3-keto-9-hydroxy-23,24-dinor-4-cholen-22-oic acid | 63502-99-8

• 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: 3-keto-9-hydroxy-23,24-dinor-4-cholen-22-oic acid
• 英文别名: 9alpha-Hydroxy-3-oxo-23,24-bisnorchol-4-en-22-oic acid；(2S)-2-[(8S,9R,10S,13S,14S,17R)-9-hydroxy-10,13-dimethyl-3-oxo-2,6,7,8,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]propanoic acid
• CAS: 63502-99-8
• 化学式: C₂₂H₃₂O₄
• 分子量: 360.494
• InChiKey: JHVIIDLZSOMCBJ-MPITXTFFSA-N

物化性质

• 沸点：
  540.6±43.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  胆固醇 在 microorganism SCM-1 from the mutant NRRL B-8119 of Mycobacterium fortuitum (ATCC 6842) by treatment with N-methyl-N'-nitro-N-nitrosoguanidine 作用下， 生成 9α-羟基-4-雄甾烯-3,17-二酮 、 9α,17β-dihydroxy-4-androsten-3-one 、 9,22-dihydroxy-23,24-dinor-4-cholen-3-one 、 3-keto-9-hydroxy-23,24-dinor-4-cholen-22-oic acid
  参考文献：
  名称：

  Microbial degradation of the phytosterol side-chain to 24-oxo products

  摘要：

  A mutant of the potent sterol degrader Mycobacterium fortuitum (ATCC 6842) has been isolated which is defective in its ability to degrade both the steroid nucleus and sterol side-chains that are branched at the 24-position. Bioconversions of phytosterol mixtures by this mutant resulted in the accumulation of the novel 24-oxo intermediates 9-hydroxy-27-nor-4-cholestene-3,24-dione (II) and 9-hydroxy-26,27-dinor-4-cholestene-3,24-dione (III). Under the same conditions, cholesterol is degraded mainly to 9-hydroxy-4-androstene-3,17-dione (I) by this organism.

  DOI：

  10.1016/0039-128x(80)90055-0

文献信息

• Microbial degradation of the phytosterol side-chain to 24-oxo products
  作者：John C. Knight、Merle G. Wovcha

  DOI：10.1016/0039-128x(80)90055-0

  日期：1980.12

  A mutant of the potent sterol degrader Mycobacterium fortuitum (ATCC 6842) has been isolated which is defective in its ability to degrade both the steroid nucleus and sterol side-chains that are branched at the 24-position. Bioconversions of phytosterol mixtures by this mutant resulted in the accumulation of the novel 24-oxo intermediates 9-hydroxy-27-nor-4-cholestene-3,24-dione (II) and 9-hydroxy-26,27-dinor-4-cholestene-3,24-dione (III). Under the same conditions, cholesterol is degraded mainly to 9-hydroxy-4-androstene-3,17-dione (I) by this organism.