JP2014205642A - C-S lyase inhibitor - Google Patents

Abstract

【選択図】なし[PROBLEMS] To provide a CS lyase activity inhibitor, a deodorant agent, and a method for suppressing the generation of odor, which have a high odor generation suppression effect.
A CS lyase inhibitor comprising one or more compounds selected from a carbonyl compound and an alcohol compound represented by the general formula (1), a composition for suppressing odor production and a deodorant containing the CS lyase inhibitor, and A method for suppressing odor production in which a certain amount of CS lyase inhibitor is applied to soot [X represents O or OH, and the broken line represents a double bond when X is O, and a single bond when X is OH. R ¹ , R ¹ ′, R ² , R ³ and R ⁴ represent H, OH, an alkyl group, an alkenyl group or an alkenyloxy group, and R ¹ and R ⁴ , R ² and R ³ , R ³ and R ⁴ May form a cyclic structure with adjacent C atoms. However, when X is O, R ¹ 'does not exist].

[Selection figure] None

Description

  The present invention relates to C-S lyase inhibitors.

  With increasing awareness of etiquette in recent years, an increasing number of people are concerned about sweat and body odor. Sweat is secreted from almost all parts of the body, but among them sweat of the heel is easy for bacteria to grow and smell. For this reason, the number of people who care about the odor of themselves and others is increasing.

  Odors (also called odors) generated from the armpits can be broadly divided into sour and steamed odors (called sweat odors, acid odors, etc.) and apocrine odors (also called “wakiga”). In particular, the apocrine odor is caused by secretions derived from the apocrine sweat glands distributed under the cocoon, and is a complex and strong odor, so it is particularly easily perceived by the person himself / herself. Therefore, there is a strong demand for materials that suppress the generation of apocrine odor.

  For example, Patent Document 1 discloses a deodorant agent containing a specific amino acid compound as an amino acid β-lyase enzyme activity inhibitor. Patent Document 2 discloses that a specific compound contained in a eucalyptus extract has an effect of eliminating 3-mercapto-3-methylhexane-1-ol, which is one of the causative substances of apocrine odor. Has been.

  By the way, the apocrine odor mainly consists of (1) sulfur-like odors and (2) animal and spicy odors, and the main causative components are 3-mercapto-3- Alcohol compounds having a thiol group at the 3-position represented by methylhexane-1-ol (hereinafter these compounds are also referred to as 3-mercaptoalcohol compounds), and the latter is represented by 3-hydroxy-3-methylhexanoic acid. It is known that it is a β-hydroxy acid compound (Patent Document 3).

In addition, among the apocrine odors, (1) Staphylococcus lentus is a bacterium that has a high ability to produce 3-mercaptoalcohol compounds that are the causative agent of sulfur-like and odorous odors. Is known (Patent Document 4).

  Therefore, it is conceivable to use a substance with high antibacterial properties against the above-mentioned fungus to suppress the stench, but when the cell membrane of the fungus is destroyed by using such a bactericidal agent, the enzyme in the fungus body is released. As a result, a 3-mercaptoalcohol compound is produced, and eventually there is a problem that the bad smell cannot be suitably suppressed. In addition, when a biofilm is formed, the antibacterial agent may not work.

  On the other hand, masking with a so-called fragrance that coats malodors with a fragrance is generally well known. However, when a bad odor and a fragrance are mixed, it may give off a bad odor, and especially when using a fragrance as a masking agent for a bad smell, in order to obtain a long-lasting feeling of the masking effect, it has a masking effect against the bad smell and is It is necessary to select a fragrance that remains for a long time. For this reason, there was a problem that the fragrance | flavor which can be used was restricted and the freedom degree of design of a fragrance was low.

International Publication No. 91/05541 Pamphlet JP 2010-248120 A JP 2004-309454 A JP 2010-252710 A

  In such a situation, the present inventors have decided not to sterilize the odor-producing bacteria or mask the odor-causing component, but to effectively suppress the odor by the CS lyase enzyme contained in Staphylococcus lentus. The idea was to suppress the generation of odor-causing components by inhibiting the activity.

  Accordingly, the present invention provides a CS lyase activity inhibitor that has a high effect of suppressing the generation of the odor-causing component itself, and a composition and deodorant for suppressing odor production containing the CS lyase activity inhibitor. It is an object of the present invention to provide a method for suppressing the generation of bad odor.

  The present inventors have found that the activity of C-S lyase is inhibited by a carbonyl compound or alcohol compound having a specific structure. And furthermore, with these CS lyase activity inhibitors, it is possible to suppress the production of 3-mercaptoalcohol compounds from the odor precursors actually present in human axilla, and by blending a certain amount into the deodorant agent, It has been found that the effect of suppressing the generation of bad odor can be imparted.

  The present invention provides a C-S lyase inhibitor comprising one or more compounds selected from carbonyl compounds and alcohol compounds represented by the general formula (1).

[Wherein, X represents an oxygen atom or a hydroxyl group, and the broken line represents a double bond when X is an oxygen atom, and a single bond when X is a hydroxyl group. R ¹ , R ¹ ′, R ² , R ^3, and R ⁴ represent a hydrogen atom, a hydroxyl group, or a linear, branched, or cyclic alkyl group, alkenyl group, or alkenyloxy group, and R ¹ , R ⁴ , R ² And R ³ , R ³ and R ⁴ may be combined together to form a cyclic structure with adjacent carbon atoms. However, R ¹ ′ does not exist when X is an oxygen atom. ]

  Further, although not included in the above structure, it has been found that terpineol, dihydromyrsenol, and tricyclodecenyl acetate also inhibit the activity of C-S lyase. That is, the present invention provides a C—S lyase inhibitor comprising one or more compounds selected from terpineol, dihydromyrsenol and tricyclodecenyl acetate.

  Furthermore, the present invention provides a composition for suppressing odor production, which contains the C—S lyase inhibitor described above.

  Furthermore, the present invention provides a deodorant agent containing the C-S lyase inhibitor.

  Furthermore, the present invention provides a method for suppressing the generation of odor by applying the C-S lyase inhibitor to the axilla part in a range of 0.1 μg to 10,000 μg.

  According to the present invention, it is possible to effectively suppress the generation of odor.

[CS lyase inhibitor]
In the present invention, the CS lyase inhibitor means that the enzyme activity is increased by adding 0.05% by mass to a reaction solution containing 0.5% by mass of an enzyme solution obtained from 140 mg of Staphylococcus lentus H292 strain. It means that it was shown that more than 60% was suppressed. Among them, those in which the enzyme activity is inhibited by 80% or more are more preferable.

  The method for obtaining Staphylococcus lentus used for screening for the above-mentioned CS lyase inhibitor is not particularly limited, and may be commercially available, or collected from human skin (preferably under human eyelids). It may be a thing. It is preferable to use a strain having a higher ability to produce a 3-mercaptoalcohol compound. From this point, Staphylococcus lentus strain H292 is a preferable example. Staphylococcus lentus strain H292 was issued on February 20, 2009 at the National Institute of Advanced Industrial Science and Technology Patent Biological Deposit Center (1-1-1 Tsukuba Center Tsukuba, Ibaraki Pref.) Deposited at P-21774.

  The C-S lyase inhibitor of the present invention comprises one or more compounds selected from carbonyl compounds and alcohol compounds represented by the general formula (1).

[Wherein, X represents an oxygen atom or a hydroxyl group, and the broken line represents a double bond when X is an oxygen atom, and a single bond when X is a hydroxyl group. R ¹ , R ¹ ′, R ² , R ^3, and R ⁴ represent a hydrogen atom, a hydroxyl group, or a linear, branched, or cyclic alkyl group, alkenyl group, or alkenyloxy group, and R ¹ , R ⁴ , R ² And R ³ , R ³ and R ⁴ may be combined together to form a cyclic structure with adjacent carbon atoms. However, R ¹ ′ does not exist when X is an oxygen atom. ]

In the general formula (1), when R ¹ , R ¹ ′, R ² , R ³ and R ⁴ are an alkyl group, an alkenyl group or an alkeneoxy group, their carbon number is preferably 1-12.

