threo-(7R,8R)-guaiacylglycerol-8-vanillin ether | 631922-79-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: threo-(7R,8R)-guaiacylglycerol-8-vanillin ether
• 英文别名: (7R,8R)-guaiacylglycerol 8-vanillin ether；4-[(1R,2R)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3-methoxybenzaldehyde
• CAS: 631922-79-7
• 化学式: C₁₈H₂₀O₇
• 分子量: 348.353
• InChiKey: BRWKQWFEHBAUSN-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  rac-(7R,8R)-guaiacylglycerol 8-vanillin ether 在 Daicel Chiralpak AD-H chiral column 作用下， 以 正己烷 、 异丙醇 为溶剂， 生成 threo-(7R,8R)-guaiacylglycerol-8-vanillin ether 、 (7S,8S)-guaiacylglycerol 8-vanillin ether
  参考文献：
  名称：

  Chiral resolution and neuroprotective activities of enantiomeric 8-O-4′ neolignans from the fruits of Crataegus pinnatifida Bge

  摘要：

  Five pairs of enantiomeric 8-O-4' neolignans (1a/1b-5a/5b), including seven new compounds (1a/1b, 2a, 3a, 4a/4b and 5b), were obtained from the fruits of Crataegus pinnatifida Bge. Their structures were determined by comprehensive spectroscopic analyses. The absolute configurations of the enantiomers were determined by comparison of the experimental ECD with the calculated data. Additionally, all the enantiomeric neolignans were evaluated for their neuroprotective activity against H2O2-induced cell injury in human neuroblastoma SH-SY5Y cells, and most of them showed potent selective neuroprotective activity. Especially, 3b (72.98%) showed the best protective effect, better than 3a (63.49%) and trolox (62.86%) at 25 mu M.

  DOI：

  10.1016/j.fitote.2019.05.003