Formation of furan and methylfuran by maillard-type reactions in model systems and food.
The formation of furan and 2-methylfuran was studied in model systems based on sugars and selected amino acids. Both compounds were preferably formed under roasting conditions in closed systems yielding up to 330 micromol of furan and 260 micromol of 2-methylfuran per mol of precursor. The amounts obtained under pressure cooking conditions were much lower, usually below 20 micromol/mol, except for 2-furaldehyde, which yielded 70-100 micromol/mol of furan. Labeling studies indicated two major formation pathways for both furans: (i) from the intact sugar skeleton and (ii) by recombination of reactive C(2) and/or C(3) fragments. Under roasting conditions in the absence of amino acids, furan was mainly formed from the intact sugar skeleton. Formic and acetic acid were identified as byproducts of sugar degradation, indicating the split off of C(1) and/or C(2) units from hexoses. The presence of alanine, threonine, or serine promoted furan formation by the recombination of C(2) fragments, such as acetaldehyde and glycolaldehyde, which may originate from both sugars and amino acids. In aqueous solution, about half of furan was generated by the recombination of sugar fragments. 2-Methylfuran was preferably formed in the presence of amino acids by aldol-type reactions of C(2) and C(3) fragments with lactaldehyde as a key intermediate, the Strecker aldehyde of threonine. The total furan levels in cooked vegetables were increased by spiking with hexoses. However, in pumpkin puree, only about 20% of furan was formed from sugars, preferably from the intact carbon skeleton.
Limacher
Anita
A
Nestlé Product Technology Center Orbe, 1350 Orbe, Switzerland, Institute of Food Science and Nutrition, ETH Zurich, Schmelzbergstrasse 9, 8092 Zurich.
Kerler
Josef
J
Davidek
Tomas
T
Schmalzried
Frank
F
Blank
Imre
I
D000596:Amino Acids / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry; D005504:Food Analysis; D005511:Food Handling / Q000379:methods; D005662:Furaldehyde / Q000031:analogs & derivatives* / Q000032:analysis / Q000138:chemical synthesis; D005663:Furans / Q000032:analysis / Q000138:chemical synthesis*; D006358:Hot Temperature; D015416:Maillard Reaction; D008956:Models, Chemical; D011312:Pressure
D000596:Amino Acids; D002241:Carbohydrates; D005663:Furans; C048065:5-methyl-2-furfural; D005662:Furaldehyde; C039281:furan