JP2022534871A - Nicotine composition, method for producing same, and aerosol-generating article comprising same - Google Patents

Abstract

The present invention provides nicotine compositions containing a high ratio of desirable compounds to undesirable compounds. the nicotine composition comprises a non-aqueous solvent, at least 0.2 weight percent nicotine based on the weight of the nicotine composition, a first weight ratio of (β-ionone + β-damascenone) to (phenol) greater than 0.25; and a second weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine)*100)) to (nicotine) greater than 5 x 10-4. Also, heating the tobacco starting material at an extraction temperature of 100 degrees Celsius to 160 degrees Celsius for at least 90 minutes; collecting volatile compounds released from the tobacco starting material during the heating; Also provided is a nicotine composition prepared by a method comprising forming a liquid tobacco extract comprising a volatile compound and forming a nicotine composition from the liquid tobacco extract. [Selection drawing] Fig. 1

Description

The present invention relates to nicotine compositions.

Aerosol generation systems for delivering aerosols to users are known that include an atomizer configured to generate an inhalable aerosol from a liquid composition, such as a liquid nicotine composition. Some known aerosol-generating systems comprise a thermal atomizer, such as an electric heater, configured to heat and vaporize a liquid composition to generate an aerosol. One popular type of electrically heated aerosol generating system is the electronic cigarette. Other known aerosol generation systems include non-thermal atomizers configured to generate an aerosol from a liquid composition using, for example, impinging jets, ultrasound, or vibrating mesh technology.

Nicotine compositions may be produced by an extraction process in which nicotine and other volatile flavor compounds are extracted from tobacco materials and collected in a suitable solvent to form a liquid tobacco extract.

Methods are known for producing liquid tobacco extracts from tobacco materials.

Liquid tobacco extracts may be produced by a high temperature extraction process in which nicotine and other volatile flavor compounds are extracted from tobacco material and collected in a suitable solvent to form a natural liquid tobacco extract.

As an example, an alternative process is known in which the tobacco material is substantially boiled in water for several hours or days to form a vapor phase and the distillate obtained by condensation of the vapor phase is collected in a vessel. Over time, an oily, waxy layer containing a high proportion of non-polar compounds accumulates on the surface of the distillate.

The aqueous portion, which builds up a waxy layer on top and contains nicotine and other water-soluble compounds, is recycled to the boiler. A non-polar co-solvent may optionally be fed to the boiler with the aqueous portion to increase the extraction yield. On the other hand, the waxy phase is collected to finally form the primary product of one such hydrodistillation process. These products are often called "tobacco essential oils" and contain a high proportion of non-polar compounds (fatty acids, neophytadiene, etc.) present in tobacco. Tobacco essential oil obtained by one such method typically does not contain nicotine.

It is also known to subject tobacco material to an extraction process involving the use of volatile non-polar solvents. Examples of suitable solvents include short alkanes, cyclic or acyclic, as well as chlorinated solvents such as dichloromethane. In one such process, excess solvent may be evaporated by controlled heating under vacuum. This is typically done in the presence of ethanol, which has a higher boiling point than the extraction solvent, so that even trace amounts of extraction solvent can be detected.

The primary product of one such solvent-assisted extraction process is often referred to as "tobacco absolute" and may contain trace amounts of ethanol. It is a waxy product containing a highly concentrated mixture of mostly non-polar compounds that can be extracted using a particular solvent, and generally contains nicotine, which is generally relatively Present in high concentrations.

An alternative extraction process involves contacting the tobacco material with a solvent under supercritical conditions, such as supercritical carbon dioxide. One such process, disclosed in US Patent Publication No. 2013/160777, relies on the principle that volatiles within a feedstock contacted with a supercritical fluid can partition into the supercritical phase. After dissolution of any soluble material, the supercritical fluid containing the dissolved material can be removed and the dissolved constituents of the feed material can be separated from the supercritical fluid. The primary product of the supercritical extraction process is substantially similar to the "tobacco absolute" of solvent-assisted extraction processes carried out at lower temperatures and pressures, containing no residual solvent and high levels of waxy nonpolar and contain nicotine, which is generally present in relatively high concentrations.

In another type of extraction process, the tobacco material is immersed in a suitable solvent, such as an aerosol former, for several weeks at room temperature or below to extract the tobacco components into the solvent. In one such process, often referred to as the cold maceration process, the tobacco material is held in suspension in the extract for periods of up to weeks or even months. The resulting slurry is then filtered so that the collected liquid phase can be used to make liquid compositions for use in aerosol generating systems. However, it is generally difficult to control the extraction conditions (eg, temperature and pressure) in one such process. Additionally, the liquid phase collected upon filtration of the slurry, which represents a primary product of the cold maceration process, tends to be highly diluted and low in levels of non-polar tobacco flavor species. Additionally, the liquid phase typically contains little or no nicotine. As such, liquid extracts obtained by the cold maceration method generally need to be supplemented with additional ingredients such as nicotine salts and glycerin prior to use in aerosol generating systems.

Liquid tobacco extracts and nicotine compositions obtained by such known extraction processes may have low levels of nicotine. Furthermore, nicotine compositions obtained by such extraction processes may have low levels and low types of flavor species, particularly with respect to compounds associated with heated tobacco flavor, such as furaneol. Nicotine compositions obtained by such extraction processes may also have high levels of undesirable compounds. In general, the concentration of nicotine, flavor species, and undesirable compounds obtained by such extraction processes can be significantly affected by the tobacco type or types used as starting materials.

It is an object of the present invention to alleviate one or more of the drawbacks of nicotine compositions obtained by known processes. It would be particularly desirable to produce new and improved nicotine compositions.

The present disclosure relates to nicotine compositions. Preferably, the nicotine composition contains at least 0.2% by weight of nicotine. Preferably, the nicotine composition comprises a non-aqueous solvent. Preferably, the nicotine composition comprises a weight ratio of (β-ionone + β-damascenone) to (phenol) greater than 0.25. Preferably, the nicotine composition comprises a weight ratio of (furaneol+(2,3-diethyl-5-methylpyrazine)*100)) to (nicotine) greater than 5×10 ⁻⁴ .

The present disclosure further relates to cartridges containing nicotine compositions. The present disclosure also relates to a nicotine composition prepared by a method comprising heating the tobacco starting material to an extraction temperature of 100 degrees Celsius to 160 degrees Celsius for at least 90 minutes.

According to the present invention, a non-aqueous solvent, at least 0.2 weight percent nicotine based on the weight of the nicotine composition, a first weight ratio of (β-ionone + β-damascenone) to (phenol) greater than 0.25; and a second weight ratio of (furaneol+(2,3-diethyl-5-methylpyrazine)*100)) to (nicotine) greater than 5×10 ⁻⁴ .

Non-aqueous solvent, nicotine, a first weight ratio of (β-ionone + β-damascenone) to (phenol) greater than 0.25 and (furaneol + (2,3-diethyl-5-methylpyrazine) greater than 5 x ^10-4 )*100) to (nicotine) by heating the tobacco starting material at an extraction temperature of 100 degrees Celsius to 160 degrees Celsius for at least 90 minutes; collecting volatile compounds released from the tobacco starting material; forming a liquid tobacco extract comprising the collected volatile compounds; and optionally drying and concentrating the liquid tobacco extract to form a concentrated tobacco extract. and forming a nicotine composition from the liquid tobacco extract or concentrated tobacco extract.

The nicotine composition may be a liquid nicotine composition or a gel nicotine composition.

The nicotine composition may be for use in an aerosol generating system. In such aerosol-generating systems, the nicotine composition is typically heated within the aerosol-generating device.

As used herein, the term "aerosol-generating device" refers to a device comprising a heater element that interacts with the nicotine compositions of the present invention to generate an aerosol. During use, the volatile compounds are released from the nicotine composition by heat transfer and are entrained in the air drawn through the aerosol generator. As the released compounds cool, they condense to form an aerosol, which is inhaled by the consumer.

As the nicotine composition is heated, an aerosol containing volatile compounds collected from the tobacco starting material during the extraction process is released.

A nicotine composition may include a non-aqueous solvent, water, nicotine, and a flavorant compound.

The inventors have found that, in contrast to the products of the existing extraction processes described above, the liquid tobacco extract according to the present invention has a significantly higher content of compounds associated with the flavor of heated tobacco. . These flavor compounds are substantially absent or present only in trace amounts in the tobacco extract obtained by the maceration process, which typically also contains little or no nicotine. These flavor compounds are also generally absent or present only in trace amounts in tobacco extracts obtained using solvents, including under supercritical conditions. Similarly, tobacco essential oils obtained by distillation processes also typically have a very low content (if any) of such flavorant compounds associated with the flavor of heated tobacco.

The nicotine composition may comprise a total non-aqueous solvent content of from about 10 weight percent to about 95 weight percent. The nicotine composition is preferably about 50 weight percent to about 95 weight percent, such as about 65 weight percent to about 95 weight percent, more preferably about 70 weight percent to about 90 weight percent, most preferably about 80 weight percent. with a total non-aqueous solvent content of from to about 90 weight percent. Preferably, the non-aqueous solvent is triacetin, glycerin, propylene glycol, 1,3-propanediol, or mixtures thereof.

One skilled in the art will appreciate that weight percentages of particular ingredients are disclosed herein for nicotine compositions, liquid tobacco extracts, or concentrated tobacco extracts, and weight percentages are for each nicotine composition, liquid tobacco extract, and It will be appreciated that it is based on the weight of the particular component relative to the total weight of the tobacco extract, or concentrated tobacco extract.

The nicotine composition may comprise a total propylene glycol content of from about 10 weight percent to about 95 weight percent. The nicotine composition comprises from about 20 weight percent to about 95 weight percent, such as from about 50 weight percent to about 95 weight percent, or from about 65 weight percent to about 95 weight percent, from about 70 weight percent to about 90 weight percent, or from about 80 weight percent. It may contain a total propylene glycol content of from weight percent to about 90 weight percent.

The nicotine composition may comprise a total triacetin content of about 10 weight percent to about 95 weight percent. The nicotine composition comprises from about 20 weight percent to about 95 weight percent, such as from about 50 weight percent to about 95 weight percent, from about 70 weight percent to about 90 weight percent, or from about 65 weight percent to about 95 weight percent, or from about 80 weight percent. It may comprise a total triacetin content of from weight percent to about 90 weight percent.

The nicotine composition may comprise a total glycerin content of from about 10 weight percent to about 95 weight percent. The nicotine composition comprises from about 20 weight percent to about 95 weight percent, such as from about 50 weight percent to about 95 weight percent, or from about 65 weight percent to about 95 weight percent, from about 70 weight percent to about 90 weight percent, or from about 80 weight percent. It may contain a total glycerin content of from weight percent to about 90 weight percent.

The nicotine composition may comprise a total 1,3-propanediol content of about 10 weight percent to about 95 weight percent. The nicotine composition comprises from about 20 weight percent to about 95 weight percent, such as from about 50 weight percent to about 95 weight percent, or from about 65 weight percent to about 95 weight percent, or from about 80 weight percent to about 90 weight percent of 1, It may contain a total content of 3-propanediol.

The nicotine compositions of the present invention contain at least 0.2 weight percent nicotine. More preferably, the nicotine content in the nicotine composition is at least about 0.4 weight percent. The nicotine composition has a nicotine content of about 12 weight percent or less, such as about 10 weight percent or less, preferably about 8 weight percent or less, more preferably about 5 weight percent or less, preferably about 3.6 weight percent or less. can. Most preferably, the nicotine composition comprises from about 0.4 weight percent to 3.6 weight percent nicotine, based on the weight of the nicotine composition.

The nicotine composition may contain from 1 weight percent to 85 weight percent water. The nicotine composition may contain from 2 weight percent to 50 weight percent water. The nicotine composition may contain from 3 weight percent to 30 weight percent water. The nicotine composition may contain from 5 weight percent to 25 weight percent water. The nicotine composition may contain from 8 weight percent to 20 weight percent water. Preferably, the nicotine composition comprises 10% to 15% water by weight.

In some embodiments, nicotine compositions may include one or more water-soluble organic acids. As used herein in connection with the present invention, the term "water-soluble organic acid" refers to organic acids having a water solubility of greater than or equal to about 500 mg/ml at 20°C.

One or more water-soluble organic acids may advantageously bind nicotine in the liquid tobacco extract by forming one or more nicotine salts. One or more nicotine salts may advantageously be dissolved and stabilized in the water present in the liquid tobacco extract or in the non-aqueous solvent. This may advantageously reduce nicotine adsorption within the upper airways and enhance pulmonary nicotine delivery and retention.

More preferably, the nicotine composition contains one or more water-soluble carboxylic acids. Suitable water-soluble carboxylic acids include, but are not limited to, acetic acid, citric acid, lactic acid, levulinic acid, malic acid, malonic acid, and pyruvic acid. Most preferably the nicotine composition comprises lactic acid.

Preferably, the water-soluble organic acid content of the nicotine composition is greater than or equal to about 2 weight percent. More preferably, the water-soluble organic acid content of the nicotine composition is greater than or equal to about 3 weight percent.

The water-soluble organic acid may be acetic acid. Acetic acid from the extraction process may be present in the nicotine composition, or acetic acid may be added after the extraction process. Additional acetic acid is acetic acid added after the extraction process.

When acetic acid is added to the liquid tobacco extract to form the nicotine composition, the total content of acetic acid in the nicotine composition, including both the acetic acid from the extraction process and the additional acetic acid, is preferably about 0.5. 01 weight percent to about 8 weight percent, such as about 0.03 weight percent to about 8 weight percent, about 0.3 weight percent to about 8 weight percent, about 2 weight percent to about 8 weight percent, or about 3 weight percent to about 8 weight percent. More preferably, the total acetic acid content is from about 0.01 weight percent to about 6 weight percent, such as from about 0.03 weight percent to about 6 weight percent, from about 0.3 weight percent to about 6 weight percent, from about 2 weight percent to about 6 weight percent, or about 3 weight percent to about 6 weight percent.

Preferably, the nicotine composition has a water-soluble organic acid content of about 8 weight percent or less. More preferably, the nicotine composition has a water-soluble organic acid content of about 6 weight percent or less.

Preferably, the water-soluble organic acid content of the nicotine composition is from about 2 weight percent to about 8 weight percent. For example, the water-soluble organic acid content of the nicotine composition may be from about 2 weight percent to about 6 weight percent.

More preferably, the water-soluble organic acid content of the nicotine composition is from about 3 weight percent to about 8 weight percent. For example, the water-soluble organic acid content of the nicotine composition may be from about 3 weight percent to about 6 weight percent.

The nicotine composition may include one or more non-tobacco-derived flavoring agents. Suitable non-tobacco-derived flavorants include, but are not limited to, menthol.

