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Para-coumaric acid or para-hydroxycinnamic acid derivatives and their use in cosmetic or dermatological compositions

a technology of para-coumaric acid and para-hydroxycinnamic acid, which is applied in the direction of hair cosmetics, drug compositions, anti-noxious agents, etc., can solve the problems of irreversible damage to the genetic material of keratinocytes, formation of free radicals that are even more toxic, and not all melanins are protectiv

Inactive Publication Date: 2007-08-09
BASF BEAUTY CARE SOLUTIONS FRANCE SAS +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention describes the synthesis of new chemical derivatives of para-coumaric acid, which are molecules that can inhibit melanin synthesis. These new compounds have a strong inhibitory effect on melanin synthesis and are perfectly safe for cosmetic and dermopharmaceutical applications. The compounds can be easily incorporated into cosmetic or pharmaceutical formulations without causing any major problems. The invention also covers the use of a mixture of these compounds, which is more effective than using them individually. The compounds described in the invention are para-coumaric acid derivatives grafted onto tyramine, dopamine, or tyrosol derivatives. The invention also includes a method for synthesizing these compounds. The compounds used in the invention are the trans compounds, but the invention also covers the cis compounds or a cis / trans mixture, which contains a larger amount of trans compounds.

Problems solved by technology

However, not all melanins are protective.
Like all melanins, it is capable of reacting with certain forms of free radicals, but it can also cause the formation of free radicals that are even more toxic, and which are liable to cause irreversible damage to the genetic material of keratinocytes.
Moreover, certain disorders associated with dysfunction of the melanization unit are liable to cause hyperpigmentation, which is occasionally particularly unsightly.
However, these substances do not make it possible to obtain significant inhibitory effects on melanin synthesis.
This excessively weak activity does not make it possible to obtain strong enough effects and these substances are thus little used in cosmetic or pharmaceutical topical applications for effectively combating unsightly pigmentations.
The prior art mentions in particular the use of vitamin C (or derivatives thereof) or kojic acid (or derivatives thereof) for inhibiting tyrosinase, but these molecules are either cytotoxic at the concentration used, or of little efficacy.
However, these compositions are not entirely satisfactory as regards the efficacy of the depigmenting action.

Method used

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  • Para-coumaric acid or para-hydroxycinnamic acid derivatives and their use in cosmetic or dermatological compositions
  • Para-coumaric acid or para-hydroxycinnamic acid derivatives and their use in cosmetic or dermatological compositions
  • Para-coumaric acid or para-hydroxycinnamic acid derivatives and their use in cosmetic or dermatological compositions

Examples

Experimental program
Comparison scheme
Effect test

example 1

N-trans-feruloyldopamine(SO—I-146)

[0046]

[0047] A solution of ferulic acid (300 mg; 1.54 mmol) and of triethylamine (1.5 eq; 2.31 mmol) in DMF (3.5 mL) is cooled to 3 or 4° C. using an ice bath. An amine, 3-hydroxytyramine (dopamine) (1 eq; 1.54 mmol) is added to the medium, followed by addition of a solution of BOP (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophos-phate; (1 eq; 1.54 mmol) in dichloromethane (3.5 mL); the mixture is stirred for about thirty minutes in the ice bath and then for 20 hours at room temperature. Stirring is then stopped and the dichloromethane is evaporated off under vacuum. 30 mL of water are added to the remaining solution and the mixture obtained is extracted with ethyl acetate (3×75 mL). The organic phase is successively washed with 100 mL of 1N HCl solution, 100 mL of water and 100 mL of 1M sodium bicarbonate (NaHCO3) solution. It is then dried over sodium sulfate and evaporated to dryness. The product obtained is in the form of a w...

example 2

N-trans-feruloyl-3,4-dimethoxydopamine

[0048] The protocol derived from Example 1 is applied with ferulic acid and 2-(3,4-dimethoxyphenyl)ethylamine instead of ferulic acid and dopamine; the compound obtained is N-trans-feruloyl-3,4-dimethoxydopamine.

example 3

N-trans-feruloyltyramine

[0049] The protocol derived from Example 1 is applied with ferulic acid and tyramine instead of ferulic acid and dopamine; the compound obtained is N-trans-feruloyltyramine.

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Abstract

The invention relates to the use of para-coumaric acid or para-hydroxycinnamic acid derivatives in cosmetic or dermatological compositions, specifically to the use of at least one compound derived from para-coumaric acid having a general formula (I) below: in which, especially, Z represents an oxygen or an —NH— group; X and Y are identical and each represent a CH or CH2 group, as an active principle with depigmenting, free-radical-scavenging and / or antiinflammatory activity. The invention also relates to the use of the above compounds for cosmetic care or for the preparation of a pharmaceutical composition, especially for depigmenting an area of skin, having antiradical and / or antiinflammatory activity.

Description

[0001] This application claims priority from French patent application serial number 0511364, filed Nov. 8, 2005. FIELD OF THE INVENTION [0002] The present invention relates essentially to the use of at least one pare coumaric (also referred to as “p-coumaric” acid derivative as an active agent for the manufacture of a cosmetic or pharmaceutical, and especially a dermatological or topical composition, with depigmenting activity or with an inhibitory effect on melanogenesis, and / or with antiradical and / or antiinflammatory activity. [0003] The invention also covers cosmetic compositions or pharmaceutical and especially dermatological compositions, thus obtained, with depigmenting activity or with an inhibitory effect on melanogenesis, and / or with antiradical and / or antiinflammatory activity. [0004] The invention also covers a cosmetic care process or a therapeutic depigmentation treatment process using p-coumaric acid derivatives as depigmenting active agents. [0005] The invention als...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/21A61K31/216A61Q19/02
CPCA61K8/42A61K2800/782A61Q1/06A61Q1/10A61Q5/02A61Q17/00A61K8/55A61Q19/02A61Q19/10A61K8/37A61K8/375A61K8/463A61Q19/00A61P17/00A61P17/02A61P17/16A61P17/18A61P29/00A61P39/06A61K31/165A61K31/216A61Q19/08C07C69/73C07C235/34A61K31/12A61K8/35
Inventor OKOMBI, SABRINARIVAL, DELPHINEBOUMENDJEL, AHCENEMARIOTTE, ANNE-MARIEPERRIER, ERIC
Owner BASF BEAUTY CARE SOLUTIONS FRANCE SAS
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