Anisic acid

Structural formula
General
Surname	Anisic acid
other names	4-methoxybenzoic acid p -methoxybenzoic acid P-ANISIC ACID ( INCI )
Molecular formula	C 8 H 8 O 3
Brief description	colorless crystal needles
External identifiers / databases
CAS number 100-09-4 EC number 202-818-5 ECHA InfoCard 100,002,562 PubChem 7478 ChemSpider 10181338 DrugBank DB02795 Wikidata Q4566032
properties
Molar mass	152.15 g mol −1
Physical state	firmly
density	1.39 g cm −3
Melting point	182-185 ° C
boiling point	277 ° C
pK s value	4.47
solubility	very bad in water (approx. 0.3 g l −1 at 20 ° C) soluble in methanol, ethanol, chloroform and diethyl ether
Refractive index	1.571-1.576
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
Toxicological data	> 5000 mg kg −1 ( LD 50 ,  rat ,  oral ) > 943 mg l −1 ( EC 50 ,  crustaceans , 48 h )
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

Anisic acid is a methoxylated benzoic acid , i.e. methoxybenzoic acid and thus both a carboxylic acid and an ether . In the German-language literature, the common name anisic acid is mainly used for 4-methoxybenzoic acid, while in the English-language literature the term anisic acid is used for all three isomers of methoxybenzoic acids. A distinction is made between o -anisic acid (2-methoxybenzoic acid), m -anisic acid (3-methoxybenzoic acid) and p -anisic acid (4-methoxybenzoic acid).

Occurrence

Anisic acid is found in small amounts in the oil of anise and other plants (e.g. vanilla ).

Extraction and presentation

Anisic acid is very easily accessible through the Grignard reaction of p-bromanisole with carbon dioxide. Anisic acid can also be obtained by oxidizing 4-methoxyacetophenone with hypobromite ( unicorn reaction ).

Another very simple synthesis of anisic acid is the oxidation of anisaldehyde with an oxidizing agent such as potassium permanganate .

use

Anisic acid is used for the production of anisic acid derivatives such. B. Dronedarone used. It has a bacteriostatic effect and was previously used as an antiseptic , anti-inflammatory drug and preservative .

safety instructions

The vapors of anisic acid can only form an explosive mixture with air at very high temperatures. The flash point is 185 ° C, the ignition temperature 185 ° C and the decomposition temperature> 400 ° C.

Individual evidence

1. ↑ Entry on P-ANISIC ACID in the CosIng database of the EU Commission, accessed on December 28, 2019.
2. ↑ ^{a b c d e f g} Entry on 4-methoxybenzoic acid in the GESTIS substance database of the IFA , accessed on December 22, 2019(JavaScript required) .
3. ↑ ^{a b} Entry on anisic acid at ChemBlink , accessed on December 22, 2019.
4. ↑ CRC Handbook of Tables for Organic Compound Identification , Third Edition, 1984, ISBN 0-8493-0303-6 .
5. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-330.
6. ↑ Data sheet anisic acid (PDF) from Carl Roth , accessed on February 14, 2010.
7. ↑ Liber Herbarum Minor: anisic acid.
8. ↑ Attempt to produce anisic acid. ( Memento of the original from June 17, 2009 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. (PDF; 32 kB) 
9. ↑ Patent EP0213340 : Process for the production of carboxylic acids. Registered on July 11, 1986 , published on May 2, 1991 , applicant: Dynamit Nobel AG, inventor: Marcel Feld. ‌
10. ↑ Patent CN101993427 : New method for preparing dronedarone. Filed August 26, 2009 , published October 10, 2012 . ‌