Please use this identifier to cite or link to this item:
Title: Synthesis, structure, and tandem mass spectrometric characterization of the diastereomers of quinic acid
Authors: Deshpande, Sagar
Matei, Marius Febi
Jaiswal, Rakesh
Bassil, Bassem 
Kortz, Ulrich
Kuhnert, N.J
Affiliations: Department of Chemistry 
Keywords: Cis-quinic aci
Epi-quinic acid
Muco-quinic acid
Scyllo-quinic acid
Subjects: Coffee
Issue Date: 2016
Part of: Agricultural and food chemistry
Volume: 64
Issue: 38
Start page: 7298
End page: 7306
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.
Type: Journal Article
Appears in Collections:Department of Chemistry

Show full item record

Record view(s)

checked on Aug 9, 2022

Google ScholarTM


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.