Model studies on the pattern of volatiles generated in mixtures of amino acids, lipid-oxidation-derived aldehydes, and glucose.
The development of flavor and browning in thermally treated foods results mainly from the Maillard reaction and lipid degradation but also from the interactions between both reaction pathways. To study these interactions, we analyzed the volatile compounds resulting from model reactions of lysine or glycine with aldehydes originating from lipid oxidation [hexanal, (E)-2-hexenal, or (2E,4E)-decadienal] in the presence and absence of glucose. The main reaction products identified in these model mixtures were carbonyl compounds, resulting essentially from amino-acid-catalyzed aldol condensation reactions. Several 2-alkylfurans were detected as well. Only a few azaheterocyclic compounds were identified, in particular 5-butyl-2-propylpyridine from (E)-2-hexenal model systems and 2-pentylpyridine from (2E,4E)-decadienal model reactions. Although few reaction products were found resulting from the condensation of an amino acid with a lipid-derived aldehyde, the amino acid plays an important role in catalyzing the degradation and further reaction of these carbonyl compounds. These results suggest that amino-acid-induced degradations and further reactions of lipid oxidation products may be of considerable importance in thermally processed foods.
Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University , Coupure links 653, B-9000 Ghent, Belgium.
An
A
Adams
Vaida
V
Kitryté
Rimantas
R
Venskutonis
Norbert
N
De Kimpe
D000447:Aldehydes / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D005511:Food Handling; D008401:Gas Chromatography-Mass Spectrometry; D005947:Glucose / Q000737:chemistry*; D005998:Glycine / Q000737:chemistry; D006358:Hot Temperature; D015227:Lipid Peroxidation; D015416:Maillard Reaction; D009088:Mucoproteins / Q000737:chemistry; D055549:Volatile Organic Compounds / Q000138:chemical synthesis*
D000447:Aldehydes; D000596:Amino Acids; D009088:Mucoproteins; D055549:Volatile Organic Compounds; C010393:lysin, gastropoda; D005947:Glucose; D005998:Glycine