Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
  • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
  • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
• • 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
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
  • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
• • 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
• • 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
  • A61K8/34—Alcohols
• • 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
  • A61K8/35—Ketones, e.g. benzophenone
• • 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
  • 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
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
• • 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
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/41—Amines
• • 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
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
• • 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
  • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
• • 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
  • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
• • 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
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/10—Washing or bathing 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
• • 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
  • C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
  • C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
  • C11B9/0057—Spiro compounds
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/16—Organic compounds
  • C11D3/20—Organic compounds containing oxygen
  • C11D3/2068—Ethers
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/16—Organic compounds
  • C11D3/20—Organic compounds containing oxygen
  • C11D3/2096—Heterocyclic compounds
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/50—Perfumes
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
  • D06M13/005—Compositions containing perfumes; Compositions containing deodorants
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
  • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
  • D06M13/137—Acetals, e.g. formals, or ketals
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
  • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
  • D06M13/144—Alcohols; Metal alcoholates
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
  • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
  • D06M13/165—Ethers
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/02—Preparations for cleaning the hair
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
  • D06M2200/50—Modified hand or grip properties; Softening compositions

Definitions

• the present invention relates to perfume compositions.
• ⁇ -(2-alkylcyclohexyloxy)- ⁇ -alkanols especially 1-(2-t-butylcyclohexyloxy)-2-alkanols, have woody and amber-like odors, excellent lingering scent, and It is a useful perfume material that can be produced at low cost (JP-A-2013-151482).
• 1-(2-t-butylcyclohexyloxy)-2-butanol is widely known as amber core, a fragrance with a woody-amber-like fragrance (refreshing cypress-like fragrance) and a long lasting fragrance.
• the present invention is a fragrance preparation comprising a compound represented by formula (I).
• R 1 is an alkyl group having 1 to 5 carbon atoms
• R 2 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
• the purpose of the present invention is to provide a new flavoring agent and a new fragrance composition by studying conventional amber core manufacturing technology.
• the present inventors discovered that the low-boiling ot-butylcyclohexanone generated in the production of amber cores is an off-flavor component. On the other hand, it was newly discovered that certain ketal bodies alone have a pleasant fruity (apple-like), herbal, and minty-like aroma. In addition, the present inventors have found that a composition containing a specific concentration of the ketal body and amber core imparts a honey-like sweetness and fragrance volume to the amber core, which is a favorable effect. Based on such findings, the perfume preparation and perfume composition of the present invention were completed.
• JP-A-56-79686 discloses the following ketal compounds. This compound is reported to have an herb-like, fruit-like, and pungent odor. However, the impression of herb-like, highly irritating, and chemical scents poses the problem of low versatility in the production of mixed perfumes.
• JP-A-6-305999 discloses the following ketal compounds. Fruity, green, woody, floral, anise-like, fragrant, camphor-like, and tobacco-like odors have been reported for this compound. However, the impression of anise-like, camphor-like, and tobacco-like scents poses the problem of low versatility in the preparation of blended perfumes.
• the present invention is a fragrance preparation comprising a compound represented by formula (I).
• R 1 is an alkyl group having 1 to 5 carbon atoms
• R 2 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
• the present invention also provides a fragrance composition
• a fragrance composition comprising a compound represented by formula (II) and a compound represented by formula (I),
• the mass ratio of the compound represented by formula (II) to the compound represented by formula (I) [compound represented by formula (II): compound represented by formula (I)] is 99.99. : 0.01 or more and 98:2 or less.
• R 1 and R 3 are each independently an alkyl group having 1 to 5 carbon atoms
• R 2 and R 4 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
• a flavoring agent comprising the compound represented by the formula (I) of the present invention and a fragrance composition containing the flavoring agent have a pleasant fruity (apple-like), herbal, and minty-like scent.
• the fragrance composition containing the compound represented by the formula (II) and the compound represented by the formula (I) of the present invention is preferable because it imparts honey-like sweetness and fragrance volume to the amber core. have an effect.
• the present invention is a flavoring agent comprising the compound represented by formula (I).
• R 1 is an alkyl group having 1 to 5 carbon atoms
• R 2 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
• R 1 is an alkyl group having 1 to 4 carbon atoms
• R 2 is a methyl group or an ethyl group.
• R 1 is a tert-butyl group
• R2 is an ethyl group
• the compound represented by formula (I) can be produced, for example, by the following method.
• R 1 is an alkyl group having 1 to 5 carbon atoms
• R 2 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
• the compound of formula (X) and the compound of formula (XI) are heated under basic (eg, sodium hydroxide) conditions to obtain the compound of formula (XII).
