2-(4-hydroxyphenyl)-5,6-benzofurandione

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(4-hydroxyphenyl)-5,6-benzofurandione
• 英文别名: 2-(4-Hydroxyphenyl)-1-benzofuran-5,6-dione；2-(4-hydroxyphenyl)-1-benzofuran-5,6-dione
• 化学式: C₁₄H₈O₄
• 分子量: 240.215
• InChiKey: AKWBAQVPUVATRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  白藜芦醇 以 乙醇 为溶剂， 反应 4.0h， 生成 2,4,6-trihydroxyphenanthrene 、 2-(4-hydroxyphenyl)-5,6-benzofurandione 、 顺式白藜芦醇
  参考文献：
  名称：

  Photo-induced chemical reaction of trans-resveratrol

  摘要：

  Photo-induced chemical reaction of trans-resveratrol has been studied. UV B, liquid state and sufficient exposure time are essential conditions to the photochemical change of trans-resveratrol. Three principal compounds, cis-resveratrol, 2,4,6-phenanthrenetriol and 2-(4-hydroxyphenyl)-5,6-benzofurandione, were successively generated in the reaction solution of trans-resveratrol (0.25 mM, 100% ethanol) under 100 mu W cm(-2) UV B radiation for 4 h. cis-Resveratrol, originated from isomerization of trans-resveratrol, resulted in 2,4,6-phenanthrenetriol through photocyclisation reaction meanwhile loss of 2 H. 2,4, 6-Phenanthrenetriol played a role of photosensitizer producing singlet oxygen in the reaction pathway. The singlet oxygen triggered [4+2] cycloaddition reaction of trans-resveratrol, and then resulted in the generation of 2-(4-hydroxyphenyl)-5,6-benzofurandione through photorearrangement and oxidation reaction. The singlet oxygen reaction was closely related to the substrate concentration of trans-resveratrol in solution. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2014.08.130

文献信息

• Photo-induced chemical reaction of trans-resveratrol
  作者：Yue Zhao、Meng Shi、Jian-Hui Ye、Xin-Qiang Zheng、Jian-Liang Lu、Yue-Rong Liang

  DOI：10.1016/j.foodchem.2014.08.130

  日期：2015.3

  Photo-induced chemical reaction of trans-resveratrol has been studied. UV B, liquid state and sufficient exposure time are essential conditions to the photochemical change of trans-resveratrol. Three principal compounds, cis-resveratrol, 2,4,6-phenanthrenetriol and 2-(4-hydroxyphenyl)-5,6-benzofurandione, were successively generated in the reaction solution of trans-resveratrol (0.25 mM, 100% ethanol) under 100 mu W cm(-2) UV B radiation for 4 h. cis-Resveratrol, originated from isomerization of trans-resveratrol, resulted in 2,4,6-phenanthrenetriol through photocyclisation reaction meanwhile loss of 2 H. 2,4, 6-Phenanthrenetriol played a role of photosensitizer producing singlet oxygen in the reaction pathway. The singlet oxygen triggered [4+2] cycloaddition reaction of trans-resveratrol, and then resulted in the generation of 2-(4-hydroxyphenyl)-5,6-benzofurandione through photorearrangement and oxidation reaction. The singlet oxygen reaction was closely related to the substrate concentration of trans-resveratrol in solution. (C) 2014 Elsevier Ltd. All rights reserved.