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Journal of Lipid Research, Vol. 9, 120-128, January 1968
Copyright © 1968 by Lipid Research, Inc.

Nuclear magnetic resonance and infrared spectra of ²⁴- and C-24 saturated steroids

Terence J. Scallen and William Krueger

Departments of Biochemistry and Medicine, University of Minnesota Medical School, Minneapolis, Minnesota 55455, and Department of Biochemistry, University of New Mexico, School of Medicine, Albuquerque, New Mexico 87106

The infrared (IR) and nuclear magnetic resonance (NMR) spectra of eight ²⁴-steroids and nine C-24 saturated steroids were examined. NMR spectra allow unambiguous assignment of the biologically important ²⁴-bond; introduction of a ²⁴-bond causes the appearance of peaks at 1.60 and 1.68 associated with the C-26, C-27 isopropylidene methyls, while C-24 saturated steroids of the cholestane series possess peaks at 0.82 and 0.91 associated with the C-26, C-27 gem-dimethyls. IR spectra show a good correlation between the introduction of a ²⁴-bond and a marked decrease in intensity of a band at 1365 cm^-1. NMR and IR spectra also allow an inference about the presence and location of nuclear double bonds in Ring B of cholesterol precursors.

Supplementary key words sterols • steroids • cholesterol • biosynthesis • infrared • nuclear magnetic resonance • spectra

Submitted on June 12, 1967
Accepted on October 10, 1967

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