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Preparation of Fragrant Allyl Esters

By: Ivana Luštická, Eliška Leitmannová and Libor Cˇ ervený, Institute of Chemical Technology, Prague, Czech Republic
Posted: June 12, 2009, from the July 2009 issue of P&F magazine.

This article explains the process of preparing methyl-cyclohexyloxyacetate, allylcyclohexyloxyacetate, methyl-cyclohexylpropionate and allyl-cyclohexylpropionate—the fragrant odoriferous substances used in the food and perfumery industry.

The objective of these experiments was to find suitable reaction conditions (catalyst, temperature, pressure, and catalyst amount) for the hydrogenation of methyl-phenoxyacetate to methyl-cyclohexyloxyacetate and consequently, apply the discovered conditions to the hydrogenation of methyl-cinnamate to methyl-cyclohexylpropionate. Further aim was to find a suitable basic or acidic catalyst for the transesterification of the methyl esters acquired by hydrogenation to the relevant allyl esters.

Methyl-cyclohexyloxyacetate is described with a fresh, fruity, herbal to lactone odor.1 Methyl-cyclohexylpropionate is characterized with a fresh, fruity-green odor, whereas the fragrance of allyl-cyclohexyloxyacetate is perceived to be fruity and pineapplelike.1,2 Allyl-cyclohexylpropionate is a substance whose aroma can be expressed as sweet, pineapple.

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