Stable vitamin b6 derivative

Abstract

A compound represented by the following general formula (I) or a salt thereof: wherein R 1 represents a glycosyl group; R 2 represents —CH 2 OH, —CHO, —CH 2 NH 2 , —CH 2 -amino acid residue, or —CH 2 —OPO 2 H; and R 3 represents hydrogen atom, or —PO 3 H 2 , and methods of its use in cosmetics, medicaments, foodstuffs, and/or feeds.

1 . A compound represented by the following general formula (I) or a salt thereof: 
       
         
           
           
               
               
           
         
       
       wherein R 1  represents a glycosyl group; R 2  represents —CH 2 OH, —CHO, —CH 2 NH 2 , —CH 2 -amino acid residue, or —CH 2 -OPO 2 H; and R 3  represents hydrogen atom, or —PO 3 H 2 . 
     
     
         2 . The compound or a salt thereof according to  claim 1 , which is selected from pyridoxine 3-β-glucoside, pyridoxine 3-α-glucoside, pyridoxamine 3-β-glucoside, pyridoxamine 3-α-glucoside, pyridoxal 3-β-glucoside, pyridoxal 3-α-glucoside, pyridoxine 3-β-galactoside, pyridoxine 3-α-galactoside, N-(4-pyridoxylmethylene)-L-serine 3-β-glucoside, N-(4-pyridoxylmethylene)-L-serine 3-α-glucoside. 
     
     
         3 . A compound represented by the following general formula (IV) or a salt thereof: 
       
         
           
           
               
               
           
         
       
       wherein R 4  represents —CH 2 OH, —CHO, or —CH 2 NH 2 , or represents —CH 2 OH, —CHO, or —CH 2 NH 2  protected with a protective group; R 5  represents hydrogen atom, a protective group of hydroxyl group, a phosphate group, or a protected phosphate group; and R 6  represents a glycosyl group which may have a protective group. 
     
     
         4 . A method for preparing a compound represented by the general formula (I) or a salt thereof according to  claim 1 , which comprises reacting a compound represented by the following general formula (II) or a salt thereof: 
       
         
           
           
               
               
           
         
       
       wherein R 4  represents —CH 2 OH, —CHO, or —CH 2 NH 2 , or represents —CH 2 OH, —CHO, or —CH 2 NH 2  protected with a protective group; and R 5  represents hydrogen atom, a protective group of hydroxyl group, a phosphate group, or a protected phosphate group, with a compound represented by the following general formula (III):
   R 6 —X   (III) 
 
       wherein R 6  represents a glycosyl group which may have a protective group, and X represents a leaving group, to obtain a compound represented by the following general formula (IV) or a salt thereof: 
       
         
           
           
               
               
           
         
       
       wherein R 4  represents —CH 2 OH, —CHO, or —CH 2 NH 2 , or represents —CH 2 OH, —CHO, or —CH 2 NH 2  protected with a protective group; R 5  represents hydrogen atom, a protective group of hydroxyl group, a phosphate group, or a protected phosphate group; and R 6  represents a glycosyl group which may have a protective group, and if necessary, deprotecting the compound represented by the general formula (IV). 
     
     
         5 . A composition for a cosmetic, a medicament, a foodstuff, and/or a feed comprising a compound represented by the following general formula (V) or a salt thereof: 
       
         
           
           
               
               
           
         
       
       wherein R 7  represents a glycosyl group; R 8  represents —CH 2 OH, —CHO, —CH 2 NH 2 , —CH 2 -amino acid residue, or —CH 2 -OPO 2 H; and R 9  represents hydrogen atom, or —PO 3 H 2 . 
     
     
         6 . A method for stabilizing a vitamin contained in a cosmetic, a medicament, a foodstuff, and/or a feed by adding a compound represented by the general formula (V) or a salt thereof mentioned in  claim 5  to the cosmetic, the medicament, the foodstuff, and/or the feed. 
     
     
         7 . A composition for a cosmetic, a medicament, foodstuff, and/or a feed containing a compound represented by the general formula (V) or a salt thereof mentioned in  claim 5  and at least one kind of vitamin, wherein stability of the vitamin is improved. 
     
     
         8 . The composition for cosmetics according to  claim 5 , which is a whitening agent, an anti-aging agent, and/or an agent for suppressing wrinkle formation by exposure to ultraviolet light. 
     
     
         9 . A composition comprising (A) a compound represented by the general formula (V) according to  claim 5 , and (B) one or more kinds of substances selected from whitening agents, antioxidants, antiphlogistics, circulation accelerators, cell activation agents, and ultraviolet absorbers, which is used as a whitening agent, an anti-aging agent, and/or an agent for suppressing wrinkle formation by exposure to ultraviolet light. 
     
     
         10 . A whitening agent containing (A) a compound represented by the general formula (V) mentioned in  claim 5 , and (B) arbutin.