Skip to main content

Autoxidation and Enzymatic Oxidation of Unsaturated Lipids

  • Chapter
Anticarcinogenesis and Radiation Protection
  • 118 Accesses

Abstract

Oxygen may act not only as an oxidant to initiate free radical reactions, but it can also act as a substrate for the propagation of these reactions. The spontaneous reaction of molecular oxygen with radicals is commonly referred to as autoxidation. Autoxidation is responsible for the deterioration of many manufactured plastics and rubber goods. Rancidity and spoilage of foodstuffs is a direct result of the autoxidation of fats, which are most susceptible to air oxidation and present, to a large extent, in virtually all foods.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. A. P. Autor, Oxygen toxicity in eukaryotes. In: The Biology and Chemistry of Active Oxygen (J. V. Bannister, W. H. Bannister, Eds), pp. 139–145. Elsevier, New York, 1984.

    Google Scholar 

  2. K. U. Ingold, Peroxy radicals. Acc. Chem. Res., 2, 1–9 (1969).

    Article  CAS  Google Scholar 

  3. J. A. Howard, Free radicals (J. K. Kochi, Ed.), pp. 3–62. Wiley, New York, 1973.

    Google Scholar 

  4. G. A. Russell, Deuterium-isotope effects in the autoxidation of aralkyl hydrocarbons. Mechanism of the interaction of peroxy radicals. J. Am. Chem. Soc., 22, 3871–3877 (1957).

    Article  Google Scholar 

  5. J. A. Howard, K. U. Ingold, and M. Symonds, Absolute rate constants for hydrocarbon oxidation. VDI. The reactions of cumylperoxy radicals. Can J. Chem., 45. 1017–1022 (1968).

    Article  Google Scholar 

  6. F. Haslbeck, and W. Grosch, HPLC analysis of all positional isomers of the monohydroperoxides formed by soybean lipoxygenase during oxidation of linoleic acid. J. Food Biochem., 9, 1–3 (1985)

    Article  CAS  Google Scholar 

  7. H. W. S. Chan, V. K. Newby, and G. Levett, Metal ion-catalyzed oxidation of linoleic acid. Lipoxygenase-like regioselectivity of oxygenation. J. Chem. Soc., Chem, Commun, 82–83 (1978).

    Google Scholar 

  8. N. A. Porter, B. A. Weber, H. Weenen, and J. A. Khan, The autoxidation of polyunsaturated lipids: factors controlling the stereochemistry of product hydroperoxides. J. Am. Chem. Soc., 102. 5597–5601 (1980).

    Article  CAS  Google Scholar 

  9. Yamamoto, S. Haga, E. Niki, and Y. Kamiya, Oxidation of lipids. V. Oxidation of methyl linoleate in aqueous dispersion. Bull. Chem. Soc., Jpn. 57, 1260–1264 (1984).

    Article  Google Scholar 

  10. Y. Yamamoto, E. Niki, and Y. Kamiya, Oxidation of lipids. HI. Oxidation of methyl linoleate in solution. Lipids. 12, 870–877 (1982).

    Article  Google Scholar 

  11. N. A. Porter, Mechanisms for the autoxidation of polyunsaturated lipids. Acc. Chem. Res., 19. 262–268 (1986).

    Article  CAS  Google Scholar 

  12. E. Bascetta, F. D. Gunstone, and J. C. Walton, An electron spin resonance study of fatty acids and esters. Part 1. Hydrogen abstraction from olefinic and acetylenic long-chain esters. J, Chem. Soc., Perkin Trans. II, 603–613 (1983).

    Google Scholar 

  13. N. A. Porter, L. S. Lehman, B. A. Weber, and K. J. Smith, A unified mechanism for polyunsaturated fatty acid autoxidation: competition of peroxy radical hydrogen atom abstract, p-scission and cyclization. J. Am. Chem. Soc., 103. 6447–6455 (1981).

    Article  CAS  Google Scholar 

  14. M. R. Egmond, J. F. G. Vliegenthart, and J. Boldingh, Stereospecifity of the hydrogen abstraction at carbon atom n-8 in the oxygenation of linoleic acid by lipoxygenases from com germs and soya beans. Biochem. Biophys. Res. Commun., 48, 1055–1060 (1972).

    Article  PubMed  CAS  Google Scholar 

  15. J. K. Beckman, J. C. Gray, A. R. Brash, J. N. Lukens, and J. A. Gates, Differential effects of lipoxygenase products on FMLP and LTB4 evoked neutrophil aggregation. Lipids, 20, 357–360 (1985).

    Article  PubMed  CAS  Google Scholar 

  16. B. Samuelsson, Leukotrienes: mediators of immediate hypersensitivity reactions and inflammation. Science. 220, 568–575 (1983).

    Article  PubMed  CAS  Google Scholar 

  17. J. E. Pike, and D. R. Morton, Jr., Eds., Advances in prostaglandin, thromboxane, and leukotriene research. Vol. 14, pp. 156–157. Raven Press, New York, 1985.

    Google Scholar 

  18. N. A. Nelson, R. C. Kelly, and R. A. Johnson, Prostaglandins and the arachidonic acid cascade. Chem. Eng. News, 60 (33) 30–44 (1982).

    Article  CAS  Google Scholar 

  19. E. J. Corey, J. Simoji, and C. Shih, Synthesis of prostaglandins via a 2,3-dioxabicyclo[2.2.1]heptane (endoperoxide) intermediate. Stereochemical divergence of enzymatic and biomimetic chemical cyclization reactions. J. Am. Chem. Soc., 106, 6425–6427 (1984).

    Article  CAS  Google Scholar 

  20. N. A. Porter, P. J. Zuraw, and J. A. Sullivan, Peroxymercuration-dermercuration of lipid hydroperoxides. Tetrahedron Lett., 21, 807–810 (1984).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1987 Plenum Press, New York

About this chapter

Cite this chapter

Porter, N.A. (1987). Autoxidation and Enzymatic Oxidation of Unsaturated Lipids. In: Cerutti, P.A., Nygaard, O.F., Simic, M.G. (eds) Anticarcinogenesis and Radiation Protection. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-6462-1_2

Download citation

  • DOI: https://doi.org/10.1007/978-1-4615-6462-1_2

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4615-6464-5

  • Online ISBN: 978-1-4615-6462-1

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics