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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-01-09 12:11:21 UTC
Update Date2019-07-23 07:12:45 UTC
HMDB IDHMDB0059713
Secondary Accession Numbers
  • HMDB59713
Metabolite Identification
Common Name3-Methoxysalicylic acid
Description3-Methoxysalicylic acid, also known as O-vanillic acid or O-vanillate, 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. 3-Methoxysalicylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3-Methoxysalicylic acid has been detected, but not quantified in, evening primroses. This could make 3-methoxysalicylic acid a potential biomarker for the consumption of these foods. 3-Methoxysalicylic acid (CAS Number 877-22-5) is a beige fine crystalline powder.
Structure
Data?1563865965
Synonyms
ValueSource
O-Vanillic acidChEBI
O-VanillateGenerator
3-MethoxysalicylateGenerator
2-Hydroxy-3-methoxybenzoic acidHMDB
2-Hydroxy-3-methoxybenzoateGenerator
Chemical FormulaC8H8O4
Average Molecular Weight168.1467
Monoisotopic Molecular Weight168.042258744
IUPAC Name2-hydroxy-3-methoxybenzoic acid
Traditional Name3-methoxysalicyclic acid
CAS Registry Number877-22-5
SMILES
COC1=CC=CC(C(O)=O)=C1O
InChI Identifier
InChI=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
Chemical Taxonomy
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
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0g4i-0900000000-6c062178ed4c1c680d3eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0g4i-0900000000-6c062178ed4c1c680d3eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0g4i-3900000000-5e54c3714d2e7a9befd8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-8390000000-6e3e2e42aa8eabde97c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-85845ccd3d65e6ff7699Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0g4i-0900000000-9fd06257f865a7e1a808Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9400000000-1e3b713b8b16d20f91b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0900000000-d400f8e246374ba5e1e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-1900000000-2ce1148fc92ff320e638Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-8900000000-50427ff925d936d3bd89Spectrum
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 IDNot Available
FooDB IDFDB012172
KNApSAcK IDNot Available
Chemspider ID63328
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound70140
PDB IDNot Available
ChEBI ID68496
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]