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

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 CH 2 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.

1 . A topical composition comprising an effective amount of at least one compound derived from para-coumaric acid having a general formula (I) below:  
     
       
         
         
             
             
         
       
     
     in which: 
 Z is an oxygen or an —NH— group;  
 X and Y are identical and each represent a CH group or CH 2  group;  
 n is a number ranging from 1 to 12;  
 Ra and Rb are identical or different and represent a hydrogen atom, a linear or branched acyl group, a linear or branched, saturated or unsaturated alkyl group; a salified or non-salified sulfonyl group (SO 3 H); or a salified or non-salified phosphonate group (PO 3 H 2 );  
 R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8  are, independently of each other: a hydrogen atom; a hydroxyl group; a halogen atom; a salified or non-salified acid function; an aldehyde function; an amide function; a primary, secondary, or tertiary amine function in basic or salified form; a cyano group; a thiol group; a nitro group; a sugar (O-heteroside); a linear or branched alkoxide group; a linear or branched alkyl chain; a linear or branched alkenyl chain; a linear or branched thioalkyl chain; a linear or branched alkoxy chain; an alkenyloxy chain; a salified or non-salified sulfate group; a salified or non-salified sulfonyl group; a salified or non-salified phosphonate group; a salified or non-salified phosphate group; or a silanol group; in which the carbon-based chains may be substituted; and  
 a dermatologically acceptable carrier;  
 wherein said para-coumaric acid derivative is effective to exert a depigmenting activity, an inhibitory effect on melanogenesis, a free-radical-scavenging activity or an anti-inflamatory activity on an area of skin to which it is topically applied.  
 
   
   
       2 . The topical composition of  claim 1  wherein n is a number ranging from 2 to 12.  
   
   
       3 . The topical composition of  claim 1  wherein Ra and Rb of general formula (I) each independently represent a hydrogen atom, a linear or branched C1-12 acyl group, a salified or non-salified sulfonyl group (SO 3 H); a salified or non-salified phosphonate group (PO 3 H 2 ), or a hydrogen.  
   
   
       4 . The topical composition of  claim 1  wherein the para-coumaric acid derivative is represented by a chemical formula (II) in which the groups R 1  to R 8 , X, Y, Z and n represent the elements cited in the general formula I:  
     
       
         
         
             
             
         
       
     
     in which: 
 Z is an oxygen or an —NH— group;  
 X and Y are identical and each represent a CH group or CH 2  group;  
 n is a number ranging from 1 to 12; and  
 R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8  are, independently of each other: a hydrogen atom; a hydroxyl group; a halogen atom; a salified or non-salified acid function; an aldehyde function; an amide function; a primary, secondary, or tertiary amine function in basic or salified form; a cyano group; a thiol group; a nitro group; a sugar (O-heteroside); a linear or branched alkoxide group; a linear or branched alkyl chain; a linear or branched alkenyl chain; a linear or branched thioalkyl chain; a linear or branched alkoxy chain; an alkenyloxy chain; a salified or non-salified sulfate group; a salified or non-salified sulfonyl group; a salified or non-salified phosphonate group; a salified or non-salified phosphate group; or a silanol group; in which the carbon-based chains may be substituted.  
 
   
   
       5 . The topical composition of  claim 1  wherein the para-coumaric acid derivative is represented by chemical formula (III) below:  
     
       
         
         
             
             
         
       
     
     in which: 
 Z is an oxygen or an —NH— group;  
 X and Y are identical and each represent a CH group or CH 2  group;  
 n is a number ranging from 1 to 12; and  
 R 2 , R 3 , R 6 , and R 7  are, independently of each other: a hydrogen atom; a hydroxyl group; a halogen atom; a salified or non-salified acid function; an aldehyde function; an amide function; a primary, secondary, or tertiary amine function in basic or salified form; a cyano group; a thiol group; a nitro group; a sugar (O-heteroside); a linear or branched alkoxide group; a linear or branched alkyl chain; a linear or branched alkenyl chain; a linear or branched thioalkyl chain; a linear or branched alkoxy chain; an alkenyloxy chain; a salified or non-salified sulfate group; a salified or non-salified sulfonyl group; a salified or non-salified phosphonate group; a salified or non-salified phosphate group; or a silanol group; in which the carbon-based chains may be substituted.  
 
   
   
       6 . The topical composition of  claim 1  wherein the para-coumaric acid derivative is represented by either of the formulae (IVa and IVb) below  
     
       
         
         
             
             
         
       
     
     in which R 6  and R 7  are, independently of each other: a hydrogen atom; a hydroxyl group; a halogen atom; a salified or non-salified acid function; an aldehyde function; an amide function; a primary, secondary, or tertiary amine function in basic or salified form; a cyano group; a thiol group; a nitro group; a sugar (O-heteroside); a linear or branched alkoxide group; a linear or branched alkyl chain; a linear or branched alkenyl chain; a linear or branched thioalkyl chain; a linear or branched alkoxy chain; an alkenyloxy chain; a salified or non-salified sulfate group; a salified or non-salified sulfonyl group; a salified or non-salified phosphonate group; a salified or non-salified phosphate group; or a silanol group; in which the carbon-based chains may be substituted.  
   
   
       7 . The topical composition of  claim 6  wherein R 6  and R 7  are hydrogen.  
   
   
       8 . The topical composition of  claim 1  wherein the para-coumaric acid derivative is represented by either of the formulae (Va and Vb) below  
     
       
         
         
             
             
         
       
     
     in which R 6  and R 7  are, independently of each other: a hydrogen atom; a hydroxyl group; a halogen atom; a salified or non-salified acid function; an aldehyde function; an amide function; a primary, secondary, or tertiary amine function in basic or salified form; a cyano group; a thiol group; a nitro group; a sugar (O-heteroside); a linear or branched alkoxide group; a linear or branched alkyl chain; a linear or branched alkenyl chain; a linear or branched thioalkyl chain; a linear or branched alkoxy chain; an alkenyloxy chain; a salified or non-salified sulfate group; a salified or non-salified sulfonyl group; a salified or non-salified phosphonate group; a salified or non-salified phosphate group; or a silanol group; in which the carbon-based chains may be substituted.  
   
   
       9 . The topical composition of  claim 8  wherein R 6  and R 7  are hydrogen.  
   
   
       10 . The topical composition of  claim 1  wherein R 1 , R 4 , R 5  and R 8  represent a hydrogen.  
   
   
       11 . The topical composition of  claim 1  wherein R 2  and R 3  are a salified or unsalified hydroxyl group, a methoxy group, or a hydrogen.  
   
   
       12 . The topical composition of  claim 1  wherein R 6  and R 7  are a salified or unsalified hydroxyl group, a methoxy group, or a hydrogen.  
   
   
       13 . The topical composition of  claim 1  wherein n=2.  
   
   
       14 . The topical composition of  claim 1  wherein R 6  and R 7  are a hydroxyl group or a hydrogen atom.  
   
   
       15 . The topical composition of  claim 1  wherein the para-coumaric acid derivatives are ferulic acid derivatives in which: 
 Ra, Rb, R 1 , R 2  and R 4  represent a hydrogen atom;    R 3  represents a methoxy group;    X and Y each represent a CH group;    and n is equal to 2.    
   
   
       16 . The topical composition of  claim 15  wherein the ferulic acid derivatives correspond to formula (IIa and IIb) below;  
     
       
         
         
             
             
         
       
     
     in which: 
 R 5 , R 6 , R 7  and R 8  are, independently of each other: a hydrogen atom; a hydroxyl group; a halogen atom; a salified or non-salified acid function; an aldehyde function; an amide function; a primary, secondary, or tertiary amine function in basic or salified form; a cyano group; a thiol group; a nitro group; a sugar (O-heteroside); a linear or branched alkoxide group; a linear or branched alkyl chain; a linear or branched alkenyl chain; a linear or branched thioalkyl chain; a linear or branched alkoxy chain; an alkenyloxy chain; a salified or non-salified sulfate group; a salified or non-salified sulfonyl group; a salified or non-salified phosphonate group; a salified or non-salified phosphate group; or a silanol group; in which the carbon-based chains may be substituted.  
 
   
   
       17 . The topical composition of  claim 16  wherein R 5 , R 6 , R 7  and R 8  each represent a hydrogen atom.  
   
   
       18 . The topical composition of  claim 16  wherein R 5 , R 6  and R 8  each represent a hydrogen atom and R 7  represents a hydroxyl group.  
   
   
       19 . The topical composition of  claim 1  wherein the para-coumaric acid derivatives are caffeic acid derivatives in which: 
 Ra, Rb, R 1 , R 2  and R 4  represent a hydrogen atom;    R 3  represents a hydroxyl group;    X and Y each represent a CH group;    and n is equal to 2.    
   
   
       20 . The composition of  claim 19  wherein the caffeic acid derivatives correspond to either of the formulae (IIIa and IIIb) below:  
     
       
         
         
             
             
         
       
     
     in which: 
 R 5 , R 6 , R 7  and R 8  are, independently of each other: a hydrogen atom; a hydroxyl group; a halogen atom; a salified or non-salified acid function; an aldehyde function; an amide function; a primary, secondary, or tertiary amine function in basic or salified form; a cyano group; a thiol group; a nitro group; a sugar (O-heteroside); a linear or branched alkoxide group; a linear or branched alkyl chain; a linear or branched alkenyl chain; a linear or branched thioalkyl chain; a linear or branched alkoxy chain; an alkenyloxy chain; a salified or non-salified sulfate group; a salified or non-salified sulfonyl group; a salified or non-salified phosphonate group; a salified or non-salified phosphate group; or a silanol group; in which the carbon-based chains may be substituted.  
 
