11α,14-dihydroxy-4-pregnene-3,20-dione | 599-25-7

• 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: 11α,14-dihydroxy-4-pregnene-3,20-dione
• 英文别名: 11α,14α-dihydroxyprogesterone；11,14-Dihydroxypregn-4-ene-3,20-dione；(8R,9S,10R,11R,13R,14R,17S)-17-acetyl-11,14-dihydroxy-10,13-dimethyl-2,6,7,8,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 599-25-7；95832-17-0
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: XVNVIIRMSUKNKJ-CJAFCWQJSA-N

物化性质

• 沸点：
  522.2±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)
• 熔点：
  224-229 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  黄体酮 生成 11α,14-dihydroxy-4-pregnene-3,20-dione
  参考文献：
  名称：

  MAHATO, SHASHI B.;BANERJEE, SUKDEB;MAZUMDER, IPSITA, J. CHEM. RES. (S),(1989) N, C. 184-185

  摘要：

  DOI：

文献信息

• Metabolism of progesterone and testosterone by a Bacillus sp.
  作者：Shashi B. Mahato、Sukdeb Banerjee、Niranjan P. Sahu

  DOI：10.1016/s0039-128x(84)90180-6

  日期：1984.5

  Bacillus sp. were employed as a means of preparing potentially important derivatives of progesterone and testosterone. Each microbial metabolite was subjected to structure elucidation employing 1H and 13C nmr, mass spectral and cd analysis. Hplc was used for the determination of the percentages of the metabolites formed. The progesterone metabolites were characterised as 14-hydroxy-4-pregnene-3,20-dione

  芽孢杆菌的微生物转化。曾被用作制备潜在重要的孕酮和睾丸激素衍生物的手段。使用1H和13C nmr，质谱和cd分析对每种微生物代谢产物进行结构解析。Hplc用于确定形成的代谢物的百分比。孕酮代谢物的特征为14-羟基-4-孕烯-3,20-二酮（II），14-羟基-5α-孕烯-3,6,20-三酮（III），11α-羟基-5α -孕烷-3、6,20-三酮（IV）和11α，14-二羟基-4-孕烯-3,20-二酮（V）。睾丸激素类似物被鉴定为4-雄烯酮-3,17-二酮（VII），17β-羟基-5α-雄甾烷-3,6-二酮（VIII），14-羟基-4-雄烯酮-3,17-二酮（IX）和14、17β-二羟基-4-雄烯-3-酮（X）。
• 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.