Sterol metabolism: XXXIII. On derivation of cholesterol 7‐alkoxyl ethers
- 1 February 1975
- Vol. 10 (2) , 93-98
- https://doi.org/10.1007/bf02532162
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.Keywords
This publication has 23 references indexed in Scilit:
- Sterol metabolism. XXIII. Cholesterol oxidation by radiation-induced processesThe Journal of Organic Chemistry, 1973
- Lipids of human atheroma vii. isolation of diesters of cholest-5-ene-3β,26-diol from extracts of advanced atherosclerotic lesions of human aortaBiochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1972
- Lipids of human atheroma Part 4. Characterisation of a new group of polar sterol esters from human atherosclerotic plaquesAtherosclerosis, 1971
- Cholestanol and 26-hydroxycholesterol in normal and atherosclerotic human aortaLife Sciences, 1971
- Sterol metabolism: Part 9. 26-hydroxycholesterol levels in the human aortaAtherosclerosis, 1970
- Squalene, 26-hydroxycholesterol and 7-ketocholesterol in human atheromatous plaquesBiochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1966
- A HISTOCHEMICAL AND CHROMATOGRAPHIC STUDY OF NORMAL AND ATHEROMATOUS HUMAN ARTERIESJournal of Histochemistry & Cytochemistry, 1956
- Etherifications Accompanying Girard Treatment for the Separation of Ketonic SubstancesNature, 1946
- Untersuchungen über Organextrakte. (4. Mitteilung). Zur Kenntnis der unverseifbaren Lipoide aus SchweinemilzHelvetica Chimica Acta, 1943
- Untersuchungen über Organextrakte. (3. Mitteilung). Zur Kenntnis der unverseifbaren Lipoide aus arteriosklerotischen AortenHelvetica Chimica Acta, 1943