecticides, bleaching agents, sterilizers, repellents, and other health and hygiene detergents
• toothpaste, Quasi-drugs such as mouthwashes, bath salts, antiperspirant products, perm liquids
• miscellaneous goods such as toilet paper and tissue paper
• pharmaceuticals such as lotions, serums, creams, milky lotions, packs, foundations, powders, lipsticks, and various types of make-up
• dishwashing detergents laundry detergents, softeners, disinfectants Detergents, deodorant detergents, room air fresheners, furniture care, glass cleaners, furniture cleaners, floor cleaners, disinfectants, insecticides, bleaching agents
• the amount of the compound represented by formula (2) in the above product is not particularly limited, and the amount of the compound represented by formula (2) may vary depending on the type, properties, and sensory effects of the product to be perfumed. You can choose your blending amount.
• the compounding amount of the compound represented by formula (2) in the product is preferably 0.00001% by mass or more, more preferably 0.0001% by mass or more, and still more preferably 0.001% by mass. That's it. Also, it is preferably 80% by mass or less, more preferably 60% by mass or less, and even more preferably 40% by mass or less.
• the amount of the compound represented by formula (2) in the product may be 80% by mass or more. It may be 100% by mass.
• ⁇ Perfume composition containing the compound represented by formula (2) as an active ingredient> The compound represented by the following formula (2) of the present invention is also useful as an active ingredient of perfume compositions.
• a perfume composition containing the compound represented by formula (2) as an active ingredient is described below.
• R 3 is a linear or branched olefinic unsaturated hydrocarbon group having 3 to 4 carbon atoms
• R 4 is a linear, branched or branched hydrocarbon group having 1 to 6 carbon atoms.
• the compound represented by formula (2) has a complex scent of floral scent and other scents
• a complex fragrance of a floral fragrance and other fragrances can be imparted.
• the compound represented by formula (2) can impart strength and diffusibility of fragrance to the fragrance composition.
• the compound represented by the above formula (2) has a floral scent, and in addition, depending on the difference in R 3 or R 4 , it has a green tone, rose tone, herbal tone, woody tone, balsamic tone, fruity tone, etc.
• a perfume composition containing the compound represented by the above formula (2) as an active ingredient is a perfume composition to which, in addition to the above-described scent, strength and diffusibility of the scent are imparted.
• the "active ingredient" in the fragrance composition refers to a component that changes the fragrance of the fragrance composition, particularly a component that changes the fragrance of the fragrance composition to a preferable fragrance tone, and has the property of improving the fragrance of the fragrance composition. It refers to a component having
• the compound represented by formula (2) used as an active ingredient of the fragrance composition is the same as the compound represented by formula (2) above, and the preferred structure is also the same.
• the content of the compound represented by formula (2) in the fragrance composition may be changed as appropriate depending on the type of compound and the type and intensity of the desired fragrance.
• the content is preferably 0.001% by mass or more, more preferably 0.01% by mass or more, and still more preferably 0.1% by mass or more in the perfume composition. Also, it is preferably 90% by mass or less, more preferably 70% by mass or less, and even more preferably 50% by mass or less.
• the fragrance composition containing the compound represented by formula (2) as an active ingredient is not particularly limited as long as it contains at least one compound represented by formula (2), and two or more types of formula (2) It may contain a compound represented by.
• the perfume composition containing the compound represented by formula (2) as an active ingredient may contain the compound represented by formula (2) as an active ingredient, and other ingredients are not particularly limited, It is preferable to further contain a perfume other than the compound represented by formula (2).
• the "fragrance composition” is a composition that imparts fragrance by adding it to various cosmetics, pharmaceuticals, foods, beverages, etc., or a composition that is used as a perfume or the like by itself.
• additives such as solvents may be contained as necessary.
• fragrance composition containing the compound represented by formula (2) as an active ingredient include compounds other than the compound represented by formula (2) fragrances, surfactants, solvents, antioxidants and colorants, etc., and selected from the group consisting of fragrances other than the compound represented by formula (2), surfactants, solvents, antioxidants and colorants is preferred, and at least one selected from the group consisting of perfumes other than the compound represented by formula (2) and solvents is more preferred.
