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

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 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Solar lentigines 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020922s006lbl.pdf	Primary		Approved 8583	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 1999

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 Sources: https://pubmed.ncbi.nlm.nih.gov/17177746/	healthy, 55.8 years Health Status: healthy Age Group: 55.8 years Sex: M+F 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 Sources: https://pubmed.ncbi.nlm.nih.gov/17177746/	healthy, 55.8 years Health Status: healthy Age Group: 55.8 years Sex: M+F 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 Sources: https://pubmed.ncbi.nlm.nih.gov/17177746/	healthy, 55.8 years Health Status: healthy Age Group: 55.8 years Sex: M+F 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 Sources: https://pubmed.ncbi.nlm.nih.gov/17177746/	healthy, 55.8 years Health Status: healthy Age Group: 55.8 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/17177746/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP 303

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 303	substrate 4014 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
Aaron Chemicals	AR001MX4	http://www.aaronchem.com/150-76-5
abcr GmbH	AB117737	http://www.abcr.com/shop/en/AB117737
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	AC126000010	https://www.fishersci.com/shop/products/4-methoxyphenol-99-pure-acros-organics/AC126000010
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	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
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
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
AZEPINE	AZ0001-0119	http://azepine.com/4-methoxyphenol.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
BLD Pharm	BD98576	http://www.bldpharm.com/products/150-76-5.html
BroadPharm	BP-23487	https://www.broadpharm.com/web/product.php?catalog=BP-23487
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
Chemenu	CM116834	http://www.chemenu.com/products/CM116834
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
Chemspace	CSSB00000210503	https://chem-space.com/CSSB00000210503
Clearsynth	CS-C-00689	https://www.clearsynth.com/en/CSC00689.html
Clearsynth	CS-O-01930	http://www.clearsynth.com/en/CSO01930.html
Clearsynth	CS-T-78533	https://www.clearsynth.com/en/CST78533.html
CSNpharm	CSN19520	https://www.csnpharm.com/products/mequinol.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
eNovation Chemicals	D409324	http://www.enovationchem.com/productDetails.asp?productID=D409324
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
iChemical	EBD21056	http://www.ichemical.com/products/150-76-5.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00174589	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00174589
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
Matrix Scientific	75183	https://www.matrixscientific.com/075183.html
mcule	MCULE-7494596350	https://mcule.com/MCULE-7494596350/
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	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
Sigma-Aldrich	M18655_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/m18655?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

