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.
KeywordsNuclear Magnetic Resonance Spectrum Keto Acid Countercurrent Distribution Chromium Trioxide Hydriodic Acid
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- 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.Binder, R. G., T. H. Applewhite, M. J. Diamond and L. A. Goldblatt, JAOCS41, 108–111 (1964).Google Scholar
- 3.Smith, C. R., and R. W. Miller, Chem. Ind. (London), 1910 (1965).Google Scholar
- 5.Scholfield, C. R., J. Nowakowska and H. J. Dutton, JAOCS37, 27–30 (1960).Google Scholar
- 6.Meakins, G. D., and R. Swindells, J. Chem. Soc. 1044–1047 (1959).Google Scholar
- 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.Wilson, T. L., C. R. Smith and I. A. Wolff, JAOCS38, 696–699 (1961).Google Scholar
- 11.Smith, C. R., T. L. Wilson, R. B. Bates and C. R. Scholfield, J. Org. Chem.27, 3112–3117 (1962).Google Scholar
- 12.Bagby, M. O., C. R. Smith and I. A. Wolff, Ibid.30, 4227–4229 (1965).Google Scholar
- 17.Chisholm, M. J., and C. Y. Hopkins, JAOCS42, 49–50 (1965).Google Scholar