1.0 2010-04-08 22:10:03 UTC 2025-11-18 23:34:53 UTC FDB012206 Procyanidin B4 Occurs in Rubus fruticosus (blackberry) and Rubus idaeus (raspberry). Procyanidin B4 is found in many foods, some of which are pear, bilberry, common wheat, and green bean. C-(4a,8)-EC Catechin-(4alpha->8)-epicatechin Catechin(4a->8)epicatechin Procyanidin B4 Procyanidin dimer B4 C30H26O12 578.526 578.142426277 (2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol procyanidin B4 29106-51-2 [H][C@@]1([C@H](O)[C@H](OC2=CC(O)=CC(O)=C12)C1=CC(O)=C(O)C=C1)C1=C(O)C=C(O)C2=C1O[C@@H]([C@H](O)C2)C1=CC(O)=C(O)C=C1 InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26+,27+,28-,29-/m1/s1 XFZJEEAOWLFHDH-VUGKQVTMSA-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'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Alkyl aryl ethers B-type proanthocyanidins Benzene and substituted derivatives Catechins Catechols Hydrocarbon derivatives Oxacyclic compounds Polyols Secondary alcohols 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3'-hydroxyflavonoid 3-hydroxyflavonoid 4'-hydroxyflavonoid 5-hydroxyflavonoid 7-hydroxyflavonoid Alcohol Alkyl aryl ether Aromatic heteropolycyclic compound B-type proanthocyanidin Benzenoid Benzopyran Bi- and polyflavonoid skeleton Catechin Catechol Chromane Ether Flavan Flavan-3-ol Hydrocarbon derivative Hydroxyflavonoid Monocyclic benzene moiety Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Polyol Proanthocyanidin Secondary alcohol Condensed tannins (Proanthocyanidins) Proanthocyanidins Proanthocyanidins hydroxyflavan proanthocyanidin logp 2.29 ALOGPS logs -3.62 ALOGPS solubility 1.38e-01 g/l ALOGPS melting_point Mp 172-173° (deca-Ac) logp 3.12 ChemAxon pka_strongest_acidic 8.69 ChemAxon pka_strongest_basic -5.2 ChemAxon iupac (2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol ChemAxon average_mass 578.526 ChemAxon mono_mass 578.142426277 ChemAxon smiles [H][C@@]1([C@H](O)[C@H](OC2=CC(O)=CC(O)=C12)C1=CC(O)=C(O)C=C1)C1=C(O)C=C(O)C2=C1O[C@@H]([C@H](O)C2)C1=CC(O)=C(O)C=C1 ChemAxon formula C30H26O12 ChemAxon inchi InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26+,27+,28-,29-/m1/s1 ChemAxon inchikey XFZJEEAOWLFHDH-VUGKQVTMSA-N ChemAxon polar_surface_area 220.76 ChemAxon refractivity 146.51 ChemAxon polarizability 57.3 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 12 ChemAxon donor_count 10 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 49587 Specdb::MsMs 49588 Specdb::MsMs 49589 Specdb::MsMs 141480 Specdb::MsMs 141481 Specdb::MsMs 141482 Specdb::MsMs 2683818 Specdb::MsMs 2683819 Specdb::MsMs 2683820 Specdb::MsMs 3021996 Specdb::MsMs 3021997 Specdb::MsMs 3021998 Specdb::CMs 26263 Specdb::CMs 40170 Specdb::CMs 282501 Specdb::CMs 387481 Specdb::CMs 387482 Specdb::CMs 387483 Specdb::CMs 387484 Specdb::CMs 387485 Specdb::CMs 387486 Specdb::CMs 387487 Specdb::CMs 387488 Specdb::CMs 387489 Specdb::CMs 387490 Specdb::CMs 387491 Specdb::CMs 387492 Specdb::CMs 387493 Specdb::CMs 387494 Specdb::CMs 387495 Specdb::CMs 387496 Specdb::CMs 387497 Specdb::CMs 387498 Specdb::CMs 387499 Specdb::CMs 387500 Specdb::CMs 387501 Specdb::CMs 387502 HMDB0013690 Apple Type 1 specific Malus pumila 283210 0.00875 0.0175 0.0 mg/100 g Apple cider Type 2 specific 0.0 0.0 0.0 mg/100 g Apricot Type 1 specific Prunus armeniaca 36596 0.0 0.0 0.0 mg/100 g Avocado Type 1 specific Persea americana 3435 0.0 0.0 0.0 mg/100 g Banana Type 1 specific Musa acuminata 4641 0.0 0.0 0.0 mg/100 g Bilberry Type 1 specific Vaccinium myrtillus 180763 Black tea Type 1 1.815 1.830000083 1.799999873 mg/100 g Broad bean Type 1 specific Vicia faba 3906 18.469999 18.469998678 18.469998678 mg/100 g Carrot Type 1 specific Daucus carota ssp. sativus 79200 0.0 0.0 0.0 mg/100 g Chestnut Type 1 specific Castanea 21019 0.0 0.0 0.0 mg/100 g Chickpea Type 1 specific Cicer arietinum 3827 0.0 0.0 0.0 mg/100 g Cocoa bean Type 1 specific Theobroma cacao 3641 Common bean Type 1 specific Phaseolus vulgaris 3885 0.0 0.0 0.0 mg/100 g Common grape Type 1 specific Vitis vinifera 29760 0.1782 0.382799992 0.0 mg/100 g Common pea Type 1 specific Pisum sativum 3888 0.0 0.0 0.0 mg/100 g Common wheat Type 1 specific Triticum aestivum 4565 0.0 0.0 0.0 mg/100 g Cucurbita Type 1 specific Cucurbita 3660 0.0 0.0 0.0 mg/100 g Custard apple Type 1 specific Annona reticulata 301862 2.48 2.480000019 2.480000019 mg/100 g Eggplant Type 1 specific Solanum melongena 4111 0.0 0.0 0.0 mg/100 g European plum Type 1 specific Prunus domestica 3758 1.02 1.019999981 1.019999981 mg/100 g Fig Type 1 specific Ficus carica 3494 0.0 0.0 0.0 mg/100 g Fruits Unknown generic Garden tomato (var.) Type 1 specific Solanum lycopersicum var. lycopersicum 397755 0.0 0.0 0.0 mg/100 g Grape wine Type 2 specific 2.435032 7.292499917 0.005454545 mg/100 g Green bean Type 1 specific Phaseolus vulgaris 3885 0.0 0.0 0.0 mg/100 g Green bell pepper Type 1 specific Capsicum annuum 4072 0.0 0.0 0.0 mg/100 g Green tea Type 1 1.815 1.830000083 1.799999873 mg/100 g Green zucchini Type 1 specific Cucurbita pepo var. cylindrica 0.0 0.0 0.0 mg/100 g Herbal tea Type 1 Italian sweet red pepper Type 1 specific Capsicum annuum 4072 0.0 0.0 0.0 mg/100 g Japanese persimmon Type 1 specific Diospyros kaki 35925 0.0 0.0 0.0 mg/100 g Kiwi Type 1 specific Actinidia chinensis 3625 0.0 0.0 0.0 mg/100 g Lentils Type 1 generic Lens culinaris 3864 0.0 0.0 0.0 mg/100 g Lettuce Type 1 specific Lactuca sativa 4236 0.0 0.0 0.0 mg/100 g Lingonberry Type 1 specific Vaccinium vitis-idaea 180772 Malus (Crab apple) Type 1 specific Malus 3749 Medlar Type 1 specific Mespilus germanica 36616 0.13 0.129999995 0.129999995 mg/100 g Peach (var.) Type 1 specific Prunus persica var. persica 323852 0.13 0.129999995 0.129999995 mg/100 g Peanut Type 1 specific Arachis hypogaea 3818 Pear Type 1 specific Pyrus communis 23211 0.0 0.0 0.0 mg/100 g Pepper Type 1 specific Capsicum annuum 4072 0.0 0.0 0.0 mg/100 g Pineapple Type 1 specific Ananas comosus 4615 0.0 0.0 0.0 mg/100 g Pomegranate Type 1 specific Punica granatum 22663 0.0 0.0 0.0 mg/100 g Quince Type 1 specific Cydonia oblonga 36610 0.24 0.23999999 0.23999999 mg/100 g Red bell pepper Type 1 specific Capsicum annuum 4072 0.0 0.0 0.0 mg/100 g Red raspberry Type 1 specific Rubus idaeus 32247 Red tea Type 1 Redcurrant Type 1 specific Ribes rubrum 175228 0.0 0.0 0.0 mg/100 g Rubus (Blackberry, Raspberry) Type 1 specific Rubus 23216 0.0 0.0 0.0 mg/100 g Sherry Type 2 specific 0.356 0.356000006 0.356000006 mg/100 g Strawberry Type 1 specific Fragaria X ananassa 3747 0.13 0.129999995 0.129999995 mg/100 g Sweet bay Type 1 specific Laurus nobilis 85223 Sweet cherry Type 1 specific Prunus avium 42229 0.18 0.180000007 0.180000007 mg/100 g Tea Type 1 specific Camellia sinensis 4442 1.815 1.830000083 1.799999873 mg/100 g Yellow wax bean Type 1 specific Phaseolus vulgaris 3885 0.0 0.0 0.0 mg/100 g Yellow zucchini Type 1 specific Cucurbita pepo var. cylindrica 0.0 0.0 0.0 mg/100 g Anti dermatitic 225 A drug used to treat or prevent skin disorders or for the routine care of skin. Anti neoplastic 465 A substance that inhibits or prevents the proliferation of neoplasms. Anti-gastrotic 293 A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion. 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. Beta-adrenergic receptor blocker 727 Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter. Topoisomerase-II inhibitor 1366 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands. Vulnerary 1430 A drug used in treating and healing of wounds.