Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 68, Issue 19, Pages 5448-5454Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jafc.0c01679
Keywords
2-acetylfuran; carbonyl-amine reactions; furfural; honey; 5-hydroxymethylfurfural; Maillard reaction; pyridin-3-ols; reactive carbonyls
Funding
- Ministerio de Ciencia, Innovacion y Universidades (MCIU) from Spain
- Agencia Estatal de Investigacion (AEI) from Spain
- Fondo Europeo de Desarrollo Regional (FEDER) from the European Union [RTI2018-096632-B-100]
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The 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.
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