(20R,22R,24S)-2beta,3beta,14alpha,20,22,24-六羟基-5beta-胆甾-7-烯-6-酮 | 18089-44-6

• 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
• 中文名称: (20R,22R,24S)-2beta,3beta,14alpha,20,22,24-六羟基-5beta-胆甾-7-烯-6-酮
• 英文名称: pterosterone
• 英文别名: (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R,5S)-2,3,5-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
• CAS: 18089-44-6
• 化学式: C₂₇H₄₄O₇
• 分子量: 480.642
• InChiKey: UMMBJCYNGLCGEF-OAUIFJKNSA-N

物化性质

• 熔点：
  229-230 °C
• 沸点：
  692.7±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  138
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (20R,22R,24S)-2beta,3beta,14alpha,20,22,24-六羟基-5beta-胆甾-7-烯-6-酮 在 palladium on activated charcoal sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以88%的产率得到7,8-dihydropterosterone
  参考文献：
  名称：

  Stereoselective catalytic hydrogenation of Δ7-6-ketosteroids in the presence of sodium nitrite

  摘要：

  Catalytic hydrogenation with Pd-C as a catalyst in the presence of sodium nitrite is a simple, convenient and high yielding stereoselective reduction of olefinic function of Delta(7)-6-ketosteroids to the corresponding dihydro analogues. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00580-x
• 作为产物：
  描述：

  pterosterone 24-O-β-D-glucopyranoside 在 β-D-glucosidase 作用下， 反应 48.0h， 生成 (20R,22R,24S)-2beta,3beta,14alpha,20,22,24-六羟基-5beta-胆甾-7-烯-6-酮
  参考文献：
  名称：

  来自 Pfaffia iresinoides 的三种蜕皮甾体糖苷

  摘要：

  摘要 来自生药‘巴西人参’、黄柏的根、三种新的蜕皮甾体苷、蜕皮甾酮25-O-β-d-glucop

  DOI：

  10.1016/0031-9422(88)80422-9

文献信息

• Functional group-mediated biotransformation by Curvularia lunata NRRL 2178: synthesis of 3-dehydro-2-deoxy-ecdysteroids from the 3-hydroxy-2-mesyloxy analogues
  作者：Chatchawan Changtam、Oratai Sukcharoen、Boon-ek Yingyongnarongkul、Nitirat Chimnoi、Apichart Suksamrarn

  DOI：10.1016/j.tet.2008.01.033

  日期：2008.3

  Microbial transformation of ecdysteroids with 3-hydroxy-2-mesyloxy functional group by the fungus Curvularia lunata NRRL 2178 furnished 3-dehydro-2-deoxy analogues. The metabolites included 3-dehydro-2-deoxy analogues of 20-hydroxyecdysone, pterosterone, ponasterone A, 20-hydroxyecdysone 20,22-acetonide, shidasterone, and poststerone. The mild biotransformation conditions prevented the metabolites

  真菌 Curvularia lunata NRRL 2178 提供的 3-dehydro-2-deoxy 类似物对具有 3-hydroxy-2-mesyloxy 官能团的蜕皮甾体的微生物转化。代谢物包括 20-羟基蜕皮激素、蝶甾酮、松甾酮 A、20-羟基蜕皮激素 20,22-丙酮、shidasterone 和 poststerone 的 3-dehydro-2-deoxy 类似物。温和的生物转化条件阻止了代谢物的 C-5 差向异构化。
• Biotransformations of 20-hydroxyecdysone and analogues by Curvularia lunata NRRL 2178
  作者：Chatchawan Changtam、Oratai Sukcharoen、Boon-ek Yingyongnarongkul、Apichart Suksamrarn

  DOI：10.1016/j.steroids.2006.06.002

  日期：2006.10

  20-Hydroxyecdysone, the arthropod moulting hormone, was biotransformed by the fungus Curvularia lunata NRRL 2178 to the rare ecdysteroid, 2-dehydro-3-epi-20-hydroxyecdysone, and the novel 3 alpha,9 alpha-cyclo ecdysteroid analogue, (20R,22R)-3 beta,14 alpha,20,22,25-pentahydroxy-3 alpha,9 alpha-cyclo-5 beta-cholest-7-en-2,6-dione in 14 and 44% yields, respectively. Ponasterone A and pterosterone were similarly biotransformed to the corresponding 2-dehydro-3-epi- and 3 alpha,9 alpha-cyclo-analogues. (c) 2006 Elsevier Inc. All rights reserved.
• Stereoselective catalytic hydrogenation of Δ7-6-ketosteroids in the presence of sodium nitrite
  作者：Apichart Suksamrarn、Tanud Tanachatchairatana、Chana Sirigarn

  DOI：10.1016/s0040-4020(02)00580-x

  日期：2002.7

  Catalytic hydrogenation with Pd-C as a catalyst in the presence of sodium nitrite is a simple, convenient and high yielding stereoselective reduction of olefinic function of Delta(7)-6-ketosteroids to the corresponding dihydro analogues. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Three ecdysteroid glycosides from Pfaffia iresinoides
  作者：Nobushige Nishimoto、Yoshinori Shiobara、Shun-suke Inoue、Masumi Fujino、Tsunematsu Takemoto、Cheow Lin Yeoh、Fernando de Oliveira、Gokithi Akisue、Maria Kubota Akisue、Goro Hashimoto

  DOI：10.1016/0031-9422(88)80422-9

  日期：1988.1

  Abstract From the crude drug ‘Brazil ginseng’, the roots of Pfaffia iresinoides , three new ecdysteroid glycosides, ecdysterone 25- O -β- d -glucop

  摘要 来自生药‘巴西人参’、黄柏的根、三种新的蜕皮甾体苷、蜕皮甾酮25-O-β-d-glucop