Thermal degradation of sulforaphane in aqueous solution

J Agric Food Chem. 1999 Aug;47(8):3121-3. doi: 10.1021/jf990082e.

Abstract

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.

MeSH terms

  • Anticarcinogenic Agents / chemistry*
  • Brassica*
  • Cooking
  • Hot Temperature
  • Isothiocyanates
  • Magnetic Resonance Spectroscopy
  • Solutions
  • Spectrometry, Mass, Fast Atom Bombardment
  • Thiocyanates / chemistry*
  • Water

Substances

  • Anticarcinogenic Agents
  • Isothiocyanates
  • Solutions
  • Thiocyanates
  • Water
  • sulforafan