Biocatalytic synthesis of the non-pungent capsaicinoid olvanil from agri-food waste

Abstract

Capsaicin and simple capsaicinoids have been shown to possess multiple beneficial effects as antibacterials, anticancer agents, antioxidants or against obesity, just to name a few. Olvanil is one of the first synthetic capsaicinoid derivatives designed to activate the same receptor as natural capsaicin, without eliciting its powerful stinging or burning effects. The traditional synthetic approaches to olvanil involve the chemical conversion of vanillin into vanillylamine and a poorly atom-economic chemical amidation with an activated derivative of oleic acid. In this work, a simple biocatalytic two-step procedure has been developed and optimised to produce olvanil, starting from two biomass-derived synthons (oleic acid from vegetable oil soapstock waste and vanillin from lignin). The process employs only biobased reagents and catalysts, under mild conditions and without wasteful purifications, aligning well with the concepts of green chemistry and circular economy.