Flavonoide esters and their use notably in cosmetics
AssigneeColetica
InventorsEric Perrier, Anne-Marie Mariotte, Ahcène Boumendjel, Delphine Bresson-Rival
Life of this patent
Estimating the term…
Abstract
The invention relates to a flavonoid ester. This flavonoid ester results from the reaction product of at least one flavonoid selected from the group consisting of a flavonoid with a ketone group in the 4-position, a salt, ester or ether of such a flavonoid, and a C-heteroside and/or O-heteroside derivative of such a flavonoid, with the proviso that this flavonoid contains at least one free alcohol group, with an organic monoacid having from 3 to 30 carbon atoms. These flavonoid esters constitute useful active principles for the manufacture of cosmetic, dermopharmaceutical, pharmaceutical, dietetic or agri-foodstuff compositions.
Claims59
A method of providing cosmetic care comprising the topical application, to at least one zone of the skin of a person in need thereof, of a cosmetically effective amount of at least one flavonoid ester consisting essentially of the reaction product of:
- a) at least one flavonoid with a ketone group in the 4-position, said flavonoid component being selected from the group consisting of a flavonoid with a ketone group in the 4-position, a salt of said flavonoid, an ester of said flavonoid, an ether of said flavonoid, a C-heteroside of said flavonoid, and an O-heteroside of said flavonoid,
- said flavonoid with a ketone group in the 4-position having the following structural chemical formula (I) or (II):
- in which:
- -the groups (OR1) to (OR4) are in any position on the ring;
- -in formula (I), A is a hydrogen atom, a substituent R, a group —OH or a group —OR, and
- in formula (II), A is a hydrogen atom, a substituent R, or a group —OH, R being as defined for the radicals R1 to R4;
- -n1 and n2, which are identical or different from one another, are integers from 0 to 4, the total of n1+n2 being equal to at most 4, corresponding to the maximum number of substitutions on the ring;
- -n3 and n4, which are identical or different from one another, are integers from 0 to 5, the total of n3 +n4 being equal to a maximum of 5, representing the maximum number of substitutions on the ring;
- and
- -R1, R2, R3 and R4 are each independently a hydrogen atom, an alkyl group having from 1 to 30 carbon atoms, an acyl group with an alkyl radical having from 1 to 30 carbon atoms, an ose unsubstituted, an ose substituted by a hydrocarbon chain having from 1 to 30 carbon atoms,
- under the proviso that at least one of the substituents R is a hydrogen atom, thereby defining one free hydroxyl group;
- and the isomers of said esters;
- with
- b) an organic monoacid having from 3 to 30 carbon atoms.
A method of providing cosmetic care with an anti-elastase activity, comprising the topical application, to at least one zone of the skin of a person in need thereof, of a cosmetically anti-elastase effective amount of at least one flavonoid ester consisting essentially of the reaction product of:
- a) at least one flavonoid component selected from the group consisting of a flavonoid with a ketone group in the 4-position, a salt of said flavonoid, and ester of said flavonoid, an ether of said flavonoid, a C-heteroside of said flavonoid, and an O-heteroside of said flavonoid,
- said flavonoid with a ketone group in the 4-position having the following structural chemical formula (I) or (II):
- in which:
- -the groups (OR1) to (OR4) are in any position on the ring;
- -A is a hydrogen atom, a substituent R, a group —OH or a group —OR, R being as defined for the radicals R1 to R4;
- -n1 and n2, which are identical or different from one another, are integers from 0 to 4, the total of n1+n2 being equal to at most 4, corresponding to the maximum number of substitutions on the ring;
- -n3 and n4, which are identical or different from one another, are integers fromn 0 to 5, the total of n3+n4 being equal to a maximum of 5, representing the maximum number of substitutions on the ring;
- and
- -R1, R2, R3 and R4 are each independently a hydrogen atom, an alkyl group having from 1 to 30 carbon atoms, an acyl group with an alkyl radical having from 1 to 30 carbon atoms, an ose unsubstituted, an ose substituted by a hydrocarbon chain having from 1 to 30 carbon atoms,
- under the proviso that at least one of the substituents R is a hydrogen atom, thereby defining at least one free hydroxyl group;
- and the isomers of said esters;
- with
- b) an organic monoacid having from 3 to 30 carbon atoms.
