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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-10-13 04:33:28 UTC
HMDB IDHMDB0001169
Secondary Accession Numbers
  • HMDB01169
Metabolite Identification
Common Name4-Aminophenol
Description4-Aminophenol, also known as 4-aminobenzenol or 4-hydroxyaniline, belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety. 4-Aminophenol has been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), and milk (cow). This could make 4-aminophenol a potential biomarker for the consumption of these foods. 4-Aminophenol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 4-Aminophenol.
Structure
Data?1582752181
Synonyms
ValueSource
4-AminobenzenolChEBI
4-HydroxyanilineChEBI
p-AminophenolChEBI
p-HydroxyanilineChEBI
4-Aminophenol conjugate monoacidMeSH
4-Aminophenol hydrochlorideMeSH
4-Aminophenol monopotassium saltMeSH
4-Aminophenol monosodium saltMeSH
4-Aminophenol sulfateMeSH
4-Aminophenol sulfate (2:1)MeSH
4-Aminophenol, 18O-labeledMeSH
4-Aminophenol, 3H-labeledMeSH
4-Aminophenol, ion(1+)MeSH
p-Aminophenol phosphateMeSH
Para-aminophenolMeSH
1-amino-4-HydroxybenzeneHMDB
4-amino-1-HydroxybenzeneHMDB
ActivolHMDB
AminophenolHMDB
EnergolHMDB
Fouramine PHMDB
P-HydroxyphenylamineHMDB
ParamidophenolHMDB
ParanolHMDB
4-AminophenolKEGG
Chemical FormulaC6H7NO
Average Molecular Weight109.1259
Monoisotopic Molecular Weight109.052763851
IUPAC Name4-aminophenol
Traditional Nameaminophenol
CAS Registry Number123-30-8
SMILES
NC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2
InChI KeyPLIKAWJENQZMHA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAniline and substituted anilines
Direct ParentAniline and substituted anilines
Alternative Parents
Substituents
  • P-aminophenol
  • Aniline or substituted anilines
  • Aminophenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • 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 Point187.50 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point187.5 °CNot Available
Water Solubility16 mg/mLNot Available
LogP0.04HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility121 g/LALOGPS
logP10(0.47) g/LALOGPS
logP10(0.84) g/LChemAxon
logS10(0.04) g/LALOGPS
pKa (Strongest Acidic)10.4ChemAxon
pKa (Strongest Basic)5.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32.74 m³·mol⁻¹ChemAxon
Polarizability11.23 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]+120.98431661259
DarkChem[M-H]-117.70131661259
AllCCS[M+H]+123.7832859911
AllCCS[M-H]-120.37632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-AminophenolNC1=CC=C(O)C=C12619.5Standard polar33892256
4-AminophenolNC1=CC=C(O)C=C11311.4Standard non polar33892256
4-AminophenolNC1=CC=C(O)C=C11261.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Aminophenol,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(N)C=C11354.4Semi standard non polar33892256
4-Aminophenol,1TMS,isomer #2C[Si](C)(C)NC1=CC=C(O)C=C11535.1Semi standard non polar33892256
4-Aminophenol,2TMS,isomer #1C[Si](C)(C)NC1=CC=C(O[Si](C)(C)C)C=C11536.0Semi standard non polar33892256
4-Aminophenol,2TMS,isomer #1C[Si](C)(C)NC1=CC=C(O[Si](C)(C)C)C=C11512.7Standard non polar33892256
4-Aminophenol,2TMS,isomer #1C[Si](C)(C)NC1=CC=C(O[Si](C)(C)C)C=C11567.2Standard polar33892256
4-Aminophenol,2TMS,isomer #2C[Si](C)(C)N(C1=CC=C(O)C=C1)[Si](C)(C)C1616.4Semi standard non polar33892256
4-Aminophenol,2TMS,isomer #2C[Si](C)(C)N(C1=CC=C(O)C=C1)[Si](C)(C)C1694.9Standard non polar33892256
4-Aminophenol,2TMS,isomer #2C[Si](C)(C)N(C1=CC=C(O)C=C1)[Si](C)(C)C1691.0Standard polar33892256
4-Aminophenol,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C11583.1Semi standard non polar33892256
4-Aminophenol,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C11618.3Standard non polar33892256
4-Aminophenol,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C11522.5Standard polar33892256
4-Aminophenol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(N)C=C11570.2Semi standard non polar33892256
