Classifications

• • 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
  • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
• • 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
  • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
  • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic 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
  • A61K8/33—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
  • 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
  • A61L9/015—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone
  • A61L9/02—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air by heating or combustion
• • 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
  • A61L9/015—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone
  • A61L9/04—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air without heating
• • 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
  • A61L9/14—Disinfection, sterilisation or deodorisation of air using sprayed or atomised substances including air-liquid contact processes
• • 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
  • A61Q5/00—Preparations for care of the hair
• • 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
• • 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
  • A61Q5/12—Preparations containing hair conditioners
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
  • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
  • C07C69/78—Benzoic acid esters
• • 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
  • 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
• • C—CHEMISTRY; METALLURGY
  • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
  • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
  • C12P7/00—Preparation of oxygen-containing organic compounds
  • C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
• • C—CHEMISTRY; METALLURGY
  • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
  • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
  • C12P7/00—Preparation of oxygen-containing organic compounds
  • C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
  • C12P7/26—Ketones
• • 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
  • D06M13/12—Aldehydes; Ketones
• • 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
  • D06M13/224—Esters of carboxylic acids; Esters of carbonic acid

Definitions

• the present invention relates to a flavor or fragrance precursor which releases an aldehyde or a ketone by the action of hydrolase, a technique for lasting lingering fragrance, and a deodorization technique of releasing, as a deodorizing component, an aldehyde or a ketone by the action of a microorganism and mitigating the odor caused by microorganisms.
• Patent Literature 1 a fixative such as p-menthane-3,8-diol (Patent Literature 1) and 3-(menthoxy)-1,2-propanediol (Patent Literature 2) has been proposed.
• the flavor or fragrance is highly useful in that not only an offensive odor is reduced but also a malodor can be changed to a pleasant scent.
• a flavor or fragrance component such as aldehydes or ketones has an aromaticity and is expected to provide a sensory deodorization effect.
• aldehydes particularly, aldehydes have not only a sensuous deodorization effect but also further have a chemical deodorization effect (Patent Literature 6) and therefore, these are expected to provide a higher deodorizing effect.
• Patent Literature 1 JP-A-4-337395
• Patent Literature 2 JP-A-2002-88391
• Patent Literature 3 JP-A-2009-46442
• Patent Literature 4 JP-A-2004-315502
• Patent Literature 5 JP-A-11-286428
• Patent Literature 6 JP-A-2001-303090
• the lingering fragrance may be enhanced, but there is a problem that stabilization in a product is difficult and the application field is limited; and since a fragrance is not released unless the capsule is physically broken, a fragrance may be emitted when the lingering fragrance is not needed, or a fragrance is not given when the lingering fragrance is needed, causing a gap between the need for a fragrance and the timing of emitting a fragrance from the capsule.
• the lingering fragrance property may be somewhat enhanced, but fully satisfactory substantivity of lingering fragrance has not been obtained.
• an antimicrobial in a personal care product such as a deodorant agent, not only bacteria causing a malodor but also bacteria useful on skin are killed, and the skin flora balance may be lost.
• the indigenous skin bacteria also fulfill the role of keeping the pH weakly acidic and preventing skin infections and in view of maintaining the health of the skin, frequent use of an antimicrobial is not necessarily favorable.
• flavor or fragrance having a high fragrance intensity or extremely raise the perfuming amount, but, for example, at the start of use of a deodorant product, during use of a body cleaner, or during drying of clothing, the flavor or fragrance smells too strong, and the user may be offended.
• the present invention has been made in consideration of these conventional circumstances, and an object of the present invention is to develop a technique enabling a lingering fragrance having fresh feeling to last.
• Another object of the present invention is to develop a deodorizing method and a deodorant, which can exert a deodorizing effect on the malodor caused by microorganisms at the same timing as sufficient proliferation of microorganisms and generation of malodor.
• the present inventors have found that when a compound having a specific structure releases an aromatic aldehyde or ketone by the action of a hydrolase, the substantivity of lingering fragrance having fresh feeling is increased.
• the present inventors have found that when a compound having a specific structure releases an aldehyde or a ketone by the action of a microorganism, the odor caused by microorganisms is alleviated.
• the present invention relates to the following [1] to [17].
• each of R 1 , R 2 and R 3 independently represents a hydrogen atom, an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent, R 1 and R 2 or R 1 and R 3 may form a ring, and Ar represents an aryl group which may have a substituent), and:
• R 1 , R 2 and R 3 have the same definitions as those in formula (1), and R 1 and R 2 or R 1 and R 3 may form a ring).
• a deodorizing method including allowing a microorganism to act on a compound represented by formula (1) to release, as a deodorizing component, an aldehyde or ketone represented by formula (2) and mitigating an odor caused by microorganism:
• each of R 1 , R 2 and R 3 independently represents a hydrogen atom, an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent, R 1 and R 2 or R 1 and R 3 may form a ring, and Ar represents an aryl group which may have a substituent), and:
• R 1 , R 2 and R 3 have the same definitions as those in formula (1), and R 1 and R 2 or R 1 and R 3 may form a ring).
• microorganism is at least one selected from the group consisting of Staphylococcus bacteria, Corynebacterium bacteria, Propionibacterium bacteria, Pseudomonas bacteria, Bacillus bacteria, Moraxella bacteria, and Malassezia fungi.
• each of R 1 , R 2 and R 3 is independently a hydrogen atom, an alkyl group having 1 to 13 carbon atoms, which may have a substituent, or an alkenyl group having 2 to 13 carbon atoms, which may have a substituent.
• each of R 1 , R 2 and R 3 independently represents a hydrogen atom, an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent, R 1 and R 2 or R 1 and R 3 may form a ring, and Ar represents an aryl group which may have a substituent).
• each of R 1 , R 2 and R 3 is independently a hydrogen atom, an alkyl group having 1 to 13 carbon atoms, which may have a substituent, or an alkenyl group having 2 to 13 carbon atoms, which may have a substituent.
• each of R 1 , R 2 and R 3 independently represents a hydrogen atom, an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent, R 1 and R 2 or R 1 and R 3 may form a ring, and Ar represents an aryl group which may have a substituent).
• each of R 1 , R 2 and R 3 is independently a hydrogen atom, an alkyl group having 1 to 13 carbon atoms, which may have a substituent, or an alkenyl group having 2 to 13 carbon atoms, which may have a substituent.
