Comestible compositions comprising high potency savory flavorants, and processes for producing them
AssigneeSenomyx, Inc.
InventorsRhondi Shigemura, Qing Chen, Vincent Darmohusodo, Aaron R. Dean
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Abstract
The present invention relates to the use of certain high potency savory (“umami”) taste modifiers, as savory flavoring agents and/or enhancers of monosodium glutamate, for the preparation of foods, beverages, and other comestible compositions, and to processes for preparing food flavorant compositions for use in the preparation of comestible food and drink.
Claims29
A process of preparing N1-(2-methoxy-4-methylbenzyl)-N2-(2-(5-methylpyridin-2-yl)ethyl)oxalamide, comprising:
- a) reacting 2-methoxy-4-methylbenzylamine with 2-chloro-oxoacetate, to provide N-(2-methoxy-4-methyl-benzyl)-oxalamic acid ethyl ester;
- and
- b) reacting N-(2-methoxy-4-methyl-benzyl)-oxalamic acid ethyl ester with 245-methylpyridin-2-yl)ethamine, to provide N1-(2-methoxy-4-methylbenzyl)-N2-(5-methylpyridin-2-yl)ethyl)oxalamide.
A process for preparing N-(2,4-dimethoxybenzyl)-N′-[2-(pyridin-2-yl)ethyl]oxalamide having the formula:
- comprising the steps of:
- a) condensing 2,4-dimethoxybenzylamine or a salt thereof with a 2-chloro-2-oxoacetate ester having the formula:
- in the presence of a tertiary amine base and a solvent or solvent mixture comprising one or more of toluene, o-xylene, m-xylene, p-xylene, nitrobenzene, to form a solution of a 2-(2,4-dimethoxybenzylamino)-2-oxoacetate ester having the formula:
- wherein R is C1-C4 linear or branched alkyl;
- and
- b) reacting the solution of the 2-(2,4-dimethoxybenzylamino)-2-oxoacetate ester formed in step (a) with 2-(pyridin-2-yl)ethylamine having the formula:
- to form N-(2,4-dimethoxybenzyl)-N′-[2-(pyridin-2-yl]ethyl]oxalamide.
A process for preparing N-(2,4-dimethoxybenzyl)-N′-[2-(pyridin-2-yl)ethyl]oxalamide having the formula:
- comprising:
- a) dissolving 2,4-dimethoxybenzylamine or an ammonium salt thereof having the formula:
- in triethylamine and toluene to form an admixture;
- b) adding ethyl 2-chloro-2-oxoacetate having the formula:
- to said admixture formed in step (a) at a temperature at or below about 10° C., to form a solution of ethyl 2-(2,4-dimethoxybenzylamino)-2-oxoacetate having the formula:
- c) reacting said solution of ethyl 2-(2,4-dimethoxybenzylamino)-2-oxoacetate formed in step (b) with 2-(pyridin-2-yl)ethylamine having the formula:
- to form a reaction solution and subsequently heating the reaction solution to form N-(2,4-dimethoxybenzyl)-N′[2-(pyridin-2-yl)ethyl]oxalamide.
A process for preparing 2-H-benzo[3,4-d]1,3-dioxolan-5-yl-N-(propylbutyl)-carboxamide having the formula:
- comprising:
- a) reacting piperonylic acid having the formula:
- with a reagent capable of forming an acid chloride comprising thionyl chloride, oxalyl chloride, phosphorous oxychloride, or a mixture thereof to form piperonoyl chloride having the formula:
- b) reacting the piperonoyl chloride formed in step (a) with 4-heptylamine having the formula:
- to form 2-H-benzo[3,4-d]1,3-dioxolan-5-yl-N-(propylbutyl)-carboxamide.
Dependencies are inferred from the claim text.