| Record Information |
|---|
| Version | 2.0 |
|---|
| Creation Date | 2014-09-05 17:10:15 UTC |
|---|
| Update Date | 2014-12-24 20:26:52 UTC |
|---|
| Accession Number | T3D4577 |
|---|
| Identification |
|---|
| Common Name | Hydroquinone |
|---|
| Class | Small Molecule |
|---|
| Description | Hydroquinone, also benzene-1,4-diol, is an aromatic organic compound which is a type of phenol. 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. In human medicine, hydroquinone is used as a topical application in skin whitening to reduce the color of skin. In 2006, the United States Food and Drug Administration revoked its previous approval of hydroquinone and proposed a ban on all over-the-counter preparations. The FDA stated that hydroquinone cannot be ruled out as a potential carcinogen. This conclusion was reached based on the extent of absorption in humans and the incidence of neoplasms in rats in several studies where adult rats were found to have increased rates of tumours, including thyroid follicular cell hyperplasias, anisokaryosis, mononuclear cell leukemia, hepatocellular adenomas and renal tubule cell adenomas. Numerous studies have revealed that hydroquinone can cause exogenous ochronosis, a disfiguring disease in which blue-black pigments are deposited onto the skin, if taken orally; however, skin preparations containing the ingredient are administered topically. The FDA has classified hydroquinone currently as a safe product, as currently used. (Wikipedia) |
|---|
| Compound Type | - Cigarette Toxin
- Food Toxin
- Household Toxin
- Metabolite
- Organic Compound
- Pollutant
- Synthetic Compound
|
|---|
| Chemical Structure | |
|---|
| Synonyms | | Synonym | | 1,4-Benzenediol | | 1,4-Dihydroxy-benzeen | | 1,4-Dihydroxy-benzol | | 1,4-Dihydroxybenzen | | 1,4-Diidrobenzene | | 4-Hydroxyphenol | | a-Hydroquinone | | alpha-Hydroquinone | | b-Quinol | | Benzene-1,4-diol | | Benzohydroquinone | | Benzoquinol | | beta-Quinol | | Dihydroquinone | | Dihydroxybenzene | | Hydrochinon | | Hydrochinone | | Hydroquinol | | Hydroquinole | | Hydroquinone for synthesis | | Hydroquinone gr | | Hydroquinoue | | Idrochinone | | Melanex | | p-Benzenediol | | p-Dihydroxybenzene | | p-Dioxobenzene | | p-Dioxybenzene | | p-Hydroquinone | | p-Hydroxybenzene | | p-Hydroxyphenol | | Phiaquin | | Quinol | | Solaquin forte |
|
|---|
| Chemical Formula | C6H6O2 |
|---|
| Average Molecular Mass | 110.111 g/mol |
|---|
| Monoisotopic Mass | 110.037 g/mol |
|---|
| CAS Registry Number | 123-31-9 |
|---|
| IUPAC Name | benzene-1,4-diol |
|---|
| Traditional Name | α-hydroquinone |
|---|
| SMILES | OC1=CC=C(O)C=C1 |
|---|
| InChI Identifier | InChI=1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H |
|---|
| InChI Key | InChIKey=QIGBRXMKCJKVMJ-UHFFFAOYSA-N |
|---|
| Chemical Taxonomy |
|---|
| 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. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Benzenoids |
|---|
| Class | Phenols |
|---|
| Sub Class | Benzenediols |
|---|
| Direct Parent | Hydroquinones |
|---|
| Alternative Parents | |
|---|
| Substituents | - Hydroquinone
- 1-hydroxy-2-unsubstituted benzenoid
- Monocyclic benzene moiety
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic homomonocyclic compound
|
|---|
| Molecular Framework | Aromatic homomonocyclic compounds |
|---|
| External Descriptors | |
|---|
| Biological Properties |
|---|
| Status | Detected and Not Quantified |
|---|
| Origin | Exogenous |
|---|
| Cellular Locations | |
|---|
| Biofluid Locations | Not Available |
|---|
| Tissue Locations | - Bone Marrow
- Fibroblasts
- Kidney
- Liver
- Skin
- Stratum Corneum
|
|---|
| Pathways | Not Available |
|---|
| Applications | Not Available |
|---|
| Biological Roles | |
|---|
| Chemical Roles | Not Available |
|---|
| Physical Properties |
|---|
| State | Solid |
|---|
| Appearance | Hydroquinone is a white granular solid at room temperature and pressure. |
|---|
| Experimental Properties | | Property | Value |
|---|
| Melting Point | 172.3 °C | | Boiling Point | 286°C (546.8°F) | | Solubility | 72.0 mg/mL at 25 °C | | LogP | 0.59 |
|
|---|
| Predicted Properties | |
|---|
| Spectra |
|---|
| Spectra | | Spectrum Type | Description | Splash Key | View |
|---|
| GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0f79-2490000000-6b4fec222a3499d93790 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-03di-9800000000-c90fd4986fea9691ecbf | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-03e9-9300000000-f8b11742557329691e8a | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0f79-2490000000-6b4fec222a3499d93790 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0f79-2690000000-7306adcc7121a11d67cc | JSpectraViewer | MoNA | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-03di-5900000000-954dc96d8e3eb85b8324 | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-00e9-8950000000-512c0cf5ddc0b120ec8e | JSpectraViewer | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-03di-9600000000-e670ba090cb27367db12 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-01p6-9000000000-5fc32c7688c1612df1e7 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-000i-9000000000-c5853ce8ef225ea5c353 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - EI-B (Unknown) , Positive | splash10-03di-9800000000-c90fd4986fea9691ecbf | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-0a4i-0900000000-5635f0157cd37deb1121 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-03di-2900000000-05be113033a709130eed | JSpectraViewer | MoNA | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0900000000-8d8328e4f7cd2ebaa27d | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-1900000000-9290fcb93f170fc3143f | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01si-9200000000-9f707b9d0c4ad0b73b30 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-d3aae38632ac4c40fd4f | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0900000000-74f15490ba4f49cf8c18 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9800000000-1cb01248e88fce387578 | JSpectraViewer | | MS | Mass Spectrum (Electron Ionization) | splash10-03di-9500000000-1fa8477944a662535e76 | JSpectraViewer | MoNA | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
|
|---|
| Toxicity Profile |
|---|
| Route of Exposure | Not Available |
|---|
| Mechanism of Toxicity | Not Available |
|---|
| Metabolism | Not Available |
|---|
| Toxicity Values | Not Available |
|---|
| Lethal Dose | Not Available |
|---|
| Carcinogenicity (IARC Classification) | 3, not classifiable as to its carcinogenicity to humans. (16) |
|---|
| Uses/Sources | 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 in most photographic developers where, with the compound Metol, it reduces silver halides to elemental silver. In human medicine, hydroquinone is used as a topical application in skin whitening to reduce the color of skin. |
|---|
| Minimum Risk Level | Not Available |
|---|
| Health Effects | Not Available |
|---|
| Symptoms | Not Available |
|---|
| Treatment | Not Available |
|---|
| Normal Concentrations |
|---|
| Not Available |
|---|
| Abnormal Concentrations |
|---|
| Not Available |
|---|
| External Links |
|---|
| DrugBank ID | Not Available |
|---|
| HMDB ID | HMDB02434 |
|---|
| PubChem Compound ID | 785 |
|---|
| ChEMBL ID | CHEMBL537 |
|---|
| ChemSpider ID | 764 |
|---|
| KEGG ID | C00530 |
|---|
| UniProt ID | Not Available |
|---|
| OMIM ID | |
|---|
| ChEBI ID | 17594 |
|---|
| BioCyc ID | 236-TRICHLOROHYDROQUINONE |
|---|
| CTD ID | Not Available |
|---|
| Stitch ID | Not Available |
|---|
| PDB ID | HQE |
|---|
| ACToR ID | Not Available |
|---|
| Wikipedia Link | Hydroquinone |
|---|
| References |
|---|
| Synthesis Reference | Miyanohara, Isao; Yanagihara, Tadahisa. Hydroquinone. Jpn. Kokai Tokkyo Koho (1977), 4 pp. |
|---|
| MSDS | Link |
|---|
| General References | - 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. [15618234 ]
- 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. [11243376 ]
- 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. [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. [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. [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. [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. [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. [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. [7482585 ]
- Boyle J, Kennedy CT: Hydroquinone concentrations in skin lightening creams. Br J Dermatol. 1986 Apr;114(4):501-4. [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. [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. [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. [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. [15129564 ]
- Halliwell, Barry B., and Henrik E. Poulsen (2006). Cigarette Smoke and Oxidative Stress. Berlin: Springer. [ISBN: 978-3-540-31410-3 (Print) 978-3-540-32232-0 (Online)]
- International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
|
|---|
| Gene Regulation |
|---|
| Up-Regulated Genes | Not Available |
|---|
| Down-Regulated Genes | Not Available |
|---|
