MEQUINOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H8O2
Molecular Weight	124.1372
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(O)C=C1

InChI

InChIKey=NWVVVBRKAWDGAB-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C7H8O2
Molecular Weight	124.1372
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020922s006lbl.pdf

Mequinol (mequinol is 4-hydroxyanisole) is an active ingredient in topical drugs used for skin depigmentation. The mechanism of action of mequinol is unknown. Although mequinol is a substrate for the enzyme tyrosinase and acts as a competitive inhibitor of the formation of melanin precursors, the clinical significance of these findings is unknown.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tyrosinase 41 Target ID: CHEMBL1973 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020922s006lbl.pdf	Substrate 643

Conditions

Condition	Modality	Targets	Highest Phase	Product
Solar lentigines 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020922s006lbl.pdf	Primary		Approved 8307	SOLAGE Approved Use Mequinol is a depigmenting agent. The mechanism of depigmenting effects of mequinol remain unclear; speculations include oxidation by tyrosinase to cytotoxic products in melanocytes, a direct/selective toxic effect on melanocytes, or inhibition of melanin formation Launch Date 9.4478402E11

C_max

Value	Dose	Co-administered	Analyte	Population
9.92 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10701701/	16 μL 1 times / day steady-state, topical dose: 16 μL route of administration: Topical experiment type: STEADY-STATE co-administered:		MEQUINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
33.43 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10701701/	16 μL 1 times / day steady-state, topical dose: 16 μL route of administration: Topical experiment type: STEADY-STATE co-administered:		MEQUINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10701701/	16 μL 1 times / day steady-state, topical dose: 16 μL route of administration: Topical experiment type: STEADY-STATE co-administered:		MEQUINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
2 % 1 times / day steady, topical Recommended Dose: 2 %, 1 times / day Route: topical Route: steady Dose: 2 %, 1 times / day Co-administed with:: tretinoin(0.0001) Sources: https://pubmed.ncbi.nlm.nih.gov/17177746/	healthy, 55.8 years n = 159 Health Status: healthy Condition: solar lentigines Age Group: 55.8 years Sex: M+F Population Size: 159 Sources: https://pubmed.ncbi.nlm.nih.gov/17177746/	Disc. AE: Dermal and epidermal conditions NEC, Skin and subcutaneous tissue disorders... Other AEs: Hematuria... AEs leading to discontinuation/dose reduction: Dermal and epidermal conditions NEC (3.5%) Skin and subcutaneous tissue disorders (5.8%) Other AEs: Hematuria (3.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/17177746/

AEs

AE	Significance	Dose	Population
Hematuria	3.5%	2 % 1 times / day steady, topical Recommended Dose: 2 %, 1 times / day Route: topical Route: steady Dose: 2 %, 1 times / day Co-administed with:: tretinoin(0.0001) Sources: https://pubmed.ncbi.nlm.nih.gov/17177746/	healthy, 55.8 years n = 159 Health Status: healthy Condition: solar lentigines Age Group: 55.8 years Sex: M+F Population Size: 159 Sources: https://pubmed.ncbi.nlm.nih.gov/17177746/
Dermal and epidermal conditions NEC	3.5% Disc. AE	2 % 1 times / day steady, topical Recommended Dose: 2 %, 1 times / day Route: topical Route: steady Dose: 2 %, 1 times / day Co-administed with:: tretinoin(0.0001) Sources: https://pubmed.ncbi.nlm.nih.gov/17177746/	healthy, 55.8 years n = 159 Health Status: healthy Condition: solar lentigines Age Group: 55.8 years Sex: M+F Population Size: 159 Sources: https://pubmed.ncbi.nlm.nih.gov/17177746/
Skin and subcutaneous tissue disorders	5.8% Disc. AE	2 % 1 times / day steady, topical Recommended Dose: 2 %, 1 times / day Route: topical Route: steady Dose: 2 %, 1 times / day Co-administed with:: tretinoin(0.0001) Sources: https://pubmed.ncbi.nlm.nih.gov/17177746/	healthy, 55.8 years n = 159 Health Status: healthy Condition: solar lentigines Age Group: 55.8 years Sex: M+F Population Size: 159 Sources: https://pubmed.ncbi.nlm.nih.gov/17177746/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP 252