   
   
       21 . The topical composition of  claim 20  wherein R 5 , R 6 , R 7  and R 8  each represent a hydrogen atom.  
   
   
       22 . The topical composition of  claim 20  wherein R 5 , R 6  and R 8  each represent a hydrogen atom and R 7  represents a hydroxyl group.  
   
   
       23 . The topical composition of  claim 1  wherein the substituents Ra, Rb, R 1 , R 2 , R 4 , R 5 , R 6 , R 7  and R 8  each represent a hydrogen atom; 
 R 3  represents a hydroxyl group; and    n is equal to 2.    
   
   
       24 . The topical composition of  claim 23  wherein the para-coumaric acid derivatives correspond to either of formulae (VIa and VIb) below  
     
       
         
         
             
             
         
       
     
     in which X and Y are CH or CH 2  groups.  
   
   
       25 . The topical composition of  claim 1  wherein the para-coumaric acid derivative is extracted from a plant.  
   
   
       26 . The topical composition of  claim 25  wherein the extract is selected from at least one of the following para-coumaric acid derivatives:  
     
       
         
         
             
             
         
       
     
   
   
       27 . The topical composition of  claim 1  wherein the composition is a cosmetic composition.  
   
   
       28 . The topical composition of  claim 27  further comprising at least one other cosmetically active ingredient.  
   
   
       29 . The topical composition of  claim 1  wherein the composition is a pharmaceutical composition for the treatment of hyperpigmentation.  
   
   
       30 . A method of reducing skin pigmentation of the skin comprising applying the topical composition of  claim 1  to an area of human skin.  
   
   
       31 . A method of cosmetic care for reducing skin pigmentation in the area of application comprising topically applying the cosmetic composition of  claim 27  to at least one area of the skin tissue of an individual having hyperpigmentation.  
   
   
       32 . A method of depigmentation or melanogenesis inhibition comprising topically applying to at least one area of skin tissue of an individual in need thereof a composition comprising an effective amount of at least one para-coumaric acid derivative compound having a general formula (I) below:  
     
       
         
         
             
             
         
       
     
     in which: 
 Z is an oxygen or an —NH— group;  
 X and Y are identical and each represent a CH group or CH 2  group;  
 n is a number ranging from 1 to 12;  
 Ra and Rb are identical or different and represent a hydrogen atom, a linear or branched acyl group, a linear or branched, saturated or unsaturated alkyl group; a salified or non-salified sulfonyl group (SO 3 H); or a salified or non-salified phosphonate group (PO 3 H 2 );  
 R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8  are, independently of each other: a hydrogen atom; a hydroxyl group; a halogen atom; a salified or non-salified acid function; an aldehyde function; an amide function; a primary, secondary, or tertiary amine function in basic or salified form; a cyano group; a thiol group; a nitro group; a sugar (O-heteroside); a linear or branched alkoxide group; a linear or branched alkyl chain; a linear or branched alkenyl chain; a linear or branched thioalkyl chain; a linear or branched alkoxy chain; an alkenyloxy chain; a salified or non-salified sulfate group; a salified or non-salified sulfonyl group; a salified or non-salified phosphonate group; a salified or non-salified phosphate group; or a silanol group; in which the carbon-based chains may be substituted.  
 
   
   
       33 . A method of exerting antiradical activity, antiinflammatory activity, or both on an area of skin tissue of an individual comprising topically applying to the skin tissue a composition comprising an effective amount of at least one para-coumaric acid derivative compound having general formula (I) below:  
     
       
         
         
             
             
         
       
     
     in which: 
 Z is an oxygen or an —NH— group;  
 X and Y are identical and each represent a CH group or CH 2  group;  
 n is a number ranging from 1 to 12;  
 Ra and Rb are identical or different and represent a hydrogen atom, a linear or branched acyl group, a linear or branched, saturated or unsaturated alkyl group; a salified or non-salified sulfonyl group (SO 3 H); or a salified or non-salified phosphonate group (PO 3 H 2 );  
 R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8  are, independently of each other: a hydrogen atom; a hydroxyl group; a halogen atom; a salified or non-salified acid function; an aldehyde function; an amide function; a primary, secondary, or tertiary amine function in basic or salified form; a cyano group; a thiol group; a nitro group; a sugar (O-heteroside); a linear or branched alkoxide group; a linear or branched alkyl chain; a linear or branched alkenyl chain; a linear or branched thioalkyl chain; a linear or branched alkoxy chain; an alkenyloxy chain; a salified or non-salified sulfate group; a salified or non-salified sulfonyl group; a salified or non-salified phosphonate group; a salified or non-salified phosphate group; or a silanol group; in which the carbon-based chains may be substituted.