Record Information
Version1.0
Creation date2012-01-20 01:16:41 UTC
Update date2020-09-17 15:30:07 UTC
Primary IDFDB029989
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDihydroresveratrol
DescriptionDihydroresveratrol or 5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diol is a stilbenol where hydroxy groups at positions 1, 3 and 4' are added to 1,1'-ethane-1,2-diyldibenzene. Dihydroresveratrol is an aromatic polyketide, which contains alternating carbonyl groups and methylene groups. Dihydroresveratrol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Dihydroresveratrol, a prominent polyphenol component of red wine (PMID: 20630177), has a profound proliferative effect on hormone-sensitive tumor cell lines at picomolar concentrations. Dihydroresveratol is a derivative of resveratol and one of the main metabolites of two stereoisomers of resveratol, trans resveratrol and cis resveratrol. Dihydroresveratrol is formed in the intestine by microbial hydrogenation of trans-resveratrol (PMID: 20509689). Trans-resveratrol is a common component of fruits and berries, particularly grapes (Vitis vinifera), where it is formed as a response to the stress of weather conditions, microbe infections, or direct sunlight. Cis resveratrol is as a minor component in some berries, grapes, and wines along with trans-resveratrol (PMID: 20813524). Resveratrol has received special attention due to its diverse and potentially beneficial biological properties. The compound is currently on the market as a popular dietary supplement and is under clinical trials for treatment of some types of cancers (PMID: 25446990), metabolic syndrome, Alzheimer’s disease, type 2 diabetes, obesity (PMID: 25790328), neurologic syndrome, and some symptoms of aging.
CAS Number58436-28-5
Structure
Thumb
Synonyms
SynonymSource
3,4',5-TrihydroxybibenzylChEBI
Dihydro-resveratrolHMDB
5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diolbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.081 g/LALOGPS
logP2.45ALOGPS
logP3.6ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)9.3ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity66.34 m³·mol⁻¹ChemAxon
Polarizability24.87 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC14H14O3
IUPAC name5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diol
InChI IdentifierInChI=1S/C14H14O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h3-9,15-17H,1-2H2
InChI KeyHITJFUSPLYBJPE-UHFFFAOYSA-N
Isomeric SMILESOC1=CC=C(CCC2=CC(O)=CC(O)=C2)C=C1
Average Molecular Weight230.2592
Monoisotopic Molecular Weight230.094294314
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
  • Resorcinol
  • 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
Foods

Beverages:

Fruits and vegetables:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
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-MSDihydroresveratrol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0adi-3920000000-719fe242334d208b9ba6Spectrum
Predicted GC-MSDihydroresveratrol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-0019-0930000000-98789a2bfadb2e5294f9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-0a4i-3900000000-8401a4b05cec11937e91Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 50V, positivesplash10-0a4i-1900000000-63077beabbd74f9667daSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 6V, positivesplash10-0019-0930000000-d89311ce59a12d10e350Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, negativesplash10-00fr-0940000000-e764d7f7fec0ad95522dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, negativesplash10-004i-0590000000-c0d04f560a51a3bb619dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, negativesplash10-001i-9500000000-361c896f8255aa9a4a1dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, negativesplash10-00di-3900000000-71299800417044263bbbSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 50V, negativesplash10-001i-9000000000-35af2f10fc300befdb21Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 50V, negativesplash10-003r-9100000000-ac6d40eae4eba92c915dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 6V, negativesplash10-004i-0590000000-c0d04f560a51a3bb619dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 6V, negativesplash10-00fr-0940000000-ef1a37528e823253c1b3Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0019-0930000000-5350f748bb4caf143bc6Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0490000000-ad670ae9686c694e73c1Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-3900000000-e4d975cfe5ed55a80b23Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-00ar-5930000000-21f41106079ae20bf096Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-3900000000-1d5073ba2d9174c455ddSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-053i-0940000000-ac0deac644455c15b41cSpectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0a4i-1900000000-6510d3485dd518836d05Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0190000000-dbff90b6a63d99897a08Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-0950000000-1f3064cc04762cbfb39fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-5900000000-e5b4f11464b84f6190efSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-3f1af4fc1138d28d1e8fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0190000000-b3b2e29cac9a8f7c4f14Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0553-1920000000-bc1898e08955e5b6385aSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID185914
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB08466
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
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 ID1008
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