Procyanidin B8

Procyanidin B8

Names
IUPAC name (2R,2ʼR,3S,3ʼR,4R)-2,2'-bis(3,4-dihydroxyphenyl)-3,3ʼ,4,4ʼ-tetrahydro-2H,2ʼH-4,6ʼ-bichromene-3,3ʼ,5,5ʼ,7,7ʼ-hexol
Other names Procyanidin B8
Identifiers
3D model (Jmol)	Interactive image
ChEBI	CHEBI:75618
ChEMBL	ChEMBL451115
ChemSpider	416636
PubChem	474541
InChI InChI=1S/C30H26O12/c31-13-7-19(36)24-23(8-13)42-30(12-2-4-16(33)18(35)6-12)28(40)26(24)25-20(37)10-22-14(27(25)39)9-21(38)29(41-22)11-1-3-15(32)17(34)5-11/h1-8,10,21,26,28-40H,9H2/t21-,26+,28+,29-,30-/m1/s1 Key: GMISZFQPFDAPGI-JJYFIROESA-N InChI=1/C30H26O12/c31-13-7-19(36)24-23(8-13)42-30(12-2-4-16(33)18(35)6-12)28(40)26(24)25-20(37)10-22-14(27(25)39)9-21(38)29(41-22)11-1-3-15(32)17(34)5-11/h1-8,10,21,26,28-40H,9H2/t21-,26+,28+,29-,30-/m1/s1 Key: GMISZFQPFDAPGI-JJYFIROEBQ
SMILES O[C@@H]1Cc2c(O[C@@H]1c1ccc(O)c(O)c1)cc(O)c([C@H]1[C@H](O)[C@H](Oc3cc(O)cc(O)c13)c1ccc(O)c(O)c1)c2O
Properties
Chemical formula	C30H26O12
Molar mass	578.52 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Procyanidin B8 is a B type proanthocyanidin.

Procyanidin B8 is a catechin-(4α→6)-epicatechin dimer. It can be found in grape seeds^[1] and in beer.^[2]

References

1. Procyanidin dimers and trimers from grape seeds. Jorge M. Ricardo da Silva, Jacques Rigaud, Véronique Cheynier, Annie Cheminat and Michel Moutounet,Phytochemistry, 1991, Volume 30, Issue 4, Pages 1259–1264, doi:10.1016/S0031-9422(00)95213-0
2. Structure elucidation of proanthocyanidins: Direct synthesis and isolation from Pilsener beer. Jan Delcour, Thesis, 1985