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

Preparation method of cigarette precursor-aroma phenylpropionic ester and application thereof

A technology of phenylpropionate and phenylpropionate, which is applied in the field of preparation of phenylpropionate esters of latent aroma monomers for cigarettes, can solve the problems of short fragrance retention time and poor high temperature thermal stability, and achieve simplified post-treatment process, The effect of reducing irritation and miscellaneous gas, improving the roundness and comfort of smoke

Inactive Publication Date: 2017-05-10
HUBEI CHINA TOBACCO IND
View PDF2 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Many excellent spices have limited their wide application due to their poor high temperature thermal stability, strong volatility, and short fragrance retention time.

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
  • Preparation method of cigarette precursor-aroma phenylpropionic ester and application thereof
  • Preparation method of cigarette precursor-aroma phenylpropionic ester and application thereof
  • Preparation method of cigarette precursor-aroma phenylpropionic ester and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The preparation method of geraniyl phenylpropionate, a monomer of flavoring substance for tobacco:

[0026] Take 10mmol of geraniol and 10mmol of phenylpropionic acid dissolved in 100ml of dry dichloromethane, after stirring for 10min, add 4-dimethylaminopyridine (DMAP) (5mmol) and 1-ethyl-(3-dimethylaminopropyl base) carbodiimide hydrochloride (EDCHCl) (11 mmol), stirred at room temperature, TLC monitoring reaction (petroleum ether: ethyl acetate = 10:1, Rf = 0.5, ultraviolet 254nm color development), tracking the reaction end point. Add 50mL of water to the organic phase to wash, separate the liquids, then wash with 50mL saturated sodium chloride solution, separate the liquids, and wash the organic phase with anhydrous NaCl 2 SO 4 Dry and concentrate to give crude product. Dissolve the crude product in 50 mL of dichloromethane, add 4 g of 100-200 mesh silica gel, spin dry the sample under reduced pressure, and use 80 g of 100-200 mesh silica gel chromatography to sl...

Embodiment 2

[0028] The preparation method of geraniyl phenylpropionate, a monomer of flavoring substance for tobacco:

[0029] Take 10mmol of geraniol and 1.05mmol of phenylpropionic acid dissolved in 100ml of dry dichloromethane, after stirring for 10min, add 4-dimethylaminopyridine (DMAP) (4mmol) and 1-ethyl-(3-dimethylamino Propyl)carbodiimide hydrochloride (EDCHCl) (11mmol), stirred at room temperature, TLC monitoring reaction (petroleum ether: ethyl acetate = 10:1, Rf = 0.5, UV 254nm color development), tracking the reaction end point. Add 50mL of water to the organic phase to wash, separate the liquids, then wash with 50mL saturated sodium chloride solution, separate the liquids, and wash the organic phase with anhydrous NaCl 2 SO 4 Dry and concentrate to give crude product. Dissolve the crude product in 50 mL of dichloromethane, add 4 g of 100-200 mesh silica gel, spin dry the sample under reduced pressure, and use 80 g of 100-200 mesh silica gel chromatography to slowly elute wi...

Embodiment 3

[0031] The preparation method of the monomer phenylpropionate-beta-ionyl ester of tobacco fragrance:

[0032] In a three-necked flask, add weighed 20mmol β-ionol and 10mmol phenylpropionic acid dissolved in 200ml dry dichloromethane, after stirring for 10min, add 4-dimethylaminopyridine (DMAP) (10mmol) and 1-ethyl- (3-Dimethylaminopropyl) carbodiimide hydrochloride (EDC·HCl) (22mmol), stirring at room temperature, TLC monitoring reaction (petroleum ether: ethyl acetate=10:1, Rf=0.5, Ultraviolet 254nm color development), tracking the reaction to the end point. Add 100mL of pure water to the organic phase to wash, separate the liquid, then wash with 100mL saturated sodium chloride solution, separate the liquid, and wash the organic phase with anhydrous NaCl 2 SO 4 Dry and concentrate the crude product. The crude product was dissolved in 10 mL of dichloromethane, 7 g of 100-200 mesh silica gel was added, the sample was spin-dried under reduced pressure, and the sample was sepa...

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

The invention discloses a preparation method of cigarette precursor-aroma phenylpropionic ester. The preparation method includes steps of dissolving phenylpropionic acid and monohydric alcohol in dried methylene dichloride; stirring for 10-30 minutes, and adding 4-dimethylamino pyridine and 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride; stirring for 4-12h under room temperature; monitoring reaction by TLC and tracking the reaction end point; adding water in an organic phase and washing; separating liquid, and washing the mixture by saturated sodium chloride solution; separating liquid and drying the organic phase by anhydrous Na2SO4; concentrating and acquiring the crude product; performing column chromatography isolation to obtain the cigarette precursor-aroma phenylpropionic ester. In the invention, phenylpropionic geraniol ester, phenylpropionic-beta-ionol ester can significantly improve the addition in cigarette by comparing with geraniol and beta-ionol matrix; the external aroma variety of the cigarette is not influenced; the cigarette precursor-aroma phenylpropionic ester is applied to cigarette as the cigarette fumette, thus the cigarette thrill and offensive odor can be reduced, and the smoke roundness and comfort can be improved.

Description

technical field [0001] The invention relates to the fields of flavors and fragrances and tobacco processing, in particular to a method for preparing tobacco latent aroma monomer phenylpropionate and its application. Background technique [0002] Many excellent spices have limited their wide application due to their poor high-temperature thermal stability, strong volatility, and short fragrance retention time. Latent aroma substances are substances with large relative molecular weight and high boiling point, which have little or no aroma, but can release aroma and aroma substances through chemical hydrolysis, enzymatic hydrolysis, microbial action, pyrolysis, photolysis and other ways. compound. Because of its good safety, it is included in the category of natural spices in the world, and it is very effective to use it to prepare certain flavor food flavors. Unlike volatile and semi-volatile aroma substances, latent aroma compounds will not cause significant changes in the ...

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): C07C67/08C07C69/73A24B15/30A24B3/12
CPCC07C67/08A24B3/12A24B15/301C07C69/73
Inventor 刘华臣齐富友陈义坤刘冰罗诚浩
Owner HUBEI CHINA TOBACCO IND
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