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Methyl anthranilate, also known as MA, methyl 2-aminobenzoate, or carbomethoxyaniline, is an ester of anthranilic acid. Its chemical formula is C 8 H 9 NO 2 . It has a strong and fruity grape smell, and one of its key uses is as a flavoring agent.
Anthranilate-based insect repellents include methyl anthranilate, N,N-dimethylanthranilic acid (DMA), ethyl anthranilate (EA), and butyl anthranilate (BA).
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.
Anthranilate synthase catalyzes the change from chorismate to anthranilate. As its other substrate, it can use either glutamine or ammonia. [1] During the reaction, both a hydroxyl group and an enolpyruvyl group are removed from the aromatic ring. The enolpyruvyl group gains a proton to form pyruvate.
N-Acetylanthranilic acid is an organic compound with the molecular formula C 9 H 9 NO 3.It is an intermediate product in catabolism of quinaldine in Arthrobacter sp., and is further metabolized to anthranilic acid.
The United States Drug Enforcement Administration (DEA) maintains lists regarding the classification of illicit drugs (see DEA Schedules).It also maintains List I of chemicals and List II of chemicals, which contain chemicals that are used to manufacture the controlled substances/illicit drugs.
Hydrolysis gives carbon dioxide and anthranilic acid. Alcoholysis proceeds similarly, affording the ester: C 6 H 4 C 2 O 3 NH + ROH → C 6 H 4 (CO 2 R)(NH 2) + CO 2. Amines also effect ring-opening.
The malonic ester synthesis is a chemical reaction where diethyl malonate or another ester of malonic acid is alkylated at the carbon alpha (directly adjacent) to both carbonyl groups, and then converted to a substituted acetic acid.