Record Information
Version1.0
Creation date2010-04-08 22:15:30 UTC
Update date2019-11-26 03:19:58 UTC
Primary IDFDB021157
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name6-Hydroxyshogaol
Description6-Hydroxyshogaol 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. 6-Hydroxyshogaol is an extremely weak basic (essentially neutral) compound (based on its pKa). 6-Hydroxyshogaol has been detected, but not quantified in, herbs and spices. This could make 6-hydroxyshogaol a potential biomarker for the consumption of these foods.
CAS Number143114-93-6
Structure
Thumb
Synonyms
SynonymSource
6-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-4-decen-3-oneHMDB
6-Hydroxyshogaoldb_source
Predicted Properties
PropertyValueSource
Water Solubility0.098 g/LALOGPS
logP3.18ALOGPS
logP3.61ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)9.95ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity84.2 m³·mol⁻¹ChemAxon
Polarizability33.68 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC17H24O4
IUPAC name(4E)-6-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one
InChI IdentifierInChI=1S/C17H24O4/c1-3-4-5-14(18)9-10-15(19)8-6-13-7-11-16(20)17(12-13)21-2/h7,9-12,14,18,20H,3-6,8H2,1-2H3/b10-9+
InChI KeySEWFXECKZBLANJ-MDZDMXLPSA-N
Isomeric SMILESCCCCC(O)\C=C\C(=O)CCC1=CC(OC)=C(O)C=C1
Average Molecular Weight292.3701
Monoisotopic Molecular Weight292.167459256
Classification
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 69.84%; H 8.27%; O 21.89%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -1.7 (c, 1.81 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9650000000-e9a92ffdb0520a57df20JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9484700000-13b49ab356704bb7e710JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0190000000-e5166111300a8cdb74caJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-054x-5950000000-7b2ff27efe4c4521e7ceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9f-9410000000-2169845180ebf09200c0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-0d597d8cf9882c53e0c7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-2980000000-db88137d4e80a4c6b9feJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-5910000000-633749554bf92a2b71e7JSpectraViewer
ChemSpider ID9315994
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID11140882
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB41249
CRC / DFC (Dictionary of Food Compounds) IDHBF68-C:NMP86-R
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference