WO2018198523A1

WO2018198523A1 - N-acylamino acid derivative

Info

Publication number: WO2018198523A1
Application number: PCT/JP2018/007336
Authority: WO
Inventors: 鈴木　正浩; 英　謙二; 俊太須ヶ原; シュヴェンドゥビスワス; 直弥山戸
Original assignee: 味の素株式会社
Priority date: 2017-04-28
Filing date: 2018-02-27
Publication date: 2018-11-01

Abstract

The present invention provides a compound having excellent oil-gelling capability. More specifically, the present invention provides a compound represented by formula (1) , or a salt of the compound. [In the formula: R1 is a straight chain or branched chain monovalent hydrocarbon group having 3-17 carbon atoms; R2 is a straight chain or branched chain monovalent hydrocarbon group having 4-12 carbon atoms; R3 is a straight chain or branched chain divalent hydrocarbon group having 2-6 carbon atoms; and R4 and R5 are each independently a hydrogen atom, a straight chain or branched chain monovalent hydrocarbon group having 1-18 carbon atoms or R'-C(=O)- (here, R' is a straight chain or branched chain monovalent hydrocarbon group having 1-18 carbon atoms).]

Description

N-acylamino acid derivatives

The present invention relates to N-acylamino acid derivatives and the like.

Control the fluidity of compositions that are liquid at room temperature (eg, cosmetics, pharmaceuticals, quasi-drugs, agricultural chemicals, feeds, fertilizers, paints) and process them into a form that meets diversified uses. The method is industrially important.

Certain amino acid derivatives such as N-lauroyl-L-glutamic acid dibutylamide and N-2-ethylhexanoyl glutamic acid dibutylamide have gelling ability of oil, so that shape stabilization of solid or liquid cosmetics and / or It has been reported that it can be used for touch improvement (Patent Document 1).

International Publication No. 2003/102104

However, the acidic amino acid derivative described in Patent Document 1 has low oil gelling ability, and a large amount of acidic amino acid derivative was required for oil gelation.

Therefore, an object of the present invention is to provide a compound having an excellent gelling ability with respect to oil.

As a result of intensive studies, the present inventors have found that a specific N-acyl basic amino acid derivative has an excellent gelation ability with respect to various organic solvents including oil, and have completed the present invention.

That is, the present invention is as follows.
[1] The following formula (1):

[Where,
R ₁ is a linear or branched monovalent hydrocarbon group having 3 to 17 carbon atoms,
R ₂ is a linear or branched monovalent hydrocarbon group having 4 to 12 carbon atoms,
R ₃ is a linear or branched divalent hydrocarbon group having 2 to 6 carbon atoms,
R ₄ and R ₅ are each independently a hydrogen atom, a linear or branched monovalent hydrocarbon group having 1 to 18 carbon atoms, or R′—C (═O) — (where R 'Is a linear or branched monovalent hydrocarbon group having 1 to 18 carbon atoms. Or a salt thereof.
[2] R ₁ is a linear or branched monovalent hydrocarbon group having 7 to 13 carbon atoms,
R ₂ is a linear or branched monovalent hydrocarbon group having 4 to 10 carbon atoms,
R ₃ is a linear or branched divalent hydrocarbon group having 3 to 5 carbon atoms,
R ₄ and R ₅ are each independently a hydrogen atom, a linear or branched monovalent hydrocarbon group having 1 to 10 carbon atoms, or R′—C (═O) — (where R Is a straight-chain or branched monovalent hydrocarbon group having 1 to 10 carbon atoms.) The compound or a salt thereof according to [1].
[3] R ₁ is a linear or branched monovalent hydrocarbon group having 11 carbon atoms,
R ₂ is a linear or branched monovalent hydrocarbon group having 5 to 8 carbon atoms,
R ₃ is a linear or branched divalent hydrocarbon group having 4 carbon atoms,
R ₄ and R ₅ are each independently a hydrogen atom, a linear or branched monovalent hydrocarbon group having 1 to 4 carbon atoms, or R′—C (═O) — (where R Is a straight-chain or branched monovalent hydrocarbon group having 1 to 4 carbon atoms.) The compound or a salt thereof according to [2].
[4] The monovalent hydrocarbon group in R ₁ , R ₂ , R ₄ , R ₅ , and R ′ is alkyl, and the divalent hydrocarbon group in R ₃ is alkylene, [1] to [3 Or a salt thereof.
[5] The compound or a salt thereof according to any one of [1] to [4], wherein R ₄ and R ₅ are each a hydrogen atom.
[6] The compound is (A) N ^α -hexanoyl-N ^ε -dodecanoyl-L-lysine amide, (B) N ^α -2-ethylhexanoyl-N ^ε -dodecanoyl-L-lysine amide, or (C) N ^α A compound or a salt thereof according to any one of [1] to [5], which is -3,5,5-trimethylhexanoyl-N ^ε -dodecanoyl-L-lysine amide.
[7] Formula (1) below:

[Where,
R ₁ is a linear or branched monovalent hydrocarbon group having 3 to 17 carbon atoms,
R ₂ is a linear or branched monovalent hydrocarbon group having 4 to 12 carbon atoms,
R ₃ is a linear or branched divalent hydrocarbon group having 2 to 6 carbon atoms,
R ₄ and R ₅ are each independently a hydrogen atom, a linear or branched monovalent hydrocarbon group having 1 to 18 carbon atoms, or R′—C (═O) — (where R 'Is a linear or branched monovalent hydrocarbon group having 1 to 18 carbon atoms. ] The gel-like composition containing the compound or its salt represented by these, and an organic solvent.
[8] The gel composition of [7], wherein the organic solvent is a hydrophilic organic solvent.
[9] The gel composition of [8], wherein the hydrophilic organic solvent is a polyhydric alcohol.
[10] The gel composition of [7], wherein the organic solvent is a hydrophobic organic solvent.
[11] The gel composition of [10], wherein the hydrophobic organic solvent is an oil agent.
[12] The gel composition of [11], wherein the oil agent is one or more oil agents selected from the group consisting of hydrocarbon oils, silicone oils, ester oils, and liquid oils and fats.
[13] The gel composition according to [11] or [12], wherein the oil agent is silicone oil.
[14] The gel composition according to any one of [7] to [13], wherein the gel composition further contains a humectant.
[15] The gel composition according to any one of [7] to [14], wherein the gel composition is a cosmetic.

The compound of the present invention or a salt thereof can have an excellent gelling ability with respect to various organic solvents including oil.
The compound of the present invention or a salt thereof can also exhibit a transparent property in a gel composition prepared by mixing with an organic solvent. Therefore, the gel-like composition of the present invention can give a high-grade appearance and can avoid the visual influence on the skin. Therefore, the gel composition of the present invention has an advantage that, for example, white residue due to coating can be reduced.

(I) The compound represented by the above formula (1) or a salt thereof The present invention provides the compound represented by the above formula (1) or a salt thereof.

R ₁ is a linear or branched monovalent hydrocarbon group having 3 to 17 carbon atoms. The number of carbon atoms of the hydrocarbon group in R ₁ is preferably 15 or less, more preferably 13 or less, and even more preferably 11 or less. The number of carbon atoms of the hydrocarbon group in R ₁ may also be 5 or more, 7 or more, or 9 or more. More specifically, the number of carbon atoms of the hydrocarbon group in R ₁ may be preferably 5 to 15, more preferably 7 to 13, even more preferably 9 to 11, particularly preferably 11. The hydrocarbon group in R ₁ is saturated or unsaturated. Examples of such hydrocarbon groups include alkyl, alkenyl, and alkynyl.

