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54050 Fluka

4-Methoxyphenol

purum, ≥98.0% (HPLC)

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

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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.)

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xn
Risk Statements (Europe) 
Safety Statements (Europe) 
24/25-26-37/39-46
WGK Germany 
1
RTECS 
SL7700000
Flash Point(F) 
269.6 °F
Flash Point(C) 
132 °C

Protocols & Articles

Articles

Determination of Water Content in Hydroquinone monomethyl ether Using Karl Fischer Titration

Phenols behave differently. Most of them can be titrated in the usual manner, some are oxidized by iodine. o-Cresol shows a slight tendency towards oxidation, divalent phenols are easily oxidized. Py...
Keywords: Oxidations, Titrations

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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