Record Information
Version1.0
Creation date2010-04-08 22:09:58 UTC
Update date2018-01-25 19:40:42 UTC
Primary IDFDB012055
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAcetovanillone
DescriptionAcetovanillone, also known as 4'-hydroxy-3'-methoxyacetophenone or acetoguaiacon, is a member of the class of compounds known as alkyl-phenylketones. Alkyl-phenylketones are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Acetovanillone is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Acetovanillone is a faint, sweet, and vanillin tasting compound found in corn and garden onion, which makes acetovanillone a potential biomarker for the consumption of these food products. Acetovanillone may be a unique S.cerevisiae (yeast) metabolite.
CAS Number498-02-2
Structure
Thumb
Synonyms
SynonymSource
1-(4-Hydroxy-3-methoxyphenyl)ethanoneChEBI
4'-Hydroxy-3'-methoxyacetophenoneChEBI
4-Acetyl-2-methoxyphenolChEBI
4-Hydroxy-3-methoxyphenyl methyl ketoneChEBI
AcetoguaiaconChEBI
AcetoguaiaconeChEBI
ApocynineMeSH
ApocyninMeSH
4-Hydroxy-3-methoxyacetophenoneMeSH
-acetylguaiacolbiospider
-Hydroxy-3-methoxyphenyl methyl ketonbiospider
-Methoxy-4-acetylphenolbiospider
'-Methoxy-4'-hydroxyacetophenonebiospider
1-(4-hydroxy-3-methoxyphenyl)-ethanonebiospider
1-(4-Hydroxy-3-methoxyphenyl)-ethanone (acetovanillone)biospider
1-(4-hydroxy-3-methoxyphenyl)ethan-1-onebiospider
2-Methoxy-4-acetylphenolbiospider
3-Methoxy-4-hydroxyacetophenonebiospider
3-Metoksy-4-hydroksyacetofenonbiospider
3'-Methoxy-4'-hydroxyacetophenonebiospider
4-Acetylguaiacolbiospider
4-Hydroxy-3-methoxyphenyl methyl ketonbiospider
4'-H-3'-MAPbiospider
4'-Hydroxy-3'-methoxyacetophenone, 8CIdb_source
Acetophenone, 4'-hydroxy-3'-methoxy-biospider
ACETOPHENONE,4-HYDROXY,3-METHOXY ACETOVANILLONbiospider
Acetovanillonbiospider
Acetovanillonedb_source
Acetovanilonebiospider
Acetovanyllonbiospider
Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-biospider
Phenol, 4-acetyl-2-methoxybiospider
Vanilloyl methyl ketonedb_source
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
Chemical FormulaC9H10O3
IUPAC name1-(4-hydroxy-3-methoxyphenyl)ethan-1-one
InChI IdentifierInChI=1S/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3
InChI KeyDFYRUELUNQRZTB-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=CC(=C1)C(C)=O
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 65.05%; H 6.07%; O 28.88%DFC
Melting PointMp 115°DFC
Boiling PointBp17.5 233° (lit. gives a pressure range)DFC
Experimental Water Solubility5 mg/mL at 20 oCBEILSTEIN
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-2900000000-c2b9fc9aff1c67a83c67JSpectraViewer
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
MSMass Spectrum (Electron Ionization)splash10-0udi-4900000000-17a85dc123d088c3aa49JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC11380
Pubchem Compound ID2214
Pubchem Substance IDNot Available
ChEBI ID2781
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBJQ72-S:HCV60-D
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00002689
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID498-02-2
GoodScent IDrw1057511
SuperScent ID2214
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
NADPH-oxidase inhibitor50423 An EC 1.6.3.* (oxidoreductase acting on NADH or NADPH with oxygen as acceptor) inhibitor that interferes with the action of NAD(P)H oxidase (H2O2-forming), EC 1.6.3.1.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
vanilla
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
faint
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
vanillin
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.