Cyclohexanone oxime is a white, crystalline compound that is a key intermediate in the synthesis of caprolactam, a precursor to nylon-6. It is also used in the synthesis of other important chemicals, such as cyclohexanone, caproic acid, and adipic acid. Cyclohexanone oxime can be synthesized by reacting cyclohexanone with hydroxylamine. It has been studied for its potential applications in various fields, including organic synthesis, medicine, and materials science. Its importance arises from its versatile reactivity and the ability to undergo various transformations, leading to the formation of useful products.'
| ID Source | ID |
|---|---|
| PubMed CID | 7517 |
| CHEMBL ID | 137035 |
| SCHEMBL ID | 37995 |
| MeSH ID | M0130355 |
| Synonym |
|---|
| HMS1787F13 |
| n-cyclohexylidene-hydroxylamine |
| cyclohexanone oxime |
| (hydroxyimino)cyclohexane |
| cyclohexanone, oxime |
| 100-64-1 |
| wln: l6ytj aunq |
| nsc-6300 |
| nsc6300 |
| cyclo-hexanone, oxime |
| inchi=1/c6h11no/c8-7-6-4-2-1-3-5-6/h8h,1-5h |
| NCGC00091157-01 |
| nsc 6300 |
| einecs 202-874-0 |
| brn 1616769 |
| ccris 1383 |
| hsdb 5337 |
| ai3-07288 |
| cyclohexanone oxime, 97% |
| CHEMBL137035 |
| n-hydroxycyclohexanimine |
| STL069070 |
| n-cyclohexylidenehydroxylamine |
| AKOS000121564 |
| A800249 |
| NCGC00091157-02 |
| 4-07-00-00021 (beilstein handbook reference) |
| ec 202-874-0 |
| 2u60l00cgf , |
| unii-2u60l00cgf |
| dtxsid4021842 , |
| dtxcid701842 |
| cas-100-64-1 |
| tox21_303015 |
| NCGC00256578-01 |
| tox21_202143 |
| NCGC00259692-01 |
| (hydroxyimino)cyclohexane [hsdb] |
| hydroxyiminocyclohexane |
| SCHEMBL37995 |
| W-108950 |
| F1723-0300 |
| mfcd00001660 |
| cyclohexanone oxime, vetec(tm) reagent grade, 97% |
| cyclohexanoneoxime |
| E73607 |
| AS-14695 |
| Q1147519 |
| benzenepropanoic acid, 3-chloro-.alpha.-oxo- |
| cyclohexanone oxime;cyclohexanone, oxime;n-hydroxycyclohexanimine;cyclohexanone oxime cyclohexanone, oxime n-hydroxycyclohexanimine |
| EN300-15690 |
| SY011165 |
| cyclohexanoneoxime(chunks or pellets) |
| cyclohexan-1-one oxime |
| Z49568468 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " The toxic effects appear reversible upon cessation of exposure." | ( Toxicity of cyclohexanone oxime. I. Hematotoxicity following subacute exposure in rats. Babich, PC; Derelanko, MJ; Gad, SC; Gavigan, F; Mulder, S; Powers, WJ, 1985) | 0.65 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " All animals given intermediate dose levels (10, 25, 75, and 150 mg/kg) and one half of the animals which were dosed at the high dose (300 mg/kg) as well as one half of the controls were terminated 14 days after administration of the first dose." | ( Toxicity of cyclohexanone oxime. I. Hematotoxicity following subacute exposure in rats. Babich, PC; Derelanko, MJ; Gad, SC; Gavigan, F; Mulder, S; Powers, WJ, 1985) | 0.65 |
| "8, 2, and 5 g/kg caused dose-related reticulocytosis on the day after dosing as well as a decrease in hemoglobin in the 5-g/kg females 7 days postdosing." | ( Toxicity of cyclohexanone oxime. II. Acute dermal and subchronic oral studies. Babich, PC; Derelanko, MJ; Gad, SC; Gavigan, F; Mulder, S; Powers, WJ, 1985) | 0.65 |
| " Half of the animals from each group were euthanized at the end of the dosing schedule and the remaining animals were euthanized after a recovery period." | ( Analysis of rat bone marrow by flow cytometry following in vivo exposure to cyclohexanone oxime or daunomycin HCl. Amacher, DE; Clemo, FA; Schomaker, SJ, 2002) | 0.54 |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASE | Homo sapiens (human) | Potency | 2.2387 | 0.0032 | 45.4673 | 12,589.2998 | AID2517 |
| hypoxia-inducible factor 1 alpha subunit | Homo sapiens (human) | Potency | 54.9410 | 3.1890 | 29.8841 | 59.4836 | AID1224846 |
| GLI family zinc finger 3 | Homo sapiens (human) | Potency | 34.0811 | 0.0007 | 14.5928 | 83.7951 | AID1259369; AID1259392 |
| thyroid stimulating hormone receptor | Homo sapiens (human) | Potency | 0.0100 | 0.0013 | 18.0743 | 39.8107 | AID926; AID938 |
| glucocorticoid receptor [Homo sapiens] | Homo sapiens (human) | Potency | 0.0631 | 0.0002 | 14.3764 | 60.0339 | AID588532 |
| retinoic acid nuclear receptor alpha variant 1 | Homo sapiens (human) | Potency | 33.5796 | 0.0030 | 41.6115 | 22,387.1992 | AID1159552; AID1159553; AID1159555 |
| retinoid X nuclear receptor alpha | Homo sapiens (human) | Potency | 48.9662 | 0.0008 | 17.5051 | 59.3239 | AID1159527 |
| pregnane X nuclear receptor | Homo sapiens (human) | Potency | 61.1306 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 12.2998 | 0.0002 | 29.3054 | 16,493.5996 | AID743069 |
| peroxisome proliferator-activated receptor delta | Homo sapiens (human) | Potency | 43.6412 | 0.0010 | 24.5048 | 61.6448 | AID743215 |
