Mequinol

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

Mequinol
Clinical data
Other names4-Hydroxyanisole; para-Guaiacol
AHFS/Drugs.comInternational Drug Names
MedlinePlusa682437
Routes of
administration		Topical
ATC code
Legal status
Legal status
  • CA: Unscheduled
  • US: ℞-only and Unscheduled
  • In general: unscheduled
Identifiers
IUPAC name
  • 4-Methoxyphenol
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.246
Chemical and physical data
FormulaC7H8O2
Molar mass124.139 g·mol−1
Density1.55 g/cm3
Melting point52.5 °C (126.5 °F)
Boiling point243 °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
  (verify)

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 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]

Preparation

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

Safety

People can be exposed to 4-methoxyphenol in the workplace by breathing it in, skin absorption, swallowing it, skin contact, and eye contact. The 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. Retrieved 2 January 2015.
  2. Hudnall PM. "Hydroquinone". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_499.
  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.
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