2,3-Bis-[1-(4-hydroxy-3,5-dimethoxy-phenyl)-meth-(Z)-ylidene]-succinic acid diethyl ester | 56136-42-6

• 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: 2,3-Bis-[1-(4-hydroxy-3,5-dimethoxy-phenyl)-meth-(Z)-ylidene]-succinic acid diethyl ester
• 英文别名: diethyl (2Z,3Z)-2,3-bis[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]butanedioate
• CAS: 56136-42-6
• 化学式: C₂₆H₃₀O₁₀
• 分子量: 502.518
• InChiKey: DFHCCJWLEIUOLK-XFQWXJFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  ethyl sinapate 在 四甲基氢氧化铵 、 copper(II) nitrate 作用下， 以 乙腈 为溶剂， 以55%的产率得到2,3-Bis-[1-(4-hydroxy-3,5-dimethoxy-phenyl)-meth-(Z)-ylidene]-succinic acid diethyl ester
  参考文献：
  名称：

  Protective Effects of 4-Hydroxycinnamic Ethyl Ester Derivatives and Related Dehydrodimers against Oxidation of LDL:  Radical Scavengers or Metal Chelators?

  摘要：

  4-Hydroxycinnamate derivatives are known to be potent protectors against oxidation of low-density lipoproteins (LDL), via a combination of free radical scavenging and transition metal chelation. Through a series of 4-hydroxycinnamic ethyl ester derivatives and related 8-8 dehydrodimers, we have tried to bring out the structural requirements for radical scavenging and cupric ion chelation. We found that the monomeric compounds, except for highly lipophilic tert-butyl derivative 3, exhibited rather low radical scavenging properties. Furthermore, they did not chelate copper but, in contrast, reduced cupric ion to cuprous ion, affording the related 8-8 dehydrodimers, for which they could be considered as precursors in vitro. In the copper-dependent human LDL oxidation in vitro, the cyclic 8-8 dehydrodimer forms behaved essentially as efficient copper chelators, while related noncyclic 8-8 forms, which were found to be the best protectors, mainly acted as radical scavengers.

  DOI：

  10.1021/jf052923p

文献信息

• Protective Effects of 4-Hydroxycinnamic Ethyl Ester Derivatives and Related Dehydrodimers against Oxidation of LDL:  Radical Scavengers or Metal Chelators?
  作者：Anne Neudörffer、Jean-Pierre Desvergne、Dominique Bonnefont-Rousselot、Alain Legrand、Maurice-Bernard Fleury、Martine Largeron

  DOI：10.1021/jf052923p

  日期：2006.3.1

  4-Hydroxycinnamate derivatives are known to be potent protectors against oxidation of low-density lipoproteins (LDL), via a combination of free radical scavenging and transition metal chelation. Through a series of 4-hydroxycinnamic ethyl ester derivatives and related 8-8 dehydrodimers, we have tried to bring out the structural requirements for radical scavenging and cupric ion chelation. We found that the monomeric compounds, except for highly lipophilic tert-butyl derivative 3, exhibited rather low radical scavenging properties. Furthermore, they did not chelate copper but, in contrast, reduced cupric ion to cuprous ion, affording the related 8-8 dehydrodimers, for which they could be considered as precursors in vitro. In the copper-dependent human LDL oxidation in vitro, the cyclic 8-8 dehydrodimer forms behaved essentially as efficient copper chelators, while related noncyclic 8-8 forms, which were found to be the best protectors, mainly acted as radical scavengers.