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Showing Compound Chicoric acid (FDB012144)

Record Information
Version1.0
Creation date2010-04-08 22:10:01 UTC
Update date2019-11-26 03:06:16 UTC
Primary IDFDB012144
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameChicoric acid
DescriptionD-chicoric acid, also known as D-chicate, belongs to tetracarboxylic acids and derivatives class of compounds. Those are carboxylic acids containing exactly four carboxyl groups. D-chicoric acid is practically insoluble (in water) and a moderately acidic compound (based on its pKa). D-chicoric acid can be found in green vegetables, which makes D-chicoric acid a potential biomarker for the consumption of this food product. Cichoric acid is a hydroxycinnamic acid, an organic compound of the phenylpropanoid class and occurs in a variety of plant species. It is a derivative of both caffeic acid and tartaric acid .
CAS Number6537-80-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
D-ChicateGenerator
D-Chicic acidGenerator
2,3-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]butanedioic acid, 9CIdb_source
Cichoric aciddb_source
Dicaffeoyltartaric aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility0.043 g/LALOGPS
logP3.48ALOGPS
logP3.02ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)2.72ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area208.12 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity113.27 m³·mol⁻¹ChemAxon
Polarizability41.97 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC22H18O12
IUPAC name2,3-bis({[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})butanedioic acid
InChI IdentifierInChI=1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3-,8-4-
InChI KeyYDDGKXBLOXEEMN-VHOZIDCHSA-N
Isomeric SMILESOC(=O)C(OC(=O)\C=C/C1=CC(O)=C(O)C=C1)C(OC(=O)\C=C/C1=CC(O)=C(O)C=C1)C(O)=O
Average Molecular Weight474.3711
Monoisotopic Molecular Weight474.07982604
Classification
Description Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTetracarboxylic acids and derivatives
Direct ParentTetracarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tetracarboxylic acid or derivatives
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Monosaccharide
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 55.70%; H 3.82%; O 40.47%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSL-Chicoric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-0900000000-e41d90ab3b9e655843e8Spectrum
Predicted GC-MSL-Chicoric acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-3911001000-b4d0d0e61d24529efa2bSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0751900000-666c40c43f01514fc6352016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0951200000-b0d53c5e3a31d06f1e1d2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06sj-0910000000-a5421d18e088b260e7ad2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0200-0871900000-2624a942972fa2025a0e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0930100000-93e452919696a8a1ccbf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-0910000000-ed7ecbd57a50e1e58cd22016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID619292
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHDQ78-W:HDQ78-W
EAFUS IDNot Available
Dr. Duke IDDICAFFEOYL-TARTARIC-ACID|CHICORIC-ACID|CICHORIC-ACID
BIGG IDNot Available
KNApSAcK IDC00034818
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDChicoric_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
anti flu22587 A substance that destroys or inhibits replication of viruses.DUKE
anti HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
anti HIV-integrase23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
anti otitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti radicularDUKE
anti stomatiticDUKE
anti sunburn52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
bacteristat33282 A substance that kills or slows the growth of bacteria.DUKE
collagen-sparingDUKE
hyaluronidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
immunostimulant50847 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
phagocytoticDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
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).