Production and Purification of Esters of Polyunsaturated Fatty Acids

Abstract

The present invention includes methods for producing and purifying esters of polyunsaturated fatty acids that include reacting a composition having triglycerides with polyunsaturated fatty acid residues in the presence of an alcohol and a base to produce an ester of a polyunsaturated fatty acid from the triglycerides. The composition can be a polyunsaturated fatty acid-containing composition that has not been conventionally processed. The reacted composition can be further processed by distillation.

1 - 111 . (canceled) 
     
     
         112 . A method for making a polyunsaturated fatty acid ester from a polyunsaturated fatty acid triglyceride selected from the group consisting of docosahexaenoic acid, docosapentaenoic acid, arachidonic acid, eicosapentaenoic acid, stearidonic acid, linolenic acid, alpha linolenic acid, gamma linolenic acid, conjugated linolenic acid and mixtures thereof, comprising:
 a. reacting the triglyceride in the presence of an alcohol and a base to produce an ester of a polyunsaturated fatty acid from the triglycerids; and   b. distilling the ester to recover a fraction comprising the ester of the polyunsaturated fatty acid   
       wherein the triglyceride has not been subjected to one or more treatments selected from the group consisting of refining, desolventization, deodorization, winterization, chill filtration, and bleaching. 
     
     
         113 . The method of  claim 112 , wherein the composition comprising the triglyceride is from a source selected from the group consisting of algae, bacteria, fungi and protists. 
     
     
         114 . The method of  claim 113 , wherein the source is selected from the group consisting of a genetically modified plant and a genetically modified microorganism, wherein the genetic modification comprises the introduction of polyketide synthase genes. 
     
     
         115 . The method of  claim 114 , wherein the microorganism is a dinoflagellate of the genus  Crypthecodinium.    
     
     
         116 . The method of  claim 112 , wherein the polyunsaturated fatty acid is docosahexaenoic acid. 
     
     
         117 . The method of  claim 112 , wherein the base is a base of the formula RO-M, wherein M is a monovalent cation and RO is an alkoxide of a C1-6 alkyl alcohol. 
     
     
         118 . The method of  claim 112 , wherein the base is sodium ethoxide. 
     
     
         119 . The method of  claim 112 , wherein the alcohol is a C1-6 alkyl alcohol. 
     
     
         120 . The method of  claim 112 , wherein the alcohol is ethanol and the ester is an ethyl ester of the polyunsaturated fatty acid. 
     
     
         121 . An oil comprising at least one polyunsaturated fatty acid, and having at least about 85 wt. % of an ethyl ester of docosahexaenoic acid and 0 wt. % eicosapentaenoic acid or an ester thereof. 
     
     
         122 . The oil of  claim 121 , wherein the ethyl ester of DHA comprises from about 85 wt. % to about 96 wt. % of the oil. 
     
     
         123 . The oil of  claim 121 , wherein the ethyl ester of DHA comprises from about 90 wt. % to about 96 wt. % of the oil. 
     
     
         124 . The oil of  claim 121 , further comprising from about 0.5 wt. % up to about 1.1 wt. % DPA, and from about 0 wt. % up to about 0.7 wt. % of a C24:0 polyunsaturated fatty acid. 
     
     
         125 . An oil prepared by the process as recited in  claim 112 . 
     
     
         126 . A pharmaceutical composition comprising the oil as recited in any one of  claims 121 - 125  wherein the composition is provided as a as a pharmaceutical oral dosage form. 
     
     
         127 . Use of a pharmaceutical composition comprising the oil according to any one of  claims 121 - 125 , for the manufacture of a medicament to be administered as a pharmaceutical oral dosage form for the treatment of high levels of triglycerides in a subject. 
     
     
         128 . Use of a pharmaceutical composition comprising the oil according to any one of  claims 121 - 125 , for the manufacture of a medicament to be administered as a pharmaceutical oral dosage form for the treatment of a dementia or pre-dementia related condition in a subject.