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53960 Fluka

Hydroquinone

≥99.0% (HPLC)

Synonym: 1,4-Benzenediol, 1,4-Dihydroxybenzene, HQ

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Properties

vapor density   3.81 (vs air)
vapor pressure   1 mmHg ( 132 °C)
assay   ≥99.0% (HPLC)
autoignition temp.   930 °F
bp   285 °C(lit.)
mp   171-173 °C
  172-175 °C(lit.)
solubility   H2O: soluble50 mg/mL, clear

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Hydroquinone

meets USP testing specifications

Hydroquinone

ReagentPlus®, ≥99.5%

Hydroquinone-d<SUB>4</SUB>-(<I>ring</I>-d<SUB>4</SUB>)

98 atom % D

Safety & Documentation

Safety Information

Signal word 
Danger
Hazard statements 
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
3
RTECS 
MX3500000
Flash Point(F) 
329 °F
Flash Point(C) 
165 °C

Protocols & Articles

Peer-Reviewed Papers

References

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Chemical genetics reveals a complex functional ground state of neural stem cells Diamandis, P., et. al. Nat. Chem. Biol. 3(5), 268-273, (2007)

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Differential 12C-/13C-isotope dansylation labeling and fast liquid chromatography/mass spectrometry for absolute and relative quantification of the metabolome. Guo K and Li L Anal. Chem. 81(10), 3919-32, (2009)

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QSAR study on permeability of hydrophobic compounds with artificial membranes. Masaaki Fujikawa et al Bioorg. Med. Chem. 15, 3756-67, (2007)

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In vitro effects of aldehydes present in tobacco smoke on gene expression in human lung alveolar epithelial cells. Cheah NP, Pennings JL, Vermeulen JP, et al. Toxicol. In Vitro 27(3), 1072-81, (2013)

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Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Alessio Innocenti et al Bioorg. Med. Chem. 16, 7424-8, (2008)

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Glassy carbon electrodes modified with gold nanoparticles for the simultaneous determination of three food antioxidants. Lin X, Ni Y, and Kokot S Anal. Chim. Acta 765, 54-62, (2013)

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A split-face evaluation of a novel pigment-lightening agent compared with no treatment and hydroquinone. Draelos ZD J. Am. Acad. Dermatol. 72(1), 105-7, (2015)

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Evaluation of in vivo mutagenicity of hydroquinone in Muta™ mice. Matsumoto M, Masumori S, Hirata-Koizumi M, et al. Mutat. Res. Genet. Toxicol. Environ. Mutagen. 775-776, 94-8, (2014)

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Topical treatment of hyperpigmentation disorders. Rendon M and Horwitz S Ann. Dermatol. Venereol. 139 Suppl 4, S153-8, (2012)

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DeoxyArbutin and its derivatives inhibit tyrosinase activity and melanin synthesis without inducing reactive oxygen species or apoptosis. Chawla S, Kvalnes K, deLong MA, et al. Journal. of. Drugs in. Dermatology. 11(10), e28-34, (2012)

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In vitro inhibition of ?-carbonic anhydrase isozymes by some phenolic compounds. Sevim Beyza Oztürk Sarikaya et al Bioorg. Med. Chem. Lett. 21, 4259-62, (2011)

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Hydroquinone and its analogues in dermatology - a risk-benefit viewpoint. O'Donoghue JL J. Cosmet. Dermatol. 5(3), 196-203, (2006)

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A practical comparison of hydroquinone-containing products for the treatment of melasma. Abramovits W, Barzin S, and Arrazola P Skinmed 4(6), 371-6, (2005)

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[Protein changes in human embryonic lung fibroblasts after hydroquinone stimulation using proteomic technique]. Li X, Zhuang Z, Liu J, et al. Wei Sheng Yan Jiu 33(6), 654-7, (2004)

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[Toxicological aspects and health risks associated with hydroquinone in skin bleaching formula]. Kooyers TJ and Westerhof W Ned. Tijdschr. Geneeskd. 148(16), 768-71, (2004)

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The use of hydroquinone with facial laser resurfacing. Goldman MP J. Cutan. Laser Ther. 2(2), 73-7, (2000)

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Hydroquinone. IARC Monogr. Eval. Carcinog. Risks Hum. 71 Pt 2, 691-719, (1999)

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Carbonic anhydrase inhibitors: Inhibition of the new membrane-associated isoform XV with phenols. Alessio Innocenti et al Bioorg. Med. Chem. Lett. 18, 3593-6, (2008)

