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Record Information
Version3.6
Creation Date2006-05-22 14:17:33 UTC
Update Date2016-02-11 01:05:14 UTC
HMDB IDHMDB02040
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Methoxycinnamic acid
DescriptionEsters of p-methoxycinnamic acid are among the popular UV-B screening compounds used in various cosmetic formulations in sunscreen products.
Structure
Thumb
Synonyms
ValueSource
3-(4-Methoxyphenyl)acrylic acidChEMBL
Para-methoxycinnamic acidChEMBL
3-(4-Methoxyphenyl)acrylateGenerator
(e)-3-(4-Methoxyphenyl)prop-2-enoateGenerator
Para-methoxycinnamateGenerator
(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
4-MethoxycinnamateHMDB
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
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 KeyInChIKey=AFDXODALSZRGIH-QPJJXVBHSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Phenylpropene
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • DNA component
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point173 - 175 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.712 mg/mL at 25 °CNot Available
LogP2.68HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.55 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.52 m3·mol-1ChemAxon
Polarizability18.34 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-03du-2920000000-dece72c3ca5c90bfc547View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-12552bc1ab86525703a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00pi-5900000000-9632d41fa295f06b5381View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004u-9100000000-a6dac09530cfcfc28868View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-004i-0900000000-a59af9ca91b1d5bd7182View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-004i-7900000000-8e025153eeb590c13daaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0fb9-0900000000-c6baccb046bfcd7d6282View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-014i-1900000000-3927439c287110a6a2f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03e9-1900000000-03cba42101a868fcbdbbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03e9-1900000000-53a3d7a661e7d42fabbfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-00mo-9600000000-b0e876994fe40230d56fView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB002667
KNApSAcK IDNot Available
Chemspider ID609479
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02040
Metagene LinkHMDB02040
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 ReferencesNot Available