You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:50:56 UTC
Update Date2019-07-23 06:11:25 UTC
HMDB IDHMDB0032639
Secondary Accession Numbers
  • HMDB32639
Metabolite Identification
Common NameMethyl 4-methoxybenzoate
DescriptionMethyl 4-methoxybenzoate, also known as 4-methoxy methylbenzoate or p-anisic acid methyl ester, 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. Methyl 4-methoxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa). Methyl 4-methoxybenzoate is a sweet, anise, and balsam tasting compound. Outside of the human body, Methyl 4-methoxybenzoate is found, on average, in the highest concentration within star anises. This could make methyl 4-methoxybenzoate a potential biomarker for the consumption of these foods. A benzoate ester obtained by the formal condensation of the carboy group of 4-methoxybenzoic acid with methanol.
Structure
Data?1563862285
Synonyms
ValueSource
4-Methoxy methylbenzoateChEBI
Methyl 4-anisateChEBI
p-Methoxybenzoic acid methyl esterChEBI
4-Methoxy methylbenzoic acidGenerator
Methyl 4-anisic acidGenerator
p-Methoxybenzoate methyl esterGenerator
Methyl 4-methoxybenzoic acidGenerator
4-Methoxybenzoic acid methyl esterHMDB
Benzoic acid, 4-methoxy-, methyl esterHMDB
Benzoic acid, p-methoxy-, methyl esterHMDB
FEMA 2679HMDB
Methyl ester OF p-methoxybenzoic acidHMDB
Methyl p-anisateHMDB
Methyl p-methoxybenzoateHMDB
p-Anisic acid methyl esterHMDB
p-Anisic acid, methyl esterHMDB
Methyl p-anisic acidGenerator
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Namemethyl 4-methoxybenzoate
Traditional Namemethyl anisate
CAS Registry Number121-98-2
SMILES
COC(=O)C1=CC=C(OC)C=C1
InChI Identifier
InChI=1S/C9H10O3/c1-11-8-5-3-7(4-6-8)9(10)12-2/h3-6H,1-2H3
InChI KeyDDIZAANNODHTRB-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
  • Benzoate ester
  • Anisole
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Methyl ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Ether
  • 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 Point48 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.64 mg/mL at 20 °CNot Available
LogP2.27Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.37 g/LALOGPS
logP2.05ALOGPS
logP1.82ChemAxon
logS-2.1ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity44.55 m³·mol⁻¹ChemAxon
Polarizability17.21 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014r-6900000000-ea0c740f9da9c4c70539Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-4900000000-d64fd9a65666e73ced8aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kr-0900000000-3abbfda2a2e2a801ab8cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014r-6900000000-ea0c740f9da9c4c70539Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-4900000000-d64fd9a65666e73ced8aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kr-0900000000-3abbfda2a2e2a801ab8cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-2900000000-4554a3b4e1d463b0fd5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-5d1c09395418f0c2133eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-90fdb37cd3a74b33d68cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059i-3900000000-d89eddffdff84dcc594fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-69f4cc8bf456108754a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-ce81d76af8ef0abfc0fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05n0-5900000000-1f91c2bab5730381aa5bSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB010588
KNApSAcK IDC00030761
Chemspider ID21108577
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8499
PDB IDNot Available
ChEBI ID86903
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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.. .