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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:45:29 UTC
HMDB IDHMDB0001232
Secondary Accession Numbers
  • HMDB0062627
  • HMDB01232
  • HMDB62627
Metabolite Identification
Common Name4-Nitrophenol
Description4-Nitrophenol (also called p-nitrophenol or 4-hydroxynitrobenzene) is a phenolic compound that has a nitro group at the opposite position of the hydroxyl group on the benzene ring. It belongs to the class of organic compounds known as nitrophenols. Nitrophenols 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. 4-Nitrophenol shows two polymorphs in the crystalline state. The alpha-form is colorless pillars, unstable at room temperature, and stable toward sunlight. The beta-form is yellow pillars, stable at room temperature, and gradually turns red upon irradiation of sunlight. Usually 4-nitrophenol exists as a mixture of these two forms. 4-Nitrophenol can be used as a pH indicator and as an intermediate in the synthesis of paracetamol. Itis also used as the precursor for the preparation of phenetidine and acetophenetidine, indicators, and raw materials for fungicides. Bioaccumulation of this compound rarely occurs. In peptide synthesis, carboxylate ester derivatives of 4-nitrophenol may serve as activated components for construction of amide moieties. 4-Nitrophenol is a potentially toxic compound: it can cause eyes, skin, and respiratory tract irritations. It may also cause inflammation of those parts. It has a delayed interaction with blood and forms methaemoglobin which is responsible for methemoglobinemia -which is characterized by tissue hypoxia, as methemoglobin cannot bind oxygen-, potentially causing cyanosis, confusion, and unconsciousness. When ingested, it causes abdominal pain and vomiting. Prolonged contact with skin may cause allergic response. Genotoxicity and carcinogenicity of 4-nitrophenol are not known. The LD50 in mice is 282 mg/kg and in rats is 202 mg/kg. Outside of the human body, 4-Nitrophenol has been detected, but not quantified in cow milk. Conjugates are more polar than the parent compounds and therefore are easier to excrete in the urine.
Structure
Data?1582752185
Synonyms
ValueSource
4-HydroxynitrobenzeneChEBI
NiphenChEBI
p-HydroxynitrobenzeneChEBI
p-NitrophenolChEBI
ParanitrophenolChEBI
PNPChEBI
MononitrophenolHMDB
1-Hydroxy-4-nitrobenzeneHMDB
4-Nitrophenol, (18)O-labeled CPDHMDB
4-Nitrophenol, 1-(13)C-labeled CPDHMDB
4-Nitrophenol, manganese (2+) saltHMDB
4-Nitrophenol, silver(2+) saltHMDB
4-Nitrophenol, sodium salt, (2:1), dihydrateHMDB
4-Nitrophenol, tin (4+) saltHMDB
4-Nitrophenol, 2,6-(13)C2-labeled CPDHMDB
4-Nitrophenol, 2-(14)C-labeled CPDHMDB
4-Nitrophenol, copper(1+) saltHMDB
4-Nitrophenol, potassium saltHMDB
4-Nitrophenol, tin (2+) saltHMDB
4-Nitrophenol, 14C-labeled CPDHMDB
4-Nitrophenol, ammonium saltHMDB
4-Nitrophenol, ion(1-)HMDB
4-Nitrophenol, ion(1-) hydrideHMDB
4-Nitrophenol, sodium saltHMDB
4-Nitrophenol, 2,6-(14)C2-labeled CPDHMDB
4-Nitrophenol, aluminum saltHMDB
4-Nitrophenol, cesium saltHMDB
4-Nitrophenol, iron(3+) saltHMDB
4-Nitrophenol, lithium saltHMDB
4-Nitrophenol, manganese saltHMDB
4-Nitrophenol, zinc saltHMDB
4-Hydroxy-1-nitrobenzeneHMDB
4-NitrophenolateHMDB
4-NitrophenolHMDB
Chemical FormulaC6H5NO3
Average Molecular Weight139.1088
Monoisotopic Molecular Weight139.026943031
IUPAC Name4-nitrophenol
Traditional NameP-nitrophenol
CAS Registry Number100-02-7
SMILES
OC1=CC=C(C=C1)[N+]([O-])=O
InChI Identifier
InChI=1S/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H
InChI KeyBTJIUGUIPKRLHP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nitrophenols. Nitrophenols 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassNitrophenols
Direct ParentNitrophenols
Alternative Parents
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
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point113.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility11.6 mg/mLNot Available
LogP1.91HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.6 g/LALOGPS
logP10(1.93) g/LALOGPS
logP10(1.61) g/LChemAxon
logS10(-1.6) g/LALOGPS
