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| Names | |
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| IUPAC name
[(2R,3S,4R)-Flavan-3,3′,4′,5,7-pentol]-(4→6)-[(2R,3S)-flavan-3,3′,4′,5,7-pentol]
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| 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
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
PubChem CID
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| UNII | |
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| 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[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
- ^ Procyanidin dimers and trimers from grape seeds. Jorge M. Ricardo da Silva, Jacques Rigaud, Véronique Cheynier, Annie Cheminat and Michel Moutounet, 1991[dead link]
- ^ Structure elucidation of proanthocyanidins: Direct synthesis and isolation from Pilsener beer. Jan Delcour, 1985 Archived 2011-07-06 at the Wayback Machine
- ^ 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
This page was last edited on 6 May 2023, at 21:34