6β-羟基美雄酮 | 33526-41-9

• 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: 6β-羟基美雄酮
• 中文别名: 6Beta-羟基美雄酮；1,2,4-丁三醇-1,4-去甲酸酯
• 英文名称: 6β,17β-dihydroxy-17α-methyl-1,4-androstadien-3-one
• 英文别名: 6β,17β-dihydroxy-17α-methylandrosta-1,4-dien-3-one；6β,17β-dihydroxy-17α-methylandrost-1,4-dien-3-one；6β,17β-dihydroxy-17-methylandrosta-1,4-dien-3-one；6β-hydroxy-methandrostenolone；6β-hydroxymethandrostenolone；6β-hydroxy-methandienone；6beta-Hydroxymethandrostenolone；(6R,8R,9S,10R,13S,14S,17S)-6,17-dihydroxy-10,13,17-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
• CAS: 33526-41-9
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: OBCJFTMGLMNCTJ-INIPNLRTSA-N

物化性质

• 熔点：
  28-29 °C(Solv: ethanol (64-17-5))
• 沸点：
  481.9±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)
• 溶解度：
  乙腈：1mg/mL；乙醇：1mg/mL；甲醇：1mg/mL
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6β-羟基美雄酮 在 吡啶 、 氢氧化钾 、 三氧化硫吡啶 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 6β-hydroxy-17-epi-metandienone
  参考文献：
  名称：

  人类中17种α-甲基同化类固醇的17-表异构化：17种α-羟基-17β-甲基类固醇的代谢和合成。

  摘要：

  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

  DOI：

  10.1016/0039-128x(92)90023-3
• 作为产物：
  描述：

  美雄酮 生成 6β-羟基美雄酮
  参考文献：
  名称：

  MASSE, ROBERT;AYOTTE, CHRISTIANE;DUGAL, ROBERT, J. CHROMATOGR. BIOMED. APPL., 489,(1989) N, C. 23-50

  摘要：

  DOI：

文献信息

• Gas chromatography/chemical ionization triple quadrupole mass spectrometry analysis of anabolic steroids: ionization and collision-induced dissociation behavior
  作者：Michael Polet、Wim Van Gansbeke、Peter Van Eenoo、Koen Deventer

  DOI：10.1002/rcm.7472

  日期：2016.2.28

  detection of new anabolic steroid metabolites and new designer steroids is a challenging task in doping analysis. Switching from electron ionization gas chromatography triple quadrupole mass spectrometry (GC/EI‐MS/MS) to chemical ionization (CI) has proven to be an efficient way to increase the sensitivity of GC/MS/MS analyses and facilitate the detection of anabolic steroids. CI also extends the possibilities

  新的合成代谢类固醇代谢物和新设计的类固醇的检测在掺杂分析中是一项艰巨的任务。从电子电离气相色谱三重四极杆质谱（GC / EI-MS / MS）切换到化学电离（CI）是提高GC / MS / MS分析灵敏度并促进合成代谢类固醇检测的有效方法。CI还扩展了GC / MS / MS分析的可能性，因为分子离子由于较软的电离而保留为其质子化形式。在EI中，由于分子离子的丰度低或不存在以及广泛的（很大程度上是不可预测的）碎片，很难找到以前未知但预期的代谢物。这项工作的主要目的是研究大量合成代谢雄激素类固醇（AAS）作为其三甲基甲硅烷基衍生物的CI和碰撞诱导解离（CID）行为，以确定结构与CID片段化之间的相关性。需要澄清这些相关性，以阐明未知类固醇和新代谢产物的结构。
• Natural Product Diversification by One‐Step Biocatalysis using Human P450 3A4
  作者：Nico D. Fessner、Christopher Grimm、Matic Srdič、Hansjörg Weber、Wolfgang Kroutil、Ulrich Schwaneberg、Anton Glieder

  DOI：10.1002/cctc.202101564

  日期：2022.1.10

  Doing it all: In this study, the synthetic potential of human cytochrome P450 3A4 as a Pichia pastoris-based whole-cell biocatalyst for the diversification of natural products was successfully explored. A total of 31 authentic human metabolites of six selected natural products were isolated at a preparative 100-mg scale, many of them for the first time, revealing an unprecedented degree of diversification

  全力以赴：在这项研究中，成功​​探索了人类细胞色素 P450 3A4 作为基于毕赤酵母的全细胞生物催化剂在天然产物多样化方面的合成潜力。以 100 mg 的制备规模分离了六种选定天然产物的总共 31 种真实人体代谢物，其中许多是第一次，揭示了前所未有的多样化程度。
• Fungal transformation of methyltestosterone by the soil ascomycete Acremonium strictum to some hydroxy derivatives of 17-methylsteroid
  作者：N. Nassiri-Koopaei、M. Mogharabi、M. Amini、A. Shafiee、M. A. Faramarzi

