1.02010-04-08 22:13:15 UTC2019-11-26 03:15:06 UTCFDB017715Procyanidin C2Procyanidin c2, also known as C-(4,8)-C-(4,8)-C or procyanidin trimer c2, 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''. Procyanidin c2 is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Procyanidin c2 can be found in barley, beer, and common grape, which makes procyanidin c2 a potential biomarker for the consumption of these food products. [Catechin(4a->8)]2catechinC-(4,8)-C-(4,8)-CProcyanidin C2Procyanidin trimer C2C45H38O18866.781866.205814384(2R,3S,4R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol(2R,3S,4R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol37064-31-6O[C@H]1CC2=C(O)C=C(O)C([C@H]3[C@H](O)[C@H](OC4=C([C@H]5[C@H](O)[C@H](OC6=CC(O)=CC(O)=C56)C5=CC(O)=C(O)C=C5)C(O)=CC(O)=C34)C3=CC(O)=C(O)C=C3)=C2O[C@@H]1C1=CC(O)=C(O)C=C1InChI=1S/C45H38O18/c46-18-10-27(54)33-32(11-18)61-42(16-2-5-21(48)25(52)8-16)39(59)37(33)35-29(56)14-30(57)36-38(40(60)43(63-45(35)36)17-3-6-22(49)26(53)9-17)34-28(55)13-23(50)19-12-31(58)41(62-44(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,31,37-43,46-60H,12H2/t31-,37-,38+,39-,40-,41+,42+,43+/m0/s1MOJZMWJRUKIQGL-WNCKYJNFSA-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 polyflavonoidsOrganic compoundsPhenylpropanoids and polyketidesFlavonoidsBiflavonoids and polyflavonoidsAromatic heteropolycyclic compounds1-benzopyrans1-hydroxy-2-unsubstituted benzenoids1-hydroxy-4-unsubstituted benzenoids3'-hydroxyflavonoids3-hydroxyflavonoids4'-hydroxyflavonoids5-hydroxyflavonoids7-hydroxyflavonoidsAlkyl aryl ethersB-type proanthocyanidinsBenzene and substituted derivativesC-type proanthocyanidinsCatechinsCatecholsHydrocarbon derivativesOxacyclic compoundsPolyolsSecondary alcohols1-benzopyran1-hydroxy-2-unsubstituted benzenoid1-hydroxy-4-unsubstituted benzenoid3'-hydroxyflavonoid3-hydroxyflavonoid4'-hydroxyflavonoid5-hydroxyflavonoid7-hydroxyflavonoidAlcoholAlkyl aryl etherAromatic heteropolycyclic compoundB-type proanthocyanidinBenzenoidBenzopyranBi- and polyflavonoid skeletonC-type proanthocyanidinCatechinCatecholChromaneEtherFlavanFlavan-3-olHydrocarbon derivativeHydroxyflavonoidMonocyclic benzene moietyOrganic oxygen compoundOrganoheterocyclic compoundOrganooxygen compoundOxacyclePhenolPolyolProanthocyanidinSecondary alcoholhydroxyflavanpolyphenolproanthocyanidinlogp3.38logs-3.55solubility2.47e-01 g/llogp4.44pka_strongest_acidic8.64pka_strongest_basic-5.2iupac(2R,3S,4R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triolaverage_mass866.781mono_mass866.205814384smilesO[C@H]1CC2=C(O)C=C(O)C([C@H]3[C@H](O)[C@H](OC4=C([C@H]5[C@H](O)[C@H](OC6=CC(O)=CC(O)=C56)C5=CC(O)=C(O)C=C5)C(O)=CC(O)=C34)C3=CC(O)=C(O)C=C3)=C2O[C@@H]1C1=CC(O)=C(O)C=C1formulaC45H38O18inchiInChI=1S/C45H38O18/c46-18-10-27(54)33-32(11-18)61-42(16-2-5-21(48)25(52)8-16)39(59)37(33)35-29(56)14-30(57)36-38(40(60)43(63-45(35)36)17-3-6-22(49)26(53)9-17)34-28(55)13-23(50)19-12-31(58)41(62-44(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,31,37-43,46-60H,12H2/t31-,37-,38+,39-,40-,41+,42+,43+/m0/s1inchikeyMOJZMWJRUKIQGL-WNCKYJNFSA-Npolar_surface_area331.14refractivity219.02polarizability86.02rotatable_bond_count5acceptor_count18donor_count15physiological_charge0formal_charge0Specdb::MsMs100956Specdb::MsMs100957Specdb::MsMs100958Specdb::MsMs166434Specdb::MsMs166435Specdb::MsMs166436Specdb::MsMs3606206Specdb::MsMs3606207Specdb::MsMs3606208Specdb::MsMs3606209Specdb::MsMs3606210Specdb::MsMs3606211BarleyType 1specificHordeum vulgare4513BeerType 2specific0.030.0300000010.030000001mg/100 gCommon grapeType 1specificVitis vinifera297600.00.00.0mg/100 gangiotensin converting enzyme inhibitor18An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).antioxidant502A 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.