Preparation method for N-alkyl-2-methyl-5-formyl-3-pyrrole formate and application of N-alkyl2-methyl-5-formyl-3-pyrrole formate in cigarette flavoring

A technology of pyrrole formate and formyl, which is used in the application of cigarette flavoring, and the field of preparation of N-hydrocarbyl-2-methyl-5-formyl-3-pyrrole formate, which can solve the problem of cigarette product easy Loss of characteristics, volatilization of aroma substances, loss of aroma and other problems, to achieve the effect of plump smoke, comfortable aftertaste, and easy operation

Active Publication Date: 2015-10-07
HENAN AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology involves making certain chemical compounds from aminosulfonan chlorides (AMSC) that are used for smoking flavoring purposes. These Amsonsolutions were made through various methods such as acidification or solvent extraction techniques. By adding these materials into water containing an organic substance like alcohol, they could be converted back into different forms called salts. They also found out how this process was efficient when applied on small amounts at once. Overall, it provides a simplified way to produce specific types of molecules useful in industry related applications.

Problems solved by technology

This patent describes different types of chemical structures called naphthols with specific features like burning sensations, bitterness, taste, etc., which make up about 70% of total smoke produced through combustion processes involving various materials including peptides, amino acids, sugars, carbohydes, alkaloids, alcoholic bases, nicotine, pyridines, quinones, anthraquinone, phenolics, tannins, lignans, coumaranes, chalcone, vanillimidazoles, melamine, guanadione, synthetic rubber, polycyclopentenes, phosphorus containing unsaturated nitrosopyrrolum salts, oxynaphthaulene dimers, α-,β -unsaponutrials, cyclohexane-1 , 3-2H-3C-4N-5O-6S, 2-(methoxymorpholinium)pyran-7Zn(OH), 1 H3-1, 4-dimmers thereof, diketones, lactams, imide ester groups, sulfur atoms, oxygen atom bondings, and other similar structural elements.

Method used

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  • Preparation method for N-alkyl-2-methyl-5-formyl-3-pyrrole formate and application of N-alkyl2-methyl-5-formyl-3-pyrrole formate in cigarette flavoring

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Experimental program
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Effect test

Embodiment 1

[0036] The preparation method of N-isopropyl-2-methyl-5-formyl-3-pyrrole carboxylic acid ethyl ester of the present invention, its detailed steps are as follows:

[0037] a. First, dissolve D-glucosamine hydrochloride (645.2mg, 3mmol) in 15mL of water, add ethyl acetoacetate (468.5mg, 3.6mmol) and NaHCO after completely dissolving 3 (377.9mg, 4.5mmol); heated to 85°C for reflux reaction for 10h, TLC (developing solvent is a mixture of chloroform and methanol, the volume ratio of chloroform and methanol is 10:1) detection during the reaction; after the reaction , standing at 4°C for 24h, after standing, a white substance was precipitated, and then filtered under reduced pressure, and the white solid obtained after suction filtration was recrystallized with acetone to obtain a white solid compound Ia (2-methyl-5- 1'2'3'4'-tetrahydroxybutyl-3-pyrrole carboxylate ethyl ester) (663mg, 81%);

[0038] The mp of compound Ia: 153~154°C; 1 H NMR (D 2 O, 400MHz), δ: 1.21 (t, 3H, J=7.1Hz...

Embodiment 2

[0045] Embodiment 2: basically the same as Embodiment 1, the difference is:

[0046] The difference between the preparation method of N-isobutyl-2-methyl-5-formyl-3-pyrrolecarboxylic acid ethyl ester of the present invention and Example 1 is:

[0047] In step c: the compound II (0.2716g, 1.5mmol) obtained in step b was placed in a reaction vessel, and bromoisobutane (0.2466g, 1.80mmol), phase transfer catalyst tetrabutylammonium bromide (0.0223 g, 0.07mmol), solvent acetonitrile 7mL and anhydrous potassium carbonate (0.621g, 4.5mmol), heated up to 65°C in an oil bath for 8h, and carried out TLC during the reaction (the developing solvent was petroleum ether and ethyl acetate) The mixture, when petroleum ether and ethyl acetate are mixed, the volume ratio between the two is 3:1) detection, after the reaction, acetonitrile is evaporated under reduced pressure, 15mL water is added to the remaining reactant, potassium carbonate is dissolved after adding water , separate the organ...

Embodiment 3

[0051] Embodiment 3: basically the same as Embodiment 1, the difference is:

[0052] The difference between the preparation method of N-isoamyl-2-methyl-5-formyl-3-pyrrolecarboxylic acid ethyl ester of the present invention and Example 1 is:

[0053] In step c: the compound II (0.2716g, 1.5mmol) obtained in step b was placed in a reaction vessel, and bromoisopentane (0.2492g, 1.65mmol), phase transfer catalyst tetrabutylammonium bromide (0.0161 g, 0.05mmol), solvent acetonitrile 7.5mL and anhydrous potassium carbonate (0.621g, 4.5mmol), heated up to 65°C in an oil bath for 8h, and performed TLC during the reaction (developing solvents were petroleum ether and ethyl acetate The mixture, the volume ratio between the two when petroleum ether and ethyl acetate are mixed is 3:1) detection, after the reaction is over, acetonitrile is evaporated under reduced pressure, 20mL of water is added to the remaining reactant, and potassium carbonate is made after adding water Dissolved and ...

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Abstract

The invention discloses a preparation method for N-alkyl-2-methyl-5-formyl-3-pyrrole formate and application of N-alkyl2-methyl-5-formyl-3-pyrrole formate in cigarette flavoring. The preparation method comprises the following steps: with D-glucosamine hydrochloride as a raw material, reacting D-glucosamine hydrochloride with acetoacetic acid esters in an aqueous NaHCO3 solution so as to produce a 2-methyl-5-1',2',3',4'-tetrahydroxybutyl-3-pyrrole formate derivative; then preparing 2-methyl-5-formyl-3-pyrrole formate under the action of sodium periodate; and then reacting 2-methyl-5-formyl-3-pyrrole formate with halogenated hydrocarbon in the presence of tetrabutylammonium bromide and anhydrous potassium carbonate so as to obtain an N-alkyl-2-methyl-5-formyl-3-pyrrole formate derivative. The preparation method is simple; and after application of the prepared derivative in a cigarette, fragrance quality of the cigarette is improved, fragrance quantity is increased, fragrance becomes soft and fine, and remaining fragrance is comfortable.

Description

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Claims

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Application Information

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Owner HENAN AGRICULTURAL UNIVERSITY
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