Capsaicin is a natural defense mechanism against consumption in hot pepper plants, Capsicum. Capsaicin, 8-methy-N-vanillyl-6-nonenamide, and analog capsaicinoids cause a burning sensation by binding to transient receptor potential channels and are known to have medicinal applications. In this experiment, a derivative capsaicinoid is synthesized in two steps from Vanillin. The microscale procedure involves the preparation and reduction of an imine followed by acyl substitution to prepare the capsaicinoid and is completed in a large test tube. These reactions are essential topics in second semester undergraduate organic chemistry and provide a relevant laboratory experience.

Synthesis of capsaicin for undergraduate organic laboratory

246th National Meeting (2013)

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