• Compounds of formula (XII) can be hydrogenated in the presence of hydrogen using certain catalysts (eg palladium-containing catalysts) to give compounds of formula (I).
• the resulting compound of formula (I) can be separated and purified by distillation or column chromatography.
• the compound represented by the formula (I) can be produced using a conventionally known method, for example, the method described in JP-A-2013-151482 under the same conditions.
• the present invention also provides a fragrance composition comprising a compound represented by formula (II) and a compound represented by formula (I),
• the mass ratio of the compound represented by formula (II) to the compound represented by formula (I) [compound represented by formula (II): compound represented by formula (I)] is 99.99. : 0.01 or more and 98:2 or less. That is, the mass ratio of the compound represented by formula (I) to the compound represented by formula (II) (compound represented by formula (I)/compound represented by formula (II)) is 0.01/ It is 99.99 or more and 2/98 or less.
• R 1 and R 3 are each independently an alkyl group having 1 to 5 carbon atoms
• R 2 and R 4 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
• the mass of the compound represented by the formula (II) and the compound represented by the formula (I) is, from the viewpoint of imparting honey-like sweetness and fragrance volume to the compound represented by formula (II), It is preferably 99.97:0.03 or more, more preferably 99.95:0.05 or more, and from the viewpoint of imparting an amber-like scent of the compound represented by formula (II), preferably 99 :1 or less, more preferably 99.20:0.80 or less, still more preferably 99.50:0.50 or less.
• the mass of the compound represented by the formula (II) and the compound represented by the formula (I) is, from the viewpoint of imparting honey-like sweetness and fragrance volume to the compound represented by formula (II), It is preferably 99.99:0.01 or more and 99:1 or less, more preferably 99.97:0.03 or more and 99.20:0.80 or less, and still more preferably 99.95:0.05 or more. 99.50: 0.50 or less.
• the mass ratio of the compound represented by formula (I) to the compound represented by formula (II) is represented by formula (II ) is preferably 0.01/99.99 or more and 1/99 or less, more preferably 0.03/99.97 or more and 0 .80/99.2 or less, more preferably 0.05/99.95 or more and 0.50/99.50 or less.
• R 1 is an alkyl group having 1 to 4 carbon atoms
• R 2 is a methyl group or an ethyl group.
• R 1 is a tert-butyl group
• R2 is an ethyl group
• R 3 is an alkyl group having 1 to 4 carbon atoms
• R4 is a methyl group or an ethyl group.
• R 3 is a tert-butyl group
• R4 is an ethyl group
• R 1 is an alkyl group having 1 to 4 carbon atoms
• R 2 is a methyl group or an ethyl group
• R 3 is an alkyl group having 1 to 4 carbon atoms
• R4 is a methyl group or an ethyl group.
• R 1 is a tert-butyl group
• R 2 is an ethyl group
• R 3 is a tert-butyl group
• R4 is an ethyl group.
• the compound represented by formula (II) can be produced by a conventionally known method, for example, the method described in JP-A-4-217937.
• the compound represented by formula (II) can be produced, for example, by the following method.
• R 3 is an alkyl group having 1 to 5 carbon atoms
• R 4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
• the compound of formula (XIII) and the compound of formula (XIV) are heated in the presence of a base (eg sodium hydroxide) to give the compound of formula (XV).
• a base eg sodium hydroxide
• Compounds of formula (XV) can be hydrogenated in the presence of hydrogen with a catalyst (eg a palladium catalyst) to give compounds of formula (II).
• the flavor preparation of the present invention comprising the compound represented by the formula (I) has a pleasant fruity (apple-like), herbal, and minty-like scent, and is therefore excellent in harmony with other various perfumes. By doing so, it is possible to create a characteristic fragrance effect.
• the flavoring agent comprising the compound represented by the formula (I) of the present invention may be used as a flavoring agent other than the compound represented by the formula (I), other flavoring ingredients that are usually used, or a blended flavoring agent having a desired composition. can be combined.
• a fragrance composition containing a flavoring agent composed of the compound represented by the formula (I) of the present invention and a fragrance other than the compound represented by the formula (I) is preferable, and the formula (I) of the present invention ) and a perfume composition other than the compound represented by the formula (I) and the compound represented by the formula (II).
• fragrances other than the compound represented by the formula (I) it is possible to impart, for example, a fruity (apple-like), herbal, or minty-like fragrance to the fragrance composition of the present invention.
• the fragrance composition of the present invention containing the compound represented by the formula (I) and the compound represented by the formula (II) has honey-like sweetness and aroma compared to the compound represented by the formula (II). volume is given.
