cis-[8]-Shogaol (CHEM026455)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:59:51 UTC
Update Date2016-11-09 01:18:16 UTC
Accession NumberCHEM026455
Identification
Common Namecis-[8]-Shogaol
ClassSmall Molecule
Descriptioncis-[8]-Shogaol is found in ginger. cis-[8]-Shogaol is isolated from ginger (Zingiber officinale) [DFC] (Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(8)-ShogaolMeSH
8-ShogaolChEMBL, HMDB
cis-8-SHOGAOLHMDB
Chemical FormulaC19H28O3
Average Molecular Mass304.424 g/mol
Monoisotopic Mass304.204 g/mol
CAS Registry NumberNot Available
IUPAC Name(4E)-1-(4-hydroxy-3-methoxyphenyl)dodec-4-en-3-one
Traditional Name(4E)-1-(4-hydroxy-3-methoxyphenyl)dodec-4-en-3-one
SMILESCCCCCCC\C=C\C(=O)CCC1=CC(OC)=C(O)C=C1
InChI IdentifierInChI=1S/C19H28O3/c1-3-4-5-6-7-8-9-10-17(20)13-11-16-12-14-18(21)19(15-16)22-2/h9-10,12,14-15,21H,3-8,11,13H2,1-2H3/b10-9+
InChI KeyLGZSMXJRMTYABD-MDZDMXLPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as shogaols. These are ginger derivatives containing a shogaol moiety, which consists of a benzene ring bearing a dec-4-en-3-one moiety, a methoxyphenyl group, a hydroxyl group and at positions 1, 3, and 4, respectively.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentShogaols
Alternative Parents
Substituents
  • Shogaol
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Enone
  • Acryloyl-group
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • 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
logP5.73ChemAxon
pKa (Strongest Acidic)9.95ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity91.89 m³·mol⁻¹ChemAxon
Polarizability36.36 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ug0-9530000000-e20ef27b5280ff5ee251Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ir0-9126000000-11c9f220f1f8a0af38feSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0900000000-8af586f12af17cb2ff25Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0900000000-7e3aa5a3100bfee96dc7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0209000000-35ae835d6a02f9ab17b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufr-0924000000-c4abe8cdbf8068a61d7cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02t9-1910000000-b22f5a143d260d81210eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0109000000-d448c016b7a08fc130eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0902000000-3594da3f85e78a13d8beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05tr-3900000000-c8d1b81cba78e2a10a9eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0329000000-7442e7476f444e4b8c66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pbi-3911000000-e151599acc5597ea42f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9f-9610000000-919607f0cfb79f30b491Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0908000000-b442539b4e45c6e98ba3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-3911000000-fa105dc063b655e9adadSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-2900000000-04a7e19cb68b1421de23Spectrum
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 IDHMDB0031464
FooDB IDFDB007772
Phenol Explorer IDNot Available
KNApSAcK IDC00035035
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4946630
ChEBI IDNot Available
PubChem Compound ID6442560
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Duke, James A. (1992) Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.