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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 19:07:33 UTC
Update Date2023-02-21 17:24:09 UTC
HMDB IDHMDB0034315
Secondary Accession Numbers
  • HMDB34315
Metabolite Identification
Common Name3-(3,4-Dimethoxyphenyl)-2-propenoic acid
Description3-(3,4-Dimethoxyphenyl)-2-propenoic acid belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. 3-(3,4-Dimethoxyphenyl)-2-propenoic acid has been detected, but not quantified in, beverages and wasabis (Wasabia japonica). This could make 3-(3,4-dimethoxyphenyl)-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-(3,4-Dimethoxyphenyl)-2-propenoic acid.
Structure
Data?1677000249
Synonyms
ValueSource
3-(3,4-Dimethoxyphenyl)-2-propenoateGenerator
3-(3,4-Dimethoxyphenyl)propenoic acidMeSH
3-(3,4-Dimethoxyphenyl)propenoic acid, (e)-isomerMeSH
oo'-Dimethylcaffeic acidChEMBL, HMDB
oo'-DimethylcaffeateGenerator, HMDB
(2E)-3-(3,4-Dimethoxyphenyl)-2-propenoic acidHMDB
(2E)-3-(3,4-Dimethoxyphenyl)acrylic acidHMDB
(2E)-3-(3,4-Dimethoxyphenyl)prop-2-enoic acidHMDB
(e)-3',4'-Dimethoxycinnamic acidHMDB
(e)-3,4-Dimethoxycinnamic acidHMDB
3, 4-Dimethoxycinnamic acidHMDB
3,4-Dimethoxy-cinnamic acidHMDB
3,4-Dimethoxy-trans-cinnamic acidHMDB
3,4-Dimethoxycinnamic acidHMDB
3,4-Dimethoxycinnamic acid, 8ciHMDB
3,4-Dimethoxycinnamic acid, predominantly transHMDB
3,4-Dimethoxyphenyl-2-propenoic acidHMDB
3-(3,4-Dimethoxyphenyl)-(e)-2-propenoic acidHMDB
3-(3,4-Dimethoxyphenyl)-2-propenoic acid, 9ciHMDB
Caffeic acid dimethyl etherHMDB
Dimethyl caffeic acidHMDB
Dimethylcaffeic acidHMDB
e)-3,4-Dimethoxycinnamic acidHMDB
3,4-DimethoxycinnamateGenerator
Chemical FormulaC11H12O4
Average Molecular Weight208.2106
Monoisotopic Molecular Weight208.073558872
IUPAC Name(2E)-3-(3,4-dimethoxyphenyl)prop-2-enoic acid
Traditional Namecinnamic acid,3,4-dimethoxy
CAS Registry Number14737-89-4
SMILES
COC1=C(OC)C=C(\C=C\C(O)=O)C=C1
InChI Identifier
InChI=1S/C11H12O4/c1-14-9-5-3-8(4-6-11(12)13)7-10(9)15-2/h3-7H,1-2H3,(H,12,13)/b6-4+
InChI KeyHJBWJAPEBGSQPR-GQCTYLIASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid or derivatives
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Alkyl aryl ether
  • 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 Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point180 - 181.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility989.3 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.4 g/LALOGPS
logP2.5ALOGPS
logP1.82ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)3.87ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity55.99 m³·mol⁻¹ChemAxon
Polarizability21.38 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
DarkChem[M+H]+150.86831661259
DarkChem[M-H]-151.02131661259
DeepCCS[M+H]+151.64730932474
DeepCCS[M-H]-149.28930932474
DeepCCS[M-2H]-182.31430932474
DeepCCS[M+Na]+157.7430932474
AllCCS[M+H]+146.132859911
AllCCS[M+H-H2O]+142.032859911
AllCCS[M+NH4]+149.832859911
AllCCS[M+Na]+150.932859911
AllCCS[M-H]-146.232859911
AllCCS[M+Na-2H]-146.732859911
AllCCS[M+HCOO]-147.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-(3,4-Dimethoxyphenyl)-2-propenoic acidCOC1=C(OC)C=C(\C=C\C(O)=O)C=C13408.5Standard polar33892256
3-(3,4-Dimethoxyphenyl)-2-propenoic acidCOC1=C(OC)C=C(\C=C\C(O)=O)C=C11821.4Standard non polar33892256
3-(3,4-Dimethoxyphenyl)-2-propenoic acidCOC1=C(OC)C=C(\C=C\C(O)=O)C=C11980.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-(3,4-Dimethoxyphenyl)-2-propenoic acid,1TMS,isomer #1COC1=CC=C(/C=C/C(=O)O[Si](C)(C)C)C=C1OC2045.3Semi standard non polar33892256
3-(3,4-Dimethoxyphenyl)-2-propenoic acid,1TBDMS,isomer #1COC1=CC=C(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)C=C1OC2288.