EP0500332A2
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EP
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Novel acylamino acid compounds and a method for their production
Assignee: Food Research Institute
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Filing: 1992-02-19
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Granted: —
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Expires: 2012-02-19
Abstract
Abstract Novel N-acylamino acid compounds of the general formula (1) : R-CO-(NH-X-CO) n -OR 1 (1) are disclosed wherein (NH-X-CO) is an amino acid residue and X in (NH-X-CO) varies depending on the amino acid employed, R-CO is a saturated or an unsaturated fatty acid residue having from 6 to 24 carbon atoms, R 1 represents a hydrogen, sodium or potassium atom, or a methyl group and n is an integer of from 1 to 3, wherein at least one histidine is contained as a component amino acid. The compounds can be obtained by reacting an N-hydroxysuccinimide ester with an amino acid or a peptide. The compound has antioxidizing, emulsifying, antibacterial and chelating properties, can absorb infrared radiation and display humidity-retaining properties.
Inventors
- 👤 Hironobu Murase
- 👤 Tsutomu Kunieda
- 👤 Akihiko Nagao
- 👤 Junji Terao
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-09 22:03
CPC Classifications
C; C09; C09K; C09K15/00; C09K15/04; C09K15/16; C09K15/18; A; A23; A23B; A23B2/00; A23B2/70; A23B2/725; A23B2/729; A23B2/762; A23B2/771; A61; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/64; A61Q; A61Q17/00; A61Q17/04; C07; C07D; C07D233/00; C07D233/54; C07D233/64; C07K; C07K5/00; C07K5/04; C07K5/06; C07K5/06139; C07K5/06147; C07K5/08; C07K5/0802; C07K5/0804; C07K5/0806; A61K2800/00; A61K2800/40; A61K2800/52; A61K2800/522
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
77 words
An N-acylamino acid compound having the general formula (1): wherein (NH-X-CO) is an amino acid residue, X in (NH-X-CO) varies depending on the amino acid present, R-CO is a saturated or unsaturated fatty acid residue having from 6 to 24 carbon atoms, R 1 represents a hydrogen, sodium or potassium atom, or a methyl group, and n is an integer of from 1 to 3, wherein at least one histidine is present as a component amino acid.
Claim 2
Dependent Claim
77 words
An N-acylamino acid compound having the general formula (1): wherein (NH-X-CO) is an amino acid residue, X in (NH-X-CO) varies depending on the amino acid present, R-CO is a saturated or unsaturated fatty acid residue having from 6 to 24 carbon atoms, R 1 represents a hydrogen, sodium or potassium atom, or a methyl group, and n is an integer of from 1 to 3, wherein at least one histidine is present as a component amino acid.
Claim 3
Dependent Claim
23 words
A compound according to claim 1, wherein R-CO is a saturated or an unsaturated fatty acid residue having 8 to 20 carbon atoms.
Claim 4
Dependent Claim
18 words
A compound according to claim 1, wherein n is an integer of the value of 1 or 2.
Claim 5
Dependent Claim
42 words
A compound according to any of claims 1 to 3, wherein the amino acid is histidine, glycine, tryptophan, isoleucine, phenylalanine, methionine, cysteine, leucine, lysine, alanine, valine, proline, serine, threonine, tyrosine, asparagine, glutamine, arginine, aspartic acid, glutamic acid, beta-alanine, dopa, creatine, or ornithine.
Claim 6
Dependent Claim
19 words
A compound according to any of claims 1 to 4, wherein the compound is N-oleoyl carnosine or N-oleoyl histidine.
Claim 7
Independent Claim
127 words
A method for the production of an N-acylamino acid compound having the general formula (1): wherein (NH-X-CO) is an amino acid residue, X in (NH-X-CO) varies depending on the amino acid present, R-CO is a saturated or unsaturated fatty acid residue having from 6 to 24 carbon,atoms, R 1 represents a hydrogen, sodium or potassium atom, or methyl group, and n represents an integer of from 1 to 3, wherein at least one histidine is present as a component amino acid, the method comprising reacting an N-hydroxysuccinimide ester of the general formula (2): wherein RCO has the same meaning as defined above with an amino acid or a peptide of the general formula (3): wherein (NH-X-CO), OR 1 and n have the same meanings as defined above.
Claim 8
Independent Claim
127 words
A method for the production of an N-acylamino acid compound having the general formula (1): wherein (NH-X-CO) is an amino acid residue, X in (NH-X-CO) varies depending on the amino acid present, R-CO is a saturated or unsaturated fatty acid residue having from 6 to 24 carbon,atoms, R 1 represents a hydrogen, sodium or potassium atom, or methyl group, and n represents an integer of from 1 to 3, wherein at least one histidine is present as a component amino acid, the method comprising reacting an N-hydroxysuccinimide ester of the general formula (2): wherein RCO has the same meaning as defined above with an amino acid or a peptide of the general formula (3): wherein (NH-X-CO), OR 1 and n have the same meanings as defined above.
Claim 9
Dependent Claim
30 words
A method according to claim 7, wherein the amount of amino acid or peptide is in the range of from 0.1 to 5 mols per mol of the N-hydroxysuccinimide ester.
Claim 10
Dependent Claim
22 words
A method according to claim 6 or 7, wherein the reaction is carried out at a pH of from 7 to 12.
Claim 11
Independent Claim
22 words
A method according to any of claims 6 to 8 for preparing a compound according to any of claims 1 to 5.
Claim 12
Dependent Claim
88 words
An antioxidant or emulsifier having as an active component thereof an N-acylamino acid compound having the general formula (1): wherein (NH-X-CO) is an amino acid residue, X in (NH-X-CO) varies depending on the amino acid present, R-CO is a saturated or an unsaturated fatty acid residue having from 6 to 24 carbon atoms, R 1 represents a hydrogen, sodium or potassium atom, or a methyl group, and n is an integer of from 1 to 3, wherein at least one histidine is present as a component amino acid.
Claim 13
Dependent Claim
88 words
An antioxidant or emulsifier having as an active component thereof an N-acylamino acid compound having the general formula (1): wherein (NH-X-CO) is an amino acid residue, X in (NH-X-CO) varies depending on the amino acid present, R-CO is a saturated or an unsaturated fatty acid residue having from 6 to 24 carbon atoms, R 1 represents a hydrogen, sodium or potassium atom, or a methyl group, and n is an integer of from 1 to 3, wherein at least one histidine is present as a component amino acid.
Claim 14
Dependent Claim
24 words
An antioxidant or emulsifier according to claim 10 wherein the compound of formula (1) is as claimed in any of claims 2 to 5.
Claim 15
Dependent Claim
34 words
A cosmetic composition such as an ultra-violet radiation absorbing composition (such as a tanning or sun- blocking lotion) comprising a compound according to any of claims 1 to 5 and optionally a cosmetic carrier.
Claim 16
Dependent Claim
20 words
A foodstuff comprising a compound as claimed in any of claims 1 to 5, suitably in an anti-oxidizing effective amount.
Claim 17
Dependent Claim
24 words
A pharmaceutical composition, such as an antibacterial composition, comprising a compound according to any of claims 1 to 5 and a pharmaceutically acceptable carrier.
References Cited (Backward Citations)
No citation records indexed.
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