Abstract
Much work has been reported on the volatile oxidative products of fats and their impact on flavor deterioration, cellular damage and the decrease in safety of fatcontaining foods. However, relatively little information is available on the mechanism of hydroperoxide decomposition. Pure methyl linolenate hydroperoxides were decomposed thermally at 150 C and catalytically with ferric chloride-ascorbic acid at room temperature. The volatile decomposition products were collected on porous polymer (Tenax) traps and concentrated by gel permeation chromatography. The total volatile products showed significant differences in composition by capillary gas chromatography-mass spectrometry (GC-MS). Thermal decomposition produced much more methyl octanoate (60.1%) and less 2,4-heptadienal (0.5%) than catalytic decomposition (13.2 and 60.8%, respectively). The volatiles from the ferric chloride-ascorbic acid system also contained unique products tentatively identified by GC-MS as isomers of chloromethyl butene. These results may have important implications in evaluating precursors of flavor deterioration in vegetable oils containing linolenate and in understanding better the biological significance of lipid peroxidation.
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References
Warner, K., Frankel, E.N., Snyder, J.M., and Porter, W.L. (1986)J. Food Sci. 51, 703–708.
Stevenson, S.G., Vaisey-Genser, M., and Eskin, N.A.M. (1984)J. Am. Oil Chem. Soc. 61, 1102–1108.
Frankel, E.N., Warner, K., and Moulton, K.J. Sr. (1985)J. Am. Oil Chem. Soc. 62, 1354–1358.
Sattar, A., de Man, J.M., and Alexander, J.C. (1976)Can. Inst. Food Sci. Technol. J. 9, 108–113.
Simic, M.G., and Karel, M., eds. (1980)Autoxidation in Foods and Biological Systems, Plenum Press, New York.
Frankel, E.N. (1980)Prog. Lipid Res. 19, 1–22.
Pearson, A.M., Gray, J.I., Wolzak, A.M., and Horenstein, N.A. (1983)Food Technol. 37(7), 121–127.
Min, D.B., and Smouse, T.H., eds. (1985)Flavor Chemistry of Fats and Oils, American Oil Chemists' Society, Champaign, IL.
Pryor, W.A. (1978)Photochem. Photobiol. 28, 787–801.
Tappel, A.L. (1980) in Free Radicals in Biology (Pryor, W.A., ed.) Vol. IV, pp. 2–47, Academic Press, New York.
Grosch, W. (1976)Z. Lebensm. Unters.-Forsch. 160, 371–375.
Grosch, W. (1977)Z. Lebensm. Unters.-Forsch. 163, 4–7.
Frankel, E.N., Neff, W.E., and Selke, E. (1981)Lipids 16, 279–285.
Frankel, E.N. (1983)Prog. Lipid Res. 22, 1–33.
Frankel, E.N., Neff, W.E., and Selke, E. (1983)Lipids 18, 353–357.
Frankel, E.N. (1985)Prog. Lipid Res. 23, 197–221.
Fujimoto, K., Neff, W.E., and Frankel, E.N. (1984)Biochem. Biophys. Acta 795, 100–107.
MacGregor, J.T., Wilson, R.E., Neff, W.E., and Frankel, E.N. (1985)Food Chem. Toxicology 23, 1041–1047.
Frankel, E.N., Neff, W.E., and Selke, E. (1984)Lipids 19, 790–800.
Neff, W.E., Frankel, E.N., and Weisleder, D. (1981)Lipids 16, 439–448.
Neff, W.E., and Frankel, E.N. (1980)Lipids 15, 587–590.
Selke, E., Rohwedder, W.K., and Dutton, H.J. (1977)J. Am. Oil Chem. Soc. 54, 62–67.
Forss, D.A. (1972)Prog. Chem Fats & Other Lipids 13, 177–258.
Charalambous, G., ed. (1978)Analysis of Foods and Beverages. Headspace Techniques, Academic Press, New York.
Ioffe, B., and Vitenberg, A.G. (1982)Head-Space Analysis and Related Methods in Gas Chromatography, Wiley & Sons, New York.
Perkins, E.G., Taubold, R., and Hsieh, A. (1973)J. Am. Oil Chem. Soc. 50, 223–225.
Miyashita, K., Hara, N., Fujimoto, K., and Kaneda, T. (1985)Lipids 20, 578–587.
Frankel, E.N., Neff, W.E., and Selke, E. (1986)J. Am. Oil Chem. Soc. 63, 452 (abstract no. 271).
Binder, R.G., Applewhite, T.H., Diamond, M.J., and Goldblatt, L.A. (1964)J. Am. Oil Chem. Soc. 41, 108–111.
Kimoto, W.I., and Gaddis, A.M. (1974) J. Am. Oil Chem. Soc. 51, 307–311.
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Frankel, E.N., Neff, W.E., Selke, E. et al. Thermal and metal-catalyzed decomposition of methyl linolenate hydroperoxides. Lipids 22, 322–327 (1987). https://doi.org/10.1007/BF02534000
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DOI: https://doi.org/10.1007/BF02534000