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Effect of the benzene metabolite, hydroquinone, on interleukin-1 secretion by human monocytes in vitro. Carbonnelle P, Lison D, Leroy JY, et al. Toxicol. Appl. Pharmacol. 132(2), 220-6, (1995)

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Photoelectrochemical sensing for hydroquinone based on porphyrin-functionalized Au nanoparticles on graphene. Hu Y, Xue Z, He H, et al. Biosens. Bioelectron. 47, 45-9, (2013)

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Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species. Denis Fourches et al Chem. Res. Toxicol. 23, 171-83, (2010)

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The toxicology of hydroquinone--relevance to occupational and environmental exposure. DeCaprio AP Crit. Rev. Toxicol. 29(3), 283-330, (1999)

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The safety of hydroquinone: a dermatologist's response to the 2006 Federal Register. Levitt J J. Am. Acad. Dermatol. 57(5), 854-72, (2007)

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Nonextractable residue formation of sulfonamide antimicrobials: new insights from soil incubation experiments. Gulkowska A, Thalmann B, Hollender J, et al. Chemosphere 107, 366-72, (2014)

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Hydroquinone: an evaluation of the human risks from its carcinogenic and mutagenic properties. McGregor D Crit. Rev. Toxicol. 37(10), 887-914, (2007)

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Ultrathin CdSe nanosheets: synthesis and application in simultaneous determination of catechol and hydroquinone. Cao X, Cai X, Feng Q, et al. Anal. Chim. Acta 752, 101-5, (2012)

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Cellular apoptosis and cytotoxicity of phenolic compounds: a quantitative structure-activity relationship study. Cynthia D Selassie et al J. Med. Chem. 48, 7234-42, (2005)

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4-n-butylresorcinol, a highly effective tyrosinase inhibitor for the topical treatment of hyperpigmentation. Kolbe L, Mann T, Gerwat W, et al. J. Eur. Acad. Dermatol. Venereol. 27 Suppl 1, 19-23, (2013)

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The safety of hydroquinone. Nordlund JJ, Grimes PE, and Ortonne JP J. Eur. Acad. Dermatol. Venereol. 20(7), 781-7, (2006)

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Alteration of the oxygen-dependent reactivity of de novo Due Ferri proteins. Reig AJ, Pires MM, Snyder RA, et al. Nature Chemistry 4(11), 900-6, (2012)

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Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum. Jing Yuan et al Nat. Chem. Biol. 5, 765-71, (2009)

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Synthesis of gold nanorods and their functionalization with bovine serum albumin for optical hyperthermia. Zhang L, Xia K, Bai YY, et al. J. Biomed. Nanotechnol. 10(8), 1440-9, (2014)

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Hydroquinone regulates hemeoxygenase-1 expression via modulation of Src kinase activity through thiolation of cysteine residues. Byeon SE, Yu T, Yang Y, et al. Free Radic. Biol. Med. 57, 105-18, (2013)

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Hydroquinone modified chitosan/carbon film electrode for the selective detection of ascorbic acid. Jirimali HD, Nagarale RK, Saravanakumar D, et al. Carbohydr. Polym. 92(1), 641-4, (2013)

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Hydroquinone concentrations in skin lightening creams. Boyle J and Kennedy CT Br. J. Dermatol. 114(4), 501-4, (1986)

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Time-resolved photoelectron imaging of excited state relaxation dynamics in phenol, catechol, resorcinol, and hydroquinone. Livingstone RA, Thompson JO, Iljina M, et al. J. Chem. Phys. 137(18), 184304, (2012)

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Tyrosinase-inhibitory constituents from the twigs of Cinnamomum cassia. Tran Minh Ngoc et al J. Nat. Prod. 72, 1205-8, (2009)

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Hydroquinone therapy for post-inflammatory hyperpigmentation secondary to acne: not just prescribable by dermatologists. Chandra M, Levitt J, and Pensabene CA Acta Derm. Venereol. 92(3), 232-5, (2012)

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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). Bucks DA, McMaster JR, Guy RH, et al. J. Toxicol. Environ. Health 24(3), 279-89, (1988)

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Evaluation of anti-pigmentary effect of synthetic sulfonylamino chalcone. Woo Duck Seo et al Eur. J. Med. Chem. 45, 2010-7, (2010)

