7α,17β-dihydroxy-17-methyl-4-androsten-3-one | 972-50-9

• 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
• 英文名称: 7α,17β-dihydroxy-17-methyl-4-androsten-3-one
• 英文别名: 7α-hydroxy-17α-methyltestosterone；7α-Hydroxy-17α-methyl-testosteron；7alpha,17beta-Dihydroxy-17alpha-methylandrost-4-en-3-one；(7R,8R,9S,10R,13S,14S,17S)-7,17-dihydroxy-10,13,17-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 972-50-9
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: HBNWWAPEFHXKKT-QMNUTNMBSA-N

物化性质

• 熔点：
  190 °C
• 沸点：
  477.2±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  7α,17β-dihydroxy-17-methyl-4-androsten-3-one 在 吡啶 、 silver(l) oxide 作用下， 生成 7α-Hydroxy-17α-methyl-testosteron-7-methylether-17-propionat
  参考文献：
  名称：

  Irmscher,K. et al., Chemische Berichte, 1964, vol. 97, p. 3363 - 3373

  摘要：

  DOI：
• 作为产物：
  描述：

  17-甲睾酮 生成 7α,17β-dihydroxy-17-methyl-4-androsten-3-one
  参考文献：
  名称：

  Irmscher,K. et al., Chemische Berichte, 1964, vol. 97, p. 3363 - 3373

  摘要：

  DOI：

文献信息

• Application of α- and β-naphthoflavones as monooxygenase inhibitors of Absidia coerulea KCh 93, Syncephalastrum racemosum KCh 105 and Chaetomium sp. KCh 6651 in transformation of 17α-methyltestosterone
  作者：Tomasz Janeczko、Jarosław Popłoński、Ewa Kozłowska、Monika Dymarska、Ewa Huszcza、Edyta Kostrzewa-Susłow

  DOI：10.1016/j.bioorg.2018.03.021

  日期：2018.8

  and 9% yields, respectively. S. racemosum KCh 105 afforded 7α-, 15α- and 11α-hydroxy derivatives with yields of 45%, 19% and 17%, respectively. Chaetomium sp. KCh 6651 afforded 15α-, 11α-, 7α-, 6β-, 9α-, 14α-hydroxy and 6β,14α-dihydroxy derivatives with yields of 31%, 20%, 16%, 7%, 5%, 7% and 4%, respectively. 14α-Hydroxy and 6β,14α-dihydroxy derivatives were determined as new compounds. Effect of various

  在这项工作中，芥蓝KCh 93，Syncephalastrum racemosum KCh 105和Chaetomium sp有效地羟基化了17α-甲基睾丸激素。KCH 6651. A.犁头KCH 93得到6β-，12β-，7α-，11α-，15α羟基衍生物与分别为44％，29％，6％，5％和9分％的收率。小号。总消旋体KCh 105提供7α-，15α-和11α-羟基衍生物，产率分别为45％，19％和17％。毛毛虫sp。KCh 6651提供15α-，11α-，7α-，6β-，9α-，14α-羟基和6β，14α-二羟基衍生物，产率分别为31％，20％，16％，7％，5％，7％和4 ％， 分别。确定了14α-羟基和6β，14α-二羟基衍生物为新化合物。测试了培养基中氮和碳的各种来源对生物转化的影响，但是没有影响底物转化的程度或形成的产物的组成。添加α-或β-萘黄酮抑制了17α-甲基睾丸酮的羟化作用，但没有改变所得产物的百分比组成。
• Novel metabolites of dehydroepiandrosterone and progesterone obtained in Didymosphearia igniaria KCH 6670 culture
  作者：Tomasz Janeczko、Alina Świzdor、Jadwiga Dmochowska-Gładysz、Agata Białońska、Zbigniew Ciunik、Edyta Kostrzewa-Susłow

  DOI：10.1016/j.molcatb.2012.05.009

  日期：2012.10

  Dehydroepiandrosterone (DHEA) (10) and its five derivatives: testosterone (1), androstenedione (2), 17 alpha-methyltestosterone (6), progesterone (13) and pregnenolone (14) were subjected to microbial transformation by the filamentous fungus Didymosphaeria igniaria KCH 6670. The predominant metabolism of the incubated 5-ene steroids (10 and 14) occurred through 3 beta-hydroxy-steroid dehydrogenase/5.4-en isomerase pathways resulting in the generation of a 4-en-3-oxo system on ring-A. The transformations of C-19 steroids (1, 2, and 10) included a hydroxylation at 7 alpha position, ketone-alcohol interconversion at C-17 and reduction of the double bond at C-4 and 3-keto group to the 3 beta-alcohol with 5 alpha-stereochemistry at A/B ring. D. igniaria also carried out 6(7)-dehydrogenation and 6,7 beta-epoxidation during transformation of DHEA. Under these conditions transformation of DHEA (10) gave four products: 7 alpha-hydroxyandrost-4-en-3,17-dione (4), 17 beta-hydroxyandrost-4,6-dien-3-one (11), 17 beta-hydroxyandrost-6 beta-epoxy-4-en-3-one (12) and 3 beta,17 beta-dihydroxy-5 alpha-androstane (5). The compounds 11 and 12 are identified as DHEA metabolites for the first time. The transformation of C-21 steroids (13 and 14) led to the mixture of mono-(mainly 11 alpha- and 15 beta-) and dihydroxy- (7 alpha,15 beta-: 14 alpha,15 beta-; 11 alpha,15 beta-; 11 alpha,14 alpha-) products. 7 alpha,15 beta-Dihydroxypregnan-4-en-3,20-dione (18) and 14 alpha,15 beta-dihydroxypregnan-4-en-320-dione (19) were found to be new compounds. The main product of transformation of 17 alpha-methyltestosterone (6) was 12 beta-hydroxy-17 alpha-methyltestosterone (7). The results of these transformations demonstrate the dependence of hydroxylation position on the structure of steroid nucleus. (c) 2012 Elsevier B.V. All rights reserved.