Mequinol

Mequinol

Clinical data
Other names	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: ℞-only and Unscheduled In general: unscheduled
Identifiers
IUPAC name 4-Methoxyphenol
CAS Number	150-76-5  Y
PubChem CID	9015
IUPHAR/BPS	6827
ChemSpider	8665  Y
UNII	6HT8U7K3AM
KEGG	D04926  Y
ChEMBL	ChEMBL544  Y
CompTox Dashboard (EPA)	DTXSID4020828
ECHA InfoCard	100.005.246
Chemical and physical data
Formula	C7H8O2
Molar mass	124.139 g·mol−1
Density	1.55 g/cm3
Melting point	52.5 °C (126.5 °F)
Boiling point	243 °C (469 °F)
InChI InChI=1S/C7H8O2/c1-9-7-4-2-6(8)3-5-7/h2-5,8H,1H3 Y Key:NWVVVBRKAWDGAB-UHFFFAOYSA-N Y
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Mequinol, MeHQ or 4-methoxyphenol, is an organic compound with the formula CH₃OC₆H₄OH. It is a phenol with a methoxy group in the para position. A colorless solid, it is used in dermatology ^[1] and organic chemistry. ^[2]

Use in 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 liver 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 as a polymerisation inhibitor (e.g. acrylates or styrene monomers). ^[2]

4-Methoxyphenol can be produced from p-benzoquinone and methanol via a free radical reaction. ^{[4] [5]}

Safety

The U.S. National Institute for Occupational Safety and Health (NIOSH) has set a recommended exposure limit (REL) of 5 mg/m³ over an 8-hour workday. ^[6]

See also

• Monobenzone (benzyloxyphenol)
• Hydroquinone
• Guaiacol
• 2-Hydroxy-5-methoxybenzaldehyde

References

1. Stiefel Laboratories, Inc. "Full Prescribing Information" (PDF). US Food and Drug Administration. Archived from the original (PDF) on January 2, 2015. Retrieved 2 January 2015.
2. Hudnall PM (2000). "Hydroquinone". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_499. ISBN   978-3-527-30673-2.
3. Komen L, Zwertbroek L, Burger SJ, van der Veen JP, de Rie MA, Wolkerstorfer A (December 2013). "Q-switched laser depigmentation in vitiligo, most effective in active disease". The British Journal of Dermatology. 169 (6): 1246–51. doi:10.1111/bjd.12571. PMID   23909405. S2CID   43542975.
4. Gambarotti C, Melone L, Punta C, Shisodia SU (2013). "Selective Monoetherification of 1,4-Hydroquinone Promoted by NaNO₂". Current Organic Chemistry. 17 (10): 1108–1113. doi:10.2174/1385272811317100011.
5. US 4933504,Correale M, Panseri P, Romano U, Minisci F,"Process for the preparation of mono-ethers of hydroquinones" 
6. "4-Methoxyphenol". NIOSH Pocket Guide to Chemical Hazards. CDC. Retrieved 2015-11-20.

External links

• "Mequinol". Drug Information Portal. U.S. National Library of Medicine.