5α-<16,16-²H2>androstane-3α-ol-17-one | 89685-22-3

• 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
• 英文名称: 5α-<16,16-²H2>androstane-3α-ol-17-one
• 英文别名: <16,16-2H2>Androsterone；androsterone-d2；5alpha-Androstan-3alpha-ol-17-one-16,16-d2；(3R,5S,8R,9S,10S,13S,14S)-16,16-dideuterio-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-one
• CAS: 89685-22-3
• 化学式: C₁₉H₃₀O₂
• 分子量: 292.43
• InChiKey: QGXBDMJGAMFCBF-SNPKRAFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5α-<16,16-²H2>androstane-3α-ol-17-one 在 硼氘化钠 作用下， 以 氘代甲醇-d 为溶剂， 反应 0.5h， 生成 <16,16,17-2H3>Androstane-3α,17β-diol
  参考文献：
  名称：

  Application of gas chromatography/mass spectrometry to steroid analysis in equine sports: Problems with enzyme hydrolysis

  摘要：

  AbstractIn steroid analysis in biological fluids, cleavage of conjugates is an essential step which can be achieved by either enzymatic or chemical hydrolysis. Where conjugation with both glucuronic acid and sulphate occurs, then the use of the enzyme preparation from Helix pomatia, containing both β‐glucuronidase and aryl sulphatase activities, would appear to be advantageous. However, it has been shown that the sulphatase enzymes of Helix pomatia do not hydrolyse 17β‐sulphates and that other enzymatic activities also present in the preparation can give rise to artefact formation with certain steroids.The artefacts produced from incubation of dehydroisoandrosterone with the enzyme preparation from Helix pomatia have been identified by gas chromatography/mass spectrometry (GC/MS) as androst‐4‐ene‐3,17‐dione, androsta‐4,6‐diene‐3,17‐dioue, androst‐4‐ene‐3,6,17‐trione and 6‐hydroxyandrost‐4‐ene‐3,17‐dione. Incubation of androst‐5‐ene‐3,17‐diol produced a similar series of compounds with a 17‐hydroxy function. Semi‐quantitative GC/MS analysis has been used to determine the extent of these transformations in the presence of increasing amounts of the Helix pomatia preparation. Quantitative conversion in buffer can be obtained but the results from incubation in urine showed a marked modifying effect with minimal artefact formation. The enzyme preparation from Escherichia coli does not yield any artefacts and results are presented for the optimization of its use in the hydrolysis of the glucuronic acid conjugate of 5α‐estrane‐3β,17α‐diol, the major metabolite of nandrolone in the horse.

  DOI：

  10.1002/oms.1210271016
• 作为产物：
  描述：

  雄酮 在 氘代丙酮 、 potassium carbonate 、 氯化(1-丁基-3-甲基咪唑) 作用下， 反应 12.0h， 以74%的产率得到5α-<16,16-²H2>androstane-3α-ol-17-one
  参考文献：
  名称：

  咪唑阳离子与酮的动态共价相互作用诱导的有机催化氘化。

  摘要：

  在本文中，我们提出了一种基于咪唑鎓阳离子与酮的动态共价相互作用的新的有机催化方法。N-烷基咪唑鎓盐与丙酮d 6在含氧碱的存在下反应生成动态有机催化体系，质子化的卡宾/酮加合物作为H / D交换催化剂。已开发的pH依赖性氘代方法显示出较高的标记选择性和良好的手性官能团耐受性。在这里，我们报告了一种有效的无金属氘化的独特方法，该方法可以标记各种类型的α-酸性化合物而不会造成痕量金属污染。

  DOI：

  10.1002/adsc.202001507

文献信息

• Synthesis of deuterium-labeled 5α-androstane-3α,17β-diol and its 17β-glucuronide
  作者：Chung Bong-Chul、John P. Mallamo、Paul E. Juniewicz、Cedric H.L. Shackleton

  DOI：10.1016/0039-128x(92)90022-2

  日期：1992.11

  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.