KR102642690B1 - Nicotine composition, manufacturing method, and aerosol-generating article comprising the same - Google Patents

Abstract

The present invention provides nicotine compositions comprising a high ratio of desired to undesirable compounds. The nicotine composition comprises a non-aqueous solvent, at least 0.2% nicotine by weight based on the weight of the nicotine composition, a first weight ratio of (β-ionone + β-damascenone) to (phenol) greater than 0.25, and 5 x 10 ^- and a second weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine)*100) to (nicotine) greater than ⁴ . heating the tobacco starting material at an extraction temperature of 100° C. to 160° C. for at least 90 minutes; collecting volatile compounds released from the tobacco starting material during the heating step; forming a liquid tobacco extract comprising the collected volatile compounds; Also provided are nicotine compositions prepared by a method comprising forming the nicotine composition from the liquid extract.

Description

Nicotine composition, manufacturing method, and aerosol-generating article comprising the same

The present invention relates to nicotine compositions.

Aerosol-generating systems are known for delivering aerosols to a user, including a nebulizer configured to generate an inhalable aerosol from a liquid composition, such as a liquid nicotine composition. Some known aerosol-generating systems include thermal nebulizers, such as electric heaters, that are configured to heat and vaporize a liquid composition to generate an aerosol. One popular type of electrically heated aerosol generating system is the electronic cigarette (e-cigarette). Other known aerosol generating systems include non-thermal nebulizers configured to generate aerosols from liquid compositions using, for example, impinging jet, ultrasonic or vibrating mesh techniques.

US Patent Application Publication No. 2016/360780 (2016.12.15.) US Patent Application Publication No. 2016/106144 (2016.04.21.)

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 for producing liquid tobacco extract from tobacco materials are known.

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

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

A layer of wax accumulates, and the aqueous portion containing nicotine and other water-soluble compounds is recycled to the boiler. Non-polar co-solvents can optionally be fed to the boiler with an aqueous portion to increase extraction yield. Meanwhile, the wax phase is collected and ultimately forms the primary product of one such steam distillation process. These products are often referred to as “tobacco essential oils” and contain a high proportion of non-polar compounds found in tobacco, such as fatty acids, neophytadiene, etc. Tobacco essential oil obtained by one such method typically does not contain nicotine.

It is also known that tobacco materials undergo extraction processes involving the use of volatile non-polar solvents. Examples of suitable solvents are cyclic or acyclic short alkanes, as well as chlorinated solvents such as dichloromethane. In one such process, excess solvent can be evaporated by controlled heating under vacuum. Typically, this is performed in the presence of ethanol, which has a higher boiling point than the extraction solvent, so that even small amounts of extraction solvent can be detected.

The primary product of one such solvent-assisted extraction process is often referred to as “tobacco absolute” and may contain small amounts of ethanol. It is a waxy product and contains a highly concentrated mixture of mostly non-polar compounds that can be extracted with certain solvents, usually containing nicotine, usually present in relatively high concentrations.

An alternative extraction process involves contacting the tobacco material with a solvent under supercritical conditions, such as supercritical carbon dioxide. One such process is disclosed in US 2013/160777 and relies on the principle that volatile substances in a feed material contacted with a supercritical fluid can partition into a supercritical phase. 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 from the supercritical fluid. The primary product of a supercritical extraction process is substantially similar to the "tobacco absolute" of a solvent-assisted extraction process run at lower temperatures and pressures, contains no residual solvents, and typically has high levels of waxy, non-polar compounds. , which generally contains nicotine present in relatively high concentrations.

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

Liquid tobacco extracts and nicotine compositions obtained by these known extraction processes may have low levels of nicotine. Moreover, the nicotine compositions obtained by this extraction process may have low levels and low ranges of flavor species, especially with respect to compounds associated with the flavor of heated tobacco, such as furaneol. Nicotine compositions obtained by this extraction process may also have high levels of undesirable compounds. In general, the concentration of nicotine, flavor species and undesirable compounds obtained by this extraction process can be significantly influenced by the type or types of tobacco used as starting material.

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

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

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

According to the present invention, a nicotine composition is provided, the nicotine composition comprising a non-aqueous solvent, at least 0.2% by weight nicotine, based on the weight of the nicotine composition, and 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) of greater than 5 x 10 ^-4 .

Non-aqueous solvent, nicotine, a first weight ratio of (β-ionone + β-damascenone) to (phenol) greater than 0.25, and a second weight ratio of greater than 5 x 10 ^-4 (furaneol + (2 A nicotine composition comprising a second weight ratio of ,3-diethyl-5-methylpyrazine)*100) to (nicotine) can be prepared by heating the tobacco starting material at an extraction temperature of 100° C. to 160° C. for at least 90 minutes; collecting volatile compounds released from the tobacco starting material during the heating step; forming a liquid tobacco extract comprising the collected volatile compounds; 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-generating system. In these aerosol-generating systems, the nicotine composition is typically heated within the aerosol-generating device.

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

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

The nicotine composition may include a non-aqueous solvent, water, nicotine, and a flavor compound.

