N-(3-甲酰吡啶)-脯氨酸甲酯的合成及其卷烟加香应用研究

以3-吡啶甲酸为起始原料,经酰氯化反应制成3-吡啶甲酰氯。另以脯氨酸为原料,经酰氯化后再与甲醇反应生成相应的氨基酸甲酯盐酸盐。在室温下,以三乙胺为缚酸剂,3-吡啶甲酰氯与氨基酸甲酯经过酰化反应生成目标产物N-(3-甲酰吡啶)-脯氨酸甲酯化合物。并将其应用于卷烟加香中,以改善卷烟制品品质。化合物结构通过1HNMR、13CNMR、IR和HRMS技术进行了表征。并对产物进行热重分析以及热裂解行为研究,分析鉴定出了40多种裂解产物,其多数为致香物质。对目标物进行卷烟加香评吸,结果表明,该物质能改善卷烟吸味,减轻卷烟吸食刺激性,增强香气。

Synthesis of N- ( 3- formyl pyridine )-proline methyl ester and its Application in Unblended Cigarette

Pyridine and its derivatives are one of the most important products of Maillard reaction,and it plays a very important role in supporting the aroma of tobacco and improving the quality of cigarette smoking.A novel pyridine derivative was obtained through a series of reaction and it was applied to the cigarette flavoring in order to improve the quality of cigarette products.Using 3-pyridine carboxylic acid as materials,3-pyridine carbonyl chloride was obtained via acylation reaction.Then,using 3-pyridine carboxylic acid as materials,the acylated α-amino acid reacted with methanol to generate the corresponding amino acid ester hydrochloride.At room temperature,using triethylamine as deacid reagent,the target product N-(3-formyl pyridine)-proline methyl ester was obtained after the acylation reaction of 3-pyridine carbonyl chloride with amino acid ester.The structures of all the compounds were confirmed by 1HNMR,13CNMR,IR and HRMS spectra.Then,the applications of the ester in cigarette flavoring were studied as well.More than 40 kinds of pyrolysis products were authenticated.Most of the pyrolysis products were aroma components.The smoke panel test shows that the new compound could improve the cigarette taste and flavor and reduce smoking irritation of cigarette.