1.0 2010-04-08 22:10:06 UTC 2025-11-18 23:35:34 UTC FDB012295 Piceatannol Piceatannol, 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 . 3,3',4,5'-Stilbenetetrol, 8CI 3,3',4,5'-Tetrahydroxystilbene 4-[2-(3,5-Dihydroxyphenyl)ethenyl]-1,2-benzenediol, 9CI Astringenin NSC 365798 Piceatannol C14H12O4 244.246 244.073558866 4-[(Z)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol 4-[(Z)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol 4339-71-3 [H]\C(=C(/[H])C1=CC(O)=CC(O)=C1)C1=CC=C(O)C(O)=C1 InChI=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- CDRPUGZCRXZLFL-UPHRSURJSA-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 Catechols Hydrocarbon derivatives Organooxygen compounds Resorcinols Styrenes 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic homomonocyclic compound Benzenoid Catechol Hydrocarbon derivative Monocyclic benzene moiety Organic oxygen compound Organooxygen compound Phenol Resorcinol Stilbene Styrene polyphenol stilbenol logp 2.12 ALOGPS logs -3.40 ALOGPS solubility 9.70e-02 g/l ALOGPS logp 3.1 ChemAxon pka_strongest_acidic 8.91 ChemAxon pka_strongest_basic -5.7 ChemAxon iupac 4-[(Z)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol ChemAxon average_mass 244.246 ChemAxon mono_mass 244.073558866 ChemAxon smiles [H]\C(=C(/[H])C1=CC(O)=CC(O)=C1)C1=CC=C(O)C(O)=C1 ChemAxon formula C14H12O4 ChemAxon inchi InChI=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- ChemAxon inchikey CDRPUGZCRXZLFL-UPHRSURJSA-N ChemAxon polar_surface_area 80.92 ChemAxon refractivity 69.44 ChemAxon polarizability 24.3 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 5991 Specdb::MsMs 43125 Specdb::MsMs 43126 Specdb::MsMs 43127 Specdb::MsMs 143991 Specdb::MsMs 143992 Specdb::MsMs 143993 Specdb::MsMs 3605365 Specdb::MsMs 3605366 Specdb::MsMs 3605367 Specdb::MsMs 3605368 Specdb::MsMs 3605369 Specdb::MsMs 3605370 Common grape Type 1 specific Vitis vinifera 29760 0.0052 0.0052 0.0052 mg/100 g Grape wine Type 2 specific 0.582583 0.582583343 0.582583343 mg/100 g Red wine Type 2 Rosé wine Type 2 White wine Type 2