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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-12 22:05:42 UTC
Update Date2020-02-26 21:24:39 UTC
HMDB IDHMDB0003501
Secondary Accession Numbers
  • HMDB0006494
  • HMDB03501
  • HMDB06494
Metabolite Identification
Common Namecis-Caffeic acid
DescriptionCaffeic acid, also known as caffeate, 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. Caffeic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Caffeic acid exists in all living species, ranging from bacteria to humans. It is the precursor to ferulic acid, coniferyl alcohol, and sinapyl alcohol, all of which are significant building blocks in lignin. Outside of the human body, caffeic acid has been detected, but not quantified in, fats and oils and nuts. This could make caffeic acid a potential biomarker for the consumption of these foods. Caffeic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Caffeic acid has a variety of potential pharmacological effects in in vitro studies and in animal models, and the inhibitory effect of caffeic acid on cancer cell proliferation by an oxidative mechanism in the human HT-1080 fibrosarcoma cell line has recently been established. It occurs at high levels in black chokeberry (141 mg per 100 g) and in fairly high level in lingonberry (6 mg per 100 g).
Structure
Data?1582752279
Synonyms
ValueSource
3,4-Dihydroxycinnamic acidChEBI
CaffeateChEBI
3,4-DihydroxycinnamateGenerator
3,4-DihydroxybenzeneacrylateHMDB
3,4-Dihydroxybenzeneacrylic acidHMDB
Caffeic acid pureHMDB
CaffeicacidHMDB
cis-CaffeateHMDB
cis-Caffeic acidHMDB
Caffeic acidChEBI
(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
Chemical FormulaC9H8O4
Average Molecular Weight180.1574
Monoisotopic Molecular Weight180.042258744
IUPAC Name(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
Traditional Namecaffeicacid
CAS Registry Number4361-87-9
SMILES
OC(=O)\C=C/C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=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
Ontology
Disposition

Route of exposure:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.35Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.61 g/LALOGPS
logP1.67ALOGPS
logP1.53ChemAxon
logS-2ALOGPS
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9341000000-6dc8d392552b88bd4d8cSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9351000000-50a6f144c73d7ab2794eSpectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-2793000000-251334452407128b38bdSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9341000000-6dc8d392552b88bd4d8cSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9351000000-50a6f144c73d7ab2794eSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-2793000000-251334452407128b38bdSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0692000000-32624fa3a157a1f11cefSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001r-0900000000-c3283a4b6f6f11b66cfbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00e9-5039000000-d55c6a31e04536d33b58Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-298c46c83441485d1d70Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kr-9800000000-942c1934d3c7c395499eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-e9bdfc2dec7a449ccb11Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0900000000-b07143eccfcbf1caba0cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-0900000000-8f21d50b78f0d9fde98aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-0900000000-4013461a961ebed6fd99Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0019-2900000000-b41600c20a73cd258d40Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001r-8900000000-81ea3878c2912bdddf71Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0900000000-a1680074d0439bcd4c20Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0900000000-096221135a729c5d6aacSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0019-0900000000-98893b92962a162b2fb0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03dr-2900000000-fc2581b0410dd8cb6e71Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-000i-9200000000-0fd7b8f57372dc8172d5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03dr-2900000000-454a31169c27631fb00cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-0900000000-eb2466a330b617695c80Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-31b407ecba8c8e813fd0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-8f21d50b78f0d9fde98aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-4013461a961ebed6fd99Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0019-2900000000-71ad48cc68ef0b7fe30dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-4d70eb21dfd5dcee3360Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01wr-0900000000-eb4ac130dea5eced36c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0100-9800000000-68217b65b3cfbf177196Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-28ed8e427213908fdd9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ti-0900000000-5913f01901b92071e2fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-090u-1900000000-2454d377d14f50d8c9b2Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-4900000000-3c93f113512b8284301dSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012666
KNApSAcK IDNot Available
Chemspider ID1266077
KEGG Compound IDC01481
BioCyc IDCPD-8098
BiGG IDNot Available
Wikipedia LinkCaffeic acid
METLIN ID3316
PubChem Compound1549111
PDB IDNot Available
ChEBI ID17395
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:16870009 ]
  2. 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. [PubMed:28396925 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:
TYR
Uniprot ID:
P14679
Molecular weight:
60392.69
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
cis-Caffeic acid → Ferulic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
cis-Caffeic acid → 6-{5-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
cis-Caffeic acid → 6-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
cis-Caffeic acid → 6-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
cis-Caffeic acid → Caffeic acid 3-O-sulfatedetails