acetone oxime
N-hydroxy-2-propanimine
Identification
| Name | acetone oxime |
| IUPAC | N-propan-2-ylidenehydroxylamine |
| CAS Number | 127-06-0 |
| EINECS | 204-820-1 |
| FDA UNII | QX74TFD64T |
| Molecular Formula | C3 H7 N O |
| Molecular Weight | 73.09499000 |
| Nikkaji Number | J2.515A |
| Beilstein | 1560146 |
| XlogP3 | 0.10 (est) |
Regulatory
Physical Properties
| Appearance | white powder (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 61.00 °C. @ 760.00 mm Hg |
| Boiling Point | 136.00 °C. @ 760.00 mm Hg, 134.00 to 135.00 °C. @ 760.00 mm Hg (est) |
| Vapor Pressure | 3.120000 mmHg @ 25.00 °C. (est) |
| Flash Point | 113.00 °F. TCC ( 45.20 °C. ) (est) |
| logP (o/w) | 0.120 |
| Soluble in | water, 1.06e+005 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD50 4000 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | information only not used for fragrances or flavors |
| Recommendation for acetone oxime usage levels up to | not for fragrance use. |
| Recommendation for acetone oxime flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
acetone, oxime
acetoneoxime
acetonoxime
acetoxime
N-
hydroxy-2-propanimine
N-
hydroxypropan-2-imine
b-iso
nitrosopropane
beta-iso
nitrosopropane
propan-2-one oxime
N-
propan-2-ylidene hydroxyl amine
N-
propan-2-ylidenehydroxylamine
2-
propanone oxime
2-
propanoneoxime
servon XACT 100
PubMed:
GSK-3? activation is required for ZIP-induced disruption of learned fear
PubMed:
Antiherpetic potential of 6-bromoindirubin-3'-acetoxime (BIO-acetoxime) in human oral epithelial cells
PubMed:
Identification of GSK-3 as a Potential Therapeutic Entry Point for Epilepsy
PubMed:
Amination of tyrosine in liver cytosol protein of male F344 rats treated with 2-nitropropane, 2-nitrobutane, 3-nitropentane, or acetoxime
PubMed:
Palladium(II)-Catalyzed Acetoxime Directed ortho-Arylation of Aromatic Alcohols
PubMed:
Oxidation of the ketoxime acetoxime to nitric oxide by oxygen radical-generating systems
PubMed:
Palladium-catalyzed direct mono-aroylation of O-arylmethyl and aryl-substituted acetoxime ethers
PubMed:
Reversion of structure-activity relationships of antitumor platinum complexes by acetoxime but not hydroxylamine ligands
PubMed:
Sex and organ differences in oxidative DNA and RNA damage due to treatment of Sprague-Dawley rats with acetoxime or 2-nitropropane
PubMed:
Slow oxidation of acetoxime and methylethyl ketoxime to the corresponding nitronates and hydroxy nitronates by liver microsomes from rats, mice, and humans
PubMed:
Mixed unsymmetric oxadiazoline and/or imine platinum(II) complexes
PubMed:
An evaluation of indirubin analogues as phosphorylase kinase inhibitors
PubMed:
Vasorelaxant activity of some oxime derivatives
PubMed:
Rapid analysis of acetone in human plasma by derivatization desorption electrospray ionization
PubMed:
Synthesis and anti-inflammatory activity of novel (substituted)benzylidene acetone oxime ether derivatives: molecular modeling study
PubMed:
Induction of hyperplastic liver nodules in Wistar and MRC-Wistar rats by phenobarbital and the liver carcinogens acetoxime, 1-nitroso-5,6-dihydrouracil and 3-nitroso-2-oxazolidinone
PubMed:
Direct ortho-C-H functionalization of aromatic alcohols masked by acetone oxime ether via exo-palladacycle
PubMed:
Glycogen synthase kinase-3 plays a central role in mediating glucocorticoid-induced apoptosis
PubMed:
Acetoxime is metabolized by human and rodent hepatic cytochrome P450 enzymes to the genotoxicant and carcinogen propane 2-nitronate
PubMed:
Fine-Tuning of the RIG-I-Like Receptor/Interferon Regulatory Factor 3-Dependent Antiviral Innate Immune Response by the Glycogen Synthase Kinase 3/?-Catenin Pathway
PubMed:
Relaxant effect of oxime derivatives in isolated rat aorta: role of nitric oxide (NO) formation in smooth muscle
PubMed:
Determination of acetone in human breath by gas chromatography-mass spectrometry and solid-phase microextraction with on-fiber derivatization
PubMed:
Oxidative DNA and RNA damage in rat liver due to acetoxime: similarity to effects of 2-nitropropane
PubMed:
H/D isotopic and temperature effects in the polarized IR spectra of hydrogen-bond cyclic trimers in the crystal lattices of acetone oxime and 3,5-dimethylpyrazole
PubMed:
Photodissociation dynamics of acetoxime in gas phase
PubMed:
Synthesis of 3,5-isoxazolidinediones and 1H-2,3-benzoxazine-1,4(3H)-diones from aliphatic oximes and dicarboxylic acid chlorides
PubMed:
6-Br-5methylindirubin-3'oxime (5-Me-6-BIO) targeting the leishmanial glycogen synthase kinase-3 (GSK-3) short form affects cell-cycle progression and induces apoptosis-like death: exploitation of GSK-3 for tre
PubMed:
Synthesis, Structures, and Photocurrent Responses of Polyoxo-Titanium Clusters with Oxime Ligands: From Ti(4) to Ti(18)
PubMed:
Activation of n-3 polyunsaturated fatty acids as oxime esters: a novel approach for their exclusive incorporation into the primary alcoholic positions of the glycerol moiety by lipase
PubMed:
Nitrate formation during ozonation as a surrogate parameter for abatement of micropollutants and the N-nitrosodimethylamine (NDMA) formation potential
PubMed:
GSK3 inhibitors regulate MYCN mRNA levels and reduce neuroblastoma cell viability through multiple mechanisms, including p53 and Wnt signaling
PubMed:
Cellular accumulation and DNA interaction studies of cytotoxic trans-platinum anticancer compounds
PubMed:
Chimeric 5/35 adenovirus-mediated Dickkopf-1 overexpression suppressed tumorigenicity of CD44? gastric cancer cells via attenuating Wnt signaling
PubMed:
Oximate-substituted zirconium alkoxides
PubMed:
Nitroreduction is not involved in the genotoxicity of 2-nitropropane in cultured mammalian cells
PubMed:
Lipoamide dehydrogenase and diaphorase catalyzed conversion of some NO donors to NO and reduction of NO scavenger 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide (PTIO)
PubMed:
Fast and low-temperature sintering of silver complex using oximes as a potential reducing agent for solution-processible, highly conductive electrodes
PubMed:
Selective C(sp(3) )-H and C(sp(2) )-H Fluorination of Alcohols Using Practical Auxiliaries
PubMed:
Studies on the acetylation and NMR reassignment of indirubin derivatives
PubMed:
Inhibition of copper amine oxidases by pyridine-derived aldoximes and ketoximes
PubMed:
Vapor-phase Beckmann rearrangement of oxime molecules over H-Faujasite zeolite
PubMed:
Apposition of silica lamellae during growth of spicules in the demosponge Suberites domuncula: biological/biochemical studies and chemical/biomimetical confirmation
PubMed:
Rapid determination of acetone in human plasma by gas chromatography-mass spectrometry and solid-phase microextraction with on-fiber derivatization
PubMed:
Investigation of the chemical basis of nitroalkane toxicity: tautomerism and decomposition of propane 1- and 2-nitronate under physiological conditions
PubMed:
Synthesis, antifungal activities, and potential detoxification of N-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)thiocarbamates
PubMed:
Rapid determination of acetone in human blood by derivatization with pentafluorobenzyl hydroxylamine followed by headspace liquid-phase microextraction and gas chromatography/mass spectrometry
PubMed:
E/Z Energetics for Molecular Modeling and Design
PubMed:
Carcinogenicity test of acetoxime in MRC-Wistar rats
PubMed:
Genotoxicity of N-nitroso-N-methylurea and acetone oxime in the transgenic Drosophila carrying the human gene encoding a subunit of glutathione S-transferase
PubMed:
Nitrite formation from hydroxylamine and oximes by Pseudomonas aeruginosa
PubMed:
Novel quantum mechanical/molecular mechanical method combined with the theory of energy representation: free energy calculation for the Beckmann rearrangement promoted by proton transfers in the supercritical
PubMed:
Reaction mechanism of an intramolecular oxime transfer reaction: a computational study
PubMed:
Is the Beckmann rearrangement a concerted or stepwise reaction? A computational study
PubMed:
Sulfotransferase-mediated genotoxicity of propane 2-nitronate in cultured ovine seminal vesicle cells
PubMed:
Theoretical and experimental study of 15N NMR protonation shifts
PubMed:
Activation of propane 2-nitronate to a genotoxicant in V79-derived cell lines engineered for the expression of rat hepatic sulfotransferases
PubMed:
Comparison of kinetic properties of amine oxidases from sainfoin and lentil and immunochemical characterization of copper/quinoprotein amine oxidases
PubMed:
The formation of silkworm virus by acetoxime feeding
PubMed:
Ab initio molecular electrostatic potentials of perillartine analogues: implications for sweet-taste receptor recognition
PubMed:
Human phenol sulfotransferases hP-PST and hM-PST activate propane 2-nitronate to a genotoxicant
PubMed:
Aluminum compounds containing eta1- and/or eta5-bidentate dianionic pyrrolyl-methylamide ligands
PubMed:
An Intramolecular Nitrone-Olefin Dipolar Cycloaddition-Based Approach to Total Synthesis of the Cylindricine and Lepadiformine Marine Alkaloids
PubMed:
Pt(II)-mediated imine-nitrile coupling leading to symmetrical (1,3,5,7,9-pentaazanona-1,3,6,8-tetraenato)Pt(II) complexes containing the incorporated 1,3-diiminoisoindoline moiety
PubMed:
Synthesis and beta-adrenergic blocking activity of new aliphatic oxime ethers
PubMed:
Preparation of beta- and gamma-lactams from carbamoyl radicals derived from oxime oxalate amides
PubMed:
Regulation of endothelin-1 expression in normal and transfected endothelial cells
PubMed:
Prophage induction in lysogenic Escherichia coli with simple hydroxylamine and hydrazine compounds
PubMed:
Gas chromatographic-mass spectrometric analysis of hydroxylamine for monitoring the metabolic hydrolysis of metalloprotease inhibitors in rat and human liver microsomes
PubMed:
[Electrochemical reduction of (R)-1- hydroxyl-1-(m-hydroxylphenyl)-acetone oxime--a new method of preparing metaraminol (author's transl)]
PubMed:
[Structure of adducts prepared from nicotinamide adenine dinucleotide and their oximes]