目的 化学合成制备紫锥菊中酚酸类化合物,优化已有的合成路线,为大量制备提供基础。方法以香草醛、丙二酸、L-酒石酸二乙酯、D-奎宁酸和苯乙醇等为原料,采用直接催化法(DDC/Py、DCC/DMAP、EDCI/DMAP等成酯缩合系统)或酰氯法,通过对活性羟基或羧基的保护、脱保护,制备酚酸类化合物。通过理化性质测定,结合1H-NMR、13C-NMR及MS等波谱手段确证化合物结构。结果 通过化学合成11个酚酸类化合物,分别为:原儿茶醛、咖啡酸、阿魏酸、咖啡酸苯乙酯、咖啡酸甲酯、咖啡酸乙酯、3,4-二乙酰咖啡酸、二乙酰菊苣酸酯、L-菊苣酸、3-O-咖啡酰奎宁酸和1,5-二咖啡酰奎宁酸。结论该合成路线原料易得、操作简单,可作为天然酚酸类化合物富集的方法。
Objective To prepare phenolic acid compounds of Echinacea purpurea by chemical synthesis method, to optimize existing synthetic routes and to establish a basis for a large num- ber of preparation. Methods Applying vanillin, malonic acid, (+) -diethyl L-tartrate, D- quinie acid and phenethyl alcohol as raw materials, phenolic acid compounds were synthesized by direct catalytic method (DDC/Py, DCC/DMAP, EDCI/DMAP and other ester condensation system) or acyl chloride method, then protected and deprotected active hydroxyl or carboxyl groups. The structures were confirmed by physicochemical characters, 1H-NMR, 13C_NMR and MS spectra. Results Eleven compounds were synthesized, they were benzaldehyde, caffeic acid, ferulic acid, caffeie acid phenethyl ester, methyl caffeate, ethyl eaffeate, 3,4-diaeetyl caffeic acid, diacetyl chicory acid ester, L-cichorie acid, 3-O-eaffeoylquinie acid and 1,5-di- caffeoylquinic acid. Conclusion The chemical synthesis routes are simple and it can be used for gathering phenolic acid compounds.