20-hydroxyecdysone | 123238-67-5

• 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: 20-hydroxyecdysone
• 英文别名: 20β-hydroxyecdysone；ecdysterone；(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3S)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
• CAS: 123238-67-5
• 化学式: C₂₇H₄₄O₇
• 分子量: 480.642
• InChiKey: NKDFYOWSKOHCCO-ZPEWUMIJSA-N

物化性质

• 沸点：
  702.1±60.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 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：

  20-hydroxyecdysone 在 咪唑 、 4-二甲氨基吡啶 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Synthesis of a novel phosphate analog of 20-hydroxylecdysone with potent hypoglycemic activity

  摘要：

  A novel, water-soluble 20-hydroxylecdysono-20,22-phosphoric acid 2 and its sodium salt 3 were designed and synthesized from 20-hydroxylecdysone 1 in six steps and with 67% overall yield. The synthesized phosphoric acid 2 exhibited hypoglycemic activity 40-fold more potent than that of 20-hydroxylecdysone 1 at concentrations between 2x10-7 and 2x10-8mol/l in a glucose consumption test in HepG2 cells. At a concentration of 2x10-9mol/l, phosphoric acid 2 was still active, causing a maximum increase in glucose consumption of more than 500%, while 20-hydroxylecdysone 1 was inactive.

  DOI：

  10.1080/10286020.2011.554830
• 作为产物：
  描述：

  2β,3β,14-tris-(trimethylsilanyloxy)-5β-pregn-7-ene-6,20-dione 在 叔丁基锂 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.2h， 生成 20-hydroxyecdysone
  参考文献：
  名称：

  A facile route to 20-hydroxyecdysone and side chain homologues from poststeron

  摘要：

  A flexible approach to ecdysteroids, chain elongated at C-26 and C-27, is reported. Key features are the addition of 5-lithio 2,3-dihydrofurans (3) to poststeron (10) and a stereoselective reduction of the 22-00 group.

  DOI：

  10.1016/s0040-4020(01)80901-7

文献信息

• Hedtmann, Udo; Hobert, Kurt; Klintz, Ralf, Angewandte Chemie, 1989, vol. 101, # 10, p. 1543 - 1546
  作者：Hedtmann, Udo、Hobert, Kurt、Klintz, Ralf、Welzel, Peter、Frelek, Jadwiga、et al.

  DOI：——

  日期：——
• Synthesis of shidasterone and the unambiguous determination of its configuration at C-22
  作者：Patrick G. Roussel、Nicholas J. Turner、Laurence N. Dinan

  DOI：10.1039/c39950000933

  日期：——

  Shidasterone 1 is prepared from 2,3-isopropylidene-22-mesylate 20-hydroxyecdysone 4 by three different synthetic sequences; mechanistic considerations together with independent NOE studies reveal a (22R) configuration for Shidasterone 1.
• A facile route to 20-hydroxyecdysone and side chain homologues from poststeron
  作者：Udo Hedtmann、Ralf Klintz、Kurt Hobert、Jadwiga Frelek、Iontscho Vlahov、Peter Welzel

  DOI：10.1016/s0040-4020(01)80901-7

  日期：——

  A flexible approach to ecdysteroids, chain elongated at C-26 and C-27, is reported. Key features are the addition of 5-lithio 2,3-dihydrofurans (3) to poststeron (10) and a stereoselective reduction of the 22-00 group.
• Synthesis of a novel phosphate analog of 20-hydroxylecdysone with potent hypoglycemic activity
  作者：Dan Zhang、Min Zhang、Bao Ding、Xiao-Lin Wang、Zong-Yin Qiu、Yong Qin

  DOI：10.1080/10286020.2011.554830

  日期：2011.4

  A novel, water-soluble 20-hydroxylecdysono-20,22-phosphoric acid 2 and its sodium salt 3 were designed and synthesized from 20-hydroxylecdysone 1 in six steps and with 67% overall yield. The synthesized phosphoric acid 2 exhibited hypoglycemic activity 40-fold more potent than that of 20-hydroxylecdysone 1 at concentrations between 2x10-7 and 2x10-8mol/l in a glucose consumption test in HepG2 cells. At a concentration of 2x10-9mol/l, phosphoric acid 2 was still active, causing a maximum increase in glucose consumption of more than 500%, while 20-hydroxylecdysone 1 was inactive.