Maillard reaction of D-glucose: identification of a colored product with conjugated pyrrole and furanone rings.
Formation of colored compounds during the Maillard reaction of D-glucose with butylammonium acetate in aqueous solution has been investigated. Butylamine was used as a model compound analogous to the lysine side chains of proteins. The previously unknown, yellow product, 4-hydroxy-5-methyl-2-(N-butyl-3-hydroxy-5-(2-hydroxyethyl)pyrrolyl-2-methylidene)-2H-furan-3-one (1a), was isolated from the reaction mixtures and identified by spectroscopic data.
Lerche
Holger
H
Department of Pharmacy, University of Munich, Butenandtstrasse 7, 81377 Munich, Germany.
Pischetsrieder
Monika
M
Severin
Theodor
T
D002082:Butylamines / Q000737:chemistry; D003116:Color; D005663:Furans / Q000737:chemistry*; D005947:Glucose / Q000737:chemistry*; D006358:Hot Temperature; D009682:Magnetic Resonance Spectroscopy; D015416:Maillard Reaction; D013058:Mass Spectrometry; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry*
D002082:Butylamines; D005663:Furans; D011758:Pyrroles; D005947:Glucose