Decomposition Rate of Allyl Isothiocyanate in Aqueous Solution

Effects of changes in pH and temperature on the inhibition of Salmonella and Listeria monocytogenes by Allyl isothiocyanate

“…It seems that AITC is more inhibitory to bacteria at room temperatures because its stability is higher at this temperature. These results are consistent with earlier work where it was shown that AITC is volatile and easily decomposed to new products at elevated temperatures in the presence of water (Ohta et al, 1995;Tsao et al, 2000). The same results were found by Cheng, Hashimoto, and Uda (2004) where AITC was reduced by 84% after 12 h and was not detected after 24 h in sterile Gifu Anaerobic broth medium incubated at 37 C. Luciano and Holley (2009) also found that AITC rapidly decomposed in water at 37 C. Tsao et al (2000) found that the half-life of AITC in a sterile soil-water mixture (supernatant from 1:1 water/air-dried soil) was 43 d at 25 C which is greater than found in the present study.…”

“…AITC is unstable in aqueous solution and is easily decomposed to new compounds, particularly under alkaline conditions or at elevated temperature (Ohta, Takatani, & Kawakishi, 1995;Tsao, Yu, Friesen, Potter, & Chiba, 2000). Therefore, temperature and pH are the major factors influencing AITC stability and these factors also may influence its antimicrobial activity.…”

MTBITC mediates cell cycle arrest and apoptosis induction in human HepG2 cells despite its rapid degradation kinetics in the in vitro model

“…ITCs react rapidly, and under mild conditions with oxygen-, sulfur-, or nitrogen-centered nucleophiles to give rise to carbamates, thiocarbamates, or thiourea derivatives, respectively [Zhang and Talalay, 1994]. Ohta et al [1995] showed that allyl ITC is highly unstable in aqueous solution, its decomposition by the nucleophilic attack of water or even more of hydroxide ions against the ITC group being rapid. A study by Sommerlade et al [2006] dealing with the behavior of ITC in atmospheric surroundings demonstrated that ITCs react intensely with OH radicals to form a variety of different conversion products, which are mainly isocyanates and sulfur dioxide.…”

Effects of Ionized Cyclodextrin on Decomposition of Allyl Isothiocyanate in Alkaline Solutions

“…In alkaline solutions, it was difficult to measure kinetic parameters for the reaction, because the decomposition rate of AITC was very fast, so the reaction was done under the following conditions: the reaction was run at 5 C, because the reaction rate was depressed at low temperatures; after the reaction, sample solutions were adjusted with 2 N H 2 SO 4 solution at pH 4-5 for the stop on the reaction, and then AITC was extracted with hexane from the sample solution for supplying GC analysis. 8) It has previously been described that AITC formed an inclusion complex with -and -CD in an aqueous solution.…”

“…4) AITC is one of the isothiocyanates with biological activities, and is a very reactive and unstable compound in an aqueous solution. 5) We have investigated the depression of the decomposition of AITC in an aqueous solution (pH [2][3][4][5][6][7][8][9] and reported the suppressive effect by the formation of a cyclodextrin-allyl isotyiocyanate (CD-AITC) inclusion complex in a previous paper. 6) It is known that the secondary hydroxyl groups for CD ionize under an alkaline condition, and the interaction between the ionized CD and the included substrates occurs frequently.…”