(24R)-5β,6β-epoxy-24-ethylcholestane-3β-ol | 20835-90-9

• 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)-5β,6β-epoxy-24-ethylcholestane-3β-ol
• 英文别名: β-sitostan-5β,6β-epoxy-3β-ol；5,6β-epoxy-5β-stigmastan-3β-ol；5,6β-epoxy-5β-sitostan-3β-ol；3β-hydroxy-5,6β-epoxystigmastane；β-sitosterol 5,6-β-epoxide；5β,6β-epoxysitosterol；5beta,6beta-Epoxystigmastan-3beta-ol；(1S,2R,5S,7S,9R,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: 20835-90-9
• 化学式: C₂₉H₅₀O₂
• 分子量: 430.715
• InChiKey: ZBNPKSZFWFSSQK-FVKRCMCYSA-N

物化性质

• 沸点：
  518.1±23.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

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：

  油酸 、 (24R)-5β,6β-epoxy-24-ethylcholestane-3β-ol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以72%的产率得到[(1S,2R,5S,7S,9R,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-yl] (Z)-octadec-9-enoate
  参考文献：
  名称：

  Synthesis of highly pure oxyphytosterols and (oxy)phytosterol esters

  摘要：

  Several efficient synthetic routes giving readily access to (oxy)-sitosterol esters and (oxy)cholesterol esters derived respectively from oleic acid and from 9,10-dihydroxystearic acid were developed for the first time. This approach allowed that sufficient amounts of the latter were available in order to carry out further biological studies. (c) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.04.010
• 作为产物：
  描述：

  豆甾醇 在 吡啶 、 potassium permanganate 、 sodium carbonate 、 copper(II) sulfate 作用下， 以 甲醇 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 56.25h， 生成 (24R)-5β,6β-epoxy-24-ethylcholestane-3β-ol
  参考文献：
  名称：

  Synthesis, isolation and characterisation of β-sitosterol and β-sitosterol oxide derivatives

  摘要：

  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。

  DOI：

  10.1039/b505069c

文献信息

• 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.
• Synthesis of highly pure oxyphytosterols and (oxy)phytosterol estersPart I. Regioselective hydrogenation of stigmasterol: An easy access to oxyphytosterols
  作者：Philippe Geoffroy、Diane Julien-David、Eric Marchioni、Francis Raul、Dalal Aoudé-Werner、Michel Miesch

  DOI：10.1016/j.steroids.2008.02.004

  日期：2008.8

  The synthesis of several oxyphytosterols is described starting from stigmasterol, the key step being the regioselective hydrogenation of the 22-23 double bond of the latter. (C) 2008 Elsevier Inc. All rights reserved.
• Mori, Kenji; Fukamatsu, Kunio; Kido, Masaru, Liebigs Annalen der Chemie, 1993, # 6, p. 665 - 670
  作者：Mori, Kenji、Fukamatsu, Kunio、Kido, Masaru

  DOI：——

  日期：——
• 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.
• Denot et al., 1967, vol. 2, p. 495,509
  作者：Denot et al.

  DOI：——

  日期：——