1,4-Di-O-caffeoylquinic acid (CHEM028777)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:41:31 UTC
Update Date2016-11-09 01:18:45 UTC
Accession NumberCHEM028777
Identification
Common Name1,4-Di-O-caffeoylquinic acid
ClassSmall Molecule
Description1,4-Di-O-caffeoylquinic acid is found in herbs and spices. 1,4-Di-O-caffeoylquinic acid is isolated from flowers and leaves of Helichrysum italicum (curry plant
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,4-Di-O-caffeoylquinateGenerator
1,4-Bis-(3,4-dihydroxycinnamoyl)quinic acidHMDB
1,4-Dicaffeoylquinic acidHMDB
1,4-Dicaffeylquinic acidHMDB
NSC 91529HMDB
(1S,3R,4S,5R)-1,4-Bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylateGenerator
Chemical FormulaC25H24O12
Average Molecular Mass516.451 g/mol
Monoisotopic Mass516.127 g/mol
CAS Registry Number1182-34-9
IUPAC Name(1S,3R,4S,5R)-1,4-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid
Traditional Name(1S,3R,4S,5R)-1,4-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid
SMILESO[C@@H]1C[C@](C(=O)O)(C[C@@H](O)[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1)OC(=O)\C=C\C1=CC=C(O)C(O)=C1
InChI IdentifierInChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(32)36-23-19(30)11-25(24(34)35,12-20(23)31)37-22(33)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-31H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1
InChI KeyIYXQRCXQQWUFQV-PSEXTPKNSA-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
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Fatty acid ester
  • Cyclohexanol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Fatty acyl
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • 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 Solubility0.14 g/LALOGPS
logP2.06ALOGPS
logP2.16ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.21ChemAxon
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
Polarizability50.16 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, Positivesplash10-03du-6894100000-3cc776275036e1452e7aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01pa-5947105000-48f4ae26dfb0f19719bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02tj-0609440000-218969ac8eca3c447140Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06ri-0908300000-56da112fdf3b7309f1d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-070f-0912100000-086a2d351f0d8ecd09c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-0319470000-990109b660542b831997Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kk9-0938200000-bb497a7bc6d677084f2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-0902000000-5be08bec609d75adc06fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-b378e9bbf66017fd276bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0673-0529440000-2003b2a4a48754b76d17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0901100000-b35e0e1b7e8dada58276Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-044j-0914840000-577fddcfd51d555648b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-0930200000-01988e78a39b9187e866Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01rg-3921600000-38b4c7191e0ee9562793Spectrum
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 IDHMDB0034766
FooDB IDFDB013317
Phenol Explorer IDNot Available
KNApSAcK IDC00055091
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID22912997
ChEBI IDNot Available
PubChem Compound IDNot Available
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.