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.

1 - 8 . (canceled) 
     
     
         9 . A method of making 1-palmitoyl-3-acetylglycerol comprising the steps of:
 reacting 1-palmitoylglycerol with an acetylating agent, and   separating the 1-palmitoyl-3-acetylglycerol thus formed by crystalization,   wherein the 1-palmitoylglycerol and 1-palmitoyl-3-acetylglycerol are racemic or optically active compounds.   
     
     
         10 . The method of  claim 9 , wherein the acetylating agent is selected from the group consisting of acetylchloride, acetylbromide and the mixtures thereof. 
     
     
         11 . The method of  claim 10  wherein the amount of the acetylating agent is 1.3 to 1.4 molar equivalents relative to the 1-palmitoylglycerol. 
     
     
         12 . The method of  claim 9 , wherein the reaction of 1-palmitoylglycerol and the acetylating agent is carried out in a solvent and in the presence of an organic base, wherein the solvent is a non-polar, aprotic solvent. 
     
     
         13 . The method of  claim 12 , wherein the organic base comprises pyridine. 
     
     
         14 . The method of  claim 12 , wherein the non-polar, aprotic solvent comprises one or more of a solvent selected from dichloromethane, acetone, ethyl acetate, and mixtures of any of these. 
     
     
         15 . The method of  claim 15 , wherein the solvent comprises dichloromethane. 
     
     
         16 . The method of  claim 9 , wherein after reacting the 1-palmitoylglycerol with the acetylating agent, water and acid is added to induce a phase separation, and the organic layer is separated and filtered to obtain a filtrate. 
     
     
         17 . The method of  claim 16 , wherein the filtrate is dissolved in a saturated hydrocarbon solvent having 5-7 carbon atoms, and the solution thus obtained is cooled to precipitate crystalline 1-palmitoyl-3-acetylglycerol. 
     
     
         18 . The method of  claim 17 , wherein the crystallization temperature is 0 to 15° C. 
     
     
         19 . The method of  claim 9  wherein the 1-palmitoylglycerol and 1-palmitoyl-3-acetylglycerol each have the (R) configuration. 
     
     
         20 . Crystalline 1-palmitoyl-3-acetylglycerol. 
     
     
         21 . Crystalline 1-palmitoyl-3-acetylglycerol of  claim 20  which is rac-1-palmitoyl-3-acetylglycerol. 
     
     
         22 . Crystalline 1-palmitoyl-3-acetylglycerol of  claim 21  which is (R)-1-palmitoyl-3-acetylglycerol.