Eicosapentaenoic acid ethyl ester

Product identification for refined ethyl esters of fish oil, containing eicosapentaenoic acid ethyl ester and docosahexaenoic acid ethyl ester... 

Teramoto M, Matsuyama H, Nakai K, Uesaka T, and Ohnishi N. Eacilitated uphill transport of eicosapentaenoic acid ethyl ester through bulk and supported liquid membranes containing silver nitrate as carrier A new type of uphill transport. J Mem Sci, 1994 91(1-2) 209-213. Teramoto M, Matsuyama H, and Ohnishi N. Selective facilitated transport of benzene across supported and flowing liquid membranes containing silver nitrate as a carrier. J Mem Sci, 1990 50 269-278. 

Yamazaki K, Hamazaki T. Changes in fatty acid composition in rat blood and organs after infusion of eicosapentaenoic acid ethyl ester. Biochim Biophys Acta 1992 1128 35-43. 

Abbreviations PC, phosphatidylcholine FFA, free fatty acid EPA, eicosapentaenoic acid DHA, docosahexaenoic acid EPA-EE, eicosapentaenoic acid ethyl ester DHA-EE, docosahexaenoic acid ethyl ester CLA, conjugated linoleic acid,. 

C.W. Park, S.J. Kwon, J.J. Han, and J.S. Rhee Transesterification of phosphatidylcholine with eicosapentaenoic acid ethyl ester using phospholipase A2 in organic solvent. Biotechnology Letters 22 (2000) 147-150. 

Saito, C., Chang, K.-J.,Tamura,Y., and Yoshida, S. (1991) Ingestion of Eicosapentaenoic Acid-Ethyl Ester Renders Rabbit LDL Less Susceptible to Cu +-Catalyzed Oxidative Modification, Biochem. Biophys. Res. Commun. 175,61-67. 

Wojenski, C.M., Silver, M.J. and Walker, J. (1991) Eicosapentaenoic acid ethyl ester as an antithrombotic agent comparison to an extract of fish oil. Biochim. Biophys. Acta 1081, 33-38. 

Han, JJ, Iwasaki, Y and Yamane, T (1999) Monitoring of lipase-catalyzed transesterification between eicosapentaenoic acid ethyl ester and tricaprylin by silver ion high-performance liquid chromatography and high-temperature gas chromatography. J. Am. Oil Chem. Soc., 76,31-39. 

Mectianism of Action A combination of ethyl esters of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) that inhibits acyl coenzyme A l,2-diacylglycerol acyltransferase and increases peroxisomal oxidation in the liver. Therapeutic Effect Reduces the synthesis of triglycerides in the liver. 

Polyunsaturated fatty acids (PUFAs) have various physiological functions and are widely used as pharmaceuticals, neutraceuticals, and as food additives. The ethyl ester of eicosapentaenoic acid (EPA) has been used for the treatment of arteriosclerosis and hyperlipemia since 1991 in Japan (Hara, 1993). DHA possesses not only similar physiological activities to those of EPA, but also an important function in the brain and retina (Hung, 2007). In addition, DHA accelerates the growth of preterm infants as does arachidonic acid (Carlson et al., 1993 Lanting et al., 1994). From these reasons, DHA ethyl ester (DHAEE) is currently expected to be used as a medicine, and the development of the purification methods is desired. 

Teramoto M, Matsuyama H, and Nakai K. Separation of ethyl esters of eicosapentaenoic acid and docosahexaenoic acid by circulating liquid membranes using silver nitrate as a carrier. Uphill transport by use of temperature and solvent dependencies of distribution ratio. Sep Sci Technol, 1996 31(14) 1953-1969. 

Supercritical fluid carbon dioxide (SC-CO2) fractionation of fish oil ethyl esters (EE) was employed to prepare EE of two omega-3 fatty acids, all cis-5,8,11,14, 17-eicosapentaenoic acid (EPA) and all cis-4,7,10,13, 16,19-docosahexaenoic acid (DHA) in 90% purity and to separate the synthetic triacylglycerols (TG), trieicosapentaenoylglycerol (tri-EPA), and tridocosahexaenoyl-glycerol (tri-DHA) in > 92% purity from other reaction mixture components. In the synthesis, glycerine reacted with EE and sodium glyceroxide catalyst to form TG. 

Krokan HE, Bjerve KS, Mork E. The enteral bioavailabiUty of eicosapentaenoic acid and docosahexaenoic acid is as good from ethyl esters as from glyceryl esters in spite of lower hydrolytic rates by pancreatic lipase in vitro. Biochim Biophys Acta 1993 1168 59-67. 

Nordoy A, Barstad L. Connor Wl i, Hatcher L. Absorption of the n-3 eicosapentaenoic and docosahexaenoic acids as ethyl esters and triglycerides by humans. Am J Clin Nutr 1991 53 1185-1190. 

Paulsen JE, Elvsaas I-KO, Steffensen 1-L, Alexander J. A fish oil derived concentrate enriched in eicosapentaenoic and docosahexaenoic acid as ethyl ester suppresses the formation and growth of intestinal polyps in the Min mouse. Carcinogenesis 1997 18 1905-1910. 

Abbreviations ROS, reactive oxygen species LDL, low density lipoprotein FO, fish oil ERA, eicosapentaenoic acid DHA, docosa-hexaenoic acid GLA, y-linolenic acid EE, ethyl ester TBARS, thiobarbituric acid-reactive substances. 

Froyland, L., Vaagenes, H., Asiedu, D., Garras, A., Lie, 0. Beige, R.K. (1996). Lipidk 31 169-178. Chronic administration of eicosapentaenoic acid and docosahexaenoic acid as ethyl esters reduced plasma cholesterol and changed fatty acid composition in rat blood and organs. 

Willumsen, N.,Vaagenes, H., Asiedu, D., Lie, 0., Rustan, A.C. Berge, R.K. 1996. Lipids, 31, 579-592. Eicosapentaenoic acid but not docosahexaenoic acid (both as ethyl esters) increases mitochondrial fatty acid oxidation and upregulates 2,4-dienoyl-CoA reductase gene expression. A potential mechanism for the hypolipidemic action of fish oil in rats. 

As temperature and pressure affect the solubility, these effects can also be varied to optimise the difference in solubility. Liang and Yeh [50] studied the separation of ethyl palmitate, ethyl oleate, eicosapentaenoic acid (EPA) ethyl ester and docosahexaenoic acid (DHA) ethyl ester. They considered the phase behaviour and used the determined coefficients for the Chrastil equation to estimate the separation efficiency that can be attained. In general better separation efficiencies were achieved at higher temperatures and lower pressures. They verified their qualitative prediction through extraction of esterified fish oil and found the results correlated well. 

EPA. See Propylene glycol ethyl ether acetate Eicosapentaenoic acid Epihydrin alcohol. See Glycidol Epoxides, polymers, epoxy resins. See Epoxy resin Epoxidized butyl esters of linseed oil fatty acids. See Epoxidized linseed oil, butyl ester... 

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