4-Nitrophenol
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Basic Info
| Common Name | 4-Nitrophenol(F03461) |
| 2D Structure | |
| Description | 4-Nitrophenol is a phenolic compound that is used mainly to make fungicides and dyes, and to darken leather. It is also used in the synthesis of drugs such as paracetamol, phenetidine, and acetophenetidine. 4-Nitrophenol measurement in urine is used in biological monitoring for establishing the presence and magnitude of exposures to pesticides. (A7736) (Methods in Biotechnology, 2006,61-78) (L1661, L1662) |
| FRCD ID | F03461 |
| CAS Number | 100-02-7 |
| PubChem CID | 980 |
| Formula | C6H5NO3 |
| IUPAC Name | 4-nitrophenol |
| InChI Key | BTJIUGUIPKRLHP-UHFFFAOYSA-N |
| InChI | InChI=1S/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H |
| Canonical SMILES | C1=CC(=CC=C1[N+](=O)[O-])O |
| Isomeric SMILES | C1=CC(=CC=C1[N+](=O)[O-])O |
| Wikipedia | 4-Nitrophenol |
| Synonyms |
p-nitrophenol
p-Hydroxynitrobenzene
4-Nitrophenol
100-02-7
Phenol, 4-nitro-
Paranitrophenol
Niphen
4-Hydroxynitrobenzene
Phenol, p-nitro-
Mononitrophenol
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Phenols |
| Subclass | Nitrophenols |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Nitrophenols |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Nitrophenol - Nitrobenzene - Nitroaromatic compound - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - C-nitro compound - Organic nitro compound - Organic oxoazanium - Allyl-type 1,3-dipolar organic compound - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organooxygen compound - Organonitrogen compound - Organic oxide - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as nitrophenols. These are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both a hydroxyl group and a nitro group on two different ring carbon atoms. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 139.11 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 0 |
| Complexity | 123 |
| Monoisotopic Mass | 139.027 |
| Exact Mass | 139.027 |
| XLogP | 1.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 10 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Biogenic synthesis, optical, catalytic, and in vitro antimicrobial potential ofAg-nanoparticles prepared using Palm date fruit extract. | J Photochem Photobiol B | 2018 Jan | 29272851 |
| Modified QuEChERS method for 24 plant growth regulators in grapes using LC-MS/MS. | J Food Drug Anal | 2018 Apr | 29567233 |
| Preliminary investigation of catalytic, antioxidant, anticancer and bactericidal activity of green synthesized silver and gold nanoparticles using Actinidiadeliciosa. | J Photochem Photobiol B | 2017 May | 28454046 |
| Efficiency control of dietary pesticide intake reduction by human biomonitoring. | Int J Hyg Environ Health | 2017 Mar | 27939065 |
| An optical microplate biosensor for the detection of methyl parathion pesticideusing a biohybrid of Sphingomonas sp. cells-silica nanoparticles. | Biosens Bioelectron | 2017 Jan 15 | 27573300 |
| Comparative investigation of methionine and novel formulation Metovitanprotective effects in Wistar rats with testicular and epididymal toxicity inducedby anti-tuberculosis drugs co-administration. | Food Chem Toxicol | 2017 Jan | 27919644 |
| Guazuma ulmifolia bark-synthesized Ag, Au and Ag/Au alloy nanoparticles:Photocatalytic potential, DNA/protein interactions, anticancer activity andtoxicity against 14 species of microbial pathogens. | J Photochem Photobiol B | 2017 Feb | 28076823 |
| Anticancer, antibacterial and pollutant degradation potential of silvernanoparticles from Hyphaene thebaica. | Biochem Biophys Res Commun | 2017 Aug 26 | 28648600 |
| An Amperometric Immunosensor Based on an Ionic Liquid and Single-Walled Carbon Nanotube Composite Electrode for Detection of Tetrodotoxin in Pufferfish. | J Agric Food Chem | 2016 Sep 14 | 27508884 |
| Stimulation of Diethylnitrosamine Metabolism Reduces Its General Toxic and Hepatocarcinogenic Effects. | Bull Exp Biol Med | 2016 Nov | 27878498 |
| Identification, toxicity and control of iodinated disinfection byproducts in cooking with simulated chlor(am)inated tap water and iodized table salt. | Water Res | 2016 Jan 1 | 26474150 |
| Biosynthesis of palladium nanoparticles by using Moringa oleifera flower extract and their catalytic and biological properties. | J Photochem Photobiol B | 2016 Dec | 27776261 |
| Green synthesis of Pd/CuO nanoparticles by Theobroma cacao L. seeds extract andtheir catalytic performance for the reduction of 4-nitrophenol and phosphine-freeHeck coupling reaction under aerobic conditions. | J Colloid Interface Sci | 2015 Jun 15 | 25721860 |
| Fibrillar networks of glycyrrhizic acid for hybrid nanomaterials with catalyticfeatures. | Angew Chem Int Ed Engl | 2015 Apr 27 | 25759108 |
| Catalytic strategy for efficient degradation of nitroaromatic pesticides by usinggold nanoflower. | J Agric Food Chem | 2014 Nov 5 | 25329810 |
| Gold nanocatalyst-based immunosensing strategy accompanying catalytic reductionof 4-nitrophenol for sensitive monitoring of chloramphenicol residue. | Anal Chim Acta | 2014 Jun 9 | 24856510 |
| Target-induced formation of gold amalgamation on DNA-based sensing platform forelectrochemical monitoring of mercury ion coupling with cycling signalamplification strategy. | Anal Chim Acta | 2014 Jan 31 | 24439499 |
| Green synthesis of xanthan conformation-based silver nanoparticles: antibacterialand catalytic application. | Carbohydr Polym | 2014 Jan 30 | 24299862 |
| Hydrolytic enzymes production by Aspergillus section Nigri in presence ofbutylated hydroxyanisole and propyl paraben on peanut meal extract agar. | Rev Iberoam Micol | 2014 Apr-Jun | 23583262 |
| A derivative photoelectrochemical sensing platform for 4-nitrophenolate containedorganophosphates pesticide based on carboxylated perylene sensitized nano-TiO2. | Anal Chim Acta | 2013 Mar 5 | 23427799 |
Targets
- General Function:
- Oxygen transporter activity
- Specific Function:
- Involved in oxygen transport from the lung to the various peripheral tissues.
- Gene Name:
- HBA1
- Uniprot ID:
- P69905
- Molecular Weight:
- 15257.405 Da
- Mechanism of Action:
- The nitrite in nitrophenols causes the autocatalytic oxidation of oxyhemoglobin to hydrogen peroxide and methemoglobin. This elevation of methemoglobin levels is a condition known as methemoglobinemia, and is characterized by tissue hypoxia, as methemoglobin cannot bind oxygen.
References
- Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
- General Function:
- Oxygen transporter activity
- Specific Function:
- Involved in oxygen transport from the lung to the various peripheral tissues.
- Gene Name:
- HBD
- Uniprot ID:
- P02042
- Molecular Weight:
- 16055.41 Da
- Mechanism of Action:
- The nitrite in nitrophenols causes the autocatalytic oxidation of oxyhemoglobin to hydrogen peroxide and methemoglobin. This elevation of methemoglobin levels is a condition known as methemoglobinemia, and is characterized by tissue hypoxia, as methemoglobin cannot bind oxygen.
References
- Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
- General Function:
- Oxygen transporter activity
- Specific Function:
- The epsilon chain is a beta-type chain of early mammalian embryonic hemoglobin.
- Gene Name:
- HBE1
- Uniprot ID:
- P02100
- Molecular Weight:
- 16202.71 Da
- Mechanism of Action:
- The nitrite in nitrophenols causes the autocatalytic oxidation of oxyhemoglobin to hydrogen peroxide and methemoglobin. This elevation of methemoglobin levels is a condition known as methemoglobinemia, and is characterized by tissue hypoxia, as methemoglobin cannot bind oxygen.
References
- Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
- General Function:
- Oxygen transporter activity
- Specific Function:
- Gamma chains make up the fetal hemoglobin F, in combination with alpha chains.