• a fragrance other than the compound represented by formula (2) the fragrance can be adjusted according to the intended product.
• containing a solvent it becomes easy to dissolve and impregnate the target product, and the intensity and persistence of the fragrance can be adjusted.
• Perfume other than the compound represented by formula (2) is not particularly limited as long as it is a conventionally known perfume component, and a wide range of perfumes can be used. can be selected and used in a mixing ratio of
• Flavors other than the compound represented by formula (2) include hydrocarbons, alcohols, phenols, esters, aldehydes, ketones, acetals, ketals, ethers, nitriles, lactones, natural Essential oils, natural extracts and the like can be mentioned.
• Hydrocarbons include limonene, ⁇ -pinene, ⁇ -pinene, terpinene, cedrene, longifolene, valencene and the like.
• Alcohols include linalool, citronellol, geraniol, nerol, terpineol, dihydromyrcenol, ethyllinalool, farnesol, nerolidol, cis-3-hexenol, cedrol, menthol, borneol, ⁇ -phenylethyl alcohol, benzyl alcohol, phenyl Hexanol, 2,2,6-trimethylcyclohexyl-3-hexanol, 1-(2-t-butylcyclohexyloxy)-2-butanol, 4-isopropylcyclohexanemethanol, 4-t-butylcyclohexanol, 4-methyl-2 -(2-methylpropyl)tetrahydro
• Phenols include eugenol, thymol, vanillin and the like.
• Esters include linalyl formate, citronellyl formate, geranyl formate, n-hexyl acetate, cis-3-hexenyl acetate, linalyl acetate, citronellyl acetate, geranyl acetate, neryl acetate, terpinyl acetate, nopil Acetate, bornyl acetate, isobornyl acetate, ot-butyl cyclohexyl acetate, pt-butyl cyclohexyl acetate, tricyclodecenyl acetate, benzyl acetate, styraryl acetate, cinnamyl acetate, dimethylbenzyl carbyl acetate , 3-pentyl tetrahydropyran-4-yl acetate, citr
• Aldehydes include n-octanal, n-decanal, n-dodecanal, 2-methylundecanal, 10-undecenal, citronellal, citral, hydroxycitronellal, dimethyltetrahydrobenzaldehyde, 4(3)-(4-hydroxy- 4-methylpentyl)-3-cyclohexene-1-carbaldehyde, 2-cyclohexylpropanal, pt-butyl- ⁇ -methylhydrocinnamic aldehyde, p-isopropyl- ⁇ -methylhydrocinnamic aldehyde, p-ethyl - ⁇ , ⁇ -dimethylhydrocinnamic aldehyde, ⁇ -amyl cinnamic aldehyde, ⁇ -hexyl cinnamic aldehyde, piperonal, ⁇ -methyl-3,4-methylenedioxyhydrocin
• Ketones include methylheptenone, 4-methylene-3,5,6,6-tetramethyl-2-heptanone, amylcyclopentanone, 3-methyl-2-(cis-2-penten-1-yl)-2 -Cyclopenten-1-one, methylcyclopentenolone, roseketone, ⁇ -methylionone, ⁇ -ionone, carvone, menthone, camphor, nootkatone, benzylacetone, anisylacetone, methyl ⁇ -naphthylketone, 2,5-dimethyl -4-hydroxy-3(2H)-furanone, maltol, 7-acetyl-1,2,3,4,5,6,7,8-octahydro-1,1,6,7-tetramethylnaphthalene, muscone, civetone, cyclopentadecanone, cyclohexadecenone and the like.
• Acetals and ketals include acetaldehyde ethyl phenyl propyl acetal, citral diethyl acetal, phenyl acetaldehyde glycerin acetal, ethyl acetoacetate ethylene glycol ketal and the like.
