Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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: 2007-12-26
YUNNAN REASCEND TOBACCO TECH GRP
View PDF0 Cites 0 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

This invention relates to a method for synthesizing alpha-ketoenamine derivative cool flavoring (5-MPC). The method comprises: mixing methyl cyclopentenolone and pyrrolidine at a weight ratio of 1:(1.2-1.4), adding catalyst p-toluene sulphonic acid 0.2-0.3 wt.% of reactants, refluxing in solvent, cooling to room temperature, washing the reaction solution with saturated NaCl solution, separating the organic layer, drying with anhydrous Na2SO4, evaporating the solvent to obtain brown oil-like liquid crude product, and vacuum-distilling to obtain yellowish oil-like liquid 5-methyl-2-(1-pyrrolidinyl)-2-cyclopentene-1-one (5-MPC). The cool flavoring 5-MPC can be added into cut tobacco, toothpaste and gum at a certain amount, and has such advantages as uniform cooling effect, long effectiveness 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com