- Gene Name:
- HBG1
- Uniprot ID:
- P69891
- Molecular Weight:
- 16140.37 Da
- Mechanism of Action:
- The nitrite in nitrophenols causes the autocatalytic oxidation of oxyhemoglobin to hydrogen peroxide and methemoglobin. This elevation of methemoglobin levels is a condition known as methemoglobinemia, and is characterized by tissue hypoxia, as methemoglobin cannot bind oxygen.
References
- Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
- General Function:
- Gamma chains make up the fetal hemoglobin F, in combination with alpha chains.
- Specific Function:
- Heme binding
- Gene Name:
- HBG2
- Uniprot ID:
- P69892
- Molecular Weight:
- 16126.35 Da
- Mechanism of Action:
- The nitrite in nitrophenols causes the autocatalytic oxidation of oxyhemoglobin to hydrogen peroxide and methemoglobin. This elevation of methemoglobin levels is a condition known as methemoglobinemia, and is characterized by tissue hypoxia, as methemoglobin cannot bind oxygen.
References
- Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
- General Function:
- Oxygen transporter activity
- Gene Name:
- HBM
- Uniprot ID:
- Q6B0K9
- Molecular Weight:
- 15617.97 Da
- Mechanism of Action:
- The nitrite in nitrophenols causes the autocatalytic oxidation of oxyhemoglobin to hydrogen peroxide and methemoglobin. This elevation of methemoglobin levels is a condition known as methemoglobinemia, and is characterized by tissue hypoxia, as methemoglobin cannot bind oxygen.
References
- Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
- General Function:
- Oxygen transporter activity
- Gene Name:
- HBQ1
- Uniprot ID:
- P09105
- Molecular Weight:
- 15507.575 Da
- Mechanism of Action:
- The nitrite in nitrophenols causes the autocatalytic oxidation of oxyhemoglobin to hydrogen peroxide and methemoglobin. This elevation of methemoglobin levels is a condition known as methemoglobinemia, and is characterized by tissue hypoxia, as methemoglobin cannot bind oxygen.
References
- Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
- General Function:
- Oxygen transporter activity
- Specific Function:
- The zeta chain is an alpha-type chain of mammalian embryonic hemoglobin.
- Gene Name:
- HBZ
- Uniprot ID:
- P02008
- Molecular Weight:
- 15636.845 Da
- Mechanism of Action:
- The nitrite in nitrophenols causes the autocatalytic oxidation of oxyhemoglobin to hydrogen peroxide and methemoglobin. This elevation of methemoglobin levels is a condition known as methemoglobinemia, and is characterized by tissue hypoxia, as methemoglobin cannot bind oxygen.
References
- Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
- General Function:
- Sulfotransferase activity
- Specific Function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of catecholamines, phenolic drugs and neurotransmitters. Has also estrogen sulfotransferase activity. responsible for the sulfonation and activation of minoxidil. Is Mediates the metabolic activation of carcinogenic N-hydroxyarylamines to DNA binding products and could so participate as modulating factor of cancer risk.
- Gene Name:
- SULT1A1
- Uniprot ID:
- P50225
- Molecular Weight:
- 34165.13 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
- Gene Name:
- AR
- Uniprot ID:
- P10275
- Molecular Weight:
- 98987.9 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Oxygen transporter activity
- Specific Function:
- Involved in oxygen transport from the lung to the various peripheral tissues.LVV-hemorphin-7 potentiates the activity of bradykinin, causing a decrease in blood pressure.Spinorphin: functions as an endogenous inhibitor of enkephalin-degrading enzymes such as DPP3, and as a selective antagonist of the P2RX3 receptor which is involved in pain signaling, these properties implicate it as a regulator of pain and inflammation.
- Gene Name:
- HBB
- Uniprot ID:
- P68871
- Molecular Weight:
- 15998.34 Da
- Mechanism of Action:
- The nitrite in nitrophenols causes the autocatalytic oxidation of oxyhemoglobin to hydrogen peroxide and methemoglobin. This elevation of methemoglobin levels is a condition known as methemoglobinemia, and is characterized by tissue hypoxia, as methemoglobin cannot bind oxygen.
References
- Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]