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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 01:04:15 UTC
Update Date2021-09-26 22:57:51 UTC
HMDB IDHMDB0247918
Secondary Accession NumbersNone
Metabolite Identification
Common NameAcetovanillone
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. Acetovanillone is a faint, sweet, and vanillin tasting compound. Acetovanillone is found, on average, in the highest concentration within white wine. Acetovanillone has also been detected, but not quantified in, a few different foods, such as asparagus (Asparagus officinalis), corns (Zea mays), and garden onions (Allium cepa). This could make acetovanillone a potential biomarker for the consumption of these foods. Acetovanillone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Acetovanillone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Acetovanillone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Acetovanillone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
1-(4-Hydroxy-3-methoxyphenyl)ethanoneChEBI
4'-Hydroxy-3'-methoxyacetophenoneChEBI
4-Acetyl-2-methoxyphenolChEBI
4-Hydroxy-3-methoxyphenyl methyl ketoneChEBI
AcetoguaiaconChEBI
AcetoguaiaconeChEBI
4-Hydroxy-3-methoxyacetophenoneHMDB
ApocynineHMDB
ApocyninHMDB
2-Methoxy-4-acetylphenolHMDB
3-Methoxy-4-hydroxyphenylethanoneHMDB
3'-Methoxy-4'-hydroxyacetophenoneHMDB
3’-methoxy-4’-hydroxyacetophenoneHMDB
4-AcetylguaiacolHMDB
4’-hydroxy-3’-methoxyacetophenoneHMDB
AcetoguaiacolHMDB
AcetoguaiconeHMDB
AcetovanilloneChEBI
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name1-(4-hydroxy-3-methoxyphenyl)ethan-1-one
Traditional Nameapocynin
CAS Registry NumberNot Available
SMILES
COC1=CC(=CC=C1O)C(C)=O
InChI Identifier
InChI=1S/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3
InChI KeyDFYRUELUNQRZTB-UHFFFAOYSA-N
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
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(1.62) g/LALOGPS
logP10(1.07) g/LChemAxon
logS10(-1.7) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AcetovanilloneCOC1=CC(=CC=C1O)C(C)=O2495.9Standard polar33892256
AcetovanilloneCOC1=CC(=CC=C1O)C(C)=O1407.1Standard non polar33892256
AcetovanilloneCOC1=CC(=CC=C1O)C(C)=O1481.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Acetovanillone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-2900000000-c2b9fc9aff1c67a83c672016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetovanillone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetovanillone GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetovanillone GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-4900000000-17a85dc123d088c3aa492015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetovanillone 10V, Positive-QTOFsplash10-014i-0900000000-498ed957aa15729fb0a42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetovanillone 20V, Positive-QTOFsplash10-014i-0900000000-c1c53a9c0ce83907c31f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetovanillone 40V, Positive-QTOFsplash10-0f6t-4900000000-9523f4aee91ded7398fa2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetovanillone 10V, Negative-QTOFsplash10-014i-0900000000-dd966d68c334c4588c5a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetovanillone 20V, Negative-QTOFsplash10-014i-0900000000-f50acbb85458094718fb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetovanillone 40V, Negative-QTOFsplash10-05mn-5900000000-38c38f7aec7f03fc4aa62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetovanillone 10V, Negative-QTOFsplash10-014i-0900000000-5dea0e2df5cd18252bf02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetovanillone 20V, Negative-QTOFsplash10-066s-0900000000-4aa899ac7457495c236b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetovanillone 40V, Negative-QTOFsplash10-0006-9200000000-488dceb176525121ae132021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetovanillone 10V, Positive-QTOFsplash10-0006-9300000000-a7b7fde927bc2ff25c6e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetovanillone 20V, Positive-QTOFsplash10-0006-9100000000-fa257fa9b73b26e921ad2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetovanillone 40V, Positive-QTOFsplash10-002f-9000000000-9160fcb70adace18630c2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12618
Phenol Explorer Compound IDNot Available
FooDB IDFDB012055
KNApSAcK IDC00002689
Chemspider ID21106900
KEGG Compound IDC11380
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkApocynin
METLIN IDNot Available
PubChem Compound2214
PDB IDNot Available
ChEBI ID2781
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1057511
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]