Record Information
Version1.0
Creation date2010-04-08 22:04:45 UTC
Update date2020-09-17 15:35:28 UTC
Primary IDFDB000897
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMethyl anthranilate
DescriptionMethyl anthranilate or Methyl 2-aminobenzoate, also known as 2-carbomethoxyaniline, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Methyl anthranilate is a moderately basic compound (based on its pKa). It has a fruity grape smell, and one of its key uses is as a flavoring agent. 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. Methyl anthranilate is known to occur naturally in the Concord grapes and other Vitis labrusca grapes and hybrids thereof. It has also been detected in bergamot, black locust, champak, gardenia, jasmine, lemon, mandarin orange, neroli, oranges, rue oil, strawberry, tuberose, wisteria, galangal, and ylang ylang. It is also a primary component of the essential apple flavor, along with ethyl acetate and ethyl butyrate. Methyl anthranilate is used extensively in modern perfumery.
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSMethyl anthranilate, non-derivatized, GC-MS Spectrumsplash10-014l-9700000000-dfe3727f600ad4c1a3fcSpectrum
GC-MSMethyl anthranilate, non-derivatized, GC-MS Spectrumsplash10-0gb9-4900000000-aadfdb770e0e737f8b6aSpectrum
GC-MSMethyl anthranilate, non-derivatized, GC-MS Spectrumsplash10-014l-9700000000-dfe3727f600ad4c1a3fcSpectrum
GC-MSMethyl anthranilate, non-derivatized, GC-MS Spectrumsplash10-0gb9-4900000000-aadfdb770e0e737f8b6aSpectrum
Predicted GC-MSMethyl anthranilate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-6900000000-cbb0e5d181285b3afaaaSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-00di-0900000000-47d3bade84c5e4931d1cSpectrum
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-00di-0900000000-185dd522a1fc548b72b8Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-00di-2900000000-edbf763056e8c72de031Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-00di-3900000000-80e68c81bbbd6961e056Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-00dl-7900000000-f4d89a4912bba552a83cSpectrum
MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-006x-9500000000-4073b13420f4b0056e90Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-00r6-9300000000-c45c4c69c1883e3f44eeSpectrum
MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-00kf-9100000000-d3ce7a6d45c89cf32c04Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-014l-9000000000-c093597fba151c4609c7Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-014l-9000000000-6de4e61444f60c359ad8Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-014i-9000000000-0fd51fb715e0e72a65d3Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-014i-9000000000-b2a65db09df351a67ecaSpectrum
MS/MSLC-MS/MS Spectrum - QTOF 45V, positivesplash10-014i-9000000000-597af6cb6895ca445830Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 3V, positivesplash10-00di-0900000000-6b7e5480efd4530cb476Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-00di-0900000000-653b9ca77b6a92b0559bSpectrum
MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-00di-0900000000-3b4c970d594e7e84da2fSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0udi-0900000000-472f1d1c5d63a30785c4Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0udi-0900000000-e5870501e95fd449a7bdSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0uk9-0900000000-dcb6e65cc8cfb2f974caSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-8f28628545d92d6eba85Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-2900000000-2eab000fe93ae5bfde36Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gi3-9100000000-56145c723f7acb283feeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-53f5c61d1ffff7e9c43eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-5ddd8e2bdd8ab9a9f5f9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9700000000-5b947aa002295f2ebfaeSpectrum
NMRNot Available
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).