• the compound represented by formula (1) can release an aldehyde or ketone having aromaticity by the action of a hydrolase and increase the substantivity of a lingering fragrance having fresh feeling.
• a flavor or fragrance composition an aroma product, a laundry care product, a hair care product, a cosmetic, or a cleaner, each of which emits an aroma when allowing a hydrolysate to act thereon and causes a lingering fragrance having fresh feeling to last, can be provided.
• the compound represented by formula (1) can release an aldehyde or ketone having a deodorizing effect, represented by formula (2), by the action of a microorganism and mitigate the odor caused by microorganisms.
• a deodorant which can emit a deodorizing component when allowing a microorganism to act thereon and mitigate the offensive odor caused by microorganisms, can be provided.
• a compound represented by formula (1) is used as a flavor or fragrance precursor and by allowing a hydrolysate to act thereon, an aldehyde or a ketone, which is a compound represented by formula (2) as a flavor or fragrance component, can be emitted.
• an aldehyde or ketone which is a deodorizing component represented by formula (2), can be emitted, and this makes it possible to mitigate the odor caused by microorganisms and perform the deodorization.
• each of R 1 , R 2 and R 3 independently represents a hydrogen atom, an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent, R 1 and R 2 or R 1 and R 3 may form a ring, and Ar represents an aryl group which may have a substituent.
• R 1 , R 2 and R 3 have the same definitions as those in formula (1).
• R 1 and R 2 or R 1 and R 3 may form a ring.
• the alkyl group, the cycloalkyl group, the alkenyl group, the aryl group and the aralkyl group, each of which is represented by R 1 , R 2 and R 3 , are described. Each of these groups may have a substituent.
• the alkyl group includes, for example, a straight chain or branched alkyl group having 1 to 30 carbon atoms, preferably 1 to 13 carbon atoms.
• examples thereof include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, a n-pentyl group, a 2-pentyl group, a 3-pentyl group, a tert-pentyl group, a 2-methylbutyl group, a 3-methylbutyl group, a 2,2-dimethylpropyl group, a 1,2-dimethylpropyl group, a n-hexyl group, a 2-hexyl group, a 3-hexyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 4-methylpenty
• cycloalkyl group examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc.
• the alkenyl group includes, for example, a straight chain or branched alkenyl group having 2 to 20 carbon atoms, preferably 2 to 13 carbon atoms, and a cyclic alkenyl group having 3 to 20 carbon atoms, preferably 5 to 10 carbon atoms.
• examples of the alkenyl group include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-cyclopentenyl group, a 3-cyclopentenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, a 5-hexenyl group, a 4-methyl-3-pentenyl group, a 4,8-dimethyl-3,7-nonadienyl group, a 1-cyclohexenyl group, a 3-cyclohexenyl group, a 1,5-dimethyl-4-hexenyl group, a 1,5-dimethyl-1,4-hexa
• the aryl group includes, for example, an aryl group having 6 to 14 carbon atoms. Specifically, examples thereof include a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a biphenyl group, etc.
• aralkyl group for example, an aralkyl group having 7 to 12 carbon atoms is preferred. Specifically, examples thereof include a benzyl group, a 2-phenylethyl group, a 1-phenylpropyl group, etc.
• Each of the groups R 1 to R 3 other than a hydrogen atom may have a substituent.
• substituents include an alkenyl group, an alkynyl group, an aryl group, an aliphatic heterocyclic group, an aromatic heterocyclic group, an alkoxy group, an alkylenedioxy group, an aryloxy group, an aralkyloxy group, a heteroaryloxy group, an amino group, a substituted amino group, a nitro group, a cyano group, an alkoxycarbonyl group, a halogen atom, an alkyl halide group, etc.
• the alkenyl group as the substituent on R 1 to R 3 may be a straight chain or branched alkenyl group and includes, for example, an alkenyl group having 2 to 20 carbon atoms, preferably 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms. Specifically, examples thereof include a vinyl group, a propenyl group, a 1-butenyl group, a pentenyl group, a hexenyl group, etc.
• the alkynyl group as the substituent on R 1 to R 3 may be a straight chain or branched alkynyl group and includes, for example, an alkynyl group having 2 to 15 carbon atoms, preferably 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms. Specifically, examples thereof include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 3-butynyl group, a pentynyl group, a hexynyl group, etc.
• the aryl group as the substituent on R 1 to R 3 includes, for example, an aryl group having 6 to 14 carbon atoms. Specifically, examples thereof include a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a biphenyl group, a tolyl group, a xylyl group, a mesityl group, a methoxyphenyl group, a dimethoxyphenyl group, a fluorophenyl group, etc.
• the aliphatic heterocyclic group as the substituent on R 1 to R 3 includes, for example, a group having 2 to 14 carbon atoms and containing at least one, preferably 1 to 3, hetero atoms such as nitrogen atom, oxygen atom and sulfur atom.
• the aliphatic heterocyclic group includes a 5- or 6-membered monocyclic aliphatic heterocyclic group and a polycyclic or condensed ring aliphatic heterocyclic group.
• aliphatic heterocyclic group examples include a 2-oxo-1-pyrrolidinyl group, a piperidino group, a piperazinyl group, a morpholino group, a tetrahydrofuryl group, a tetrahydropyranyl group, a tetrahydrothienyl group, etc.
• the aromatic heterocyclic group as the substituent on R 1 to R 3 includes, for example, a group having 2 to 15 carbon atoms, preferably 3 to 11 carbon atoms, and containing at least one, preferably 1 to 3, hetero atoms such as nitrogen atom, oxygen atom and sulfur atom.
• the aromatic heterocyclic group includes a 5- or 6-membered monocyclic aromatic heterocyclic group and a polycyclic or condensed ring aromatic heterocyclic group.
• aromatic heterocyclic group examples include a furyl group, a thienyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a pyrazolinyl group, an imidazolyl group, an oxazolinyl group, a thiazolinyl group, a benzofuryl group, a benzothienyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a phtharazinyl group, a quinazolinyl group, a naphthylidinyl group, a cinnolinyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, etc.
• the alkoxy group as the substituent on R 1 to R 3 includes, for example, a straight chain or branched alkoxy group having 1 to 6 carbon atoms. Specifically, examples thereof include a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, a 2-butoxy group, an isobutoxy group, a tert-butoxy group, a n-pentyloxy group, a 2-methylbutoxy group, a 3-methylbutoxy group, a 2,2-dimethylpropoxy group, a n-hexyloxy group, a 2-methylpentyloxy group, a 3-methylpentyloxy group, a 4-methylpentyloxy group, a 5-methylpentyloxy group, etc.
• the alkylenedioxy group as the substituent on R 1 to R 3 includes, for example, an alkylenedioxy group having 1 to 3 carbon atoms. Specifically, examples thereof include a methylenedioxy group, an ethylenedioxy group, a propylenedioxy group, an isopropylidenedioxy group, etc.
• the aryloxy group as the substituent on R 1 to R 3 includes, for example, an aryloxy group having 6 to 14 carbon atoms. Specifically, examples thereof include a phenoxy group, a naphthyloxy group, an anthryloxy group, etc.
• the aralkyloxy group as the substituent group for R 1 to R 3 includes, for example, an aralkyloxy group having 7 to 12 carbon atoms. Specifically, examples thereof include a benzyloxy group, a 2-phenylethoxy group, a 1-phenylpropoxy group, a 2-phenylpropoxy group, a 3-phenylpropoxy group, a 1-phenylbutoxy group, a 2-phenylbutoxy group, a 3-phenylbutoxy group, a 4-phenylbutoxy group, a 1-phenylpentyloxy group, a 2-phenylpentyloxy group, a 3-phenylpentyloxy group, a 4-phenylpentyloxy group, a 5-phenylpentyloxy group, a 1-phenylhexyloxy group, a 2-phenylhexyloxy group, a 3-phenylhexyloxy group, a 4-phenylhexyloxy group,
• the heteroaryloxy group as the substituent on R 1 to R 3 includes, for example, a heteroaryloxy group having 2 to 14 carbon atoms and containing at least one, preferably 1 to 3, hetero atoms such as nitrogen atom, oxygen atom and sulfur atom.
• a heteroaryloxy group having 2 to 14 carbon atoms and containing at least one, preferably 1 to 3, hetero atoms such as nitrogen atom, oxygen atom and sulfur atom include a 2-pyridyloxy group, a 2-pyrazyloxy group, a 2-pyrimidyloxy group, a 2-quinolyloxy group, etc.
• Examples of the substituted amino group as the substituent on R 1 to R 3 include a mono- or dialkylamino group, such as N-methylamino group, N,N-dimethylamino group, N,N-diethylamino group, N,N-diisopropylamino group and N-cyclohexylamino group; a mono- or diarylamino group, such as N-phenylamino group, N,N-diphenylamino group, N-naphthylamino group and N-naphthyl-N-phenylamino group; and a mono- or diaralkylamino group, such as N-benzylamino group and N,N-dibenzylamino group; etc.
• a mono- or dialkylamino group such as N-methylamino group, N,N-dimethylamino group, N,N-diethylamino group, N,N-diisoprop
• the alkoxycarbonyl group as the substituent on R 1 to R 3 is preferably, for example, an alkoxycarbonyl group having 1 to 30 carbon atoms.
• examples thereof include a methoxycarbonyl group, an ethoxycarbonyl group, a n-propoxycarbonyl group, an isopropoxycarbonyl group, a n-butoxycarbonyl group, a 2-butoxycarbonyl group, an isobutoxycarbonyl group, a tert-butoxycarbonyl group, a n-pentyloxycarbonyl group, a 2-methylbutoxycarbonyl group, a 3-methylbutoxycarbonyl group, a 2,2-dimethylpropoxycarbonyl group, a n-hexyloxycarbonyl group, a 2-methylpentyloxycarbonyl group, a 3-methylpentyloxycarbonyl group, a 4-methylpentyloxycarbonyl group, a 5-methylpentyloxycarbonyl
• halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.
• the alkyl halide group as the substituent on R 1 to R 3 is preferably, for example, a perhalogenoalkyl group having 1 to 10 carbon atoms.
• a perhalogenoalkyl group having 1 to 10 carbon atoms examples thereof include a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, an undecafluoropentyl group, a heptadecafluorooctyl group, an undecafluorocyclohexyl group, a dichloromethyl group, etc.
• examples of the ring formed by R 1 and R 2 or R 1 and R 3 include a cyclopentane ring, a cyclohexane ring, an indane ring, a tetralin ring, a cyclopentene ring, a cyclohexene ring, a cycloheptene ring, an indene ring, a dihydronaphthalene ring, an octahydronaphthalene ring, a decahydronaphthalene ring, etc. These rings may be substituted with the above-described alkyl group or the like.
• examples of the ring formed by R 1 and R 2 or R 1 and R 3 include a cyclopentane ring, a cyclohexane ring, an indane ring, a tetralin ring, a cyclopentene ring, a cyclohexene ring, a cycloheptene ring, an indene ring, a dihydronaphthalene ring, an octahydronaphthalene ring, a decahydronaphthalene ring, etc. These rings may be substituted with the above-described alkyl group or the like.
• each of R 1 , R 2 and R 3 is preferably a hydrogen atom, an alkyl group having 1 to 13 carbon atoms, which may have a substituent group, or an alkenyl group having 2 to 13 carbon atoms, which may have a substituent.
• the alkyl group having 1 to 13 carbon atoms which may have a substituent, is preferably, for example, a straight chain or branched alkyl group having 1 to 13 carbon atoms.
• examples thereof include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, a n-pentyl group, a 2-pentyl group, a 3-pentyl group, a tert-pentyl group, a 2-methylbutyl group, a 3-methylbutyl group, a 2,2-dimethylpropyl group, a 1,2-dimethylpropyl group, a n-hexyl group, a 2-hexyl group, a 3-hexyl group, a 2-methylpentyl group, a 3-methylpentyl group
• alkenyl group having 2 to 13 carbon atoms which may have a substituent, for example, a straight chain or branched alkenyl group having 2 to 13 carbon atoms, and a cyclic alkenyl group having 3 to 13 carbon atoms, are preferred.
• examples thereof include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-cyclopentenyl group, a 3-cyclopentenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, a 5-hexenyl group, a 4-methyl-3-pentenyl group, a 1-octenyl group, a 2-octenyl group, a 4,8-dimethyl-3,7-nonadienyl group, a 1-cyclohexenyl group, a 3-cyclohexenyl group, a 4-methyl-3-pentenyl group, a 1,5-penten
• each of R 1 and R 2 is an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or a hydrogen atom, and R 3 is a hydrogen atom.
• the alkyl group having 1 to 8 carbon atoms is preferably, for example, a straight chain or branched alkyl group having 1 to 8 carbon atoms.
• examples thereof include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, a n-pentyl group, a 2-pentyl group, a 3-pentyl group, a tert-pentyl group, a 2-methylbutyl group, a 3-methylbutyl group, a 2,2-dimethylpropyl group, a 1,2-dimethylpropyl group, a n-hexyl group, a 2-hexyl group, a 3-hexyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 4-methylpenty
• alkenyl group having 2 to 8 carbon atoms specifically, examples thereof include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-cyclopentenyl group, a 3-cyclopentenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, a 5-hexenyl group, a 4-methyl-3-pentenyl group, a 1-octenyl group, a 2-octenyl group, a 1-cyclohexenyl group, a 3-cyclohexenyl group, a 4-methyl-3-pentenyl group, a 1,5-dimethyl-1,4
• a cyclohexene ring and a cyclohexane group are preferred.
• the substituent substituted on the cyclohexene ring and cyclohexane ring is preferably an alkyl group having 1 to 3 carbon atoms.
• the substitution may be a single substitution or a plurality of substitutions.
• the alkyl group having 1 to 3 carbon atoms is preferably, for example, a straight chain or branched alkyl group having 1 to 3 carbon atoms. Specifically, examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, etc.
• the aryl group includes, for example, an aryl group having 6 to 14 carbon atoms. Specifically, examples thereof include a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, etc.
• a phenyl group is preferred.
• the substituent which may be substituted on the aryl group includes, for example, an alkyl group having 1 to 8 carbon atoms. Specifically, examples thereof include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, a n-pentyl group, a 2-pentyl group, a 3-pentyl group, a tert-pentyl group, a 2-methylbutyl group, a 3-methylbutyl group, a 2,2-dimethylpropyl group, a 1,2-dimethylpropyl group, a n-hexyl group, a 2-hexyl group, a 3-hexyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 4-methylpentyl group, a 1,1
• a compound represented by formula (1) of the present invention particularly, in view of fragrance, fragrance emission performance and deodorizing effect, a compound represented by the following formula (3) and a compound represented by formula (4) are preferred.
• the compound represented by formula (1) used in the present invention can be easily synthesized by a known method.
• the compound represented by formula (3) can be synthesized according to the method described, for example, in Helv. Chim. Acta. 1988, 71, 1000-1004. This method can be represented by Scheme 1 below.
• the compound represented by formula (3) can be prepared by reacting a mixed solution of citronellal (compound of formula (5)), benzoic anhydride, triethylamine, and benzoate salt at a temperature ranging from 100 to 150° C.
• benzoate salt potassium benzoate and sodium benzoate are preferred.
• the thus-obtained compound of formula (3) can be isolated in the usual manner, such as extraction, distillation, recrystallization or chromatography of every sort.
• the wavy line represents either one of E and Z geometric isomers or a mixture thereof.
• the compound represented by formula (1) of the present invention can be used as a flavor or fragrance precursor.
• a hydrolysate By allowing a hydrolysate to act on the compound represented by formula (1), an aldehyde or ketone represented by formula (2), which is a flavor or fragrance component, can be released.
• the hydrolysate includes lipase, protease, amylase, glycosidase, etc., and among these, in view of hydrolysis rate, lipase is preferred.
• the lipase is not particularly limited and, as long as it is an enzyme that breaks down fat, may be a naturally occurring material or a formulated commercial product.
• the aldehyde represented by formula (2) which is a flavor or fragrance component or the later-described deodorizing component, includes a straight chain or branched aliphatic aldehyde having 6 to 13 carbon atoms, trans-2-hexenal, cis-3-hexenal, 2,6-nonadienal, cis-4-decenal, trans-4-decenal, undecylene aldehyde, trans-2-dodecenal, trimethylundecenal, 2,6,10-trimethyl-5,9-undecadienal, 2,6-dimethyl-5-heptenal, citral, citronellal, hydroxycitronellal, perillaldehyde, citronellyloxyacetaldehyde, 2,4-dimethyl-3-cyclohexenylcarboxyaldehyde, 2,4,6-trimethyl-3-cyclohexene-1-carboxyaldehyde, 5-methoxy-oc
• the ketone represented by formula (2) which is a flavor or fragrance component or the later-described deodorizing component, includes methyl amyl ketone, ethyl amyl ketone, methyl hexyl ketone, methyl nonyl ketone, methylheptenone, Koavone, camphor, carvone, menthone, isomenthone, pulegone, piperitone, fenchone, geranylacetone, cedryl methyl ketone, nootkatone, ⁇ -ionone, ⁇ -ionone, ⁇ -methylionone, ⁇ -isomethylionone, ⁇ -isomethylionone, allylionone, ⁇ -irone, ⁇ -irone, ⁇ -irone, ⁇ -damascone, ⁇ -damascone, ⁇ -damascone, damascenone, ⁇ -dinascone, ⁇ -din
• an aldehyde or ketone represented by formula (2) which is a deodorizing component, can be released.
• the microorganism that can cause the compound represented by formula (1) of the present invention to release, as a deodorizing component, an aldehyde or ketone represented by formula (2) includes Staphylococcus bacteria, Corynebacterium bacteria, Propionibacterium bacteria, Pseudomonas bacteria, Bacillus bacteria, Moraxella bacteria, Malassezia fungi, etc.
• examples thereof include Staphylococcus aureus, Staphylococcus epidermidis, Corynebacterium xerosis, Propionibacterium acnes, Pseudomonas aeruginosa, Bacillus subtilis, Moraxella osloensis, Malassezia furfur , etc.
• the compound represented by formula (1) of the present invention can be blended in a flavor or fragrance composition.
• the compound represented by formula (1) can be used singly or in combination of two or more kinds and can also be appropriately used in combination with a known flavor or fragrance component.
