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Chemical Compound Review:

PubChem21792 1-(2-aminophenyl)ethanone

Synonyms: SureCN309044, NSC-8820, A37804_ALDRICH, AG-K-87016, ACMC-209zid, ...

Zhao, G. et al., Karagül-Yüceer, Y. et al., Hoenicke, K. et al., Hoenicke, K. et al., Page, R.E. et al., et al.

Hoenicke, Simat, Steinhart, Christoph, Köhler, Schwab,

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Disease relevance of NSC8820

Use of 2-aminoacetophenone production in identification of Pseudomonas aeruginosa [1].
Transformation of 2-aminoacetophenone to ( S) -2-amino-1-phenylethanol by Arthrobacter sulfureus [2].

High impact information on NSC8820

Results of AEDA indicated o-aminoacetophenone to be a potent odorant; however, sensory descriptive sensory analysis of model aroma systems revealed that the typical odor of rennet casein was principally caused by hexanoic acid, indole, guaiacol, and p-cresol [3].
Tryptophan (Trp) and its metabolites, especially indole-3-acetic acid (IAA), are considered to be potential precursors of 2-aminoacetophenone (AAP), an aroma compound that causes an "untypical aging off-flavor" (UTA) in Vitis vinifera wines [4].
A new isolate of Arthrobacter sulfureus , when incubated at 50 g resting cells (dry cell wt) l(-1) with 50 g glucose l(-1) and 1 g 2-aminoacetophenone l(-1) in 50 mm potassium buffer (pH 7, 4 ml) at 30 degrees C, produced ( S )-2-amino-1-phenylethanol (e.e. >99%) with 75% yield in 6 h [2].
Tryptophan (Trp) and its metabolites, especially indole-3-acetic acid (IAA), are considered as potential precursors of 2-aminoacetophenone (AAP), an aroma compound which causes the "untypical aging off-flavor" (UTA) in Vitis vinifera white wines [5].
o-Aminoacetophenone is a pheromone produced by virgin honeybee queens and released with feces [6].

References

Use of 2-aminoacetophenone production in identification of Pseudomonas aeruginosa. Cox, C.D., Parker, J. J. Clin. Microbiol. (1979) [Pubmed]
Transformation of 2-aminoacetophenone to ( S) -2-amino-1-phenylethanol by Arthrobacter sulfureus. Zhao, G., Wang, J., Ma, K., Yang, L., Wu, S., Liu, Y., Sun, W. Biotechnol. Lett. (2004) [Pubmed]
Characteristic aroma components of rennet casein. Karagül-Yüceer, Y., Vlahovich, K.N., Drake, M., Cadwallader, K.R. J. Agric. Food Chem. (2003) [Pubmed]
Determination of free and conjugated indole-3-acetic acid, tryptophan, and tryptophan metabolites in grape must and wine. Hoenicke, K., Simat, T.J., Steinhart, H., Köhler, H.J., Schwab, A. J. Agric. Food Chem. (2001) [Pubmed]
Determination of tryptophan and tryptophan metabolites in grape must and wine. Hoenicke, K., Simat, T.J., Steinhart, H., Christoph, N., Köhler, H.J., Schwab, A. Adv. Exp. Med. Biol. (1999) [Pubmed]
o-Aminoacetophenone, a pheromone that repels honeybees (Apis mellifera L.). Page, R.E., Blum, M.S., Fales, H.M. Experientia (1988) [Pubmed]

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