(E)-2-hydroxy-3,5,3′,4′-tetramethoxystilbene | 1182284-01-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-2-hydroxy-3,5,3′,4′-tetramethoxystilbene
• 英文别名: (E)-2-hydroxy-3,5,3',4'-tetramethoxystilbene；2-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-4,6-dimethoxyphenol
• CAS: 1182284-01-0
• 化学式: C₁₈H₂₀O₅
• 分子量: 316.354
• InChiKey: MZAIFUDAOFIJLK-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-[(1E)-2-(3,5-二甲氧基苯基)乙烯基]-2-甲氧基苯酚 在 间氯过氧苯甲酸 作用下， 生成 (E)-2-hydroxy-3,5,3′,4′-tetramethoxystilbene
  参考文献：
  名称：

  Effect of Resveratrol-Related Stilbenoids on Biomembrane Models

  摘要：

  The interactions of the two resveratrol analogues 2-hydroxy-3,5,3',5'-tetramethoxystilbene (4) and 2-hydroxy-3,5,3',4'-tetramethoxystilbene (5) with model biomembranes were studied. The aim of this investigation was to highlight possible differences in the interactions with such biomembranes related to the minimal structural differences between these isomeric stilbenoids. In particular, different experiments on stilbenoid/biomembrane model systems using both differential scanning calorimetry (DSC) and Langmuir-Blodgett techniques were carried out to evaluate stilbenoid/multilamellar vesicle and stilbenoid/phospholipid monolayer interactions, respectively. Dimyristoylphosphatidylcholine was used as constituent of the biomembrane models and permitted the experiments to be carried out at 37 degrees C, close to body temperature. Kinetic studies were also run by DSC to evaluate the uptake of the resveratrol derivatives by the biomembrane model in an aqueous medium and when transported by a lipophilic carrier. The results indicated that both of the resveratrol analogues influenced the behavior of multilamellar vesicles and monolayers, biomembrane models, with 4 producing a larger effect than 5. These results are useful for better understanding the mechanism of action of these compounds. Moreover, the kinetic results could be of importance for future design of lipophilic delivery systems for these stilbenoids.

  DOI：

  10.1021/np400188m

文献信息

• Effect of Resveratrol-Related Stilbenoids on Biomembrane Models
  作者：Maria Grazia Sarpietro、Carmela Spatafora、Maria Lorena Accolla、Orazio Cascio、Corrado Tringali、Francesco Castelli

  DOI：10.1021/np400188m

  日期：2013.8.23

  The interactions of the two resveratrol analogues 2-hydroxy-3,5,3',5'-tetramethoxystilbene (4) and 2-hydroxy-3,5,3',4'-tetramethoxystilbene (5) with model biomembranes were studied. The aim of this investigation was to highlight possible differences in the interactions with such biomembranes related to the minimal structural differences between these isomeric stilbenoids. In particular, different experiments on stilbenoid/biomembrane model systems using both differential scanning calorimetry (DSC) and Langmuir-Blodgett techniques were carried out to evaluate stilbenoid/multilamellar vesicle and stilbenoid/phospholipid monolayer interactions, respectively. Dimyristoylphosphatidylcholine was used as constituent of the biomembrane models and permitted the experiments to be carried out at 37 degrees C, close to body temperature. Kinetic studies were also run by DSC to evaluate the uptake of the resveratrol derivatives by the biomembrane model in an aqueous medium and when transported by a lipophilic carrier. The results indicated that both of the resveratrol analogues influenced the behavior of multilamellar vesicles and monolayers, biomembrane models, with 4 producing a larger effect than 5. These results are useful for better understanding the mechanism of action of these compounds. Moreover, the kinetic results could be of importance for future design of lipophilic delivery systems for these stilbenoids.