JP7436518B2 - Nicotine composition, method for producing the same, and aerosol-generating article comprising the same - Google Patents

Description

NICOTINE COMPOSITIONS FIELD OF THE INVENTION The present invention relates to nicotine compositions.

Aerosol generation systems for delivering an aerosol to a user 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 generation systems include 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 generation system is the electronic cigarette. Other known aerosol generation systems include non-thermal atomizers configured to generate aerosols from liquid compositions using, for example, impinging jets, ultrasound, or vibrating mesh techniques.

Nicotine compositions may be produced by an extraction process in which nicotine and other volatile flavor compounds are extracted from tobacco material 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 extract 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, alternative processes are known in which 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 part, on which a waxy layer accumulates 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 along with the aqueous portion to increase the extraction yield. On the other hand, the waxy phase is collected and ultimately forms the primary product of one such water distillation process. These products are often referred to as "tobacco essential oils" and contain high proportions 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 traces 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 that contains a highly concentrated mixture of mostly non-polar compounds that can be extracted using specific solvents and generally contains nicotine, which is generally relatively Present in high concentrations.

An alternative extraction process involves contacting tobacco material with a solvent under supercritical conditions (such as supercritical carbon dioxide). One such process is disclosed in US Pat. After dissolution of any soluble material, the supercritical fluid containing the dissolved material can be removed and the dissolved components of the feed material can be separated and removed 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 a high level of waxy, non-polarized It typically has a sexual compound and also contains nicotine, which is generally present in relatively high concentrations.

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

Liquid tobacco extracts and nicotine compositions obtained by such known extraction processes may have low levels of nicotine. Additionally, nicotine compositions obtained by such extraction processes may have low levels and a low variety 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. Generally, the concentration of nicotine, flavor species, and undesirable compounds obtained by such extraction processes can be significantly influenced by the type of tobacco or tobaccos used as starting material.

The aim of the present invention is to alleviate one or more disadvantages of nicotine compositions obtained by known processes. It is particularly preferred to produce new and improved nicotine compositions.

TECHNICAL FIELD This disclosure relates to nicotine compositions. Preferably, the nicotine composition comprises at least 0.2% by weight nicotine. Preferably, the nicotine composition includes 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 nicotine compositions prepared by a method comprising heating tobacco starting material at an extraction temperature of 100 degrees Celsius to 160 degrees Celsius for at least 90 minutes.

According to the 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 5×10 ⁻⁴ )*100) to (nicotine), the nicotine composition comprises 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 containing 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 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 generation system. In such aerosol generation systems, the nicotine composition is typically heated within the aerosol generation device.

As used herein, the term "aerosol generator" refers to a device that includes a heater element that interacts with the nicotine composition of the present invention to produce an aerosol. During use, volatile compounds are released from the nicotine composition by heat transfer and entrained into the air drawn through the aerosol generator. As the released compounds cool, they condense to form an aerosol that is inhaled by consumers.

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

A nicotine composition can include a non-aqueous solvent, water, nicotine, and a flavoring compound.

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

The nicotine composition can include a total non-aqueous solvent content of about 10 weight percent to about 95 weight percent. The nicotine composition preferably contains 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. Contains a total content of non-aqueous solvents of up to about 90 weight percent. Preferably, the non-aqueous solvent is triacetin, glycerin, propylene glycol, 1,3-propanediol, or a mixture thereof.

Those skilled in the art will appreciate that the weight percentages of certain ingredients are disclosed herein with respect to nicotine compositions, liquid tobacco extracts, or concentrated tobacco extracts; It will be understood that it is based on the weight of the particular ingredient relative to the total weight of the tobacco extract or concentrated tobacco extract.

The nicotine composition can include a total propylene glycol content of about 10 weight percent to about 95 weight percent. The nicotine composition can be about 20 weight percent to about 95 weight percent, such as about 50 weight percent to about 95 weight percent, or about 65 weight percent to about 95 weight percent, about 70 weight percent to about 90 weight percent, or about 80 weight percent The total content of propylene glycol can be from weight percent to about 90 weight percent.

The nicotine composition can include a total triacetin content of about 10 weight percent to about 95 weight percent. The nicotine composition may contain about 20 weight percent to about 95 weight percent, such as about 50 weight percent to about 95 weight percent, about 70 weight percent to about 90 weight percent, or about 65 weight percent to about 95 weight percent, or about 80 weight percent to about 95 weight percent. The total content of triacetin can be from weight percent to about 90 weight percent.

The nicotine composition can include a total glycerin content of about 10 weight percent to about 95 weight percent. The nicotine composition can be about 20 weight percent to about 95 weight percent, such as about 50 weight percent to about 95 weight percent, or about 65 weight percent to about 95 weight percent, about 70 weight percent to about 90 weight percent, or about 80 weight percent The total content of glycerin can be from weight percent to about 90 weight percent.

The nicotine composition can include a total content of 1,3-propanediol from about 10 weight percent to about 95 weight percent. The nicotine composition may contain 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. The total content of 3-propanediol may be included.

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. It is possible. Most preferably, the nicotine composition comprises 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 contains 10 weight percent to 15 weight percent water.

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 an organic acid that has a water solubility of about 500 mg/ml or greater at 20<0>C.

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

More preferably, the nicotine composition includes 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 includes lactic acid.

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

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 a nicotine composition, the total content of acetic acid in the nicotine composition, including both acetic acid derived from the extraction process and additional acetic acid, is preferably about 0. 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 It is approximately 8% by weight. More preferably, the total content of acetic acid is about 0.01 weight percent to about 6 weight percent, such as about 0.03 weight percent to about 6 weight percent, about 0.3 weight percent to about 6 weight percent, about 2 weight percent. Weight percent to about 6 weight percent, or about 3 weight percent to about 6 weight percent.

Preferably, the water-soluble organic acid content of the nicotine composition is about 8 weight percent or less. More preferably, the water-soluble organic acid content of the nicotine composition is 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 flavorants. Suitable non-tobacco derived flavorants include, but are not limited to, menthol.

Preferably, the nicotine composition has a non-tobacco-derived flavorant content of about 4 weight percent or less. More preferably, the nicotine composition has a non-tobacco-derived flavorant content of about 3 weight percent or less.

The nicotine composition is analyzed by gas chromatography to determine the liquid content. The weight of each compound within a 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 composition of the present invention, the first weight ratio of (β-ionone + β-damascenone) to (phenol) is greater than 0.25. The above ratio will be higher when the amount of the desired flavoring compounds β-ionone and β-damascenone is high or when 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 for example 2 to 10 or 2 to 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 composition of the invention, the second weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine)*100)) to (nicotine) is greater than 5x10 ^-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 between 8x10 ^-4 and 9x10 ^-3 , or between 1x10 ^-3 and 5x10 ^-3 It is.

