Document Detail


Formation of furan and methylfuran by maillard-type reactions in model systems and food.
MedLine Citation:
PMID:  18439018     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Anita Limacher; Josef Kerler; Tomas Davidek; Frank Schmalzried; Imre Blank
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of agricultural and food chemistry     Volume:  56     ISSN:  0021-8561     ISO Abbreviation:  J. Agric. Food Chem.     Publication Date:  2008 May 
Date Detail:
Created Date:  2008-06-16     Completed Date:  2008-07-28     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  0374755     Medline TA:  J Agric Food Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  3639-47     Citation Subset:  IM    
Affiliation:
Nestlé Product Technology Center Orbe, 1350 Orbe, Switzerland, Institute of Food Science and Nutrition, ETH Zurich, Schmelzbergstrasse 9, 8092 Zurich.
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MeSH Terms
Descriptor/Qualifier:
Amino Acids / chemistry
Carbohydrates / chemistry
Food Analysis*
Food Handling / methods
Furaldehyde / analogs & derivatives*,  analysis,  chemical synthesis
Furans / analysis,  chemical synthesis*
Hot Temperature
Maillard Reaction*
Models, Chemical
Pressure
Chemical
Reg. No./Substance:
0/Amino Acids; 0/Carbohydrates; 0/Furans; 110-00-9/furan; 620-02-0/5-methyl-2-furfural; 98-01-1/Furaldehyde

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