Record Information
Version1.0
Creation date2011-03-30 21:42:25 UTC
Update date2015-07-21 06:56:04 UTC
Primary IDFDB021778
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameChavicol glucoside
DescriptionChavicol O-beta-glucopyranoside, also known as 4-(2-propenyl)phenol, 9CI, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Chavicol O-beta-glucopyranoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Chavicol O-beta-glucopyranoside is a sweet tasting compound.
CAS Number64703-98-6
Structure
Thumb
Synonyms
SynonymSource
Chavicol O-b-glucopyranosideGenerator
Chavicol O-β-glucopyranosideGenerator
4-(2-Propenyl)phenol, 9ciHMDB
O-b-GlucopyranosideHMDB
4-(2-Propenyl)phenol, 9CI; O-b-Glucopyranosidedb_source
Predicted Properties
PropertyValueSource
Water Solubility19.3 g/LALOGPS
logP0.29ALOGPS
logP0.5ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.38 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity74.47 m³·mol⁻¹ChemAxon
Polarizability30.37 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H20O6
IUPAC name2-(hydroxymethyl)-6-[4-(prop-2-en-1-yl)phenoxy]oxane-3,4,5-triol
InChI IdentifierInChI=1S/C15H20O6/c1-2-3-9-4-6-10(7-5-9)20-15-14(19)13(18)12(17)11(8-16)21-15/h2,4-7,11-19H,1,3,8H2
InChI KeyBGWWYZXBGAKMRB-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OC2=CC=C(CC=C)C=C2)C(O)C(O)C1O
Average Molecular Weight296.319
Monoisotopic Molecular Weight296.125988364
Classification
Description belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • O-glycosyl compound
  • Phenoxy compound
  • Phenol ether
  • Monocyclic benzene moiety
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 60.80%; H 6.80%; O 32.40%DFC
Melting PointMp 149°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]15D -56.3 (c, 0.4 in MeOH)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, Positivesplash10-0pe9-8980000000-7ed20283277969f7df8eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00xr-1211390000-8c5eaa7097ea240facbfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-0960000000-267805db5350347a6067JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-f4346692bfaf69aba604JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ku-5900000000-40aeb7b204f21e9d1fbbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000t-0890000000-ae5895c67e57ff1b4aa4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0910000000-f31a0c0998dc7b906176JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2900000000-bfefc1e972fb52d34e3aJSpectraViewer
ChemSpider ID23194209
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID44338426
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB41617
CRC / DFC (Dictionary of Food Compounds) IDHGQ74-N:NMQ06-Y
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 IDrw1600531
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
Flavours
FlavorCitations
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference