Deodorant, cosmetic preparation, or deodorizing method

Abstract

The present invention addresses the problem of providing: a novel compound capable of eliminating or deodorizing α,β-unsaturated aldehydes such as 2-nonenal; and a deodorant or the like which contains the compound.　Provided is a compound represented by formula (I) or a salt thereof. (In formula (I), R1 is NHNH2, NH2, OH, or OR7; R2 is a hydrogen atom or a C1-C4 alkyl group; R3 is a hydrogen atom, NR8R9, or a C1-C4 alkyl group; R4 is a hydrogen atom or a C1-C4 alkyl group; R5 is a hydrogen atom or a C1-C4 alkyl group; R6 is NH2, (CH2)mNH2, OH, or SH; R7 is a C1-C4 alkyl group; R8 is a hydrogen atom or a C1-C4 alkyl group; R9 is a hydrogen atom or a C1-C4 alkyl group; m is an integer of 1-4; and n is an integer of 0-3.)

Description

Deodorant, cosmetic, or deodorizing method

[0001] The present invention relates to a compound having a deodorizing effect, a deodorizer for odorous components containing an α,β-unsaturated aldehyde such as nonenal or diacetyl, a cosmetic containing the deodorizer, and a method for deodorizing odorous components containing the α,β-unsaturated aldehyde or diacetyl.

[0002] As society continues to age in recent years, body odor, particularly "body odor associated with aging," which is unique to middle-aged and elderly people, has become recognized as a social problem, and there is a growing need for deodorant products that can eliminate body odor. It is known that "body odor associated with aging" is closely related to α,β-unsaturated aldehydes such as octenal and nonenal. A known causative agent of "body odor associated with aging" is 2-nonenal (hereinafter also referred to as "2-NE"), a malodorous substance that is generated when 9-hexadecenoic acid (palmitoleic acid), which increases in the sebum of middle-aged and elderly people, is oxidized and decomposed by lipid peroxides or by bacteria resident on the skin (Non-Patent Documents 1 and 2). Because 2-NE is water-insoluble and fat-soluble, dissolving only in oils and organic solvents, it is difficult to remove from the skin by bathing or ordinary skin cleansing. Furthermore, if 2-NE adheres to clothing from the skin, it is difficult to remove by simply washing the clothing. Therefore, in order to suppress body odor, it is desirable to remove 2-NE that has formed on the skin.

[0003] Diacetyl, which has a buttery odor, is known to cause off-flavors in beverages and other beverages, significantly affecting the flavor of the product. In particular, in the sake brewing industry, minute differences in concentration on the order of ppb can affect the aroma of a product, making sensitive quantification of diacetyl concentration useful for quality evaluation and product development. Furthermore, diacetyl is known to be a causative agent of middle-aged oily odor, and its removal is also desirable for suppressing body odor.

[0004] Techniques for removing body odor include, for example, a deodorant containing a water-soluble polymer having an amine structure that reduces odorous components including nonenal (see Patent Document 1), a body odor suppression composition characterized by containing an imidazole dipeptide compound and / or a salt thereof as an active ingredient (see Patent Document 2), and a four-polyphenol mixed extract that combines oolong tea extract, sweet tea extract, and known deodorizing extracts such as green tea extract and persimmon tannin extract to reduce body odor (see Non-Patent Document 2, above). However, the reduction of the odor of α,β-unsaturated aldehydes such as nonenal was not satisfactory. Furthermore, the method of extracting carnosines from fish described in Patent Document 2 was extremely difficult and impractical.

[0005] Carnosine and its analogs have been investigated for the purpose of eliminating 4-hydroxynonenal (HNE) in the brain. For example, carnosine analogs containing histidine with a diol group or a hydrazide group have been proposed (see Non-Patent Document 3). Furthermore, the present inventors independently developed carnosine hydrazide (CNN) and reported that CNN acts on HNE in the brain (see Non-Patent Document 4).

[0006] JP 2017-055815 A JP 2008-187928 A

[0007] Shinichiro Haze et al., J. Invest. Dermatol., 116, 520-524, 2001 Iwao Ryuguchi et al.: Journal of the Odor and Smell Environment Society, 43(5) 362-366, 2012Andrea Guiotto et al., J. Med. Chem., 48, 6156-6161, 2005K. Noguchi et al. al, Eur. J. Med. Chem., 163, 207-214, 2019

[0008] An object of the present invention is to provide a novel compound capable of eliminating or deodorizing α,β-unsaturated aldehydes such as 2-nonenal or diacetyl, and to provide a deodorant or the like containing the compound.

[0009] The active ingredients contained in currently commercially available deodorant products are mainly of three types: (a) odorant adsorbents, (b) disinfectants that suppress the production of odorants, and (c) fragrances that mask odors. In the course of an intensive search for new compounds capable of eliminating or deodorizing 2-nonenal, the present inventors worked to develop a component that converts the malodorous substance 2-nonenal into another substance through a chemical reaction. They then discovered that structural modification of the imidazole group in the CNN synthesized by the present inventors makes it possible to eliminate or deodorize 2-NE and even diacetyl, which are substances that cause aging odor, and thus completed the present invention.

[0010] That is, the present invention is as follows: [1] A compound represented by the following formula (I): or a salt thereof. 1 is NHNH2, NH2, OH, or OR 7 It is. 2 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 3 is a hydrogen atom, NR 8 R 9 or an alkyl group having 1 to 4 carbon atoms. 4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 5 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 6 is NH2, (CH2) m NH2, OH, or SH. R 7 is an alkyl group having 1 to 4 carbon atoms. 8 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 9 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. m is an integer of 1 to 4, and n is an integer of 0 to 3. [2] R in the formula (I) 1 is OH or NHNH2, R 3 is a hydrogen atom or NH, R 6 [3] The compound or salt thereof according to the above [1], wherein is NH2, (CH2)3NH2, or OH. or a salt thereof (wherein R 1 is NHNH2, NH2, OH, or OR 7It is. 2 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 3 is a hydrogen atom, NR 8 R 9 or an alkyl group having 1 to 4 carbon atoms. 4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 5 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 6 is NH2, (CH2) m NH2, OH, or SH. R 7 is an alkyl group having 1 to 4 carbon atoms. 8 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 9 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. m is an integer of 1 to 4, and n is an integer of 0 to 3. A deodorizer for an odor component containing an α,β-unsaturated aldehyde or diacetyl, comprising the following as an active ingredient. [4] The deodorizer according to [3] above, characterized in that the α,β-unsaturated aldehyde or diacetyl is 2-nonenal. [5] R in formula (I) 1 is OH or NHNH2, R 3 is a hydrogen atom or NH, R 6 is NH2, (CH2)3NH2, or OH. [6] The deodorant according to any one of [3] to [5] above, which is for suppressing body odor. [7] A cosmetic containing the deodorant according to any one of [3] to [6] above. [8] A deodorizing method, characterized by contacting an object containing an α,β-unsaturated aldehyde or diacetyl with the deodorant according to any one of [3] to [6] above.