When R ₁ is alkyl, the alkyl is a linear or branched alkyl having 3 to 17 carbon atoms. Examples and preferred examples of the number of carbon atoms of alkyl in R ₁ are the same as the number of carbon atoms of the hydrocarbon group described above in R ₁ . Examples of the alkyl in R ₁ include propyl (eg, n-propyl, iso-propyl), butyl (eg, n-butyl, iso-butyl, sec-butyl, tert-butyl), pentyl (eg, n-pentyl). , Iso-pentyl, neo-pentyl, 1-ethylpropyl), hexyl (eg, n-hexyl, iso-hexyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 2- Ethylbutyl), heptyl (eg, n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 1,1-dimethylpentyl, 2,2-dimethylpentyl, 3,3-dimethylpentyl, 2-ethyl Pentyl), octyl (eg, n-octyl, 1-methylheptyl, 2-methylheptyl, 3-methylheptyl, 1, 1-dimethylhexyl, 2,2-dimethylhexyl, 3,3-dimethylhexyl, 2-ethylhexyl), nonyl (eg, n-nonyl, 3,5,5-trimethylhexyl), decanyl (eg, n-decanyl) , Undecanyl (eg, n-undecanyl), dodecanyl (eg, n-dodecanyl), tridecanyl (eg, n-tridecanyl), tetradecanyl (eg, n-tetradecanyl), pentadecanyl (eg, n-pentadecanyl), hexadecanyl (eg, n-hexadecanyl), and heptadecanyl (eg, n-heptadecanyl).

When R ₁ is alkenyl, the alkenyl is a straight or branched alkenyl having 3 to 17 carbon atoms. Examples and preferred examples of the number of carbon atoms of alkenyl in R ₁ are the same as the number of carbon atoms of the hydrocarbon group described above in R ₁ . Examples of alkenyl in R ₁ include propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, and heptadecenyl.

When R ₁ is alkynyl, alkynyl is straight-chain or branched alkynyl having 3 to 17 carbon atoms. Examples and preferred examples of the number of carbon atoms of alkynyl in R ₁ are the same as the number of carbon atoms of the hydrocarbon group described above in R ₁ . Examples of alkynyl for R ₁ include propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, decynyl, undecynyl, dodecynyl, tridecynyl, tetradecynyl, pentadecynyl, hexadecynyl, and heptadecynyl.

Preferably, R ₁ is linear or branched alkyl having 3 to 17 carbon atoms. Examples and preferred examples of the number of carbon atoms of alkyl in R ₁ are the same as the number of carbon atoms of the hydrocarbon group described above in R ₁ . Specific examples of such alkyl are as described above.

R ₂ is a linear or branched monovalent hydrocarbon group having 4 to 12 carbon atoms. The number of carbon atoms of the hydrocarbon group in R ₂ is preferably 10 or less, more preferably 9 or less, and even more preferably 8 or less. The number of carbon atoms of the hydrocarbon group in R ₂ may also be 5 or more. More specifically, the number of carbon atoms of the hydrocarbon group in R ₂ may be preferably 4 to 10, more preferably 4 to 9, and even more preferably 5 to 8. The hydrocarbon group in R ₂ is saturated or unsaturated. Examples of such hydrocarbon groups include alkyl, alkenyl, and alkynyl.

When R ₂ is alkyl, alkyl is linear alkyl or branched having 4 to 12 carbon atoms. Examples and preferred examples of the number of carbon atoms of alkyl in R ₂ are the same as the number of carbon atoms of the hydrocarbon group described above in R ₂ . Examples of the alkyl for R ₂ include butyl (eg, n-butyl, iso-butyl, sec-butyl, tert-butyl), pentyl (eg, n-pentyl, iso-pentyl, neo-pentyl, 1-ethylpropyl). ), Hexyl (eg, n-hexyl, iso-hexyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 2-ethylbutyl), heptyl (eg, n-heptyl, 1-dimethyl) Methylhexyl, 2-methylhexyl, 3-methylhexyl, 1,1-dimethylpentyl, 2,2-dimethylpentyl, 3,3-dimethylpentyl, 2-ethylpentyl), octyl (eg, n-octyl, 1- Methylheptyl, 2-methylheptyl, 3-methylheptyl, 1,1-dimethylhexyl, 2,2-dimethylhexyl, 3,3-dimethylhexyl, 2-ethylhexyl, 3,5,5-trimethylpentyl), nonyl (eg, n-nonyl, 3,5,5-trimethylhexyl), decanyl (eg, n-decanyl), undecanyl ( Examples include n-undecanyl) and dodecanyl (eg, n-dodecanyl).

When R ₂ is alkenyl, the alkenyl is linear or branched alkenyl having 4 to 12 carbon atoms. Examples and preferred examples of the number of carbon atoms of alkenyl in R ₂ are the same as the number of carbon atoms of the hydrocarbon group described above in R ₂ . Examples of alkenyl for R ₂ include butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, and dodecenyl.

When R ₂ is alkynyl, alkynyl is straight-chain or branched alkynyl having 4 to 12 carbon atoms. Examples and preferred examples of the number of carbon atoms of alkynyl in R ₂ are the same as the number of carbon atoms of the hydrocarbon group described above in R ₂ . Examples of alkynyl for R ₂ include butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, decynyl, undecynyl, and dodecynyl.

Preferably, R ₂ is a linear or branched alkyl having 4 to 12 carbon atoms. Examples and preferred examples of the number of carbon atoms of alkyl in R ₂ are the same as the number of carbon atoms of the hydrocarbon group described above in R ₂ . Specific examples of such alkyl are as described above.

R ₃ is a linear or branched (preferably linear) divalent hydrocarbon group having 2 to 6 carbon atoms. The number of carbon atoms of the divalent hydrocarbon group in R ₃ may preferably be 5 or less. The number of carbon atoms of the divalent hydrocarbon group for R ₃ may also be 3 or more. More specifically, the number of carbon atoms of the divalent hydrocarbon group in R ₁ may be preferably 3 to 5, more preferably 4. The divalent hydrocarbon group for R ₃ is saturated or unsaturated. Examples of such hydrocarbon groups include alkylene, alkenylene, and alkynylene.

When R ₃ is alkylene, alkylene is straight-chain or branched (preferably straight-chain) alkylene having 2 to 6 carbon atoms. Examples and preferred examples of the number of carbon atoms of the alkylene in R ₃ are the same as the number of carbon atoms of the hydrocarbon groups described above in R _3. Examples of the alkylene in R ₃ include ethylene, propylene (eg, n-propylene, iso-propylene), butylene (eg, n-butylene, iso-butylene, sec-butylene, tert-butylene), pentylene (eg, n -Pentylene, iso-pentylene, neo-pentylene, 1-ethylpropylene), hexylene (eg, n-hexylene, iso-hexylene, 1,1-dimethylbutylene, 2,2-dimethylbutylene, 3,3-dimethylbutylene, 2-ethylbutylene).

When R ₃ is alkenylene, the alkenylene is a linear or branched (preferably linear) alkenylene having 2 to 6 carbon atoms. Examples and preferred examples of the number of carbon atoms of alkenylene in R ₃ are the same as the number of carbon atoms of the hydrocarbon group described above in R ₃ . Examples of alkenylene in R ₃ include ethylenylene, propynylene, butenylene, pentenylene, and hexenylene.

When R ₃ is alkynylene, the alkynylene is a linear or branched (preferably linear) alkynylene having 2 to 6 carbon atoms. Examples and preferred examples of the number of carbon atoms of alkynylene in R ₃ are the same as the number of carbon atoms of the hydrocarbon group described above in R ₃ . Examples of the alkynylene in R ₃ include ethynylene, propynylene, butynylene, pentynylene, and hexynylene.

Preferably, R ₃ is a linear or branched (preferably linear) alkylene having 2 to 6 carbon atoms. Examples and preferred examples of the number of carbon atoms of alkylene in R ₃ are the same as the number of carbon atoms of the hydrocarbon group described above in R ₃ . Specific examples of such alkylene are as described above.

In certain embodiments, R ₃ may be n-butylene. When R ₃ is n-butylene, the compound represented by the above formula (1) corresponds to an N-acyl lysine amide derivative.