4-Aminophenol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=CC=C(O)C=C11769.8Semi standard non polar33892256
4-Aminophenol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12005.0Semi standard non polar33892256
4-Aminophenol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C11975.7Standard non polar33892256
4-Aminophenol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C11856.5Standard polar33892256
4-Aminophenol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C2085.4Semi standard non polar33892256
4-Aminophenol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C2122.1Standard non polar33892256
4-Aminophenol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C1875.2Standard polar33892256
4-Aminophenol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C12298.6Semi standard non polar33892256
4-Aminophenol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C12252.6Standard non polar33892256
4-Aminophenol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C11922.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4-Aminophenol EI-B (Non-derivatized)splash10-0a4i-6900000000-9c5bfea7a6ff3c8450012017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Aminophenol EI-B (Non-derivatized)splash10-0pe9-9300000000-8ff47e2157f6fbfe67542017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Aminophenol GC-EI-TOF (Non-derivatized)splash10-0f79-1890000000-c8247060f46131c693d12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Aminophenol GC-EI-TOF (Non-derivatized)splash10-03di-1927000000-b873199d9ac85605a4df2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Aminophenol EI-B (Non-derivatized)splash10-0a4i-6900000000-9c5bfea7a6ff3c8450012018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Aminophenol EI-B (Non-derivatized)splash10-0pe9-9300000000-8ff47e2157f6fbfe67542018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Aminophenol GC-EI-TOF (Non-derivatized)splash10-0f79-1890000000-c8247060f46131c693d12018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Aminophenol GC-EI-TOF (Non-derivatized)splash10-03di-1927000000-b873199d9ac85605a4df2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Aminophenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-5900000000-e64da39e73e3c0ea696c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Aminophenol GC-MS (1 TMS) - 70eV, Positivesplash10-060r-6900000000-2c6cd652b49e26ce3fce2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Aminophenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Aminophenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9700000000-00bffb48fd955696bccc2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Aminophenol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-03di-3900000000-906f96b14dfdad2310de2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Aminophenol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-014i-9000000000-d56be0077647bc66e9622012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Aminophenol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-014i-9000000000-937794addf5b73c988e92012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Aminophenol LC-ESI-QFT , positive-QTOFsplash10-03di-2900000000-1d20b6ad92e8fe4dcb552017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Aminophenol 35V, Positive-QTOFsplash10-03di-2900000000-5950ca2352822bea4a012021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Aminophenol 35V, Positive-QTOFsplash10-02tc-9300000000-3524fecaa931f284564b2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminophenol 10V, Positive-QTOFsplash10-03di-0900000000-da3b2114d9298a0363e72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminophenol 20V, Positive-QTOFsplash10-03di-1900000000-b43943b1e137b2912b0f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminophenol 40V, Positive-QTOFsplash10-00lr-9000000000-8ca8655366b90d8f42df2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminophenol 10V, Negative-QTOFsplash10-0a4i-0900000000-28f35dbe83fee57d4a702017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminophenol 