Anthranilic acid

Anthranilic acid
	C=black, H=white, O=red, N=blue
Names
	Preferred IUPAC name 2-Aminobenzoic acid
	Systematic IUPAC name 2-Aminobenzenecarboxylic acid
	Other names Anthranilic acid; o-Aminobenzoic acid; 2-Aminobenzoic acid; Vitamin L1; Anthranilate (conjugate base); 2-AA, 2AA, AA;
Identifiers
CAS Number	118-92-3 ;
3D model (JSmol)	Interactive image;
3DMet	B00027;
Beilstein Reference	471803
ChEBI	CHEBI:30754 ;
ChEMBL	ChEMBL14173 ;
ChemSpider	222 ;
DrugBank	DB04166 ;
ECHA InfoCard	100.003.898
EC Number	204-287-5;
Gmelin Reference	3397
KEGG	C00108 ;
PubChem CID	227;
RTECS number	CB2450000;
UNII	0YS975XI6W;
CompTox Dashboard (EPA)	DTXSID8020094 ;
	InChI InChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10) Key: RWZYAGGXGHYGMB-UHFFFAOYSA-N ; InChI=1/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10) Key: RWZYAGGXGHYGMB-UHFFFAOYAS;
	SMILES O=C(O)c1ccccc1N;
Properties
Chemical formula	C7H7NO2
Molar mass	137.138 g·mol−1
Appearance	white or yellow solid
Odor	odorless
Density	1.412 g/cm3
Melting point	146 to 148 °C (295 to 298 °F; 419 to 421 K)
Boiling point	200 °C (392 °F; 473 K) (sublimes)
Solubility in water	0.572 g/100 mL (25 °C)
Solubility	very soluble in chloroform, pyridine ; soluble in ethanol, ether, ethyl ether ; slightly soluble in trifluoroacetic acid, benzene
log P	1.21
Vapor pressure	0.1 Pa (52.6 °C)
Acidity (pKa)	2.17 (amino; H2O); 4.85 (carboxyl; H2O);
Magnetic susceptibility (χ)	-77.18·10−6 cm3/mol
Refractive index (nD)	1.578 (144 °C)
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	-380.4 KJ/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H318, H319
Precautionary statements	P264, P280, P305+P351+P338, P310, P337+P313
NFPA 704 (fire diamond)	2 1 0
Flash point	> 150 °C (302 °F; 423 K)
Autoignition; temperature	> 530 °C (986 °F; 803 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	1400 mg/kg (oral, rat)
Safety data sheet (SDS)	External MSDS
Legal status	BR: Class D1 (Drug precursors);
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Anthranilic acid is an aromatic acid with the formula C₆H₄(NH₂)(CO₂H) and has a sweetish taste.^[5]^[6]^[7] The molecule consists of a benzene ring, ortho-substituted with a carboxylic acid and an amine. As a result of containing both acidic and basic functional groups, the compound is amphoteric. Anthranilic acid is a white solid when pure, although commercial samples may appear yellow. The anion [C₆H₄(NH₂)(CO₂)]⁻, obtained by the deprotonation of anthranilic acid, is called anthranilate. Anthranilic acid was once thought to be a vitamin and was referred to as vitamin L₁ in that context, but it is now known to be non-essential in human nutrition.^[8]

^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 748. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.
^ IPCS
^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
^ Acton, Q. Ashton (2013). Aminobenzoic Acids—Advances in Research and Application (2013 ed.). Atlanta: ScholarlyEditions. p. 23. ISBN 9781481684842 – via Google Books.
^ Hardy, Mark R. (1997). "Glycan Labeling with the Flurophores 2-Aminobenzamide and Antranilic Acid". In Townsend, R. Reid; Hotchkiss, Arland T. Jr. (eds.). Techniques in Glycobiology. Marcel Dekker, Inc. p. 360. ISBN 9780824798222 – via Google Books.
^ The Merck Index, 10th Ed. (1983), p.62., Rahway: Merck & Co.
^ Davidson, Michael W. (2004). "Anthranilic Acid (Vitamin L)]". Florida State University. Retrieved November 20, 2019.

[iupac2013-1] "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 748. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[CRC97-2] Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.

[3] IPCS

[4] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.

[5] Acton, Q. Ashton (2013). Aminobenzoic Acids—Advances in Research and Application (2013 ed.). Atlanta: ScholarlyEditions. p. 23. ISBN 9781481684842 – via Google Books.

[6] Hardy, Mark R. (1997). "Glycan Labeling with the Flurophores 2-Aminobenzamide and Antranilic Acid". In Townsend, R. Reid; Hotchkiss, Arland T. Jr. (eds.). Techniques in Glycobiology. Marcel Dekker, Inc. p. 360. ISBN 9780824798222 – via Google Books.

[7] The Merck Index, 10th Ed. (1983), p.62., Rahway: Merck & Co.

[8] Davidson, Michael W. (2004). "Anthranilic Acid (Vitamin L)]". Florida State University. Retrieved November 20, 2019.

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