Record Information
Version1.0
Creation date2010-04-08 22:05:28 UTC
Update date2019-11-26 02:57:47 UTC
Primary IDFDB002667
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nametrans-p-Methoxycinnamic acid
Description4-Methoxycinnamic acid, also known as p-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 is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Methoxycinnamic acid is found, on average, in the highest concentration within turmerics. 4-Methoxycinnamic acid has also been detected, but not quantified in, milk (cow) and wild celeries. This could make 4-methoxycinnamic acid a potential biomarker for the consumption of these foods.
CAS Number830-09-1
Structure
Thumb
Synonyms
SynonymSource
4-MethoxycinnamateGenerator
3-(4-Methoxyphenyl)acrylic acidHMDB
Para-methoxycinnamic acidHMDB
3-(4-Methoxyphenyl)acrylateHMDB
Para-methoxycinnamateHMDB
(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 saltHMDB
4-Methoxycinnamate, (e)-isomerHMDB
4-Methoxycinnamate, (Z)-isomerHMDB
4-Methoxycinnamate, zinc saltHMDB
4-Methoxycinnamate, zirconium saltHMDB
e-p-Methoxycinnamic acidHMDB
4-Methoxycinnamate, calcium saltHMDB
4-Methoxycinnamate, magnesium saltHMDB
4-Methoxycinnamate, potassium saltHMDB
4-Methoxycinnamate, sodium saltHMDB
(2E)-3-(4-Methoxyphenyl)prop-2-enoateHMDB
(2E)-3-(4-Methoxyphenyl)-2-propenoic acidHMDB
(e)-3-(4-Methoxyphenyl)-2-propenoic acidHMDB
(e)-4-Methoxycinnamic acidHMDB
(e)-p-Methoxycinnamic acidHMDB
3-(4-Methoxyphenyl)propenoic acidHMDB
4'-Methoxycinnamic acidHMDB
4-Methyoxycinnamic acidHMDB
4’-methoxycinnamic acidHMDB
trans-3-(4-Methoxyphenyl)-2-propenoic acidHMDB
trans-p-Methoxycinnamic acidHMDB
trans-p-MethoxycinnamateHMDB
4-Methoxycinnamic acidMeSH
(2E)-3-(4-methoxyphenyl)prop-2-enoic acidbiospider
(E)-3-(4-Methoxy-phenyl)-acrylic acidbiospider
(E)-3-(4-Methoxyphenyl)acrylatebiospider
(E)-3-(4-Methoxyphenyl)acrylic acidbiospider
(E)-p-Methoxycinnamic acidbiospider
3-(4-Methoxyphenyl)-2-propenoic acid, 9CIdb_source
3-(4-methoxyphenyl)acrylic acidbiospider
3-(4-methoxyphenyl)prop-2-enoic acidbiospider
P-Methoxy ciannamateHMDB
P-Methoxy ciannamic acidHMDB
para-Methoxycinnamatebiospider
para-Methoxycinnamic acidbiospider
trans-2-Propenoic acid, 3-(4-methoxyphenyl)-biospider
trans-3-(4-Methoxyphenyl)acrylic acidbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.55 g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H10O3
IUPAC name(2E)-3-(4-methoxyphenyl)prop-2-enoic acid
InChI IdentifierInChI=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
Isomeric SMILESCOC1=CC=C(\C=C\C(O)=O)C=C1
Average Molecular Weight178.1846
Monoisotopic Molecular Weight178.062994186
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 67.41%; H 5.66%; O 26.94%DFC
Melting PointMp 188-189.5° (174°)DFC
Boiling PointNot Available
Experimental Water Solubility1.97 mg/mL at 25 oCSTEPHEN,H & STEPHEN,T (1963)
Experimental logP2.68HANSCH,C ET AL. (1995)
Experimental pKapKa 4.54 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-03gi-1900000000-cc8f6e9174dff780d643Spectrum
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-24fa3ff739ff064312abSpectrum
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-8900000000-5b42adf83e422cffefb6Spectrum
GC-MStrans-p-Methoxycinnamic acid, 1 TMS, GC-MS Spectrumsplash10-03du-2920000000-dece72c3ca5c90bfc547Spectrum
GC-MStrans-p-Methoxycinnamic acid, non-derivatized, GC-MS Spectrumsplash10-004i-0900000000-a59af9ca91b1d5bd7182Spectrum
GC-MStrans-p-Methoxycinnamic acid, non-derivatized, GC-MS Spectrumsplash10-004i-7900000000-6075ede461ba4ee4c7cdSpectrum
GC-MStrans-p-Methoxycinnamic acid, non-derivatized, GC-MS Spectrumsplash10-004i-1900000000-e899894a8c3562db43a5Spectrum
GC-MStrans-p-Methoxycinnamic acid, non-derivatized, GC-MS Spectrumsplash10-03du-2920000000-dece72c3ca5c90bfc547Spectrum
Predicted GC-MStrans-p-Methoxycinnamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03gi-1900000000-cc8f6e9174dff780d643Spectrum
Predicted GC-MStrans-p-Methoxycinnamic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0080-9650000000-bb37ec4824ae491674e5Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-12552bc1ab86525703a0Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00pi-5900000000-9632d41fa295f06b5381Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004u-9100000000-a6dac09530cfcfc28868Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-004i-0900000000-a59af9ca91b1d5bd7182Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-004i-7900000000-8e025153eeb590c13daaSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0fb9-0900000000-c6baccb046bfcd7d6282Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-014i-1900000000-3927439c287110a6a2f1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03e9-1900000000-03cba42101a868fcbdbbSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03e9-1900000000-53a3d7a661e7d42fabbfSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-00mo-9600000000-b0e876994fe40230d56fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00lr-1900000000-32372664024a7a1cba27Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0fb9-0900000000-c6baccb046bfcd7d6282Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-1900000000-3927439c287110a6a2f1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03e9-1900000000-03cba42101a868fcbdbbSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03e9-1900000000-53a3d7a661e7d42fabbfSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00mo-9600000000-1dd0b8897a3d399d48fcSpectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00lr-1900000000-32372664024a7a1cba27Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0900000000-2c4cab05840440c8ef92Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-f0f239b49fe3cc116d97Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0900000000-d7031d18cf315b765cbfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9800000000-881ce76bbf7add1a8162Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-0d57f82612687cf62c68Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-0900000000-c2111775e672e2666fbdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02u3-1900000000-295574bc9205dd1a7c79Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0900000000-1ec7c0e6355205904aebSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID609479
ChEMBL IDCHEMBL95770
KEGG Compound IDNot Available
Pubchem Compound ID699414
Pubchem Substance IDNot Available
ChEBI ID48541
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02040
CRC / DFC (Dictionary of Food Compounds) IDCMP73-U:CMZ41-H
EAFUS IDNot Available
Dr. Duke IDP-METHOXY-CINNAMIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti pyretic35493 A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hemolyticDUKE
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).