Abstract
The extent of oxidation of ethyl esters of eicosapentaenoic (EPA) and docosahexaenoic acids (DHA) was compared quantitatively with that of ethyl linoleate (Lo) and ethyl linolenate (Ln) by oxygen uptake and formation of conjugated diene, hydroperoxide and secondary oxidation products. EPA and DHA esters were oxidized rapidly even at 5 C in the dark after an induction period of 3–4 days, while the induction periods of Ln and Lo esters were 20 days and more than 60 days, respectively. Oxygen uptake of EPA and DHA esters after the induction period was 5.2 and 8.5 times faster than that of ethyl Ln, respectively. Hydroperoxides of EPA and DHA esters are much less stable than those of ethyl Lo. The peroxide value is not necessarily a good indication of oxidation in these polyenoic acids because a considerable amount of secondary products is formed at the early stage of oxidation. Polymers were found to be major secondary products in these polyenoic esters.
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References
Dyerberg, J., and H.O. Bang,Lancet 2:433 (1979).
Lossonczy, T.O.,Am. J. Clin. Nutr. 31:1340 (1978).
Kinsella, J.E.,Food Technology 40 (2):89 (1986).
Lands, W.E.M., inFish and Human Health, edited by W.E.M. Lands, Academic Press, Orlando, 1986, p. 129.
Kaneda, T., H. Sakurai and S. Ishii,J. Biochem. (Japan) 42:561 (1955).
Andrews, J.S., W.H. Griffith, J.F. Mead and R.A. Stein,J. Nutr. 70:199 (1960).
Frankel, E.N.,Prog. Lipid Res. 19:1 (1980).
Frankel, E.N., Ibid.:197 (1985).
Yamamoto, Y., N. Saeki, S. Haga, E. Niki and Y. Kamiya,Bull. Chem. Soc. Jpn. 57:3177 (1984).
Yamauchi, R., T. Yamada, K. Kato and Y. Ueno,Agric. Biol. Chem. 47:2897 (1983).
Yamauchi, R., T. Yamada, K. Kato and Y. Ueno, Ibid.:2077 (1985).
Vanrollins, M., and R.C. Murphy,J. Lipid Research 25:507 (1984).
Higuchi, T., M. Hatano and K. Zama,Bull. Fac. Fish. Hokkaido Univ. 28:212 (1977).
Keppler, J.G., S. Sparreboom, J.B.A. Stroink and J.D. von Mikusch,J. Am. Oil Chem. Soc. 36:308 (1959).
Mattews, N.L., W.R. Borde and J.B. Brown, Ibid.:1064, (1941).
Chan, H.W.-S., Ibid.:100 (1977).
Official Methods and Recommended Practices of the American Oil Chemists’ Society, AOCS, Champaign, IL, Tentative Method Cd 8-53 (1960).
Miyashita, K., K. Fujimoto and T. Kaneda,Agric. Biol. Chem. 46:751 (1982).
Holman, R.T., and O.C. Elmer,J. Am. Oil Chem. Soc. 24:127 (1947).
Lea, C.H.,J. Sci. Food Agric. 3:586 (1952).
Neff, W.E., E.N. Frankel and D. Weisleder,Lipids 16:439 (1981).
Coxon, D.T., K.R. Price and H.W.-S. Chan,Chem. Phys. Lipids 28:365 (1981).
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Cho, SY., Miyashita, K., Miyazawa, T. et al. Autoxidation of ethyl eicosapentaenoate and docosahexaenoate. J Am Oil Chem Soc 64, 876–879 (1987). https://doi.org/10.1007/BF02641498
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DOI: https://doi.org/10.1007/BF02641498