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Title

Conversion of 5-Hydroxymethylfurfural into 6-(Hydroxymethyl)pyridin-3-ol: A Pathway for the Formation of Pyridin-3-ols in Honey and Model Systems

AuthorsHidalgo, Francisco J. ; Lavado-Tena, Cristina M.; Zamora, Rosario
Keywords2-acetylfuran
carbonyl-amine reactions
furfural
honey
5-hydroxymethylfurfural
Maillard reaction
pyridin-3-ols
reactive carbonyls
Issue Date22-Apr-2020
PublisherAmerican Chemical Society
CitationJournal of Agricultural and Food Chemistry 68 (19): 5448–5454 (2020)
AbstractThe formation of 6-(hydroxymethyl)pyridin-3-ol by ring expansion of 5-(hydroxymethyl)furfural (HMF) in the presence of ammonia-producing compounds was studied to determine the routes of formation of pyridin-3-ols in foods. 6-(Hydroxymethyl)pyridin-3-ol was produced from HMF in model systems, mostly at neutral pH values, as a function of reaction times and temperature and with an activation energy (Ea) of 74 ± 3 kJ/mol, which was higher than that of HMF disappearance (43 ± 4 kJ/mol). A reaction pathway is proposed, which is general for the formation of pyridin-3-ols from 2-oxofurans. Thus, it explains the conversions of furfural into pyridin-3-ol and of 2-acetylfuran into 2-methylpyridin-3-ol, which were also studied. When honey and sugarcane honey were heated, they produced different pyridin-3-ols, although 6-(hydroxymethyl)pyridin-3-ol was the pyridine-3-ol produced to the highest extent. Obtained results suggest that formation of pyridin-3-ols in foods is unavoidable when 2-oxofurans are submitted to thermal heating and ammonia (or ammonia-producing compounds) is present.
Description10 Figuras
Publisher version (URL)http://dx.doi.org/10.1021/acs.jafc.0c01679
URIhttp://hdl.handle.net/10261/212622
ISSN0021-8561
E-ISSN1520-5118
Appears in Collections:(IG) Artículos
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