pKa (Strongest Acidic)7.07ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.36 m³·mol⁻¹ChemAxon
Polarizability12.22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.431661259
DarkChem[M+H]+129.431661259
DarkChem[M-H]-127.11531661259
DarkChem[M-H]-127.11531661259
AllCCS[M+H]+128.40132859911
AllCCS[M-H]-122.09732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-NitrophenolOC1=CC=C(C=C1)[N+]([O-])=O2647.2Standard polar33892256
4-NitrophenolOC1=CC=C(C=C1)[N+]([O-])=O1523.2Standard non polar33892256
4-NitrophenolOC1=CC=C(C=C1)[N+]([O-])=O1528.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Nitrophenol,1TMS,isomer #1C[Si](C)(C)OC1=CC=C([N+](=O)[O-])C=C11488.5Semi standard non polar33892256
4-Nitrophenol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C([N+](=O)[O-])C=C11754.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol EI-B (Non-derivatized)splash10-00kr-9200000000-6a367c2627bf30cad1632017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol EI-B (Non-derivatized)splash10-00or-9500000000-a23a22fc3222413259042017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol EI-B (Non-derivatized)splash10-000i-9400000000-670d24ff2b2b121a7ab82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol EI-B (Non-derivatized)splash10-000i-9400000000-b5aea5436a88b29179e92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol EI-B (Non-derivatized)splash10-05n0-9300000000-f284a324180bf4d7ffc22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol EI-B (Non-derivatized)splash10-0006-2009127011-85632179856636169d282017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol GC-EI-TOF (Non-derivatized)splash10-0f6t-1900000000-70af7d7902cd35a26f292017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol EI-B (Non-derivatized)splash10-00kr-9200000000-6a367c2627bf30cad1632018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol EI-B (Non-derivatized)splash10-00or-9500000000-a23a22fc3222413259042018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol EI-B (Non-derivatized)splash10-000i-9400000000-670d24ff2b2b121a7ab82018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol EI-B (Non-derivatized)splash10-000i-9400000000-b5aea5436a88b29179e92018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol EI-B (Non-derivatized)splash10-05n0-9300000000-f284a324180bf4d7ffc22018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol EI-B (Non-derivatized)splash10-0006-2009127011-85632179856636169d282018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol GC-EI-TOF (Non-derivatized)splash10-0f6t-1900000000-70af7d7902cd35a26f292018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol EI-B (Non-derivatized)splash10-00kr-9200000000-6a367c2627bf30cad1632018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol EI-B (Non-derivatized)splash10-00or-9500000000-a23a22fc3222413259042018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol EI-B (Non-derivatized)splash10-000i-9400000000-670d24ff2b2b121a7ab82018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol EI-B (Non-derivatized)splash10-000i-9400000000-b5aea5436a88b29179e92018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol EI-B (Non-derivatized)splash10-05n0-9300000000-f284a324180bf4d7ffc22018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol EI-B (Non-derivatized)splash10-0006-2009127011-85632179856636169d282018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol GC-EI-TOF (Non-derivatized)splash10-0f6t-1900000000-70af7d7902cd35a26f292018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol EI-B (Non-derivatized)splash10-00kr-9200000000-6a367c2627bf30cad1632018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nitrophenol EI-B (Non-derivatized)splash10-00or-9500000000-a23a22fc3222413259042018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Nitrophenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-7900000000-d4915e2347113b56d32c2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Nitrophenol GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9800000000-7bde61a3b7f0a23ddd412017-10-06Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00kr-9300000000-d76f14df8da868057d442014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenol Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-00dl-0900000000-653240f82298b3880e702012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenol Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-014l-9100000000-1dd6a69ee33aeb4207a32012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenol Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-014r-9000000000-397a0913b382e58ae4182012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenol EI-B (HITACHI RMU-7M) , Positive-QTOFsplash10-00kr-9200000000-039471e02c3307757a0c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenol EI-B (HITACHI RMU-6M) , Positive-QTOFsplash10-00or-9500000000-a23a22fc3222413259042012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenol EI-B (Unknown) , Positive-QTOFsplash10-000i-9400000000-12717928037244536b6b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenol EI-B (HITACHI M-60) , Positive-QTOFsplash10-000i-9400000000-f133ed564f0a12bd38712012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenol EI-B (HITACHI M-80) , Positive-QTOFsplash10-05n0-9300000000-d39a8dbf21962717a2ee2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenol LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0002-9200000000-bff0a2a3c15629cc6ec22012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenol LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-052r-0900000000-1279a141e229fec8dbd42012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenol LC-ESI-QTOF , negative-QTOFsplash10-052r-0900000000-1279a141e229fec8dbd42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenol LC-ESI-QTOF , positive-QTOFsplash10-0002-9200000000-bff0a2a3c15629cc6ec22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenol 20V, Positive-QTOFsplash10-00r6-9300000000-5cb2a9e8e318ca2474fd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenol 10V, Positive-QTOFsplash10-00di-1900000000-0c7b180f083127156f272021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenol 90V, Negative-QTOFsplash10-0a4i-0900000000-c41839802d48c97c72b72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenol 75V, Negative-QTOFsplash10-0a4i-0900000000-465b86a7fa9c91aea0912021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenol 15V, Negative-QTOFsplash10-052r-0900000000-7545ed558dcbc5a7a3862021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenol 30V, Negative-QTOFsplash10-052r-0900000000-24c57afe8ccf403e589b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nitrophenol 35V, Negative-QTOFsplash10-0a4r-2900000000-396ebc9986624989747e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenol 10V, Positive-QTOFsplash10-0006-0900000000-d01a64d09fb568b883b12016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenol 20V, Positive-QTOFsplash10-001i-0900000000-58e0d9a2ff9a60a8c4f62016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenol 40V, Positive-QTOFsplash10-01q9-2900000000-fbf4f5da283a46ec8ed82016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenol 10V, Negative-QTOFsplash10-000i-0900000000-3c17676b62ba6a9be8d52016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenol 20V, Negative-QTOFsplash10-000i-0900000000-4dcec4bcef5be284e7382016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nitrophenol 40V, Negative-QTOFsplash10-002r-3900000000-de3f2773a5601a2eec1b2016-09-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Intestine
  • Liver
  • Placenta
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04417
Phenol Explorer Compound IDNot Available
FooDB IDFDB022503
KNApSAcK IDNot Available
Chemspider ID955
KEGG Compound IDC00870
BioCyc IDP-NITROPHENOL
BiGG ID36247
Wikipedia Link4-Nitrophenol
METLIN ID4100
PubChem Compound980
PDB IDNot Available
ChEBI ID16836
Food Biomarker OntologyNot Available
VMH ID4NPH
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceFache, Eric; Righini, Sebastien. Preparation of a nitrophenol. Fr. Demande (2004), 35 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Ozawa S, Shimizu M, Katoh T, Miyajima A, Ohno Y, Matsumoto Y, Fukuoka M, Tang YM, Lang NP, Kadlubar FF: Sulfating-activity and stability of cDNA-expressed allozymes of human phenol sulfotransferase, ST1A3*1 ((213)Arg) and ST1A3*2 ((213)His), both of which exist in Japanese as well as Caucasians. J Biochem. 1999 Aug;126(2):271-7. [PubMed:10423517 ]
