1.0 2010-04-08 22:05:25 UTC 2025-11-18 22:38:11 UTC FDB002541 Pinosylvin Pinosylvin, also known as 5-[(Z)-2-phenylvinyl]benzene-1,3-diol, 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. Pinosylvin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Pinosylvin can be found in beer and grape wine, which makes pinosylvin a potential biomarker for the consumption of these food products. Pinosylvin is a pre-infectious stilbenoid toxin (i.e. synthesized prior to infection), contrary to phytoalexins which are synthesized during infection. It is present in the heartwood of Pinaceae. It is a fungitoxin protecting the wood from fungal infection. It is also found in Gnetum cleistostachyum . (E)-3,5-stilbenediol (E)-5-(2-Phenylethenyl)-1,3-benzenediol (trans)-3,5-stilbenediol 1-(3,5-Dihydroxyphenyl)-2-phenylethylene 1,3-Benzenediol, 5-(2-phenylethenyl)- 1,3-Benzenediol, 5-(2-phenylethenyl)-, (E)- 1,3-Benzenediol, 5-(2-phenylethenyl)-, (E)- (9CI) 3,5-Stilbenediol 3,5-Stilbenediol, (E)- 5-(2-phenylethenyl)-1,3-benzenediol 5-(2-Phenylethenyl)-1,3-benzenediol, 9CI 5-(2-phenylethenyl)benzene-1,3-diol 5-(2-phenylvinyl)benzene-1,3-diol 5-[(1E)-2-phenylethenyl]benzene-1,3-diol 5-[(E)-2-phenylvinyl]benzene-1,3-diol 5-Styrylresorcinol Pinosylvin Pinosylvine trans-3,5-Dihydroxystilbene C14H12O2 212.2439 212.083729628 5-[(Z)-2-phenylethenyl]benzene-1,3-diol cis-pinosylvin 102-61-4 OC1=CC(\C=C/C2=CC=CC=C2)=CC(O)=C1 InChI=1S/C14H12O2/c15-13-8-12(9-14(16)10-13)7-6-11-4-2-1-3-5-11/h1-10,15-16H/b7-6- YCVPRTHEGLPYPB-SREVYHEPSA-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 Hydrocarbon derivatives Organooxygen compounds Resorcinols Styrenes 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 Styrene pinosylvin logp 3.28 ALOGPS logs -3.65 ALOGPS solubility 4.81e-02 g/l ALOGPS logp 3.71 ChemAxon pka_strongest_acidic 9.16 ChemAxon pka_strongest_basic -5.7 ChemAxon iupac 5-[(Z)-2-phenylethenyl]benzene-1,3-diol ChemAxon average_mass 212.2439 ChemAxon mono_mass 212.083729628 ChemAxon smiles OC1=CC(\C=C/C2=CC=CC=C2)=CC(O)=C1 ChemAxon formula C14H12O2 ChemAxon inchi InChI=1S/C14H12O2/c15-13-8-12(9-14(16)10-13)7-6-11-4-2-1-3-5-11/h1-10,15-16H/b7-6- ChemAxon inchikey YCVPRTHEGLPYPB-SREVYHEPSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 65.47 ChemAxon polarizability 22.6 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 77277 Specdb::MsMs 77278 Specdb::MsMs 77279 Specdb::MsMs 137367 Specdb::MsMs 137368 Specdb::MsMs 137369 36011 Beer Type 2 specific 0.0 0.0 0.0 mg/100 g Grape Type 1 specific Vitis 3603 Grape wine Type 2 specific 0.0 0.0 0.0 mg/100 g Peanut Type 1 specific Arachis hypogaea 3818