Chemistry of Natural Compounds

, Volume 12, Issue 5, pp 525–528 | Cite as

Tautomerism of the α-hydroxydienic acids of the seed oil of Artemisia absinthium

  • N. T. Ul'chenko
  • É. I. Gigienova
  • A. U. Umarov
Article
  • 20 Downloads

Summary

On investigating the α-hydroxydienic acids of the oil of the seeds ofArtemisia absinthium, we observed tautomeric transformations of the free α-hydroxydienic systems. It has been shown that the tautomerism of these systems is the result not only of a dynamic but also of a static conjugation effect. 11-Hydroxyoctadecatrans,trans-9,12-dienoic acid, which is formed by the geometric and position isomerization of α-hydroxyoctadecadienoic acids with the trans,cis conjugation of the ethylenic bonds and is relatively stable in the presence of a static conjugation effect has been detected.

Keywords

Methyl Ester Azelaic Acid Conjugation Effect Ethylenic Bond Enoic Acid 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    C. Y. Hopkins and M. J. Chisholm, Can. J. Chem.,43, 3160 (1965).CrossRefGoogle Scholar
  2. 2.
    R. G. Powell, C. R. Smith, C. A. Glass, and I. A. Wolff, J. Org. Chem.,30, 610 (1965).CrossRefGoogle Scholar
  3. 3.
    G. R. Powell, C. R. Smith, and I. A. Wolff, J. Org. Chem.,32, 1442 (1967).CrossRefGoogle Scholar
  4. 4.
    É. I. Gigienova, N. T. Ul'chenko, and A. U. Umarov, Khim. Prirodn. Soedin., 701 (1974).Google Scholar
  5. 5.
    M. J. Chisholm and C. Y. Hopkins, Can. J. Chem.,38, 2500 (1960).CrossRefGoogle Scholar
  6. 6.
    R. H. De Wolfe and W. G. Young, Chem. Rev.,56, 753 (1956).CrossRefGoogle Scholar
  7. 7.
    T. I. Temnikova, A Course of the Theoretical Principles of Organic Chemistry [in Russian], Leningrad (1968), p. 672.Google Scholar
  8. 8.
    L. J. Morris, R. T. Holman, and K. Fontell, J. Am. Oil Chemists' Soc.,37, 323 (1960).CrossRefGoogle Scholar
  9. 9.
    R. Kleiman, G. F. Spencer, L. W. Tjarks, and F. R. Earle, Lipids,6, 617 (1971).CrossRefGoogle Scholar

Copyright information

© Plenum Publishing Corporation 1977

Authors and Affiliations

  • N. T. Ul'chenko
  • É. I. Gigienova
  • A. U. Umarov

There are no affiliations available

Personalised recommendations