• the fragrance composition of the present invention containing the compound represented by the formula (I) and the compound represented by the formula (II) is other than the compound represented by the formula (I) and the compound represented by the formula (II).
• the perfume of (1) it is possible to combine other commonly used perfume components and a compounded perfume having a desired composition.
• the scent and honey-like sweetness of the compound represented by the formula (II) and the volume of the scent can be applied to the perfume composition of the present invention. That is, the compound represented by the formula (I) of the present invention and the fragrance composition containing the compound represented by the formula (II) are represented by the compound represented by the formula (I) and the formula (II) It is preferable that the composition further contains a perfume other than the compound.
• perfumes that can be used in combination with the perfume of the present invention comprising the compound represented by formula (I) include alcohols, hydrocarbons, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, Fragrance ingredients such as carvone, lactone, nitrile, amine, Schiff base, natural essential oil and natural extract (except for the compound represented by formula (I)) can be mentioned. That is, the present invention provides alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, nitriles, compounds other than the compounds represented by the formula (I) and the compounds represented by the formula (II).
• a perfume composition comprising one or more of amines, natural essential oils and natural extracts, and the perfume of the present invention.
• R 1 and R 3 are each independently an alkyl group having 1 to 5 carbon atoms
• R 2 and R 4 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
• the ratio (compound represented by formula (I)/other perfume) is preferably 0.01/99.99 or more, more preferably 0.1/99. 9 or more, more preferably 1/99 or more, and from the same viewpoint, preferably 1/2 or less, more preferably 1/3 or less, still more preferably 1/4 or less, preferably 0.01/99 0.99 or more and 1/2 or less, more preferably 0.1/99.9 or more and 1/3 or less, and still more preferably 1/99 or more and 1/4 or less.
• the content of the flavoring agent composed of the compound represented by formula (I) is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, more preferably 0.2% by mass or more, preferably 20% by mass or less, more preferably 15% by mass or less, even more preferably 10% by mass or less, preferably 0.01% by mass % or more and 20 mass % or less, more preferably 0.1 mass % or more and 15 mass % or less, and still more preferably 0.2 mass % or more and 10 mass % or less.
• the compound represented by the formula (I) and the compound represented by the formula (II) include alcohols, hydrocarbons, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, carvone, lactones, nitriles, amines, Schiff bases, natural essential oils and natural extracts, etc. However, the compound represented by the formula (I) and the compound represented by the formula (II) are excluded).
• alcohols phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, nitriles, amines, natural essential oils and natural extracts are preferred in the perfume composition.
• Alcohols include aliphatic alcohols, terpene alcohols, aromatic alcohols, and other alcohols. Among these, aliphatic alcohols are preferred.
• Terpene alcohols include linalool, ethyl linalool, citronellol, hydroxycitronellol, geraniol, tetrahydrogeraniol, nerol, terpineol, ⁇ -terpineol, dihydromyrcenol, farnesol, nerolidol, cedrol, menthol, and borneol.
• Aromatic alcohols include phenylethyl alcohol, benzyl alcohol, dimethylbenzylcarbinol, phenylethyldimethylcarbinol, phenylhexanol, and the like.
• Aliphatic alcohols include cis-3-hexenol, 1-(2,2,6-trimethylcyclohexyl)-3-hexanol, sandal mysole core (trade name of Kao Corporation, 2-methyl-4-(2,2, 3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol), Ambercore (trade name of Kao Corporation, 1-(2-t-butylcyclohexyloxy)-2-butanol), Magnol ( Kao Corporation trade name, a mixture containing ethylnorbonylcyclohexanol as a main component), undecapertol (Givaudan trade name, 4-methyl-3-decen-5-ol), isobornylcyclohexanol, terpirosa ( Kao Corporation trade name, 3,6-dimethyl-2-heptanol) and the like.
• amber core is excluded from the "perfume composition of the present invention containing a compound represented by formula (I) and a
• glycols such as dipropylene glycol, florosa (trade name of Givaudan, chemical name: 4-methyl-2-(2-methylpropyl)tetrahydro-2H-4-pyranol), maltol, ethyl maltol, and the like. mentioned.
• hydrocarbons examples include limonene, ⁇ -pinene, ⁇ -pinene, terpinene, cedrene, longifolene, and valencene.
• Phenols include guaiacol, eugenol, dihydroeugenol, isoeugenol, thymol, paracresol, vanillin, ethylvanillin, and the like.
• Esters include aliphatic carboxylic acid esters, aromatic carboxylic acid esters, and other carboxylic acid esters.
• Aliphatic carboxylic acids forming aliphatic carboxylic acid esters include linear and branched carboxylic acids having 1 to 18 carbon atoms, among which carboxylic acids having 1 to 6 carbon atoms such as formic acid, acetic acid and propionic acid. , especially acetic acid.