• Examples of the known flavor or fragrance component include natural essential oils, such as lemon oil, orange oil, lime oil, bergamot oil, lavandin oil, lavender oil, geranium oil, rose oil and sandalwood oil; hydrocarbons, such as ⁇ -pinene, ⁇ -pinene, limonene, p-cymene and thujone; aliphatic alcohols, such as octanol and p-tert-butylcyclohexanol; terpene-based alcohols, such as menthol, citronellol and geraniol; aromatic alcohols, such as benzyl alcohol and phenylethyl alcohol; aliphatic aldehydes; terpene-based aldehydes; aromatic aldehydes; acetals; chain ketones; cyclic ketones, such as damascone, ⁇ -ionone and methylionone; terpene-based ketones, such as carvone, men
• a solvent for example, ethanol, isopropyl alcohol, ethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, pentylene glycol, hexylene glycol, polyethylene glycol, diethyl phthalate, isopropyl myristate, triethyl citrate, benzyl benzoate, glycerin, triacetin, benzyl alcohol, paraffin, isoparaffin, a rosin ester derivative such as Hercolyn, etc., glycol ethers such as 3-methoxy-3-methyl-1-butanol, ethyl carbitol (diethylene glycol monoethyl ether), ethylene glycol monomethyl ether, propylene glycol monomethyl ether, ethylene glycol monoethyl ether, dipropylene glycol monomethyl ether, tripropylene glycol methyl ether, dipropylene glycol dimethyl methyl ether, dipropylene glycol di
• a known component such as higher alcohol, surfactant, antioxidant, ultraviolet absorber, chelating agent, solubilizing agent, stabilizing agent, cooling sensation agent, preservative, antimicrobial, bactericide, fungicide, insecticidal component and coloring matter, may be further mixed, if desired.
• the blending amount of the compound represented by formula (1) of the present invention in the flavor or fragrance composition is not strictly restricted and can be variously changed according to use of the flavor or fragrance composition.
• the blending amount of the compound represented by formula (1) of the present invention in the flavor or fragrance composition is preferably from 0.1 to 95.0% by mass, more preferably from 0.5 to 80.0% by mass.
• the compound represented by formula (1) of the present invention can be used, individually or in combination of two or more kinds, for a product, such as aroma product, laundry care product, hair care product, cosmetic or cleaner.
• the product such as aroma product, laundry care product, hair care product, cosmetic or cleaner
• a compounded flavor or fragrance for the purpose of letting the fragrance emitted from the product itself, the fragrance during use of the product, and the lingering fragrance from clothing, hair or skin be more favorable
• a fragrance impregnated body prepared by impregnating an inorganic porous material such as silica gel or calcium silicate or an organic porous material such as celluloses, with a flavor or fragrance
• a fragrance inclusion body prepared by the inclusion of a flavor or fragrance in ⁇ -cyclodextrin, ⁇ -cyclodextrin, ⁇ -cyclodextrin, hydroxypropylated ⁇ -dextrin, highly branched cyclic dextrin, etc.
• a known flavor or fragrance precursor, pro-fragrance, fragrance precursor, pro-perfume, etc. such as silicic acid ester compound, fatty acid ester compound, acetal compound, hemiacetal compound, Schiff base compound, hemiaminal compound or hydrazone compound, each of which can release a flavor or fragrance component.
• Examples of the aroma product include a perfume, eau de cologne, a liquid air freshener, a gel air freshener, a powder air freshener, an impregnated air freshener, a mist spray air freshener, an aerosol spray air freshener, a plug-in air freshener, an incense stick, a candle, etc.
• laundry care product examples include a mist spray for clothing, a spray for clothing, a detergent, a fabric softener, etc.
• Examples of the hair care product include a hair shampoo, a hair rinse, a hair conditioner, a hair treatment, a hair tonic, a hair styling agent, a hair dye, a permanent waving agent, a hair growth agent, a hair cologne, etc.
• Examples of the cosmetic include a lotion, a milky lotion, a cosmetic cream, a soap, a liquid soap, a facial cleanser, a sunscreen, an antiperspirant, a bath additive, a lipstick, a foundation, etc.
• the cleaner examples include a toilet cleaner, a toilet bowl cleaner, a glass cleaner, a dishwashing detergent, a washing machine cleaner, a drain cleaner, a bathroom cleaner, etc.
• the compound represented by formula (1) of the present invention releases a flavor or fragrance component by the action of a hydrolase and therefore, is particularly useful when a product having blended therein the compound represented by formula (1) of the present invention is used in combination with a product having blended therein a hydrolysate.
• the method for using the products in combination is not particularly limited but includes a method of using a mutual combination of laundry care products, hair care products, or cosmetics.
• examples of the method include (A) a method of using a combination of a cleaner for clothing, in which a lipase is blended, and a mist spray for clothing, a spray for clothing, a fabric softener, etc., in which the compound represented by formula (1) of the present invention is blended, and (B) a method of using a combination of a cleaner for clothing, in which the compound represented by formula (1) of the present invention is blended, and a mist spray for clothing, a spray for clothing, a fabric softener, etc., in which a lipase is blended.
• examples of the method include (A) a method of using a combination of a shampoo in which a lipase is blended, and a hair rinse, a hair conditioner, a hair treatment, a hair styling agent, a hair growth agent, a hair cologne, etc., in which the compound represented by formula (1) of the present invention is blended, and (B) a method of using a combination of a shampoo in which the compound represented by formula (1) of the present invention is blended, and a hair rinse, a hair conditioner, a hair treatment, a hair styling agent, a hair growth agent, a hair cologne, etc., in which a lipase is blended.
• the blending amount of the compound represented by formula (1) of the present invention in each product is not strictly restricted and can be variously changed according to use thereof.
• the blending amount of the compound represented by formula (1) of the present invention in each product is preferably from 0.0001 to 10% by mass, more preferably from 0.001 to 5% by mass.
• the compound represented by formula (1) of the present invention can be used, singly or in combination of two or more kinds, for a deodorant.
• the deodorant of the present invention can be used after optionally blending one kind or two or more kinds of known components selected from a cleaner, an antimicrobial, a fungicide, a deodorant, a natural essential oil, a flavor or fragrance, an aroma material, a cooling sensation agent, a warming sensation agent, a rust inhibitor, an antifoaming agent, a pH adjusting agent, water, a solvent, a propellant, a surfactant, an insecticide, a repellent, an insect repellent, a water repellent, a degrading enzyme, an antistatic agent, a coloring matter, an ultraviolet absorber, a preservative, a chelating agent, an antioxidant, a thickener, a gellant, a water-absorbing resin, activated carbon, silica, a porous material, a resin, paper, felt, a higher alcohol, an inorganic salt, etc., and formulating the blend.
