Record Information
Version1.0
Creation date2010-04-08 22:04:51 UTC
Update date2019-11-26 02:56:03 UTC
Primary IDFDB001170
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(-)-Quinic acid
DescriptionOccurs in coffee beans and many other plant sources. Food acidulant with good taste characteristics, use limited by cost Quinic acid is an organic acid which is found in cinchona bark and elsewhere in plants. 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 and Shikimic acid are key intermediates in the biosynthesis of aromatic compounds in living systems. Quinic acid can also be made synthetically by hydrolysis of chlorogenic acid. Quinic acid is implicated in the perceived acidity of coffee.; Quinic acid, C7H12O6 is a crystalline acid obtained from cinchona bark, coffee beans, and other plant products and made synthetically by hydrolysis of chlorogenic acid. Quinic acid is also implicated in the perceived acidity of coffee.; This acid is a versatile chiral starting material for the synthesis of new pharmaceuticals. A new medicament for the treatment of influenza A and B strains called Tamiflu has been successfully developed and launched into the market recently.
CAS Number77-95-2
Structure
Thumb
Synonyms
SynonymSource
(-)-QuinateGenerator
(-)-Quinic acidbiospider
(1R,3R,4R,5R)-(-)-Tetrahydroxycyclohexanecarboxylic acidbiospider
(1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acidmanual
ChinateHMDB
Chinic acidHMDB
D-(-)-Quinic acidbiospider
D-Quinic acidbiospider
KinateHMDB
Kinic acidHMDB
L-QuinateHMDB
L-Quinic acidHMDB
N-(2-Phenylethyl)-acetamidebiospider
N-AcetylphenylethylamineHMDB
N-Qcetylphenylethylaminebiospider
QuinateHMDB
Quinic acidmanual
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
Polarizability17.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H12O6
IUPAC name1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid
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)
InChI KeyAAWZDTNXLSGCEK-UHFFFAOYSA-N
Isomeric SMILESOC1CC(O)(CC(O)C1O)C(O)=O
Average Molecular Weight192.1666
Monoisotopic Molecular Weight192.063388116
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 43.75%; H 6.29%; O 49.95%DFC
Melting PointMp 162-163°DFC
Boiling PointNot Available
Experimental Water Solubility290 mg/mL at 9 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP1.19RADZICKA,A & WOLFENDEN,R (1988)
Experimental pKapKa 3.58 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]26D -42.1 (H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(-)-Quinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002f-9600000000-5fad8732698ac44de438Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002g-0900000000-59471dc3f2bf86989e30Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0900000000-d0b09550df3fa08a1420Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-5900000000-ab505f7c0b75a85ee3cdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0900000000-fe8d862acce93dd7eb84Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-3900000000-f7e8be1495cce9a344aeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05bb-9700000000-e16830e0be835671623bSpectrum
NMRNot Available
ChemSpider ID16498843
ChEMBL IDNot Available
KEGG Compound IDC06746
Pubchem Compound ID6508
Pubchem Substance IDNot Available
ChEBI ID17521
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03072
CRC / DFC (Dictionary of Food Compounds) IDHBH46-E:BVJ24-C
EAFUS IDNot Available
Dr. Duke ID(-)-QUINIC-ACID|QUINIC-ACID|QUINIC-ACIC
BIGG IDNot Available
KNApSAcK IDC00001201
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDQuinic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
cholereticDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.