• Ethers include anethole, ⁇ -naphthylmethyl ether, ⁇ -naphthylethyl ether, limonene oxide, rose oxide, 1,8-cineol, racemic or optically active dodecahydro-3a,6,6,9a-tetramethylnaphtho [2,1-b]furan and the like.
• Nitriles include citronellyl nitrile and the like.
• Lactones include ⁇ -nonalactone, ⁇ -undecalactone, ⁇ -decalactone, ⁇ -jasmolactone, coumarin, cyclopentadecanolide, cyclohexadecanolide, ambrettolide, ethylene brassylate, 11-oxa hexadecanolide and the like.
• Natural essential oils and extracts include orange, lemon, bergamot, mandarin, peppermint, spearmint, lavender, chamomile, rosemary, eucalyptus, sage, basil, rose, geranium, jasmine, ylang ylang, anise, clove, ginger and nutmeg. , cardamom, cedar, cypress, sandalwood, vetiver, patchouli, labdanum, and the like.
• Solvents include dipropylene glycol, diethyl phthalate, ethylene glycol, propylene glycol, methyl myristate, triethyl citrate and the like.
• Surfactants include polyoxyethylene lauryl sulfate ether and the like.
• a fragrance composition containing the compound represented by formula (2) as an active ingredient can be used as a fragrance ingredient for various products.
• Products in which the fragrance composition can be used include, for example, fragrance products such as perfumes and colognes; shampoos, conditioners, hair tonics, hair creams, mousses, gels, pomades, sprays and other hair cosmetics; Skin cosmetics such as water, beauty essence, cream, milky lotion, mask, foundation, face powder, lipstick, and various types of make-up; dishwashing detergent, laundry detergent, softeners, disinfectant detergent, deodorant detergent, indoor Air Fresheners, Furniture Care, Glass Cleaners, Furniture Cleaners, Floor Cleaners, Disinfectants, Insecticides, Bleachers, Disinfectants, Repellents, and Other Hygiene Detergents; Toothpastes, Mouthwashes, Bath Salts, Antiperspirant Products , quasi-drugs such as perm solution; miscellaneous goods such as toilet paper and tissue paper; medicines, etc.;
• the amount of the fragrance composition to be blended in the above product is not particularly limited, and the amount of the fragrance composition to be blended can be selected according to the type, properties and sensory effects of the product to be scented.
• the amount of the fragrance composition in the product is preferably 0.00001% by mass or more, more preferably 0.0001% by mass or more, and even more preferably 0.001% by mass or more. Also, it is preferably 80% by mass or less, more preferably 60% by mass or less, and even more preferably 40% by mass or less.
• the blending amount of the fragrance composition in the product may be 80% by mass or more, or may be 100% by mass.
• a compound represented by the following formula (2) can be used as a fragrance.
• R 3 is a linear or branched olefinic unsaturated hydrocarbon group having 3 to 4 carbon atoms
• R 4 is a linear, branched or branched hydrocarbon group having 1 to 6 carbon atoms.
• the compound represented by the above formula (2) has a complex scent of floral scent and other scents, it can be used as a perfume.
• the compound represented by the above formula (2) has a floral fragrance, and in addition, green tone, rose tone, herbal tone, woody tone, balsamic tone, fruity tone, etc. depending on the difference in R 3 or R 4 . It can also be used as a fragrance because it also exhibits an odor at the same time.
• the compound represented by formula (2) that can be used as a fragrance is the same as the compound represented by formula (2) above, and the preferred structure is also the same.
• the method for producing the compound represented by formula (1) is not particularly limited, and may be appropriately selected from conventionally known methods and used. Moreover, the method for producing the compound represented by formula (2) is not particularly limited, and may be appropriately selected from conventionally known methods and used. Preferred examples of the method for producing the compound represented by Formula (1) are given below. In the method for producing the compound represented by formula (2), R 1 in formula (3) and formula (4) of the method for producing the compound represented by formula (1) shown below is replaced with R 3 and R 2 is read as R4 .