  2. Sharaev PN, Gabdrakhmanova NK, Strelkova TN, Sakhabutdinova EP: [Detection of N-acetyl-beta-D-hexosaminidase in urine]. Klin Lab Diagn. 2004 May;(5):40-2. [PubMed:15230116 ]
  3. Anderson RJ, Garcia MJ, Liebentritt DK, Kay HD: Localization of human blood phenol sulfotransferase activities: novel detection of the thermostable enzyme in granulocytes. J Lab Clin Med. 1991 Nov;118(5):500-9. [PubMed:1940590 ]
  4. Kayamori Y, Katayama Y: Enzymatic method for assaying calcium in serum and urine with porcine pancreatic alpha-amylase. Clin Chem. 1994 May;40(5):781-4. [PubMed:8174252 ]
  5. Pacifici GM, Temellini A, Castiglioni M, D'Alessandro C, Ducci A, Giuliani L: Interindividual variability of the human hepatic sulphotransferases. Chem Biol Interact. 1994 Jun;92(1-3):219-31. [PubMed:8033255 ]
  6. Bowers GN Jr, McComb RB, Christensen RG, Schaffer R: High-purity 4-nitrophenol: purification, characterization, and specifications for use as a spectrophotometric reference material. Clin Chem. 1980 May;26(6):724-9. [PubMed:7371150 ]
  7. Bellavite P, Andrioli G, Guzzo P, Arigliano P, Chirumbolo S, Manzato F, Santonastaso C: A colorimetric method for the measurement of platelet adhesion in microtiter plates. Anal Biochem. 1994 Feb 1;216(2):444-50. [PubMed:8179202 ]
  8. Pacifici GM: Sulfation of drugs and hormones in mid-gestation human fetus. Early Hum Dev. 2005 Jul;81(7):573-81. Epub 2004 Dec 8. [PubMed:16009282 ]
  9. Vitarius JA, Sultatos LG: Kinetic mechanism of the detoxification of the organophosphate paraoxon by human serum A-esterase. Drug Metab Dispos. 1994 May-Jun;22(3):472-8. [PubMed:8070326 ]
  10. Pacifici GM, Marchi G: Interindividual variability of phenol- and catechol-sulphotransferases in platelets from adults and newborns. Br J Clin Pharmacol. 1993 Dec;36(6):593-7. [PubMed:12959278 ]
  11. Osnes T, Sandstad O, Skar V, Osnes M: beta-Glucuronidase in common duct bile, methodological aspects, variation of pH optima and relation to gallstones. Scand J Clin Lab Invest. 1997 Jul;57(4):307-15. [PubMed:9249878 ]
  12. Young WF Jr, Okazaki H, Laws ER Jr, Weinshilboum RM: Human brain phenol sulfotransferase: biochemical properties and regional localization. J Neurochem. 1984 Sep;43(3):706-15. [PubMed:6589361 ]
  13. Leng G, Lewalter J: Role of individual susceptibility in risk assessment of pesticides. Occup Environ Med. 1999 Jul;56(7):449-53. [PubMed:10472315 ]
  14. Belanger G, Beaulieu M, Levesque E, Hum DW, Belanger A: Expression and characterization of a novel UDP-glucuronosyltransferase, UGT2B9, from cynomolgus monkey. DNA Cell Biol. 1997 Oct;16(10):1195-205. [PubMed:9364930 ]
  15. Birk AV, Broekman MJ, Gladek EM, Robertson HD, Drosopoulos JH, Marcus AJ, Szeto HH: Role of extracellular ATP metabolism in regulation of platelet reactivity. J Lab Clin Med. 2002 Sep;140(3):166-75. [PubMed:12271274 ]
  16. Rossi AM, Maggini V, Fredianelli E, Di Bello D, Pietrabissa A, Mosca F, Barale R, Pacifici GM: Phenotype-genotype relationships of SULT1A1 in human liver and variations in the IC50 of the SULT1A1 inhibitor quercetin. Int J Clin Pharmacol Ther. 2004 Oct;42(10):561-7. [PubMed:15516026 ]
  17. Reiter C, Mwaluko G, Dunnette J, Van Loon J, Weinshilboum R: Thermolabile and thermostable human platelet phenol sulfotransferase. Substrate specificity and physical separation. Naunyn Schmiedebergs Arch Pharmacol. 1983 Sep;324(2):140-7. [PubMed:6139755 ]
  18. Bravo R, Caltabiano LM, Fernandez C, Smith KD, Gallegos M, Whitehead RD Jr, Weerasekera G, Restrepo P, Bishop AM, Perez JJ, Needham LL, Barr DB: Quantification of phenolic metabolites of environmental chemicals in human urine using gas chromatography-tandem mass spectrometry and isotope dilution quantification. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jun 25;820(2):229-36. Epub 2005 Apr 26. [PubMed:15899376 ]

Only showing the first 10 proteins. There are 13 proteins in total.

