sodium 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-olate | 79054-98-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: sodium 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-olate
• CAS: 79054-98-1
• 化学式: C₁₅H₉O₇*Na
• 分子量: 324.222
• InChiKey: VSHCBHOZVKIMJI-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.64
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  134.19
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  槲皮素 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 sodium 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-olate
  参考文献：
  名称：

  Acidity of Hydroxyl Groups: An Overlooked Influence on Antiradical Properties of Flavonoids

  摘要：

  The reactions of 10 flavonoids with 2,2-diphenyl-1-picrylhydrazyl radical (dpph(center dot)) carried out in alcohols always occur significantly faster than ill acidified alcohols or in dioxane. These fast kinetics benefit from the contribution of the electron transfer from a flavonoid anion to a radical, a mechanism known as Sequential Proton-Loss Electron-Transfer (SPLET), which adds to the kinetics of single-step Hydrogen Atom Transfer (HAT)/Proton Coupled Electron Transfer (PCET) processes (see Acc. Chem. Res. 2007, 40, 222.). The domination of SPLET over HAT/PCET in case of a flavonoid reacting with electron-deficient radicals Such as peroxyls or dpph(center dot) in polar solvents explains the enhancement of antioxidant activity of 3-hydroxyflavone. It also elucidates the great acceleration in the reactions of dpph(center dot) with quercetin, morin, galangin, and 7,8-hydroxyflavone. The analysis of structure-acidity and structure-activity relationships for 10 flavonoids clearly indicates that hydroxyl group at position 7 is the most acidic site. Thus, in polar solvents this group can participate in radical reaction via SPLET. In nonpolar solvents the most active site in quercetin (a flavonoid antioxidant commonly found in plants) is 3',4'-dihydroxyl moiety and HAT/PCET occurs. However, in ionization-supporting solvents an anion formed at position 7 is responsible for very fast kinetics of quercetin/dpph(center dot) reaction because both mechanisms participate: HAT (from catechol moiety in ring B) and SPLET (from ionized 7-hydroxyl in ring A). Because of conjugation of rings A, B, and C the final structure of the formed quercetin radical (or quercetin anion radical) is the same for the SPLET and HAT/PCET mechanisms.

  DOI：

  10.1021/jo802716v