R ₄ and R ₅ are each independently a hydrogen atom, a linear or branched monovalent hydrocarbon group having 1 to 18 carbon atoms, or R′—C (═O) — (where R 'Is a linear or branched monovalent hydrocarbon group having 1 to 18 carbon atoms. The number of carbon atoms of the hydrocarbon group in R ₄ and R ₅ and R ′ is preferably 1 to 14, more preferably 1 to 10, still more preferably 1 to 6, and particularly preferably 1 It may be ~ 4. The hydrocarbon groups in R ₄ and R ₅ and R ′ are saturated or unsaturated. Examples of such hydrocarbon groups include alkyl, alkenyl, and alkynyl.

When R ₄ and / or R ₅ and / or R ′ is alkyl, the alkyl is a linear or branched alkyl having 1 to 18 carbon atoms. Examples and preferred examples of the number of carbon atoms of alkyl in R ₄ and / or R ₅ and / or R ′ are the same as the number of carbon atoms of the hydrocarbon group described above in R ₄ and R ₅ and R ′. Examples of alkyl in R ₄ and / or R ₅ and / or R ′ include, for example, methyl, ethyl, propyl (eg, n-propyl, iso-propyl), butyl (eg, n-butyl, iso-butyl, sec -Butyl, tert-butyl), pentyl (eg, n-pentyl, iso-pentyl, neo-pentyl, 1-ethylpropyl), hexyl (eg, n-hexyl, iso-hexyl, 1,1-dimethylbutyl, 2 , 2-dimethylbutyl, 3,3-dimethylbutyl, 2-ethylbutyl), heptyl (eg, n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 1,1-dimethylpentyl, 2, 2-dimethylpentyl, 3,3-dimethylpentyl, 2-ethylpentyl), octyl (eg, n-octyl, 1-methyl) Tilheptyl, 2-methylheptyl, 3-methylheptyl, 1,1-dimethylhexyl, 2,2-dimethylhexyl, 3,3-dimethylhexyl, 2-ethylhexyl), nonyl (eg, n-nonyl, 3,5,5) 5-trimethylhexyl), decanyl (eg, n-decanyl), undecanyl (eg, n-undecanyl), dodecanyl (eg, n-dodecanyl), tridecanyl (eg, n-tridecanyl), tetradecanyl (eg, n-tetradecanyl) , Pentadecanyl (eg, n-pentadecanyl), hexadecanyl (eg, n-hexadecanyl), heptadecanyl (eg, n-heptadecanyl), and octadecanyl (eg, n-octadecanyl).

When R ₄ and / or R ₅ and / or R ′ is alkenyl, the alkenyl is straight-chain or branched alkenyl having 2 to 18 carbon atoms. Examples and preferred examples of the number of carbon atoms of alkenyl in R ₄ and / or R ₅ and / or R ′ are the same as the number of carbon atoms of the aforementioned hydrocarbon group in R ₄ and R ₅ and R ′. Examples of alkenyl in R ₄ and / or R ₅ and / or R ′ include, for example, ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl , Heptadecenyl, and octadecenyl.

When R ₄ and / or R ₅ and / or R ′ is alkynyl, alkynyl is straight-chain or branched alkynyl having 2 to 18 carbon atoms. Examples and preferred examples of the number of carbon atoms of alkynyl in R ₄ and / or R ₅ and / or R ′ are the same as the number of carbon atoms of the above-mentioned hydrocarbon group in R ₄ and R ₅ and R ′. Examples of alkynyl in R ₄ and / or R ₅ and / or R ′ include, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, decynyl, undecynyl, dodecynyl, tridecynyl, tetradecynyl, pentadecynyl, hexadecynyl , Heptadecynyl, and octadecynyl.

Preferably, R ₄ and R ₅ each independently represent a hydrogen atom, a linear or branched alkyl having 1 to 18 carbon atoms, or R′—C (═O) — (where R ′ is And straight-chain or branched alkyl having 1 to 18 carbon atoms. R ₄ and R _5, and R 'examples and preferred examples of the number of carbon atoms of the alkyl in the, R ₄ and R _5, and R' is the same as the number of carbon atoms of the hydrocarbon groups described above in. Specific examples of such alkyl are as described above. More preferably, R ₄ and R ₅ are each a hydrogen atom.

Examples of the salt include a salt with an inorganic acid, a salt with an organic acid, a salt with an inorganic base, a salt with an organic base, and a salt with an amino acid. Examples of the salt with an inorganic acid include salts with hydrogen chloride, hydrogen bromide, phosphoric acid, sulfuric acid, and nitric acid. Examples of salts with organic acids include formic acid, acetic acid, trifluoroacetic acid, lactic acid, tartaric acid, fumaric acid, oxalic acid, maleic acid, citric acid, succinic acid, malic acid, benzenesulfonic acid, and p-toluenesulfonic acid. Of the salt. Examples of the salt with an inorganic base include alkali metals (eg, sodium, potassium), alkaline earth metals (eg, calcium, magnesium), and other metals such as zinc and aluminum, and salts with ammonium. . Examples of the salt with an organic base include salts with trimethylamine, triethylamine, propylenediamine, ethylenediamine, pyridine, ethanolamine, monoalkylethanolamine, dialkylethanolamine, diethanolamine, and triethanolamine. Examples of salts with amino acids include salts with basic amino acids (eg, arginine, histidine, lysine, ornithine) and acidic amino acids (eg, aspartic acid, glutamic acid).

Preparation of the compound represented by the above formula (1) can be appropriately performed based on the following reactions 1 and 2.

First, reaction 1 will be described.
Compound represented by the above formula (3) [wherein R ₁ and R ₃ are the same as those of the compound represented by the above formula (1). R _x is a monovalent hydrocarbon group (preferably alkyl) as described above for R ₁ and R ₂ . ] Is a raw material of reaction 1. The synthesis of the compound represented by the above formula (3) has been reported previously [eg, Suzuki, M. et al. et al. , Chem. Commun. 19, 2012-2013 (2001)]. The compound represented by the above formula (3) is converted to X—C (═O) —R ₂ , wherein R ₂ is the same as that of the compound represented by the above formula (1). X is a leaving group (eg, a halogen atom such as a chlorine atom). ] To produce a compound represented by the above formula (2). For example, the reaction can be performed in an appropriate solvent (eg, tetrahydrofuran) by appropriately adding an amine (eg, an alkylamine such as triethylamine). The reaction can also be carried out at a suitable temperature (eg, 15 to 40 ° C.) for several hours (eg, 1 to 8 hours). The compound represented by the above formula (2) can be appropriately purified by any purification method (eg, recrystallization) used in the field of organic synthesis.

Next, reaction 2 will be described.
The compound represented by the above formula (2) obtained in the reaction 1 is changed to NH (R ₄ ) (R ₅ ) [wherein R ₄ and R ₅ are those of the compound represented by the above formula (1). Is the same. ] To produce a compound represented by the above formula (1). For example, the reaction can be performed in a suitable solvent (eg, an alcohol such as methanol). The reaction can also be carried out at a suitable temperature (eg, 40 to 70 ° C.) for several hours to several days (eg, one week). The compound represented by the above formula (2) can be appropriately purified by any purification method used in the field of organic synthesis.

(II) Gel-like composition The present invention provides a gel-like composition. The gel composition of the present invention contains a compound represented by the formula (1) or a salt thereof, and an organic solvent. The details of the compound represented by the formula (1) or a salt thereof are as described above.

The organic solvent is a hydrophilic organic solvent, a hydrophobic organic solvent, or a mixture thereof.

The hydrophilic organic solvent is a solvent of an organic compound having a solubility in water of 1% (wt) or more (preferably 3% (wt) or more). As the hydrophilic organic solvent, any hydrophilic organic compound solvent can be used. As the hydrophilic organic solvent, a hydrophilic organic solvent having a moisturizing action is preferable. Examples of the hydrophilic organic solvent having a moisturizing action include solvents of polyhydric alcohols and other hydrophilic organic compounds having a moisturizing action.

Examples of the polyhydric alcohol include dihydric alcohols (eg, ethylene glycol, propylene glycol, 1,3-propanediol, 1,2-butylene glycol, 1,3-butylene glycol, 2,3-butylene glycol, 1, 4-butanediol, 2-butene-1,4-diol, 1,5-pentanediol, 1,2-pentanediol, isoprene glycol, hexylene glycol, diethylene glycol, dipropylene glycol), trihydric alcohol (eg, glycerin) , Trimethylolpropane), tetrahydric alcohols (eg, diglycerin, pentaerythritol, 1,2,6-hexanetriol), higher valent alcohols, and salts thereof (eg, salts as described above). It is done. Examples of higher valence alcohols include sugar alcohols (eg, monosaccharide alcohols such as sorbitol and mannitol, disaccharide alcohols such as trehalose, and polysaccharide alcohols such as hyaluronic acid), and divalent to tetravalent alcohols as described above. Examples include alcohol polymers (eg, polyglycol, polyglycerin) and salts thereof (eg, salts as described above). The polyhydric alcohol is preferably a dihydric to tetrahydric alcohol, and more preferably a dihydric or trihydric alcohol. One or more polyhydric alcohols can be used in combination.

Examples of the solvent of other hydrophilic organic compound having a moisturizing action include cyclic sulfone compounds (eg, sulfolane).

The hydrophobic organic solvent refers to a solvent of an organic compound having a solubility in water of less than 1% (wt) (preferably 0.1% (wt) or less). Examples of the hydrophobic organic solvent include an oil agent and a solvent of any organic compound other than the oil agent. Examples of the oil agent include hydrocarbon oil, silicone oil, ester oil, liquid oil and fat, higher fatty acid, and higher alcohol.

Hydrocarbon oil is a saturated or unsaturated hydrocarbon compound. Examples of the hydrocarbon oil include hydrocarbon compounds having 7 or more carbon atoms, preferably 10 or more, and more preferably 12 or more. The hydrocarbon oil may also be a hydrocarbon compound having 30 or fewer, 25 or fewer, or 20 or fewer carbon atoms. Such a hydrocarbon compound may have a substituent (eg, an alkyl group such as methyl). Examples of the hydrocarbon oil include paraffinic oil (eg, paraffin, liquid paraffin, isoparaffin, cycloparaffin), fuel oil (eg, light oil, heavy oil, petroleum, kerosene, gasoline, mixed oil), hydrocarbon chain (linear chain) Or a compound having a branched chain (eg, decane, undecane, dodecane (eg, n-dodecane), tridecane, tetradecane, pentadecane, hexadecane, squalane), a benzene ring compound (eg, benzene, toluene, alkyl benzoate (C12- And compounds having a hydrocarbon ring (aromatic or non-aromatic) such as 15)).

Examples of silicone oil include polysiloxane. Specific examples of polysiloxanes include linear polysiloxanes (eg, dimethylpolysiloxane, methylphenylpolysiloxane, diphenylpolysiloxane) and cyclic polysiloxanes (eg, cyclomethicone, cyclotetrasiloxane, cyclopentasiloxane, cyclohexasiloxane). , Modified polysiloxane (eg, amino-modified polysiloxane, polyether-modified polysiloxane, alkyl-modified polysiloxane).

Ester oil is an ester produced by the reaction of monohydric or polyhydric alcohol and carboxylic acid.

A mono- or polyhydric alcohol is a straight, branched or cyclic (monocyclic or bicyclic such as condensed ring) saturated or unsaturated hydrocarbon moiety (eg, hydrocarbon chain) having 1 or more carbon atoms. It may be a monohydric or polyhydric alcohol having Examples of the monohydric or polyhydric alcohol include monohydric or polyhydric alcohols having a hydrocarbon moiety having 1 to 30 carbon atoms. The number of carbon atoms may be, for example, 2 or more, preferably 3 or more. The number of carbon atoms may also be 25 or less, or 20 or less. The valence of the polyhydric alcohol is, for example, 2 to 6, preferably 2 or 3. Specific examples of the monohydric alcohol include methyl alcohol, ethyl alcohol, propyl (eg, n-propyl, iso-propyl) alcohol, butyl (n-butyl, iso-butyl, sec-butyl, tert-butyl) alcohol, and pentyl. Alcohol, hexyl alcohol, heptyl alcohol, octyl alcohol, nonyl alcohol, decanyl alcohol, undecanyl alcohol, lauryl alcohol, cetyl alcohol, stearyl alcohol, myristyl alcohol, oleyl alcohol, lanolin alcohol, cholesterol, phytosterol, hexyl decanol, iso Stearyl alcohol is mentioned. Specific examples of the polyhydric alcohol include ethylene glycol, propylene glycol, and glycerin.

The carboxylic acid is a monovalent or polyvalent carboxylic acid. Examples of the monovalent carboxylic acid include saturated or unsaturated fatty acids having 1 to 30 carbon atoms. The number of carbon atoms of the monovalent carboxylic acid may be, for example, 2 or more, preferably 3 or more. The number of carbon atoms of the monovalent carboxylic acid may also be 25 or less, or 20 or less. Specific examples of monovalent carboxylic acids include methanic acid (formic acid), ethanoic acid (acetic acid), propanoic acid (propionic acid), butanoic acid (butyric acid), pentanoic acid (valeric acid), hexanoic acid (caproic acid), heptane Acid, octanoic acid (caprylic acid), nonanoic acid (pelargonic acid), decanoic acid (capric acid), undecanoic acid (undecylic acid), dodecanoic acid (lauric acid), tridecanoic acid (tridecylic acid), tetradecanoic acid (myristic acid) Pentadecanoic acid (pentadecylic acid), hexadecanoic acid (palmitic acid), and octadecanoic acid (stearic acid). Examples of the polyvalent carboxylic acid include saturated or unsaturated acids having 1 to 30 carbon atoms. The number of carbon atoms of the polyvalent carboxylic acid may be, for example, 2 or more, preferably 3 or more. The number of carbon atoms of the polyvalent carboxylic acid may also be 25 or less, or 20 or less. The valence of the polyvalent carboxylic acid is, for example, 2 to 6, preferably 2 or 3. Specific examples of the polyvalent carboxylic acid include succinic acid, citric acid, tartaric acid, malic acid, maleic acid, fumaric acid, adipic acid, glutamic acid, and aspartic acid.

Specific examples of esters of monohydric alcohols and carboxylic acids include fatty acid ester oils as liquid oils (eg, cetyl ethylhexanoate, ethylhexyl palmitate, isopropyl myristate, isopropyl palmitate, tri (caprylic acid / capric acid) Fatty acid esters and polyhydric alcohol fatty acid esters such as glyceryl and triethylhexanoin], acyl amino acid esters [eg, lauroyl sarcosine isopropyl (Eldue (registered trademark) SL-205), N-lauroyl-L-glutamate di (cholesteryl / octyl) Dodecyl), hexyldecyl myristoylmethylaminopropionate, dihexyldecyl lauroylglutamate, diisostearyl lauroylglutamate, dioctyldodecyl lauroylglutamate, lauro Bis-glutamate (hexyldecyl / octyldodecyl), dioctyldecyl lauroylglutamate, dioctyldecyl stearoylglutamate), and phytosterol ester oils (eg N-lauroyl-L-glutamate di (phytosteryl / 2-octyldodecyl)), Semi-solid oils include cholesterol ester oils (eg, cholesteryl isostearate, cholesteryl hydroxystearate, macadamia nut oil fatty acid cholesteryl, N-lauroyl-L-glutamate di (cholesteryl / behenyl / octyldodecyl)), phytosterol ester oils (eg, N-lauroyl-L-glutamate di (phytosteryl / behenyl / 2-octyldodecyl), myristoylmethyl-β-alanine (phytosteryl) (Lu / decyltetradecyl), phytosteryl isostearate, phytosteryl oleate], dipentaerythritol fatty acid ester oils [eg, dipentaerythritol hexaoxystearate, dipentaerythritol rosinate].

