Related Experiment Video
Updated: Aug 13, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
New aspects on the formation and analysis of acrylamide
Peter Schieberle1, Peter Köhler, Michael Granvog
1Lehrstuhl für Lebensmittelchemie der Technischen Universität München, Lichtenbergstrasse 4, D-85748 Garching, Germany. Peter.Schieberle@Lrz.tum.de
Abstract:
The effectiveness of different compounds in the generation of acrylamide (AA) from asparagine, was determined by reacting asparagine with mono-, di- and polysaccharides, as well as four different oxo-compounds known to be involved in carbohydrate metabolism/degradation. Quantitation of AA formed either under aqueous conditions or in low water model systems revealed glucose and 2-oxopropionic acid as the most effective compounds in AA generation, when reacted in model systems with a low water content (about 1 mol-% yield). Interestingly, heating of asparagine in the presence of 2-oxopropionic acid generated quite high amounts of 3-aminopropionamide (3-APA), which itself effectively generated AA upon heating in aqueous solution, as well as in low water systems. Because this is the first report on amounts of 3-APA generated by Maillard-type reactions, the general role of 3-APA as key intermediate in AA formation is discussed in detail. In addition, first results on the development and application of an HPLC/fluorescence method for AA quantitation are presented.
Related Concept Videos
Anionic Chain-Growth Polymerization: Overview
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
Aldehydes and Ketones with Amines: Enamine Formation Mechanism
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Structures of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...