Preferably, the nicotine composition has a non-tobacco-derived flavor content of no greater than about 4 weight percent. More preferably, the nicotine composition has a non-tobacco-derived flavor content of no greater than about 3 weight percent.

The nicotine composition is analyzed by gas chromatography to determine liquid content. The weight of each compound within the nicotine composition may be reported as micrograms per gram of nicotine composition. The weight ratios of the compounds within the nicotine compositions described herein can then be calculated.

In the nicotine compositions of the present invention, a first weight ratio of (β-ionone + β-damascenone) to (phenol) is greater than 0.25. The above ratio will be higher if the amount of the desired flavor compounds β-ionone and β-damascenone is high or if the amount of phenol is low.

Preferably, the first weight ratio of (β-ionone + β-damascenone) to (phenol) is greater than 0.5, more preferably greater than 1, even more preferably greater than 1.5, most preferably 2 greater than, for example, 2-10 or 2-5.

Furaneol and 2,3-diethyl-5-methylpyrazine are desirable flavor compounds included in the nicotine compositions of the present invention. For example, furaneol is a desirable compound derived from heat treating the inherent reducing sugar content of tobacco plant material with other tobacco plant components. Bright tobacco typically has a much higher reducing sugar content (up to 25% by weight) than burley tobacco.

In the nicotine compositions of the present invention, a second weight ratio of (furaneol+(2,3-diethyl-5-methylpyrazine)*100)) to (nicotine) is greater than 5×10 ⁻⁴ . Such a ratio provides a good sensory profile. Preferably, the second weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine)*100)) to (nicotine) is from 8x10 ^-4 to 9x10 ^-3 , or from 1x10 ^-3 to 5x10 ^-3 is.

The nicotine compositions of the present invention have greater than 1.5 (β-ionone + β-damascenone) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)- It may have a weight ratio of N-nitrosoanatabine + (R,S)-N-nitrosoanabasine + N-nitrosonornicotine + ((2-furanmethanol)/600)).

The above ratios are higher when the amounts of the desired flavor compounds β-ionone and β-damascenone are high, or when the amounts of TSNA and 2-furanmethanol are low.

(β-ionone + β-damascenone) versus (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R,S)-N) -nitrosoanabasine + N-nitrosonornicotine + ((2-furanmethanol)/600)) weight ratio is greater than 0.2, such as greater than 0.5, such as from 1 to 10 or from about 1.5 to about 6 may be used. Preferably, the weight ratio is from about 2 to about 4.

The nicotine composition may contain other desirable compounds derived directly from natural tobacco, many of which are flavorants. Nicotine compositions include acetic acid, vanillin, 2-ethyl-3,5-dimethylpyrazine, 2-methylbutanoic acid, 3-methylbutanoic acid, 3-methyl-2,4-nonanedione, 2-methoxyphenol, 2-phenylethanol, It may contain one or more of eugenol, and sotolone.

The nicotine composition includes β-ionone. The nicotine composition contains at least 0.100 micrograms of β-ionone per gram of nicotine composition, preferably at least 0.200 micrograms of β-ionone per gram of nicotine composition, more preferably per gram of nicotine composition It may contain at least 0.300 micrograms of β-ionone, most preferably at least 0.400 micrograms of β-ionone per gram of nicotine composition. In preferred embodiments, the nicotine composition contains at least 0.500 micrograms of β-ionone per gram of nicotine composition, more preferably at least 0.600 micrograms of β-ionone per gram of nicotine composition, even more preferably contains at least 0.700 micrograms of β-ionone per gram of nicotine composition, most preferably at least 0.800 micrograms of β-ionone per gram of nicotine composition. In particularly preferred embodiments, the nicotine composition contains at least 0.9 micrograms of β-ionone per gram of nicotine composition, preferably at least 1.00 micrograms of β-ionone per gram of nicotine composition, more preferably at least 1.00 micrograms of β-ionone per gram of nicotine composition. at least 1.10 micrograms of β-ionone per gram of nicotine composition, even more preferably at least 1.20 micrograms of β-ionone per gram of nicotine composition, most preferably at least 1.20 micrograms of β-ionone per gram of nicotine composition; Contains 30 micrograms of β-ionone. The weight ratio of (β-ionone) to (phenol) is greater than 0.150, such as greater than 0.200, preferably greater than 0.400, more preferably greater than 0.600, most preferably 0.800 may be greater than, for example, greater than 1.20. (β-ionone) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R,S)-N-nitrosoanatabine) The weight ratio of basine + N-nitrosonornicotine + ((2-furanmethanol)/600) is greater than 0.300, such as greater than 0.500, preferably greater than 0.750, more preferably greater than 1.00. greater than, most preferably greater than 1.20, for example may be greater than 1.80.

The nicotine composition includes β-damascenone. The nicotine composition contains at least 0.100 micrograms of β-damascenone per gram of nicotine composition, preferably at least 0.350 micrograms of β-damascenone per gram of nicotine composition, more preferably per gram of nicotine composition It may contain at least 0.600 micrograms of β-damascenone, most preferably at least 0.850 micrograms of β-damascenone per gram of nicotine composition. In preferred embodiments, the nicotine composition contains at least 1.10 micrograms of β-damascenone per gram of nicotine composition, more preferably at least 1.35 micrograms of β-damascenone per gram of nicotine composition, even more preferably contains at least 1.60 micrograms of β-damascenone per gram of nicotine composition, most preferably at least 1.85 micrograms of β-damascenone per gram of nicotine composition. In particularly preferred embodiments, the nicotine composition contains at least 2.10 micrograms of β-damascenone per gram of nicotine composition, preferably at least 2.35 micrograms of β-damascenone per gram of nicotine composition, more preferably at least 2.35 micrograms of β-damascenone per gram of nicotine composition. at least 2.60 micrograms of β-damascenone per gram of nicotine composition, even more preferably at least 2.75 micrograms of β-damascenone per gram of nicotine composition, most preferably at least 2.60 micrograms of β-damascenone per gram of nicotine composition; Contains 90 micrograms of β-damascenone. The weight ratio of (β-damascenone) to (phenol) is greater than 0.250, such as greater than 0.300, preferably greater than 0.700, more preferably greater than 1.00, most preferably 1.30 may be greater than, for example, greater than 1.60. (β-damascenone) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R,S)-N-nitrosoanatabine) The weight ratio of basine + N-nitrosonornicotine + ((2-furanmethanol)/600) is greater than 0.300, such as greater than 0.700, preferably greater than 1.00, more preferably greater than 1.50. more, most preferably more than 2.20, for example it may be more than 2.70.

The weight ratio of (β-ionone+β-damascenone) to (nicotine) is greater than 5.00×10 ⁻⁵ , such as greater than 1.00×10 ^{−4 , preferably greater than 2.00×10 −4 ,} more preferably 4.00×10 ⁻⁴ , most preferably 6.00×10 ⁻⁴ , for example 7.00×10 ⁻⁴ .

The nicotine composition includes furaneol. The nicotine composition comprises at least 0.0100 micrograms of furaneol per gram of nicotine composition, preferably at least 0.100 micrograms of furaneol per gram of nicotine composition, more preferably at least 0.300 micrograms of furaneol per gram of nicotine composition It may contain micrograms of furaneol, most preferably at least 0.500 micrograms of furaneol per gram of nicotine composition. In preferred embodiments, the nicotine composition comprises at least 0.700 micrograms of furaneol per gram of nicotine composition, more preferably at least 0.900 micrograms of furaneol per gram of nicotine composition, even more preferably nicotine composition Contains at least 1.10 micrograms of furaneol per gram, most preferably at least 1.30 micrograms of furaneol per gram of nicotine composition. In a particularly preferred embodiment, the nicotine composition comprises at least 1.50 micrograms of furaneol per gram of nicotine composition, preferably at least 1.80 micrograms of furaneol per gram of nicotine composition, more preferably nicotine composition 1 It comprises at least 2.00 micrograms of furaneol per gram, even more preferably at least 2.20 micrograms of furaneol per gram of nicotine composition, and most preferably at least 2.40 micrograms of furaneol per gram of nicotine composition. The weight ratio of (furaneol) to (phenol) is greater than 0.400, such as greater than 0.600, preferably greater than 0.800, more preferably greater than 1.00, most preferably greater than 1.10 , for example, may exceed 1.30. (furaneol) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R,S)-N-nitrosoanabasine + N) -nitrosonornicotine + ((2-furanmethanol)/600) weight ratio is greater than 0.600, such as greater than 0.800, preferably greater than 1.00, more preferably greater than 1.50, Most preferably above 2.00, for example it may be above 2.10.

The nicotine composition includes 2,3-diethyl-5-methylpyrazine. The nicotine composition contains at least 3.00×10 ⁻³ micrograms of 2,3-diethyl-5-methylpyrazine per gram of nicotine composition, preferably at least 5.00×10 ⁻³ micrograms per gram of nicotine composition. grams of 2,3-diethyl-5-methylpyrazine, more preferably at least 9.00×10 ⁻³ micrograms of 2,3-diethyl-5-methylpyrazine per gram of nicotine composition, most preferably nicotine composition It may contain at least 1.50×10 ⁻² micrograms of 2,3-diethyl-5-methylpyrazine per gram. In preferred embodiments, the nicotine composition contains at least 2.50×10 ⁻² micrograms of 2,3-diethyl-5-methylpyrazine per gram of nicotine composition, more preferably at least 3.50×10 ⁻² per gram of nicotine composition. ² micrograms of 2,3-diethyl-5-methylpyrazine, even more preferably at least 5.00×10 ⁻² micrograms of 2,3-diethyl-5-methylpyrazine per gram of nicotine composition, most preferably nicotine composition containing at least 7.50×10 ⁻² micrograms of 2,3-diethyl-5-methylpyrazine per gram of material. In a particularly preferred embodiment, the nicotine composition comprises at least 9.00×10 ⁻² micrograms of 2,3-diethyl-5-methylpyrazine per gram of nicotine composition, preferably at least 0.100 micrograms per gram of nicotine composition. grams of 2,3-diethyl-5-methylpyrazine, more preferably at least 0.200 micrograms of 2,3-diethyl-5-methylpyrazine per gram of nicotine composition, even more preferably per gram of nicotine composition At least 0.300 micrograms of 2,3-diethyl-5-methylpyrazine, most preferably at least 0.400 micrograms of 2,3-diethyl-5-methylpyrazine per gram of nicotine composition. The weight ratio of (2,3-diethyl-5-methylpyrazine) to (phenol) is greater than 0.0200, such as greater than 0.0300, preferably greater than 0.300, more preferably greater than 0.400 , most preferably above 0.500, eg may be above 0.600. (2,3-diethyl-5-methylpyrazine) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R, the weight ratio of S)-N-nitrosoanabasine + N-nitrosonornicotine + ((2-furanmethanol)/600) is greater than 0.0300, such as greater than 0.0400, preferably greater than 0.100, More preferably above 0.500, most preferably above 0.800, for example it may be above 0.900.

Nicotine compositions may include acetic acid. Preferably, the acetic acid comes from the extraction process, although additional acetic acid may be added after the extraction process, as previously described herein. Acetic acid is a desirable compound that lubricates the generated aerosol and reduces irritation.

The nicotine composition contains at least 300 micrograms of acetic acid per gram of nicotine composition, preferably at least 500 micrograms of acetic acid per gram of nicotine composition, more preferably at least 700 micrograms of acetic acid per gram of nicotine composition, most Preferably, each gram of nicotine composition may contain at least 900 micrograms of acetic acid. In preferred embodiments, the nicotine composition contains at least 1200 micrograms of acetic acid per gram of nicotine composition, more preferably at least 1500 micrograms of acetic acid per gram of nicotine composition, even more preferably at least 1500 micrograms of acetic acid per gram of nicotine composition. 2000 micrograms of acetic acid, most preferably at least 2500 micrograms of acetic acid per gram of nicotine composition. In particularly preferred embodiments, the nicotine composition contains at least 3000 micrograms of acetic acid per gram of nicotine composition, preferably at least 3500 micrograms of acetic acid per gram of nicotine composition, more preferably at least 4000 micrograms of acetic acid per gram of nicotine composition. micrograms of acetic acid, even more preferably at least 4500 micrograms of acetic acid per gram of nicotine composition, and most preferably at least 5000 micrograms of acetic acid per gram of nicotine composition. The (acetic acid) to (phenol) weight ratio may be greater than 1500, such as greater than 2000, preferably greater than 2500, more preferably greater than 3000, most preferably greater than 3100, such as greater than 5000. (acetic acid) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R,S)-N-nitrosoanabasine + N) -Nitrosonornicotine + ((2-furanmethanol)/600) weight ratio is greater than 2100, such as greater than 2800, preferably greater than 3000, more preferably greater than 4000, most preferably greater than 5500, such as , may exceed 7500.

Nicotine compositions may include vanillin. The nicotine composition contains at least 3.00×10 ⁻² micrograms vanillin per gram nicotine composition, preferably at least 5.00×10 ⁻² micrograms vanillin per gram nicotine composition, more preferably at least 5.00×10 −2 micrograms vanillin per gram nicotine composition It may contain at least 7.00×10 ⁻² micrograms of vanillin, most preferably at least 9.00×10 ⁻² micrograms of vanillin per gram of nicotine composition. In preferred embodiments, the nicotine composition comprises at least 0.100 micrograms of vanillin per gram of nicotine composition, more preferably at least 0.200 micrograms of vanillin per gram of nicotine composition, even more preferably nicotine composition Contains at least 0.300 micrograms of vanillin per gram, most preferably at least 0.400 micrograms of vanillin per gram of nicotine composition. In a particularly preferred embodiment, the nicotine composition comprises at least 0.500 micrograms of vanillin per gram of nicotine composition, preferably at least 0.600 micrograms of vanillin per gram of nicotine composition, more preferably nicotine composition 1 It comprises at least 0.700 micrograms of vanillin per gram, even more preferably at least 0.800 micrograms of vanillin per gram of nicotine composition, and most preferably at least 0.900 micrograms of vanillin per gram of nicotine composition. The (vanillin) to (phenol) weight ratio may be greater than 1500, such as greater than 2000, preferably greater than 2500, more preferably greater than 3000, most preferably greater than 3100, such as greater than 5000. (vanillin) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R,S)-N-nitrosoanabasine + N) -nitrosonornicotine + ((2-furanmethanol)/600) weight ratio is greater than 0.110, such as greater than 0.150, preferably greater than 0.160, more preferably greater than 0.200, Most preferably above 0.300, for example it may be above 0.500.

