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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-28 21:53:21 UTC
Update Date2020-02-26 21:26:55 UTC
HMDB IDHMDB0006915
Secondary Accession Numbers
  • HMDB06915
Metabolite Identification
Common Name2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid
Description2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid, also known as 4,alpha-dihydroxycinnamic acid or 4-hydroxy-enol-phenylpyruvate, belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid. 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid exists in all living organisms, ranging from bacteria to humans. In humans, 2-hydroxy-3-(4-hydroxyphenyl)propenoic acid is involved in the metabolic disorder called hawkinsinuria. 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 2-hydroxy-3-(4-hydroxyphenyl)propenoic acid a potential biomarker for the consumption of these foods. 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid.
Structure
Data?1582752415
Synonyms
ValueSource
4,alpha-Dihydroxycinnamic acidChEBI
4-Hydroxy-enol-phenylpyruvateKegg
4,a-DihydroxycinnamateGenerator
4,a-Dihydroxycinnamic acidGenerator
4,alpha-DihydroxycinnamateGenerator
4,Α-dihydroxycinnamateGenerator
4,Α-dihydroxycinnamic acidGenerator
4-Hydroxy-enol-phenylpyruvic acidGenerator
2-Hydroxy-3-(4-hydroxyphenyl)propenoateGenerator
Chemical FormulaC9H8O4
Average Molecular Weight180.1574
Monoisotopic Molecular Weight180.042258744
IUPAC Name(2Z)-2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoic acid
Traditional Name4,α-dihydroxycinnamic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C(\O)=C\C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-5,10-11H,(H,12,13)/b8-5-
InChI KeyGQYBCIHRWMPOOF-YVMONPNESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpyruvic acid derivatives
Direct ParentPhenylpyruvic acid derivatives
Alternative Parents
Substituents
  • Cinnamic acid
  • Cinnamic acid or derivatives
  • Coumaric acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Hydroxycinnamic acid or derivatives
  • Enol-phenylpyruvate
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocarboxylic acid or derivatives
  • Enol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.81 g/LALOGPS
logP10(1.28) g/LALOGPS
logP10(1.31) g/LChemAxon
logS10(-2.4) g/LALOGPS
pKa (Strongest Acidic)3.16ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.01 m³·mol⁻¹ChemAxon
Polarizability17.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acidOC(=O)C(\O)=C\C1=CC=C(O)C=C13375.9Standard polar33892256
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acidOC(=O)C(\O)=C\C1=CC=C(O)C=C11701.6Standard non polar33892256
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acidOC(=O)C(\O)=C\C1=CC=C(O)C=C11896.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)/C(O)=C/C1=CC=C(O)C=C12011.0Semi standard non polar33892256
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid,1TMS,isomer #2C[Si](C)(C)O/C(=C\C1=CC=C(O)C=C1)C(=O)O2025.2Semi standard non polar33892256
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid,1TMS,isomer #3C[Si](C)(C)OC1=CC=C(/C=C(\O)C(=O)O)C=C12004.5Semi standard non polar33892256
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)/C(=C/C1=CC=C(O)C=C1)O[Si](C)(C)C2053.6Semi standard non polar33892256
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)/C(O)=C/C1=CC=C(O[Si](C)(C)C)C=C12050.2Semi standard non polar33892256
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid,2TMS,isomer #3C[Si](C)(C)O/C(=C\C1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O2088.7Semi standard non polar33892256
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)/C(=C/C1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C2071.7Semi standard non polar33892256
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C(O)=C/C1=CC=C(O)C=C12270.6Semi standard non polar33892256
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O/C(=C\C1=CC=C(O)C=C1)C(=O)O2278.9Semi standard non polar33892256
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C(\O)C(=O)O)C=C12311.3Semi standard non polar33892256
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C(=C/C1=CC=C(O)C=C1)O[Si](C)(C)C(C)(C)C2529.5Semi standard non polar33892256
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)/C(O)=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12550.3Semi standard non polar33892256
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)O/C(=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O2596.6Semi standard non polar33892256
2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C(=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C2764.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-1900000000-10c51d0329cb2a35dbb82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid GC-MS (3 TMS) - 70eV, Positivesplash10-00gi-6259000000-cdf2744454615081e02f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid 10V, Positive-QTOFsplash10-0bu0-0900000000-a08730e02c84f43e79262017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid 20V, Positive-QTOFsplash10-0a4i-0900000000-2eb4f2eaa5d547249a3e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid 40V, Positive-QTOFsplash10-0a6r-7900000000-63f2942443ac7bfdce482017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid 10V, Negative-QTOFsplash10-004i-0900000000-8576bdecf0b58e989df62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid 20V, Negative-QTOFsplash10-0a4i-0900000000-46e515a63da5ddf92de92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid 40V, Negative-QTOFsplash10-0a4i-0900000000-3c0a27f480b5bb59093c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid 10V, Negative-QTOFsplash10-004i-0900000000-02f0fa9241cf4b1591c72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid 20V, Negative-QTOFsplash10-00di-9800000000-0e7b12140d77aa62a5122021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid 40V, Negative-QTOFsplash10-0api-4900000000-6f21f2ecdec85109e7d52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid 10V, Positive-QTOFsplash10-01qi-0900000000-28cf4812bb35ce056a152021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid 20V, Positive-QTOFsplash10-0a4r-1900000000-bd40f97e341181046c0f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid 40V, Positive-QTOFsplash10-004i-9200000000-c7f40face58730829b4a2021-09-22Wishart LabView Spectrum
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 IDFDB024152
KNApSAcK IDNot Available
Chemspider ID552441
KEGG Compound IDC05350
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound636708
PDB IDNot Available
ChEBI ID27683
Food Biomarker OntologyNot Available
VMH IDM00643
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in cell surface binding
Specific function:
Pro-inflammatory cytokine. Involved in the innate immune response to bacterial pathogens. The expression of MIF at sites of inflammation suggests a role as mediator in regulating the function of macrophages in host defense. Counteracts the anti-inflammatory activity of glucocorticoids. Has phenylpyruvate tautomerase and dopachrome tautomerase activity (in vitro), but the physiological substrate is not known. It is not clear whether the tautomerase activity has any physiological relevance, and whether it is important for cytokine activity.
Gene Name:
MIF
Uniprot ID:
P14174
Molecular weight:
12476.19
Reactions
4-Hydroxyphenylpyruvic acid → 2-Hydroxy-3-(4-hydroxyphenyl)propenoic aciddetails