Showing metabocard for 4-Hydroxycinnamic acid (BMDB0002035)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:50:14 UTC
Update Date2020-05-11 20:02:33 UTC
MCDB ID BMDB0002035
Secondary Accession Numbers
  • BMDB02035
Metabolite Identification
Common Name4-Hydroxycinnamic acid
Descriptiontrans-4-Coumaric acid, also known as 4-hydroxycinnamic acid or trans-p-hydroxycinnamate, 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. trans-4-Coumaric acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. trans-4-Coumaric acid exists in all living species, ranging from bacteria to humans.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(2E)-3-(4-Hydroxyphenyl)acrylic acidChEBI
(e)-3-(4-Hydroxyphenyl)-2-propenoic acidChEBI
(e)-p-Coumaric acidChEBI
(e)-p-Hydroxycinnamic acidChEBI
4'-HYDROXYCINNAMIC ACIDChEBI
Naringeninic acidChEBI
p-Coumaric acidChEBI
trans-p-Coumaric acidChEBI
trans-p-Coumarinic acidChEBI
trans-p-HydroxycinnamateChEBI
trans-p-Hydroxycinnamic acidChEBI
trans-4-HydroxycinnamateKegg
4-HydroxycinnamateKegg
(2E)-3-(4-Hydroxyphenyl)acrylateGenerator
(e)-3-(4-Hydroxyphenyl)-2-propenoateGenerator
(e)-p-CoumarateGenerator
(e)-p-HydroxycinnamateGenerator
4'-HYDROXYCINNAMateGenerator
NaringeninateGenerator
p-CoumarateGenerator
trans-p-CoumarateGenerator
trans-p-CoumarinateGenerator
4-Coumaric acid, (e)-isomerMeSH
4-Coumaric acid, (Z)-isomerMeSH
4-Coumaric acid, disodium saltMeSH
p-Coumaryl alcoholMeSH
p-Hydroxycinnamic acidMeSH
Para-coumaric acidMeSH
trans-3-(4'-Hydroxyphenyl)-2-propenoic acidMeSH
trans-HPPAMeSH
3-(4-Hydroxyphenyl)-2-propenoateHMDB
3-(4-Hydroxyphenyl)-2-propenoic acidHMDB
3-(4-Hydroxyphenyl)acrylateHMDB
3-(4-Hydroxyphenyl)acrylic acidHMDB
4-CoumarateHMDB
4-Hydroxy cinnamateHMDB
4-Hydroxy cinnamic acidHMDB
4-HydroxyphenylpropenoateHMDB
4-Hydroxyphenylpropenoic acidHMDB
b-[4-Hydroxyphenyl]acrylateHMDB
b-[4-Hydroxyphenyl]acrylic acidHMDB
beta-[4-Hydroxyphenyl]acrylateHMDB
beta-[4-Hydroxyphenyl]acrylic acidHMDB
cis-P-CoumarateHMDB
HydroxycinnamateHMDB
Hydroxycinnamic acidHMDB
P-CumarateHMDB
P-Cumaric acidHMDB
P-HydroxycinnamateHMDB
P-HydroxyphenylacrylateHMDB
P-Hydroxyphenylacrylic acidHMDB
Para coumarateHMDB
Para coumaric acidHMDB
Para-coumarateHMDB
4-Hydroxycinnamic acidChEBI
trans-4-CoumarateGenerator, HMDB
(2E)-3-(4-Hydroxyphenyl)-2-propenoic acidHMDB
(2E)-3-(4-Hydroxyphenyl)prop-2-enoic acidHMDB
(E)-3-(4-Hydroxyphenyl)acrylic acidHMDB
(E)-4-Hydroxycinnamic acidHMDB
4’-Hydroxycinnamic acidHMDB
p-Cumaric acidHMDB
p-Hydroxy-trans-cinnamic acidHMDB
p-Hydroxyphenylacrylic acidHMDB
p-trans-Coumaric acidHMDB
trans-3-(4-Hydroxyphenyl)-2-propenoic acidHMDB
trans-4-Coumaric acidHMDB
β-[4-Hydroxyphenyl]acrylic acidHMDB
Chemical FormulaC9H8O3
Average Molecular Weight164.158
Monoisotopic Molecular Weight164.047344122
IUPAC Name(2E)-3-(4-hydroxyphenyl)prop-2-enoic acid
Traditional Namecoumaric acid
CAS Registry Number7400-08-0
SMILES
OC(=O)\C=C\C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+
InChI KeyNGSWKAQJJWESNS-ZZXKWVIFSA-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-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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point211.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.79SANGSTER (1994)
Predicted Properties
PropertyValueSource
logP1.74ALOGPS
logP1.83ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4ChemAxon
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
Polarizability16.43 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014m-1981000000-e7648e85764a445a919c2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-066v-3791000000-a5712bbe8401ef499b5a2014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-8900000000-3bb023f80c1f54a16adc2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03xr-5900000000-a364c62c9122c0fbe6de2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014m-1981000000-e7648e85764a445a919c2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-066v-3791000000-a5712bbe8401ef499b5a2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014m-1891000000-d8804981d3918cac534d2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-2900000000-7075c3e10f9df528109e2016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00xu-6390000000-3110f0f6eb462a38bb642017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-b58aab08954c973df04e2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-0900000000-3ddb41572ba36a950e372012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-0900000000-ccac7f071084bc6600952012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-3900000000-5dc8af06da0120779cff2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00kf-9500000000-9187edc4498ab4345e5a2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-0900000000-3d831c6acd9d3188de2f2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-fbb6439b7d012045f3a82012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0002-0900000000-9e18d43a8d86f9b9e72b2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-014i-0900000000-c45397049a7ba500b3322017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-b58aab08954c973df04e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-3ddb41572ba36a950e372017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-ccac7f071084bc6600952017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-3900000000-5dc8af06da0120779cff2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kf-9500000000-9187edc4498ab4345e5a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-3d831c6acd9d3188de2f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-fbb6439b7d012045f3a82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0900000000-9e18d43a8d86f9b9e72b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-c6491d0aaba639e3ae072021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0002-0900000000-9e18d43a8d86f9b9e72b2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-014i-0900000000-a183cce49af676c95d4e2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-1f13fa0e7a24be298cfb2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9200000000-206402014014906dbe292021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-03di-8900000000-3bb023f80c1f54a16adc2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00kb-3900000000-1118928776a5a6e213db2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0002-0900000000-c5faa58d353ca1466c3c2017-09-14View Spectrum
MSMass Spectrum (Electron Ionization)splash10-03xr-6900000000-348f5c7c030570e0612f2015-03-01View Spectrum
1D NMR1H NMR Spectrum (1D, DMSO, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, DMSO, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0002035
DrugBank IDDB04066
Phenol Explorer Compound ID500
FoodDB IDFDB002593
KNApSAcK IDC00000152
Chemspider ID553148
KEGG Compound IDC00811
BioCyc IDCOUMARATE
BiGG ID36077
Wikipedia LinkP-Coumaric_acid
METLIN ID6450
PubChem Compound637542
PDB IDNot Available
ChEBI ID32374
References
Synthesis ReferenceBen-Bassat, Arie; Sariaslani, Fateme Sima; Huang, Lisa L.; Patnaik, Ranjan; Lowe, David J. Fermentative preparation of para-hydroxycinnamic acid and cinnamic acid at alkaline ph. U.S. Pat. Appl. Publ. (2005), 23 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. [PubMed:14168161 ]