Record Information
Version1.0
Creation date2010-04-08 22:05:28 UTC
Update date2018-05-28 18:34:04 UTC
Primary IDFDB002667
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nametrans-p-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 is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Methoxycinnamic acid is found, on average, in the highest concentration in turmerics. 4-Methoxycinnamic acid has also been detected, but not quantified in, 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
4-Methoxycinnamic acidMeSH
(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
(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
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-03du-2920000000-dece72c3ca5c90bfc547JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0900000000-a59af9ca91b1d5bd7182JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-7900000000-6075ede461ba4ee4c7cdJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-1900000000-e899894a8c3562db43a5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03du-2920000000-dece72c3ca5c90bfc547JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03gi-1900000000-cc8f6e9174dff780d643JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0080-9650000000-bb37ec4824ae491674e5JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-12552bc1ab86525703a0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00pi-5900000000-9632d41fa295f06b5381JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004u-9100000000-a6dac09530cfcfc28868JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-004i-0900000000-a59af9ca91b1d5bd7182JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-004i-7900000000-8e025153eeb590c13daaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0fb9-0900000000-c6baccb046bfcd7d6282JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-014i-1900000000-3927439c287110a6a2f1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03e9-1900000000-03cba42101a868fcbdbbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03e9-1900000000-53a3d7a661e7d42fabbfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-00mo-9600000000-b0e876994fe40230d56fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00lr-1900000000-32372664024a7a1cba27JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0fb9-0900000000-c6baccb046bfcd7d6282JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-1900000000-3927439c287110a6a2f1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03e9-1900000000-03cba42101a868fcbdbbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03e9-1900000000-53a3d7a661e7d42fabbfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00mo-9600000000-1dd0b8897a3d399d48fcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00lr-1900000000-32372664024a7a1cba27JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0900000000-2c4cab05840440c8ef92JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-f0f239b49fe3cc116d97JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0900000000-d7031d18cf315b765cbfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9800000000-881ce76bbf7add1a8162JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-0d57f82612687cf62c68JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-0900000000-c2111775e672e2666fbdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02u3-1900000000-295574bc9205dd1a7c79JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
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).