Lipids

, Volume 1, Issue 4, pp 268–273 | Cite as

Keto fatty acids formCuspidaria pterocarpa seed oil

  • C. R. SmithJr.
Article

Abstract

The seed oil ofCuspidaria pterocarpa contains three keto fatty acids with unusually long carbon chains: 15-oxo-cis-18-tetracosenoic (5.4%), 17-oxo-cis-20-hexacosenoic (13.4%), and 19-oxo-cis-22-octacosenoic (3.3%) acids. These acids were isolated by countercurrent distribution of the corresponding methyl esters. Their structures were established by oxidative degradation, by reduction to known compounds, and by nuclear magnetic resonance and infrared spectra.

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References

  1. 1.
    Hilditch, T. P., and P. N. Williams, “Chemical Constitution of Natural Fats,” 4th ed., John Wiley, New York, 1964, p 635.Google Scholar
  2. 2.
    Binder, R. G., T. H. Applewhite, M. J. Diamond and L. A. Goldblatt, JAOCS41, 108–111 (1964).Google Scholar
  3. 3.
    Smith, C. R., and R. W. Miller, Chem. Ind. (London), 1910 (1965).Google Scholar
  4. 4.
    Miwa, T. K., K. L. Mikolajczak, F. R. Earle and I. A. Wolff, Anal. Chem.32, 1739–1742 (1960).CrossRefGoogle Scholar
  5. 5.
    Scholfield, C. R., J. Nowakowska and H. J. Dutton, JAOCS37, 27–30 (1960).Google Scholar
  6. 6.
    Meakins, G. D., and R. Swindells, J. Chem. Soc. 1044–1047 (1959).Google Scholar
  7. 7.
    Francis, F., and S. H. Piper, J. Am. Chem. Soc.61, 577–581 (1939).CrossRefGoogle Scholar
  8. 8.
    von Rudloff, E., Can. J. Chem.34, 1413–1418 (1956).CrossRefGoogle Scholar
  9. 9.
    Hopkins, C. Y., in “Progress in the Chemistry of Fats and Other Lipids”, R. T. Holman, ed., Vol. 8, Part 2, p 239.Google Scholar
  10. 10.
    Wilson, T. L., C. R. Smith and I. A. Wolff, JAOCS38, 696–699 (1961).Google Scholar
  11. 11.
    Smith, C. R., T. L. Wilson, R. B. Bates and C. R. Scholfield, J. Org. Chem.27, 3112–3117 (1962).Google Scholar
  12. 12.
    Bagby, M. O., C. R. Smith and I. A. Wolff, Ibid.30, 4227–4229 (1965).Google Scholar
  13. 13.
    von Rudloff, E., Can. J. Chem.43, 1784–1791 (1965).CrossRefGoogle Scholar
  14. 14.
    Yamada, M., and P. K. Stumpf, Biochem. Biophys. Res. Commun.14, 165–171 (1964).PubMedCrossRefGoogle Scholar
  15. 15.
    James, A. T., H. C. Hadaway and J. P. W. Webb, Biochem. J.95, 448–452 (1965).PubMedGoogle Scholar
  16. 16.
    Chisholm, M. J., and C. Y. Hopkins, Can. J. Chem.43, 2566–2570 (1965), and references cited therein.CrossRefGoogle Scholar
  17. 17.
    Chisholm, M. J., and C. Y. Hopkins, JAOCS42, 49–50 (1965).Google Scholar

Copyright information

© American Oil Chemists’ Society 1966

Authors and Affiliations

  • C. R. SmithJr.
    • 1
  1. 1.Northern Regional Research LaboratoryPeoria

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