• Examples of aromatic carboxylic acids that form aromatic carboxylic acid esters include benzoic acid, anisic acid, phenylacetic acid, cinnamic acid, salicylic acid, and anthranilic acid.
• Alcohols that form aliphatic and aromatic esters include straight and branched chain aliphatic alcohols having 1 to 5 carbon atoms and the perfume ingredient alcohols described above.
• Formic acid esters include linalyl formate, citronellyl formate, geranyl formate, and the like.
• Acetates include ethyl acetate, isoamyl acetate (isopentyl acetate), benzyl acetate, hexyl acetate, phenyl acetate, p-cresyl acetate, cis-3-hexenyl acetate, linalyl acetate, citronellyl acetate, geranyl acetate, neryl acetate, terpinyl acetate, nopyr acetate, bornyl acetate, isobornyl acetate, acetyl eugenol, acetyl isoeugenol, o-tert-butylcyclohexyl acetate, p-tert-butylcyclohexyl acetate, tricyclodecenyl acetate, phenylethyl Acetate, styralyl acetate, cinnamyl acetate, dimethylbenz
• Propionate esters include ethyl propionate, citronellyl propionate, tricyclodecenyl propionate, benzyl propionate, styralyl propionate, helvetride (trade name of Firmenich, 2-[1-( 3,3-dimethylcyclohexyl)ethoxy]-2-methylpropyl)propionate and the like.
• Butyric acid esters such as citronellyl butyrate, dimethylbenzylcarbyl n-butyrate, isoamyl n-butyrate, n-amyl n-butyrate, etc.; isobutyric acid esters such as tricyclodecenyl isobutyrate and phenoxyethyl isobutyrate. rates and the like.
• Valerate esters include methyl valerate, ethyl valerate, butyl valerate, amyl valerate, benzyl valerate, phenylethyl valerate, etc.; hexanoate esters include methylhexanoate, ethylhexanoate, allylhexa noate, linalyl hexanoate, citronellyl hexanoate and the like.
• heptanoic acid esters examples include methylheptanoate and allylheptanoate.
• nonenoic acid esters examples include methyl 2-nonenoate, ethyl 2-nonenoate, ethyl 3-nonenoate and the like.
• Benzoates include methyl benzoate, benzyl benzoate, 3,6-dimethyl benzoate and the like.
• Cinnamic acid esters include methyl cinnamate, benzyl cinnamate, and the like.
• salicylates examples include methyl salicylate, n-hexyl salicylate, cis-3-hexenyl salicylate, cyclohexyl salicylate, and benzyl salicylate.
• brassylate esters include ethylene brassylate and the like.
• Tiglic acid esters include geranyl tiglate, 1-hexyl tiglate, cis-3-hexenyl tiglate, and the like.
• Jasmonates include methyl jasmonate and the like; dihydrojasmonates include MDJ (trade name of Kao Corporation, methyl dihydrojasmonate, methyl (2-pentyl-3-oxocyclopentyl) acetate) and the like.
• glycidic acid esters examples include methyl 2,4-dihydroxy-ethylmethylphenylglycidate and 4-methylphenylethylglycidate.
• anthranilic acid esters examples include methyl anthranilate, ethyl anthranilate, and dimethyl anthranilate.
• glycolic acid esters examples include allyl cyclohexyl glycolate.
• esters include ethyl safranate (Givaudan, trade name, ethyl dihydrocyclogelate), porenate (Kao Corporation, trade name, ethyl-2-cyclohexylpropionate), flutate (Kao Corporation, trade name, ethyl tricyclo[5.2.1.0 2.6 ]decane-2-carboxylate), ethyl acetoacetate, fructone (IFF trade name, ethyl 2-(2-methyl-1,3-dioxolan-2-yl) acetate) ), manzanate (trade name of Givaudan, ethyl 2-methylpentanoate), ethyl 2-methylbutyrate, allylcyclohexylpropionate, and the like.
• ethyl safranate Givaudan, trade name, ethyl dihydrocyclogelate
• porenate Kao Corporation, trade name, ethyl-2-
• Rifarome (trade name of IFF, cis-3-hexenylmethyl carbonate), Jasmacikrat (trade name of Kao Corporation, methyl-cyclooctyl carbonate), Floramat (trade name of Kao Corporation, ethyl-2-t- butyl cyclohexyl carbonate) and the like.
