The identification of a novel C27 diene, cholesta-5,8-dien-3 beta-OL, in tissues of rats given AY-9944 (trans-1,4-bis(2-dichlorobenzylaminoethyl)cyclohexane) in pregnancy.

Treatment of pregnant rats with AY-9944, a drug interfering with the last steps of cholesterol biosynthesis, accumulated cholesterol precursors in brain and liver of newborn animals. Different sterol profiles were found in these organs. Along with cholesterol and cholesta-5,7-dien-3 beta-ol, present in both tissues, liver was found to contain a hitherto unreported sterol, absent in brain. The structure of cholesta-5,8-dien-3 beta-ol was attributed to this compound by mass spectrometric, 1H, and 13C NMR analysis.