Lipids

, Volume 12, Issue 1, pp 99–104

Autoxidation of methyl linoleate. Separation and analysis of isomeric mixtures of methyl linoleate hydroperoxides and methyl hydroxylinoleates

  • Henry W. -S. Chan
  • Gordon Levett
Regular Papers

Abstract

The mixture of conjugated diene hydroperoxide isomers obtained from autoxidation of methyl linoleate was separated by high performance liquid chromatography (HPLC). Four major isomers were obtained from adsorption chromatography and identified as the 9 and 13 positional isomers having thetrans-trans andcis-trans configurations. The latter geometrical isomers have thetrans double bond adjacent to the hydroperoxide group. The hydroxy compounds (methyl hydroxylinoleates) obtained from the hydroperoxides by NaBH4 reduction were similarly separated but with improved resolution. This is the first instance of the complete separation of these compounds and provides a rapid method for their analysis. Unlike adsorption chromatography, reversed-phase chromatography separates the mixtures only according to the geometrical isomerism of the double bonds and not according to the position of the hydroxy or hydroperoxide function.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Chan, H.W.-S., and F.A.A. Prescott Biochim. Biophys. Acta 380:141 (1975).PubMedGoogle Scholar
  2. 2.
    Gardner, H.W., Lipids 10:248 (1975).Google Scholar
  3. 3.
    Funk, M.O., R. Isaac, and N.A. Porter, Lipids 11:113 (1976).PubMedGoogle Scholar
  4. 4.
    Hamberg, M., Anal. Biochem. 43:515 (1971).PubMedCrossRefGoogle Scholar
  5. 5.
    Bergström, S., Arkiv. Kemi. Mineral Geol. 21A:1 (1945).Google Scholar
  6. 6.
    Privett, O.S., W.O. Lundberg, N.A. Khan, W.E. Tolberg, and D.H. Wheeler, JAOCS 30:61 (1953).Google Scholar
  7. 7.
    Cannon, J.A., K.T. Zilch, S.C. Burket, and H.J. Dutton, Ibid. 29:447 (1952).Google Scholar
  8. 8.
    Sephton, H.H., and D.A. Sutton, Ibid. 33:263 (1956).Google Scholar
  9. 9.
    Banks, A., S. Fazakerley, J.N. Keay, and J.G.M. Smith, Nature 184:816 (1959).CrossRefGoogle Scholar
  10. 10.
    Chan, H.W.-S., C.T. Costaras, F.A.A. Prescott, and P.A.T. Swoboda, Biochim. Biophys. Acta 398:347 (1975).PubMedGoogle Scholar
  11. 11.
    Scott, C.D., and N.E. Lee J. Chromatogr. 42:263 (1969).CrossRefGoogle Scholar
  12. 12.
    Hornstein, I., and R.F. Crowe, Anal. Chem. 34:1037 (1962).CrossRefGoogle Scholar
  13. 13.
    Zilch, K.T., H.J. Dutton, and J.C. Cowan, JAOCS 29:244 (1952).Google Scholar
  14. 14.
    Chan, H.W.-S., F.A.A. Prescott, and P.A.T. Swoboda, Ibid. 53:572 (1976).Google Scholar
  15. 15.
    Tallent, W.H., J. Harris, and I.A. Wolff, Tet. Letters, 36:4329 (1966).CrossRefGoogle Scholar
  16. 16.
    Gardner, H.W. and D. Weisleder, Lipids 7:191 (1972).CrossRefGoogle Scholar
  17. 17.
    Gunstone, F.D. and W.C. Russell, J. Chem. Soc. 3782 (1955).Google Scholar
  18. 18.
    Ahlers, N.H.E., R.A. Brett, and N.G. McTaggart, J. Appl. Chem. 3:433 (1953).CrossRefGoogle Scholar
  19. 19.
    Jackson, J.E., R.F. Paschke, W. Tolberg, H.M. Boyd, and D.H. Wheeler, JAOCS 29:229 (1952).Google Scholar
  20. 20.
    Lundberg, W.O., J.R. Chipault, and M.J. Hendrickson, Ibid. 26:109 (1949).Google Scholar
  21. 21.
    British Standard 684: Methods of Analysis of Oils and Fats, 1958, p. 84.Google Scholar
  22. 22.
    Morris, L.J., R.T. Holman, and K. Fontell, JAOCS 37:323 (1960).Google Scholar

Copyright information

© American Oil Chemists’ Society 1977

Authors and Affiliations

  • Henry W. -S. Chan
    • 1
  • Gordon Levett
    • 1
  1. 1.Agricultural Research CouncilFood Research InstituteColney LaneUK

Personalised recommendations