ABSTRACT

Naturally occurring sinapic acid is a valuable synthon for many high-value applications (e.g. cosmetic, pharmaceutic) that can be found in numerous plants, especially Brasiccacea species (e.g. rapeseed, mustard). It has been demonstrated that alkaline extraction of matter rich in sinapic acid resulted in the conversion of sinapic acid into 6-hydroxy-5,7-dimethoxy-2-naphtanoic acid (DMNA). Although DMNA could be a potential alternative to petro-based naphtanoic acid used in polymers, untill now, no reliable (bio)synthetic procedure existed to synthesize it at the preparative-scale. Herein, starting from sinapic acid, we describe a very simple one-pot two-step chemo-enzymatic pathway to DMNA – and reaction intermediaries bislactone (BL) and thomasidioic acid (TA) – at gram scale using a simple filtration as purification step. Green metrics – Process Mass Index and EcoScale – have been determined to assess the sustainability of this new process. Finally, the antiradical activities of DMNA, BL and TA have been evaluated.

摘要

天然存在的芥子酸是一种有价值的合成子，可用于许多高价值应用（例如化妆品、药物），可在许多植物中找到，尤其是芸苔属种（例如油菜籽、芥菜）。已经证明，对富含芥子酸的物质进行碱性提取导致芥子酸转化为 6-羟基-5,7-二甲氧基-2-萘酸 (DMNA)。尽管 DMNA 可能是聚合物中使用的石油基萘酸的潜在替代品，但到目前为止，还没有可靠的（生物）合成程序在制备规模上合成它。在这里，从芥子酸开始，我们描述了一种非常简单的一锅两步化学酶促途径，以克级的方式使用简单的过滤作为纯化步骤，以克级的方式生成 DMNA 和反应中间体双内酯 (BL) 和 thomasidioic acid (TA)。已确定绿色指标——工艺质量指数和生态规模——来评估这一新工艺的可持续性。最后，评估了 DMNA、BL 和 TA 的抗自由基活性。