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|Title:||Synthesis, Structure, and Tandem Mass Spectrometric Characterization of the Diastereomers of Quinic Acid||Authors:||Deshpande, Sagar
Matei, Marius Febi
|Affiliations:||Department of Chemistry||Keywords:||Cis-quinic aci
|Subjects:||Coffee||Issue Date:||2016||Part of:||Agricultural and food chemistry||Volume:||64||Issue:||38||Start page:||7298||End page:||7306||Abstract:||
Quinic acid possess eight possible stereoisomers, which occur both naturally and as products of thermal food processing. In this contribution, we have selectively synthesized four isomers, namely, epi-quinic acid, muco-quinic acid, cis-quinic acid, and scyllo-quinic acid, to develop a tandem LC-MS method identifying all stereoisomeric quinic acids. Four derivatives have been unambiguously characterized by single-crystal X-ray crystallography. The missing diastereomers of quinic acid were obtained by nonselective isomerization of (−)-quinic acid using acetic acid/concentrated H2SO4 allowing chromatographic separation and assignment of all diastereomers of quinic acid. We report for the first time that a full set of stereoisomers are reliably distinguishable on the basis of their tandem mass spectrometric fragment spectra as well as their elution order. A rationale for characteristic fragmentation mechanisms is proposed. In this study, we also observed that muco-quinic acid, scyllo-quinic acid, and epi-quinic acid are present in hydrolyzed Guatemalan roasted coffee sample as possible products of roasting.
|Appears in Collections:||Department of Chemistry|
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