4-Nitrosophenol, also known as p-nitrosophenol, is a highly reactive organic compound with a nitro group (-NO2) at the para position to the hydroxyl group (-OH) on a benzene ring. It is a crucial intermediate in the synthesis of various pharmaceuticals, dyes, and other organic compounds. 4-Nitrosophenol is synthesized by the nitrosation of phenol using nitrous acid or by the oxidation of 4-aminophenol. It exists in equilibrium with its tautomer, 4-quinone monoxime. 4-Nitrosophenol exhibits potent antimicrobial activity and is a powerful inhibitor of enzymes such as cytochrome c oxidase. Its highly reactive nature makes it a useful reagent in organic synthesis, but also poses challenges in handling and storage due to its tendency to decompose and form hazardous byproducts. Due to its biological activity and synthetic importance, 4-Nitrosophenol continues to be extensively studied for its potential applications in medicinal chemistry, material science, and environmental chemistry.'
4-nitrosophenol: RN given refers to unlabeled parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 7729 |
| CHEMBL ID | 104353 |
| CHEMBL ID | 3276923 |
| SCHEMBL ID | 232995 |
| SCHEMBL ID | 107699 |
| MeSH ID | M0092820 |
| Synonym |
|---|
| p-nitrosophenol |
| 4-nitrosophenol |
| phenol, p-nitroso- |
| 104-91-6 |
| nsc-3124 |
| quinone monoxime |
| phenol, 4-nitroso- |
| nitrosophenol |
| wln: qr dno |
| nsc3124 |
| quinone oxime |
| quinone 4-oxime |
| p-quinone monooxime |
| nsc-239647 |
| nsc239647 |
| quinone monooxime |
| 1,4-benzoquinone 4-oxime |
| 637-62-7 |
| p-benzoquinone, monooxime |
| p-benzoquinone 4-oxime |
| wln: l6v dyj dunq |
| 4-hydroxyimino-2,5-cyclohexadiene-1-one |
| p-quinone monoxime |
| 2,4-dione, monooxime |
| 2, 4-hydroxyimino- |
| brn 2040595 |
| 2,5-cyclohexadiene-1,4-dione, monooxime |
| 2,5-cyclohexadien-1-one, 4-hydroxyimino- |
| nsc 239647 |
| hsdb 5362 |
| nsc 3124 |
| brn 1856695 |
| ccris 4710 |
| 4-nitrosofenol [czech] |
| 1,4-benzoquinone monoxime |
| p-chinonmonoxim [czech] |
| einecs 203-251-6 |
| para-nitrosophenol |
| ai3-19026 |
| inchi=1/c6h5no2/c8-6-3-1-5(7-9)2-4-6/h1-4,8h |
| jstcpnfnkicnno-uhfffaoysa- |
| 4-nitroso-phenol |
| CHEMBL104353 |
| FT-0662579 |
| N0374 |
| A801099 |
| NCGC00249111-01 |
| 4-hydroxyimino-cyclohexa-2,5-dien-1-one |
| dtxcid405991 |
| cas-104-91-6 |
| tox21_303059 |
| NCGC00257216-01 |
| dtxsid0025991 , |
| tox21_201754 |
| NCGC00259303-01 |
| AKOS006230373 |
| AKOS006311740 |
| 55eb58h2up , |
| p-chinonmonoxim |
| 4-07-00-02073 (beilstein handbook reference) |
| 4-nitrosofenol |
| unii-55eb58h2up |
| 4-benzoquinone monoxime |
| FT-0631578 |
| p-benzoquinone monoxime |
| 4-nitrosophenol [mi] |
| 4-nitrosophenol [hsdb] |
| nitrosophenol, 4- |
| SCHEMBL232995 |
| CHEMBL3276923 |
| SCHEMBL107699 |
| mono-nitroso phenol |
| benzoquinone oxime |
| AM86242 |
| benzoquinone monooxime |
| W-108801 |
| STL453714 |
| mfcd00002329 |
| 4-(hydroxyimino)cyclohexa-2,5-dien-1-one |
| DTXSID0075287 |
| 4-nitrosophenol (wetted with ca. 40% water) (unit weight on dry weight basis) |
| Q27261304 |
| D95331 |
| 4-nitrosophenol (wetted with ca. 40% water) |
| CS-0366469 |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Luciferase | Photinus pyralis (common eastern firefly) | Potency | 77.8251 | 0.0072 | 15.7588 | 89.3584 | AID1224835 |
| GLI family zinc finger 3 | Homo sapiens (human) | Potency | 9.6885 | 0.0007 | 14.5928 | 83.7951 | AID1259369 |
| AR protein | Homo sapiens (human) | Potency | 47.4242 | 0.0002 | 21.2231 | 8,912.5098 | AID1259243 |
| estrogen receptor 2 (ER beta) | Homo sapiens (human) | Potency | 59.7035 | 0.0006 | 57.9133 | 22,387.1992 | AID1259377 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 60.2296 | 0.0002 | 29.3054 | 16,493.5996 | AID743075 |
| aryl hydrocarbon receptor | Homo sapiens (human) | Potency | 49.8374 | 0.0007 | 23.0674 | 1,258.9301 | AID743085; AID743122 |
| thyroid stimulating hormone receptor | Homo sapiens (human) | Potency | 66.9885 | 0.0016 | 28.0151 | 77.1139 | AID1259385 |
| activating transcription factor 6 | Homo sapiens (human) | Potency | 53.6864 | 0.1434 | 27.6121 | 59.8106 | AID1159516 |
| Histone H2A.x | Cricetulus griseus (Chinese hamster) | Potency | 64.6710 | 0.0391 | 47.5451 | 146.8240 | AID1224845 |