Specific examples of esters of polyhydric alcohols and carboxylic acids include glycolide (eg, ethylene glycol di-2-ethylhexanoate, N-alkyl glycol monoisostearate, neopentyl glycol dicaprate, tripropylene glycol pivalate). Glycerides [eg, di-2-heptylundecanoic acid glycerin, diisostearic acid glycerin, tri-2-ethylhexanoic acid glycerin (triethylhexanoin), trioctanoic acid glycerin, triisopalmitic acid glycerin], tri (capryl / caprin / myristin / Stearic acid) and partially hydrogenated triglycerides such as glyceryl and hydrogenated oil.

Liquid oil is a biological liquid oil such as vegetable oil. Specific examples of liquid oils include soybean oil, linseed oil, castor oil, avocado oil, camellia oil, corn oil, rice oil, olive oil, rapeseed oil, sesame oil, wheat germ oil, sasanqua oil, safflower oil, cottonseed oil, jojoba And vegetable oils such as oil.

Examples of higher fatty acids include saturated or unsaturated fatty acids having 8 or more carbon atoms. The higher fatty acids may also have 30 or fewer, 25 or fewer, or 20 or fewer carbon atoms. The higher fatty acid may have a linear, branched or cyclic (preferably linear or branched) structure. Specific examples of the higher fatty acid include lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, isostearic acid, linoleic acid, and linolenic acid.

Examples of higher alcohols include alcohols having 6 or more carbon atoms. The higher alcohol may have a linear, branched or cyclic structure. As the higher alcohol, an alcohol having 8 or more carbon atoms is preferable, an alcohol having 10 or more carbon atoms is more preferable, and an alcohol having 12 or more carbon atoms is particularly preferable. The higher alcohol may also have 30 or fewer, 25 or fewer, or 20 or fewer carbon atoms. Specific examples of higher alcohols include hexyl alcohol, heptyl alcohol, octyl alcohol, nonyl alcohol, decanyl alcohol, undecanyl alcohol, lauryl alcohol, cetyl alcohol, stearyl alcohol, myristyl alcohol, oleyl alcohol, lanolin alcohol, cholesterol, phytosterol. Hexyl decanol and isostearyl alcohol.

The content of the compound represented by the formula (1) or a salt thereof in the gel composition of the present invention is determined by the compound represented by the formula (1) or the salt alone, or the compound represented by the formula (1) or There is no particular limitation as long as the gelling ability of the organic solvent can be improved by the combination of the salt and other components. Examples of such components include other gelling agents (eg, dibutyllauroylglutamide) and thickeners (eg, those described later). In the gel composition of the present invention, when the compound represented by the formula (1) or a salt thereof is used in combination with other components, the organic solvent can be gelled while reducing the content of other components. When the compound represented by the formula (1) or a salt thereof is used in combination with other components, the content of the compound represented by the formula (1) or a salt thereof is determined by the amount of other components due to gelation of the organic solvent. The amount is not particularly limited as long as the amount can contribute to the reduction of the content. For example, when the compound represented by the formula (1) or a salt thereof and another component are used in combination, the compound represented by the formula (1) or a salt thereof and the other component in the gel composition of the present invention The weight ratio of is not particularly limited, but the other component is, for example, less than 4 parts by weight, preferably less than 2 parts by weight with respect to 1 part by weight of the compound represented by the formula (1) or a salt thereof. More preferably, it may be less than 1 part by weight, still more preferably less than 0.75 part by weight, particularly preferably less than 0.5 part by weight or less than 0.25 part by weight.

More specifically, the gel composition of the present invention is obtained by the compound represented by formula (1) or a salt thereof alone, or by the combination of the compound represented by formula (1) or a salt thereof and other components. The content of the compound represented by the formula (1) or a salt thereof in formula (1) varies depending on the type and amount of the compound represented by the formula (1) or a salt thereof, an organic solvent, and other components. It may be 0.01% (wt) or more, preferably 0.1% (wt) or more, more preferably 1% (wt) or more, and even more preferably 2% (wt) or more. The content may also be 80% (wt) or less, preferably 50% (wt) or less, more preferably 30% (wt) or less, and even more preferably 20% (wt) or less. More specifically, the content is, for example, 0.01 to 80% (wt), preferably 0.1 to 50% (wt), more preferably 1 to 30% (wt), and even more preferably 2 to 20 % (Wt) may be sufficient. The gel composition of the present invention may contain one or more compounds represented by the formula (1) or salts thereof (eg, two, three, four).

The content of the organic solvent in the gel composition of the present invention is, for example, 1% (wt) or more, preferably 5% (wt) or more, more preferably 10% (wt) or more, and even more preferably 20% (wt). It may be the above. The content may also be, for example, 99.99% (wt) or less, preferably 95% (wt) or less, more preferably 90% (wt) or less, and even more preferably 80% (wt) or less. More specifically, the content is, for example, 1 to 99.99% (wt), preferably 5 to 95% (wt), more preferably 10 to 90% (wt), and still more preferably 20 to 80% ( wt). The gel composition of the present invention may contain one or more (eg, 2, 3, 4) organic solvents.

In the gel composition of the present invention, although it varies depending on the presence or absence of other components and the type and amount of the compound represented by the formula (1) or a salt thereof, an organic solvent, and other components, The amount of the compound represented by the formula (1) or a salt thereof is, for example, 0.001 mg or more, preferably 0.01 mg or more, more preferably 0.05 mg or more, still more preferably 0.1 mg or more, and particularly preferably It may be 1 mg or more. Such an amount may also be, for example, 999.0 mg or less, preferably 500 mg or less, more preferably 100 mg or less, even more preferably 50 mg or less, particularly preferably 20 mg or less. More specifically, the amount of the compound represented by the formula (1) or a salt thereof with respect to 1 mL of the organic solvent is, for example, 0.001 to 999.0 mg, preferably 0.01 to 500 mg, more preferably 0.05 to It may be 100 mg, still more preferably 0.1 to 50 mg, particularly preferably 1 to 20 mg.

The gel composition of the present invention may further contain moisture. The moisture in the gel composition of the present invention can be imparted by adding an aqueous solution to the compound represented by the formula (1) or a salt thereof, and an organic solvent. The aqueous solution may or may not have a buffer capacity. Examples of the aqueous solution include water (eg, distilled water, sterile distilled water, purified water, physiological saline), phosphoric acid aqueous solution (buffer solution), Tris-hydrochloric acid buffer solution, TE (Tris-EDTA) buffer solution, carbonate- Bicarbonate buffer, boric acid aqueous solution (buffer), tartaric acid aqueous solution (buffer), hydrochloric acid-potassium chloride buffer, glycine-hydrochloric acid buffer, glycine-sodium hydroxide buffer, citric acid aqueous solution (buffer), citrate Examples thereof include an acid-phosphate buffer solution and an acetic acid aqueous solution (buffer solution). The moisture in the composition of the present invention may be derived from one or more (eg, two, three, four) aqueous solutions.

The moisture content in the gel composition of the present invention is not particularly limited, but for example, 1% (wt) or more, preferably 10% (wt) or more, more preferably 25% (wt) or more, and even more. Preferably, it may be 40% (wt) or more, particularly preferably 50% (wt) or more. The moisture content is also, for example, 95% (wt) or less, preferably 90% (wt) or less, more preferably 85% (wt) or less, even more preferably 80% (wt) or less, particularly preferably 75% (wt ) It may be the following. More specifically, the water content is, for example, 1 to 95% (wt), preferably 10 to 90% (wt), more preferably 25 to 85% (wt), and even more preferably 40 to 80% (wt). ), Particularly preferably 50 to 75% (wt).

The gel composition of the present invention has one or more kinds (eg, two, three, four, etc.) having any action (eg, biological action, or chemical action) in addition to the components described above. Seed) active ingredient may be further included. Examples of such active ingredients include low molecular compounds.