  As the compound represented by the general formula (1), a carbonyl compound represented by the general formula (1-1) and an alcohol compound represented by the general formula (1-2) are preferable.

[Wherein R ¹ , R ² , R ³ and R ⁴ represent a hydrogen atom, a hydroxyl group, a linear, branched or cyclic alkyl group, an alkenyl group or an alkenyloxy group, and R ¹ and R ⁴ , R ² And R ³ , R ³ and R ⁴ may be combined together to form a cyclic structure with adjacent carbon atoms. ]

In general formula (1-1), R ¹ is preferably an alkyl group having 1 to 10 carbon atoms, an alkenyl group, or an alkenyloxy group. R ² is preferably a hydrogen atom or an alkyl group or alkenyl group having 1 to 5 carbon atoms. R ³ is preferably an alkyl group or alkenyl group having 1 to 10 carbon atoms. R ⁴ is preferably a hydrogen atom, a hydroxyl group, or an alkyl group having 1 to 3 carbon atoms. When R ¹ and R ⁴ , R ² and R ³ , R ³ and R ⁴ form a cyclic structure with adjacent carbon atoms, the cyclic structure is preferably a 5- or 6-membered ring, and the side chain You may have. The carbonyl compound represented by the general formula (1-1) has at least one cyclic structure formed by such two groups, or a cyclic alkyl group or alkenyl group in the molecule. preferable.

〔式中、Ｒ¹、Ｒ¹'、Ｒ²，Ｒ³及びＲ⁴は、水素原子又は直鎖、分岐鎖若しくは環状のアルキル基若しくはアルケニル基を示す。〕

[Wherein R ¹ , R ¹ ′, R ² , R ³ and R ⁴ represent a hydrogen atom, a linear, branched or cyclic alkyl group or alkenyl group. ]

In general formula (1-2), R ¹ is preferably a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an alkenyl group. R ¹ ′ is preferably a hydrogen atom and an alkyl group having 1 to 3 carbon atoms, more preferably a hydrogen atom and a methyl group. The R ² and R ^3, preferably an alkyl group having a hydrogen atom and 1 to 3 carbon atoms, more preferably a hydrogen atom. R ⁴ is preferably a hydrogen atom and an alkyl group or alkenyl group having 1 to 5 carbon atoms. When R ¹ , R ¹ ′, R ² , R ³ and R ⁴ are an alkyl group or an alkenyl group, it is preferably a chain.

  Examples of the carbonyl compound represented by the general formula (1-1) that has been confirmed to have a CS lyase inhibitory action satisfying the above conditions in the present invention include cis jasmon, nootkatone, α-ionone, β-ionone, α- Examples include methylionone, γ-methylionone, α-damascone, benzaldehyde, β-damacenone, and cis-3-hexenyl salicylate. Further, in the present invention, the alcohol compound represented by the general formula (1-2) that has been confirmed to have a CS lyase inhibitory action satisfying the above conditions includes linalool, nerolidol, geraniol, and trans-2-hexenol. Can be mentioned.

  Although not included in the above structure, it was confirmed that terpineol, dihydromyrsenol, and tricyclodecenyl acetate also exhibited C-S lyase inhibitory action satisfying the above conditions.

  In the present invention, any of the above C-S lyase inhibitors can be contained in the composition for suppressing odor generation, either alone or in combination of two or more. In addition, by adding an effective amount of the C-S lyase inhibitor or the odor production-suppressing composition of the present invention to the deodorant agent, the production of odor-causing components can be suppressed and a high deodorizing effect can be exhibited.

[Composition for suppressing odor production]
The content of the CS lyase inhibitor in the composition for suppressing odor production according to the present invention is such that the concentration of the CS lyase inhibitor is 0.0001% by mass or more, further 0.001% by mass or more when used, that is, when applied to the axilla. Furthermore, it is preferable to be 0.01% by mass or more, 1% by mass or less, further 0.3% by mass or less, and further 0.1% by mass or less.

