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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:32:07 UTC
Update Date2022-03-07 02:52:15 UTC
HMDB IDHMDB0029696
Secondary Accession Numbers
  • HMDB29696
Metabolite Identification
Common 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.
Structure
Data?1582753452
Synonyms
ValueSource
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
HQMME
hydroxyquinone methyl ether
HQMME; hydroxyquinone methyl etherHMDB
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

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point53 °CNot Available
Boiling Point243.00 to 245.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility40 mg/mL at 25 °CNot Available
LogP1.58Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+126.16231661259
DarkChem[M-H]-122.79831661259
DeepCCS[M+H]+126.52130932474
DeepCCS[M-H]-122.78830932474
DeepCCS[M-2H]-160.14730932474
DeepCCS[M+Na]+135.38830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MequinolCOC1=CC=C(O)C=C12120.3Standard polar33892256
MequinolCOC1=CC=C(O)C=C11182.9Standard non polar33892256
MequinolCOC1=CC=C(O)C=C11200.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Mequinol,1TMS,isomer #1COC1=CC=C(O[Si](C)(C)C)C=C11287.0Semi standard non polar33892256
Mequinol,1TBDMS,isomer #1COC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C11515.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Mequinol EI-B (Non-derivatized)splash10-00du-9300000000-7365fadaa1b55aee92c02017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Mequinol EI-B (Non-derivatized)splash10-0ab9-3900000000-b24cf2309ebe14f7ea372017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Mequinol EI-B (Non-derivatized)splash10-05gi-8900000000-22bed3d3611c3a5cd0d62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Mequinol EI-B (Non-derivatized)splash10-0ab9-3900000000-b406ffca43dc64f803562017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Mequinol EI-B (Non-derivatized)splash10-05fr-3900000000-5f100d415313d60a9ba02017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Mequinol EI-B (Non-derivatized)splash10-00du-9300000000-7365fadaa1b55aee92c02018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Mequinol EI-B (Non-derivatized)splash10-0ab9-3900000000-b24cf2309ebe14f7ea372018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Mequinol EI-B (Non-derivatized)splash10-05gi-8900000000-22bed3d3611c3a5cd0d62018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Mequinol EI-B (Non-derivatized)splash10-0ab9-3900000000-b406ffca43dc64f803562018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Mequinol EI-B (Non-derivatized)splash10-05fr-3900000000-5f100d415313d60a9ba02018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mequinol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-7900000000-55f898f30c9805b4268e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mequinol GC-MS (1 TMS) - 70eV, Positivesplash10-00ea-6900000000-adc42694c52a9cf1ab972017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mequinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mequinol 10V, Positive-QTOFsplash10-004i-0900000000-3d4bc54dec9d0d2bf71d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mequinol 20V, Positive-QTOFsplash10-004i-1900000000-cd190cc17b12c804fb8d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mequinol 40V, Positive-QTOFsplash10-0691-9200000000-f98954ef6d73d4d0fc192015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mequinol 10V, Negative-QTOFsplash10-00di-0900000000-3cb1894d95675088e7b22015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mequinol 20V, Negative-QTOFsplash10-00di-0900000000-125ba3d5d60e387415e52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mequinol 40V, Negative-QTOFsplash10-0a4i-9600000000-c374964c5ebd2e35933e2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mequinol 10V, Negative-QTOFsplash10-00di-0900000000-ee9e9b8403f62cfc7fdf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mequinol 20V, Negative-QTOFsplash10-00dl-5900000000-b042371b5dd653689b362021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mequinol 40V, Negative-QTOFsplash10-0ufu-9000000000-f159f82bc0ae0498fa492021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mequinol 10V, Positive-QTOFsplash10-004i-0900000000-c91956e06e080706e4b92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mequinol 20V, Positive-QTOFsplash10-00kb-9100000000-4d814c03b4eb6b3e4ad72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mequinol 40V, Positive-QTOFsplash10-0j7m-9000000000-91642d9378817b499b9b2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
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
FooDB 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
MarkerDB IDNot Available
Good Scents IDrw1027421
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.. .