Quinic acid (CHEM022803)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:54:10 UTC
Update Date2016-11-09 01:17:35 UTC
Accession NumberCHEM022803
Identification
Common NameQuinic acid
ClassSmall Molecule
DescriptionQuinic acid is a sugar acid. It is also a cyclitol, a cyclic polyol. More specifically, quinic acid is a crystalline acid obtained from cinchona bark, coffee beans, tobacco leaves, carrot leaves, apples, peaches, pears, plums, vegetables etc. Quinic acid can also be made synthetically by hydrolysis of chlorogenic acid. Quinic acid is implicated in the perceived acidity of coffee.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
QuinateGenerator
(1R,3R,4S)-1,3,4,5-Tetrahydroxycyclohexane-1-carboxylateHMDB
(-)-QuinateHMDB
(-)-Quinic acidHMDB
ChinateHMDB
Chinic acidHMDB
D-Quinic acidHMDB
KinateHMDB
Kinic acidHMDB
L-QuinateHMDB
L-Quinic acidHMDB
Chemical FormulaC7H12O6
Average Molecular Mass192.167 g/mol
Monoisotopic Mass192.063 g/mol
CAS Registry Number77-95-2
IUPAC Name(1R,3R,4S)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid
Traditional Name(1R,3R,4S)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid
SMILESOC1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=O
InChI IdentifierInChI=1S/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4?,5-,7+/m1/s1
InChI KeyAAWZDTNXLSGCEK-RKGSPJAZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentQuinic acids and derivatives
Alternative Parents
Substituents
  • Quinic acid
  • Cyclohexanol
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility765 g/LALOGPS
logP-2.5ALOGPS
logP-2.7ChemAxon
logS0.6ALOGPS
pKa (Strongest Acidic)3.46ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area118.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity39.71 m³·mol⁻¹ChemAxon
Polarizability17.17 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9800000000-fe303752b78b547d4e54Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-000i-5101950000-4c2d01cb772e2291e41aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002g-0900000000-59471dc3f2bf86989e30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0900000000-d0b09550df3fa08a1420Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-5900000000-ab505f7c0b75a85ee3cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0900000000-fe8d862acce93dd7eb84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-3900000000-f7e8be1495cce9a344aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05bb-9700000000-e16830e0be835671623bSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003072
FooDB IDFDB001170
Phenol Explorer IDNot Available
KNApSAcK IDC00001201
BiGG IDNot Available
BioCyc IDQUINATE
METLIN ID3329
PDB IDNot Available
Wikipedia LinkQuinic_acid
Chemspider ID16498843
ChEBI ID17521
PubChem Compound ID6508
Kegg Compound IDC00296
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Nagai, Naoshi; Kuboyama, Hisaharu; Enya, Masahiro. Method for preparation of quinic acid and its esters. Jpn. Kokai Tokkyo Koho (2000), 7 pp.
2. Wittemer SM, Ploch M, Windeck T, Muller SC, Drewelow B, Derendorf H, Veit M: Bioavailability and pharmacokinetics of caffeoylquinic acids and flavonoids after oral administration of Artichoke leaf extracts in humans. Phytomedicine. 2005 Jan;12(1-2):28-38.
3. Akesson C, Lindgren H, Pero RW, Leanderson T, Ivars F: Quinic acid is a biologically active component of the Uncaria tomentosa extract C-Med 100. Int Immunopharmacol. 2005 Jan;5(1):219-29.