You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB01809
NameZingerone
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionZingerone, also known as [0]-paradol or vanillylacetone, 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. Zingerone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
  • (4-Hydroxy-3-methoxyphenyl)ethyl methyl ketone
  • [0]-Paradol
  • 2-Butanone, 4-(4-hydroxy-3-methoxyphenyl)-
  • 3-Methoxy-4-hydroxybenzylacetone
  • 4-(4-Hydroxy-3-methoxyphenyl)-2-butanone
  • 4-(4-hydroxy-3-methoxyphenyl)butan-2-one
  • 4-Hydroxy-3-methoxybenzylacetone
  • 4(4-Hydroxy-3-methoxyphenyl)-2-butanone
  • Gingerone
  • Vanillylacetone
  • Zingerone (vanillyl acetone)
  • zingerone [3-(4-hydroxy-3-methoxyphenyl)butan-2-one]
  • Zingiberone
  • (0)-Paradol
  • 2-(4-Hydroxy-3-methoxyphenyl)ethyl methyl ketone
  • 4-(3-Methoxy-4-hydroxyphenyl)-2-butanone
  • 4-(3-Methoxy-4-hydroxyphenyl)butan-2-one
  • Zingherone
  • 4-(4-Hydroxy-3-methoxy-phenyl)-butan-2-one
  • 4-(4-Hydroxy-3-methoxyphenyl)-2-butanone, 9ci, 8ci
  • FEMA 3124
  • Vanillyl acetone
  • [0]Paradol
  • 0 Paradol
CAS number122-48-5
WeightAverage: 194.2271
Monoisotopic: 194.094294314
InChI KeyOJYLAHXKWMRDGS-UHFFFAOYSA-N
InChIInChI=1S/C11H14O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h5-7,13H,3-4H2,1-2H3
IUPAC Name4-(4-hydroxy-3-methoxyphenyl)butan-2-one
Traditional IUPAC Namezingerone
Chemical FormulaC11H14O3
SMILESCOC1=C(O)C=CC(CCC(C)=O)=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
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ketone
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point40.5 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.57 g/LALOGPS
logP2.02ALOGPS
logP1.92ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)9.95ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.96 m³·mol⁻¹ChemAxon
Polarizability20.95 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
AnimalFDB010527
CloveFDB010527
GingerFDB010527
PhenolicFDB010527
SpicyFDB010527
SweetFDB010527
VanillaFDB010527
WoodyFDB010527
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, Positivesplash10-0006-5900000000-42ac2a1b364f92df5152JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9370000000-988fce303c33c65d61c8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-4c68e7e311ed162223a5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004s-1900000000-e0ac7417df02644e0761JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f9l-7900000000-2f6d6b18947145fb0dbfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-8f3da5e61712d1ffacb3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-2900000000-53b85d6dc1005c5d4df0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5900000000-f12fadc90e8da514347fJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID68657
HMDB IDHMDB0032590
Pubchem Compound ID13733135
Kegg IDC17497
ChemSpider ID28952
FOODB IDFDB010527
Wikipedia IDZingerone
BioCyc IDNot Available