• a cleaner an antimicrobial, a fungicide, a deodorant
• Examples of the known component include a cleaner such as alkylamine oxide, alkylamine, alkyl polyglycoside, naphthalenesulfonic acid-formalin condensate, hydrolyzed collagen peptide salt, acylmethyltaurine salt, N-acylamino acid salt, alkyl sulfate, ether carboxylate, ether sulfonate, alkyltrimethylammonium chloride, dialkyltrimethylammonium chloride, alkylamine salt, alkyl amidopropyl amino oxide, alkyl betaine, acetic acid betaine, fatty acid soap, etc.; an antimicrobial or fungicide such as 4-chloro-3,5-xylenol, isopropylmethylphenol, thymol, hinokitiol, phenol-based compound, polyphenol, catechin, tannin, natural product containing these, natural product containing their derivative, etc., 2-(4′-thiazolyl)-benzimidazole
• a fragrance impregnated body prepared by impregnating an inorganic porous material such as silica gel, calcium silicate, etc., or an organic porous material such as celluloses, etc., with a flavor or fragrance
• a fragrance inclusion body prepared by the inclusion of a flavor or fragrance in ⁇ -cyclodextrin, ⁇ -cyclodextrin, ⁇ -cyclodextrin, hydroxypropylated ⁇ -dextrin, highly branched cyclic dextrin, etc.
• a known aroma material for example, flavor or fragrance precursor, pro-fragrance, fragrance precursor, pro-perfume, etc., such as silicic acid ester compound, fatty acid ester compound, acetal compound, hemiacetal compound, Schiff base compound, hemiaminal compound, hydrazone compound, etc., which can release a flavor or fragrance component
• a rust inhibitor such as trisodium citrate, ammonium citrate, sodium nitrite
• a liquefied gas such as dimethyl ether, CFC (Chloro Fluoro Carbon), HCFC (Hydro Chloro Fluoro Carbon), HFC (Hydro Fluoro Carbon), etc.
• a compressed gas such as nitrogen, carbon dioxide, compressed air, nitrous oxide, etc.
• a surfactant such as polyoxyethylene alkyl ether, polyoxyethylene-polyoxypropylene copolymer, hydrogenated caster oil, sorbitan fatty acid ester, etc.
• Examples of the formulated deodorant of the present invention includes a deodorizing mist, a deodorizing spray, a liquid deodorant, a gel deodorant, a solid deodorant, a sheet-shaped deodorant, a granular deodorant, a beads deodorant, a powder deodorant, a smoke deodorant, a deodorant for toilet odor, a deodorant for urine odor, a deodorant for body odor, a deodorant for sweat odor, a deodorant for foot odor, a deodorant for scalp odor, a deodorant for aging odor, a deodorant for nursing care, a deodorant for raw garbage odor, a fabric deodorizer, a deodorant for damp-dry odor, a deodorant for laundry care, a deodorant for shoe cupboards, a shoe deodorizer, an entrance deodorizer, a room deodorizer, a bedroom deodorizer, a car freshener, a de
• the deodorant of the present invention can be used in a product such as aroma product, laundry care product, hair care product, cosmetic, oral care product, hygiene product, insecticide, insect repellent, dehumidifying agent, cleaner, etc.
• the aroma product examples include a liquid air freshener, a gel air freshener, a powder air freshener, an impregnated air freshener, a beads air freshener, a paper air freshener, a permeable film air fresher, a plug-type air freshener, a fan-type air freshener, an ultrasonic air freshener, a water-absorbing polymer air freshener, a mist spray air freshener, an aerosol spray air freshener, a plug-in air freshener, an incense stick, a candle, a reed diffuser, etc., in which a deodorizing function is imparted.
• laundry care product examples include a mist spray for clothing, a spray for clothing, a detergent, a fabric softener, an anti-wrinkle agent, etc., in which a deodorizing function is imparted.
• Examples of the hair care product include a hair shampoo, a hair rinse, a hair conditioner, a hair treatment, a hair tonic, a hair styling agent, a hair dye, a permanent waving agent, a hair growth agent, a hair lotion, a hair spray, etc., in which a deodorizing function is imparted.
• Examples of the cosmetic include a lotion, a milky lotion, a cosmetic cream, a soap, a liquid soap, a facial cleanser, a sunscreen, an antiperspirant, a bath additive, a lipstick, a foundation, etc., in which a deodorizing function is imparted.
• Examples of the oral care product include a toothpaste, a mouthwash, a mouth spray, a mouth freshener, a denture care product, a breath freshening product, etc., in which a deodorizing function is imparted.
• Examples of the hygiene product include a paper diaper, a sanitary product, wet tissue, tissue paper, toilet paper, a mask, etc., in which a deodorizing function is imparted.
• the cleaner examples include a toilet cleaner, a toilet bowl cleaner, a glass cleaner, a dishwashing detergent, a washing machine cleaner, a drain cleaner, a bathroom cleaner, a denture etc., in which a deodorizing function is imparted.
• the blending amount of the compound represented by formula (1) of the present invention in each product is not strictly restricted and can be variously changed according to use thereof.
• the blending amount of the compound represented by formula (1) of the present invention in each product is preferably from 0.0001 to 10% by mass, more preferably from 0.001 to 5% by mass.
• reaction was quenched by adding toluene and water.
• the reaction solution was extracted with toluene, and the organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution and water. After drying the organic layer over sodium sulfate, the filtrate was concentrated under reduced pressure to obtain a crude product.
• the resulting crude product was purified by silica gel column chromatography to obtain 1.90 g of the target product.
• reaction was quenched by adding toluene and water.
• the reaction solution was extracted with toluene, and the organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution and water. After drying the organic layer over sodium sulfate, the filtrate was concentrated under reduced pressure to obtain a crude product.
• the resulting crude product was purified by silica gel column chromatography to obtain 13.26 g of the target product.
• reaction was quenched by adding toluene and water.
• the reaction solution was extracted with toluene, and the organic layer was washed with 1 N hydrochloric acid, a saturated sodium hydrogencarbonate aqueous solution and saturated brine. After drying the organic layer over sodium sulfate, the filtrate was concentrated under reduced pressure to obtain a crude product.
• the resulting crude product was purified by silica gel column chromatography to obtain 1.60 g of the target product.
• reaction was quenched by adding toluene and water.
• the reaction solution was extracted with toluene, and the organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution and water. After drying the organic layer over sodium sulfate, the filtrate was concentrated under reduced pressure to obtain a crude product.
• the resulting crude product was purified by silica gel column chromatography to obtain 9.38 g of the target product.
• reaction was quenched by adding toluene and water.