A method of providing cosmetic care with free radical inhibiting activity, comprising the topical application, to at least one zone of the skin of a person in need thereof, of a cosmetically anti-elastase effective amount of a flavonoid ester consisting essentially of the reaction product of:
- a) at least on flavonoid component selected from the group consisting of a flavonoid with a ketone group in the 4-position, a salt of said flavonoid, an ester of said flavonoid, an ether of said flavonoid, a C-heteroside of said flavonoid, and an O-heteroside of said flavonoid,
- said flavonoid with a ketone group in the 4-position having the following structural chemical formula (I) or (II):
- in which:
- -the groups (OR1) to (OR4) are in any position on the ring;
- -in formula (I), A is a hydrogen atom, a substituent R, a group —OH or a group —OR, and
- in formula (II), A is a hydrogen atom, a substituent R, or a group —OH, R being as defined for the radicals R1 to R4;
- -n1 and n2, which are identical or different from one another, are integers from 0 to 4, the total of n1+n2 being equal to at most 4, corresponding to the maximum number of substitutions on the ring;
- -n3 and n4, which are identical or different from one another, are integers from 0 to 5, the total of n3+n4 being equal to a maximum of 5, representing the maximum number of substitutions on the ring;
- and
- -R1, R2, R3 and R4 are each independently a hydrogen atom, an alkyl group having from 1 to 30 carbon atoms, an acyl group with an alkyl radical having from 1 to 30 carbon atoms, an ose unsubstituted, an ose substituted by a hydrocarbon chain having from 1 to 30 carbon atoms;
- under the proviso that at least one of the substituents R is a hydrogen atom, thereby defining at least one free hydroxyl group;
- and the isomers of said esters;
- with
- b) an organic monoacid having from 3 to 30 carbon atoms.
A method of providing cosmetic care selected from the group consisting of an anti-wrinkle effect, a stimulating effect on the synthesis of components of the extracellular matrix, a toning effect, and an improving effect on the elasticity of the skin, comprising the topical application, to zones of the skin of a person in need thereof, of an effective amount for said cosmetic care of at least one flavonoid ester selected from the group consisting of quercetin lauryl pentaacylated, quercetin palmityl pentaacylated, quercetin pentabutyrilacylated, hesperitin dilaurylacylated, hesperitin monolaurylacylated, hesperitin dilaurylacylated, hesperitin dipalmitylacylated, hesperitin tripalmitylacylated, hesperitin tributyrilacylated, hesperitin tristearylacylated, hesperitin trioleoylacylated, hesperitin trilinoleoylacylated, hesperitin trilinolenoylacylated, hesperitin triundecylenoylacylated, hesperitin heptanoylacylated, hesperitin trisuccinylacylated, apigenin trilaurylacylated, naringenin triacylated, hesperidin octalaurylacylated, hesperidin octapalmitylacylated, naringin octalaurylacylated, diosmin laurylacylated and rutin laurylacylated.
A method of providing cosmetic care comprising the topical application, to at least one zone of the skin of a person in need thereof, of an effective amount of at least one flavonoid ester selected from the group consisting of hesperitin dilaurylacylated, hesperitin monolaurylacylated, hesperitin dilaurylacylated, hesperitin dipalmitylacylated, hesperitin tripalmitylacylated, hesperitin tributyrilacylated, hesperitin tristearylacylated, hesperitin trioleoylacylated, hesperitin trilinoleoylacylated, hesperitin trilinolenoylacylated, hesperitin triundecylenoylacylated, hesperitin heptanoylacylated, hesperitin trisuccinylacylated, apigenin trilaurylacylated, naringenin triacylated, hesperidin octalaurylacylated, hesperidin octapalmitylacylated, naringin octalaurylacylated, diosmin laurylacylated and rutin laurylacylated.
Dependencies are inferred from the claim text.