Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H6O2 |
| Molecular Weight | 110.1106 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC=C(O)C=C1
InChI
InChIKey=QIGBRXMKCJKVMJ-UHFFFAOYSA-N
InChI=1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H
| Molecular Formula | C6H6O2 |
| Molecular Weight | 110.1106 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including:
https://en.wikipedia.org/wiki/Hydroquinone
Curator's Comment: description was created based on several sources, including:
https://en.wikipedia.org/wiki/Hydroquinone
Hydroquinone, aka benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. Its chemical structure features two hydroxyl groups bonded to a benzene ring in a para position. It is a white granular solid. Substituted derivatives of this parent compound are also referred to as hydroquinones. The name "hydroquinone" was coined by Friedrich Wöhler in 1843. In human medicine, hydroquinone is used as a topical application in skin whitening to reduce the color of skin. It does not have the same predisposition to cause dermatitis as metol does. 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 (variation in nuclei sizes), mononuclear cell leukemia, hepatocellular adenomas and renal tubule cell adenomas. One of the components in TRI-LUMA Cream, hydroquinone, is a depigmenting agent, and may interrupt one or more steps in the tyrosine-tyrosinase pathway of melanin synthesis. However, the mechanism of action of the active ingredients in TRI-LUMA Cream in the treatment of melasma is unknown.
Originator
Sources: http://everything.explained.today/Hydroquinone/
Curator's Comment: Friedrich Wöhler in 1843
Approval Year
Doses
| Dose | Population | Adverse events |
|---|---|---|
4 % 1 times / day multiple, topical Recommended Dose: 4 %, 1 times / day Route: topical Route: multiple Dose: 4 %, 1 times / day Sources: |
unhealthy, 41.4 Health Status: unhealthy Age Group: 41.4 Sex: M+F Sources: |
Disc. AE: Application site erythema, Redness facial... AEs leading to discontinuation/dose reduction: Application site erythema Sources: Redness facial Telangiectasia (grade 3-4) Rosacea Facial flushing Acne Acne papular Acne aggravated Skin irritation Peeling Perioral dermatitis Facial hair increased Dry skin Saliva discolouration |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Acne aggravated | Disc. AE | 4 % 1 times / day multiple, topical Recommended Dose: 4 %, 1 times / day Route: topical Route: multiple Dose: 4 %, 1 times / day Sources: |
unhealthy, 41.4 Health Status: unhealthy Age Group: 41.4 Sex: M+F Sources: |
| Acne papular | Disc. AE | 4 % 1 times / day multiple, topical Recommended Dose: 4 %, 1 times / day Route: topical Route: multiple Dose: 4 %, 1 times / day Sources: |
unhealthy, 41.4 Health Status: unhealthy Age Group: 41.4 Sex: M+F Sources: |
| Acne | Disc. AE | 4 % 1 times / day multiple, topical Recommended Dose: 4 %, 1 times / day Route: topical Route: multiple Dose: 4 %, 1 times / day Sources: |
unhealthy, 41.4 Health Status: unhealthy Age Group: 41.4 Sex: M+F Sources: |
| Application site erythema | Disc. AE | 4 % 1 times / day multiple, topical Recommended Dose: 4 %, 1 times / day Route: topical Route: multiple Dose: 4 %, 1 times / day Sources: |
unhealthy, 41.4 Health Status: unhealthy Age Group: 41.4 Sex: M+F Sources: |
| Dry skin | Disc. AE | 4 % 1 times / day multiple, topical Recommended Dose: 4 %, 1 times / day Route: topical Route: multiple Dose: 4 %, 1 times / day Sources: |
unhealthy, 41.4 Health Status: unhealthy Age Group: 41.4 Sex: M+F Sources: |
| Facial flushing | Disc. AE | 4 % 1 times / day multiple, topical Recommended Dose: 4 %, 1 times / day Route: topical Route: multiple Dose: 4 %, 1 times / day Sources: |
unhealthy, 41.4 Health Status: unhealthy Age Group: 41.4 Sex: M+F Sources: |
| Facial hair increased | Disc. AE | 4 % 1 times / day multiple, topical Recommended Dose: 4 %, 1 times / day Route: topical Route: multiple Dose: 4 %, 1 times / day Sources: |
unhealthy, 41.4 Health Status: unhealthy Age Group: 41.4 Sex: M+F Sources: |
| Peeling | Disc. AE | 4 % 1 times / day multiple, topical Recommended Dose: 4 %, 1 times / day Route: topical Route: multiple Dose: 4 %, 1 times / day Sources: |
unhealthy, 41.4 Health Status: unhealthy Age Group: 41.4 Sex: M+F Sources: |
| Perioral dermatitis | Disc. AE | 4 % 1 times / day multiple, topical Recommended Dose: 4 %, 1 times / day Route: topical Route: multiple Dose: 4 %, 1 times / day Sources: |
unhealthy, 41.4 Health Status: unhealthy Age Group: 41.4 Sex: M+F Sources: |
