1.0 2012-01-20 01:16:41 UTC 2025-11-19 03:00:05 UTC FDB029989 Dihydroresveratrol Dihydroresveratrol 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-diol C14H14O3 230.2592 230.094294314 5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diol dihydroresveratrol 58436-28-5 OC1=CC=C(CCC2=CC(O)=CC(O)=C2)C=C1 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 HITJFUSPLYBJPE-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. Stilbenes Organic compounds Phenylpropanoids and polyketides Stilbenes Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Benzene and substituted derivatives Hydrocarbon derivatives Organooxygen compounds Resorcinols 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic homomonocyclic compound Benzenoid Hydrocarbon derivative Monocyclic benzene moiety Organic oxygen compound Organooxygen compound Phenol Resorcinol Stilbene Bibenzyls Diphenyl ethers, biphenyls, dibenzyls and stilbenes Diphenyl ethers, biphenyls, dibenzyls and stilbenes stilbenol logp 2.45 ALOGPS logs -3.45 ALOGPS solubility 8.12e-02 g/l ALOGPS logp 3.6 ChemAxon pka_strongest_acidic 9.3 ChemAxon pka_strongest_basic -5.4 ChemAxon iupac 5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diol ChemAxon average_mass 230.2592 ChemAxon mono_mass 230.094294314 ChemAxon smiles OC1=CC=C(CCC2=CC(O)=CC(O)=C2)C=C1 ChemAxon formula C14H14O3 ChemAxon inchi 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 ChemAxon inchikey HITJFUSPLYBJPE-UHFFFAOYSA-N ChemAxon polar_surface_area 60.69 ChemAxon refractivity 66.34 ChemAxon polarizability 24.87 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 5553 Specdb::CMs 146425 Specdb::MsMs 239617 Specdb::MsMs 239618 Specdb::MsMs 239619 Specdb::MsMs 241672 Specdb::MsMs 241673 Specdb::MsMs 241674 Specdb::MsMs 1470969 Specdb::MsMs 1470970 Specdb::MsMs 1470971 Specdb::MsMs 1471024 Specdb::MsMs 1471244 Specdb::MsMs 1471245 Specdb::MsMs 1471246 Specdb::MsMs 1471247 Specdb::MsMs 1471248 Specdb::MsMs 1471249 Specdb::MsMs 1471251 Specdb::MsMs 1471256 Specdb::MsMs 2226324 Specdb::MsMs 2227275 Specdb::MsMs 2227429 Specdb::MsMs 2228368 Specdb::MsMs 2228757 Specdb::MsMs 2229631 Specdb::MsMs 2229864 Red wine Type 2 White wine Type 2