Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2023-02-21 17:15:29 UTC |
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HMDB ID | HMDB0001169 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 4-Aminophenol |
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Description | 4-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. |
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Structure | InChI=1S/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2 |
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Synonyms | Value | Source |
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4-Aminobenzenol | ChEBI | 4-Hydroxyaniline | ChEBI | p-Aminophenol | ChEBI | p-Hydroxyaniline | ChEBI | 4-Aminophenol conjugate monoacid | MeSH | 4-Aminophenol hydrochloride | MeSH | 4-Aminophenol monopotassium salt | MeSH | 4-Aminophenol monosodium salt | MeSH | 4-Aminophenol sulfate | MeSH | 4-Aminophenol sulfate (2:1) | MeSH | 4-Aminophenol, 18O-labeled | MeSH | 4-Aminophenol, 3H-labeled | MeSH | 4-Aminophenol, ion(1+) | MeSH | p-Aminophenol phosphate | MeSH | Para-aminophenol | MeSH | 1-amino-4-Hydroxybenzene | HMDB | 4-amino-1-Hydroxybenzene | HMDB | Activol | HMDB | Aminophenol | HMDB | Energol | HMDB | Fouramine P | HMDB | P-Hydroxyphenylamine | HMDB | Paramidophenol | HMDB | Paranol | HMDB | 4-Aminophenol | KEGG |
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Chemical Formula | C6H7NO |
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Average Molecular Weight | 109.1259 |
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Monoisotopic Molecular Weight | 109.052763851 |
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IUPAC Name | 4-aminophenol |
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Traditional Name | aminophenol |
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CAS Registry Number | 123-30-8 |
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SMILES | NC1=CC=C(O)C=C1 |
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InChI Identifier | InChI=1S/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2 |
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InChI Key | PLIKAWJENQZMHA-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Aniline and substituted anilines |
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Direct Parent | Aniline and substituted anilines |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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4-Aminophenol,1TMS,isomer #1 | C[Si](C)(C)OC1=CC=C(N)C=C1 | 1354.4 | Semi standard non polar | 33892256 | 4-Aminophenol,1TMS,isomer #2 | C[Si](C)(C)NC1=CC=C(O)C=C1 | 1535.1 | Semi standard non polar | 33892256 | 4-Aminophenol,2TMS,isomer #1 | C[Si](C)(C)NC1=CC=C(O[Si](C)(C)C)C=C1 | 1536.0 | Semi standard non polar | 33892256 | 4-Aminophenol,2TMS,isomer #1 | C[Si](C)(C)NC1=CC=C(O[Si](C)(C)C)C=C1 | 1512.7 | Standard non polar | 33892256 | 4-Aminophenol,2TMS,isomer #1 | C[Si](C)(C)NC1=CC=C(O[Si](C)(C)C)C=C1 | 1567.2 | Standard polar | 33892256 | 4-Aminophenol,2TMS,isomer #2 | C[Si](C)(C)N(C1=CC=C(O)C=C1)[Si](C)(C)C | 1616.4 | Semi standard non polar | 33892256 | 4-Aminophenol,2TMS,isomer #2 | C[Si](C)(C)N(C1=CC=C(O)C=C1)[Si](C)(C)C | 1694.9 | Standard non polar | 33892256 | 4-Aminophenol,2TMS,isomer #2 | C[Si](C)(C)N(C1=CC=C(O)C=C1)[Si](C)(C)C | 1691.0 | Standard polar | 33892256 | 4-Aminophenol,3TMS,isomer #1 | C[Si](C)(C)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1 | 1583.1 | Semi standard non polar | 33892256 | 4-Aminophenol,3TMS,isomer #1 | C[Si](C)(C)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1 | 1618.3 | Standard non polar | 33892256 | 4-Aminophenol,3TMS,isomer #1 | C[Si](C)(C)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1 | 1522.5 | Standard polar | 33892256 | 4-Aminophenol,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C(N)C=C1 | 1570.2 | Semi standard non polar | 33892256 | 4-Aminophenol,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC1=CC=C(O)C=C1 | 1769.8 | Semi standard non polar | 33892256 | 4-Aminophenol,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1 | 2005.0 | Semi standard non polar | 33892256 | 4-Aminophenol,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1 | 1975.7 | Standard non polar | 33892256 | 4-Aminophenol,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1 | 1856.5 | Standard polar | 33892256 | 4-Aminophenol,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C | 2085.4 | Semi standard non polar | 33892256 | 4-Aminophenol,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C | 2122.1 | Standard non polar | 33892256 | 4-Aminophenol,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C | 1875.2 | Standard polar | 33892256 | 4-Aminophenol,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1 | 2298.6 | Semi standard non polar | 33892256 | 4-Aminophenol,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1 | 2252.6 | Standard non polar | 33892256 | 4-Aminophenol,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1 | 1922.5 | Standard polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - 4-Aminophenol EI-B (Non-derivatized) | splash10-0a4i-6900000000-9c5bfea7a6ff3c845001 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 4-Aminophenol EI-B (Non-derivatized) | splash10-0pe9-9300000000-8ff47e2157f6fbfe6754 