1.0 2010-04-08 22:12:38 UTC 2025-11-19 01:49:43 UTC FDB016778 Proanthocyanidin A2 Isolated from cassia bark (Cinnamomum aromaticum). Proanthocyanidin A2 is found in many foods, some of which are herbs and spices, cinnamon, avocado, and lingonberry. (+)-Proanthocyanidin A2 EC-(4b,8)(2b,7)-EC Epicatechin-(2b->7,4b->8)-epicatechin Epicatechin-(2beta->7,4beta->8)-epicatechin Proanthocyanidin A-2 Proanthocyanidin A2 Procyanidin A2 Procyanidin dimer A2 Procyanidoepicatechin Procyanidol A2 C31H26O12 590.5309 590.142426296 (1R,5R,6R,13S,21R)-13-(3,4-dihydroxy-5-methylphenyl)-5-(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol (1R,5R,6R,13S,21R)-13-(3,4-dihydroxy-5-methylphenyl)-5-(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol 41743-41-3 CC1=C(O)C(O)=CC(=C1)[C@@]12OC3=CC(O)=CC(O)=C3[C@@H]([C@H]1O)C1=C3O[C@@H]([C@H](O)CC3=C(O)C=C1O2)C1=CC=C(O)C(O)=C1 InChI=1S/C31H26O12/c1-11-4-13(6-20(37)27(11)39)31-30(40)26(24-19(36)7-14(32)8-22(24)42-31)25-23(43-31)10-17(34)15-9-21(38)28(41-29(15)25)12-2-3-16(33)18(35)5-12/h2-8,10,21,26,28,30,32-40H,9H2,1H3/t21-,26-,28-,30-,31+/m1/s1 DWMJRBXZWVVPDB-UYVQOXPASA-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-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 3'-hydroxyflavonoids 3-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids A-type proanthocyanidins Alkyl aryl ethers Catechins Catechols Hydrocarbon derivatives Ketals Meta cresols Ortho cresols Oxacyclic compounds Polyols Pyranochromenes Pyranoflavonoids Secondary alcohols Toluenes 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3'-hydroxyflavonoid 3-hydroxyflavonoid 4'-hydroxyflavonoid 5-hydroxyflavonoid 7-hydroxyflavonoid A-type proanthocyanidin Acetal Alcohol Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Benzopyran Bi- and polyflavonoid skeleton Catechin Catechol Chromane Ether Flavan Flavan-3-ol Hydrocarbon derivative Hydroxyflavonoid Ketal M-cresol Monocyclic benzene moiety O-cresol Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Polyol Proanthocyanidin Pyranochromene Pyranoflavonoid Secondary alcohol Toluene logp 2.52 ALOGPS logs -3.72 ALOGPS solubility 1.13e-01 g/l ALOGPS melting_point Mp 300° logp 4.1 ChemAxon pka_strongest_acidic 8.73 ChemAxon pka_strongest_basic -3.9 ChemAxon iupac (1R,5R,6R,13S,21R)-13-(3,4-dihydroxy-5-methylphenyl)-5-(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol ChemAxon average_mass 590.5309 ChemAxon mono_mass 590.142426296 ChemAxon smiles CC1=C(O)C(O)=CC(=C1)[C@@]12OC3=CC(O)=CC(O)=C3[C@@H]([C@H]1O)C1=C3O[C@@H]([C@H](O)CC3=C(O)C=C1O2)C1=CC=C(O)C(O)=C1 ChemAxon formula C31H26O12 ChemAxon inchi InChI=1S/C31H26O12/c1-11-4-13(6-20(37)27(11)39)31-30(40)26(24-19(36)7-14(32)8-22(24)42-31)25-23(43-31)10-17(34)15-9-21(38)28(41-29(15)25)12-2-3-16(33)18(35)5-12/h2-8,10,21,26,28,30,32-40H,9H2,1H3/t21-,26-,28-,30-,31+/m1/s1 ChemAxon inchikey DWMJRBXZWVVPDB-UYVQOXPASA-N ChemAxon polar_surface_area 209.76 ChemAxon refractivity 149.24 ChemAxon polarizability 58.11 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 12 ChemAxon donor_count 9 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 66990 Specdb::MsMs 66991 Specdb::MsMs 66992 Specdb::MsMs 124710 Specdb::MsMs 124711 Specdb::MsMs 124712 HMDB37655 #<Reference:0x000055ce3053cfb0> American cranberry Type 1 specific Vaccinium macrocarpon 13750 4.1 4.1 4.1 mg/100 g Apple Type 1 specific Malus pumila 283210 Avocado Type 1 specific Persea americana 3435 Ceylon cinnamon Type 1 specific Cinnamomum verum 128608 Chinese cinnamon Type 1 specific Cinnamomum aromaticum 119260 Cinnamon Type 1 specific Cinnamomum 13428 European cranberry Type 1 specific Vaccinium oxycoccos 516948 0.13 0.13 0.13 mg/100 g Herbs and Spices Unknown generic Lingonberry Type 1 specific Vaccinium vitis-idaea 180772 2.11 2.11 2.11 Peanut Type 1 specific Arachis hypogaea 3818 Anti bacterial 145 A substance that kills or slows the growth of bacteria. Anti capillary-fragility 160 Anti elastase 250 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. Anti enzymatic 264 Anti erythemic 268 A drug used to treat or prevent skin disorders or for the routine care of skin. Anti glucuronidase 302 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. Anti peroxidant 519 Anti-inflammatory 370 A substance that reduces or suppresses inflammation. 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-proteolytic 556 Anti-viral 689 A substance that destroys or inhibits replication of viruses. Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. Sunscreen 1337 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Venotonic 1420 Vulnerary 1430 A drug used in treating and healing of wounds.