193956-42-2

Upstream product

• 130021-73-7 methyl 3,4-O-cyclohexylidenequinate 
• 193888-32-3 3,4-O-cyclohexylidene-5-oxoquinate 
• 901129-88-2 methyl 3,5-di-O-(tert-butyldimethylsilyl)-4-O-methanesulfonylquinate 
• 35949-53-2 (-)-4,5-cyclohexylidenequinic acid lactone 
• 191916-39-9 methyl (-)-quinate 
• 135711-62-5 methyl quinicate 
• 213250-58-9 (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-oxocyclohexanecarboxylic acid methyl ester 
• 193888-33-4 methyl 3,4-O-cyclohexylidene-epi-quinate 
• 77-95-2 D-(-)-quinic acid 

Downstream Products

• 1190866-20-6 methyl (1rn,3R,4sn,5S)-3,4,5-tri[(tert-butyldimethylsilyl)oxy]-1-hydroxycyclohexane-1-carboxylate 

Relevant academic research and scientific papers

Synthesis, Structure, and Tandem Mass Spectrometric Characterization of the Diastereomers of Quinic Acid

(-)-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.

New and efficient enantiospecific synthesis of (-)-methyl 5-epi-shikimate and methyl 5-epi-quinate from (-)-quinic acid

(-)-Methyl 5-epi-shikimate and methyl 5-epi-quinate were synthesized efficiently from readily available and inexpensive (-)quinic acid 1 as a common starting material on a new, short and simple sequence of reactions.