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Identification
YMDB IDYMDB01677
NameE-4-Propenyl-2-methoxyphenol
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionIsoeugenol, also known as propenylgualacol, 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. Based on a literature review a significant number of articles have been published on Isoeugenol.
Structure
Thumb
Synonyms
  • (E)-2-methoxy-4-(prop-1-enyl)phenol
  • (E)-Isoeugenol
  • 2-methoxy-4-(1-propenyl)phenol
  • 2-Methoxy-4-[(1E)-1-propenyl]phenol
  • 4-(1-Propenyl)-2-methoxyphenol (trans-isoeugenol)
  • 4-Vinylguaiacol
  • iso-Eugenol 2
  • Isoeugenol (E)
  • Isoeugenol (I)
  • Isoeugenol (II)
  • Isoeugenol E
  • Isoeugenol trans-form
  • Isoeugenol Z
  • Phenol, 2-methoxy-4-(1-propenyl)-, (E)-
  • Phenol, 2-methoxy-4-propenyl-, (E)-
  • trans-2-methoxy-4-(1-propenyl)phenol
  • trans-2-Methoxy-4-propenylphenol
  • trans-Isoeugenol
  • trans-p-Propenylquaiacol
  • 2-Methoxy-4-propenylphenol
  • 3-Methoxy-4-hydroxy-1-propen-1-ylbenzene
  • 3-Methoxy-4-hydroxypropenylbenzene
  • 4-Hydroxy-3-methoxy-1-propenylbenzene
  • Propenylgualacol
  • trans-4-Propenylgualacol
  • 2-Methoxy-4-(prop-1-en-1-yl)phenol
  • (e)-2-Methoxy-4- (1-propenyl)-phenol
  • (e)-2-Methoxy-4-(1-propenyl)-phenol
  • (e)-2-Methoxy-4-propenyl-phenol
  • 1-(3-Methoxy-4-hydroxyphenyl)-1-propane
  • 1-Hydroxy-2-methoxy-4-propen-1-ylbenzene
  • 2-Methoxy-4-(1-propenyl)-phenol
  • 2-Methoxy-4-(1-propenyl)phenol (acd/name 4.0)
  • 2-Methoxy-4-propenyl-phenol
  • 2-Methoxy-4-[(1E)-prop-1-en-1-yl]phenol
  • 4-Hydroxy-3-methoxy-1-propen-1-ylbenzene
  • 4-Hydroxy-3-methoxypropenylbenzene
  • Isoeugenol, (e)-isomer
  • Isoeugenol
  • (E)-2-Methoxy-4-(1-propenyl)phenol
  • (E)-2-Methoxy-4-(prop-1-en-1-yl)phenol
  • 1-(3-Methoxy-4-hydroxyphenyl)-1-propene
  • 2-Methoxy-4(E)-1-propenylphenol
  • 2-Methoxy-4-(1-propen-1-yl)phenol
  • 2-Methoxy-4-(1E)-1-propen-1-ylphenol
  • 2-Methoxy-4-[(E)-1-propenyl]phenol
  • 3-Methoxy-4-hydroxy-1-propenylbenzene
  • 4-(1-Propenyl) Guaiacol
  • 4-Hydroxy-3-methoxy-beta-methylstyrene
  • 4-Hydroxy-3-methoxy-β-methylstyrene
  • 4-Propenylguaiacol
  • iso-Eugenol
  • trans-4-Propenylguaiacol
  • trans-p-Propenylguaiacol
CAS number5932-68-3
WeightAverage: 164.2011
Monoisotopic: 164.083729628
InChI KeyBJIOGJUNALELMI-ONEGZZNKSA-N
InChIInChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3+
IUPAC Name2-methoxy-4-[(1E)-prop-1-en-1-yl]phenol
Traditional IUPAC Nameisoeugenol
Chemical FormulaC10H12O2
SMILESCOC1=CC(\C=C\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
  • Styrene
  • 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 point33.5 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.36 g/LALOGPS
logP2.79ALOGPS
logP2.64ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)10.01ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.86 m³·mol⁻¹ChemAxon
Polarizability18.3 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
CarnationFDB012403
CloveFDB012403
FloralFDB012403
FlowerFDB012403
PhenolicFDB012403
SpicyFDB012403
SweetFDB012403
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)splash10-03di-5900000000-d5e9036e83fd9c1033b0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-4900000000-f0dd30e91dc041336262JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-1900000000-1530d67ee6f2740c4978JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-5900000000-d5e9036e83fd9c1033b0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-4900000000-f0dd30e91dc041336262JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-1900000000-1530d67ee6f2740c4978JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ds-1900000000-54cb7bf6efac012f1f93JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-7790000000-39afffdef59235ab22a4JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-0019-0900000000-95d2bb40c1282fcc841bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-0a4i-0900000000-66bdcdfc1f3c9d7059efJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-0a4i-2900000000-1eef4e3fa8cc372a7bd0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-000i-0900000000-568dabede3d6d65eef27JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000i-0900000000-704d8c207b799f62a165JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0079-1900000000-dc5eb5b27b41f37fff51JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-00du-6900000000-724fc19b181ae95ed7f0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-0006-9400000000-e33fcab9c4877cbfaaa8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-00kf-9100000000-7581434dd013744b10feJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-014l-9000000000-a332174b204c08062e14JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-014i-9000000000-eca4e980b9dcfbfa0d88JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-51b1ddd89b75760804fbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-59e54fb66a534d3ff6dcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-92bea35f22ee86583e9fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-976746f8642ed9cede8fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-aeeef853384070786115JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9400000000-28c3454817ba3f918700JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-ba4c51d900ead0baa741JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-b71be30e0aefb9374dd3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0535-4900000000-dc2d63615991af22ecd9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0900000000-6f75a3780b4d03c3f78fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00m3-2900000000-f418214add56c19743eaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00or-9000000000-95268ee51bd407edd9b8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-8db47caa9667c101bd0fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03ds-0900000000-c240e3167c4ef90295d0JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0ik9-7900000000-d378eaa3d6e1b33ea92eJSpectraViewer | 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 ID50545
HMDB IDHMDB0005802
Pubchem Compound ID332
Kegg IDC10469
ChemSpider ID21106129
FOODB IDFDB012403
WikipediaIsoeugenol
BioCyc IDNot Available