2-hydroxy-6-(4-hydroxy-3-methoxybenzoyloxy)-4-methoxyphenyl-2-oxoacetic acid | 457600-83-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 2-hydroxy-6-(4-hydroxy-3-methoxybenzoyloxy)-4-methoxyphenyl-2-oxoacetic acid
• 英文别名: {2-[(3',4'-dihydroxybenzoil)oxy]-4,6-dihydroxyphenyl}(oxo) acetic acid；2-{2-[(3,4-dihydroxybenzoyl)oxy]-4,6-dihydroxyphenyl}-2-oxoacetic acid；2-Protocatechuoyloxy-4,6-dihydroxy-phenyl-glyoxylsaeure
• CAS: 457600-83-8
• 化学式: C₁₅H₁₀O₉
• 分子量: 334.239
• InChiKey: DJPSPQCSINGUAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.0
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  161.59
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  甲醇 、 槲皮素 以9.4 mg的产率得到{2-[(3',4'-dihydroxybenzoil)oxy]-4,6-dihydroxyphenyl}(oxo)methyl acetate
  参考文献：
  名称：

  Radiolysis of Quercetin in Methanol Solution:  Observation of Depside Formation

  摘要：

  Radiolysis of the flavonol quercetin, a natural antioxidant, was performed in methanol. The degradation process was followed by HPLC analyses. The major product was, identified as a depside (Q1) by NMR and LC-MS. The G(Q1) radiolytic factor was plotted versus them initial concentration of quercetin. This radiolytic process was attributed to the CH3O. radicals presented in the irradiated medium. The proposed mechanism invoked a stereospecific oxidation of the 3-hydroxyl group of quercetin which led to C-ring opening and to the formation of the depside Q1. In presence of water, Q1 was transformed into another depside, q2, by an inverse esterification reaction. A chemical equilibrium was observed between Q1 and Q2. The comprehension. of the radiolytic process of quercetin in methanol solution is of importance. Indeed, the same type of oxidative reactions could occur on flavonoids during preservation of food by ionizing radiation.

  DOI：

  10.1021/jf020165m

文献信息

• Radiolysis of Quercetin in Methanol Solution:  Observation of Depside Formation
  作者：Abdelghafour Marfak、Patrick Trouillas、Daovy-Paulette Allais、Yves Champavier、Claude-Alain Calliste、Jean-Luc Duroux

  DOI：10.1021/jf020165m

  日期：2002.8.1

  Radiolysis of the flavonol quercetin, a natural antioxidant, was performed in methanol. The degradation process was followed by HPLC analyses. The major product was, identified as a depside (Q1) by NMR and LC-MS. The G(Q1) radiolytic factor was plotted versus them initial concentration of quercetin. This radiolytic process was attributed to the CH3O. radicals presented in the irradiated medium. The proposed mechanism invoked a stereospecific oxidation of the 3-hydroxyl group of quercetin which led to C-ring opening and to the formation of the depside Q1. In presence of water, Q1 was transformed into another depside, q2, by an inverse esterification reaction. A chemical equilibrium was observed between Q1 and Q2. The comprehension. of the radiolytic process of quercetin in methanol solution is of importance. Indeed, the same type of oxidative reactions could occur on flavonoids during preservation of food by ionizing radiation.