EP0176217A1
Expired / Lapsed
EP
⏱️ 0.0 years remaining
Pyroglutamic acid esters, their synthesis and use in topical products
Assignee: Unilever PLC
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Filing: 1985-08-16
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Granted: —
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Expires: 2005-08-16
Abstract
Abstract Esters of pyroglutamic acid having the structure: where R' and R" are the same or different and are each represented by H or the grouping where n is an interger of from 1 to 3 w is zero, or an integer of from 1 to 21 x is zero, or an integer of from 1 to 4 y is zero, or an integer of from 1 to 2 z is zero, or an integer of from 1 to 4 provided that the total number of of carbon atoms in each of said grouping will not exceed 22; and provided also that when the subgrouping. (CH=CH) is present, then the total number of carbon atoms in said grouping will be from 16 to 22. Synthesis, and uses of the said esters in topical compositions are also grovided.
Inventors
- 👤 John Gordon Black
- 👤 Ian Richard Scott
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-03 16:50
CPC Classifications
A; A61; A61Q; A61Q19/00; A61Q19/007; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/49; A61K8/4906; A61K8/4913; A61P; A61P17/00; A61P3/00; C; C07; C07D; C07D207/00; C07D207/02; C07D207/18; C07D207/22; C07D207/24; C07D207/26; C07D207/273; C07D207/277; C07D207/28
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
123 words
Esters of pyroglutamic acid having the structure: where R' and R" are the same or different and are each represented by H or the grouping where n is an interger of from 1 to 3 w is zero, or an integer of from 1 to 21 x is zero, or an integer of from 1 to 4 y is zero, or an integer of from 1 to 2 z is zero, or an integer of from 1 to 4 provided that the total number of of carbon atoms in each of said grouping will not exceed 22; and provided also that when the subgrouping (CH=CH) is present, then the total number of carbon atoms in said grouping will be from 16 to 22.
Claim 2
Dependent Claim
123 words
Esters of pyroglutamic acid having the structure: where R' and R" are the same or different and are each represented by H or the grouping where n is an interger of from 1 to 3 w is zero, or an integer of from 1 to 21 x is zero, or an integer of from 1 to 4 y is zero, or an integer of from 1 to 2 z is zero, or an integer of from 1 to 4 provided that the total number of of carbon atoms in each of said grouping will not exceed 22; and provided also that when the subgrouping (CH=CH) is present, then the total number of carbon atoms in said grouping will be from 16 to 22.
Claim 3
Dependent Claim
60 words
An ester according to claim 1, in which the grouping is chosen from: methyl ethyl propyl iso-propyl butyl iso-butyl tert-butyl valeryl iso-valeryl caproyl heptyl caprylyl capryl lauryl myristyl palmityl stearyl arachidyl behenyl hydroxy methyl 2-hydroxy ethyl 2-hydroxy propyl 3-hydroxy propyl 2-hydroxy butyl 3-hydroxy butyl 4-hydroxy butyl 5-hydroxy valeryl 6-hydroxy caproyl 2,3-dihydroxy propyl 2,3-dihydroxy butyl 12-hydroxy stearyl linoleoyl linolenoyl, and arachidonyl.
Claim 4
Dependent Claim
66 words
An ester according to claim 1 or 2 chosen from: 2-pyroglutamyl propionic acid methyl-2-pyroglutamyl acetate ethyl-2-pyroglutamyl propionate ethyl-2-pyroglutamyl n-butyrate ethyl-2-pyroglutamyl iso-butyrate ethyl-2-pyroglutamyl n-valerate ethyl-2-pyroglutamyl n-caproate ethyl-2-pyroglutamyl n-heptylate ethyl-2-pyroglutamyl n-caprylate ethyl-2-pyroglutamyl n-pelargonate ethyl-2-pyroglutamyl-3-hydroxybutyrate iso-propyl-2-pyroglutamyl propionate iso-propyl-2-pyroglutamyl n-caprylate n-propyl-2-pyroglutamyl propionate n-propyl-2-pyroglutamyl n-caprylate glyceryl mono(2-pyroglutamyl propionate) glyceryl di(2-pyroglutamyl propionate) stearyl-2-pyroglutamyl propionate 12-hydroxystearyl-2-pyroglutamyl propionate stearyl-2-pyroglutamyl stearate palmityl-2-pyroglutamyl propionate linoleoyl-2-pyroglutamyl propionate linoleoyl-2-pyroglutamyl n-caprylate glyceryl mono(2-pyroglutamyl n-caprylate) lauryl-2-pyroglutamyl n-caprylate, and stearyl-2-pyroglutamyl n-caprylate.
Claim 5
Dependent Claim
42 words
A process for the synthesis of esters of pyroglutamic acid according to claim 1, 2 or 3, which comprises the steps of: (i) reacting pyroglutamic acid with an ester having the structure: (ii) and isolating the ester of pyroglutamic acid so obtained.
Claim 6
Dependent Claim
63 words
A process for the synthesis of esters of pyroglutamic acid according to claim 1, 2 or 3, which comprises the steps of: (i) reacting pyroglutamic acid with an alpha hydroxy acid having the structure: to form an ester having the structure: (ii) condensing the ester (3) with an alcohol having the structure R'OH (iii) and isolating the ester of pyroglutamic acid so obtained.
Claim 7
Dependent Claim
23 words
A process according to claim 4 or 5, in which pyroglutamic acid and the ester are reacted in the presence of a solvent.
Claim 8
Dependent Claim
25 words
A process according to claim 4, 5 or 6 in which pyroglutamic acid and the ester are reacted in the presence of a drying agent.
Claim 9
Dependent Claim
41 words
A composition for topical treatment to human skin which comprises an effective amount of from 0.01 to 99% by weight of an ester of pyroglutamic acid according to claim 1, 2 or 3, together with a physiologically and cosmetically acceptable diluent.
Claim 10
Dependent Claim
12 words
A composition according to claim 8 which further comprises a sunscreen agent.
Claim 11
Dependent Claim
16 words
A composition according to claim 8 or 9, which is a solution, dispersion, gel or cream.
References Cited (Backward Citations)
DE2102172A1
Cited
CH591505A5
Cited
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