• Aldehydes include n-octanal, n-nonanal, n-decanal, n-dodecanal, 2-methylundecanal, 10-undecenal, citronellal, citral, hydroxycitronellal, and tripral (IFF trade name, 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde), Cyclovertal (Kao Corporation trade name, dimethyl-3-cyclohexenyl-1-carboxaldehyde), benzaldehyde, phenylacetaldehyde, phenylpropylaldehyde, cinnamic Aldehyde, dimethyltetrahydrobenzaldehyde, Brugeonal (trade name of Givaudan, 3-(4-tert-butylphenyl)propanal), Lyral (trade name of IFF, hydroxymyracaldehyde), Polenal II (trade name of Kao Corporation,
• ketones include methylheptenone, dimethyloctenone, 3-octanone, hexylcyclopentanone, dihydrojasmon, belluton (trade name of Firmenich, 2,2,5-trimethyl-5-pentylcyclopentanone), and nectaryl (trade name of Givaudan).
• acetals include acetaldehyde ethyl phenyl propyl acetal, citral diethyl acetal, phenylacetaldehyde glyceryl acetal, ethyl acetoacetate ethylene glycol acetal, boazambrenforte (trade name of Kao Corporation, ethoxymethylcyclododecyl ether), troenane (trade name of Kao Corporation).
• Ethers include cedryl methyl ether, estragole, anethole, ⁇ -naphthyl methyl ether, ⁇ -naphthyl ethyl ether, limonene oxide, rose oxide, nerol oxide, 1,8-cineole, rose furan, ambroxan (Kao stock Company trade name, [3aR-(3a ⁇ ,5a ⁇ ,9a ⁇ ,9b ⁇ )]dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan), Herbervale (Kao Corporation trade name, 3, 3,5-trimethylcyclohexyl ethyl ether), galaxolide (trade name of IFF, hexamethylhexahydrocyclopentabenzopyran), phenylacetaldehyde dimethylacetal and the like.
• Carboxylic acids include benzoic acid, phenylacetic acid, cinnamic acid, hydrocinnamic acid, butyric acid, 2-hexenoic acid and the like.
• Lactones include ambretlide, ⁇ -decalactone, ⁇ -decalactone, ⁇ -valerolactone, ⁇ -nonalactone, ⁇ -undecalactone, ⁇ -hexalactone, ⁇ -jasmolactone, whiskey lactone, coumarin, cyclopentadeca nolide, cyclohexadecanolide, 11-oxahexadecanolide, butylidenephthalide, and the like.
• Nitriles include tridecene-2-nitrile, geranyl nitrile, citronellyl nitrile, dodecane nitrile and the like.
• Amines include indole, skatole, 6-methylquinoline, 6-isopropylquinoline, isobutylquinoline and the like.
• Schiff bases include aurantiol, ligandral, and the like.
• Natural essential oils and extracts include orange, lemon, lime, bergamot, vanilla, mandarin, peppermint, spearmint, lavender, galbanum, chamomile, rosemary, eucalyptus, sage, basil, rose, rockrose, geranium, jasmine and ylang. Natural oils such as ylang, anise, clove, ginger, nutmeg, cardamom, cedar, cypress, vetiver, patchouli, hay, lemongrass, labdanum, grapefruit, elemi oil, concrete, absolutes, resinoids, oleoresins, tinctures, infusions , balsam and the like.
• the content of these other fragrances can be appropriately selected depending on the type of the blended fragrance, the type of the desired fragrance, the strength of the fragrance, etc., but each is preferably is 0.0001% by mass or more, more preferably 0.001% by mass or more, and preferably 99.99% by mass or less, more preferably 80% by mass or less.
• the total content of other fragrances in the composition containing the fragrance composition of the present invention is preferably 5% by mass or more, more preferably 50% by mass or more, and preferably 99.99% by mass or less, More preferably, it is 99.95% by mass or less.
• the total amount of the compound represented by the formula (I) and the compound represented by the formula (II) and the mass ratio (total amount / amount of other fragrance) of these other fragrances is It is preferably 0.01/99.99 or more, more preferably 0.1/99.9 or more, still more preferably 1/99 or more from the viewpoint of exhibiting the function, and from the same viewpoint, preferably 1/2 Below, more preferably 1/3 or less, still more preferably 1/4 or less, preferably 0.01/99.99 or more and 1/2 or less, more preferably 0.1/99.9 or more and 1/3 or less , more preferably 1/99 or more and 1/4 or less.
• the content of the compound represented by formula (I) is preferably 0.01% by mass or more, more preferably 0.1% by mass, from the viewpoint of exhibiting the function as a flavoring agent.
• more preferably 0.2% by mass or more preferably 20% by mass or less, more preferably 15% by mass or less, still more preferably 10% by mass or less, preferably 0.01% by mass or more and 20% by mass
• the perfume composition of the present invention can be combined as a base with an oil agent that itself does not have an odor.
