Procyanidin C1

Procyanidin C1
Chemical structure of procyanidin C1
Names
IUPAC name
(2R,2ʼR,2ʼʼR,3R,3ʼR,3ʼʼR,4R,4ʼS)-2,2ʼ,2ʼʼ-tris(3,4-dihydroxyphenyl)-3,3ʼ,3ʼʼ,4,4ʼ,4ʼʼ-hexahydro-2H,2ʼH,2ʼʼH-4,8ʼ:4ʼ,8ʼʼ-terchromene-3,3ʼ,3ʼʼ,5,5ʼ,5ʼʼ,7,7ʼ,7ʼʼ-nonol
Other names
Procyanidin C1
Procyanidol C1
Epicatechin-(4.beta.-->8)epicatechin-(4.beta.-->8)epicatechin
Epicatechin-(4β→8)-epicatechin--(4β→8)-epicatechin
Identifiers
37064-30-5 YesY=
3D model (Jmol) Interactive image
ChEBI CHEBI:75643
ChEMBL ChEMBL290632
ChemSpider 148540
KEGG C17624
PubChem 169853
Properties
C45H38O18
Molar mass 866.77 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 C1 is a B type proanthocyanidin. It is an epicatechin trimer found in grape (Vitis vinifera).[1]

Chemical synthesis

The stereoselective synthesis of seven benzylated proanthocyanidin trimers (epicatechin-(4β-8)-epicatechin-(4β-8)-epicatechin trimer (procyanidin C1), catechin-(4α-8)-catechin-(4α-8)-catechin trimer (procyanidin C2), epicatechin-(4β-8)-epicatechin-(4β-8)-catechin trimer and epicatechin-(4β-8)-catechin-(4α-8)-epicatechin trimer derivatives) can be achieved with TMSOTf-catalyzed condensation reaction, in excellent yields. The structure of benzylated procyanidin C2 was confirmed by comparing the 1H NMR spectra of protected procyanidin C2 that was synthesized by two different condensation approaches. Finally, deprotection of (+)-catechin and (-)-epicatechin trimers derivatives gives four natural procyanidin trimers in good yields.[2]

See also

References

  1. ↑ Proanthocyanidin composition of red Vitis vinifera varieties from the Douro valley during ripening : Influence of cultivation altitude. Mateus Nuno, Marques Sara, Goncalves Ana C., Machado José M. and De Freitas Victor, American journal of enology and viticulture, 2001, vol. 52, no2, pp. 115-121, INIST:1129642
  2. ↑ Efficient Stereoselective Synthesis of Proanthocyanidin Trimers with TMSOTf-Catalyzed Intermolecular Condensation. Akiko Saito, Akira Tanaka, Makoto Ubukata and Noriyuki Nakajima, Synlett, 2004, volume 6, pages 1069-1073, doi:10.1055/s-2004-822905


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