Synthesis of the putative metabolites of plant sterols: (24R)- and (24S)-24-methyl-5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrols and 24-ethyl-5 beta-cholestane-3 alpha,7 alpha,12 alpha,24 xi-tetrol.
This report describes the synthesis of (24R)- and (24S)-24-methyl-5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrols and 24-ethyl-5 beta-cholestane-3 alpha,7 alpha,12 alpha,24 xi-tetrol starting from cholic acid. The bile alcohols epimeric at C-24 were resolved by analytical and preparative thin-layer chromatography and characterized by gas-liquid chromatography and mass spectrometry. These epimeric bile alcohols may be useful for studying the transformation of beta-sitosterol to cholic acid.
D000818:Animals; D002777:Cholestanols / Q000138:chemical synthesis*; D006801:Humans; D010840:Phytosterols / Q000138:chemical synthesis* / Q000378:metabolism; D012855:Sitosterols / Q000378:metabolism
D002777:Cholestanols; D010840:Phytosterols; D012855:Sitosterols; C025473:gamma-sitosterol; C042879:24-methylcholestane-3,7,12,25-tetrol; C042880:24-ethylcholestane-3,7,12,24-tetrol