9α,17β-dihydroxy-4-androsten-3-one | 18841-73-1

• 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: 9α,17β-dihydroxy-4-androsten-3-one
• 英文别名: 9α,17β-dihydroxyandrost-4-en-3-one；9,17β-dihydroxy-4-androsten-3-one；9α-hydroxytestosterone；9α-Hydroxy-testosteron；(17|A)-9,17-dihydroxyandrost-4-en-3-one；(8S,9R,10S,13S,14S,17S)-9,17-dihydroxy-10,13-dimethyl-2,6,7,8,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 18841-73-1
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: UKICFXLKLKVHMC-KOUJMVCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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

反应信息

• 作为产物：
  描述：

  黄体酮 生成 9α,17β-dihydroxy-4-androsten-3-one
  参考文献：
  名称：

  Microbiological Transformations. VII. The Hydroxylation of Steroids at C-9

  摘要：

  DOI：

  10.1021/ja01483a030

文献信息

• 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
• Steroid 9α-Hydroxylation during Testosterone Degradation by RestingRhodococcus equiCells
  作者：Yong-ung Kim、Jaehong Han、Sang Sup Lee、Kuniyoshi Shimizu、Yuji Tsutsumi、Ryuichiro Kondo

  DOI：10.1002/ardp.200600175

  日期：2007.4

  conversion pathway of testosterone to androst‐4‐ene‐3,17‐dione and 9α‐hydroxy androstane metabolites, 9α‐hydroxyandrost‐4‐ene‐3,17‐dione and 9α,17β‐dihydroxyandrost‐4‐en‐3‐one was proposed for the ring degradation in steroids by a minimal liquid medium (NMMP)‐dispersed Rhodococcus equi ATCC 14887. The microorganism produced 9α‐hydroxy androstane metabolites from testosterone at high conversion ratio

  睾酮转化为雄甾醇-4-烯-3,17-二酮和9α-羟基雄甾烷代谢物、9α-羟基雄甾醇-4-烯-3,17-二酮和9α、17β-二羟基雄甾醇-烯-43的转化途径一种被提议用于通过最小液体介质 (NMMP) 分散的马红球菌 ATCC 14887 在类固醇中进行环降解。该微生物以高转化率从睾酮中产生 9α-羟基雄甾烷代谢物，而无需添加环降解抑制剂。几种基于NMMP的培养基对微生物转化的影响相似，其中9α-羟基雄甾醇-4-烯-3,17-二酮和9α、17β-二羟基雄甾醇-4-烯-3-one的摩尔产率分别约为. 3 到 47% 和大约 分别为 3% 到 11%，而营养肉汤，一种丰富的培养基，基本上没有积累。在这个证据的基础上，
• Process for the preparation of 9(11)-dehydroandrostanes
  申请人：GIST-BROCADES N.V.

  公开号：EP0253415A1

  公开（公告）日：1988-01-20

  A 9(ll)-dehydroandrostane is prepared from the corresponding 9-alpha-hydroxyandrostane in good yield by boiling a solution of the former compound with p-toluene­sulfonic acid or naphtalenesulfonic acid in the presence of silica gel.

  在硅胶存在下，将前一种化合物与对甲苯磺酸或萘磺酸的溶液沸腾，可从相应的 9-α-羟基雄甾烷制备出 9(ll)-脱氢雄甾烷，收率很高。
• Process for the preparation of 9(11)-dehydro steroids
  申请人：ROUSSEL-UCLAF

  公开号：EP0294911B1

  公开（公告）日：1992-10-14
• Microbial degradation of the phytosterol side-chain to 24-oxo products
  作者：John C. Knight、Merle G. Wovcha

  DOI：10.1016/0039-128x(80)90055-0

  日期：1980.12

  A mutant of the potent sterol degrader Mycobacterium fortuitum (ATCC 6842) has been isolated which is defective in its ability to degrade both the steroid nucleus and sterol side-chains that are branched at the 24-position. Bioconversions of phytosterol mixtures by this mutant resulted in the accumulation of the novel 24-oxo intermediates 9-hydroxy-27-nor-4-cholestene-3,24-dione (II) and 9-hydroxy-26,27-dinor-4-cholestene-3,24-dione (III). Under the same conditions, cholesterol is degraded mainly to 9-hydroxy-4-androstene-3,17-dione (I) by this organism.