Synthesis and pyrolysis of two novel pyrrole ester flavor precursors,Journal of Heterocyclic Chemistry

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Synthesis and pyrolysis of two novel pyrrole ester flavor precursors
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2022-03-13 , DOI: 10.1002/jhet.4479
Wenpeng Fan ₁ , Wenjuan Chu ₂ , Haiying Tian ₂ , Zhan Zhang ₂ , Yingjie Feng ₂ , Ziting Gao ₁ , Biao Cheng ₁ , Xiaoming Ji ₁ , Miao Lai ₁

Affiliation

In order to develop the high-temperature-released pyrrole aroma, two novel flavors precursors of methyl 2-methyl-5-(((2-methylbutanoyl)oxy)methyl)-1-propyl-1H-pyrrole-3-carboxylate and methyl 2-methyl-5-(((2-methylbutanoyl)oxy)methyl)-1-propyl-1H-pyrrole-3-carboxylate were synthesized using glucosamine hydrochloride and methyl acetoacetate as raw materials through cyclization, oxidation, alkylation, reduction, and esterification. The target compounds were characterized by nuclear magnetic resonance (¹H NMR, ¹³C NMR), infrared spectroscopy (IR) and high-resolution mass spectrometry (HRMS). Thermogravimetry (TG), differential scanning calorimeter (DSC) and the pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS) methods were used to analyze the heating-stability of the target compounds, and the pyrolysis mechanism was inferred. Py-GC/MS results indicated that some fragrance compounds were formed during thermal degradation such as 2-methylbutyric acid, 2-methylbutyrate, alkylpyrroles, and benzoic acid, which were important aroma components or flavor additives. This provided a theoretical reference for the application of pyrrole ester in cigarette and heat-processed food flavoring.

中文翻译：

两种新型吡咯酯风味前体的合成与热解

为了开发高温释放吡咯香气，2-甲基-5-(((2-甲基丁酰基)氧基)甲基)-1-丙基-1H-吡咯-3-羧酸甲酯和甲基的两种新型香料前体以氨基葡萄糖盐酸盐和乙酰乙酸甲酯为原料，经环合、氧化、烷基化、还原和酯化。目标化合物通过核磁共振( ¹ H NMR, ¹³C NMR)、红外光谱 (IR) 和高分辨率质谱 (HRMS)。采用热重(TG)、差示扫描量热仪(DSC)和热解-气相色谱/质谱(Py-GC/MS)方法对目标化合物的热稳定性进行分析，并推断其热解机理。Py-GC/MS结果表明，在热降解过程中形成了一些芳香化合物，如2-甲基丁酸、2-甲基丁酸、烷基吡咯和苯甲酸，它们是重要的香气成分或风味添加剂。这为吡咯酯在卷烟及热加工食品香精中的应用提供了理论参考。

更新日期：2022-03-13

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