6-oxo-24-methylcholestanol | 134982-58-4

• 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: 6-oxo-24-methylcholestanol
• 英文别名: 3β-hydroxy-24ξ-methyl-5α-cholestan-6-one；(3S,5S,8S,9S,10R,13R,14S,17R)-17-[(2R)-5,6-dimethylheptan-2-yl]-3-hydroxy-10,13-dimethyl-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
• CAS: 134982-58-4
• 化学式: C₂₈H₄₈O₂
• 分子量: 416.688
• InChiKey: NBJZGNFIZZWBOJ-HZPHPELVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3β-acetoxy-24-methyl-5α-cholestan-6-one 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以53%的产率得到6-oxo-24-methylcholestanol
  参考文献：
  名称：

  Conversion of 24-methylcholesterol to 6-oxo-24-methylcholestanol, a putative intermediate of the biosynthesis of brassinosteroids, in cultured cells of Catharanthus roseus

  摘要：

  Early steps of brassinosteroid biosynthesis were investigated using cultured cells of Catharanthus roseus. In the cells, 24-methylcholesterol was the major sterol component which accounted for 50% of total sterols and was assumed to be the possible biosynthetic precursor of brassinolide. [C-13(5)] and/or [C-14]24-methylcholesterol were prepared by the cultured cells in the presence of compactin, a mevalonic acid biosynthetic inhibitor. The endogenous metabolites of the labelled 24-methylcholesterol, 24-methylcholestanol, 6 alpha-hydroxy-24-methyIcholestanol (24-methyl-5 alpha-cholestane-3 beta,6 alpha-diol), and 6-oxo-24-methylcholestanol (3 beta-hydroxy-24-methyl-5 alpha-cholestan-6-one were identified by full-scan GC-mass spectrometry. The biosynthetic sequence of 24-methylcholesterol-->24-methylcholestanol--> 6 alpha-hydroxy-24-methylcholestanol-->6-oxo-24-methylcholestanol was established in cultured cells of C. roseus by feeding experiments using labelled 24-methylcholestanol and 6 alpha-hydroxy-24-methylcholestanol. This sequence probably constitutes an early part of the biosynthetic pathway of brassinolide, as introduction of vicinal hydroxyls in the side chain (C-22R and C-23R) of 6-oxo-24-methylcholestanol will yield teasterone. This is the first report of the natural occurrence of 6 alpha-hydroxy-24-methylcholestanol.

  DOI：

  10.1016/0031-9422(95)00579-v