3Methoxyiminopregn 4en20one | 26612-47-5

• 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: 3Methoxyiminopregn 4en20one
• 英文别名: 1-[(8S,9S,10R,13S,14S,17S)-3-methoxyimino-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 26612-47-5
• 化学式: C₂₂H₃₃NO₂
• 分子量: 343.51
• InChiKey: GUFBCZIJEDGOPT-GFJXEVPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 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：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  黄体酮 、 甲氧基胺盐酸盐 以 吡啶 为溶剂， 反应 1.0h， 生成 3Methoxyiminopregn 4en20one
  参考文献：
  名称：

  Sodium ascorbate improves yield of urinary steroids during hydrolysis with Helix pomatia juice

  摘要：

  Urinary steroid profile analysis requires enzymatic hydrolysis of glucuronide and sulfate conjugates and this is achieved simultaneously using Helix pomatia juice (HPJ), but steroids with 3 beta-hydroxy-5-ene structure undergo transformation and yield of 5 alpha-reduced corticosteroid glucuronides is poor. We describe the use of sodium ascorbate to solve these problems and provide a basis for its mode of action.Steroid conjugates were extracted from urine, hydrolyzed in acetate buffer with HPJ and sodium ascorbate and analyzed as methyloxime-trimethylsilylether derivatives by gas chromatography-mass spectrometry. Ranges of temperature, pH and ascorbate, substrate and HPJ concentrations were compared for urine and pure standards. Activity of other antioxidants and that of bacterial cholesterol oxidase were examined. Helix pomatia enzyme preparations from different commercial sources were compared.Loss of 3 beta-hydroxy-5-ene steroids was enzyme-dependant, since it required HPJ, was saturable, subject to substrate competition and heat-inactivated. Products were 3-oxo-4-ene steroids and 4,6-diene and 6-oxy derivatives of these but the latter were not formed from 3-oxo-4-ene precursors. Ascorbate, other antioxidants or oxygen exclusion diminished activity. These characteristics were shared by cholesterol oxidase. Yield of 5 alpha-reduced steroids was diminished by pre-incubation of HPJ before ascorbate addition and this was reversed if ascorbate was added to the pre-incubation mixture.We conclude that transformation of 3 beta-hydroxy-5-ene steroids by HPJ is due to cholesterol oxidase and is diminished by antioxidants or oxygen denial. Yield of 5 alpha-reduced steroids is low due to oxidative damage of P-glucuronidase during hydrolysis, prevented by ascorbate. These features are shared by most commercial Helix pomatia enzyme preparations tested. (C) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.11.001