Process for preparing compositions containing unsaturated lactones, products produced thereby and organoleptic uses of said products

摘要

Described is a process for the preparation of compositions of matter containing unsaturated lactones defined according to the generic structure: <IMAGE> wherein R represents C6 alkyl or alkenyl; and X represents C2, C4 or C6 alkylene or alkenylene; with the provisos that R is C6 alkyl when X is alkenylene and R is C6 alkenyl when X is alkylene by means of the sequential steps of (i) fermentation of castor oil or ricinoleic acid using a microorganism selected from the group consisting of: Candida petrophilum, ATCC 20226; Candida oleophila, ATCC 20177; Candida sp., ATCC 20504; and Candida sake, ATCC 28137 whereby gamma hydroxydecanoic acid and a mixture of other acids defined according to the generic structure: <IMAGE> is formed wherein Y represents an oxo-saturated, oxo-unsaturated or di-unsaturated C9, C11 or C13 moiety according to the reaction: <IMAGE> <IMAGE> (ii) lactonization of the resulting gamma hydroxydecanoic acid by means of simultaneous acidification and heating according to the reaction: <IMAGE> +TR <IMAGE> and (iii) lactonization (via distillation) of one or more of the resulting acids defined according to the structure: <IMAGE> to form one or more lactones defined according to the generic structure: <IMAGE> according to the reaction: <IMAGE> <IMAGE> wherein the sum of the number of carbon atoms in the X moiety and in the R moiety is equal to the number of carbon atoms in the Y moiety minus 1. Also described are the products produced according to such process as well as their organoleptic utilities for augmenting or enhancing the aroma or taste of consumable materials selected from the group consisting of perfume compositions, colognes, perfumed articles, perfumed polymers, foodstuffs, chewing gums, medicinal products, toothpastes, chewing tobaccos and smoking tobaccos.