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Synthesis and pyrolysis of various novel pyrrole ester fragrance precursors
Flavour and Fragrance Journal ( IF 2.1 ) Pub Date : 2023-04-17 , DOI: 10.1002/ffj.3747 Pengyu Li 1 , Haiying Tian 2 , Lu Han 2 , Huaiqi Li 2 , Yuhang Ji 1 , Jinchu Yang 2 , Miao Lai 1 , Wenjuan Chu 2 , Xiaoming Ji 1
Flavour and Fragrance Journal ( IF 2.1 ) Pub Date : 2023-04-17 , DOI: 10.1002/ffj.3747 Pengyu Li 1 , Haiying Tian 2 , Lu Han 2 , Huaiqi Li 2 , Yuhang Ji 1 , Jinchu Yang 2 , Miao Lai 1 , Wenjuan Chu 2 , Xiaoming Ji 1
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Due to the disadvantages of low fragrance threshold and high volatility of pyrrole monomer under high-temperature process in tobacco or food, it cannot meet the market requirements. In order to develop pyrrole flavour precursors, 2,5-dimethyl-N-pyrroleacetic acid was synthesized by the Paal–Knorr reaction using 2,5-hexanedione and glycine as raw materials. Various pyrrole fragrance precursors such as 2-ethyl-4-oxo-4H-pyran-3-yl 2-(2,5-dimethyl-1H-pyrrol-1-yl)acetate (5a), 4-formyl-2-methoxyphenyl 2-(2,5-dimethyl-1H-pyrrol-1-yl)acetate (5b), pyridine-2-ylmethyl 2-(2,5-dimethyl-1H-pyrrol-1-yl)acetate (5c) and thiophen-2-ylmethyl 2-(2,5-dimethyl-1H-pyrrol-1-yl)acetate (5d) were synthesized by esterification from 2,5-dimethyl-N-pyrroleacetic acid with ethyl maltol, vanillin, 2-pyridinemethanol and 2-thiophenemethanol, respectively. As part of the study, IR, NMR and HRMS were used to characterize the target compounds. Using gas chromatography–mass spectrometry-olfactometer (GC–MS-O), the pyrrole esters obtained were evaluated for the characteristics of their aromas. The thermal stability was analysed using thermogravimetric analysis and pyrolysis gas chromatography/mass spectrometry. In addition, the pyrolysis mechanism was speculated. With TG-DTG results, the main mass loss phase of 5a occurred between 108°C and 450°C, with a dramatic mass loss reduction of 83.07%. At 118.60°C and 450°C, 5b showed a mass loss reduction of 60.80%. Furthermore, according to the Py-GC/MS analysis results, compounds 5a and 5b formed 8 and 7 pyrolysis products. The main pyrolysis products of 5a and 5b were 1-ethyl-2,5-dimethyl-1H-pyrrole, ethyl maltol, and vanillin, which are all aroma components used to blend cigarette smoke, can slow down the rate at which aromas are lost and mask unpleasant smoke. Study results provide a reference for the tobacco industry to further develop new high-temperature release aroma ingredients.
中文翻译：
多种新型吡咯酯类香精前体的合成与裂解
由于吡咯单体在烟草或食品中高温加工时香味阈值低、挥发性大等缺点，不能满足市场需求。为了开发吡咯风味前体，以2,5-己二酮和甘氨酸为原料，采用Paal-Knorr反应合成了2,5-二甲基-N-吡咯乙酸。各种吡咯香料前体，例如 2-ethyl-4-oxo-4H-pyran-3-yl 2-(2,5-dimethyl-1H-pyrrol-1-yl)acetate ( 5a )、4-formyl-2 - methoxyphenyl 2-(2,5-二甲基-1H-吡咯-1-基)乙酸酯 ( 5b )、吡啶-2-基甲基 2-(2,5-二甲基-1H-吡咯-1-基) 乙酸酯 ( 5c ) 和噻吩-2-ylmethyl 2-(2,5-dimethyl-1H-pyrrol-1-yl)acetate ( 5d)分别由2,5-二甲基-N-吡咯乙酸与乙基麦芽酚、香草醛、2-吡啶甲醇和2-噻吩甲醇酯化合成。作为研究的一部分，IR、NMR 和 HRMS 用于表征目标化合物。使用气相色谱 - 质谱 - 嗅觉计（GC-MS-O），评估获得的吡咯酯的香气特征。使用热重分析和热解气相色谱/质谱分析热稳定性。此外，还推测了热解机理。根据 TG-DTG 结果， 5a的主要质量损失阶段发生在 108°C 和 450°C 之间，质量损失显着减少 83.07%。在 118.60°C 和 450°C 时，5b表明质量损失减少了 60.80%。此外，根据 Py-GC/MS 分析结果，化合物5a和5b形成8和7热解产物。5a和5b的主要热解产物为1-乙基-2,5-二甲基-1H-吡咯、乙基麦芽酚和香草醛，这些都是用于调配卷烟烟气的香气成分，可以减缓香气的流失速度并掩盖难闻的烟雾。研究结果为烟草行业进一步开发新型高温释香成分提供了参考。
更新日期：2023-04-17
中文翻译：
多种新型吡咯酯类香精前体的合成与裂解
由于吡咯单体在烟草或食品中高温加工时香味阈值低、挥发性大等缺点，不能满足市场需求。为了开发吡咯风味前体，以2,5-己二酮和甘氨酸为原料，采用Paal-Knorr反应合成了2,5-二甲基-N-吡咯乙酸。各种吡咯香料前体，例如 2-ethyl-4-oxo-4H-pyran-3-yl 2-(2,5-dimethyl-1H-pyrrol-1-yl)acetate ( 5a )、4-formyl-2 - methoxyphenyl 2-(2,5-二甲基-1H-吡咯-1-基)乙酸酯 ( 5b )、吡啶-2-基甲基 2-(2,5-二甲基-1H-吡咯-1-基) 乙酸酯 ( 5c ) 和噻吩-2-ylmethyl 2-(2,5-dimethyl-1H-pyrrol-1-yl)acetate ( 5d)分别由2,5-二甲基-N-吡咯乙酸与乙基麦芽酚、香草醛、2-吡啶甲醇和2-噻吩甲醇酯化合成。作为研究的一部分，IR、NMR 和 HRMS 用于表征目标化合物。使用气相色谱 - 质谱 - 嗅觉计（GC-MS-O），评估获得的吡咯酯的香气特征。使用热重分析和热解气相色谱/质谱分析热稳定性。此外，还推测了热解机理。根据 TG-DTG 结果， 5a的主要质量损失阶段发生在 108°C 和 450°C 之间，质量损失显着减少 83.07%。在 118.60°C 和 450°C 时，5b表明质量损失减少了 60.80%。此外，根据 Py-GC/MS 分析结果，化合物5a和5b形成8和7热解产物。5a和5b的主要热解产物为1-乙基-2,5-二甲基-1H-吡咯、乙基麦芽酚和香草醛，这些都是用于调配卷烟烟气的香气成分，可以减缓香气的流失速度并掩盖难闻的烟雾。研究结果为烟草行业进一步开发新型高温释香成分提供了参考。
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