Record Information
Version1.0
Creation date2010-04-08 22:10:02 UTC
Update date2019-11-26 03:06:19 UTC
Primary IDFDB012172
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Hydroxy-3-methoxybenzoic acid
Description2-hydroxy-3-methoxybenzoic acid, also known as O-vanillic acid or O-vanillate, belongs to M-methoxybenzoic acids and derivatives class of compounds. Those are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. 2-hydroxy-3-methoxybenzoic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 2-hydroxy-3-methoxybenzoic acid can be found in evening primrose, which makes 2-hydroxy-3-methoxybenzoic acid a potential biomarker for the consumption of this food product.
CAS Number877-22-5
Structure
Thumb
Synonyms
SynonymSource
O-Vanillic acidChEBI
O-VanillateGenerator
3-MethoxysalicylateGenerator
2-Hydroxy-3-methoxybenzoic acidHMDB
2-Hydroxy-3-methoxybenzoateGenerator
3-Hydroxy-m-anisic acidbiospider
3-Methoxysalicylic aciddb_source
Benzoic acid, 2-hydroxy-3-methoxy-biospider
Benzoic acid, 2-hydroxy-3-methoxy- (9CI)biospider
Guaiacol-3-carboxylic aciddb_source
m-Anisic acid, 2-hydroxy-biospider
o-Vanillic aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility3.86 g/LALOGPS
logP1.87ALOGPS
logP1.82ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.55ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.76 m³·mol⁻¹ChemAxon
Polarizability15.73 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC8H8O4
IUPAC name2-hydroxy-3-methoxybenzoic acid
InChI IdentifierInChI=1S/C8H8O4/c1-12-6-4-2-3-5(7(6)9)8(10)11/h2-4,9H,1H3,(H,10,11)
InChI KeyAUZQQIPZESHNMG-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC=CC(C(O)=O)=C1O
Average Molecular Weight168.1467
Monoisotopic Molecular Weight168.042258744
Classification
Description belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentM-methoxybenzoic acids and derivatives
Alternative Parents
Substituents
  • M-methoxybenzoic acid or derivatives
  • Salicylic acid
  • Salicylic acid or derivatives
  • Hydroxybenzoic acid
  • Methoxyphenol
  • Benzoic acid
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Vinylogous acid
  • 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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 57.14%; H 4.80%; O 38.06%DFC
Melting PointMp 152° (anhyd.)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP1.94HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0g4i-0900000000-6c062178ed4c1c680d3eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0g4i-0900000000-6c062178ed4c1c680d3eJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0g4i-3900000000-5e54c3714d2e7a9befd8JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-8390000000-6e3e2e42aa8eabde97c1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-85845ccd3d65e6ff7699JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0g4i-0900000000-9fd06257f865a7e1a808JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9400000000-1e3b713b8b16d20f91b8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-d400f8e246374ba5e1e6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-1900000000-2ce1148fc92ff320e638JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-8900000000-50427ff925d936d3bd89JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID70140
Pubchem Substance IDNot Available
ChEBI ID545918
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHFB57-G:HDX14-J
EAFUS IDNot Available
Dr. Duke IDO-VANILLIC-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 / 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).