Hydroquinone
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Basic Info
| Common Name | Hydroquinone(F05460) |
| 2D Structure | |
| 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) |
| FRCD ID | F05460 |
| CAS Number | 123-31-9 |
| PubChem CID | 785 |
| Formula | C6H6O2 |
| IUPAC Name | benzene-1,4-diol |
| InChI Key | QIGBRXMKCJKVMJ-UHFFFAOYSA-N |
| InChI | InChI=1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H |
| Canonical SMILES | C1=CC(=CC=C1O)O |
| Isomeric SMILES | C1=CC(=CC=C1O)O |
| Wikipedia | Hydroquinone |
| Synonyms |
1,4-benzenediol
4-Hydroxyphenol
hydroquinone
Benzene-1,4-diol
123-31-9
Quinol
1,4-Dihydroxybenzene
p-Benzenediol
p-Hydroquinone
p-Hydroxyphenol
|
| Classifies |
Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Phenols |
| Subclass | Benzenediols |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Hydroquinones |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Hydroquinone - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as hydroquinones. These are compounds containing a hydroquinone moiety, which consists of a benzene ring with a hydroxyl groups at positions 1 and 4. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 110.112 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 0 |
| Complexity | 54.9 |
| Monoisotopic Mass | 110.037 |
| Exact Mass | 110.037 |
| XLogP | 0.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 8 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.6352 |
| Human Intestinal Absorption | HIA+ | 0.9928 |
| Caco-2 Permeability | Caco2+ | 0.9253 |
| P-glycoprotein Substrate | Non-substrate | 0.7758 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9820 |
| Non-inhibitor | 0.9875 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8828 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8220 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8167 |
| CYP450 2D6 Substrate | Non-substrate | 0.9048 |
| CYP450 3A4 Substrate | Non-substrate | 0.7496 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8444 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9071 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9781 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8778 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8867 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7776 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8717 |
| Non-inhibitor | 0.9606 | |
| AMES Toxicity | Non AMES toxic | 0.9512 |
| Carcinogens | Non-carcinogens | 0.7573 |
| Fish Toxicity | Low FHMT | 0.5531 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.7355 |
| Honey Bee Toxicity | High HBT | 0.7990 |
| Biodegradation | Ready biodegradable | 0.7313 |
| Acute Oral Toxicity | II | 0.7495 |
| Carcinogenicity (Three-class) | Non-required | 0.5519 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.2325 | LogS |
| Caco-2 Permeability | 1.5782 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0465 | LD50, mol/kg |
| Fish Toxicity | 1.8853 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3447 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Two-dimensional MoS2 as a nano-binder for ssDNA: Ultrasensitive aptamer basedamperometric detection of Ochratoxin A. | Mikrochim Acta | 2018 Feb 7 | 29594615 |
| The Usefulness of Non-Toxic Plant Metabolites in the Control of Bacterial Proliferation. | Probiotics Antimicrob Proteins | 2017 Sep | 28357646 |
| Phenolics from Mikania micrantha and Their Antioxidant Activity. | Molecules | 2017 Jul 8 | 28698451 |
| Anti-Inflammatory Activity of Citric Acid-Treated Wheat Germ Extract in Lipopolysaccharide-Stimulated Macrophages. | Nutrients | 2017 Jul 10 | 28698513 |
| Application of pristine and doped SnO<sub>2</sub> nanoparticles as a matrix for agro-hazardous material (organophosphate) detection. | Sci Rep | 2017 Feb 14 | 28195202 |
| Paracetamol biodegradation by activated sludge and photocatalysis and its removal by a micelle-clay complex, activated charcoal, and reverse osmosis membranes. | Environ Technol | 2016 Oct | 26852629 |
| The Nitrite-Scavenging Properties of Catechol, Resorcinol, and Hydroquinone: A Comparative Study on Their Nitration and Nitrosation Reactions. | J Food Sci | 2016 Nov | 27741359 |
