新型潜香化合物2,3-吡嗪二羧酸薄荷醇酯的热裂解分析

Pyrolysis Analysis of Novel Latent Fragrant Compounds -2,3-Pyrazinedicarboxlic Acid Menthyl Ester

  • 摘要: 为开发高温释放型烟用香料添加剂,本研究以2,3-吡嗪二羧酸和薄荷醇为原料,N,N′-二环己基碳酰亚胺(DCC)为缩合剂,4-二甲氨基吡啶(DMAP)为催化剂,经酯化反应制备了新型潜香目标化合物2,3-吡嗪二羧酸薄荷醇酯。该化合物经X射线单晶衍射、核磁共振波谱(1H NMR,13C NMR)、红外光谱(IR)和高分辨质谱(HRMS)表征后,结合同步热稳定性分析,采用在线热裂解气相色谱/质谱(Py-GC/MS)法对裂解产物进行定性和半定量分析,并初步推测了其可能的裂解机理。结果表明:在主要热失重区间268.5~334.9 ℃范围内,目标化合物基本分解完全,熔融温度为140.9 ℃,裂解温度为315.9 ℃;共鉴定出目标化合物的46种裂解产物,主要有薄荷烯、薄荷醇和吡嗪等多种对烟草香味有重要作用的致香成分。该方法能够方便、快速地分离鉴定高温食品香料添加剂的热裂解产物,可为该添加剂在烟草中的加香应用提供理论参考。

     

    Abstract: In order to develop the heat-release type of tobacco flavor additives, 2, 3-pyrazinedicarboxylic acid menthyl ester was prepared through esterification using 2, 3-pyrazinedicarboxylic acid and menthol as raw material, N, N′-dicyclohexylcarbodiimide (DCC) as condensing agent and 4-dimethylaminopyridine (DMAP) as catalyst. The structure of the target compound was characterized by X-ray single crystal diffraction, 1H NMR, 13C NMR, IR and HRMS. Combined with simultaneous thermal stability analysis, the fragmentation products of the target compound were qualitatively and semi-quantitatively analyzed by on-line pyrolysis-gas chromatography-mass spectrometry (Py-GC/MS) at three temperature levels of 300, 600 and 900 ℃, respectively. The possible fragmentation mechanism was initially speculated. The results show that the sample target compound is nearly decomposed in the range of major thermal weight loss occurred from 268.5 ℃ to 334.9 ℃. The melting temperature is 140.9 ℃, and the pyrolysis temperature is 315.9 ℃. 46 kinds of fragmentation products are identified, mainly including 3-p-menthene, menthol and pyrazine, which are aroma components and play an important role in tobacco flavor. This method is an accurate and quick way to isolate and identify the fragmentation products of hot food spices additives, which can provide a reliable theoretical reference for the additives in application of tobacco flavoring.

     

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