Caffeic acid (CHEM003161)

Record Information
Version1.0
Creation Date2014-08-29 05:52:27 UTC
Update Date2026-05-14 17:19:28 UTC
Accession NumberCHEM003161
Identification
Common NameCaffeic acid
ClassSmall Molecule
Description
Caffeic acid is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food. (1).
Contaminant Sources
  • Cosmetic Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 2B
  • T3DB toxins
  • Tobacco Smoke Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Animal Toxin
  • Cigarette Toxin
  • Ester
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,4-Dihydroxycinnamic acidChEBI
CaffeateChEBI
Caffeic acidChEBI
3,4-DihydroxycinnamateGenerator
cis-CaffeateGenerator
3,4-DihydroxybenzeneacrylateHMDB
3,4-Dihydroxybenzeneacrylic acidHMDB
Caffeic acid pureHMDB
CaffeicacidHMDB
(2Z)-3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
(Z)-3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
(Z)-Caffeic acidHMDB
3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
3-(3,4-Dihydroxyphenyl)propenoic acidHMDB
4-(2'-Carboxyvinyl)-1,2-dihydroxybenzeneHMDB
4-(2-Carboxyethenyl)-1,2-dihydroxybenzeneHMDB
4-(2’-carboxyvinyl)-1,2-dihydroxybenzeneHMDB
DHCAHMDB
Isocaffeic acidHMDB
cis-3,4-Dihydroxycinnamic acidHMDB
cis-Caffeic acidHMDB
Chemical FormulaC9H8O4
Average Molecular Mass180.157 g/mol
Monoisotopic Mass180.042 g/mol
CAS Registry Number331-39-5
IUPAC Name(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
Traditional Namecaffeicacid
SMILESOC(=O)\C=C/C1=CC=C(O)C(O)=C1
InChI IdentifierInChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2-
InChI KeyQAIPRVGONGVQAS-RQOWECAXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Platelet
  • Prostate
  • Stratum Corneum
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point225°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
logP1.53ChemAxon
pKa (Strongest Acidic)3.14ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.02 m³·mol⁻¹ChemAxon
Polarizability16.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (12)
Uses/SourcesThis is a toxic chemical found in cigarettes or generated by tobacco combustion.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0003501
FooDB IDFDB012666
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-8098
METLIN ID3316
PDB IDNot Available
Wikipedia LinkCaffeic acid
Chemspider ID1266077
ChEBI ID17395
PubChem Compound ID1549111
Kegg Compound IDC01481
YMDB IDYMDB01645
ECMDB IDM2MDB005541
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.
2. Mennen LI, Sapinho D, Ito H, Bertrais S, Galan P, Hercberg S, Scalbert A: Urinary flavonoids and phenolic acids as biomarkers of intake for polyphenol-rich foods. Br J Nutr. 2006 Jul;96(1):191-8.
3. Kawaguchi H, Katsuyama Y, Danyao D, Kahar P, Nakamura-Tsuruta S, Teramura H, Wakai K, Yoshihara K, Minami H, Ogino C, Ohnishi Y, Kondo A: Caffeic acid production by simultaneous saccharification and fermentation of kraft pulp using recombinant Escherichia coli. Appl Microbiol Biotechnol. 2017 Jul;101(13):5279-5290. doi: 10.1007/s00253-017-8270-0. Epub 2017 Apr 10.
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19812218
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19952409
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24088646
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24138287
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24206679