The nicotine compositions of the present invention contain greater than 1.5 (β-ionone + β-damascenone) to (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 will be higher when the amounts of the desired flavor compounds β-ionone and β-damascenone are higher, or when the amounts of TSNA and 2-furanmethanol are lower.

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

The nicotine composition may also include other desirable compounds derived directly from natural tobacco, many of which are flavoring agents. The nicotine composition includes 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 include one or more of eugenol, and sotolone.

The nicotine composition includes beta-ionone. The nicotine composition comprises 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 at least 0.200 micrograms of β-ionone 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 a preferred embodiment, the nicotine composition comprises 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 comprises 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 comprises 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 1.10 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. For example, it may exceed 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. most preferably greater than 1.20, such as greater than 1.80.

The nicotine composition includes β-damascenone. The nicotine composition comprises 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 at least 0.350 micrograms of β-damascenone 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 a preferred embodiment, the nicotine composition comprises 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 comprises 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 Still more preferably 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 2.75 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. For example, it may exceed 1.60. (β-damasenone) 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 1.50. most preferably greater than 2.20, such as greater 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 greater than ^6.00x10-4 , such as greater than ^7.00x10-4 .

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 has 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 still At least 1.10 micrograms of furaneol per gram, and most preferably at least 1.30 micrograms of furaneol per gram of nicotine composition. In particularly preferred embodiments, the nicotine composition contains 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, and more preferably at least 1.80 micrograms of furaneol per gram of nicotine composition. 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 - the weight ratio of nitrosonol nicotine + ((2-furanmethanol)/600) is greater than 0.600, such as greater than 0.800, preferably greater than 1.00, more preferably greater than 1.50; Most preferably it exceeds 2.00, for example it may exceed 2.10.

The nicotine composition includes 2,3-diethyl-5-methylpyrazine. The nicotine composition contains at least 3.00 x 10 ^-3 micrograms of 2,3-diethyl-5-methylpyrazine per gram of nicotine composition, preferably at least 5.00 x 10 ^-3 micrograms per gram of nicotine composition. grams of 2,3-diethyl-5-methylpyrazine, more preferably at least 9.00 x 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 x 10 ^-2 micrograms of 2,3-diethyl-5-methylpyrazine per gram. In a preferred embodiment, the nicotine composition contains at least 2.50 x 10 ^-2 micrograms of 2,3-diethyl-5-methylpyrazine per gram of nicotine composition, more preferably at least 3.50 x 10 -2 micrograms of 2,3-diethyl-5-methylpyrazine per gram of nicotine composition ^{. 2} micrograms of 2,3-diethyl-5-methylpyrazine, even more preferably at least 5.00x10 ^-2 micrograms of 2,3-diethyl-5-methylpyrazine per gram of nicotine composition, most preferably Contains at least 7.50 x 10 ^-2 micrograms of 2,3-diethyl-5-methylpyrazine per gram of material. In particularly preferred embodiments, the nicotine composition comprises at least 9.00x10 ^-2 micrograms of 2,3-diethyl-5-methylpyrazine per gram of nicotine composition, preferably at least 0.10 micrograms of 2,3-diethyl-5-methylpyrazine 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 greater than 0.500, for example may be greater than 0.600. (2,3-diethyl-5-methylpyrazine) 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 0.0300, such as greater than 0.0400, preferably greater than 0.100, More preferably it exceeds 0.500, most preferably it exceeds 0.800, for example it may exceed 0.900.

The nicotine composition may include acetic acid. Preferably, the acetic acid is derived from the extraction process, but additional acetic acid may be added after the extraction process, as described herein above. 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 at least 700 micrograms of acetic acid per gram of nicotine composition. Preferably, each gram of nicotine composition will contain at least 900 micrograms of acetic acid. In a preferred embodiment, 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 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. It contains 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 weight ratio of (acetic acid) to (phenol) 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 - the weight ratio of nitrosonolnicotine + ((2-furanmethanol)/600) 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 comprises at least 3.00x10 ^-2 micrograms of vanillin per gram of nicotine composition, preferably at least 5.00x10 -2 micrograms of vanillin per gram of nicotine composition, more preferably at least 5.00x10 ^-2 micrograms of vanillin per gram of nicotine composition. It may contain at least 7.00 x 10 ^-2 micrograms of vanillin, most preferably at least 9.00 x 10 ^-2 micrograms of vanillin per gram of nicotine composition. In preferred embodiments, the nicotine composition has 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 still It contains at least 0.300 micrograms of vanillin per gram, and most preferably at least 0.400 micrograms of vanillin per gram of nicotine composition. In particularly preferred embodiments, the nicotine composition contains 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 at least 1 gram of nicotine composition. It comprises at least 0.700 micrograms vanillin per gram, even more preferably at least 0.800 micrograms vanillin per gram nicotine composition, and most preferably at least 0.900 micrograms vanillin per gram nicotine composition. The weight ratio of (vanillin) to (phenol) 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 - the weight ratio of nitrosonolnicotine + ((2-furanmethanol)/600) is greater than 0.110, such as greater than 0.150, preferably greater than 0.160, more preferably greater than 0.200, Most preferably it exceeds 0.300, for example it may exceed 0.500.

The nicotine composition 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-ethyl-3,5-dimethylpyrazine per gram of nicotine composition. It may also contain ethyl-3,5-dimethylpyrazine. In a preferred embodiment, the nicotine composition contains at least 0.500 micrograms of 2-ethyl-3,5-dimethylpyrazine per gram of nicotine composition, more preferably at least 0.700 micrograms of 2-ethyl-3,5-dimethylpyrazine 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 of 2-ethyl-3,5-dimethylpyrazine per gram of nicotine composition. Contains grams of 2-ethyl-3,5-dimethylpyrazine. In particularly preferred embodiments, 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 of 2-ethyl-3,5-dimethylpyrazine 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 microgram of 2-ethyl-3,5-dimethylpyrazine 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 greater than 2.00, for example may be greater than 2.50. (2-ethyl-3,5-dimethylpyrazine) 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 0.500, such as greater than 0.750, preferably greater than 1.00, More preferably it exceeds 2.00, most preferably it exceeds 3.00, for example it may exceed 3.50.

