Ethyl docosahexaenoate

Maruyama, K., Shimada, Y., Baba,T., Ooguri,T., Sugihara, A.,Tominaga, Y., and Mori-yama, S. 2000. Purification of ethyl docosahexaenoate through selective alcoholysis with immobilized Rhizomucor miehei lipase. J. Jpn. Oil Chem. Soc., 49, 793-799. 

Shimada, Y., Sugihara, A., Yodono, S., Nagao, T., Maruyama, K., Nakano, H., Komemushi, S., and Tominaga, Y. 1997c. Enrichment of ethyl docosahexaenoate by selective alcoholysis with immobilized Rhizopus delemar lipase./. Ferment. Bioeng., 84,138-143. 

As desirable products have similar molecular weights (ethyl docosahexaenoate is 356, and ethyl eicosapentaenoate is 330), it is clear that this type of fish oil product cleanup is best done at the oil stage to avoid losses at the same time as contaminant removal, which is carried out as described above. However, dimers and/or other polymeric and/or colored materials may be left behind if wiped wall equipment is used in its capacity of a simple and inefficient short-path still for the ethyl esters only. This process will produce a water-white distillate product. Regrettably, it is not an efficient way to separate ethyl-EPA from ethyl-DHA. 

Obtained by digitizing the graph in the original article Synonyms (all Z)-4,7,10,13,16,19-Docosa hexaenoic acid ethyl ester Ethyl docosahexaenoate Source Liong, K. Foster, N. Ting, S. Ind. Eng. Chem.Res. (1992), 31(1), 400-4. 

Docosahexaenoic acid ethyl ester Ethyl docosahexaenoate D-90, D-91... 

FIGURE 1.21 Effect of initial molar ratio of various fatty acid esters to a-CD on the inclusion fraction of fatty acid esters in a-CD. O CAPME, A CPRME, MYRME, <> LINME, V EPAEE, DHAEE. Abbreviations CAPME, -caproic acid methyl ester CPRME, n-caprylic acid methyl ester LINME, linoleic acid methyl ester EPAEE, ethyl eicosapentae-noate DHAEE, ethyl docosahexaenoate. (From Yoshii, H. et ah, Oyo Toshitsu Kagaku, 42, 243, 1995. With permission.)... 

H. Matsuyama, Y. Kitamura, Y. Doi, S. Ohtsuka, Y. Matsuba and T. Okihara, Facilitated transport of ethyl docosahexaenoate through solution-cast perfluorosulfo-nated ionomer membranes, J. Appl. Polym. Sci., 1999, 73, 961-968. 

Ethyl docosahexaenoate-treated foetal rat brain preparations exhibited an almost 70 % decrease in the amount of 5,5 -dimethyl-l.pyrroline-N-oxide-OH adducts compared to those from ethyl oleate-treated animals (Green et al. 2001). The decreased lipid peroxide production, as well as increased production of prostaglandin Ej and nitric oxide by the foetal brain following ethyl docosahexaenoate administration could be mimicked by a synthetic qui-none possessing both hydroxyl radical producing and lipid peroxide propagation inhibiting properties. 

Figure 5. Oxidative stability of ethyl docosahexaenoate in super pure water (open triangle), NaCl solution (open circle),cathodic solution just after electrolysis (solid circle) and cathodic solution after incubation for 7 days (solid triangle). (A) Decrease in unoxidized linoleate. (B) Formation of peroxides.

Lovaza (omega-3-acid ethyl esters) is a prescription form of concentrated fish oil EPA 465 mg and docosahexaenoic acid 375 mg. The daily dose is 4 g/day, which can be taken as four 1-g capsules once daily or two 1-g capsules twice daily. This product lowers triglycerides by 14% to 30% and raises HDL by about 10%. 

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. 

Martinez M., Vazquez E., Garcia-Silva M. T., Manzanares J., Bertran J. M., Castello F., and Mougan I. (2000). Therapeutic effects of docosahexaenoic acid ethyl ester in patients with generalized peroxisomal disorders. Am. J. Clin. Nutr. 71 376S-385S. 

The separation of two fatty ethyl esters (GLA y-linolenic ethyl ester and DHA docosahexaenoic ethyl ester) has been carried out on the pilot plant. 

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

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. 

Beckermann, B., Beneke, M. and Seitz, I. (1990) Comparative bioavailability of eicosapen-taenoic acid and docosahexaenoic acid from triglycerides, free fatty acids and ethyl esters in volunteers. Arzneimittelforschung. 40 700-704. 

Krokan, H.E., Bjerve, K.S. and Mork, E. (1993) The enteral bioavailability of eicosapen-taenoic acid and docosahexaenoic acids is as good from ethyl ester as from glyceryl ester in spite of lower hydrolytic rates by pancreatic lipase in vitro. Biochim. Biophys. Acta. 1168 59-67. 

Martinez, M. and Vazquez, E. (1998) MRI evidence that docosahexaenoic acid ethyl ester improves myelination in generalized peroxisomal disorders. Neurology. 51 26-32. 

Nordoy, A., Barstad, L., Connor, W.E. and Hatcher, L. (1991) Absorption of the n-3 eicosa-pentaenoic and docosahexaenoic acids as ethyl esters and triglycerides by humans. Am. J. Clin. Nutr. 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. 

A by-prodnct in esterification of FAs and glycerol is water. Meanwhile, reaction of FAEEs and glycerol by-produces ethanol (EtOH). Reaction under reduced pressure removes EtOH more easily than water thns, glycerolysis of EAEEs proceeds more efficiently compared with esterification of FAs and glycerol. When glycerolysis of docosahexaenoic acid ethyl ester (DHAEE) was condncted under reduced pressure using Pseudomonas lipase immobilized on calcinm carbonate, the content of partial acylglycerols reached 53 wt% (Rosn et al. 1998). 

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