Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 59, Issue 20, Pages 11058-11062Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jf202448v
Keywords
2-Alkylfurans; lipid oxidation; amino acids; alpha,beta-unsaturated aldehydes
Funding
- Research Foundation Flanders (Belgium) (FWO-Vlaanderen)
- Aspirant Fellowship
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The formation of 2-alkylfurans from the corresponding lipid-derived alpha,beta-unsaturated aldehydes under dry-roasting conditions was investigated in detail. The addition of an amino acid to an alpha,beta-unsaturated aldehyde drastically increased 2-alkylfiiran formation. Peptides and proteins as well were able to catalyze 2-alkylfuran formation from the corresponding alpha,beta-unsaturated aldehydes. Further investigation of 2-alkylfuran formation showed the need of oxidizing conditions and the involvement of radicals in the reaction. This way, the formation of 2-methylfuran from 2-pentenal, 2-ethylfuran from 2-hexenal, 2-propylfuran from 2-heptenal, 2-butylfuran from 2-octenal, 2-pentylfuran from 2-nonenal, and 2-hexylfuran from 2-decenal was shown. The impact of amino acids on 2-allcylfuran formation from lipid-derived alpha,beta-unsaturated aldehydes represents an interesting example of the complex role of amino acids in the multitude of chemical reactions occurring during thermal processing of lipid-rich foods.
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