The nicotine composition 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 at least 1.0 micrograms of 2-methylbutanoic acid per gram of nicotine composition. It may include at least 3.00 micrograms of 2-methylbutanoic acid per gram, and most preferably at least 5.00 micrograms of 2-methylbutanoic acid per gram of nicotine composition. In a preferred embodiment, 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; More preferably at least 8.00 micrograms of 2-methylbutanoic acid per gram of nicotine composition, and 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. 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, and most preferably at least 14.0 micrograms of 2-methylbutanoic acid per 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. , most preferably greater than 30.0, such as greater than 32.0.

The nicotine composition 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 at least 1 ml of nicotine composition. 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 a preferred embodiment, 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; More preferably at least 10.0 micrograms of 3-methylbutanoic acid per gram of nicotine composition, and 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. 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, and most preferably at least 30.0 micrograms of 3-methylbutanoic acid per 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, and 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. , most preferably greater than 65.0, such as greater than 70.0.

The nicotine composition may include 3-methyl-2,4-nonanedione. The nicotine composition comprises at least 6.00x10 ^-3 micrograms of 3-methyl-2,4-nonanedione per gram of nicotine composition, preferably at least 8.00x10 ^-3 micrograms of 3-methyl 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. 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 particularly preferred embodiments, 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 greater than 0.225, for example may be greater than 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 more than 0.035, for example more than 0.040, preferably more than 0.080, more preferably may be greater than 0.090, most preferably greater than 0.100, for example greater than 0.130.

The nicotine composition 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, and more preferably at least 0.300 micrograms of 2-methoxyphenol per gram of nicotine composition. 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 a preferred embodiment, 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; More preferably at least 0.900 micrograms of 2-methoxyphenol per gram of nicotine composition, and most preferably 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. 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, and most preferably at least 2.50 micrograms of 2-methoxyphenol per 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. For example, it may exceed 4.50. (2-methoxyphenol) 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 1.40, such as greater than, preferably greater than 1.80, more preferably greater than 2.00, Most preferably it exceeds 3.00, for example it may exceed 6.00.

The nicotine composition 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 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 a preferred embodiment, the nicotine composition contains 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 More preferably at least 11.0 micrograms of 2-phenylethanol per gram of nicotine composition, and 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. 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, and most preferably at least 17.0 micrograms of 2-phenylethanol per 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, and 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-nitrosoanatabine + (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. , most preferably greater than 17.0, such as greater than 35.0.

The nicotine composition 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 has 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 still It contains at least 0.200 micrograms of eugenol per gram, most preferably at least micrograms of eugenol per gram of nicotine composition. In particularly preferred embodiments, 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 at least 1 gram of nicotine composition. 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 weight ratio of (eugenol) to (phenol) 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 - the weight ratio of nitrosonolnicotine + ((2-furanmethanol)/600) 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 exceeds 0.550, for example it may exceed 1.50.

The nicotine composition may include sotolone. The nicotine composition contains at least 3.00x10 ^-3 micrograms of sotolone per gram of nicotine composition, preferably at least 5.00x10 -3 micrograms of sotolone per gram of nicotine composition, more preferably at least 5.00x10 ^-3 micrograms of sotolone per gram of nicotine composition. It may contain at least 7.00 x 10 ^-3 micrograms of sotolone, most preferably at least 9.00 x 10 ^-3 micrograms of sotolone per gram of nicotine composition. In preferred embodiments, the nicotine composition contains at least 0.0100 micrograms of sotolon per gram of nicotine composition, more preferably at least 0.0200 micrograms of sotolone per gram of nicotine composition, even more preferably still It contains at least 0.0300 micrograms of sotolone per gram, and most preferably at least micrograms of sotolone per gram of nicotine composition. In particularly preferred embodiments, the nicotine composition contains 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 at least 1 gram of sotolone per gram of nicotine composition. It contains at least 0.0600 micrograms of sotolon 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. (Sotolon) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R,S)-N-nitrosoanabasine +N - the weight ratio of nitrosonolnicotine + ((2-furanmethanol)/600) 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 exceeds 0.0700, for example it may exceed 0.0750.

Apart from phenol, TSNA, NNK, NAT, NAB and NNN, and 2-furanmethanol, other undesirable compounds that may be present in nicotine compositions but are minimized by the extraction methods described herein include , formaldehyde (derived from sugars) 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 -toludine, etc.).

The nicotine composition may contain 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. of phenol, 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. It may contain 2.00 micrograms of phenol.

The nicotine composition may contain 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 still 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 may contain 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 nicotine composition, 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, each gram of nicotine composition may contain up to 0.300 micrograms of NAT.

The nicotine composition may contain 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 nicotine composition, 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 may contain up to 1.60 micrograms of N-nitrosonol nicotine (NNN) per gram of nicotine composition, such as up to 1.60 micrograms 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 up to 0.300 micrograms of NNN per gram of nicotine composition. It may contain up to 0.200 micrograms of NNN per gram.

The nicotine composition may contain up to 1500 micrograms of 2-furanmethanol per gram of nicotine composition, such as up to 1200 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 up to 900 micrograms of 2-furanmethanol per gram of nicotine composition It may contain up to 700 micrograms of 2-furanmethanol per gram.

The nicotine composition may contain up to 60 micrograms of formaldehyde per gram of nicotine composition, such as up to 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 may contain up to 60 micrograms of acetaldehyde per gram of nicotine composition, such as up to 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 may contain up to 5.00 micrograms of catechol per gram of nicotine composition, such as up to micrograms of catechol per gram of nicotine composition, preferably up to 4.00 micrograms of catechol per gram of nicotine composition, More preferably at most 3.00 micrograms of catechol per gram of nicotine composition, even more preferably at most 2.00 micrograms of catechol per gram of nicotine composition, and most preferably at most 1.00 micrograms of catechol per gram of nicotine composition. May contain micrograms of catechol.

The nicotine composition may contain 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 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. It may contain 0.700 micrograms of hydroquinone.

The nicotine composition may contain 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 may contain 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 may contain 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 may contain 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 preferably 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 contain 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, and most preferably up to 70 micrograms of acetamide per gram of nicotine composition. .

The nicotine composition may contain 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.

The nicotine composition can be produced from liquid tobacco extract from a tobacco starting material consisting of a single type of natural tobacco. The tobacco starting material may include a blend of two or more types of natural tobacco. Alternatively, the nicotine composition comprises a first tobacco starting material consisting of a first single type of natural tobacco that is extracted to form a first extract, and a second tobacco starting material that is extracted to form a second extract. A liquid tobacco extract may be produced from a blend produced from a second tobacco starting material consisting of a second single type of natural tobacco extracted to produce a first extract and a second The extracts 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, the proportion of Burley tobacco may be increased if it is desired to provide relatively high levels of nicotine.

