Record Information
Version1.0
Creation date2010-04-08 22:09:12 UTC
Update date2018-01-23 19:10:11 UTC
Primary IDFDB010588
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMethyl 4-methoxybenzoate
DescriptionMethyl 4-methoxybenzoate, also known as p-anisic acid methyl ester or 4-methoxy methylbenzoate, 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. Methyl 4-methoxybenzoate is found, on average, in the highest concentration in star anises. Methyl 4-methoxybenzoate has also been detected, but not quantified in, . This could make methyl 4-methoxybenzoate a potential biomarker for the consumption of these foods.
CAS Number121-98-2
Structure
Thumb
Synonyms
SynonymSource
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
4-methoxy methylbenzoatebiospider
Methyl 4-methoxybenzoatedb_source
Methyl ester of p-methoxybenzoic acidbiospider
P-anisic acid methyl esterbiospider
P-anisic acid, methyl esterbiospider
P-methoxybenzoic acid methyl esterbiospider
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H10O3
IUPAC namemethyl 4-methoxybenzoate
InChI IdentifierInChI=1S/C9H10O3/c1-11-8-5-3-7(4-6-8)9(10)12-2/h3-6H,1-2H3
InChI KeyDDIZAANNODHTRB-UHFFFAOYSA-N
Isomeric SMILESCOC(=O)C1=CC=C(OC)C=C1
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 65.05%; H 6.07%; O 28.88%DFC
Melting PointMp 48°DFC
Boiling PointBp20 160°DFC
Experimental Water Solubility0.643 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP2.27HANSCH,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)splash10-014r-6900000000-ea0c740f9da9c4c70539JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-4900000000-d64fd9a65666e73ced8aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kr-0900000000-3abbfda2a2e2a801ab8cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014r-6900000000-ea0c740f9da9c4c70539JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-4900000000-d64fd9a65666e73ced8aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kr-0900000000-3abbfda2a2e2a801ab8cJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-2900000000-4554a3b4e1d463b0fd5eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-5d1c09395418f0c2133eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-90fdb37cd3a74b33d68cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059i-3900000000-d89eddffdff84dcc594fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-69f4cc8bf456108754a4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-ce81d76af8ef0abfc0fdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05n0-5900000000-1f91c2bab5730381aa5bJSpectraViewer
ChemSpider ID21108577
ChEMBL IDCHEMBL1762668
KEGG Compound IDNot Available
Pubchem Compound ID8499
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB32639
CRC / DFC (Dictionary of Food Compounds) IDFFR17-A:FFR18-B
EAFUS ID2247
Dr. Duke IDMETHYL-ANISATE
BIGG IDNot Available
KNApSAcK IDC00030761
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1032091
SuperScent ID8499
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 / Bioactivities
DescriptorIDDefinitionReference
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
anise
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
balsam
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
melon
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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).