6β-hydroperoxyprogesterone | 65179-38-6

• 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: 6β-hydroperoxyprogesterone
• CAS: 65179-38-6
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: LXKCPPXLWVKVDI-CXICGXRGSA-N

物化性质

• 沸点：
  513.6±50.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  progesterone-3-ethanolimine 在 potassium phosphate buffer 、 xanthine oxidase (EC 1.2.3.2) 、 黄嘌呤 作用下， 反应 0.5h， 以4.4%的产率得到4-孕烯-6-beta-醇-3,20-二酮
  参考文献：
  名称：

  Peroxidation in position C-6 of progesterone-3-ethanolimine is increased by the presence of enzymes generating oxygen radicals

  摘要：

  The generation of 6-oxygenated (6-beta-hydroxy, 6-beta-hydroperoxy, and 6-oxo) progesterone derivatives during the hydrolysis of progesterone-3-ethanolimine has been shown to be increased in the presence of xanthine/xanthine oxidase. The combination of xanthine/xanthine oxidase with other enzymes and/or reagents that catalyze transformation (or formation) of oxygen radicals suggested that the most likely oxygen species participating in the 6-oxygenation was the protonated acid of the superoxide anion, i.e., the hydroperoxy radical. The suggestion was further supported by experiments with oxygen scavengers. However, the data presented do not rule out a radical propagation reaction since the steroid compound used may be more reactive than the scavengers tested. A stimulation of 6-oxygenation of progesterone-3-ethanolimine by NADPH-supplemented rat liver microsomes was found. This reaction was inhibited by the only oxygen scavenger (reduced glutathione) found to be effective in the xanthine/xanthine oxidase experiments. The similarities between the two oxygenation systems may implicate a mechanism for 6-beta-hydroperoxidation of 3-oxo-4-ene steroids in rat liver microsomes.

  DOI：

  10.1016/0039-128x(90)90061-f