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N-substituted-p-menthane-3-carboxamide and uses thereof

An alkyl and methyl technology, which is applied in the field of N-substituted-p-menthane-3-carboxamide and its uses, can solve the problems of weakening the use of volatility and the like

Inactive Publication Date: 2009-11-18
GIVAUDAN NEDERLAND SERVICES +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although menthol is well established as a physiological cooling agent, its strong minty odor and its relatively high volatility impair its use in some compositions

Method used

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  • N-substituted-p-menthane-3-carboxamide and uses thereof
  • N-substituted-p-menthane-3-carboxamide and uses thereof
  • N-substituted-p-menthane-3-carboxamide and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Example 1: 2-isopropyl-5-methyl-cyclohexanecarboxylic acid (2-hydroxy-2-phenylethyl)- Preparation of amides

[0069] To a solution of 1.5 g of 2-amino-1-phenylethanol in 15 g of dichloromethane was added 2 g of triethylamine at room temperature. To this solution was gradually added 2 g of p-menthane-3-carbonyl chloride at room temperature without cooling or heating. The reaction mixture started to reflux at 35°C during the dropwise addition. Stirring was continued for 1 hour at room temperature. The mixture was diluted with 25 g of ether and washed twice with 50 ml of 5% hydrochloric acid solution. After discarding the aqueous layer, the organic layer was washed twice with saturated sodium bicarbonate solution. The solvent was evaporated to obtain 2 g of 2-isopropyl-5-methyl-cyclohexanecarboxylic acid (2-hydroxy-2-phenylethyl)-amide. using mass spectrometry, 1 H NMR and 13 C NMR confirmed the molecular structure.

Embodiment 2

[0070] Example 2: Preparation of 2-isopropyl-5-methyl-cyclohexanecarboxylic acid phenylethyl-amide

[0071] To a solution of 1.5 g of 2-phenylethylamine in 15 g of p-menthane-3-carbonyl chloride was added 2 g of triethylamine at room temperature. To this solution was gradually added 2 g of menthyl chloride at room temperature without cooling or heating. The reaction mixture started to reflux at 35°C during the dropwise addition. Stirring was continued for 1 hour at room temperature. The mixture was diluted with 25 g of ether and washed twice with 50 ml of 5% hydrochloric acid solution. After discarding the aqueous layer, the organic layer was washed twice with saturated sodium bicarbonate solution. The solvent was evaporated to give a very viscous residue. The product crystallized after cooling to 0°C. Some pentane was added and the product was filtered. The product was washed once with pentane and dried in a vacuum oven at 60° C. / 10 mbar. Yield: 1 g of 95% pure 2-iso...

Embodiment 3

[0072] Embodiment 3: the comparative sensory evaluation of embodiment 1 product

[0073] Prepare four aqueous solutions:

[0074] The menthol of A.20ppm;

[0075] Gained product is dissolved in the solution A in the embodiment 1 of B.2ppm;

[0076] C. 20 ppm of WS-3 was dissolved in solution A; and

[0077] D. 2ppm of WS-3 was dissolved in Solution A.

[0078] These solutions were tasted and evaluated by a panel of perfumers. Another generally consistent result, as follows: Solution A was described as: "Cooling"; Solution B was described as: "Initial cooling with a high burst", "Long-lasting cooling", "Cool feeling throughout the mouth sensation", "some heat sensation"; solution C was described as: "more neutral cooling sensation than B", "not as intense as B's cooling effect", "not as long lasting as B's cooling effect"; solution D was described as : "more neutral cold feeling than B", "not as strong as B's cooling effect", "not as long-lasting as B's cooling effect"; ...

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Abstract

The present invention relates to substances and compositions having a physiological cooling effect on the skin and the mucosa of the body, especially of the oral cavity, throat and nose. More in particular, the present invention relates to N- substituted-p-menthane-3-carboxamides represented by the following formula (I): and esters thereof. These substances are capable of imparting and / or enhancing a physiological cooling effect in a product in which they are incorporated, much more effectively than the heretofore known N-substituted-p-menthane-3-carboxamides.

Description

field of invention [0001] The present invention relates to substances and compositions having a physiological cooling effect on the skin and mucous membranes of the body, especially the mucous membranes of the mouth, throat and nose. More specifically, the present invention relates to N-substituted-p-menthane-3-carboxamides and in particular to flavor and / or fragrance compositions comprising this substance for imparting or Use to enhance the physiological cooling effect, and consumer products containing such substances. Background of the invention [0002] In flavors and fragrances used in consumer products such as food, beverages, tobacco products and personal care products, for physiological cooling activity on the nervous system of the body, especially on the skin and oral mucosa, i.e. similar to that obtained with menthol Compounds have always been of great interest. [0003] This compound may be added to ingestible formulations, tobacco products, and / or products appli...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A23L1/226C07C233/00A61Q11/00A24B15/30A23L27/20
CPCA24B15/301A61Q11/00C07C2101/02A23L1/22657A61Q5/02A61K8/42C07C233/60A61K2800/244A61Q19/00A61Q15/00C07C2101/14A23L1/226C07C233/58A23G4/06A23L27/20A23L27/204C07C2601/02C07C2601/14A61P25/00
Inventor S·富勒S·通德尔C·温克尔H·雷内斯
Owner GIVAUDAN NEDERLAND SERVICES
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