Procyanidin B8

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
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
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