• an oil allows the fragrance components to be uniformly mixed, is easy to be blended into products, and facilitates the fragrance of an appropriate intensity.
• the oils include polyhydric alcohols such as ethylene glycol, propylene glycol, butylene glycol and dipropylene glycol; esters such as isopropyl myristate, dibutyl adipate and diethyl sebacate; hydrocarbons such as liquid paraffin and squalane; Surfactants such as oxyethylene alkyl ethers and sorbitan fatty acid esters are included.
• polyhydric alcohols and esters are preferable as the oil agent, and dipropylene glycol and isopropyl myristate are more preferable, from the viewpoint of solubility of all perfume ingredients.
• the content of such an oil agent in the fragrance composition is preferably 0.01% by mass or more, more preferably 1% by mass or more, still more preferably 5% by mass or more, and preferably 95% by mass or less, more preferably 90% by mass. % by mass or less, more preferably 80% by mass or less.
• the present invention also provides a detergent composition containing the perfume composition of the present invention, a cosmetic containing the perfume composition of the present invention, and a fiber treatment composition containing the perfume composition of the present invention.
• the detergent composition of the present invention is preferably a body detergent composition, a laundry detergent composition, or a hard surface detergent composition, more preferably a body detergent composition or a laundry detergent composition. , a laundry detergent composition is more preferred.
• body cleansing compositions include skin cleansing compositions, hair cleansing compositions, and soap compositions, with skin cleansing compositions being preferred.
• cleaning compositions for hard surfaces include all purpose cleaners and dish cleaning compositions.
• a softener composition is preferable as the fiber treatment composition of the present invention.
• Perfume, milky lotion, lotion, and sunscreen are preferable as the cosmetic of the present invention, and perfume is more preferable.
• the detergent composition of the present invention preferably contains an anionic surfactant, and further includes a nonionic surfactant, a pH adjuster, a viscosity adjuster, a solvent, an oil, Preservatives, water, etc. can be blended.
• the fiber treatment composition of the present invention preferably contains a cationic surfactant, and may further contain pH adjusters, solvents, oils, preservatives, water, and the like. can.
• the perfume of the present invention can contain solvents, water, etc. in addition to the perfume composition of the present invention.
• the flavoring agent comprising the compound represented by formula (I) and the flavoring composition of the present invention containing the flavoring agent have a pleasant fruity (apple-like), herbal, and minty-like scent. Furthermore, the fragrance composition of the present invention containing the compound represented by the formula (I) and the compound represented by the formula (II) imparts honey-like sweetness and fragrance volume to the amber core. You can give a new impression.
• the present invention provides the perfume composition of the present invention or the perfume composition of the present invention (“the perfume composition of the present invention containing a perfume composition comprising a compound represented by formula (I)” and “the perfume composition of the present invention represented by formula (I)
• the detergent composition is preferably a body detergent composition, a laundry detergent composition, or a hard surface detergent composition, more preferably a body detergent composition or a laundry detergent composition, and is more preferably a detergent composition for clothing.
• the body cleansing composition include skin cleansing compositions, hair cleansing compositions, and soap compositions, with skin cleansing compositions being preferred.
• the hard surface cleaning composition include all-purpose cleaners and tableware cleaning compositions. Perfume is preferable as the cosmetic.
• a softening agent composition is preferable as the fiber treatment composition.
• the perfume composition of the present invention is preferably 0.0001% by mass or more, more preferably 0.001% by mass or more, relative to the detergent composition, cosmetic or softener composition. It is used in an amount of preferably 30% by mass or less, more preferably 20% by mass or less, even more preferably 10% by mass or less, 1% by mass or less, and more preferably 0.1% by mass or less.
• this perfume composition is formulated with other ingredients as a perfume material, the sparkling impression of the top of the citrus scent, and the green and woody nuances along with the floral scent. A new impression can be given by adding a natural floral feeling like being in a flower shop.
• the perfume composition of the present invention may be combined with an oil agent that itself has no odor.
• the oil agent is the same as described in the perfume composition.
• the perfume composition of the present invention may contain, as other perfumes, other commonly used perfume components or blended perfumes of desired compositions. Such other perfumes are the same as those described in the perfume composition.
• a fragrance preparation comprising a compound represented by formula (I).
