Resveratrol glycolate and tartrate derivatives and synthetic methods therefor

Patent metadata

Field	Value
Publication number	US-10717698-B2
Application number	US-201716081842-A
Country	US
Kind code	B2
Filing date	Mar 6, 2017
Priority date	Mar 7, 2016
Publication date	Jul 21, 2020
Grant date	Jul 21, 2020

Abstract

The present invention relates to compounds of ester derivative of resveratrol, compositions comprising ester derivatives of resveratrol, processes for synthesizing an ester of resveratrol, and use thereof.

First claim

What is claimed is:

1. A compound of the formula:

wherein each R is independently selected from:

with the proviso that all R cannot simultaneously be —OH and all R cannot be simultaneously (ii).

2. The compound of claim 1 wherein two R are independently (i) and one R is (ii) and the compound is a resveratrol monoglycolate selected from the group consisting of 3-glycolate-5-4′-dihydroxystilbene; 5-glycolate-3,4′dihydroxystilbene; U and 4′-glycolate-3,5-dihydroxystilbene.

3. The compound of claim 1 wherein one R is (i) and two R are (ii) and the compound is a resveratrol diglycolate selected from the group consisting of 3,5-diglycolate-4′-hydroxystilbene; 3,4′-diglycolate-5-hydroxystilbene; and 3,4′-diglycolate-5-hydroxystilbene; 4′5-diglycolate-3-hydroxystilbene.

4. A composition comprising the compound of claim 1 in the form of a mixture wherein:
two R are independently (i) and one R is (ii) and the compound is a resveratrol monoglycolate selected from the group consisting of 3-glycolate-5-4′-dihydroxystilbene; 5-glycolate-3,4′dihydroxystilbene; 4′-glycolate-3,5-dihydroxystilbene; and mixtures thereof; and
one R is (i) and two R are (ii) and the compound is a resveratrol diglycolate selected from the group consisting of 3,5-diglycolate-4′-hydroxystilbene; 3,4′-diglycolate-5-hydroxystilbene; 3,4′-diglycolate-5-hydroxystilbene; 4′5-diglycolate-3-hydroxystilbene; and mixtures thereof; and.

5. The composition of claim 4 additionally comprising resveratrol.

6. The compound of claim 1 wherein two of R are (i) and one of R is (iii) and the compound is a resveratrol monotartrate selected from the group consisting of 3-tartrate-5-4′-dihydroxystilbene; 5-tartrate-3,4′dihydroxystilbene; and 4′-tartrate-3,5-dihydroxystilbene.

7. The compound of claim 1 wherein one of R is (i) and two of R are (iii) and the compound is a resveratrol ditartrate selected from the group consisting of 3,5-ditartrate-4′-hydroxystilbene; 3,4′-ditartrate-5-hydroxystilbene; 3,4′-ditartrate-5-hydroxystilbene; and 4′5-ditartrate-3-hydroxystilbene.

8. The compound of claim 1 wherein three of R are (iii) and the compound is resveratrol tritartrate or 3,5,4′-tritartrate stilbene.

9. A composition comprising the compound of claim 1 in the form of a mixture of where:
two of R are (i) and one of R is (iii) and the compound is a resveratrol monotartrate selected from the group consisting of 3-tartrate-5-4′-dihydroxystilbene; 5-tartrate-3,4′dihydroxystilbene; 4′-tartrate-3,5-dihydroxystilbene; and mixtures thereof,
one R is (i) and two of R are (iii) and the compound is resveratrol ditartrate and the compound is a resveratrol ditartrate selected from the group consisting of 3,5-ditartrate-4′-hydroxystilbene; 3,4′-ditartrate-5-hydroxystilbene; 3,4′-ditartrate-5-hydroxystilbene; 4′5-ditartrate-3-hydroxystilbene; and mixtures thereof,
three R are (iii) and the compound is resveratrol tritartrate or 3,5,4′-tritartrate stilbene.

10. The composition of claim 9 additionally comprising resveratrol.

11. A method for synthesizing glycolic acid esters of resveratrol comprising the steps of:
a) deprotonating resveratrol by reacting with a base,
b) preparing alpha hydroxyl protected glycolic acid by:
(i) reacting the alpha hydroxyl group of glycolic acid with compound having a protecting donor group to form a protected alpha hydroxy glycolic acid
(ii) reacting (i) with halogen donor compound to form a reactive alpha hydroxyl acyl halide,

c) reacting (a) and (b) to form alpha hydroxyl protected resveratrol glycolate; and
d) deprotecting the protected alpha hydroxyl groups to form resveratrol glycolate.

12. A method for synthesizing tartaric acid esters of resveratrol comprising the steps of:
(a) deprotonating resveratrol by reacting with a base,
(b) preparing alpha hydroxyl protected tartaric acid anhydride by:
(i) dehydrating tartaric acid to form a reactive tartaric acid anhydride,
(ii) simultaneously reacting the alpha hydroxyl groups with a compound having a protecting donor group to form a protected tartaric acid anhydride,

(c) reacting (a) and (b) to form alpha hydroxyl protected resveratrol tartrate; and
(d) deprotecting the protected alpha hydroxyl groups to form resveratrol tartrate.

13. The composition of claim 4 in the form of a cream, serum, solution, dispersion, emulsion or lotion.

14. The composition of claim 9 in the form of a cream, serum, solution, dispersion, emulsion or lotion.

Assignees

• Elc Man Llc

Inventors

• Mohammadi Fatemeh
• Tavasoli Elham

Classifications

• A61Q19/00 Primary

  Preparations for care of the skin · CPC title

• A61K8/375

  the alcohol moiety containing more than one hydroxy group · CPC title

• C09B23/148

  Stilbene dyes containing the moiety -C6H5-CH=CH-C6H5 (stilbene azo dyes C09B29/00) · CPC title

• C07C67/317 Primary

  by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups · CPC title

• C07C69/675

  of saturated hydroxy-carboxylic acids · CPC title