Resveratrol Ferulate Compounds, Compositions Containing The Compounds, And Methods Of Using The Same

• US 20100215755A1
• Filed: 05/07/2010
• Published: 08/26/2010
• Est. Priority Date: 09/08/2007
• Status: Active Grant

• Current Assignee: Daniela Bratescu, Faterneh Mohammadi, Fred Daneshyar, Julius R. Zeccuhino
• Original Assignee: Daniela Bratescu, Faterneh Mohammadi, Fred Daneshyar, Julius R. Zeccuhino
• Inventors: Daneshyar, Fred, Zeccuhino, Julius R., Mohammadi, Faterneh, Bratescu, Daniela
• Granted Patent: US 9,220,669 B2
• Time in Patent Office: Days
• US Class Current: 424/489
• CPC Class Codes: A61K 2800/31 Anhydrous
• CPC Class Codes: A61K 2800/522 Antioxidants; Radical scavengers
• CPC Class Codes: A61K 8/375 the alcohol moiety containing more than one hydroxy group
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 17/18 Antioxidants, e.g. antiradicals preparations for protection against sunlight A61Q17/00
• CPC Class Codes: A61P 39/06 Free radical scavengers or antioxidants
• CPC Class Codes: A61Q 1/02 Preparations containing skin colorants, e.g. pigments preparations in powder form A61Q1/12
• CPC Class Codes: A61Q 19/02 for chemically bleaching or whitening the skin
• CPC Class Codes: A61Q 19/08 Anti-ageing preparations

Abstract

The present invention relates to methods of using topical or cosmetic compositions containing resveratrol ferulates for skin lightening and anti-aging applications and method of synthesizing resveratrol ferulates.

Claims

1. A method for skin lightening, preventing or reducing skin aging, and/or reducing reactive oxygen species in the skin comprising applying to the skin a cosmetic composition comprising an ester of resveratrol with an aliphatic or aromatic carboxylic acid in a topically or cosmetically acceptable carrier.

2. The method of claim 1, wherein the cosmetic composition is applied to selected areas of skin with hyperpigmentation to reduce hyperpigmentation in such selected areas.

3. The method of claim 1, wherein the cosmetic composition is applied to facial skin to achieve skin lightening, anti-aging, and antioxidant effects thereon.

4. The method of claim 1, wherein the resveratrol ester is a resveratrol ferulate having the formula of:

wherein X, Y, and Z are independently selected from the group consisting of hydrogen or feruloyl, provided that at least one of X, Y, and Z is feruloyl.

5. The method of claim 4, wherein the resveratrol ferulate is selected from the group consisting of resveratrol mono-ferulates, resveratrol di-ferulates, resveratrol tri-ferulate, and mixtures thereof.

6. The method of claim 4, wherein resveratrol ferulate is present in the cosmetic composition in an amount ranging from about 0.001% to about 20% by total weight of the composition.

7. The method of claim 4, wherein resveratrol ferulate is encapsulated by one or more vesicles, microspheres, nanospheres, capsules, or mixtures thereof.

8. The method of claim 1, wherein the topically or cosmetically acceptable carrier is an emulsion comprising an aqueous phase and an oil phase.

9. The method of claim 8, wherein the resveratrol ester is dispersed or solubilized in the aqueous phase of the emulsion.

10. The method of claim 8, wherein the resveratrol ester is dispersed or solubilized in the oil phase of the emulsion.

11. The method of claim 1, wherein the topically or cosmetically acceptable carrier is anhydrous.

12. A method for synthesizing resveratrol ferulates comprising:

(a) forming a first solution containing resveratrol;

(b) forming a second solution containing ferulic acid;

(c) forming a third solution containing a liquid-phase acid;

(d) mixing the first, second, and third solutions to form a liquid mixture; and

(e) heating the liquid mixture to form solid crystals containing resveratrol ferulates.

13. The method of claim 12, wherein the liquid-phase acid is selected from the group consisting of sulfuric acid, phosphoric acid, sulfonic acid, and p-toluene sulfonic acid.

14. The method of claim 12, wherein the liquid-phase acid is p-toluene sulfonic acid.

15. The method of claim 12, wherein the first, second and third solutions contain tetarhydrophuran as a solvent.

16. The method of claim 15, wherein additional tetrahydrofuran is added into the liquid mixture during the heating.

17. The method of claim 12, wherein the resveratrol ferulates so formed are a mixture comprising resveratrol mono-ferulates, resveratrol di-ferulates, and resveratrol tri-ferulate.