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The identification of cyclic (or crown) B-type proanthocyanidins in wine was recently reported; this identification has unlocked new possibilities for their application to wine quality evaluation. Here, cyclic and non-cyclic B-type proanthocyanidins, along with other phenolic compounds as well as sensory and oenological parameters, were characterized in eleven Pinot Noir wines. The wines were produced from grapes harvested in different vineyards and under different winemaking conditions. With Principal Component Analysis (PCA) based on the cyclic proanthocyanidins or their relative proportions, it was possible to differentiate the wines according to specific winemaking conditions. Moreover, cyclic proanthocyanidins were related to the overall sensory quality of Pinot Noir wines.