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Identification
YMDB IDYMDB01631
NameAcetovanillone
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionAcetovanillone (or apocynin) is a natural organic compound structurally related to vanillin. It has been isolated from a variety of plant sources and is being studied for its variety of pharmacological properties.
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
DescriptionThis compound belongs to the class of chemical entities known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen 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