General Description
Colorless liquid with a fruity odor. Insoluble in water.
Reactivity Profile
ETHYL ANTHRANILATE(87-25-2) may hydrolyze under acidic and basic conditions.
Air & Water Reactions
This compound should be protected from air and light. Insoluble in water.
Fire Hazard
Flash point data for this chemical are not available. ETHYL ANTHRANILATE is probably combustible.
Chemical Properties
colourless liquid
Chemical Properties
Ethyl anthranilate has a faint, orange-flower odor and similar taste.
Occurrence
Reported found in grapes, orange juice, orange peel oil, starfruit and Vitis labrusca L.
Definition
ChEBI: Ethyl 2-aminobenzoate is a benzoate ester.
Preparation
By esterification of anthranilic acid with ethanol in the presence of acid catalysts; by reacting sodium hypochlorite with
an alkaline solution of phthalimide
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).
