CN115448884B - A cooling agent for tobacco products and its preparation method and application - Google Patents

Abstract

The present invention discloses a cooling agent for tobacco products and a preparation method and application thereof, and belongs to the technical field of tobacco cooling agents. The cooling agent has a structure shown in Formula I. The present invention introduces a carbonyl imidazole structure into menthol to obtain a colorless oily menthol oxycarbonyl imidazole cooling agent. The cooling agent releases its aroma slowly and is easy to add, and can provide a more lasting, deep and impactful cooling taste. Adding the cooling agent to heat-not-burn tobacco products can improve the quality of smoke and improve people's smoking experience.

Description

A cooling agent for tobacco products and its preparation method and application

Technical Field

The invention relates to the technical field of tobacco cooling agents, and in particular to a cooling agent for tobacco products and a preparation method and application thereof.

Background technique

Heat-not-burn cigarettes use an electric heating device to heat the atomized matrix section to 200-400°C, thus producing a sensory experience similar to that of traditional cigarettes. Compared with the combustion temperature of traditional cigarettes (usually over 800°C), the heating temperature of tobacco has been significantly reduced. It is this lower smoking temperature that greatly reduces the release of tar and harmful substances produced by high temperatures, which meets people's health needs and has gradually become a research and development hotspot for tobacco companies.

At present, there are relatively few types of heat-not-burn tobacco products, and there are certain gaps in quantity, type, and quality compared with traditional cigarettes, mainly in terms of product mist (smoke concentration and release), aroma (aroma flavor and release), taste (mouthfeel), etc. Among them, the characteristics of aroma substance flavor and release uniformity significantly affect the smoking experience and largely determine the quality of heat-not-burn tobacco products. Therefore, people often improve the quality of heat-not-burn tobacco products by optimizing the taste and release characteristics of aroma substances.

Tobacco cooling agents are a general term for chemical substances that are used in various tobacco products to produce a cooling effect and have weak medicinal properties. As an important additive to mint cigarettes, they can mask the bitter taste of cigarettes, make the taste fresh, improve the coordination and softness of cigarette smoke, reduce oral and throat irritation, and greatly improve people's smoking experience. Therefore, they are widely used in the cigarette industry.

Existing tobacco cooling agents are mainly menthol and its derivatives, such as monomenthyl succinate, dimenthyl malate, and WS series cooling agents. Among them, compared with menthol, cooling agents derived from menthol have a longer-lasting and deeper cooling effect, and can provide a cooling effect with no or weak aroma but a stronger impact. Therefore, the development of a menthol derivative cooling agent suitable for heat-not-burn cigarettes is crucial to improving the smoke quality of heat-not-burn tobacco products and people's smoking experience.

Summary of the invention

In view of this, the technical problem to be solved by the present invention is to provide a cooling agent for tobacco products and a preparation method and application thereof. The cooling agent of the present invention can provide a more lasting, deep and impactful cooling taste.

In order to achieve the above purpose, the technical solution adopted by the present invention is as follows:

The present invention provides a cooling agent for tobacco products, wherein the cooling agent has a structure shown in Formula I:

The compound of the structure shown in Formula I of the present invention has a chemical name of menthoxycarbonyl imidazole. By introducing the carbonyl imidazole structure into menthol, the aroma of the cooling agent is released slowly, and a more lasting, deep and impactful cooling taste can be provided.

The invention provides a method for preparing a cooling agent for tobacco products. Menthol and N, N'-carbonyldiimidazole are mixed and reacted under the action of an organic base catalyst to obtain the cooling agent.

The preparation method of the tobacco product cooling agent provided by the present invention comprises the following specific steps:

1) mixing menthol and N,N'-carbonyldiimidazole uniformly to obtain a mixed system;

2) adding an organic base catalyst into the mixed system to cause a condensation reaction to obtain the cooling agent.

The reaction equation of the reaction is:

The present invention has no particular limitation on the order of mixing in step 1) of the above preparation method.

In a specific embodiment of the present invention, menthol is first dissolved in a reaction solvent, and then N,N'-carbonyldiimidazole is slowly added to allow for thorough mixing.

Preferably, the molar ratio of menthol to N,N'-carbonyldiimidazole is 1:(1-4).

Preferably, the reaction solvent is selected from one or more of dichloromethane, ethyl acetate, tetrahydrofuran, toluene and acetonitrile.

In a specific embodiment of the present invention, the reaction solution is ethyl acetate.

Preferably, the organic base catalyst is selected from one or more of pyridine, 4-dimethylaminopyridine and triethylamine.

Preferably, the molar ratio of the organic base catalyst to menthol is 1:(10-100).

In a specific embodiment of the present invention, the organic base catalyst is pyridine, and the molar ratio of pyridine to menthol is 1:20.

Preferably, the reaction temperature is room temperature, specifically 20-50°C.

Preferably, the reaction time is 2 to 3 hours.

The present invention also provides the use of the menthyloxycarbonyl imidazole compound shown in the above formula I as a cooling agent for tobacco products.

Preferably, the tobacco product is a heat-not-burn tobacco product. Adding the cooling agent to the heat-not-burn tobacco product can provide a long-lasting cool and more harmonious smoke.

The present invention also provides a heat-not-burn tobacco product, comprising the heat-not-burn tobacco product and a cooling agent added to the heat-not-burn tobacco product.

Preferably, the cooling agent is the above cooling agent or the cooling agent prepared by the above preparation method.

Compared with the prior art, the present invention introduces a carbonyl imidazole structure into menthol to obtain a colorless oily menthol oxycarbonyl imidazole cooling agent. The cooling agent releases its aroma slowly, is easy to add, and can provide a more lasting, deep and impactful cooling taste. Adding the cooling agent to heat-not-burn tobacco products can significantly improve the smoke quality and improve people's smoking experience.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG1 is a high-resolution mass spectrum of menthyloxycarbonylimidazole;

FIG2 is a ¹ H NMR diagram of menthyloxycarbonylimidazole;

FIG3 is a ¹³ C NMR chart of menthyloxycarbonylimidazole.

Detailed ways

The menthol, N,N'-carbonyldiimidazole, ethyl acetate and organic base catalyst pyridine described in the present invention are all commercially available products.

To further illustrate the present invention, the cooling agent for the heat-not-burn tobacco product and the preparation method thereof provided by the present invention are described in detail below in conjunction with the examples.

Example 1

10 mmol of menthol was added to a 100 mL round-bottom flask, and 40 mL of ethyl acetate was added as a reaction solvent. The mixture was stirred magnetically under an ice bath until the menthol was completely dissolved. Then, 12 mmol of N, N'-carbonyldiimidazole (CDI) was slowly added to the reaction system. 0.5 mmol of pyridine (Py) was dissolved in 10 mL of ethyl acetate and the mixture was dripped into the round-bottom flask within 5 minutes. The ice bath was removed and the mixture was allowed to react at room temperature. After the reaction was complete as detected by TLC, the reaction solution was washed with water, concentrated, and then distilled under reduced pressure to obtain a colorless viscous liquid, i.e., the product, menthyloxycarbonylimidazole, with a yield of 89% and a purity of 98%.

The characterization data of the product structure are as follows:

1) High resolution mass spectrometry (HR-MS) analysis:

The HR-MS of the product menthyloxycarbonyl imidazole was measured on a Bruker En Apex ultra 7.0 FT-MS mass spectrometer.

The results of high-resolution mass spectrometry analysis are shown in Figure 1. The mass-to-charge ratio of menthyloxycarbonylimidazole is: [M+H] ⁺ m/z 251.1760.

2) Nuclear magnetic resonance hydrogen spectrum analysis of the product:

The hydrogen nuclear magnetic resonance spectrum of menthyloxycarbonylimidazole was obtained by testing with a Bruker AV400 superconducting nuclear magnetic resonance instrument.

The results of hydrogen nuclear magnetic resonance spectrum analysis are shown in Figure 2: ¹ H NMR (400 MHz, Chloroform-d) δ 8.06 (s, 1H), 7.36 (s, 1H), 6.99 (s, 1H), 4.85-4.79 (m, 1H), 2.11-2.09 (m, 1H), 1.88-1.83 (m, 1H), 1.70-1.66 (m, 2H), 1.51-1.46 (m, 2H), 1.13-1.00 (m, 2H), 0.89-0.76 (m, 7H), 0.75 (d, J=6.99 Hz, 3H).

3) NMR carbon spectrum analysis of the product:

The carbon NMR spectrum of menthyloxycarbonylimidazole was obtained by using a Bruker AV400 superconducting NMR instrument.

The results of carbon nuclear magnetic resonance spectrum analysis are shown in Figure 3: ¹³ C NMR (101 MHz, Chloroform-d) δ 148.3, 137.0, 130.5, 117.1, 79.4, 47.0, 40.6, 33.9, 31.4, 26.5, 23.5, 21.9, 20.6, 16.4.

Example 2

Menthyloxycarbonylimidazole cooling agent was dissolved in food-grade ethanol, added to tobacco powder at a ratio of 0.02wt%, pressed into tablets, cut into shreds and made into heat-not-burn cigarettes. Professional smoking evaluation found that the heat-not-burn cigarettes with added menthyloxycarbonylimidazole cooling agent showed obvious and lasting cooling feeling, more uniform and consistent release before and after, smooth smoke and more harmonious aroma.

Comparative Example 1

Menthol cooling agent is dissolved in food grade ethanol, added to tobacco powder at a ratio of 0.02wt%, pressed into sheets, cut into shreds and made into heat-not-burn cigarettes. Professional smoking evaluation found that the heat-not-burn cigarettes with menthol cooling agent added have no obvious cooling sensation and the cooling sensation is short-lived.

Professional smoking testers referred to the national standard (sensory technical requirements) GB5606.4-2005 and scored the sensory quality of heat-not-burn cigarettes based on the characteristics of the cigarettes. The results are shown in Table 1.

Table 1

The above results are taken from the average of the sensory quality scores of 7 professional tasters.

In summary, the menthol oxycarbonyl imidazole cooling agent of the present invention effectively improves the effect of the cooling agent by introducing a carbonyl imidazole group into menthol, and can provide a more lasting, deep and impactful cooling taste. Adding the cooling agent to heat-not-burn cigarettes can improve the smoke quality and improve people's smoking experience.

The above embodiments are only used to help understand the method and core idea of the present invention. It should be noted that, for those skilled in the art, several improvements and modifications can be made to the present invention without departing from the principles of the present invention, and these improvements and modifications also fall within the scope of protection of the claims of the present invention.

Claims (7)

1. A heat-not-burn tobacco product, characterized in that it comprises a heat-not-burn tobacco product and a cooling agent added to the heat-not-burn tobacco product; The cooling agent has a structure shown in Formula I: 2. The heat-not-burn tobacco product according to claim 1, characterized in that the cooling agent is prepared according to the following method: Menthol and N,N'-carbonyldiimidazole are mixed and reacted under the action of an organic base catalyst to obtain the cooling agent. 3 . The heat-not-burn tobacco product according to claim 2 , wherein the molar ratio of menthol to N,N′-carbonyldiimidazole is 1:(1-4). 4. The heat-not-burn tobacco product according to claim 2, characterized in that the reaction solvent is selected from one or more of dichloromethane, ethyl acetate, tetrahydrofuran, toluene, and acetonitrile. 5. The heat-not-burn tobacco product according to claim 2, characterized in that the organic base catalyst is selected from one or more of pyridine, 4-dimethylaminopyridine, and triethylamine; The molar ratio of the organic base catalyst to menthol is 1:(10-100). 6. The heat-not-burn tobacco product according to claim 2, characterized in that the temperature of the reaction is room temperature. 7. The heat-not-burn tobacco product according to claim 2, characterized in that the reaction time is 2 to 3 hours.