4-Aminophenylacetic acid

Chemical properties

light yellow to beige powder. Soluble in alcohols and alkalis, slightly soluble in hot water.

The Uses of 4-Aminophenylacetic acid

4-Aminophenylacetic acid, is used as a non-translocated competitive inhibitor of the epithelial peptide transporter PepT1. It can be detected using HPLC, NMR techniques.

Preparation

p-aminophenylacetic acid is obtained by the reduction of 4-nitrophenylacetic acid. In a reactor, water, 4-nitrophenylacetic acid, and acetic acid are added. The mixture is stirred and heated to 90-95℃. Iron powder is added in portions and refluxed for 2 hours. The mixture is cooled to 40-50℃ and neutralized with sodium carbonate to pH=9, then filtered. The filtrate is further neutralized with acetic acid until pH=4, resulting in the precipitation of 4-aminophenylacetic acid. The yield is 95%.

Benefits

4-Aminophenylacetonitrile (4-APAN) is an arylacetonitrile and an active substrate for arylacetonitrilase, which gives 4-aminophenylacetic acid (4-APAA) on hydrolysis. 4-APAA is a precursor of 4-acetylaminophenylacetic acid, used in treating rheumatoid arthritis and actarit drugs. 4-APAA also possesses tuberculostatic activity and is helpful as a fibrinolysis inhibitor. In addition to the medical importance of this acid, several derivatives and compounds obtained from 4-APAA showed antimicrobial activity[1].

Purification Methods

Crystallise the acid from hot water (60-70mL/g). [Beilstein 14 III 1182.]

References

[1] BEDAIRAHMED H. Preparation of 4-aminophenylacetic acid derivatives with promising antimicrobial activity.[J]. Acta Pharmaceutica, 2006, 56 3: 273-284.
[2] MENGYIFAN ZareRichard N GnanamaniElumalai. One-Step Formation of Pharmaceuticals Having a Phenylacetic Acid Core Using Water Microdroplets.[J]. Journal of the American Chemical Society, 2023, 145 14: 7724-7728. DOI:10.1021/jacs.3c00773.

References

[1] Neerja Thakur. “Bioprocess Development for the Synthesis of 4-Aminophenylacetic Acid Using Nitrilase Activity of Whole Cells of Alcaligenes faecalis MTCC 12629.” Catalysis Letters 149 10 (2019): 2854–2863.