WO2018198523A1 - Dérivé d'acide n-acylamino - Google Patents

Dérivé d'acide n-acylamino Download PDF

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Publication number
WO2018198523A1
WO2018198523A1 PCT/JP2018/007336 JP2018007336W WO2018198523A1 WO 2018198523 A1 WO2018198523 A1 WO 2018198523A1 JP 2018007336 W JP2018007336 W JP 2018007336W WO 2018198523 A1 WO2018198523 A1 WO 2018198523A1
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carbon atoms
hydrocarbon group
linear
acid
monovalent hydrocarbon
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PCT/JP2018/007336
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English (en)
Japanese (ja)
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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
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味の素株式会社
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Publication of WO2018198523A1 publication Critical patent/WO2018198523A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/31—Hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere

Definitions

  • the present invention relates to N-acylamino acid derivatives and the like.
  • 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).
  • Patent Document 1 has low oil gelling ability, and a large amount of acidic amino acid derivative was required for oil gelation.
  • an object of the present invention is to provide a compound having an excellent gelling ability with respect to oil.
  • 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 Is a straight-chain 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 Is a straight-chain or branched monovalent hydrocarbon group having 1 to 4 carbon atoms.)
  • R 1 , R 2 , R 4 , R 5 , and R ′ is alkyl
  • the divalent hydrocarbon group in R 3 is alkylene, [1] to [3 Or a salt thereof.
  • R 4 and R 5 are each a hydrogen atom.
  • the compound is (A) N ⁇ -hexanoyl-N ⁇ -dodecanoyl-L-lysine amide, (B) N ⁇ -2-ethylhexanoyl-N ⁇ -dodecanoyl-L-lysine amide, or (C) N ⁇ A compound or a salt thereof according to any one of [1] to [5], which is -3,5,5-trimethylhexanoyl-N ⁇ -dodecanoyl-L-lysine amide.
  • 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 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.
  • 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.
  • 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).
  • 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 .
  • alkenyl in R 1 examples include propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, and heptadecenyl.
  • 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 .
  • alkynyl for R 1 examples include propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, decynyl, undecynyl, dodecynyl, tridecynyl, tetradecynyl, pentadecynyl, hexadecynyl, and heptadecynyl.
  • 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.
  • 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
  • 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.
  • 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.
  • 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.
  • 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.
  • alkylene in R 3 examples 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).
  • propylene eg, n-propylene, iso-propylene
  • butylene eg, n-butylene, iso-butylene, sec-butylene, tert-butylene
  • pentylene eg, n -Pentylene, iso-
  • 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.
  • 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.
  • 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.
  • R 3 may be 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.
  • 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 ′.
  • alkyl in R 4 and / or R 5 and / or R ′ examples 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-dimethylp
  • 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 ′.
  • 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.
  • 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 ′.
  • alkynyl in R 4 and / or R 5 and / or R ′ examples include, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, decynyl, undecynyl, dodecynyl, tridecynyl, tetradecynyl, pentadecynyl, hexadecynyl , Heptadecynyl, and octadecynyl.
  • 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).
  • 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 . ]
  • 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).
  • the reaction can be performed in an appropriate solvent (eg, tetrahydrofuran) by appropriately adding an amine (eg, an alkylamine such as triethylamine).
  • 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.
  • 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. ]
  • 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.
  • 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).
  • any hydrophilic organic compound solvent can be used.
  • 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.
  • polyhydric alcohol examples 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).
  • dihydric alcohols eg, ethylene glycol, propylene glycol, 1,3-propanediol, 1,2-buty
  • 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.
  • sugar alcohols eg, monosaccharide alcohols such as sorbitol and mannitol, disaccharide alcohols such as trehalose, and polysaccharide alcohols such as hyaluronic acid
  • 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.
  • 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.
  • 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).
  • hydrocarbon oil examples 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)).
  • paraffinic oil eg, paraffin, liquid paraffin, isoparaffin, cycloparaffin
  • fuel oil eg, light oil, heavy oil, petroleum, kerosene, gasoline, mixed oil
  • hydrocarbon chain linear
  • silicone oil examples include polysiloxane.
  • 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.
  • the monohydric alcohol examples 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.
  • 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.
  • 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).
  • methanic acid formic acid
  • ethanoic acid acetic acid
  • propanoic acid propanoic 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.
  • 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, dioctyldodec
  • 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).
  • 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.
  • 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.
  • higher fatty acids examples 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.
  • higher alcohols include alcohols having 6 or more carbon atoms.
  • the higher alcohol may have a linear, branched or cyclic structure.
  • 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.
  • 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).
  • the organic solvent can be gelled while reducing the content of 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • aqueous solution examples 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.
  • 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.
  • 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.
  • low molecular weight compound examples 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.
  • 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 (
  • 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.
  • 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.
  • vitamin C vitamin C glycosides such as L-ascorbic acid 2-glycoside
  • cysteine eg., cysteine, tranexamic acid, hydroquinone, arbutin, ceramide, kojic acid, ellagic acid, plant Extracts as well as their salts are mentioned.
  • whitening agents include vitamin C, vitamin
  • 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.
  • thickener examples include carrageenan, dextrin, methylcellulose, ethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, polyacrylic acid, polymethacrylic acid, carboxyvinyl polymer (carbomer), (acrylic acid / alkyl acrylate ( C10-30)) copolymers, xanthan gum.
  • the stabilizer examples include ascorbic acid, sodium pyrosulfite, and EDTA.
  • pH adjuster examples include aqueous solutions (buffer solutions) as described above, acidic substances such as hydrochloric acid, and basic substances such as sodium hydroxide.
  • preservatives examples include ethyl paraoxybenzoate, sodium benzoate, salicylic acid, sorbic acid, parabens (such as methylparaben and propylparaben), and sodium bisulfite.
  • UV inhibitors examples include UV absorbers (eg, t-butylmethoxydibenzoylmethane, ethylhexyl methoxycinnamate, oxybenzone-3), and UV scattering agents (eg, titanium oxide, zinc oxide).
  • UV absorbers eg, t-butylmethoxydibenzoylmethane, ethylhexyl methoxycinnamate, oxybenzone-3
  • UV scattering agents eg, titanium oxide, zinc oxide
  • fragrances examples include limonene, citral, menthol, rose oil, and rose oil.
  • the pigment examples 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
  • 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).
  • a composition that is liquid at room temperature eg, cosmetics, pharmaceuticals, quasi-drugs, agricultural chemicals, feeds, fertilizers, paints, or other raw materials.
  • Can roll eg, cosmetics, pharmaceuticals, quasi-drugs, agricultural chemicals, feeds, fertilizers, paints, or other raw materials.
  • 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).
  • a desired part eg, skin, hair, hair, scalp
  • a subject eg, mammal such as a human, bird, reptile, etc.
  • 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).
  • the gel composition of the present invention may be a humectant.
  • 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.
  • 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.
  • cosmetics or external preparations for the skin include emulsions, lotions, creams, gels, cosmetics, and face masks.
  • cosmetics or external preparations for hair include hair emulsions, hair treatments, hair conditioners, shampoos, and hair lotions.
  • 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.
  • 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%).
  • Production Example 1B Synthesis of N ⁇ - 2-ethylhexanoyl-N ⁇ -dodecanoyl-L-lysine-ethyl ester Using 2-ethylhexanoyl chloride as the alkanoyl chloride, N ⁇ -2-ethylhexanoyl-N ⁇ -Dodecanoyl-L-lysine-ethyl ester was synthesized (yield: 94%).
  • Production Example 1C Synthesis of N ⁇ -3,5,5-trimethylhexanoyl-N ⁇ -dodecanoyl-L-lysine-ethyl ester Using 3,5,5-trimethylhexanoyl chloride as the alkanoyl chloride, N ⁇ - 3,5,5-Trimethylhexanoyl-N ⁇ -dodecanoyl-L-lysine-ethyl ester was synthesized (yield: 97%).
  • 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 ⁇ -dodecanoyl-L-lysine-ethyl ester (yield: 95%).
  • 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 ⁇ -2-ethylhexanoyl-N ⁇ -dodecanoyl-L-lysine-ethyl ester (yield: 90%).
  • 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
  • Compound C was synthesized using N ⁇ -3,5,5-trimethylhexanoyl-N ⁇ -dodecanoyl-L-lysine-ethyl ester synthesized in 1C (yield: 97%).
  • 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.
  • 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.
  • 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”.
  • 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.
  • 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
  • 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.
  • 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.
  • 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.

