Mequinol

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Mequinol
Clinical data
Synonyms	4-Hydroxyanisole; para-Guaiacol
AHFS/Drugs.com	International Drug Names
MedlinePlus	a682437
Routes of; administration	Topical
ATC code	D11AX06 (WHO) ;
Legal status
Legal status	CA: Unscheduled ; US: Rx-only, Unscheduled ; In general: unscheduled;
Identifiers
	IUPAC name 4-Methoxyphenol;
CAS Number	150-76-5 ;
PubChem CID	9015;
ChemSpider	8665 ;
UNII	6HT8U7K3AM;
KEGG	D04926 ;
ChEMBL	ChEMBL544 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C7H8O2
Molar mass	124.13722 g/mol
Density	1.55 g/cm3
Melting point	52.5 °C (126.5 °F)
Boiling point	243 °C (469.4 °F)
	InChI InChI=1S/C7H8O2/c1-9-7-4-2-6(8)3-5-7/h2-5,8H,1H3 ; Key:NWVVVBRKAWDGAB-UHFFFAOYSA-N ;
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Mequinol, or 4-Methoxyphenol, is a phenol used in dermatology^[1] and organic chemistry.^[2]

Uses

Dermatology

Mequinol is a common active ingredient in topical drugs used for skin depigmentation. As a topical drug Mequinol is often mixed with tretinoin, a topical retinoid. A common formulation for this drug is an ethanolic solution of 2% Mequinol and 0.01% tretinoin by mass.^[1] Dermatologists commonly prescribe the drug to treat solar lentigines, liver spots, or age spots.

Lower dosages of mequinol have been used in conjunction with a Q-switched laser to depigment skin in patients with disseminated idiopathic vitiligo.^[3]

Organic chemistry

In organic chemistry 4-Methoxyphenol is used to inhibit the radical polymerization of monomers (e.g. acrylates or styrene monomers).^[2]

Preparation

4-Methoxyphenol is produced from p-benzoquinone and methanol via a free radical reaction.^[4]^[5]

References

↑ ^1.0 ^1.1 Stiefel Laboratories, Inc. "Full Prescribing Information" (PDF). US Food and Drug Admistration. Retrieved 2 January 2015.
↑ ^2.0 ^2.1 Hudnall, Phillip M. (2000). "Hydroquinone". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a13_499.
↑ Komen, L.; Zwertbroek, L.; Burger, S.J.; van der Veen, J.P.W.; de Rie, M.A.; Wolkerstorfer, A. (2013). "Q-switched laser depigmentation in vitiligo, most effective in active disease". British Journal of Dermatology. 169 (6): 1246–1251. doi:10.1111/bjd.12571.
↑ Cristian, Gambarotti; Lucio, Melone; Carlo, Punta; Suresh Udhavrao, Shisodia (2013). "Selective Monoetherification of 1,4-Hydroquinone Promoted by NaNO₂". Current Organic Chemistry. 17 (10): 1108–1113.
↑ Correale, Mariano; Panseri, Pietro; Romano, Ugo; Minisci, Francesco. "Process for the preparation of mono-ethers of hydroquinones US4933504A". Google Patents. Enichem Synthesis S.P.A. Retrieved 2 January 2015.

[FDA-1] 1.0 ^1.1 Stiefel Laboratories, Inc. "Full Prescribing Information" (PDF). US Food and Drug Admistration. Retrieved 2 January 2015.

[Ullmann-2] 2.0 ^2.1 Hudnall, Phillip M. (2000). "Hydroquinone". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a13_499.

[3] Komen, L.; Zwertbroek, L.; Burger, S.J.; van der Veen, J.P.W.; de Rie, M.A.; Wolkerstorfer, A. (2013). "Q-switched laser depigmentation in vitiligo, most effective in active disease". British Journal of Dermatology. 169 (6): 1246–1251. doi:10.1111/bjd.12571.

[4] Cristian, Gambarotti; Lucio, Melone; Carlo, Punta; Suresh Udhavrao, Shisodia (2013). "Selective Monoetherification of 1,4-Hydroquinone Promoted by NaNO₂". Current Organic Chemistry. 17 (10): 1108–1113.

[5] Correale, Mariano; Panseri, Pietro; Romano, Ugo; Minisci, Francesco. "Process for the preparation of mono-ethers of hydroquinones US4933504A". Google Patents. Enichem Synthesis S.P.A. Retrieved 2 January 2015.

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