Procyanidin B6
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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] | |
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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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). Y verify (what is YN ?) Infobox references |
Chemical compound
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
- ^ 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.
- ^ Structure elucidation of proanthocyanidins: Direct synthesis and isolation from Pilsener beer. Jan Delcour, 1985 Archived 2011-07-06 at the Wayback Machine
- ^ 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.
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Types of procyanidins
- Dimers : Procyanidin A1
- A2
- Trimers:Cinnamtannin B1
- Tetramers: Arecatannin A2
- Dimers : Procyanidin B1
- B2
- B3
- B4
- B5
- B6
- B8
- D (ent-Epicatechin(4α→8)catechin)
- Trimers: Arecatannin B1 (epicatechin-(4β→8)-epicatechin-(4β→6)-catechin)
- Procyanidin C1 (epicatechin-(4β→8)-epicatechin-(4β→8)-epicatechin)
- Procyanidin C2 (catechin-(4α→8)-catechin-(4α→8)-catechin)
- Tetramers : Cinnamtannin A2
- Arecatannins
- Arecatannin A1
- Arecatannin A3
- Arecatannin B2
- Arecatannin C1