• R 1 is an alkyl group having 1 to 5 carbon atoms
• R 2 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
• R 1 is a tert-butyl group
• R 2 is an ethyl group
• R 1 and R 3 are each independently an alkyl group having 1 to 5 carbon atoms
• R 2 and R 4 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
• a fragrance agent consisting of a compound represented by formula (I), and alcohols, phenols, esters, carbonates, aldehydes, ketones, other than compounds represented by formulas (I) and (II),
• One or more of acetal, ether, lactone, nitrile, amine, natural essential oil and natural extract (hereinafter simply referred to as other perfume) mass ratio (amount of compound represented by formula (I) / total of other perfume) amount) is 0.01/99.99 or more and 1/2 or less, the fragrance composition according to ⁇ 3>.
• One or more of acetal, ether, lactone, nitrile, amine, natural essential oil and natural extract (hereinafter simply referred to as other perfume) mass ratio (amount of compound represented by formula (I) / total of other perfume) amount) is 0.1/99.9 or more and 1/3 or less, the fragrance composition according to ⁇ 3> or ⁇ 4>.
• a fragrance agent consisting of a compound represented by formula (I), and alcohols, phenols, esters, carbonates, aldehydes, ketones, other than compounds represented by formulas (I) and (II),
• One or more of acetal, ether, lactone, nitrile, amine, natural essential oil and natural extract (hereinafter simply referred to as other perfume) mass ratio (amount of compound represented by formula (I) / total of other perfume) amount) is 1/99 or more and 1/4 or less, the fragrance composition according to any one of ⁇ 3> to ⁇ 5>.
• the content of the flavoring agent composed of the compound represented by formula (I) is 0.01% by mass or more and 20% by mass or less, any of ⁇ 3> to ⁇ 6> Perfume composition as described.
• the content of the flavoring agent composed of the compound represented by formula (I) is 0.1% by mass or more and 15% by mass or less, any of ⁇ 3> to ⁇ 7> Perfume composition as described.
• ⁇ 9> Described in any of ⁇ 3> to ⁇ 8>, wherein the content of the flavoring agent comprising the compound represented by formula (I) in the fragrance composition is 0.2% by mass or more and 10% by mass or less perfume composition.
• a detergent composition comprising the perfume composition according to any one of ⁇ 3> to ⁇ 9>.
• a fiber treatment composition comprising the perfume composition according to any one of ⁇ 3> to ⁇ 9>.
• ⁇ 13> A method of using the flavoring agent described in ⁇ 1> or ⁇ 2> as a perfuming ingredient.
• R 1 and R 3 are each independently an alkyl group having 1 to 5 carbon atoms
• R 2 and R 4 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
• the mass ratio of the compound represented by formula (II) to the compound represented by formula (I) [compound represented by formula (II): compound represented by formula (I)] is The fragrance composition according to ⁇ 14> or ⁇ 15>, wherein 99.97:0.03 or more and 99.20:0.80 or less.
• the mass ratio of the compound represented by formula (II) to the compound represented by formula (I) [compound represented by formula (II): compound represented by formula (I)] is The fragrance composition according to any one of ⁇ 14> to ⁇ 16>, wherein 99.95:0.05 or more and 99.50:0.50 or less.
• ⁇ 22> The total amount of the compound represented by formula (I) and the compound represented by formula (II), and the compounds other than the compounds represented by formula (I) and formula (II), alcohol, phenol, One or more of esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, nitriles, amines, natural essential oils and natural extracts (hereinafter simply referred to as other fragrances) mass ratio (formula (I) and formula (II).
• ⁇ 24> The fragrance composition according to any one of ⁇ 14> to ⁇ 23>, wherein the content of the compound represented by formula (I) in the fragrance composition is 0.01% by mass or more and 20% by mass or less. .
• ⁇ 25> The fragrance composition according to any one of ⁇ 14> to ⁇ 24>, wherein the content of the compound represented by formula (I) in the fragrance composition is 0.1% by mass or more and 15% by mass or less. .
• ⁇ 26> The fragrance composition according to any one of ⁇ 14> to ⁇ 25>, wherein the content of the compound represented by formula (I) in the fragrance composition is 0.2% by mass or more and 10% by mass or less. .
• ⁇ 27> A cosmetic containing the fragrance composition according to any one of ⁇ 14> to ⁇ 26>.
• a detergent composition comprising the perfume composition according to any one of ⁇ 14> to ⁇ 26>.
• a fiber treatment composition comprising the perfume composition according to any one of ⁇ 14> to ⁇ 26>.
• ⁇ 30> A method of using the perfume composition according to any one of ⁇ 14> to ⁇ 26> as a perfuming ingredient.
• % means “% by mass” unless otherwise specified. Moreover, the mass of the catalyst is the mass in a dry state.
• GC device Agilent Technologies Inc. 7890B, flame ionization detector Column: When analyzing the yield, DB-1 (capillary column, 100% dimethylpolysiloxane, inner diameter 0.25 mm, length 30 m, film thickness 0.25 ⁇ m, manufactured by Agilent Technologies, Inc.) was used.
