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Identification
YMDB IDYMDB01430
Name2-methoxyphenol
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionGuaiacol (2-methoxyphenol) is a naturally occurring organic compound with the formula C6H4(OH)(OCH3). Although it is biosynthesized by a variety of organisms, this colorless aromatic oil is usually derived from guaiacum or wood creosote. Samples darken upon exposure to air and light. Guaiacol is present in wood smoke, resulting from the pyrolysis of lignin. The compound contributes to the flavor of many compounds, e.g. roasted coffee. [Wikipedia]
Structure
Thumb
Synonyms
  • 1-Hydroxy-2-methoxybenzene
  • 2-Hydroxyanisole
  • 2-Methoxy phenol (guiacol)
  • 2-methoxy-Phenol
  • 2-methoxyphenol (guaiacol)
  • 4-(3-Hydroxy-1-propenyl)-2-methoxyphenol
  • Anastil
  • Catechol monomethyl ether
  • Coniferol
  • Coniferyl alcohol
  • Creodon
  • Guaiacol
  • Guaiastil
  • Guaicol
  • Guaicolina
  • Guajakol
  • Guajol
  • Guasol
  • guiacol
  • Methoxyphenol
  • Methylcatachol
  • Methylcatechol
  • o-Guaiacol
  • o-Guiacol
  • o-Hydroxyanisole
  • o-methoxy-Phenol
  • o-Methoxyphenol
  • O-Methyl catechol
  • ortho-Guaiacol
  • Phenol, 2-methoxy-
  • Phenol, o-methoxy-
  • Pyrocatechol monomethyl ether
  • Pyroguaiac acid
  • 2-Methoxyphenol
  • Guaiacol (liquid) extra pure
  • 2-Hydroxy-anisole
  • Catechol, methyl
  • Methyl catechol
  • 2-Methoxyl-4-vinylphenol
CAS number90-05-1
WeightAverage: 124.1372
Monoisotopic: 124.0524295
InChI KeyLHGVFZTZFXWLCP-UHFFFAOYSA-N
InChIInChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3
IUPAC Name2-methoxyphenol
Traditional IUPAC Nameguaiacol
Chemical FormulaC7H8O2
SMILESCOC1=CC=CC=C1O
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
  • 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
Physical Properties
StateLiquid
Charge0
Melting point28 °C
Experimental Properties
PropertyValueReference
Water Solubility18.7 mg/mL at 15 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP1.32 [HANSCH,C ET AL. (1995)]PhysProp
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-6900000000-49cb804087a42b1d1a22JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ab9-5900000000-b580cbc25d4176ce3894JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0pir-9700000000-f1436b3de82cff342b65JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05fr-4900000000-c09a31d9523d2eab5598JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-283fdedfda9e853e0cacJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-6900000000-49cb804087a42b1d1a22JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ab9-5900000000-b580cbc25d4176ce3894JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0pir-9700000000-f1436b3de82cff342b65JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05fr-4900000000-c09a31d9523d2eab5598JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-283fdedfda9e853e0cacJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-8900000000-562c1e6a4f3289578f75JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fl0-7900000000-93aa107b2b3f584b3e44JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positivesplash10-0a4i-6900000000-49cb804087a42b1d1a22JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0ab9-5900000000-b580cbc25d4176ce3894JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0pir-9700000000-12606badb77d4257635dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-6b7a2fdf4e9a28ec6045JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2900000000-ff014b7b55a5237cf91eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9100000000-8785b2e2d86c6294a754JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-8856c60866e810389af7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1900000000-8db14d5e5710471f76a7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9400000000-bc0d3592d62ec26dad6fJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0ac0-9800000000-5e89a9881e848e1b6c90JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Mahadevan, K., Farmer, L. (2006). "Key odor impact compounds in three yeast extract pastes." J Agric Food Chem 54:7242-7250.16968089
Synthesis Reference:Chen, Jiehua; Xu, Baocai; Zhang, Hong; Ye, Jianfeng. Method for preparing guaiacol from catechol and dimethyl carbonate. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 6pp.
External Links:
ResourceLink
CHEBI ID28591
HMDB IDHMDB01398
Pubchem Compound ID460
Kegg IDC00590
ChemSpider ID447
FOODB IDFDB011885
WikipediaGuaiacol
BioCyc IDCPD-400