Procyanidin B6

Procyanidin B6

Names
Other names Procyanidin B6
Identifiers
ChEBI	CHEBI:75619
ChemSpider	416635
Jmol interactive 3D	Image
PubChem	474540
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+/m0/s1 Key: GMISZFQPFDAPGI-ZBRHZRBFSA-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+/m0/s1 Key: GMISZFQPFDAPGI-ZBRHZRBFBC
SMILES Oc1ccc(cc1O)[C@H]5Oc6cc(O)c([C@@H]3c2c(cc(O)cc2O)O[C@@H]([C@H]3O)c4ccc(O)c(O)c4)c(O)c6C[C@@H]5O
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 B6 is a B type proanthocyanidin.

Procyanidin B6 is a catechin-(4α→6)-catechin dimer. It can be found in grape seeds^[1] and in beer.^[2]

Chemical synthesis

Molar equivalents of synthetic (2R,3S,4R or S)-leucocyanidin and (+)-catechin condense with exceptional rapidity at pH 5 under ambient conditions to give the all-trans-[4,8]- and [4,6]-bi-[(+)-catechins] (procyanidins B3 and B6) the all-trans-[4,8:4,8]- and [4,8:4,6]-tri-[(+)-catechins] (procyanidin C2 and isomer).^[3]

References

1. Procyanidin dimers and trimers from grape seeds. Jorge M. Ricardo da Silva, Jacques Rigaud, Véronique Cheynier, Annie Cheminat and Michel Moutounet, 1991
2. Structure elucidation of proanthocyanidins: Direct synthesis and isolation from Pilsener beer. Jan Delcour, 1985
3. Synthesis of condensed tannins. Part 9. The condensation sequence of leucocyanidin with (+)-catechin and with the resultant procyanidins. Jan. A. Delcour, Daneel Ferreira and David G. Roux, J. Chem. Soc., Perkin Trans. 1, 1983, pages 1711-1717, doi:10.1039/P19830001711