Anthranilic acid

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Anthranilic acid
IUPAC name	2-aminobenzoic acid
Other names	vitamin L1, Anthranilate
Identifiers
CAS number	[118-92-3]
Properties
Molecular formula	C7H7NO2
Molar mass	137.136 g/mol
Density	1.4 g/cm3
Melting point	146-148 °C
Boiling point	Sublimes[1]
Solubility in water	0.6 g/L
Solubility	Hot water
Hazards
MSDS	External (html)
R-phrases	R36 R37
S-phrases	S26 S39
Flash point	>150 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Anthranilic acid is the organic compound with the formula C₆H₄(NH₂)CO₂H. 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. Because these two groups are polar, this organic compound is highly soluble in water. It is sometimes referred to as vitamin L.

Contents 1 Biological role 2 Uses 3 See also 4 References

[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 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]

[edit] See also

• Kynureninase

[edit] References

1. ^ IPCS
2. ^ Logullo, F. M.; Seitz, A. H.; Friedman, L. (1973). "Benzenediazonium-2-carboxy- and Biphenylene". Org. Synth.; Coll. Vol. 5: 54. 

v • d • e Amino acid metabolism intermediates K→acetyl-CoA lysine→ Saccharopine - Allysine - Alpha-aminoadipate - Alpha-ketoadipic acid - Glutaryl-CoA - Glutaconyl-CoA - Crotonyl-CoA - Beta-hydroxybutyryl-CoA leucine→ Alpha-ketoisocaproic acid - Isovaleryl-CoA - 3-Methylcrotonyl-CoA - 3-Methylglutaconyl-CoA - HMG-CoA tryptophan→alanine→ N'-Formylkynurenine - Kynurenine - Anthranilic acid - 3-hydroxykynurenine - 3-Hydroxyanthranilic acid - 2-Amino-3-carboxymuconic semialdehyde - 2-aminomuconic semialdehyde - 2-Aminomuconic acid - Glutaryl-CoA G→glutamate histidine→ Urocanic acid - Imidazol-4-one-5-propionic acid - Formiminoglutamic acid - Glutamate-1-semialdehyde proline→ 1-Pyrroline-5-carboxylic acid arginine→ Ornithine - Putrescine - Agmatine G→propionyl-CoA methionine→ S-Adenosyl methionine - S-Adenosyl-L-homocysteine - Homocysteine - Cystathionine - alpha-Ketobutyric acid isoleucine→ 2,3-Dihydroxy-3-methylpentanoic acid - 2-Methylbutyryl-CoA - Tiglyl-CoA - 2-methylacetoacetyl-CoA valine→ Alpha-ketoisovalerate - Isobutyryl-CoA - Methacrylyl-CoA - 3-Hydroxyisobutyryl-CoA - 3-Hydroxyisobutyrate - 2-methyl-3-oxopropanoate threonine→ Alpha-ketobutyric acid propionyl-CoA→ Methylmalonyl-CoA G→fumarate phenylalanine→tyrosine→ 4-Hydroxyphenylpyruvic acid - Homogentisic acid - 4-Maleylacetoacetate Other cysteine+glutamate→glutathione gamma-Glutamylcysteine glycine→creatine Glycocyamine - Phosphocreatine - Creatinine Other Glycerate 3-phosphate (serine) - Cysteine sulfinic acid see also enzymes, disorders