  In the composition for suppressing odor production according to the present invention, a surfactant is added from the viewpoint of having a combined effect such that a CS lyase inhibitor can easily penetrate into cells of a microorganism and also has an effect on intracellular enzymes. It is preferable. The surfactant used in the present invention is not limited as long as it has the above-described effects. Specifically, a nonionic surfactant, an amphoteric surfactant, a cationic surfactant, and an anionic surfactant are used. Although it can mention, it is preferable that a nonionic surfactant is included at least.

  A solvent can be further blended in the composition for suppressing odor production of the present invention. Any solvent can be used as long as it can be blended in cosmetics, and examples thereof include water and water-soluble organic solvents. Triethylene glycol, 3-methyl-1,3-butanediol, 2-methyl-2,4-butanediol, ethylene glycol monophenyl ether, dipropylene glycol, ethylene glycol from the viewpoint of further enhancing the deodorizing effect on mercapto alcohol , Propylene glycol, diethylene glycol, 1,3-butanediol, and polyethylene glycol are preferred.

  The composition for suppressing odor production according to the present invention is a variety of other components commonly used in cosmetics, such as oils, alcohols, chelating agents, pH adjusters, bactericides, antibacterial agents, antiseptics, thickeners, and pigments. In addition to fragrances, components such as deodorant bases, moisturizers, softeners, keratin protective agents, medicinal agents, antioxidants, metal salts and metal ions can be arbitrarily selected as long as the effects of the present invention are not impaired. It can mix | blend and formulate.

[Deodorant]
The content of the CS lyase inhibitor in the deodorant agent of the present invention varies depending on the form of the deodorant agent and cannot be uniformly defined. For example, in the case of a stick or powder type deodorant agent, 0.0001% by mass or more, Is preferably 0.001% by mass or more, further 0.01% by mass or more, 1% by mass or less, more preferably 0.3% by mass or less, and further preferably 0.1% by mass or less. In addition, for example, in the case of a deodorant agent of a lotion type (roll-on type, natural spray (spray type bottle) type without impregnation, impregnated sheet type, etc.), 0.00005% by mass or more, further 0.0005% by mass or more, and further 0.005 It is preferably not less than 0.5% by mass, not more than 0.5% by mass, more preferably not more than 0.15% by mass, further preferably not more than 0.05% by mass. Further, for example, in the case of a spray-type deodorant containing a propellant, 0.00001% by mass or more, further 0.0001% by mass or more, further 0.001% by mass or more, 0.1% by mass or less, further 0.03% by mass or less, Is preferably 0.01% by mass or less.

(Fragrance)
In addition to the CS lyase inhibitor of the present invention, an arbitrary fragrance can be blended with the deodorant of the present invention. Specifically, “Fundamentals of perfumes and fragrances” (by Nakajima Motoki, edited by Sangyo Tosho Co., Ltd., June 21, 1995), “Synthetic perfumes-Chemistry and product knowledge” (by Motoichi Into, Chemical Industry) The fragrances described in Nikkansha, March 25, 2005, and the revised edition), “Perfume and Flavor Chemicals” (by Stefan Arctender, self-published, 1969) can be used.

(Water, organic solvent)
Furthermore, when the CS lyase inhibitor of the present invention is blended in a deodorant agent, it is more preferable to use a combination of water and a water-soluble organic solvent as a medium.

Examples of the above water-soluble organic solvents include
Alcohols such as ethanol, 1-propanol, 2-propanol, butyl alcohol;
Ethylene glycol, 1,2-propanediol, 1,3-butanediol, 3-methyl-1,3-butanediol, hexylene glycol, 2-ethyl-1,3-hexanediol, glycerin, diethylene glycol, triethylene glycol , Glycols such as dipropylene glycol, diglycerin, polyethylene glycol, polypropylene glycol;
And ethers such as ethylene glycol ethyl ether, ethylene glycol methyl ether, ethylene glycol butyl ether, ethylene glycol monophenyl ether, and diethylene glycol ethyl ether.
From the viewpoint of further enhancing the deodorizing effect on mercapto alcohol, triethylene glycol, 3-methyl-1,3-butanediol, ethylene glycol monophenyl ether, dipropylene glycol, ethylene glycol, 1,2-propanediol, diethylene glycol, 1 1,3-butanediol and polyethylene glycol are preferred.