| Laccase oxidation and removal of toxicants released during combustion processes. | Chemosphere | 2016 Feb | 26408262 |
| Experimental investigation of electro-rheological properties of modeled vegetable oils. | J Food Sci Technol | 2016 Feb | 27162414 |
| New High-performance Liquid Chromatography-DAD Method for Analytical Determination of Arbutin and Hydroquinone in Rat Plasma. | Indian J Pharm Sci | 2015 Sep-Oct | 26798166 |
| Crystal structure of PnpCD, a two-subunit hydroquinone 1,2-dioxygenase, reveals anovel structural class of Fe2+-dependent dioxygenases. | J Biol Chem | 2015 Oct 2 | 26304122 |
| Enzymatic amplification detection of peanut allergen Ara h1 using a stem-loop DNAbiosensor modified with a chitosan-mutiwalled carbon nanotube nanocomposite andspongy gold film. | Talanta | 2015 Jan | 25281135 |
| Biomolecule-free, selective detection of o-diphenol and its derivatives withWS2/TiO2-based photoelectrochemical platform. | Anal Chem | 2015 | 25844499 |
| Characterization of suspected illegal skin whitening cosmetics. | J Pharm Biomed Anal | 2014 Mar | 24334193 |
| Potential involvement of chemicals in liver cancer progression: an alternativetoxicological approach combining biomarkers and innovative technologies. | Toxicol In Vitro | 2014 Dec | 24997295 |
| Rapid screening of multiple antibiotic residues in milk using disposableamperometric magnetosensors. | Anal Chim Acta | 2014 Apr 11 | 24745735 |
| Marine hydroquinone zonarol prevents inflammation and apoptosis in dextran sulfate sodium-induced mice ulcerative colitis. | PLoS One | 2014 | 25409433 |
| Non-toxic melanin production inhibitors from Garcinia livingstonei (Clusiaceae). | J Ethnopharmacol | 2013 Sep 16 | 23891889 |
| Development and validation of a fast chromatographic method for screening and quantification of legal and illegal skin whitening agents. | J Pharm Biomed Anal | 2013 Sep | 23708434 |
| An electrochemical magneto immunosensor (EMIS) for the determination of paraquat residues in potato samples. | Anal Bioanal Chem | 2013 Sep | 23887278 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
- Gene Name:
- CA1
- Uniprot ID:
- P00915
- Molecular Weight:
- 28870.0 Da
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide. Participates in pH regulation. May be involved in the control of cell proliferation and transformation. Appears to be a novel specific biomarker for a cervical neoplasia.
- Gene Name:
- CA9
- Uniprot ID:
- Q16790
- Molecular Weight:
- 49697.36 Da
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA12
- Uniprot ID:
- O43570
- Molecular Weight:
- 39450.615 Da
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
- General Function:
- Metal ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA14
- Uniprot ID:
- Q9ULX7
- Molecular Weight:
- 37667.37 Da
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA3
- Uniprot ID:
- P07451
- Molecular Weight:
- 29557.215 Da
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina and retina epithelium, and acid release in the choriocapillaris in the choroid.
- Gene Name:
- CA4
- Uniprot ID:
- P22748
- Molecular Weight:
- 35032.075 Da
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide. Low activity.
- Gene Name:
- CA5A
- Uniprot ID:
- P35218
- Molecular Weight:
- 34750.21 Da
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA5B
- Uniprot ID:
- Q9Y2D0
- Molecular Weight:
- 36433.43 Da
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide. Its role in saliva is unknown.
- Gene Name:
- CA6
- Uniprot ID:
- P23280
- Molecular Weight:
- 35366.615 Da
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA7
- Uniprot ID:
- P43166
- Molecular Weight:
- 29658.235 Da
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye. Contributes to intracellular pH regulation in the duodenal upper villous epithelium during proton-coupled peptide absorption. Stimulates the chloride-bicarbonate exchange activity of SLC26A6.
- Gene Name:
- CA2
- Uniprot ID:
- P00918
- Molecular Weight:
- 29245.895 Da
References
- Innocenti A, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. doi: 10.1016/j.bmc.2008.06.013. Epub 2008 Jun 13. [18579385 ]