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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-02-26 19:02:50 UTC
Update Date2019-07-23 07:12:51 UTC
HMDB IDHMDB0059763
Secondary Accession Numbers
  • HMDB59763
Metabolite Identification
Common Name3,4-Dimethoxybenzoic acid
Description3,4-Dimethoxybenzoic acid, also known as 3,4-dimethylprotocatechuate or veratric acid, belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group. 3,4-Dimethoxybenzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3,4-Dimethoxybenzoic acid has been detected, but not quantified in, corianders and olives. This could make 3,4-dimethoxybenzoic acid a potential biomarker for the consumption of these foods. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.
Structure
Data?1563865971
Synonyms
ValueSource
3,4-Dimethylprotocatechuic acidChEBI
Dimethylprotocatechuic acidChEBI
Veratric acidChEBI
Veratrumenoic acidChEBI
Veratrylic acidChEBI
3,4-DimethylprotocatechuateGenerator
DimethylprotocatechuateGenerator
VeratrateGenerator
VeratrumenoateGenerator
VeratrylateGenerator
3,4-DimethoxybenzoateGenerator
Veratric acid, potassium saltMeSH
Veratric acid, sodium saltMeSH
Veratric acid, sodium salt, (11)C-labeledMeSH
3,4-Dimethoxybenzoic acidHMDB
Chemical FormulaC9H10O4
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
IUPAC Name3,4-dimethoxybenzoic acid
Traditional Nameveratric acid
CAS Registry NumberNot Available
SMILES
COC1=C(OC)C=C(C=C1)C(O)=O
InChI Identifier
InChI=1S/C9H10O4/c1-12-7-4-3-6(9(10)11)5-8(7)13-2/h3-5H,1-2H3,(H,10,11)
InChI KeyDAUAQNGYDSHRET-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentP-methoxybenzoic acids and derivatives
Alternative Parents
Substituents
  • P-methoxybenzoic acid or derivatives
  • M-methoxybenzoic acid or derivatives
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Benzoic acid
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • Alkyl aryl ether
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.64 g/LALOGPS
logP1.52ALOGPS
logP1.32ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)4.14ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.24 m³·mol⁻¹ChemAxon
Polarizability17.92 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]+142.87531661259
DarkChem[M-H]-141.83431661259
DeepCCS[M+H]+138.230932474
DeepCCS[M-H]-134.37330932474
DeepCCS[M-2H]-171.62830932474
DeepCCS[M+Na]+147.16730932474
AllCCS[M+H]+139.132859911
AllCCS[M+H-H2O]+134.932859911
AllCCS[M+NH4]+143.132859911
AllCCS[M+Na]+144.232859911
AllCCS[M-H]-137.432859911
AllCCS[M+Na-2H]-138.332859911
AllCCS[M+HCOO]-139.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4-Dimethoxybenzoic acidCOC1=C(OC)C=C(C=C1)C(O)=O2707.5Standard polar33892256
3,4-Dimethoxybenzoic acidCOC1=C(OC)C=C(C=C1)C(O)=O1553.7Standard non polar33892256
3,4-Dimethoxybenzoic acidCOC1=C(OC)C=C(C=C1)C(O)=O1679.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4-Dimethoxybenzoic acid,1TMS,isomer #1COC1=CC=C(C(=O)O[Si](C)(C)C)C=C1OC1707.1Semi standard non polar33892256
3,4-Dimethoxybenzoic acid,1TBDMS,isomer #1COC1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C1OC1946.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3,4-Dimethoxybenzoic acid EI-B (Non-derivatized)splash10-001i-6900000000-4a8e98b69d84f09a207d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dimethoxybenzoic acid EI-B (Non-derivatized)splash10-001i-4900000000-cb469c325f86dcaebb632017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dimethoxybenzoic acid EI-B (Non-derivatized)splash10-001i-6900000000-4a8e98b69d84f09a207d2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Dimethoxybenzoic acid EI-B (Non-derivatized)splash10-001i-4900000000-cb469c325f86dcaebb632018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dimethoxybenzoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fs9-1900000000-7b7b6ee16c41bbeb8ea72017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dimethoxybenzoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9660000000-f0ac17b7c31703cdd68b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dimethoxybenzoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dimethoxybenzoic 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 - 3,4-Dimethoxybenzoic acid Linear Ion Trap , negative-QTOFsplash10-000i-0900000000-b278ebee06358e45a4842017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid Linear Ion Trap , negative-QTOFsplash10-000i-0900000000-65cc74d2e20865936db92017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 10V, Positive-QTOFsplash10-001i-0900000000-68319718835cc95c3de12016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 20V, Positive-QTOFsplash10-001i-0900000000-3112f03abf5146b7fdbc2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 40V, Positive-QTOFsplash10-0ff1-6900000000-ed8884f3fcc1216b34a32016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 10V, Negative-QTOFsplash10-001i-0900000000-6b3b62b879aa4d5e208e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 20V, Negative-QTOFsplash10-0080-0900000000-10547cd32070770340ff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 40V, Negative-QTOFsplash10-05ir-7900000000-c21b16fa3776d40078512016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 10V, Positive-QTOFsplash10-000i-0900000000-c50ac015643e0db698cd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 20V, Positive-QTOFsplash10-0019-0900000000-796d5f48c5cee4880d652021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 40V, Positive-QTOFsplash10-0ff0-9600000000-ae900b44493c1d0734372021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 10V, Negative-QTOFsplash10-001i-0900000000-49a059652c5c432bc06e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 20V, Negative-QTOFsplash10-000i-0900000000-2d692dbb4687b9ffd7942021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethoxybenzoic acid 40V, Negative-QTOFsplash10-052f-9300000000-cf393361be800fb908b22021-09-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 ID419
FooDB IDFDB000222
KNApSAcK IDNot Available
Chemspider ID6854
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7121
PDB IDTWO
ChEBI ID296881
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Shin SW, Jung E, Kim S, Lee KE, Youm JK, Park D: Antagonist effects of veratric acid against UVB-induced cell damages. Molecules. 2013 May 10;18(5):5405-19. doi: 10.3390/molecules18055405. [PubMed:23666007 ]
  2. Pham NH, Baldo BA, Manfredi M, Zerboni R: Fine structural specificity differences of trimethoprim allergenic determinants. Clin Exp Allergy. 1996 Oct;26(10):1155-60. [PubMed:8911701 ]