Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-05-22 14:17:53 UTC |
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Update Date | 2023-02-21 17:16:24 UTC |
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HMDB ID | HMDB0002434 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Hydroquinone |
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Description | Hydroquinone, also known as benzene-1,4-diol, is an aromatic organic compound which is a type of phenol, having the chemical formula C6H4(OH)2. Its chemical structure has two hydroxyl groups bonded to a benzene ring in a para position. Hydroquinone is commonly used as a biomarker for benzene exposure. The presence of hydroquinone in normal individuals stems mainly from direct dietary ingestion, catabolism of tyrosine and other substrates by gut bacteria, ingestion of arbutin-containing foods, cigarette smoking, and the use of some over-the-counter medicines. Hydroquinone is a white granular solid at room temperature and pressure. The hydroxyl groups of hydroquinone are quite weakly acidic. Hydroquinone can lose an H+ from one of the hydroxyls to form a monophenolate ion or lose an H+ from both to form a diphenolate ion. Hydroquinone has a variety of uses principally associated with its action as a reducing agent which is soluble in water. It is a major component of most photographic developers where, with the compound Metol, it reduces silver halides to elemental silver. |
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Structure | InChI=1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H |
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Synonyms | Value | Source |
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1,4-Benzenediol | ChEBI | 1,4-Dihydroxybenzene | ChEBI | 4-Hydroxyphenol | ChEBI | Benzene-1,4-diol | ChEBI | Eldoquin | ChEBI | p-Benzenediol | ChEBI | p-Hydroquinone | ChEBI | p-Hydroxyphenol | ChEBI | Quinol | ChEBI | Artra | MeSH | Eldopaque | MeSH | Esoterica | MeSH | Hidroquilaude | MeSH | Hidroquin | MeSH | Hidroquinona isdin | MeSH | Licostrata | MeSH | Lustra | MeSH | Melanasa | MeSH | Melanex | MeSH | Melpaque | MeSH | Melquin | MeSH | Neostrata HQ | MeSH | Phiaquin | MeSH | Solaquin | MeSH | Ultraquin | MeSH | beta-Quinol | MeSH | Hydroquinone, copper (1+) salt | MeSH | Hydroquinone, lead (2+) salt (2:1) | MeSH | Hydroquinone, monocopper (2+) salt | MeSH | 1,4-Dihydroxy-benzeen | HMDB | 1,4-Dihydroxy-benzol | HMDB | 1,4-Dihydroxybenzen | HMDB | 1,4-Diidrobenzene | HMDB | a-Hydroquinone | HMDB | alpha-Hydroquinone | HMDB | b-Quinol | HMDB | Benzohydroquinone | HMDB | Benzoquinol | HMDB | Dihydroquinone | HMDB | Dihydroxybenzene | HMDB | Hydrochinon | HMDB | Hydrochinone | HMDB | Hydroquinol | HMDB | Hydroquinole | HMDB | Hydroquinone for synthesis | HMDB | Hydroquinone GR | HMDB | Hydroquinoue | HMDB | Idrochinone | HMDB | p-Dihydroxybenzene | HMDB | P-Dioxobenzene | HMDB | p-Dioxybenzene | HMDB | P-Hydroxybenzene | HMDB | Solaquin forte | HMDB | Eldoquin forte | MeSH, HMDB | Stratus brand 1 OF hydroquinone | MeSH, HMDB | ICN brand 1 OF hydroquinone | MeSH, HMDB | Plough brand 2 OF hydroquinone | MeSH, HMDB | Eldopaque forte | MeSH, HMDB | ICN brand 4 OF hydroquinone | MeSH, HMDB | Black and white | MeSH, HMDB | ICN brand 2 OF hydroquinone | MeSH, HMDB | ICN brand 3 OF hydroquinone | MeSH, HMDB | Plough brand 1 OF hydroquinone | MeSH, HMDB | Stratus brand 2 OF hydroquinone | MeSH, HMDB | 1,4-Benzoquinol | PhytoBank | 1,4-Phenylenediol | PhytoBank | 1,4-p-Benzenediol | PhytoBank | p-Dihydroquinone | PhytoBank | p-Phenylenediol | PhytoBank | p-Quinol | PhytoBank |
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Chemical Formula | C6H6O2 |
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Average Molecular Weight | 110.1106 |
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Monoisotopic Molecular Weight | 110.036779436 |
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IUPAC Name | benzene-1,4-diol |
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Traditional Name | α-hydroquinone |
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CAS Registry Number | 123-31-9 |
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SMILES | OC1=CC=C(O)C=C1 |
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InChI Identifier | InChI=1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H |
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InChI Key | QIGBRXMKCJKVMJ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as hydroquinones. Hydroquinones are compounds containing a hydroquinone moiety, which consists of a benzene ring with a hydroxyl groups at positions 1 and 4. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Phenols |
