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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:59 UTC
Update Date2019-07-23 05:45:35 UTC
HMDB IDHMDB0002641
Secondary Accession Numbers
  • HMDB02641
Metabolite Identification
Common Name2-Hydroxycinnamic acid
Description2-Hydroxycinnamic acid (CAS: 583-17-5), also known as o-coumaric acid, is a hydroxy derivative of cinnamic acid. Cinnamic acid and its derivatives are used as important components in flavours, perfumes, synthetic indigo, and pharmaceuticals. There are three isomers of coumaric acid: o-coumaric acid, m-coumaric acid, and p-coumaric acid. These isomers differ by the position of the hydroxy substitution. p-Coumaric acid is the most abundant isomer in nature (Wikipedia).
Structure
Data?1563860735
Synonyms
ValueSource
(2E)-3-(2-Hydroxyphenyl)-2-propenoic acidChEBI
(2E)-3-(2-HYDROXYPHENYL)acrylIC ACIDChEBI
(e)-2-Hydroxycinnamic acidChEBI
(e)-3-(2-Hydroxy-phenyl)-acrylic acidChEBI
(e)-3-(2-Hydroxyphenyl)-2-propenoic acidChEBI
(e)-O-Hydroxycinnamic acidChEBI
2-CoumarateChEBI
2-Coumaric acidChEBI
2-HydroxycinnamateChEBI
O-Coumaric acidChEBI
O-Hydroxy-trans-cinnamic acidChEBI
trans-2-HydroxycinnamateChEBI
trans-2-Hydroxycinnamic acidChEBI
trans-O-Hydroxycinnamic acidChEBI
(2E)-3-(2-Hydroxyphenyl)-2-propenoateGenerator
(2E)-3-(2-HYDROXYPHENYL)acrylateGenerator
(e)-2-HydroxycinnamateGenerator
(e)-3-(2-Hydroxy-phenyl)-acrylateGenerator
(e)-3-(2-Hydroxyphenyl)-2-propenoateGenerator
(e)-O-HydroxycinnamateGenerator
O-CoumarateGenerator
O-Hydroxy-trans-cinnamateGenerator
trans-O-HydroxycinnamateGenerator
3-(2-Hydroxyphenyl)prop-2-enoateHMDB
3-(2-Hydroxyphenyl)prop-2-enoic acidHMDB
O-HydroxycinnamateHMDB
O-Hydroxycinnamic acidHMDB
Ortho-hydroxycinnamateHMDB
Ortho-hydroxycinnamic acidHMDB
trans-O-CoumarateHMDB
trans-O-Coumaric acidHMDB
2-Hydroxycinnamic acid, (Z)-isomerHMDB
2-Hydroxycinnamic acid, (e)-isomerHMDB
trans-2-CoumarateHMDB
2-Hydroxycinnamic acidGenerator
(E)-3-(2-Hydroxyphenyl)acrylic acidHMDB
3-(2-Hydroxyphenyl)-2-propenoic acidHMDB
Chemical FormulaC9H8O3
Average Molecular Weight164.158
Monoisotopic Molecular Weight164.047344122
IUPAC Name(2E)-3-(2-hydroxyphenyl)prop-2-enoic acid
Traditional NameO-coumaric acid
CAS Registry Number614-60-8
SMILES
OC(=O)\C=C\C1=C(O)C=CC=C1
InChI Identifier
InChI=1S/C9H8O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6,10H,(H,11,12)/b6-5+
InChI KeyPMOWTIHVNWZYFI-AATRIKPKSA-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
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • 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
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.15 g/LALOGPS
logP1.9ALOGPS
logP1.83ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4.04ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.04 m³·mol⁻¹ChemAxon
Polarizability16.11 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-0910000000-9e0bdbf6d6389288e318JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00dj-9710000000-829ded288e3ec8312160JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00dj-9710000000-8fb7bb39d916f7402980JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0296-2941000000-b85ebef8eb8c276f220fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9800000000-3650ee76a1293cba7523JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0910000000-9e0bdbf6d6389288e318JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-9710000000-829ded288e3ec8312160JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-9710000000-8fb7bb39d916f7402980JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0296-2941000000-b85ebef8eb8c276f220fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0910000000-c783499d6f33717b71caJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-2900000000-3a06c14b7e8999427ad9JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00y3-6390000000-a82ff5bd6498e3c478eaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-9e4823d321cfe6f5e5a4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-0900000000-efd5de4e7fe4032816f6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-0900000000-44e81c2c735a93efc7d7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014l-7900000000-977a2bb08508d16be531JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00kf-9300000000-fe9b4a0aa3b23d5c2eb5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0fdn-4900000000-dcfe2b032cf6bbee16b3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-adbaf7b04487b18191e0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-d368e3c354c7b05a949fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-efd5de4e7fe4032816f6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-44e81c2c735a93efc7d7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014l-7900000000-a641b2c2528f829e8ac1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kf-9300000000-fe9b4a0aa3b23d5c2eb5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-adbaf7b04487b18191e0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0900000000-2ca69c9285dedaa2f424JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0900000000-55078e8ec591840fb594JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0fdn-4900000000-95f5386456c1c353a111JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-ba0915b2f87da989c92bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-fd2da9ac5865a50fc50cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gdu-9300000000-3baee6b4124fba79677eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-69f05779283af436427dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-1900000000-0bc76f24c2abf6670fc0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9600000000-a2981a5342a71b94ce69JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-014j-8900000000-8e96a9ec1b9d035d3edbJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.904 +/- 0.337 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.188 +/- 0.059 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.339 +/- 0.088 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.366 +/- 0.164 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.521 +/- 0.278 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.58 +/- 0.184 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified3.528 +/- 3.295 uMAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.213 +/- 0.099 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01650
Phenol Explorer Compound ID462
FoodDB IDFDB011258
KNApSAcK IDC00002729
Chemspider ID553146
KEGG Compound IDC01772
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkO-Coumaric_acid
METLIN ID6727
PubChem Compound637540
PDB IDNot Available
ChEBI ID18125
References
Synthesis ReferenceAdams, Roger; Bockstahler, Theodore E. Preparation and reactions of o-hydroxycinnamic acids and esters. Journal of the American Chemical Society (1952), 74 5346-8.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Todoriki H, Hayashi T, Naruse H: High-performance liquid chromatographic method for screening disorders of aromatic acid metabolism using a multi-detection system. J Chromatogr. 1984 Oct 12;310(2):273-81. [PubMed:6511847 ]