[0011] The compound of the present invention can reduce α,β-unsaturated aldehydes or diacetyl. Furthermore, by using a deodorizer for odorous components containing α,β-unsaturated aldehydes or diacetyl of the present invention, it becomes possible to eliminate α,β-unsaturated aldehydes or diacetyl such as 2-nonenal and to deodorize the odor.

[0012] FIG. 1 shows the results of investigating the nonenal scavenging activity using compounds SF359 and SF360 in Example 2. FIG. 2 shows the results of investigating the deodorizing effect using compound SF360 in Example 3. FIG. 3 shows the results of investigating the nonenal scavenging activity using compounds SF359, SF360, and an existing deodorizing ingredient in Example 4. FIG. 4 shows the results of investigating the deodorizing strength of nonenal using compounds SF359, SF360, and an existing deodorizing ingredient in Example 4. FIG. 5 shows the results of investigating the deodorizing effect using compound SF359 or SF359 hydrochloride in Example 6. FIG. 6 shows the results of investigating the deodorizing effect using compound SF359 hydrochloride in Example 6, with incubation times of 10, 20, 40, and 60 minutes. FIG. 7 shows the results of investigating the scavenging effect when compound SF359 was sprayed onto a cloth impregnated with 2-nonenal in Example 7. FIG. 8 shows the results of examining the diacetyl scavenging activity using compound SF359 in Example 8.

[0013] The contents of all patent and non-patent literature cited herein are hereby incorporated by reference in their entirety.

[0014] The compound of the present invention is not particularly limited as long as it is a compound represented by the following formula (I) or a salt thereof, and hereinafter may be referred to as "the compound of the present invention."

[0015] or a salt thereof. 1 is NHNH2, NH2, OH, or OR 7 It is. 2 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 3 is a hydrogen atom, NR 8 R 9 or an alkyl group having 1 to 4 carbon atoms. 4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 5 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 6 is NH2, (CH2) m NH2, OH, or SH. R 7 is an alkyl group having 1 to 4 carbon atoms. 8is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 9 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, m is an integer of 1 to 4, and n is an integer of 0 to 3.

[0016] The deodorizer of the present invention for odorous components containing an α,β-unsaturated aldehyde is not particularly limited as long as it is a deodorizer for odorous components containing an α,β-unsaturated aldehyde or diacetyl, and contains the compound of the present invention as an active ingredient, and hereinafter may be referred to as the "deodorizer of the present invention."

[0017] The cosmetic of the present invention is not particularly limited as long as it contains the deodorant of the present invention, and hereinafter it will also be referred to as "the cosmetic of the present invention." Furthermore, the deodorizing method of the present invention is not particularly limited as long as it is a deodorizing method characterized by contacting the deodorant of the present invention with an object containing an α,β-unsaturated aldehyde or diacetyl, and hereinafter it will also be referred to as "the deodorizing method of the present invention."

[0018] (Compound) Each group of the compound represented by general formula (I) in this specification will be explained below.

[0019] The alkyl group having 1 to 4 carbon atoms is not particularly limited as long as it is a linear or branched alkyl group having 1 to 4 carbon atoms, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, and a t-butyl group. In this specification, "n-" indicates normal, "s-" indicates secondary, and "t-" indicates tertiary.

[0020] R in the formula (I) 1 is OH or NHNH2, R 3 is a hydrogen atom or NH, R 6 is preferably NH2, (CH2)3NH2, or OH, and n is 1. Furthermore, R 1 is NHNH2, R 3 is a hydrogen atom or NH, R 6is NH2, (CH2)3NH2, or OH, and n is 1. Specifically, preferred compounds represented by formula (I) above include the compound represented by formula (I-1) below ((S)-3-amino-N-(6-amino-1-hydrazineyl-1-oxohexan-2-yl)propanamide), the compound represented by formula (I-2) ((S)-3-amino-N-(3-amino-1-hydrazineyl-1-oxopropan-2-yl)propanamide), and the compound represented by formula (I-3) ((S)-3-amino-N-(1-hydrazineyl-3-hydroxy-1-oxopropan-2-yl)propanamide). In this specification, the compound represented by formula (I-1) may be referred to as compound SF359, the compound represented by formula (I-2) as compound SF360, and the compound represented by formula (I-3) as compound SF361.

[0021]

[0022]

[0023]

[0024] These compounds or salts thereof can be produced by known production methods using known compounds or commercially available products as raw materials.

[0025] For example, when n is 1, the compound represented by general formula (I) can be obtained by condensing an amine-protected alanine such as Cbz-β-alanine (N-carbobenzoxy-β-alanine) as a starting material with an amino acid methyl ester derivative using a condensing agent, and then converting it into a hydrazide using hydrazine or the like, followed by deprotection, but the present invention is not limited to these. Note that Cbz is an amine (NH ２) is a benzyloxycarbonyl group. Examples of the protecting group include alkoxycarbonyl groups such as Cbz, as well as Boc and Fmoc groups. Examples of the condensing agent include 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) and N,N-dicyclohexylcarbodiimide (DCC). The deprotection method can be adjusted appropriately depending on the protecting group. When the protecting group is a Cbz group, the deprotection reaction can be carried out by a hydrogenation reaction using a palladium-on-carbon (Pd—C) catalyst in a similar solution. When the protecting group is a Boc group, the deprotection reaction can usually be carried out in a solution containing a solvent having a hydroxyl group, such as water, methanol, or ethanol, under acidic conditions or by heating. The reaction product can then be isolated and purified by column purification or crystallization.

