Procyanidin B8

Procyanidin B8 is a B type proanthocyanidin.

Procyanidin B8
Names
IUPAC name
[(2R,3S,4R)-Flavan-3,3′,4′,5,7-pentol]-(4→6)-[(2R,3R)-flavan-3,3′,4′,5,7-pentol]
Preferred IUPAC name
(2R,2′R,3S,3′R,4R)-2,2′-Bis(3,4-dihydroxyphenyl)-3,3′,4,4′-tetrahydro-2H,2′H-[4,6′-bi-1-benzopyran]-3,3′,5,5′,7,7′-hexol
Other names
Procyanidin B8
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
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 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
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