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid GC-MS (1 TMS)splash10-00kf-3960000000-34c5d57d812515baaafb2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid EI-B (Non-derivatized)splash10-0a4i-2490000000-78337df021d790d762642017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid GC-MS (Non-derivatized)splash10-00kf-3960000000-34c5d57d812515baaafb2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ox-0910000000-eeb5b1709ec7624fdb7f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-02mi-7490000000-edf5b2b209c673b4df3e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid LC-ESI-qTof , Positive-QTOFsplash10-02u1-0900000000-558cee09a88e70dca3462017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid LC-ESI-QTOF , negative-QTOFsplash10-0pb9-0980000000-e16c634ed57b16445ae62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid LC-ESI-QTOF , positive-QTOFsplash10-0006-0900000000-c0812e599929d0f5cba22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid LC-ESI-QTOF , positive-QTOFsplash10-0006-1900000000-622684d383a32a359a5f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid LC-ESI-QTOF , positive-QTOFsplash10-00lv-3900000000-f5ea19d5df85348292d02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid LC-ESI-QTOF , positive-QTOFsplash10-00l6-7900000000-b961cf178e856ed647122017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid LC-ESI-QTOF , positive-QTOFsplash10-0006-2930000000-65aac7f397aedcc13f822017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid , positive-QTOFsplash10-02u1-0900000000-558cee09a88e70dca3462017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid , positive-QTOFsplash10-0006-1900000000-1a0556432e074f5a76502017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid 6V, Positive-QTOFsplash10-0006-0930000000-2d088285911c576e4f2c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid 6V, Positive-QTOFsplash10-0f7k-1900000000-84ea25158e7e59605f212021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid 10V, Positive-QTOFsplash10-0006-0900000000-9401c48c3c030e3549902021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid 10V, Positive-QTOFsplash10-0006-0930000000-6107890e9920f527c3ca2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid 10V, Positive-QTOFsplash10-0006-0900000000-3e7f8074e17791ae80de2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid 10V, Positive-QTOFsplash10-0006-0920000000-c644e987798bdbe75ec72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid 30V, Positive-QTOFsplash10-0f7k-1900000000-fa87d6da133accb95d652021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid 50V, Positive-QTOFsplash10-00or-9100000000-fcb4ebb3a9207aad72502021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid 50V, Positive-QTOFsplash10-000l-9400000000-e6ce82dffb59b45e00f82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid 30V, Positive-QTOFsplash10-000w-2900000000-db288be2343c93680a592021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid 10V, Positive-QTOFsplash10-0a4l-0970000000-369346126e3564c557972016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid 20V, Positive-QTOFsplash10-08fu-0910000000-9e0e50d0d6030e69901a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid 40V, Positive-QTOFsplash10-071i-3900000000-5205ddde3fd807f955862016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid 10V, Negative-QTOFsplash10-0a4i-0290000000-64b73c7fb097501a5bac2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid 20V, Negative-QTOFsplash10-0a4i-0950000000-9e26b1adf0ca2a461f0f2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(3,4-Dimethoxyphenyl)-2-propenoic acid 40V, Negative-QTOFsplash10-06r5-1900000000-99c1208279666ccbed092016-08-04Wishart 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 Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.465 +/- 0.064 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.568 +/- 0.054 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.419 +/- 0.06 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.523 +/- 0.146 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.572 +/- 0.034 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.674 +/- 0.043 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.564 +/- 0.061 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.564 +/- 0.062 uMAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.166 +/- 0.019 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 ID502
FooDB IDFDB012665
KNApSAcK IDC00033558
Chemspider ID626174
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound717531
PDB IDNot Available
ChEBI ID86549
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1417471
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.. .