• the reaction solution was extracted with toluene, and the organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution and water. After drying the organic layer over sodium sulfate, the filtrate was concentrated under reduced pressure to obtain a crude product.
• the resulting crude product was purified by silica gel column chromatography to obtain 1.85 g of the target product.
• the fragrance emission amount was determined from the difference between the peak area of the obtained fragrance emitting compound and the peak area of the control. The results are shown in Table 1.
• Lipex 100L produced by Novozymes, and AY “Amano” 30SD produced by Amano Enzyme Inc. were used as the lipase preparation.
• Example 1-7 Example 1-8
• Example 1-9 Compound Compound Compound Compound Compound Compound of of of Example 1-3
• Example 1-1 Example 1-2
• Example 1-3 Fragrance 76,407,359 12,076,381 5,098,870 16,031,669 emission amount Fragrance menthone hexenal citral citral emitting compound Lipase Lipex 100L AY “Amano” preparation 30SD
• a shampoo was prepared according to a formulation shown in Table 2.
• a hair bundle of 10 cm in length was cleaned using the prepared shampoo and rinsed with tap water. After drying at room temperature for 15 hours, about 0.3 g of an aqueous 1% lipase preparation solution was sprayed onto the hair bundle, and the scent on the hair bundle was smelled to examine the presence or absence of fragrance emission from hair.
• As the lipase preparation AY “Amano” 30SD produced by Amano Enzyme Inc. was used.
• citronellal emits a fragrance when lipase is allowed to act on the hair after drying, which was obtained using the shampoo prepared in Example 1-10.
• 2,6-dimethyl-5-heptenal emits a fragrance when lipase is allowed to act on the hair after drying, which was obtained using the shampoo prepared in Example 1-11.
• a hair conditioner was prepared according to a formulation shown in Table 3.
• a hair bundle of 10 cm in length was treated with the hair conditioner prepared and rinsed with tap water. After drying at room temperature for 15 hours, about 0.3 g of an aqueous 1% lipase preparation solution was sprayed onto the hair bundle, and the scent on the hair bundle was smelled to examine the presence or absence of fragrance emission from hair.
• As the lipase preparation AY “Amano” 30SD produced by Amano Enzyme Inc. was used.
• citronellal emits a fragrance when lipase is allowed to act on the hair after drying, which was obtained using the hair conditioner prepared in Example 1-12.
• 2,6-dimethyl-5-heptenal emits a fragrance when lipase is allowed to act on the hair after drying, which was obtained using the hair conditioner prepared in Example 1-13.
• a liquid detergent was prepared according to a formulation shown in Table 4.
• a cotton towel was cleaned with the liquid detergent prepared and rinsed with tap water. After drying at room temperature for 15 hours, about 0.3 g of an aqueous 1% lipase preparation solution was sprayed onto the towel, and the scent on the towel was smelled to examine the presence or absence of fragrance emission from towel.
• As the lipase preparation AY “Amano” 30SD produced by Amano Enzyme Inc. was used.
• citronellal emits a fragrance when lipase is allowed to act on the towel after drying, which was obtained using the liquid detergent prepared in Example 1-14.
• 2,6-dimethyl-5-heptenal emits a fragrance when lipase is allowed to act on the towel after drying, which was obtained using the liquid detergent prepared in Example 1-15.
• a softener was prepared according to a formulation shown in Table 5.
• a cotton towel was treated with the softener prepared and rinsed with tap water. After drying at room temperature for 15 hours, about 0.3 g of an aqueous 1% lipase preparation solution was sprayed onto the towel, and the scent on the towel was smelled to examine the presence or absence of fragrance emission from towel.
• As the lipase preparation AY “Amano” 30SD produced by Amano Enzyme Inc. was used.
• Example 1-16 Tri(oxyethylene)methylammonium 18 18 methylsulfate fatty acid ester Polyoxyethylene(23) lauryl ether 3 3 Propylene glycol 3 3 Calcium chloride 0.05 0.05 Compound of Example 1-4 0.5 — Compound of Example 1-5 — 0.5 Deionized water 75.45 75.45 Total (% by mass) 100 100
• citronellal emits a fragrance when lipase is allowed to act on the towel after drying, which was obtained using the softener prepared in Example 1-16.
• 2,6-dimethyl-5-heptenal emits a fragrance when lipase is allowed to act on the towel after drying, which was obtained using the softener prepared in Example 1-17.
• Flavor or Fragrance Composition
• a flavor or fragrance composition was prepared according to a formulation shown in Table 6.
• a liquid detergent in which lipase is blended or not blended was prepared according to a formulation shown in Table 7.
• a softener was prepared according to a formulation shown in Table 8.
• Lipex 100L produced by Novozymes was used as the lipase preparation.
• Example Comparative Comparative 1-22 Example 1-3 1-23
• Example 1-4 Example 1-5 Liquid detergent blending of non-blending blending of non-blending blending of lipase of lipase lipase of lipase lipase Softener
• Example Example Comparative 1-20 1-20 1-21 1-21 Example 1-2 Fragrance during 3.3 2.8 3.1 2.8 2.6 intensity drying after 2.6 1.2 2.4 1.1 1 drying Fresh during 3.4 2.6 3.6 2.6 2.5 feeling drying after 2.8 0.6 3 0.7 0.5 drying
• reaction was quenched by adding toluene and water.
• the reaction solution was extracted with toluene, and the organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution and water. After drying the organic layer over sodium sulfate, the filtrate was concentrated under reduced pressure to obtain a crude product.
• the resulting crude product was purified by silica gel column chromatography to obtain 1.90 g of the target product.
• reaction was quenched by adding toluene and water.
• the reaction solution was extracted with toluene, and the organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution and water. After drying the organic layer over sodium sulfate, the filtrate was concentrated under reduced pressure to obtain a crude product.
• the resulting crude product was purified by silica gel column chromatography to obtain 13.26 g of the target product.
• reaction was quenched by adding toluene and water.
• the reaction solution was extracted with toluene, and the organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution and water. After drying the organic layer over sodium sulfate, the filtrate was concentrated under reduced pressure to obtain a crude product.
• the resulting crude product was purified by silica gel column chromatography to obtain 9.38 g of the target product.
• reaction was quenched by adding toluene and water.
• the reaction solution was extracted with toluene, and the organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution and water. After drying the organic layer over sodium sulfate, the filtrate was concentrated under reduced pressure to obtain a crude product.
