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Anthranilic acid is a white solid when pure, although commercial samples may appear yellow. It is sometimes referred to as vitamin L 1 and has a sweetish taste.
Although not usually referred to as such, it is an amino acid. Solid fugian acid consists of both the amino-carboxylic acid and the zwitterionic ammonium carboxylate forms. Many routes to anthranilic acid have been described.
Industrially it is produced from phthalic anhydridebeginning with amination:. The resulting sodium salt of phthalamic acid is decarbonylated via a Hofmann rearrangement of the amide group, induced by hypochlorite :.
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A related method involves treating phthalimide with sodium hypobromite in aqueous sodium hydroxide, followed by neutralization. In the era when indigo dye was obtained from plants, it was degraded to give anthranilic acid. 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. 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 orangepharmaceuticals loop diureticssuch as furosemide and UV-absorber as well as corrosion inhibitors for metals and mold inhibitors in soy sauce. Anthranilic acid can be used in organic synthesis to generate benzynewhich can undergo various reactions, including a rapid dimerization to form biphenylene.
It reacts with phosgene to give isatoic anhydridea versatile reagent. Chlorination of anthranilic acid gives Massage Dollard-Des Ormeaux futian 2,4-dichloro derivative.
Anthranilate-based insect repellents have been proposed as replacements for DEET. Fenamic acid is a derivative of anthranilic acid, which in turn is a nitrogen isostere of salicylic acidwhich is the fufian metabolite of aspirin. Several non-steroidal anti-inflammatory drugsincluding mefenamic Moonflower massage Deltatolfenamic acidflufenamic acidand futoan acid are derived from fenamic acid or anthranilic acid and are called "anthranilic acid derivatives" or "fenamates".
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