Enzymes

General function:
Involved in arylesterase activity
Specific function:
Has low activity towards the organophosphate paraxon and aromatic carboxylic acid esters. Rapidly hydrolyzes lactones such as statin prodrugs (e.g. lovastatin). Hydrolyzes aromatic lactones and 5- or 6-member ring lactones with aliphatic substituents but not simple lactones or those with polar substituents.
Gene Name:
PON3
Uniprot ID:
Q15166
Molecular weight:
39607.185
Reactions
Parathion + Water → Diethylthiophosphate + 4-Nitrophenoldetails
Paraoxon + Water → Diethylphosphate + 4-Nitrophenoldetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPP
Uniprot ID:
P05187
Molecular weight:
57953.31
Reactions
4-Nitrophenyl phosphate + Water → 4-Nitrophenol + Phosphatedetails
General function:
Involved in arylesterase activity
Specific function:
Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxylic acid esters. Mediates an enzymatic protection of low density lipoproteins against oxidative modification and the consequent series of events leading to atheroma formation.
Gene Name:
PON1
Uniprot ID:
P27169
Molecular weight:
39730.99
Reactions
Parathion + Water → Diethylthiophosphate + 4-Nitrophenoldetails
Paraoxon + Water → Diethylphosphate + 4-Nitrophenoldetails
General function:
Involved in arylesterase activity
Specific function:
Capable of hydrolyzing lactones and a number of aromatic carboxylic acid esters. Has antioxidant activity. Is not associated with high density lipoprotein. Prevents LDL lipid peroxidation, reverses the oxidation of mildly oxidized LDL, and inhibits the ability of MM-LDL to induce monocyte chemotaxis.
Gene Name:
PON2
Uniprot ID:
Q15165
Molecular weight:
39380.535
Reactions
Parathion + Water → Diethylthiophosphate + 4-Nitrophenoldetails
Paraoxon + Water → Diethylphosphate + 4-Nitrophenoldetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPI
Uniprot ID:
P09923
Molecular weight:
56811.695
Reactions
4-Nitrophenyl phosphate + Water → 4-Nitrophenol + Phosphatedetails
General function:
Involved in catalytic activity
Specific function:
This isozyme may play a role in skeletal mineralization.
Gene Name:
ALPL
Uniprot ID:
P05186
Molecular weight:
57304.435
Reactions
4-Nitrophenyl phosphate + Water → 4-Nitrophenol + Phosphatedetails
General function:
Involved in hydrolase activity
Specific function:
Involved in osteopontin/bone sialoprotein dephosphorylation. Its expression seems to increase in certain pathological states such as Gaucher and Hodgkin diseases, the hairy cell, the B-cell, and the T-cell leukemias.
Gene Name:
ACP5
Uniprot ID:
P13686
Molecular weight:
36598.47
General function:
Involved in acid phosphatase activity
Specific function:
A non-specific tyrosine phosphatase that dephosphorylates a diverse number of substrates under acidic conditions (pH 4-6) including alkyl, aryl, and acyl orthophosphate monoesters and phosphorylated proteins. Has lipid phosphatase activity and inactivates lysophosphatidic acid in seminal plasma. Isoform 2: the cellular form also has ecto-5'-nucleotidase activity in dorsal root ganglion (DRG) neurons. Generates adenosine from AMP which acts as a pain suppressor. Acts as a tumor suppressor of prostate cancer through dephosphorylation of ERBB2 and deactivation of MAPK-mediated signaling.
Gene Name:
ACPP
Uniprot ID:
P15309
Molecular weight:
44565.715
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPPL2
Uniprot ID:
P10696
Molecular weight:
57376.515
Reactions
4-Nitrophenyl phosphate + Water → 4-Nitrophenol + Phosphatedetails
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
Reactions
4-Nitrophenol + NADPH + Oxygen → 4-Nitrocatechol + NADP + Waterdetails

Only showing the first 10 proteins. There are 13 proteins in total.