Δ5-androsten-3β-ol-17-one-3-sulfate (triethylammonium salt) | 20997-98-2

• 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: Δ5-androsten-3β-ol-17-one-3-sulfate (triethylammonium salt)
• 英文别名: Δ⁵-androsten-3β-ol-17-one-3-sulfate (triethylammonium salt)；3β-sulfooxyandrost-5-en-17-one triethylammonium salt；dehydroepiandrosterone-3-sulfate triethylammonium salt；Δ⁵-androsten-3β-ol-17-one 3-sulfuric acid ester (triethylammonium salt)
• CAS: 20997-98-2
• 化学式: C₆H₁₅N*C₁₉H₂₈O₅S
• 分子量: 469.686
• InChiKey: ZGEDAFNFZXIHDK-ZJTJBYBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  83.91
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  去氢表雄酮 、 三氧化硫-三乙胺复合物 在 吡啶 作用下， 以63%的产率得到Δ5-androsten-3β-ol-17-one-3-sulfate (triethylammonium salt)
  参考文献：
  名称：

  A simple method for the small scale synthesis and solid-phase extraction purification of steroid sulfates

  摘要：

  Steroid sulfates are a major class of steroid metabolite that are of growing importance in fields such as anti-doping analysis, the detection of residues in agricultural produce or medicine. Despite this, many steroid sulfate reference materials may have limited or no availability hampering the development of analytical methods. We report simple protocols for the rapid synthesis and purification of steroid sulfates that are suitable for adoption by analytical laboratories. Central to this approach is the use of solid-phase extraction (SPE) for purification, a technique routinely used for sample preparation in analytical laboratories around the world. The sulfate conjugates of sixteen steroid compounds encompassing a wide range of steroid substitution patterns and configurations are prepared, including the previously unreported sulfate conjugates of the designer steroids furazadrol (17 beta-hydroxyandrostan[2,3-d]isoxazole), isofurazadrol (17 beta-hydroxyandrostan[3,2-c]isoxazole) and trenazone (17 beta-hydroxyestra-4,9-dien-3-one). Structural characterization data, together with NMR and mass spectra are reported for all steroid sulfates, often for the first time. The scope of this approach for small scale synthesis is highlighted by the sulfation of 1 mu g of testosterone (17 beta-hydroxyandrost-4-en-3-one) as monitored by liquid chromatography-mass spectrometry (LCMS). (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.09.006

文献信息

• A fusion method for the preparation of steroid sulfates
  作者：John P. Dusza、Joseph P. Joseph、Seymour Bernstein

  DOI：10.1016/0039-128x(85)90080-7

  日期：1985.3

  A method for the preparation of steroid triethylammonium sulfates is outlined which involves the fusion of triethylamine-sulfur trioxide and steroids. Experimental details are presented which define the process as a thermal equilibrium resulting in the preferential sulfation of aliphatic hydroxyl groups. Sulfation of an aromatic hydroxyl group can be achieved in the absence of an aliphatic hydroxyl group. With excess reagent both types of hydroxyl groups in the same molecule can be sulfated.