[0026] When n is 0, 2, or 3, the compounds can be synthesized in the same manner as above using Cbz-glycine, Cbz-GABA, or 5-(Carbobenzoxyamino)valeric Acid, respectively.

[0027] An example of synthesis of the compound represented by general formula (I) using Cbz-β-alanine as a starting material is shown below.

[0028]

[0029] In the above-mentioned route a), Cbz-β-alanine (compound A), a diaminoalkanoic acid methyl ester, and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) are dissolved in dichloromethane and reacted to condense Cbz-β-alanine with an amino acid methyl ester derivative to obtain compound B.

[0030] In the above route b), compound B obtained in a) is dissolved in ethanol, and hydrazine is added thereto to cause a reaction to obtain compound C.

[0031] In the above-mentioned route c), the compound C obtained in the above route b) is dissolved in ethanol, hydrogenated with palladium-supported carbon (Pd / C), and then stirred to react and deprotect, thereby obtaining a compound D. Note that the compound D is a compound having R=(CH ２ )３ NH ２ In this case, SF359 and R = NH ２ When R=OH, it is SF360, and when R=OH, it is SF361.

[0032] In each of the above a), b), and c), the reaction temperature can be 0 to 50° C., preferably 0 to 40° C., and more preferably room temperature, and the reaction time can be 1 to 48 hours, preferably 3 to 24 hours, and more preferably 6 to 18 hours.

[0033] The salts used herein are not particularly limited, and examples thereof include hydrohalide salts such as hydrochloride and hydrobromide; lower alkylsulfonates such as methanesulfonate, trifluoromethanesulfonate, and ethanesulfonate; allylsulfonates such as benzenesulfonate and p-toluenesulfonate; organic acid salts such as fumarate, succinate, citrate, tartrate, oxalate, and maleate; and amino acid salts such as glutamate and aspartate, with hydrochloride being preferred.

[0034] The compounds of the present invention and salts thereof have one or more asymmetric centers in their structural formulas, and may exist as two or more optical isomers and diastereomers, and the present invention encompasses all of the optical isomers and mixtures containing them in any ratio. Furthermore, the compounds of the present invention and salts thereof may exist as two geometric isomers derived from a carbon-carbon double bond in their structural formulas, and the present invention encompasses all of the geometric isomers and mixtures containing them in any ratio.

[0035] Furthermore, the compounds of the present invention and salts thereof may exist in multiple tautomers, and the present invention encompasses all of the tautomers and mixtures thereof in any ratio.

[0036] The compound represented by formula (I) forms a covalent bond with α,β-unsaturated aldehydes, such as 2-nonenal (2-NE), which is a causative substance of aging odor, and changes the α,β-unsaturated aldehyde to a different structure, in other words, eliminates the aldehyde, thereby suppressing the odor derived from the α,β-unsaturated aldehyde, thereby exhibiting a deodorizing effect. Examples of the α,β-unsaturated aldehyde include 2-nonenal, 2-octenal, and 2-hexenal, with 2-nonenal being preferred.

[0037] This shows the process by which 9-hexadecenoic acid (palmitoleic acid) present in the sebum of middle-aged and elderly people is broken down to produce trans-2-nonenal.

[0038] Furthermore, the compound described in the above formula (I) forms a covalent bond with diacetyl, a substance that causes aged odor, and changes diacetyl to a different structure, in other words, eliminates diacetyl, thereby suppressing the odor derived from diacetyl and thereby exhibiting a deodorizing effect.

[0039] (Deodorant) The deodorant of the present invention may contain the compound of the present invention, and may be prepared, for example, by dissolving the compound of the present invention in a solvent. The solvent for dissolving the compound of the present invention is not particularly limited, but examples thereof include water, methanol, ethanol, etc.

[0040] The deodorant of the present invention may be used alone or in combination with an existing detergent or fabric softener or its active ingredient, depending on the purpose. Examples of existing detergents or fabric softeners include, but are not limited to, powder synthetic detergents, liquid synthetic detergents, powder laundry detergents, liquid laundry detergents, and fabric softeners. Examples of active ingredients of existing detergents or fabric softeners include, but are not limited to, anionic surfactants such as linear alkylbenzene sulfonates and alkyl ether sulfates; nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyalkylene alkyl ethers, and polyoxyalkylene alkylamines; and cationic surfactants such as alkyltrimethylammonium chloride and dialkyldimethylammonium chloride.

[0041] The deodorant of the present invention can be used to suppress body odor, for example, in clothing or bedding to which 2-nonenal or diacetyl has adhered. Examples of the clothing include undershirts, T-shirts, dress shirts, blouses, trousers, skirts, training wear, hats, handkerchiefs, towels, knitwear, socks, underwear, tights, etc., and examples of the bedding include futons, futon covers, sheets, pillows, pillowcases, blankets, electric blankets, towel blankets, etc.

[0042] When using the deodorizer of the present invention to deodorize clothing or bedding, a method can be used in which a cleaning solution containing the deodorizer of the present invention is prepared and the clothing or bedding is washed with the cleaning solution, or the cleaning solution is sprayed onto the clothing or bedding.

[0043] The temperature for the washing can be set arbitrarily depending on the purpose, but is preferably in the range of 5 to 40° C. The washing method may include soaking, kneading, beating, stirring, etc.

[0044] The concentration of the compound of the present invention in the deodorant of the present invention may be suitably selected depending on the state of the object to be deodorized, and is not particularly limited, but is preferably in the range of 0.001 to 10% by weight, more preferably in the range of 0.01 to 1% by weight.

[0045] The deodorant of the present invention can be used for cleansing the skin. The form in which it is used for cleansing the skin is not particularly limited, and examples thereof include facial cleanser, shampoo, soap, body soap, and sweat wipes. Preferred embodiments include facial cleanser, shampoo, soap, and body soap. By using the deodorant of the present invention for cleansing the skin, the compound of the present invention acts on 2-nonenal or diacetyl, which are the cause of body odor associated with aging, thereby removing or washing away 2-nonenal or diacetyl from the skin, thereby effectively suppressing body odor associated with aging. These forms of skin cleansing compositions containing the compound of the present invention as an active ingredient can be produced by appropriately referring to known production methods.

