1.0 2010-04-08 22:04:30 UTC 2019-11-26 02:54:36 UTC FDB000264 5-8'-Dehydrodiferulic acid 5-8'-dehydrodiferulic acid 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. 5-8'-dehydrodiferulic acid is practically insoluble (in water) and a moderately acidic compound (based on its pKa). 5-8'-dehydrodiferulic acid can be found in a number of food items such as corn, common wheat, rye, and semolina, which makes 5-8'-dehydrodiferulic acid a potential biomarker for the consumption of these food products. 8,5'-Diferulic acid is a non cyclic type of diferulic acid. It is the predominant diferulic acid in sugar beet pulp. It is also found in barley, in maize bran and rye. 8-5'-Diferulic acid has also been identified to be covalently linked to carbohydrate moieties of the arabinogalactan-protein fraction of gum arabic . C20H18O8 386.3521 386.100167552 (2E)-2-{5-[(1Z)-2-carboxyeth-1-en-1-yl]-2-hydroxy-3-methoxyphenyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid (2E)-2-{5-[(1Z)-2-carboxyeth-1-en-1-yl]-2-hydroxy-3-methoxyphenyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid COC1=CC(\C=C/C(O)=O)=CC(\C(=C/C2=CC(OC)=C(O)C=C2)C(O)=O)=C1O InChI=1S/C20H18O8/c1-27-16-9-11(3-5-15(16)21)8-14(20(25)26)13-7-12(4-6-18(22)23)10-17(28-2)19(13)24/h3-10,21,24H,1-2H3,(H,22,23)(H,25,26)/b6-4-,14-8+ DEPVSDIYICBTJE-FGDQGFBNSA-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 Alkyl aryl ethers Anisoles Carbonyl compounds Carboxylic acids Cinnamic acids Coumaric acids and derivatives Dicarboxylic acids and derivatives Hydrocarbon derivatives Hydroxycinnamic acids Methoxybenzenes Methoxyphenols Organic oxides Phenoxy compounds Styrenes 1-hydroxy-2-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxylic acid Carboxylic acid derivative Cinnamic acid Cinnamic acid or derivatives Coumaric acid or derivatives Dicarboxylic acid or derivatives Ether Hydrocarbon derivative Hydroxycinnamic acid Hydroxycinnamic acid or derivatives Methoxybenzene Methoxyphenol Monocyclic benzene moiety Organic oxide Organic oxygen compound Organooxygen compound Phenol Phenol ether Phenoxy compound Stilbene Styrene logp 3.11 ALOGPS logs -4.35 ALOGPS solubility 1.74e-02 g/l ALOGPS logp 3.04 ChemAxon pka_strongest_acidic 2.85 ChemAxon pka_strongest_basic -4.6 ChemAxon iupac (2E)-2-{5-[(1Z)-2-carboxyeth-1-en-1-yl]-2-hydroxy-3-methoxyphenyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid ChemAxon average_mass 386.3521 ChemAxon mono_mass 386.100167552 ChemAxon smiles COC1=CC(\C=C/C(O)=O)=CC(\C(=C/C2=CC(OC)=C(O)C=C2)C(O)=O)=C1O ChemAxon formula C20H18O8 ChemAxon inchi InChI=1S/C20H18O8/c1-27-16-9-11(3-5-15(16)21)8-14(20(25)26)13-7-12(4-6-18(22)23)10-17(28-2)19(13)24/h3-10,21,24H,1-2H3,(H,22,23)(H,25,26)/b6-4-,14-8+ ChemAxon inchikey DEPVSDIYICBTJE-FGDQGFBNSA-N ChemAxon polar_surface_area 133.52 ChemAxon refractivity 101.4 ChemAxon polarizability 37.5 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 90114 Specdb::MsMs 90115 Specdb::MsMs 90116 Specdb::MsMs 153192 Specdb::MsMs 153193 Specdb::MsMs 153194 Specdb::MsMs 3596926 Specdb::MsMs 3596927 Specdb::MsMs 3596928 Specdb::MsMs 3596929 Specdb::MsMs 3596930 Specdb::MsMs 3596931 Common wheat Type 1 specific Triticum aestivum 4565 1.392 1.392000079 1.392000079 mg/100 g Corn Type 1 specific Zea mays 4577 8.2775 8.277500153 8.277500153 mg/100 g Hard wheat Type 1 specific Triticum durum 4567 0.081962 0.081962499 0.081962499 mg/100 g Rye Type 1 specific Secale cereale 4550 1.6155 2.70000001 0.531000018 mg/100 g Semolina Type 2 specific 6.131747 6.131747448 6.131747448 mg/100 g