Showing Compound Methyl anthranilate (FDB000897)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:45 UTC

Update date

2020-09-17 15:35:28 UTC

Primary ID

FDB000897

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Methyl anthranilate

Description

Methyl 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 Number

134-20-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-(Methoxycarbonyl)aniline	ChEBI
2-Aminobenzoic acid methyl ester	ChEBI
2-Carbomethoxyaniline	ChEBI
Anthranilic acid methyl ester	ChEBI
Methyl O-aminobenzoate	ChEBI
O-Aminobenzoic acid methyl ester	ChEBI
O-Carbomethoxyaniline	ChEBI
O-Methyl anthranilate	ChEBI
2-Aminobenzoate methyl ester	Generator
Anthranilate methyl ester	Generator
Methyl O-aminobenzoic acid	Generator
O-Aminobenzoate methyl ester	Generator
O-Methyl anthranilic acid	Generator
Methyl 2-aminobenzoic acid	Generator
Carbomethoxyaniline	HMDB
FEMA 2682	HMDB
Methyl ester OF O-aminobenzoic acid	HMDB
O-amino Methyl benzoate	HMDB
Methyl anthranilic acid	Generator
Methyl 2-aminobenzoate	db_source
Methyl anthranilate	manual
o-Amino methyl benzoate	biospider

Predicted Properties

Property	Value	Source
Water Solubility	5.07 g/L	ALOGPS
logP	1.6	ALOGPS
logP	1.8	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	19.4	ChemAxon
pKa (Strongest Basic)	2.12	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	42.78 m³·mol⁻¹	ChemAxon
Polarizability	15.22 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C8H9NO2

IUPAC name

methyl 2-aminobenzoate

InChI Identifier

InChI=1S/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3

InChI Key

VAMXMNNIEUEQDV-UHFFFAOYSA-N

Isomeric SMILES

COC(=O)C1=CC=CC=C1N

Average Molecular Weight

151.1626

Monoisotopic Molecular Weight

151.063328537

Classification

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

benzoate ester (CHEBI:73244 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Flavoring agent

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 63.57%; H 6.00%; N 9.27%; O 21.17%	DFC
Melting Point	Mp 24-25°	DFC
Boiling Point	Bp15 133.5°	DFC
Experimental Water Solubility	2.85 mg/mL at 25 oC	BEILSTEIN
Experimental logP	1.88	HANSCH,C ET AL. (1995)
Experimental pKa	pKa 2.32 (25°, 1% EtOH aq.)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Methyl anthranilate, non-derivatized, GC-MS Spectrum	splash10-014l-9700000000-dfe3727f600ad4c1a3fc	Spectrum
GC-MS	Methyl anthranilate, non-derivatized, GC-MS Spectrum	splash10-0gb9-4900000000-aadfdb770e0e737f8b6a	Spectrum
GC-MS	Methyl anthranilate, non-derivatized, GC-MS Spectrum	splash10-014l-9700000000-dfe3727f600ad4c1a3fc	Spectrum
GC-MS	Methyl anthranilate, non-derivatized, GC-MS Spectrum	splash10-0gb9-4900000000-aadfdb770e0e737f8b6a	Spectrum
Predicted GC-MS	Methyl anthranilate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-6900000000-cbb0e5d181285b3afaaa	Spectrum
Predicted GC-MS	Methyl anthranilate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-00di-0900000000-47d3bade84c5e4931d1c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-00di-0900000000-185dd522a1fc548b72b8	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-00di-2900000000-edbf763056e8c72de031	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-00di-3900000000-80e68c81bbbd6961e056	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-00dl-7900000000-f4d89a4912bba552a83c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-006x-9500000000-4073b13420f4b0056e90	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-00r6-9300000000-c45c4c69c1883e3f44ee	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-00kf-9100000000-d3ce7a6d45c89cf32c04	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-014l-9000000000-c093597fba151c4609c7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 33V, positive	splash10-014l-9000000000-6de4e61444f60c359ad8	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 35V, positive	splash10-014i-9000000000-0fd51fb715e0e72a65d3	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-014i-9000000000-b2a65db09df351a67eca	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 45V, positive	splash10-014i-9000000000-597af6cb6895ca445830	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 3V, positive	splash10-00di-0900000000-6b7e5480efd4530cb476	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-00di-0900000000-653b9ca77b6a92b0559b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-00di-0900000000-3b4c970d594e7e84da2f	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-0udi-0900000000-472f1d1c5d63a30785c4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-0udi-0900000000-e5870501e95fd449a7bd	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-0uk9-0900000000-dcb6e65cc8cfb2f974ca	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-8f28628545d92d6eba85	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uk9-2900000000-2eab000fe93ae5bfde36	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gi3-9100000000-56145c723f7acb283fee	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-53f5c61d1ffff7e9c43e	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-5ddd8e2bdd8ab9a9f5f9	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9700000000-5b947aa002295f2ebfae	2016-08-04	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

13858096

ChEMBL ID

CHEMBL1493986

KEGG Compound ID

Not Available

Pubchem Compound ID

8635

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB29703

CRC / DFC (Dictionary of Food Compounds) ID

BLS86-X:BLS88-Z

EAFUS ID

2250

Dr. Duke ID

ANTHRANILIC-ACID-METHYL-ESTER

BIGG ID

Not Available

KNApSAcK ID

C00034600

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

134-20-3

GoodScent ID

rw1008211

SuperScent ID

8635

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
honey	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	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	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
lime	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
grapefruit	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
strawberry	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
medicinal	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
fruity	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
grape	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
orange flower	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
neroli	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter	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