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A sustainable preparative-scale chemo-enzymatic synthesis of 6-hydroxy-5,7-dimethoxy-2-naphthoic acid (DMNA) from sinapic acid
Published in Green Chemistry Letters and Reviews, 2022
Amandine L. Flourat, Nour Zeaiter, Erwan Vallée, V. P. Thinh Nguyen, Sami Fadlallah, Florent Allais
6-Hydroxy-5,7-dimethoxy-2-naphthoic acid (DMNA) was first assumed as a natural product found in the alkaline extract of the heartwood of Ulmus thomasii Sarg (Figure 1) (7). However, the natural occurrence of this compound is questionable due to the observation of Charlton and Lee who suggested that DMNA is an oxidized product of SA under strongly alkaline conditions (8). Interestingly, the structure of DMNA shows a high similarity to that of 6-hydroxy-2-naphthoic acid (NA) (Figure 1), a petroleum-based chemical commonly used for the production of the high-value-added liquid crystal polymer Vectra® (9–11). Moreover, the antimicrobial activity of some DMNA analogs has been reported (12, 13). Considering the aforementioned data, we believe that DMNA could be a potential renewable building block for biobased chemicals and materials that can replace other NA analogs issued from limited fossil resources.