  DOI：10.1007/s10600-013-0703-0

  日期：2013.9

  The ascomycete Acremonium strictum was used for the biotransformation of methyltestosterone (1), a pharmaceutical steroid substance, into some steroid derivatives (6β-hydroxy-17α-methyltestosterone (2), 6β,12β-dihydroxy-17α-methyltestosterone (3), 7β-hydroxy-17α-methyltestosterone (4), 6β,17β-dihydroxy-17α-methylandrosta-1,4-dien-3-one (5), and 3,17β-dihydroxy-17α-methylestra-1,3,5(10)-triene (6).

  子囊菌 Acremonium strictum 用于将药用类固醇物质甲基睾酮 (1) 生物转化为一些类固醇衍生物 (6β-羟基-17α-甲基睾酮 (2)、6β,12β-二羟基-17α-甲基睾酮 (3)、7β -羟基-17α-甲基睾酮 (4)、6β,17β-dihydroxy-17α-methylandrosta-1,4-dien-3-one (5) 和 3,17β-dihydroxy-17α-methylestra-1,3,5( 10)-三烯(6)在添加1mM底物的沙氏葡萄糖肉汤(SDB)中进行发酵，温度和通气速率分别调整为30℃和150rpm。观察到 C-6β、C-7β 和 C-12β 的羟基化、1,2-脱氢和环 A 芳构化。最佳发酵条件，如温度、底物浓度、pH、孵育时间和通气，发现分别为 25°C、1 mM、pH 6.5、6 天和 150 rpm，最大生物转化为 1。
• Metabolism of anabolic steroids in humans: Synthesis of 6β-hydroxy metabolites of 4-chloro-1,2-dehydro-17α-methyltestosterone, fluoxymesterone, and metandienone
  作者：Willi Schänzer、Steve Horning、Manfred Donike

  DOI：10.1016/0039-128x(95)00008-e

  日期：1995.4

  Hydroxylation at position 6 beta of testosterone I (17 beta-hydroxyandrost-4-en-3-one) and the anabolic steroids 17 alpha-methyltestosterone II (17 beta-hydroxy-17 alpha-methylandrost-4-en-3-one), metandienone III (17 beta-hydroxy-17 alpha-methylandrosta-1, ,4-dien-3-one), 4-chloro-1,2-dehydro-17 alpha-methyltestosterone IV (4-chloro-17 beta-hydroxy-17 alpha-methylandrosta-1 ,4-dien-3-one), and fluoxymesterone V (9-fluoro-11 beta, 17 beta-dihydroxy-17 alpha-methylandrost-4-en-3-one) was achieved via light-induced autooxidation of the corresponding trimethylsilyl 3,5-dienol ethers dissolved in isopropanol or ethanol. The reaction further yielded the 6 alpha-hydroxy isomer in low amounts. The 6 beta-hydroxy isomers of I-V and the 6 alpha-hydroxy isomers of I, III, and IV were isolated and characterized by H-1 and C-13 NMR, high-performance liquid chromatography, gas chromatography, and mass spectrometry. Human excretion studies with single administered doses of boldenone (17 beta-hydroxyandrosta-1,4-dien-3-one), 4-chloro-1,2 -dehydro-17 alpha-methyltestosterone, fluoxymesterone, metandienone, 17 alpha-methyltestosterone, and [16, 16, 17-H-2(3)]testosterone showed that 6 beta-hydroxylation is the major metabolic pathway in the metabolism of 4-chloro-1,2-dehydro-17 alpha-methyltestosterone, fluoxymesterone, and metandienone, whereas for boldenone, 17 alpha-methyltestosterone, and testosterone, 6 beta-hydroxylation is negligable.
• Steroids? transformations in culture
  作者：A BARTMANSKA、J DMOCHOWSKAGLADYSZ、E HUSZCZA

  DOI：10.1016/j.steroids.2004.11.011

  日期：2005.3

  The application of Penicillium notation genus for biotransformations of steroids has been investigated. The reactions observed include insertion of an oxygen atom into D-ring of steroids, 15 alpha-hydroxylation of 17 alpha-methyl testosterone derivatives, ester bond hydrolysis, and degradation of a testosterone derivatives side chain.Microbial production of testolactones, the biologically active compounds. was also achieved using this strain in up to 98% yield. (c) 2005 Elsevier Inc. All rights reserved.