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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:38:15 UTC
Update Date2022-03-07 02:56:50 UTC
HMDB IDHMDB0041005
Secondary Accession Numbers
  • HMDB41005
Metabolite Identification
Common Name1'-Acetoxychavicol acetate
Description1'-Acetoxychavicol acetate 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. 1'-Acetoxychavicol acetate has been detected, but not quantified in, herbs and spices. This could make 1'-acetoxychavicol acetate a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 1'-Acetoxychavicol acetate.
Structure
Data?1563863613
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 Weight234.2479
Monoisotopic Molecular Weight234.089208936
IUPAC Name1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate
Traditional Name1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate
CAS Registry Number52946-22-2
SMILES
CC(=O)OC(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
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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point325.40 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility233.4 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.900 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+155.90331661259
DarkChem[M-H]-153.92531661259
DeepCCS[M+H]+153.49230932474
DeepCCS[M-H]-151.13430932474
DeepCCS[M-2H]-184.14430932474
DeepCCS[M+Na]+159.58530932474
AllCCS[M+H]+153.932859911
AllCCS[M+H-H2O]+150.032859911
AllCCS[M+NH4]+157.432859911
AllCCS[M+Na]+158.432859911
AllCCS[M-H]-154.832859911
AllCCS[M+Na-2H]-155.132859911
AllCCS[M+HCOO]-155.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1'-Acetoxychavicol acetateCC(=O)OC(C=C)C1=CC=C(OC(C)=O)C=C12564.7Standard polar33892256
1'-Acetoxychavicol acetateCC(=O)OC(C=C)C1=CC=C(OC(C)=O)C=C11729.1Standard non polar33892256
1'-Acetoxychavicol acetateCC(=O)OC(C=C)C1=CC=C(OC(C)=O)C=C11686.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1'-Acetoxychavicol acetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0900000000-1abea45849299f24ade52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1'-Acetoxychavicol acetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1'-Acetoxychavicol acetate 10V, Positive-QTOFsplash10-002u-0950000000-bab1e5d60064ed54fd6b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1'-Acetoxychavicol acetate 20V, Positive-QTOFsplash10-004l-0900000000-f79652ac903a15e56eb42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1'-Acetoxychavicol acetate 40V, Positive-QTOFsplash10-001j-1900000000-962bbdcd8eeb60b29c292017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1'-Acetoxychavicol acetate 10V, Negative-QTOFsplash10-000x-1960000000-cdce662dd688b22d71d92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1'-Acetoxychavicol acetate 20V, Negative-QTOFsplash10-000x-2920000000-086e7d1ca558654bc9992017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1'-Acetoxychavicol acetate 40V, Negative-QTOFsplash10-052e-6900000000-bb4d8adbbf61bce889072017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1'-Acetoxychavicol acetate 10V, Positive-QTOFsplash10-000l-0970000000-81735b3654a481b063112021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1'-Acetoxychavicol acetate 20V, Positive-QTOFsplash10-0036-1900000000-9b5975ebd113945e0e7c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1'-Acetoxychavicol acetate 40V, Positive-QTOFsplash10-0007-2900000000-699c26c2e1a06248898e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1'-Acetoxychavicol acetate 10V, Negative-QTOFsplash10-0a4l-9620000000-6a6a1fa37916a3b9a0ea2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1'-Acetoxychavicol acetate 20V, Negative-QTOFsplash10-0a4i-9100000000-f44a6f5a57c94e8e8e932021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1'-Acetoxychavicol acetate 40V, Negative-QTOFsplash10-052f-9300000000-ef559bb25482dcb0b3862021-09-22Wishart LabView Spectrum
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 IDFDB020865
KNApSAcK IDC00031531
Chemspider ID354584
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound400072
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1466351
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:22226652 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .