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.

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Combinatorial chemistry was used to extend the knowledge of beer thiols by synthesizing 13 mercapto primary alcohols and 6 other compounds (mercapto ketones and corresponding alcohols). Their respective mass spectra, retention indices on two columns, odor descriptors, and best estimated-gas chromatography-lowest amounts detected sniffing (BE-GC-LoADS) are reported. The descriptor "cheese", commonly associated with mercapto aldehydes and thioesters, was rarely used for mercapto alcohols or mercapto ketones. Polyfunctional thiols containing at least six carbon atoms usually gave a delicate odor of rhubarb/carrot, whereas most of the mercapto primary alcohols of intermediate size were described as onion-like, plastic-like, or pungent. Sensorial analysis of beers spiked with copper(II) ions allowed confirmation of the participation of thiols in the overall odor of fresh beer. The finding of 4-mercapto-4-methyl-2-pentanone and 3-mercaptohexanol in an XAD-2 Amberlite resin beer extract indicates a requirement for a more efficient thiol extraction procedure allowing identification of relevant polyfunctional thiols for brewing scientists.

"Spanish style" Moroccan green table olives were screened for potent odorants by gas chromatography-olfactometry/aroma extraction dilution analysis of a representative Likens-Nickerson extract. (Z)-3-Hexenal [flavor dilution factor (FD) = 256], (E,E)-2,4-decadienal (FD = 128), and (E,Z)-2,4-decadienal (FD = 64) were revealed to confer green and coriander/paraffin oil odors to both fruit and oil extracts, whereas guaiacol (FD = 128) imparted a bad olive, phenolic note. Methional (3-methylthiopropionaldehyde, FD = 128) and several terpenes (FD