17β-methyl-5β-androstane-3α,17α-diol | 88729-26-4

• 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: 17β-methyl-5β-androstane-3α,17α-diol
• 英文别名: "17beta-Methyl-5beta-androstane-3alpha,17alphalpha-diol"；(3R,5R,8R,9S,10S,13S,14S,17R)-10,13,17-trimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS: 88729-26-4
• 化学式: C₂₀H₃₄O₂
• 分子量: 306.489
• InChiKey: QGKQXZFZOIQFBI-ULWYFIRJSA-N

物化性质

• 沸点：
  418.1±18.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 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：

  17β-methyl-5β-androstane-3α,17α-diol 在 硫酸氢铵 、 碳酸氢铵 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 以 水 为溶剂， 生成 17β-methyl-5β-androstane-3α,17α-diol 3-sulfate
  参考文献：
  名称：

  磺基共轭代谢物的表征和定量，用于检测甲基睾酮滥用并通过 LC-MS 直接识别。

  摘要：

  甲基睾酮（MT）是兴奋剂控制分析中发现的最常被滥用的合成代谢雄激素类固醇之一。 MT 在人体中的代谢产生多种 І 相代谢物及其相应的 Ⅱ 相结合物。先前的研究假设17α-甲基-5β-雄甾烷-3α,17β-二醇(S2)的3α-磺基缀合物是MT的主要硫酸盐代谢物，检测窗口超过10天。然而，迄今为止，尚未对该代谢物的结构进行最终直接且明确的确认。在本研究中，我们建立了一种检测和识别 S2 的方法，使用液相色谱联用串联质谱 (LC-MS/MS) 进行完整分析，无需复杂的样品预处理。一项体外研究得出了所有 3-硫酸化 17-甲基雄甾烷-3,17-二醇非对映异构体的 LC-MS/MS 参考保留时间，从而可以对潜在检测到的代谢物进行准确的结构分配。在对一名健康男性志愿者进行的体内排泄研究中，单次口服 10 mg MT 后证实了代谢物 S2 的存在。参考标准是化学合成的，通过精确质谱 (MS) 和核磁共振

  DOI：

  10.1016/j.jsbmb.2024.106527
• 作为产物：
  描述：

  17-亚甲基-4-雄甾烯-3-酮 在 Lindlar's catalyst sodium tetrahydroborate 、 氢气 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 1.0h， 生成 17β-methyl-5β-androstane-3α,17α-diol
  参考文献：
  名称：

  Proton magnetic resonance spectra of 17ξ-Hydroxy-17ξ-methyl-5ξ-androstane C-3 ketone and c-3ξ alcohol isomers in chloroform-d and pyridine-d5

  摘要：

  17 alpha-Hydroxy-17 beta-methyl-5 beta-androstan-3-one,17 beta-methyl-5 alpha-androstane-3 alpha,17 alpha-diol,17 beta-methyl-5 alpha-androstane-3 beta,17 alpha-diol,17 alpha-methyl-5 beta-androstane-3 beta,17 beta-diol,17 beta-methyl-5 beta-androstane-3 alpha,17 alpha-diol and 17 beta-methyl-5 beta-androstane-3 beta,17 alpha-diol were synthesized for the first time. 1H NMR spectra of all four 17 xi-hydroxy/17 xi-methyl C-3 ketones and all eight C-3 alcohols were recorded in chloroform-d and pyridine-d5. Pyridine-induced chemical shifts are discussed. Thin-layer chromatographic data are given.

  DOI：

  10.1016/0039-128x(83)90088-0

文献信息

• 17-Epimerization of 17α-methyl anabolic steroids in humans: metabolism and synthesis of 17α-hydroxy-17β-methyl steroids
  作者：Willi Schänzer、Georg Opfermann、Manfred Donike

  DOI：10.1016/0039-128x(92)90023-3

  日期：1992.11

  chromatography as trimethylsilyl derivatives from a capillary SE-54 or OV-1 column 70-170 methylen units before the corresponding 17 alpha-methyl epimer. The electron impact mass spectra of the underivatized and trimethylsilylated epimers are in most cases identical and only for I, II, and V was a differentiation between the 17-epimers possible. 1H nuclear magnetic resonance (NMR) spectra show for the 17 beta-methyl

