3β-acetoxy-18α,19α-epoxylupan-21β-ol | 1417802-19-7

• 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-acetoxy-18α,19α-epoxylupan-21β-ol
• 英文别名: 18β,19β-epoxy-21β-hydroxylupan-3β-yl acetate；[(1R,2R,5S,7S,8R,10S,11S,14R,15R,18S,20R)-7-hydroxy-1,2,5,15,19,19-hexamethyl-8-propan-2-yl-9-oxahexacyclo[12.8.0.02,11.05,10.08,10.015,20]docosan-18-yl] acetate
• CAS: 1417802-19-7
• 化学式: C₃₂H₅₂O₄
• 分子量: 500.762
• InChiKey: ZNASWLDXPDGIID-OZKXJHANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-18α,19α-epoxylupan-21β-ol 、 乙酸酐 在 吡啶 作用下， 反应 24.0h， 生成 3β,21β-diacetoxy-18α,19α-epoxylupane
  参考文献：
  名称：

  Officinatrione: an unusual (17S)-17,18-seco-lupane skeleton, and four novel lupane-type triterpenoids from the roots of Taraxacum officinale

  摘要：

  Novel 5 lupane-type of triterpenois, i.e., 3 beta-acetoxy-18 alpha,19 alpha-epoxylupan-21 beta-ol (1), 18 alpha,19 alpha-epoxy-21 beta-hydroxylupan-3-one (2), lup-18-ene-3,21-dione (3), lupa-18,21-dien-3 beta-yl acetate (4), and (17S)-17,18-seco-lup-19(21)-ene-3,18,22-trione (5), named officinatrione, as well as 16 known compounds from the roots of Taraxacum officinale collected in Takatsuki city, Osaka, Japan. Of the above compounds, 5 was the first lupane-type triterpene, of which the D-ring was open to form a nine-membered ring. Compounds 2 and 5 exhibited moderate cytotoxic activities against L1210 cell line (IC50 10.5 and 10.1 mu M). (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.001