Thermal degradation of sulforaphane in aqueous solution.
Sulforaphane, a cancer chemopreventive agent identified from broccoli, was degraded in an aqueous solution at 50 and 100 degrees C. The reaction mixtures were extracted with methylene chloride and analyzed by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). Dimethyl disulfide, S-methyl methylthiosulfinate, S-methyl methylthiosulfonate, methyl (methylthio)methyl disulfide, 1,2,4-trithiolane, 4-isothiocyanato-1-(methylthio)-1-butene, and 3-butenyl isothiocyanate were identified as volatile decomposition products. After methylene chloride extraction, the aqueous layer was dried and silica gel column chromatography was used to separate and purify the nonvolatile decomposition products. The major thermal degradation compound was determined by (1)H NMR, (13)C NMR, and FAB-MS as N, N'-di(4-methylsulfinyl)butyl thiourea. A possible mechanism for the formation of these products is proposed.
Jin
Y
Y
Department of Food Science and Center for Advanced Food Technology, Cook College, Rutgers University, New Brunswick, New Jersey 08901-8520, USA.
Wang
M
M
Rosen
R T
RT
Ho
C T
CT
D016588:Anticarcinogenic Agents / Q000737:chemistry*; D001937:Brassica; D003296:Cooking; D006358:Hot Temperature; D017879:Isothiocyanates; D009682:Magnetic Resonance Spectroscopy; D012996:Solutions; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013454:Sulfoxides; D013861:Thiocyanates / Q000737:chemistry*; D014867:Water
D016588:Anticarcinogenic Agents; D017879:Isothiocyanates; D012996:Solutions; D013454:Sulfoxides; D013861:Thiocyanates; D014867:Water; C016766:sulforaphane