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S-glutathionyl-(chloro)hydroquinone reductases: a new class of glutathione transferases functioning as oxidoreductases. Belchik SM and Xun L Drug Metab. Rev. 43(2), 307-16, (2011)

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Air to lung partition coefficients for volatile organic compounds and blood to lung partition coefficients for volatile organic compounds and drugs. Michael H Abraham et al Eur. J. Med. Chem. 43, 478-85, (2008)

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Pyronane monoterpenoids from the fruit of Gardenia jasminoides. Quan Cheng Chen et al J. Nat. Prod. 71, 995-9, (2008)

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Label-free electrochemical immunosensor for prostate-specific antigen based on silver hybridized mesoporous silica nanoparticles. Wang H, Zhang Y, Yu H, et al. Anal. Biochem. 434(1), 123-7, (2013)

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Role of proton-coupled electron transfer in the redox interconversion between benzoquinone and hydroquinone. Song N, Gagliardi CJ, Binstead RA, et al. J. Am. Chem. Soc. 134(45), 18538-41, (2012)

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Effects of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its ester derivatives on biofilm formation by two oral pathogens, Porphyromonas gingivalis and Streptococcus mutans. Charles Bodet et al Eur. J. Med. Chem. 43, 1612-20, (2008)

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Skin lightening preparations and the hydroquinone controversy. Draelos ZD Dermatol. Ther. 20(5), 308-13, (2007)

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Hydroxylation of phenol to hydroquinone catalyzed by a human myeloperoxidase-superoxide complex: possible implications in benzene-induced myelotoxicity. Subrahmanyam VV, Kolachana P, and Smith MT Free Radic. Res. Commun. 15(5), 285-96, (1991)

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p38 MAPK/PP2Acα/TTP pathway on the connection of TNF-α and caspases activation on hydroquinone-induced apoptosis. Liu WH, Chou WM, and Chang LS Carcinogenesis 34(4), 818-27, (2013)

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Hydroquinone-induced miR-122 down-regulation elicits ADAM17 up-regulation, leading to increased soluble TNF-α production in human leukemia cells with expressed Bcr/Abl. Chen YJ and Chang LS Biochem. Pharmacol. 86(5), 620-31, (2013)

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Analogues of N-hydroxy-N'-phenylthiourea and N-hydroxy-N'-phenylurea as inhibitors of tyrosinase and melanin formation. Marc Criton et al Bioorg. Med. Chem. Lett. 18, 3607-10, (2008)

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Changes in DNA methylation of erythroid-specific genes in K562 cells exposed to phenol and hydroquinone. Li Y, Wu XR, Li XF, et al. Toxicology 312, 108-14, (2013)

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An ortho-carbonyl substituted hydroquinone derivative is an anticancer agent that acts by inhibiting mitochondrial bioenergetics and by inducing G₂/M-phase arrest in mammary adenocarcinoma TA3. Urra FA, Martínez-Cifuentes M, Pavani M, et al. Toxicol. Appl. Pharmacol. 267(3), 218-27, (2013)

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The percutaneous absorption of hydroquinone (HQ) through rat and human skin in vitro. Barber ED, Hill T, and Schum DB Toxicol. Lett. 80(1-3), 167-72, (1995)

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Melanin synthesis inhibitors from Lespedeza cyrtobotrya. Maya Mori-Hongo et al J. Nat. Prod. 72, 63-71, (2009)

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Combination of fractional erbium-glass laser and topical therapy in melasma resistant to triple-combination cream. Tourlaki A, Galimberti MG, Pellacani G, et al. J. Dermatolog. Treat. 25(3), 218-22, (2014)

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Degradation of paracetamol by Pseudomonas aeruginosa strain HJ1012. Hu J, Zhang LL, Chen JM, et al. J. Environ. Sci. Health. A. Tox. Hazard. Subst. Environ. Eng. 48(7), 791-9, (2013)

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Caspase-dependent and -independent mechanisms in apoptosis induced by hydroquinone and catechol metabolites of remoxipride in HL-60 cells. Inayat-Hussain SH, McGuinness SM, Johansson R, et al. Chem. Biol. Interact. 128(1), 51-63, (2000)

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Melanin synthesis inhibitors from Lespedeza floribunda. Maya Mori-Hongo et al J. Nat. Prod. 72, 194-203, (2009)

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Syntheses of hydroxy substituted 2-phenyl-naphthalenes as inhibitors of tyrosinase. Suhee Song et al Bioorg. Med. Chem. Lett. 17, 461-4, (2007)