The nicotine composition may be a liquid tobacco extract resulting from an extraction process, where the liquid tobacco extract includes a non-aqueous solvent, water, nicotine, and flavoring 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, liquid tobacco extract produced by the extraction process can be used to create nicotine compositions containing 10-20 mg of nicotine per milliliter without the need for nicotine addition. The term "liquid tobacco extract" describes the direct product of the extraction process from tobacco material. Therefore, liquid tobacco extract typically consists of natural constituents separated from, removed from, or derived from natural tobacco material using tobacco extraction processing conditions and techniques. Contains mixtures. Therefore, in one such process, extracted tobacco components are removed from the natural tobacco material and separated from unextracted tobacco components. Liquid tobacco extract is thus derived from a tobacco starting material and consists of a mixture of natural tobacco components extracted or formed during the extraction process, typically containing one or more materials other than the tobacco starting material, e.g. It is combined with the extraction solvent used during the extraction process. Preferably, the extraction solvent is an aerosol former.

As used herein, the term "aerosol former" refers to an object that facilitates the formation of an aerosol in use and that is preferably substantially resistant to thermal decomposition at the operating temperature of the aerosol-generating article or device. Refers to a compound or a 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), and aliphatic esters of monocarboxylic, dicarboxylic or polycarboxylic acids (dimethyl dodecanedioate, dimethyl tetradecanedioate, etc.).

The nicotine composition may include liquid tobacco extract resulting from an extraction process to which additional nicotine has been added. In the nicotine composition according to the 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 a preferred embodiment, 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 include liquid tobacco extract resulting from an extraction process with the addition of additional non-aqueous solvents. In the nicotine composition according to the invention, at least 50 weight percent of the non-aqueous extraction solvent content in the nicotine composition, based on the total weight of the nicotine composition, is derived from the liquid tobacco extract rather than being added after extraction. Obtainable. In a preferred embodiment, at least 80 weight percent of the non-aqueous extraction solvent 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 non-aqueous extraction solvent 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 include liquid tobacco extract resulting from an extraction process with the addition of additional water. In the nicotine composition according to the invention, at least 50 weight percent of the water 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 a preferred embodiment, 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 include liquid tobacco extract resulting from an extraction process to which additional flavoring compounds have been added. In the nicotine composition according to the invention, at least 50 weight percent of the desired tobacco flavor species content in the nicotine composition, based on the total weight of the nicotine composition, is added in the liquid tobacco extract rather than added after extraction. can be obtained from. In a preferred embodiment, at least 80 weight percent of the desired flavor species 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 desired flavor species 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 desired flavor species 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 a preferred embodiment, 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 of the 2,3-diethyl-5-methylpyrazine content in the nicotine composition, based on the total weight of the nicotine composition, is added to the liquid rather than added after extraction. It can be obtained from tobacco extract. In a preferred embodiment, at least 80 weight percent of the 2,3-diethyl-5-methylpyrazine content in the nicotine composition, based on the total weight of the nicotine composition, is added to the liquid tobacco rather than added after extraction. Obtained from extract. More preferably, at least 90 weight percent of the 2,3-diethyl-5-methylpyrazine content in the nicotine composition, based on the total weight of the nicotine composition, is added to the liquid tobacco extract rather than added after extraction. obtained from things. Even more preferably, 100 weight percent of the 2,3-diethyl-5-methylpyrazine content in the nicotine composition, based on the total weight of the nicotine composition, is added to the liquid tobacco extract rather than added after extraction. obtained from things.

The nicotine composition may include a further processed, particularly concentrated, liquid tobacco extract. 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 flavoring compounds as described above may be added to the liquid or concentrated tobacco extract to form a nicotine composition.

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

Preferably, the nicotine composition is produced from liquid tobacco extract. The liquid tobacco extract advantageously provides an improved liquid tobacco extract with a significantly improved balance of desirable and undesirable compounds, and thus an improved nicotine composition. Preferably, it is produced using an extraction method with an extraction temperature within a certain range, combined with a heating duration. In particular, the extraction method provides a liquid tobacco extract and nicotine composition with a maximized ratio of desirable compounds to undesirable compounds for the tobacco starting material. For example, the use of a specific combination of extraction temperature and time as defined allows optimizing the levels of nicotine and flavoring compounds, while reducing the concentration of furans, phenols and phenolic compounds, and tobacco-specific Minimize levels of undesirable compounds such as nitrosamines (TSNA).

Therefore, the liquid tobacco extract and nicotine composition obtained by one such method exhibits significant compositional differences with respect to the tobacco extract and nicotine composition obtained by existing extraction processes and, when heated, currently It can be used as or for the preparation of e-liquids to generate aerosols with distinct composition and flavor characteristics compared to available e-liquids. In particular, the liquid tobacco extract and nicotine compositions obtained by the method according to the invention are superior to the available aerosols produced from existing liquid nicotine compositions, such as those produced by conventional cigarettes or heated non-combustible devices. It may be used to generate an aerosol that provides the taste of heated tobacco more closely resembling the aerosol generated with the heating of tobacco.

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 include 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, 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 include liquid tobacco extract, where the liquid tobacco extract is a concentrated tobacco extract. Concentrated tobacco extract is a liquid tobacco extract that has been concentrated in 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 about 50 weight percent to about 95 weight percent liquid tobacco extract. Most preferably, the nicotine composition comprises about 60 weight percent to about 95 weight percent liquid tobacco extract. In some particularly preferred embodiments, the nicotine composition comprises about 70 weight percent to about 95 weight percent liquid tobacco extract, even more preferably 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 about 40 weight percent to about 90 weight percent liquid tobacco extract. Even more preferably, the nicotine composition comprises 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 about 70 weight percent to about 90 weight percent liquid tobacco extract, even more preferably 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 about 40 weight percent to about 85 weight percent liquid tobacco extract. Even more preferably, the nicotine composition comprises about 85 weight percent to about 90 weight percent liquid tobacco extract. Most preferably, the nicotine composition comprises about 60 weight percent to about 85 weight percent liquid tobacco extract. In some particularly preferred embodiments, the nicotine composition comprises about 70 weight percent to about 85 weight percent liquid tobacco extract, even more preferably 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 include up to about 100 weight percent liquid tobacco extract. In some embodiments, nicotine compositions can be formed directly from liquid tobacco extract without the need for the addition of additional non-aqueous solvents, flavors, or nicotine. That is, the nicotine composition may include 100 weight percent liquid tobacco extract. In some embodiments, the liquid tobacco extract is a concentrated tobacco extract, and the nicotine composition can include 100 weight percent of the 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 comprising liquid tobacco extract may include additional non-aqueous solvents. Additional non-aqueous solvents are non-aqueous solvents added after the extraction step. The additional non-aqueous solvent is a solvent that supplements 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 include an additional non-aqueous solvent. The total content of non-aqueous solvents in the nicotine composition includes the non-aqueous extraction solvent and additional non-aqueous solvents, if present, as described above.