• the resulting crude product was purified by silica gel column chromatography to obtain 1.85 g of the target product.
• reaction was quenched by adding toluene and water.
• the reaction solution was extracted with toluene, and the organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution and water. After drying the organic layer over sodium sulfate, the filtrate was concentrated under reduced pressure to obtain a crude product.
• the resulting crude product was purified by silica gel column chromatography to obtain 0.56 g of the target product.
• reaction was quenched by adding toluene and water.
• the reaction solution was extracted with toluene, and the organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution and water. After drying the organic layer over sodium sulfate, the filtrate was concentrated under reduced pressure to obtain a crude product.
• the resulting crude product was purified by silica gel column chromatography to obtain 2.01 g of the target product.
• Staphylococcus aureus strain NBRC12732 Staphylococcus epidermidis strain JCM2414T, Corynebacterium xerosis strain JCM1324, Pseudomonas aeruginosa strain NBRC13275, Bacillus subtilis strain NBRC3134, and Moraxella osloensis strain
• shaking culture was performed at 30° C. for 20 hours. 3 mL of the resulting preculture solution was transferred to a vial bottle, and 10 mg of each of the compounds of Examples 2-2 to 2-6 was mixed, followed by hermetically sealing the bottle. Thereafter, shaking culture was further performed at 30° C. for 20 hours.
• a peak area of the deodorizing compound was obtained by performing GC/MS analysis of the head space component contained in the vial bottle having 3 mL of microorganism culture solution in which 10 mg of each of the compound of Examples 2-2 to 2-6 was mixed.
• a microorganism culture solution having not mixed therein each of the compounds of Examples 2-2 to 2-6 was used as the control, and a peak area of the control was obtained by the same method as above.
• the difference between the peak area of the deodorizing compound and the peak area of the control was calculated as the deodorizing component emission amount, and the results are shown in Tables 10 to 12.
• Example 2-7 Example 2-8 Example 2-9 Example 2-10 Compound Compound of Compound of Compound of Example 2-3
• Example 2-4 Example 2-5
• Example 2-6 Deodorizing citronellal 2,6-dimethyl-5- trimethylhexanal octanal component heptenal Deodorizing 1,064,240,572 132,554,000 189,916,125 129,928,279 component emission amount
• the compound represented by formula (1) according to the present invention releases, as a deodorizing component, an aldehyde represented by formula (2) by the action of Staphylococcus epidermidis, Corynebacterium xerosis, Pseudomonas aeruginosa, Bacillus subtilis, Moraxella osloensis , or Propionibacterium acnes .
• a gauze impregnated with Triolein 1 g, Tricaproin 1 g and Androsterone 0.5 g was set as a substrate in a petri dish of 33 mm in diameter ⁇ . Furthermore, 1 mL of Staphylococcus aureus test bacterial solution (1 ⁇ 10 9 cfu/mL) previously prepared in 0.9% physiological saline containing 0.2% L-leucine as a substrate was mixed with 3.5 ⁇ L of the compound of Example 2-3, and the resulting mixture was uniformly impregnated into the gauze that was set. A cover was put on the petri dish and after hermetically sealing it, culture was performed at 37° C. for 20 hours. The level of odor comfort/discomfort of the gauze after culturing was sensorily evaluated by ten expert panelists according to the following criteria. The evaluation score was determined by averaging the evaluated values of the expert panelists.
• Comparative Example 2-1 evaluation was made on gauze subjected to the same culturing without mixing the compound of Example 2-3. The results are shown in Table 13.
• a deodorizing mist was prepared according to a formulation shown in Table 14.
• Example 2-19 Compound of Example 2-1 1 — Compound of Example 2-3 — 1 Polyoxyethylene(60) hydrogenated 3 3 caster oil Deionized water 96 96 Total (% by mass) 100 100
• a cleaned right-foot sock made of man-made fiber was sprayed with 0.6 g of each of deodorizing mists obtained in Examples 2-19 and 2-20.
• a cleaned left-foot sock made of man-made fiber, which was not sprayed with deodorizing mist was used.
• the level of odor comfort/discomfort of the sock before wearing as well as after wearing for 15 hours was sensorily evaluated by ten expert panelists according to criteria. As for the criteria, the criteria of Example 2-18 was used. The evaluation score was determined by averaging the evaluated values of the expert panelists. The results are shown in Table 15.
• Example 2-21 Example 2-22 (sprayed with (sprayed with deodorizing mist deodorizing mist obtained in Comparative obtained in Comparative Example 2-19)
• Example 2-2 Example 2-20)
• Example 2-3 Sock right foot left foot right foot left foot Level of before 0 0 0 0 comfort/ wearing discomfort after 15 1.8 ⁇ 2.2 1.5 ⁇ 2 hours
• Example and Comparative Example the sock before wearing was substantially odorless.
• a deodorizing spray was prepared according to a formulation shown in Table 16.
• a sweaty shirt was prepared by wearing a cleaned cotton shirt and exercising vigorously. The shirt was put in a plastic bag and left standing at room temperature for 12 hours in a hermetically sealed state. After taking out the shirt from the plastic bag, 1 g of the deodorizing spray obtained in Example 2-23 was sprayed onto the right-side portion of the shirt. In Comparative Example, the deodorizing spray was not sprayed onto the left-side portion of the shirt. Thereafter, the shirt was left standing for 3 hours. The level of odor comfort/discomfort in the right-side portion and left-side portion of the shirt was sensorily evaluated by ten expert panelists according to criteria. As for the criteria, the criteria of Example 2-18 was used. The evaluation score was determined by averaging the evaluated values of the expert panelists. The results are shown in Table 17.
• the left-side portion of the shirt not sprayed with the deodorizing spray of the present invention emitted odor and caused discomfort, but in the right-side portion of the shirt sprayed with the deodorizing spray of the present invention, offensive odor was not sensed. It could be confirmed that a deodorizing component is released from the compound represented by formula (1) and the unpleasant sensation is thereby alleviated.
• a deodorizing liquid detergent was prepared according to a formulation shown in Table 18.
• a deodorizing softener was prepared according to a formulation shown in Table 19.
• the compound represented by formula (1) can release an aldehyde or ketone that is a fragrance component by the action of a hydrolysate, the compound can be used as a flavor or fragrance precursor and is useful.
• the lingering fragrance having fresh feeling can be caused to last on the clothing, hair or skin, and the compound has applicability in the flavor or fragrance industry.

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• 2018
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