1.0 2010-04-08 22:05:01 UTC 2025-11-18 22:32:09 UTC FDB001594 Malvidin 3-(6''-p-caffeyglucoside) Malvidin 3-(6''-p-caffeyglucoside) is a member of the class of compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. Anthocyanidin 3-o-6-p-coumaroyl glycosides are anthocyanidin 3-O-glycosides where the carbohydrate moiety is esterified at the C6 position 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''-p-caffeyglucoside) is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Malvidin 3-(6''-p-caffeyglucoside) can be synthesized from cis-caffeic acid. Malvidin 3-(6''-p-caffeyglucoside) can also be synthesized into malvidin. Malvidin 3-(6''-p-caffeyglucoside) can be found in common grape, which makes malvidin 3-(6''-p-caffeyglucoside) a potential biomarker for the consumption of this food product. Malvidin 3-(6''-p-caffeyglucoside) may be a unique S.cerevisiae (yeast) metabolite. C32H31O15 655.5795 655.166295322 3-{[(2S,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)-1λ⁴-chromen-1-ylium 3-{[(2S,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)-1λ⁴-chromen-1-ylium 129016-23-5 COC1=CC(=CC(OC)=C1O)C1=[O+]C2=C(C=C1O[C@@H]1O[C@H](COC(=O)\C=C\C3=CC(O)=C(O)C=C3)[C@@H](O)[C@H](O)[C@H]1O)C(O)=CC(O)=C2 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-KWNZYCHBSA-O belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. 2'-Hydroxychalcones Organic compounds Phenylpropanoids and polyketides Linear 1,3-diarylpropanoids Chalcones and dihydrochalcones Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Acryloyl compounds Alkyl aryl ethers Anisoles Aryl ketones Benzoyl derivatives Cinnamylphenols Dimethoxybenzenes Enones Hydrocarbon derivatives Methoxyphenols Organic oxides Phenoxy compounds Styrenes Vinylogous acids 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2'-hydroxychalcone Acryloyl-group Alkyl aryl ether Alpha,beta-unsaturated ketone Anisole Aromatic homomonocyclic compound Aryl ketone Benzenoid Benzoyl Cinnamylphenol Dimethoxybenzene Enone Ether Hydrocarbon derivative Ketone M-dimethoxybenzene Methoxybenzene Methoxyphenol Monocyclic benzene moiety Organic oxide Organic oxygen compound Organooxygen compound Phenol Phenol ether Phenoxy compound Styrene Vinylogous acid Chalcones and dihydrochalcones 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-{[(2S,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)-1λ⁴-chromen-1-ylium ChemAxon average_mass 655.5795 ChemAxon mono_mass 655.166295322 ChemAxon smiles COC1=CC(=CC(OC)=C1O)C1=[O+]C2=C(C=C1O[C@@H]1O[C@H](COC(=O)\C=C\C3=CC(O)=C(O)C=C3)[C@@H](O)[C@H](O)[C@H]1O)C(O)=CC(O)=C2 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-KWNZYCHBSA-O ChemAxon polar_surface_area 238.2 ChemAxon refractivity 170.73 ChemAxon polarizability 64.98 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 13 ChemAxon donor_count 8 ChemAxon physiological_charge 0 ChemAxon formal_charge 1 ChemAxon Specdb::MsMs 44418 Specdb::MsMs 44419 Specdb::MsMs 44420 Specdb::MsMs 110376 Specdb::MsMs 110377 Specdb::MsMs 110378 Common grape Type 1 specific Vitis vinifera 29760