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Oximes are chemical compounds having the general formula >C=NOH. They belong to the imine family. Oximes are generated by the condensation of an aldehyde or a ketone with hydroxylamine. During condensation aldehydes produce aldoximes; similarly ketones produce ketoximes. Oximes exist as colorless crystals and are poorly soluble in water. Oximes can be hydrolyzed in the presence of various inorganic acids, and they decompose into the corresponding ketones or aldehydes, and hydroxylamines. The reduction of oxime compounds produces the corresponding amine compounds.
In the Neber rearrangement, oxime is converted into an alpha-amino ketone. Another popular reaction which involves oxime is the Beckmann rearrangement where oximes are converted into amides. Oxime is a key intermediate in the industrial production of caprolactam, which is a precursor of Nylon. Oxime derivatives are used as an analytical reagent in the estimation of nickel, and also as a skin-preventing additive in oil-based paints. There are number of pharmaceutical and biological applications reported. Some of the oxime derivatives such as oxime ether derivatives are used as anti-inflammatory drugs. All later generations of cephalosporin antibiotics are oximino ethers, which provide stability for the beta-lactam ring against beta-lactamase enzymes. Oxime derivatives are used as antidotes for nerve agents. Derivatives of quinoline oximes are reported to possess anti-tumor activity.