In organic chemistry, an oxime is an organic compound belonging to the imines, with the general formula RR’C=N−OH, where R is an organic side-chain and R' may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O-substituted oximes form a closely related family of compounds. Amidoximes are oximes of amides (R1C(=O)NR2R3) with general structure R1C(=NOH)NR2R3.
Oximes are usually generated by the reaction of hydroxylamine with aldehydes (R−CH=O) or ketones (RR’C=O). The term oxime dates back to the 19th century, a combination of the words oxygen and imine.[1]
^The name "oxime" is derived from "oximide" (i.e., oxy- + amide). According to the German organic chemist Victor Meyer (1848–1897) – who, with Alois Janny, synthesized the first oximes – an "oximide" was an organic compound containing the group (=N−OH) attached to a carbon atom. The existence of oximides was questioned at the time (ca. 1882). (See page 1164 of: Victor Meyer und Alois Janny (1882a) "Ueber stickstoffhaltige Acetonderivate" (On nitrogenous derivatives of acetone), Berichte der Deutschen chemischen Gesellschaft, 15: 1164–1167.) However, in 1882, Meyer and Janny succeeded in synthesizing methylglyoxime (CH3C(=NOH)CH(=NOH)), which they named "Acetoximsäure" (acetoximic acid) (Meyer & Janny, 1882a, p. 1166). Subsequently, they synthesized 2-propanone, oxime ((CH3)2C=NOH), which they named "Acetoxim" (acetoxime), in analogy with Acetoximsäure. From Victor Meyer and Alois Janny (1882b) "Ueber die Einwirkung von Hydroxylamin auf Aceton" (On the effect of hydroxylamine on acetone), Berichte der Deutschen chemischen Gesellschaft, 15: 1324–1326, page 1324: "Die Substanz, welche wir, wegen ihrer nahen Beziehungen zur Acetoximsäure, und da sie keine sauren Eigenschaften besitzt, vorläufig Acetoxim nennen wollen, …" (The substance, which we – on account of its close relations to acetoximic acid, and since it possesses no acid properties – will, for the present, name "acetoxime," … )
In organic chemistry, an oxime is an organic compound belonging to the imines, with the general formula RR’C=N−OH, where R is an organic side-chain and...
Phosgene oxime, or CX, is an organic compound with the formula Cl2C=N−OH. It is a potent chemical weapon, specifically a nettle agent. The compound itself...
Milbemycin oxime, sold under the brand name Interceptor among others, is a veterinary medication from the group of milbemycins, used as a broad spectrum...
Cyclohexanone oxime is an organic compound containing the functional group oxime. This colorless solid is an important intermediate in the production of...
Benzaldehyde oxime is an organic compound with the formula C7H7NO. Benzaldehyde oxime can be synthesized from benzaldehyde and hydroxylamine hydrochloride...
Methylethyl ketone oxime is the organic compound with the formula C2H5C(NOH)CH3. This colourless liquid is the oxime derivative of methyl ethyl ketone...
Progesterone oxime, or progesterone monoxime, is an oxime conjugate of progesterone and may refer to: Progesterone 3-oxime (3-(hydroxyimino)pregn-4-en-3-one)...
Chloroacetophenone oxime is the oxime derivative of chloroacetophenone. It's produced by reaction of chloroacetophenone with hydroxylamine. It has powerful...
Acetone oxime (acetoxime) is the organic compound with the formula (CH3)2CNOH. It is the simplest example of a ketoxime. It is a white crystalline solid...
synthesised from cyclohexanone (1), which is first converted to its oxime (2). Treatment of this oxime with acid induces the Beckmann rearrangement to give caprolactam...
an oxime functional group to substituted amides. The rearrangement has also been successfully performed on haloimines and nitrones. Cyclic oximes and...
progestogen oximes have not been marketed: EIDD-036 (progesterone 20-oxime; P4-20-O) EIDD-1723 (progesterone 20E-[O-[(phosphonooxy)methyl]oxime] sodium salt)...
(Z)-phenylacetaldehyde oxime ⇌ {\displaystyle \rightleftharpoons } phenylacetonitrile + H2O Hence, this enzyme has one substrate, (Z)-phenylacetaldehyde oxime, and two...
substrate for ethyl nitrite. Alkyl nitrites are also used in the formation of oximes with the stronger carbon acids and acid or base catalysis for example in...
across the trisubstituted double bond. This species is then converted to the oxime with a base, and the hydroxylamine is removed to give the ketone-containing...
sanguineus). It is taken by mouth. Lotilaner in combination with milbemycin oxime is sold under the brand name Credelio Plus. It is used in dogs to treat...
Oxime V is a chemical compound that has been studied as a potential sweetener. Oxime V was first reported in 1976 as a synthetic analog of the artificial...
being self-limiting and of short duration, (in combination with milbemycin oxime): vomiting, diarrhea, lethargy, anorexia, and pruritus were observed in...
hydroxylamine is used in the synthesis of cyclohexanone oxime, a precursor to Nylon 6. The treatment of this oxime with acid induces the Beckmann rearrangement to...
abstraction, free radical recombination, and tautomerization to form an oxime. Selectivity for the δ-hydrogen is a result of the conformation of the 6-membered...
cyclohexanone supply is converted to cyclohexanone oxime. In the presence of sulfuric acid catalyst, the oxime rearranges to caprolactam, a precursor to nylon...
include ivermectin (trade names Stromectol, Ivermec and others) or milbemycin oxime (Interceptor) for heartworms, imidacloprid and moxidectin (Advocate), fipronil...
pyruvate oxime + acetone ⇌ {\displaystyle \rightleftharpoons } pyruvate + acetone oxime Thus, the two substrates of this enzyme are pyruvate oxime and acetone...
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