Nicotine compositions may include 2-ethyl-3,5-dimethylpyrazine. The nicotine composition comprises at least 0.0800 micrograms of 2-ethyl-3,5-dimethylpyrazine per gram of nicotine composition, preferably at least 0.100 micrograms of 2-ethyl-3 per gram of nicotine composition, 5-dimethylpyrazine, more preferably at least 0.200 micrograms of 2-ethyl-3,5-dimethylpyrazine per gram of nicotine composition, most preferably at least 0.300 micrograms of 2- It may contain ethyl-3,5-dimethylpyrazine. In a preferred embodiment, the nicotine composition comprises at least 0.500 micrograms of 2-ethyl-3,5-dimethylpyrazine per gram of nicotine composition, more preferably at least 0.700 micrograms per gram of nicotine composition. 2-ethyl-3,5-dimethylpyrazine, even more preferably at least 0.900 micrograms of 2-ethyl-3,5-dimethylpyrazine per gram of nicotine composition, most preferably at least micrograms per gram of nicotine composition gram of 2-ethyl-3,5-dimethylpyrazine. In a particularly preferred embodiment, the nicotine composition comprises at least 1.10 micrograms of 2-ethyl-3,5-dimethylpyrazine per gram of nicotine composition, preferably at least 1.30 micrograms per gram of nicotine composition. 2-ethyl-3,5-dimethylpyrazine, more preferably at least 1.50 micrograms of 2-ethyl-3,5-dimethylpyrazine per gram of nicotine composition, even more preferably at least 1 per gram of nicotine composition .70 micrograms of 2-ethyl-3,5-dimethylpyrazine, most preferably at least 1.90 micrograms of 2-ethyl-3,5-dimethylpyrazine per gram of nicotine composition. The weight ratio of (2-ethyl-3,5-dimethylpyrazine) to (phenol) is greater than 0.100, such as greater than 0.400, preferably greater than 1.00, more preferably greater than 1.50 , most preferably above 2.00, eg may be above 2.50. (2-ethyl-3,5-dimethylpyrazine) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R, the weight ratio of S)-N-nitrosoanabasine + N-nitrosonornicotine + ((2-furanmethanol)/600) is greater than 0.500, such as greater than 0.750, preferably greater than 1.00, More preferably above 2.00, most preferably above 3.00, for example it may be above 3.50.

Nicotine compositions may include 2-methylbutanoic acid. The nicotine composition comprises at least 1.00 micrograms of 2-methylbutanoic acid per gram of nicotine composition, preferably at least 2.00 micrograms of 2-methylbutanoic acid per gram of nicotine composition, more preferably nicotine composition 1 It may contain at least 3.00 micrograms of 2-methylbutanoic acid per gram, most preferably at least 5.00 micrograms of 2-methylbutanoic acid per gram of nicotine composition. In preferred embodiments, the nicotine composition comprises at least 6.00 micrograms of 2-methylbutanoic acid per gram of nicotine composition, more preferably at least 7.00 micrograms of 2-methylbutanoic acid per gram of nicotine composition, and still More preferably it contains at least 8.00 micrograms of 2-methylbutanoic acid per gram of nicotine composition, most preferably at least micrograms of 2-methylbutanoic acid per gram of nicotine composition. In particularly preferred embodiments, the nicotine composition comprises at least 9.00 micrograms of 2-methylbutanoic acid per gram of nicotine composition, preferably at least 10.0 micrograms of 2-methylbutanoic acid per gram of nicotine composition, more Preferably at least 12.0 micrograms of 2-methylbutanoic acid per gram of nicotine composition, even more preferably at least 14.0 micrograms of 2-methylbutanoic acid per gram of nicotine composition, most preferably 1 gram of nicotine composition Contains at least 15.0 micrograms of 2-methylbutanoic acid per serving. The weight ratio of (2-methylbutanoic acid) to (phenol) is greater than 7.00, such as greater than 9.00, preferably greater than 15.0, more preferably greater than 17.0, most preferably greater than 20.0. It may be greater than 0, for example greater than 21.0. (2-methylbutanoic acid) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R,S)-N-nitroso The weight ratio of anabasine + N-nitrosonornicotine + ((2-furanmethanol)/600) is greater than 12.0, such as greater than 17.0, preferably greater than 20.0, more preferably 25.0 and most preferably greater than 30.0, for example may be greater than 32.0.

Nicotine compositions may include 3-methylbutanoic acid. The nicotine composition comprises at least 2.00 micrograms of 3-methylbutanoic acid per gram of nicotine composition, preferably at least 3.00 micrograms of 3-methylbutanoic acid per gram of nicotine composition, more preferably nicotine composition 1 It may contain at least 4.00 micrograms of 3-methylbutanoic acid per gram, most preferably at least 5.00 micrograms of 3-methylbutanoic acid per gram of nicotine composition. In preferred embodiments, the nicotine composition comprises at least 6.00 micrograms of 3-methylbutanoic acid per gram of nicotine composition, more preferably at least 8.00 micrograms of 3-methylbutanoic acid per gram of nicotine composition, and still More preferably, it contains at least 10.0 micrograms of 3-methylbutanoic acid per gram of nicotine composition, most preferably at least micrograms of 3-methylbutanoic acid per gram of nicotine composition. In particularly preferred embodiments, the nicotine composition comprises at least 15.0 micrograms of 3-methylbutanoic acid per gram of nicotine composition, preferably at least 20.0 micrograms of 3-methylbutanoic acid per gram of nicotine composition, more Preferably at least 25.0 micrograms of 3-methylbutanoic acid per gram of nicotine composition, even more preferably at least 30.0 micrograms of 3-methylbutanoic acid per gram of nicotine composition, most preferably 1 gram of nicotine composition Contains at least 35.0 micrograms of 3-methylbutanoic acid per serving. The weight ratio of (3-methylbutanoic acid) to (phenol) is greater than 11.0, such as greater than 15.0, preferably greater than 20.0, more preferably greater than 30.0, most preferably greater than 50.0. It may be greater than 0, for example greater than 51.0. (3-methylbutanoic acid) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R,S)-N-nitroso The weight ratio of anabasine + N-nitrosonornicotine + ((2-furanmethanol)/600) is greater than 18.0, such as greater than 40.0, preferably greater than 50.0, more preferably 60.0 and most preferably greater than 65.0, for example may be greater than 70.0.

Nicotine compositions may include 3-methyl-2,4-nonanedione. The nicotine composition contains at least 6.00×10 ⁻³ micrograms of 3-methyl-2,4-nonanedione per gram of nicotine composition, preferably at least 8.00×10 ⁻³ micrograms of 3-methyl-2,4-nonanedione per gram of nicotine composition. - 2,4-nonanedione, more preferably at least 9.00x10 ^-3 micrograms of 3-methyl-2,4-nonanedione per gram of nicotine composition, most preferably at least 0.0100 micrograms per gram of nicotine composition of 3-methyl-2,4-nonanedione. In a preferred embodiment, the nicotine composition contains at least 0.0300 micrograms of 3-methyl-2,4-nonanedione per gram of nicotine composition, more preferably at least 0.0500 micrograms of 3-methyl-2,4-nonanedione per gram of nicotine composition. -methyl-2,4-nonanedione, even more preferably at least 0.0700 micrograms of 3-methyl-2,4-nonanedione per gram of nicotine composition, most preferably at least 3 micrograms per gram of nicotine composition -methyl-2,4-nonanedione. In a particularly preferred embodiment, the nicotine composition comprises at least 0.0900 micrograms of 3-methyl-2,4-nonanedione per gram of nicotine composition, preferably at least 0.100 micrograms of 3-methyl-2,4-nonanedione per gram of nicotine composition. -methyl-2,4-nonanedione, more preferably at least 0.150 micrograms of 3-methyl-2,4-nonanedione per gram of nicotine composition, even more preferably at least 0.200 micrograms per gram of nicotine composition gram of 3-methyl-2,4-nonanedione, most preferably at least 0.250 micrograms of 3-methyl-2,4-nonanedione per gram of nicotine composition. the weight ratio of (3-methyl-2,4-nonanedione) to (phenol) is greater than 0.100, such as greater than 0.125, preferably greater than 0.150, more preferably greater than 0.250; Most preferably it is above 0.225, for example it may be above 0.250. (3-methyl-2,4-nonanedione) vs. 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R,S) - the weight ratio of N-nitrosoanabasine + N-nitrosonornicotine + ((2-furanmethanol)/600) is greater than 0.035, such as greater than 0.040, preferably greater than 0.080, more preferably may be greater than 0.090, most preferably greater than 0.100, such as greater than 0.130.

Nicotine compositions may include 2-methoxyphenol. The nicotine composition comprises at least 0.150 micrograms of 2-methoxyphenol per gram of nicotine composition, preferably at least 0.300 micrograms of 2-methoxyphenol per gram of nicotine composition, more preferably nicotine composition 1 It may contain at least 0.500 micrograms of 2-methoxyphenol per gram, most preferably at least 0.600 micrograms of 2-methoxyphenol per gram of nicotine composition. In preferred embodiments, the nicotine composition comprises at least 0.700 micrograms of 2-methoxyphenol per gram of nicotine composition, more preferably at least 0.800 micrograms of 2-methoxyphenol per gram of nicotine composition, and still More preferably, it contains at least 0.900 micrograms of 2-methoxyphenol per gram of nicotine composition, and most preferably contains at least micrograms of 2-methoxyphenol per gram of nicotine composition. In particularly preferred embodiments, the nicotine composition comprises at least 1.00 micrograms of 2-methoxyphenol per gram of nicotine composition, preferably at least 1.50 micrograms of 2-methoxyphenol per gram of nicotine composition, more Preferably at least 2.00 micrograms of 2-methoxyphenol per gram of nicotine composition, even more preferably at least 2.50 micrograms of 2-methoxyphenol per gram of nicotine composition, most preferably 1 gram of nicotine composition Contains at least 3.00 micrograms of 2-methoxyphenol per serving. The weight ratio of (2-methoxyphenol) to (phenol) is greater than 0.0900, such as greater than 1.00, preferably greater than 1.50, more preferably greater than 2.00, most preferably greater than 3.00. It may be greater than 00, for example greater than 4.50. (2-methoxyphenol) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitroso anatabine + (R,S)-N-nitroso the weight ratio of anabasine + N-nitrosonornicotine + ((2-furanmethanol)/600) is greater than 1.40, such as greater than, preferably greater than 1.80, more preferably greater than 2.00, Most preferably above 3.00, for example it may be above 6.00.

Nicotine compositions may include 2-phenylethanol. The nicotine composition comprises at least 1.50 micrograms of 2-phenylethanol per gram of nicotine composition, preferably at least 3.00 micrograms of 2-phenylethanol per gram of nicotine composition, more preferably nicotine composition 1 It may contain at least 5.00 micrograms of 2-phenylethanol per gram, most preferably at least 7.00 micrograms of 2-phenylethanol per gram of nicotine composition. In preferred embodiments, the nicotine composition comprises at least 9.00 micrograms of 2-phenylethanol per gram of nicotine composition, more preferably at least 10.0 micrograms of 2-phenylethanol per gram of nicotine composition, and still More preferably, it contains at least 11.0 micrograms of 2-phenylethanol per gram of nicotine composition, most preferably at least micrograms of 2-phenylethanol per gram of nicotine composition. In particularly preferred embodiments, the nicotine composition comprises at least 13.0 micrograms of 2-phenylethanol per gram of nicotine composition, preferably at least 15.0 micrograms of 2-phenylethanol per gram of nicotine composition, more Preferably at least 16.0 micrograms of 2-phenylethanol per gram of nicotine composition, even more preferably at least 17.0 micrograms of 2-phenylethanol per gram of nicotine composition, most preferably 1 gram of nicotine composition Contains at least 18.0 micrograms of 2-phenylethanol per serving. The weight ratio of (2-phenylethanol) to (phenol) is greater than 3.00, such as greater than 5.00, preferably greater than 8.00, more preferably greater than 9.00, most preferably greater than 10.00. It may be greater than 0, for example greater than 25.0. (2-phenylethanol) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitroso anatabine + (R,S)-N-nitroso The weight ratio of anabasine + N-nitrosonornicotine + ((2-furanmethanol)/600) is greater than 10.0, such as greater than 13.0, preferably greater than 14.0, more preferably 15.0 and most preferably greater than 17.0, for example may be greater than 35.0.

Nicotine compositions may include eugenol. The nicotine composition comprises at least 0.0600 micrograms of eugenol per gram of nicotine composition, preferably at least 0.0650 micrograms of eugenol per gram of nicotine composition, more preferably at least 0.0700 micrograms of eugenol per gram of nicotine composition It may contain micrograms of eugenol, most preferably at least 0.0800 micrograms of eugenol per gram of nicotine composition. In preferred embodiments, the nicotine composition comprises at least 0.0900 micrograms of eugenol per gram of nicotine composition, more preferably at least 0.100 micrograms of eugenol per gram of nicotine composition, even more preferably nicotine composition Contains at least 0.200 micrograms of eugenol per gram, most preferably at least micrograms of eugenol per gram of nicotine composition. In a particularly preferred embodiment, the nicotine composition comprises at least 0.300 micrograms of eugenol per gram of nicotine composition, preferably at least 0.400 micrograms of eugenol per gram of nicotine composition, more preferably nicotine composition 1 It comprises at least 0.500 micrograms of eugenol per gram, even more preferably at least 0.600 micrograms of eugenol per gram of nicotine composition, and most preferably at least 0.700 micrograms of eugenol per gram of nicotine composition. The (eugenol) to (phenol) weight ratio is greater than 0.100, such as greater than 0.0500, preferably greater than 0.150, more preferably greater than 0.250, most preferably greater than 0.300 , for example, may exceed 1.20. (eugenol) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R,S)-N-nitrosoanabasine + N) -nitrosonornicotine + ((2-furanmethanol)/600) weight ratio is greater than 0.0200, such as greater than 0.0250, preferably greater than 0.0300, more preferably greater than 0.500, Most preferably it is above 0.550, for example it may be above 1.50.

The nicotine composition may contain sotolone. The nicotine composition contains at least 3.00×10 ⁻³ micrograms of sotolone per gram of nicotine composition, preferably at least 5.00×10 ⁻³ micrograms of sotolone per gram of nicotine composition, more preferably at least 5.00×10 −3 micrograms of sotolone per gram of nicotine composition. It may contain at least 7.00×10 ⁻³ micrograms of sotolone, most preferably at least 9.00×10 ⁻³ micrograms of sotolone per gram of nicotine composition. In preferred embodiments, the nicotine composition comprises at least 0.0100 micrograms of sotolone per gram of nicotine composition, more preferably at least 0.0200 micrograms of sotolone per gram of nicotine composition, even more preferably nicotine composition. Contains at least 0.0300 micrograms of sotolone per gram, most preferably at least micrograms of sotolone per gram of nicotine composition. In a particularly preferred embodiment, the nicotine composition comprises at least 0.0400 micrograms of sotolone per gram of nicotine composition, preferably at least 0.0500 micrograms of sotolone per gram of nicotine composition, more preferably nicotine composition 1. containing at least 0.0600 micrograms of sotolone per gram, even more preferably at least 0.0700 micrograms of sotolone per gram of nicotine composition, and most preferably at least 0.0800 micrograms of sotolone per gram of nicotine composition. The weight ratio of (sotolone) to (phenol) is greater than 0.0200, such as greater than 0.0400, preferably greater than 0.150, more preferably greater than 0.0450, most preferably greater than 0.0500 , for example, may exceed 0.0510. (sotolone) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R,S)-N-nitrosoanabasine + N) -nitrosonornicotine + ((2-furanmethanol)/600) weight ratio is greater than 0.0300, such as greater than 0.0400, preferably greater than 0.0500, more preferably greater than 0.0600, Most preferably it is above 0.0700, for example it may be above 0.0750.

