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Sterol metabolism: XXXIII. On derivation of cholesterol 7‐alkoxyl ethers
Author(s) -
Kulig Martin J.,
Teng Jon I.,
Smith Leland L.
Publication year - 1975
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02532162
Subject(s) - chemistry , epimer , beta (programming language) , sterol , organic chemistry , alkyl , methanol , alpha (finance) , diol , alkoxy group , stereochemistry , cholesterol , biochemistry , medicine , construct validity , nursing , computer science , patient satisfaction , programming language
Abstract The facile acid‐catalyzed conversion of cholest‐5‐ene‐3β,7α‐diol (but not of cholest‐5‐ene‐3β, 7β‐diol) in methanol or ethanol solution to the corresponding 7α‐methyl or 7α‐ethyl ethers and epimerization of the 7α‐alkyl ethers to the corresponding 7β‐alkyl ethers were established. The epimeric cholest‐5‐ene‐3β, 7‐diols, their 7‐methyl ethers, and their 7‐ethyl ethers are readily interconverted in acidified solvents, the quasiequatorial 7β‐epimer predominating in each case. Both 7α‐ and 7β‐alkyl ethers may be encountered as artifacts in analyses of sterol mixtures from mammalian tissues.