Menthol derivative and cooling agent composition comprising the same

A technology of menthol derivatives and compositions, applied in the fields of beverages or foods, bathing agents or medicines, cosmetics, cosmetic products, and sensory stimulant compositions, which can solve the problem of insufficient and unsatisfactory retention of cooling effects, etc. question

Active Publication Date: 2007-04-18
上海高砂·鉴臣香料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The above-mentioned traditionally recommended cooling agents have a certain degree of cool

Method used

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  • Menthol derivative and cooling agent composition comprising the same
  • Menthol derivative and cooling agent composition comprising the same
  • Menthol derivative and cooling agent composition comprising the same

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example

[0065] Product Synthesis Examples and Examples were measured with the following equipment.

[0066] NMR spectroscopy:

[0067] 1 H-NMR: AM-400 (400 MHz), produced by BRUKER Inc.

[0068] External standard: tetramethylsilane

[0069] Gas Chromatography (GC):

[0070] HP 6890, produced by HEWLETT PACKARD Inc.

[0071] Chromatographic column: NEUTRABOND-1, produced by GL Science Inc. (inner diameter×height=0.25mm×30m).

[0072] Mass spectrometry (MS):

[0073] M-80 mass spectrometer, manufactured by Hitachi Ltd. (ionization voltage 20 eV).

Embodiment 1

[0075] [Synthesis of 2-(2-1-menthoxyethyl)ethanol]

[0076] (1) Synthesis of 1-menthoxyethanol

[0077]

[0078] First, add 100.0g (0.64mol) of 1-menthol and 42.7g (0.32mol) of anhydrous aluminum chloride into the reactor, replace with nitrogen, then add 500ml of toluene and stir the mixture. The mixture was brought to 5°C. And when the temperature of the solution was kept at 5-10° C., 57 g of ethylene oxide was further added. After the addition was complete, the mixture was stirred at room temperature for an additional 1 hour to complete the reaction. Next, the reaction solution was cooled again, and washed with 150 ml of a 10% aqueous hydrochloric acid solution while maintaining the temperature at 20°C or lower. The reaction solution was washed with 50 ml of saturated aqueous sodium bicarbonate solution, then with 100 ml of saturated brine, and the water was removed with sodium sulfate, and the solvent was recovered under reduced pressure to obtain 123.1 g of crude 1-m...

Embodiment 2

[0088] [Preparation of 2-(2-1-menthoxyethyl)ethanol with NaH]

[0089] The 100ml capacity four-necked flask of Dimroth condenser and thermometer is installed, the 1-menthol of 78.0g (0.5mol) and the NaH (60%) of 20g (0.5mol) are housed, after replacing with nitrogen, add 160ml toluene. The mixture was heated to reflux and stirred for 2 hours. The reaction solution, from which no hydrogen evolution was observed, was cooled to 60° C., at which temperature 44 g (1.0 mol) of ethylene oxide was added within 1 hour. After reflux and stirring for 2 hours, the reaction solution was cooled again and washed with 100 ml of 1% aqueous hydrochloric acid while maintaining the temperature at 10°C or lower. Then, the reaction solution was washed with 50 ml of saturated aqueous sodium bicarbonate, then with 100 ml of saturated brine, water was removed with sodium sulfate, and the solvent was recovered under reduced pressure, then distilled, separated, and reclaimed unreacted 1-menthol and 2-...

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PUM

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Abstract

The invention relates to innovative menthol derivatives which are represented by the general formula (I) below and are excellent in a cooling effect and cool retaining effect, cooling agent compositions comprising the menthol derivatives, and sensory stimulation agent compositions containing the cooling agent compositions, as well as fragrance compositions, beverage or food products, cosmetic products, toiletry products, bathing agents, and pharmaceutical products containing the cooling agent compositions or sensory stimulation agent compositions. (general formula (I)) wherein R<1> represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an acyl group having 1 to 5 carbon atoms; R<2> and R<3> independently represent an alkylene group having 2 to 5 carbon atoms and optionally having a substituent; double dotted line represents a single bond or a double bond; and n is an integer of 1 to 3.

Description

technical field [0001] The present invention relates to a novel menthol derivative and a cooling agent composition containing the menthol derivative. Further, the present invention relates to a sensory stimulating agent composition containing a cooling agent composition and a fragrance composition, a cooling agent composition containing Beverages or foods, cosmetic products, toilet products, bath preparations or pharmaceuticals, or sensory stimulant compositions. Background technique [0002] Traditionally, the skin, mouth, nasal cavity and throat have a cool feeling (cool and refreshing feeling) and a cool feeling (cold and refreshing feeling), that is: cooling agents have been used in toothpaste, candy (such as chewing gum, candy, etc.), tobacco, creams and cosmetics. As a fragrance that imparts sensations such as cool and refreshing, or cold and refreshing: 1-menthol (L-menthol) has been widely used. However, 1-menthol also has disadvantages such as insufficient cooling...

Claims

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Application Information

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IPC IPC(8): A61K8/33A61Q13/00A61Q19/00A61Q11/00C07C43/196C07C43/184A23L27/00A23L27/20A61K8/00A61K8/39A61Q5/02A61Q19/10C07C43/18C07C43/188C09K3/00
CPCA61K8/39A61K2800/244A61Q5/02A61Q11/00A61Q13/00A61Q19/00A61Q19/10C07C43/196C07C2101/14C07C2601/14A61K8/34
Inventor 石田贤哉相田高松田洋幸谷中史弘
Owner 上海高砂·鉴臣香料有限公司
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