Model Reactions on the Stability of Disulfides in Heated Foods

Bis(2-methyl-3-furyl) disulfide (MFT-MFT) and bis(2-furfuryl) disulfide (FFT-FFT) dissolved either in benzene or in water were heated at 100 °C for 2 h. In benzene, 2-methyl-3-furanthiol and 2-furfurylthiol were formed when the hydrogen donor 1,4-cyclohexadiene or 1,4-hexadiene or the antioxidant BHT was present. In water, MFT-MFT, FFT-FFT, and also cystine were hydrolyzed with formation of the corresponding thiols, which were trapped by the reaction with 4-vinylpyridine. Labeling experiments and the measurement of EPR spectra gave an insight into the mechanism of the disulfide cleavage.