Record Information
Version1.0
Creation date2010-04-08 22:04:45 UTC
Update date2019-11-26 02:55:36 UTC
Primary IDFDB000897
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMethyl anthranilate
DescriptionMethyl 2-aminobenzoate, also known as 2-carbomethoxyaniline or 2-(methoxycarbonyl)aniline, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Methyl 2-aminobenzoate is a moderately basic compound (based on its pKa). Methyl 2-aminobenzoate is a bitter, flower, and fruity tasting compound. Methyl 2-aminobenzoate has been detected, but not quantified in, several different foods, such as tea, fruits, limes, cereals and cereal products, and cocoa and cocoa products. This could make methyl 2-aminobenzoate a potential biomarker for the consumption of these foods.
CAS Number134-20-3
Structure
Thumb
Synonyms
SynonymSource
2-(Methoxycarbonyl)anilineChEBI
2-Aminobenzoic acid methyl esterChEBI
2-CarbomethoxyanilineChEBI
Anthranilic acid methyl esterChEBI
Methyl O-aminobenzoateChEBI
O-Aminobenzoic acid methyl esterChEBI
O-CarbomethoxyanilineChEBI
O-Methyl anthranilateChEBI
2-Aminobenzoate methyl esterGenerator
Anthranilate methyl esterGenerator
Methyl O-aminobenzoic acidGenerator
O-Aminobenzoate methyl esterGenerator
O-Methyl anthranilic acidGenerator
Methyl 2-aminobenzoic acidGenerator
CarbomethoxyanilineHMDB
FEMA 2682HMDB
Methyl ester OF O-aminobenzoic acidHMDB
O-Amino methyl benzoateHMDB
Methyl anthranilic acidGenerator
Methyl 2-aminobenzoatedb_source
Methyl anthranilatemanual
o-Amino methyl benzoatebiospider
Predicted Properties
PropertyValueSource
Water Solubility5.07 g/LALOGPS
logP1.6ALOGPS
logP1.8ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)19.4ChemAxon
pKa (Strongest Basic)2.12ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.78 m³·mol⁻¹ChemAxon
Polarizability15.22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC8H9NO2
IUPAC namemethyl 2-aminobenzoate
InChI IdentifierInChI=1S/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3
InChI KeyVAMXMNNIEUEQDV-UHFFFAOYSA-N
Isomeric SMILESCOC(=O)C1=CC=CC=C1N
Average Molecular Weight151.1626
Monoisotopic Molecular Weight151.063328537
Classification
Description belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Aminobenzoic acid or derivatives
  • Benzoate ester
  • Benzoyl
  • Aniline or substituted anilines
  • Vinylogous amide
  • Methyl ester
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • 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 stateLiquid
Physical DescriptionNot Available
Mass CompositionC 63.57%; H 6.00%; N 9.27%; O 21.17%DFC
Melting PointMp 24-25°DFC
Boiling PointBp15 133.5°DFC
Experimental Water Solubility2.85 mg/mL at 25 oCBEILSTEIN
Experimental logP1.88HANSCH,C ET AL. (1995)
Experimental pKapKa 2.32 (25°, 1% EtOH aq.)DFC
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)splash10-014l-9700000000-dfe3727f600ad4c1a3fcJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gb9-4900000000-aadfdb770e0e737f8b6aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9700000000-dfe3727f600ad4c1a3fcJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gb9-4900000000-aadfdb770e0e737f8b6aJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-6900000000-cbb0e5d181285b3afaaaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-8f28628545d92d6eba85JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-2900000000-2eab000fe93ae5bfde36JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gi3-9100000000-56145c723f7acb283feeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-53f5c61d1ffff7e9c43eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-5ddd8e2bdd8ab9a9f5f9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9700000000-5b947aa002295f2ebfaeJSpectraViewer
ChemSpider ID13858096
ChEMBL IDCHEMBL1493986
KEGG Compound IDNot Available
Pubchem Compound ID8635
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29703
CRC / DFC (Dictionary of Food Compounds) IDBLS86-X:BLS88-Z
EAFUS ID2250
Dr. Duke IDANTHRANILIC-ACID-METHYL-ESTER
BIGG IDNot Available
KNApSAcK IDC00034600
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID134-20-3
GoodScent IDrw1008211
SuperScent ID8635
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
honey
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
flower
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
lemon
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
lime
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
grapefruit
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
strawberry
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
medicinal
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
grape
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
orange flower
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
neroli
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).