| Redness facial | Disc. AE | 4 % 1 times / day multiple, topical Recommended Dose: 4 %, 1 times / day Route: topical Route: multiple Dose: 4 %, 1 times / day Sources: |
unhealthy, 41.4 Health Status: unhealthy Age Group: 41.4 Sex: M+F Sources: |
| Rosacea | Disc. AE | 4 % 1 times / day multiple, topical Recommended Dose: 4 %, 1 times / day Route: topical Route: multiple Dose: 4 %, 1 times / day Sources: |
unhealthy, 41.4 Health Status: unhealthy Age Group: 41.4 Sex: M+F Sources: |
| Saliva discolouration | Disc. AE | 4 % 1 times / day multiple, topical Recommended Dose: 4 %, 1 times / day Route: topical Route: multiple Dose: 4 %, 1 times / day Sources: |
unhealthy, 41.4 Health Status: unhealthy Age Group: 41.4 Sex: M+F Sources: |
| Skin irritation | Disc. AE | 4 % 1 times / day multiple, topical Recommended Dose: 4 %, 1 times / day Route: topical Route: multiple Dose: 4 %, 1 times / day Sources: |
unhealthy, 41.4 Health Status: unhealthy Age Group: 41.4 Sex: M+F Sources: |
| Telangiectasia | grade 3-4 Disc. AE |
4 % 1 times / day multiple, topical Recommended Dose: 4 %, 1 times / day Route: topical Route: multiple Dose: 4 %, 1 times / day Sources: |
unhealthy, 41.4 Health Status: unhealthy Age Group: 41.4 Sex: M+F Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Different effects of genistein and resveratrol on oxidative DNA damage in vitro. | 2002-01-15 |
|
| Hepatic and pulmonary microsomal benzene metabolism in CYP2E1 knockout mice. | 2001-12-28 |
|
| Cytochrome P450 isozymes involved in the metabolism of phenol, a benzene metabolite. | 2001-12-15 |
|
| A study on grafting and characterization of HMDI-modified calcium hydrogenphosphate. | 2001-12 |
|
| Release of iron from ferritin by metabolites of benzene and superoxide radical generating agents. | 2001-11-30 |
|
| Alanine-scanning of the 50's loop in the Clostridium beijerinckii flavodoxin: evaluation of additivity and the importance of interactions provided by the main chain in the modulation of the oxidation-reduction potentials. | 2001-11-13 |
|
| Benzene-free synthesis of hydroquinone. | 2001-11-07 |
|
| Total synthesis and determination of the absolute configuration of coscinosulfate. A new selective inhibitor of Cdc25 protein phosphatase. | 2001-11-02 |
|
| Reversal of mitomycin C resistance by overexpression of bioreductive enzymes in Chinese hamster ovary cells. | 2001-11-01 |
|
| GC-MS analysis of hydrophobic root exudates of sorghum and implications on the parasitic plant Striga asiatica. | 2001-11 |
|
| [Effect of C27-steroids on lipid peroxidation in rat liver mitochondria]. | 2001-10-20 |
|
| Self-assembly of novel [3]- and [2]rotaxanes with two different ring components: donor-acceptor and hydrogen bonding interactions and molecular-shuttling behavior. | 2001-10-19 |
|
| Photochemistry of methoxyhydroquinone and methoxy-p-benzoquinone in solution related to the photoyellowing of the lignocellulosics. | 2001-10 |
|
| Validated methods for direct determination of hydroquinone glucuronide and sulfate in human urine after oral intake of bearberry leaf extract by capillary zone electrophoresis. | 2001-09-25 |
|
| Validated method for the determination of hydroquinone in human urine by high-performance liquid chromatography-coulometric-array detection. | 2001-09-15 |
|
| Inhibition of DNA cross-linking by mitomycin C by peroxidase-mediated oxidation of mitomycin C hydroquinone. | 2001-09-14 |
|
| Differential involvement of caspases in hydroquinone-induced apoptosis in human leukemic hl-60 and jurkat cells. | 2001-09-01 |
|
| Electrochemical oxidation of ochratoxin A: correlation with 4-chlorophenol. | 2001-09 |
|
| Oxidation of hydroquinones by the versatile ligninolytic peroxidase from Pleurotus eryngii. H2O2 generation and the influence of Mn2+. | 2001-09 |
|
| Structure of an active soluble mutant of the membrane-associated (S)-mandelate dehydrogenase. | 2001-08-21 |
|
| Dual-mode "co-conformational" switching in catenanes incorporating bipyridinium and dialkylammonium recognition sites. | 2001-08-17 |
|
| Mn(III) center availability as a rate controlling factor in the oxidation of phenol and sulfide on delta-MnO2. | 2001-08-15 |
|
| Surface NADH oxidase of HeLa cells lacks intrinsic membrane binding motifs. | 2001-08-15 |
|
| Benzene metabolites antagonize etoposide-stabilized cleavable complexes of DNA topoisomerase IIalpha. | 2001-08-01 |
|
| Concerted action of DT-diaphorase and superoxide dismutase in preventing redox cycling of naphthoquinones: an evaluation. | 2001-08 |
|
