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HomeProduct name listETHYL ANTHRANILATE

ETHYL ANTHRANILATE

Synonym(s):Benzocaine impurity D (PhEur);Ethyl anthranilate

  • CAS NO.:87-25-2
  • Empirical Formula: C9H11NO2
  • Molecular Weight: 165.19
  • MDL number: MFCD00007711
  • EINECS: 201-735-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-24 21:11:45
ETHYL ANTHRANILATE Structural

What is ETHYL ANTHRANILATE?

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.

The Uses of ETHYL ANTHRANILATE

Perfumery and flavors, similar to methyl anthranilate.

The Uses of ETHYL ANTHRANILATE

Ethyl 2-aminobenzoate is used as a reactant in the amination of aryl chlorides, bromides, and triflates.

Preparation

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

Definition

ChEBI: Ethyl 2-aminobenzoate is a benzoate ester.

General Description

Colorless liquid with a fruity odor. Insoluble in water.

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.

Properties of ETHYL ANTHRANILATE

Melting point: 13-15 °C (lit.)
Boiling point: 129-130 °C/9 mmHg (lit.)
Density  1.117 g/mL at 25 °C (lit.)
vapor density  5.7 (vs air)
refractive index  n20/D 1.564(lit.)
FEMA  2421 | ETHYL ANTHRANILATE
Flash point: >230 °F
storage temp.  Keep in dark place,Inert atmosphere,Room temperature
solubility  Insoluble in water but soluble in organic solvents
form  Clear liquid
pka 2.20±0.10(Predicted)
Specific Gravity 1.1170
color  Light yellow
Odor at 100.00 %. sweet floral grape orangeblossom wintergreen
JECFA Number 1535
BRN  878874
Stability: Stable. Combustible. Incompatible with acids, bases, oxidizing agents.
CAS DataBase Reference 87-25-2(CAS DataBase Reference)
EPA Substance Registry System Ethyl anthranilate (87-25-2)

Safety information for ETHYL ANTHRANILATE

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H303:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for ETHYL ANTHRANILATE

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