Related Experiment Video
Updated: Jun 4, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Identification of Lactose-Derived α-Dicarbonyl Compounds in Dairy Products and Elucidation of Their Formation
Yuri Nomi1, Takuma Anazawa1, Kazumi Shinzawa1
1Faculty of Applied Life Sciences, Niigata University of Pharmacy and Medical and Life Sciences, Niigata 956-8603, Japan.
Abstract:
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.
Related Concept Videos
Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives
Intramolecular Aldol Reaction
C–C Bond Formation: Aldol Condensation Overview
β-Dicarbonyl Compounds via Crossed Claisen Condensations
Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids
Aldol Condensation vs Claisen Condensation

