You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:38:19 UTC
Update Date2019-07-23 06:33:33 UTC
HMDB IDHMDB0041006
Secondary Accession Numbers
  • HMDB41006
Metabolite Identification
Common Name1'-Acetoxychavicol
Description1'-Acetoxychavicol belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. An acetate ester that is chavicol acetate substituted by an acetoxy group at position 1'. 1'-Acetoxychavicol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 1'-Acetoxychavicol has been detected, but not quantified in, herbs and spices and root vegetables. This could make 1'-acetoxychavicol a potential biomarker for the consumption of these foods.
Structure
Data?1563863613
Synonyms
ValueSource
(AlphaS)-4-(acetyloxy)-alpha-ethenylbenzenemethanolChEBI
(AlphaS)-4-(acetyloxy)-a-ethenylbenzenemethanolGenerator
(AlphaS)-4-(acetyloxy)-α-ethenylbenzenemethanolGenerator
1'-Acetoxychavicol acetic acidGenerator
Chemical FormulaC13H14O4
Average Molecular Weight234.2479
Monoisotopic Molecular Weight234.089208936
IUPAC Name(1S)-1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate
Traditional Name1'-acetoxychavicol acetate
CAS Registry Number151986-17-3
SMILES
CC(=O)O[C@@H](C=C)C1=CC=C(OC(C)=O)C=C1
InChI Identifier
InChI=1S/C13H14O4/c1-4-13(17-10(3)15)11-5-7-12(8-6-11)16-9(2)14/h4-8,13H,1H2,2-3H3/t13-/m0/s1
InChI KeyJAMQIUWGGBSIKZ-ZDUSSCGKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol esters
Sub ClassNot Available
Direct ParentPhenol esters
Alternative Parents
Substituents
  • Phenol ester
  • Benzyloxycarbonyl
  • Phenoxy compound
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.58ALOGPS
logP2.05ChemAxon
logS-3.3ALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity61.99 m³·mol⁻¹ChemAxon
Polarizability24.06 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0900000000-1abea45849299f24ade5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002u-0950000000-bab1e5d60064ed54fd6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-0900000000-f79652ac903a15e56eb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-1900000000-962bbdcd8eeb60b29c29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-1960000000-cdce662dd688b22d71d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000x-2920000000-086e7d1ca558654bc999Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052e-6900000000-bb4d8adbbf61bce88907Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB020866
KNApSAcK IDC00002711
Chemspider ID106419
KEGG Compound IDC10426
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound119104
PDB IDNot Available
ChEBI ID469
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .