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 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 8429	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 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 270

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 270	substrate 3367 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
Depigmentation therapy in vitiligo universalis with topical 4-methoxyphenol and the Q-switched ruby laser.	2000 May	10775851
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
Arrest of cell cycle by inhibition of ribonucleotide reductase induces accumulation of NAD+ by Mn2+-supplemented growth of Corynebacterium ammoniagenes.	2003 Jan	12882290
Antioxidant activity and characterization of volatile constituents of Taheebo (Tabebuia impetiginosa Martius ex DC).	2003 Jan 1	12502424
[Hygienic standards of the occupational air quality established by the Experts on Chemical Agents, 2002].	2004	15156761
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
Correlation of in vitro chemopreventive efficacy data from the human epidermal cell assay with animal efficacy data and clinical trial plasma levels.	2005 Jun 1	15786488
Site-specific H/D exchange of p-methoxyphenol studied by resonant two-photon ionization and mass-analyzed threshold ionization spectroscopy.	2005 Oct 27	16866397
An investigation of the reduction in aqueous acetonitrile of 4-methoxybenzenediazonium ion by the tetrakis(acetonitrile)Cu(I) cation catalysed by hydrogenphosphate dianion.	2007 Feb 21	17285177
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
Quantification of organic eluates from polymerized resin-based dental restorative materials by use of GC/MS.	2007 May 1	17127109
Subcellular localization and cytoplasmic complex status of endogenous Keap1.	2007 Oct	17903176
Electrochemical oxidation characteristics of p-substituted phenols using a boron-doped diamond electrode.	2007 Sep 15	17948806
Efficient synthesis and properties of novel near-infrared electrochromic anthraquinone imides.	2008 Feb 21	18205375
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
In vivo anti-inflammatory action of eugenol on lipopolysaccharide-induced lung injury.	2010 Apr	20075264
Pi-selective stationary phases: (II) Adsorption behaviour of substituted aromatic compounds on n-alkyl-phenyl stationary phases.	2010 Aug 13	20537339
Depigmentation therapy in vitiligo universalis with cryotherapy and 4-hydroxyanisole.	2010 Mar	20447090

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 15 15:00:06 GMT 2023` Edited by `admin` on `Fri Dec 15 15:00:06 GMT 2023`
Record UNII	6HT8U7K3AM
Record Status	`Validated (UNII)`
Record Version

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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