(Other ingredients)
The deodorant agent of the present invention can contain an antiperspirant, a disinfectant, another deodorant and the like. Antiperspirants include, for example, chlorohydroxyaluminum, zinc paraphenolsulfonate, aluminum hydroxychloride, aluminum chloride, aluminum sulfate, aluminum citrate, aluminum acetate, basic aluminum chloride, aluminum phenolsulfonate, α-naphthol disulfonic acid Aluminum, sodium perborate, aluminum zirconium octachlorohydrate, aluminum zirconium pentachlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium trichlorohydrate, zirconium chlorohydrate, potassium aluminum sulfate, allantochlorohydroxyaluminum, basic Aluminum bromide, aluminum naphthalene sulfonic acid, Group of aluminum iodide, zinc oxide. Among them, aluminum chlorohydrate, para zinc phenolsulfonate is preferred.

  The antiperspirant can be used alone or in combination of two or more, and the content in the deodorant of the present invention is preferably 0.1% by mass or more, more preferably 1% by mass or more, It is preferably 30% by mass or less, more preferably 15% by mass or less.

  Examples of bactericides include benzalkonium chloride, triclosan, isopropylmethylphenol, 3,4,4-trichlorocarbanilide, triethyl citrate, benzethonium chloride, alkyltrimethylammonium chloride, resorcin, phenol, sorbic acid, salicylic acid, Examples include hexachlorophene, chlorhexidine gluconate, chlorhexidine isopropylmethylphenol hydrochloride, silver-supported zeolite, and silver-supported silica. Two or more of these may be used. Preferred are benzalkonium chloride, triclosan, and isopropylmethylphenol. The content of the disinfectant is 0.01% by mass or more, more preferably 0.1% by mass or more, and preferably 1% by mass or less, and more preferably 0.5% by mass or less, from the viewpoint of the deodorant effect with respect to the entire deodorant composition. .

  Examples of other deodorants include zinc oxide and activated carbon. Two or more of these may be used.

  In the deodorant of the present invention, in addition to the above-described components, other components used for cosmetics, for example, cooling agents, powder components, water-soluble components, liquid fats and oils, in a range not impairing the effects of the present invention, Solid fats, waxes, hydrocarbon oils, higher fatty acids, higher alcohols, ester oils, silicone oils, anionic surfactants, cationic surfactants, amphoteric surfactants, nonionic surfactants, humectants, water-soluble polymers, Thickeners, film agents, UV absorbers, sequestering agents, sugars, amino acids, organic amines, polymer emulsions, pH adjusters, skin nutrients, vitamins, antioxidants, antioxidant aids, etc. as required Can be appropriately contained.

(Form)
The dosage form of the deodorant agent of the present invention is not particularly limited, and examples thereof include an aerosol system, a solution system, a solubilization system, an emulsification system, a water-oil two-layer system, and a water-oil-powder three-layer system. Examples of product forms include lotion, mist type, aerosol type, roll-on type, stick type, and body paper. Among them, roll-on type and stick type dosage forms are preferable.

(PH)
The pH of the deodorant of the present invention is preferably adjusted to 3 to 5 from the viewpoint of application to the skin, and is preferably adjusted to pH 3 to 4 in consideration of containing an antiperspirant. When the deodorant agent is a water-oil two-layer system or a water-oil-powder three-layer system, the pH of the water layer is measured.

[Method of suppressing the generation of odor]
The CS lyase inhibitor of the present invention can effectively suppress the generation of odor derived from 3-mercaptoalcohol, which is a sulfur-like odor, by applying it to the body surface, particularly the axilla.

The CS lyase inhibitor is preferably applied to the axilla in an amount of 0.1 μg or more, more preferably 1 μg or more, and 10,000 μg or less, more preferably 3000 μg or less. In addition, the CS lyase inhibitor is 0.01 ppm or more, further 0.1 ppm or more, further 1 ppm or more, 100,000 ppm or less, more preferably 10000 ppm or less, and even 1000 ppm or less with respect to sweat in the axilla. It is preferable to apply to.
Specifically, for example, when applying a deodorant containing a CS lyase inhibitor, the application amount of the CS lyase inhibitor is 0.1 μg or more, further 1 μg or more, 10000 μg or less, further 3000 μg or less to the axilla. It is preferable to apply so that it becomes.

