87-25-2

Preparation

By esterification of anthranilic acid with ethanol in the presence of acid catalysts; by reacting sodium hypochlorite with an alkaline solution of phthalimide

Air & Water Reactions

ETHYL ANTHRANILATE should be protected from air and light. Insoluble in water.

Reactivity Profile

ETHYL ANTHRANILATE may hydrolyze under acidic and basic conditions.

Fire Hazard

Flash point data for ETHYL ANTHRANILATE are not available. ETHYL ANTHRANILATE is probably combustible.

Pharmacology

Ethyl anthranilate behaved as a local anaesthetic, as measured by depression of muscle twitch, but was 50% less effective than the m- and p-aminobenzoate isomers. All three compounds potentiated the initial phase of caffeine-induced contracture of frog sartorius muscle, but the o-isomer had no effect on the peak tension of the contracture (Friedman, Bianchi & Weiss. 1974). It was proposed that the o-amino group has both steric and polar effects, its bulk preventing the inhibitory action of the carbonyl group on the caffeine-induced contracture of sartorius muscle, while the lone electron pair of the nitrogen atom induces a contracture on its own accord and potentiates a caffeine-induced contracture (Friedman, 1975). Ethyl anthranilate (0-1 mmol/litre) decreased the frequency of the electric-organ discharges of the electric fish, Gnathonemus moori, but did not affect the individual pulse amplitudes, indicating that the compound acted on the pacemaker cells of the mesencephalic command nucleus (Walsh & Schopp, 1966).

Safety Profile

Moderately toxic by ingestion. A skin irritant. Combustible liquid. When heated to decomposition it emits toxic fumes of NOx.

General Description

Colorless liquid with a fruity odor. Insoluble in water.