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Method for synthesizing cool flavour agent (5-MPC) of derivative of alpha ketone enamine, and application

The technology of a ketoenamine and a synthesis method, which is applied in the field of daily chemical products, can solve the problems of short duration of cooling sensation and strong eye irritation, and achieve the effects of obvious comfort, uniform cooling taste and long duration.

Inactive Publication Date: 2009-10-21
YUNNAN REASCEND TOBACCO TECH GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Traditionally, (-) menthol is used as a cooling agent, but menthol has a higher volatility, and the duration of the cool feeling is shorter, and it is more irritating to human eyes

Method used

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  • Method for synthesizing cool flavour agent (5-MPC) of derivative of alpha ketone enamine, and application
  • Method for synthesizing cool flavour agent (5-MPC) of derivative of alpha ketone enamine, and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Get methylcyclopentenolone (MCP) 33.6g, tetrahydropyrrolidine 40.3g, p-toluenesulfonic acid 0.15g, benzene 370g (5 times of reaction mass), methylcyclopentenolone and tetrahydropyrrole mixed with alkanes, added catalyst p-toluenesulfonic acid, rapidly heated to reflux state, and refluxed for 5 hours. 2 SO 4 Drying, evaporate the solvent under reduced pressure with a rotary evaporator to obtain the crude product 5-MPC of brown-yellow oily liquid. The crude product is subjected to vacuum distillation, and the collected temperature is a cut at 106 ° C / 6-8 mbar to obtain a light yellow oily liquid. 5-MPC products.

[0019] The product was characterized by infrared spectrum, mass spectrum and nuclear magnetic resonance spectrum:

[0020] 5-MPC is a light yellow oily liquid.

[0021] IR,v max (cm -1 ): 3060.7, 2966.3, 2927.3, 2870.4, 2854.0 (-CH 2 -, -CH 3 ), 1702.2 (C=O), 1612.3 (C=C), 1487.2, 1458.9, 1387.8, 1351.7, 1332.1, 1317.3 (-CH 2 -, -CH 3 )

[0022] MS (EI...

Embodiment 2

[0028] Get methylcyclopentenolone (MCP) 33.6g, tetrahydropyrrolidine 43.7g, p-toluenesulfonic acid 0.2g, benzene 370g (5 times of reaction mass), methylcyclopentenolone and tetrahydropyrrole mixed with alkanes, added the catalyst p-toluenesulfonic acid, rapidly heated to the reflux state, the reflux time was 6 hours, cooled to room temperature after the reaction was completed, the reaction solution was washed with saturated brine, the organic layer was separated, and then washed with anhydrous Na 2 SO 4 Drying, evaporate the solvent under reduced pressure with a rotary evaporator to obtain the crude product 5-MPC of brown-yellow oily liquid. The crude product is subjected to vacuum distillation, and the collected temperature is a cut at 106 ° C / 6-8 mbar to obtain a light yellow oily liquid. 5-MPC products. The product is characterized by infrared spectrum, mass spectrum and nuclear magnetic resonance spectrum, which is the same as that of Example 1 and will not be repeated he...

Embodiment 3

[0030] Get methylcyclopentenolone (MCP) 33.6g, tetrahydropyrrolidine 47.0g, p-toluenesulfonic acid 0.24g, benzene 404g (5 times of reaction mass), methylcyclopentenolone and tetrahydropyrrole mixed with alkanes, added catalyst p-toluenesulfonic acid, rapidly heated to reflux state, reflux time was 7 hours, cooled to room temperature after the reaction was completed, the reaction solution was washed with saturated brine, the organic layer was separated, and then washed with anhydrous Na 2 SO 4 Drying, evaporate the solvent under reduced pressure with a rotary evaporator to obtain the crude product 5-MPC of brown-yellow oily liquid. The crude product is subjected to vacuum distillation, and the collected temperature is a cut at 106 ° C / 6-8 mbar to obtain a light yellow oily liquid. 5-MPC products. The product is characterized by infrared spectrum, mass spectrum and nuclear magnetic resonance spectrum, which is the same as that of Example 1 and will not be repeated here.

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Abstract

The invention relates to a method for synthesizing a cooling agent (5-MPC) of α-ketoenamine derivatives. It is characterized in that methylcyclopentenolone and tetrahydropyrrolidine are used as raw materials, mixed according to a mass ratio of 1:1.2 to 1.4, and a catalyst p-toluenesulfonic acid of 0.2-0.3% of the total amount of reaction materials is added, and the solvent is refluxed. After cooling to room temperature, the reaction solution was washed with saturated brine, and the organic layer was separated, then dried with anhydrous Na2SO4, and the solvent was evaporated to obtain a crude product of a brownish-yellow oily liquid, which was distilled under reduced pressure to obtain a pale yellow oily Liquid: 5-methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one product (5-MPC). The non-menthol cooling agent 5-MPC synthesized by the invention is respectively applied in shredded cigarette tobacco, toothpaste and chewing gum at a certain concentration, and has the effects of uniform cool taste, long duration and obvious comfort.

Description

technical field [0001] The present invention relates to the technical field of daily chemical products, in particular to α-ketoenamine derivatives [5-methyl-2-(1-pyrrolidinyl)-2-cyclopentenen-1-one (abbreviated as 5 -MPC)] the synthetic method of cooling agent and its application. Background technique [0002] Cooling agent is an important class of organic raw materials in the fields of food industry, daily chemical industry, tobacco industry and pharmaceutical industry, and has become an indispensable additive in people's daily life, especially in chewing gum, cigarettes, food and skin care products. It is inseparable from the cooling agent. And, from the food industry, cosmetics industry and pharmaceutical industry at home and abroad at present, the market is increasing year by year to the demand of cooling agent. [0003] Traditionally, (-) menthol is used as a cooling agent, but the volatility of menthol is higher, the duration of cool feeling is shorter, and it is mor...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/08A24B15/38
Inventor 陈永宽成会玲倪军杨伟祖古昆谢冰
Owner YUNNAN REASCEND TOBACCO TECH GRP
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