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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
o-aminobenzoic acid, 2-aminobenzoic acid, vitamin L1, Anthranilate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.898 Edit this at Wikidata
KEGG
  • 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
Appearance white or yellow solid
Density 1.4 g/cm3
Melting point 146–148 °C[1]
5.7 g/L (25 °C)
Solubility Hot water, ethanol and ether
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).
☒N verify (what is checkY☒N ?)

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

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