Apart from phenol, TSNA, NNK, NAT, NAB and NNN, and 2-furanmethanol, other undesirable compounds that may be present in the nicotine composition but are minimized by the extraction methods described herein include , formaldehyde (from sugar) and acetaldehyde, phenolic compounds (such as catechol, m-cresol, o-cresol and p-cresol), and nitrogen-containing compounds (ammonia, acetamide, pyridine, 3-aminobiphenyl, 4-aminobiphenyl and o -toludin (o-toludine, etc.).

The nicotine composition contains up to 12.0 micrograms of phenol per gram of nicotine composition, such as up to 10.0 micrograms of phenol per gram of nicotine composition, preferably up to 8.00 micrograms of phenol per gram of nicotine composition more preferably up to 6.00 micrograms of phenol per gram of nicotine composition, even more preferably up to 4.00 micrograms of phenol per gram of nicotine composition, most preferably up to 4.00 micrograms of phenol per gram of nicotine composition May contain 2.00 micrograms of phenol.

The nicotine composition contains up to 0.045 micrograms of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) per gram of nicotine composition, e.g. 0.040 micrograms of NNK, preferably up to 0.035 micrograms of NNK per gram of nicotine composition, more preferably up to 0.030 micrograms of NNK per gram of nicotine composition, even more preferably nicotine composition It may contain up to 0.025 micrograms of NNK per gram, most preferably up to 0.020 micrograms of NNK per gram of nicotine composition.

The nicotine composition contains up to 2.00 micrograms of (R,S)-N-nitrosoanatabine (NAT) per gram of nicotine composition, such as up to micrograms of NAT per gram of nicotine composition, preferably nicotine composition up to 1.50 micrograms of NAT per gram of substance, more preferably up to 1.00 micrograms of NAT per gram of nicotine composition, even more preferably up to 0.500 micrograms of NAT per gram of nicotine composition; Most preferably, up to 0.300 micrograms of NAT may be included per gram of nicotine composition.

The nicotine composition contains up to 1.60 micrograms of (R,S)-N-nitrosoanabasine (NAB) per gram of nicotine composition, such as up to micrograms of NAB per gram of nicotine composition, preferably nicotine composition up to 1.20 micrograms of NAB per gram of substance, more preferably up to 0.500 micrograms of NAB per gram of nicotine composition, even more preferably up to 0.300 micrograms of NAB per gram of nicotine composition, Most preferably, each gram of nicotine composition may contain up to 0.200 micrograms of NAB.

The nicotine composition contains up to 1.60 micrograms of N-nitrosonornicotine (NNN) per gram of nicotine composition, such as up to 1 microgram of NNN per gram of nicotine composition, preferably up to 1 microgram of NNN per gram of nicotine composition. .20 micrograms of NNN, more preferably up to 0.500 micrograms of NNN per gram of nicotine composition, even more preferably up to 0.300 micrograms of NNN per gram of nicotine composition, most preferably nicotine composition It may contain up to 0.200 micrograms of NNN per gram.

The nicotine composition comprises up to 1500 micrograms of 2-furanmethanol per gram of nicotine composition, such as up to 1500 micrograms of 2-furanmethanol per gram of nicotine composition, preferably up to 1200 micrograms of 2-furanmethanol per gram of nicotine composition. 2-furanmethanol, more preferably up to 1000 micrograms of 2-furanmethanol per gram of nicotine composition, even more preferably up to 900 micrograms of 2-furanmethanol per gram of nicotine composition, most preferably nicotine composition May contain up to 700 micrograms of 2-furanmethanol per gram.

The nicotine composition contains up to 60 micrograms of formaldehyde per gram of nicotine composition, such as up to 50 micrograms of formaldehyde per gram of nicotine composition, preferably up to 50 micrograms of formaldehyde per gram of nicotine composition, more preferably nicotine. It may contain up to 40 micrograms of formaldehyde per gram of composition, even more preferably up to 30 micrograms of formaldehyde per gram of nicotine composition, and most preferably up to 20 micrograms of formaldehyde per gram of nicotine composition.

The nicotine composition contains up to 60 micrograms of acetaldehyde per gram of nicotine composition, such as up to 55 micrograms of acetaldehyde per gram of nicotine composition, preferably up to 55 micrograms of acetaldehyde per gram of nicotine composition, more preferably nicotine It may contain up to 45 micrograms of acetaldehyde per gram of composition, even more preferably up to 35 micrograms of acetaldehyde per gram of nicotine composition, and most preferably up to 30 micrograms of acetaldehyde per gram of nicotine composition.

the nicotine composition contains up to 5.00 micrograms of catechol per gram of nicotine composition, such as up to 4.00 micrograms of catechol per gram of nicotine composition, preferably up to 4.00 micrograms of catechol per gram of nicotine composition; More preferably up to 3.00 micrograms of catechol per gram of nicotine composition, even more preferably up to 2.00 micrograms of catechol per gram of nicotine composition, most preferably up to 1.00 micrograms per gram of nicotine composition May contain micrograms of catechol.

The nicotine composition contains up to 1.00 micrograms of hydroquinone per gram of nicotine composition, such as up to 0.950 micrograms of hydroquinone per gram of nicotine composition, preferably up to 0.900 micrograms of hydroquinone per gram of nicotine composition of hydroquinone, more preferably up to 0.850 micrograms of hydroquinone per gram of nicotine composition, even more preferably up to 0.800 micrograms of hydroquinone per gram of nicotine composition, most preferably up to 0.800 micrograms of hydroquinone per gram of nicotine composition May contain 0.700 micrograms of hydroquinone.

The nicotine composition contains up to 1.30 micrograms of m-cresol per gram of nicotine composition, such as up to 1.20 micrograms of m-cresol per gram of nicotine composition, preferably up to 1 microgram of m-cresol per gram of nicotine composition. .00 micrograms of m-cresol, more preferably up to 0.800 micrograms of m-cresol per gram of nicotine composition, even more preferably up to 0.600 micrograms of m-cresol per gram of nicotine composition, Most preferably, each gram of nicotine composition may contain up to 0.500 micrograms of m-cresol.

The nicotine composition contains up to 1.60 micrograms of o-cresol per gram of nicotine composition, such as up to 1.30 micrograms of o-cresol per gram of nicotine composition, preferably up to 1 microgram of o-cresol per gram of nicotine composition. .10 micrograms of o-cresol, more preferably up to 0.800 micrograms of o-cresol per gram of nicotine composition, even more preferably up to 0.600 micrograms of o-cresol per gram of nicotine composition; Most preferably, each gram of nicotine composition may contain up to 0.400 micrograms of o-cresol.

The nicotine composition contains up to 2.10 micrograms of p-cresol per gram of nicotine composition, such as up to 1.50 micrograms of p-cresol per gram of nicotine composition, preferably up to 1 microgram of p-cresol per gram of nicotine composition. .20 micrograms of p-cresol, more preferably up to 1.00 micrograms of p-cresol per gram of nicotine composition, even more preferably up to 0.900 micrograms of p-cresol per gram of nicotine composition; Most preferably, each gram of nicotine composition may contain up to 0.700 micrograms of p-cresol.

The nicotine composition contains up to 350 micrograms of ammonia per gram of nicotine composition, such as up to 300 micrograms of ammonia per gram of nicotine composition, preferably up to 275 micrograms of ammonia per gram of nicotine composition, more preferably It may contain up to 250 micrograms of ammonia per gram of nicotine composition, even more preferably up to 200 micrograms of ammonia per gram of nicotine composition, and most preferably up to 175 micrograms of ammonia per gram of nicotine composition.

The nicotine composition contains up to 250 micrograms of acetamide per gram of nicotine composition, such as up to 225 micrograms of acetamide per gram of nicotine composition, preferably up to 200 micrograms of acetamide per gram of nicotine composition, more preferably may comprise up to 150 micrograms of acetamide per gram of nicotine composition, even more preferably up to 100 micrograms of acetamide per gram of nicotine composition, most preferably up to 70 micrograms of acetamide per gram of nicotine composition .

The nicotine composition contains up to 45 micrograms of pyridine per gram of nicotine composition, such as up to 35 micrograms of pyridine per gram of nicotine composition, preferably up to 25 micrograms of pyridine per gram of nicotine composition, more preferably It may contain up to 20 micrograms of pyridine per gram of nicotine composition, even more preferably up to 15 micrograms of pyridine per gram of nicotine composition, and most preferably up to 10 micrograms of pyridine per gram of nicotine composition.

A nicotine composition may be produced from a liquid tobacco extract from a tobacco starting material consisting of a single type of natural tobacco. The tobacco starting material may comprise a blend of two or more types of natural tobacco. Alternatively, the nicotine composition forms a first tobacco starting material consisting of a first single type of natural tobacco extracted to form a first extract, and a second extract. may be produced from a liquid tobacco extract from a blend produced from a second tobacco starting material consisting of a second tobacco starting material consisting of a second single type of natural tobacco extracted to produce the first extract and the second are blended to form a liquid tobacco extract. Two or more extracts may be blended in this manner to form a liquid tobacco extract. The ratio of different tobacco types can be adapted depending on the desired characteristics of the aerosol generated from the nicotine composition. For example, if it is desired to provide a relatively high level of nicotine, the percentage of burley tobacco may be increased.

The nicotine composition may be a liquid tobacco extract resulting from an extraction process, the liquid tobacco extract comprising a non-aqueous solvent, water, nicotine, and flavor compounds. Liquid tobacco extracts can advantageously be used directly to provide nicotine compositions for use in electronic cigarettes or other aerosol generating systems. The nicotine composition may be a liquid tobacco extract resulting from the extraction process without the addition of additional nicotine. The nicotine composition may be a liquid tobacco extract resulting from the extraction process without the addition of additional flavor compounds. The nicotine composition may be a liquid tobacco extract resulting from the extraction process without the addition of additional non-aqueous solvents. The nicotine composition may be a liquid tobacco extract resulting from the extraction process without the addition of additional water.

For example, the liquid tobacco extract produced by the extraction process can be used to make nicotine compositions containing 10-20 mg nicotine per milliliter without requiring the addition of nicotine. The term "liquid tobacco extract" describes the direct product of the extraction process from tobacco material. Therefore, liquid tobacco extracts are typically separated from, removed from, or derived from natural tobacco materials using tobacco extraction processing conditions and techniques. Contains mixtures. Therefore, in one such process, the extracted tobacco constituents are removed from the natural tobacco material and separated from the non-extracted tobacco constituents. Thus, liquid tobacco extracts are derived from tobacco starting materials and consist of a mixture of natural tobacco constituents extracted or formed during the extraction process, typically one or more materials other than tobacco starting materials, such as It is combined with the extraction solvent used during the extraction process and the like. Preferably, the extraction solvent is an aerosol former.

The term "aerosol former" as used herein refers to a material that facilitates the formation of an aerosol during use and preferably is substantially resistant to thermal decomposition at the operating temperatures of the aerosol-generating article or aerosol-generating device. It refers to a compound or mixture of compounds. Examples of suitable aerosol formers include polyhydric alcohols such as propylene glycol, triethylene glycol, 1,3-propanediol, 1,3-butanediol, and glycerin, esters of polyhydric alcohols such as glycerol monoacetate, diacetate or triacetate, etc.), and aliphatic esters of mono-, di- or polycarboxylic acids (dimethyl dodecanedioate, dimethyl tetradecanedioate, etc.).

The nicotine composition may comprise a liquid tobacco extract resulting from an extraction process with added nicotine. In the nicotine composition according to the present invention, at least 50 weight percent of the nicotine content in the nicotine composition, based on the total weight of the nicotine composition, may be obtained from the liquid tobacco extract rather than being added after extraction. can. In preferred embodiments, at least 80 weight percent of the nicotine content in the nicotine composition, based on the total weight of the nicotine composition, is obtained from the liquid tobacco extract rather than being added after extraction. Even more preferably, at least 90 weight percent of the nicotine content in the nicotine composition, based on the total weight of the nicotine composition, is obtained from the liquid tobacco extract rather than being added after extraction.

The nicotine composition may comprise a liquid tobacco extract resulting from an extraction process with the addition of additional non-aqueous solvents. In the nicotine composition according to the present invention, at least 50 weight percent, based on the total weight of the nicotine composition, of the non-aqueous extraction solvent content in the nicotine composition is from the liquid tobacco extract, rather than being added after extraction. Obtainable. In preferred embodiments, at least 80 weight percent, based on the total weight of the nicotine composition, of the non-aqueous extraction solvent content in the nicotine composition is obtained from the liquid tobacco extract rather than being added after extraction. Even more preferably, at least 90 weight percent, based on the total weight of the nicotine composition, of the non-aqueous extraction solvent content in the nicotine composition is obtained from the liquid tobacco extract rather than being added after extraction.

The nicotine composition may comprise a liquid tobacco extract resulting from the extraction process with the addition of additional water. In the nicotine composition according to the present invention, at least 50 weight percent, based on the total weight of the nicotine composition, of the water content in the nicotine composition can be obtained from the liquid tobacco extract rather than being added after extraction. . In preferred embodiments, at least 80 weight percent of the water content in the nicotine composition, based on the total weight of the nicotine composition, is obtained from the liquid tobacco extract rather than being added after extraction. Even more preferably, at least 90 weight percent of the water content in the nicotine composition, based on the total weight of the nicotine composition, is obtained from the liquid tobacco extract rather than being added after extraction. Even more preferably, 100 weight percent of the nicotine content in the nicotine composition, based on the total weight of the nicotine composition, is obtained from the liquid tobacco extract rather than being added after extraction.

The nicotine composition may comprise a liquid tobacco extract resulting from the extraction process to which additional flavoring compounds have been added. In the nicotine composition according to the present invention, at least 50 weight percent, based on the total weight of the nicotine composition, of the desired tobacco flavor content in the nicotine composition is a liquid tobacco extract rather than added after extraction. can be obtained from In preferred embodiments, at least 80 weight percent, based on the total weight of the nicotine composition, of the desired flavor seed content in the nicotine composition is obtained from the liquid tobacco extract rather than being added after extraction. More preferably, at least 90 weight percent, based on the total weight of the nicotine composition, of the desired flavor seed content in the nicotine composition is obtained from the liquid tobacco extract rather than being added after extraction. Even more preferably, 100 weight percent of the desired flavor seed content in the nicotine composition, based on the total weight of the nicotine composition, is obtained from the liquid tobacco extract rather than being added after extraction.

