Abstract
Fatty acid analysis of autoxidized cod-liver oil with a peroxide value of 192 showed significant degradation of only eicosapentaenoic, docosapentaenoic, and docosahexaenoic acids of the linolenate family. Purified, mildly autoxidized cod-liver oil with a peroxide value of 28, methyl eicosapentaenoate, and methyl docosahexaenoate produced carbonyl patterns in agreement with the accepted mechanism for olefinic autoxidation. In all cases the major products were propanal andn-pent-2-enal as predicted, andn-hex-2-enal andn-hept-2-enal as reported in the literature for linolenate. In addition, the same cod-liver oil, which had been heated to 188C in vacuum for 1 hr to decompose completely the hydroperoxides before carbonyl analysis, showed the presence ofn-hepta-2,4-dienal as predicted.
Similar content being viewed by others
References
Derrick, N. M., and L. A. Wishner, Lipids2, 133–136 (1967).
Schwartz, D. P., H. S. Haller and M. Keeney, Anal. Chem.35, 2191–2194 (1963).
Schwartz, D. P., and O. W. Parks, Ibid.33, 1396–1398 (1961).
Schwartz, D. P., O. W. Parks and M. Keeney, Ibid.34, 669–671 (1962).
Corbin, E. A., D. P. Schwartz and M. Keeney, J. Chromatog.3, 322–329 (1960).
Farmer, E. H, G. F. Bloomfield, A. Sundralingam and D. A. Sutton, Trans. Faraday Soc.38, 348–356 (1942).
Bell, E. R., H. J. Raley, F. F. Rust, F. H. Seubold and W. E. Vaughan, Disc. Faraday Soc.10, 242–249 (1951).
Keeney, M., “Symposium on Foods: Lipids and Their Oxidation” Avi Publishing Company, Westport, Conn., 1962, p. 79.
Frankel, E. N., C. D. Evans, D. G. McConnell, E. Selke and H. J. Dutton, J. Org. Chem.26, 4663–4669 (1961).
Frankel, E. N., “Symposium on Foods: Lipids and Their Oxidation,” Avi Publishing Company, Westport, Conn., 1962, p. 51.
Kawahara, F. K., H. J. Dutton and J. C. Cowan, JAOCS29, 633–636 (1952).
Gaddis, A. M., R. Ellis and G. T. Currie,Ibid.38, 371–375 (1961).
Official Methods of AOCS, Cd 8-53 (1960).
Lea, C. H., and A. Hobson-Frohock, J. Sci. Agr.16, 18–27 (1965).
Official Methods of AOCS, Ce 2-66 (1966).
Lillard, D. A., and E. A. Day, JAOCS41, 549–552 (1964).
Fukuzumi, K., T. Miyakawa and H. Morohira, Ibid.42, 717–720 (1965).
Barclay, J. A., E. J. Hamley and K. White, Biochem. J.88, 14 (1963).
Author information
Authors and Affiliations
About this article
Cite this article
Fisher, M.P., Wishner, L.A. Autoxidation of tissue lipids. II. Monocarbonyl compounds formed by the autoxidation of methyl eicosapentaenoate, methyl docosahexaenoate, and cod-liver oil. Lipids 3, 88–90 (1968). https://doi.org/10.1007/BF02530975
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02530975