Preparation and pyrolysis of two Amadori analogues as flavor precursors

• Published in: Journal of analytical and applied pyrolysis Vol. 160; p. 105357
• Main Authors: Li, Rui, Yin, Xiaoqing, Zhang, Shiyi, Yang, Jinchu, Zhao, Mingqin
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01.11.2021
• Subjects: Amadori analogue; Flavor precursor; Maillard reaction; Thermal pyrolysis; Maillard reaction; Thermal pyrolysis; Amadori analogue; Flavor precursor
• ISSN: 0165-2370; 1873-250X
• DOI: 10.1016/j.jaap.2021.105357

Amadori compounds, produced during Maillard reaction, are considered as precursors of flavor compounds. On the basis of Amadori compounds, herein two Amadori analogues, di-O-isopropylidene-2,3:4,5-β-D-fructopyranosyl alanine ester (A-ARP) and di-O-isopropylidene-2,3:4,5-β-D-fructopyranosyl proline ester (P-ARP), were chemically synthesized and their possibility as flavor precursors was evaluated by thermogravimetry (TG), derivative thermogravimetry (DTG), differential scanning calorimetry (DSC), and pyrolysis gas chromatography-mass spectrometry (Py-GC/MS). TG-DTG analyses indicated that the samples were stable at room temperature, and the largest mass-loss rates (Tp) were at 208 and 278 °C, respectively. Upon thermal pyrolysis, the major flavor substances were butan-2-one, ethyl propionate, furfural, and dl-limonene for A-ARP, while 2,5-dimethylfuran, heptan-2-one, acetophenone, and 1H-pyrrole for P-ARP. The flavor profiles are different from that of corresponding Amadori compounds, and are influenced by pyrolytic temperatures. These results provide one method to regulate the species and amounts of the degraded flavor products. Finally, the possible mechanisms of the pyrolytic processes are proposed. [Display omitted] •Two Amadori analogues are chemically synthesized in a yield up to 70%.•The pyrolytic products of Amadori analogues are mainly furans, pyrroles and ketones.•Amadori analogue can be potential alternative to Amadori compound as flavor precursor.•The pyrolytic degradation of proline moiety likely forms pyrroles and pyrrolidines.