Document Detail

Degradation of the coffee flavor compound furfuryl mercaptan in model Fenton-type reaction systems.
MedLine Citation:
PMID:  11929297     Owner:  NLM     Status:  MEDLINE    
The stability of the coffee flavor compound furfuryl mercaptan has been investigated in aqueous solutions under Fenton-type reaction conditions. The impact of hydrogen peroxide, iron, ascorbic acid, and ethylenediaminetetraacetic acid was studied in various combinations of reagents and temperature. Furfuryl mercaptan reacts readily under Fenton-type reaction conditions, leading to up to 90% degradation within 1 h at 37 degrees C. The losses were lower when one or more of the reagents was omitted or the temperature decreased to 22 degrees C. Volatile reaction products identified were mainly dimers of furfuryl mercaptan, difurfuryl disulfide being the major compound. In addition, a large number of nonvolatile compounds was observed with molecular masses in the range of 92-510 Da. The formation of hydroxyl and carbon-centered radicals was indicated by electron paramagnetic resonance spectra using alpha-(4-pyridyl-1-oxide)-N-tert-butylnitrone or 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline-N-oxide as spin traps. Whereas *OH was generated by Fenton-type reactions, the C-centered radical is probably a secondary product of the reaction of *OH with various organic molecules, the reaction with furfuryl mercaptan appearing to be the most important. No evidence for S-centered radicals was seen in the spin-trapping experiments, but a sulfur-containing radical was detected when measurements were made at 77 K in the absence of spin traps.
Imre Blank; Ederlinda C Pascual; Stéphanie Devaud; Laurent B Fay; Richard H Stadler; Chahan Yeretzian; Bernard A Goodman
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of agricultural and food chemistry     Volume:  50     ISSN:  0021-8561     ISO Abbreviation:  J. Agric. Food Chem.     Publication Date:  2002 Apr 
Date Detail:
Created Date:  2002-04-03     Completed Date:  2002-05-29     Revised Date:  2007-11-15    
Medline Journal Info:
Nlm Unique ID:  0374755     Medline TA:  J Agric Food Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  2356-64     Citation Subset:  IM    
Nestec Ltd., Nestlé Research Center, Vers-chez-les-Blanc, P.O. Box 44, CH-1000 Lausanne 26, Switzerland.
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MeSH Terms
Ascorbic Acid / pharmacology
Coffee / chemistry*
Drug Stability
Edetic Acid / pharmacology
Electron Spin Resonance Spectroscopy
Free Radicals
Furans / chemistry*
Hydrogen Peroxide / chemistry*,  pharmacology
Hydroxyl Radical / chemistry
Indicators and Reagents
Iron / chemistry*,  pharmacology
Spin Labels
Sulfhydryl Compounds / chemistry*
Reg. No./Substance:
0/Coffee; 0/Fenton's reagent; 0/Free Radicals; 0/Furans; 0/Indicators and Reagents; 0/Spin Labels; 0/Sulfhydryl Compounds; 3352-57-6/Hydroxyl Radical; 50-81-7/Ascorbic Acid; 60-00-4/Edetic Acid; 7439-89-6/Iron; 7722-84-1/Hydrogen Peroxide; 98-02-2/furfuryl mercaptan

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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