19-hydroxydihydrotestosterone | 2026-82-6

• 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: 19-hydroxydihydrotestosterone
• 英文别名: 17β,19-dihydroxy-5α-androstan-3-one；17β,19-Dihydroxy-5α-androstan-3-on；17-Hydroxyandrostan-19-ol-3-one；(5S,8R,9S,10R,13S,14S,17S)-17-hydroxy-10-(hydroxymethyl)-13-methyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• CAS: 2026-82-6
• 化学式: C₁₉H₃₀O₃
• 分子量: 306.445
• InChiKey: ZCXLTIZTHGOSFH-GLOHGQAKSA-N

物化性质

• 沸点：
  460.9±30.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  19-hydroxydihydrotestosterone 在 lithium aluminium tetrahydride 作用下， 生成 5α-androstane-3β,17β,19-triol
  参考文献：
  名称：

  Steroids. CCLXXVIII.¹ Reductions of 19-Substituted Androst-4-en-3-ones and Related Compounds

  摘要：

  DOI：

  10.1021/jo01018a019
• 作为产物：
  描述：

  3-oxo-19-(tetrahydropyran-2'-yl-oxy)-5α-androstan-17β-yl acetate 在 盐酸 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 4.08h， 生成 19-hydroxydihydrotestosterone
  参考文献：
  名称：

  Oxidation of Dihydrotestosterone by Human Cytochromes P450 19A1 and 3A4

  摘要：

  Dihydrotestosterone is a more potent androgen than testosterone and plays an important role in endocrine function. We demonstrated that, like testosterone, dihydrotestosterone can be oxidized by human cytochrome P450 (P450) 19A1, the steroid aromatase. The products identified include the 19-hydroxy- and 19-oxo derivatives and the resulting Delta(1,10)-, Delta(5,10)-, and Delta(9,10)-dehydro 19-norsteroid products (loss of 19-methyl group). The overall catalytic efficiency of oxidation was similar to 10-fold higher than reported for 3 alpha-reduction by 3 alpha-hydroxysteroid dehydrogenase, the major enzyme known to deactivate dihydrotestosterone. These and other studies demonstrate the flexibility of P450 19A1 in removing the 1- and 2-hydrogens from 19-norsteroids, the 2-hydrogen from estrone, and (in this case) the 1-, 5 beta-, and 9 beta-hydrogens of dihydrotestosterone. Incubation of dihydrotestosterone with human liver microsomes and NADPH yielded the 18- and 19-hydroxy products plus the Delta(1,10)-dehydro 19-nor product identified in the P450 19A1 reaction. The 18- and 19-hydroxylation reactions were attributed to P450 3A4, and 18- and 19-hydroxydihydrotestosterone were identified in human plasma and urine samples. The change in the pucker of the A ring caused by reduction of the Delta(4,5) bond is remarkable in shifting the course of hydroxylation from the 6 beta-, 2 beta-, 1 beta-, and 15 beta-methylene carbons (testosterone) to the axial methyl groups (18, 19) in dihydrotestosterone and demonstrates the sensitivity of P450 3A4, even with its large active site, to small changes in substrate structure.

  DOI：

  10.1074/jbc.m112.390047

文献信息

• Synthesis of and chemical model reaction studies with 3-deoxyandrogens: evidence supporting a 2, 3-enolization hypothesis in human placental aromatase catalysis
  作者：Soonsin S. Oh、Cecil H. Robinson

  DOI：10.1039/p19940002237

  日期：——

  A number of hitherto undescribed Δ2- and Δ3-3-deoxy-5α-androgen derivatives (17β,19-diols 12 and 13, 19-hydroxy-17-ketones 16 and 17, 19-oxo-17-ketones 18 and 19) were synthesized in good yield. The lithium-ammonia reduction of 19-(tetrahydropyran-2-yloxy)androst-4-ene-3, 17-dione 7 followed by Shapiro reaction allowed easy construction of both Δ2- and Δ3-3-deoxy-5α-steroid systems. An improved synthesis

  许多迄今未描述的Δ 2 -和Δ 3 -3脱氧5α雄激素衍生物（17β，19-二醇12和13，19-羟基-17-酮16和17，19氧代-17-酮18和19）以高收率合成。锂-氨还原的19-（四氢吡喃-2-基氧基）雄甾-4-烯-3- -3,17-二酮7接着夏皮罗反应允许易于施工两个Δ的2 -和Δ 3 -3脱氧5α类固醇系统。已知的Δ的改进的合成4 -3- deoxyandrogen衍生物（28，30，31）以高产量完成。19位羟基的掩蔽，以产生Δ是必要4以良好的收率-3- deoxyandrogen系统，在对比的是帐户化合物的早期合成的28和30通过Numazawa。在芳香动作第三氧化处理的化学模型进行反应与Δ 2 - ，Δ 3 - ，Δ 4 -和Δ 2,4 -3-脱氧-19-氧代- 17-酮甾族化合物（18，19，31和5分别）。结果示出了用于两个Δ需要2 -和Δ 4，以便产生Δ-unsat
• US4071625A
  申请人：——

  公开号：US4071625A

  公开（公告）日：1978-01-31
• Steroids. CCLXXVIII.¹ Reductions of 19-Substituted Androst-4-en-3-ones and Related Compounds
  作者：L. H. Knox、E. Blossey、H. Carpio、L. Cervantes、P. Crabbé、E. Velarde、J. A. Edwards

  DOI：10.1021/jo01018a019

  日期：1965.7
• Oxidation of Dihydrotestosterone by Human Cytochromes P450 19A1 and 3A4
  作者：Qian Cheng、Christal D. Sohl、Francis K. Yoshimoto、F.Peter Guengerich

  DOI：10.1074/jbc.m112.390047

  日期：2012.8

  Dihydrotestosterone is a more potent androgen than testosterone and plays an important role in endocrine function. We demonstrated that, like testosterone, dihydrotestosterone can be oxidized by human cytochrome P450 (P450) 19A1, the steroid aromatase. The products identified include the 19-hydroxy- and 19-oxo derivatives and the resulting Delta(1,10)-, Delta(5,10)-, and Delta(9,10)-dehydro 19-norsteroid products (loss of 19-methyl group). The overall catalytic efficiency of oxidation was similar to 10-fold higher than reported for 3 alpha-reduction by 3 alpha-hydroxysteroid dehydrogenase, the major enzyme known to deactivate dihydrotestosterone. These and other studies demonstrate the flexibility of P450 19A1 in removing the 1- and 2-hydrogens from 19-norsteroids, the 2-hydrogen from estrone, and (in this case) the 1-, 5 beta-, and 9 beta-hydrogens of dihydrotestosterone. Incubation of dihydrotestosterone with human liver microsomes and NADPH yielded the 18- and 19-hydroxy products plus the Delta(1,10)-dehydro 19-nor product identified in the P450 19A1 reaction. The 18- and 19-hydroxylation reactions were attributed to P450 3A4, and 18- and 19-hydroxydihydrotestosterone were identified in human plasma and urine samples. The change in the pucker of the A ring caused by reduction of the Delta(4,5) bond is remarkable in shifting the course of hydroxylation from the 6 beta-, 2 beta-, 1 beta-, and 15 beta-methylene carbons (testosterone) to the axial methyl groups (18, 19) in dihydrotestosterone and demonstrates the sensitivity of P450 3A4, even with its large active site, to small changes in substrate structure.