Mequinol

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 459851915

| IUPAC_name = 4-Methoxyphenol

| image = 4-Methoxyphenol.png

| width = 100px

| tradename =

| Drugs.com = {{drugs.com|international|mequinol}}

| MedlinePlus = a682437

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA = Unscheduled

| legal_UK =

| legal_US = Rx-only

| legal_US_comment = and Unscheduled

| legal_status = Unscheduled

| routes_of_administration = Topical

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| IUPHAR_ligand = 6827

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 150-76-5

| ATC_prefix = D11

| ATC_suffix = AX06

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C7H8O2/c1-9-7-4-2-6(8)3-5-7/h2-5,8H,1H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = NWVVVBRKAWDGAB-UHFFFAOYSA-N

| PubChem = 9015

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 8665

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 6HT8U7K3AM

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D04926

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 544

| C=7 | H=8 | O=2

| synonyms = 4-Hydroxyanisole; para-Guaiacol

| density = 1.55

| melting_point = 52.5

| boiling_point = 243

| solubility =

| specific_rotation =

}}

Mequinol, MeHQ or 4-methoxyphenol, is an organic compound with the formula {{chem2|CH3OC6H4OH}}. It is a phenol with a methoxy group in the para position. A colorless solid, it is used in dermatology{{cite web |last= Stiefel Laboratories, Inc. |title= Full Prescribing Information |url= http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020922s006lbl.pdf |archive-url= https://web.archive.org/web/20150102134755/http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020922s006lbl.pdf |url-status= dead |archive-date= January 2, 2015 |publisher= US Food and Drug Administration |access-date= 2 January 2015 }} and organic chemistry.{{Ullmann |last1= Hudnall |first1= Phillip M. | name-list-style = vanc |title= Hydroquinone |date=2000 |doi= 10.1002/14356007.a13_499}}

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. 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.{{cite journal | vauthors = Komen L, Zwertbroek L, Burger SJ, van der Veen JP, de Rie MA, Wolkerstorfer A | title = Q-switched laser depigmentation in vitiligo, most effective in active disease | journal = The British Journal of Dermatology | volume = 169 | issue = 6 | pages = 1246–51 | date = December 2013 | pmid = 23909405 | doi = 10.1111/bjd.12571 | s2cid = 43542975 }}

Organic chemistry

In organic chemistry 4-methoxyphenol is used as a polymerisation inhibitor (e.g. acrylates or styrene monomers).

4-Methoxyphenol can be produced from p-benzoquinone and methanol via a free radical reaction.{{cite journal| vauthors = Gambarotti C, Melone L, Punta C, Shisodia SU |title= Selective Monoetherification of 1,4-Hydroquinone Promoted by NaNO₂ |journal= Current Organic Chemistry |date=2013 |volume=17 |issue=10 |pages= 1108–1113 |doi=10.2174/1385272811317100011}}{{cite patent|inventor = Correale M, Panseri P, Romano U, Minisci F |title= Process for the preparation of mono-ethers of hydroquinones |country=US |number= 4933504}}

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.{{Cite web |publisher= CDC |work= NIOSH Pocket Guide to Chemical Hazards |title= 4-Methoxyphenol |url= https://www.cdc.gov/niosh/npg/npgd0390.html |access-date= 2015-11-20 }}

References

External links

{{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/mequinol | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Mequinol }}

Category:4-Hydroxyphenyl compounds

Category:4-Methoxyphenyl compounds