2-Aminoacetophenone

Chemical properties

2-Aminoacetophenone, also known as o-aminoacetophenone or 2-AA, is a yellow to yellow-brown liquid that has a grape-like odor. Aminoacetophenone is a pheromone produced by virgin honeybee queens and released in feces. The pheromone repels and is used to terminate agonistic interactions between queens and workers. A grape-like odor of 2-aminoacetophenone is of diagnostic importance in detecting the growth of Pseudomonas aeruginosa in culture and in burn wounds.

Occurrence

Reported present in chestnut honey (>154 ppb)*; green tea and wine (0.7 to 12.8 μg/L).

The Uses of 2-Aminoacetophenone

2′-Aminoacetophenone may be used as an analytical standard for the determination of the analyte in livestock particulate matter, and grape-derived beverages by gas chromatography-mass spectrometry-olfactometry (GC-MS-O) and GC-MS, respectively.

Definition

ChEBI: 2-Aminoacetophenone is an aromatic ketone that is acetophenone in which one of the ortho hydrogens of the phenyl group has been replaced by an amino group.

Preparation

Synthesis of 2-Aminoacetophenone by reaction of methyl lithium with Isatoic anhydride in an anhydrous or nearly anhydrous solvent at a reaction temperature of -50°C or less.

Synthesis Reference(s)

Journal of the American Chemical Society, 76, p. 4561, 1954 DOI: 10.1021/ja01647a016
Journal of Heterocyclic Chemistry, 24, p. 297, 1987 DOI: 10.1002/jhet.5570240201
Journal of the American Chemical Society, 105, p. 943, 1983 DOI: 10.1021/ja00342a050
The Journal of Organic Chemistry, 45, p. 4926, 1980 DOI: 10.1021/jo01312a021
The Journal of Organic Chemistry, 22, p. 358, 1957 DOI: 10.1021/jo01355a002

General Description

2′-Aminoacetophenone is one of the key volatile flavor components of masa corn flour products. It is also reported to be responsible for the grape-like odor in culture media growing Pseudomonas aeruginosa.