Record Information
Version1.0
Creation date2010-04-08 22:04:29 UTC
Update date2018-05-29 00:12:45 UTC
Primary IDFDB000222
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3,4-Dimethoxybenzoic acid
Description3,4-dimethoxybenzoic acid, also known as veratric acid or 3,4-dimethylprotocatechuic acid, belongs to P-methoxybenzoic acids and derivatives class of compounds. Those 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 slightly soluble (in water) and a weakly acidic compound (based on its pKa). 3,4-dimethoxybenzoic acid can be synthesized from benzoic acid. 3,4-dimethoxybenzoic acid is also a parent compound for other transformation products, including but not limited to, 3beta-[(O-beta-D-glucopyranosyl-(1->4)-O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranosyl)oxy]-17alpha-hydroxy-16beta-[(O-(2-O-3,4-dimethoxybenzoyl-beta-D-xylopyranosyl)-(1->3)-2-O-acetyl-alpha-L-arabinopyranosyl)oxy]cholest-5-en-22-one, 3beta-[(beta-D-glucopyranosyl)oxy]-17alpha-hydroxy-16beta-[(O-(2-O-3,4-dimethoxybenzoyl-beta-D-xylopyranosyl)-(1->3)-2-O-acetyl-alpha-L-arabinopyranosyl)oxy]cholest-5-en-22-one, and 3beta-[(O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranosyl)oxy]-17alpha-hydroxy-16beta-[(O-(2-O-3,4-dimethoxybenzoyl-beta-D-xylopyranosyl)-(1->3)-2-O-acetyl-alpha-L-arabinopyranosyl)oxy]cholest-5-en-22-one. 3,4-dimethoxybenzoic acid can be found in coriander and olive, which makes 3,4-dimethoxybenzoic acid a potential biomarker for the consumption of these food products.
CAS Number93-07-2
Structure
Thumb
Synonyms
SynonymSource
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-Dimethoxy-benzoic acidbiospider
Benzoic acid, 3,4-dimethoxy-biospider
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H10O4
IUPAC name3,4-dimethoxybenzoic acid
InChI IdentifierInChI=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
Isomeric SMILESCOC1=C(OC)C=C(C=C1)C(O)=O
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
Classification
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point181 oC
Boiling PointNot Available
Experimental Water Solubility0.5 mg/mL at 14 oCBEILSTEIN
Experimental logP1.61HANSCH,C ET AL. (1995)
Experimental pKa4.36
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID7121
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID419
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke ID3,4-DIMETHOXY-BENZOIC-ACID|VERATRIC-ACID
BIGG IDNot Available
KNApSAcK IDC00035926
HET 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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
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).