Anthranilic acid

Anthranilic acid
IUPAC name 2-aminobenzoic acid
Other names o-aminobenzoic acid, 2-aminobenzoic acid, vitamin L1, Anthranilate
Identifiers
CAS number	118-92-3 Y
ChemSpider	222 Y
DrugBank	DB04166
KEGG	C00108 Y
ChEBI	CHEBI:30754 Y
ChEMBL	CHEMBL14173 Y
Jmol-3D images	Image 1 Image 2
SMILES O=C(O)c1ccccc1N c1ccc(c(c1)C(=O)O)N
InChI InChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10) Y Key: RWZYAGGXGHYGMB-UHFFFAOYSA-N Y InChI=1/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10) Key: RWZYAGGXGHYGMB-UHFFFAOYAS
Properties
Molecular formula	C7H7NO2
Molar mass	137.14 g mol−1
Appearance	white or yellow solid
Density	1.4 g/cm3
Melting point	146–148 °C[1]
Solubility in water	5.7 g/L (25 °C)
Solubility	Hot water, ethanol and ether
Hazards
MSDS	External MSDS
R-phrases	R36 R37
S-phrases	S26 S39
NFPA 704	1 2 0
Flash point	>150 °C
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Anthranilic acid (or o-amino-benzoic acid) is an organic compound with the molecular formula C₇H₇NO₂. The molecule consists of a benzene ring, hence is classed as aromatic, with two adjacent, or "ortho-" functional groups, a carboxylic acid and an amine. The compound is consequently amphoteric, although it is not usually referred to as an amino-acid. In appearance, anthranilic acid is a white solid when pure, although commercial samples may appear yellow. It may be sensitive to prolonged exposure to air and light. It is flammable and will produce nitrogen oxide fumes when burning.

It is sometimes referred to as vitamin L₁, and has a sweetish taste^[2]

Synthesis

There are many different ways to make anthranilic acid. One method is by treating phthalimide with sodium hypobromite in aqueous sodium hydroxide, followed by neutralization.^[3]

Biological role

Anthranilic acid is biosynthesized from chorismic acid. It is the precursor to the amino acid tryptophan via the attachment of phosphoribosyl pyrophosphate to the amine group.

Uses

Industrially, anthranilic acid is used as an intermediate for production of dyes, pigments, and saccharin. It and its esters are used in preparing perfumes to imitate jasmine and orange, pharmaceuticals (loop diuretics e.g. furosemide) and UV-absorber as well as corrosion inhibitors for metals and mold inhibitors in soya sauce.

Anthranilic acid can be used in organic synthesis to generate the benzyne intermediate.^[4]

It is also a DEA List I Chemical because of its use in making the now-widely outlawed euphoric sedative drug methaqualone (Quaalude, Mandrax).^[5]

See also

• Kynureninase

References

1. ^ IPCS
2. ^ The Merck Index, 10th Ed. (1983), p.62., Rahway: Merck & Co.
3. ^ Vogel's Textbook of Practical Organic Chemistry, 4th Ed., (B. S. Furniss et al., Eds.) (1978), p.666, London: Longman.
4. ^ Logullo, F. M.; Seitz, A. H.; Friedman, L. (1973), "Benzenediazonium-2-carboxy- and Biphenylene", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv5p0054 ; Coll. Vol. 5: 54 
5. ^ Angelos SA, Meyers JA. The isolation and identification of precursors and reaction products in the clandestine manufacture of methaqualone and mecloqualone. Journal of Forensic Sciences. 1985 Oct;30(4):1022-47. PMID 3840834