Menthyl half acid ester derivatives, processes for preparing same, and uses thereof for their cooling/refreshing effect in consumable materials
AssigneeInternational Flavors & Fragrances Inc.
InventorsMark L. Dewis, Michelle E. Huber, Michael V. Cossette
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Abstract
Described is a genus of menthyl half acid ester derivatives having the structure: and processes for producing same, wherein n is an integer of from 1 to 5; wherein X is either —OR″ or —NRR′; wherein R″ is hydrogen, C1-C5 lower alkyl or C3-C6 lower alkenyl; wherein R is hydrogen, C1-C5 lower alkyl, 2-hydroxyethyl or cyclopropyl and wherein R′ is hydrogen, methyl or ethyl; with the proviso that when X is —OR″, n is an integer of from 3 to 5, having utility for augmenting, enhancing or imparting a taste or cooling effect or refreshing effect in or to an ingestible or topical composition.
Claims38
A process for augmenting, enhancing or imparting a taste or cooling effect or refreshing effect to a consumable material selected from the group consisting of a foodstuff, a beverage, a chewing gum, an oral care product, a nasal care product, a cologne, a skin care product, a hair care product, a topical cosmetic product and a medicinal product comprising the step of adding to said consumable material a taste- or cooling effect- or refreshing effect-augmenting, enhancing or imparting quantity and concentration of at least one menthyl half acid ester derivative having the structure:
- wherein n is an integer of from 1 to 5;
- wherein X is selected from the group consisting of —OR″ and —NRR′;
- wherein R″ is hydrogen, C1-C5 lower alkyl or C3-C6 lower alkenyl;
- wherein R is hydrogen, C1-C5 lower alkyl, 2-hydroxyethyl or cyclopropyl and wherein R′ is hydrogen, methyl or ethyl;
- with the proviso that when X is —OR″, n is an integer of from 3 to 5.
A process for producing a menthyl half acid ester derivative having the structure:
- comprising the steps of admixing a compound having the structure:
- with an inert solvent to form a solution;
- then admixing the resulting solution with an aliphatic or aromatic tertiary amine base at a temperature in the range of from about 0° C. to about 30° C.;
- then admixing the resulting product with an oxalyl dihalide while maintaining the reaction temperature in the range of from about 5° C. to about 30° C. thereby forming an intermediate;
- then admixing the resulting intermediate with an amine having the formula RR′NH at a temperature in the range of from about 0° C. to about 30° C.;
- and then isolating the compound having the structure:
- from the resulting product wherein n is an integer of from 1 to 5;
- wherein R is hydrogen, C1-C5 lower alkyl, 2-hydroxyethyl or cyclopropyl and wherein R′ is hydrogen, methyl or ethyl.
A process for producing a menthyl half acid ester derivative having the structure:
- comprising the steps of admixing a compound having the structure:
- with an inert solvent to form a solution;
- admixing the resulting solution with a lower alkyl haloformate at a temperature in the range of from about 0° C. up to about 30° C. whereby an intermediate is formed;
- then cooling the resulting intermediate-containing product to a temperature in the range of from about −30° C. to about +5° C.;
- then admixing the resulting intermediate-containing product with an aliphatic or aromatic tertiary amine while maintaining the temperature of the mixture at from about −15° C. to about +5° C.;
- filtering the resulting mixture;
- cooling the filtrate to a temperature in the range of from about −15° C. to about +5° C.;
- admixing the resulting product with an amine having the formula RR′NH at a temperature in the range of from about 0° C. to about 30° C.;
- and then isolating the compound having the structure:
- from the resulting reaction product, wherein n is an integer of from 1 up to 5;
- wherein R is hydrogen, C1-C5 lower alkyl, 2-hydroxyethyl or cyclopropyl and wherein R′ is hydrogen, methyl or ethyl.
A process for producing a menthyl half acid ester derivative having the structure:
- comprising the steps of admixing a compound having the structure:
- with an inert solvent to form a solution;
- then admixing the resulting solution with an aliphatic or aromatic tertiary amine base at a temperature in the range of from about 0° C. to about 30° C.;
- then admixing the resulting product with an oxalyl dihalide, maintaining the reaction temperature in the range of from about 5° C. up to about 30° C. thereby forming an intermediate;
- then admixing the resulting intermediate with an amine having the formula RR′NH at a temperature in the range of from about 0° C. to about 30° C.;
- and then isolating the compound having the structure:
- from the resulting reaction product wherein n is an integer of from 1 to 5;
- wherein R is hydrogen, C1-C5 lower alkyl, 2-hydroxyethyl or cyclopropyl and wherein R′ is hydrogen, methyl or ethyl.
A process for producing a menthyl half acid ester having the structure:
- comprising the steps of admixing a compound having the structure:
- with an inert solvent to form a solution;
- admixing the resulting solution with a lower alkyl haloformate at a temperature in the range of from about 0° C. to about 30° C. whereby an intermediate is formed;
- then cooling the resulting intermediate-containing product to a temperature in the range of from about −30° C. to about +5° C.;
- then admixing the resulting intermediate-containing product with an aliphatic or aromatic tertiary amine while maintaining the temperature of the mixture at from about −15° C. to about +5° C.;
- filtering the resulting mixture;
- cooling the filtrate to a temperature in the range of from about −15° C. to about +5° C.;
- admixing the resulting product with an amine having the formula RR′NH at a temperature in the range of from about 0° C. to about 30° C.;
- and then isolating the compound having the structure:
- from the resulting reaction product, wherein n is an integer of from 1 to 5;
- wherein R is hydrogen, C1-C5 lower alkyl, 2-hydroxyethyl or cyclopropyl and wherein R′ is hydrogen, methyl or ethyl.
A menthyl half acid ester derivative having the structure:
- wherein n is an integer of from 1 to 5;
- wherein R is hydrogen, C1-C5 lower alkyl, 2-hydroxyethyl or cyclopropyl and wherein R′ is hydrogen, methyl or ethyl.
Dependencies are inferred from the claim text.