Origin of 2,3-Pentanedione and 2,3-Butanedione in d-Glucose/l-Alanine Maillard Model Systems

Abstract

Model studies using independently labeled D-[(13)C]glucoses and L-[(13)C]alanines have indicated that 2,3-butanedione is formed by a single pathway involving only glucose carbon atoms, whereas 2, 3-pentanedione is formed by two pathways, one involving glucose carbon atoms (10%) and the other (90%) through the participation of C2'-C3' atoms of L-alanine and a C(3) carbon unit from D-glucose. Analysis of label incorporation into selected mass spectral fragments of 2,3-pentanedione have indicated that the C(3) carbon unit originates either from C1-C2-C3 or from C4-C5-C6 fragments of D-glucose. In addition, model studies with pyruvaldehyde and glyceraldehyde have implicated these intermediates as plausible C(3) glucose carbon units capable of producing 2,3-pentanedione upon reaction with L-alanine. The labeling studies have also confirmed a previously identified chemical transformation of alpha-keto aldehydes affected by the amino acid that leads to the addition of the C-2 atom of the amino acid to the aldehydic carbon atom of alpha-keto aldehydes.

Basic Chemistry and Process Conditions for Reaction Flavours with Particular Focus on Maillard‐Type Reactions

“…Yaylayan and Keyhani (1999) investigated the origin of these two dicarbonyl compounds in glucose/alanine Maillard model systems under pyrolytic conditions. Using labelled glucose or alanine, the authors showed that 90% of the formed pentanedione requires the participation of the C2/C3 atoms of alanine, whereas diacetyl was derived from the sugar chain only.…”

Development of Maillard Reaction Related Characteristics During Malt Roasting

“…7). The vicinal diketones diacetyl and 2,3-pentanedione are also Maillard reaction products, formed by retro-aldolisation or cleavage 26 . The curves for these vicinal diketones show a sharper peak (Fig.…”

Sensory and Instrumental Flavour Analysis of Wort Brewed with Dark Specialty Malts

“…Nevertheless, these vicinal diketones have also been detected in different Maillard model systems. In the cascade of Maillard reactions, diacetyl and 2,3-pentanedione can be formed by retro-aldolisation or cleavage 47 . These reactive intermediates possess a much higher browning activity than monosaccharides 20 .…”