[0046] (Cosmetics) The cosmetics of the present invention are those that contain the deodorant of the present invention and are applied to the skin or the like for the purpose of moisturizing, cleansing, or beautifying the skin's appearance. Examples include deodorant cosmetics such as antiperspirant sprays, antiperspirant wet sheets, and roll-on sticks; basic cosmetics such as facial cleansers, lotions, creams, emulsions, serums, packs, and cleansers; makeup cosmetics such as foundations, lipsticks, eye shadows, lip balms, lip glosses, lip liners, blushers, waxes, perfumes, solid perfumes, nail enamels, and mascaras; hair cosmetics such as shampoos, conditioners, and treatments; shaving lotions, after-sun lotions, body lotions, body oils, soaps, body washes, and bath additives. Preferred embodiments include cosmetics in spray containers, wet sheet cosmetics, roll-on sticks, shampoos, and body washes. The present cosmetic product is preferably a soap, body wash, shampoo, facial cleanser, or the like, which is intended to suppress body odor associated with aging and can be removed or washed off from the skin upon use. These cosmetic products can effectively suppress body odor associated with aging by removing or washing off 2-nonenal from the skin through the action of the present compound with 2-nonenal, which is the cause of body odor associated with aging. The present cosmetic product can be produced by appropriately referring to known production methods for cosmetics.

[0047] In addition, the present cosmetic preparation may contain various additives, as needed. Examples of such additives include moisturizers, whitening agents, soaps, anti-inflammatory agents, cooling agents, UV absorbers, UV scattering agents, vitamins, plant extracts, skin astringents, cell activators, vasodilators, blood circulation promoters, skin function enhancers, bactericides (antibacterial agents), pH adjusters, thickeners, antioxidants, chelating agents, surfactants, emulsifiers, colorants (dyes, pigments), fragrances, and preservatives. The various ingredients that can be used in the cosmetic preparation may be appropriately selected from ingredients available in the relevant technical field. These ingredients may be selected from, but are not limited to, the list of cosmetic ingredient names published by the Japan Cosmetic Industry Association and cosmetic ingredients registered in the International Nomenclature for Cosmetic Ingredients (INCI) by the Personal Care Products Council (PCPC).

[0048] The form of the cosmetic composition of the present invention is not particularly limited as long as it can be applied to the skin, and examples thereof include paste, mousse, gel, liquid, emulsion, suspension, cream, ointment, aerosol, spray, liniment, etc. Furthermore, when the cosmetic composition of the present invention is in the form of a liquid, emulsion, or suspension, it may be impregnated into a sheet substrate such as a nonwoven fabric.

[0049] The cosmetic composition is suitable for preventing body odor, particularly body odor associated with aging, and is applied to areas of the skin where body odor, particularly body odor associated with aging, is a concern, such as the armpits, chest, back, back of the neck, around the ears, or scalp.

[0050] The amount and frequency of application of the present cosmetic to the skin are determined appropriately depending on the content of the active ingredient of the present compound, the strength of body odor, etc. For example, it is recommended to apply the cosmetic to the skin once or 2 to 5 times a day, applying it to 1 cm of skin. ２ The amount of the compound of the present invention that is applied to the skin is about 0.01 ng to 10 μg, preferably 0.1 ng to 1 μg, and more preferably 0.2 ng to 0.5 μg, per 100g of the compound.

[0051] (Deodorizing method) The deodorizing method of the present invention is characterized by bringing the deodorant of the present invention into contact with an object containing an α,β-unsaturated aldehyde or diacetyl, and examples of the object containing an α,β-unsaturated aldehyde or diacetyl include the above-mentioned clothing, bedding, and skin.

[0052] The method of contacting the deodorant of the present invention with the object may include spraying, applying or immersing the deodorant on the object.

[0053] The present invention will be explained in more detail below with reference to examples, but the technical scope of the present invention is not limited to these examples.

[0054] Example 1 Compounds SF359, SF360, and SF361 were synthesized according to the following scheme.

[0055]

[0056] [Synthesis of SF359] (1) Reaction a) Methyl N 6 -[(benzyloxy)carbonyl]-N 2 -(3-{[(benzyloxy)carbonyl]amino}propanoyl)-L-lysinate (compound B-1)

[0057]

[0058] H-Lys(Z)-OMe, HCl 1 (500 mg, 1.70 mmol), N-Carbobenzoxy-β-alanine (377 mg, 1.70 mmol; Compound A), EDC·HCl (391 mg, 2.04 mmol), and 4-(dimethylamino)pyridine (DMAP) (208 mg, 1.70 mmol) were dissolved in CHCl (20 mL) at 0 °C and stirred overnight at room temperature. After stirring, 30 mL of CHCl was added and the mixture was washed with 1 M HCl solution (2 × 50 mL), 1 M NaOH solution (2 × 50 mL), and saturated brine (1 × 50 mL). The resulting organic layer was dried over NaSO and concentrated under reduced pressure to give Compound B-1 (white solid, 692 mg, 82%).

[0059] ​1 1H NMR (600 MHz, CDCl3) δ: 1.22 (m, 2H, CH2), 1.29 - 1.44 (m, 2H, CH2), 1.45 - 1.76 (m, 2H, CH2), 2.32 (t, 2H, J = 5.4 Hz, CH2), 3.02 (d, 2H, J = 6.2 Hz, CH2), 3.31 (t, 2H, J = 5.4 Hz, CH2), 3.57 (s, 3H, CH3), 4.42 (dd, 1H, J = 7.3, 4.7 Hz, CH), 4.96 (s, 4H, CH2 x 2), 5.31 (s, 1H, NH), 5.70 (s, 1H, NH), 6.83 (s, 1H, NH), 7.12 - 7.32 (m, 10H, CH x 10) 13 13C NMR (150 MHz, CDCl3) δ: 22.41, 29.26, 31.41, 35.76, 37.25, 40.37, 52.07, 52.31, 66.51, 127.89, 127.98, 128.01, 128.05, 128.15, 128.32, 128.36, 128.46, 128.50, / / 136.67, 136.71, 156.62, 156.76, 171.67, 172.92 FAB-MS (m / z) calcd for C 26 H 34 N3O7 500.2397. Found: 500.2422 [M+H]+

[0060] (2) Reaction b) Benzyl (S)-{3-[(6-{[(benzyloxy)carbonyl]amino}-1-hydrazineyl-1-oxohexan-2-yl)amino]-3-oxopropyl}carbamate (Compound C-1)

[0061]

[0062] Note: There seems to be an incomplete part in the "13C NMR" data in the original, where some numbers are separated by " / / ", which might need further clarification in the original content for a more accurate translation.Compound B-1 (692 mg, 1.39 mmol) was dissolved in EtOH (50 ml), hydrazine monohydrate (5 ml) was added, and the mixture was stirred overnight. The reaction mixture was then concentrated. Cold EtOH was added, and the precipitate was filtered off with suction to give compound C-1 (white solid, 430 mg, 62%).

