|
| | ETHYL ANTHRANILATE Basic information |
| Product Name: | ETHYL ANTHRANILATE | | Synonyms: | FEMA 2421;ETHYL ANTHRANILATE;ETHYL O-AMINOBENZOATE;ETHYL 2-AMINOBENZOATE;2-AMINOBENZOIC ACID ETHYL ESTER;ethyl-o-amino;o-(Ethoxycarbonyl)aniline;o-aminobenzoicacid,ethylester | | CAS: | 87-25-2 | | MF: | C9H11NO2 | | MW: | 165.19 | | EINECS: | 201-735-1 | | Product Categories: | Aromatic Esters | | Mol File: | 87-25-2.mol |  |
| | ETHYL ANTHRANILATE Chemical Properties |
| 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) | | FEMA | 2421 | ETHYL ANTHRANILATE | | refractive index | n20/D 1.564(lit.) | | Fp | >230 °F | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | solubility | Insoluble in water but soluble in organic solvents | | pka | 2.20±0.10(Predicted) | | form | Clear liquid | | 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) |
| 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). |
| | ETHYL ANTHRANILATE Usage And Synthesis |
| 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. |
| | ETHYL ANTHRANILATE Preparation Products And Raw materials |
| Raw materials | Sodium hypochlorite-->Anthranilic acid-->DIALIFOS | | Preparation Products | Bentazone-->1,2-DIHYDRO-4-HYDROXY-2-OXO-3-QUINOLINECARBOXYLIC ACID ETHYL ESTER-->4-CHLORO-2-CHLOROMETHYLQUINAZOLINE-->2-ETHOXYCARBONYLPHENYL ISOTHIOCYANATE-->1H-[1]-BENZAZEPHE-2,5(3H, 4H)-DIONE-->4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER-->2-[(4-ETHOXY-1,4-DIOXOBUTYL)AMINO]BENZOIC ACID ETHYL ESTER-->Purino[8,7-b]quinazoline-2,4,6(1H,3H,11H)-trione, 1,3-dimethyl- (9CI)-->ethyl N-salicyloylanthranilate |
|
