Structural elucidation of condensed tannin from the bark waste of Acacia crassicarpa plantation wood in Indonesia

Recently, Acacia crassicarpa has been planted in peatland areas with acidic soil in Indonesia for use in pulp and paper materials. Its bark is not suitable to produce bleached pulp; hence, it is discarded as waste. Meanwhile, in South Africa and other countries, Acacia mearnsii has been planted for a long time, and its bark extracts have been used as a leather tanning agent. First, the structure of condensed tannin from the bark waste of A. crassicarpa is characterized. The yield of the extracts obtained from A. crassicarpa using a 70% acetone aqueous solution (7% based on bark weight) is less than that obtained from A. mearnsii (34%). A novel flavan dimer from the condensed tannin, specific to A. crassicarpa , is isolated from the bark extracts. To the best of our knowledge, this dimer is a new compound as evidenced from pyrolysis–gas chromatography–mass spectrometry and nuclear magnetic resonance analyses; it corresponds to a gallocatechin–catechin flavan dimer with the absence of one oxygen atom at the 3C of the pyran ring. In addition, 2,4,6-trimethoxybenzoic acid methyl ester is identified as a novel pyrolysis product obtained from the cleavage of the pyran ring.