The additional non-aqueous solvent may be an aerosol former. Preferably, the additional non-aqueous solvent is triacetin, glycerin, propylene glycol, 1,3-propanediol, or a mixture thereof.

In embodiments where the nicotine composition includes an additional non-aqueous solvent, the nicotine composition can include up to 90 weight percent of the additional non-aqueous solvent. Preferably, the nicotine composition contains no more than 80 weight percent of additional non-aqueous solvent. More preferably, the nicotine composition comprises no more than 70 weight percent of additional non-aqueous solvent. In preferred embodiments, the nicotine composition comprises up to about 60 weight percent of additional non-aqueous solvent, more preferably up to about 50 weight percent of additional non-aqueous solvent, and even more preferably up to about 40 weight percent of additional non-aqueous solvent. Contains an aqueous solvent. In particularly preferred embodiments, the nicotine composition comprises up to about 35 weight percent of additional non-aqueous solvent, more preferably up to about 30 weight percent of additional non-aqueous solvent, even more preferably up to about 25 weight percent of additional non-aqueous solvent. A non-aqueous solvent, most preferably up to 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 as herein described. A concentrated tobacco extract containing the desired flavor compounds derived from the described extraction process, with a balance of 1.8 weight percent of other ingredients.

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 includes 20 weight percent glycerin as an additional non-aqueous solvent and 80 weight percent concentrated tobacco extract; the concentrated tobacco extract comprises 84 weight percent propylene glycol; 1.8 weight percent others, including 12.5 weight percent water, 1.2 weight percent nicotine, 0.5 weight percent acetic acid, and the desired flavoring compounds derived from the extraction process described herein. Including the balance of ingredients. Thus, the nicotine composition of this exemplary embodiment includes 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 the desired flavor compounds derived from the extraction process described herein. The composition includes a total content of non-aqueous solvents of 87.2 weight percent, the non-aqueous solvents including glycerin and propylene glycol.

The nicotine composition may be a gel nicotine composition. Since nicotine can irritate the skin, it is desirable to prevent possible nicotine leakage by trapping it within a 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 a 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 higher than the gelling temperature. The melting temperature of the gel is preferably higher than 50 degrees Celsius, 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 begins to flow.

Gel nicotine compositions may include suitable gelling agents. Preferably, the gel nicotine composition comprises 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, and more preferably from about 0.8 weight percent to about 1 weight percent gelling agent.

The gel nicotine composition may include liquid tobacco extract. Preferably, the gel nicotine composition contains 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, and even more preferably from about 70 percent to about 99.5 percent liquid tobacco extract. It comprises 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 include a concentrated tobacco extract. Preferably, the gel nicotine composition contains 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, and even more preferably from about 70 percent to about 99.5 percent concentrated tobacco extract. Contains 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 contains 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. Preferably, the additional non-aqueous solvent is 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 additional non-aqueous solvents, if present. The gel nicotine composition can include a total non-aqueous solvent content of about 10 weight percent to about 95 weight percent. The gel nicotine composition preferably contains 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 total non-aqueous solvent content. Preferably, the non-aqueous solvent is triacetin, glycerin, propylene glycol, 1,3-propanediol, or a mixture thereof.

Gel nicotine compositions may contain from 1 weight percent to 85 weight percent water. Gel nicotine compositions 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. Gel nicotine compositions may contain from 8 weight percent to 20 weight percent water. The gel nicotine composition may contain 10 weight percent to 15 weight percent water.

The gel nicotine composition contains 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. may 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 includes 80 weight percent liquid tobacco extract, 19 weight percent additional non-aqueous solvent, and 1 percent agar. In this exemplary embodiment, the nicotine composition includes 19 weight percent glycerin as an additional non-aqueous solvent, and 80 weight percent liquid tobacco extract, where the liquid tobacco extract comprises 59 weight percent glycerin, 37 weight percent .5 weight percent water, 1.2 weight percent nicotine, 0.5 weight percent acetic acid, and 1.8 weight percent other, including the desired flavoring compounds derived from the extraction process described herein. Including the balance of ingredients. Accordingly, the nicotine composition of this exemplary embodiment includes 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 a balance of 1.44 weight percent of other ingredients, including the desired flavor compounds derived from the extraction process described herein.

Nicotine compositions according to the invention may be provided in cartridges for use in aerosol generation systems. The cartridge may include 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 include, for example, a heater and a liquid transport element configured to transfer the nicotine composition to the heater. The liquid transport element may include a capillary core. 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, a 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 described herein for use in an aerosol generation system.

It is possible to adjust the characteristics of the nicotine composition and the resulting aerosol produced from the nicotine composition and delivered to the consumer through control of the parameters of the extraction process.

According to the invention, 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% nicotine, prepared by a method comprising the steps of: forming a liquid tobacco extract containing collected volatile compounds; and forming a nicotine composition from the liquid tobacco extract. a first weight ratio of (β-ionone + β-damascenone) to (phenol) greater than 5×10 ⁻⁴ and (furaneol + (2,3-diethyl-5-methylpyrazine)*100) to (nicotine) A nicotine composition is provided that includes a second weight ratio.

As discussed above, the nicotine composition can be produced from liquid tobacco extract from a tobacco starting material consisting of a single type of natural tobacco. The tobacco starting material may include a blend of two or more types of natural tobacco. Alternatively, the nicotine composition comprises a first tobacco starting material consisting of a first single type of natural tobacco that is extracted to form a first extract, and a second tobacco starting material that is extracted to form a second extract. A liquid tobacco extract may be produced from a blend produced from a second tobacco starting material consisting of a second single type of natural tobacco extracted to produce a first extract and a second The extracts 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, the proportion of Burley tobacco may be increased if it is desired to provide relatively high levels of nicotine.

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, the leaves, midribs, stems and petioles. used for. In particular, natural tobacco may be derived from fully cured tobacco material, Burley tobacco material, Orient tobacco material, Maryland tobacco material, dark tobacco material, dark fired tobacco material, Rustica tobacco material, as well as other rare or specialty tobacco materials. or blends thereof. As explained in more detail below, the tobacco material may be whole (eg, whole tobacco leaves), shredded, cut, 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 within a defined range of 100 degrees Celsius to 160 degrees Celsius. may be heated separately at different extraction temperatures, 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 leaf, tobacco stem, reconstituted tobacco, cast tobacco, extruded tobacco, or tobacco-derived pellets.

In the process of preparing the tobacco starting material, the tobacco is preferably ground or cut to reduce the size of the tobacco particles within the tobacco starting material. This may advantageously improve the uniformity 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 carried out before the heating step, it may advantageously increase the amount of certain desirable 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 It has been found to increase the amount of flavor compounds extracted from the starting material.

In the process of preparing the natural tobacco material, the tobacco is preferably not subjected to any treatment adapted to alter the pH of the tobacco. In particular, in the process of preparing the natural tobacco material, the tobacco is not subjected to any treatment adapted to significantly increase the pH of the tobacco. For example, natural tobacco material is not contacted with an aqueous solution containing an alkali or alkaline earth metal salt. Advantageously, maintaining tobacco materials in a less modified state may provide a more authentic or natural flavor profile that may be perceived by consumers. I know it. In addition, subjecting the natural tobacco material to a treatment adapted to increase the pH of the tobacco, such as an alkali treatment, prior to heating the tobacco material as part of the extraction process, may provide the desired heating effect in the liquid tobacco extract. The inventors have found that tobacco flavor compounds lead to reduced levels of tobacco flavor compounds. As an example, not subjecting natural tobacco material to alkali treatment may result in a lower weight ratio of (β-ionone + β-damascenone) to (phenol) in liquid tobacco extract compared to equivalent alkali-treated natural tobacco material. It has been found to be associated with a significant increase in

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

In other embodiments, the tobacco starting material may include one or more additional ingredients, such as, for example, a non-aqueous solvent or added water or both. An example of a suitable solvent is propylene glycol.

Thus, the tobacco starting material comprises 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. Can be a percentage. 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. It can be. In further embodiments, the moisture content of the tobacco starting material is 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 tobacco starting materials.

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

The extraction temperature and duration of heating will depend on 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 can be selected within the range defined above. By controlling the combination of extraction temperature and time, the liquid tobacco extract can be tailored to the desired properties of the aerosol generated from the nicotine composition. In particular, the ratio of specific tobacco compounds within the nicotine composition is determined in part through the selection of extraction parameters to maximize the ratio of desirable to undesirable tobacco compounds within the liquid tobacco extract and nicotine composition. can be adjusted.

For a particular tobacco compound, the variation in the level of compound release with extraction temperature during the extraction process can be easily 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 for different tobacco types.

Additionally, the levels of desirable tobacco flavor compounds such as β-damascenone and β-ionone released from tobacco materials 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 such flavor compounds is typically within the range of 100 degrees Celsius to 160 degrees Celsius so that the level of desired flavor compounds in the extraction process can be effectively optimized.

Methods in which tobacco materials are immersed for several weeks in a suitable liquid solvent, such as an aerosol former, at room temperature or below, in order to extract tobacco components into the solvent, typically contain less than the content of the compositions of the invention. A much lower component content is also obtained. Extraction processes in which the tobacco material is immersed in a suitable solvent, such as an aerosol former, at or below room temperature, which is not present in tobacco, do not generate thermally generated compounds after the Maillard reaction has taken place. One such compound that is thermally generated after the Maillard reaction occurs is furaneol. Furaneol is derived from the heat treatment of the natural 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 that there is a direct correlation between the extraction temperature and the level of furaneol released, which varies significantly. As described herein, the peak extraction temperature for these flavor compounds is typically 100 degrees Celsius so that the levels of these desirable flavor compounds can be effectively optimized in the extraction process. ~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 the levels of phenol, other phenolic compounds, and TSNA, and in the case of bright tobacco, to the levels of furan and formaldehyde. Often the threshold temperature is within the range of 100 degrees Celsius to 160 degrees Celsius, so the levels of undesirable compounds can be effectively controlled in the extraction process.

It has been found by the inventors of the present invention that for a particular tobacco type, the level of certain undesirable nitrogen compounds, such as TSNA, released during extraction is dependent 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 TSNA released during the extraction process. Burley tobacco, on the other hand, typically has a much higher content of nitrogen compounds, and the amount of TSNA released upon heating varies markedly depending on extraction temperature, with the level of TSNA released varying significantly with extraction temperature. It is found that there is a direct correlation between

It has also been found by the inventors of the present invention that for a particular tobacco type, the level of 2-furan methanol, a particular undesirable furan 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 depending on the 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 the level of 2-furanmethanol released from bright tobacco increases with increasing extraction temperature 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. If the tobacco starting material is heated to temperatures above this range, the resulting composition will have a much higher weight of phenol to β-ionone and β-damascenone and a lower weight of phenol to β-ionone and β-damascenone. 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, these undesirable compounds originate in relatively high amounts from tobaccos that are high in nitrogen compounds, such as Burley tobacco, and the amount of TSNA released upon heating depends on the extraction temperature. It is found that the extraction temperature varies significantly and there is a direct correlation between the extraction temperature and the level of TSNA released.

As described herein, 2-furanmethanol is derived in relatively high amounts from tobacco with a high reducing sugar content, such as bright tobacco, and the amount of 2-furanmethanol released upon heating is It is found that there is a direct correlation between the extraction temperature and the level of 2-furanmethanol released, which varies significantly depending on the extraction temperature.

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. If the tobacco starting material is heated above this range, in the resulting composition the weight of TSNA and 2-furanmethanol relative to the weight of β-ionone and β-damascenone is much higher and lower (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 TSNA are typically present in A higher percentage is derived from burley tobacco compared to bright tobacco. Certain desirable flavoring 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. Certain undesirable compounds, such as , 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 composition of the present invention is preferably produced from a blend of different tobacco types. Preferably, the nicotine composition is derived from Burley and Bright tobaccos. The 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, if 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 may be released. There is sex.

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, and more preferably at least about 125 degrees Celsius.

The extraction temperature is preferably about 150 degrees Celsius or less, more preferably about 145 degrees Celsius or less, more preferably about 140 degrees Celsius or less, and most preferably about 135 degrees Celsius or less. .

