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.

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.

Abstract: In one embodiment of the invention, a rope tender is rotatably affixed to the center pull on the tower to carry the rope over wakeboard racks. The rope tender is clamped to the center pull on the tower by a clamp. The rope is then pulled through an end loop on the rope tender and attached to the center pull on the tower. In one embodiment, the rope tender is looped one or more times in the middle to achieve a flexible, spring effect for the rope tender. The rope may also be pulled through the middle loop for support.

Abstract: A process for interconversion between WS-1 and neo-WS-1 by heating to a temperature in a range of from 60 degrees Celsius to 250 degrees Celsius. The heating can be done in the presence of an acid catalyst. Starting from practically pure (=98%) WS-1, or mixtures of WS-1 and neo-WS-1, practically pure (=98%) neo-WS-1 can be obtained. Starting from practically pure (=98%) neo-WS-1, or mixtures of WS-1 and neo-WS-1, practically pure (=98%) WS-1 can be obtained.

Abstract: A process for making neo-enriched p-menthane intermediates is disclosed. Lewis acid-catalyzed rearrangement of an oxaspiro compound provides an aldehyde mixture comprising normal (II) and neo (III) p-menthane-3-aldehydes: with the neo aldehyde (III) as the major product. The aldehyde mixture is readily oxidized to provide the corresponding carboxylic acids, and the acids are easily converted to a host of neo-enriched p-menthane esters or amides. The esters and amides are valuable as physiological coolants.

Abstract: 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.

Abstract: 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.

Abstract: In one embodiment of the invention, a rope tender is rotatably affixed to the center pull on the tower to carry the rope over wakeboard racks. The rope tender is clamped to the center pull on the tower by a clamp. The rope is then pulled through an end loop on the rope tender and attached to the center pull on the tower. In one embodiment, the rope tender is looped one or more times in the middle to achieve a flexible, spring effect for the rope tender. The rope may also be pulled through the middle loop for support.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: 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 C6-C20 alcohol 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.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: 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 C6-C20 alcohol 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.

Abstract: 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.

Abstract: 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.