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Formation of alpha-dicarbonyl compounds in beer during storage of Pilsner.

Journal of agricultural and food chemistry (2008-05-09)
Adriana Bravo, Julio C Herrera, Erika Scherer, Yon Ju-Nam, Heinrich Rübsam, Jorge Madrid, Carsten Zufall, Rafael Rangel-Aldao
RESUMEN

With the aim of determining the formation of alpha-dicarbonyl intermediates during beer aging on the shelf, alpha-dicarbonyls were identified and quantified after derivatization with 1,2-diaminobenze to generate quinoxalines. The sensory effects of alpha-dicarbonyls were evaluated by the quantification of key Strecker aldehydes and by GC-olfactometry (GCO)analysis of beer headspace using solid phase microextraction. Four alpha-dicarbonyls, reported here for the first time, were detected in fresh and aged beers, three were derived from the 2,3-enolization pathway of mono- and disaccharides, and the fourth was derived from the epimerization of 3-deoxy-2-hexosulose. Ten alpha-dicarbonyls were quantified during beer processing and during different periods of beer aging at 28 degrees C. The aging periods were from 15 to 105 days. During beer aging, 1-deoxydiuloses were produced and degraded, while 1,4-dideoxydiuloses were produced at the highest rates. The GCO analysis indicated that forced beer aging increased the amounts of furaneol, trans-2-nonenal, and phenylacetaldehyde. The blockage of alpha-dicarbonyls inhibited the accumulation of sensory-active aldehydes in the beer headspace.

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Sigma-Aldrich
4-Hydroxy-2,5-dimethyl-3(2H)-furanone, ≥98%, FCC, FG
Sigma-Aldrich
trans-2-Nonenal, 95%
Sigma-Aldrich
4-Hydroxy-2,5-dimethyl-3(2H)-furanone, ≥99.0% (GC)
Sigma-Aldrich
4-Hydroxy-2,5-dimethyl-3(2H)-furanone, natural, ≥98%, FG
Sigma-Aldrich
3-Deoxyglucosone, ≥75% (TLC)
Supelco
4-Hydroxy-2,5-dimethyl-3(2H)-furanone, analytical standard