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Identification
YMDB IDYMDB01613
Name4-Allyl-2-methoxyphenol
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionEugenol, also known as 4-allylguaiacol or 1,3,4-eugenol, 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. Eugenol is an extremely weak basic (essentially neutral) compound (based on its pKa). Eugenol exists in all eukaryotes, ranging from yeast to humans. Eugenol is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 1-Hydroxy-2-methoxy-4-allylbenzene
  • 1-Hydroxy-2-methoxy-4-prop-2-enylbenzene
  • 1-Hydroxy-2-methoxy-4-propenylbenzene
  • 1,3,4-Eugenol
  • 1'-Acetoxyeugenol acetate
  • 2-Hydroxy-5-allylanisole
  • 2-Methoxy-1-hydroxy-4-allylbenzene
  • 2-Methoxy-4-(2-propenyl)phenol
  • 2-Methoxy-4-(2-propenyl)phenyl
  • 2-Methoxy-4-(3-propenyl)phenol
  • 2-methoxy-4-(prop-2-en-1-yl)phenol
  • 2-Methoxy-4-allylphenol
  • 2-Methoxy-4-prop-2-enylphenol
  • 2-Metoksy-4-allilofenol
  • 4-(2-Propenyl)-2-methoxyphenol (eugenol)
  • 4-(Acetyloxy)-alpha-ethenyl-3-methoxybenzenemethanol acetate
  • 4-Allyl-1-hydroxy-2-methoxybenzene
  • 4-allyl-2-methoxy-Phenol
  • 4-allyl-2-methoxyphenol
  • 4-allyl-2-methoxyphenol (eugenol)
  • 4-Allyl-2-rnethoxyphenol (eugenol)
  • 4-Allylcatechol 2-methyl ether
  • 4-Allylcatechol-2-methyl ether
  • 4-Allylguaiacol
  • 4-Hydroxy-3-methoxy-1-allylbenzene
  • 4-Hydroxy-3-methoxyallylbenzene
  • 5-Allylguaiacol
  • Allylguaiacol
  • Caryophyllic acid
  • Engenol
  • Eugenic acid
  • Eugenol
  • Eugenol (2-Methoxy-4-(2-propenyl)phenol)
  • Eugenol (natural)
  • Eugenol [usan]
  • P-allylguaiacol
  • P-eugenol
  • Phenol, 2-methoxy-4-(2-propenyl)-
  • Phenol, 4-allyl-2-methoxy-
  • Synthetic eugenol
  • 1-Allyl-3-methoxy-4-hydroxybenzene
  • 1-Allyl-4-hydroxy-3-methoxybenzene
  • 2-Methoxy-4-(2-propen-1-yl)phenol
  • Caryophyllate
  • Eugenate
CAS number97-53-0
WeightAverage: 164.2011
Monoisotopic: 164.083729628
InChI KeyRRAFCDWBNXTKKO-UHFFFAOYSA-N
InChIInChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
IUPAC Name2-methoxy-4-(prop-2-en-1-yl)phenol
Traditional IUPAC Nameeugenol
Chemical FormulaC10H12O2
SMILESCOC1=CC(CC=C)=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-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-9.1 °C
Experimental Properties
PropertyValueReference
Water Solubility2.46 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP2.27 [SANGSTER (1993)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.44 g/LALOGPS
logP2.66ALOGPS
logP2.61ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)9.94ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.79 m³·mol⁻¹ChemAxon
Polarizability17.9 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
CinnamonFDB012171
CloveFDB012171
HoneyFDB012171
SpicyFDB012171
SweetFDB012171
WoodyFDB012171
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)splash10-0ik9-5900000000-3d3a9e4f250074741003JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-2900000000-395df8510f0db4933abeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-6900000000-1afdd3b83f6832b11f70JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-4900000000-1d96ae8b031e47e13112JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ik9-6900000000-def0c646d72c040b58daJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-0900000000-dfa64951eb648f5c9df1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ik9-5900000000-3d3a9e4f250074741003JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-2900000000-395df8510f0db4933abeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-6900000000-1afdd3b83f6832b11f70JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-4900000000-1d96ae8b031e47e13112JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ik9-6900000000-def0c646d72c040b58daJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-0900000000-dfa64951eb648f5c9df1JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ms-1900000000-da27a86009649c155318JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-8790000000-0d0c6f0e58d7dc3e5620JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0900000000-4541582e8f6395e2fa87JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-84f950d2fc0742e324d5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ab9-0900000000-4c037643a10913a70f5eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-83f8f32dfd9b94fb1d24JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-2900000000-c65a2dab49b8ebb431daJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-65a67ccd1df0d2f1796fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-9d2a857e8a482a061127JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-9c846765367542bf4db1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fr6-9500000000-98fcaf3ccca850c34bd3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-835320dc79855273af7fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-3a70eb9601589d9108a1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052e-4900000000-1c4834945c53d64bab3bJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0il0-6900000000-ff0dc492bab70317bb2aJSpectraViewer | MoNA
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 ID4917
HMDB IDHMDB05809
Pubchem Compound ID3314
Kegg IDC10427
ChemSpider ID13876103
FOODB IDFDB012171
Wikipedia IDEugenol
BioCyc IDNot Available