6β,24α-dihydroxypregn-4-ene-3,20-dione | 599-27-9

• 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: 6β,24α-dihydroxypregn-4-ene-3,20-dione
• 英文别名: pregn-4-ene-6β,14α-diol-3,20-dione；6β,14α-dihydroxyprogesterone；6β,14-dihydroxy-pregn-4-ene-3,20-dione；6β,14-Dihydroxy-pregn-4-en-3,20-dion；(6R,8R,9S,10R,13R,14R,17S)-17-acetyl-6,14-dihydroxy-10,13-dimethyl-2,6,7,8,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 599-27-9
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: LQCNIUSTCXGYKI-PIABYFCUSA-N

物化性质

• 熔点：
  246-249 °C
• 沸点：
  525.7±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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

• 作为反应物：
  描述：

  6β,24α-dihydroxypregn-4-ene-3,20-dione 在 氢氧化钾 作用下， 生成 14-hydroxy-5α-pregnane-3,6,20-trione
  参考文献：
  名称：

  Camerino et al., Gazzetta Chimica Italiana, 1953, vol. 83, p. 684,690

  摘要：

  DOI：
• 作为产物：
  描述：

  progesterone 生成 6β,24α-dihydroxypregn-4-ene-3,20-dione
  参考文献：
  名称：

  Camerino et al., Gazzetta Chimica Italiana, 1953, vol. 83, p. 684,690

  摘要：

  DOI：

文献信息

• Microbial hydroxylation of steroids. Part 12. Hydroxylation of testosterone and related steroids by <i>Gnomonia</i><i>fructicola</i> ATCC 11430
  作者：Herbert L. Holland、Frances M. Brown、P. Chinna Chenchaiah、Michael J. Chernishenko、Shaheer H. Khan、J. Appa Rao

  DOI：10.1139/v89-044

  日期：1989.2.1

  The fungus Gnomoniafructicola ATCC 11430 hydroxylates testosterone at C-2β in 40–60% yield. The enzyme involved has been shown to be an inducible CO sensitive, cyanide insensitive oxygenase, with a requirement for theΔ⁴-3-ketosteroid substrate functionality. The use of 2α- and 2β-deuterium labelled substrates has shown that hydrogen loss from C-2 during 2β hydroxylation is isotope dependent and non-stereospecific. This is interpreted in terms of a Δ^2,4-dienolic enzyme-bound intermediate form of the substrate. Keywords: Gnomoniafructicola, hydroxylation, steroids, testosterone.

  真菌Gnomoniafructicola ATCC 11430以40-60%的产率在C-2β处对睾酮进行羟基化。所涉及的酶已被证明是一种可诱导的CO敏感、氰化物不敏感的氧化酶，需要Δ4-3-酮类固醇底物的功能性。使用2α-和2β-氘标记底物表明，在2β羟基化过程中，C-2处的氢损失是同位素依赖的，且不具有立体特异性。这被解释为底物的Δ2,4-二烯醇酶结合中间体形式。关键词：Gnomoniafructicola、羟基化、类固醇、睾酮。
• Microbial transformation of steroids: Contribution to 14α-hydroxylations
  作者：Shang-hui Hu、Gilles Genain、Robert Azerad

  DOI：10.1016/0039-128x(95)00006-c

  日期：1995.4

  The regioselective and stereoselective hydroxylation of steroids by fungal strains previously known for their hydroxylation capabilities, such as Thamnostylum (= Helicostylum) piriforme ATCC 8992, Mucor griseocyanus ATCC 1207a, Actinomucor elegans (= Mucor parasiticus) MMP 3122 (Mucorales), and Zygodesmus sp. ATCC 14716, was investigated with special interest for the 14 alpha-hydroxylation reaction

  以前以其羟基化能力而闻名的真菌菌株对类固醇的区域选择性和立体选择性羟基化，例如 Thamnostylum (= Helicostylum) piriforme ATCC 8992、Mucor griseocyanus ATCC 1207a、Actinomucor elegans (= Mucor parasiticus) MMP 3122 (MMP. ATCC 14716 对 14 α-羟基化反应特别感兴趣。初步筛选表明，其中一些微生物足以产生以下类固醇的 14 种 α-羟基化衍生物：孕酮、5 β-孕烷-3,20-二酮、3 β-羟基-5 β-孕烷-20 -one、3 beta-hydroxy-5 beta-17 (alpha H)-etianic酸甲酯、androst-4-ene-3,17-dione 和睾酮。大约 20 种代谢物已通过硅胶色谱法和半制备型反相 HPLC 分离和纯化。这些代谢物已通过
• Tanabe et al., Chemical and pharmaceutical bulletin, 1959, vol. 7, p. 811,815
  作者：Tanabe et al.

  DOI：——

  日期：——
• Biotransformations of steroid compounds by Chaetomium sp. KCH 6651
  作者：Tomasz Janeczko、Jadwiga Dmochowska-Gładysz、Edyta Kostrzewa-Susłow、Agata Białońska、Zbigniew Ciunik

  DOI：10.1016/j.steroids.2009.02.006

  日期：2009.8

  Biotransformations of steroid compounds: androstenedione, testosterone. progesterone, pregnenolone and DHEA using Chaetomium sp. 1 KCH 6651 strain as a biocatalyst were investigated. The microorganism proved capable of selective hydroxylation of the steroid substrates. Androstenedione was converted to 14 alpha-hydroxynadrost-4-en-3,17-dione (in over 75% yield) and 6 beta-hydroxyandrost-4-en-3,17-dione (in low yield), while testosterone underwent regioselective hydroxylation at 6 beta position. Progesterone was transformed to a single product-6 beta-,14 alpha-dihydroxypregnan-4-en-3,20-dione in high yield, whereas biotransformation of DHEA resulted in the formation of 7 alpha-hydroxy derivative, which was subsequently converted to 7 alpha-hydroxyandrost-4-en-3,17-dione. (C) 2009 Elsevier Inc. All rights reserved.
• Tsuda et al., 1959, vol. 5, p. 7,8
  作者：Tsuda et al.

  DOI：——

  日期：——