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Preparation method of cigarette precursor-aroma monomer 3-phenylacrylates and application thereof

A technology of phenylacrylic acid and monomer, which is applied in the field of preparation of 3-phenylacrylic acid ester, a latent aroma monomer for cigarettes, can solve the problems of poor thermal stability at high temperature, short fragrance retention time, etc. The effect of simplifying the post-treatment process and improving the reaction yield

Active Publication Date: 2017-03-08
HUBEI CHINA TOBACCO IND
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  • 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

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  • Preparation method of cigarette precursor-aroma monomer 3-phenylacrylates and application thereof
  • Preparation method of cigarette precursor-aroma monomer 3-phenylacrylates and application thereof
  • Preparation method of cigarette precursor-aroma monomer 3-phenylacrylates and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] The preparation method of tobacco fragrance monomer 3-phenylacrylate-β-ionol ester:

[0022] Take 10mmol β-ionol and 10mmol 3-phenylacrylic acid dissolved in 100ml of dry dichloromethane, after stirring for 10min, add 4-dimethylaminopyridine (DMAP) (5mmol) 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 with petroleum ether: ethy...

Embodiment 2

[0024] The preparation method of tobacco fragrance monomer 3-phenylacrylate-β-ionol ester:

[0025] Take 10mmol β-ionol and 10.5mmol 3-phenylacrylic acid dissolved in 100ml dry dichloromethane, after stirring for 10min, add 4-dimethylaminopyridine (DMAP) (4mmol) and 1-ethyl-(3-dimethyl Aminopropyl) carbodiimide hydrochloride (EDCHCl) (11mmol), stirring at room temperature, TLC monitoring reaction (petroleum ether: ethyl acetate = 10:1, Rf = 0.5, UV 254nm color development), tracking the end of the reaction . 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 with petroleum ether: ...

Embodiment 3

[0027] The preparation method of tobacco fragrance monomer 3-phenylacrylate-β-ionol ester:

[0028] Take 10.5mmol β-ionol and 10mmol 3-phenylacrylic acid dissolved in 100ml dry dichloromethane, after stirring for 10min, add 4-dimethylaminopyridine (DMAP) (6mmol) and 1-ethyl-(3-dimethyl Aminopropyl) carbodiimide hydrochloride (EDCHCl) (12mmol), stirring at room temperature, TLC monitoring reaction (petroleum ether: ethyl acetate = 10:1, Rf = 0.5, ultraviolet 254nm color development), tracking the end of the reaction . 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 with petroleu...

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Abstract

The invention relates to a preparation method of cigarette precursor-aroma monomer 3-phenylacrylates. The preparation method comprises the following steps of taking 3-cinnamic acid and beta-ionol into dry methylene dichloride; performing stirring for 10 minutes to 30 minutes; adding 4-dimethylamino pyridine and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride; performing stirring at room temperature for 4 to 12h; monitoring the reaction by TLC; tracking the reaction terminal point; adding water into an organic phase for washing; performing liquid separation; then, performing washing by saturated sodium chloride solution; performing liquid separation; drying the organic phase by absolute Na2SO4; performing concentration to obtain a coarse product; performing column chromatography separation; obtaining 3-cinnamic acid-beta-ionol ester. Compared with beta-ionol precursors, the 3-cinnamic acid-beta-ionol ester prepared by the method has the advantages that the addition in the cigarette can be obviously improved; the exterior aroma varieties of the cigarette cannot be influenced; when the 3-cinnamic acid-beta-ionol ester is applied to the cigarette, the irritation of the cigarette and the miscellaneous gas in the cigarette can be reduced; the smoke gas smoothness and the comfortable performance of the cigarette can be improved.

Description

technical field [0001] The invention relates to the fields of flavors and fragrances and tobacco processing, in particular to a preparation method and application of latent aroma monomer 3-phenylacrylates for tobacco. 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 th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/618A24B3/12A24B15/34
CPCA24B3/12A24B15/34C07C67/08C07C69/618
Inventor 刘华臣陈义坤齐富友柯炜昌刘冰
Owner HUBEI CHINA TOBACCO IND