Preparation method of 1-palmitoyl-3-acetylglycerol, and preparation method of 1-palmitoyl-2-linoleoyl-3-acetylglycerol using same

Abstract

Disclosed are a method for preparing 1-palmitoyl-3-acetylglycerol in high purity and high yield without a purification process using a column chromatography, and a method for preparing 1-palmitoyl-2-linoleoyl-3-acetylglycerol in high purity and high yield using the same as a key intermediate. The method for preparing 1-palmitoyl-3-acetyl glycerol comprises the steps of: forming a reaction mixture including 1-palmitoyl-3-acetyl glycerol of the Formula 1 in the specification by reacting 1-palmitoylglycerol of the Formula 2 in the specification and an acetylating agent; and separating the optically active 1-palmitoyl-3-acetylglycerol by crystallizing the reaction mixture in a saturated hydrocarbon solvent having 5 to 7 carbon atoms.

What is claimed is: 
     
         1 . A method for preparing 1-palmitoyl-3-acetylglycerol comprising the steps of:
 forming a reaction mixture including 1-palmitoyl-3-acetylglycerol represented by the following Formula 1 by reacting 1-palmitoylglycerol represented by the following Formula 2 and an acetylating agent; and   separating the optically active 1-palmitoyl-3-acetylglycerol by crystallizing the reaction mixture in a saturated hydrocarbon solvent having 5 to 7 carbon atoms,   
       
         
           
           
               
               
           
         
         wherein the compounds of the above formula 1 and 2 are racemic or optically active compounds. 
       
     
     
         2 . The method for preparing 1-palmitoyl-3-acetylglycerol according to  claim 1 , wherein the acetylating agent is selected from the group consisting of acetylchloride, acetylbromide and the mixtures thereof, and the amount of the acetylating agent is 1.3 to 1.4 equivalents with respect to 1-palmitoylglycerol. 
     
     
         3 . The method for preparing 1-palmitoyl-3-acetylglycerol according to  claim 1 , wherein the amount of the saturated hydrocarbon solvent is 2.5 to 5 times in volume ratio with respect to the weight of the reaction mixture (volume/weight), and the crystallization temperature is 0 to 15° C. 
     
     
         4 . A method for preparing 1-palmitoyl-2-linoleoyl-3-acetylglycerol comprising the steps of:
 forming a reaction mixture including 1-palmitoyl-3-acetylglycerol represented by the following Formula 1 by reacting 1-palmitoylglycerol represented by the following Formula 2 and an acetylating agent;   separating the 1-palmitoyl-3-acetylglycerol by crystallizing the reaction mixture in a saturated hydrocarbon solvent having 5 to 7 carbon atoms,   preparing a mixed anhydride by reacting linoleic acid and pivaloyl chloride in a non-polar organic solvent in the presence of an organic base; and   preparing 1-palmitoyl-2-linoleoyl-3-acetylglycerol represented by the following Formula 3 by reacting the 1-palmitoyl-3-acetylglycerol and the mixed anhydride in the presence of 4-dimethylaminopyridine,   
       
         
           
           
               
               
           
         
         wherein the compounds of the above formula 1, 2 and 3 are racemic or optically active compounds. 
       
     
     
         5 . The method for preparing 1-palmitoyl-2-linoleoyl-3-acetylglycerol according to  claim 4 , wherein the acetylating agent is selected from the group consisting of acetylchloride, acetylbromide and the mixtures thereof, and the amount of the acetylating agent is 1.3 to 1.4 equivalents with respect to 1-palmitoylglycerol. 
     
     
         6 . The method for preparing 1-palmitoyl-2-linoleoyl-3-acetylglycerol according to  claim 4 , wherein the amount of the saturated hydrocarbon solvent is 2.5 to 5 times in volume ratio with respect to the weight of the reaction mixture (volume/weight), and the crystallization temperature is 0 to 15° C. 
     
     
         7 . The method for preparing 1-palmitoyl-2-linoleoyl-3-acetylglycerol according to  claim 4 , wherein the amount of the linoleic acid is 1 to 1.05 equivalents with respect to the 1-palmitoyl-3-acetylglycerol, the amount of the pivaloyl chloride is 0.97 to 1 equivalents with respect to the linoleic acid, the amount of the organic base is 2 to 3 equivalents with respect to the 1-palmitoylglycerol, the amount of the non-polar organic solvent is 10 to 15 times in volume ratio with respect to the weight of the 1-palmitoyl-3-acetylglycerol, and the amount of the 4-dimethylamino pyridine is 1 to 10 parts by mole with respect to 100 parts by mole of the 1-palmitoyl-3-acetylglycerol. 
     
     
         8 . The method for preparing 1-palmitoyl-2-linoleoyl-3-acetylglycerol according to  claim 4 , wherein the organic base is triethylamine, and the non-polar organic solvent is selected from the group consisting of saturated hydrocarbon solvents having 5 to 7 carbon atoms and the mixtures thereof.