Girish Mahajan (Editor)

Procyanidin C1

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Molar mass
  
866.77 g/mol

Formula
  
C45H38O18

Procyanidin C1 httpsuploadwikimediaorgwikipediacommonsthu

Procyanidin C1 is a B type proanthocyanidin. It is an epicatechin trimer found in grape (Vitis vinifera).

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.

References

Procyanidin C1 Wikipedia