title: Occurrence of polyfunctional thiols in fresh lager beers.
abstract: Polyfunctional thiols are known to have a strong impact on the overall aroma of many fermented foods. Surprisingly, very little data is available on their occurrence in beer. A specific extraction with p-hydroxymercuribenzoic acid was performed on four different fresh light-protected lager beers. gas chromatography-olfactometry, gas chromatography-mass spectrometry, and gas chromatography-pulsed-flame photometer detector analyses of the extracts revealed the presence of more than 10 polyfunctional thiols. All of them were absent from wort, suggesting a key role of the H(2)S excreted by yeasts. 3-Methyl-2-buten-1-thiol, 2-mercapto-3-methylbutanol, 3-mercapto-3-methylbutanol seem to be created from hop allylic alcohols via four different mechanisms: nucleophilic substitution, addition-elimination, and radical anti-Markovnikov or electrophilic Markovnikov additions. 1,4 Addition of hydrogen sulfide to wort alpha,beta-unsaturated aldehydes or ketones may explain the synthesis of 1-mercapto-3-pentanol, 3-mercaptohexanol, and 4-mercapto-4-methyl-2-pentanone through fermentation. Finally, 2-mercaptoethanol, 3-mercaptopropanol, and their corresponding acetates may derive from Ehrlich degradation of sulfur amino acids, while 2-methyl-3-furanthiol should be logically issued from Maillard reactions.
authors.affiliation: Université Catholique de Louvain, Unité de Brasserie et des Industries Alimentaires, Croix du Sud 2 Bte 7, B-1348 Louvain-la-Neuve, Belgium.
authors.forename: C
authors.initials: C
authors.lastname: Vermeulen
authors.forename: I
authors.initials: I
authors.lastname: Lejeune
authors.forename: T T H
authors.initials: TT
authors.lastname: Tran
authors.forename: S
authors.initials: S
authors.lastname: Collin
mesh_terms: D001515:Beer / Q000032:analysis*; D002849:Chromatography, Gas; D005285:Fermentation; D008401:Gas Chromatography-Mass Spectrometry; D009812:Odorants / Q000032:analysis; D012903:Smell; D013438:Sulfhydryl Compounds / Q000032:analysis*
chemical_list: D013438:Sulfhydryl Compounds