The term “low molecular weight compound” refers to a compound having a molecular weight of 1500 or less. The low molecular compound is a natural compound or a synthetic compound. The molecular weight of the low molecular weight compound may be 1200 or less, 1000 or less, 900 or less, 800 or less, 700 or less, 600 or less, 500 or less, 400 or less, or 300 or less. The molecular weight of the low molecular compound may also be 30 or more, 40 or more, or 50 or more. Examples of the low molecular weight compound include amino acids, oligopeptides, vitamins, nucleosides, nucleotides, oligonucleotides, monosaccharides, oligosaccharides, lipids, fatty acids, and metabolites thereof, and salts thereof (eg, salts as described above). ). Such low molecular weight compounds may be moisturizers, whitening agents, or hair restorers.

Examples of humectants include pyrrolidone carboxylic acid, 3-acetyl-2-ethoxycarbonyl-2-methyl-1,3-thiazolidine-4-carboxylic acid, amino acids (eg, glutamic acid, aspartic acid, arginine, lysine, histidine, ornithine, Glycine, alanine, valine, leucine, isoleucine, serine, threonine, asparagine, glutamine, cysteine, cystine, methionine, phenylalanine, tyrosine, tryptophan, proline, hydroxyproline), glycylglycine, alanylglutamine, dipeptide-2 (valyltryptophan) ), Dipeptide-4 (cystenylglycine), dipeptide-8 (alanylhydroxyproline), dipeptide-9 (glutamyllysine), dipeptide-11 (cystenyllysine), dipep De -17 (glycyl proline), dipeptide -19 (isoleucyl glutamic acid), and salts (e.g., the above-mentioned salts). One or more moisturizers can be used in combination.

Examples of whitening agents include vitamin C, vitamin C derivatives (eg, vitamin C glycosides such as L-ascorbic acid 2-glycoside), cysteine, tranexamic acid, hydroquinone, arbutin, ceramide, kojic acid, ellagic acid, plant Extracts as well as their salts are mentioned. One type or two or more types of whitening agents can be used in combination.

Examples of hair growth agents include pantothenic acid and its derivatives, allantoin, biotin, mononitroguaiacol, adenosine, pentadecanoic acid glyceride, dialkyl monoamine derivatives, coleus extract, chlorophyll, photosensitizer, estradiol, ethinyl estradiol, pyridoxine hydrochloride, thioxolone, minoxidil , Sulfur, organic sulfur substances, dipeptide-9 (glutamyl lysine), and salts thereof. One or two or more hair restorers can be used in combination.

The gel composition of the present invention may also contain other components such as a thickener, a stabilizer, a pH adjuster, a preservative, an ultraviolet light inhibitor, a fragrance, and a pigment. Specific types and amounts of these components can be appropriately set.

Examples of the thickener include carrageenan, dextrin, methylcellulose, ethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, polyacrylic acid, polymethacrylic acid, carboxyvinyl polymer (carbomer), (acrylic acid / alkyl acrylate ( C10-30)) copolymers, xanthan gum.

Examples of the stabilizer include ascorbic acid, sodium pyrosulfite, and EDTA.

Examples of the pH adjuster include aqueous solutions (buffer solutions) as described above, acidic substances such as hydrochloric acid, and basic substances such as sodium hydroxide.

Examples of preservatives include ethyl paraoxybenzoate, sodium benzoate, salicylic acid, sorbic acid, parabens (such as methylparaben and propylparaben), and sodium bisulfite.

Examples of UV inhibitors include UV absorbers (eg, t-butylmethoxydibenzoylmethane, ethylhexyl methoxycinnamate, oxybenzone-3), and UV scattering agents (eg, titanium oxide, zinc oxide).

Examples of the fragrances include limonene, citral, menthol, rose oil, and rose oil.

Examples of the pigment include organic pigments (eg, red pigments such as red 201, blue pigments such as blue 404, orange pigments such as orange 203, yellow pigments such as yellow 205, and green pigments such as green 3). , Organic lake pigments such as zirconium lake, natural pigments such as chlorophyll), and inorganic pigments (eg, white pigments such as titanium oxide, colored pigments such as iron oxide, extender pigments such as talc, pearl pigments such as mica). It is done.

The gel-like composition of the present invention controls the fluidity of a composition that is liquid at room temperature (eg, cosmetics, pharmaceuticals, quasi-drugs, agricultural chemicals, feeds, fertilizers, paints, or other raw materials). Can roll.

The gel composition of the present invention is also effective in a desired part (eg, skin, hair, hair, scalp) of a subject (eg, mammal such as a human, bird, reptile, etc.) (eg, 1 mg). To 100 g) can be used. Preferably, the gel composition of the present invention is applied to humans. The state of the subject to which the gel composition of the present invention is applied may be such that the site has a healthy state, or the site has an abnormal state (eg, disease). Also good. Examples of such abnormal states include rough skin, dry skin, scales, disorder of turnover, and skin diseases (eg, dermatitis such as atopic dermatitis).

Preferably, the gel composition of the present invention may be a humectant. In this case, the gel composition of the present invention preferably contains a hydrophilic organic solvent having a moisturizing action (eg, polyhydric alcohol) as the organic solvent. The gel composition of the present invention may further contain other humectant as described above in addition to the polyhydric alcohol. When the gel composition of the present invention is a moisturizing agent, the moisturizing agent of the present invention can exert an excellent effect in preventing, suppressing, or improving conditions such as rough skin through the moisturizing action. Wrinkle, anti-smudge, or anti-freckle effect can also be exhibited.

The gel composition of the present invention is also a cosmetic or an external preparation. The cosmetic or external preparation of the present invention can be made into a preparation in any form applicable to a desired site (eg, skin, hair, scalp) according to a conventional method.

The cosmetic or external preparation of the present invention can be preferably used as a cosmetic or external preparation for the skin, hair, or scalp. Examples of cosmetics or external preparations for the skin include emulsions, lotions, creams, gels, cosmetics, and face masks. Examples of cosmetics or external preparations for hair include hair emulsions, hair treatments, hair conditioners, shampoos, and hair lotions. Examples of cosmetics or external preparations for the scalp include hair restorers. Examples of preferable cosmetics include leave-on cosmetics, emulsions, lotions, creams, gels, cosmetics, and face masks. Preferable external preparations include, for example, ointments, creams, mousses, and gels.

Next, the present invention will be described in more detail with reference to examples. However, the present invention is not limited to the following examples.

Production Example 1: General Synthetic Method of N ^α -Alkanoyl-N ^ε -dodecanoyl-L-lysine-ethyl ester The synthesis of N ^ε -dodecanoyl-L-lysine-ethyl ester has been reported [Suzuki, M. et al. et al. , Chem. Commun. 19, 2012-2013 (2001)].
Next, N ^ε -dodecanoyl-L-lysine-ethyl ester was dissolved in dehydrated tetrahydrofuran solution (100 ml), and triethylamine (40 mmol) was added. Various alkanoyl chlorides (11 mmol) were slowly added with stirring in an ice bath, followed by stirring at room temperature for 6 hours. After hot filtration, the filtrate was evaporated to dryness. The obtained white solid was recrystallized from ethanol-ether to obtain the target substance.

Preparation 1A: N ^alpha - hexanoyl -N ^epsilon - dodecanoyl -L- lysine - using hexanoyl chloride as a synthesis alkanoyl chloride ethyl ester, N ^alpha - hexanoyl -N ^epsilon - dodecanoyl -L- lysine - Synthesis of the ethyl ester (Yield: 95%).

FT-IR (measurement by KBr method): v = 3309 cm ⁻¹ (ν NH, amide A), 1744 cm ⁻¹ (ν C═O, ester), 1641 cm ⁻¹ (ν C═O, amide I), 1540 cm ⁻¹ (δ NH, amide II).

