Chlorine-containing Compounds Derived from Saccharides in Protein Hydrolysates. II. Levulinic Acid Esters in Soybean Meal Hydrolysates

Abstract Volatile constituents of traditionally manufactured soybean meal hydrolysates, widely used as seasonings, were analysed by gas chromatography and gas chromatography/mass spectrometry. Two isomeric esters, 3-chloro-2-hydroxy-1-propyl and 3-chloro-1-hydroxy-2-propyl levulinate, derived from 3-chloro-1,2-propanediol arising from residual lipids and levulinic acid formed via 5-hydroxymethyl-2-furancarboxaldehyde from saccharides were newly identified as volatile constituents of these commodities being present at a level of 0.6 to 1.1 mg/kg. These esters totally decomposed in alkaline media and were not detected in hydrolysates treated with sodium hydroxide.