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 252	substrate 3264 Sources: https://journals.sagepub.com/doi/pdf/10.3109/10915818509078686	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	NO22939	https://www.001chemical.com/chem/150-76-5
3B Scientific (Wuhan) Corp	3B3-032693	http://www.3bsc.com/index/pro_info.php?id=53957
AA Blocks	AA001M5C	http://www.aablocks.com/goods/Goods/detail?id=AA001M5C
AHH Chemical co.,ltd	MT-42627	http://www.ahhchemical.com/product/MT-42627.html
AK Scientific, Inc. (AKSCI)	69106	http://www.aksci.com/item_detail.php?cat=69106
AZEPINE	AZ0001-0119	http://azepine.com/4-methoxyphenol.html
Aaron Chemicals	AR001MX4	http://www.aaronchem.com/150-76-5
AbMole Bioscience	M2839	http://www.abmole.com/products/mequinol.html
Acadechem	ACDS-029888	http://www.acadechemical.com/product/104587
Aceschem	ACS010307	https://www.aceschem.com/catalog/150-76-5.html
Achemica	ACMC-1BYTI	http://www.achemica.com/prodinfo/?id=75425
Achemo Scientific Limited	AC-30404	http://www.achemo.com/search/?Keyword= 150-76-5
Achemtek	0104-018824	http://www.achemtek.com/150-76-5
Acros Organics	AC126000051	https://www.fishersci.com/shop/products/4-methoxyphenol-99-pure-acros-organics-4/AC126000051
Acros Organics	AC126000250	https://www.fishersci.com/shop/products/4-methoxyphenol-99-pure-acros-organics-5/AC126000250
Acros Organics	AC126000010	https://www.fishersci.com/shop/products/4-methoxyphenol-99-pure-acros-organics/AC126000010
Acros Organics	AC126001000	https://www.fishersci.com/shop/products/4-methoxyphenol-99-pure-acros-organics/AC126001000
Acros Organics	AC126005000	https://www.fishersci.com/shop/products/4-methoxyphenol-99-pure-acros-organics/AC126005000
Alfa Aesar	A14845	https://www.alfa.com/en/catalog/A14845/
Alfa Chemistry	ACM150765	https://materials.alfachemic.com/product/4-methoxyphenol-cas-150-76-5-325660.html
Alfa Chemistry	AP150765	https://reagents.alfa-chemistry.com/product/4-methoxyphenol-cas-150-76-5-5422.html
Alichem	19146626	http://www.alichem.com/en/products/150-76-5.html
Allbio Pharm Co., Ltd	AD09818	http://www.allbiopharm.com/product/n/AD09818
Angene	AGN-PC-0A3NO4	http://www.angenechemical.com/productshow/AGN-PC-0A3NO4.html
Anward	ANW-21297	http://www.anward.com/pro_result/17064
ApexBio Technology	B1968	http://www.apexbt.com/mequinol.html
Ark Pharm	AK-46469	http://www.arkpharminc.com/products/150-76-5.html
Aromalake	LS10474	http://www.aromalake.com/4-Methoxyphenol-p651.html
Aromsyn	AS04576	http://www.aromsyn.com/product/AS04576.html
Aurora Fine Chemicals LLC	K02.105.255	http://online.aurorafinechemicals.com/info?ID=K02.105.255
Aurum Pharmatech LLC	M-5917	http://www.Aurumpharmatech.com/Product/ProductDetails/M_5917
Avantor Inc	200000-640	https://us.vwr.com/store/product/7514655/hydroquinone-monomethyl-ether
Avantor Inc	200000-642	https://us.vwr.com/store/product/7514655/hydroquinone-monomethyl-ether
Avantor Inc	700000-438	https://us.vwr.com/store/product/7829553/hydroquinone-monomethyl-ether-98
Avantor Inc	700000-442	https://us.vwr.com/store/product/7829553/hydroquinone-monomethyl-ether-98
Avantor Inc	TCM0123-100G	https://us.vwr.com/store/product/9986502/hydroquinone-monomethyl-ether-99-0
BLD Pharm	BD98576	http://www.bldpharm.com/products/150-76-5.html
BioCrick	BCC4797	http://www.biocrick.com/Mequinol-BCC4797.html
BioSynth	Q-200491	https://www.biosynth.com/en/products/chemical-intermediates/advanced-intermediates/products/Q-200491.html
BroadPharm	BP-23487	https://www.broadpharm.com/web/product.php?catalog=BP-23487
CSNpharm	CSN19520	https://www.csnpharm.com/products/mequinol.html
Capot Chemical	2276	http://www.capotchem.com/en/2276.htm
Capot Chemical	PubChem2276	http://www.capotchem.com/en/2276.htm
