5alpha-雄甾烷-3alpha,17beta-二醇-16,16,17-D3 | 79037-33-5

• 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
• 中文名称: 5alpha-雄甾烷-3alpha,17beta-二醇-16,16,17-D3
• 英文名称: 5α-<16,16,17-²H3>androstane-3α,17β-diol
• 英文别名: (3R,5S,8R,9S,10S,13S,14S,17S)-16,16,17-Trideuterio-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 79037-33-5
• 化学式: C₁₉H₃₂O₂
• 分子量: 295.438
• InChiKey: CBMYJHIOYJEBSB-IAUVTJTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-硝基苯甲酰氯 、 5alpha-雄甾烷-3alpha,17beta-二醇-16,16,17-D3 在 奎宁环 作用下， 以 苯 为溶剂， 生成
  参考文献：
  名称：

  Studies on neurosteroids XVIII

  摘要：

  The liquid chromatography-mass spectrometry (LC-MS) methods were developed and validated for the determination of testosterone (T) in the brain and serum of rats and of Sa-androstane-3 alpha,17 beta-diol (ADIOL), a metabolite of T, in the brain of rats. After derivatization of T with 2-hydrazino-1-methylpyridine and of ADIOL with p-nitrobenzoyl chloride, the detection sensitivities of T and ADIOL using LC-MS were increased 70- and 400-times superior to those of intact T and intact ADIOL, respectively. Those LC-MS methods are specific and reliable for the analysis of trace amounts of T and ADIOL in small amounts of samples. The animal studies using the developed methods showed that the brain and serum levels of T and the brain levels of ADIOL were not changed by stress or ethanol administration but the concentration ratio of the brain T to serum T in the stressed rats was higher than that in untreated rats. The low levels of endogenous AIDOL in brain of stressed and unrestrained rats found in this study demonstrated that the contribution to anesthetic and anxiolytic effects of ADIOL via gamma-aminobutyric acid type A receptors may be negligible. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.03.003
• 作为产物：
  描述：

  雄酮 在 硼氘化钠 、 重水 、 sodium methylate 作用下， 以 四氢呋喃 、 氘代甲醇 为溶剂， 反应 7.33h， 生成 5alpha-雄甾烷-3alpha,17beta-二醇-16,16,17-D3
  参考文献：
  名称：

  Synthesis of deuterium-labeled 5α-androstane-3α,17β-diol and its 17β-glucuronide

  摘要：

  Using unlabeled androsterone as starting material, 5 alpha-[16,16-2H2]androstan-3 alpha-ol-17-one was synthesized by exchange using deuterated potassium methoxide. This labeled androsterone product was reduced by sodium borodeuteride, which gave predominantly trideuterated 5 alpha-androstane-3 alpha, 17 beta-diol. The labeled androstanediol was conjugated with glucuronide by using the Koenig-Knorr reaction with methyl-1-bromo-1-deoxy-2,3,4-tri-O-acetyl-alpha-D-glucopyranosuronate . The dominant product was identified by thermospray high-performance liquid chromatography/mass spectrometry (MS) and electrospray MS as 5 alpha-[16,16,17-2H3]androstane-3 alpha, 17 beta-diol, 17 beta-glucuronide.

  DOI：

  10.1016/0039-128x(92)90022-2