1'S-Acetoxychavicol acetate (CHEM034147)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 04:42:03 UTC
Update Date2016-11-09 01:21:04 UTC
Accession NumberCHEM034147
Identification
Common Name1'S-Acetoxychavicol acetate
ClassSmall Molecule
Description1-(4-Hydroxyphenyl)-2-propen-1-ol; (±)-form, Di-Ac is found in herbs and spices. 1-(4-Hydroxyphenyl)-2-propen-1-ol; (±)-form, Di-Ac is a constituent of Alpinia galanga (greater galangal).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1'-Acetoxychavicol acetic acidGenerator
(1S)-1-[4-(Acetyloxy)phenyl]prop-2-en-1-yl acetateHMDB
(AlphaS)-4-(acetyloxy)-alpha-ethenylbenzenemethanolHMDB
1's-1'-Acetoxychavicol acetateHMDB
Galangal acetateHMDB
1-[4-(Acetyloxy)phenyl]prop-2-en-1-yl acetic acidGenerator
1's-Acetoxychavicol acetic acidGenerator
Chemical FormulaC13H14O4
Average Molecular Mass234.248 g/mol
Monoisotopic Mass234.089 g/mol
CAS Registry Number52946-22-2
IUPAC Name1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate
Traditional Name1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate
SMILESCC(=O)OC(C=C)C1=CC=C(OC(C)=O)C=C1
InChI IdentifierInChI=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
InChI KeyJAMQIUWGGBSIKZ-UHFFFAOYSA-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 DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Polarizability24.28 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0900000000-1abea45849299f24ade5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-0970000000-81735b3654a481b06311Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0036-1900000000-9b5975ebd113945e0e7cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-2900000000-699c26c2e1a06248898eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-9620000000-6a6a1fa37916a3b9a0eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9100000000-f44a6f5a57c94e8e8e93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9300000000-ef559bb25482dcb0b386Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0041005
FooDB IDFDB020865
Phenol Explorer IDNot Available
KNApSAcK IDC00031531
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID354584
ChEBI IDNot Available
PubChem Compound ID400072
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Weerakkody NS, Smith WM, Mikkelsen D, Waanders J, Kerven G, Caffin N, Dykes GA, Turner MS: Purified 1'acetoxychavicol acetate (1'ACA) from galangal spice affects membrane fatty acid composition and triggers a cell envelope stress response in Staphylococcus aureus. Int J Antimicrob Agents. 2012 Mar;39(3):269-71. doi: 10.1016/j.ijantimicag.2011.11.010. Epub 2012 Jan 9.
2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.