Synthesis and photoprotective properties of new salicylic and vanillic acid derivatives

Abstract

A simple one-step procedure for synthesis of new derivatives of phenolic acids was developed. As the starting materials salicylic acid, vanillic acid and alkyl haloalkanoates were applied. The reactions were carried out in N,N-dimethylformamide (DMF) in the presence of anhydrous potassium carbonate. Conditions for regioselective synthesis of target compounds were established. The esters 3a-h were obtained in great yields and were characterized by MS, 1 H and 13 C NMR spectra. Their photoprotective activity was evaluated in vitro by spectrophotometric method. The study revealed that the tested compounds are moderate UVB absorbers, but could be used to augment the effect of other photoprotective agents. Their SPF values were in the range from 3.63 to 4.26 for salicylates 3a-d and from 3.03 to 3.51 for vanillates.

Preliminary Phytochemical Profile and Bioactivity of Inga jinicuil Schltdl & Cham. ex G. Don

“…Regarding the analysis of the UV-Vis spectra of Peaks 10 , 11 , 14 , and 16 , it was possible to associate them with previous reports for terpene derivatives [ 24 ]. Likewise, Peaks 13 and 17 were consistent with bibliographical data of epigallocatechin gallate derivatives [ 28 ], and Peak 15 may be associated with vanillic acid derivatives [ 29 , 30 ]. Finally, the absorption bands of Peaks 19 , 20 , and 21 were associated with salicylate derivatives [ 31 ].…”

Synthesis and Molecular Docking Based Exploration of Salicylic Acid Derivatives

“…Salicylic acid can be used to synthesize aspirin which further can be used to synthesize the derivative of indoles. The literature reviews of salicylic acid derivatives enlightened us about numbers of medicinal, pharmacological or therapeutic activities [5][6][7][8][9][10][11][12][13][14][15][16][17].…”