Hexanoic acid (6aS,7S,7aR,11aR,12aS)-1,2,3-tris-benzyloxy-9-(4-methoxy-phenyl)-5-oxo-6a,7,7a,11,11a,12a-hexahydro-5H-6,8,10,12-tetraoxa-benzo[a]anthracen-7-yl ester | 646999-66-8

• 分子结构分类: 有机化合物
• 英文名称: Hexanoic acid (6aS,7S,7aR,11aR,12aS)-1,2,3-tris-benzyloxy-9-(4-methoxy-phenyl)-5-oxo-6a,7,7a,11,11a,12a-hexahydro-5H-6,8,10,12-tetraoxa-benzo[a]anthracen-7-yl ester
• CAS: 646999-66-8
• 化学式: C₄₈H₄₈O₁₁
• 分子量: 800.903
• InChiKey: TWXNMEBDAWVHNW-BNULMVNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.02
• 重原子数：
  59.0
• 可旋转键数：
  16.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  117.21
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Hexanoic acid (6aS,7S,7aR,11aR,12aS)-1,2,3-tris-benzyloxy-9-(4-methoxy-phenyl)-5-oxo-6a,7,7a,11,11a,12a-hexahydro-5H-6,8,10,12-tetraoxa-benzo[a]anthracen-7-yl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 以72%的产率得到norbergenin 4-caproate
  参考文献：
  名称：

  Synthesis and neuroprotective activity of bergenin derivatives with antioxidant activity

  摘要：

  Norbergenin, which is the O-demethyl derivative of bergenin, the main component of Mallotus japonicus, has been found to show moderate antioxidant activity (IC50 13 muM in DPPH radical scavenging; 32 muM in superoxide anion scavenging). Modification of sugar part on norbergenin by coupling with a variety of fatty acids was employed for increasing its antioxidant activity. Selective esterification of hydroxyl groups on the sugar part enhanced greatly antioxidant activity. The most potent one is norbergenin 11-caproate, which not only exhibits stronger antioxidant activity than that of catechin but also prevents neuronal death at 10 muM on the primary culture of rat cortical neurons in DM EM supplemented with N2. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00666-1
• 作为产物：
  描述：

  在 4-二甲氨基吡啶 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 吡啶 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 73.0h， 生成 Hexanoic acid (6aS,7S,7aR,11aR,12aS)-1,2,3-tris-benzyloxy-9-(4-methoxy-phenyl)-5-oxo-6a,7,7a,11,11a,12a-hexahydro-5H-6,8,10,12-tetraoxa-benzo[a]anthracen-7-yl ester
  参考文献：
  名称：

  Synthesis and neuroprotective activity of bergenin derivatives with antioxidant activity

  摘要：

  Norbergenin, which is the O-demethyl derivative of bergenin, the main component of Mallotus japonicus, has been found to show moderate antioxidant activity (IC50 13 muM in DPPH radical scavenging; 32 muM in superoxide anion scavenging). Modification of sugar part on norbergenin by coupling with a variety of fatty acids was employed for increasing its antioxidant activity. Selective esterification of hydroxyl groups on the sugar part enhanced greatly antioxidant activity. The most potent one is norbergenin 11-caproate, which not only exhibits stronger antioxidant activity than that of catechin but also prevents neuronal death at 10 muM on the primary culture of rat cortical neurons in DM EM supplemented with N2. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00666-1