LAUSR

Benzoic acid and its derivatives are compounds with significant benefits for human health, due to their biological and pharmacological properties, such as being antioxidant, anti‐inflammatory, anticancer, and neuroprotective. Benzoic compounds are present in human daily diet, for example, in fruit and vegetables. However, it is described that, when ingested, these natural compounds are distributed throughout our body, resulting in high variability or not clinically relevant responses, and consequently being difficult to cross the biological barriers and to accumulate in a specific target. Lipophilization of phenolic acids, namely, by introducing a spacer constituted by aliphatic chain with a variable number of carbon atoms, is one of the strategies often used to improve their hydrophobicity and overcome some of the limitations. Within this framework, a complete structural elucidation by one‐ and two‐dimensional (1D and 2D, respectively) NMR, mass spectroscopy, and X‐ray techniques of a series of bromobenzamides of our library containing different spacer length (6‐, 8‐ and 10‐carbon aliphatic chain) and different substituents in the aromatic ring (Scheme 1) were found to be relevant. Finally, to complete the study, single crystal X‐ray crystallographic analysis of Compound 8 (N‐(6‐bromohexyl)‐3,4,5‐trimethoxybenzamide) was carried out.