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US 2016/0355463 A1Published application
Physiological cooling compounds
AssigneeSymrise AG
InventorsGennadiy G. Kolomeyer, David J. Sitko, Joe W. Snow
Life of this patent
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Abstract
Physiological cooling compounds of the structure: where R1 is p-menthyl or 2,3,4-trimethylpent-3-yl group and R2-R8 are hydrogen or alkyl groups. The combination of R2-R8 is such that the N-alkyl group is a branched C5 alkyl or branched or linear C6-C8 alkyl group. The new carboxamides are valuable sensory ingredients which provide long-lasting cooling sensation and freshness in personal care, oral care, cosmetic products, pharmaceutical preparations, confectionary, food and beverages.
Claims24
A compound of the formula:
- wherein R1 is selected from the group consisting of p-menthyl and 2,3,4-trimethylpent-3-yl group, and
- wherein X is an alkylamine moiety, having an alkyl group selected from the group consisting of a branched C5 alkyl, a linear C6-C8 alkyl group, and a branched C6-C8 alkyl group.
A method comprising:
- converting at least one carboxylic acid to at least one chloroanhydride;
- and
- reacting the at least one chloroanhydride with at least one amine to produce at least one compound of the formula:
- wherein R1 is selected from the group consisting of p-menthyl and 2,3,4-trimethylpent-3-yl group, and
- wherein X is an alkylamine moiety having an alkyl group selected from the group consisting of a branched C5 alkyl, a linear C6-C8 alkyl group, and a branched C6-C8 alkyl group.
2 more elements
A product produced by a process comprising:
- converting at least one carboxylic acid selected from the group consisting of p-menthane-3-carboxylic acid, and 2,3-dimethyl-2-(propan-2-yl)butanoic acid, and combinations thereof to at least one chloroanhydride in the presence of one selected from the group consisting of thionyl chloride, phosphorus trichloride, and combinations thereof;
- and
- reacting the at least one chloroanhydride with at least one selected from the group consisting of tertiary-amylamine, isoamylamine, neopentylamine, 1,2-dimethylpropylamine, 2-aminopentane, 2-methylbutylamine, 3-aminopentane, hexylamine, 4-methyl-2-aminopentane, heptylamine, 2-aminoheptane, octylamine, 2-ethylhexylamine, 2-amino-6-methylheptane, and t-octylamine, and combinations thereof.
Dependencies are inferred from the claim text.