2,3-bis(4-hydroxy-3,5-dimethoxybenzylidene)succinic acid

• 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(4-hydroxy-3,5-dimethoxybenzylidene)succinic acid
• 英文别名: (2E,3E)-2,3-bis[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]butanedioic acid
• 化学式: C₂₂H₂₂O₁₀
• 分子量: 446.411
• InChiKey: NTOZEZMSPMOENI-ACFHMISVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 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 74.0h， 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

文献信息

• Sinapate Dehydrodimers and Sinapate−Ferulate Heterodimers in Cereal Dietary Fiber
  作者：Mirko Bunzel、John Ralph、Hoon Kim、Fachuang Lu、Sally A. Ralph、Jane M. Marita、Ronald D. Hatfield、Hans Steinhart

  DOI：10.1021/jf020910v

  日期：2003.2.1

  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.