香豆素-3-甲酸丁香酚酯的合成、表征及在烟草中的应用

Synthesis and Characterization of Coumarin-3-Carboxylic Acid Eugenol Ester and Its Use in Cigarette as a Flavor

为开发稳定的烟用香料前驱体,以香豆素-3-甲酸、丁香酚合成了香豆素-3-甲酸丁香酚酯,产物的结构经红外光谱(IR)、核磁共振氢谱(1HNMR)、核磁共振碳谱(13CNMR)、高分辨率质谱(HMRS)和综合热分析确证。采用热解-GC/MS对该化合物的热解产物进行分离鉴定,并初步进行了卷烟加香试验。结果表明:①600℃时,香豆素-3-甲酸丁香酚酯的热解产物中共鉴定出22种成分,主要为烯类、烷类、酸类、酚类;②鉴定出丁香酚,表明香豆素-3-甲酸丁香酚酯能在卷烟燃吸温度下释放出一定量的丁香酚;③香豆素-3-甲酸丁香酚酯具有改善和修饰卷烟香气,增加甜韵和豆香香韵,减轻刺激性的作用。因此,香豆素-3-甲酸和丁香酚可以作为香料前驱体应用于卷烟加香。

In order to develop a new cigarette flavor precursor, coumarin-3-carboxylic acid eugenol ester was synthesized from coumarin-3-carboxylic acid and eugenol. The structure of the title compound was characterized by IR, ^1HNMR, ^13CNMR, HRMS and thermal analysis. The pyrolysis products were identified by means of pyrolysis-GC/MS, and the effect of the title compound on the flavor of cigarettes by smoking was evaluated. The results show that： （1） 22 compounds were identified at 600℃, and most of them were alkenes, alkanes, acids, and phenolic substances; （2） eugenol was identified, indicating that coumarin-3-carboxylic acid eugenol ester can release a certain amount of eugenol at the smoke temperature; （3） eugenol coumarin-3-carboxylic acid ester can improve and modify the flavor, enhance the notes of sweet aroma and bean aroma., and reduce the biting taste of cigarette smoke. Therefore, coumarin-3-carboxylic acid eugenol ester can be used in cigarette as an excellent flavor precursor.