(24R)-5α,6α-epoxy-24-ethylcholestane-3β-ol | 53034-66-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (24R)-5α,6α-epoxy-24-ethylcholestane-3β-ol
• 英文别名: β-sitostan-5α,6α-epoxy-3β-ol；5,6α-epoxy-5α-stigmastan-3β-ol；5,6α-epoxy-5α-sitostan-3β-ol；5α,6α-epoxysitostan-3β-ol；β-sitosterol 5,6-α-epoxide；5,6α-epoxysitosterol；5alpha,6alpha-Epoxystigmastan-3beta-ol；(1S,2R,5S,7R,9S,11S,12S,15R,16R)-15-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-5-ol
• CAS: 53034-66-5
• 化学式: C₂₉H₅₀O₂
• 分子量: 430.715
• InChiKey: ZBNPKSZFWFSSQK-RUEXPLNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (24R)-5α,6α-epoxy-24-ethylcholestane-3β-ol 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以72%的产率得到6β-chloro-5α-stigmastane-3β,5-diol
  参考文献：
  名称：

  On the cytotoxity of oxidized phytosterols isolated from photoautotrophic cell cultures of Chenopodium rubrum tested on meal-worms Tenebrio molitor

  摘要：

  Cell injury-as evoked by oxidative stress, insect attack or ageing-causes lipid peroxidation of polyunsaturated acids, e.g. linoleic acid. Hydroperoxides (LOOH) so produced transform fatty acids, terpenes and sterols to epoxides. We describe a bioassay to determine the cytotoxity of sterol oxidation products by measuring the mortality of meal-worms (Tenebrio molitor) after injection of diluted test compounds. LOOH was tested in concentrations from 10(-5) M up to 10(-3) M and developed recognizable mortality (25%, 10(-2) M, 23 hr). A direct relation between activity and concentration was observed. 5,6-Epoxides of phytosterols and derived 3,5,6-trihydroxysteranes have been isolated from Chenopodium rubrum cell cultures. Using 5,6-epoxycholesterol and 3,5,6-trihydroxycholestane as standards of known bioactivity, the toxicity of epoxides of sitosterol and stigmasterol, as well as the trihydroxy compounds thereof, was checked. The phytosterol derivatives are by a factor of five less active than the corresponding cholesterol oxidation products. 5,6-Epoxides and 5.6-chlorohydrins showed half of the activity of the corresponding 3,5,6-trihydroxyphytosterols. These developed highest cytotoxity (40% mortality in 5 x 10(-3) M solution after 23 hr). The activity of 5,6 alpha- and 5,6 beta-epoxides was found to be equal. Metabolism and proposed biological function of oxidized phytosterols is discussed. (C) 1998 Elsevier Science Ltd. All rights Reserved.

  DOI：

  10.1016/s0031-9422(97)00622-5
• 作为产物：
  描述：

  植物甾醇 在 间氯过氧苯甲酸 作用下， 生成 (24R)-5α,6α-epoxy-24-ethylcholestane-3β-ol
  参考文献：
  名称：

  类固醇与硒代碳水化合物的立体选择性糖结合†

  摘要：

  在这项工作中讨论了将通过硒原子连接的糖和类固醇骨架结合在一起的方法。通过将胆固醇，孕烯醇酮，豆甾醇和谷固醇用不同的硒代吡喃糖苷和呋喃糖苷进行立体选择性亲核取代，可获得一系列6β和3α糖缀合的类固醇。

  DOI：

  10.1039/c6ra21485a

文献信息

• [EN] PROCESS FOR THE PREPARATION OF STEROL DERIVATIVES<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE DÉRIVÉS DE STÉROL
  申请人：INST NAT SANTE RECH MED

  公开号：WO2013076257A1

  公开（公告）日：2013-05-30

  The present invention relates to a process for the preparation of sterol derivatives comprising the reaction of an α-epoxy compound with an amine in an alcohol comprising 3 to 5 carbon atoms as a solvent.

