TW202200544A - Arecoline salt and preparation method and product thereof - Google Patents

Abstract

The invention relates to an arecoline salt and preparation method and product thereof. The arecoline salt is a benzoic acid salt of arecoline. Its structural formula is as follows:

．

Description

Arecoline salt and preparation method and product thereof

The invention belongs to the technical field of chemical synthesis, and relates to an arecoline salt, a preparation method and products thereof.

Arecoline, chemical name "1,2,5,6-tetrahydro-1-methyl-3-picolinate methyl ester", oily liquid, has cholinergic effect. Arecoline is a compound with great application value, and its preparation method and application have always attracted people's attention.

，其中X為檳榔鹼與苯甲酸的莫耳比。A first aspect of the present invention provides a kind of arecoline salt, and the arecoline salt is the benzoate of arecoline, and its structural formula is as follows:

, where X is the molar ratio of arecoline to benzoic acid.

In some embodiments, the value range of X is 0<X≦10, preferably 0<X≦8, more preferably 0<X≦6, further preferably 0<X≦5, further It is preferable that it is 0<X≦3, and it is more preferable that it is 0<X≦2.

。In some embodiments, the structural formula of the arecoline salt is:

.

。In some embodiments, the structural formula of the arecoline salt is:

.

。In some embodiments, the structural formula of the arecoline salt is:

.

。In some embodiments, the structural formula of the arecoline salt is:

.

A second aspect of the present invention provides a preparation method of arecoline salt, the method comprising: placing arecoline in a reaction vessel, adding benzoic acid for dissolution reaction under stirring and heating conditions, to obtain arecoline salt;

，其中X為檳榔鹼與苯甲酸的莫耳比。The structural formula of the prepared arecoline salt is as follows:

, where X is the molar ratio of arecoline to benzoic acid.

In some embodiments, the heating temperature is 20°C to 100°C, preferably 20°C to 80°C, more preferably 40°C to 80°C, further preferably 50°C to 80°C, further preferably 50°C ~70°C.

In some embodiments, the value range of X is 0<X≦10, preferably 0<X≦8, more preferably 0<X≦6, further preferably 0<X≦5, further It is preferable that it is 0<X≦3, and it is more preferable that it is 0<X≦2.

。In some embodiments, the structural formula of the prepared arecoline salt is:

.

。In some embodiments, the structural formula of the prepared arecoline salt is:

.

。In some embodiments, the structural formula of the prepared arecoline salt is:

.

。In some embodiments, the structural formula of the prepared arecoline salt is:

.

A third aspect of the present invention provides a preparation method of arecoline salt, the method comprising the steps:

Arecoline hydrobromide adds water to dissolve, obtains arecoline hydrobromide aqueous solution;

After adjusting the arecoline hydrobromide aqueous solution to be alkaline, extract with an organic solvent to obtain an organic solvent layer and an aqueous layer;

Get the organic solvent layer, add benzoic acid to dissolve reaction, obtain arecoline salt;

，其中X為檳榔鹼與苯甲酸的莫耳比。The structural formula of described arecoline salt is as follows:

, where X is the molar ratio of arecoline to benzoic acid.

In some embodiments, it further comprises: taking the organic solvent layer, adding water for back extraction and adjusting the aqueous phase to be alkaline, to obtain a secondary organic solvent layer and an aqueous layer;

Take the secondary organic solvent layer, add benzoic acid to dissolve and react to obtain arecoline salt.

In some embodiments, the pH value of the adjusted water phase is 7-10, preferably 7-9.5, more preferably 7-9, still more preferably 7.5-9, still more preferably 8 to 9.

In some embodiments, after drying the secondary organic solvent layer, benzoic acid is added for dissolution reaction to obtain arecoline salt.

In some embodiments, the desiccant is selected from at least one of phosphorus pentoxide, silica gel, caustic soda, lime, soda lime, anhydrous calcium chloride, anhydrous sodium sulfate, and anhydrous magnesium sulfate; preferably, anhydrous sodium sulfate is used.

In some embodiments, the obtained arecoline salt is concentrated and dried to improve the purity of the arecoline salt.

In some embodiments, the pH value of the adjusted arecoline hydrobromide aqueous solution is 7-10, preferably 7-9.5, more preferably 7-9, further preferably 7.5-9, and further preferably 8 to 9.

In some embodiments, the organic solvent is selected from at least one of the following: ethyl acetate, benzene, toluene, xylene, petroleum ether, methyl ether, diethyl ether, methyl tert-butyl ether, dichloromethane, chloroform , ethyl acetate, tetrahydrofuran, n-butanol; preferably ethyl acetate.

In some embodiments, the value range of X is 0<X≦10, preferably 0<X≦8, more preferably 0<X≦6, further preferably 0<X≦5, further It is preferable that it is 0<X≦3, and it is more preferable that it is 0<X≦2.

。In some embodiments, the structural formula of the prepared arecoline salt is:

.

。In some embodiments, the structural formula of the prepared arecoline salt is:

.

。In some embodiments, the structural formula of the prepared arecoline salt is:

.

。In some embodiments, the structural formula of the prepared arecoline salt is:

.

A fourth aspect of the present invention provides an article comprising the arecoline salt.

In some embodiments, the article is an aerosol-forming substrate for being aerosolized to generate an aerosol for ingestion; or the article is a popcorn, chewing gum, or beverage.

In some embodiments, the aerosol-forming substrate is a liquid phase for atomization to generate Aerosol.

In some embodiments, the aerosol-generating substrate is a solid phase configured to generate an aerosol for inhalation when heated below the ignition point.

One or more embodiments are exemplified by the pictures in the corresponding drawings, and these exemplified descriptions do not constitute limitations on the embodiments.

The present invention will be further described with reference to the following examples.

Embodiment 1:

，其中X為檳榔鹼與苯甲酸的莫耳比。Embodiment one of the present invention provides a kind of arecoline salt, and the arecoline salt is the benzoate of arecoline, and its structural formula is as follows:

, where X is the molar ratio of arecoline to benzoic acid.

In some embodiments, the value range of X is 0<X≦10, preferably 0<X≦8, more preferably 0<X≦6, further preferably 0<X≦5, further It is preferable that it is 0<X≦3, and it is more preferable that it is 0<X≦2.

，即檳榔鹼與苯甲酸的莫耳比為0.5。In some embodiments, the structural formula of the arecoline salt is:

, that is, the molar ratio of arecoline to benzoic acid is 0.5.

，即檳榔鹼與苯甲酸的莫耳比為1。In some embodiments, the structural formula of the arecoline salt is:

, that is, the molar ratio of arecoline to benzoic acid is 1.

，即檳榔鹼與苯甲酸的莫耳比為1.5。In some embodiments, the structural formula of the arecoline salt is:

, that is, the molar ratio of arecoline to benzoic acid is 1.5.

，即檳榔鹼與苯甲酸的莫耳比為2。In some embodiments, the structural formula of the arecoline salt is:

, that is, the molar ratio of arecoline to benzoic acid is 2.

Embodiment 2:

Embodiment 2 of the present invention provides a preparation method of arecoline salt, the method comprising: placing arecoline in a reaction vessel, adding benzoic acid for dissolution reaction under stirring and heating conditions, to obtain arecoline salt;

，其中X為檳榔鹼與苯甲酸的莫耳比。The structural formula of the prepared arecoline salt is as follows:

, where X is the molar ratio of arecoline to benzoic acid.

In some embodiments, the heating temperature is 20°C to 100°C, preferably 20°C to 80°C, more preferably 40°C to 80°C, further preferably 50°C to 80°C, further preferably 50°C ~70°C.

In some embodiments, the value range of X is 0<X≦10, preferably 0<X≦8, more preferably 0<X≦6, further preferably 0<X≦5, further It is preferable that it is 0<X≦3, and it is more preferable that it is 0<X≦2.

In one example, arecoline is placed in a reaction vessel, and benzoic acid is added in a ratio that the molar ratio of arecoline and benzoic acid is 0.5, heated to 50° C., stirred and dissolved to obtain arecoline salt.

。The structural formula of the prepared arecoline salt is:

.

In one example, arecoline is placed in a reaction vessel, and benzoic acid is added in a ratio that the molar ratio of arecoline and benzoic acid is 1, heated to 60° C., stirred and dissolved to obtain arecoline salt.

。The structural formula of the prepared arecoline salt is:

.

In an example, arecoline is placed in a reaction vessel, and benzoic acid is added in a ratio that the molar ratio of arecoline and benzoic acid is 1.5, heated to 65° C., stirred and dissolved to obtain arecoline salt.

。The structural formula of the prepared arecoline salt is

.

In one example, arecoline is placed in a reaction vessel, and benzoic acid is added in a ratio that the molar ratio of arecoline and benzoic acid is 2, heated to 70° C., stirred and dissolved to obtain arecoline salt.

。The structural formula of the prepared arecoline salt is:

.

Embodiment three:

The third embodiment of the present invention provides a preparation method of arecoline salt, the method comprising the steps:

Arecoline hydrobromide adds water to dissolve, obtains arecoline hydrobromide aqueous solution;

After adjusting the arecoline hydrobromide aqueous solution to be alkaline, extract with an organic solvent to obtain an organic solvent layer and an aqueous layer;

Get the organic solvent layer, add benzoic acid to dissolve reaction, obtain arecoline salt;

，其中X為檳榔鹼與苯甲酸的莫耳比。The structural formula of described arecoline salt is as follows:

, where X is the molar ratio of arecoline to benzoic acid.

In some embodiments, it further comprises: taking the organic solvent layer, adding water for back extraction and adjusting the aqueous phase to be alkaline, to obtain a secondary organic solvent layer and an aqueous layer;

Take the secondary organic solvent layer, add benzoic acid to dissolve and react to obtain arecoline salt.

In some embodiments, the pH value of the adjusted water phase is 7-10, preferably 7-9.5, more preferably 7-9, still more preferably 7.5-9, still more preferably 8 to 9.

In some embodiments, after drying the secondary organic solvent layer, benzoic acid is added for dissolution reaction to obtain arecoline salt.

In some embodiments, the desiccant is selected from at least one of phosphorus pentoxide, silica gel, caustic soda, lime, soda lime, anhydrous calcium chloride, anhydrous sodium sulfate, and anhydrous magnesium sulfate; preferably, anhydrous sodium sulfate is used.

Specifically, taking ethyl acetate as an example, since ethyl acetate can dissolve a small amount of water, and the water contains impurities such as Na+, Br-, OH-, etc., it is necessary to remove the water in the organic solvent. Anhydrous sodium sulfate is selected as a water scavenger, which can combine with water to form crystal water. The following table shows the comparison of residual bromine before and after adding anhydrous sodium sulfate. solvent name whether to add AFS Test Strength Bromine residues Na ₂ SO ₄ no 63.1 ≈500ppm Yes 6.7 <10ppm

In some embodiments, the obtained arecoline salt is concentrated and dried to improve the purity of the arecoline salt.

Specifically, the yield of the arecoline salt obtained by the aforementioned preparation process is about 90%, the loss rate is small, and the scale-up loss rate increases. The purity of arecoline salt is about 95%, and the main impurity is the residual organic solvent, such as: ethyl acetate. After the concentration and drying process, the purity can reach more than 99%.

In some embodiments, the pH value of the adjusted arecoline hydrobromide aqueous solution is 7-10, preferably 7-9.5, more preferably 7-9, further preferably 7.5-9, and further preferably 8 to 9.

Specifically, the principle of the preparation process is to adjust the pH value of the solution to make the dissociated alkaloids into free forms, and then achieve the separation effect according to the different distribution coefficients of the free alkaloids in water and organic solvents. Through the experimental pre-test, the pH value of the aqueous solution of arecoline hydrobromide is neutral, and the free alkaloid is less if the pH value is not adjusted, and the extraction rate is low. When the pH value is adjusted to above 10, the extraction rate is not significantly improved, and the alkalinity is too strong, which increases the risk of NaOH residues, so it is appropriate to adjust the pH value to 8-9. And in the back extraction, also need to adjust the pH value, otherwise, the yield is low.

In some embodiments, the organic solvent is selected from at least one of the following: ethyl acetate, benzene, toluene, xylene, petroleum ether, methyl ether, diethyl ether, methyl tert-butyl ether, dichloromethane, chloroform , ethyl acetate, tetrahydrofuran, n-butanol; preferably ethyl acetate.

In some embodiments, the value range of X is 0<X≦10, preferably 0<X≦8, more preferably 0<X≦6, further preferably 0<X≦5, further It is preferable that it is 0<X≦3, and it is more preferable that it is 0<X≦2.

In one example, arecoline hydrobromide is added to water for dissolution to obtain an aqueous arecoline hydrobromide solution; sodium hydroxide is added to adjust the pH value of the arecoline hydrobromide aqueous solution to 8 to 9, and then extracted with ethyl acetate , obtain the ethyl acetate layer and the water layer; take the ethyl acetate layer and add water to carry out back extraction, and add sodium hydroxide to adjust the pH value of the water phase to be 8 to 9, and obtain the ethyl acetate layer and the water layer again; After the ethyl acetate layer is dried by anhydrous sodium sulfate, the molar ratio of arecoline and benzoic acid is 1 and benzoic acid is added to dissolve to obtain arecoline salt.

。The structural formula of the prepared arecoline salt is:

.

Physical and chemical analysis:

The arecoline salt prepared by the preparation method of this example is a viscous yellow oily substance, and the color gradually deepens when placed at room temperature.

Fig. 1 is the 3D molecular structural formula schematic diagram of the arecoline salt prepared by the preparation method of this example;

Fig. 2 is the infrared spectrum schematic diagram of the arecoline salt prepared by the preparation method of this example;

Fig. 3 is the infrared spectrum schematic diagram of benzoic acid;

Fig. 4 is the infrared spectrum schematic diagram of arecoline;

Fig. 5 is the proton nuclear magnetic resonance spectrum schematic diagram of the arecoline salt prepared by the preparation method of this example;

Fig. 6 is the carbon nuclear magnetic resonance spectrum schematic diagram of the arecoline salt prepared by the preparation method of this example.

In one example, arecoline hydrobromide is added into water for dissolution to obtain an aqueous arecoline hydrobromide solution; sodium hydroxide is added to adjust the pH value of the arecoline hydrobromide aqueous solution to 8 to 9, and then extracted with dichloromethane , obtain the dichloromethane layer and the water layer; take the dichloromethane layer and add water to carry out back extraction, and add sodium hydroxide to adjust the pH value of the aqueous phase to 8 to 9, and obtain the dichloromethane layer and the water layer again; After the dichloromethane layer is dried by anhydrous magnesium sulfate, benzoic acid is added to dissolve in a molar ratio of arecoline and benzoic acid to 0.5 to obtain arecoline salt.

。The structural formula of the prepared arecoline salt is:

.

The schematic diagram of the 3D molecular structure, the schematic diagram of the infrared spectrum, the schematic diagram of the hydrogen nuclear magnetic resonance spectrum, and the schematic diagram of the carbon nuclear magnetic resonance spectrum of the arecoline salt prepared by the preparation method of this example are similar to those shown in Fig. 1-Fig. Figure 6 for understanding.

In one example, arecoline hydrobromide is added to water for dissolution to obtain an aqueous arecoline hydrobromide solution; sodium hydroxide is added to adjust the pH value of the arecoline hydrobromide aqueous solution to 7 to 9, and then extracted with ethyl acetate , obtain the ethyl acetate layer and the water layer; take the ethyl acetate layer and add water to carry out back extraction, and add sodium hydroxide to adjust the pH value of the water phase to be 7 to 9, and obtain the ethyl acetate layer and the water layer again; After the ethyl acetate layer is dried by anhydrous sodium sulfate, benzoic acid is added to dissolve in a molar ratio of arecoline and benzoic acid to 1.5 to obtain arecoline salt.

。The structural formula of the prepared arecoline salt is

.

The schematic diagram of the 3D molecular structure, the schematic diagram of the infrared spectrum, the schematic diagram of the hydrogen nuclear magnetic resonance spectrum, and the schematic diagram of the carbon nuclear magnetic resonance spectrum of the arecoline salt prepared by the preparation method of this example are similar to those shown in Fig. 1-Fig. Figure 6 for understanding.

In one example, arecoline hydrobromide is added into water for dissolution to obtain an aqueous arecoline hydrobromide solution; sodium hydroxide is added to adjust the pH value of the arecoline hydrobromide aqueous solution to 7-10, and then extracted with ethyl acetate , obtain the ethyl acetate layer and the water layer; take the ethyl acetate layer and add water to carry out back extraction, and add sodium hydroxide to adjust the pH value of the water phase to be 7 to 10, and obtain the ethyl acetate layer and the water layer again; After the ethyl acetate layer is dried by anhydrous sodium sulfate, the molar ratio of arecoline and benzoic acid is 2 and benzoic acid is added to dissolve to obtain arecoline salt.

。The structural formula of the prepared arecoline salt is:

.

The schematic diagram of the 3D molecular structure, the schematic diagram of the infrared spectrum, the schematic diagram of the hydrogen nuclear magnetic resonance spectrum, and the schematic diagram of the carbon nuclear magnetic resonance spectrum of the arecoline salt prepared by the preparation method of this example are similar to those shown in Fig. 1-Fig. Figure 6 for understanding.

Embodiment four:

The fourth embodiment of the present invention provides the use of an arecoline salt in the preparation of an aerosol-forming substrate.

Wherein, the structural formula of arecoline salt and the preparation method thereof can refer to the content described in the foregoing embodiments, and will not be repeated here.

In some embodiments, when preparing the aerosol-forming substrate, based on the total mass of the aerosol-forming substrate, the mass percentage of the arecoline salt is 0.2%-15%, preferably 1%-15% , more preferably 2% to 15%, still more preferably 2% to 10%, still more preferably 2% to 5%, still more preferably 2% to 4%.

In some embodiments, when preparing the aerosol-forming substrate, the item added to the arecoline salt includes a solvent.

In some embodiments, the solvent is selected from at least one of the following: 1,2-propanediol, 1,3-propanediol, glycerol, polyethylene glycol 200, polyethylene glycol 400, dipropylene glycol acetal, ethanol, water , Triethyl citrate, triacetin, caprylic acid glyceride, isopropyl alcohol, orange oil, lemon oil, peppermint oil, palm oil, peanut oil, corn oil, salad oil.

In some embodiments, the solvent includes glycerol, and the mass percentage of the glycerol is 0-90%.

In some embodiments, the solvent includes propylene glycol, and the mass percentage of the propylene glycol is 9% to 99.8%.

In some embodiments, the article added to the arecoline salt further includes a fragrance.

In some embodiments, the fragrance is selected from at least one of: nerol, trans-2-hexenol, linalool, benzyl alcohol, 1-hexanol, leaf alcohol, alpha-terpineol, incense maltol, beta-phenethyl alcohol, linalool oxide, geraniol, isoamyl alcohol, octanol, hexanol, decyl alcohol, cinnamyl alcohol, heptanol, eugenol, maltol, ethyl maltol, thyme Phenol, isoeugenol, 2-methylbutyric acid, malic acid, n-valeric acid, n-hexanoic acid, edible acetic acid, n-octanoic acid, strawberry acid, butyric acid, citric acid, propionic acid, 3-methylvaleric acid, isopentyl acid, isoamyl acetate, amyl formate, geranyl formate, butyl formate, benzyl formate, folate formate, gamma-decalactone, butyl-nononolactone, gamma-caprylactone, gamma-enantholactone , gamma-undecalactone, butyl-dodecalactone, benzaldehyde, strawberry aldehyde, cinnamaldehyde, furfural, citral, acetaldehyde, 3-methylthiopropanal, natural 3-mercapto-2-methylpentanal Aldehyde, isobutyraldehyde, trans-2-octenal, trans-2-nonenal, trans-2-decenal, trans,trans-2,4-heptadienal, 2,5-dimethyl Pyrazine, 2-Acetylfuran, 2-ethyl-3(5 or 6)-dimethylpyrazine, 2,3,5,6-tetramethylpyrazine, 2,3,5-trimethylpyrazine Pyrazine, 2-Acetylpyrazine, Acetophenone, β-Ionone, Trakelenone No. 2 (Firmenich), Butanedione, M-Ionone, Acetoin (Acetyl Methyl alcohol), acetoin (acetyl methyl alcohol), methyl heptenone, vanillin, ethyl vanillin, dihydrocoumarin, raspberry ketone, anisole, methyl cedar ether, methyl alcohol Alkyl-2-methyl-3-furyl disulfide, oil of wintergreen, oil of clove buds, oil of tenfold orange, rosewood oil, geranium oil, oil of bitter almond, oil of clove basil, ethyl vanillin, dimethicone Hydrocoumarin, Raspberry Ketone, Rich Vanillin, Turmeric Extract, Peruvian Extract, Oak Extract, Espresso Supercritical Extract (Water Soluble), Cocoa Extract, Coffee Tincture, Duhuo Tincture, Pandan extract, vanilla extract, labdanum extract, iris oil or extract, jasmine extract, tree moss extract (amber), tamarind extract, zimbabwe extract, tobacco essential oil, burley Extract, flue-cured tobacco pure oil A, flue-cured tobacco butt incense extract, sun-cured tobacco butt incense extract.

It should be noted that the flavoring agent is not limited to the substances listed above, and all flavoring agents complying with the FEMA code and the CAS code can be applied.

In some embodiments, the articles added to the arecoline salts do not contain nicotine and/or nicotine salts.

Embodiment five:

The fifth embodiment of the present invention provides an aerosol-forming substrate, and the aerosol-forming substrate includes an arecoline salt and a solvent.

Wherein, the structural formula of arecoline salt and the preparation method thereof can refer to the content described in the foregoing embodiments, and will not be repeated here.

In some embodiments, based on the total mass of the aerosol-forming substrate, the mass percentage of the arecoline salt is 0.2% to 15%, preferably 1% to 15%, more preferably 2% to 15%, further It is preferably 2% to 10%, more preferably 2% to 5%, still more preferably 2% to 4%.

In some embodiments, when the aerosol-forming substrate is nebulized into an aerosol, at least about 80% of the arecoline salt is in the aerosol.

In some embodiments, when the aerosol-forming substrate is atomized into an aerosol, based on the total mass of the aerosol, the mass percentage of the arecoline salt is 0.1%-12%, preferably 0.8%-12% %, more preferably 1.5% to 12%, still more preferably 1.5% to 8%, still more preferably 1.5% to 4.5%, still more preferably 1.5% to 3.5%.

In some embodiments, the solvent is selected from at least one of the following: 1,2-propanediol, 1,3-propanediol, glycerol, polyethylene glycol 200, polyethylene glycol 400, dipropylene glycol acetal, ethanol, water , Triethyl citrate, triacetin, caprylic acid glyceride, isopropyl alcohol, orange oil, lemon oil, peppermint oil, palm oil, peanut oil, corn oil, salad oil.

In some embodiments, the solvent includes glycerol, and the mass percentage of glycerol in the aerosol-forming substrate is 0-90%.

In some embodiments, the solvent includes propylene glycol, and the mass percentage of propylene glycol in the aerosol-forming substrate is 9% to 99.8%.

In some embodiments, the aerosol-forming substrate further includes a fragrance.

In some embodiments, the fragrance is selected from at least one of: nerol, trans-2-hexenol, linalool, benzyl alcohol, 1-hexanol, leaf alcohol, alpha-terpineol, incense maltol, beta-phenethyl alcohol, linalool oxide, geraniol, isoamyl alcohol, octanol, hexanol, decyl alcohol, cinnamyl alcohol, heptanol, eugenol, maltol, ethyl maltol, thyme Phenol, isoeugenol, 2-methylbutyric acid, malic acid, n-valeric acid, n-hexanoic acid, edible acetic acid, n-octanoic acid, strawberry acid, butyric acid, citric acid, propionic acid, 3-methylvaleric acid, isopentyl acid, isoamyl acetate, amyl formate, geranyl formate, butyl formate, benzyl formate, folate formate, gamma-decalactone, butyl-nononolactone, gamma-caprylactone, gamma-enantholactone , gamma-undecalactone, butyl-dodecalactone, benzaldehyde, strawberry aldehyde, cinnamaldehyde, furfural, citral, acetaldehyde, 3-methylthiopropanal, natural 3-mercapto-2-methylpentanal Aldehyde, isobutyraldehyde, trans-2-octenal, trans-2-nonenal, trans-2-decenal, trans,trans-2,4-heptadienal, 2,5-dimethyl Pyrazine, 2-Acetylfuran, 2-ethyl-3(5 or 6)-dimethylpyrazine, 2,3,5,6-tetramethylpyrazine, 2,3,5-trimethylpyrazine Pyrazine, 2-Acetylpyrazine, Acetophenone, β-Ionone, Trakelenone No. 2 (Firmenich), Butanedione, M-Ionone, Acetoin (Acetyl Methyl alcohol), acetoin (acetyl methyl alcohol), methyl heptenone, vanillin, ethyl vanillin, dihydrocoumarin, raspberry ketone, anisole, methyl cedar ether, methyl alcohol Alkyl-2-methyl-3-furyl disulfide, oil of wintergreen, oil of clove buds, oil of tenfold orange, rosewood oil, geranium oil, oil of bitter almond, oil of clove basil, ethyl vanillin, dimethicone Hydrocoumarin, Raspberry Ketone, Rich Vanillin, Turmeric Extract, Peruvian Extract, Oak Extract, Espresso Supercritical Extract (Water Soluble), Cocoa Extract, Coffee Tincture, Duhuo Tincture, Pandan extract, vanilla extract, labdanum extract, iris oil or extract, jasmine extract, tree moss extract (amber), tamarind extract, zimbabwe extract, tobacco essential oil, burley Extract, flue-cured tobacco pure oil A, flue-cured tobacco butt incense extract, sun-cured tobacco butt incense extract.

It should be noted that the flavoring agent is not limited to the substances listed above, and all flavoring agents complying with the FEMA code and the CAS code can be applied.

In some embodiments, the aerosol-forming matrix is free of nicotine and/or nicotine salts.

1. Atomization comparison test

Experimental test method:

Arecoline salt (the benzoate of arecoline), the solvent is a mixture of glycerol and propylene glycol in a mass ratio of 1:1. The comparative example selects arecoline hydrobromide (the hydrobromide of arecoline), and the solvent selects the mixture of glycerin and propylene glycol with a mass ratio of 1:1.

Use a smoking machine to smoke in accordance with international standards, and use a Cambridge filter to collect the aerosol from the aerosol-forming matrix. The mass of arecoline salt in the test aerosol is m1. Then test the mass of arecoline salt in the remaining aerosol-forming matrix as m2, and the mass of total arecoline salt in the aerosol-forming matrix as m0, and calculate the conversion rate k=m1/(m0-m2).

Among them, the international standards involved can refer to:

CORESTA RECOMMENDED METHOD Nº 81, Afnor standardization XP D90-300-3, International Standard ISO 20768:2018 and PD CEN/TR 17236:2018.

The parameters for smoking e-cigarettes are as follows: Puff Duration 3.0s±0.1s Puff Volume 55mL±0.3mL Puff Frequency 30s±0.5s Puff of Each Group 20 Group Interval Time 300s±120s Maximum Flow 18.5mL/s±0.1mL/s Pressure Drop <50hPa Group 5 Total Number of Puffs 100 Total Duration of Vaporization 300s

Arecoline salt experimental test results: Example Arecoline salt content (%) k Arecoline salt content in aerosol (%) 1 1% 88% 0.88% 2 3% 85% 2.55% 3 5% 90% 4.50% 4 10% 80% 8.00% 5 15% 81% 12.15%

Comparative experimental test results: Example Arecoline hydrobromide content (%) k Content of arecoline hydrobromide in aerosol (%) 1 Arecoline Hydrobromide 1% 79% 0.8% 2 Arecoline Hydrobromide 3% 75% 2.2% 3 Arecoline Hydrobromide 5% 62% 3.1% 4 Arecoline Hydrobromide 10% 56% 5.6% 5 Arecoline Hydrobromide 15% 50% 7.5%

It can be seen from the above experimental test results that the conversion rate of arecoline salt is significantly higher than that of arecoline hydrobromide, and the conversion rate in different concentrations (1% to 15%) is relatively stable, and arecoline salt can be completely atomized normally come out.

2. Comparison test of smoking experience:

Select the same content (3%) of arecoline salt and arecoline hydrobromide to carry out the smoking experience test, through the evaluation of multiple people's smoking, in terms of pleasure, increased heart rate, ruddy face, body heat, slightly sweating, etc. 0-5 points for scoring.

Experimental test results of smoking experience: name pleasure increased heart rate Red face, hot body, slight sweating 3% arecoline salt 4 4 5 3% arecoline hydrobromide 2 1 2

It can be seen from the above experimental test results that arecoline salt with the same content (3%) is significantly better than hydrobromic acid in terms of pleasure, increased heart rate, flushed face, body heat, and slight sweating. Arecoline.

Embodiment six:

Embodiment 6 of the present invention provides an aerosol generating system, including an atomizing device and the aerosol-forming substrate described in Embodiment 5;

The atomizing device is configured to atomize the aerosol-forming substrate to form an aerosol.

In some embodiments, the atomizing device is a heated atomizing device.

In some embodiments, the nebulizing device is an ultrasonic nebulizing device.

In some embodiments, the aerosol-forming base includes arecoline salt, glycerol, and propylene glycol.

In some embodiments, the oscillation frequency of the ultrasonic atomizing device is greater than 1 MHz.

In some embodiments, the atomizing device is an air-compressed atomizing device or a press-type atomizing device.

In some embodiments, the aerosol-forming matrix includes arecoline salt, ethanol, and water.

Embodiment 7:

The seventh embodiment of the present invention provides the use of an arecoline salt in the manufacture of aerosol-generating products.

Wherein, the aerosol-generating product is used to be heated to generate an aerosol for inhalation. The structural formula of arecoline salt and the preparation method thereof can refer to the contents described in the foregoing embodiments, which will not be repeated here.

In some embodiments, when manufacturing the aerosol-generating product, based on the total mass of the raw materials of the aerosol-generating product, the mass percentage of the arecoline salt is 0.2% to 15%, preferably 1% to 15%. 15%, more preferably 2% to 15%, still more preferably 2% to 10%, still more preferably 2% to 5%, still more preferably 2% to 4%, more preferably 3% to 4%.

In some embodiments, when manufacturing the aerosol-generating article, the items added to the arecoline salt include: aerosols, binders, and vegetable fibers.

In some embodiments, when manufacturing the aerosol-generating product, based on the total mass of the raw materials of the aerosol-generating product, the mass percentage of the atomizing agent is 5% to 30%, preferably 10% to 30%. 30%, more preferably 10% to 25%, still more preferably 15% to 25%.

In some embodiments, the nebulizer is selected from at least one of the following: 1,2-propanediol, 1,3-propanediol, glycerol, polyethylene glycol 200, polyethylene glycol 400, dipropylene glycol acetal, ethanol , water, triethyl citrate, triacetin, caprylic glyceride, isopropyl alcohol, orange oil, lemon oil, peppermint oil, palm oil, peanut oil, corn oil, salad oil.

In some embodiments, when manufacturing the aerosol-generating product, based on the total mass of the raw materials of the aerosol-generating product, the mass percentage of the binder is 1%-20%, preferably 1%-15% %, more preferably 1% to 10%, still more preferably 3% to 10%, still more preferably 5% to 10%.

In some embodiments, the binder is selected from at least one of the following: carboxymethyl cellulose, hydroxypropyl methyl cellulose, polyvinyl alcohol, rosin, xanthan gum, gum arabic, guar gum, chitosan Sugar, pectin, locust bean gum, starch, sodium alginate, shellac.

In some embodiments, when manufacturing the aerosol-generating product, based on the total mass of the raw materials of the aerosol-generating product, the mass percentage of the plant fiber is 40% to 80%, preferably 40% to 70%. %, more preferably 50% to 70%, still more preferably 50% to 65%, still more preferably 50% to 60%.

In some embodiments, the plant fiber is selected from at least one of the following: betel nut fiber, wood pulp fiber, hemp pulp fiber, cotton pulp fiber, bagasse pulp fiber, bamboo pulp fiber, coconut pulp fiber.

In some embodiments, the article added to the arecoline salt further includes a fragrance.

In some embodiments, the fragrance is selected from at least one of: nerol, trans-2-hexenol, linalool, benzyl alcohol, 1-hexanol, leaf alcohol, alpha-terpineol, incense maltol, beta-phenethyl alcohol, linalool oxide, geraniol, isoamyl alcohol, octanol, hexanol, decyl alcohol, cinnamyl alcohol, heptanol, eugenol, maltol, ethyl maltol, thyme Phenol, isoeugenol, 2-methylbutyric acid, malic acid, n-valeric acid, n-hexanoic acid, edible acetic acid, n-octanoic acid, strawberry acid, butyric acid, citric acid, propionic acid, 3-methylvaleric acid, isopentyl acid, isoamyl acetate, amyl formate, geranyl formate, butyl formate, benzyl formate, folate formate, gamma-decalactone, butyl-nononolactone, gamma-caprylactone, gamma-enantholactone , gamma-undecalactone, butyl-dodecalactone, benzaldehyde, strawberry aldehyde, cinnamaldehyde, furfural, citral, acetaldehyde, 3-methylthiopropanal, natural 3-mercapto-2-methylpentanal Aldehyde, isobutyraldehyde, trans-2-octenal, trans-2-nonenal, trans-2-decenal, trans,trans-2,4-heptadienal, 2,5-dimethyl Pyrazine, 2-Acetylfuran, 2-ethyl-3(5 or 6)-dimethylpyrazine, 2,3,5,6-tetramethylpyrazine, 2,3,5-trimethylpyrazine Pyrazine, 2-Acetylpyrazine, Acetophenone, β-Ionone, Trakelenone No. 2 (Firmenich), Butanedione, M-Ionone, Acetoin (Acetyl Methyl alcohol), acetoin (acetyl methyl alcohol), methyl heptenone, vanillin, ethyl vanillin, dihydrocoumarin, raspberry ketone, anisole, methyl cedar ether, methyl alcohol Alkyl-2-methyl-3-furyl disulfide, oil of wintergreen, oil of clove buds, oil of tenfold orange, rosewood oil, geranium oil, oil of bitter almond, oil of clove basil, ethyl vanillin, dimethicone Hydrocoumarin, Raspberry Ketone, Rich Vanillin, Turmeric Extract, Peruvian Extract, Oak Extract, Espresso Supercritical Extract (Water Soluble), Cocoa Extract, Coffee Tincture, Duhuo Tincture, Pandan extract, vanilla extract, labdanum extract, iris oil or extract, jasmine extract, tree moss extract (amber), tamarind extract, zimbabwe extract, tobacco essential oil, burley Extract, flue-cured tobacco pure oil A, flue-cured tobacco butt incense extract, sun-cured tobacco butt incense extract.

It should be noted that the flavoring agent is not limited to the substances listed above, and all flavoring agents complying with the FEMA code and the CAS code can be applied.

In some embodiments, the articles added to the arecoline salt do not contain tobacco components.

In some embodiments, the method of making the aerosol-generating article includes one of a papermaking method, a dry-laid papermaking method, a thick stock method, and a rolling method.

Embodiment eight:

The eighth embodiment of the present invention provides an aerosol-generating product, the raw materials of which include arecoline salt, an atomizing agent, a binder and a plant fiber.

Wherein, the aerosol-generating product is used to be heated to generate an aerosol for inhalation. The structural formula of arecoline salt and the preparation method thereof can refer to the contents described in the foregoing embodiments, which will not be repeated here.

In some embodiments, based on the total mass of the raw materials, the mass percentage of the arecoline salt is 0.2% to 15%, preferably 1% to 15%, more preferably 2% to 15%, further preferably 2% % to 10%, more preferably 2% to 5%, still more preferably 2% to 4%, more preferably 3% to 4%.

In some embodiments, based on the total mass of the raw materials, the mass percentage of the atomizing agent is 5%-30%, preferably 10%-30%, more preferably 10%-25%, further preferably 15% % to 25%.

In some embodiments, the nebulizer is selected from at least one of the following: 1,2-propanediol, 1,3-propanediol, glycerol, polyethylene glycol 200, polyethylene glycol 400, dipropylene glycol acetal, ethanol , water, triethyl citrate, triacetin, caprylic glyceride, isopropyl alcohol, orange oil, lemon oil, peppermint oil, palm oil, peanut oil, corn oil, salad oil.

In some embodiments, based on the total mass of the raw materials, the mass percentage of the binder is 1%-20%, preferably 1%-15%, more preferably 1%-10%, further preferably 3% ~10%, more preferably 5% to 10%.

In some embodiments, the binder is selected from at least one of the following: carboxymethyl cellulose, hydroxypropyl methyl cellulose, polyvinyl alcohol, rosin, xanthan gum, gum arabic, guar gum, shell Polysaccharides, pectin, locust bean gum, starch, sodium alginate, shellac.

In some embodiments, based on the total mass of the raw materials, the mass percentage of the plant fiber is 40%-80%, preferably 40%-70%, more preferably 50%-70%, further preferably 50% to 65%, more preferably 50 to 60%.

In some embodiments, the plant fiber is selected from at least one of the following: betel nut fiber, wood pulp fiber, hemp pulp fiber, cotton pulp fiber, bagasse pulp fiber, bamboo pulp fiber, coconut pulp fiber.

In some embodiments, the feedstock further includes a fragrance.

In some embodiments, the fragrance is selected from at least one of: nerol, trans-2-hexenol, linalool, benzyl alcohol, 1-hexanol, leaf alcohol, alpha-terpineol, incense maltol, beta-phenethyl alcohol, linalool oxide, geraniol, isoamyl alcohol, octanol, hexanol, decyl alcohol, cinnamyl alcohol, heptanol, eugenol, maltol, ethyl maltol, thyme Phenol, isoeugenol, 2-methylbutyric acid, malic acid, n-valeric acid, n-hexanoic acid, edible acetic acid, n-octanoic acid, strawberry acid, butyric acid, citric acid, propionic acid, 3-methylvaleric acid, isopentyl acid, isoamyl acetate, amyl formate, geranyl formate, butyl formate, benzyl formate, folate formate, gamma-decalactone, butyl-nononolactone, gamma-caprylactone, gamma-enantholactone , gamma-undecalactone, butyl-dodecalactone, benzaldehyde, strawberry aldehyde, cinnamaldehyde, furfural, citral, acetaldehyde, 3-methylthiopropanal, natural 3-mercapto-2-methylpentanal Aldehyde, isobutyraldehyde, trans-2-octenal, trans-2-nonenal, trans-2-decenal, trans,trans-2,4-heptadienal, 2,5-dimethyl Pyrazine, 2-Acetylfuran, 2-ethyl-3(5 or 6)-dimethylpyrazine, 2,3,5,6-tetramethylpyrazine, 2,3,5-trimethylpyrazine Pyrazine, 2-Acetylpyrazine, Acetophenone, β-Ionone, Trakelenone No. 2 (Firmenich), Butanedione, M-Ionone, Acetoin (Acetyl Methyl alcohol), acetoin (acetyl methyl alcohol), methyl heptenone, vanillin, ethyl vanillin, dihydrocoumarin, raspberry ketone, anisole, methyl cedar ether, methyl alcohol Alkyl-2-methyl-3-furyl disulfide, oil of wintergreen, oil of clove buds, oil of tenfold orange, rosewood oil, geranium oil, oil of bitter almond, oil of clove basil, ethyl vanillin, dimethicone Hydrocoumarin, Raspberry Ketone, Rich Vanillin, Turmeric Extract, Peruvian Extract, Oak Extract, Espresso Supercritical Extract (Water Soluble), Cocoa Extract, Coffee Tincture, Duhuo Tincture, Pandan extract, vanilla extract, labdanum extract, iris oil or extract, jasmine extract, tree moss extract (amber), tamarind extract, zimbabwe extract, tobacco essential oil, burley Extract, flue-cured tobacco pure oil A, flue-cured tobacco butt incense extract, sun-cured tobacco butt incense extract.

It should be noted that the flavoring agent is not limited to the substances listed above, and all flavoring agents complying with the FEMA code and the CAS code can be applied.

In some embodiments, the feedstock does not contain tobacco components.

Example 1:

To prepare heat not burn cigarettes, follow these steps:

Step 1: Preparation of the sheet substrate. Select the solid residue of betel nut extract, soak it in water, the water temperature is 60～80 ℃, the soaking time is 0.5～2h, filter, and then the filtered solid is beaten to obtain a slurry, and the slurry is weighed in parts by weight 50～70 parts, 3-10 parts of solid binder, mix evenly, send the mixed slurry to a paper machine for molding, and dry to a moisture content of about 10-15% to obtain a sheet base;

Wherein, the solid binder can be carboxymethyl cellulose, hydroxypropyl methyl cellulose, polyvinyl alcohol, rosin, xanthan gum, gum arabic, guar gum, chitosan, pectin, locust bean gum, starch , one or more of sodium alginate and shellac.

Step 2: Prepare a coating solution. Weigh 1 to 50 parts of arecoline salt, 2 to 20 parts of spice, and 40 to 80 parts of atomizing agent by weight, and mix them evenly to obtain a coating solution;

Wherein, the atomizing agent is a mixture of glycerol and propylene glycol, and the mixing ratio is 3-5:1.

Step 3: Coating the sheet substrate. The coating solution obtained in step 2 is weighed according to 25% to 40% of the weight of the sheet base obtained in step 1, and the coating solution is sprayed on the sheet base, and allowed to stand for 40 to 60 h under constant temperature and humidity conditions to obtain arecoline salt-containing plant flakes;

Step 4: Preparation of heat-not-burn cigarettes. The plant flakes obtained in step 3 are made into cigarette sticks according to the size, and the cigarette sticks are connected with the filter tip to obtain the heat-not-burn cigarettes containing arecoline salt.

        抽吸時間(溫度)  成分      1s(℃) 2s(℃) 3s(℃) 檳榔鹼鹽 153.1 228.3 241.1 The heat-not-burn cigarettes prepared by the above preparation method are heated by an aerosol generating device (resistance heating is used in the heating method), and an infrared thermal imager is used to test the temperature of the surface of the heating body in a working state. The test results are shown in the following table.

Suction Time (Temperature) Composition 1s(℃) 2s(℃) 3s(℃) arecoline salt 153.1 228.3 241.1

It can be seen from the test results that the arecoline salts in cigarettes can be atomized between 150°C and 250°C and generate smokable aerosols.

Smoking and sensory quality evaluation with ordinary heat-not-burn cigarettes: the heat-not-burn cigarettes prepared by the above preparation method can ingest arecoline and produce similar effects of chewing betel nut, with lower irritation.

Embodiment nine:

The ninth embodiment of the present invention provides the use of arecoline salt in the preparation of a liquid composition for quick beads; wherein, the quick beads comprise a frangible shell and the liquid composition, and the liquid composition is arranged on the inside the broken shell. For the structural formula of arecoline salt and its preparation method, reference may be made to the contents described in the foregoing embodiments, which will not be repeated here.

In some embodiments, based on the total mass of the liquid composition, the mass percentage of the arecoline salt is 0.2% to 15%, preferably 1% to 15%, more preferably 2% to 15%, further preferably It is 2% to 10%, more preferably 2% to 5%, still more preferably 2% to 4%, and more preferably 3% to 4%.

In some embodiments, when preparing the liquid composition, the item added to the arecoline salt includes an atomizing agent.

In some embodiments, based on the total mass of the liquid composition, the mass percentage of the atomizing agent is 5% to 30%, preferably 10% to 30%, more preferably 10% to 25%, further preferably 15% to 25%.

In some embodiments, the nebulizer is selected from at least one of the following: 1,2-propanediol, 1,3-propanediol, glycerol, polyethylene glycol 200, polyethylene glycol 400, dipropylene glycol acetal, ethanol , water, triethyl citrate, triacetin, caprylic glyceride, isopropyl alcohol, orange oil, lemon oil, peppermint oil, palm oil, peanut oil, corn oil, salad oil.

In some embodiments, the article added to the arecoline salt further includes a fragrance.

In some embodiments, the fragrance is selected from at least one of: nerol, trans-2-hexenol, linalool, benzyl alcohol, 1-hexanol, leaf alcohol, alpha-terpineol, incense maltol, beta-phenethyl alcohol, linalool oxide, geraniol, isoamyl alcohol, octanol, hexanol, decyl alcohol, cinnamyl alcohol, heptanol, eugenol, maltol, ethyl maltol, thyme Phenol, isoeugenol, 2-methylbutyric acid, malic acid, n-valeric acid, n-hexanoic acid, edible acetic acid, n-octanoic acid, strawberry acid, butyric acid, citric acid, propionic acid, 3-methylvaleric acid, isopentyl acid, isoamyl acetate, amyl formate, geranyl formate, butyl formate, benzyl formate, folate formate, gamma-decalactone, butyl-nononolactone, gamma-caprylactone, gamma-enantholactone , gamma-undecalactone, butyl-dodecalactone, benzaldehyde, strawberry aldehyde, cinnamaldehyde, furfural, citral, acetaldehyde, 3-methylthiopropanal, natural 3-mercapto-2-methylpentanal Aldehyde, isobutyraldehyde, trans-2-octenal, trans-2-nonenal, trans-2-decenal, trans,trans-2,4-heptadienal, 2,5-dimethyl Pyrazine, 2-Acetylfuran, 2-ethyl-3(5 or 6)-dimethylpyrazine, 2,3,5,6-tetramethylpyrazine, 2,3,5-trimethylpyrazine Pyrazine, 2-Acetylpyrazine, Acetophenone, β-Ionone, Trakelenone No. 2 (Firmenich), Butanedione, M-Ionone, Acetoin (Acetyl Methyl alcohol), acetoin (acetyl methyl alcohol), methyl heptenone, vanillin, ethyl vanillin, dihydrocoumarin, raspberry ketone, anisole, methyl cedar ether, methyl alcohol Alkyl-2-methyl-3-furyl disulfide, oil of wintergreen, oil of clove buds, oil of tenfold orange, rosewood oil, geranium oil, oil of bitter almond, oil of clove basil, ethyl vanillin, dimethicone Hydrocoumarin, Raspberry Ketone, Rich Vanillin, Turmeric Extract, Peruvian Extract, Oak Extract, Espresso Supercritical Extract (Water Soluble), Cocoa Extract, Coffee Tincture, Duhuo Tincture, Pandan extract, vanilla extract, labdanum extract, iris oil or extract, jasmine extract, tree moss extract (amber), tamarind extract, zimbabwe extract, tobacco essential oil, burley Extract, flue-cured tobacco pure oil A, flue-cured tobacco butt incense extract, sun-cured tobacco butt incense extract.

It should be noted that the flavoring agent is not limited to the substances listed above, and all flavoring agents complying with the FEMA code and the CAS code can be applied.

In some embodiments, the articles added to the arecoline salts do not contain nicotine and/or nicotine salts.

In some embodiments, the explosive beads are embedded in an aerosol-generating article.

In some embodiments, the raw material of the aerosol-generating article does not contain tobacco components.

Embodiment ten:

The tenth embodiment of the present invention provides an explosive bead, comprising a frangible shell and a liquid composition, and the liquid composition is arranged in the frangible shell;

Wherein, the liquid composition includes arecoline salt and atomizing agent. For the structural formula of arecoline salt and its preparation method, reference may be made to the contents described in the foregoing embodiments, which will not be repeated here.

In some embodiments, based on the total mass of the liquid composition, the mass percentage of the arecoline salt is 0.2% to 15%, preferably 1% to 15%, more preferably 2% to 15%, further It is preferably 2% to 10%, more preferably 2% to 5%, still more preferably 2% to 4%, and more preferably 3% to 4%.

In some embodiments, based on the total mass of the liquid composition, the mass percentage of the atomizing agent is 5% to 30%, preferably 10% to 30%, more preferably 10% to 25%, further preferably 15% to 25%.

In some embodiments, the nebulizer is selected from at least one of the following: 1,2-propanediol, 1,3-propanediol, glycerol, polyethylene glycol 200, polyethylene glycol 400, dipropylene glycol acetal, ethanol , water, triethyl citrate, triacetin, caprylic glyceride, isopropyl alcohol, orange oil, lemon oil, peppermint oil, palm oil, peanut oil, corn oil, salad oil.

In some embodiments, the liquid composition further includes a fragrance.

In some embodiments, the fragrance is selected from at least one of: nerol, trans-2-hexenol, linalool, benzyl alcohol, 1-hexanol, leaf alcohol, alpha-terpineol, incense maltol, beta-phenethyl alcohol, linalool oxide, geraniol, isoamyl alcohol, octanol, hexanol, decyl alcohol, cinnamyl alcohol, heptanol, eugenol, maltol, ethyl maltol, thyme Phenol, isoeugenol, 2-methylbutyric acid, malic acid, n-valeric acid, n-hexanoic acid, edible acetic acid, n-octanoic acid, strawberry acid, butyric acid, citric acid, propionic acid, 3-methylvaleric acid, isopentyl acid, isoamyl acetate, amyl formate, geranyl formate, butyl formate, benzyl formate, folate formate, gamma-decalactone, butyl-nononolactone, gamma-caprylactone, gamma-enantholactone , gamma-undecalactone, butyl-dodecalactone, benzaldehyde, strawberry aldehyde, cinnamaldehyde, furfural, citral, acetaldehyde, 3-methylthiopropanal, natural 3-mercapto-2-methylpentanal Aldehyde, isobutyraldehyde, trans-2-octenal, trans-2-nonenal, trans-2-decenal, trans,trans-2,4-heptadienal, 2,5-dimethyl Pyrazine, 2-Acetylfuran, 2-ethyl-3(5 or 6)-dimethylpyrazine, 2,3,5,6-tetramethylpyrazine, 2,3,5-trimethylpyrazine Pyrazine, 2-Acetylpyrazine, Acetophenone, β-Ionone, Trakelenone No. 2 (Firmenich), Butanedione, M-Ionone, Acetoin (Acetyl Methyl alcohol), acetoin (acetyl methyl alcohol), methyl heptenone, vanillin, ethyl vanillin, dihydrocoumarin, raspberry ketone, anisole, methyl cedar ether, methyl alcohol Alkyl-2-methyl-3-furyl disulfide, oil of wintergreen, oil of clove buds, oil of tenfold orange, rosewood oil, geranium oil, oil of bitter almond, oil of clove basil, ethyl vanillin, dimethicone Hydrocoumarin, Raspberry Ketone, Rich Vanillin, Turmeric Extract, Peruvian Extract, Oak Extract, Espresso Supercritical Extract (Water Soluble), Cocoa Extract, Coffee Tincture, Duhuo Tincture, Pandan extract, vanilla extract, labdanum extract, iris oil or extract, jasmine extract, tree moss extract (amber), tamarind extract, zimbabwe extract, tobacco essential oil, burley Extract, flue-cured tobacco pure oil A, flue-cured tobacco butt incense extract, sun-cured tobacco butt incense extract.

It should be noted that the flavoring agent is not limited to the substances listed above, and all flavoring agents complying with the FEMA code and the CAS code can be applied.

In some embodiments, the liquid composition does not contain nicotine and/or nicotine salts.

Embodiment eleven:

The eleventh embodiment of the present invention provides an aerosol-generating product, including the explosive beads described in the tenth embodiment.

In some embodiments, the raw material of the aerosol-generating article does not contain tobacco components.

In this embodiment, the aerosol-generating article may be prepared using a papermaking method, a dry-laid method, a thick stock method, or a rolling method. Specifically, for the raw materials of the aerosol-generating product and the preparation steps thereof, reference may be made to the contents described in the foregoing embodiments.

Explosive beads can be implanted into the filter section (not limited to this position) of HNB cigarettes through the filter rod embedding technology (not limited to this technology), and when in use, the smoker can squeeze the explosive beads to ingest betel nut Substances such as alkalis.

It should be noted that, in this embodiment, there are no special restrictions on the components of the fragile shell and the preparation process thereof, as well as the preparation process of the explosive beads, and techniques well known to those with ordinary knowledge in the technical field to which the present invention pertains can be used, namely Can.

Example 1:

The liquid composition in the popped beads was prepared according to the following formula: arecoline salt 10wt%, caprylic acid glyceride 80wt%, menthol 10wt%.

Preparation method: weigh the arecoline salt of the above formula weight, add caprylic acid glyceride and menthol under stirring, and make after mixing.

The explosive beads containing Example 1 were implanted into heat-not-burn cigarettes, and the heat-not-burn cigarettes containing no explosive beads were smoked and evaluated for sensory quality: the heat-not-burn cigarettes containing the explosive beads of Example 1 could Arecoline is ingested and produces a similar effect to chewing betel nut with less irritation.

Embodiment 12:

The twelfth embodiment of the present invention provides the use of arecoline salt in the manufacture of chewing gum. For the structural formula of arecoline salt and its preparation method, reference may be made to the contents described in the foregoing embodiments, which will not be repeated here.

In some embodiments, when manufacturing the chewing gum, based on the total mass of the raw materials of the chewing gum, the mass percentage of the arecoline salt is 0.02% to 2%, preferably 0.02% to 1.6%, more preferably 0.02% to 1.6%. 0.02% to 1.2%, more preferably 0.02% to 1%, still more preferably 0.1% to 1%, still more preferably 0.2% to 1%, still more preferably 0.4% to 1%.

In some embodiments, the item added to the arecoline salt in the manufacture of the chewing gum comprises a gum base.

In some embodiments, when manufacturing the chewing gum, based on the total mass of the raw materials of the chewing gum, the mass percentage of the gum base is 20%-75%, preferably 20%-70%, more preferably 20% % to 60%, more preferably 20% to 50%, still more preferably 25% to 50%, still more preferably 30% to 50%, still more preferably 35% to 50%, still more preferably 35% to 45%.

In some embodiments, the item added to the arecoline salt further includes a sweetener.

In some embodiments, the sweetener is selected from at least one of the following: white sugar, rock sugar, sucrose, maltose, corn syrup, glucose syrup, fructose, maltodextrin, polydextrose, xylitol, sorbitol , Maltitol, Erythritol, Aspartame, Acesulfame K, Sucralose, Stevioside, Neotame.

In some embodiments, when manufacturing the chewing gum, based on the total mass of the raw materials of the chewing gum, the mass percentage of the sweetener is 20%-75%, preferably 20%-70%, more preferably 20% to 60%, more preferably 20% to 50%, more preferably 25% to 50%, still more preferably 25% to 40%, still more preferably 25% to 35%, still more preferably 30% to 35% .

In some embodiments, the article added to the arecoline salt further includes a filler material.

In some embodiments, the filler material is selected from at least one of: sodium carbonate, sodium bicarbonate, potassium carbonate, calcium carbonate, dicalcium phosphate, sodium dihydrogen phosphate.

In some embodiments, when manufacturing the chewing gum, based on the total mass of the raw materials of the chewing gum, the mass percentage of the filler material is 0.03%-23%, preferably 0.03%-20%, more preferably 0.03% % to 15%, more preferably 0.03% to 10%, more preferably 0.5% to 10%, still more preferably 1% to 10%, still more preferably 1.5% to 10%, further preferably 2% to 8%, More preferably, it is 2% to 6%.

In some embodiments, the item added to the arecoline salt further includes a flavoring agent.

In some embodiments, the flavoring agent is selected from at least one of the following: mint, spearmint, cinnamon, borneol, essence.

Thirteenth implementation:

The thirteenth embodiment of the present invention provides a chewing gum, the raw materials of which include arecoline salt and gum base. For the structural formula of arecoline salt and its preparation method, reference may be made to the contents described in the foregoing embodiments, which will not be repeated here.

In some embodiments, based on the total mass of the raw materials, the mass percentage of the arecoline salt is 0.02% to 2%, preferably 0.02% to 1.6%, more preferably 0.02% to 1.2%, further preferably 0.02% % to 1%, more preferably 0.1% to 1%, still more preferably 0.2% to 1%, still more preferably 0.4% to 1%.

In some embodiments, based on the total mass of the raw materials, the mass percentage of the gum base is 20%-75%, preferably 20%-70%, more preferably 20%-60%, further preferably 20% ~50%, more preferably 25% to 50%, still more preferably 30% to 50%, still more preferably 35% to 50%, still more preferably 35% to 45%.

In some embodiments, the feedstock further includes a sweetener.

In some embodiments, the sweetener is selected from at least one of the following: white sugar, rock sugar, sucrose, maltose, corn syrup, glucose syrup, fructose, maltodextrin, polydextrose, xylitol, sorbitol , Maltitol, Erythritol, Aspartame, Acesulfame K, Sucralose, Stevioside, Neotame.

In some embodiments, based on the total mass of the raw materials, the mass percentage of the sweetener is 20%-75%, preferably 20%-70%, more preferably 20%-60%, further preferably 20% % to 50%, more preferably 25% to 50%, still more preferably 25% to 40%, still more preferably 25% to 35%, still more preferably 30% to 35%.

In some embodiments, the feedstock further includes filler material.

In some embodiments, the filler material is selected from at least one of: sodium carbonate, sodium bicarbonate, potassium carbonate, calcium carbonate, dicalcium phosphate, sodium dihydrogen phosphate.

In some embodiments, based on the total mass of the raw materials, the mass percentage of the filler material is 0.03%-23%, preferably 0.03%-20%, more preferably 0.03%-15%, further preferably 0.03% ~10%, more preferably 0.5% to 10%, still more preferably 1% to 10%, still more preferably 1.5% to 10%, still more preferably 2% to 8%, still more preferably 2% to 6%.

In some embodiments, the feedstock further includes a flavoring agent.

In some embodiments, the flavoring agent is selected from at least one of the following: mint, spearmint, cinnamon, borneol, essence.

Example 1:

The chewing gum was prepared according to the following formula: gum base 54wt%, powdered sugar 23wt%, glucose syrup 14wt%, potassium carbonate 4wt%, mint flavor 3wt%, menthol 1wt%, arecoline salt 1wt%.

Preparation method: heat the gum base to 70-105°C, put it into a mixer and stir, add powdered sugar, and let the temperature drop to 60-80°C, then add buffer pair, additives, glucose syrup, arecoline salt, and finally roll flakes , formed into finished products.

Example 2:

The xylitol chewing gum was prepared according to the following formula: gum base 54wt%, xylitol 23wt%, non-sucrose 14wt%, potassium carbonate 4wt%, mint flavor 3wt%, menthol 1wt%, arecoline salt 1wt%.

Preparation method: heat the gum base to 70～105℃, put it into a mixer and stir, add xylitol and non-sucrose, and let the temperature drop to 60～80℃, then add buffer pair, additives, arecoline salt, and finally roll into flakes , formed into finished products.

Eating and sensory quality evaluation of the chewing gum prepared by the above preparation method and ordinary chewing gum: the chewing gum prepared by the above preparation method can produce a similar effect of chewing betel nut, with low irritation and better taste. Since the chewing gum does not contain lime powder and cellulose, the problems of abrasion and irritation of the oral mucosa and inducing oral diseases that exist when chewing betel nut are avoided.

Embodiment fourteen:

The fourteenth embodiment of the present invention provides the use of an arecoline salt in the preparation of beverages. For the structural formula of arecoline salt and its preparation method, reference may be made to the contents described in the foregoing embodiments, which will not be repeated here.

In some embodiments, when preparing the beverage, based on the total mass of the beverage, the mass percentage of the arecoline salt is 0.01%-0.5%, preferably 0.01%-0.4%, more preferably 0.01% ~0.3%, more preferably 0.01% to 0.2%, still more preferably 0.05% to 0.2%.

In some embodiments, when preparing the beverage, the item added to the arecoline salt includes water.

In some embodiments, when preparing the beverage, the mass percentage of the water is 75%-90% based on the total mass of the beverage.

In some embodiments, when preparing the beverage, the items added to the arecoline salt further include functional ingredients.

In some embodiments, the functional ingredient is selected from at least one of the following: Luo Han Guo concentrated juice, natural menthol, licorice concentrated juice, honeysuckle concentrated juice, chrysanthemum extract, pueraria root extract, loquat puree.

In some embodiments, based on the total mass of the beverage, the mass percentage of the functional ingredient is 0.5% to 2%.

In some embodiments, when preparing the beverage, the items added to the arecoline salt further include an acidity regulator.

In some embodiments, the acidity regulator is selected from at least one of: tartaric acid, malic acid, citric acid, sodium citrate.

In some embodiments, when preparing the beverage, the mass percentage of the acidity regulator is 0.1% to 5% based on the total mass of the beverage.

In some embodiments, when preparing the beverage, the items added to the arecoline salt further include a sweetener.

In some embodiments, the sweetener is selected from at least one of the following: white sugar, rock sugar, sucrose, maltose, corn syrup, glucose syrup, fructose, maltodextrin, polydextrose, xylitol, sorbitol , Maltitol, Erythritol, Aspartame, Acesulfame K, Sucralose, Stevioside, Neotame.

In some embodiments, when preparing the beverage, the mass percentage of the sweetener is 0.5% to 5% based on the total mass of the beverage.

In some embodiments, when preparing the beverage, the items added to the arecoline salt further include an antioxidant.

In some embodiments, the antioxidant is selected from at least one of the following: ascorbic acid, sodium erythorbate, vitamin C, vitamin E.

In some embodiments, when the beverage is prepared, the mass percentage of the antioxidant is 0.05% to 0.15% based on the total mass of the beverage.

In some embodiments, when preparing the beverage, the items added to the arecoline salt further include a preservative.

In some embodiments, the preservative is selected from at least one of: sodium benzoate, sodium sorbate, potassium sorbate.

In some embodiments, when preparing the beverage, the mass percentage of the preservative is 0.01%-0.05% based on the total mass of the beverage.

In some embodiments, when preparing the beverage, the items added to the arecoline salt further include flavorings.

In some embodiments, when preparing the beverage, based on the total mass of the beverage, the mass percentage of the food essence is 0.5% to 5%.

Embodiment fifteen:

The fifteenth embodiment of the present invention provides a beverage, the raw materials of which include arecoline salt and water. For the structural formula of arecoline salt and its preparation method, reference may be made to the contents described in the foregoing embodiments, which will not be repeated here.

In some embodiments, based on the total mass of the beverage, the mass percentage of the arecoline salt is 0.01%-0.5%, preferably 0.01%-0.4%, more preferably 0.01%-0.3%, further preferably It is 0.01% to 0.2%, more preferably 0.05% to 0.2%.

In some embodiments, the mass percentage of the water is 75% to 90% based on the total mass of the beverage.

In some embodiments, the feedstock further includes functional ingredients.

In some embodiments, the functional ingredient is selected from at least one of the following: Luo Han Guo concentrated juice, natural menthol, licorice concentrated juice, honeysuckle concentrated juice, chrysanthemum extract, pueraria root extract, loquat puree.

In some embodiments, the mass percentage of the functional ingredient is 0.5% to 2%. In some embodiments, the feedstock further includes an acidity regulator.

In some embodiments, the acidity regulator is selected from at least one of: tartaric acid, malic acid, citric acid, sodium citrate.

In some embodiments, the mass percentage of the acidity regulator is 0.1% to 5%.

In some embodiments, the feedstock further includes a sweetener.

In some embodiments, the sweetener is selected from at least one of the following: white sugar, rock sugar, sucrose, maltose, corn syrup, glucose syrup, fructose, maltodextrin, polydextrose, xylitol, sorbitol , Maltitol, Erythritol, Aspartame, Acesulfame K, Sucralose, Stevioside, Neotame.

In some embodiments, the mass percentage of the sweetener is 0.5% to 5%.

In some embodiments, the feedstock further includes an antioxidant.

In some embodiments, the antioxidant is selected from at least one of the following: ascorbic acid, sodium erythorbate, vitamin C, vitamin E.

In some embodiments, the mass percentage of the antioxidant is 0.05% to 0.15%.

In some embodiments, the feedstock also includes a preservative.

In some embodiments, the preservative is selected from at least one of: sodium benzoate, sodium sorbate, potassium sorbate.

In some embodiments, the mass percentage of the preservative is 0.01% to 0.05%.

In some embodiments, the raw materials also include flavorings.

In some embodiments, the mass percentage of the edible flavor is 0.5% to 5%.

Example 1:

The beverage is prepared according to the following formula: arecoline salt 0.1wt%, water 88wt%, honeysuckle concentrated juice 1wt%, licorice concentrated juice 1wt%, citric acid 2wt%, sodium citrate 2wt%, steviol glycoside 3wt%, vitamin C 0.05wt% %, sodium sorbate 0.05wt%, edible flavor 2.8wt%.

Preparation method: fully mix arecoline salt with water, honeysuckle concentrate juice, licorice concentrate juice, citric acid, sodium citrate, stevioside, vitamin C, sodium sorbate, and edible essence to prepare a beverage.

The beverage prepared by the above preparation method retains a variety of nutrients beneficial to the human body in honeysuckle and licorice, the beverage is rich in ingredients such as arecoline, areca polyphenols, etc. Phlegm to relieve cough, relieve pain and other effects.

This written description uses the embodiments to disclose the invention, including the best mode, and also to enable those of ordinary skill in the art to which the invention pertains to make and use the invention. The patentable scope of the invention is defined by the scope of the patent application, and may include other examples that occur to those skilled in the art to which this invention pertains. Such other embodiments do not differ if such other embodiments have structural elements that do not differ from the literal language of the claimed scope, or if such other embodiments include equivalent structural elements with insubstantial differences from the literal language of the claimed scope. Examples are intended to be within the scope of the claimed scope. To the extent that it does not create inconsistency, all citations referenced herein are incorporated herein by reference.

1 is a schematic diagram of a 3D molecular structure of arecoline salt provided by an embodiment of the present invention. Fig. 2 is the infrared spectrum schematic diagram of arecoline salt provided by the embodiment of the present invention. 3 is a schematic diagram of an infrared spectrum of benzoic acid provided by an embodiment of the present invention. 4 is a schematic diagram of an infrared spectrum of arecoline provided by an embodiment of the present invention. 5 is a schematic diagram of a hydrogen nuclear magnetic resonance spectrum of arecoline salt provided by an embodiment of the present invention. Fig. 6 is the carbon nuclear magnetic resonance spectrum schematic diagram of arecoline salt provided by the embodiment of the present invention.

Claims (29)

A kind of arecoline salt, wherein said arecoline salt is the benzoate of arecoline, and its structural formula is as follows:

, where X is the molar ratio of arecoline to benzoic acid. The arecoline salt according to claim 1, wherein the value range of X is 0<X≦10, preferably 0<X≦8, more preferably 0<X≦6, further preferably 0 <X≦5, more preferably 0<X≦3, and even more preferably 0<X≦2. The arecoline salt as claimed in claim 2, wherein the structural formula of the arecoline salt is:

. The arecoline salt as claimed in claim 2, wherein the structural formula of the arecoline salt is:

. The arecoline salt as claimed in claim 2, wherein the structural formula of the arecoline salt is:

. The arecoline salt as claimed in claim 2, wherein the structural formula of the arecoline salt is:

. A preparation method of arecoline salt, the method comprising: placing arecoline in a reaction vessel, adding benzoic acid for dissolution reaction under stirring and heating conditions to obtain arecoline salt; the structural formula of the prepared arecoline salt is as follows:

, where X is the molar ratio of arecoline to benzoic acid. The preparation method according to claim 7, wherein the heating temperature is 20°C to 100°C, preferably 20°C to 80°C, more preferably 40°C to 80°C, further preferably 50°C to 80°C °C, more preferably 50°C to 70°C. The preparation method according to claim 7 or 8, wherein the value range of X is 0<X≦10, preferably 0<X≦8, more preferably 0<X≦6, and even more preferably 0<X≦5, more preferably 0<X≦3, and even more preferably 0<X≦2. The preparation method as claimed in claim 9, wherein the structural formula of the arecoline salt prepared is:

. The preparation method as claimed in claim 9, wherein the structural formula of the arecoline salt prepared is:

. The preparation method as claimed in claim 9, wherein the structural formula of the arecoline salt prepared is:

. The preparation method as claimed in claim 9, wherein the structural formula of the arecoline salt prepared is:

. A preparation method of arecoline salt, the method comprising: adding arecoline hydrobromide to water for dissolving to obtain an aqueous arecoline hydrobromide solution; after adjusting the arecoline hydrobromide aqueous solution to be alkaline, extracting with an organic solvent to obtain an organic Solvent layer and water layer; Get organic solvent layer, add benzoic acid dissolution reaction, obtain arecoline salt; The structural formula of described arecoline salt is as follows:

, where X is the molar ratio of arecoline to benzoic acid. The preparation method according to claim 14, further comprising: taking the organic solvent layer, adding water for back extraction, and adjusting the water phase to be alkaline to obtain a secondary organic solvent layer and a water layer; taking the secondary organic solvent layer , adding benzoic acid to dissolve the reaction to obtain arecoline salt. The preparation method according to claim 15, wherein the pH value of the adjusted aqueous phase is 7-10, preferably 7-9.5, more preferably 7-9, still more preferably 7.5- 9, more preferably 8-9. The preparation method according to claim 15 or 16, wherein after drying the secondary organic solvent layer, benzoic acid is added for dissolution reaction to obtain arecoline salt. The preparation method according to claim 17, wherein the desiccant is selected from at least one of phosphorus pentoxide, silica gel, caustic soda, lime, soda lime, anhydrous calcium chloride, anhydrous sodium sulfate, anhydrous magnesium sulfate; preferably anhydrous Sodium sulfate. The preparation method according to any one of claims 14 to 18, wherein the obtained arecoline salt is subjected to concentration and drying treatment to improve the purity of the arecoline salt. The preparation method according to any one of claims 14 to 19, wherein the organic solvent is selected from at least one of the following: ethyl acetate, benzene, toluene, xylene, petroleum ether, methyl ether, diethyl ether, methyl tert-butyl ether, dichloromethane, chloroform, ethyl acetate, tetrahydrofuran, n-butanol; preferably ethyl acetate. The preparation method according to any one of claims 14 to 20, wherein the value range of X is 0<X≦10, preferably 0<X≦8, more preferably 0<X≦6, and further It is preferable that it is 0<X≦5, it is more preferable that it is 0<X≦3, and it is more preferable that it is 0<X≦2. The preparation method as claimed in claim 21, wherein the structural formula of the arecoline salt prepared is:

. The preparation method as claimed in claim 21, wherein the structural formula of the arecoline salt prepared is:

. The preparation method as claimed in claim 21, wherein the structural formula of the arecoline salt prepared is:

. The preparation method as claimed in claim 21, wherein the structural formula of the arecoline salt prepared is:

. An areca-flavored product, wherein the product comprises the arecoline salt according to any one of claims 1 to 6. The article of claim 27, wherein the article is an aerosol-forming substrate for being aerosolized to generate an aerosol for inhalation; or the article is a popcorn, chewing gum, or a beverage. The product according to claim 28, wherein the aerosol-forming substrate is a liquid phase, which is used for any one of a heating atomizing device, an ultrasonic atomizing device, an air-compressed atomizing device, and a pressing-type atomizing device. Nebulized to generate an aerosol. The article of claim 28, wherein the aerosol-generating substrate is a solid phase configured to generate an aerosol for inhalation when heated below the ignition point.

Images