Anthranilic acid

Anthranilic acid
IUPAC name

2-aminobenzoic acid
Other names

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
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 is the organic compound with the formula C6H4(NH2)COOH. This amino acid is a white solid when pure, although commercial samples may appear yellow. The molecule consists of a benzene ring with two adjacent functional groups, a carboxylic acid and an amine. It is sometimes referred to as vitamin L. it has a sweetish taste, it is flammable and will produce nitrogen oxide fumes when burning, it may be sensitive to prolonged exposure to air and light.

Contents

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

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.[2]

It is also a DEA List I Chemical because of its use in making the now-widely outlawed euphoric sedative drug methaqualone (Quaalud, Mandrax).[3]

See also

References

  1. ^ IPCS
  2. ^ 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 
  3. ^ 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
K→acetyl-CoA
G
other
Other

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m(A16/C10),i(k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)
biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i