scutellarin ethyl ester

• 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: scutellarin ethyl ester
• 英文别名: ethyl (2S,3S,4S,5R,6S)-6-[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylate
• 化学式: C₂₃H₂₂O₁₂
• 分子量: 490.42
• InChiKey: RJAAYFVWCWJJMM-KHYDEXNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  192
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  红盏花素 在 potassium iodide 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 scutellarin ethyl ester
  参考文献：
  名称：

  Prodrugs of scutellarin: Ethyl, benzyl and N,N-diethylglycolamide ester synthesis, physicochemical properties, intestinal metabolism and oral bioavailability in the rats

  摘要：

  In an effort to enhance the oral bioavailability of scutellarin, ethyl, benzyl and N,N-diethylglycolamide ester of scutellarin were synthesized. The hydrolysis of the prodrugs follows first-order kinetics in aqueous solution, and produced a V-shaped pH profile. The N,N-diethylglycolamide ester is highly susceptible to enzymatic hydrolysis in human plasma (t(1/2) approximate to 7 min) with a high stability in aqueous solution (t(1/2) approximate to 16 day, pH 4.2). Compared with the solubility of scutellarin, the solubility of glycolamide ester was about ten times in pH 4.0 buffer, and about thirty five times in water. Its apparent partition coefficient increased significantly from -2.56 to 1.48. Glycolamide ester of scutellarin was chosen to investigate the intestinal metabolism and in vivo bioavailability Degradation studies in the intestinal tract content and homogenates indicated intestinal metabolism before absorption was a crucial obstacle for the prodrug. N,N-Diethylglycolamide ester can be protected from the degradation in the intestinal lumen by an emulsion. A significant increase in the plasma AUC and C-max of the prodrug emulsion was observed in rats, compared with that of the scutellarin-cyclodextrin complex (P < 0.01). The emulsion of N,N-diethylglycolamide ester produces a 1.58-fold enhancement in apparent bioavailability and 1.4-fold increase in the absolute bioavailability compared to the scutallarin-cyclodextrin complex. (c) 2006 Published by Elsevier B.V.

  DOI：

  10.1016/j.ejps.2006.07.007

文献信息

• An efficient, scalable approach to hydrolyze flavonoid glucuronides via activation of glycoside bond
  作者：Xue-Yang Jiang、Xin-Chen Li、Wen-Yuan Liu、Yun-Hui Xu、Feng Feng、Wei Qu

  DOI：10.1016/j.tet.2017.02.039

  日期：2017.4

  glucuronides into corresponding aglycones posed some significant challenges. To improve acid-catalyzed hydrolysis process of flavonoid glucuronide, structures of glucuronide, hydrolysis parameters and post-processing were optimized. The optimized condition was performed by hydrolysis flavonoid glycoside methyl ester in a mixed solvent consisting of 2 mol/L H2SO4/EtOH/H2O (1/8/1, v/v/v) at 95 °C for 7 h

  将类黄酮葡糖醛酸苷水解成相应的糖苷配基面临一些重大挑战。为了改善酸催化类黄酮葡糖醛酸的水解过程，优化了葡糖醛酸的结构，水解参数和后处理工艺。通过在由2 mol / LH 2 SO 4 / EtOH / H 2 O（1 /8/ 1，v / v / v）组成的混合溶剂中于95°C水解类黄酮糖苷甲基酯7 h并导致高达90％的糖苷配基收率，最小的副产物形成和温和的水解条件。此外，优化的方法避免了繁琐的纯化步骤，并且使用经济的和可商购的试剂易于在较大规模下进行。
• Prodrugs of scutellarin: Ethyl, benzyl and N,N-diethylglycolamide ester synthesis, physicochemical properties, intestinal metabolism and oral bioavailability in the rats
  作者：Feng Cao、Jian-Xin Guo、Qi-Neng Ping、Zheng-Gen Liao

  DOI：10.1016/j.ejps.2006.07.007

  日期：2006.12

  In an effort to enhance the oral bioavailability of scutellarin, ethyl, benzyl and N,N-diethylglycolamide ester of scutellarin were synthesized. The hydrolysis of the prodrugs follows first-order kinetics in aqueous solution, and produced a V-shaped pH profile. The N,N-diethylglycolamide ester is highly susceptible to enzymatic hydrolysis in human plasma (t(1/2) approximate to 7 min) with a high stability in aqueous solution (t(1/2) approximate to 16 day, pH 4.2). Compared with the solubility of scutellarin, the solubility of glycolamide ester was about ten times in pH 4.0 buffer, and about thirty five times in water. Its apparent partition coefficient increased significantly from -2.56 to 1.48. Glycolamide ester of scutellarin was chosen to investigate the intestinal metabolism and in vivo bioavailability Degradation studies in the intestinal tract content and homogenates indicated intestinal metabolism before absorption was a crucial obstacle for the prodrug. N,N-Diethylglycolamide ester can be protected from the degradation in the intestinal lumen by an emulsion. A significant increase in the plasma AUC and C-max of the prodrug emulsion was observed in rats, compared with that of the scutellarin-cyclodextrin complex (P < 0.01). The emulsion of N,N-diethylglycolamide ester produces a 1.58-fold enhancement in apparent bioavailability and 1.4-fold increase in the absolute bioavailability compared to the scutallarin-cyclodextrin complex. (c) 2006 Published by Elsevier B.V.