Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Topical Compositions Containing Phosphorylated Polyphenols

Inactive Publication Date: 2008-04-24
AJINOMOTO OMNICHEM SA +1
View PDF12 Cites 79 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0003]The present invention provides topical compositions comprising at least one phosphorylated polyphenol and a topically acceptable carrier; these compositions provide a greater stability of biological activity as well as compositional integrity than is possible with an unmodified polyphenol. The compositions of the invention are particularly useful in, among other uses, methods for scavenging free radicals on the skin, and treating and reducing the symptoms of aging on the skin. The invention also provides a method of delayed release of polyphenols on the skin which comprises applying to the skin a composition containing at least one phosphorylated polyphenol and a topically acceptable carrier. The invention also provides a method for rendering water-soluble an insoluble polyphenol which comprises phosphorylating the insoluble polyphenol to an extent sufficient to render the polyphenol water-soluble.

Problems solved by technology

Ironically, however, these protective molecules themselves are susceptible to damage from external sources.
These versatile compounds are highly susceptible to degradation by exposure to heat or light, frequently resulting in discoloration of the composition in which they are contained, as well as diminishing their efficacy when applied to the skin.
Because of this weakness, the true scope of their utility has not yet fully been realized.
Compositions containing unprotected polyphenols are not likely to deliver their complete biological potential, and the provision of protective packaging or special handling necessary to preserve their activity is too costly to be commercially feasible on a large scale.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Topical Compositions Containing Phosphorylated Polyphenols
  • Topical Compositions Containing Phosphorylated Polyphenols
  • Topical Compositions Containing Phosphorylated Polyphenols

Examples

Experimental program
Comparison scheme
Effect test

example 1

Phosphorylation of Grape Seed Tannin

[0061]100.0 g. of grape seed tannin (TANFOS 167-134)) was dissolved in 300 mL of water at room temperature under nitrogen atmosphere. The solution was brought to a pH of 9 with NaOH 29%, and 26.6 mL phosphorous oxychloride was added to the solution over a period of 1.5 hours. During this addition, more NaOH 29% was added to maintain the pH at 9. After the addition, the reaction mixture was stirred overnight, and analysed by HPLC. The product was then acidified with HCl 25% to a pH of 3.1 and isolated via spray drying to obtain a pink powder.

example 2

Phosphorylation of Resveratrol

[0062]The structure of the compound known as resveratrol (3,4,5-trihydroxystilbene) is as follows:

[0063]Phosphorylation can be achieved, for example, by the procedure disclosed by Pettit et al., J. Med. Chem. 2002, 45, 2534-2542). A solution of resveratrol (25 mmols, 5.7 g) and dimethylaminopyridine (7.5 mmols, 0.93 g) in 100 mL of acetonitrile is cooled under nitrogen up to −10° C. After 10 minutes, CCl4 (375 mmol, 36.2 mL) and DIEA (159 mmols; 27.7 mL) and the mixture maintained under stirring for 30 minutes. Dibenzylphosphite (113 mmols, 25.0 mL) is added and the mixture stirred for an additional 12 hours at room temperature. The course of the reaction is monitored by TLC (Silica F254, eluent ethyl acetate / n-hexane 80 / 20 v / v). One liter 0.5 M KH2PO4 is added, and the mixture then extracted with ethyl acetate. The resulting product, tri(dibenzylphosphate) resveratrol is purified by filtration on a silica gel, washing first with a mixture of ethyl acet...

example 3

Solubility of Resveratrol Triphosphate

[0066]The water solubility of resveratrol is tested at pH 7 in 1 mM potassium phosphate buffer at room temperature. Ten mg of resveratrol (M.W. 228.24) are suspended in 10 ml of buffer. This suspension, corresponding to a concentration of 1 g / l or 4.38 mM, is agitated for 24 hours in a rotary shaker at 25° C. in the dark. The sample is centrifuged at 14,000 rpm for 5 minutes and an OD of 6.26 is determined at 305 nm wavelength at which the ε mM of resveratrol has a value of 28.1. Assuming complete solubility of resveratrol, the OD that should have been obtained is 123.1 (4.38×28.1). With an observed OD of 6.26, the percentage of dissolved resveratrol is 5.1% (6.26×100 / 123.1) or 5.1 mg / l.

[0067]In contrast, the solubility and stability of the resveratrol triphosphate tested under the same conditions, in water of different pH, in the range of 4 to 9, at room temperature. The solubility of the resveratrol triphosphate is observed to be >30% w / v, sho...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
Solubility (mass)aaaaaaaaaa
Hydrolysableaaaaaaaaaa
Login to View More

Abstract

The present invention provides topical compositions containing phosphorylated polyphenols in combination with a topically acceptable carrier. The compositions of the invention provide a means for delayed delivery of the polyphenol to keratinous tissues, such as skin, hair and nails, with enzymes of the keratinous tissue dephosphorylating the polyphenol, and returning it to its native active form. The compositions are particularly useful in the regulation of skin conditions.

Description

FIELD OF THE INVENTION[0001]The invention relates to compositions for application to the skin. In particular, the invention relates to topical compositions containing stabilized polyphenol compounds.BACKGROUND OF THE INVENTION[0002]The group of compounds known as polyphenols exhibit a wide variety of biological activities, and are widely used in topical formulations for treatment of the skin. One particularly widely exploited function of many polyphenols is as antioxidants. In this role, these compounds can serve two roles: they can protect the compositions in which they are delivered from oxidative degradation, as well as providing protection to the skin to which they are applied from the ravages of free radicals. Ironically, however, these protective molecules themselves are susceptible to damage from external sources. These versatile compounds are highly susceptible to degradation by exposure to heat or light, frequently resulting in discoloration of the composition in which they...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): A61K31/665A61K31/661A61K36/61A61K36/752A61K36/87A61P17/00
CPCA61K31/66A61K36/00A61K36/87A61K2300/00A61P17/00A61P17/06A61P17/08A61P17/10A61P35/00A61K31/327A61K31/33
Inventor DECLERCQ, LIEVECORSTJENS, HUGOMAES, DANIELVAN BRUSSEL, WILLYSCHELKENS, GEERT
Owner AJINOMOTO OMNICHEM SA
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com