  本发明涉及一种用于制备甾醇衍生物的方法，包括在含有3至5个碳原子的醇溶剂中，将α-环氧化合物与胺反应的过程。
• Synthesis, isolation and characterisation of β-sitosterol and β-sitosterol oxide derivatives
  作者：Florence O. McCarthy、Jay Chopra、Alan Ford、Sean A. Hogan、Joe P. Kerry、Nora M. O'Brien、Eileen Ryan、Anita R. Maguire

  DOI：10.1039/b505069c

  日期：——

  β-Sitosterol is the most prevalent plant cholesterol derivative (phytosterol) and can undergo similar oxidation to cholesterol, leading to β-sitosterol oxides. The biological impact of phytosterol oxides has only been evaluated in a phytosterol blend (usually of β-sitosterol, campesterol, stigmasterol and dihydrobrassicasterol). The lack of pure phytosterols, including β-sitosterol, hinders the collection of significant toxicity data on the individual β-sitosterol oxides. An efficient synthetic route to multi-gram quantities of pure β-sitosterol is described here, together with the first syntheses and characterisation of pure β-sitosterol oxides.

  δ-谷甾醇是最常见的植物胆固醇衍生物（植物甾醇），可发生与胆固醇类似的氧化作用，生成δ-谷甾醇氧化物。植物固醇氧化物的生物影响只在植物固醇混合物（通常包括δ-谷甾醇、坎贝酯醇、豆甾醇和二氢巴西甾醇）中进行过评估。由于缺乏纯植物甾醇（包括δ-谷甾醇），因此无法收集有关单个δ-谷甾醇氧化物的重要毒性数据。本文介绍了多克纯δ-谷甾醇的高效合成路线，以及纯δ-谷甾醇氧化物的首次合成和表征。
• Synthesis of New Alkylaminooxysterols with Potent Cell Differentiating Activities: Identification of Leads for the Treatment of Cancer and Neurodegenerative Diseases
  作者：Philippe de Medina、Michael R. Paillasse、Bruno Payré、Sandrine Silvente-Poirot、Marc Poirot

  DOI：10.1021/jm901063e

  日期：2009.12.10

  We describe here the syntheses and the biological properties of new alkylaminooxysterols. Compounds were synthesized through the trans-diaxial aminolysis of 5,6-alpha-epoxysterols with various natural amines including histamine, putrescine, spermidine, or spermine. The regioselective synthesis of these 16 new 5 alpha-hydroxyl-6 beta-aminoalkylsterols is presented. Compounds were first screened for dendrite outgrowth and cytotoxicity in vitro, and two leads were selected and further characterized. 5 alpha-Hydroxy-6 beta-[2-(1-H-imidazol-4-yl)ethylamino]cholestan -3 beta-ol, called dendrogenin A, induced growth control, differentiation, and the death of tumor cell lines representative of various cancers including metastatic melanoma and breast cancer. 5 alpha-hydroxyl-6 beta-[3-(4-aminobutylamino)propylamino]cholest-7-en-3 beta-ol, called dendrogenin B, induced neurite outgrowth on various cell lines, neuronal differentiation in pluripotent cells, and survival of normal neurones at nanomolar concentrations. In summary, we report that two new alkylaminooxysterols, dendrogenin A and dendrogenin B, are the first members of a class of compounds that induce cell differentiation at nanomolar concentrations and represent promising new leads for the treatment of cancer or neurodegenerative diseases.
• SOUTH AFRICAN GEOMORPHOLOGY: CRITICAL CHOICES FOR THE FUTURE
  作者：H. R. BECKEDAHL、P. D. SUMNER、G. GARLAND

  DOI：10.1080/03736245.2002.9713765

  日期：2002.3
• Gram-scale chromatographic purification of β-sitosterolSynthesis and characterization of β-sitosterol oxides
  作者：X ZHANG、P GEOFFROY、M MIESCH、D JULIENDAVID、F RAUL、D AOUDEWERNER、E MARCHIONI

  DOI：10.1016/j.steroids.2005.06.003

  日期：2005.12.1

  An effective purification method for P-sitosterol was developed starting from a commercial source of a phytosterol mixture using preparative adsorption column chromatography. P-Sitosterol (>= 95% purity) was obtained on a gram-scale. Thus, the synthesis of six P-sitosterol oxides, including 7 alpha-hydroxy, 7 beta-hydroxy, 5,6 alpha-epoxy, 5,6 beta-epoxy, 7-keto, and 5 alpha,6 beta-dihydroxysitosterol, were successfully carried out. The spectral characteristics of all the synthetic intermediates and target compounds (similar to 95% purity) were well-documented. (c) 2005 Elsevier Inc. All rights reserved.