Anthranilic acid methyl ester

Structural formula
General
Surname	Anthranilic acid methyl ester
other names	2-aminobenzoic acid methyl ester Methyl anthranilate
Molecular formula	C 8 H 9 NO 2
Brief description	colorless to yellowish solid with a fruity odor
External identifiers / databases
CAS number 134-20-3 EC number 205-132-4 ECHA InfoCard 100,004,667 PubChem 8635 Wikidata Q420894
properties
Molar mass	151.16 g mol −1
Physical state	firmly
density	1.17 g cm −3 (25 ° C)
Melting point	24 ° C
boiling point	256 ° C
Vapor pressure	<300 hPa (50 ° C)
solubility	heavy in water (2.79 g l −1 at 23 ° C)
Refractive index	1.5824 (20 ° C, 589 nm)
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 319 P: 305 + 351 + 338
Toxicological data	2910 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Anthranilic acid methyl ester is a chemical compound from the group of carboxylic acid esters and aminobenzenes .

Occurrence

The compound occurs naturally in cocoa, coffee, grapes, grapefruit, jasmine, lemons, limes, strawberries and mandarins as well as in many flower oils (e.g. neroli , ylang-ylang oil ).

Extraction and presentation

Anthranilic acid methyl ester can be prepared by esterifying anthranilic acid with methanol or by reacting isatoic anhydride with methanol.

properties

It is a flammable, colorless to yellowish solid with a fruity odor that is sparingly soluble in water. The substance is liquid or solid, depending on the room temperature, whereby a contaminated product can also be liquid at lower temperatures. Its aqueous solution has a pH of 7.5–8 (20 ° C). It shows a bluish fluorescence under UV light.

Anthranilic acid methyl ester forms flammable vapor-air mixtures at higher temperatures. The compound has a flash point of 123 ° C. The ignition temperature is 530 ° C. The substance therefore falls into temperature class T1.

use

Anthranilic acid methyl ester is used as a perfume for ointments and for the production of synthetic fragrances. It is used in a wide variety of flower perfumes. However, its use in perfumes for soaps and cosmetics is limited because it causes discoloration. It is used in aromatic compositions (e.g. in grape and citrus aromas). It also serves as a starting material in the synthesis of the active pharmaceutical ingredient benzydamine .

Individual evidence

1. ↑ ^{a b c d e f g h i j k l} Entry on methyl anthranilate in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
2. ↑ ^{a b c} Data sheet of anthranilic acid methyl ester (PDF) from Merck , accessed on April 9, 2012.
3. ↑ Data sheet Methyl anthranilate, natural (US), ≥ 98% from Sigma-Aldrich , accessed on April 9, 2012 ( PDF ).
4. ↑ ^{a b c} Ullmann's Encyclopedia of Industrial Chemistry - Flavors and Fragrances - doi : 10.1002 / 14356007.a11_141 .
5. ↑ ^{a b} Entry on Methyl anthranilate in the Hazardous Substances Data Bank , accessed July 27, 2012.
6. ^ A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th edition (2001) Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 .