Identification of Lactose-Derived α-Dicarbonyl Compounds in Dairy Products and Elucidation of Their Formation Mechanism

α-Dicarbonyl compounds (α-DCs) generated from carbohydrates play a key role in food quality and safety as precursors. Lactose contributes to α-DCs generation in dairy products; however, α-DCs with intact lactose carbons have not been investigated so far. This study aimed to identify lactose-derived α-DCs, clarify the mechanism of its formation using model incubations, and investigate the distribution and contents of α-DCs in dairy products. From the heated lactose and lysine solution, four new α-DCs derivatives were isolated by column chromatography and preparative HPLC and identified as lactosone, 1-deoxylactosone (1-DL) and its epimer, and 1,5-dideoxylactoson-4-ene (1,5-DDLE) by MS and NMR analyses. 1-DL, 1-DL epimer, and 1,5-DDLE were specifically formed from Amadori compounds of lactose and could be indicators of lactose-associated Maillard reaction. These α-DCs were abundantly contained in thermally processed dairy products, especially infant formulas and whey protein, and affected by ingredients and manufacturing process.