| Primary multiple miliary osteoma cutis and exogenous ochronosis. | 2001-08 |
|
| Effect of pre-treatment on the surface and electrochemical properties of screen-printed carbon paste electrodes. | 2001-08 |
|
| Effects of all-trans retinoic acid on melanogenesis in pigmented skin equivalents and monolayer culture of melanocytes. | 2001-08 |
|
| Highly concentrated phenolic wastewater treatment by the photo-Fenton reaction, mechanism study by FTIR-ATR. | 2001-08 |
|
| Protein adducts of 1,4-benzoquinone and benzene oxide among smokers and nonsmokers exposed to benzene in China. | 2001-08 |
|
| Abiotic Fe(III) induced mineralization of phenolic substances. | 2001-08 |
|
| The influence of pH and cadmium sulfide on the photocatalytic degradation of 2-chlorophenol in titanium dioxide suspensions. | 2001-08 |
|
| Role of hydrogen bonding interactions to N(3)H of the flavin mononucleotide cofactor in the modulation of the redox potentials of the Clostridium beijerinckii flavodoxin. | 2001-07-31 |
|
| Inhibitory effect of copper(II) on zinc(II)-induced aggregation of amyloid beta-peptide. | 2001-07-27 |
|
| Strong supramolecular-based magnetic exchange in pi-stacked radicals. Structure and magnetism of a hydrogen-bonded verdazyl radical:hydroquinone molecular solid. | 2001-07-25 |
|
| [Depigmentation for cosmetic purposes: prevalence and side-effects in a female population in Senegal]. | 2001-07-19 |
|
| Pharmacokinetic studies in Tg.AC and FVB mice administered [14C] benzene either by oral gavage or intradermal injection. | 2001-07-15 |
|
| Purification and characterization of glutathione conjugate reductase: a component of the tetrachlorohydroquinone reductive dehalogenase system from Phanerochaete chrysosporium. | 2001-07-15 |
|
| Studies on porphyrin-quinhydrone complexes: molecular recognition of quinone and hydroquinone in solution. | 2001-06-29 |
|
| Role of aromatic stacking interactions in the modulation of the two-electron reduction potentials of flavin and substrate/product in Megasphaera elsdenii short-chain acyl-coenzyme A dehydrogenase. | 2001-06-26 |
|
| Electrogenic proton transfer in Rhodobacter sphaeroides reaction centers: effect of coenzyme Q(10) substitution by decylubiquinone in the Q(B) binding site. | 2001-06-15 |
|
| Surface control of oxidation by an adsorbed Ru(IV)-oxo complex. | 2001-06-06 |
|
| Isolation and study of some properties of laccase from the basidiomycetes Cerrena maxima. | 2001-06 |
|
| [Sensitization to resorcinol in a prescription verrucide preparation: unusual systemic clinical features and prevalence]. | 2001-05 |
|
| Electron self-exchange in the solid-state: cocrystals of hydroquinone and bipyridyl triazole. | 2001-03-28 |
|
| Melasma treated with hydroquinone, tretinoin, and a fluorinated steroid. | 2001-03 |
|
| Exogenous ochronosis. An update on clinical features, causative agents and treatment options. | 2001 |
|
| Hypoxia and oxidative stress. Tumour hypoxia--therapeutic considerations. | 2001 |
|
| Two-photon ionization thresholds of matrix-assisted laser desorption/ionization matrix clusters. | 2001 |
|
| Use of in vitro assays to assess hematotoxic effects of environmental compounds. | 2001 |
Patents
| Substance Class |
Chemical
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| Record UNII |
XV74C1N1AE
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Validated (UNII)
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NCI_THESAURUS |
C45175
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Food Contact Sustance Notif, (FCN No.) |
FCN NO. 1246
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NDF-RT |
N0000175851
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CFR |
21 CFR 176.170
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N0000175850
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QD11AX11
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N0000175854
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D11AX11
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m6115
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CHEMBL537
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Hydroquinone
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HYDROQUINONE
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C031927
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SALT/SOLVATE -> PARENT |
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PARENT -> METABOLITE |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |
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