Thermal degradation of 2-furoic acid and furfuryl alcohol as pathways in the formation of furan and 2-methylfuran in food. (15th January 2020)

• Record Type: Journal Article
• Authors: Delatour, Thierry; Huertas-Pérez, José F.; Dubois, Mathieu; Theurillat, Xanthippe; Desmarchelier, Aurélien; Ernest, Marion; Stadler, Richard H.
• Is Part Of: Food chemistry. Volume 303(2020)
• Publication Date: 2020-01-15
• Subjects: Furan -- 2-Methylfuran -- 2-Furoic acid -- Furfuryl alcohol -- Thermal degradation -- Coffee -- Food; Food -- Analysis -- Periodicals; Food -- Composition -- Periodicals; 664
• DOI: 10.1016/j.foodchem.2019.125406
• Languages: English
• ISSNs: 0308-8146

Abstract

Highlights: Decomposition of 2-furoic acid under dry conditions at 190 °C affords furan. Degradation of furfuryl alcohol at 190 °C (dry conditions) furnishes 2-methylfuran. In roasted coffee, level of 2-furoic acid correlates with that of furfuryl alcohol. Some lipid components appear to be precursors of furfuryl alcohol in food. Abstract: This study reports the heat-induced formation of furan by decarboxylation of 2-furoic acid, and 2-methylfuran by dehydration of furfuryl alcohol under dry conditions. Model systems were incubated at temperatures up to 190 °C, followed by quantitative determination of furan and 2-methylfuran performed by isotope dilution headspace gas chromatography-mass spectrometry. Results show that 2-furoic acid decarboxylation and furfuryl alcohol dehydration are activated as from about 140–160 °C. Furfuryl alcohol and 2-furoic acids were measured in a selection of roasted coffee products by isotope dilution liquid chromatography-high resolution mass spectrometry, and the data evidenced a strong correlation between the two compounds, suggesting an intimate mechanistic relationship between them. The possible oxidation of furfuryl alcohol to furfural and 2-furoic acid in heated food is raised with particular emphasis on coffee roasting. These findings are relevant for better understanding the formation of furan and alkylfurans in food, and ultimately opening avenues for mitigation.