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. It has been found that an extraction temperature of about 130 degrees Celsius provides 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, and more preferably at least about 120 minutes. This extraction time is long enough to efficiently extract the desired tobacco flavor compounds to provide a nicotine composition that can produce an aerosol with 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 taken to raise the temperature of the tobacco starting material to the extraction temperature.

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

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

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

Furthermore, the use of a flow of inert gas (such as nitrogen) under mild overpressure within the extraction equipment has the advantage of preventing the presence of oxygen within the extraction equipment. This can also be achieved by performing a 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 material would be clearly undesirable as it would present a major safety risk within the manufacturing environment. However, the inventors note that even limited and partial combustion of natural tobacco material may lead to a reduction in the quality of the tobacco extract that can be obtained by this method (which would be undesirable). I found it.

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

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

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.

It has been found that the addition of water or steam to tobacco during extraction increases the yield of extracted components. However, excessive addition of water or steam leads to processing difficulties (such as stickiness of the tobacco material).

Suitable heating methods for carrying out heating of tobacco starting materials are known to those skilled in the art and include, but are not limited to, carbonization, 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 tobacco starting materials.

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

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

Preferably, the step of collecting volatile compounds uses an absorption technique in which the volatile compounds are trapped in a non-aqueous solvent. For example, a stream of inert gas containing volatile compounds may be directed into 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 a mixture thereof. The non-aqueous extraction solvent may be a polyhydric alcohol. The use of aerosol formers as non-aqueous extraction solvents can be beneficial as the aerosol formers can be retained as diluents 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 necessary.

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

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

In addition, liquid aerosol formers advantageously serve to capture flavor-related compounds, regardless of their polarity and volatility. Moreover, during the fourth (drying) step, the liquid aerosol former not only helps to prevent the loss of most volatile fractions, but also absorbs the liquid natural tobacco extract in order to obtain a concentrated tobacco extract. Favors the selective removal of excess water from the extract.

The use of PG as an aerosol former for the condensation and collection step has the additional advantage that the PG exerts antimicrobial activity by reducing the water activity of the aqueous solution. Thus, by adjusting the content of PG in a liquid natural tobacco extract, it is also possible to ensure that the extract is substantially free of any microbial activity.

The liquid natural tobacco extract obtained at the end of the collection process is typically a homogeneous liquid. Such a homogeneous liquid may be stored for a limited period of time (up to about 4 weeks) holding period before undergoing an optional drying step. The composition of a liquid natural 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. Includes the amount of aerosol former used (if any).

Preferably, the non-aqueous extraction solvent is maintained at a temperature below 0 degrees Celsius to optimize the transfer of volatile compounds to the non-aqueous extraction solvent. Preferably, the non-aqueous extraction solvent is maintained 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, collecting volatile compounds may be performed using condensation techniques, where the volatile compounds are condensed and the condensate is collected. Condensation of volatile compounds may be carried out using any suitable equipment, for example in a cooling column. If the volatile compounds are collected by condensation, 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 may be performed using adsorption techniques in which volatile compounds are adsorbed onto the surface of a solid adsorbent material such as activated carbon. The adsorbed compounds are then transferred into a non-aqueous extraction solvent.

Optionally, forming the liquid tobacco extract includes a filtration step.

Optionally, forming the liquid tobacco extract includes a blending step in which extracts from different tobacco starting materials are combined.

In this method, the next step is to form a liquid tobacco extract from the collected volatile compounds. The nature of this step may depend on the collection method. "Collected volatile compounds" typically comprises 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 method described herein provides 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 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. Provided is a liquid tobacco extract having the following properties. Preferably, the non-aqueous extraction solvent is triacetin, glycerin, propylene glycol, 1,3-propanediol, or a mixture 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 the need for additional nicotine addition. Nicotine compositions can advantageously be formed directly from the liquid tobacco extract resulting from the extraction process without the need for the addition of additional flavor compounds. Nicotine compositions can advantageously be formed directly from liquid tobacco extract without the need for the addition of additional non-aqueous solvents. For example, liquid tobacco extract produced by the extraction process may be used to create nicotine compositions containing 10-20 mg of nicotine per milliliter without the need for nicotine addition.

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

As mentioned above, when volatile compounds are collected by absorption in a non-aqueous extraction solvent, in order to concentrate the solution, a liquid tobacco extract is formed, since the liquid solvent can include both the non-aqueous extraction solvent and water. It is preferred to dry solutions of volatile compounds in liquid solvents. This can be done, for example, to reach the desired concentration of nicotine or flavor compounds. Drying can include 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 may be performed using any suitable means, including but not limited to.

The solution of volatile compounds in a liquid solvent forming the liquid tobacco extract is preferably concentrated by drying in a drying step to form a concentrated tobacco extract. Concentrated tobacco extract 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 the volatile compound 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, a solution of a volatile compound in a liquid solvent is heated under vacuum, preferably at a temperature of at least about 70 degrees Celsius. In another embodiment, a solution of a volatile compound in a liquid solvent is heated to a temperature of at least about 35 degrees Celsius under a flow of air, preferably with a flow of 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 dried at a temperature of about 35 degrees Celsius to about 95 degrees Celsius, more preferably about 35 degrees Celsius to about 90 degrees Celsius, even more preferably about 35 degrees Celsius to about 85 degrees Celsius, most preferably It can be heated to 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 a pressure of about 200 mbar or less. In the drying step, the liquid tobacco extract may be heated at a pressure of at least about 20 mbar.

Alternatively, during the drying process, the liquid tobacco extract may be heated under a stream of air. The liquid tobacco extract may be heated under a flow of air of at least about 10 kg/h. The liquid tobacco extract may be heated under a flow of air 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. Concentrated tobacco extracts contain up to about 20 weight percent water. Preferably, the concentrated tobacco extract contains 8 weight percent to 15 weight percent water, based on the weight of the concentrated tobacco extract.

The drying step may include a concentrated tobacco product having a non-aqueous extraction solvent content of from about 65 weight percent to about 95 weight percent, preferably from about 65 weight percent to about 85 weight percent, and most preferably from about 75 weight percent to about 85 weight percent. Provide extract. Preferably, the non-aqueous extraction solvent is triacetin, glycerin, propylene glycol, 1,3-propanediol, or a mixture 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. The present invention provides a concentrated tobacco extract that can be used as a tobacco extract.

Concentrated tobacco extract can be used directly to form nicotine compositions without the need for additional nicotine addition. Concentrated tobacco extract can be used directly to form nicotine compositions without the need for the addition of additional non-aqueous solvents. Concentrated tobacco extract can be used directly to form nicotine compositions without the need for additional water addition. Concentrated tobacco extract can be used directly to form nicotine compositions without the need for the addition of additional flavoring agents.

