Furan could be formed by heating of L–ascorbic acid, amino acids, reducing
sugars, and fatty acids. Nevertheless, the mechanism of formation of furan
derivatives differs among each other but all are formed by heating of one or two
of the precursors. Furan and its derivatives give a positive benefit tothe sensory
properties of heated food but also have toxic and in some cases mutagenic effects.
Moreover, the polymerization of furfuryl alcohol as furan derivative contributes to
the formation of the brown colour in heated foods, besides Maillard and
caramelization reactions. During heating of food, furfuryl alcohol is formed
through degradation of quinic acid or 1,2–enediols. Furfuryl alcohol is a
mutagenic compound. In acid conditions it is able to polymerize and form
aliphatic polymers that show a brown colour. In addition, some of those furans
still remain in the liver or kidney whichcan be metabolized forming toxic or
mutagenic compounds that bind to proteins or DNA. In this research project it was
shown that the HPLC using gradient elution with methanol and water can be used
for the identification and quantification of HMF, furfuryl alcohol, and furfural in a
single run. Instant coffee powder, ready–to–drink filter coffee, and cappuccino
contain 5–hydroxymethylfurfural (HMF), furfuryl alcohol, and furfural. Dried
plums and raisins also contain HMF and furfural. Crisp bread contains furfuryl
alcohol and HMF. Besides that, goat cheese contains furfuryl alcohol and cola
beverage contains HMF. The analysed samples were provided by the Norwegian Institute of Public Health investigating the exposure to these substances in
Norway.
Furthermore, here we show that furfuryl alcohol polymerizes in a model system
by incubationin 1 M HCl at room temperature. Some of the reaction products are
oligomers with dimers, trimers, tetramers, and pentamers having a methylene
linkagebeing identified. The degree of polymerization and the amount of those
furfuryl alcohol oligomers increases with increasing reaction time. The results of
this model system were used to characterize the polymerization of furfuryl alcohol
during roasting of coffee. The coffee was roasted at 210 °C for 2, 3, 4, 5, and 6
min using a home coffee roaster. Furfuryl alcohol and its dimer were found in
coffee after 2 and 3 min of roasting reaching a maximum amount after 4 min;
probably due to further reactions the dimeric furfuryl alcohol concentration starts
to decrease after 4 min. We propose that the polymers of furfuryl alcohol
contribute to the brown colour of roasted foods. In urine, the 5–hydroxymethyl–
2–furoic acid as metabolite of HMF and 2–furoic acid as metabolite of furfuryl
alcohol and furfural can be analysed by HPLC separation and 5-methyl furoic acid
as metabolite of 5-methylfurfural and 5-methyl furfuryl alcohol only can be
analysed by LC/MS/MS after alkaline treatment to hydrolyse the glycine
conjugates
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