[0063] 1 H NMR (600MHz, DMSO) δ: 1.15 - 1.28(m, 2H, CH2), 1.34 - 1.39(m, 2H, CH2), 1.43 - 1.60(m, 2H, CH2), 2.29(t, 2H, J = 7.2 Hz, CH2), 2.94(dd, 2H, J = 6.8, 6.0 Hz, CH2), 3.20(dd, 2H, J = 7.0, 6.0 Hz, CH2), 4.16(dt, 1H, J = 8.5, 5.7 Hz, CH), 4.19(s, 2H, NH2), 5.00(dt, 4H, J = 20.0, 4.0 Hz, CH2 x 2), 7.20(s, 2H, NH x 2), 7.28 - 7.38(m, 10H, CH x 10), 7.98(s, 1H, NH), 9.09(t, 1H, J = 19.9 Hz, NH) 13 C NMR (150 MHz, DMSO) δ: 22.64, 29.07, 31.82, 35.41, 37.06, 40.13, 51.13, 65.09, 65.17, 127.29, 127.69, 128.16, 128.31, 137.17, 137.27, 155.97, 156.05, 170.11, 170.9511 FAB-MS (m / z) calcd for C 25 H 34 N5O6 500.2509. Found: 500.2528 [M+H]+

[0064] (3) Reaction c) (S)-3-αAmino-N-(6-amino-1-hydrazineyl-1-oxohexan-2-yl)propanamide (compound SF359)

[0065] ​

[0066] Compound C-1 (267 mg, 0.54 mmol) was dissolved in EtOH (15 ml) and HO (15 ml), and 10% Pd / C (114 mg, 1.07 mmol) was added. The mixture was purged with hydrogen and stirred overnight. The reaction mixture was filtered through Celite, and the filtrate was concentrated to obtain SF359 (not the hydrochloride salt). The residue was then dissolved in EtOH (10 ml) and HO (1 ml), and a hydrogen chloride-1,4-dioxane solution (2.4 mL) was added at 0 °C. The precipitate was collected to obtain compound SF359 hydrochloride (orange solid, 74 mg, 52%).

[0067] 1 H NMR (600MHz, DMSO) δ: 1.29 - 1.78(m, 6H, CH2), 2.62(t, 2H, J = 7.2 Hz, CH2), 2.76(d, 2H, J = 6.4 Hz, CH2), 2.97(dd, 2H, J = 6.4, 6.1 Hz, CH2), 4.32(td, 1H, J = 8.2, 5.3 Hz, CH), 8.11(s, 6H, NH2 x 3), 8.62(s, 1H, NH), 11.29(s, 1H, NH) 13 C NMR (150 MHz, DMSO) δ: 22.16, 26.26, 30.65, 31.96, 35.04, 38.28, 40.04, 55.97, 169.76, 170.95 FAB-MS (m / z) calcd for C9H 22 N5O2 232.1774. Found: 232.1761 [M+H]+

[0068] [Synthesis of SF360] (1) Reaction a) Methyl (S)-3-{[(benzyloxy)carbonyl]amino}-2-(3-{[(benzyloxy)carbonyl]amino}propanamido)propanoate (Compound B-2)

[0069]

[0070] ​H-Dap(Z)-OMe (938 mg, 3.72 mmol), N-Carbobenzoxy-β-alanine (826 mg, 3.72 mmol; compound A), and DMAP (454 mg, 3.72 mmol) were dissolved in THF (100 mL) at 0 °C. N,N-Dicyclohexylcarbodiimide (DCC) (921 mg, 4.46 mmol) was added and stirred overnight. Then, an equal amount of oxalic acid was added to the DCC and stirred vigorously for 10 min, filtered, and concentrated. After concentration, the mixture was dissolved in AcOEt and washed with saturated NaHCO3 solution (3 × 50 mL) and saturated brine (100 mL). The resulting organic layer was dried over Na2SO4, and the solvent was removed. The residue was purified by column chromatography (hexane:AcOEt = 1:5) to give compound B-2 (white solid, 889 mg, 71%).

[0071] 1 H NMR (600MHz, CDCl3) δ: 2.34 - 2.49(m, 2H, CH2), 3.48(d, 2H, J = 4.2 Hz, CH2), 3,53 - 3.67(m, 2H, CH2), 3.73(s, 3H, CH3), 4.61(q, 1H, J = 5.5 Hz, CH), 5.05(dd, 4H, J = 23.3, 11.3 Hz, CH2 x 2), 5.20(s, 1H, NH), 5.51(s, 1H, NH), 6.64(s, 1H, NH), 7.33(m, 10H, , CH x 10) 13 C NMR (150 MHz, DMSO) δ: 36.20, 37.18, 42.36, 52.77, 53.46, 66.70, 67.16, 128.02, 128.06, 128.15, 128.26, 128.49, 128.54, 136.20, 136.57, 156.61, 156.86, 170.65, 171.62 FAB-MS (m / z) calcd for C 23 H 28 N3O7 458.1927. Found: 458.1941 [M+H]+

[0072] ​(2) Reaction b) Benzyl (S)-[2-(3-{[(benzyloxy)carbonyl]amino}propanamido)-3-hydrazineyl-3-oxopropyl]carbamate (Compound C-2)

[0073]

[0074] Compound B-2 (955 mg, 2.09 mmol) was dissolved in EtOH (40 mL), and hydrazine monohydrate (5 mL) was added. After stirring overnight, the reaction mixture was cooled to -20 °C. The resulting solid was filtered under suction, washed several times with cold ethanol, and then dried to obtain compound C-2 (white solid, 817 mg, 86%).

