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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:32:07 UTC
Update Date2020-02-26 21:44:12 UTC
HMDB IDHMDB0029696
Secondary Accession Numbers
  • HMDB29696
Metabolite Identification
Common NameMequinol
DescriptionMequinol, also known as 4-hydroxyanisole or 4-methoxyphenol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Mequinol is an extremely weak basic (essentially neutral) compound (based on its pKa). Mequinol is a phenolic tasting compound. Outside of the human body, Mequinol has been detected, but not quantified in, anises and sweet marjorams. This could make mequinol a potential biomarker for the consumption of these foods. Conversely, tretinoin has been observed to serve as a potent inhibitor of mammalian GSTs and to be capable of reducing the level of intracellular GSH in various cells . Such products are not indicated for oral ingestion . Nevertheless, skin cells are naturally capable of protecting themselves against such cytotoxic entities by endogenous intracellular glutathione (GSH) . Regardless, it is consequently by way of this seemingly negative and damaging pharmacodynamic profile by which the mechanism of action of mequinol is sometimes described . Urine samples from melanoma patients treated with mequinol were analyzed and various mequinol metabolites were identified, including 3,4-dihydroxyanisole, the two o-methyl derivatives 3-hydroxy-4-methoxyanisole and 4-hydroxy-3-methoxyanisole, and even hydroquinone which may have originated at least partly from mequinol . It is used as an inhibitor for acrylic monomers and acrylonitirles, as a stabilizer for chlorinated hydrocarbons and ethyl cellulose, as an ultraviolet inhibitor, as a chemical intermediate in the manufacture of antioxidants, pharmaceuticals, plasticizers, and dyestuffs . Mequinol is in fact considered a melanocytotoxic chemical which when oxidized in melanocytes results in the formation of toxic entities like quinones .
Structure
Data?1582753452
Synonyms
ValueSource
4-HydroxyanisoleHMDB
HQMME; hydroxyquinone methyl etherHMDB
Menthyl anthranilateHMDB
Novo-dermoquinonaHMDB
Leucodine bHMDB
BMS-181158P-GuaiacolHMDB
p-HydroxyanisoleHMDB
4-MethoxyphenolHMDB
4HAHMDB
LeucobasalHMDB
MechinolumHMDB
Menthyl anthranilic acidHMDB
1-Hydroxy-4-methoxybenzeneHMDB
4-Methoxy-phenolHMDB
HydroxyanisoleHMDB
Hydroxyquinone methyl etherHMDB
Mequinol, inn, usanHMDB
mono Methyl ether hydroquinoneHMDB
Monomethyl ether hydroquinoneHMDB
p-HydroxymethoxybenzeneHMDB
p-MethoxyphenolHMDB
Para-methoxyphenolHMDB
4-Hydroxyanisole, sodium saltMeSH
Hydroquinone monomethyl etherMeSH
4-Hydroxyanisole, potassium saltMeSH
Hydroquinone methyl etherMeSH
Leucodinine bMeSH
HQMME
Chemical FormulaC7H8O2
Average Molecular Weight124.1372
Monoisotopic Molecular Weight124.0524295
IUPAC Name4-methoxyphenol
Traditional Namemethoxyphenol
CAS Registry Number150-76-5
SMILES
COC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C7H8O2/c1-9-7-4-2-6(8)3-5-7/h2-5,8H,1H3
InChI KeyNWVVVBRKAWDGAB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • 4-alkoxyphenol
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point53 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility40 mg/mL at 25 °CNot Available
LogP1.58Not Available
Predicted Properties
PropertyValueSource
Water Solubility36.1 g/LALOGPS
logP1.31ALOGPS
logP1.51ChemAxon
logS-0.54ALOGPS
pKa (Strongest Acidic)9.94ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.5 m³·mol⁻¹ChemAxon
Polarizability12.76 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00du-9300000000-7365fadaa1b55aee92c0Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ab9-3900000000-b24cf2309ebe14f7ea37Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05gi-8900000000-22bed3d3611c3a5cd0d6Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ab9-3900000000-b406ffca43dc64f80356Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05fr-3900000000-5f100d415313d60a9ba0Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00du-9300000000-7365fadaa1b55aee92c0Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ab9-3900000000-b24cf2309ebe14f7ea37Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05gi-8900000000-22bed3d3611c3a5cd0d6Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ab9-3900000000-b406ffca43dc64f80356Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05fr-3900000000-5f100d415313d60a9ba0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-7900000000-55f898f30c9805b4268eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ea-6900000000-adc42694c52a9cf1ab97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-3d4bc54dec9d0d2bf71dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1900000000-cd190cc17b12c804fb8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0691-9200000000-f98954ef6d73d4d0fc19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-3cb1894d95675088e7b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-125ba3d5d60e387415e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9600000000-c374964c5ebd2e35933eSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB09516
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000886
KNApSAcK IDC00035022
Chemspider ID8665
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMequinol
METLIN IDNot Available
PubChem Compound9015
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .