diethyl (E,E)-2,3-bis(3,5-dimethoxy-4-hydroxybenzylidene)succinate | 56136-37-9

• 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: diethyl (E,E)-2,3-bis(3,5-dimethoxy-4-hydroxybenzylidene)succinate
• 英文别名: bis-((E)-4-hydroxy-3,5-dimethoxy-benzylidene)-succinic acid diethyl ester；Bis-((E)-4-hydroxy-3,5-dimethoxy-benzyliden)-bernsteinsaeure-diaethylester；Phebalarin；diethyl (2E,3E)-2,3-bis[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]butanedioate
• CAS: 56136-37-9
• 化学式: C₂₆H₃₀O₁₀
• 分子量: 502.518
• InChiKey: DFHCCJWLEIUOLK-BEQMOXJMSA-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

• 作为反应物：
  描述：

  diethyl (E,E)-2,3-bis(3,5-dimethoxy-4-hydroxybenzylidene)succinate 在 sodium hydroxide 作用下， 反应 24.0h， 生成 2,3-bis(4-hydroxy-3,5-dimethoxybenzylidene)succinic acid
  参考文献：
  名称：

  Sinapate Dehydrodimers and Sinapate−Ferulate Heterodimers in Cereal Dietary Fiber

  摘要：

  Two 8-8-coupled sinapic acid dehydrodimers and at least three sinapate-ferulate heterodimers have been identified as saponification products from different insoluble and soluble cereal grain dietary fibers. The two 8-8-disinapates were authenticated by comparison of their GC retention times and mass spectra with authentic dehydrodimers synthesized from methyl or ethyl sinapate using two different single-electron metal oxidant systems. The highest amounts (481 mug/g) were found in wild rice insoluble dietary fiber. Model reactions showed that it is unlikely that the dehydrodisinapates detected are artifacts formed from free sinapic acid during the saponification procedure. The dehydrodisinapates presumably derive from radical coupling of sinapate-polymer esters in the cell wall; the radical coupling origin is further confirmed by finding 8-8 and 8-5 (and possibly 8-O-4) sinapate-ferulate cross-products. Sinapates therefore appear to have an analogous role to ferulates in cross-linking polysaccharides in cereal grains and presumably grass cell walls in general.

  DOI：

  10.1021/jf020910v
• 作为产物：
  描述：

  3,5-二甲氧基-4-羟基肉桂酸 在 吡啶 、 sodium hydroxide 、 manganese triacetate 、 乙酰氯 作用下， 以 1,4-二氧六环 为溶剂， 反应 50.0h， 生成 diethyl (E,E)-2,3-bis(3,5-dimethoxy-4-hydroxybenzylidene)succinate
  参考文献：
  名称：

  Sinapate Dehydrodimers and Sinapate−Ferulate Heterodimers in Cereal Dietary Fiber

  摘要：

  Two 8-8-coupled sinapic acid dehydrodimers and at least three sinapate-ferulate heterodimers have been identified as saponification products from different insoluble and soluble cereal grain dietary fibers. The two 8-8-disinapates were authenticated by comparison of their GC retention times and mass spectra with authentic dehydrodimers synthesized from methyl or ethyl sinapate using two different single-electron metal oxidant systems. The highest amounts (481 mug/g) were found in wild rice insoluble dietary fiber. Model reactions showed that it is unlikely that the dehydrodisinapates detected are artifacts formed from free sinapic acid during the saponification procedure. The dehydrodisinapates presumably derive from radical coupling of sinapate-polymer esters in the cell wall; the radical coupling origin is further confirmed by finding 8-8 and 8-5 (and possibly 8-O-4) sinapate-ferulate cross-products. Sinapates therefore appear to have an analogous role to ferulates in cross-linking polysaccharides in cereal grains and presumably grass cell walls in general.

  DOI：

  10.1021/jf020910v

文献信息

• 4-Hydroxycinnamic Ethyl Ester Derivatives and Related Dehydrodimers:  Relationship between Oxidation Potential and Protective Effects against Oxidation of Low-Density Lipoproteins
  作者：Anne Neudörffer、Dominique Bonnefont-Rousselot、Alain Legrand、Maurice-Bernard Fleury、Martine Largeron

  DOI：10.1021/jf035068n

  日期：2004.4.1

  dehydrodimer derivatives, noncyclized 8-8 diphenol dehydrodimers followed the same aforementioned sequence order and were found to be better antioxidants than their monomer counterparts. A good correlation between the inhibitory concentration and the oxidation potential was established among all these derivatives. However, a significantly deviating behavior was observed with the 8-5 dihydrobenzofuran and the

  已将一系列单体和二聚的4-羟基肉桂酸乙酯衍生物的电化学氧化潜力与其对铜催化的人类低密度脂蛋白（LDL）氧化的抗氧化活性进行了比较。在一系列羟基肉桂酸酯单体衍生物中，氧化电位和IC50值均按以下顺序降低：芥子酸酯>阿魏酸酯>对香豆酸酯。在4-羟基肉桂酸酯脱氢二聚体衍生物中，未环化的8-8二酚脱氢二聚体遵循相同的上述序列顺序，并且被发现比其单体对应物是更好的抗氧化剂。在所有这些衍生物之间建立了抑制浓度和氧化电位之间的良好相关性。然而，用8-5二氢苯并呋喃和8-8二氢萘酚环状脱氢二聚体观察到明显偏离的行为，尽管它们的氧化电势与非环化的8-8脱氢二聚体非常接近，但它们对铜催化的人LDL的活性较低。相反，在Trolox等效抗氧化剂容量（TEAC）分析系统中，发现8-8二氢萘酚脱氢二聚体是最有效的自由基清除剂。最后，在一系列研究的脱氢二聚体中，可以得出结论，无论使用何种体外测试系统，（a）所有测试的脱