¹ H-NMR (400 MHz, CDCl ₃ (TMS standard), rt): ¹ H-NMR (400 MHz, CDCl ₃ , TMS): δ = 0.86-0.91 (m, 6H), 1. 26-1.42 (m, 25H), 1.51-1.66 (m, 6H), 1.68-1.94 (m, 2H), 2.18 (t, J = 7.5 Hz, 2H ), 2.25 (t, J = 7.3 Hz, 2H), 3.17-3.31 (m, 2H), 4.22 (q, J = 7.1 Hz, 2H), 4.37-4 .42 (m, 1H), 5.73 (t, J = 5.6 Hz, 1H), 6.21 (d, J = 7.8 Hz, 1H).

Calculated (%) elemental analysis of C ₂₆ H ₅₀ N ₂ O ₄ (454.69): C, 68.68; H, 11.08; N, 6.16.
Found (%): C, 68.62; H, 11.75; N, 6.22.

Production Example 1B: Synthesis of N ^α- 2-ethylhexanoyl-N ^ε -dodecanoyl-L-lysine-ethyl ester Using 2-ethylhexanoyl chloride as the alkanoyl chloride, N ^α -2-ethylhexanoyl-N ^ε -Dodecanoyl-L-lysine-ethyl ester was synthesized (yield: 94%).

FT-IR (measurement by KBr method): v = 3306 cm ⁻¹ (ν NH, amide A), 1725 cm ⁻¹ (ν C═O, ester), 1640 cm ⁻¹ (ν C═O, amide I), 1536 cm ⁻¹ (δ NH, amide II).

¹ H-NMR (400 MHz, CDCl ₃ (TMS standard), rt.): ¹ H-NMR (400 MHz, CDCl ₃ , TMS): δ = 0.85-0.92 (m, 9H), 1. 26-1.41 (m, 25H), 1.51-1.63 (m, 8H), 1.71-1.94 (m, 2H), 2.02-2.10 (m, 1H), 2.15 (t, J = 7.4 Hz, 2H), 3.19-3.30 (m, 2H), 4.14 (q, J = 7.2 Hz, 2H), 4.40-4.48 (M, 1H), 5.76 (t, J = 5.6 Hz, 1H), 6.27 (d, J = 7.8 Hz, 1H).

_{_{_{_{C 28 H 54 N 2 O 4}}}} (482.41) Elementary analysis Calculated (%): C, 69.66; H, 11.27; N, 5.80.
Found (%): C, 69.77; H, 11.39; N, 5.76.

Production Example 1C: Synthesis of N ^α -3,5,5-trimethylhexanoyl-N ^ε -dodecanoyl-L-lysine-ethyl ester Using 3,5,5-trimethylhexanoyl chloride as the alkanoyl chloride, N ^α- 3,5,5-Trimethylhexanoyl-N ^ε -dodecanoyl-L-lysine-ethyl ester was synthesized (yield: 97%).

FT-IR (measurement by KBr method): v = 3309 cm ⁻¹ (ν NH, amide A), 1747 cm ⁻¹ (ν C═O, ester), 1640 cm ⁻¹ (ν C═O, amide I), 1543 cm ⁻¹ (δ NH, amide II).

¹ H-NMR (400 MHz, CDCl ₃ (TMS standard), rt): δ = 0.86-0.91 (m, 12H), 0.95-0.97 (m, 3H), 1. 21-1.31 (m, 21H), 1.34-1.41 (m, 2H), 1.50-1.60 (m, 4H), 1.71-1.93 (m, 2H), 1.96-2.05 (m, 2H), 2.14 (t, J = 7.4 Hz, 2H), 2.19-2.28 (m, 1H), 3.17-3.33 (m , 2H), 4.17 (q, J = 7.0 Hz, 2H), 4.38-4.44 (m, 1H), 5.81 (t, J = 5.6 Hz, 1H), 6.27. (D, J = 7.8 Hz, 1H).

Calculated (%) elemental analysis of C ₂₉ H ₅₆ N ₂ O ₄ (496.42): C, 70.12; H, 11.36; N, 5.64.
Found (%): C, 70.31; H, 12.27; N, 5.63.

Production Example 2: General Synthesis Method of N ^α -Alkanoyl-N ^ε -dodecanoyl-L-lysineamide A bottle that can withstand internal pressure using about 70 mL of methanol (concentration of about 15-17%) containing ammonia by an ammonia spraying method 10 mmol of N ^α -alkanoyl-N ^ε -dodecanoyl-L-lysine-ethyl ester was dissolved in, sealed and stirred at 55 ° C. for 1 week. About 250 mL of methanol was added to the reaction solution, heated to make it transparent, concentrated under reduced pressure, dissolved in ethanol again, and concentrated under reduced pressure. The desired product was obtained by drying under reduced pressure.

Preparation 2A: N ^alpha - hexanoyl -N ^epsilon - dodecanoyl -L- Synthesis of a lysine amide (A) N ^alpha - alkanoyl -N ^epsilon - dodecanoyl -L- lysine - as ethyl ester, N synthesized in Preparation Example 1A ^alpha - Compound A was synthesized using hexanoyl-N ^ε -dodecanoyl-L-lysine-ethyl ester (yield: 95%).

FT-IR (measurement by KBr method): v = 3385 cm ⁻¹ (ν NH, amine), 3296 cm ⁻¹ (ν NH, amide A), 1673 cm ⁻¹ (ν C═O, amide I), 1628 cm ⁻¹ (ν C═O, amide I), 1547 cm ⁻¹ (δ NH, amide II).

¹ H-NMR (400 MHz, CDCl ₃ (TMS standard), rt): δ = 0.86-0.91 (m, 6H), 1.26-1.42 (m, 22H), 1. 51-1.66 (m, 6H), 1.68-1.94 (m, 2H), 2.16 (t, J = 7.5 Hz, 2H), 2.24 (t, J = 7.3 Hz) , 2H), 3.17-3.37 (m, 2H), 4.37-4.42 (m, 1H), 5.34 (br, 1H), 5.63 (br, 1H), 6. 36-6.40 (m, 2H).

_{_{_{_{C 24 H 47 N 3 O 3}}}} (425.65) Elementary analysis Calculated (%): C, 67.72; H, 11.13; N, 9.87.
Found (%): C, 67.99; H, 11.23; N, 9.97.

Preparation 2B: N ^{alpha-2-ethyl-hexanoyl} -N ^epsilon - dodecanoyl -L- lysine amide synthesis N ^alpha of (B) - alkanoyl -N ^epsilon - dodecanoyl -L- lysine - as ethyl ester, synthesized in Preparation Example 1B Compound B was synthesized using N ^α -2-ethylhexanoyl-N ^ε -dodecanoyl-L-lysine-ethyl ester (yield: 90%).

FT-IR (measurement by KBr method): v = 3389 cm ⁻¹ (ν NH, amine), 3302 cm ⁻¹ (ν NH, amide A), 1673 cm ⁻¹ (ν C═O, amide I), 1633 cm ⁻¹ (ν C═O, amide I), 1548 cm ⁻¹ (δ NH, amide II).

¹ H-NMR (400 MHz, CDCl ₃ (TMS standard), rt): δ = 0.85-0.90 (m, 9H), 1.26-1.42 (m, 22H), 1. 51-1.66 (m, 8H), 1.68-1.94 (m, 2H), 2.02-2.09 (m, 1H), 2.16 (t, J = 7.4 Hz, 2H ), 3.19-3.34 (m, 2H), 4.42-4.48 (m, 1H), 5.44 (br, 1H), 5.71 (br, 1H), 6.36- 6.40 (m, 2H).

_{_{_{_{C 26 H 51 N 3 O 3}}}} (453.70) Elementary analysis Calculated (%): C, 68.83; H, 11.33; N, 9.26.
Found (%): C, 69.15; H, 12.08; N, 9.31.

Preparation 2C: N ^alpha -3,5,5-trimethyl hexanoyl -N ^epsilon - dodecanoyl -L- synthesis of a lysine amide (C) N ^alpha - alkanoyl -N ^epsilon - dodecanoyl -L- lysine - as ethyl ester, Preparation Compound C was synthesized using N ^α -3,5,5-trimethylhexanoyl-N ^ε -dodecanoyl-L-lysine-ethyl ester synthesized in 1C (yield: 97%).