Chem Scene	CS-W019963	http://www.chemscene.com/150-76-5.html
ChemMol	1032247	http://www.chemmol.com/chemmol/1032247.html
ChemMol	1033837	http://www.chemmol.com/chemmol/1033837.html
ChemMol	30109569	http://www.chemmol.com/chemmol/30109569.html
ChemMol	44008890	http://www.chemmol.com/chemmol/44008890.html
ChemMol	49407120	http://www.chemmol.com/chemmol/49407120.html
Chemenu	CM116834	http://www.chemenu.com/products/CM116834
Chemspace	CSSB00000210503	https://chem-space.com/CSSB00000210503
Clearsynth	CS-O-01930	http://www.clearsynth.com/en/CSO01930.html
Clearsynth	CS-C-00689	https://www.clearsynth.com/en/CSC00689.html
Clearsynth	CS-T-78533	https://www.clearsynth.com/en/CST78533.html
DAOGE BIOPHARMA	DG21-14391	https://www.daogechem.com/product/150-76-5.html
DC Chemicals	DC37132	http://www.dcchemicals.com//product_show-Mequinol.html
Debye Scientific	DB-003965	http://www.debyesci.com/DB-003965.html
Enamine	Z1262246146	https://www.enaminestore.com/catalog/Z1262246146
Finetech	FT-0618865	http://www.finetechnology-ind.com/prod/detail/pub/150-76-5.html
Glentham Life Sciences	GK5518	http://www.glentham.com/products/product/GK5518/
Hairui	HR2276	http://www.hairuichem.com/en/product/150-76-5.html
Hefei Hirisun Pharmatech Co., Ltd	HR013123	http://www.hirisunpharm.com/150-76-5.html
LGC Standards	DRE-C15081450	https://www.lgcstandards.com/US/en/p/DRE-C15081450
LGC Standards	LGCFOR1131.00	https://www.lgcstandards.com/US/en/p/LGCFOR1131.00
LGC Standards	MM1131.00	https://www.lgcstandards.com/US/en/p/MM1131.00
Lab Network	LN00174589	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00174589
Matrix Scientific	75183	https://www.matrixscientific.com/075183.html
MedChem Express	HY-30270	https://www.medchemexpress.com/mequinol.html
Molcore	CS22939	https://www.molcore.com/product/150-76-5
Oakwood	78679	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=63853&ExtHyperLink=1
Otava	2826230	https://search.otavachemicals.com/#!/search?query=2826230&type=code&base=dbb
Parchem	26211	http://www.parchem.com/chemical-supplier-distributor/Hydroquinone-Monomethyl-Ether-016211.aspx
Renno Tech	RP19570	http://www.rennotech.com/product_show.asp?id=25327
Sigma-Aldrich	M18655_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/m18655?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	13-1980_SAJ	https://www.sigmaaldrich.com/catalog/product/saj/131980?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	54050_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/54050?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	92264_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/92264?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S014231	http://www.sinfoobiotech.com/product/1017629
Smolecule	S534995	http://www.smolecule.com/products/s534995
TCI (Tokyo Chemical Industry)	M0123	http://www.tcichemicals.com/eshop/en/us/commodity/M0123/index.html
THE BioTek	bt-274775	https://www.thebiotek.com/product/inhibitors/bt-274775
Vitas-M Laboratory	BBL019135	http://www.request.vitasmlab.biz/index.php?option=com_search_stk&Itemid=22&stk=BBL019135&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
VladaChem	VL143239	https://www.vladachem.com/product.php?products=150-76-5
VladaChem	VL163309	https://www.vladachem.com/product.php?products=150-76-5
VladaChem	VL274665-100G	https://www.vladachem.com/product.php?products=150-76-5
Yuhao Chemical	LQ0608	http://www.chemyuhao.com/150-76-5.html
abcr GmbH	AB117737	http://www.abcr.com/shop/en/AB117737
eNovation Chemicals	D409324	http://www.enovationchem.com/productDetails.asp?productID=D409324
iChemical	EBD21056	http://www.ichemical.com/products/150-76-5.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-7494596350	https://mcule.com/MCULE-7494596350/

PubMed

Title	Date	PubMed
Catalytic effect of soil colloids on the reaction between CrVI and p-methoxyphenol.	2001	11202717
Degradation of isoxaben in soils and an aqueous system.	2001 Nov	11757733
Speciation of gas-phase and fine particle emissions from burning of foliar fuels.	2002 Jun 1	12075778
Enhancement of the depigmenting effect of hydroquinone and 4-hydroxyanisole by all-trans-retinoic acid (tretinoin): the impairment of glutathione-dependent cytoprotection?	2003	12771467
Anise oil as para-methoxyamphetamine (PMA) precursor.	2003 Apr 23	12742705
A combination of ultrasound and oxidative enzyme: sono-biodegradation of substituted phenols.	2003 Jul	12818389
Antinociceptive properties of chloromaleinimides and their sulphonyl derivatives.	2004 Apr	15065079
Effect of phenolic mediators and humic acid on cyprodinil transformation in presence of birnessite.	2004 Jun	15207604
On the etiology of contact/occupational vitiligo.	2004 Jun	15140065
Purification and characterization of tyrosinase from gill tissue of Portabella mushrooms.	2004 Mar	15016563
Structural close-related aromatic compounds have different effects on laccase activity and on lcc gene expression in the ligninolytic fungus Trametes sp. I-62.	2004 Oct	15341917
Site-specific H/D exchange of p-methoxyphenol studied by resonant two-photon ionization and mass-analyzed threshold ionization spectroscopy.	2005 Oct 27	16866397
The combination of 2% 4-hydroxyanisole (mequinol) and 0.01% tretinoin effectively improves the appearance of solar lentigines in ethnic groups.	2006 Sep	17177746
Separation of molecular tracers sorbed onto atmospheric particulate matter by flash chromatography.	2007 Mar	17260135
A novel melanin inhibitor: hydroperoxy traxastane-type triterpene from flowers of Arnica montana.	2007 May	17473428
Urinary methoxyphenol biomarkers and woodsmoke exposure: comparisons in rural Guatemala with personal CO and kitchen CO, levoglucosan, and PM2.5.	2007 May 15	17547167
Subcellular localization and cytoplasmic complex status of endogenous Keap1.	2007 Oct	17903176
Suppression of interleukin-2 gene expression by isoeugenol is mediated through down-regulation of NF-AT and NF-kappaB.	2007 Sep	17630204
Electrochemical oxidation characteristics of p-substituted phenols using a boron-doped diamond electrode.	2007 Sep 15	17948806
Laser flash photolysis study of the triplet reactivity of beta-lapachones.	2008 Apr	18385890
Mequinol 2%/tretinoin 0.01% topical solution for the treatment of melasma in men: a case series and review of the literature.	2008 Feb	18441773
Efficient synthesis and properties of novel near-infrared electrochromic anthraquinone imides.	2008 Feb 21	18205375
Metabolic bioactivation and toxicity of ethyl 4-hydroxybenzoate in human SK-MEL-28 melanoma cells.	2008 May	17847068
The mechanism of the phosphoramidite synthesis of polynucleotides.	2008 Sep 21	18802632
Topical treatment of melasma.	2009	20101327
Peroxidase-mediated degradation of perfluorooctanoic acid.	2009 Feb	18808217
Urinary levoglucosan as a biomarker of wood smoke exposure: observations in a mouse model and in children.	2009 Jan	19165390
Production of o-diphenols by immobilized mushroom tyrosinase.	2009 Jan 15	19047003
Increase in the levels of chaperone proteins by exposure to beta-estradiol, bisphenol A and 4-methoxyphenol in human cells transfected with estrogen receptor alpha cDNA.	2009 Jun	19269315
Tris{2-meth-oxy-6-[(4-methyl-phen-yl)iminiometh-yl]phenolate-κO,O'}tris-(thio-cyanato-κN)europium(III).	2009 Nov 21	21578663
Development and evaluation of kinetic spectrophotometric assays for horseradish peroxidase by catalytic coupling of paraphenylenediamine and mequinol.	2009 Oct	19822971
(E)-2-[(4-Ethoxy-phen-yl)imino-meth-yl]-4-methoxy-phenol.	2009 Oct 10	21578305
6,6'-Dimeth-oxy-2,2'-[(E,E')-(4-chloro-m-phenyl-ene)bis-(nitrilo-methyl-idyne)]diphenol.	2009 Sep 30	21578010
Antioxidant activity of colored rice bran obtained at different milling yields.	2010	20877150
Radical-scavenging activity and cytotoxicity of p-methoxyphenol and p-cresol dimers.	2010 Feb 26	20335966
Heterogeneous reaction of gaseous ozone with aqueous iodide in the presence of aqueous organic species.	2010 May 20	20415500
Structure and vibrational frequencies of 6,7-dimethoxy-1,4-dihydro-1,3-quinoxalinedione based on density functional theory calculations: The role of pi-electron conjugation and back-donation.	2010 Sep 15	20538512

