Chemistry of Natural Compounds

, Volume 3, Issue 6, pp 312–319 | Cite as

Mass spectrometry of steroid systems

XI. Determination of the configuration of steroid alcohols
  • N. S. Vul'fson
  • V. I. Zaretskii
  • V. G. Zaikin


1. The mass spectra of epimeric tertiary alcohols of the D-homoestrane series and the acetates and 17a-trideuteromethyl analogs corresponding to them have been studied. A new approach to the determination of the configuration of tertiary steroid alcohols has been proposed in which the trideuteromethyl analogs of the epimeric alcohols are subjected to mass-spectrometric analysis. The presence in the mass spectrum of an epimer of a doublet of peaks M-H2O and M-DOH indicates the a-alkyl-e-OH configuration, while the presence in the spectrum of an intense M-H2O peak shows the presence of an axial OH group.

2. The mass spectra of the epimeric secondary alcohols of the pregnane series taken with the use of a system of introducing the sample into the ion source has been investigated. It has been shown that the mass spectra of alcohols containing an a-OH group in rings C and D differ markedly from the spectra of the e-OH epimers with respect to the ratio of the intensities of the peaks M-H2O and M+.


Mass Spectrum Hydroxyprogesterone Tertiary Alcohol Exocyclic Double Bond Pregnane Series 


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Copyright information

© The Faraday Press, Inc 1969

Authors and Affiliations

  • N. S. Vul'fson
    • 1
  • V. I. Zaretskii
    • 1
  • V. G. Zaikin
    • 1
  1. 1.Institute of the Chemistry of Natural Compounds, AS USSRUSSR

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