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The effects of Sophora angustifolia and other natural plant extracts on melanogenesis and melanin transfer in human skin cells. Singh SK, Baker R, Wibawa JI, et al. Exp. Dermatol. 22(1), 67-9, (2013)

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Induced differentiation of HL-60 promyelocytic leukemia cells to monocyte/macrophages is inhibited by hydroquinone, a hematotoxic metabolite of benzene. Oliveira NL and Kalf GF Blood 79(3), 627-33, (1992)

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Hydroquinone increases 5-hydroxymethylcytosine formation through ten eleven translocation 1 (TET1) 5-methylcytosine dioxygenase. Coulter JB, O'Driscoll CM, and Bressler JP J. Biol. Chem. 288(40), 28792-800, (2013)

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The vitamin K oxidoreductase is a multimer that efficiently reduces vitamin K epoxide to hydroquinone to allow vitamin K-dependent protein carboxylation. Rishavy MA, Hallgren KW, Wilson LA, et al. J. Biol. Chem. 288(44), 31556-66, (2013)

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Successful treatment of hydroquinone-resistant melasma using topical methimazole. Malek J, Chedraoui A, Nikolic D, et al. Dermatol. Ther. 26(1), 69-72, (2013)

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Clinical efficacy and safety of a multimodality skin brightener composition compared with 4% hydroquinone. Makino ET, Herndon JH, Sigler ML, et al. Journal. of. Drugs in. Dermatology. 11(12), 1478-82, (2012)

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Comparison of the repair of DNA damage induced by the benzene metabolites hydroquinone and p-benzoquinone: a role for hydroquinone in benzene genotoxicity. Gaskell M, McLuckie KI, and Farmer PB Carcinogenesis 26(3), 673-80, (2005)

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Application of physiologically-based toxicokinetic modelling in oral-to-dermal extrapolation of threshold doses of cosmetic ingredients. Gajewska M, Worth A, Urani C, et al. Toxicol. Lett. 227(3), 189-202, (2014)

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Clinical efficacy and safety of a multimodality skin brightener composition compared with 4% hydroquinone. Makino ET, Mehta RC, Garruto J, et al. Journal. of. Drugs in. Dermatology. 12(3), s21-6, (2013)

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Reactivity and biological activity of the marine sesquiterpene hydroquinone avarol and related compounds from sponges of the order Dictyoceratida. Sladić D and Gasić MJ Molecules 11(1), 1-33, (2006)

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Comparative study of hydroquinone-free and hydroquinone-based hyperpigmentation regimens in treating facial hyperpigmentation and photoaging. Fabi SG and Goldman MP Journal. of. Drugs in. Dermatology. 12(3), S32-7, (2013)

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Evaluation of a hydroquinone-free skin brightening product using in vitro inhibition of melanogenesis and clinical reduction of ultraviolet-induced hyperpigmentation. Makino ET, Mehta RC, Banga A, et al. Journal. of. Drugs in. Dermatology. 12(3), s16-20, (2013)

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Electrochemical microdevice for on-site determination of rice freshness. Koyachi E, Kojima K, Qiu X, et al. Biosens. Bioelectron. 42, 640-5, (2013)

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Discovery of novel SERCA inhibitors by virtual screening of a large compound library. Christopher Elam et al Eur. J. Med. Chem. 46, 1512-23, (2011)

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Hydroquinone, a benzene metabolite, and leukemia: a case report and review of the literature. Regev L, Wu M, Zlotolow R, et al. Toxicol. Ind. Health 28(1), 64-73, (2012)

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Convenient QSAR model for predicting the complexation of structurally diverse compounds with beta-cyclodextrins. Alfonso Pérez-Garrido et al Bioorg. Med. Chem. 17, 896-904, (2009)

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Synthesis and anti-inflammatory activity of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its ester derivatives. Francesco Epifano et al Bioorg. Med. Chem. Lett. 17, 5709-14, (2007)

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Laccase immobilized onto poly(GMA-MAA) microspheres for p-benzenediol removal from wastewater. Li C, Lou Y, Wan Y, et al. Water Sci. Technol. 67(10), 2287-93, (2013)

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Treatment of melasma and the use of intense pulsed light: a review. Zaleski L, Fabi S, and Goldman MP Journal. of. Drugs in. Dermatology. 11(11), 1316-20, (2012)

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Studies on depigmenting activities of dihydroxyl benzamide derivatives containing adamantane moiety. Ho Sik Rho et al Bioorg. Med. Chem. Lett. 19, 1532-3, (2009)

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Identification of a potent and noncytotoxic inhibitor of melanin production. Soonho Hwang et al Bioorg. Med. Chem. 18, 5602-9, (2010)

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A newly synthesized, potent tyrosinase inhibitor: 5-(6-hydroxy-2-naphthyl)-1,2,3-benzenetriol. Jehun Choi et al Bioorg. Med. Chem. Lett. 20, 4882-4, (2010)

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Hydroquinone for skin lightening: safety profile, duration of use and when should we stop? Tse TW J. Dermatolog. Treat. 21(5), 272-5, (2010)

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Cytotoxicity of dental compounds towards human oral squamous cell carcinoma and normal oral cells. Koh T, Machino M, Murakami Y, et al. In Vivo 27(1), 85-95, (2013)

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Resveratrol inhibited hydroquinone-induced cytotoxicity in mouse primary hepatocytes. Wang DH, Ootsuki Y, Fujita H, et al. Int. J. Environ. Res. Public Health 9(9), 3354-64, (2012)

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Improving a self-curing dental resin by eliminating oxygen, hydroquinone and water from its curing process. Keh ES, Hayakawa I, Takahashi H, et al. Dent. Mater. J. 21(4), 373-82, (2002)

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Tolerance and efficacy of a product containing ellagic and salicylic acids in reducing hyperpigmentation and dark spots in comparison with 4% hydroquinone. Dahl A, Yatskayer M, Raab S, et al. Journal. of. Drugs in. Dermatology. 12(1), 52-8, (2013)

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Efficacy of hydroquinone-free skin-lightening cream for photoaging. Dreher F, Draelos ZD, Gold MH, et al. J. Cosmet. Dermatol. 12(1), 12-7, (2013)

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Final amended safety assessment of hydroquinone as used in cosmetics. Andersen FA, Bergfeld WF, Belsito DV, et al. Int. J. Toxicol. 29(6 Suppl), 274S-87, (2010)

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Treating epidermal melasma with a 4% hydroquinone skin care system plus tretinoin cream 0.025%. Grimes P and Watson J Cutis. 91(1), 47-54, (2013)

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Comparison of a skin-lightening cream targeting melanogenesis on multiple levels to triple combination cream for melasma. Monheit GD and Dreher F Journal. of. Drugs in. Dermatology. 12(3), 270-4, (2013)

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α-Tocopheryl succinate pre-treatment attenuates quinone toxicity in prostate cancer PC3 cells. Bellezza I, Grottelli S, Gatticchi L, et al. Gene 539(1), 1-7, (2014)

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Acne and skin bleaching in Lomé, Togo. Kombaté K, Mouhari-Toure A, Saka B, et al. Int. J. Dermatol. 51 Suppl 1, 27-9, 30-2, (2012)

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Risk assessment of free hydroquinone derived from Arctostaphylos Uva-ursi folium herbal preparations. de Arriba SG, Naser B, and Nolte KU Int. J. Toxicol. 32(6), 442-53, (2013)

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[Topical treatment of hyperpigmentation disorders]. Rendon M and Horwitz S Ann. Dermatol. Venereol. 139 Suppl 3, S102-7, (2012)

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Hydroquinone: environmental pollution, toxicity, and microbial answers. Enguita FJ and Leitão AL Biomed Res. Int. 2013, 542168, (2013)

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Hydroquinone-induced exogenous ochronosis in Chinese--two case reports and a review. Tan SK, Sim CS, and Goh CL Int. J. Dermatol. 47(6), 639-40, (2008)

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Hypothesis: phenol and hydroquinone derived mainly from diet and gastrointestinal flora activity are causal factors in leukemia. McDonald TA, Holland NT, Skibola C, et al. Leukemia 15(1), 10-20, (2001)

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Merck 14,4808

Beil. 6,IV,5712

Fieser 5,341

Aldrich MSDS 1, 1050:A / Corp MSDS 1 (1), 1900:B / FT-IR 2 (2), 1892:A / FT-IR 1 (1), 1107:D / FT-NMR 1 (2), 304:C / IR-Spectra (2), 594:F / IR-Spectra (3), 666:C / NMR-Reference 2 (1), 902:B / RegBook 1 (1), 1301:A / Sax 6, 1553 / Sigma FT-IR 1 (2), 618:B / Structure Index 1, 198:B:6 / Vapor Phase 3, 1041:B

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