  17个β-二醇（XIX）（也是VI，VII和XI的代谢物），17个α-甲基-5α-雄甾烷3β，17个β-二醇（XX），17个α-甲基-5β-雄烷醇-3 alpha，17 beta-diol（XXI）（也是V，VII和VIII的代谢物），17 alpha-methyl-5 beta-androstane-3 beta，17 beta-diol（XXII）和17 beta-hydroxy -7α，17α-二甲基-5β-雄烷-3-酮（XXIII）是通过17β-硫酸盐合成的，该硫酸盐在水中自发水解成几种脱水产物，再合成为17α-羟基-17β-甲基差向异构体。通过使17β-羟基-17α-甲基甾族化合物与三氧化硫吡啶配合物反应来制备17β-硫酸盐。在相应的17个α-甲基差向异构体之前，从毛细管SE-54或OV-1色谱柱的70-170个亚甲基单元中，将17种β-甲基差向异构体作为三甲基甲硅烷基衍生物从气
• Alternative long-term markers for the detection of methyltestosterone misuse
  作者：C. Gómez、O.J. Pozo、J. Marcos、J. Segura、R. Ventura

  DOI：10.1016/j.steroids.2012.10.008

  日期：2013.1

  Methyltestosterone (MT) is one of the most frequently detected anabolic androgenic steroids in doping control analysis. MT misuse is commonly detected by the identification of its two main metabolites excreted as glucuronide conjugates, 17 alpha-methyl-5 alpha-androstan-3 alpha,17 beta-diol and 17 alpha-methyl-5 beta-androstan-3 alpha,17 beta-diol. The detection of these metabolites is normally performed by gas chromatography-mass spectrometry, after previous hydrolysis with beta-glucuronidase enzymes, extraction and derivatization steps. The aim of the present work was to study the sulphate fraction of MT and to evaluate their potential to improve the detection of the misuse of the drug in sports. MT was administered to healthy volunteers and urine samples were collected up to 30 days after administration. After an extraction with ethyl acetate, urine extracts were analysed by liquid chromatography tandem mass spectrometry using electrospray ionisation in negative mode by monitoring the transition m/z 385 to m/z 97. Three diol sulphate metabolites (S1, S2 and S3) were detected. Potential structures for these metabolites were proposed after solvolysis and mass spectrometric experiments: S1, 17 alpha-methyl-5 beta-androstan-3 alpha,17 beta-diol 3 alpha-sulphate; S2, 17 beta-methyl-5 alpha-androstan-3 alpha,17 alpha-diol 3 alpha-sulphate; and S3, 17 beta-methyl-5 beta-androstan-3 alpha,17 alpha-diol 3 alpha-sulphate. Synthesis of reference compounds will be required in order to confirm the structures. The retrospectivity of these sulphate metabolites in the detection of MT misuse was compared with the obtained with previously described metabolites. Metabolite S2 was detected up to 21 days after MT administration, improving between 2 and 3 times the retrospectivity of the detection compared to the last long-term metabolite of MT previously described, 17 alpha-hydroxy-17 beta-methylandrostan-4,6-dien-3-one. (c) 2012 Elsevier Inc. All rights reserved.
• OPHTHALMIC LUBRICATING SPRAY
  申请人：Salzman Ira Jason

  公开号：US20180055943A1

  公开（公告）日：2018-03-01

  An ophthalmic composition for administration as a spray to the eye is provided. The ophthalmic composition comprises a lubricant comprising hydroxypropyl methylcellulose (HPMC), mineral oil, and sterile water. The ophthalmic composition is also configured as a delivery vehicle for administration of ophthalmic pharmaceuticals to the eye. A method of treating keratoconjunctivitis sicca by administering the ophthalmic composition is also provided.
• US9981041B2
  申请人：——

  公开号：US9981041B2

  公开（公告）日：2018-05-29
• Proton magnetic resonance spectra of 17ξ-Hydroxy-17ξ-methyl-5ξ-androstane C-3 ketone and c-3ξ alcohol isomers in chloroform-d and pyridine-d5
  作者：John F. Templeton、Chung-Ja Choi Jackson

  DOI：10.1016/0039-128x(83)90088-0

  日期：1983.4

  17 alpha-Hydroxy-17 beta-methyl-5 beta-androstan-3-one,17 beta-methyl-5 alpha-androstane-3 alpha,17 alpha-diol,17 beta-methyl-5 alpha-androstane-3 beta,17 alpha-diol,17 alpha-methyl-5 beta-androstane-3 beta,17 beta-diol,17 beta-methyl-5 beta-androstane-3 alpha,17 alpha-diol and 17 beta-methyl-5 beta-androstane-3 beta,17 alpha-diol were synthesized for the first time. 1H NMR spectra of all four 17 xi-hydroxy/17 xi-methyl C-3 ketones and all eight C-3 alcohols were recorded in chloroform-d and pyridine-d5. Pyridine-induced chemical shifts are discussed. Thin-layer chromatographic data are given.