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Showing Compound Chicoric acid (FDB012144)

Record Information
Version1.0
Creation date2010-04-08 22:10:01 UTC
Update date2025-11-18 23:34:16 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 IDHMDB0033938
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 An agent that prevents or treats influenza virus infections, reducing symptoms and complications. Its biological role involves blocking viral replication, and its therapeutic applications include prophylaxis and treatment of flu outbreaks. Key medical uses include reducing the risk of flu-related hospitalizations and mortality, especially in high-risk populations such as the elderly and young children.DUKE
Anti HIV22587 An agent that prevents the replication of the Human Immunodeficiency Virus (HIV), used to treat and manage HIV infection and Acquired Immunodeficiency Syndrome (AIDS), reducing viral load and slowing disease progression.DUKE
Anti HIV-integrase23924 An agent that blocks HIV integrase, an enzyme crucial for viral DNA integration into host cells, preventing HIV replication. Therapeutically, it's used to treat HIV-1 infection, often in combination with other antiretrovirals, to suppress viral loads and slow disease progression.DUKE
Anti otitic52217 An agent that reduces inflammation and infection in the ear, commonly used to treat otitis media (middle ear infection) and other ear disorders, promoting hearing health and alleviating symptoms such as pain and discomfort.DUKE
Anti radicularAn agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.DUKE
Anti-stomatiticAn agent that relieves inflammation of the mucous membrane of the mouth, reducing oral discomfort and pain. Its biological role is to soothe and protect the mucosa, with therapeutic applications in managing mouth ulcers, oral thrush, and other stomatitis-related conditions. Key medical uses include treating oral inflammation, irritation, and infections.DUKE
Anti sunburn52217 An agent that protects the skin from sun damage, reducing inflammation and preventing burns. Its biological role is to absorb or reflect UV radiation, therapeutic applications include preventing skin cancer and photoaging, and key medical uses include treating sunburn, premature aging, and skin discoloration.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
Bacteristat33282 An agent that inhibits bacterial growth, reducing the proliferation of microorganisms without killing them. Therapeutically, bacteristats are used to treat infections, preventing the spread of bacteria and allowing the host's immune system to clear the infection. Key medical uses include treating urinary tract infections, acne, and other bacterial infections where bactericidal agents may not be necessary.DUKE
Collagen-sparingAn agent that preserves collagen, reducing its degradation and promoting tissue repair. It plays a biological role in maintaining skin and joint health. Therapeutically, it has applications in wound healing, osteoarthritis, and skin rejuvenation, with key medical uses in dermatology and orthopedics to prevent tissue damage and promote regeneration.DUKE
Hyaluronidase inhibitor23924 An agent that blocks the activity of hyaluronidase, an enzyme that breaks down hyaluronic acid. This inhibition helps maintain hyaluronic acid levels, reducing inflammation and improving tissue hydration, with therapeutic applications in ophthalmology, dermatology, and oncology, and key medical uses in treating dry eye, wrinkles, and certain cancers.DUKE
Immunostimulant50847 An agent that stimulates the immune system, enhancing its response to infections and diseases. Therapeutically, it boosts the body's natural defenses, commonly used to treat immunodeficiency disorders, prevent infections, and support cancer treatment, as well as manage chronic conditions like hepatitis and HIV.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
PhagocytoticAn agent that engulfs and internalizes solid particles or cells through phagocytosis, playing a key role in immune defense. Therapeutically, it aids in removing pathogens and debris, with medical applications in treating infections and inflammatory disorders.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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).