肉桂酸Vc酯和肉桂酸异Vc酯的合成及其性能研究

Study on the synthesis and properties of L-ascorbyl cinnamate and D-isoascorbyl cinnamate

肉桂酰氯分别与Vc(L-抗坏血酸)和异Vc(D-异抗坏血酸)反应,得到肉桂酸Vc酯1和肉桂酸异Vc酯2,1和2的结构经IR、1H NMR、13C NMR和EI-MS确证。用分光光度法测试了产物清除DPPH自由基、羟基自由基和超氧阴离子自由基性能,用孔穴扩散法测试了产物对金黄葡萄球菌、大肠杆菌、枯草芽孢杆菌和细黄链霉菌的抗菌性能。结果表明,当受试物的摩尔浓度相同时,产物1和2清除上述三种自由基的能力分别比Vc和异Vc略有提高;当给药量为2 mg·mL-1时,产物1和2对上述四种菌种的抑菌效果与肉桂酸、山梨酸钾和苯甲酸钠大致相当。

L-ascorbyl cinnamate 1 and D-isoascorbyl cinnamate 2 were synthesized by the reaction of cinnanaoyl chloride with L-ascorbic acid and D-isoascorbic acid,respectively. The structures of 1 and 2 were confirmed by IR,^1H NMR,^13 C NMR and EI- MS. The scavenging activity of 1 and 2 on DPPH free-radical, hydroxyl free-radical and superoxide anion free-radical was tested by UV-Vis spectrophotonaetry, and the anti-microbial activity of 1 and 2 against Staphyloecocus anreus, Escherichia coli, Bacillus subtilis and Streptonayees microflavus was tested by peptide-agarose diffusion assay. It was found that 1 and 2 had higher scavenging activity than that of the corresponding L-ascorbic acid and D-isoaseorbie acid, respectively, when the molar concentration of tested samples was the same. It was also found that both 1 and 2 had the anti-microbial activity similar to that of cinnanaie acid,potassiuna sorbate and sodium benzoate when the concentration of tested samples was 2mg·mL^-1.