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 4-Aminophenol GC-EI-TOF (Non-derivatized) | splash10-0f79-1890000000-c8247060f46131c693d1 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 4-Aminophenol GC-EI-TOF (Non-derivatized) | splash10-03di-1927000000-b873199d9ac85605a4df | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 4-Aminophenol EI-B (Non-derivatized) | splash10-0a4i-6900000000-9c5bfea7a6ff3c845001 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 4-Aminophenol EI-B (Non-derivatized) | splash10-0pe9-9300000000-8ff47e2157f6fbfe6754 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 4-Aminophenol GC-EI-TOF (Non-derivatized) | splash10-0f79-1890000000-c8247060f46131c693d1 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 4-Aminophenol GC-EI-TOF (Non-derivatized) | splash10-03di-1927000000-b873199d9ac85605a4df | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Aminophenol GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-5900000000-e64da39e73e3c0ea696c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Aminophenol GC-MS (1 TMS) - 70eV, Positive | splash10-060r-6900000000-2c6cd652b49e26ce3fce | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Aminophenol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Aminophenol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0a4i-9700000000-00bffb48fd955696bccc | 2014-09-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - 4-Aminophenol Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-03di-3900000000-906f96b14dfdad2310de | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 4-Aminophenol Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-014i-9000000000-d56be0077647bc66e962 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 4-Aminophenol Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-014i-9000000000-937794addf5b73c988e9 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 4-Aminophenol LC-ESI-QFT , positive-QTOF | splash10-03di-2900000000-1d20b6ad92e8fe4dcb55 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 4-Aminophenol 35V, Positive-QTOF | splash10-03di-2900000000-5950ca2352822bea4a01 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 4-Aminophenol 35V, Positive-QTOF | splash10-02tc-9300000000-3524fecaa931f284564b | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Aminophenol 10V, Positive-QTOF | splash10-03di-0900000000-da3b2114d9298a0363e7 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Aminophenol 20V, Positive-QTOF | splash10-03di-1900000000-b43943b1e137b2912b0f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Aminophenol 40V, Positive-QTOF | splash10-00lr-9000000000-8ca8655366b90d8f42df | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Aminophenol 10V, Negative-QTOF | splash10-0a4i-0900000000-28f35dbe83fee57d4a70 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Aminophenol 20V, Negative-QTOF | splash10-0a4i-0900000000-6aa4cd1a9d2a859fa70b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Aminophenol 40V, Negative-QTOF | splash10-0a7i-9300000000-177dcaf10b9e95cb409c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Aminophenol 10V, Positive-QTOF | splash10-03di-0900000000-c89e2460dc3caf4abe05 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Aminophenol 20V, Positive-QTOF | splash10-014i-9100000000-b0a8e0715ece78a9716d | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Aminophenol 40V, Positive-QTOF | splash10-0159-9000000000-aed714f11873786e9c3a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Aminophenol 10V, Negative-QTOF | splash10-0a4i-0900000000-875d8abd6f6773a40634 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Aminophenol 20V, Negative-QTOF | splash10-0a4i-0900000000-875d8abd6f6773a40634 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Aminophenol 40V, Negative-QTOF | splash10-0f6x-9200000000-17afc5bcee8bb56bc9e8 | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental) | 2012-12-04 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 10.00 (0.03-20.00) uM | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022462 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 392 |
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KEGG Compound ID | C02372 |
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BioCyc ID | CPD-259 |
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BiGG ID | Not Available |
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Wikipedia Link | 4-Aminophenol |
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METLIN ID | 6051 |
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PubChem Compound | 403 |
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PDB ID | Not Available |
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ChEBI ID | 17602 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1198931 |
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References |
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Synthesis Reference | Zhu, 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. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - 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 ]
- Clark PM, Clark JD, Wheatley T: Urine discoloration after acetaminophen overdose. Clin Chem. 1986 Sep;32(9):1777-8. [PubMed:3742803 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
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