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甾醇代谢:XXXIII. 关于胆固醇7-烷氧基醚的衍生化

Sterol metabolism: XXXIII. On derivation of cholesterol 7-alkoxyl ethers.

作者信息

Kulig M J, Teng J I, Smith L L

出版信息

Lipids. 1975 Feb;10(2):93-8. doi: 10.1007/BF02532162.

DOI:10.1007/BF02532162
PMID:1117809
Abstract

The facile acid-catalyzed conversion of cholest-5-ene-3 beta, 7 alpha-diol (but not of cholest-5-ene-3 beta, 7 beta-diol) in methanol or ethanol solution to the corresponding 7 alpha-methyl or 7 alpha-ethyl ethers and epimerization of the 7 alpha-alkyl ethers to the corresponding 7 beta-alkyl ethers were established. The epimeric cholest-5-ene-3 beta, 7-diols, their 7-methyl ethers, and their 7-ethyl ethers are readily interconverted in acidified solvents, the quasiequatorial 7 beta-epimer predominating in each case. Both 7 alpha- and 7 beta-alkyl ethers may be encountered as artifacts in analyses of sterol mixtures from mamalian tissues.

摘要

已证实,在甲醇或乙醇溶液中,胆甾-5-烯-3β,7α-二醇(但胆甾-5-烯-3β,7β-二醇不行)可通过简便的酸催化转化为相应的7α-甲基或7α-乙基醚,且7α-烷基醚会差向异构化为相应的7β-烷基醚。差向异构的胆甾-5-烯-3β,7-二醇、其7-甲基醚和7-乙基醚在酸化溶剂中很容易相互转化,每种情况下准赤道面的7β-差向异构体占主导。在分析哺乳动物组织中的甾醇混合物时,7α-和7β-烷基醚都可能作为假象出现。

相似文献

1
Sterol metabolism: XXXIII. On derivation of cholesterol 7-alkoxyl ethers.甾醇代谢:XXXIII. 关于胆固醇7-烷氧基醚的衍生化
Lipids. 1975 Feb;10(2):93-8. doi: 10.1007/BF02532162.
2
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J Biol Chem. 1980 Apr 25;255(8):3565-70.
3
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Capillary column gas-liquid chromatographic resolution of oxidized cholesterol derivatives.
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Characterization of by-products derived from cholesterol during methanolysis and simultaneous quantitative analysis of cholesterol and fatty acids by gas-liquid chromatography.甲醇解过程中胆固醇衍生副产物的表征以及通过气液色谱法对胆固醇和脂肪酸进行同步定量分析
Jpn J Exp Med. 1973 Apr;43(2):157-62.
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Sterol metabolism. 28. Biosynthesis and accumulation of cholest-5-ene-3beta, 24-diol (cerebrosterol) in developing rat brain.甾醇代谢。28. 发育中大鼠脑内胆甾-5-烯-3β,24-二醇(脑甾醇)的生物合成与积累。
Biochim Biophys Acta. 1974 May 29;348(2):189-96. doi: 10.1016/0005-2760(74)90230-6.

本文引用的文献

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Studies in the sterol group; 7-substituted cholesterol derivatives and their stereochemistry; esters of the epimeric 7-hydroxycholesterols.甾醇类研究;7-取代胆固醇衍生物及其立体化学;差向异构7-羟基胆固醇的酯类
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A histochemical and chromatographic study of the lipid distribution in human arteries.
人体动脉脂质分布的组织化学与色谱研究
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[The analysis of sterols from biological substances by thin layer chromatography and by gas chromatography. Application to the study of diseases caused by atherosclerosis].[通过薄层色谱法和气相色谱法对生物物质中的甾醇进行分析。在动脉粥样硬化所致疾病研究中的应用]
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Steroids. XXX. Some properties of the cholest-5-ene-3-beta, 7xi-diols and their esters.类固醇。XXX。胆甾-5-烯-3-β,7ξ-二醇及其酯的某些性质。
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Isolation and identification of cholesteryl alkyl ethers from bovine cardiac muscle.
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Cholestanol and 26-hydroxycholesterol in normal and atherosclerotic human aorta.正常和动脉粥样硬化人类主动脉中的胆甾烷醇和26-羟基胆固醇。
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