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

a technology of ferulate and resveratrol, which is applied in the field of new chemical compounds as well as cosmetic or pharmaceutical compositions, can solve the problems of general instability of cosmetic formulations, reduced melanin total amount in the skin, and less desirable, and achieve the effect of stable cosmetic compositions

Inactive Publication Date: 2009-03-12
ELC MANAGEMENT LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0013]In another aspect, the present invention is related to 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 or pharmaceutical composition comprising resveratrol ferulate in a cosmetically or pharmaceutically acceptable carrier.
[0015]In still another aspect, the present invention relates to a method for skin lightening, preventing or reducing skin aging, and / or reducing reactive oxygen species, e.g. with singlet oxygen scavenging ability, in the skin comprising applying to the skin a cosmetic or pharmaceutical composition comprising an ester of resveratrol and an aliphatic or aromatic carboxylic acid in a cosmetically or pharmaceutically acceptable carrier.

Problems solved by technology

Although the heterogeneous distribution of melanin in the skin, for example, in the form of freckles or moles, is considered by some as a defining characteristic of beautiful skin, such “beauty marks”, on the other hand, often are found to be less desirable by others who seek to lighten these darkened areas of the skin.
For example, tyrosinase inhibitors, such as kojic acid, interfere with the synthesis of melanin in the melanocytes of the skin, therefore reducing the total amount of melanin in the skin.
However, one problem with resveratrol is that it is generally unstable in cosmetic formulations.
Accordingly, if used in cosmetic formulas, it can only be used in very small amounts.
If present in too large an amount, the resveratrol will hydrolyze and cause the cosmetic formulation into which it is incorporated to become discolored.
However, ferulic acid readily undergoes undesirable decomposition at a relatively low temperature and lacks long-term stability.
Therefore, formulation of ferulic acid into cosmetic compositions has proven to be generally difficult, due to issues related to product stability and shelf life.

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of Resveratrol Ferulates by Liquid-Phase Esterification

[0186]91.3 grams of resveratrol (approximately 0.4 M) was first dissolved in 300 ml of tetrahydrofuran (THF) to form a first solution. 77.7 grams of ferulic acid (approximately 0.4 M) was dissolved in 300 ml of THF to form a second solution. 0.1 gram of p-toluene sulfuric acid was dissolved in 20 ml of THF to form a third solution. The first, second, and third solutions were then transferred into a 1000 ml round-bottom flask equipped with a condenser, followed by addition of 10 ml of benzene. The liquid mixture was heated until boiling, and the boiling was continued under reflux for 5 hours to collect 50 ml of distillate. Next, 50 ml of THF and 10 ml of benzene were added into the liquid mixture, which was continued to be heated under reflux for another 5 hours to collect another 50 ml of distillate. Another 50 ml of THF and 10 ml of benzene were added into the liquid mixture, followed by continuous heating of the liqu...

example 2

Antioxidant Activity of Resveratrol Ferulates

[0190]Resveratrol Ferulates of the present invention demonstrated surprising and expected efficacy in reducing endogenous reactive oxygen species (ROS), primarily hydrogen peroxide (H2O2), in normal human epidermal keratinocyte (NHEK) cell cultures.

[0191]Specifically, NHEK cells were cultured and plated, followed by treatment with Resveratrol Ferulates at concentrations of about 10 μM, 25 μM, and 50 μM. As comparative examples, some NHEK cells were separated treated with resveratrol at a concentration of about 25 μM. Further as control examples, some NHEK cells were maintained without treatment with either Resveratrol Ferulates or resveratrol. Four samples of NHEK cells were provided for each treatment. After overnight incubation of the cell cultures, dichlorodihydrofluorescein diacetate was added thereinto. Dichlorodihydrofluorescein diacetate is a useful fluorogenic reagent for detecting reactive oxygen species in cells. Upon oxidation ...

example 3

Non-Cytotoxicity of Resveratrol Ferulates

[0193]Metabolism in viable cells produces “reducing equivalents” such as NADH or NADPH. These reducing compounds pass their electrons to an intermediate electron transfer reagent that can reduce a tetrazolium product, MTS [(3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfopheny-1)-2H-tetrazolium], into an aqueous, soluble formazan product. At death, cells rapidly lose the ability to reduce tetrazolium products. The production of the colored formazan product, therefore, is proportional to the number of viable cells in culture. In other words, light absorbance by formazan produced in the cell culture can be used as an indicator of the cell viability.

[0194]Specifically, NHEK cells were cultured and plated, followed by treatment with Resveratrol Ferulates at concentrations of about 10 μM, 25 μM, and 50 μM. As comparative examples, some NHEK cells were separated treated with resveratrol at concentrations of about 25 μM and 50 μM. ...

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Abstract

The present invention relates to cosmetic compositions containing resveratrol ferulate in a topically acceptable carrier. Such compositions are particularly effective for skin lightening and anti-aging applications and have excellent color stability and extended shelf life.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application claims priority to U.S. Provisional Patent Application No. 60 / 970,943 filed on Sep. 8, 2007 and U.S. Provisional Patent Application No. 61 / 029,600 filed on Feb. 19, 2008.FIELD OF THE INVENTION[0002]The present invention relates to new chemical compounds as well as to cosmetic or pharmaceutical compositions containing such new compounds. More specifically, the present invention relates to resveratrol ferulate compounds and compositions containing such compounds in a cosmetically or pharmaceutically acceptable carrier for achieving skin lightening, anti-aging, and antioxidant effects. The compositions of the present invention exhibit not only excellent skin lightening, anti-aging, and antioxidant effects, but also surprising and unexpected color stability and extended shelf life.BACKGROUND OF THE INVENTION[0003]The human skin is variously colored, showing individual variations even within racial groups. The appearance of th...

Claims

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Application Information

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IPC IPC(8): A61K31/192C07C65/38A61Q19/02A61P17/18
CPCA61K8/375A61K2800/31A61Q19/08A61Q1/02A61Q19/02A61K2800/522A61P17/00A61P17/18A61P39/06
Inventor BRATESCU, DANIELAMOHAMMADI, FATEMEHZECCHINO, JULIUS R.DANESHYAR, FRED
Owner ELC MANAGEMENT LLC
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