Formation of 4(5)-methylimidazole and its precursors, α-dicarbonyl compounds, in Maillard model systems. 2013

Hae Won Jang, and Yaping Jiang, and Matt Hengel, and Takayuki Shibamoto
Department of Environmental Toxicology, University of California, Davis, California 95616, United States.

Glyoxal, methylglyoxal, and diacetyl formed from sucrose alone and from a D-glucose/ammonia Maillard model system were analyzed by gas chromatography. They are known as precursors of 4(5)-methylimidazole (MI). Glyoxal and methylglyoxal formed more in acidic conditions than in basic conditions, whereas diacetyl formed the most at the highest basic condition of pH 12. Glyoxal formation from sucrose ranged from 0.33 to 32.90 μg/g under four different time and temperature conditions. Amounts of glyoxal, methylglyoxal, and diacetyl formed in Maillard model systems ranged from 2.98 to 46.12 μg/mL, from 8.27 to 156.61 μg/mL, and from 14.94 to 1588.45 μg/mL, respectively. 4(5)-MI formation in the same model systems ranged from 28.56 to 1269.71 μg/mL. Addition of sodium sulfite reduced formation of these chemicals significantly. Total α-dicarbonyl compounds in 12 commercial soft drinks ranged from 5.75 to 50.72 μg/mL. 4(5)-MI was found in levels ranging from 1.76 to 28.11 ng/mL in 10 commercial soft drinks.

UI MeSH Term Description Entries
D007093 Imidazoles Compounds containing 1,3-diazole, a five membered aromatic ring containing two nitrogen atoms separated by one of the carbons. Chemically reduced ones include IMIDAZOLINES and IMIDAZOLIDINES. Distinguish from 1,2-diazole (PYRAZOLES).
D011765 Pyruvaldehyde An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals. Acetylformaldehyde,Methylglyoxal,Oxopropanal,Pyruvic Aldehyde,Aldehyde, Pyruvic
D002253 Carbonated Beverages Drinkable liquids combined with or impregnated with CARBON DIOXIDE. Carbonated Drinks,Soda Pop,Soft Drinks,Beverage, Carbonated,Beverages, Carbonated,Carbonated Beverage,Carbonated Drink,Drink, Carbonated,Drink, Soft,Drinks, Carbonated,Drinks, Soft,Pop, Soda,Pops, Soda,Soda Pops,Soft Drink
D002273 Carcinogens Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included. Carcinogen,Oncogen,Oncogens,Tumor Initiator,Tumor Initiators,Tumor Promoter,Tumor Promoters,Initiator, Tumor,Initiators, Tumor,Promoter, Tumor,Promoters, Tumor
D002849 Chromatography, Gas Fractionation of a vaporized sample as a consequence of partition between a mobile gaseous phase and a stationary phase held in a column. Two types are gas-solid chromatography, where the fixed phase is a solid, and gas-liquid, in which the stationary phase is a nonvolatile liquid supported on an inert solid matrix. Chromatography, Gas-Liquid,Gas Chromatography,Chromatographies, Gas,Chromatographies, Gas-Liquid,Chromatography, Gas Liquid,Gas Chromatographies,Gas-Liquid Chromatographies,Gas-Liquid Chromatography
D003931 Diacetyl Carrier of aroma of butter, vinegar, coffee, and other foods. 2,3-Butanedione,Biacetyl,Diketobutane,Dimethyldiketone,Dimethylglyoxal,2,3 Butanedione
D005511 Food Handling Any aspect of the operations in the preparation, processing, transport, storage, packaging, wrapping, exposure for sale, service, or delivery of food. Food Processing,Handling, Food,Processing, Food
D005947 Glucose A primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. It is used therapeutically in fluid and nutrient replacement. Dextrose,Anhydrous Dextrose,D-Glucose,Glucose Monohydrate,Glucose, (DL)-Isomer,Glucose, (alpha-D)-Isomer,Glucose, (beta-D)-Isomer,D Glucose,Dextrose, Anhydrous,Monohydrate, Glucose
D006037 Glyoxal A 2-carbon aldehyde with carbonyl groups on both carbons. Ethanedial,Ethanedione
D006358 Hot Temperature Presence of warmth or heat or a temperature notably higher than an accustomed norm. Heat,Hot Temperatures,Temperature, Hot,Temperatures, Hot

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