  With respect to the embodiments described above, preferred aspects of the present invention will be further disclosed below.

<1>
A CS lyase inhibitor comprising one or more compounds selected from carbonyl compounds and alcohol compounds represented by the general formula (1).

[Wherein, X represents an oxygen atom or a hydroxyl group, and the broken line represents a double bond when X is an oxygen atom, and a single bond when X is a hydroxyl group. R ¹ , R ¹ ′, R ² , R ^3, and R ⁴ represent a hydrogen atom, a hydroxyl group, or a linear, branched, or cyclic alkyl group, alkenyl group, or alkenyloxy group, and R ¹ , R ⁴ , R ² And R ³ , R ³ and R ⁴ may be combined together to form a cyclic structure with adjacent carbon atoms. However, R ¹ ′ does not exist when X is an oxygen atom. ]

<2>
The compound represented by the general formula (1) is preferably cis-jasmon, nootkatone, β-ionone, α-damascone, benzaldehyde, α-ionone, α-methylionone, γ-methylionone, β-damasenone, salicylic acid cis-3 The CS lyase inhibitor according to <1>, which is selected from hexenyl, linalool, nerolidol, geraniol, and trans-2-hexenol.

<3>
<1> or <2> a composition for suppressing odor production containing the CS lyase inhibitor according to <2>.

<4>
The concentration of the CS lyase inhibitor during use is preferably 0.0001% by mass or more, more preferably 0.001% by mass or more, more preferably 0.01% by mass or more, and preferably 1% by mass or less, more preferably 0.3% by mass. % Or less, more preferably 0.1% by mass or less.

<5>
Preferably, the composition for suppressing odor production according to <3> or <4>, further comprising a surfactant, more preferably a nonionic surfactant.

<6>
Preferably, further a solvent, more preferably triethylene glycol, 3-methyl-1,3-butanediol, 2-methyl-2,4-butanediol, ethylene glycol monophenyl ether, dipropylene glycol, ethylene glycol, propylene glycol The composition for suppressing odor production according to any one of <3> to <5>, comprising one or more solvents selected from styrene, diethylene glycol, 1,3-butanediol, and polyethylene glycol

<7>
A deodorant agent comprising the CS lyase inhibitor according to <1> or <2>.

<8>
It is a stick or powder type, and the CS lyase inhibitor content is preferably 0.0001% by mass or more, more preferably 0.001% by mass or more, more preferably 0.01% by mass or more, and preferably 1% by mass or less. More preferably, it is 0.3 mass% or less, More preferably, it is 0.1 mass% or less, The deodorant agent as described in <7>.

<9>
It is a lotion type, and the content of the CS lyase inhibitor is preferably 0.00005% by mass or more, more preferably 0.0005% by mass or more, more preferably 0.005% by mass or more, and preferably 0.5% by mass or less, The deodorant agent according to <7>, preferably 0.15% by mass or less, more preferably 0.05% by mass or less.

<10>
It is a spray type containing a propellant, and the content of the CS lyase inhibitor is preferably 0.00001% by mass or more, more preferably 0.0001% by mass or more, further preferably 0.001% or more, and preferably 0.1% by mass. Hereinafter, the deodorant agent according to <7>, more preferably 0.03% by mass or less, and still more preferably 0.01% by mass or less.

<11>
Preferably, further a solvent, more preferably triethylene glycol, 3-methyl-1,3-butanediol, 2-methyl-2,4-butanediol, ethylene glycol monophenyl ether, dipropylene glycol, ethylene glycol, propylene glycol The deodorant agent according to any one of <7> to <10>, which contains one or more solvents selected from diethylene glycol, 1,3-butanediol, and polyethylene glycol

<12>
The CS lyase inhibitor according to <1> or <2> is preferably 0.1 μg or more, more preferably 1 μg or more, preferably 10,000 μg or less, more preferably 3000 μg or less with respect to the axilla part. The method for suppressing the generation of bad odor to be applied.

