Millennium Specialty Chemicals, Inc.

Symrise, Inc.

Millenium Specialty Chemicals, Inc.

Renessenz, LLC

Joe W Snow

Mark B Erman

Patrick J Whelan

Gennadiy Kolomeyer

David Sitko

Bernard J Kane

Mikhail Y Lebedev

Melissa J Williams

Gary P Sanders

Mikhail Y Levedev

Physiological cooling compounds of the structure: where Ris p-menthyl or 2,3,4-trimethylpent-3-yl group and R-Rare hydrogen or alkyl groups. The combination of R-Ris such that the N-alkyl group is a branched Calkyl or branched or linear C-Calkyl 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.

Physiological cooling compounds

A method of imparting a physiological cooling effect to a consumer product is disclosed. The method comprises formulating into the consumer product a composition comprising at least one lactoyl ester of menthyl lactate. Also disclosed is a method of providing physiological cooling by contacting skin or mucous membranes with the lactoyl ester compositions. Coolants comprising the lactoyl esters and additional coolants are also disclosed. The lactoyl esters are conveniently prepared from menthol and lactic acid.

Physiological coolants based on lactoyl esters of menthyl lactate

A process for making menthyl glutarate is disclosed. The process comprises reacting excess glutaric acid and menthol to produce a mixture comprising monomenthyl glutarate (MMG) and dimenthyl glutarate (DMG), wherein the weight ratio of glutaric acid to menthol is from 1.0 to 1.6 and the resulting mixture comprises from 60 to 70 wt. % of MMG and from 30 to 40 wt. % of DMG.

Process for making menthyl glutarate

A method for stabilizing menthyl lactate is disclosed. The method comprises combining water with a solution comprising menthyl lactate and a water-miscible organic solvent in amounts effective to precipitate menthyl lactate from the resulting aqueous mixture. The aqueous precipitation method is simple to practice, and it provides menthyl lactate having remarkably improved storage stability.

Method for stabilizing menthyl lactate

Clear aqueous compositions comprising water, a hydrophobic organic compound, and from about 2 to about 50 wt. % of a solubilizer are disclosed. The solubilizer is an alkali metal or alkaline earth metal salt of a monoester of a saturated C-Calcohol and a saturated dicarboxylic acid. The monoester salts are remarkably effective for solubilizing a wide variety of hydrophobic organic compounds in water to provide aqueous compositions that have excellent stability and outstanding clarity. The compositions are valuable for the cosmetic, agrochemical, coatings, pharmaceutical, and flavor & fragrance industries.

Aqueous compositions containing monoester salts

The present invention provides, in one aspect, a physiological cooling composition comprising at least one cyclohexane carboxamide, at least one acyclic carboxamide, and at least one stereoisomer of menthyl lactate. In another aspect, disclosed is a method for producing such composition. In still another aspect, disclosed are various consumer products comprising a physiological cooling composition comprising at least one cyclohexane carboxamide, at least one acyclic carboxamide, and at least one stereoisomer of menthyl lactate.

Physiological cooling compositions

A process for making monomenthyl esters of dicarboxylic acids is disclosed. Menthol reacts with a saturated, cyclic anhydride in the presence of a base catalyst under conditions effective to produce a mixture of mono- and bis-menthyl esters in which the molar ratio of mono- to bis-menthyl esters is enhanced compared with the ratio of esters produced in a similar uncatalyzed process.

Process for making monomenthyl esters

A simple, high-yield process for making menthyl lactate (ML) is disclosed. Menthol and lactic acid react to produce a mixture comprising menthyl lactate and one or more higher lactoyl esters of ML. Hydrolysis of the esterification mixture follows in the presence of aqueous base under conditions effective to convert the higher lactoyl esters to menthyl lactate. Coincidentally, the conditions minimize hydrolysis of menthyl lactate to menthol, thereby maximizing the overall yield of ML.

Menthyl lactate process

Process for obtaining alpha-campholenic aldehyde

A process for obtaining a nitrile represented by formula RCN, comprising contacting a corresponding aldehyde represented by formula RCHO with (i) ammonia or ammonium hydroxide, and (ii) hydrogen peroxide, in the presence of a transition metal or a transition metal compound.

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Jacksonville, FL, United States of America

Joe W Snow