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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:33 UTC
Update Date2020-06-15 17:04:52 UTC
HMDB IDHMDB0002040
Secondary Accession Numbers
  • HMDB02040
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 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 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.
Structure
Data?1582752225
Synonyms
ValueSource
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
4-Methoxycinnamic acidMeSH
trans-p-MethoxycinnamateGenerator
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 Number943-89-5
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

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
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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-03du-2920000000-dece72c3ca5c90bfc547Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0900000000-a59af9ca91b1d5bd7182Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-7900000000-6075ede461ba4ee4c7cdSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-1900000000-e899894a8c3562db43a5Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03du-2920000000-dece72c3ca5c90bfc547Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03gi-1900000000-cc8f6e9174dff780d643Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0080-9650000000-bb37ec4824ae491674e5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-12552bc1ab86525703a0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00pi-5900000000-9632d41fa295f06b5381Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004u-9100000000-a6dac09530cfcfc28868Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-004i-0900000000-a59af9ca91b1d5bd7182Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-004i-7900000000-8e025153eeb590c13daaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0fb9-0900000000-c6baccb046bfcd7d6282Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-014i-1900000000-3927439c287110a6a2f1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03e9-1900000000-03cba42101a868fcbdbbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03e9-1900000000-53a3d7a661e7d42fabbfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-00mo-9600000000-b0e876994fe40230d56fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00lr-1900000000-32372664024a7a1cba27Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0fb9-0900000000-c6baccb046bfcd7d6282Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-1900000000-3927439c287110a6a2f1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03e9-1900000000-03cba42101a868fcbdbbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03e9-1900000000-53a3d7a661e7d42fabbfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00mo-9600000000-1dd0b8897a3d399d48fcSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00lr-1900000000-32372664024a7a1cba27Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0900000000-2c4cab05840440c8ef92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-f0f239b49fe3cc116d97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0900000000-d7031d18cf315b765cbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9800000000-881ce76bbf7add1a8162Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-0d57f82612687cf62c68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-0900000000-c2111775e672e2666fbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02u3-1900000000-295574bc9205dd1a7c79Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.693 +/- 0.228 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.475 +/- 0.218 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.752 +/- 0.225 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.762 +/- 0.324 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.52 +/- 0.192 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.555 +/- 0.17 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.435 +/- 0.204 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified2.941 +/- 2.612 uMAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.02 +/- 0.006 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
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 ReferencesNot Available

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
4-Methoxycinnamic acid → 3,4,5-trihydroxy-6-{[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}oxane-2-carboxylic aciddetails