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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:53:37 UTC
Update Date2023-02-21 17:25:55 UTC
HMDB IDHMDB0037644
Secondary Accession Numbers
  • HMDB37644
Metabolite Identification
Common Name3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid
Description3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid has been detected, but not quantified in, common wheats (Triticum aestivum). This could make 3-(2-hydroxy-3-methoxyphenyl)-2-propenoic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid.
Structure
Data?1677000355
Synonyms
ValueSource
3-(2-Hydroxy-3-methoxyphenyl)-2-propenoateGenerator
2-Hydroxy-3-methoxycinnamic acidHMDB
3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid, 9ciHMDB
O-Ferulic acidHMDB
Orthoferulic acidHMDB
(2E)-3-(2-Hydroxy-3-methoxyphenyl)prop-2-enoateGenerator
O-FerulateGenerator
Chemical FormulaC10H10O4
Average Molecular Weight194.184
Monoisotopic Molecular Weight194.057908808
IUPAC Name(2E)-3-(2-hydroxy-3-methoxyphenyl)prop-2-enoic acid
Traditional Name(2E)-3-(2-hydroxy-3-methoxyphenyl)prop-2-enoic acid
CAS Registry Number3626-94-6
SMILES
COC1=CC=CC(\C=C\C(O)=O)=C1O
InChI Identifier
InChI=1S/C10H10O4/c1-14-8-4-2-3-7(10(8)13)5-6-9(11)12/h2-6,13H,1H3,(H,11,12)/b6-5+
InChI KeyVZFPHVWLPRCAGD-AATRIKPKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Ether
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point183 - 184 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility7191 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.08 g/LALOGPS
logP1.74ALOGPS
logP1.67ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.8ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.5 m³·mol⁻¹ChemAxon
Polarizability19.21 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+144.32630932474
DeepCCS[M-H]-141.72330932474
DeepCCS[M-2H]-177.25930932474
DeepCCS[M+Na]+152.69630932474
AllCCS[M+H]+142.132859911
AllCCS[M+H-H2O]+137.932859911
AllCCS[M+NH4]+146.032859911
AllCCS[M+Na]+147.132859911
AllCCS[M-H]-140.332859911
AllCCS[M+Na-2H]-140.932859911
AllCCS[M+HCOO]-141.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acidCOC1=CC=CC(\C=C\C(O)=O)=C1O3404.4Standard polar33892256
3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acidCOC1=CC=CC(\C=C\C(O)=O)=C1O1816.3Standard non polar33892256
3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acidCOC1=CC=CC(\C=C\C(O)=O)=C1O1859.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid,1TMS,isomer #1COC1=CC=CC(/C=C/C(=O)O[Si](C)(C)C)=C1O1988.6Semi standard non polar33892256
3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid,1TMS,isomer #2COC1=CC=CC(/C=C/C(=O)O)=C1O[Si](C)(C)C1971.9Semi standard non polar33892256
3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid,2TMS,isomer #1COC1=CC=CC(/C=C/C(=O)O[Si](C)(C)C)=C1O[Si](C)(C)C2000.9Semi standard non polar33892256
3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid,1TBDMS,isomer #1COC1=CC=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=C1O2238.8Semi standard non polar33892256
3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid,1TBDMS,isomer #2COC1=CC=CC(/C=C/C(=O)O)=C1O[Si](C)(C)C(C)(C)C2274.9Semi standard non polar33892256
3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid,2TBDMS,isomer #1COC1=CC=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C2515.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-004m-0900000000-e7de9cfa895e19d3fdd32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00di-7494000000-7d3805761509b289208e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 10V, Positive-QTOFsplash10-002b-0900000000-b2737e2bb2b3e29d1c2d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 20V, Positive-QTOFsplash10-0002-1900000000-f08a169de3bec4e33b422016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 40V, Positive-QTOFsplash10-00vi-9800000000-ef30f17684674bad19952016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 10V, Negative-QTOFsplash10-0006-0900000000-6d81c5b753e9fb1528062016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 20V, Negative-QTOFsplash10-0006-0900000000-f7079d7a24d15f4eaabd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 40V, Negative-QTOFsplash10-0564-2900000000-de98d89bab6dc657443f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 10V, Positive-QTOFsplash10-002b-0900000000-97ce251989919a56b8692021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 20V, Positive-QTOFsplash10-0002-0900000000-43e9cd0a4c68c7d83c9c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 40V, Positive-QTOFsplash10-01ba-7900000000-aefd94e0ed8c4e65f01f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 10V, Negative-QTOFsplash10-0002-0900000000-2bddd554f2682b7c0b412021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 20V, Negative-QTOFsplash10-001i-0900000000-21fb08b2b2af109ffe262021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid 40V, Negative-QTOFsplash10-001i-0900000000-8487a6507ca1e209de5d2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB016760
KNApSAcK IDNot Available
Chemspider ID4575887
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5463156
PDB IDNot Available
ChEBI ID173938
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1862801
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .