Acetovanillone (YMDB01631)

Identification
YMDB IDYMDB01631
NameAcetovanillone
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionAcetovanillone, also known as acetoguaiacon or apocynine, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Based on a literature review a small amount of articles have been published on Acetovanillone.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-(4-Hydroxy-3-methoxyphenyl)-ethanone (acetovanillone)
  • 1-(4-Hydroxy-3-methoxyphenyl)ethanone
  • 2-Methoxy-4-acetylphenol
  • 3-Methoxy-4-hydroxyacetophenone
  • 3-Metoksy-4-hydroksyacetofenon
  • 3'-Methoxy-4'-hydroxyacetophenone
  • 4-Acetyl-2-methoxyphenol
  • 4-Acetylguaiacol
  • 4-Hydroxy-3-methoxyacetophenone
  • 4-Hydroxy-3-methoxyphenyl methyl keton
  • 4-Hydroxy-3-methoxyphenyl methyl ketone
  • 4'-Hydroxy-3'-methoxyacetophenone
  • Acetoguaiacon
  • Acetoguaiacone
  • Acetophenone, 4'-hydroxy-3'-methoxy-
  • Acetovanillone
  • Acetovanilone
  • Acetovanyllon
  • Apocynin
  • Apocynine
  • Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-
  • Phenol, 4-acetyl-2-methoxy
  • 3-Methoxy-4-hydroxyphenylethanone
  • 3’-methoxy-4’-hydroxyacetophenone
  • 4’-hydroxy-3’-methoxyacetophenone
  • Acetoguaiacol
  • Acetoguaicone
CAS numberNot Available
WeightAverage: 166.1739
Monoisotopic: 166.062994186
InChI KeyDFYRUELUNQRZTB-UHFFFAOYSA-N
InChIInChI=1S/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3
IUPAC Name1-(4-hydroxy-3-methoxyphenyl)ethan-1-one
Traditional IUPAC Nameapocynin
Chemical FormulaC9H10O3
SMILESCOC1=CC(=CC=C1O)C(C)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Methoxyphenol
  • Acetophenone
  • Phenoxy compound
  • Methoxybenzene
  • Aryl alkyl ketone
  • Anisole
  • Phenol ether
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Ether
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point115 °C
Experimental Properties
PropertyValueReference
Water Solubility5 mg/mL at 20 oC [BEILSTEIN]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.04 g/LALOGPS
logP1.62ALOGPS
logP1.07ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)8.27ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.9 m³·mol⁻¹ChemAxon
Polarizability16.94 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
FaintFDB012055
SweetFDB012055
VanillaFDB012055
VanillinFDB012055
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, Positivesplash10-0fk9-2900000000-c2b9fc9aff1c67a83c67JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-498ed957aa15729fb0a4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-c1c53a9c0ce83907c31fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6t-4900000000-9523f4aee91ded7398faJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-dd966d68c334c4588c5aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-f50acbb85458094718fbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mn-5900000000-38c38f7aec7f03fc4aa6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-5dea0e2df5cd18252bf0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066s-0900000000-4aa899ac7457495c236bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-488dceb176525121ae13JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9300000000-a7b7fde927bc2ff25c6eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9100000000-fa257fa9b73b26e921adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-9000000000-9160fcb70adace18630cJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0udi-4900000000-17a85dc123d088c3aa49JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C 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 NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H 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 ID2781
HMDB IDHMDB0247918
Pubchem Compound ID2214
Kegg IDC11380
ChemSpider ID21106900
FOODB IDFDB012055
Wikipedia IDApocynin
BioCyc IDNot Available