New insight into the formation mechanism of 2-furfurylthiol in the glucose-cysteine reaction with ribose. (May 2021)

• Record Type: Journal Article
• Authors: Liu, Huan; Wang, Zhenyu; Hui, Teng; Fang, Fei; Zhang, Dequan
• Is Part Of: Food research international. Volume 143(2021)
• Publication Date: 2021-05
• Subjects: 2-Furfuthiol -- Glucose -- Ribose -- Formation mechanism -- CAMOLA; Food -- Analysis -- Periodicals; Food industry and trade -- Periodicals; Food industry and trade -- Canada -- Periodicals; Food Technology -- Periodicals; Food -- Periodicals; Food-Processing Industry -- Periodicals; Aliments -- Industrie et commerce -- Périodiques; Aliments -- Industrie et commerce -- Canada -- Périodiques; Aliments -- Recherche -- Périodiques; Food industry and trade; Canada; Periodicals; Electronic journals; 664.005
• DOI: 10.1016/j.foodres.2021.110295
• Languages: English
• ISSNs: 0963-9969

Abstract

Graphical abstract: Highlights: Model reaction system and food system were applied to conduct the study. CAMOLA technical approach was used to clarify formation pathway of aroma compound. 2-Furfural and 2-furanmethanol were key intermediates for 2-furfurylthiol. 2-Furfurylthiol was mainly generated from an intact C5 glucose skeleton. 2-Furfurylthiol was formed in glucose-ribose-cysteine reaction by addition effect. Abstract: The molecular formation mechanism of 2-furfurylthiol in the glucose-cysteine reaction is not reported. Knowledge of the molecular interaction of glucose and ribose on the generation of 2-furfurylthiol is still unclear. The carbon module labeling (CAMOLA) technical approach was applied to elucidate the formation mechanism of 2-furfurylthiol in the glucose-cysteine reaction. The effect of ribose on the glucose-cysteine reaction was also evaluated. The results showed that 2-furfural and 2-furanmethanol were important intermediates for the formation of 2-furfurylthiol. Irrespective of the heating time, 2-furfurylthiol was mainly generated from an intact C5 glucose skeleton (88–89%), whereas the recombination of glucose fragments had minimal contribution. 2-Furfural could be generated from the Maillard reaction between glucose and cysteine or glucose alone, which further formed 2-furanmethanol. Immediately, 2-furfurylthiol could arise from the reaction of 2-furanmethanol and H2 S from cysteine. Moreover, the reaction of glucose, ribose, and cysteine could generate 2-furfural, 2-furanmethanol, and 2-furfurylthiol by an addition effect confirmed by the model reaction and food system.