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Record Information
Version2.0
Created at2022-03-10 18:36:53 UTC
Updated at2024-09-03 04:22:56 UTC
NP-MRD IDNP0044867
Natural Product DOIhttps://doi.org/10.57994/3036
Secondary Accession NumbersNone
Natural Product Identification
Common 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 is a non-cannabinoid estrogenic compound found in cannabis (PMID: 6991645 ). 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.
Structure
Thumb
Synonyms
ValueSource
3,4',5-TrihydroxybibenzylChEBI
Dihydro-resveratrolMeSH
Chemical FormulaC14H14O3
Average Mass230.2592 Da
Monoisotopic Mass230.09429 Da
IUPAC Name5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diol
Traditional Namedihydroresveratrol
CAS Registry NumberNot Available
SMILES
OC1=CC=C(CCC2=CC(O)=CC(O)=C2)C=C1
InChI Identifier
InChI=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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)bernd.schmidt@uni-potsdam.deUniversity of PotsdamBernd Schmidt2024-07-05View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)bernd.schmidt@uni-potsdam.deUniversity of PotsdamBernd Schmidt2024-07-05View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)bernd.schmidt@uni-potsdam.deUniversity of PotsdamBernd Schmidt2024-07-05View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)bernd.schmidt@uni-potsdam.deUniversity of PotsdamBernd Schmidt2024-07-05View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, CD3OD, experimental)bernd.schmidt@uni-potsdam.deUniversity of PotsdamBernd Schmidt2024-07-05View Spectrum
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Chemical Taxonomy
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.45ALOGPS
logP3.6ChemAxon
logS-3.4ALOGPS
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
HMDB IDHMDB0240498
DrugBank IDDB08466
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029989
KNApSAcK IDC00002879
Chemspider IDNot Available
KEGG Compound IDC10255
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDihydro-resveratrol
METLIN IDNot Available
PubChem Compound185914
PDB IDNot Available
ChEBI ID4582
Good Scents IDNot Available
References
General References
  1. Montes R, Garcia-Lopez M, Rodriguez I, Cela R: Mixed-mode solid-phase extraction followed by acetylation and gas chromatography mass spectrometry for the reliable determination of trans-resveratrol in wine samples. Anal Chim Acta. 2010 Jul 12;673(1):47-53. doi: 10.1016/j.aca.2010.05.021. Epub 2010 Jun 4. [PubMed:20630177 ]
  2. Juan ME, Alfaras I, Planas JM: Determination of dihydroresveratrol in rat plasma by HPLC. J Agric Food Chem. 2010 Jun 23;58(12):7472-5. doi: 10.1021/jf100836j. [PubMed:20509689 ]
  3. Gakh AA, Anisimova NY, Kiselevsky MV, Sadovnikov SV, Stankov IN, Yudin MV, Rufanov KA, Krasavin MY, Sosnov AV: Dihydro-resveratrol--a potent dietary polyphenol. Bioorg Med Chem Lett. 2010 Oct 15;20(20):6149-51. doi: 10.1016/j.bmcl.2010.08.002. Epub 2010 Aug 5. [PubMed:20813524 ]
  4. van der Made SM, Plat J, Mensink RP: Resveratrol does not influence metabolic risk markers related to cardiovascular health in overweight and slightly obese subjects: a randomized, placebo-controlled crossover trial. PLoS One. 2015 Mar 19;10(3):e0118393. doi: 10.1371/journal.pone.0118393. eCollection 2015. [PubMed:25790328 ]
  5. Aiyedun PO, Sonibare MA, Ajiboye CO, Gueye B, Paliwal R, Albach DC, Nchiozem-Ngnitedem VA, Schmidt B: Phytoecdysteroids from Dioscorea dumetorum (Kunth) Pax. and their antioxidant and antidiabetic activities. Fitoterapia. 2024 Jun 28;177:106103. doi: 10.1016/j.fitote.2024.106103. [PubMed:38945493 ]