551-93-9

Chemical Properties

2?-Aminoacetophenone 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).

Uses

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ChEBI: An aromatic ketone that is acetophenone in which one of the ortho hydrogens of the phenyl group has been replaced by an amino group.

Synthesis Reference(s)

Journal of the American Chemical Society, 76, p. 4561, 1954 DOI: 10.1021/ja01647a016Journal of Heterocyclic Chemistry, 24, p. 297, 1987 DOI: 10.1002/jhet.5570240201Journal of the American Chemical Society, 105, p. 943, 1983 DOI: 10.1021/ja00342a050The Journal of Organic Chemistry, 45, p. 4926, 1980 DOI: 10.1021/jo01312a021The 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.{9] It is also reported to be responsible for the grape-like odor in culture media growing Pseudomonas aeruginosa.

Who Evaluation

Evaluation year: 2012

Consumer Uses

ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.