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Showing Compound Piceatannol (FDB012295)

Record Information
Version1.0
Creation date2010-04-08 22:10:06 UTC
Update date2019-11-26 03:06:32 UTC
Primary IDFDB012295
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePiceatannol
DescriptionPiceatannol, also known as (Z)-3,5,3',4'-tetrahydroxystilbene, is a member of the class of compounds known as stilbenes. Stilbenes are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Piceatannol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Piceatannol can be synthesized from cis-stilbene. Piceatannol can also be synthesized into cis-astringin. Piceatannol can be found in common grape and grape wine, which makes piceatannol a potential biomarker for the consumption of these food products. Piceatannol is a stilbenoid, a type of phenolic compound .
CAS Number4339-71-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(Z)-3,5,3',4'-TetrahydroxystilbeneChEBI
3,3',4,5'-Stilbenetetrol, 8CIdb_source
3,3',4,5'-Tetrahydroxystilbenedb_source
4-[2-(3,5-Dihydroxyphenyl)ethenyl]-1,2-benzenediol, 9CIdb_source
Astringenindb_source
NSC 365798db_source
Piceatannoldb_source
Predicted Properties
PropertyValueSource
Water Solubility0.097 g/LALOGPS
logP2.12ALOGPS
logP3.1ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)8.91ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity69.44 m³·mol⁻¹ChemAxon
Polarizability24.3 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC14H12O4
IUPAC name4-[(Z)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol
InChI IdentifierInChI=1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1-
InChI KeyCDRPUGZCRXZLFL-UPHRSURJSA-N
Isomeric SMILES[H]\C(=C(/[H])C1=CC(O)=CC(O)=C1)C1=CC=C(O)C(O)=C1
Average Molecular Weight244.246
Monoisotopic Molecular Weight244.073558866
Classification
Description Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Styrene
  • Resorcinol
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 68.85%; H 4.95%; O 26.20%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPiceatannol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-0690000000-50e7f72f479a8b6f10a4Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0190000000-ba683912843d4fe87a702016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0690000000-84fddb6ca6d69b5c7c812016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-4910000000-c3f282dac8a7f5eb07cd2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-328195abcb348d62bbb32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0190000000-1eebbf80fc971e14314b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0m06-1960000000-bef8ef7244293d115d7c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-129caff3cb8f807f0c462021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05bb-0940000000-e091c3104a7f4d22b2cf2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-1900000000-0c2cf497a3e42dc1e04b2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-c3ceff739ebba19f299c2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0190000000-c26868bfc8b623440adb2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0910000000-4614afc2f810361b06a82021-10-21View 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 ID582
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHFR82-M:HFR82-M
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— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.