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 IDYMDB01631
NameAcetovanillone
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionAcetovanillone, also known as acetoguaiacon, 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. Acetovanillone is an extremely weak basic (essentially neutral) compound (based on its pKa). Acetovanillone may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
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
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
Polarizability16.95 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
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
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 IDNot Available
Pubchem Compound ID2214
Kegg IDC11380
ChemSpider ID21106900
FOODB IDFDB012055
Wikipedia IDApocynin
BioCyc IDNot Available