18,19-diacetoxyvoucapane | 1204592-11-9

• 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: 18,19-diacetoxyvoucapane
• 英文别名: [(4aR,6aS,7R,11aS,11bR)-4-(acetyloxymethyl)-7,11b-dimethyl-1,2,3,4a,5,6,6a,7,11,11a-decahydronaphtho[2,1-f][1]benzofuran-4-yl]methyl acetate
• CAS: 1204592-11-9
• 化学式: C₂₄H₃₄O₅
• 分子量: 402.531
• InChiKey: WCUQSUMSQVCOON-WWQQZRQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  voucapan-18,19-diol 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以90%的产率得到18,19-diacetoxyvoucapane
  参考文献：
  名称：

  Cytotoxic, anti-proliferative and antimicrobial furanoditerpenoids from Stuhlmania moavi

  摘要：

  The furanoditerpenoids voucapane, voucapane-6 alpha,7 alpha-diol, voucapane-18,19-diol and 18-hydroxyvoucapan-19-al were isolated from the cytotoxic stem and root bark extracts of Stuhlmania moavi Verdc. (Ceasalpiniaceae) and their structures established based on analysis of spectroscopic data. The compounds exhibited anti-proliferative, cytotoxic, antibacterial and antifungal activities, 18-hydroxyvoucapan-19-al showing the highest anti-proliferative and cytotoxic properties. Voucapane-18,19-diol was only mildly active but the activity was enhanced for its 18,19-di-(4-methyl)-benzenesulphonate. Some of these results thus corroborate the traditional medicinal uses of the crude extracts for the treatment of skin infections. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.08.017