| Cellular tumor antigen p53 | Homo sapiens (human) | Potency | 59.7035 | 0.0023 | 19.5956 | 74.0614 | AID651631 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID15024 | Concentration distributed until decomposition of N-acetyl-N-hydroxy-p-aminophenol at pH 10.5 | 1980 | Journal of medicinal chemistry, Mar, Volume: 23, Issue:3 | Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen. |
| AID15027 | Concentration distributed until decomposition of N-acetyl-N-hydroxy-p-aminophenol at pH 7.6 | 1980 | Journal of medicinal chemistry, Mar, Volume: 23, Issue:3 | Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen. |
| AID15028 | Concentration distributed until decomposition of N-acetyl-N-hydroxy-p-aminophenol at pH 8.2 | 1980 | Journal of medicinal chemistry, Mar, Volume: 23, Issue:3 | Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen. |
| AID15026 | Concentration distributed until decomposition of N-acetyl-N-hydroxy-p-aminophenol at pH 7.2 | 1980 | Journal of medicinal chemistry, Mar, Volume: 23, Issue:3 | Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen. |
| AID15023 | Concentration distributed until decomposition of N-acetyl-N-hydroxy-p-aminophenol at pH 10 | 1980 | Journal of medicinal chemistry, Mar, Volume: 23, Issue:3 | Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen. |
| AID15025 | Concentration distributed until decomposition of N-acetyl-N-hydroxy-p-aminophenol at pH 6.8 | 1980 | Journal of medicinal chemistry, Mar, Volume: 23, Issue:3 | Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen. |
| AID15029 | Concentration distributed until decomposition of N-acetyl-N-hydroxy-p-aminophenol at pH 9.6 | 1980 | Journal of medicinal chemistry, Mar, Volume: 23, Issue:3 | Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen. |
| AID1148273 | Antitumor activity against mouse Sarcoma 180 cells allografted in Swiss mouse assessed as survival time at 150 mg/kg, ip three doses were given at 24 hrs interval starting 24 hrs after allograft injection relative to control | 1978 | Journal of medicinal chemistry, Jan, Volume: 21, Issue:1 | Nitrogen analogues of 1,4-benzoquinones. Activities against the ascitic sarcoma 180 of mice. |
| AID1148238 | Antitumor activity against mouse Sarcoma 180 cells allografted in Swiss mouse assessed as survival at 150 mg/kg, ip three doses were given at 24 hrs interval starting 24 hrs after allograft injection measured after 5 days | 1978 | Journal of medicinal chemistry, Jan, Volume: 21, Issue:1 | Nitrogen analogues of 1,4-benzoquinones. Activities against the ascitic sarcoma 180 of mice. |
| AID1148298 | Redox potential of the compound in octanol-water solution | 1978 | Journal of medicinal chemistry, Jan, Volume: 21, Issue:1 | Nitrogen analogues of 1,4-benzoquinones. Activities against the ascitic sarcoma 180 of mice. |
| AID1148232 | Acute toxicity in single ip dosed Swiss mouse assessed as death up to 5 days | 1978 | Journal of medicinal chemistry, Jan, Volume: 21, Issue:1 | Nitrogen analogues of 1,4-benzoquinones. Activities against the ascitic sarcoma 180 of mice. |
| AID1148288 | Antitumor activity against mouse Sarcoma 180 cells allografted in Swiss mouse at 150 mg/kg, ip three doses were given at 24 hrs interval starting 24 hrs after allograft injection relative to control | 1978 | Journal of medicinal chemistry, Jan, Volume: 21, Issue:1 | Nitrogen analogues of 1,4-benzoquinones. Activities against the ascitic sarcoma 180 of mice. |
| AID1148262 | Antitumor activity against mouse Sarcoma 180 cells allografted in Swiss mouse assessed as cure at 150 mg/kg, ip three doses were given at 24 hrs interval starting 24 hrs after allograft injection measured after 60 days | 1978 | Journal of medicinal chemistry, Jan, Volume: 21, Issue:1 | Nitrogen analogues of 1,4-benzoquinones. Activities against the ascitic sarcoma 180 of mice. |
| AID1148248 | Antitumor activity against mouse Sarcoma 180 cells allografted in Swiss mouse assessed as weight gain at 150 mg/kg, ip three doses were given at 24 hrs interval starting 24 hrs after allograft injection measured after 3 days relative to control | 1978 | Journal of medicinal chemistry, Jan, Volume: 21, Issue:1 | Nitrogen analogues of 1,4-benzoquinones. Activities against the ascitic sarcoma 180 of mice. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 8 (53.33) | 18.7374 |
| 1990's | 4 (26.67) | 18.2507 |
| 2000's | 2 (13.33) | 29.6817 |
| 2010's | 1 (6.67) | 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 (53.10) 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] | ||