Moisture Property and Thermal Behavior of Two Novel Synthesized Polyol Pyrrole Esters in Tobacco

• Published in: ACS omega Vol. 8; no. 5; pp. 4716 - 4726
• Main Authors: Fan, Wenpeng, Tian, Haiying, Chen, Hongli, Chu, Wenjuan, Han, Lu, Li, Pengyu, Gao, Ziting, Ji, Xiaoming, Lai, Miao
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 07.02.2023
• ISSN: 2470-1343; 2470-1343
• DOI: 10.1021/acsomega.2c06683

To overcome the shortcomings of high relative humidity and harmful oxidation products from traditional humectants, excellent humectants and flavor precursors were reported herein. Glucosamine hydrochloride was used as the starting material for the cyclization, oxidation, and alkylation processes that produced pyrrole acid. Then, esterification occurred with polyol catalyzed by EDC and DMAP to give the target compounds 2-(2,3-dihydroxypropyl) 4-methyl 5-methyl-1-propyl-1H-pyrrole-2,4-dicarboxylate (Gpe) and (2-hydroxypropyl) 4-methyl 5-methyl-1-propyl-1H-pyrrole-2,4-dicarboxylate (Ppe). Nuclear magnetic resonance (1H NMR, 13C NMR), infrared spectroscopy (IR), and high-resolution mass recorded spectrometry (HRMS) were used to confirm the two novel polyol pyrrole ester compounds. When Gpe and Ppe were added to the tobacco shred, low-field nuclear magnetic resonance (LF-NMR) imaging was applied to assess the hygroscopicity and moisturizing capacity. Furthermore, thermogravimetry (TG) and pyrolysis–gas chromatography/mass spectrometry (Py-GC/MS) techniques were applied to study their thermal behaviors. These results showed that the target compounds (Gpe and Ppe) are good humectants with thermal properties of high-temperature stability and flavor release.