The Chemical Structure of Aceritannin (Acertannin). I. Determination of the Location of Two Galloyl Groups in Aceritannin

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Examinations were made on the chemical structure of aceritannin (acertannin), an oligogalloylated, crystalline tannin, C₂₀H₂₀O₁₃·2H₂O, m.p. 164∼166°, [α]¹²_D +20°(Me₂CO and EtOH, each), which was first isolated by Perkin and Uyeda from the leaves of Acer Ginnala MAXIM. It has now been proved that aceritannin should be formulated as 3, 6-di-O-galloyl-1, 5-anhydro-D-glucitol, i.e., no other than 1-deoxy derivative of 3, 6-di-O-galloyl-D-glucopyranose, a compound first isolated by Freudenberg (Ber., 52, 1238 (1919)) as one of the partial hydrolysis products of chebulinic acid, and later, unequivocally synthesized by Schmidt and Schach (Ann., 571, 29(1951)).