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4-Ethyl-2-methoxyphenol (YMDB01615)

Identification
YMDB IDYMDB01615
Name4-Ethyl-2-methoxyphenol
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description4-Ethyl-2-methoxyphenol is a volatile phenol found in wines spoiled with the Brettanomyces wild yeast. It is produced by Brettanomyces as a result of enzymatic conversion of vinylphenols derived from cinnamic acids naturally present in the grape must. At low concentrations, this compound is thought to add to wine complexity, but at high concentrations the wine is considered spoiled and has been described as animal, barnyard, stable, phenolic, and mousy. [PMID: 17850808, PMID: 17676867]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-Hydroxy-2-methoxy-4-allylbenzene
  • 1-Hydroxy-2-methoxy-4-prop-2-enylbenzene
  • 1-Hydroxy-2-methoxy-4-propenylbenzene
  • 1'-Acetoxyeugenol acetate
  • 2-Hydroxy-5-allylanisole
  • 2-Methoxy-1-hydroxy-4-allylbenzene
  • 2-Methoxy-4-(2-propenyl)phenol
  • 2-Methoxy-4-(3-propenyl)phenol
  • 2-methoxy-4-(prop-2-en-1-yl)phenol
  • 2-Methoxy-4-allylphenol
  • 2-Methoxy-4-ethylphenol
  • 2-Methoxy-4-prop-2-enylphenol
  • 4-(Acetyloxy)-alpha-ethenyl-3-methoxybenzenemethanol acetate
  • 4-Allyl-1-hydroxy-2-methoxybenzene
  • 4-allyl-2-methoxy-Phenol
  • 4-allyl-2-methoxyphenol
  • 4-Allylcatechol 2-methyl ether
  • 4-Allylcatechol-2-methyl ether
  • 4-Allylguaiacol
  • 4-ethyl guiacol
  • 4-Ethyl-2-methoxyphenol
  • 4-ethyl-2-methoxyphenol (4-ethylguaiacol)
  • 4-Ethyl-2-metoxy phenol
  • 4-Ethylguaiacol
  • 4-Hydroxy-3-methoxy ethylbenzene
  • 4-Hydroxy-3-methoxy-1-allylbenzene
  • 4-Hydroxy-3-methoxyallylbenzene
  • 5-Allylguaiacol
  • Allylguaiacol
  • Caryophyllic acid
  • Engenol
  • ethylguiacol (4-ethyl-2-methoxyphenol)
  • Eugenic acid
  • Eugenol
  • guaiacol, 4-ethyl
  • P-allylguaiacol
  • p-Ethyl-2-methoxyphenol
  • p-Ethylguaiacol
  • P-eugenol
  • Phenol, 2-methoxy-4-(2-propenyl)-
  • Phenol, 2-methoxy-4-ethyl
  • Phenol, 4-ethyl-2-methoxy-
  • Synthetic eugenol
  • 1-Hydroxy-2-methoxy-4-ethylbenzene
  • 4-Ethyl-2-methoxy-phenol
  • 4-Ethyl-guaiacol
  • 4-Hydroxy-3-methoxyethylbenzene
  • 4-Hydroxy-3-methoxyphenylethane
  • FEMA 2436
  • Guaiacyl ethane
  • Homocresol
CAS number2785-89-9
WeightAverage: 152.1904
Monoisotopic: 152.083729628
InChI KeyCHWNEIVBYREQRF-UHFFFAOYSA-N
InChIInChI=1S/C9H12O2/c1-3-7-4-5-8(10)9(6-7)11-2/h4-6,10H,3H2,1-2H3
IUPAC Name4-ethyl-2-methoxyphenol
Traditional IUPAC Name4-ethylguaiacol
Chemical FormulaC9H12O2
SMILESCCC1=CC=C(O)C(OC)=C1
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-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
StateSolid
Charge0
Melting point-7 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.41 g/LALOGPS
logP2.36ALOGPS
logP2.47ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)10.3ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.14 m³·mol⁻¹ChemAxon
Polarizability16.75 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
BaconFDB019887
CloveFDB019887
PhenolicFDB019887
SmokyFDB019887
SpiceFDB019887
SpicyFDB019887
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fe0-1900000000-309cbcd4c3b5c618be96JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-7970000000-0c5781b2a64e9da81fc1JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-2a9371bb243c77e192e6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1900000000-85d8006a41fe7e064e95JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-9200000000-22e200002e86f96c1187JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-0f4955d3a66c1c69cc27JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-acb830966ea966b2ef30JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0553-7900000000-03acff5e7f7c4a1400a3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0900000000-5da9cfbe875826c8990fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufr-4900000000-a3c7ad0be273d13bb026JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fvr-9000000000-81e6db59083c8f5d738fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-3cd265ceef2fb5f5db20JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0900000000-037544de7548b6280b04JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054o-9300000000-ef78296cecf47c0a1643JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-000i-9700000000-746fbad678716b9e066eJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB0040175
Pubchem Compound ID3314
Kegg IDC10427
ChemSpider ID56245
FOODB IDFDB019887
Wikipedia IDNot Available
BioCyc IDNot Available