一锅煮法由芦丁合成槲皮素五丙酸酯

Synthesis of Quercetin Penta-acrylate from Rutin by One-pot Procedure

采用一锅煮法由芦丁直接合成槲皮素酯。以芦丁为原料,浓硫酸作催化剂,65℃与丙酸酐反应,TLC板监测反应完毕,过滤、氯仿/甲醇重结晶。IR中ν-OH峰明显减弱,说明槲皮素的五个羟基发生了反应,νc=o位于1760.0cm^(-1),酯羰基峰明显增强,νc-o位于1240.0cm^(-1)、变宽增强;~1H-NMR中槲皮素的3-OH、5-OH、7-OH、3′-OH、4′-OH上面的氢全部消失,说明与丙酸酐发生了酯化反应,同时,出现五组丙酰基的甲基峰和亚甲基峰;MS中583.1为槲皮素五丙酸酯的分子离子峰。芦丁与丙酸酐反应可以得到槲皮素五丙酸酯。

The one-pot procedure was use to prepare the quercetin ester from rutin directly. The product was synthesized at 65 ℃ with rutin and propionic anhydride as raw materials and the concentrated sulfuric acid as catalyst. During the process, the reaction was monitored by TLC plate and the filtered products was recrystallized from the mixture of chloroform and methanol. The strength of the peak of ν-OHin IR decreased significantly which indicated that the five hydroxyl groups of quercetin had reacted. In addition, the strength of the peak of the νc=olocated at 1760.0cm-1increased obviously. The width of peak of νc=olocated at 1240.0cm-1was wider and the strength increased. Besides, all the hydrogens of 3-OH, 5-OH, 7-OH,3’-OH, 4’-OH of quercetin in 1H-NMR disappeared which indicated that the propionic anhydride had reacted with quercetin by esterification reac-tion. Meanwhile, the five groups of methyl and methylene peaks of propionyl appeared. Moreover, the molecular ion peak located at 583.1 of quercetin penta-acrylate was found in MS. The quercetin penta-acrylate could be synthesized by the reaction between rutin with propionic anhydride.