Record Information
Version1.0
Creation date2010-04-08 22:05:27 UTC
Update date2020-02-24 19:10:34 UTC
Primary IDFDB002627
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3,4-Dicaffeoylquinic acid
Description3,4-Di-O-caffeoylquinic acid, also known as 34-dicaffeoylquinate or isochlorogenic acid b, 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. 3,4-Di-O-caffeoylquinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 3,4-Di-O-caffeoylquinic acid is found, on average, in the highest concentration within a few different foods, such as coffee, robusta coffee, and arabica coffee and in a lower concentration in potato. 3,4-Di-O-caffeoylquinic acid has also been detected, but not quantified in, asian pears and coffee and coffee products. This could make 3,4-di-O-caffeoylquinic acid a potential biomarker for the consumption of these foods.
CAS Number14534-61-3
Structure
Thumb
Synonyms
SynonymSource
3,4-Di-O-caffeoylquinateGenerator
34-Dicaffeoylquinic acidHMDB
Rel-34-dicaffeoylquinic acidHMDB
34-DicaffeoylquinateHMDB
Rel-34-dicaffeoylquinateHMDB
3,4-Dicaffeoylquinic acidHMDB
4,5-Di-O-caffeoylquinic acid?HMDB
Isochlorogenic acid bHMDB
Quinic acid 3,4-di-O-caffeateHMDB
Isochlorogenate bGenerator
3,4-DICQAMeSH
3,4-Di-O-caffeoylquinic acidMeSH
Methyl-3,5-di-O-caffeoylquinateMeSH
Methyl 3,5-di-O-caffeoyl quinateMeSH
3,4-DicaffeoylquinateGenerator
4-DicaffeoylquinateGenerator
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
Polarizability49.4 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC25H24O12
IUPAC name(1S,3R,4R,5R)-3,4-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid
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-PSEXTPKNSA-N
Isomeric 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
Average Molecular Weight516.4509
Monoisotopic Molecular Weight516.126776232
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
  • 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 Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Foods

Fruits and vegetables:

Beverages:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 58.14%; H 4.68%; O 37.17%DFC
Melting PointMp 234-238° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]28D -225 (MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS3,4-Dicaffeoylquinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-3389700000-7dcc3b1e654e56b19d20Spectrum
Predicted GC-MS3,4-Dicaffeoylquinic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03ea-3911516000-d9bd68d1a51a6b546dd4Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-0900000000-70307c420de286ff63f6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Negativesplash10-0uk9-0809000000-dfca1cb13e0f8d4db4fcSpectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0uk9-0905000000-5e5c2229f9cfab32c5ccSpectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0900000000-b4947fc39d5cbfac96abSpectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0900000000-b65d937e99b4ef96e5a5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02tj-0519740000-b04a785b68fb9d08aa90Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08g0-0809300000-2e08acb59c4f6e3ce1cdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0706-0923100000-7e4a6c1a9bba7e4e3fbaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gi0-0408960000-3a7fa77d468d42c82839Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pkc-0639400000-050fab9868fda476be78Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06vi-0925000000-16885448c5705d89b725Spectrum
NMRNot Available
ChemSpider ID4445093
ChEMBL IDCHEMBL249448
KEGG Compound IDC10468
Pubchem Compound ID5281780
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID527
DrugBank IDNot Available
HMDB IDHMDB30705
CRC / DFC (Dictionary of Food Compounds) IDCMS81-K:CMS81-K
EAFUS IDNot Available
Dr. Duke IDISOCHLOROGENIC-ACID-B|3,4-DICAFFEOYL-QUINIC-ACID
BIGG IDNot Available
KNApSAcK IDC00002751
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite ID527
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti peroxidantDUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— 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.