PubMed

Title	Date	PubMed
The influence of fibrous elastomer structure and porosity on matrix organization.	2010-12-22	21203510
Pairwise substitution effects, inter- and intramolecular hydrogen bonds in methoxyphenols and dimethoxybenzenes. Thermochemistry, calorimetry, and first-principles calculations.	2010-12-16	21086965
Rate coefficients for the gas-phase reaction of hydroxyl radicals with 2-methoxyphenol (guaiacol) and related compounds.	2010-11-04	20919717
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.	2010-09-15	20538512
Molecular characteristics of Kraft-AQ pulping lignin fractionated by sequential organic solvent extraction.	2010-08-16	21152286
Pi-selective stationary phases: (II) Adsorption behaviour of substituted aromatic compounds on n-alkyl-phenyl stationary phases.	2010-08-13	20537339
Synthesis and characterization of amine bridged bis(phenolate) lanthanide aryloxides and their application in the polymerization of lactide.	2010-08-07	20520920
Hydrogen hyperfine splitting constants for phenoxyl radicals by DFT methods: regression analysis unravels hydrogen bonding effects.	2010-07-21	20480076
Surface photochemistry of pesticides containing 4-chlorophenoxyl chromophore.	2010-07-15	20334970
Application of ex situ dynamic nuclear polarization in studying small molecules.	2010-06-14	20454737
Heterogeneous reaction of gaseous ozone with aqueous iodide in the presence of aqueous organic species.	2010-05-20	20415500
In vivo anti-inflammatory action of eugenol on lipopolysaccharide-induced lung injury.	2010-04	20075264
Depigmentation therapy in vitiligo universalis with cryotherapy and 4-hydroxyanisole.	2010-03	20447090
Strategic distribution of protective proteins within bran layers of wheat protects the nutrient-rich endosperm.	2010-03	20061449
Amperometric phenol biosensor based on horseradish peroxidase entrapped PVF and PPy composite film coated GC electrode.	2010-03	19224403
Radical-scavenging activity and cytotoxicity of p-methoxyphenol and p-cresol dimers.	2010-02-26	20335966
Marine natural meroterpenes: synthesis and antiproliferative activity.	2010-02-23	20390109
Structure-toxicity relationship of phenolic analogs as anti-melanoma agents: an enzyme directed prodrug approach.	2010-02-12	19944085
Measurement of phenols dearomatization via electrolysis: the UV-Vis solid phase extraction method.	2010-02	19922974
Antioxidant activity of colored rice bran obtained at different milling yields.	2010	20877150
The hunt for natural skin whitening agents.	2009-12-10	20054473
Tris{2-meth-oxy-6-[(4-methyl-phen-yl)iminiometh-yl]phenolate-κO,O'}tris-(thio-cyanato-κN)europium(III).	2009-11-21	21578663
(E)-2-[(4-Ethoxy-phen-yl)imino-meth-yl]-4-methoxy-phenol.	2009-10-10	21578305
Development and evaluation of kinetic spectrophotometric assays for horseradish peroxidase by catalytic coupling of paraphenylenediamine and mequinol.	2009-10	19822971
6,6'-Dimeth-oxy-2,2'-[(E,E')-(4-chloro-m-phenyl-ene)bis-(nitrilo-methyl-idyne)]diphenol.	2009-09-30	21578010
Mechanisms regulating skin pigmentation: the rise and fall of complexion coloration.	2009-09-15	19865532
Simulation of IR and Raman spectra of p-hydroxyanisole and p-nitroanisole based on scaled DFT force fields and their vibrational assignments.	2009-09-15	19523872
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.	2009-06	19269315
Current and emerging therapy for the management of vitiligo.	2009-03-12	21436965
Peroxidase-mediated degradation of perfluorooctanoic acid.	2009-02	18808217
Production of o-diphenols by immobilized mushroom tyrosinase.	2009-01-15	19047003
Urinary levoglucosan as a biomarker of wood smoke exposure: observations in a mouse model and in children.	2009-01	19165390
Topical treatment of melasma.	2009	20101327
Antiproliferative effects of honey and of its polyphenols: a review.	2009	19636435
Reaction of phenols with the 2,2-diphenyl-1-picrylhydrazyl radical. Kinetics and DFT calculations applied to determine ArO-H bond dissociation enthalpies and reaction mechanism.	2008-12-05	18991378
Results of a residential indoor PM2.5 sampling program before and after a woodstove changeout.	2008-10	18665872
The mechanism of the phosphoramidite synthesis of polynucleotides.	2008-09-21	18802632
Analytic quantification of the bleaching effect of a 4-hydroxyanisole-tretinoin combination on actinic lentigines.	2008-09	19112802
Assessing urinary levoglucosan and methoxyphenols as biomarkers for use in woodsmoke exposure studies.	2008-08-25	18511108
Essential explanation of the strong mineralization performance of boron-doped diamond electrodes.	2008-07-01	18678026
A highly specific BODIPY-based fluorescent probe for the detection of hypochlorous acid.	2008-06-05	18447382
An efficient protocol for the enantioselective preparation of a key polyfunctionalized cyclohexane. New access to (R)- and (S)-4-Hydroxy-2-cyclohexenone and (R)- and (S)-trans-cyclohex-2-ene-1,4-diol.	2008-05-02	18363375
Metabolic bioactivation and toxicity of ethyl 4-hydroxybenzoate in human SK-MEL-28 melanoma cells.	2008-05	17847068
Laser flash photolysis study of the triplet reactivity of beta-lapachones.	2008-04	18385890
Efficient synthesis and properties of novel near-infrared electrochromic anthraquinone imides.	2008-02-21	18205375
Mequinol 2%/tretinoin 0.01% topical solution for the treatment of melasma in men: a case series and review of the literature.	2008-02	18441773
Subcellular localization and cytoplasmic complex status of endogenous Keap1.	2007-10	17903176
Electrochemical oxidation characteristics of p-substituted phenols using a boron-doped diamond electrode.	2007-09-15	17948806
Suppression of interleukin-2 gene expression by isoeugenol is mediated through down-regulation of NF-AT and NF-kappaB.	2007-09	17630204
Physico-chemical studies on the evaluation of the antioxidant activity of herbal extracts and active principles of some Indian medicinal plants.	2007-05	18398494

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

Name

Type

Language

P-HYDROXYANISOLE

Preferred Name

English

MEQUINOL

Official Name

English

SOLAGE COMPONENT MEQUINOL

Common Name

English

4-Methoxyphenol

Systematic Name

English

Mequinol [WHO-DD]

Common Name

English

4-HYDROXYANISOLE

Systematic Name

English

MEQUINOL [ORANGE BOOK]

Common Name

English

MEQUINOL [MART.]

Common Name

English

NSC-4960

Code

English

MEQUINOL [USAN]

Common Name

English

PHENOL, 4-METHOXY-

Systematic Name

English

BMS-181158

Code

English

MEQUINOL [HSDB]

Common Name

English

mequinol [INN]

Common Name

English

MEQUINOL [VANDF]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C78284