14,17-二羟基雄甾-1,4-二烯-3-酮 | 58105-34-3

• 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
• 中文名称: 14,17-二羟基雄甾-1,4-二烯-3-酮
• 英文名称: 14α,17β-dihydroxyandrosta-1,4-dien-3-one
• 英文别名: 14α,17β-dihydroxyandrost-1,4-dien-3-one；14α-hydroxy-1-dehydrotestosterone；14alpha,17beta-Dihydroxyandrosta-1,4-dien-3-one；(8R,9S,10R,13R,14R,17S)-14,17-dihydroxy-10,13-dimethyl-7,8,9,11,12,15,16,17-octahydro-6H-cyclopenta[a]phenanthren-3-one
• CAS: 58105-34-3
• 化学式: C₁₉H₂₆O₃
• 分子量: 302.414
• InChiKey: AMMCJHLYDWYYKQ-XNIJUTNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  雄烯二酮 以 丙酮 为溶剂， 反应 48.0h， 生成 14Α-羟基睾酮 、 14,17-二羟基雄甾-1,4-二烯-3-酮
  参考文献：
  名称：

  The identification of 14α,17β-dihydroxyandrost-4-en-3-one monohydrate and 14α, l7β-dihydroxyandrosta-1,4-dien-3-one monohydrate, metabolites of androstenedione in Mucor piriformis

  摘要：

  The microorganism Mucor piriformis transforms androst-4-ene-3,17-dione into a major and several minor metabolites. X-ray crystallographic analysis of two of these metabolites was undertaken to determine unambiguously their composition and chirality. Crystals belong to the orthorhombic space-group P2(1)2(1)2(1), with a = 7.199(4) angstrom and a = 6.023(3) angstrom, b = 11.719(3) angstrom and b = 13.455(4) angstrom, c = 20.409(3) angstrom and c = 20.702(4) angstrom for the two title compounds, respectively. The structures have been refined to final R values of 0.060 and 0.040, respectively.

  DOI：

  10.1016/0039-128x(91)90033-r

文献信息

• The hydroxylation of testosterone and some relatives by Cephalosporium aphidicola
  作者：James R. Hanson、Habib Nasir、Aslam Parvez

  DOI：10.1016/0031-9422(95)00968-x

  日期：1996.5

  The fungus Cephalosporium aphidicola has been shown to hydroxylate testosterone, 19-nortestosterone, 1-dehydrotestosterone, 1 alpha-methyltestosterone, androst-4-en-3-one, androst-4-en-3,17-dione and 17 alpha-methyltestosterone predominantly at the C-6 beta position with a minor hydroxylation occurring at the C-14 alpha position. 19-Nortestosterone was also hydroxylated at the C-10 beta position. In contrast to the hydroxylation of progesterone by this organism, hydroxylation at C-11 alpha was a minor pathway.