As an example, at least 50 weight percent of the furaneol content in the nicotine composition, based on the total weight of the nicotine composition, can be obtained from the liquid tobacco extract rather than being added after extraction. In preferred embodiments, at least 80 weight percent of the furaneol content in the nicotine composition, based on the total weight of the nicotine composition, is obtained from the liquid tobacco extract rather than being added after extraction. More preferably, at least 90 weight percent of the furaneol content in the nicotine composition, based on the total weight of the nicotine composition, is obtained from the liquid tobacco extract rather than being added after extraction. Even more preferably, 100 weight percent of the furaneol content in the nicotine composition, based on the total weight of the nicotine composition, is obtained from the liquid tobacco extract rather than being added after extraction.

As another example, at least 50 weight percent, based on the total weight of the nicotine composition, of the 2,3-diethyl-5-methylpyrazine content in the nicotine composition is liquid It can be obtained from tobacco extract. In preferred embodiments, at least 80 weight percent, based on the total weight of the nicotine composition, of the 2,3-diethyl-5-methylpyrazine content in the nicotine composition is liquid tobacco, rather than being added after extraction. Obtained from extracts. More preferably, at least 90 weight percent, based on the total weight of the nicotine composition, of the 2,3-diethyl-5-methylpyrazine content in the nicotine composition is added to the liquid tobacco extraction rather than being added after extraction. obtained from things. Even more preferably, 100 weight percent, based on the total weight of the nicotine composition, of the 2,3-diethyl-5-methylpyrazine content in the nicotine composition is not added post-extraction, but is liquid tobacco extraction. obtained from things.

The nicotine composition may comprise a liquid tobacco extract that has been further processed, especially concentrated. Preferably, the nicotine composition is a concentrated liquid tobacco extract obtained by drying the liquid tobacco extract in a drying process such as the drying process described herein. Additional non-aqueous solvents, water, nicotine, and flavor compounds as described above may be added to the liquid tobacco extract or concentrated tobacco extract to form a nicotine composition.

As an example, in a nicotine composition according to the present invention, at least 50 weight percent, based on the total weight of the nicotine composition, of the furaneol content in the nicotine composition is obtained from tobacco extract rather than added after extraction. be able to. In preferred embodiments, at least 80 weight percent of the furaneol content in the nicotine composition, based on the total weight of the nicotine composition, is obtained from the tobacco extract rather than being added after extraction. Even more preferably, at least 90 weight percent of the furaneol content in the nicotine composition, based on the total weight of the nicotine composition, is obtained from the tobacco extract rather than being added after extraction.

As another example, in a nicotine composition according to the present invention, at least 50 weight percent, based on the total weight of the nicotine composition, of the 2,3-diethyl-5-methylpyrazine content in the nicotine composition is Rather than being added, it can be obtained from the tobacco extract. In a preferred embodiment, at least 80 weight percent, based on the total weight of the nicotine composition, of the 2,3-diethyl-5-methylpyrazine content in the nicotine composition is added after extraction, rather than added after extraction. obtained from things. Even more preferably, at least 90 weight percent, based on the total weight of the nicotine composition, of the 2,3-diethyl-5-methylpyrazine content in the nicotine composition is tobacco extraction, rather than being added after extraction. obtained from things.

Preferably, the nicotine composition is produced from a liquid tobacco extract. The liquid tobacco extract advantageously provides an improved liquid tobacco extract, and thus an improved nicotine composition, having a significantly improved balance of desirable and undesirable compounds. It is preferably produced using an extraction method with an extraction temperature within a certain range in combination with a heating duration. In particular, the extraction method provides liquid tobacco extracts and nicotine compositions having a maximized ratio of desirable compounds to undesirable compounds in the tobacco starting material. For example, the use of specific combinations of extraction temperatures and times as defined allows optimizing the levels of nicotinic and flavorant compounds, while furan, phenol and phenolic compounds, and tobacco-specific Minimize levels of undesirable compounds such as nitrosamines (TSNAs).

Therefore, liquid tobacco extracts and nicotine compositions obtained by one such method exhibit significant compositional differences with respect to tobacco extracts and nicotine compositions obtained by existing extraction processes, and when heated, presently It can be used as an aerosol-generating e-liquid with distinct composition and flavor characteristics compared to available e-liquids or for the preparation of e-liquids. In particular, the liquid tobacco extracts and nicotine compositions obtained by the method according to the present invention are more efficient than available aerosols produced from existing liquid nicotine compositions by conventional cigarettes or by heated non-combustion devices. It may be used to generate an aerosol that provides a heated tobacco taste that more closely resembles the aerosol generated with heating tobacco within.

The nicotine composition may be a liquid nicotine composition or a gel nicotine composition.

The nicotine composition may include liquid tobacco extract.

The nicotine composition may comprise at least about 10 weight percent liquid tobacco extract. Preferably, the nicotine composition comprises at least about 20 weight percent liquid tobacco extract. More preferably, the nicotine composition comprises at least about 30 weight percent liquid tobacco extract. In preferred embodiments, the nicotine composition comprises at least about 40 weight percent liquid tobacco extract, more preferably at least about 50 weight percent liquid tobacco extract, and even more preferably at least about 60 weight percent liquid tobacco extract. include. In particularly preferred embodiments, the nicotine composition comprises at least about 65 weight percent liquid tobacco extract, more preferably at least about 70 weight percent liquid tobacco extract, and even more preferably at least about 75 weight percent liquid tobacco extract. , most preferably at least about 80 weight percent liquid tobacco extract.

In some embodiments, the nicotine composition may comprise a liquid tobacco extract, and the liquid tobacco extract is a concentrated tobacco extract. A concentrated tobacco extract is a liquid tobacco extract that has been concentrated by a drying process, such as the drying process described herein. The nicotine composition comprises at least about 10 weight percent concentrated tobacco extract, at least about 20 weight percent concentrated tobacco extract, at least about 30 weight percent concentrated tobacco extract, at least about 40 weight percent concentrated tobacco extract, at least About 50 weight percent concentrated tobacco extract, preferably at least about 60 weight percent concentrated tobacco extract, more preferably at least about 70 weight percent concentrated tobacco extract, even more preferably at least about 75 weight percent concentrated tobacco extract and most preferably at least about 80 weight percent concentrated tobacco extract.

In some embodiments, the nicotine composition comprises from about 40 weight percent to about 95 weight percent liquid tobacco extract. More preferably, the nicotine composition comprises from about 40 weight percent to about 95 weight percent liquid tobacco extract. Even more preferably, the nicotine composition comprises from about 50 weight percent to about 95 weight percent liquid tobacco extract. Most preferably, the nicotine composition comprises from about 60 weight percent to about 95 weight percent liquid tobacco extract. In some particularly preferred embodiments, the nicotine composition comprises from about 70 weight percent to about 95 weight percent liquid tobacco extract, even more preferably from about 80 weight percent to about 95 weight percent liquid tobacco extract. The liquid tobacco extract may be a concentrated tobacco extract.

In some embodiments, the nicotine composition comprises from about 40 weight percent to about 90 weight percent liquid tobacco extract. More preferably, the nicotine composition comprises from about 40 weight percent to about 90 weight percent liquid tobacco extract. Even more preferably, the nicotine composition comprises from about 50 weight percent to about 90 weight percent liquid tobacco extract. Most preferably, the nicotine composition comprises from about 60 weight percent to about 90 weight percent liquid tobacco extract. In some particularly preferred embodiments, the nicotine composition comprises from about 70 weight percent to about 90 weight percent liquid tobacco extract, even more preferably from about 80 weight percent to about 90 weight percent liquid tobacco extract. The liquid tobacco extract may be a concentrated tobacco extract.

In some embodiments, the nicotine composition comprises from about 40 weight percent to about 85 weight percent liquid tobacco extract. More preferably, the nicotine composition comprises from about 40 weight percent to about 85 weight percent liquid tobacco extract. Even more preferably, the nicotine composition comprises from about 85 weight percent to about 90 weight percent liquid tobacco extract. Most preferably, the nicotine composition comprises from about 60 weight percent to about 85 weight percent liquid tobacco extract. In some particularly preferred embodiments, the nicotine composition comprises from about 70 weight percent to about 85 weight percent liquid tobacco extract, even more preferably from about 80 weight percent to about 85 weight percent liquid tobacco extract. The liquid tobacco extract may be a concentrated tobacco extract.

The nicotine composition may comprise up to about 100 weight percent liquid tobacco extract. In some embodiments, the nicotine composition can be formed directly from liquid tobacco extract without requiring the addition of additional non-aqueous solvents, flavorants, or nicotine. That is, the nicotine composition may comprise 100 weight percent liquid tobacco extract. In some embodiments, the liquid tobacco extract is a concentrated tobacco extract and the nicotine composition may comprise 100 weight percent concentrated tobacco extract. In embodiments where the nicotine composition comprises 100 weight percent liquid tobacco extract or 100 weight percent concentrated tobacco extract, no additional non-aqueous solvent is present.

Alternatively, in some embodiments, nicotine compositions including liquid tobacco extract may include additional non-aqueous solvents. Additional non-aqueous solvents are non-aqueous solvents added after the extraction step. Additional non-aqueous solvents are solvents that supplement the non-aqueous extraction solvent present in the liquid tobacco extract. In embodiments where the liquid tobacco extract is a concentrated tobacco extract, the nicotine composition comprising the concentrated tobacco extract may contain additional non-aqueous solvents. The total content of non-aqueous solvents in the nicotine composition includes the non-aqueous extraction solvent and any additional non-aqueous solvents, if any, as described above.

Additional non-aqueous solvents may be aerosol formers. The additional non-aqueous solvent is preferably triacetin, glycerin, propylene glycol, 1,3-propanediol, or mixtures thereof.

In embodiments where the nicotine composition comprises an additional non-aqueous solvent, the nicotine composition may comprise 90 weight percent or less of the additional non-aqueous solvent. Preferably, the nicotine composition comprises 80 weight percent or less of additional non-aqueous solvent. More preferably, the nicotine composition contains no more than 70 weight percent additional non-aqueous solvent. In a preferred embodiment, the nicotine composition contains no more than about 60 weight percent additional non-aqueous solvent, more preferably no more than about 50 weight percent additional non-aqueous solvent, and even more preferably no more than about 40 weight percent additional non-aqueous solvent. Contains aqueous solvents. In a particularly preferred embodiment, the nicotine composition comprises no more than about 35 weight percent additional non-aqueous solvent, more preferably no more than about 30 weight percent additional non-aqueous solvent, even more preferably no more than about 25 weight percent additional A non-aqueous solvent, most preferably containing no more than about 20 weight percent liquid tobacco extract.

In one exemplary embodiment, the nicotine composition comprises 84 weight percent propylene glycol, 12.5 weight percent water, 1.2 weight percent nicotine, 0.5 weight percent acetic acid, and A concentrated tobacco extract containing 1.8 weight percent balance of other ingredients, including desirable flavor compounds derived from the described extraction process.

In one exemplary embodiment, the nicotine composition comprises 80 weight percent concentrated tobacco extract and 20 weight percent additional non-aqueous solvent. In this exemplary embodiment, the nicotine composition comprises 20 weight percent glycerin as an additional non-aqueous solvent and 80 weight percent concentrated tobacco extract, wherein the concentrated tobacco extract comprises 84 weight percent propylene glycol, 12.5 weight percent water, 1.2 weight percent nicotine, 0.5 weight percent acetic acid, and 1.8 weight percent other containing desirable flavor compounds derived from the extraction process described herein. Including the balance of the ingredients of Thus, the nicotine composition of this exemplary embodiment is 20 weight percent glycerin, 67.2 weight percent propylene glycol, 10 weight percent water, 0.96 weight percent nicotine, 0.4 weight percent acetic acid , and the balance of other ingredients at 1.44 weight percent, including desirable flavor compounds derived from the extraction process described herein. The composition comprises a total non-aqueous solvent content of 87.2 weight percent, the non-aqueous solvent comprising glycerin and propylene glycol.

The nicotine composition may be a gel nicotine composition. Since nicotine can be irritating to the skin, it is desirable to prevent possible nicotine leakage by entrapping the nicotine within the gel at room temperature. Such gels are described, for example, in WO2018/019543A1.

Advantageously, the gel nicotine composition comprises a thermoreversible gel. This means that the gel becomes fluid when heated to the melting temperature and becomes a gel again at the gelling temperature. The gelling temperature is preferably room temperature or higher and atmospheric pressure or higher. Atmospheric pressure means a pressure of 1 atmosphere. Preferably, the melting temperature is above the gelling temperature. The dissolution temperature of the gel is preferably higher than 50 degrees Celsius or 60 degrees Celsius or 70 degrees Celsius, more preferably higher than 80 degrees Celsius. Melting temperature in this context means the temperature at which the gel is no longer solid and starts to flow.

A gel nicotine composition may include a suitable gelling agent. Gelnicotine compositions preferably comprise agar, agarose, sodium alginate, or gellan gum. Most preferably, the gel nicotine composition comprises agar. Preferably, the gel nicotine composition comprises from about 0.5 weight percent to about 5 weight percent gelling agent, more preferably from about 0.8 weight percent to about 1 weight percent gelling agent.

A gel nicotine composition may include a liquid tobacco extract. Preferably, the gel nicotine composition comprises from about 50 percent to about 99.5 percent liquid tobacco extract, more preferably from about 60 percent to about 99.5 percent liquid tobacco extract, even more preferably from about 70 percent to About 99.5 percent liquid tobacco extract, most preferably about 80 percent to about 99.5 percent liquid tobacco extract.

The liquid tobacco extract may be a concentrated tobacco extract, such that the gel nicotine composition may comprise a concentrated tobacco extract. Preferably, the gel nicotine composition comprises from about 50 percent to about 99.5 percent concentrated tobacco extract, more preferably from about 60 percent to about 99.5 percent concentrated tobacco extract, even more preferably from about 70 percent to About 99.5 percent concentrated tobacco extract, most preferably about 80 percent to about 99.5 percent concentrated tobacco extract.

Gel nicotine compositions may include additional non-aqueous solvents. Preferably, the gel nicotine composition comprises about 5 percent to about 49.5 percent, more preferably about 10 percent to about 40 percent, even more preferably about 15 percent to about 30 percent, most preferably about 20 percent to about Contains 30 percent additional non-aqueous solvent. Additional non-aqueous solvents are preferably glycerin, propylene glycol, triacetin, 1,3-propanediol, or mixtures thereof.

The total content of non-aqueous solvents in the gel nicotine composition includes the non-aqueous extraction solvent and any additional non-aqueous solvents if present. The gel nicotine composition may comprise a total non-aqueous solvent content of from about 10 weight percent to about 95 weight percent. Gel nicotine compositions are preferably about 50 weight percent to about 95 weight percent, such as about 65 weight percent to about 95 weight percent, more preferably about 70 weight percent to about 90 weight percent, most preferably about 80 weight percent. percent to about 90 percent by weight of non-aqueous solvent. Preferably, the non-aqueous solvent is triacetin, glycerin, propylene glycol, 1,3-propanediol, or mixtures thereof.

The gel nicotine composition may contain from 1 weight percent to 85 weight percent water. The gel nicotine composition may contain from 2 weight percent to 50 weight percent water. Preferably, the gel nicotine composition may contain from 3 weight percent to 30 weight percent water. The gel nicotine composition may contain from 8 weight percent to 20 weight percent water. The gel nicotine composition may comprise 10 weight percent to 15 weight percent water.

A gel nicotine composition comprises at least 0.2 weight percent nicotine. More preferably, the nicotine content in the gel nicotine composition is at least about 0.4 weight percent. The gel nicotine composition has a nicotine content of about 12 weight percent or less, such as about 10 weight percent or less, preferably about 8 weight percent or less, more preferably about 5 weight percent or less, preferably about 3.6 weight percent or less. can have Most preferably, the gel nicotine composition comprises about 0.4 weight percent to 3.6 weight percent nicotine.

In one exemplary embodiment, the gel nicotine composition comprises 80 weight percent liquid tobacco extract, 19 weight percent additional non-aqueous solvent, and 1 percent agar. In this exemplary embodiment, the nicotine composition comprises 19 weight percent glycerin as the additional non-aqueous solvent, and 80 weight percent liquid tobacco extract, wherein the liquid tobacco extract comprises 59 weight percent glycerin, 37 weight percent 0.5 weight percent water, 1.2 weight percent nicotine, 0.5 weight percent acetic acid, and 1.8 weight percent other ingredients, including desirable flavor compounds derived from the extraction process described herein. Including balance of ingredients. Thus, the nicotine composition of this exemplary embodiment contains 66.2 weight percent glycerin, 30 weight percent water, 0.96 weight percent nicotine, 0.4 weight percent acetic acid, 1 percent agar, and Contains 1.44 weight percent balance of other ingredients, including desirable flavor compounds derived from the extraction process described herein.

A nicotine composition according to the invention may be provided in a cartridge for use in an aerosol generating system. The cartridge may comprise an atomizer configured to generate an aerosol from the nicotine composition. The atomizer may be a thermal atomizer configured to heat the nicotine composition to generate an aerosol. A thermal atomizer may, for example, comprise a heater and a liquid-conveying element configured to move the nicotine composition to the heater. The liquid-conveying element may comprise a capillary wick. Alternatively, the atomizer may be a non-thermal atomizer configured to generate an aerosol from the nicotine composition by means other than heating. For example, the non-thermal atomizer may be an impinging jet atomizer, an ultrasonic atomizer, or a vibrating mesh atomizer.

A cartridge containing a nicotine composition may be used in conjunction with any suitable aerosol generating device that includes a housing configured to receive at least a portion of the cartridge. The aerosol generator may include a battery and control electronics.

The nicotine composition may be a gel nicotine composition or a liquid nicotine composition as described herein for use in an aerosol generating system.

The characteristics of the nicotine composition, as well as the resulting aerosol generated from the nicotine composition and delivered to the consumer, can be adjusted through control of the parameters of the extraction process.

According to the present invention, the steps of heating the tobacco starting material at an extraction temperature of 100 degrees Celsius to 160 degrees Celsius for at least 90 minutes and collecting volatile compounds released from the tobacco starting material during the heating step. , a non-aqueous solvent, nicotine, and 0.25, prepared by a method comprising forming a liquid tobacco extract comprising the collected volatile compounds; and forming a nicotine composition from the liquid tobacco extract. and a first weight ratio of (β- ^ionone + β-damascenone) to (phenol) greater than A nicotine composition is provided that includes a second weight ratio.

As discussed above, the nicotine composition may be produced from a liquid tobacco extract from tobacco starting material consisting of a single type of natural tobacco. The tobacco starting material may comprise a blend of two or more types of natural tobacco. Alternatively, the nicotine composition forms a first tobacco starting material consisting of a first single type of natural tobacco extracted to form a first extract, and a second extract. may be produced from a liquid tobacco extract from a blend produced from a second tobacco starting material consisting of a second tobacco starting material consisting of a second single type of natural tobacco extracted to produce the first extract and the second are blended to form a liquid tobacco extract. Two or more extracts may be blended in this manner to form a liquid tobacco extract. The ratio of different tobacco types can be adapted depending on the desired characteristics of the aerosol generated from the nicotine composition. For example, if it is desired to provide a relatively high level of nicotine, the percentage of burley tobacco may be increased.

The term "natural tobacco" is used herein in the context of the present invention to describe any part of any plant member of the genus Nicotiana, including but not limited to leaves, midribs, stems and petioles. used for In particular, natural tobacco is derived from full-cure tobacco material, burley tobacco material, orient leaf tobacco material, Maryland tobacco material, dark tobacco material, dark fired tobacco material, rustica tobacco material, and other rare or specialty tobacco materials. or blends thereof. As described in more detail below, the tobacco material may be whole (eg, whole tobacco leaves), shredded, chopped, or ground.

When it is desired to produce a nicotine composition from a combination of two or more different tobacco types to form a liquid tobacco extract, the tobacco types are selected within the defined range of 100 degrees Celsius to 160 degrees Celsius. or the mixture of tobacco types may be heated together at a single extraction temperature within that range.

The tobacco starting material may be solid tobacco material such as powder, leaf scraps or pieces, or intact leaves. Alternatively, the tobacco starting material may be a liquid tobacco material such as a dough, gel, slurry or suspension.

The tobacco starting material may be derived from any suitable tobacco material including, but not limited to, tobacco leaves, tobacco stems, reconstituted tobacco, cast tobacco, extruded tobacco, or tobacco-derived pellets.

In the process of preparing the tobacco starting material, tobacco is preferably crushed or cut to reduce the size of tobacco particles within the tobacco starting material. This may advantageously improve the homogeneity of heating of the tobacco starting material and the efficiency of extraction.

The tobacco starting material may optionally be dried prior to the heating step to reduce the moisture content of the tobacco starting material. Drying of the tobacco starting material may be performed by any suitable chemical or physical drying process. Alternatively, water may be added to the tobacco starting material prior to the heating step to increase the moisture content of the tobacco starting material.

Preparing the tobacco starting material may include impregnating the tobacco starting material with an aerosol former. If this impregnation of the tobacco starting material is performed prior to the heating step, this may advantageously increase the amount of certain desired tobacco compounds released from the tobacco starting material upon heating. For example, impregnation of tobacco starting material with glycerin has been found to advantageously increase the amount of nicotine extracted from the tobacco starting material. In another embodiment, impregnation of the tobacco starting material with a non-aqueous extraction solvent that is also an aerosol former, such as propylene glycol, glycerin, 1,3-propanediol, triacetin, or mixtures thereof, advantageously results in tobacco It has been found to increase the amount of flavor compounds extracted from the starting material.

Preferably, in the process of preparing the natural tobacco material, the tobacco is not subjected to any treatment adapted to alter the pH of the tobacco. In particular, in the process of preparing natural tobacco material, the tobacco is not subjected to any treatment adapted to significantly increase the pH of the tobacco. For example, the natural tobacco material is not contacted with an aqueous solution containing salts of alkali or alkaline earth metals. Advantageously, maintaining the tobacco material in a less modified state may provide a more authentic or natural flavor profile that may be perceived by consumers. I know it. Additionally, subjecting the natural tobacco material to a treatment adapted to increase the pH of the tobacco, such as an alkaline treatment, prior to heating the tobacco material as part of the extraction process, may provide the desired heated tobacco in the liquid tobacco extract. The inventors have found that this leads to a reduction in the level of tobacco flavor compounds. As an example, not subjecting the natural tobacco material to alkali treatment may reduce the weight ratio of (β-ionone + β-damascenone) to (phenol) in the liquid tobacco extract compared to the corresponding alkali-treated natural tobacco material. It has been found to be associated with significant increases.

In a preferred embodiment, the tobacco starting material consists of natural tobacco. Thus, the tobacco starting material may have a moisture content of about 11 percent by weight (a moisture content typically found in natural tobacco materials).

In other embodiments, the tobacco starting material may contain one or more additional ingredients such as, for example, non-aqueous solvents and/or added water. Examples of suitable solvents include propylene glycol.

Accordingly, the tobacco starting material is at least about 40 weight percent natural tobacco material, or at least about 60 weight percent natural tobacco material, or at least about 80 weight percent natural tobacco material, or at least about 90 weight percent natural tobacco material; or at least about 95 weight percent natural tobacco material.

In some embodiments, the moisture content of the tobacco starting material is from about 3 weight percent to about 60 weight percent, more preferably from about 3 weight percent to about 20 weight percent, even more preferably from about 3 weight percent to about 12 weight percent. It can be a percent. In other embodiments, the moisture content of the tobacco starting material is from about 5 weight percent to about 60 weight percent, more preferably from about 5 weight percent to about 20 weight percent, even more preferably from about 5 weight percent to about 12 weight percent. can be In a further embodiment, the tobacco starting material has a moisture content of from about 8 weight percent to about 60 weight percent, more preferably from about 8 weight percent to about 20 weight percent, even more preferably from about 8 weight percent to about 12 weight percent. could be.

In some embodiments, the non-aqueous solvent content is at least about 5 weight percent, or at least about 10 weight percent, or at least about 15 weight percent, or at least about 20 weight percent, or at least about 25 weight percent, or at least It may be about 30 weight percent, or at least about 35 weight percent, or at least about 40 weight percent.

Optionally, the tobacco starting material may be enzymatically digested prior to the heating step. This has been found to provide a significant increase in the yield of specific flavor compounds from the tobacco starting material.

The tobacco starting material may optionally be analyzed prior to the heating step to determine the reducing sugar content of the composition, eg alkaloids. This information about the composition can be usefully used to select an appropriate extraction temperature.

The extraction temperature and duration of heating will depend on factors such as the type of tobacco, other possible components of the tobacco starting material, the desired level of nicotine, or the desired composition of the nicotine composition formed from the liquid tobacco extract. Depending on factors, it may be selected within the ranges defined above. By controlling the combination of extraction temperature and time, the liquid tobacco extract can be tailored according to the desired properties of the aerosol generated from the nicotine composition. In particular, the ratio of specific tobacco compounds within the nicotine composition can be adjusted to some extent through the selection of extraction parameters to maximize the ratio of desirable and undesirable tobacco compounds within the liquid tobacco extract and nicotine composition. can be adjusted.

For a particular tobacco compound, variations in the level of compound release with extraction temperature during the extraction process can be readily determined for any given tobacco starting material. For example, it has been shown that the level of nicotine released from tobacco starting materials typically increases with increasing extraction temperature. The rate of increase has been found to vary with different tobacco types.

Also, the levels of desirable tobacco flavor compounds such as β-damascenone and β-ionone released from the tobacco material increase with increasing extraction temperature up to a certain peak extraction temperature, after which these levels begin to decrease. was found. The peak extraction temperature for these flavor compounds is typically in the range of 100 degrees Celsius to 160 degrees Celsius so that the level of desired flavor compounds in the extraction method can be effectively optimized.

The method of immersing the tobacco material in a suitable liquid solvent, such as an aerosol former, at room temperature or below for several weeks to extract the tobacco constituents into the solvent typically requires less than the content of the composition of the present invention. also yields much lower component contents. An extraction process in which the tobacco material is immersed in a suitable solvent, such as an aerosol former, at room temperature or below does not generate compounds that are not present in tobacco but are thermally generated after the Maillard reaction has taken place. One such compound that is thermally generated after the Maillard reaction has taken place is furaneol. Furaneol is derived from heat treating the inherent reducing sugar content of tobacco plant material with other tobacco plant components.

Bright tobacco typically has a much higher reducing sugar content (up to 25% by weight) than burley tobacco, and the amount of furaneol released upon heating of bright tobacco depends on the extraction temperature. It is found to vary significantly and that there is a direct correlation between the extraction temperature and the level of furaneol released. As described herein, the peak extraction temperature for such flavor compounds is typically 100 degrees Celsius so that the level of such desirable flavor compounds in the extraction process can be effectively optimized. to 160 degrees Celsius.

A number of undesirable tobacco compounds have been found to increase slowly with increasing extraction temperature up to a threshold temperature, above which a rapid increase is observed. This applies, for example, to levels of phenol, other phenolic compounds, and TSNAs, and in the case of bright tobacco, to furan and formaldehyde levels. Often the threshold temperature is in the range of 100 degrees Celsius to 160 degrees Celsius, so the level of undesirable compounds can be effectively controlled in the extraction process.

It has been found by the inventors of the present invention that for certain tobacco types, the level of certain undesirable nitrogen compounds, such as TSNA, released during extraction depends on the extraction temperature. For bright tobacco, the content of nitrogen compounds is typically very low, and increasing the extraction temperature has little effect on the amount of TSNAs released during the extraction process. Burley tobacco, on the other hand, typically has a much higher content of nitrogen compounds, and the amount of TSNAs released upon heating varies significantly with extraction temperature, with both extraction temperature and the level of TSNAs released. It is found that there is a direct correlation between

It has also been found by the inventors of the present invention that for certain tobacco types, the level of a particular undesirable furan, 2-furanmethanol, released during extraction depends on the extraction temperature. For burley tobacco, the reducing sugar content is typically very low (less than 2% by weight), and increasing the extraction temperature has little effect on the level of 2-furanmethanol released during the extraction process. . Bright tobacco, on the other hand, typically has a much higher reducing sugar content (up to 25% by weight), and the amount of 2-furanmethanol released upon heating varies significantly with extraction temperature. , it is found that there is a direct correlation between the extraction temperature and the level of 2-furanmethanol released. The extent to which increased extraction temperature increases the level of 2-furanmethanol released from bright tobacco may vary for each tobacco type.

As described herein, during the heating step in the extraction process, the tobacco starting material is heated to an extraction temperature of about 100 degrees Celsius to about 160 degrees Celsius. When the tobacco starting material is heated to temperatures above this range, the resulting compositions have much higher phenol to β-ionone and β-damascenone weights and lower β-ionone and β-damascenone to phenol weights. A weight ratio is provided.

4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), (R,S)-N-nitrosoanatabine (NAT), (R,S)-N-nitrosoanabasine (NAB) and N-nitrosonornicotine (NNN) are TSNAs. As described herein, relatively high amounts of these undesirable compounds are derived from tobacco high in nitrogen compounds, such as burley tobacco, and the amount of TSNAs released upon heating varies depending on the extraction temperature. A direct correlation between the extraction temperature and the level of TSNA released is found.

As described herein, relatively high amounts of 2-furanmethanol are derived from tobacco with high reducing sugar content, such as bright tobacco, and the amount of 2-furanmethanol released upon heating is It is found to vary significantly with extraction temperature, with a direct correlation between extraction temperature and the level of 2-furanmethanol released.

As described herein, during the heating step in the extraction process, the tobacco starting material is heated to an extraction temperature of about 100 degrees Celsius to about 160 degrees Celsius. When the tobacco starting material is heated above this range, the weight of TSNA and 2-furanmethanol relative to the weight of β-ionone and β-damascenone is much higher and lower in the resulting composition (β- ionone + β-damascenone) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R,S)-N-nitrosoanatabine) A weight ratio of basine (NAB) and N-nitrosonornicotine (NNN) + (2-furanmethanol)/600) is provided.

Although nicotine is typically present in higher weight percentages in extracts produced from burley tobacco compared to bright tobacco, certain undesirable nitrogen compounds such as TSNAs are typically present in A higher proportion is derived from burley tobacco compared to bright tobacco. Certain desirable flavor compounds, such as furaneol, are derived from reducing sugars and are typically present in higher amounts in bright tobacco compared to burley tobacco due to the higher reducing sugars in bright tobacco. , 2-furanmethanol, are also derived from reducing sugars and are typically present in higher amounts in bright tobacco compared to burley tobacco. Therefore, the nicotine compositions of the present invention are preferably produced from a blend of different tobacco types. Preferably, the nicotine composition is derived from burley and bright tobacco. Bright tobacco can be one or more of Orient leaf tobacco and full-cure tobacco.

During the heating step, the tobacco starting material is heated to an extraction temperature of about 100 degrees Celsius to about 160 degrees Celsius. Below this range, insufficient concentrations of nicotine and certain flavor compounds are released from the tobacco starting material such that the resulting liquid tobacco extract lacks the desired flavor characteristics. On the other hand, when tobacco starting materials are heated to temperatures above this defined range, unacceptably high levels of certain undesirable tobacco compounds such as phenol, TSNA and 2-furanmethanol can be released. have a nature.

Preferably, the extraction temperature is at least about 110 degrees Celsius, more preferably at least about 115 degrees Celsius, more preferably at least about 120 degrees Celsius, more preferably at least about 125 degrees Celsius.

The extraction temperature is preferably no greater than about 150 degrees Celsius, more preferably no greater than about 145 degrees Celsius, more preferably no greater than about 140 degrees Celsius, and most preferably no greater than about 135 degrees Celsius. .

For example, the extraction temperature may be about 110 degrees Celsius to 150 degrees Celsius, or about 120 degrees Celsius to about 140 degrees Celsius, or about 125 degrees Celsius to about 135 degrees Celsius, or about 130 degrees Celsius. An extraction temperature of about 130 degrees Celsius has been found to provide a particularly optimized ratio of desirable and undesirable compounds in the liquid tobacco extract.

The tobacco starting material is heated at the extraction temperature for at least about 30 minutes, or at least about 60 minutes, or at least about 90 minutes, more preferably at least about 120 minutes. This extraction time is long enough to be able to efficiently extract the desired tobacco flavor compounds to provide a nicotine composition capable of producing an aerosol with the desired flavor characteristics.

The tobacco starting material is heated at the extraction temperature for preferably no more than about 270 minutes, more preferably no more than about 180 minutes.

For example, the tobacco starting material may be heated for about 90 minutes to about 270 minutes, or about 120 minutes to about 180 minutes.

The heating times indicated above correspond to the duration of time that the tobacco starting material is heated at the extraction temperature and do not include the time it takes to raise the temperature of the tobacco starting material to the extraction temperature.

Generally, any moisture present in the natural tobacco material is released along with the volatile species in the form of vapors as the natural tobacco material is heated.

The heating step is preferably performed in an inert atmosphere. For example, natural tobacco material may be heated in a stream of inert gas or in a stream of a combination of inert gas and water or steam. A stream of inert gas such as nitrogen is preferably passed through the tobacco starting material during the heating step. Alternatively, the heating step may be performed under vacuum.

The inventors have found that natural tobacco materials in an inert atmosphere are freed from the volatile tobacco compounds released into the inert gas stream during the heating process, with the result that the inert gas acts as a carrier for the volatile components. It has been found to be advantageous to heat the The inert gas stream serves to carry vapors generated by evaporation of the moisture content of the natural tobacco material and volatile species (including particularly nicotine, and/or flavor-related compounds, or both) from the extraction equipment.

Furthermore, the use of a stream of inert gas (such as nitrogen) under light overpressure in the extraction equipment has the advantage of preventing the presence of oxygen in the extraction equipment. This can also be accomplished by performing the heating step under vacuum. These advantages are desirable in that they prevent the risk of any combustion (even partial combustion) of the natural tobacco material during the heating process. Uncontrolled combustion of natural tobacco materials would clearly be undesirable as it would present a major safety risk within the manufacturing environment. However, the inventors have found that even limited and partial combustion of natural tobacco material may (and may be undesirable) lead to a reduction in the quality of the tobacco extract obtainable by the present method. I found

While not wishing to be bound by theory, it is understood that preventing combustion of natural tobacco material also prevents the formation of any undesirable combustion by-products. Further, when conditions that would promote combustion of the natural tobacco material are prevented, the natural tobacco material can be treated with a tobacco-containing substrate (e.g., homogenized tobacco material) typically in a "heated non-combustible" article. It is effectively heated under conditions that somewhat mimic the conditions under which it is heated. As a result, selective extraction of the flavor-imparting volatile species responsible for the taste consumers associate with heated tobacco is advantageously preferred.

Therefore, extraction efficiency, product quality, and manufacturing safety are advantageously enhanced by performing the second heating step in an inert atmosphere.

The inert gas flow rate may be optimized based on the size and geometry of the extraction chamber. A relatively high flow rate of inert gas may advantageously further improve the efficiency of extraction from the tobacco starting material.

The addition of water or steam to the tobacco during extraction has been found to increase the yield of extracted constituents. However, excessive addition of water or steam leads to processing difficulties, such as stickiness of the tobacco material.

Suitable heating methods for effecting heating of tobacco starting materials are known to those skilled in the art and include, but are not limited to, dry distillation, steam distillation, vacuum distillation, flash distillation, and thin film steam distillation.

Optionally, the tobacco starting material may be enzymatically digested prior to the heating step. This has been found to provide a significant increase in the yield of specific flavor compounds from the tobacco starting material.

The tobacco starting material may optionally be analyzed prior to the heating step to determine the reducing sugar content of the composition, eg alkaloids. This information about the composition can be usefully used to select an appropriate extraction temperature.

Volatile compounds released from the tobacco starting material during heating of the tobacco starting material are collected using any suitable technique. As noted above, when the tobacco starting material is heated in an inert gas stream, volatile compounds are collected from the inert gas stream. Different collection methods will be known to those skilled in the art.

The step of collecting the volatile compounds preferably uses absorption techniques in which the volatile compounds are entrapped in a non-aqueous solvent. For example, a stream of inert gas containing volatile compounds may be directed to a container of non-aqueous extraction solvent. Preferably, the non-aqueous extraction solvent is an aerosol former. Preferably, the non-aqueous solvent is triacetin, glycerin, propylene glycol (PG), 1,3-propanediol, or mixtures thereof. The non-aqueous extraction solvent may be a polyhydric alcohol. The use of an aerosol former as a non-aqueous extraction solvent can be beneficial as it can retain the aerosol former as a diluent in the final liquid tobacco extract and nicotine composition. This means that an additional step to remove the non-aqueous extraction solvent is not necessarily required.

In a preferred embodiment, volatile compounds are collected by condensation and the resulting condensate is added to a liquid aerosol former, preferably PG.

Addition of a liquid aerosol former, especially PG, advantageously prevents the condensed volatile compounds from separating into two phases or forming an emulsion (as some tobacco ingredients tend to do). may prevent Without wishing to be bound by theory, the solubility of a tobacco component in an aqueous extract (i.e., the aqueous fraction of a liquid naturally occurring tobacco extract) depends primarily on its polarity, its concentration, and its aqueous The inventors have observed that it depends on the pH of the extract, which may vary depending on the tobacco type. As a result, if the amount of aerosol former is not sufficient, the liquid naturally occurring tobacco extract tends to form an oily layer on the surface. These oily materials condense at different locations on the capture device and the collection process is performed. The addition of a liquid aerosol former such as PG helps prevent formation of such layers and favors homogenization of the liquid naturally occurring tobacco extract. This in turn helps prevent the loss of desirable flavor-related compounds during the fourth (drying) step, where such compounds may undesirably deposit on equipment surfaces.

In addition, liquid aerosol formers advantageously help entrap flavor-relevant compounds, regardless of their polarity and volatility. Furthermore, during the fourth (drying) step, the liquid aerosol former not only helps prevent loss of the most volatile fraction, but also the liquid naturally occurring tobacco extract to obtain a concentrated tobacco extract. Favors selective removal of excess water from the extract.

The use of PG as an aerosol former for the condensation-collection process has the additional advantage that PG exerts antimicrobial activity by reducing the water activity of aqueous solutions. Therefore, by adjusting the content of PG in the liquid, naturally occurring tobacco extract, it is also possible to ensure that the extract does not undergo substantially any microbial activity.

The liquid naturally occurring tobacco extract obtained at the end of the collection step is typically a homogeneous liquid. Such homogeneous liquids may be stored for a limited holding period (up to about 4 weeks) before undergoing an optional drying step. The composition of a liquid naturally occurring tobacco extract depends on a number of variables, including the nature of the natural tobacco material, the moisture content in the natural tobacco material, and the amount of water used to prepare the natural tobacco material. Included is the amount of aerosol former used, if any.

The non-aqueous extraction solvent is preferably kept at a temperature below 0 degrees Celsius to optimize the transfer of volatile compounds to the non-aqueous extraction solvent. The non-aqueous extraction solvent is preferably kept at a temperature of -10 degrees Celsius or higher. Temperatures below these values can lead to undesirable freezing phenomena.

As an alternative to absorption techniques, the step of collecting volatile compounds may be carried out using condensation techniques in which the volatile compounds are condensed and the condensate is collected. Condensation of volatile compounds may be performed using any suitable device, for example in a cooling column. If the volatile compounds are collected by condensation, the step of forming the liquid tobacco extract may include adding the condensate to a non-aqueous extraction solvent such as an aerosol former.

As a further alternative, the step of collecting volatile compounds can be performed using adsorption techniques in which the volatile compounds are adsorbed onto the surface of a solid adsorbent material such as activated carbon. The adsorbed compounds are then transferred into the non-aqueous extraction solvent.

Optionally, forming the liquid tobacco extract comprises a filtering step.

Optionally, forming the liquid tobacco extract comprises blending, in which extracts derived from different tobacco starting materials are combined.

In the method, the next step is forming a liquid tobacco extract from the collected volatile compounds. The nature of this step may depend on the collection method. "Collected volatile compounds" typically comprise a solution of tobacco-derived volatile compounds in a non-aqueous extraction solvent.

The extraction method provides a liquid tobacco extract containing greater than about 20 weight percent water, based on the weight of the liquid tobacco extract. Generally, the liquid tobacco extract may contain at least about 40 weight percent water. The liquid tobacco extract may contain from about 40 weight percent to about 70 weight percent water.

The extraction methods described herein provide a liquid tobacco extract having a nicotine content of at least 0.2 weight percent. More preferably, the nicotine content in the liquid tobacco extract is at least about 0.4 weight percent. The liquid tobacco extract may have a nicotine content of about 10 weight percent or less, more preferably about 8 weight percent or less, more preferably about 5 weight percent or less, and most preferably about 3.6 weight percent or less. Most preferably, the liquid tobacco extract contains from about 0.4 weight percent to 3.6 weight percent nicotine, based on the weight of the liquid tobacco extract.

The extraction methods described herein have a non-aqueous extraction solvent content of about 25 weight percent to about 65 weight percent, preferably about 30 weight percent to 60 weight percent, most preferably about 35 weight percent to about 55 weight percent. provides a liquid tobacco extract that can have Preferably, the non-aqueous extraction solvent is triacetin, glycerin, propylene glycol, 1,3-propanediol, or mixtures thereof.

In the method, the next step involves forming a nicotine composition from the liquid tobacco extract.

The nicotine composition can advantageously be formed directly from the liquid tobacco extract resulting from the extraction process without requiring the addition of additional nicotine. The nicotine composition can advantageously be formed directly from the liquid tobacco extract resulting from the extraction process without requiring the addition of further flavor compounds. A nicotine composition can advantageously be formed directly from a liquid tobacco extract without the need for the addition of additional non-aqueous solvents. For example, the liquid tobacco extract produced by the extraction process can be used to make nicotine compositions containing 10-20 mg nicotine per milliliter without requiring the addition of nicotine.

Alternatively, the liquid tobacco extract may be subjected to additional processing steps to form the nicotine composition. Even when subjected to such additional steps, the nicotine composition may be formed without the need to add additional nicotine or flavor compounds. Preferably, the liquid tobacco extract may be concentrated in the drying step herein to form a concentrated tobacco extract, and the concentrated tobacco extract may be used to form a nicotine composition. Preferably, additional non-aqueous solvent may be added to the liquid tobacco extract or concentrated tobacco extract to form the nicotine composition.

As noted above, when the volatile compounds are collected by absorption in the non-aqueous extraction solvent, the liquid solvent may contain both the non-aqueous extraction solvent and water, thus concentrating the solution to form a liquid tobacco extract. It is preferred to dry the solution of the volatile compound in the liquid solvent. This can be done, for example, to reach the desired concentration of nicotine or flavor compound. Drying includes desiccation, molecular sieving, freeze-drying, phase separation, distillation, membrane permeation, controlled crystallization and filtration of water, reverse hygroscopicity, ultracentrifugation, liquid chromatography, reverse osmosis or chemical drying. It can be performed using any suitable means, including but not limited to.

The solution of volatile compounds in the liquid solvent forming the liquid tobacco extract is preferably concentrated by drying in the drying step to form a concentrated tobacco extract. Concentrated tobacco extracts may be used to form nicotine compositions.

In the drying step, a solution of volatile compounds in a liquid solvent is heated to evaporate at least some of the water to obtain a concentrated tobacco extract. To this end, a solution of volatile compounds in a liquid solvent may be heated to a temperature and for a period of time such that the water content in the tobacco extract is reduced by at least about 60 percent.

In one embodiment, the solution of the volatile compound in the liquid solvent is heated under vacuum, preferably at a temperature of at least about 70 degrees Celsius. In another embodiment, the solution of the volatile compound in the liquid solvent is heated at a temperature of at least about 35 degrees Celsius under a stream of air, preferably an air stream having relatively low humidity. A concentrated tobacco extract can thus be obtained. One such concentrated tobacco extract typically contains less than about 20 weight percent water.

In the drying step, the liquid tobacco extract is heated from about 35 degrees Celsius to about 95 degrees Celsius, more preferably from about 35 degrees Celsius to about 90 degrees Celsius, even more preferably from about 35 degrees Celsius to about 85 degrees Celsius, most preferably It can be heated from about 35 degrees Celsius to about 80 degrees Celsius.

In the drying step, the liquid tobacco extract may be heated under reduced pressure. The liquid tobacco extract may be heated at pressures up to about 200 mbar. In the drying step, the liquid tobacco extract may be heated at a pressure of at least about 20 mbar.

Alternatively, the liquid tobacco extract may be heated under a stream of air during the drying process. The liquid tobacco extract may be heated under an air flow of at least about 10 kg/h. The liquid tobacco extract may be heated under an air flow of at least about 15 kg/h. The relative humidity of the air stream may be about 50 percent or less, preferably about 25 percent or less.

After the drying process, the liquid tobacco extract is called concentrated tobacco extract. The concentrated tobacco extract contains no more than about 20 weight percent water. Preferably, the concentrated tobacco extract comprises 8 weight percent to 15 weight percent water, based on the weight of the concentrated tobacco extract.

The drying step may have a non-aqueous extraction solvent content of from about 65 weight percent to about 95 weight percent, preferably from about 65 weight percent to 85 weight percent, most preferably from about 75 weight percent to about 85 weight percent. Provide an extract. Preferably, the non-aqueous extraction solvent is triacetin, glycerin, propylene glycol, 1,3-propanediol, or mixtures thereof.

The drying step has a nicotine content of at least about 0.2 weight percent nicotine, preferably from about 0.5 weight percent to about 12 weight percent nicotine, and most preferably from about 2 weight percent to about 8 weight percent nicotine. A concentrated tobacco extract is provided.

Concentrated tobacco extracts can be used directly to form nicotine compositions without requiring the addition of additional nicotine. Concentrated tobacco extracts can be used directly to form nicotine compositions without requiring the addition of additional non-aqueous solvents. Concentrated tobacco extracts can be used directly to form nicotine compositions without requiring the addition of additional water. Concentrated tobacco extracts can be used directly to form nicotine compositions without the need for the addition of additional flavorants.

Preferably, additional non-aqueous solvent may be added to the liquid tobacco extract or concentrated tobacco extract to form the nicotine composition.

The nicotine composition can have any of the preferred characteristics previously described herein.

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

Example 1
The tobacco starting material is prepared from fully cured bright tobacco material. The tobacco material is cut to form tobacco pieces having dimensions of 2.5 millimeters by 2.5 millimeters, and the tobacco pieces are loaded into the extraction chamber without compression. The tobacco starting material is heated to a temperature of 130 degrees Celsius in the extraction chamber for 3 hours. During heating, a stream of nitrogen is passed through the extraction chamber at a rate of about 40 liters/minute.

Volatile compounds released from the tobacco starting material during the heating process are collected by absorption into a liquid solvent formed from propylene glycol at minus 10 degrees Celsius and agitation at 750 rpm.

The nicotine composition of Example 1 is a liquid tobacco extract obtained directly from an extraction process at a temperature of 130 degrees Celsius for 3 hours. The nicotine composition includes phenol, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, (R,S)-N-nitrosoanatabine, (R,S)-N-nitrosoanatabine It provides optimized levels of desirable flavor compounds such as β-damascenone and β-ionone versus undesirable compounds such as vasine, N-nitrosonornicotine, and 2-furanmethanol. The nicotine composition further provides a level of desirable flavor compounds such as furaneol and 2,3-diethyl-5-methylpyrazine versus nicotine. Specifically, in the nicotine composition, the weight ratio of (β-ionone + β-damascenone) to (phenol) is greater than 0.25 and (furaneol + (2,3-diethyl-5-methylpyrazine)*100) ) to (nicotine) weight ratio is greater than 5×10 −4 .

Example 2
This example provides two nicotine compositions according to the invention, both of which undergo an extraction process at a temperature of 130 degrees Celsius for 3 hours, followed by drying to reduce the moisture level of the liquid tobacco extract to about 6 percent. A concentrated tobacco extract obtained from the process. The concentrated tobacco extract is then used directly to form the nicotine composition. In both nicotine compositions, the weight ratio of (β-ionone + β-damascenone) to (phenol) was greater than 0.25 and (furaneol + (2,3-diethyl-5-methylpyrazine)*100)) to ( nicotine) weight ratio is greater than 5 x 10-4.

Example 2a
Example 2a relates to a concentrated tobacco extract derived from fully cured bright tobacco material. The contents of the liquid tobacco extract of Example 2a are as follows.
- Nicotine: 0.53% w/w
- Propylene glycol: 91.8% w/w
- Water: 6.3% w/w
- Balance (including flavors detailed in Table 1 below): 1.57% w/w

Example 2b
Example 2b relates to a concentrated tobacco extract derived from Burley tobacco material. The contents of the liquid tobacco extract of Example 2b are as follows.
- Nicotine: 1.82% w/w
- Propylene glycol: 89.6% w/w
- Water: 5.7% w/w
- Balance (including flavors detailed in Table 1 below): 2.88% w/w

The nicotine compositions of Examples 2a and 2b according to the present invention consisted of phenol, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, (R,S)-N-nitrosoanatabine, ( Contains acceptably low levels of undesirable compounds such as R,S)-N-nitrosoanabasine, N-nitrosonornicotine, and 2-furanmethanol.

Example 3
This example provides three nicotine compositions according to the present invention, each of which reduced the moisture level of the liquid tobacco extract to about 12.5 percent following an extraction process at a temperature of 130 degrees Celsius for 3 hours. It is a concentrated tobacco extract obtained from a drying process. The concentrated tobacco extract is then used directly to form the nicotine composition. In these nicotine compositions, the weight ratio of (β-ionone + β-damascenone) to (phenol) is greater than 0.25 and (furaneol + (2,3-diethyl-5-methylpyrazine)*100)) to ( nicotine) weight ratio is greater than 5×10 −4 .

Example 3a
Example 3a relates to a concentrated tobacco extract derived from orient leaf bright tobacco material. The contents of the concentrated tobacco extract of Example 3a are as follows.
- Nicotine: 0.4% w/w
- Propylene glycol: 84% w/w
- Acetic acid: 1.0% w/w
- Water: 12.5% w/w
- Balance (including flavors): 2.1% w/w

Example 3b
Example 3b relates to a concentrated tobacco extract derived from fully cured bright tobacco material. The contents of the concentrated tobacco extract of Example 3b are as follows.
- Nicotine: 1.2% w/w
- Propylene glycol: 84% w/w
- Acetic acid: 1.0% w/w
- Water: 12.5% w/w
- Balance (including flavors): 1.3% w/w

Example 3c
Example 3c relates to a concentrated tobacco extract derived from Burley tobacco material. The contents of the concentrated tobacco extract of Example 3c are as follows.
- Nicotine: 2.6% w/w
- Propylene glycol: 84% w/w
- Acetic acid: 0.5% w/w
- Water: 12.5% w/w
- Balance (including flavors): 0.4% w/w

The nicotine composition of Example 3 contains phenol, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, (R,S)-N-nitrosoanatabine, (R,S)- It provides optimized levels of desirable flavor compounds such as β-damascenone and β-ionone versus undesirable compounds such as N-nitrosoanabasine, N-nitrosonornicotine, and 2-furanmethanol. The nicotine composition further provides a level of desirable flavor compounds such as furaneol and 2,3-diethyl-5-methylpyrazine versus nicotine.

Example 4
The liquid tobacco extract of Example 1 was concentrated in a drying process to reduce the moisture level of the liquid tobacco extract to about 15 percent.
Glycerin is added to the resulting concentrated liquid tobacco extract to form a nicotine composition such that the nicotine composition contains, based on the weight of the nicotine composition, 20 weight percent glycerin and 80 weight percent It contained liquid tobacco extract.

Example 5
Example 5 relates to a nicotine composition in gel form according to the invention. A gel nicotine composition is formed from the liquid tobacco extract of Example 1. The content of the gel nicotine composition is as follows.
- Liquid Tobacco Extract of Example 1: 99.0% w/w
・ Agar: 1.0% w/w

Example 6
Three tobacco starting materials according to the present invention are each prepared from a fully cured bright tobacco material (6A), a Burley tobacco material (6B), and an orient leaf tobacco material (6C).

Each one of the three tobacco materials is cut to form tobacco pieces having dimensions of 2.5 millimeters by 2.5 millimeters, and the tobacco pieces are loaded into the extraction chamber without compression. be done.

Each one of the tobacco starting materials is heated to a temperature of 130 degrees Celsius for 120 minutes in the extraction chamber. During heating, a stream of nitrogen is passed through the extraction chamber at a flow rate of 2 liters/minute.

Volatile compounds released from each tobacco starting material during the heating process are collected by absorption into a liquid solvent formed from polypropylene glycol at 0 degrees Celsius.

A liquid tobacco extract is obtained directly from such an extraction process. Each liquid extract obtained from each one of the three tobacco starting materials was then concentrated under vacuum (50 mbar) at 55 degrees Celsius until reaching a moisture content of 12 percent ± 2 percent. be done.

In all three liquid extracts according to inventions 6A, 6B, and 6C, the (β-ionone + β-damascenone) to (phenol) weight ratio is consistently and significantly above 2.0. Furthermore, in all three liquid extracts according to inventions 6A, 6B, and 6C, the weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine)*100)) to (nicotine) was consistent and Remarkably above 1×10 ⁻³ . Furthermore, in all three liquid extracts according to inventions 6A, 6B, and 6C, (β-ionone + β-damascenone) versus (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + The weight ratio of (R,S)-N-nitrosoanatabine + (R,S)-N-nitrosoanabasine + N-nitrosonornicotine + ((2-furanmethanol)/600)) was consistently and significantly exceed 3.

Comparative Examples Two tobacco starting materials are prepared from fully cured bright tobacco materials (CE1, CE2). Two additional tobacco starting materials are prepared from burley tobacco materials (CE3, CE4). Each of the four starting tobacco materials is cut to form tobacco strips having dimensions of 2.5 millimeters by 2.5 millimeters.

Tobacco pieces are mixed with an alkaline solution of potassium carbonate in water to reach a predetermined pH for each tobacco material. One such alkaline treatment of starting tobacco material is described in US2016/360780.

More specifically, the tobacco starting materials CE1 and CE3 are mixed with an alkaline solution of potassium carbonate in water to reach pH 8, and the tobacco starting materials CE2 and C4 are mixed with an alkaline solution of potassium carbonate in water to reach pH 9.5. mixed with

After such alkaline treatment, the tobacco pieces of each tobacco starting material are loaded into the extraction chamber without compaction. Each tobacco starting material is heated in an extraction chamber to a temperature of 130 degrees Celsius for 120 minutes. During heating, a stream of nitrogen is passed through the extraction chamber at a rate of about 2 liters/minute.

Volatile compounds released from each tobacco starting material during the heating process are collected by absorption into a liquid solvent formed from polypropylene glycol at 0 degrees Celsius.

A liquid tobacco extract is obtained directly from such an extraction process. Each liquid extract obtained from each one of the four tobacco starting materials was then concentrated under vacuum (50 mbar) at 55 degrees Celsius to reach a moisture content of 12 percent ± 2 percent. be done.

In all four liquid extracts from Comparative Examples CE1, CE2, CE3, and CE4, the weight ratio of (β-ionone + β-damascenone) to (phenol) is consistently and significantly below 0.25. Furthermore, the weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine)*100)) to (nicotine) was consistent in all four liquid extracts from Comparative Examples CE1, CE2, CE3, and CE4. and significantly below 5×10 ⁻⁴ .

Claims (15)

A nicotine composition comprising: a non-aqueous solvent; at least 0.2 weight percent nicotine based on the weight of said nicotine composition; and a second weight ratio of (furaneol+(2,3-diethyl-5-methylpyrazine)*100)) to (nicotine) greater than 5×10 ⁻⁴ . said first weight ratio is greater than 0.5, more preferably greater than 1, even more preferably greater than 1.5, most preferably greater than 2, such as from 2 to 10 or from 2 to 5; 2. A nicotine composition according to claim 1. A nicotine composition according to any of claims 1 or 2, wherein said second weight ratio is between 8x10 ^-4 and 9x10 ^-3 . A nicotine composition according to any preceding claim, wherein the nicotine composition comprises from 0.4 weight percent to 3.6 weight percent nicotine based on the weight of the nicotine composition. further comprising a third weight ratio, wherein said third weight ratio is (β-ionone + β-damascenone) to (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R ,S)-N-nitrosoanatabine + (R,S)-N-nitrosoanabasine + N-nitrosonornicotine + ((2-furanmethanol)/600)), and the third weight ratio nicotine composition according to any of claims 1 to 4, wherein the nicotine composition is greater than 1.5. A nicotine composition according to any preceding claim, wherein said nicotine composition is derived from Burley and Bright tobacco. 7. The nicotine composition of claim 6, wherein said bright tobacco is one or more of Orient leaf tobacco and full-cure tobacco. A nicotine composition according to any preceding claim, wherein the non-aqueous solvent is glycerin, propylene glycol, triacetin, 1,3-propanediol, or mixtures thereof. of acetic acid, vanillin, 2-ethyl-3,5-dimethylpyrazine, 2-methylbutanoic acid, 3-methylbutanoic acid, 3-methyl-2,4-nonanedione, 2-methoxyphenol, 2-phenylethanol, eugenol, and sotolone A nicotine composition according to any preceding claim, further comprising one or more of: A nicotine composition according to any preceding claim, wherein the nicotine composition comprises at least 300 micrograms of acetic acid per gram of the nicotine composition. 9. The nicotine composition of claim 8, comprising from about 80 weight percent to about 90 weight percent of said non-aqueous solvent and from about 10 weight percent to about 15 weight percent water, based on the weight of said nicotine composition. A nicotine composition according to any preceding claim, wherein the nicotine composition is a liquid nicotine composition. A nicotine composition according to any preceding claim, wherein said nicotine composition is a gel nicotine composition. A cartridge containing a nicotine composition according to any one of claims 1-13. Non-aqueous solvent, nicotine, a first weight ratio of (β-ionone + β-damascenone) to (phenol) greater than 0.25 and (furaneol + (2,3-diethyl-5-methylpyrazine) greater than 5 x ^10-4 )*100) to (nicotine), comprising:
heating the tobacco starting material at an extraction temperature of 100 degrees Celsius to 160 degrees Celsius for at least 90 minutes;
collecting volatile compounds released from the tobacco starting material during the heating;
forming a liquid tobacco extract comprising the collected volatile compounds;
forming said nicotine composition from said liquid tobacco extract.