山梨酸苯丙氨酸乙酯的合成及抑菌活性

以山梨酸、苯丙氨酸和乙醇为原料,合成了山梨酸苯丙氨酸乙酯。通过单因素实验和正交实验,探讨了反应时间、反应温度、苯丙氨酸和氯化亚砜的摩尔比对苯丙氨酸乙酯盐酸盐合成产率的影响,并优化了工艺参数。合成苯丙氨酸乙酯盐酸盐最佳工艺条件为:反应时间3.5h,反应温度60℃,苯丙氨酸和氯化亚砜的摩尔比1∶3.2。抑菌实验结果表明,山梨酸苯丙氨酸乙酯对大肠杆菌、枯草芽孢杆菌、金黄色葡萄球菌和牛奶酸败混合菌的最低抑菌浓度分别为2.50、0.75、2.00、2.50mmol/L,其抑菌效果要优于山梨酸。在碱性条件下,山梨酸苯丙氨酸乙酯依然具有较高的抑菌活性,可把长牛奶酸败混合菌的生长适应期延长至36h。 

Synthesis and antibacterial activity of ethyl N-[1-oxo-2, 4-hexadien-1-yl]-L-phenylalaninate

A novel antibacterial agent, ethyl N-[1-oxo-2, 4-hexadien-1-yl]-L-phenylalaninate was synthesized.Excellent synthetic yield were studied through optimization of the conditions, such as reaction time, temperature and the ratio of L-phenylalaninate and SOCl2.When the reaction time was 3.5h, the reaction temperature was 60℃, the ratio of L-phenylalaninate and SOCl2 was 1∶3.2, the synthetic yield of L-phenylalaninate ethyl ester hydrochloride could reach 93.8%.The antimicrobial activity of ethyl N-[1-oxo-2, 4-hexadien-1-yl]-L- phenylalaninate against Escherichia coli, Bacillus subtili, Staphylococcus aureus the mixed bacteria from rancidity milk was studied and its minimum inhibitory concentrations of ethyl N-[1-oxo-2, 4-hexadien-1-yl]- L-phenylalaninate against these bacterial strains were 2.50, 0.75, 2.00 and 2.50mmol/L respectively.Its antibacterial activity was much better than sorbic acid.At the same time, ethyl N-[1-oxo-2, 4-hexadien-1-yl]-L-phenylalaninate still exhibited good antibacterial activity in alkaline condition.The growth adaptation period of the mixed bacteria from rancidity milk could be prolonged to 36h.