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Chemistry of Natural Compounds

, Volume 22, Issue 6, pp 657–661 | Cite as

Hydrogen bonds of 5α-cholestanols and their ethers

  • D. V. Ioffe
  • L. F. Strelkova
  • I. M. Ginzburg
Article
  • 16 Downloads

Abstract

It has been shown by IR spectroscopy that the equatorial oxygen atoms of cholestanol and its methyl ether possess a greater capacity for forming H bonds as proton acceptors than the axial atoms of the corresponding epimeric compounds. The constants of the equilibrium phenol + ether ⇄ H-complex (1:1) in CCl4 at room temperature are 13 and 7 liter/mole, respectively, for the methyl esters of cholestanol and of epicholestanol.

Keywords

Methyl Ether Diosgenin Cholestanol Steroid Glycoside Tigogenin 

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Literature cited

  1. 1.
    D. B. Ioffe, Usp. Khim.,55, 333 (1986).CrossRefGoogle Scholar
  2. 2.
    B. M. Craven, Nature (London),260, 727 (1976).CrossRefGoogle Scholar
  3. 3.
    B. M. Craven, Acta Crystallogr.,35B, 1123 (1979).CrossRefGoogle Scholar
  4. 4.
    R. A. Demel, R. R. Bruckdorfer, and L. L. M. van Deenen, Biochim. Biophys. Acta,255, 311 (1972).CrossRefGoogle Scholar
  5. 5.
    B. De Kruijff and R. A. Demel, Biochim. Biophys. Acta,339, 57 (1974).CrossRefGoogle Scholar
  6. 6.
    H. Brockerhoff, Lipids,9, 645 (1974).CrossRefGoogle Scholar
  7. 7.
    C. H. Huang, Lipids,12, 348 (1977).CrossRefGoogle Scholar
  8. 8.
    F. T. Presti, R. J. Pace and S. I. Chan, Biochemistry,21, 3831 (1982).CrossRefGoogle Scholar
  9. 9.
    M. Kunst, D. van Duijn, and P. Bordewij, Recl Recl. Trav. Chim.,98, 262 (1979).CrossRefGoogle Scholar
  10. 10.
    B. De Kruijff, R. A. Demel, A. J. Slotboom, L. L. M. van Deenen, and A. F. Rosenthal, Biochim. Biophys. Acta,307, 1 (1973).CrossRefGoogle Scholar
  11. 11.
    R. A. Demel and B. De Kruijff, Biochim. Biophys. Acta,457, 10 (1976).CrossRefGoogle Scholar
  12. 12.
    R. A. Demel, A. K. Lala, S. Nauda, and L. L. M. van Deenen, Biochim. Biophys. Acta,771, 142 (1984).CrossRefGoogle Scholar
  13. 13.
    E. L. Eliel, N. L. Allinger, S. J. Angyal, and G. A. Morrison, Conformational Analysis, Interscience, New York (1965).Google Scholar
  14. 14.
    D. H. R. Barton, Q. Rev.,10, 44 (1956).CrossRefGoogle Scholar
  15. 15.
    L. Fieser and M. Fieser, Steroids, Reinhold, New York (1959).Google Scholar
  16. 16.
    D. V. Ioffe and I. M. Ginzburg, Khim. Prir. Soedin., 49 (1983).Google Scholar
  17. 17.
    Organic Syntheses [Russian translation], Moscow, Vol. 2 (1949), p. 195.Google Scholar
  18. 18.
    F. C. Chang and R. T. Blickenstaff, J. Am. Chem. Soc.,80, 2906 (1958).CrossRefGoogle Scholar
  19. 19.
    E. Muller and W. Rundell, Angew. Chem.,70, 105 (1958).CrossRefGoogle Scholar

Copyright information

© Plenum Publishing Corporation 1987

Authors and Affiliations

  • D. V. Ioffe
  • L. F. Strelkova
  • I. M. Ginzburg

There are no affiliations available

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