Anthranilic acid
| Anthranilic acid | |
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2-aminobenzoic acid |
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Other names
vitamin L1, Anthranilate |
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| Identifiers | |
| CAS number | 118-92-3  |
| ChemSpider | 222 |
| DrugBank | DB04166 |
| KEGG | C00108 |
| ChEBI | CHEBI:30754 |
| ChEMBL | CHEMBL14173 |
| Jmol-3D images | Image 1 Image 2 |
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| 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
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| Flash point | >150 °C |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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.
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[edit] 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.
[edit] 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]
[edit] See also
[edit] References
- ^ IPCS
- ^ 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
- ^ 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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