| v-jun sarcoma virus 17 oncogene homolog (avian) | Homo sapiens (human) | Potency | 51.9536 | 0.0578 | 21.1097 | 61.2679 | AID1159526; AID1159528 |
| heat shock protein beta-1 | Homo sapiens (human) | Potency | 52.6430 | 0.0420 | 27.3789 | 61.6448 | AID743210; AID743228 |
| nuclear factor erythroid 2-related factor 2 isoform 1 | Homo sapiens (human) | Potency | 66.8242 | 0.0006 | 27.2152 | 1,122.0200 | AID651741 |
| caspase-1 isoform alpha precursor | Homo sapiens (human) | Potency | 39.8107 | 0.0003 | 11.4484 | 31.6228 | AID900 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID329621 | Dermal toxicity in CBA/Ca mouse assessed as skin sensitization stimulation index by measuring increase in [3H]thymidine incorporation at 20% w/v administered on ear dorsum by local lymph node assay relative to control | 2008 | Journal of medicinal chemistry, Apr-24, Volume: 51, Issue:8 | Oximes: metabolic activation and structure-allergenic activity relationships. |
| AID329619 | Dermal toxicity in CBA/Ca mouse assessed as skin sensitization stimulation index by measuring increase in [3H]thymidine incorporation at 5% w/v administered on ear dorsum by local lymph node assay relative to control | 2008 | Journal of medicinal chemistry, Apr-24, Volume: 51, Issue:8 | Oximes: metabolic activation and structure-allergenic activity relationships. |
| AID329625 | Toxicity in human liver microsomes assessed as formation of -15 Dalton ketone derived glutathione conjugates by GSH trapping technique | 2008 | Journal of medicinal chemistry, Apr-24, Volume: 51, Issue:8 | Oximes: metabolic activation and structure-allergenic activity relationships. |
| AID329622 | Dermal toxicity in CBA/Ca mouse assessed as drug level inducing 3 times increase in skin sensitization stimulation index by measuring [3H]thymidine incorporation relative to control | 2008 | Journal of medicinal chemistry, Apr-24, Volume: 51, Issue:8 | Oximes: metabolic activation and structure-allergenic activity relationships. |
| AID329624 | Toxicity in mouse liver microsomes assessed as formation of monooxidized +16 Dalton glutathione conjugates by GSH trapping technique | 2008 | Journal of medicinal chemistry, Apr-24, Volume: 51, Issue:8 | Oximes: metabolic activation and structure-allergenic activity relationships. |
| AID329618 | Dermal toxicity in CBA/Ca mouse assessed as skin sensitization stimulation index by measuring increase in [3H]thymidine incorporation at 1% w/v administered on ear dorsum by local lymph node assay relative to control | 2008 | Journal of medicinal chemistry, Apr-24, Volume: 51, Issue:8 | Oximes: metabolic activation and structure-allergenic activity relationships. |
| AID329623 | Toxicity in human liver microsomes assessed as formation of monooxidized +16 Dalton glutathione conjugates by GSH trapping technique | 2008 | Journal of medicinal chemistry, Apr-24, Volume: 51, Issue:8 | Oximes: metabolic activation and structure-allergenic activity relationships. |
| AID329617 | Dermal toxicity in CBA/Ca mouse assessed as skin sensitization stimulation index by measuring increase in [3H]thymidine incorporation at 0.1% w/v administered on ear dorsum by local lymph node assay relative to control | 2008 | Journal of medicinal chemistry, Apr-24, Volume: 51, Issue:8 | Oximes: metabolic activation and structure-allergenic activity relationships. |
| AID329620 | Dermal toxicity in CBA/Ca mouse assessed as skin sensitization stimulation index by measuring increase in [3H]thymidine incorporation at 10% w/v administered on ear dorsum by local lymph node assay relative to control | 2008 | Journal of medicinal chemistry, Apr-24, Volume: 51, Issue:8 | Oximes: metabolic activation and structure-allergenic activity relationships. |
| AID329626 | Toxicity in mouse liver microsomes assessed as formation of -15 Dalton ketone derived glutathione conjugates by GSH trapping technique | 2008 | Journal of medicinal chemistry, Apr-24, Volume: 51, Issue:8 | Oximes: metabolic activation and structure-allergenic activity relationships. |
| AID588519 | A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities | 2011 | Antiviral research, Sep, Volume: 91, Issue:3 | High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors. |
| AID540299 | A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis | 2010 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21 | Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 3 (21.43) | 18.7374 |
| 1990's | 2 (14.29) | 18.2507 |
| 2000's | 4 (28.57) | 29.6817 |
| 2010's | 5 (35.71) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.
| This Compound (50.54) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 15 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||