Procyanidin B6

Procyanidin B6
Chemical structure of procyanidin B6
Chemical structure of procyanidin B6
Names
IUPAC name
[(2R,3S,4R)-Flavan-3,3′,4′,5,7-pentol]-(4→6)-[(2R,3S)-flavan-3,3′,4′,5,7-pentol]
Systematic IUPAC name
(2R,3S,4R)-2-(3,4-Dihydroxyphenyl)-3-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-6-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Other names
Procyanidin B6
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • 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
  • 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
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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Procyanidin B6 is a B type proanthocyanidin.

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

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).

References

  1. ↑ Ricardo Da Silva, Jorge M.; Rigaud, Jacques; Cheynier, Véronique; Cheminat, Annie; Moutounet, Michel (January 1991). "Procyanidin dimers and trimers from grape seeds". Phytochemistry. 30 (4): 1259–1264. Bibcode:1991PChem..30.1259R. doi:10.1016/S0031-9422(00)95213-0.
  2. ↑ Structure elucidation of proanthocyanidins: Direct synthesis and isolation from Pilsener beer. Jan Delcour, 1985 Archived 2011-07-06 at the Wayback Machine
  3. ↑ Delcour, Jan. A.; Ferreira, Daneel; Roux, David G. (1983). "Synthesis of condensed tannins. Part 9. The condensation sequence of leucocyanidin with (+)-catechin and with the resultant procyanidins". Journal of the Chemical Society, Perkin Transactions 1: 1711-1717. doi:10.1039/P19830001711.