1.0 2010-04-08 22:04:25 UTC 2025-11-18 22:15:57 UTC FDB000055 Malvidin 3-(6''-caffeoyl-glucoside) Malvidin 3-(6''-caffeoyl-glucoside) is a member of the class of compounds known as flavonoid 3-o-p-coumaroyl glycosides. Flavonoid 3-o-p-coumaroyl glycosides are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring. Malvidin 3-(6''-caffeoyl-glucoside) is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Malvidin 3-(6''-caffeoyl-glucoside) can be found in grape wine, which makes malvidin 3-(6''-caffeoyl-glucoside) a potential biomarker for the consumption of this food product. Malvidin 3-O-(6''-caffeoyl-glucoside) C32H31O15 655.5795 655.166295322 3-{[(3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1lambda4-chromen-1-ylium 3-{[(3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1lambda4-chromen-1-ylium [H][C@]1(COC(=O)\C=C\C2=CC(O)=C(O)C=C2)OC(OC2=CC3=C(C=C(O)C=C3O)[O+]=C2C2=CC(OC)=C(O)C(OC)=C2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O InChI=1S/C32H30O15/c1-42-22-8-15(9-23(43-2)27(22)38)31-24(12-17-19(35)10-16(33)11-21(17)45-31)46-32-30(41)29(40)28(39)25(47-32)13-44-26(37)6-4-14-3-5-18(34)20(36)7-14/h3-12,25,28-30,32,39-41H,13H2,1-2H3,(H4-,33,34,35,36,37,38)/p+1/t25-,28-,29+,30-,32?/m1/s1 LIEHUFTYLLDHTI-FCOFYTSKSA-O belongs to the class of organic compounds known as flavonoid 3-o-p-coumaroyl glycosides. These are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring. Flavonoid 3-O-p-coumaroyl glycosides Organic compounds Phenylpropanoids and polyketides Flavonoids Flavonoid glycosides Aromatic heteropolycyclic compounds 1-benzopyrans 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 3'-O-methylated flavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Acetals Alkyl aryl ethers Anisoles Anthocyanidin-3-O-glycosides Anthocyanidins Carbonyl compounds Catechols Cinnamic acid esters Coumaric acids and derivatives Dimethoxybenzenes Enoate esters Fatty acid esters Flavonoid-3-O-glycosides Heteroaromatic compounds Hydrocarbon derivatives Methoxyphenols Monocarboxylic acids and derivatives Monosaccharides O-glycosyl compounds Organic cations Organic oxides Oxacyclic compounds Oxanes Phenoxy compounds Polyols Secondary alcohols Styrenes 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3p-methoxyflavonoid-skeleton 4'-hydroxyflavonoid 5-hydroxyflavonoid 7-hydroxyflavonoid Acetal Alcohol Alkyl aryl ether Alpha,beta-unsaturated carboxylic ester Anisole Anthocyanidin Anthocyanidin-3-o-glycoside Anthocyanin Aromatic heteropolycyclic compound Benzenoid Benzopyran Carbonyl group Carboxylic acid derivative Carboxylic acid ester Catechol Cinnamic acid ester Cinnamic acid or derivatives Coumaric acid or derivatives Dimethoxybenzene Enoate ester Ether Fatty acid ester Fatty acyl Flavonoid 3-o-6-p-coumaroyl-glycoside Flavonoid-3-o-glycoside Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Hydroxycinnamic acid or derivatives Hydroxyflavonoid M-dimethoxybenzene Methoxybenzene Methoxyphenol Monocarboxylic acid or derivatives Monocyclic benzene moiety Monosaccharide O-glycosyl compound Organic cation Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Phenol Phenol ether Phenoxy compound Polyol Secondary alcohol Styrene logp 3.31 ALOGPS logs -4.09 ALOGPS solubility 5.61e-02 g/l ALOGPS logp 3.3 ChemAxon pka_strongest_acidic 6.38 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac 3-{[(3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1lambda4-chromen-1-ylium ChemAxon average_mass 655.5795 ChemAxon mono_mass 655.166295322 ChemAxon smiles [H][C@]1(COC(=O)\C=C\C2=CC(O)=C(O)C=C2)OC(OC2=CC3=C(C=C(O)C=C3O)[O+]=C2C2=CC(OC)=C(O)C(OC)=C2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O ChemAxon formula C32H31O15 ChemAxon inchi InChI=1S/C32H30O15/c1-42-22-8-15(9-23(43-2)27(22)38)31-24(12-17-19(35)10-16(33)11-21(17)45-31)46-32-30(41)29(40)28(39)25(47-32)13-44-26(37)6-4-14-3-5-18(34)20(36)7-14/h3-12,25,28-30,32,39-41H,13H2,1-2H3,(H4-,33,34,35,36,37,38)/p+1/t25-,28-,29+,30-,32?/m1/s1 ChemAxon inchikey LIEHUFTYLLDHTI-FCOFYTSKSA-O ChemAxon polar_surface_area 238.2 ChemAxon refractivity 170.73 ChemAxon polarizability 63.93 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 14 ChemAxon donor_count 8 ChemAxon physiological_charge 0 ChemAxon formal_charge 1 ChemAxon Specdb::MsMs 55341 Specdb::MsMs 55342 Specdb::MsMs 55343 Specdb::MsMs 110472 Specdb::MsMs 110473 Specdb::MsMs 110474 Grape wine Type 2 specific 0.186004 0.186004102 0.186004102 mg/100 g