1.0 2010-04-08 22:06:26 UTC 2025-11-18 22:57:48 UTC FDB004901 Proanthocyanidins Proanthocyanidins, also known as zangrado or polyhydroxyflavan-3-ol, is a member of the class of compounds known as biflavonoids and polyflavonoids. Biflavonoids and polyflavonoids are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Proanthocyanidins is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Proanthocyanidins can be found in a number of food items such as roselle, allspice, cocoa bean, and sweet bay, which makes proanthocyanidins a potential biomarker for the consumption of these food products. Proanthocyanidins were discovered in 1947 by Jacques Masquelier, who developed and patented techniques for the extraction of oligomeric proanthocyanidins from pine bark and grape seeds. Often associated with consumer products made from cranberries, grape seeds or red wine, proanthocyanidins were once proposed as factors inhibiting urinary tract infections in women, but this research has been refuted by expert scientific committees . Proanthocyanidin C31H28O12 592.553 592.158076342 (2R,3R,4R)-4-[(3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol (2R,3R,4R)-4-[(3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol 18206-61-6 [H][C@@]1(O)CC2=C(OC1([H])C1=CC(O)=C(OC)C(O)=C1)C(=C(O)C=C2O)[C@@]1([H])C2=C(O)C=C(O)C=C2O[C@]([H])(C2=CC=C(O)C=C2)[C@]1([H])O InChI=1S/C31H28O12/c1-41-31-20(37)6-13(7-21(31)38)28-22(39)10-16-17(34)11-19(36)25(30(16)43-28)26-24-18(35)8-15(33)9-23(24)42-29(27(26)40)12-2-4-14(32)5-3-12/h2-9,11,22,26-29,32-40H,10H2,1H3/t22-,26-,27-,28?,29-/m1/s1 JPFCOVZKLAXXOE-XBNSMERZSA-N belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Biflavonoids and polyflavonoids Organic compounds Phenylpropanoids and polyketides Flavonoids Biflavonoids and polyflavonoids Aromatic heteropolycyclic compounds 1-benzopyrans 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 3'-hydroxyflavonoids 3-hydroxyflavonoids 4'-O-methylated flavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Alkyl aryl ethers Anisoles B-type proanthocyanidins Epigallocatechins Hydrocarbon derivatives Methoxybenzenes Methoxyphenols Oxacyclic compounds Phenoxy compounds Polyols Resorcinols Secondary alcohols 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3'-hydroxyflavonoid 3-hydroxyflavonoid 4'-hydroxyflavonoid 4p-methoxyflavonoid-skeleton 5-hydroxyflavonoid 7-hydroxyflavonoid Alcohol Alkyl aryl ether Anisole Aromatic heteropolycyclic compound B-type proanthocyanidin Benzenoid Benzopyran Bi- and polyflavonoid skeleton Catechin Chromane Epigallocatechin Ether Flavan Flavan-3-ol Hydrocarbon derivative Hydroxyflavonoid Methoxybenzene Methoxyphenol Monocyclic benzene moiety Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Phenol ether Phenoxy compound Polyol Proanthocyanidin Resorcinol Secondary alcohol logp 2.42 ALOGPS logs -3.80 ALOGPS solubility 9.39e-02 g/l ALOGPS logp 3.26 ChemAxon pka_strongest_acidic 8.86 ChemAxon pka_strongest_basic -3.5 ChemAxon iupac (2R,3R,4R)-4-[(3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol ChemAxon average_mass 592.553 ChemAxon mono_mass 592.158076342 ChemAxon smiles [H][C@@]1(O)CC2=C(OC1([H])C1=CC(O)=C(OC)C(O)=C1)C(=C(O)C=C2O)[C@@]1([H])C2=C(O)C=C(O)C=C2O[C@]([H])(C2=CC=C(O)C=C2)[C@]1([H])O ChemAxon formula C31H28O12 ChemAxon inchi InChI=1S/C31H28O12/c1-41-31-20(37)6-13(7-21(31)38)28-22(39)10-16-17(34)11-19(36)25(30(16)43-28)26-24-18(35)8-15(33)9-23(24)42-29(27(26)40)12-2-4-14(32)5-3-12/h2-9,11,22,26-29,32-40H,10H2,1H3/t22-,26-,27-,28?,29-/m1/s1 ChemAxon inchikey JPFCOVZKLAXXOE-XBNSMERZSA-N ChemAxon polar_surface_area 209.76 ChemAxon refractivity 150.99 ChemAxon polarizability 58.52 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 12 ChemAxon donor_count 9 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 92091 Specdb::MsMs 92092 Specdb::MsMs 92093 Specdb::MsMs 155649 Specdb::MsMs 155650 Specdb::MsMs 155651 Specdb::MsMs 3601181 Specdb::MsMs 3601182 Specdb::MsMs 3601183 Specdb::MsMs 3601184 Specdb::MsMs 3601185 Specdb::MsMs 3601186 26267 Allspice Type 1 specific Pimenta dioica 375272 Apricot Type 1 specific Prunus armeniaca 36596 Avocado Type 1 specific Persea americana 3435 Ceylon cinnamon Type 1 specific Cinnamomum verum 128608 Cherimoya Type 1 specific Annona cherimola 49314 Cocoa bean Type 1 specific Theobroma cacao 3641 Common buckwheat Type 1 specific Fagopyrum esculentum 3617 Ginkgo nuts Type 1 specific Ginkgo biloba 3311 Roselle Type 1 specific Hibiscus sabdariffa 183260 Star anise Type 1 specific Illicium verum 124778 Sweet bay Type 1 specific Laurus nobilis 85223 Anti bacterial 145 A substance that kills or slows the growth of bacteria. Anti CVI 213 Anti histaminic 331 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists. Anti periodontal 514 Anti proliferant 547 Anti retinopathic 580 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti septic 603 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti-alopecic 104 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-atherosclerotic 138 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. Anti-diabetic 228 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-edemic 248 Anti-ischemic 377 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-oxidant 502 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. Anti-plaque 531 Anti-stroke 633 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-viral 689 A substance that destroys or inhibits replication of viruses. Antitumor 672 A substance that inhibits or prevents the proliferation of neoplasms. Beta-glucuronidase inhibitor 729 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Capillariprotective 760 Cardioprotective 769 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. Collagenase inhibitor 823 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Collagenic 824 Deodorant 870 Elastase inhibitor 897 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Gram(-)icide 963 A substance that kills or slows the growth of bacteria. Gram(+)icide 962 A substance that kills or slows the growth of bacteria. Hepatoprotective 981 Any compound that is able to prevent damage to the liver. Hyaluronidase inhibitor 998 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Hypoglycemic 1017 A drug which lowers the blood glucose level. Ornithine-decarboxylase inhibitor 1175 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Tyrosine kinase inhibitor 1253 Vasodilator 1413 A drug used to cause dilation of the blood vessels. Vasorelaxant 1417