Synthesis of 2-Allylphenyl Cinnamate and Brine Shrimp Lethality Test Activity Evaluation

Abstract

Synthesis of 2-allylphenyl cinnamate has been done via coupling reaction between cinnamic acid and 2-allyl phenol catalyzed by DCC/DMAP. Their preliminary toxicity activity evaluation was calculated using Brine Shrimp Lethality Test (BSLT) method. Synthesis of the title compound was performed in 2 steps. Firstly, trans methyl cinnamate isolated from Alpinia malaccensis was hydrolyzed to cinnamic acid using 2 M ethanolic NaOH to gave trans cinnamic acid. Secondly coupling reaction of cinnamic acid and 2-allyl phenol was conducted using DCC as activator and DMAP as catalyst in cyclohexane. Structure elucidation was performed using LC-MS, 1H-NMR and 13C-NMR. Spectroscopic data collected were confirmed that product obtained from coupling reaction is 2-allylphenyl cinnamate. Brine shrimp lethality test (BSLT) activity evaluation of this compound showed that 2-allylphenyl cinnamate with LC50 100.796 μg/mL has higher activity compared to their starting material with LC50 120.470 μg/mL