7-羟基睾酮 | 62-83-9

• 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: 7-羟基睾酮
• 中文别名: 偏磷酸钡
• 英文名称: 7α,17β-dihydroxyandrost-4-en-3-one
• 英文别名: 4-androsten-7α,17β-diol-3-one；7α-hydroxymethyltestosterone；7α-hydroxytestosterone；7α-Hydroxy-testosteron；7alpha-Hydroxytestosterone；(7R,8R,9S,10R,13S,14S,17S)-7,17-dihydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 62-83-9
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: RNCGWYKXAJCOLD-JUKXBMAYSA-N

物化性质

• 熔点：
  218-220 °C
• 沸点：
  478.0±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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,S36/37/39,S53
• 危险类别码：
  R40,R61

反应信息

• 作为反应物：
  描述：

  7-羟基睾酮 在 羟胺 作用下， 以 水 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: A screening approach to detect forbidden treatments

  摘要：

  Estradiol benzoate (EB) has been one of the most widely used estrogenic agents in animal husbandry, as a way of exogenously introducing the natural hormone estradiol-17 beta into the animal organism. Estradiol was previously employed to induce anabolic effects or reproductive improvements in cattle. However, the employment of EB in European countries has been permanently forbidden by Directive 2008/97/EC to guarantee consumers' health. Despite this prohibition, the control of estradiol-17 beta and its esters continues to be a difficult task for residue-monitoring plans in European Communities because official analyses of natural thresholds for hormones in cattle have not yet been established, leading to a lack of confirmation for any exogenous administration of natural hormones. Several researchers have worked on excretion profiles of metabolites, variation in specific hormonal ratios and metabolomic fingerprints after hormonal treatments. This research focuses on the possible existence of disturbances in the serum profile of animals treated with EB in terms of steroid sex hormones (androgens, oestrogens and progestogens), by investigating the serum levels of several of these hormones. The serum samples were collected from three groups of cows: one treated with an intramuscular injection of EB, one treated with a combination of intravaginal EB and progesterone and a control (non-treated) group. The samples have been analysed by a validated high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) method, and 17 natural hormones were identified and quantified. Subsequently, data from the serum profiles were submitted for statistic and multivariate analysis, and it was possible to observe a manifest variation between animal groups. The obtained results can help in the development of a viable screening tool for monitoring purposes in cattle. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.12.005
• 作为产物：
  描述：

  7α-(dimethylfluorosilyl)-17β-hydroxyandrost-4-en-3-one 在 potassium fluoride 、 间氯过氧苯甲酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以98%的产率得到7-羟基睾酮
  参考文献：
  名称：

  通过共轭添加甲硅烷基铜酸酯试剂合成羟基化甾体激素。

  摘要：

  研究了通过将Fleming的甲硅烷基-杯酸酯试剂（PhMe2Si）2CuLi，一种被掩蔽的羟基缀合到适当的烯酮中来合成几种羟基化的类固醇。通过这种方法，从17个β-羟基雄甾烯-4,6-dien-3-one（1a）以良好的收率获得了7个α-羟基睾丸激素（7），尽管对17个β-羟基雄甾烯-1,4-dien-3的反应相似-一（8）产生低产率的1α-羟基睾丸酮（13）的主要原因是苯基甲硅烷基中间体向卤代硅烷的转化率低。以类似的方式从3 beta-hydroxy-5 alpha-pregn-16-en-20-one和5 alpha-cholestane-1获得3 beta，16 alpha-Dihydroxy-5 alpha-pregnan-20-one（18b）。通过共轭加成甲硅烷基，还原羰基官能团，由1-en-3-one（14）生成alpha，3 alpha-diol（17），

  DOI：

  10.1016/0039-128x(94)90102-3

文献信息

• Dehydroepiandrosterone (DHEA) congeners for prevention and/or treatment of ulcers
  申请人：——

  公开号：US20040121991A1

  公开（公告）日：2004-06-24

  The present invention is related to acute therapeutic uses of dehydroepiandrosterone (DHEA) congeners. These uses include methods for treating or preventing ulcers which comprise administering to a subject either at risk or in need thereof having an ulcer a therapeutic amount of DHEA congener.

  本发明涉及脱氢表雄酮（DHEA）类似物的急性治疗用途。这些用途包括治疗或预防溃疡的方法，包括向患有溃疡风险或需要治疗的受试者施用治疗量的DHEA类似物。
• Biotransformation of methyltestosterone by the filamentous fungus Mucor racemosus
  作者：M. Torshabi、M. Badiee、M. A. Faramarzi、H. Rastegar、H. Forootanfar、E. Mohit

  DOI：10.1007/s10600-011-9830-7

  日期：2011.3

  Fungi have proved to be powerful biocatalysts in steroid biotransformations. In the present study, the soil isolate filamentous fungus Mucor racemosus was applied for bioconversion of methyltestosterone (1), an anabolic steroid, in a five-day fermentation. Microbial metabolites were purified chromatographically and identified on the basis of their spectral data as 7α-hydroxymethyltestosterone (2), 15α-hydroxymethyltestosterone (3), and 12,15α-dihydroxymethyltestosterone (4). Observed modifications were hydroxylations at C-7α, C-12, and 15α-positions. Best fermentation condition for production of hydroxylated derivatives was found to be 25°C at 150 rpm for 5 days with a substrate concentration of 1 mg/mL.

  真菌已被证明是类固醇生物转化过程中强有力的生物催化剂。在本研究中，土壤分离丝状真菌 Mucor racemosus 在为期五天的发酵中被用于生物转化同化类固醇甲基睾酮（1）。微生物代谢产物经色谱纯化，并根据其光谱数据鉴定为 7α-羟甲基睾酮（2）、15α-羟甲基睾酮（3）和 12,15α-二羟甲基睾酮（4）。观察到的修饰为 C-7α、C-12 和 15α 位的羟基化。生产羟基化衍生物的最佳发酵条件为 25°C、150 rpm、5 天，底物浓度为 1 mg/mL。
• Process for the preparation of 7.alpha.-hydroxylated steroids
  申请人：Hoffmann-La Roche Inc.

  公开号：US04220716A1

  公开（公告）日：1980-09-02

  A fermentation process for the preparation of 7.alpha.-hydroxylated steroids utilizing strains of the genus Mucor is disclosed. The 7.alpha.-hydroxylated steroids are useful intermediates for the synthesis of chenodeoxycholic acid as well as steroidal hormones.

  本发明揭示了利用Mucor属菌株进行制备7α-羟基化类固醇的发酵过程。7α-羟基化类固醇是合成降脱氧胆酸以及类固醇激素的有用中间体。
• Process for the manufacture of hydroxylated steroids
  申请人：Hoffmann-La Roche, Inc.

  公开号：US04336332A1

  公开（公告）日：1982-06-22

  The invention relates to a process for producing 7.sub..alpha. -hydroxylated steroids by fermenting or reacting a steroid to be hydroxylated with microorganisms of the genus Botryodiplodia or enzyme extracts thereof until hydroxylation occurs. The invention process produces steroid compounds which are pharmacologically valuable substances.

  本发明涉及一种通过使用属于Botryodiplodia属微生物或其酶提取物与待羟化类固醇进行发酵或反应的过程来生产7.sub..alpha.-羟基化类固醇的方法。本发明的过程生产出具有药理学价值的类固醇化合物。
• METHOD FOR BIOCATALYSIS USING FILAMENTOUS FUNGI
  申请人：Reese Paul B.

  公开号：US20090246850A1

  公开（公告）日：2009-10-01

  A method is disclosed in which filamentous fungi are macerated and encapsulated in an inert matrix to form beads, which can be used to promote reactions carried out by the fungi. The beads are useful, e.g., for producing compounds and compound libraries.

  本发明公开了一种方法，其中纤维状真菌被磨碎并封装在惰性基质中形成珠子，可用于促进真菌所进行的反应。这些珠子可用于生产化合物和化合物库等领域。