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Sub Class | Benzenediols |
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Direct Parent | Hydroquinones |
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Alternative Parents | |
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Substituents | - Hydroquinone
- 1-hydroxy-2-unsubstituted benzenoid
- Monocyclic benzene moiety
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- 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 | Property | Value | Reference |
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Melting Point | 172.3 °C | Not Available | Boiling Point | 286.00 to 288.00 °C. @ 760.00 mm Hg | The Good Scents Company Information System | Water Solubility | 72 mg/mL at 25 °C | Not Available | LogP | 0.59 | HANSCH,C ET AL. (1995) |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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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 - Hydroquinone GC-MS (2 TMS) | splash10-0f79-2490000000-6b4fec222a3499d93790 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Hydroquinone EI-B (Non-derivatized) | splash10-03di-9800000000-c90fd4986fea9691ecbf | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Hydroquinone EI-B (Non-derivatized) | splash10-03e9-9300000000-f8b11742557329691e8a | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Hydroquinone GC-MS (Non-derivatized) | splash10-0f79-2490000000-6b4fec222a3499d93790 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Hydroquinone GC-EI-TOF (Non-derivatized) | splash10-0f79-2690000000-7306adcc7121a11d67cc | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hydroquinone GC-MS (Non-derivatized) - 70eV, Positive | splash10-03di-5900000000-954dc96d8e3eb85b8324 | 2017-07-27 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hydroquinone GC-MS (2 TMS) - 70eV, Positive | splash10-00e9-8950000000-512c0cf5ddc0b120ec8e | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hydroquinone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hydroquinone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-03di-9500000000-1fa8477944a662535e76 | 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 - Hydroquinone Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-03di-9600000000-e670ba090cb27367db12 | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroquinone Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-01p6-9000000000-5fc32c7688c1612df1e7 | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroquinone Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-000i-9000000000-c5853ce8ef225ea5c353 | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroquinone EI-B (Unknown) , Positive-QTOF | splash10-03di-9800000000-c90fd4986fea9691ecbf | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroquinone , negative-QTOF | splash10-0a4i-0900000000-5635f0157cd37deb1121 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroquinone , positive-QTOF | splash10-03di-2900000000-05be113033a709130eed | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroquinone 20V, Negative-QTOF | splash10-0a4i-9600000000-e0d15b2e4ea35a7a76be | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroquinone 20V, Positive-QTOF | splash10-01r6-9000000000-946504408977df40269a | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroquinone 10V, Negative-QTOF | splash10-0a4i-0900000000-c16180dd26c127563155 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroquinone 40V, Positive-QTOF | splash10-03dl-9000000000-cea1cb486f12ea31e3a1 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroquinone 10V, Positive-QTOF | splash10-01ox-9000000000-3a9d5710c88793e698f1 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroquinone 40V, Negative-QTOF | splash10-0006-9000000000-60eeaa79bff371773b2e | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroquinone 20V, Negative-QTOF | splash10-0a4i-0900000000-3a9e293da186985db7fa | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroquinone 40V, Negative-QTOF | splash10-0pb9-9000000000-84bb0a9b4c3cd16da2a7 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroquinone 10V, Negative-QTOF | splash10-0a4i-7900000000-2256214c81a3e04e01b7 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroquinone 10V, Positive-QTOF | splash10-03di-0900000000-8d8328e4f7cd2ebaa27d | 2015-05-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroquinone 20V, Positive-QTOF | splash10-03di-1900000000-9290fcb93f170fc3143f | 2015-05-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroquinone 40V, Positive-QTOF | splash10-01si-9200000000-9f707b9d0c4ad0b73b30 | 2015-05-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroquinone 10V, Negative-QTOF | splash10-0a4i-0900000000-d3aae38632ac4c40fd4f | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroquinone 20V, Negative-QTOF | splash10-0a4i-0900000000-74f15490ba4f49cf8c18 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroquinone 40V, Negative-QTOF | splash10-0a4i-9800000000-1cb01248e88fce387578 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroquinone 10V, Negative-QTOF | splash10-0a4i-0900000000-9f2c82efe2cba7470e17 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroquinone 20V, Negative-QTOF | splash10-0a4i-0900000000-9f2c82efe2cba7470e17 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroquinone 40V, Negative-QTOF | splash10-0f6x-9000000000-8213c13cc381b346f976 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroquinone 10V, Positive-QTOF | splash10-03di-0900000000-fd10fd64675560620b8d | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | 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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Disease References | Uremia |
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- Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
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General References | - McDonald TA, Holland NT, Skibola C, Duramad P, Smith MT: Hypothesis: phenol and hydroquinone derived mainly from diet and gastrointestinal flora activity are causal factors in leukemia. Leukemia. 2001 Jan;15(1):10-20. [PubMed:11243376 ]
- Gaskell M, McLuckie KI, Farmer PB: Comparison of the repair of DNA damage induced by the benzene metabolites hydroquinone and p-benzoquinone: a role for hydroquinone in benzene genotoxicity. Carcinogenesis. 2005 Mar;26(3):673-80. Epub 2004 Dec 23. [PubMed:15618234 ]
- Inayat-Hussain SH, McGuinness SM, Johansson R, Lundstrom J, Ross D: Caspase-dependent and -independent mechanisms in apoptosis induced by hydroquinone and catechol metabolites of remoxipride in HL-60 cells. Chem Biol Interact. 2000 Aug 15;128(1):51-63. [PubMed:10996300 ]
- Carbonnelle P, Lison D, Leroy JY, Lauwerys R: Effect of the benzene metabolite, hydroquinone, on interleukin-1 secretion by human monocytes in vitro. Toxicol Appl Pharmacol. 1995 Jun;132(2):220-6. [PubMed:7540334 ]
- Keh ES, Hayakawa I, Takahashi H, Watanabe A, Iwasaki Y, Akiyoshi K, Nakabayashi N: Improving a self-curing dental resin by eliminating oxygen, hydroquinone and water from its curing process. Dent Mater J. 2002 Dec;21(4):373-82. [PubMed:12608426 ]
- Subrahmanyam VV, Kolachana P, Smith MT: Hydroxylation of phenol to hydroquinone catalyzed by a human myeloperoxidase-superoxide complex: possible implications in benzene-induced myelotoxicity. Free Radic Res Commun. 1991;15(5):285-96. [PubMed:1666626 ]
- Li X, Zhuang Z, Liu J, Huang H, Wei Q, Yang X: [Protein changes in human embryonic lung fibroblasts after hydroquinone stimulation using proteomic technique]. Wei Sheng Yan Jiu. 2004 Nov;33(6):654-7. [PubMed:15727168 ]
- Bucks DA, McMaster JR, Guy RH, Maibach HI: Percutaneous absorption of hydroquinone in humans: effect of 1-dodecylazacycloheptan-2-one (azone) and the 2-ethylhexyl ester of 4-(dimethylamino)benzoic acid (Escalol 507). J Toxicol Environ Health. 1988;24(3):279-89. [PubMed:3260963 ]
- Barber ED, Hill T, Schum DB: The percutaneous absorption of hydroquinone (HQ) through rat and human skin in vitro. Toxicol Lett. 1995 Oct;80(1-3):167-72. [PubMed:7482585 ]
- Boyle J, Kennedy CT: Hydroquinone concentrations in skin lightening creams. Br J Dermatol. 1986 Apr;114(4):501-4. [PubMed:3964548 ]
- Nilsson LB: High sensitivity determination of the remoxipride hydroquinone metabolite NCQ-344 in plasma by coupled column reversed-phase liquid chromatography and electrochemical detection. Biomed Chromatogr. 1998 Mar-Apr;12(2):65-8. [PubMed:9568272 ]
- Oliveira NL, Kalf GF: Induced differentiation of HL-60 promyelocytic leukemia cells to monocyte/macrophages is inhibited by hydroquinone, a hematotoxic metabolite of benzene. Blood. 1992 Feb 1;79(3):627-33. [PubMed:1732008 ]
- Wester RC, Melendres J, Hui X, Cox R, Serranzana S, Zhai H, Quan D, Maibach HI: Human in vivo and in vitro hydroquinone topical bioavailability, metabolism, and disposition. J Toxicol Environ Health A. 1998 Jun 26;54(4):301-17. [PubMed:9638901 ]
- Kooyers TJ, Westerhof W: [Toxicological aspects and health risks associated with hydroquinone in skin bleaching formula]. Ned Tijdschr Geneeskd. 2004 Apr 17;148(16):768-71. [PubMed:15129564 ]
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