1.02012-01-20 01:16:41 UTC2020-09-17 15:30:07 UTCFDB029989DihydroresveratrolDihydroresveratrol 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.5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diolC14H14O3230.2592230.0942943145-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-dioldihydroresveratrol58436-28-5OC1=CC=C(CCC2=CC(O)=CC(O)=C2)C=C1InChI=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,1-2H2HITJFUSPLYBJPE-UHFFFAOYSA-N 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.StilbenesOrganic compoundsPhenylpropanoids and polyketidesStilbenesAromatic homomonocyclic compounds1-hydroxy-2-unsubstituted benzenoids1-hydroxy-4-unsubstituted benzenoidsBenzene and substituted derivativesHydrocarbon derivativesOrganooxygen compoundsResorcinols1-hydroxy-2-unsubstituted benzenoid1-hydroxy-4-unsubstituted benzenoidAromatic homomonocyclic compoundBenzenoidHydrocarbon derivativeMonocyclic benzene moietyOrganic oxygen compoundOrganooxygen compoundPhenolResorcinolStilbeneBibenzylsDiphenyl ethers, biphenyls, dibenzyls and stilbenesDiphenyl ethers, biphenyls, dibenzyls and stilbenesstilbenollogp2.45logs-3.45solubility8.12e-02 g/llogp3.6pka_strongest_acidic9.3pka_strongest_basic-5.4iupac5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diolaverage_mass230.2592mono_mass230.094294314smilesOC1=CC=C(CCC2=CC(O)=CC(O)=C2)C=C1formulaC14H14O3inchiInChI=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,1-2H2inchikeyHITJFUSPLYBJPE-UHFFFAOYSA-Npolar_surface_area60.69refractivity66.34polarizability24.87rotatable_bond_count3acceptor_count3donor_count3physiological_charge0formal_charge0Specdb::CMs5553Specdb::CMs146425Specdb::MsMs239617Specdb::MsMs239618Specdb::MsMs239619Specdb::MsMs241672Specdb::MsMs241673Specdb::MsMs241674Specdb::MsMs1470969Specdb::MsMs1470970Specdb::MsMs1470971Specdb::MsMs1471024Specdb::MsMs1471244Specdb::MsMs1471245Specdb::MsMs1471246Specdb::MsMs1471247Specdb::MsMs1471248Specdb::MsMs1471249Specdb::MsMs1471251Specdb::MsMs1471256Specdb::MsMs2226324Specdb::MsMs2227275Specdb::MsMs2227429Specdb::MsMs2228368Specdb::MsMs2228757Specdb::MsMs2229631Specdb::MsMs2229864Red wineType 2White wineType 2