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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 17:50:44 UTC
Update Date2019-07-23 06:11:21 UTC
HMDB IDHMDB0032604
Secondary Accession Numbers
  • HMDB32604
Metabolite Identification
Common Name2-Methoxybenzoic acid
Description2-Methoxybenzoic acid, also known as 2-methoxy-benzoate or O-anisic acid, belongs to the class of organic compounds known as o-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 2 of the benzene ring is replaced by a methoxy group. 2-Methoxybenzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-Methoxybenzoic acid has been detected, but not quantified in, several different foods, such as american butterfish, abiyuchs, lemon grass, beans, and triticales. This could make 2-methoxybenzoic acid a potential biomarker for the consumption of these foods. 2-Methoxybenzoic acid is a flavouring agent 2-Methoxybenzoic acid, o-anisic acid, or orth2-Methoxybenzoic acid is an organic compound which is an ortho carboxylic acid.
Structure
Data?1563862281
Synonyms
ValueSource
2-Anisic acidChEBI
2-Methoxy-benzoic acidChEBI
O-Anisic acidChEBI
O-Methoxybenzoic acidChEBI
Ortho-methoxybenzoic acidChEBI
Salicylic acid methyl etherChEBI
2-AnisateGenerator
2-Methoxy-benzoateGenerator
O-AnisateGenerator
O-MethoxybenzoateGenerator
Ortho-methoxybenzoateGenerator
Salicylate methyl etherGenerator
2-MethoxybenzoateGenerator
BENZOIC ACID,2-methoxyHMDB
FEMA 3943HMDB
O-Anisic acid, 8ciHMDB
O-Methoxy benzoic acidHMDB
O-Methylsalicylic acidHMDB
2-Methoxybenzoic acid, sodium saltHMDB
O-MethylsalicylateGenerator
2-Methoxybenzoic acidMeSH
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Name2-methoxybenzoic acid
Traditional Nameo-anisic acid
CAS Registry Number579-75-9
SMILES
COC1=CC=CC=C1C(O)=O
InChI Identifier
InChI=1S/C8H8O3/c1-11-7-5-3-2-4-6(7)8(9)10/h2-5H,1H3,(H,9,10)
InChI KeyILUJQPXNXACGAN-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 2 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentO-methoxybenzoic acids and derivatives
Alternative Parents
Substituents
  • O-methoxybenzoic acid or derivatives
  • Benzoic acid
  • Anisole
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point106 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5 mg/mL at 30 °CNot Available
LogP1.59Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.01 g/LALOGPS
logP1.67ALOGPS
logP1.47ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)3.73ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.78 m³·mol⁻¹ChemAxon
Polarizability14.78 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0pki-9600000000-fbe367b85c1ed8dc75aaSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0pki-9600000000-fbe367b85c1ed8dc75aaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zgr-6900000000-a3ee33481c72ea8b2e88Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-9420000000-3dc31e496fbaeb3ac3bfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-2ec02738512fec538d47Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-3900000000-d6fc6b20fe7614a09f5cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004l-9000000000-616484432f9d11c3ac1eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ikc-9000000000-d2000913539e4a48bd80Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-12ccf8ba5a601f24ec99Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-6aea479dc8cb85208bc7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-cfade89e06a07686d38aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-03695276db5701bc1976Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-e0698fddeefa01c9865aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-b29a23c8ebbae598f143Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-7406abcc953b6b810b16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-8b12afbeeb635686fe9eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-c4f59c065297775b6bd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9200000000-b8ba4fc1f6366c6a4e3cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0900000000-d7d003cd059bac93e850Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1900000000-f5f063192382e0bba545Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-9400000000-3ba06e7b78fa225f347fSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.692 +/- 0.319 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.717 +/- 0.23 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified1.212 +/- 0.327 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified2.211 +/- 1.052 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.355 +/- 0.115 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.49 +/- 0.133 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.426 +/- 0.111 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.56 +/- 0.125 uMAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.085 +/- 0.014 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 IDNot Available
FoodDB IDFDB010544
KNApSAcK IDNot Available
Chemspider ID10892
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkO-Methoxybenzoic_acid
METLIN IDNot Available
PubChem Compound11370
PDB IDNot Available
ChEBI ID421840
Food Biomarker OntologyNot Available
VMH IDNot Available
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.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
2-Methoxybenzoic acid → 3,4,5-trihydroxy-6-(2-methoxybenzoyloxy)oxane-2-carboxylic aciddetails
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
Reactions
2-Methoxybenzoic acid → 2-{[hydroxy(2-methoxyphenyl)methylidene]amino}acetic aciddetails