Abstract
Racemic helenynolic acid has been prepared from crepenynic acid by epoxidation followed by base-catalyzed rearrangement. This may be the pathway by which helenynolic acid is produced inHelichrysum bracteatum seed oil from the crepenynic acid also present. A reinvestigation of the epoxy acids in this oil has shown thatcis-9,10-epoxyoctadec-12-ynoic acid accompanies the coronaric acid previously identified.
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Gunstone, F. D., Chem. Ind. (London) 1966:1551.
Conacher, H. B. S., and F. D. Gunstone, Chem. Phys. Lipids 3:191 (1969).
Powell, R. G., C. R. Smith, Jr. and I. A. Wolff, JAOCS 42:165 (1965).
Powell, R. G., C. R. Smith, Jr., C. A. Glass and I. A. Wolff, J. Org. Chem. 30:610 (1965).
Cymerman Craig, J., S. K. Roy, R. G. Powell and C. R. Smith, Jr., Ibid. 30:4342 (1965).
Metcalfe, L. D., and A. A. Schmitz, Anal. Chem. 33:363 (1961).
Tulloch, A. P., and B. M. Craig, JAOCS 41:222 (1964).
Cope, A. C., and B. D. Tiffany, J. Am. Chem. Soc. 73:4158 (1951).
Gunstone, F. D., J. Chem. Soc. 1954: 1611.
Morris, L. J. Chem. Ind. (London) 1962: 1238.
Gunstone, F. D., D. Kilcast, R. G. Powell and G. M. Taylor, Chem. Commun. 1967:295.
Powell, R. G., C. R. Smith, Jr. and I. A. Wolff, Lipids 2:172 (1967).
Morris, L. J., and M. O. Marshall, Chem. Ind. (London) 1966:1493.
Morris, L. J., R. T. Holman and K. Fontell, JAOCS 37:323 (1960).
Tallent, W. H., J. Harris, I. A. Wolff and R. E. Lundin, Tetrahedron Letters 1966:4329.
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Part XXI, Chem. Phys. Lipids 3:203 (1969).
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Conacher, H.B.S., Gunstone, f.D. Fatty acids: XXII1 partial synthesis of racemic helenynolic acid from crepenynic acid by a possible biosynthetic route and the discovery ofcis-9,10-epoxyoctadec-12-ynoic acid inHelichrysum bracteatum seed oil2 . Lipids 5, 137–141 (1970). https://doi.org/10.1007/BF02531108
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DOI: https://doi.org/10.1007/BF02531108