FT-IR (measurement by KBr method): v = 3383 cm ⁻¹ (ν NH, amine), 3302 cm ⁻¹ (ν NH, amide A), 1675 cm ⁻¹ (ν C═O, amide I), 1630 cm ⁻¹ (ν C═O, amide I), 1548 cm ⁻¹ (δ NH, amide II).

¹ H-NMR (400 MHz, CDCl ₃ (TMS standard), rt): δ = 0.86-0.91 (m, 12H), 0.95-0.97 (m, 3H), 1. 22-1.29 (m, 18H), 1.34-1.43 (m, 2H), 1.50-1.63 (m, 4H), 1.71-1.93 (m, 2H), 1.98-2.07 (m, 2H), 2.16 (t, J = 7.4 Hz, 2H), 2.22-2.29 (m, 1H), 3.17-3.36 (m , 2H), 4.38-4.44 (m, 1H), 5.44 (br, 1H), 5.71 (br, 1H), 6.47-6.54 (m, 2H).

_{_{_{_{C 27 H 53 N 3 O 3}}}} (467.73) Elementary analysis Calculated (%): C, 69.33; H, 11.42; N, 8.98.
Found (%): C, 69.89; H, 12.07; N, 8.81.

Examples 1 to 14: Preparation of test samples The test samples of Examples 1 to 14 were prepared as described in Test Examples described later.

Test Example 1: Evaluation of gelation ability of various samples with respect to various liquid organic solvents The gelation ability of various samples (Examples 1 to 14) with respect to various liquid organic solvents was evaluated. First, the compounds of the present invention (Production Examples 1 to 3) were precisely weighed in a test tube with a lid and added in an amount of 1 mg each, and 1 ml of various liquid organic solvents were added and heated until completely dissolved uniformly with a lid. After dissolution, it was left in a thermostatic bath at 25 ° C. for 2 hours, and the state was observed with the naked eye. If the gelation is incomplete, add a compound. If it is completely gelled, add a liquid organic solvent. The minimum amount of compound (mg) required to gel each liquid organic solvent per ml. Asked. However, the maximum amount of the compound to be added was up to 200 mg with respect to 2 ml of the liquid organic medium, and the organic solvent that remained liquid in this state and the organic solvent that had crystallized and precipitated were evaluated as “not gelled”. In this test example, the solvent did not flow out even when the test tube was tilted, and the gel that was not deformed even when tapped was judged as a gel.

The amount of various compounds necessary for gelling 1 ml of various liquid organic solvents was evaluated according to the following criteria.
Necessary amount of compound is 10 mg or less: having a very favorable degree of gelation ability (a)
Necessary amount of compound is 10 to 20 mg: having a preferable degree of gelation ability (b)
Necessary amount of compound is 21 to 25 mg: having a certain standard gelling ability (c)
Necessary amount of compound is 26 mg or more: gelling ability

If the evaluation is a to c, it can be evaluated that the gelation ability exceeds a certain standard. The gelation ability of evaluation a or b is desirable.

As a result, it was shown that the compounds A, B and C of the present invention have excellent gelling ability with respect to various organic solvents (including general cosmetic oils) (Table 1).

Test Example 2: Evaluation of properties of gel composition Next, properties of the gel composition were evaluated. The sample of Example 10 (Compound B), which showed the best results in the test examples, was used for evaluating the properties of the gel composition.

First, Compound B (Production Example 2) was precisely weighed into a test tube with a lid (made of glass), 1 mg was added, 1 ml of methylphenylpolysiloxane was added, and the mixture was covered and heated until completely dissolved. After dissolution, it was left in a thermostatic bath at 25 ° C. for 2 hours, and the formed gel composition was observed with the naked eye. If the opposite side of the test tube was visible through the gel composition, the gel composition was judged to be transparent. As a result, it was confirmed that the gel composition obtained in Example 10 (Compound B) was transparent.

The compound of the present invention or a salt thereof is useful as a raw material for cosmetics, for example.
The gel composition of the present invention is useful, for example, as a cosmetic and its raw material.

Claims

Following formula (1):

[Where,
R 1 is a linear or branched monovalent hydrocarbon group having 3 to 17 carbon atoms,
R 2 is a linear or branched monovalent hydrocarbon group having 4 to 12 carbon atoms,
R 3 is a linear or branched divalent hydrocarbon group having 2 to 6 carbon atoms,
R 4 and R 5 are each independently a hydrogen atom, a linear or branched monovalent hydrocarbon group having 1 to 18 carbon atoms, or R′—C (═O) — (where R 'Is a linear or branched monovalent hydrocarbon group having 1 to 18 carbon atoms. Or a salt thereof.
R 1 is a linear or branched monovalent hydrocarbon group having 7 to 13 carbon atoms,
R 2 is a linear or branched monovalent hydrocarbon group having 4 to 10 carbon atoms,
R 3 is a linear or branched divalent hydrocarbon group having 3 to 5 carbon atoms,
R 4 and R 5 are each independently a hydrogen atom, a linear or branched monovalent hydrocarbon group having 1 to 10 carbon atoms, or R′—C (═O) — (where R 2. The compound or a salt thereof according to claim 1, wherein 'is a linear or branched monovalent hydrocarbon group having 1 to 10 carbon atoms.
R 1 is a linear or branched monovalent hydrocarbon group having 11 carbon atoms,
R 2 is a linear or branched monovalent hydrocarbon group having 5 to 8 carbon atoms,
R 3 is a linear or branched divalent hydrocarbon group having 4 carbon atoms,
R 4 and R 5 are each independently a hydrogen atom, a linear or branched monovalent hydrocarbon group having 1 to 4 carbon atoms, or R′—C (═O) — (where R The compound or a salt thereof according to claim 2, wherein 'is a linear or branched monovalent hydrocarbon group having 1 to 4 carbon atoms.
The monovalent hydrocarbon group in R 1 , R 2 , R 4 , R 5 , and R ′ is alkyl, and the divalent hydrocarbon group in R 3 is alkylene. Or a salt thereof.
The compound or a salt thereof according to any one of claims 1 to 4, wherein R 4 and R 5 are each a hydrogen atom.
The compound is (A) N α -hexanoyl-N ε -dodecanoyl-L-lysine amide, (B) N α -2-ethylhexanoyl-N ε -dodecanoyl-L-lysine amide, or (C) N α -3, The compound or a salt thereof according to any one of claims 1 to 5, which is 5,5-trimethylhexanoyl-N ε -dodecanoyl-L-lysine amide.
Following formula (1):

[Where,
R 1 is a linear or branched monovalent hydrocarbon group having 3 to 17 carbon atoms,
R 2 is a linear or branched monovalent hydrocarbon group having 4 to 12 carbon atoms,
R 3 is a linear or branched divalent hydrocarbon group having 2 to 6 carbon atoms,
R 4 and R 5 are each independently a hydrogen atom, a linear or branched monovalent hydrocarbon group having 1 to 18 carbon atoms, or R′—C (═O) — (where R 'Is a linear or branched monovalent hydrocarbon group having 1 to 18 carbon atoms. ] The gel-like composition containing the compound or its salt represented by these, and an organic solvent.
The gel composition according to claim 7, wherein the organic solvent is a hydrophilic organic solvent.
The gel composition according to claim 8, wherein the hydrophilic organic solvent is a polyhydric alcohol.
The gel composition according to claim 7, wherein the organic solvent is a hydrophobic organic solvent.
The gel composition according to claim 10, wherein the hydrophobic organic solvent is an oil agent.
The gel composition according to claim 11, wherein the oil agent is one or more oil agents selected from the group consisting of hydrocarbon oil, silicone oil, ester oil, and liquid oil.
The gel composition according to claim 11 or 12, wherein the oil agent is silicone oil.
The gel composition according to any one of claims 7 to 13, wherein the gel composition further contains a humectant.
The gel composition according to any one of claims 7 to 14, wherein the gel composition is a cosmetic.