Procyanidin C2
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| Other names
C-(4,8)-C-(4,8)-C
Procyanidin trimer C2 Catechin-(4alpha→8)-Catechin-(4alpha→8)-Catechin Catechin-(4α→8)-catechin-(4α→8)-catechin Trimer C2 |
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3D model (JSmol)
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| ChEBI | |
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| Properties | |
| C45H38O18 | |
| Molar mass | 866.74 g/mol |
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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 C2 is a B type proanthocyanidin trimer, a type of condensed tannin.
Procyanidin C2 is found in grape seeds (Vitis vinifera) and wine, in barley (Hordeum vulgare),malt and beer, in Betula spp., in Pinus radiata, in Potentilla viscosa, in Salix caprea or in Cryptomeria japonica.
The contents in barley grain of trimeric proanthocyanidins, including procyanidin C2, range from 53 to 151 μg catechin equivalents/g.
Proanthocyanidin oligomers, extracted from grape seeds, have been used for the experimental treatment of androgenic alopecia. When applied topically, they promote hair growth in vitro, and induce anagen in vivo. Procyanidin C2 is the subtype of extract most effective.
Experiments showed that both procyanidin C2 and Pycnogenol (French maritime pine bark extract) increase TNF-α secretion in a concentration- and time-dependent manner. These results demonstrate that procyanidins act as modulators of the immune response in macrophages.
In the presence of procyanidin C2, the red color of the anthocyanin oenin appears more stable. However, the HPLC chromatogram shows a decrease in the amplitude of the peaks of oenin and procyanidin C2. Concomitantly, a new peak appears with a maximal absorption in the red region. This newly formed pigment probably comes from the condensation of oenin and procyanidin C2.
A stereoselective synthesis of benzylated catechin trimer under intermolecular condensasion is achieved using equimolar amount of dimeric catechin nucleophile and monomeric catechin electrophile catalyzed by AgOTf or AgBF4. The coupled product can be transformed into procyanidin C2 by a known procedure.
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