• DB-1 capillary column, 100% dimethylpolysiloxane, inner diameter 0.25 mm, length 30 m, film thickness 0.25 ⁇ m, manufactured by Agilent Technologies, Inc.
• DB-WAX capillary column, polyethylene glycol, inner diameter 0.25 mm, length 30 m, film thickness 0.25 ⁇ m, manufactured by Agilent Technologies
• Carrier gas He, 1.5 mL/min
• Injection conditions 300°C, split ratio 100/1
• Injection amount 1 ⁇ L
• Detection conditions FID method, 300°C
• Column temperature conditions Starting from 80°C, the temperature was raised to 300°C at a rate of 10°C/min. After that, it was held at 300° C. for 10 minutes.
• Example 1 As a result of evaluating the odor of the fragrance composition obtained in Example 1 (composition of 6-t-butyl-2-ethyl-1,4-dioxaspiro[4,5]decane alone), fruity, apple-like, honey It was confirmed to have a pleasant aroma as a flavoring agent, with a sweetness like mint and slightly herbal, mint-like, and wood-like aspects. No chemical-like stimulus, tobacco-like, or leather-like odor was perceived, confirming high versatility when used as a mixed perfume.
• volume means strength, depth, and fullness of fragrance, and volume is preferable for fragrances.
• the perfume composition of the present invention exhibited the effect of imparting honey-like sweetness and fragrance volume while maintaining strong amber-like, wood-like, and slightly camphor-like scents. .
• Example 10 Formulation Example 1
• a sensory evaluation of the product was carried out. The sensory evaluation was carried out by the same method as in Examples 1-9 and Comparative Example 1.
• Table 4 shows the results obtained. Regarding the evaluation result, the degree of effect is relatively evaluated on a scale of 5, and the higher the value, the better.
• Example 11 Formulation Example 2] 6-t-Butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) obtained in Reference Example 3 was added to 925 parts by mass of a pear-flavored perfume having the following composition. A sensory evaluation of the composition was carried out. The sensory evaluation was performed by the same method as that for evaluating Examples 1-10 and Comparative Examples 1-2. Table 7 shows the results obtained. Regarding the evaluation result, the degree of effect is relatively evaluated on a scale of 5, and the higher the value, the better.
• Example 12 Formulation Example 3
• a sensory evaluation of the product was carried out. The sensory evaluation was performed by the same method as that for evaluating Examples 1-11 and Comparative Examples 1-3. Table 10 shows the results obtained. Regarding the evaluation result, the degree of effect is relatively evaluated on a scale of 5, and the higher the value, the better.
• Example 13 Formulation Example 4
• a sensory evaluation of the product was carried out. The sensory evaluation was performed by the same method as that for evaluating Examples 1-12 and Comparative Examples 1-4. The results obtained are shown in Table 13. Regarding the evaluation result, the degree of effect is relatively evaluated on a scale of 5, and the higher the value, the better.
• Example 14 Formulation Example 5
• a sensory evaluation of the product was carried out. The sensory evaluation was performed by the same method as that for evaluating Examples 1-13 and Comparative Examples 1-5. The results obtained are shown in Table 16. Regarding the evaluation result, the degree of effect is relatively evaluated on a scale of 5, and the higher the value, the better.
• Example 15 Formulation Example 6
• a sensory evaluation of the product was carried out. The sensory evaluation was performed by the same method as that for evaluating Examples 1-14 and Comparative Examples 1-6. The results obtained are shown in Table 19. Regarding the evaluation result, the degree of effect is relatively evaluated on a scale of 5, and the higher the value, the better.
• Example 16 Formulation Example 7] 1-(2-t-butylcyclohexyloxy)-2-butanol (4) obtained in Reference Example 2 and 1-(2-t-butylcyclohexyloxy)-2-butanol (4) obtained in Reference Example 3 were added to 730 parts by mass of a green apple-like mixed perfume having the following composition. A sensory evaluation was carried out on the composition to which 6-t-butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) was added. The sensory evaluation was performed by the same method as that for evaluating Examples 1-15 and Comparative Examples 1-7. The results obtained are shown in Table 22. Regarding the evaluation result, the degree of effect is relatively evaluated on a scale of 5, and the higher the value, the better.
• the flavoring agent comprising the compound of formula (I) of the present invention and the flavoring composition containing the flavoring agent, it is possible to provide a flavoring composition with a preferable fruity (apple-like), herbal, or minty-like scent.
• the perfume composition containing the compound of formula (I) and the compound of formula (II) imparts honey-like sweetness and odor volume to the amber core.

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• 2022
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