Skip to main content
SpringerLink
Log in

Products of unsaturated fatty acid oxidation catalyzed by hematin compounds

  • Technical
  • Published:
Journal of the American Oil Chemists’ Society

Summary

A study has been made of the initial and secondary products resulting from the hematin catalyzed decomposition of hydroperoxides. The initial product was found to be the alkoxy free-radical produced by the homolytic cleavage of the O-OH bond of the hydroperoxide. The system was arranged so that the alkoxy radicals reacted with a hydrogen donor as they were formed to produce the corresponding alcohol. The alcohol was then identified by standard physical and chemical procedures.

The secondary products resulting from the hematin catalyzed decomposition of linoleate hydroperoxide in the absence of oxygen were found to be composed principally of oxirane, hydroxyl, and carbonyl compounds. Cleavage of the carbon chain, loss of conjugated double bonnds, and polymerization also took place. Reactions to account for these products were proposed, along with a general mechanism of hematin catalysis.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. George, P., in “Advances in Catalysis”, vol. IV, p. 367, Academic Press, New York (1952).

    Google Scholar 

  2. Henick, A. S., Benca, M. F., and Mitchell, J. H. Jr., J. Am. Oil Chemists' Soc.,31, 88 (1954).

    Article  CAS  Google Scholar 

  3. Hock, H., and Lang, S., Ber.,77, 257 (1944).

    Google Scholar 

  4. Holman, R. T., and Greenberg, S. I., Arch. Biochem. and Biophys.,49, 49 (1954).

    Article  CAS  Google Scholar 

  5. Kharasch, M. S., Fono, A., and Nudenberg, W., J. Org. Chem.,15, 763 (1950).

    Article  CAS  Google Scholar 

  6. Knight, H. B., and Swern, Daniel, J. Am. Oil Chemists' Soc.,26, 366 (1949).

    CAS  Google Scholar 

  7. Lundberg, W. O., and Chipault, J. R., J. Am. Chem. Soc.,69, 833 (1947).

    Article  CAS  Google Scholar 

  8. Maier, V. P., and Tappel, A. L., J. Am. Oil Chemists' Soc.,36, 8–12 (1959).

    Article  CAS  Google Scholar 

  9. O'Connor, R. T., J. Am. Oil Chemists' Soc.,31, 1 (1956).

    Google Scholar 

  10. Ogg, C. L., Porter, W. L., and Willits, C. O., Ind. Eng. Chem.,17, 394 (1945).

    Article  CAS  Google Scholar 

  11. Paschke, R. F., Jackson, J. E., and Wheeler, D. H., Ind. Eng. Chem.,44, 1113, (1953).

    Article  Google Scholar 

  12. Shreve, O. D., Heether, W. R., Knight, H. B., and Swern, Daniel, Anal. Chem.,22, 1261 (1950).

    Article  CAS  Google Scholar 

  13. Swern, Daniel, Findley, T. W., Billen, G. W., and Scanlan, J. T., Anal. Chem.,19, 414 (1947).

    Article  CAS  Google Scholar 

  14. Tappel, A. L., Boyer, P. D., and Lundberg, W. O., J. Biol. Chem.,199, 267 (1952).

    PubMed  CAS  Google Scholar 

  15. Tappel, A. L., Arch. Biochem. and Biophys.,44, 387 (1953).

    Article  Google Scholar 

  16. Tappel, A. L., J. Biol. Chem.,217, 721 (1955).

    PubMed  CAS  Google Scholar 

Download references

Author information

Author notes

  1. Vincent P. Maier (General Foods Fellow 1955–57)

    Present address: U.S.D.A. Fruit and Vegetable Laboratory, Pasadena, Calif.

Authors and Affiliations

  1. Department of Food Technology, University of California, Davis, California

    Vincent P. Maier (General Foods Fellow 1955–57) & A. L. Tappel

Authors
  1. Vincent P. Maier
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. L. Tappel
    View author publications

    You can also search for this author in PubMed Google Scholar

About this article

Cite this article

Maier, V.P., Tappel, A.L. Products of unsaturated fatty acid oxidation catalyzed by hematin compounds. J Am Oil Chem Soc 36, 12–15 (1959). https://doi.org/10.1007/BF02540258

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02540258

Keywords

Search

Navigation