Thermal Decomposition of Methyl Linoleate and Methyl Linolenate Hydroperoxides Analyzed by Capillary Gas Chromatography

  • Edwin N. Frankel
  • Edward Selke
  • William E. Neff
Part of the Basic Life Sciences book series (BLSC, volume 49)


Much work has been reported on the volatile oxidation products of unsaturated fats because they cause rancidity in foods and cellular damage in the body. Decomposition of fatty ester hydroperoxides creates a wide range of carbonyl compounds, hydrocarbons, furans, and other materials that contribute to flavor deterioration of foods and that are implicated in biological oxidation. Interaction of some of these degradation products with DNA, proteins, and enzymes may be involved in cell-damaging reactions.2–4 Although fatty acid hydroperoxides are the recognized precursors of volatile secondary products, relatively little information is available on the mechanism of their decorposition. New information on the volatile lipid oxidation products is needed to better evaluate precursors of oxidative deterioration in lipid-containing foods and to understand the biological significance of lipid peroxidation.


Methyl Linoleate Fatty Acid Hydroperoxide Linolenate Hydroperoxide Dynamic Headspace Volatile Decomposition Product 
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  1. 1.
    E.N. Frankel, Volatile lipid oxidation products, Prog. Lipid Res. 22:1 (1982).CrossRefGoogle Scholar
  2. 2.
    W.A. Pryor, The formation of free radicals and the consequences of their reactions in vivo, Photochem. Photobiol. 28:787 (1978).PubMedCrossRefGoogle Scholar
  3. 3.
    A.L. Tappel, Measurement of and protection from invivo lipid peroxidation, in: “Free Radicals in Biology,” Vol. IV, W.A. Pryor, ed., Academic Press, New York (1980).Google Scholar
  4. 4.
    E.N. Frankel, Biological significance of secondary lipid oxidation products, Free Rad. Res. Commun. 3:213 (1987).CrossRefGoogle Scholar
  5. 5.
    E.N. Frankel, W.E. Neff, E. Selke, E., and D.D. Brooks, Thermal and metal-catalyzed decomposition of methyl linolenate hydroperoxides, Lipids 22:322 (1987).CrossRefGoogle Scholar
  6. 6.
    E. Selke and E.N. Frankel, Dynamic headspace capillary gas Chromatographic analysis of soybean volatiles, J. Am. Oil Cham. Soc. 64:749 (1987).CrossRefGoogle Scholar
  7. 7.
    E.N. Frankel, W.E. Neff, and E. Selke, Analysis of autoxidized fats by gas chroamatography-mass spectrometry: VII. Volatile thermal decomposition products of pure hydroperoxides from autoxidized and photosensitized oxidized methyl oleate, linoleate, and linolenate, Lipids 16:279 (1981).CrossRefGoogle Scholar
  8. 8.
    W.E. Neff, E.N. Frankel, and D. Weisleder, High-pressure liquid dhromatography of autoxidized lipids: II. Hydroperoxy-cyclic peroxides and other secondary products from methyl linolenate, Lipids 16:439 (1981).CrossRefGoogle Scholar
  9. 9.
    E. Selke, W.K. Rohwedder, and H.J. Dutton, Volatile components from triolein heated in air, J. Am. Oil Chem. Soc., 54:62 (1977).CrossRefGoogle Scholar
  10. 10.
    E.N. Frankel, W.E. Neff, and E. Selke, Analysis of autoxidized fats by gas chroamatography-mass spectrometry. IX. Homolytic vs. heterolytic cleavage of primary and secondary oxidation products, Lipids 19:790 (1984).CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1988

Authors and Affiliations

  • Edwin N. Frankel
    • 1
  • Edward Selke
    • 1
  • William E. Neff
    • 1
  1. 1.U. S. Department of AgricultureNorthern Regional Research CenterPeoriaUSA

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