Novel Skin Lightening Agents, Compositions and Methods

Abstract

Compounds of formula I, process for making same, and cosmetic compositions and methods of skin lightening using compounds of formula I as skin lightening agents: Where each A 1 and/or A 2 independently is ═H or COR, CO 2 R, CONHR, the latter three having the following formula A: where R═C 1 -C 18 saturated or unsaturated, linear or branched, hydrocarbon; and each Y 1 and/or Y 2 independently is H; C 1 -C 18 saturated or unsaturated hydrocarbon; or OZ, where Z=H or COR 1 , CO 2 R 1 , CONHR 1 of formula B: and where R 1 ═C 1 -C 18 saturated or unsaturated, linear or branched, hydrocarbon; X is Carbon, Nitrogen, Sulfur, or Oxygen; and N is in integer between 0 and 2.

1 - 13 . (canceled) 
   
   
       14 . A compound of general formula I 
     
       
         
         
             
             
         
       
     
     Wherein
 each A 1  and/or A 2  independently is ═H, COR, CO 2 R, CONHR where R═C 1 -C 18  saturated or unsaturated hydrocarbon; and 
 each Y 1  and/or Y 2  independently is H, C 1 -C 18  saturated or unsaturated hydrocarbon, or OZ where Z=H, COR 1 , CO 2 R 1 , CONHR 1  and wherein R 1 ═C 1 -C 18  saturated or unsaturated hydrocarbon; 
 X is Carbon, Nitrogen, Sulfur, or Oxygen; and 
 N is in integer between 0 and 2. 
 
   
   
       15 . The compound of  claim 14 , having a general formula II: 
     
       
         
         
             
             
         
       
     
   
   
       16 . A compound of  claim 14 , having the formula III: 
     
       
         
         
             
             
         
       
     
   
   
       17 . The compound of  claim 16 , wherein the hydroxy groups of said compound are esterified with an acid selected from the group consisting of ferulic acid, vanillic acid, sebacic acid, azaleic acid, benzoic acid, caffeic acid, coumaric acid, salicylic acid, cysteine, cystine, lactic acid, glycolic acid and mixtures thereof. 
   
   
       18 . A process for synthesizing 4-[2′-(1′,3′-dithiacyclopenty)]-1,3-dihydroxybenzene, 4-[2′-(1′,3′-dithiacyclohexy)]-1,3-dihydroxybenzene, 4-[2′-(1′,3′-dithiacyclohepty)]-1,3-dihydroxybenzene, or mixtures thereof comprising:
 reacting   (a) 2,4-dihydroxy benzaldehyde; with   (b) 1,2-Dimercaptoethane, 1,3-Dimercaptopropane, 1,4-Dimercaptobutane, or mixtures thereof, respectively;   in the presence of an acid catalyst;   wherein said acid catalyst is selected from the group consisting of methane sulfonic acid, p-toluene sulfonic acid, sulfuric acid, hydrochloric acid, acidic resins and mixtures thereof.