5α-hydroxy-6β-[2-hydroxyethylsulfanyl]cholestan-3β-ol | 1379475-28-1

• 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: 5α-hydroxy-6β-[2-hydroxyethylsulfanyl]cholestan-3β-ol
• CAS: 1379475-28-1
• 化学式: C₂₉H₅₂O₃S
• 分子量: 480.796
• InChiKey: JCIWKRLLPFKYGY-OYYJYTPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.29
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.69
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-巯基乙醇 、 胆固醇-5Alpha,6Alpha-环氧化物 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以23%的产率得到5α-hydroxy-6β-[2-hydroxyethylsulfanyl]cholestan-3β-ol
  参考文献：
  名称：

  Surprising unreactivity of cholesterol-5,6-epoxides towards nucleophiles

  摘要：

  We recently established that drugs used for the treatment and the prophylaxis of breast cancers, such as tamoxifen, were potent inhibitors of cholesterol-5,6-epoxide hydrolase (ChEH), which led to the accumulation of 5,6 alpha-epoxy-cholesterol (5,6 alpha-EC) and 5,6 beta-epoxy-cholesterol (5,6 beta-EC). This could be considered a paradox because epoxides are known as alkylating agents with putative carcinogenic properties. We report here that, as opposed to the carcinogen styrene-oxide, neither of the ECs reacted spontaneously with nucleophiles. Under catalytic conditions, 5,6 beta-EC remains unreactive whereas 5,6 alpha-EC gives cholestan-3 beta,5 alpha-diol-6 beta-substituted compounds. These data showed that 5,6-ECs are stable epoxides and unreactive toward nucleophiles in the absence of a catalyst, which contrasts with the well-known reactivity of aromatic and aliphatic epoxides.(jlr) These data rule out 5,6-EC acting as spontaneous alkylating agents. In addition, these data support the existence of a stereoselective metabolism of 5,6 alpha-EC.-Paillasse, M. R., N. Saffon, H. Gornitzka, S. Silvente-Poirot, M. Poirot, and P. de Medina. Surprising unreactivity of cholesterol-5,6-epoxides towards nucleophiles. J. Lipid Res. 2012. 53: 718-725.

  DOI：

  10.1194/jlr.m023689