6β,7α-diacetoxylabda-8,13E-dien-15-ol. | 273212-70-7

• 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: 6β,7α-diacetoxylabda-8,13E-dien-15-ol.
• 英文别名: [(1S,2S,4aS,8aS)-2-acetyloxy-4-[(E)-5-hydroxy-3-methylpent-3-enyl]-3,4a,8,8-tetramethyl-1,2,5,6,7,8a-hexahydronaphthalen-1-yl] acetate
• CAS: 273212-70-7
• 化学式: C₂₄H₃₈O₅
• 分子量: 406.563
• InChiKey: QQJGTXJPLKSUKT-DZBWUNPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6β,7α-diacetoxylabda-8,13E-dien-15-ol. 、 乙酸酐 在 吡啶 作用下， 反应 16.0h， 以90%的产率得到(13E)-6β,7α,15-triacetoxy-labda-8,13-diene
  参考文献：
  名称：

  Bioactive Metabolites from the South African Marine Mollusk Trimusculus costatus

  摘要：

  A reinvestigation of extracts of the endemic South African intertidal limpet Trimusculus costatus yielded the known labdane diterpenes 6 beta,7 alpha-diacetoxylabda-8,13E-dien-15-ol (1) and 2 alpha,6 beta,7 alpha-triacetoxylabda-8,13E-dien-15-ol (2) and three new metabolites, 6 beta,7 alpha,15-triacetoxylabda-8,13E-diene (3), 3 alpha,11-dihydroxy-9,11-seco-cholest-4,7-dien-6,9-dione (4), and cholest-7-en-3,5,7-triol (5). Chiral derivatization and X-ray analysis were used to confirm the labdane absolute configuration of 2. Compounds 1, 2 and 4 exhibited moderate activity (3-25 mu M) against the WHCO1 human esophageal cancer cell line.

  DOI：

  10.1021/np070612y

文献信息

• Bioactive Metabolites from the South African Marine Mollusk <i>Trimusculus costatus</i>
  作者：Albert W. W. van Wyk、Christopher A. Gray、Catherine E. Whibley、Omolaja Osoniyi、Denver T. Hendricks、Mino R. Caira、Michael T. Davies-Coleman

  DOI：10.1021/np070612y

  日期：2008.3.1

  A reinvestigation of extracts of the endemic South African intertidal limpet Trimusculus costatus yielded the known labdane diterpenes 6 beta,7 alpha-diacetoxylabda-8,13E-dien-15-ol (1) and 2 alpha,6 beta,7 alpha-triacetoxylabda-8,13E-dien-15-ol (2) and three new metabolites, 6 beta,7 alpha,15-triacetoxylabda-8,13E-diene (3), 3 alpha,11-dihydroxy-9,11-seco-cholest-4,7-dien-6,9-dione (4), and cholest-7-en-3,5,7-triol (5). Chiral derivatization and X-ray analysis were used to confirm the labdane absolute configuration of 2. Compounds 1, 2 and 4 exhibited moderate activity (3-25 mu M) against the WHCO1 human esophageal cancer cell line.