Patents

Sample Use Guides

In Vivo Use Guide

Apply Solagé to the solar lentigines using the applicator tip while avoiding application to the surrounding skin. Use twice daily, morning and evening at least 8 hours apart, or as directed by a physician. Patients should not shower or bathe the treatment areas for at least 6 hours after application of Solagé. Special caution should be taken when applying Solagé to avoid the eyes, mouth, paranasal creases, and mucous membranes.

Route of Administration: Topical

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 16 15:53:14 UTC 2022` Edited by `admin` on `Fri Dec 16 15:53:14 UTC 2022`
Record UNII	6HT8U7K3AM
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

MEQUINOL

Official Name

English

SOLAGE COMPONENT MEQUINOL

Common Name

English

4-Methoxyphenol

Systematic Name

English

Mequinol [WHO-DD]

Common Name

English

MEQUINOL [ORANGE BOOK]

Common Name

English

MEQUINOL COMPONENT OF SOLAGE

Common Name

English

MEQUINOL [MART.]

Common Name

English

P-HYDROXYANISOLE

Official Name

English

NSC-4960

Code

English

MEQUINOL [USAN]

Common Name

English

PHENOL, 4-METHOXY-

Systematic Name

English

BMS-181158

Code

English

P-HYDROXYANISOLE [INCI]

Common Name

English

MEQUINOL [HSDB]

Common Name

English

mequinol [INN]

Common Name

English

MEQUINOL [VANDF]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C78284