• an isobutyric acid ester having an alkenoyloxy group at the ⁇ position (compound represented by formula (1)) can be produced by reacting an ⁇ -hydroxyisobutyric acid ester with an unsaturated acid anhydride.
• the reaction formula of this reaction is shown in the following formula (3).
• R 1 is a linear or branched olefinic unsaturated hydrocarbon group having 2 to 4 carbon atoms
• R 2 is a linear, branched or cyclic hydrocarbon group having 1 to 6 carbon atoms. Indicates an alkyl group.
• an isobutyric acid ester having an alkenoyloxy group at the ⁇ -position (a compound represented by formula (1)) is obtained.
• the reaction formula of this reaction is shown in the following formula (4).
• R 1 is a linear or branched olefinic unsaturated hydrocarbon group having 2 to 4 carbon atoms
• R 2 is a linear, branched or cyclic hydrocarbon group having 1 to 6 carbon atoms. Indicates an alkyl group.
• the catalysts, reaction methods, reaction conditions, and reactors used in these reactions can be conventionally known catalysts, reaction methods, reaction conditions, and reactors, and are not particularly limited.
• a method for purifying the obtained isobutyric acid ester having an alkenoyloxy group at the ⁇ -position is also a known purification method. can be adopted.
• reaction yield (%) [(number of moles of ester produced in reaction solution) / (number of moles of raw material ester in charge solution)] x 100%
• GC apparatus "Agilent 7890B" (manufactured by Agilent, trade name) GC measurement conditions
• MS device "JMS-T200 GCx-plus” (manufactured by JEOL Ltd., product name)
• MS measurement conditions chemical ionization method Ionization voltage: 200 V
• Ion source 200°C
• Detector voltage 2100V
• Reagent gas Isobutane
• isopropyl ⁇ -hydroxyisobutyrate was obtained with a reaction yield of 98.4% by the reaction of the following formula (5).
• distillation under reduced pressure was performed to obtain 77.7 g of isopropyl ⁇ -hydroxyisobutyrate as a fraction at 40 mmHg and 65°C (purity by GC analysis (hereinafter also referred to as GC purity): 99.6%) was obtained.
• Example 1 Synthesis and evaluation of aroma of isopropyl ⁇ -methacryloyloxyisobutyrate> 14.6 g of isopropyl ⁇ -hydroxyisobutyrate synthesized in Synthesis Example 1 and 58 mg of iron (III) chloride (manufactured by Alfa Aesar) were charged into a 50 mL glass flask equipped with a stirrer, condenser and dropping device. While stirring at room temperature, 15.3 g of methacrylic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was slowly added dropwise.
• Examples 2 to 4 Synthesis and evaluation of aroma of various ⁇ -alkenoyloxyisobutyric acid esters> Using the same reactor as in Example 1, ⁇ -hydroxyisobutyrate (isopropyl ⁇ -hydroxyisobutyrate synthesized in Synthesis Example 1 or secondary butyl ⁇ -hydroxyisobutyrate synthesized in Synthesis Example 2), iron chloride (III ) (manufactured by Alfa Aesar) at 0.03 mol% for each ⁇ -hydroxyisobutyrate, and various acid anhydrides corresponding to the obtained ⁇ -alkenoyloxyisobutyrate for each ⁇ -hydroxyisobutyrate.
• ⁇ -hydroxyisobutyrate isopropyl ⁇ -hydroxyisobutyrate synthesized in Synthesis Example 1 or secondary butyl ⁇ -hydroxyisobutyrate synthesized in Synthesis Example 2
• iron chloride (III ) manufactured by Alfa Aesar
• Example 5 Synthesis of isopropyl ⁇ -(3-methyl-2-butenoyloxy)isobutyrate and evaluation of aroma>
• Acetic anhydride manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.
• 3-methylcrotonic acid manufactured by Tokyo Chemical Industry Co., Ltd. 23.5 g were placed in a 100 mL glass flask equipped with a stirrer, a distillation head, and a condenser tube. filled.