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Abstract

La présente invention concerne un composé ayant une excellente capacité de gélification d'huile. La présente invention concerne plus particulièrement un composé représenté par la formule (1), ou un sel de celui-ci. [Dans la formule : R1 est un groupe hydrocarboné monovalent à chaîne droite ou ramifiée ayant 3 à 17 atomes de carbone ; R2 est un groupe hydrocarboné monovalent à chaîne droite ou ramifiée ayant 4 à 12 atomes de carbone ; R3 est un groupe hydrocarboné divalent à chaîne droite ou ramifiée ayant 2 à 6 atomes de carbone ; et R4 et R5 représentent chacun indépendamment un atome d'hydrogène, un groupe hydrocarboné monovalent à chaîne droite ou ramifiée ayant 1 à 18 atomes de carbone ou R'-C(=O)- (R' étant une chaîne droite ou un groupe hydrocarboné monovalent à chaîne ramifiée ayant de 1 à 18 atomes de carbone).]
PCT/JP2018/007336 2017-04-28 2018-02-27 Dérivé d'acide n-acylamino WO2018198523A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3969087A (en) * 1974-08-07 1976-07-13 Ajinomoto Co., Ltd. Gels of nonpolar liquids with N-acyl amino acids and derivatives thereof as gelling agents
JPS51125677A (en) * 1974-08-07 1976-11-02 Ajinomoto Co Inc Method of solidifying organic modium
JPS51127002A (en) * 1975-04-08 1976-11-05 Bayer Ag Carboxylic amide preparation method thereof and pharmaceutical composition and medicine containing same
WO2007078013A1 (fr) * 2006-01-06 2007-07-12 Ajinomoto Co., Inc. Agent gelifiant
WO2010090354A1 (fr) * 2009-02-09 2010-08-12 味の素株式会社 Epaississant pour la production de détergents solides
WO2013118896A1 (fr) * 2012-02-09 2013-08-15 味の素株式会社 Dérivé d'acide aminé basique

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3969087A (en) * 1974-08-07 1976-07-13 Ajinomoto Co., Ltd. Gels of nonpolar liquids with N-acyl amino acids and derivatives thereof as gelling agents
JPS51125677A (en) * 1974-08-07 1976-11-02 Ajinomoto Co Inc Method of solidifying organic modium
JPS51127002A (en) * 1975-04-08 1976-11-05 Bayer Ag Carboxylic amide preparation method thereof and pharmaceutical composition and medicine containing same
WO2007078013A1 (fr) * 2006-01-06 2007-07-12 Ajinomoto Co., Inc. Agent gelifiant
WO2010090354A1 (fr) * 2009-02-09 2010-08-12 味の素株式会社 Epaississant pour la production de détergents solides
WO2013118896A1 (fr) * 2012-02-09 2013-08-15 味の素株式会社 Dérivé d'acide aminé basique

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE CAS [o] 31 August 1985 (1985-08-31), retrieved from STN Database accession no. 93981-25-0 *

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