4,5-Di-O-caffeoylquinic acid (CHEM024718)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:52:46 UTC
Update Date2016-11-09 01:17:56 UTC
Accession NumberCHEM024718
Identification
Common Name4,5-Di-O-caffeoylquinic acid
ClassSmall Molecule
Description4,5-Di-O-caffeoylquinic acid is found in arabica coffee. 4,5-Di-O-caffeoylquinic acid is isolated from coffee and Brazilian propoli
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4,5-Di-O-caffeoylquinateGenerator
Methyl 3,5-di-O-caffeoyl quinateMeSH
3,4-Di-O-caffeoylquinic acidMeSH
3,4-Dicaffeoylquinic acidMeSH
Isochlorogenic acid bMeSH
3,4-DICQAMeSH
Methyl-3,5-di-O-caffeoylquinateMeSH
4,5-Bis(3,4-dihydroxycinnamoyl)quinic acidHMDB
4,5-DCQAHMDB
4,5-Dicaffeoylquinic acidHMDB
Isochlorogenic acid cHMDB
(1R,3R,4S,5R)-3,4-Bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylateGenerator
Chemical FormulaC25H24O12
Average Molecular Mass516.451 g/mol
Monoisotopic Mass516.127 g/mol
CAS Registry Number57378-72-0
IUPAC Name(1R,3R,4S,5R)-3,4-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid
Traditional Name(1R,3R,4S,5R)-3,4-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid
SMILESO[C@@H]1C[C@@](O)(C[C@@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)=O
InChI IdentifierInChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1
InChI KeyUFCLZKMFXSILNL-RVXRWRFUSA-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
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Tricarboxylic acid or derivatives
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Cyclohexanol
  • Fatty acid ester
  • Phenol
  • Fatty acyl
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Alpha-hydroxy acid
  • Benzenoid
  • Tertiary alcohol
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic 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 Solubility0.12 g/LALOGPS
logP2.05ALOGPS
logP2.16ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.31ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area211.28 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity126.76 m³·mol⁻¹ChemAxon
Polarizability49.94 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-3389700000-7dcc3b1e654e56b19d20Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03ea-3911516000-d9bd68d1a51a6b546dd4Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0g73-0902010000-11f6f7fbb3b572bd769aSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0900000000-50993e3c8828bf603233Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0900000000-104e706220fc04250af0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014i-0002090000-b472c8ddd10824f1d990Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03di-0920000000-b0b8e436b6fb5d980895Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0906410000-90e978928c9b1442e515Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0922300000-fc8396e636117100c450Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00g3-0900000000-03c7d39838b9afe8eadeSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0v6r-0917040000-8d2f186578e2e1bffabcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02tj-0519740000-b04a785b68fb9d08aa90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08g0-0809300000-2e08acb59c4f6e3ce1cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0706-0923100000-7e4a6c1a9bba7e4e3fbaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gi0-0408960000-3a7fa77d468d42c82839Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pkc-0639400000-050fab9868fda476be78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06vi-0925000000-16885448c5705d89b725Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-ebf2d34d44c137ef516eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-ea9988b0f6e7059ddd4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-044s-2900100000-714238e9a42dbb25a321Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0200090000-8775d8353995e6be8248Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-0809020000-ae55bb86009e4c612f88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0901100000-2d1ed565ddf2cb11c6ebSpectrum
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 IDHMDB0030707
FooDB IDFDB002629
Phenol Explorer IDNot Available
KNApSAcK IDC00034768
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4976335
ChEBI ID390480
PubChem Compound ID6474309
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.