6alpha-羟基睾酮 | 2944-87-8

• 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: 6alpha-羟基睾酮
• 中文别名: 4-雄烯-6a,17b-二醇-3-酮；6α-羟基睾酮
• 英文名称: 6alpha-Hydroxytestosterone
• 英文别名: 6α,17β-dihydroxyandrost-4-ene-3-one；4-androstene-6α,17β-diol-3-one；6α-Hydroxytestosterone；6α-Hydroxy-testosteron；(6S,8R,9S,10R,13S,14S,17S)-6,17-dihydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 2944-87-8
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: XSEGWEUVSZRCBC-QXROXWLYSA-N

物化性质

• 沸点：
  479.8±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)
• 溶解度：
  少许溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S22,S36
• 危险类别码：
  R20/21/22,R40,R63

反应信息

• 作为反应物：
  描述：

  N-甲基-N-(三甲基硅烷基)三氟乙酰胺 、 6alpha-羟基睾酮 在 咪唑 、 potassium acetate 作用下， 生成 (6S,8R,9S,10R,13S,14S,17S)-10,13-Dimethyl-3,6,17-tris-trimethylsilanyloxy-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene
  参考文献：
  名称：

  Metabolism of anabolic steroids in humans: Synthesis of 6β-hydroxy metabolites of 4-chloro-1,2-dehydro-17α-methyltestosterone, fluoxymesterone, and metandienone

  摘要：

  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.

  DOI：

  10.1016/0039-128x(95)00008-e
• 作为产物：
  描述：

  在 盐酸 作用下， 以 异丙醇 为溶剂， 反应 0.33h， 以400 mg的产率得到6,17-二羟基-6b,17b-雄甾-4-烯-3-酮
  参考文献：
  名称：

  Metabolism of anabolic steroids in humans: Synthesis of 6β-hydroxy metabolites of 4-chloro-1,2-dehydro-17α-methyltestosterone, fluoxymesterone, and metandienone

  摘要：

  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.

  DOI：

  10.1016/0039-128x(95)00008-e

文献信息

• Method for redox reaction using an old yellow enzyme
  申请人：Glieder Anton

  公开号：US20090117613A1

  公开（公告）日：2009-05-07

  A method of selective biooxidation to non activated carbon-hydrogen bonds of substances using a Geobacillus kaustophilus ‘Old Yellow Enzyme’ is provided”. It is shown that OYEs can be used to facilitate the biooxydation of substances, such as testosterone. It is also shown that OYE can introduce double bonds to form alpha, betaalpha, beta desaturated ketones. Furthermore, it is also shown that the use of OYEs allows for the production of oxidized substances in one step reactions, which are otherwise not accessible or only accessible after complex and inefficient multi-step reactions. In addition, the OYE used shows high stability (e.g. at high temperature, or in long lasting bioconversions). An exemplary embodiment is provided showing the use of an OYE to convert testosterone to 6α-hydroxytestosterone.

  提供了一种使用Geobacillus kaustophilus的“Old Yellow Enzyme”进行选择性生物氧化非活化碳氢键物质的方法。结果表明，OYEs可用于促进物质（如睾酮）的生物氧化作用。同时，OYE还可以引入双键形成α，βα，β不饱和酮。此外，使用OYEs还可以通过一步反应生产氧化物质，否则只能通过复杂且低效的多步反应获得或无法获得。此外，所使用的OYE显示出高稳定性（例如在高温或长时间的生物转化中）。提供了一个示例实施方案，显示使用OYE将睾酮转化为6α-羟基睾酮。
• Modulation of cytochrome P450 reductase activity
  申请人：——

  公开号：US20040010809A1

  公开（公告）日：2004-01-15

  The present invention relates to non-human transgenic animals, tissues and/or cells derived therefrom having depleted or ablated cytochrome P450 reductase (CPR) expression, methods of producing such animals, tissues and/or cells, and methods of using such animals, tissues and/or cells. Non-human transgenic animals, tissues and or cells derived therefrom of the present invention may be used for, but non exclusively, in both in vivo and in vitro screening of therapeutic agents, drug development, drug metabolism/disposition studies and studying disease states, pregnancy, fetal development, modulation of hormone function and hormone levels, and other pathways and/or substrate metabolism in which cytochrome P450 plays a role.

  本发明涉及细胞色素P450还原酶（CPR）表达减少或消失的非人类转基因动物、组织和/或由此衍生的细胞，生产这种动物、组织和/或细胞的方法，以及使用这种动物、组织和/或细胞的方法。本发明衍生的非人类转基因动物、组织和/或细胞可用于（但不限于）治疗剂的体内和体外筛选、药物开发、药物代谢/处置研究和疾病状态研究、妊娠、胎儿发育、激素功能和激素水平的调节，以及细胞色素 P450 在其中发挥作用的其他途径和/或底物代谢。
• Studies on Bacillus stearothermophilus
  作者：S. Al-Awadi、M. Afzal、S. Oommen

  DOI：10.1016/j.steroids.2004.12.003

  日期：2005.4

  The impact of chemical enhancers on the biotransformation of testosterone has been exploited. Application of crude cell concentrates to produce Bacillus stearothermophilus-mediated bioconversion of testosterone at 65 degrees C for 72 h has been examined. After incubation, the xenobiotic substrate was added to the concentrated whole cell suspensions. The enhancer molecules were included in the whole cell suspension. The resultant products, after extraction into an organic solvent, were purified by thin layer chromatography and identification was carried out through spectroscopic data. Five steroid metabolites 9,10-seco-4-androstene-3,9,17-trione, 5 alpha-androstan-3,6,17-trione, 17 beta-hydroxy-5 alpha-androstan-3,6-dione, 3 beta,17 beta-dihydroxyandrost-4-ene-6-one and 17 beta-hydroxyandrost-4,6-diene-3-one were identified as biotransformation products of testosterone. A possible biosynthetic route for these bioconversion products is postulated. (c) 2005 Elsevier Inc. All rights reserved.
• Cryopreservation of Hepatocytes
  申请人：Arseniev Lubomir

  公开号：US20080280357A1

  公开（公告）日：2008-11-13

  The invention relates to processes for the preparation of liver cells for cryopreservation, processes for cryopreservation of isolated liver cells and processes for the preparation of a culture of cryopreserved isolated liver cells.
• METHOD OF BIOOXIDATION USING AN OLD YELLOW ENZYME
  申请人：Glieder Anton

  公开号：US20090117612A1

  公开（公告）日：2009-05-07

  A method for a chemoselective and regioselective enzyme mediated oxidation of carbon-hydrogen bonds of substrates using a Geobacillus kaustophilus ‘Old Yellow Enzyme’ is provided. It is shown that OYEs can be used to facilitate the bioxidation of substrates, such as testosterone. It is also shown that the use of OYEs allows for the production of oxidized substrates in one step reactions, which are otherwise not accessible or only accessible after complex and inefficient multi-step reactions. In addition, the OYE used shows high stability at high temperature. An exemplary embodiment is provided showing the use of an OYE to convert testosterone to 6α-hydroxytestosterone.