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Derivative of new type menthol, preparation method and application

A menthol derivative and menthol technology are applied in the direction of cyanide reaction preparation, organic compound preparation, chemical instruments and methods, etc., which can solve the problems of cumbersome operation and increased cost of synthesis reaction, so as to enhance drug efficacy and promote economic development. The effect of skin absorption

Inactive Publication Date: 2007-02-21
SHANTOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage is that the cost of the synthesis reaction increases and the operation is cumbersome.

Method used

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  • Derivative of new type menthol, preparation method and application
  • Derivative of new type menthol, preparation method and application
  • Derivative of new type menthol, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: Invention of the compound and its synthesis, taking N,N-dimethylglycine menthyl ester as an example.

[0035] (1) Synthesis of Menthyl Chloroacetate

[0036] In a 50 mL three-neck flask, place 4.69 g of menthol, and add 2.6 mL of chloroacetyl chloride dropwise while stirring at room temperature, and continue stirring at room temperature for 2 h after the dripping is completed. The reaction solution was saturated NaHCO 3 The solution was adjusted to weak alkalinity, the organic layer was separated, the aqueous layer was extracted with ether or ethyl acetate, the combined organic layers were washed with saturated brine, and anhydrous Na 2 SO 4 Dry overnight, evaporate the solvent, and perform column chromatography (silica gel: 100-300 mesh), using chloroform as the eluent, and evaporate the eluent to obtain 5.81 g of a colorless liquid with a yield of 83.2%. The infrared spectrum data of product are as follows:

[0037] IR (KBr) v: 2957, 2871, 1758, 1736...

Embodiment 2

[0041] Embodiment 2: Invention of the compound and its synthesis, taking N,N-diethylglycine menthyl ester as an example.

[0042] (1) Synthesis of Menthyl Chloroacetate

[0043] In a 50mL three-necked flask, add 1.56g menthol, 1.04g chloroacetic acid and 25mL cyclohexane respectively, and add catalyst 0.15g SnCl 2 Solid, reflux 2h, filter, and the filtrate is saturated with Na 2 CO 3 The solution was adjusted to be weakly alkaline, the organic layer was separated, the aqueous layer was extracted with ether, the combined organic layers were washed with saturated brine, and anhydrous Na 2 SO 4 Dry overnight, evaporate the solvent, use chloroform as the eluent, perform column chromatography (silica gel: 100-300 mesh), evaporate the eluent, and obtain 2.06 g of a colorless liquid with a yield of 88.9%.

[0044] (2) Synthesis of N, N-diethylglycine menthyl ester

[0045] Add 7.8 mL of diethylamine to 6.98 g of menthol chloroacetate, stir the reaction at room temperature for 2 ...

Embodiment 3

[0047] Embodiment 3: Invention of the compound and its synthesis, taking N,N-dimethylglycine menthyl ester as an example.

[0048] In a 50mL three-necked flask, add 6.98g menthol, 3.71g N,N-dimethylglycine and 25mL cyclohexane respectively, and add 0.51g SnCl 2 Solid, refluxed for 2.5h, filtered, and the filtrate was washed with saturated Na 2 CO 3 The solution was adjusted to be weakly alkaline, the organic layer was separated, the aqueous layer was extracted with ether, the combined organic layers were washed with saturated brine, and anhydrous Na 2 SO 4 Dry overnight, evaporate the solvent, use chloroform as the eluent, perform column chromatography (silica gel: 100-300 mesh), evaporate the eluent, and obtain 9.37 g of a colorless liquid with a yield of 86.9%.

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Abstract

This invention relates to methods for preparing new menthol derivatives, i.e., N, N-dimethyl menthol glycinate, N, N-diethyl menthol glycinate and N, N-dihydroxyethyl menthol glycinate. This invention comprises three different methods for synthesizing menthol derivatives. Method 1 comprises: reacting chloroacetyl chloride and menthol at room temperature for 1-3 h, and reacting with amine at room temperature for 1-3 h to obtain the target products. Method 2 comprises: refluxing chloroacetic acid and menthol in cyclohexane in the presence of a Lewis acid catalyst for 1-3 h, and reacting with amine at room temperature for 1-3 h to obtain the target products. Method 3 comprises: refluxing N,N-disubstituted glycine and menthol in cyclohexane in the presence of a Lewis acid catalyst for 1-3 h to obtain the target products. The new menthol derivatives can be used as transdermal agents.

Description

technical field [0001] The present invention relates to 3 kinds of new menthol derivatives: N, N-dimethylglycine menthol ester, N, N-diethylglycine menthol ester and N, N-dihydroxyethylglycine menthol ester, which Preparation method and application as transdermal agent in the preparation of pharmaceuticals or cosmetics. Background technique [0002] N, N-disubstituted glycine esters are a new class of biodegradable transdermal agents. Experimental studies show that: N, N-dimethylglycine decyl ester and N, N-dimethylglycine-(E)-3,7-dimethyl-2,6-octadienyl ester promote the percutaneous absorption of drug indomethacin The drug effect is several times of Azone (1-n-dodecylazacycloheptanone-2) (1. Li Weijie, Xu Zunle, Wang Bo, Journal of Sun Yat-Sen University (Natural Science Edition), 2003, 42 (6), 44-46, 50; 2. Li Weijie, Xu Zunle, Chemical Research and Application, 2005, 17(6), 762-765). Such compounds can be applied to creams, ointments and liniments in medicines and cos...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/08C07C229/12A61K47/16A61K8/44
Inventor 李伟杰王子元肖叶玉许遵乐陆豫
Owner SHANTOU UNIV
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