2003/05/02 by Michael Schwarz, Tobias C. Wabnitz, Peter Winterhalter · 5 citations
Agricultural and Biological Sciences · Biochemistry, Genetics and Molecular Biology · #Fermentation and Sensory Analysis #Plant biochemistry and biosynthesis #Biochemical and biochemical processes
paper · doi:10.1021/jf0340963
openalex publication_date 2003/05/02 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/08
On the basis of observations from Vitis vinifera cv. Pinotage wines and experiments performed in model wine medium, a new chemical pathway responsible for the formation of anthocyanin-vinylphenol adducts in red wines is described. Until now, these pigments have been considered to be reaction products of anthocyanins and vinylphenols, the latter being generated during fermentation by enzymatic decarboxylation of the respective cinnamic acids. The mechanism of the novel pathway, involving intact hydroxycinnamic acid and anthocyanin, is explained. Only cinnamic acids with electron-donating substituents on the aromatic ring, such as coumaric acid, ferulic acid, caffeic acid, and sinapic acid, undergo this conversion, as they stabilize an intermediately formed carbenium ion. Decarboxylation and oxidation of the pyran moieties are the final steps in the generation of the corresponding 4-vinylphenol, 4-vinylguaiacol, 4-vinylcatechol, and 4-vinylsyringol adducts of anthocyanins in red wine.