p‐Menthandiol‐vanillin acetals: synthesis and study of their chemo‐sensorial properties

Abstract

A study on the synthesis of a number of p‐menthandiols‐vanillin(isovanillin) acetals derivatives is reported here. Properties of the compounds prepared were crudely investigated by tasting and by focusing on their chemesthetic effect. In particular some of these acetals showed a definite warming effect. In order to investigate correlation between chemical structure and biological activity, a large number of the aforementioned acetals were prepared by means of the targeted modification of the p‐menthane framework. This approach revealed that structural modifications considerably affect the chemesthetic properties of these compounds, allowing the identification of two kinds of sensorially active chemical frameworks. The potential of these findings in the design of new food additives featuring a warming/tingling effect is discussed. Copyright © 2013 John Wiley & Sons, Ltd.

Corymbia citriodora: A Valuable Resource from Australian Flora for the Production of Fragrances, Repellents, and Bioactive Compounds

“…Chemesthetic acetal agents made from p-menthane diols and vanillin/isovanillin were synthesized and evaluated for their ability to induce a hot/cold sensation, or for their unique taste/smell [67]. Among the starting materials to be acetylated, 18 produced by the acid-catalyzed cyclization of (+)-1 was utilized.…”