Showing metabocard for 4-Methoxycinnamic acid (BMDB0002040)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:50:19 UTC
Update Date2020-04-22 15:09:30 UTC
MCDB ID BMDB0002040
Secondary Accession Numbers
  • BMDB02040
Metabolite Identification
Common Name4-Methoxycinnamic acid
Description4-Methoxycinnamic acid, also known as para-methoxycinnamate or O-methyl-p-coumarate, belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. 4-Methoxycinnamic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-MethoxycinnamateGenerator
3-(4-Methoxyphenyl)acrylic acidChEMBL, HMDB
Para-methoxycinnamic acidChEMBL, HMDB
3-(4-Methoxyphenyl)acrylateGenerator, HMDB
Para-methoxycinnamateGenerator, HMDB
(e)-3-(4-Methoxyphenyl)acrylateHMDB
(e)-3-(4-Methoxyphenyl)acrylic acidHMDB
3-(4-Methoxy-phenyl)-acrylateHMDB
3-(4-Methoxy-phenyl)-acrylic acidHMDB
3-(4-Methoxyphenyl)-2-propenoateHMDB
3-(4-Methoxyphenyl)-2-propenoic acidHMDB
4-Methoxy cinnamateHMDB
4-Methoxy cinnamic acidHMDB
O-Methyl-P-coumarateHMDB
O-Methyl-P-coumaric acidHMDB
P-Hydroxy methyl cinnamateHMDB
P-Methoxy ciannamateHMDB
P-Methoxy ciannamic acidHMDB
P-MethoxycinnamateHMDB
P-Methoxycinnamic acidHMDB
trans-4-MethoxycinnamateHMDB
trans-4-Methoxycinnamic acidHMDB
4-Methoxycinnamate, aluminum saltMeSH, HMDB
4-Methoxycinnamate, (e)-isomerMeSH, HMDB
4-Methoxycinnamate, (Z)-isomerMeSH, HMDB
4-Methoxycinnamate, zinc saltMeSH, HMDB
4-Methoxycinnamate, zirconium saltMeSH, HMDB
e-P-Methoxycinnamic acidMeSH, HMDB
4-Methoxycinnamate, calcium saltMeSH, HMDB
4-Methoxycinnamate, magnesium saltMeSH, HMDB
4-Methoxycinnamate, potassium saltMeSH, HMDB
4-Methoxycinnamate, sodium saltMeSH, HMDB
(2E)-3-(4-Methoxyphenyl)prop-2-enoateGenerator, HMDB
4-Methoxycinnamic acidMeSH
(2E)-3-(4-Methoxyphenyl)-2-propenoic acidHMDB
(E)-3-(4-Methoxyphenyl)-2-propenoic acidHMDB
(E)-3-(4-Methoxyphenyl)acrylic acidHMDB
(E)-4-Methoxycinnamic acidHMDB
(E)-p-Methoxycinnamic acidHMDB
3-(4-Methoxyphenyl)propenoic acidHMDB
4'-Methoxycinnamic acidHMDB
4-Methyoxycinnamic acidHMDB
4’-Methoxycinnamic acidHMDB
O-Methyl-p-coumaric acidHMDB
p-Methoxycinnamic acidHMDB
trans-3-(4-Methoxyphenyl)-2-propenoic acidHMDB
trans-p-Methoxycinnamic acidHMDB
trans-p-MethoxycinnamateGenerator, HMDB
Chemical FormulaC10H10O3
Average Molecular Weight178.1846
Monoisotopic Molecular Weight178.062994186
IUPAC Name(2E)-3-(4-methoxyphenyl)prop-2-enoic acid
Traditional Namep-methoxy-cinnamic acid
CAS Registry Number830-09-1
SMILES
COC1=CC=C(\C=C\C(O)=O)C=C1
InChI Identifier
InChI=1S/C10H10O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-7H,1H3,(H,11,12)/b7-4+
InChI KeyAFDXODALSZRGIH-QPJJXVBHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassCinnamic acids
Direct ParentCinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point173 - 175 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.71 mg/mL at 25 °CNot Available
LogP2.68HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP2.37ALOGPS
logP1.98ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)4.11ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.52 m³·mol⁻¹ChemAxon
Polarizability18.34 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-MS (1 TMS)splash10-03du-2920000000-dece72c3ca5c90bfc5472014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0900000000-a59af9ca91b1d5bd71822017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-7900000000-6075ede461ba4ee4c7cd2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-1900000000-e899894a8c3562db43a52017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03du-2920000000-dece72c3ca5c90bfc5472017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03gi-1900000000-cc8f6e9174dff780d6432017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0080-9650000000-bb37ec4824ae491674e52017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-12552bc1ab86525703a02012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00pi-5900000000-9632d41fa295f06b53812012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004u-9100000000-a6dac09530cfcfc288682012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-004i-0900000000-a59af9ca91b1d5bd71822012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-004i-7900000000-8e025153eeb590c13daa2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0fb9-0900000000-c6baccb046bfcd7d62822012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-014i-1900000000-3927439c287110a6a2f12012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03e9-1900000000-03cba42101a868fcbdbb2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03e9-1900000000-53a3d7a661e7d42fabbf2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-00mo-9600000000-b0e876994fe40230d56f2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00lr-1900000000-32372664024a7a1cba272017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0fb9-0900000000-c6baccb046bfcd7d62822017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-1900000000-3927439c287110a6a2f12017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03e9-1900000000-03cba42101a868fcbdbb2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03e9-1900000000-53a3d7a661e7d42fabbf2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00mo-9600000000-1dd0b8897a3d399d48fc2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00lr-1900000000-32372664024a7a1cba272017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0900000000-2c4cab05840440c8ef922017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03di-0900000000-3954121d114e7a1254012021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-f0f239b49fe3cc116d972017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0900000000-d7031d18cf315b765cbf2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9800000000-881ce76bbf7add1a81622017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-0d57f82612687cf62c682017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-0900000000-c2111775e672e2666fbd2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02u3-1900000000-295574bc9205dd1a7c792017-09-01View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Not Available2012-12-05View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0002040
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002667
KNApSAcK IDNot Available
Chemspider ID609479
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6453
PubChem Compound699414
PDB IDNot Available
ChEBI ID260249
References
Synthesis ReferencePuscaru, E.; Zotta, V.; Serper, Ana; Popescu, Margareta; Hociung, Jana; Gasmet, Ana; Spataru, Rodica. The N-methyl series of piperazine. II. Cinnamic acid derivatives. Farmacia (Bucharest, Romania) (1961), 9 345-50.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. [PubMed:27999311 ]