Allithiolanes: Nine groups of a newly discovered family of sulfur compounds responsible for the bitter off-taste of processed onion

0493036 - BC 2019 RIV US eng J - Journal Article
Kubec, R. - Štefanová, I. - Moos, Martin - Urajová, Petra - Kuzma, Marek - Zápal, Jakub
Allithiolanes: Nine groups of a newly discovered family of sulfur compounds responsible for the bitter off-taste of processed onion.
Journal of Agricultural and Food Chemistry. Roč. 66, č. 33 (2018), s. 8783-8794. ISSN 0021-8561. E-ISSN 1520-5118
R&D Projects: GA MŠMT(CZ) LM2015055; GA MŠMT(CZ) LO1416; GA MŠMT(CZ) LO1509
Institutional support: RVO:60077344 ; RVO:61388971
Keywords : allithiolane * Allium cepa * bitter
OECD category: Biochemistry and molecular biology; Agriculture (MBU-M)
Impact factor: 3.571, year: 2018
https://pubs.acs.org/doi/10.1021/acs.jafc.8b03118

The compounds responsible for the bitter off-taste of processed onion (Allium cepa) were studied. Using a series of sensory-guided HPLC fractionations, the existence of nine groups of hitherto unknown sulfur compounds has been revealed. On the basis of spectroscopic data (MS, NMR, and IR), it was found that these compounds, trivially named allithiolanes A-I, are members of a large family of structurally closely related derivatives of 3,4-dimethylthiolane S-oxide, with the general formulas of CxHyO2S4, CxHyO3S5, and CxHyO4S6, (x = 10-18, y = 18-30). The presence of multiple stereoisomers was observed for each group of allithiolanes. Allithiolanes possess an unpleasantly bitter taste with detection thresholds in the range of 15-30 ppm. Formation pathways of these newly discovered sulfur compounds were proposed.
Permanent Link: http://hdl.handle.net/11104/0286738