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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:50:56 UTC
Update Date2023-02-21 17:22:33 UTC
HMDB IDHMDB0032639
Secondary Accession Numbers
  • HMDB32639
Metabolite Identification
Common NameMethyl 4-methoxybenzoate
DescriptionMethyl 4-methoxybenzoate, also known as 4-methoxy methylbenzoate or methyl 4-anisate, 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 a sweet, anise, and balsam tasting compound. Methyl 4-methoxybenzoate is found, on average, in the highest concentration within star anises (Illicium verum). This could make methyl 4-methoxybenzoate a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Methyl 4-methoxybenzoate.
Structure
Data?1677000153
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, MeSH
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
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point48 °CNot Available
Boiling Point244.00 to 245.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.64 mg/mL at 20 °CNot Available
LogP2.27Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+137.85331661259
DarkChem[M-H]-137.42831661259
DeepCCS[M+H]+136.76630932474
DeepCCS[M-H]-133.49930932474
DeepCCS[M-2H]-170.59530932474
DeepCCS[M+Na]+146.13430932474
AllCCS[M+H]+135.432859911
AllCCS[M+H-H2O]+131.032859911
AllCCS[M+NH4]+139.532859911
AllCCS[M+Na]+140.732859911
AllCCS[M-H]-135.632859911
AllCCS[M+Na-2H]-136.732859911
AllCCS[M+HCOO]-138.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Methyl 4-methoxybenzoateCOC(=O)C1=CC=C(OC)C=C12098.6Standard polar33892256
Methyl 4-methoxybenzoateCOC(=O)C1=CC=C(OC)C=C11340.4Standard non polar33892256
Methyl 4-methoxybenzoateCOC(=O)C1=CC=C(OC)C=C11393.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methyl 4-methoxybenzoate EI-B (Non-derivatized)splash10-014r-6900000000-ea0c740f9da9c4c705392017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl 4-methoxybenzoate EI-B (Non-derivatized)splash10-000i-4900000000-d64fd9a65666e73ced8a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl 4-methoxybenzoate EI-B (Non-derivatized)splash10-00kr-0900000000-3abbfda2a2e2a801ab8c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl 4-methoxybenzoate EI-B (Non-derivatized)splash10-014r-6900000000-ea0c740f9da9c4c705392018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl 4-methoxybenzoate EI-B (Non-derivatized)splash10-000i-4900000000-d64fd9a65666e73ced8a2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl 4-methoxybenzoate EI-B (Non-derivatized)splash10-00kr-0900000000-3abbfda2a2e2a801ab8c2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl 4-methoxybenzoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-2900000000-4554a3b4e1d463b0fd5e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl 4-methoxybenzoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 10V, Positive-QTOFsplash10-014i-0900000000-5d1c09395418f0c2133e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 20V, Positive-QTOFsplash10-014i-0900000000-90fdb37cd3a74b33d68c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 40V, Positive-QTOFsplash10-059i-3900000000-d89eddffdff84dcc594f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 10V, Negative-QTOFsplash10-014i-0900000000-69f4cc8bf456108754a42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 20V, Negative-QTOFsplash10-014i-0900000000-ce81d76af8ef0abfc0fd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 40V, Negative-QTOFsplash10-05n0-5900000000-1f91c2bab5730381aa5b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 10V, Positive-QTOFsplash10-066r-0900000000-acee10ded01e8444992f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 20V, Positive-QTOFsplash10-052r-1900000000-b7caaa239ca1956148ef2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 40V, Positive-QTOFsplash10-114r-9400000000-0bbc122fec993ec920172021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 10V, Negative-QTOFsplash10-014i-0900000000-5dea0e2df5cd18252bf02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 20V, Negative-QTOFsplash10-0aor-0900000000-d21fad1db4d47d8572ad2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 40V, Negative-QTOFsplash10-0btc-9100000000-f077fac91afffdb6eb742021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
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 IDNot Available
Good Scents IDrw1032091
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.. .