Record Information
Version1.0
Creation date2010-04-08 22:04:45 UTC
Update date2020-02-24 19:10:16 UTC
Primary IDFDB000886
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMequinol
DescriptionMequinol, also known as 4-hydroxyanisole or leucodinine b, 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 a phenolic tasting compound. Mequinol has been detected, but not quantified in, anises (Pimpinella anisum) and sweet marjorams (Origanum majorana). This could make mequinol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Mequinol.
CAS Number150-76-5
Structure
Thumb
Synonyms
SynonymSource
4-HydroxyanisoleMeSH
4-Hydroxyanisole, potassium saltMeSH
4-Hydroxyanisole, sodium saltMeSH
Leucodinine bMeSH
Hydroquinone methyl etherMeSH
Hydroquinone monomethyl etherMeSH
p-HydroxyanisoleMeSH
Para-methoxyphenolMeSH
Menthyl anthranilateChEMBL, HMDB
novo-DermoquinonaChEMBL, HMDB
Leucodine bChEMBL, HMDB
BMS-181158P-GuaiacolChEMBL, HMDB
4-MethoxyphenolChEMBL, HMDB
4HAChEMBL, HMDB
LeucobasalChEMBL, HMDB
MechinolumChEMBL, HMDB
Menthyl anthranilic acidGenerator, HMDB
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
HQMMENot Available
hydroxyquinone methyl etherNot Available
HQMME; hydroxyquinone methyl etherHMDB
Mequinol, INN, USANdb_source
Mono methyl ether hydroquinonebiospider
P-hydroxymethoxybenzenebiospider
P-methoxyphenolbiospider
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
Chemical FormulaC7H8O2
IUPAC name4-methoxyphenol
InChI IdentifierInChI=1S/C7H8O2/c1-9-7-4-2-6(8)3-5-7/h2-5,8H,1H3
InChI KeyNWVVVBRKAWDGAB-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC=C(O)C=C1
Average Molecular Weight124.1372
Monoisotopic Molecular Weight124.0524295
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 67.73%; H 6.50%; O 25.78%DFC
Melting PointMp 53°DFC
Boiling PointBp12 128°DFC
Experimental Water Solubility40 mg/mL at 25 oCCHEMICALS INSPECTION AND TESTING INSTITU (1992)
Experimental logP1.58HANSCH,C ET AL. (1995)
Experimental pKapKa1 10.12 (25°, 0.1M KCl)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSMequinol, non-derivatized, GC-MS Spectrumsplash10-00du-9300000000-7365fadaa1b55aee92c0Spectrum
GC-MSMequinol, non-derivatized, GC-MS Spectrumsplash10-0ab9-3900000000-b24cf2309ebe14f7ea37Spectrum
GC-MSMequinol, non-derivatized, GC-MS Spectrumsplash10-05gi-8900000000-22bed3d3611c3a5cd0d6Spectrum
GC-MSMequinol, non-derivatized, GC-MS Spectrumsplash10-0ab9-3900000000-b406ffca43dc64f80356Spectrum
GC-MSMequinol, non-derivatized, GC-MS Spectrumsplash10-05fr-3900000000-5f100d415313d60a9ba0Spectrum
GC-MSMequinol, non-derivatized, GC-MS Spectrumsplash10-00du-9300000000-7365fadaa1b55aee92c0Spectrum
GC-MSMequinol, non-derivatized, GC-MS Spectrumsplash10-0ab9-3900000000-b24cf2309ebe14f7ea37Spectrum
GC-MSMequinol, non-derivatized, GC-MS Spectrumsplash10-05gi-8900000000-22bed3d3611c3a5cd0d6Spectrum
GC-MSMequinol, non-derivatized, GC-MS Spectrumsplash10-0ab9-3900000000-b406ffca43dc64f80356Spectrum
GC-MSMequinol, non-derivatized, GC-MS Spectrumsplash10-05fr-3900000000-5f100d415313d60a9ba0Spectrum
Predicted GC-MSMequinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-7900000000-55f898f30c9805b4268eSpectrum
Predicted GC-MSMequinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ea-6900000000-adc42694c52a9cf1ab97Spectrum
Predicted GC-MSMequinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-3d4bc54dec9d0d2bf71dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1900000000-cd190cc17b12c804fb8dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0691-9200000000-f98954ef6d73d4d0fc19Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-3cb1894d95675088e7b2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-125ba3d5d60e387415e5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9600000000-c374964c5ebd2e35933eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-ee9e9b8403f62cfc7fdfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-5900000000-b042371b5dd653689b36Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufu-9000000000-f159f82bc0ae0498fa49Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-c91956e06e080706e4b9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-9100000000-4d814c03b4eb6b3e4ad7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0j7m-9000000000-91642d9378817b499b9bSpectrum
NMRNot Available
ChemSpider ID8665
ChEMBL IDCHEMBL544
KEGG Compound IDNot Available
Pubchem Compound ID9015
Pubchem Substance IDNot Available
ChEBI ID113474
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29696
CRC / DFC (Dictionary of Food Compounds) IDBLQ78-M:BLQ83-K
EAFUS IDNot Available
Dr. Duke IDHYDROQUINONE-METHYL-ETHER|HYDROQUINONE-MONOMETHYL-ETHER
BIGG IDNot Available
KNApSAcK IDC00035022
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1027421
SuperScent IDNot Available
Wikipedia IDMequinol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
phenolic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).