Mequinol

Last updated
Mequinol
4-Methoxyphenol.png
Clinical data
Other names4-Hydroxyanisole; para-Guaiacol
AHFS/Drugs.com International Drug Names
MedlinePlus a682437
Routes of
administration
Topical
ATC code
Legal status
Legal status
  • CA:Unscheduled
  • US: ℞-only and Unscheduled
  • In general: unscheduled
Identifiers
  • 4-Methoxyphenol
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.005.246 OOjs UI icon edit-ltr-progressive.svg
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=1S/C7H8O2/c1-9-7-4-2-6(8)3-5-7/h2-5,8H,1H3 Yes check.svgY
  • Key:NWVVVBRKAWDGAB-UHFFFAOYSA-N Yes check.svgY
   (verify)

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]

Contents

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

Related Research Articles

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<span class="mw-page-title-main">Monobenzone</span> Chemical compound

Monobenzone, also called 4-(Benzyloxy)phenol and monobenzyl ether of hydroquinone (MBEH) is an organic chemical in the phenol family with chemical formula C6H5CH2OC6H4OH. It is used as a topical drug for medical depigmentation. It is a colourless solid that is classified as the monobenzyl ether of hydroquinone. Monobenzone is soluble in alcohol, benzene, and diethyl ether, and practically insoluble in water.

Clindamycin/tretinoin is a topical gel used in the treatment of acne. The two active ingredients are the antibiotic clindamycin phosphate (1.2%) and tretinoin (0.025%), a retinoid. The two active ingredients perform different functions, the clindamycin is active against gram-positive bacteria, including streptococci and penicillin-resistant staphylococci. The Tretinoin element acts to reduce the amount of oil released by oil glands in skin as well as encouraging skin cell replenishment. The topical treatment is stored in 2, 30, and 60 gram tubes and should be stored at 25°C (77°F), with the tube tightly shut away from light. Side effects may include peeling, redness, dryness, itching and photosensitivity. Also, topical clindamycin may rarely cause diarrhea or colitis. Sun exposure while using this preparation can cause skin irritation.

References

  1. 1 2 Stiefel Laboratories, Inc. "Full Prescribing Information" (PDF). US Food and Drug Administration. Retrieved 2 January 2015.
  2. 1 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.