[0075] 1 H NMR (600MHz, DMSO) δ: 2.31(dt, 2H, J = 7.2, 1.9 Hz, CH2), 3.20(dd, 4H, J = 6.5, 2.5 Hz, CH2 x 2), 4.18(s, 2H, NH2), 4.31(dd, 1H, J = 7.6, 5.8 Hz, CH), 5.02(s, 4H, CH2 x 2), 7.15(s, 1H, NH), 7.21(s, 1H, NH), 7.28 - 7.39(m, 10H, CH x 10), 7.92(d, 1H, J = 8.3 Hz, NH), 9.13(s, 1H, NH), 13 C NMR (150 MHz, DMSO) δ: 35.54, 36.92, 40.05, 42.35, 51.57, 65.21, 65.37, 127.67, 127.70, 127.73, 128.30, 137.03, 137.15, 156.00, 156.22, 168.91, 170.32 FAB-MS (m / z) calcd for C 22 H 28 N5O6 458.2040. Found: 458.1998 [M+H]+

[0076] ​(3) Reaction c) (S)-3-Amino-N-(3-amino-1-hydrazineyl-1-oxopropan-2-yl)propanamide (compound SF360)

[0077]

[0078] Compound C-2 (817 mg, 1.79 mmol) was dissolved in EtOH (160 mL) and HO (35 mL), and 10% Pd / C (380 mg, 3.57 mmol) was added. The atmosphere was replaced with hydrogen and the mixture was stirred for 24 hours. The reaction mixture was filtered through Celite, and the filtrate was concentrated to give compound SF360 (yellow, clear liquid, 300 mg, 90%).

[0079] 1 H NMR (600MHz, DMSO) δ: 2.13 - 2.28(m, 2H, CH2), 2.64 - 2.81(m, 4H, CH2 x 2), 4.22(dd, 1H, J = 6.7, 6.4 Hz, CH), 7.98(d, 1H, J = 7.8 Hz, NH), 9.3(s, 1H, NH) 13 C NMR (DMSO) δ: 43.36, 43.85, 53.62, 54.58, 170.03, 171.82 FAB-MS (m / z) calcd for C6H 16 N5O2 190.1304. Found: 190.1319 [M+H]+

[0080] [Synthesis of SF361] (1) Reaction a) Methyl O-benzyl-N-(3-{[(benzyloxy)carbonyl]amino}propanoyl)-L-serinate (Compound B-3)

[0081]

[0082] ​H-Ser(Bzl)-OMe, HCl (2.00 g, 8.14 mmol), N-Carbobenzoxy-β-alanine (1.81 g, 8.14 mmol: Compound A), and DMAP (0.99 g, 8.14 mmol) were dissolved in THF (100 ml) at 0 °C. N,N-dicyclohexylcarbodiimide (DCC) (2.02 g, 9.77 mmol) was added and stirred overnight. Then, an equal amount of oxalic acid was added to the DCC and stirred vigorously for 10 minutes, filtered, and concentrated. After concentration, the mixture was dissolved in AcOEt and washed with saturated NaHCO3 solution (3 × 50 ml) and saturated brine (1 × 100 ml). The resulting organic layer was dried over Na2SO4, and the solvent was removed. The residue was purified by column chromatography (Hexane: AcOEt = 1:5) to give compound B-3 (white solid, 3.15 g, 93%).

[0083] 1 H NMR (600MHz, CDCl3) δ: 2.34 - 2.49 (m, 2H, CH2), 3.33 - 3.47 (m, 2H, CH2), 3.63 (s, 3H, CH3), 3.72 (qd, 2H, J = 9.9, 3.3 Hz, CH2), 4.42 (dd, 2H, J = 27.6, 12.2 Hz, CH2), 4.71 - 4.76 (m, 1H, CH), 5.03 (s, 2H, CH2), 5.84 (t, 1H, J = 5.7 Hz, NH), 7.03 (d, 1H, J = 8.1 Hz, NH), 7.20 - 7.33 (m, 10H, CH x 10) 13 C NMR (200 MHz, CDCl3) δ: 35.75, 37.19, 52.51, 52.64, 66.51, 69.48, 73.19, 127.69, 127.93, 127.95, 128.00, 128.46, 136.73, 137.47, 156.53, 170.74, 171.56 FAB-MS (m / z) calcd for C 22 H 26N2O6 415.1869. Found: 415.1887 [M+H]+

[0084] (2) Reaction b) Benzyl (S)-(3-{[3-(benzyloxy)-1-hydrazineyl-1-oxopropan-2-yl]amino}-3-oxopropyl)carbamate (Compound C-3)

[0085]

[0086] Compound B-3 (3.88 g, 9.35 mmol) was dissolved in EtOH (40 mL), and hydrazine monohydrate (5 mL) was added. After stirring overnight, the reaction mixture was cooled to −20° C. The resulting solid was filtered by suction, washed several times with cold ethanol, and then dried to obtain compound C-3 (white solid, 2.27 g, 58%).

[0087] 1 H NMR (600MHz, DMSO) δ: 2.29 - 2.40 (m, 2H, CH2), 3.17 - 3.24 (m, 2H, CH2), 3.55 (dd, 2H, J = 6.1, 2.4 Hz, CH2), 4.26 (s, 2H, NH2), 4.47 (d, 2H, J = 1.9 Hz, CH2), 4.51 (dd, 1H, J = 8.3, 6.1 Hz, CH), 5.01 (s, 2H, CH2), 7.21 (t, 1H, J = 5.5 Hz, NH), 7.33 (m, 10H, CH x 10), 8.12 (d, 1H, J = 8.3 Hz, NH), 9.23 (s, 1H, NH) 13 C NMR (150 MHz, DMSO) δ: 35.35, 36.97, 51.22, 65.19, 69.71, 71.95, 127.40, 127.47, 127.70, 127.74, 128.18, 128.32, 137.14, 138.10, 155.98, 168.72, 170.31 FAB-MS (m / z) calcd for C 21 H 26N4O5 415.1981. Found: 415.2006 [M+H]+

[0088] (3) Reaction c) (S)-3-Amino-N-(1-hydrazineyl-3-hydroxy-1-oxopropan-2-yl)propanamide (compound SF361)

[0089]

[0090] Compound C-3 (1.01 g, 2.41 mmol) was dissolved in EtOH (100 mL) and HO (50 mL), and 10% Pd / C (514 mg, 4.83 mmol) was added. The atmosphere was replaced with hydrogen and the mixture was stirred for 24 hours. The reaction mixture was filtered through Celite, and the filtrate was concentrated to give compound SF361 (orange solid, 107 mg, 22%).

