Related Experiment Video
Updated: Dec 29, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Process-induced formation of imidazoles in selected foods
Pascal Mottier1, Claudia Mujahid1, Adrienne Tarres1
1Nestlé Research Center, Vers-chez-les-Blanc, 1000 Lausanne 26, Switzerland.
Abstract:
The presence of 4-methylimidazole (4-MEI), 2-methylimidazole (2-MEI) and 2-acetyl-4-tetrahydroxybutylimidazole (THI) in some foods may result from the usage of caramel colorants E150c and E150d as food additives. This study demonstrates that alkylimidazoles are also byproducts formed from natural constituents in foods during thermal processes. A range of heat-processed foods that are known not to contain caramel colorants were analyzed by isotope dilution LC-MS/MS to determine the contamination levels. Highest 4-MEI concentrations (up to 466µg/kg) were observed in roasted barley, roasted malt and cocoa powders, with the concomitant presence of 2-MEI and/or THI in some cases, albeit at significantly lower levels. Low amounts of 4-MEI (<20µg/kg) were also detected in cereal-based foods such as breakfast cereals and bread toasted to a brown color (medium toasted). The occurrence of 4-MEI in certain processed foods is therefore not a reliable indicator of the presence of the additives E150c or E150d.
Related Concept Videos
Aldehydes and Ketones with Amines: Imine Formation Mechanism
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
2° Amines to N-Nitrosamines: Reaction with NaNO2
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...