20V, Negative-QTOFsplash10-0a4i-0900000000-6aa4cd1a9d2a859fa70b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminophenol 40V, Negative-QTOFsplash10-0a7i-9300000000-177dcaf10b9e95cb409c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminophenol 10V, Positive-QTOFsplash10-03di-0900000000-c89e2460dc3caf4abe052021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminophenol 20V, Positive-QTOFsplash10-014i-9100000000-b0a8e0715ece78a9716d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminophenol 40V, Positive-QTOFsplash10-0159-9000000000-aed714f11873786e9c3a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminophenol 10V, Negative-QTOFsplash10-0a4i-0900000000-875d8abd6f6773a406342021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminophenol 20V, Negative-QTOFsplash10-0a4i-0900000000-875d8abd6f6773a406342021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Aminophenol 40V, Negative-QTOFsplash10-0f6x-9200000000-17afc5bcee8bb56bc9e82021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Epidermis
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified10.00 (0.03-20.00) uMAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022462
KNApSAcK IDNot Available
Chemspider ID392
KEGG Compound IDC02372
BioCyc IDCPD-259
BiGG IDNot Available
Wikipedia Link4-Aminophenol
METLIN ID6051
PubChem Compound403
PDB IDNot Available
ChEBI ID17602
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1198931
References
Synthesis ReferenceZhu, Jianliang; Yang, Ying; Xu, Jinlai; Gu, Zhiqiang; Zhang, Xiaowei; Zheng, Zhigang; Li, Jianlin; Hao, Xiangyang. Method for preparation of p-aminophenol. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 6 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lampinen M, Bondesson U, Fredriksson E, Hedeland M: Validation of a method for quantification of ketobemidone in human plasma with liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jun 15;789(2):347-54. [PubMed:12742125 ]
  2. Clark PM, Clark JD, Wheatley T: Urine discoloration after acetaminophen overdose. Clin Chem. 1986 Sep;32(9):1777-8. [PubMed:3742803 ]
  3. Kanishchev PA, Bereza NM, Seniuk VF, Perevziaka AV: [Quantitative determination of blood loss from the gastrointestinal tract using Metol in chronic diseases of the digestive organs]. Lab Delo. 1989;(3):36-8. [PubMed:2469837 ]
  4. Xu Y, Halsall B, Heineman WR: Heterogeneous enzyme immunoassay of alpha-fetoprotein in maternal serum by flow-injection amperometric detection of 4-aminophenol. Clin Chem. 1990 Nov;36(11):1941-4. [PubMed:1700742 ]
  5. Bomhard EM, Herbold BA: Genotoxic activities of aniline and its metabolites and their relationship to the carcinogenicity of aniline in the spleen of rats. Crit Rev Toxicol. 2005 Dec;35(10):783-835. [PubMed:16468500 ]
  6. Nohynek GJ, Duche D, Garrigues A, Meunier PA, Toutain H, Leclaire J: Under the skin: Biotransformation of para-aminophenol and para-phenylenediamine in reconstructed human epidermis and human hepatocytes. Toxicol Lett. 2005 Sep 15;158(3):196-212. [PubMed:15890478 ]
  7. Van Bocxlaer JF, Clauwaert KM, Lambert WE, De Leenheer AP: Quantitative colorimetric determination of urinary p-aminophenol with an automated analyzer. Clin Chem. 1997 Apr;43(4):627-34. [PubMed:9105264 ]
  8. Gil EP, Tang HT, Halsall HB, Heineman WR, Misiego AS: Competitive heterogeneous enzyme immunoassay for theophylline by flow-injection analysis with electrochemical detection of p-aminophenol. Clin Chem. 1990 Apr;36(4):662-5. [PubMed:2138937 ]
  9. Arndt CA, Colvin OM, Balis FM, Lester CM, Johnson G, Poplack DG: Intrathecal administration of 4-hydroperoxycyclophosphamide in rhesus monkeys. Cancer Res. 1987 Nov 15;47(22):5932-4. [PubMed:3664493 ]
  10. Hegedus ZL, Nayak U: Para-aminophenol and structurally related compounds as intermediates in lipofuscin formation and in renal and other tissue toxicities. Arch Int Physiol Biochim Biophys. 1991 Feb;99(1):99-105. [PubMed:1713494 ]