Synthesis of novel 2-methyl-3-furyl sulfide flavor derivatives as efficient preservatives

Abstract

Foodborne microbial infestation seriously threatens food security, and the development of low-risk food preservatives is highly needed in food production. For discovering novel flavor molecules with antiseptic function, novel 2-methyl-3-furyl sulfide flavor derivatives were synthesized and evaluated. A wide range of 2-methyl-3-furyl sulfide derivatives were synthesized by reactions of 2-methyl-3-furyl disulfide with cyclic ethers, amides, ketones, and epoxides. All of these compounds have special aroma characteristics and low aroma thresholds. The antimicrobial activity of these compounds against test foodborne bacterial or fungal strains (Escherichia coli, Bacillus subtilis, Staphylococcus aureus, Salmonella paratyphi, Listeria monocytogenes, Vibrio parahemolyticus, Penicillium italicum, Aspergillus niger, Mucor racemosus, Rhizopus oryzae) was examined. It was found that fifteen compounds (3a, 3b, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l, 3m, 5a, 5b, 5f) have antimicrobial activity against different foodborne bacterial or fungal strains. Significantly, the antimicrobial activity of the flavor compounds (3b, 3d, 3e, 3i, 3j, 3l, 3m) is better than that of the control group (penicillin, amphotericin B and thiram), and they are promising preservatives for food production.