Reference Example 1: Confirmation of decomposition products of odor precursor
0.05 mL of 2-amino-7-hydroxy-5-methyl-5-propyl-4-thia-1-heptanoic acid aqueous solution (0.2 μM), 0.1 mL of an enzyme extract derived from Staphylococcus lentus obtained by the method described later Add 0.05 mL of pyridoxal phosphate (1 mM aqueous solution) and 0.2 mL of 0.5 mass% potassium phosphate buffer (50 mM, pH 8.1) to distilled water to make 1.25 mL, warm to 37 ° C, and leave for 20 hours did. The sample after standing was confirmed to have a bad odor derived from 3-mercapto-3-methylhexane-1-ol. Further, the sample was analyzed, and it was confirmed that the content of 2-amino-7-hydroxy-5-methyl-5-propyl-4-thia-1-heptanoic acid was reduced and pyruvic acid was produced.
From this, the substrate 2-amino-7-hydroxy-5-methyl-5-propyl-4-thiaheptanoic acid is degraded by an enzyme derived from Staphylococcus lentus, and pyruvic acid and 3-mercapto-3-methyl It was confirmed that hexane-1-ol was produced. That is, it was confirmed that the enzyme degrading the substrate was CS lyase. From now on, instead of 2-amino-7-hydroxy-5-methyl-5-propyl-4-thia-1-heptanoic acid, benzylcysteine, which is well known as a substrate for CS lyase, is used as a substrate for evaluation. It was decided.

Example 1 Measurement of CS Lyase Inhibitory Effect in Model Evaluation System for Various Compounds <Preparation of Enzyme Extract>
Staphylococcus lentus strain H292 was inoculated into 200 mL of SCD liquid medium and cultured at 35 ° C. for 16 hours. The cells were submerged by centrifugation and the supernatant was discarded. After adding physiological saline and mixing, the operation of sunk the cells again by centrifugation and discarding the supernatant (washing the cells) was performed twice to obtain 140 mg of cells. After adding 0.7 mL of 0.1 M potassium phosphate buffer (KPB; pH 7.2), microbeads were added and stirred (1800 rpm, 10 minutes × twice) to destroy the cell membrane. After centrifuging again, insoluble matter was removed, and the resulting liquid (about 1 mL) was taken out and diluted 10-fold (w / w) with pure water as an enzyme extract and used in the next experiment.

<Evaluation of various materials>
20 μL of benzylcysteine (10 mM aqueous solution) and 10 μL of a 1% by mass DPG solution of a compound to be evaluated (evaluation sample) were mixed and heated to 30 ° C.
On the other hand, 10 μL of Staphylococcus lentus H292 enzyme extract, 10 μL of pyridoxal phosphate (1 mM aqueous solution), 20 μL of 0.5% by weight borate buffer (50 mM, pH 8.5) are added to distilled water to 170 μL to reach 30 ° C. Warmed up.
A mixture of these two liquids (0.2 mL) was allowed to stand at 30 ° C. for 20 hours. After adding 5 μL of trichloroacetic acid, the mixture was neutralized with 60 μL of ammonium carbonate water. The pyruvic acid contained in the sample was quantified by LC-MS / MS under the following conditions.

LC-MS / MS conditions Column: Inertsil ODS-3, 5μm, 2.1mmID, 25cm
Developing solution: water (80%) methanol (20%) mixture (2 mM ammonium acetate)

Further, as a control (blank), the amount of pyruvic acid produced in the following test was quantified without adding an evaluation sample.
That is, 20 μL of benzylcysteine (10 mM aqueous solution) and 10 μL of DPG were mixed and heated to 30 ° C. On the other hand, 10 μL of Staphylococcus lentus H292 enzyme extract, 10 μL of pyridoxal phosphate (1 mM aqueous solution), 20 μL of 0.5 mass% borate buffer (50 mM, pH 8.5) are added to distilled water to 170 μL, and added to 30 ° C. Warm up. A mixture of these two liquids (0.2 mL) was allowed to stand at 30 ° C. for 20 hours. After adding 5 μL of trichloroacetic acid, the mixture was neutralized with 60 μL of ammonium carbonate water. The pyruvic acid contained in the sample was quantified by LC-MS / MS under the above conditions.

