Faced with the increasing demand from both the cosmetic industries and consumers for bio-based, safe and natural skin products, sinapoyl-L-malate, widely described for its UV protection in plants, appears to be an excellent alternative to substitute chemical filters in sunscreens. Unfortunately, the only synthetic routes described in the literature were not only tedious but also exhibit a strong negative environmental impact, thus seriously limiting the industrialization and commercialization of sinapoyl-L-malate. Herein, a shorter and greener synthetic pathway involving Meldrum's acid opening with unprotected naturally occurring hydroxy acids and its subsequent Knoevenagel-Doebner condensation with biomass-derived p-hydroxybenzaldehydes was designed and developed. This two-step procedure, whom sustainability has been assessed using green metrics (atom economy (AE), process atom economy (PAE), E-factor and LCA), is a great alternative to the already reported procedures and allows the access to sinapoyl-L-malate and several analogs in average to good yield. The study of the anti-UV properties, stability against UV radiation, radical scavenging and antimicrobial activities of the targets revealed attractive properties as photostable UV filters, antioxidants and preservatives. Moreover, the water solubility brought by the free carboxylic acids facilitates the incorporation of these molecules in cosmetic formulations. Finally, their innocuousness toward endocrine disruption was demonstrated.

中文翻译：

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快速和可持续的两步合成芥子酸左旋苹果酸及其类似物：致力于非内分泌干扰性生物基和水溶性生物活性化合物

面对化妆品行业和消费者对基于生物的，安全的和天然的皮肤产品的日益增长的需求，以植物中的紫外线防护而被广泛描述的sinapoyl- L-苹果酸酯似乎是替代防晒霜中化学过滤器的绝佳替代品。不幸的是，文献中描述的唯一合成路线不仅繁琐而且还表现出强烈的负面环境影响，从而严重限制了芥子酸L-苹果酸的工业化和商业化。本文中，一条较短且绿色的合成途径包括：用未保护的天然羟基酸打开麦德鲁姆酸，然后其与生物质衍生的p的Knoevenagel-Doebner缩合-羟基苯甲醛的设计和开发。此分两步程序已使用绿色指标（原子经济性（AE），过程原子经济性（PAE），E因子和LCA）评估了可持续性，是已报告程序的绝佳替代方案，可使用辛那普利-苹果酸L和平均数的类似物达到良好的收率。对目标物的抗紫外线性能，抗紫外线辐射的稳定性，自由基清除和抗菌活性的研究显示出作为光稳定的紫外线滤光片，抗氧化剂和防腐剂的诱人特性。此外，由游离羧酸带来的水溶性促进了这些分子在化妆品制剂中的掺入。最后，证明了它们对内分泌破坏无害。