Synthesis of coenzyme Q10, ubiquinone

Abstract

Processes for the stereospecific synthesis of coenzyme Q10, ubiquinone, are disclosed; a semi synthetic procedure using solanesol derived from tobacco waste as the starting material. The process of the invention results in high yields of isometrically useful compositions containing the optically pure isomers.

I claim:  
     
         1 . A stereospecific synthesis of optically pure trans (E) isomer of coenzyme Q 10 having the formula  
       
         
           
           
               
               
           
         
       
       which comprises extracting solanesol from tobacco dust and using said solanesol as the starting material for carrying out the following sequence of reactions  
       
         
           
           
               
               
           
         
       
       separately carrying out the following reactions:  
       
         
           
           
               
               
           
         
       
       thereafter reacting the isodecaprenol and 2,3,-dimethoxy-5-methyl-hydroquinone to form the optical pure ubiquinone  
       
         
           
           
               
               
           
         
       
     
     
         2 . Method of treating impaired or damaged tissue in humans and animals which comprises administering a composition comprising as the principal active ingredient a therapeutically effective amount of optically pure trans (E) isomer of coenzyme Q 10 (2,3-dimethoxy-5-methyl-6-decaprenyl-beuoquinone) in admixture with a pharmaceutically acceptable carrier.  
     
     
         3 . The method of  claim 2  wherein said composition is administered orally.  
     
     
         4 . The method of  claim 3  wherein said composition is administered in an amount of 15-400 mg pro die.  
     
     
         5 . The method of  claim 3  wherein said composition is administered in an amount of 100-200 mg pro die.  
     
     
         6 . The method of  claim 3  wherein said composition is administered in an amount of 15-30 mg pro die.  
     
     
         7 . The method of  claim 3  wherein said composition is in tablet form.  
     
     
         8 . The method of  claim 3  wherein said composition is in liquid form.  
     
     
         9 . The method of  claim 2  wherein said composition is administered by topical application.  
     
     
         10 . The method of  claim 9  wherein said composition contains the optically pure coenyme Q 10 in an amount of 0.1-10%.  
     
     
         11 . The method of  claim 9  wherein said composition contains the optically pure coenzyme Q 10 in an amount of 0.25-1%.  
     
     
         12 . The method of  claim 9  wherein said composition is to be used as a cosmetic and said optically pure coenzyme Q 10 is present in an amount of 0.0001 to 0.1%.  
     
     
         13 . The method of  claim 2  wherein said pharmaceutically acceptable carrier is a vegetable oil.  
     
     
         14 . The method of  claim 9  wherein said composition is formulated as a paste, cream, ointment, gel, lotion or unguent.  
     
     
         15 . The stereospecific optically pure trans (E) isomer of coenzyme Q 10 produced by the process of  claim 1.