(+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one (CHEM023295)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 20:57:23 UTC
Update Date2016-11-09 01:17:40 UTC
Accession NumberCHEM023295
Identification
Common Name(+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one
ClassSmall Molecule
Description(+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one is found in beverages. (+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one is found in kava (Piper methysticum). FDA advises against use of kava in food due to potential risk of severe liver damage (2002
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC14H16O4
Average Molecular Mass248.274 g/mol
Monoisotopic Mass248.105 g/mol
CAS Registry Number52247-81-1
IUPAC Name5-hydroxy-4-methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one
Traditional Name5-hydroxy-4-methoxy-6-(2-phenylethyl)-5,6-dihydropyran-2-one
SMILESCOC1=CC(=O)OC(CCC2=CC=CC=C2)C1O
InChI IdentifierInChI=1S/C14H16O4/c1-17-12-9-13(15)18-11(14(12)16)8-7-10-5-3-2-4-6-10/h2-6,9,11,14,16H,7-8H2,1H3
InChI KeyVJCNEDVMYQCMBK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassKavalactones
Sub ClassNot Available
Direct ParentKavalactones
Alternative Parents
Substituents
  • Kavalactone
  • Dihydropyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Vinylogous ester
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Solubility1.33 g/LALOGPS
logP1.93ALOGPS
logP1.87ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)12.87ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity67.49 m³·mol⁻¹ChemAxon
Polarizability26.17 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-0536-9530000000-a488163ec5c48c7a46fbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9220000000-1adf6da0e5c6894e8b73Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1390000000-f753eb289d81bcfea4baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014l-3920000000-88c1c9875b067e37030bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-7900000000-625c9170ea4ef190dbffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0290000000-55c35b6e7f90b7f0acc7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9340000000-f4f90fef482ea541be38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-a0ae12a774ae15948b98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0390000000-93e8b27c7be16db2503fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-5900000000-51d4299d087afdbd604cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9400000000-761308f567c06adedf3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0790000000-e7ab5232365d04d117f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-4930000000-76868864f1222774db0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056u-9410000000-ef2bfe7941278461f64aSpectrum
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 IDHMDB0029575
FooDB IDFDB000731
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID499979
ChEBI ID174280
PubChem Compound ID575067
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.