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54050 Sigma-Aldrich

4-Methoxyphenol

purum, ≥98.0% (HPLC)

Synonym: 4-Hydroxyanisole, 4-MP, HQMME, Hydroquinone monomethyl ether, MEHQ, MQ-F, p-Guaiacol

  • CAS Number 150-76-5

  • Linear Formula CH3OC6H4OH

  • Molecular Weight 124.14

  •  Beilstein Registry Number 507924

  •  EC Number 205-769-8

  •  MDL number MFCD00002332

  •  PubChem Substance ID 24878473

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Properties

Related Categories Building Blocks, C6 to C8, Chemical Synthesis, Organic Building Blocks, Oxygen Compounds,
vapor density   4.3 (vs air)
vapor pressure   <0.01 mmHg ( 20 °C)
grade   purum
assay   ≥98.0% (HPLC)
autoignition temp.   789 °F
impurities   ≤2% hydroquinone dimethyl ether
bp   243 °C(lit.)
mp   54-56 °C
  55-57 °C(lit.)

Description

Other Notes

Same product — same quality — now Sigma-Aldrich brand

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Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
Personal Protective Equipment 
WGK Germany 
1
RTECS 
SL7700000
Flash Point(F) 
269.6 °F
Flash Point(C) 
132 °C

Protocols & Articles

Peer-Reviewed Papers

References

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Analytic quantification of the bleaching effect of a 4-hydroxyanisole-tretinoin combination on actinic lentigines. Piérard-Franchimont C, Henry F, Quatresooz P, et al. Journal. of. Drugs in. Dermatology. 7(9), 873-8, (2008)

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The combination of 2% 4-hydroxyanisole (mequinol) and 0.01% tretinoin effectively improves the appearance of solar lentigines in ethnic groups. Draelos ZD J. Cosmet. Dermatol. 5(3), 239-44, (2006)

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New drugs 04, part 1. Hussar DA Nursing 34(2), 56-62; quiz 63-4, (2004)

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A promising new treatment for solar lentigines. Colby SI, Schwartzel EH, Huber FJ, et al. Journal. of. Drugs in. Dermatology. 2(2), 147-52, (2003)

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Subcellular localization and cytoplasmic complex status of endogenous Keap1. Watai Y, Kobayashi A, Nagase H, et al. Genes Cells 12(10), 1163-78, (2007)

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Calculating virtual log P in the alkane/water system (log P(N)(alk)) and its derived parameters deltalog P(N)(oct-alk) and log D(pH)(alk). Giulia Caron et al J. Med. Chem. 48, 3269-79, (2005)

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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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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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Antioxidant activity and characterization of volatile constituents of Taheebo (Tabebuia impetiginosa Martius ex DC). Park BS, Lee KG, Shibamoto T, et al. J. Agric. Food Chem. 51(1), 295-300, (2003)

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Effect of hydrogen peroxide on the three-dimensional polymer network in composites. Durner J, Stojanovic M, Urcan E, et al. Dent. Mater. 27(6), 573-80, (2011)

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Peroxidase-mediated removal of a polychlorinated biphenyl using natural organic matter as the sole cosubstrate. Colosi LM, Burlingame DJ, Huang Q, et al. Environ. Sci. Technol. 41(3), 891-6, (2007)

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Increase in the levels of chaperone proteins by exposure to beta-estradiol, bisphenol A and 4-methoxyphenol in human cells transfected with estrogen receptor alpha cDNA. Kita K, Jin YH, Sun Z, et al. Toxicol. In Vitro 23(4), 728-35, (2009)

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Measurement of phenols dearomatization via electrolysis: the UV-Vis solid phase extraction method. Vargas R, Borrás C, Mostany J, et al. Water Res. 44(3), 911-7, (2010)

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Application of ex situ dynamic nuclear polarization in studying small molecules. Ludwig C, Marin-Montesinos I, Saunders MG, et al. Phys. Chem. Chem. Phys. 12(22), 5868-71, (2010)

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Biochemical basis of 4-hydroxyanisole induced cell toxicity towards B16-F0 melanoma cells. Moridani MY Cancer Lett. 243(2), 235-45, (2006)

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Improved thin-layer chromatography bioautographic assay for the detection of actylcholinesterase inhibitors in plants. Yang ZD, Song ZW, Ren J, et al. Phytochem. Anal. 22(6), 509-15, (2011)

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Synthesis and preliminary in vitro biological evaluation of 4-[(4-hydroxyphenyl)sulfanyl]but-3-en-2-one, a 4-mercaptophenol derivative designed as a novel bifunctional antimelanoma agent. Paolo Ruzza et al J. Med. Chem. 52, 4973-6, (2009)

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Simulation of IR and Raman spectra of p-hydroxyanisole and p-nitroanisole based on scaled DFT force fields and their vibrational assignments. Krishnakumar V and Prabavathi N Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 74(1), 154-61, (2009)

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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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Safety and efficacy of combined use of 4-hydroxyanisole (mequinol) 2%/tretinoin 0.01% solution and sunscreen in solar lentigines. Ortonne JP, Camacho F, Wainwright N, et al. Cutis. 74(4), 261-4, (2004)

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Radical-scavenging activity and cytotoxicity of p-methoxyphenol and p-cresol dimers. Kadoma Y, Murakami Y, Ogiwara T, et al. Molecules 15(3), 1103-12, (2010)

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Treatment of hyperpigmentation. Rossi AM and Perez MI Facial Plast. Surg. Clin. North Am. 19(2), 313-24, (2011)

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Mequinol 2%/tretinoin 0.01% topical solution for the treatment of melasma in men: a case series and review of the literature. Keeling J, Cardona L, Benitez A, et al. Cutis. 81(2), 179-83, (2008)

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Mequinol 2%/tretinoin 0.01% solution: an effective and safe alternative to hydroquinone 3% in the treatment of solar lentigines. Jarratt M Cutis. 74(5), 319-22, (2004)

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Antioxidant activity of colored rice bran obtained at different milling yields. Fujita A, Fujitake H, Kawakami K, et al. J. Oleo Sci. 59(10), 563-8, (2010)

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Arrest of cell cycle by inhibition of ribonucleotide reductase induces accumulation of NAD+ by Mn2+-supplemented growth of Corynebacterium ammoniagenes. Abbouni B, Elhariry HM, and Auling G Biotechnol. Lett. 25(2), 143-7, (2003)

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Development and evaluation of kinetic spectrophotometric assays for horseradish peroxidase by catalytic coupling of paraphenylenediamine and mequinol. Nagaraja P, Shivakumar A, and Kumar Shrestha A Anal. Sci. 25(10), 1243-8, (2009)

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Unprecedented chemiluminescence behaviour during peroxyoxalate chemiluminescence of oxalates with fluorescent or electron-donating aryloxy groups. Koike R, Kato Y, Motoyoshiya J, et al. Luminescence 21(3), 164-73, (2006)

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Depigmentation therapy in vitiligo universalis with cryotherapy and 4-hydroxyanisole. Di Nuzzo S and Masotti A Clin. Exp. Dermatol. 35(2), 215-6, (2010)

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Enhancement of the depigmenting effect of hydroquinone and 4-hydroxyanisole by all-trans-retinoic acid (tretinoin): the impairment of glutathione-dependent cytoprotection? Kasraee B, Handjani F, and Aslani FS Dermatology 206(4), 289-91, (2003)

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Beil. 6,IV,5717

Fieser 13,181

Aldrich MSDS 1, 1191:C / Corp MSDS 1 (2), 2263:A / FT-IR 1 (1), 1079:A / FT-IR 2 (2), 1847:D / FT-NMR 1 (2), 254:B / IR-Spectra (2), 578:G / IR-Spectra (3), 649:A / NMR-Reference 2 (1), 902:D / RegBook 1 (1), 1271:K / Sax 6, 1554 / Sigma FT-IR 1 (2), 714:A / Structure Index 1, 193:B:5 / Vapor Phase 3, 1011:D

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