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Lack of regioselectivity in formation of oxohydroxyoctadecenoic acids from the 9- or 13-hydroperoxide of linoleic acid

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Lipids

Abstract

Either 9-hydroperoxy-trans-10,cis-12-octadecadienoic acid or 13-hydroperoxy-cis-9,trans-11-octadecadienoic acid was treated with the catalyst, cysteine-FeCl3, in the presence of oxygen. Oxohydroxyoctadecenoic acids were among the many products formed as a result of hydroperoxide decomposition. A mixture of 9(13)-oxo-13(9)-hydroxy-trans-11(10)-octadecenoic acids (δ-ketols) was produced from either isomeric hydroperoxide. The formation of isomeric δ-ketols from 9-hydroxy-trans-12,13-epoxy-trans-10-octadecenoic acid (epoxyol), a known product of 13-hydroperoxy-cis-9,trans-11-octadecadienoic acid decomposition, implies that the epoxyol is an intermediate. The mechanism was elucidated by the facile conversion of the epoxyol (methyl ester_ to methyl 9(13)-oxo-13(9)-hydroxy-trans-11(10)-octadecenoates with a Lewis acid, BF3-etherate.

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References

  1. Gardner, H.W., R. Kleiman, and D. Weisleder, Lipids 9:696 (1974).

    Article  CAS  Google Scholar 

  2. Sessa, D.J., H.W. Gardner, R. Kleiman, and D. Weisleder, Lipids 12:613 (1977).

    Article  PubMed  CAS  Google Scholar 

  3. Gardner, H.W., R. Kleiman, and D. Weisleder, Lipids 13:246 (1978).

    CAS  Google Scholar 

  4. Gardner, H.W., K. Eskins, G.W. Grams, and G.E. Inglett, Lipids 324 (1972).

  5. Hamberg, M., and B. Gotthammar, Lipids 8:737 (1973).

    Article  CAS  Google Scholar 

  6. Hamber, M., Lipid 10:87 (1975).

    Article  Google Scholar 

  7. Garssen, G.J., G.A. Veldink, J.F.G. Vliegenthart, and J. Boldingh, Eur. J. Biochem. 62:33 (1976).

    Article  PubMed  CAS  Google Scholar 

  8. Gardner, H.W., and R. Kleiman, Lipids 12:941 (1977).

    Article  CAS  Google Scholar 

  9. Gardner, H.W., Communication at 14th World Congress, International Society for Fat Research, Brighton, U.K., September 17–21, 1978.

  10. Gardner, H.W., Lipids 10:248 (1975).

    Article  CAS  Google Scholar 

  11. Chan, H.W.-S., C.T. Costaras, F.A.A. Prescott, and P.A.T. Swoboda, Biochim. Biophys. Acta 398:347 (1975).

    PubMed  CAS  Google Scholar 

  12. Chan, H.W.-S., G. Levett, and J.A. Matthew, J. Chem. Soc. Chem. Commun. 1978:756.

  13. Daly, J.W., D.M. Jerina, and B. Witkop, Experientia 28:1129 (1972).

    Article  PubMed  CAS  Google Scholar 

  14. Gardner, H.W., Lipids 14:208 (1979).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Northern Regional Research Center, Agricultural Research, Science and Education Administration, U.S. Department of Agriculture, 61604, Peoria, Illinois

    H. W. Gardner & R. Kleiman

Authors
  1. H. W. Gardner
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  2. R. Kleiman
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The mention of firm names or trade products does not imply that they are endorsed or recomended by the U.S. Department of Agriculture over other firms or similar products not mentioned.

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Gardner, H.W., Kleiman, R. Lack of regioselectivity in formation of oxohydroxyoctadecenoic acids from the 9- or 13-hydroperoxide of linoleic acid. Lipids 14, 848–851 (1979). https://doi.org/10.1007/BF02534127

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  • DOI: https://doi.org/10.1007/BF02534127

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