Degradation of coffee flavor compound furfuryl mercaptan in fenton-type model systems

Blank, Imre; Pascual, Ederlinda C.; Devaud, Stéphanie; Fay, Laurent B.; Stadler, Richard H.; Yeretzian, Chahan; Goodman, Bernard A.

doi:10.1021/jf011329m

Publication type:	Article in scientific journal
Type of review:	Peer review (publication)
Title:	Degradation of coffee flavor compound furfuryl mercaptan in fenton-type model systems
Authors:	Blank, Imre Pascual, Ederlinda C. Devaud, Stéphanie Fay, Laurent B. Stadler, Richard H. Yeretzian, Chahan Goodman, Bernard A.
DOI:	10.1021/jf011329m
Published in:	Journal of Agricultural and Food Chemistry
Volume(Issue):	50
Issue:	8
Page(s):	2356
Pages to:	2364
Issue Date:	2002
Publisher / Ed. Institution:	American Chemical Society
ISSN:	0021-8561 1520-5118
Language:	English
Subjects:	Coffee; Aroma
Subject (DDC):	663: Beverage technology
Abstract:	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°C. The losses were lower when one or more of the reagents was omitted or the temperature decreased to 22°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.
URI:	https://digitalcollection.zhaw.ch/handle/11475/5517
Fulltext version:	Published version
License (according to publishing contract):	Licence according to publishing contract
Departement:	Life Sciences and Facility Management
Organisational Unit:	Institute of Chemistry and Biotechnology (ICBT)
Appears in collections:	Publikationen Life Sciences und Facility Management

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Blank, I., Pascual, E. C., Devaud, S., Fay, L. B., Stadler, R. H., Yeretzian, C., & Goodman, B. A. (2002). Degradation of coffee flavor compound furfuryl mercaptan in fenton-type model systems. Journal of Agricultural and Food Chemistry, 50(8), 2356–2364. https://doi.org/10.1021/jf011329m

Blank, I. et al. (2002) ‘Degradation of coffee flavor compound furfuryl mercaptan in fenton-type model systems’, Journal of Agricultural and Food Chemistry, 50(8), pp. 2356–2364. Available at: https://doi.org/10.1021/jf011329m.

I. Blank et al., “Degradation of coffee flavor compound furfuryl mercaptan in fenton-type model systems,” Journal of Agricultural and Food Chemistry, vol. 50, no. 8, pp. 2356–2364, 2002, doi: 10.1021/jf011329m.

BLANK, Imre, Ederlinda C. PASCUAL, Stéphanie DEVAUD, Laurent B. FAY, Richard H. STADLER, Chahan YERETZIAN und Bernard A. GOODMAN, 2002. Degradation of coffee flavor compound furfuryl mercaptan in fenton-type model systems. Journal of Agricultural and Food Chemistry. 2002. Bd. 50, Nr. 8, S. 2356–2364. DOI 10.1021/jf011329m

Blank, Imre, Ederlinda C. Pascual, Stéphanie Devaud, Laurent B. Fay, Richard H. Stadler, Chahan Yeretzian, and Bernard A. Goodman. 2002. “Degradation of Coffee Flavor Compound Furfuryl Mercaptan in Fenton-Type Model Systems.” Journal of Agricultural and Food Chemistry 50 (8): 2356–64. https://doi.org/10.1021/jf011329m.

Blank, Imre, et al. “Degradation of Coffee Flavor Compound Furfuryl Mercaptan in Fenton-Type Model Systems.” Journal of Agricultural and Food Chemistry, vol. 50, no. 8, 2002, pp. 2356–64, https://doi.org/10.1021/jf011329m.