• 3-Methylcrotonic anhydride was prepared by heating and stirring at 90° C. and 30 to 60 hPa for 10 hours under reduced pressure while removing the resulting acetic acid from the top of the tower.
• Examples 6 and 7 Synthesis and evaluation of aroma of various isopropyl ⁇ -alkenoyloxyisobutyrates> Using the same reaction apparatus as in Example 5, acetic anhydride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), isopropyl ⁇ -hydroxyisobutyrate prepared in Synthesis Example 1, and isopropyl ⁇ -alkenoyloxyisobutyrate obtained were prepared.
• the GC purities, E/Z ratios, E-isomer NMR spectral analysis results, and E-isomer GC-MS analysis results of the obtained various isopropyl ⁇ -alkenoyloxyisobutyrates are shown below. Further, the obtained various isopropyl ⁇ -alkenoyloxyisobutyrates were evaluated for aroma by the method described later. Table 1 shows the results of the fragrance evaluation.
• Example 8 Synthesis and evaluation of aroma of isopropyl ⁇ -2-butenoyloxyisobutyrate>
• 2-butyric acid manufactured by Tokyo Chemical Industry Co., Ltd.
• 20 mL of diethyl ether manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.
• 5% palladium / barium sulfate Tokyo Kasei Kogyo Co., Ltd.
• 0.18 mL of quinoline manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.
• Table 1 shows the results of evaluating the aroma of the isobutyric acid ester compounds having an alkenoyloxy group at the ⁇ -position obtained in Examples 1 to 8 by a perfumer.
• Example 9 Fruity Herbal Type Perfume Composition> A fragrance composition was prepared by adding 35 parts by mass of isopropyl ⁇ -methacryloyloxyisobutyrate obtained in Example 1 to 965 parts by mass of the fragrance composition having the composition shown in Table 2. According to fragrance evaluation by a perfumer, by adding isopropyl ⁇ -methacryloyloxyisobutyrate of Example 1 to the fragrance composition having the composition shown in Table 2, it was possible to impart a strong green feeling and fruity feeling. . As a result, it was possible to obtain a fruity herbal type perfume composition that can be used for household items such as cleaners.
• Natural essential oil-like magnolia type fragrance composition A fragrance composition was prepared by adding 100 parts by mass of isopropyl ⁇ -2-methyl-2-butenoyloxyisobutyrate obtained in Example 7 to 900 parts by mass of a fragrance composition having the composition shown in Table 3. According to fragrance evaluation by a perfumer, by adding isopropyl ⁇ -2-methyl-2-butenoyloxyisobutyrate of Example 7 to the fragrance composition having the composition shown in Table 3, the diffusibility of the fragrance increased. It rose and became a mixed fragrance with a spread in the top note. As a result, it was possible to obtain a natural essential oil-like magnolia-type fragrance composition that can be used as a base fragrance with a natural image.
• the isobutyric acid ester compound having an alkenoyloxy group at the ⁇ -position of the present invention has a complex fragrance of floral fragrance and other fragrances. It can be seen that it is possible to obtain a fragrance composition containing the above-described fragrance as a component and imparting strength and diffusibility to the fragrance in addition to the above fragrance. From this, the isobutyric acid ester compound having an alkenoyloxy group at the ⁇ -position of the present invention is useful as an active ingredient of a fragrance composition, and the obtained fragrance composition can be used as desired by blending in various products. can exhibit the fragrance-imparting property.
• the isobutyric acid ester compound having an alkenoyloxy group at the ⁇ -position of the present invention has a complex fragrance of a floral fragrance and other fragrances, and thus is found to be useful as a fragrance.
• the isobutyric acid ester compound having an alkenoyloxy group at the ⁇ -position of the present invention has a floral scent, and in addition, depending on the difference in the unsaturated hydrocarbon group and the alkyl group, it has green tone, rose tone, herbal tone, and woody tone. , balsamic tone, and fruity tone at the same time. Therefore, the isobutyric acid ester compound having an alkenoyloxy group at the ⁇ -position of the present invention is useful as a fragrance and can be suitably used as a fragrance.

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