Eicosapentaenoic acid preparation

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. 

Table 3. M- and C-NMR data for the eicosapentaenoic acid derivatives (E-1 and E-2) isolated from alkali-treated EPA prepared by treatment with 70 i 5% humidity at 40 2 C for 6 months according to the methods of ICH stability testing.

LTBj (135) has been prepared biosynthetically from eicosapentaenoic acid... 

Breivik, H, Haraldsson, GG and Kristinsson, B (1997) Preparation of highly purified concentrates of eicosapentaenoic acid and docosahexaenoic acid. J. Am. Oil Chem. Soc., lA, 1425-1429. 

Tokiwa, S., Kanazawa, A., and Teshima, S. (1981) Preparation of Eicosapentaenoic and Docosahexaenoic Acids by Reversed Phase High Performance Liquid Chromatography, Bull. Jpn. Soc. Sci. Fish. 47,675-6n. 

Production of TAG enriched with polyunsaturated fatty acids (PUFA) via lipase catalysis in codliver oil has also been described (Haraldsson et ah, 1989). Preparation of y-linolenic acid enriched TAG via rapeseed lipases (Syed Rahmatullah et aL, 1994 Jachmanian and Mukerjee, 1996) and microbial lipases (Akoh et aL, 1995, 1996) has also been reported. Incorporation of eicosapentaenoic and docosahexaenoic acids into peanut oil via transesterification catalysed by microbial lipases has been reported by Sridhar and Lakshminarayana (1992). According to Wada and Koizumi (1986) and Kimoto et aL (1994) interesterification of fish oils to form TAG containing PUFA in the 2-position rather than the 1,3-positions increases the oxidative stability of the modified oil as compared to its original counterpart. 

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