50459-25-1

Basic information

• Product Name: (-)-methyl 4-epi-quinate
• Synonyms: (-)-methyl 4-epi-quinate
• CAS NO: 50459-25-1
• Molecular Weight: 206.196
• Mol File: 50459-25-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (-)-methyl 4-epi-quinate(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-methyl 4-epi-quinate(50459-25-1)
• EPA Substance Registry System: (-)-methyl 4-epi-quinate(50459-25-1)

Safety Data

• Hazardous Substances Data: 50459-25-1(Hazardous Substances Data)

Upstream product

• 213250-58-9 (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-oxocyclohexanecarboxylic acid methyl ester 
• 135711-62-5 methyl quinicate 
• 67-56-1 methanol 
• 77-95-2 (1R,3R,4R,5R)-(-)-quinic acid 
• 191916-39-9 methyl (-)-quinate 
• 77-95-2 D-(-)-quinic acid 

Downstream Products

• 640-06-2 (1S,3R,4S,5R)-1,3,4-trihydroxycyclohexane-1,5-carbolactone 

Relevant articles and documents

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.