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Anthranilic acid

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Anthranilic acid
Skeletal formula
Ball-and-stick model
Names
IUPAC name
2-aminobenzoic acid
Other names
vitamin L1, Anthranilate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.898 Edit this at Wikidata
  • InChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10) checkY
    Key: RWZYAGGXGHYGMB-UHFFFAOYSA-N checkY
  • InChI=1/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)
    Key: RWZYAGGXGHYGMB-UHFFFAOYAS
  • O=C(O)c1ccccc1N
  • c1ccc(c(c1)C(=O)O)N
Properties
C7H7NO2
Molar mass 137.138 g·mol−1
Density 1.4 g/cm3
Melting point 146–148 °C[1]
5.7 g/L (25 °C)
Solubility Hot water
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point >150 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Anthranilic acid is the organic compound with the formula C6H4(NH2)COOH. This amino acid is 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.

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 eg. 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". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 5, p. 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
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