ETHYL ANTHRANILATE Property

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)

color 

Light yellow

Specific Gravity

1.1170

Odor

at 100.00 %. sweet floral grape orangeblossom wintergreen

Odor Type

floral

JECFA Number

1535

BRN 

878874

Stability:

Stable. Combustible. Incompatible with acids, bases, oxidizing agents.

LogP

2.57

CAS DataBase Reference

87-25-2(CAS DataBase Reference)

EPA Substance Registry System

Ethyl anthranilate (87-25-2)

Safety

Hazard Codes 

Xi

Risk Statements 

36/38

Safety Statements 

26-36

WGK Germany 

2

RTECS 

DG2448000

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29224999

Hazardous Substances Data

87-25-2(Hazardous Substances Data)

Toxicity

The acute oral LD₅₀ value in rats was reported as 3.75 g/kg (3.32-4.18 g/kg) and the acute dermal LD₅₀ value in rabbits exceeded 5 g/kg (Moreno, 1975).

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H303May be harmfulif swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

ETHYL ANTHRANILATE Chemical Properties,Usage,Production

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.

Uses

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

Uses

Perfumery and flavors, similar to methyl anthranilate.

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.