Condensed tannins are responsible for astringency and bitterness and participate in the color stability of red wines. During wine making and aging, they undergo chemical changes including, for example, acetaldehyde-induced polymerization. Following this study, the ethylidene-bridged flavan-3-ols were monitored in different vintage wines made from grapes collected in the same vineyard in three wineries in Bordeaux, Pauillac, and Saint Julien. Flavan-3-ol ethylidene bridges were quantified by wine 2,2'-ethylidenediphloroglucinol (EDP) phloroglucinolysis. This method was based upon the analysis of EDP, a product formed after acid-catalyzed cleavage of wine flavan-3-ols in the presence of excess phloroglucinol. The flavan-3-ol ethylidene bridges were then compared to flavan-3-ol contents (phloroglucinolysis), phenolic contents, and color measurements. Low amounts of flavan-3-ol ethylidene bridges (0.8-2.5 mg L(-1)) were quantified in wines. Flavan-3-ol ethylidene bridges represent less than 4% of flavan-3-ol bonds, but the proportion of these linkages relative to native interflavan bonds increased with wine age. This proportion correlated with pigmented polymers.