2-(3,4-dioleoyloxyphenyl)-4-oxo-4H-chromene-3,5,7-trioleate | 252013-41-5

• 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: 2-(3,4-dioleoyloxyphenyl)-4-oxo-4H-chromene-3,5,7-trioleate
• 英文别名: pentaoleoyl quercetin；[2-[(Z)-octadec-9-enoyl]oxy-4-[3,5,7-tris[[(Z)-octadec-9-enoyl]oxy]-4-oxochromen-2-yl]phenyl] (Z)-octadec-9-enoate
• CAS: 252013-41-5
• 化学式: C₁₀₅H₁₇₀O₁₂
• 分子量: 1624.5
• InChiKey: CAKJCRRTDTZRKB-GLPREEDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  39.5
• 重原子数：
  117
• 可旋转键数：
  86
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  158
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  油酰氯 、 槲皮素 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以60%的产率得到2-(3,4-dioleoyloxyphenyl)-4-oxo-4H-chromene-3,5,7-trioleate
  参考文献：
  名称：

  槲皮素脂肪酯的合成，分子表征和初步抗氧化活性评估

  摘要：

  AbstractQuercetin shows interesting pharmacological effects, but its use in topical applications is limited by its low skin permeability and solubility. In this work, the synthesis of highly lipophilic quercetin esters with oleic, linoleic and linolenic acid useful as topical quercetin prodrugs is reported. Partial OH esterification is advisable to maintain the antioxidant activity of these compounds; tetraesters and triesters can be achieved by modulating the reaction conditions utilized for the total esterification of quercetin. The chemical structures of the esters were proven by spectroscopic techniques; quantum chemical NMR calculation were mandatory to unequivocally assign the free position in triesters. Finally, the antioxidant activity of all the synthesized compounds was determined by the 2,2‐diphenyl‐1‐picryl‐hydrazyl method and by 2,2‐azinobis(3‐ethyl‐benzothiazoline‐6‐sulfonic acid) assay.

  DOI：

  10.1007/s11746-013-2314-0

文献信息

• Synthesis, Molecular Characterization and Preliminary Antioxidant Activity Evaluation of Quercetin Fatty Esters
  作者：Francesca Mainini、Alessandro Contini、Donatella Nava、Paola Antonia Corsetto、Angela Maria Rizzo、Elisabetta Agradi、Elena Pini

  DOI：10.1007/s11746-013-2314-0

  日期：2013.11

  AbstractQuercetin shows interesting pharmacological effects, but its use in topical applications is limited by its low skin permeability and solubility. In this work, the synthesis of highly lipophilic quercetin esters with oleic, linoleic and linolenic acid useful as topical quercetin prodrugs is reported. Partial OH esterification is advisable to maintain the antioxidant activity of these compounds; tetraesters and triesters can be achieved by modulating the reaction conditions utilized for the total esterification of quercetin. The chemical structures of the esters were proven by spectroscopic techniques; quantum chemical NMR calculation were mandatory to unequivocally assign the free position in triesters. Finally, the antioxidant activity of all the synthesized compounds was determined by the 2,2‐diphenyl‐1‐picryl‐hydrazyl method and by 2,2‐azinobis(3‐ethyl‐benzothiazoline‐6‐sulfonic acid) assay.