[0091] 1 H NMR (600MHz, DMSO) δ: 2.25 (ddt, 2H, J = 17.2, 14.0, 7.1 Hz, CH2), 2.77 (m, 2H, CH2), 3.56 (m, 2H, CH2), 4.26 (m, 1H, CH), 8.00 (d, 1H, J = 7.1Hz, NH), 9.34 (s, 1H, NH) 13 C NMR (150 MHz, DMSO) δ: 37.63, 37.94, 54.02, 61.58, 169.17, 171.48 FAB-MS (m / z) calcd for C6H 14 N4O3 191.1144 Found: 191.1128 [M+H]+

[0092] Example 2 (2-nonenal scavenging activity) SF359 or SF360, one of the compounds synthesized in Example 1, was used to examine the scavenging activity of 2-nonenal, a causative substance of aging odor. 2-nonenal (4 mM / 400 μL: Tokyo Chemical Industry Co., Ltd.) was mixed with deodorant compounds SF359 or SF360 (0, 4, 16, 40 mM / 400 μL), vortexed for 5 seconds, and then incubated at 37°C for 60 minutes with shaking (120 rpm). The remaining amount of 2-nonenal was then measured using HPLC (Column: COSMOSIL Packed Column 5C18-MS-II 4.6 ID × 150 mm, 25°C, methanol / distilled water (80 / 20 (v / v)), flow rate: 0.50 mL / min). Nonenal was dissolved in ethanol, and the deodorizing compound was dissolved in purified water. The results are shown in Figure 1. In Figure 1, 1:0, 1:1, 1:4, and 1:10 represent the concentrations of the deodorizing compound at 0, 4, 16, and 40 mM / 400 μL, respectively.

[0093] 1, it was confirmed that both compounds SF359 and SF360 had concentration-dependent 2-nonenal scavenging activity. Furthermore, for compound SF359, the scavenging activity was 42.7% at a 1:4 ratio and 6.1% at a 1:10 ratio compared to a 1:0 ratio, while for compound SF360, the scavenging activity was 18% at a 1:4 ratio and 3.8% at a 1:10 ratio compared to a 1:0 ratio, demonstrating extremely high deodorizing activity. These results suggest that compounds SF359 and SF360 capture 2-nonenal.

[0094] Example 3 (Deodorizing Effect of 2-Nonenal) The deodorizing effect of 2-nonenal was examined by a sensory test using compound SF360. 2-Nonenal (1 mM, 0.5 ml) and compound SF360 (0, 1, 2, 4, 10 mM, 0.5 ml each) were added to a 10 mL vial, vortexed for 5 seconds, placed in an incubator at 37°C, and gently stirred with a stirrer. The odor intensity of each sample was evaluated by eight odor judges every hour for up to 6 hours. The results are shown in Figure 2. The odor intensity (six-point scale) is as follows: "Odorless": 0 points, "Barely detectable odor (detection threshold concentration)": 1 point, "Weak odor that is recognizable (recognition threshold concentration)": 2 points, "Easily detectable odor": 3 points, "Strong odor": 4 points, "Strong odor": 5 points

[0095] 2, the sensory test confirmed that compound SF360 exhibits a concentration-dependent deodorizing effect. In particular, compared to 1:0, at 1:4 the odor was weak enough to be identified, and at 1:10 the odor was reduced to a barely detectable level, demonstrating extremely high deodorizing activity.

[0096] Example 4 (Comparison of 2-nonenal elimination activity and deodorizing effect with existing deodorizing ingredients) The 2-nonenal elimination activity and deodorizing effect of compounds SF359 and SF360 synthesized in Example 1 above were compared with existing deodorizing ingredients. 2-Nonenal (4 mM / 400 μL: Tokyo Chemical Industry Co., Ltd.) was mixed with the deodorizing compounds 0.10% SF359 and 0.10% SF360, as well as existing deodorizing ingredients 5% cos-20 (PANCIL® COS-20: Release Scientific Industries Co., Ltd.), 5% ba210-1 (PANCIL ba210-1: Release Scientific Industries Co., Ltd.), 5% ps-m (PANCIL ps-m: Release Scientific Industries Co., Ltd.), 25% trehalose, and 1% black cumin (Oryza Oil & Fat Chemical Co., Ltd.) (0, 4, 16, and 40 mM / 400 μL). The mixture was vortexed for 5 seconds and then incubated at 37°C for 60 minutes with shaking (120 rpm). The remaining amount of 2-nonenal was then measured using HPLC (column: COSMOSIL Packed Column 5C18-MS-II 4.6 ID x 150 mm, 25°C, methanol / distilled water (80 / 20 (v / v)), flow rate: 0.50 mL / min). Nonenal was dissolved in ethanol, and the deodorizing compound was dissolved in purified water. The results are shown in Figure 3. In Figure 3, the (-) on the far left is a control without the deodorizing compound. Furthermore, the odor intensity of each of the above samples was evaluated by eight panelists, including an odor judge. The results are shown in Figure 4.

[0097] 3, it was confirmed that compounds SF359 and SF360 eliminated 2-nonenal at extremely low concentrations compared to existing deodorizing ingredients. Furthermore, it was confirmed from FIG. 4 that compounds SF359 and SF360 had a deodorizing effect on 2-nonenal at extremely low concentrations compared to existing deodorizing ingredients.

[0098] Example 5 (Product Obtained by Reacting SF359 with 2-Nonenal) In order to confirm the bond between SF359 and 2-nonenal, the mass of the product obtained by reacting SF359 synthesized in Example 1 with 2-nonenal was measured using a JEOL JMS-700 N (manufactured by JEOL Ltd.).

[0099] SF359 (10 mg, 0.043 mmol) and 2-NE (0.72 μl, 0.0043 mmol) were dissolved in 3 mL of EtOH and 3 mL of purified water, stirred at 37°C for 1 hour, and then extracted with AcOEt (3 × 10 mL). The resulting organic layer was dried over Na2SO4, the solvent was removed, and FAB-HRMS analysis was performed. A peak at M / Z 354.2841 was observed. This result indicates that compound C, which formed a covalent bond between SF359 and 2-nonenal, was identified. 18 H 35 This was consistent with the M+1 peak corresponding to N5O2 (353.2791).

[0100] Example 6 (2-Nonenal-Scavenging Activity of SF359 Hydrochloride) SF359 was used in Examples 2 to 4, but to compare whether SF359 hydrochloride had any difference in 2-nonenal-scavenging activity and reactive chemical activity compared to free SF359, evaluation was performed by HPLC measurement in the same manner as in Example 2 above.

[0101] 2-NE (4 mM) was mixed with SF359 or SF359 hydrochloride at concentrations of 0%, 0.02%, 0.08%, and 0.20%, respectively, and the mixture was vortexed for 5 seconds and then incubated at 37°C for 60 minutes with shaking (120 rpm). The odor was then confirmed, and the remaining amount of 2-NE was measured using HPLC. 2-NE was dissolved in EtOH, and the deodorizing compound was dissolved in purified water. The results are shown in Figure 5.

[0102] Furthermore, the amount of remaining 2-NE was measured using SF359 hydrochloride in the same manner as above, except that the incubation time was changed from 60 minutes to 10 minutes, 20 minutes, 40 minutes, and 60 minutes. The results are shown in Figure 6.

[0103] As shown in Figure 5, it was confirmed that SF359 hydrochloride, like compound SF359, had a concentration-dependent 2-nonenal elimination activity to a similar extent. Furthermore, as shown in Figure 6, it was confirmed that the deodorizing effect decreased as the incubation time decreased compared to 60 minutes of incubation, but that the remaining amount of 2-NE was reduced to almost half even after 10 minutes of incubation.

[0104] Example 7 (Elimination effect on cloth impregnated with 2-nonenal) 500 μL of 0.4 mM 2-NE was impregnated into the center of a 5 cm square piece of cotton cloth. 4 mM SF359 was placed in a spray bottle and sprayed once (200 μL) onto the cloth impregnated with 2-NE. Six panelists evaluated the odor immediately after spraying and 5 minutes later on a 3-point scale. Commercially available fragrance-free Febreze (registered trademark: P&G) was used as a control. The results are shown in Figure 7.

[0105] When Febreze, a commercially available deodorizer, was used, there was no deodorizing effect immediately after spraying, and the odor level had decreased to 2.17 five minutes after spraying. On the other hand, when SF359 was used, the odor level was 1.83 immediately after spraying and had decreased to 1.5 five minutes later. Therefore, it was confirmed that SF359 has a high deodorizing effect even on fabrics soaked in 2-nonenal.

[0106] Example 8 (Evaluation of diacetyl scavenging activity of SF359) In the above examples, the scavenging of 2-nonenal was evaluated, but the activity of chemical reaction with diacetyl, a substance that causes middle-aged oily odor, was also evaluated using HPLC.

[0107] Diacetyl (4 mM / 400 μL) and the deodorizing compound SF359 (0, 40, 80, 120, 200 mM / 400 μL) were mixed (diacetyl:SF359 = 1:0, 1:10, 1:20, 1:30, 1:50), vortexed for 5 seconds, and then incubated at 37°C for 60 minutes with shaking (120 rpm). Next, o-phenylenediamine (9.98 mg, 0.0923 mmol) as a derivatization reagent and zirconium chloride (2.41 mg, 0.0103 mmol) as a catalyst were added to each solution. The mixture was incubated at room temperature for 5 minutes with shaking (120 rpm). The mixture was diluted 1 / 20 with a 1:4 mixture of MeOH and distilled water and the remaining amount of diacetyl was measured using HPLC (Column: COSMOSIL Packed Column 5C18-MS-II 4.6 ID x 150 mm (Nacalai Tesque) at 25 °C, MeOH / distilled water (20 / 80 (v / v)), flow rate: 0.40 mL / min). Diacetyl was dissolved in EtOH, and SF359 was dissolved in purified water. The reaction between diacetyl and o-phenylenediamine is as follows. The results of measuring the remaining amount of diacetyl using HPLC are shown in Figure 8.

[0108]

[0109] The results of the HPLC measurement in FIG. 8 revealed that SF359 eliminated diacetyl in a concentration-dependent manner.

Claims

1. Formula (I): or a salt thereof. 1 is NHNH2, NH2, OH, or OR 7 It is. 2 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 3 is a hydrogen atom, NR 8 R 9 or an alkyl group having 1 to 4 carbon atoms. 4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 5 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 6 is NH2, (CH2) m NH2, OH, or SH. R 7 is an alkyl group having 1 to 4 carbon atoms. 8 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 9 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, m is an integer of 1 to 4, and n is an integer of 0 to 3.

2. R in the formula (I) 1 is OH or NHNH2, R 3 is a hydrogen atom or NH, R 6 2. The compound or salt thereof according to claim 1, wherein is NH2, (CH2)3NH2, or OH.

3. Formula (I): or a salt thereof (wherein R 1 is NHNH2, NH2, OH, or OR 7 It is. 2 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 3 is a hydrogen atom, NR 8 R 9 or an alkyl group having 1 to 4 carbon atoms. 4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 5 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 6 is NH2, (CH2) m NH2, OH, or SH. R 7 is an alkyl group having 1 to 4 carbon atoms. 8 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 9 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. m is an integer of 1 to 4, and n is an integer of 0 to 3.

4. The deodorant according to claim 3, wherein the α,β-unsaturated aldehyde or diacetyl is 2-nonenal.

5. R in the formula (I) 1 is OH or NHNH2, R 3 is a hydrogen atom or NH, R 6 5. The deodorant according to claim 3, wherein is NH2, (CH2)3NH2, or OH.

6. The deodorant according to any one of claims 3 to 5, which is used to suppress body odor.

7. A cosmetic containing the deodorant according to any one of claims 3 to 6.

8. A deodorizing method comprising contacting an object containing an α,β-unsaturated aldehyde or diacetyl with the deodorizer according to any one of claims 3 to 6.

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