9,20-Dihydroxyecdysone | 157977-59-8

• 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: 9,20-Dihydroxyecdysone
• 英文别名: (2β,3β,9α,14α,20R,22R)-2,3,9,14,20,22,25-heptahydroxy-5β-cholest-7-en-6-one；9α,20-dihydroxyecdysone；9alpha,20-Dihydroxyecdysone；(2S,3R,5R,9S,10S,13R,14S,17S)-2,3,9,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,5,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
• CAS: 157977-59-8
• 化学式: C₂₇H₄₄O₈
• 分子量: 496.642
• InChiKey: AHHRNGCAWAPZKG-GLRNUJIGSA-N

物化性质

• 熔点：
  269-271 °C
• 沸点：
  735.8±60.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  35
• 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：
  159
• 氢给体数：
  7
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (2β,3β,9α,14α,20R,22R)-9,14,25-trihydroxy-2,3:20,22-diisopropylidenedioxy-5β-cholest-7-en-6-one 在 水 、 溶剂黄146 作用下， 反应 12.0h， 以41%的产率得到9,20-Dihydroxyecdysone
  参考文献：
  名称：

  Stereoselective synthesis of 9α-hydroxylated ecdysteroids

  摘要：

  Treatment of ecdysteroids with excess of TBAF in THF was shown to proceed with stereoselective oxidation at the 9 alpha position of the carbon skeleton. The stereochemistry of the products was confirmed by X-ray analysis. Using this method. 9 alpha-hydroxyecdysteroids were obtained in good yield. The results open a route to novel type of natural and modified steroids that are difficult to access otherwise. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.10.011

文献信息

• Base-catalyzed autoxidation of 20-hydroxyecdysone: Synthesis of calonysterone and 920-dihydroxyecdysone
  作者：Apichart Suksamrarn、Penpan Ganpinyo、Chatriwat Sommechai

  DOI：10.1016/s0040-4039(00)73380-6

  日期：1994.6

  Base-catalyzed autoxidation of 20-hydroxyecdysone (2) gave an unusually modified ecdysteroid calonysterone (1) and 9,20-dihydroxyecdysone (4).

  碱催化20-羟基蜕皮激素的自氧化（2）得到了异常修饰的蜕皮甾体钙酮固酮（1）和9,20-二羟基蜕皮激素（4）。
• Oxidized Metabolites of 20-Hydroxyecdysone and Their Activity on Skeletal Muscle Cells: Preparation of a Pair of Desmotropes with Opposite Bioactivities
  作者：József Csábi、Tusty-Jiuan Hsieh、Feria Hasanpour、Ana Martins、Zoltán Kele、Tamás Gáti、András Simon、Gábor Tóth、Attila Hunyadi

  DOI：10.1021/acs.jnatprod.5b00249

  日期：2015.10.23

  Increasing the activation of protein kinase B (Akt) has been suggested as a key signaling step in the nonhormonal anabolic activity of the phytoecdysteroid 20-hydroxyecdysone (20E) in mammals. Base-catalyzed autoxidation of this compound was shown previously to yield interesting B-ring-modified analogues. Herein is reported a thorough study on this reaction, resulting in the preparation and complete NMR spectroscopic assignments of calonysterone (5) and its previously overlooked desmotropic pair (7), along with two new sensitive metabolites of 20E. The two isomers showed considerable stability in solution. Time dependency of the reaction for yield optimization is also presented; by means of analytical HPLC, the two desmotropes can reach a maximum combined yield of >90%. The activity of these compounds on Akt phosphorylation was tested in murine skeletal muscle cells. Compounds 2 and 5 showed more potent activity than 20E in increasing Akt activation, while compound 7 exerted an opposite effect. As such, the present study provides the first direct evidence for a pair of desmotropes exerting significantly different bioactivities.