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trans-p-Methoxycinnamic acid (FDB002667)

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 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 found, on average, in the highest concentration within turmerics (Curcuma longa). 4-Methoxycinnamic acid has also been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), milk (cow), and wild celeries (Apium graveolens). This could make 4-methoxycinnamic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Methoxycinnamic acid.
CAS Number830-09-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
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
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
Predicted GC-MStrans-p-Methoxycinnamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-12552bc1ab86525703a02012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00pi-5900000000-9632d41fa295f06b53812012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004u-9100000000-a6dac09530cfcfc288682012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-004i-0900000000-a59af9ca91b1d5bd71822012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-004i-7900000000-8e025153eeb590c13daa2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0fb9-0900000000-c6baccb046bfcd7d62822012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-014i-1900000000-3927439c287110a6a2f12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03e9-1900000000-03cba42101a868fcbdbb2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03e9-1900000000-53a3d7a661e7d42fabbf2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-00mo-9600000000-b0e876994fe40230d56f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00lr-1900000000-32372664024a7a1cba272017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0fb9-0900000000-c6baccb046bfcd7d62822017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-1900000000-3927439c287110a6a2f12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03e9-1900000000-03cba42101a868fcbdbb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03e9-1900000000-53a3d7a661e7d42fabbf2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00mo-9600000000-1dd0b8897a3d399d48fc2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00lr-1900000000-32372664024a7a1cba272017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0900000000-2c4cab05840440c8ef922017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03di-0900000000-3954121d114e7a1254012021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-f0f239b49fe3cc116d972017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0900000000-d7031d18cf315b765cbf2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9800000000-881ce76bbf7add1a81622017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-0d57f82612687cf62c682017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-0900000000-c2111775e672e2666fbd2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02u3-1900000000-295574bc9205dd1a7c792017-09-01View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
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).