肉桂酸 4-(4-乙酰基-5-甲基-2-吡咯基)-2′3′4′-三羟基丁酯的合成及其卷烟加香应用研究

Synthesis of 4-(4-acetyl-5-methyl-1H-pyrrol-2-yl)-2′3′4′-trihydroxybutyl cinnamate and its Application in Unblended Cigarette

摘要:

摘要：碱性条件下，以氨基葡萄糖盐酸盐与乙酰丙酮为原料，在水溶液中加热回流，得到2-甲基-3-乙酰基-5-1′2′3′4′-四羟丁基吡咯。并以此为原料，以DCC为的缩合剂，与肉桂酸反应合成了目标化合物肉桂酸 4-(4-乙酰基-5-甲基-2-吡咯基）-2′3′4′-三羟基丁酯，通过1H NMR、13C NMR、IR、HRMS等方法对产物的结构进行了验证。研究了目标物在300°C，600°C，900°C的热裂解行为，并对目标物进行卷烟加香研究，结果表明：目标化合物可裂解出苯甲醛、2-甲基吡啶、金合欢醇等香气成分，按烟丝质量0.2%添加该物质可起到改善卷烟的吃味与香气质，降低刺激性，改善余味的作用。

Abstract:

Abstract: Under alkaline conditions in aqueous solution, 2-methyl -3-acetyl-5-1′,2′,3′,4′-tetrahydroxy butyl pyrrole were obtained by the reaction of D-glucosamine hydrochloride with acetyl acetone at reflux temperature, then take this chemical compound as raw material, reacted with cinnamic acid to synthesis the 4-(4-acetyl-5-methyl-1H-pyrrol-2-yl)-2,3,4-trihydroxybutyl cinnamate in the presence of DCC which was used as dehydrating agent. Its structure was characterized and verified by 1H NMR, 13C NMR, IR, and HRMS spectral analysis. Then the pyrolysis of the target product at 300, 600, 900°C respectively, and the application of the oil in cigarette flavoring were studied as well. The results showed that benzaldehyde, 2-methyl pyridine, farnesol and so on were detected at three temperatures. It is proved that when the target was ammount to 0.2% in tobacco, which could play an important role in enhancing the aroma quality and volume of smoke, reducing irritancy and improving the aftertaste.