3β,22α,28-triacetoxyracemosol C | 13844-00-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3β,22α,28-triacetoxyracemosol C
• 英文别名: 3,21,22,28-tetra-O-acetyl-jegosapogenol；3β.21β.22α.28-tetraacetoxy-oleanen-(12)-ol-(16α)；(4aR)-5t-Hydroxy-3c.4t.10c-triacetoxy-2.2.6at.6bc.9.9.12ac-heptamethyl-4ar-acetoxymethyl-(8atH.12btH.14bcH)-Δ¹⁴-eicosahydro-picen；16α-Hydroxy-3β,21β,22α,28-tetraacetoxy-oleanen-(12); Jegosapogenol-tetraacetat；Theasapogenin-B-tetraacetat；[(3R,4R,4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-3,4,10-triacetyloxy-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-4a-yl]methyl acetate
• CAS: 13844-00-3
• 化学式: C₃₈H₅₈O₉
• 分子量: 658.873
• InChiKey: GRWPECBRTNHOOY-LZUIWSLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  47
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  21β-acetoxy-3β,16α,22α,28-tetrahydroxyolean-12-ene 、 乙酸酐 在 吡啶 作用下， 以1 mg的产率得到3β,22α,28-triacetoxyracemosol C
  参考文献：
  名称：

  α-Glucosidase inhibitory monoacylated polyhydroxytriterpenoids from the fruits of Barringtonia racemosa

  摘要：

  Chemical investigation of a lipophilic CHCl3 extract of the dried fruits of Barringtonia racemosa resulted in the isolation of two unusual monoacylated polyhydroxy oleanane triterpenoid congeners named racemosols C-D (1-2) along with three known compounds. Their structures were determined by comprehensive spectroscopic analysis coupled with chemical modifications as 2 beta-acetoxy-3 beta, 16 alpha,22 alpha,28-tetrahydroxyolean-12-ene (1) and 22 alpha-(2-methylbutyryl)-3 beta, 15 alpha,16 alpha,21 beta,28-pentahydroxyolean-12-ene (2). Compounds (1-3, 1a, and 2a) were subjected to alpha-glucosidase inhibitory assay and 1 showed the most potent alpha-glucosidase inhibition with an IC50 value of 5.6 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.01.193

文献信息

• The structure of jegosapogenol
  作者：T. Nakano、H. Hasegawa、T. Fukumaru、S. Tobinaga、Carl Bjerassi、L.J. Durham、H. Budzikiewicz

  DOI：10.1016/s0040-4039(00)71552-8

  日期：1967.1
• Schrutka-Rechtenstamm, Roswitha; Robien, W.; Jurenitsch, J., Pharmazie, 1988, vol. 43, # 3, p. 208 - 210
  作者：Schrutka-Rechtenstamm, Roswitha、Robien, W.、Jurenitsch, J.

  DOI：——

  日期：——
• Sone, Acta Phytochimica, 1934, vol. 8, p. 23
  作者：Sone

  DOI：——

  日期：——
• Dimbi, Makoso Zeza; Kapundu, Mpuza; Darimont, Edmond, Bulletin des Societes Chimiques Belges, 1985, vol. 94, # 2, p. 141 - 148
  作者：Dimbi, Makoso Zeza、Kapundu, Mpuza、Darimont, Edmond、Warin, Roger、Delaude, Clement、Huls, Robert

  DOI：——

  日期：——