Record Information
Version1.0
Creation date2010-04-08 22:08:22 UTC
Update date2020-09-17 15:33:36 UTC
Primary IDFDB009011
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBeechwood, creosote (fagus spp.)
DescriptionGuajol or Guaiacol, also known as 2-hydroxyanisole or 2-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. Guaiacol is a phenolic compound with a methoxy group and is the monomethyl ether of catechol. Guaiacol is a sweet, medicinal, and phenolic tasting compound. Guaiacol is found in the highest concentration within a few different foods, such as sesames, coffee, and white wines and in a lower concentration in peppermints. Guaiacol has also been detected, but not quantified in white mustards, peppers, red bell peppers, cherry tomato, turmerics. Guaiacol is readily oxidized by the heme iron of peroxidases including the peroxidase of cyclooxygenase (COX) enzymes. It therefore serves as a reducing co-substrate for COX reactions. Guaiacol is a phenolic natural product first isolated from Guaiac resin and the oxidation of lignin. It is a yellowish aromatic oil that is now commonly derived from guaiacum or wood creosote. It is used medicinally as an expectorant, antiseptic, and local anesthetic. Guaiacol is used in traditional dental pulp sedation and has the property of inducing cell proliferation; guaiacol is a potent scavenger of reactive oxygen radicals and its radical scavenging activity may be associated with its effect on cell proliferation (PMID: 16152729). Guaiacol is used in the preparation of synthetic vanillin. Guaiacol is also present in wood smoke, as a product of pyrolysis of lignin. Guaiacol has been found in the urine of patients with neuroblastoma and pheochromocytoma. (PMID 4344880, 16152729)
CAS Number8021-39-4
Structure
Thumb
Synonyms
SynonymSource
1-Hydroxy-2-methoxybenzeneChEBI
2-HydroxyanisoleChEBI
Catechol monomethyl etherChEBI
O-MethoxyphenolChEBI
CreodonKegg
2-MethoxyphenolHMDB
2-Methoxy-phenolHMDB
AnastilHMDB
Guaiacol (liquid) extra pureHMDB
GuaiastilHMDB
GuaicolHMDB
GuaicolinaHMDB
GuajakolHMDB
GuajolHMDB
GuasolHMDB
GuiacolHMDB
MethoxyphenolHMDB
MethylcatacholHMDB
MethylcatecholHMDB
O-GuaiacolHMDB
O-HydroxyanisoleHMDB
O-Methoxy-phenolHMDB
O-Methyl catecholHMDB
Pyrocatechol monomethyl etherHMDB
Pyroguaiac acidHMDB
2-Hydroxy-anisoleHMDB
Catechol, methylHMDB
Methyl catecholHMDB
2-Methoxyl-4-vinylphenolHMDB
GuaiacolHMDB
Creosote, woodmanual
Predicted Properties
PropertyValueSource
Water Solubility67.4 g/LALOGPS
logP1.32ALOGPS
logP1.51ChemAxon
logS-0.27ALOGPS
pKa (Strongest Acidic)9.98ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.5 m³·mol⁻¹ChemAxon
Polarizability12.69 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H8O2
IUPAC name2-methoxyphenol
InChI IdentifierInChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3
InChI KeyLHGVFZTZFXWLCP-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=CC=C1
Average Molecular Weight124.139
Monoisotopic Molecular Weight124.052429498
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
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 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:

Biological location:

Source:

Role

Environmental role:

Industrial application:

Foods
  • Cocoa and cocoa products
  • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateliquid
    Physical DescriptionNot Available
    Mass CompositionNot Available
    Melting PointNot Available
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    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
    EI-MSMass Spectrum (Electron Ionization)splash10-0ac0-9800000000-5e89a9881e848e1b6c90Spectrum
    GC-MSBeechwood, creosote (fagus spp.), non-derivatized, GC-MS Spectrumsplash10-0a4i-6900000000-49cb804087a42b1d1a22Spectrum
    GC-MSBeechwood, creosote (fagus spp.), non-derivatized, GC-MS Spectrumsplash10-0ab9-5900000000-b580cbc25d4176ce3894Spectrum
    GC-MSBeechwood, creosote (fagus spp.), non-derivatized, GC-MS Spectrumsplash10-0pir-9700000000-f1436b3de82cff342b65Spectrum
    GC-MSBeechwood, creosote (fagus spp.), non-derivatized, GC-MS Spectrumsplash10-05fr-4900000000-c09a31d9523d2eab5598Spectrum
    GC-MSBeechwood, creosote (fagus spp.), non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-283fdedfda9e853e0cacSpectrum
    GC-MSBeechwood, creosote (fagus spp.), non-derivatized, GC-MS Spectrumsplash10-0a4i-6900000000-49cb804087a42b1d1a22Spectrum
    GC-MSBeechwood, creosote (fagus spp.), non-derivatized, GC-MS Spectrumsplash10-0ab9-5900000000-b580cbc25d4176ce3894Spectrum
    GC-MSBeechwood, creosote (fagus spp.), non-derivatized, GC-MS Spectrumsplash10-0pir-9700000000-f1436b3de82cff342b65Spectrum
    GC-MSBeechwood, creosote (fagus spp.), non-derivatized, GC-MS Spectrumsplash10-05fr-4900000000-c09a31d9523d2eab5598Spectrum
    GC-MSBeechwood, creosote (fagus spp.), non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-283fdedfda9e853e0cacSpectrum
    Predicted GC-MSBeechwood, creosote (fagus spp.), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-8900000000-562c1e6a4f3289578f75Spectrum
    Predicted GC-MSBeechwood, creosote (fagus spp.), 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fl0-7900000000-93aa107b2b3f584b3e44Spectrum
    Predicted GC-MSBeechwood, creosote (fagus spp.), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positivesplash10-0a4i-6900000000-49cb804087a42b1d1a22Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0ab9-5900000000-b580cbc25d4176ce3894Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0pir-9700000000-12606badb77d4257635dSpectrum
    MS/MSLC-MS/MS Spectrum - n/a 8V, negativesplash10-0a4i-0900000000-053a1c4e865e710614d5Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-6b7a2fdf4e9a28ec6045Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2900000000-ff014b7b55a5237cf91eSpectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9100000000-8785b2e2d86c6294a754Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-8856c60866e810389af7Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1900000000-8db14d5e5710471f76a7Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9400000000-bc0d3592d62ec26dad6fSpectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-7b4303f129d3e70a570eSpectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-9100000000-3ec9cfe154e8a98b3596Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w29-9000000000-ba9e4cd4adef59feb26eSpectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-ee9e9b8403f62cfc7fdfSpectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-4900000000-d36c74cf39c4ddda0024Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gbc-9000000000-1b43386dae7e3252cd81Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    2D NMR[1H,13C] 2D NMR SpectrumSpectrum
    ChemSpider IDNot Available
    ChEMBL IDNot Available
    KEGG Compound IDNot Available
    Pubchem Compound IDNot Available
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer IDNot Available
    DrugBank IDNot Available
    HMDB IDNot Available
    CRC / DFC (Dictionary of Food Compounds) IDNot Available
    EAFUS ID292
    Dr. Duke IDNot Available
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    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
    FlavoursNot Available
    Files
    MSDSNot Available
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference