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Showing Compound 2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) (FDB020980)

Record Information
Version1.0
Creation date2010-04-08 22:15:23 UTC
Update date2019-11-26 03:19:43 UTC
Primary IDFDB020980
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside)
Description2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. 2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) has been detected, but not quantified in, green vegetables. This could make 2-hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside) a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside).
CAS Number84888-58-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
{3,4,5-trihydroxy-6-[(3-methyl-4-oxo-4H-pyran-2-yl)oxy]oxan-2-yl}methyl (2E)-3-phenylprop-2-enoic acidGenerator
2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucopyranoside)manual
2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside)manual
Predicted Properties
PropertyValueSource
Water Solubility0.75 g/LALOGPS
logP0.89ALOGPS
logP1.86ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area131.75 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity113.55 m³·mol⁻¹ChemAxon
Polarizability41.34 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H22O9
IUPAC name{3,4,5-trihydroxy-6-[(3-methyl-4-oxo-4H-pyran-2-yl)oxy]oxan-2-yl}methyl (2E)-3-phenylprop-2-enoate
InChI IdentifierInChI=1S/C21H22O9/c1-12-14(22)9-10-27-20(12)30-21-19(26)18(25)17(24)15(29-21)11-28-16(23)8-7-13-5-3-2-4-6-13/h2-10,15,17-19,21,24-26H,11H2,1H3/b8-7+
InChI KeyJRUMXTPQUYPUHC-BQYQJAHWSA-N
Isomeric SMILESCC1=C(OC2OC(COC(=O)\C=C\C3=CC=CC=C3)C(O)C(O)C2O)OC=CC1=O
Average Molecular Weight418.394
Monoisotopic Molecular Weight418.126382302
Classification
Description Belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassCinnamic acid esters
Direct ParentCinnamic acid esters
Alternative Parents
Substituents
  • Cinnamic acid ester
  • Glycosyl compound
  • O-glycosyl compound
  • Styrene
  • Fatty acid ester
  • Pyranone
  • Monocyclic benzene moiety
  • Monosaccharide
  • Oxane
  • Pyran
  • Fatty acyl
  • Benzenoid
  • Vinylogous ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Heteroaromatic compound
  • Secondary alcohol
  • Cyclic ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Acetal
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 60.28%; H 5.30%; O 34.42%DFC
Melting PointMp 163-163.7°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]22D -96.8 (c, 1.37 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0kai-5891200000-84fd51c76d33ecab6a4aSpectrum
Predicted GC-MS2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside), 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00yi-4622449000-96c3aa142159d0592ce4Spectrum
Predicted GC-MS2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Hydroxy-3-methyl-4H-pyran-4-one O-(6E-cinnamoyl-b-D-glucoside), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0920200000-0c5c9d38f473aa38385b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-1910000000-5c4d43213d51a64e71742017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-a336fc76fba3f03e89c92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004j-1910200000-6df66343fa5bab4b31f32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-3900000000-8fff9289de06832c3a4c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f92-7900000000-230e56fe23ed168c364b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-1910600000-e476d488c10c1f6f96612021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0m31-1910000000-5e417bfa35527801c5d82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2900000000-e68a18516f49a22464fa2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-5e9301e7eae75f61107e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03ed-1900000000-11f4a78fbff30e31b4f02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9300000000-7eb2b91836231810c3722021-09-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB41098
CRC / DFC (Dictionary of Food Compounds) IDNHN33-G:NHN34-H
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