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

The nicotine composition may have any of the preferred characteristics described herein above.

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

Example 1
The tobacco starting material is prepared from Full Cure Bright tobacco material. The tobacco material is cut to form tobacco pieces having dimensions of 2.5 mm x 2.5 mm, and the tobacco pieces are loaded into the extraction chamber without compression. The tobacco starting material is heated in an extraction chamber for 3 hours to a temperature of 130 degrees Celsius. During heating, a flow of nitrogen passes through the extraction chamber at a flow rate of approximately 40 liters/min.

The 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 -10 degrees Celsius and with stirring at 750 rpm.

The nicotine composition of Example 1 is a liquid tobacco extract obtained directly from a 3 hour extraction process at a temperature of 130 degrees Celsius. 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 basine, 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 5x10-4.

Example 2
This example provides two nicotine compositions according to the present invention, both of which require an extraction process of 3 hours at a temperature of 130 degrees Celsius, followed by drying to reduce the moisture level of the liquid tobacco extract to about 6 percent. The concentrated tobacco extract obtained from the process. The concentrated tobacco extract is then used directly to form a nicotine composition. In both 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 x 10-4.

Example 2a
Example 2a relates to a concentrated tobacco extract derived from Flucure Bright tobacco material. The content of liquid tobacco extract of Example 2a is as follows.
・Nicotine: 0.53% w/w
・Propylene glycol: 91.8% w/w
・Water: 6.3% w/w
- Balance (including flavoring agents 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 content of liquid tobacco extract of Example 2b is as follows.
・Nicotine: 1.82% w/w
・Propylene glycol: 89.6% w/w
・Water: 5.7% w/w
Balance (including flavoring agents detailed in Table 1 below): 2.88% w/w

The nicotine compositions of Examples 2a and 2b according to the invention include 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 consists of an extraction process of 3 hours at a temperature of 130 degrees Celsius, followed by reducing the moisture level of the liquid tobacco extract to about 12.5 percent. This is a concentrated tobacco extract obtained from the drying process. The concentrated tobacco extract is then used directly to form a nicotine composition. In these nicotine compositions, the weight ratio of (β-ionone + β-damascenone) to (phenol) is greater than 0.25, and the weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine)*100)) to ( Nicotine) weight ratio is greater than 5x10-4.

Example 3a
Example 3a relates to a concentrated tobacco extract derived from Orient Leaf Bright tobacco material. The content of the concentrated tobacco extract of Example 3a is 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 flavoring agents): 2.1% w/w

Example 3b
Example 3b relates to a concentrated tobacco extract derived from Flucure Bright tobacco material. The content of the concentrated tobacco extract of Example 3b is 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 flavoring agents): 1.3% w/w

Example 3c
Example 3c relates to a concentrated tobacco extract derived from Burley tobacco material. The content of the concentrated tobacco extract of Example 3c is 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 flavoring agents): 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 20 weight percent glycerin and 80 weight percent glycerin, based on the weight of the nicotine composition. Contains liquid tobacco extract.

Example 5
Example 5 relates to a nicotine composition in the form of a gel 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 prepared from Flucure Bright tobacco material (6A), Burley tobacco material (6B), and Orient leaf tobacco material (6C), respectively.

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

Each piece of tobacco starting material is heated in an extraction chamber for 120 minutes to a temperature of 130 degrees Celsius. During heating, a flow of nitrogen passes through the extraction chamber at a flow rate of 2 liters/min.

The 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.

Liquid tobacco extracts are obtained directly from such extraction processes. 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 weight ratio of (β-ionone + β-damascenone) to (phenol) is consistently and significantly above 2.0. Moreover, 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) is consistent and Significantly exceeds 1×10 ^-3 . Furthermore, in all three liquid extracts according to inventions 6A, 6B and 6C, (β-ionone + β-damascenone) vs. (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 More than 3.

Comparative Example Two tobacco starting materials are prepared from Full Cure Bright tobacco materials (CE1, CE2). Two further tobacco starting materials are prepared from Burley tobacco material (CE3, CE4). Each of the four starting tobacco materials is cut to form tobacco strips having dimensions of 2.5 mm x 2.5 mm.

The 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 US 2016/360780.

More specifically, tobacco starting materials CE1 and CE3 are mixed with an alkaline solution of potassium carbonate in water to reach a pH of 8, and tobacco starting materials CE2 and C4 are mixed with an alkaline solution of potassium carbonate in water to reach a pH of 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 to a temperature of 130 degrees Celsius for 120 minutes in an extraction chamber. During heating, a flow of nitrogen passes through the extraction chamber at a flow rate of approximately 2 liters/min.

The 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.

Liquid tobacco extracts are obtained directly from such extraction processes. Each liquid extract obtained from each one of the four 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 four liquid extracts according to 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) is consistent in all four liquid extracts according to comparative examples CE1, CE2, CE3, and CE4. and significantly less than 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, a first of greater than 0.25 (β-ionone + β-damascenone) to (phenol); 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; The nicotine composition of claim 1. The nicotine composition according to any of claims 1 or 2, wherein the second weight ratio is between 8x10 ^-4 and 9x10 ^-3 . A nicotine composition according to any of claims 1 to 3, 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, said third weight ratio being (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 The nicotine composition according to any one of claims 1 to 4, wherein the nicotine composition has a value of greater than 1.5. The nicotine composition according to any of claims 1 to 5, wherein the nicotine composition is derived from Burley tobacco and Bright tobacco. 7. The nicotine composition of claim 6, wherein the bright tobacco is one or more of orient leaf tobacco and full cure tobacco. The nicotine composition according to any of claims 1 to 7, wherein the non-aqueous solvent is glycerin, propylene glycol, triacetin, 1,3-propanediol, or a mixture 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. Nicotine composition according to any of claims 1 to 8, 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 about 80 weight percent to about 90 weight percent of the non-aqueous solvent and about 10 weight percent to about 15 weight percent water, based on the weight of the nicotine composition. The nicotine composition according to any of claims 1 to 11, wherein the nicotine composition is a liquid nicotine composition. The nicotine composition according to any one of claims 1 to 11, wherein the nicotine composition is a gel nicotine composition. A cartridge comprising the nicotine composition according to any one of claims 1 to 13. A method for preparing a nicotine composition according to any one of claims 1 to 13, 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 step;
forming a liquid tobacco extract containing the collected volatile compounds;
forming the nicotine composition from the liquid tobacco extract;
method including.