Buy O-amino benzoic acid Cas 118-92-3

Buy O-amino benzoic acid Cas 118-92-3

Anthranilic acid is an aromatic acid with the formula C₆H₄(NH₂)(CO₂H) and has a sweetish taste.^[5][6][7] The molecule consists of a benzene ring, ortho-substituted with a carboxylic acid and an amine. As a result of containing both acidic and basic functional groups, the compound is amphoteric. Anthranilic acid is a white solid when pure, although commercial samples may appear yellow. The anion [C₆H₄(NH₂)(CO₂)]⁻, obtained by the deprotonation of anthranilic acid, is called anthranilate. Anthranilic acid was once thought to be a vitamin and was referred to as vitamin L₁ in that context, but it is now known to be non-essential in human nutrition. Buy O-amino benzoic acid Cas 118-92-3

Although not usually referred to as such, it is an amino acid. Solid anthranilic acid typically consists of both the amino-carboxylic acid and the zwitterionic ammonium carboxylate forms, and has a monoclinic crystal structure with space group P2₁.^[9] It is triboluminescent.^[10] Above 81 °C (178 °F; 354 K), it converts to an orthorhombic form with space group Pbca, which is not triboluminescent; a non-triboluminescent monoclinic phase with similar structure is also known. 

O-Aminobenzoic Acid Uses, Dosage, Side Effects and more

In 1840-1841, Carl Julius Fritzsche was able to extract and crystallize two acids from the products of reaction of indigo dye with caustic potash, which he called chrysanilic and anthranilic acids after their colors before purification (golden yellow and black respectively) and the plant anil (Indigofera suffruticosa).^[11][12] The former was identified as ortho-carboxy anil of indoxyl-2-aldehyde only in 1910^[13] while the latter was identified as salicylamide already in 1843 by Cahours.^[14]

Many routes to anthranilic acid have been described. Industrially it is produced from phthalic anhydride, beginning with amination:

C₆H₄(CO)₂O + NH₃ + NaOH → C₆H₄(C(O)NH₂)CO₂Na + H₂O

The resulting sodium salt of phthalamic acid is decarbonylated via a Hofmann rearrangement of the amide group, induced by hypochlorite:^[15]

C₆H₄(C(O)NH₂)CO₂Na + HOCl → C₆H₄NH₂CO₂H + NaCl + CO₂

A related method involves treating phthalimide with sodium hypobromite in aqueous sodium hydroxide, followed by neutralization.^[16] In the era when indigo dye was obtained from plants, it was degraded to give anthranilic acid.

Anthranilic acid was first obtained by base-induced degradation of indigo.^[17]

Anthranilic acid is biosynthesized from chorismic acid by the action of anthranilate synthase. In organisms capable of tryptophan synthesis, anthranilate is a precursor to the amino acid tryptophan via the attachment of phosphoribosyl pyrophosphate to the amine group. After then, cyclization occurs to produce indole.

Industrially, anthranilic acid is an intermediate in the production of azo dyes and saccharin. It and its esters are used in preparing perfumes to mimic jasmine and orange, pharmaceuticals (loop diuretics, such as furosemide) and UV-absorber as well as corrosion inhibitors for metals and mold inhibitors in soy sauce.

Anthranilate-based insect repellents have been proposed as replacements for DEET.

Fenamic acid is a derivative of anthranilic acid,^[18]: 235 which in turn is a nitrogen isostere of salicylic acid, which is the active metabolite of aspirin.^[18]: 235 Several non-steroidal anti-inflammatory drugs, including mefenamic acid, tolfenamic acid, flufenamic acid, and meclofenamic acid are derived from fenamic acid or anthranilic acid and are called “anthranilic acid derivatives” or “fenamates”.