Reinvestigation of the reaction between 2-furancarboxaldehyde and 4-hydroxy-5-methyl-3(2H)-furanone.
The reaction between 2-furancarboxaldehyde and 4-hydroxy-5-methyl-3(2H)-furanone was reinvestigated as a part of a systematic study on low molecular weight colored compounds from the Maillard reaction. In acetic acid/piperidine, besides 2-(2-furanylmethylene)-4-hydroxy-5-methyl-3(2H)-furanone (1) and 5-[2-(2-furanyl)ethenyl]-2-(2-furanylmethylene)-4-hydroxy-5-methyl -3( 2H)-furanone (2), four novel compounds, 15a, 15b, 16a, and 16b, were isolated and characterized. These compounds are produced from two molecules of furanone 1 and one molecule of 2-furancarboxaldehyde, and a mechanism is proposed for their formation. Compounds 1, 15a, 15b, 16a, and 16b are formed also by reacting 2-furancarboxaldehyde and 4-hydroxy-5-methyl-3(2H)-furanone in water at pH 3 and 2, whereas 2 was never detected. The formation of these compounds was studied also in xylose/lysine and xylose/glycine model systems.
Ravagli
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Dipartimento di Scienze Molecolari Agroalimentari, Sezione di Chimica, Università di Milano, via Celoria 2, I-20133 Milano, Italy.
Boschin
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Scaglioni
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Arnoldi
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D002851:Chromatography, High Pressure Liquid; D005662:Furaldehyde / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D015416:Maillard Reaction; D013058:Mass Spectrometry
D005663:Furans; D005662:Furaldehyde; C113254:4-hydroxy-5-methyl-3(2H)-furanone