  According to the following formula, the amount of pyruvic acid obtained in the blank was taken as 100%, and the proportion of the amount of pyruvic acid decreased by adding the evaluation sample was taken as the C-S lyase inhibition rate. The results are shown in Table 1.

As shown in Table 1, L-citronellol, which is a compound similar in structure to geraniol but lacking a double bond at the β-position, did not show a CS lyase inhibitory effect. Similarly, tetrahydrolinalol, which is a compound having a skeletal structure similar to linalool but not containing a double bond, did not have a CS lyase inhibitory effect. From these results, in a group having a specific similar molecular structure, a carbonyl compound and an alcohol compound having no double bond at the β-position have no deodorizing effect and a carbonyl compound and an alcohol having a double bond at the β-position. The compound is presumed to have a CS lyase inhibitory effect.
In this test, the amount of the evaluation sample relative to the substrate in the test solution is about 2 to 3 times in molar ratio, and there is no effect or weakness in masking the odor derived from the S compound generated by the evaluation sample. Despite being speculated, there was a deodorizing effect. This is presumed to be because the decomposition of the odor precursor was suppressed.

Example 2 Measurement of CS Lyase Inhibitory Effect in Model Evaluation System for Specific Perfume CS lyase inhibition rate was measured for terpineol, dihydromyrcenol and tricyclodecenyl acetate in the same manner as in Example 1. The results are shown in Table 2.

Formulation Example 1 Stick type deodorant agent According to the following formulation, the activity of CS lyase is inhibited by blending the stick type deodorant agent with the compound having a CS lyase inhibition rate of 60% or more in Example 1 as a fragrance. The generation of odor can be suppressed.

Formulation Example 2 Lotion-type (roll-on) deodorant agent According to the following formulation, a roll-on-type deodorant agent is blended with a fragrance having an inhibition rate of 60% or more in Example 1 as a fragrance. It inhibits and can suppress the generation of odor.

Formulation Example 3 Lotion Type (Natural Spray) Deodorant According to the following formulation, the activity of CS lyase is added to the lotion type deodorant by adding the fragrance having an inhibition rate of 60% or more in Example 1 as a fragrance. Can be suppressed, and the generation of odor can be suppressed. This solution can be used as a lotion as it is.

Claims (6)

A CS lyase inhibitor comprising one or more compounds selected from carbonyl compounds and alcohol compounds represented by the general formula (1).

[Wherein, X represents an oxygen atom or a hydroxyl group, and the broken line represents a double bond when X is an oxygen atom, and a single bond when X is a hydroxyl group. R ¹ , R ¹ ′, R ² , R ^3, and R ⁴ represent a hydrogen atom, a hydroxyl group, or a linear, branched, or cyclic alkyl group, alkenyl group, or alkenyloxy group, and R ¹ , R ⁴ , R ² And R ³ , R ³ and R ⁴ may be combined together to form a cyclic structure with adjacent carbon atoms. However, R ¹ ′ does not exist when X is an oxygen atom. ]   The compound represented by the general formula (1) is cis-jasmon, nootkatone, β-ionone, α-damascone, benzaldehyde, α-ionone, α-methylionone, γ-methylionone, β-damasenone, cis-3-hexenyl salicylate. The CS lyase inhibitor according to claim 1, which is selected from linalool, nerolidol, geraniol and trans-2-hexenol.   A C-S lyase inhibitor comprising one or more compounds selected from terpineol, dihydromyrcenol and tricyclodecenyl acetate.   A composition for suppressing odor production, comprising the C-S lyase inhibitor according to any one of claims 1 to 3.   The deodorant agent containing the C-S lyase inhibitor in any one of Claims 1-3.   A method for suppressing odor production, wherein the C-S lyase inhibitor according to any one of claims 1 to 3 is applied to the axilla part in an amount of 0.1 µg to 10,000 µg.