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

The nicotine composition may include a total content of non-aqueous solvents from about 10% to about 95% by weight. The nicotine composition is preferably about 50% to about 95% by weight, for example about 65% to about 95% by weight, more preferably about 70% to about 90% by weight, most preferably about 80% by weight. % to about 90% by weight of the total content of non-aqueous solvents. The non-aqueous solvent is preferably triacetin, glycerin, propylene glycol, 1,3-propanediol, or mixtures thereof.

Those skilled in the art will recognize that when the weight percentage of a particular ingredient is disclosed herein with reference to a nicotine composition, liquid tobacco extract or concentrated tobacco extract, the weight percentage is of the specific ingredient relative to the total weight of the respective nicotine composition, liquid tobacco extract or concentrated tobacco extract. You will understand that it is based on weight.

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

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

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

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

The nicotine composition of the present invention contains at least 0.2% nicotine by weight. More preferably, the nicotine content in the nicotine composition is at least about 0.4% by weight. The nicotine composition will have a nicotine content of up to about 12% by weight, such as up to about 10% by weight, preferably up to about 8% by weight, more preferably up to about 5% by weight, preferably up to about 3.6% by weight. You can. Most preferably, the nicotine composition comprises about 0.4% to 3.6% nicotine by weight, based on the weight of the nicotine composition.

The nicotine composition may include 1% to 85% water by weight. The nicotine composition may include 2% to 50% water by weight. The nicotine composition may include 3% to 30% water by weight. The nicotine composition may include 5% to 25% water by weight. The nicotine composition may include 8% to 20% water by weight. The nicotine composition preferably contains 10% to 15% water by weight.

In some embodiments, nicotine compositions may include one or more water-soluble organic acids. As used herein in connection with the present invention, the term “water-soluble organic acid” describes an organic acid that has a water solubility of at least about 500 mg/ml at 20°C.

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

More preferably, the nicotine composition includes at least one water-soluble carboxylic acid. 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 nicotine composition has a water-soluble organic acid content of at least about 2% by weight. More preferably, the nicotine composition has a water-soluble organic acid content of at least about 3% by weight.

The water-soluble organic acid may be acetic acid. Acetic acid derived 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 a liquid tobacco extract to form a nicotine composition, the total weight of acetic acid in the nicotine composition, including both acetic acid derived from the extraction process and additional acetic acid, preferably ranges from about 0.01% to about 8% by weight. , for example, from about 0.03% to about 8% by weight, from about 0.3% to about 8% by weight, from about 2% to about 8% by weight, or from about 3% to about 8% by weight. More preferably, the total acetic acid content is about 0.01% to about 6% by weight, such as about 0.03% to about 6% by weight, about 0.3% to about 6% by weight, about 2% to about 6% by weight. %, or from about 3% to about 6% by weight.

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

Preferably, the nicotine composition has a water-soluble organic acid content of about 2% to about 8% by weight. For example, the nicotine composition may have a water-soluble organic acid content of about 2% to about 6% by weight.

More preferably, the nicotine composition has a water-soluble organic acid content of about 3% to about 8% by weight. For example, the nicotine composition may have a water-soluble organic acid content of about 3% to about 6% by weight.

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

Preferably, the nicotine composition has a non-tobacco derived flavoring content of about 4% or less by weight. More preferably, the nicotine composition has a non-tobacco derived flavoring content of less than about 3% by weight.

The nicotine composition is analyzed by gas chromatography to determine the content of the liquid. The weight of each compound in the nicotine composition can be reported as micrograms per gram of nicotine composition. The weight ratio of the compounds in the nicotine composition, as 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 ratio is higher when the amount of the preferred flavor compounds β-ionone and β-damascenone is higher, or when the amount of phenol is lower.

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

Furaneol and 2,3-diethyl-5-methylpyrazine are preferred flavor compounds contained in the nicotine compositions of the present invention. For example, furaneol is a preferred compound derived from heat treatment of 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 present invention, the second weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine)*100) to (nicotine) is greater than 5 x 10 ^-4 . This ratio provides a good sensory profile. Preferably, the weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine)*100) to (nicotine) is 8 x 10 ^-4 to 9 x 10 ^-3 , or 1 x 10 ^-3 to 5 x 10 ^-3 .

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

The ratio is higher when the amounts of the preferred flavor compounds β-ionone and β-damascenone are higher, or when the amounts of TSNA and 2-furanmethanol are lower.

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

The nicotine composition may 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, and 2-phenyl. It may contain one or more of ethanol, eugenol, and sotolone.

The nicotine composition includes β-ionone. The nicotine composition contains at least 0.100 micrograms β-ionone per gram of nicotine composition, preferably at least 0.200 micrograms β-ionone per gram of nicotine composition, more preferably at least 0.300 micrograms β-ionone per gram of nicotine composition. paddy, most preferably at least 0.400 micrograms of β-ionone per gram of nicotine composition. In a preferred embodiment, the nicotine composition contains at least 0.500 micrograms β-ionone per gram of nicotine composition, more preferably at least 0.600 micrograms β-ionone per gram of nicotine composition, even more preferably at least 0.600 micrograms β-ionone per gram of nicotine composition. and at least 0.700 micrograms of β-ionone, most preferably at least 0.800 micrograms of β-ionone per gram of nicotine composition. In a particularly preferred embodiment, the nicotine composition contains at least 0.9 micrograms β-ionone per gram of nicotine composition, preferably at least 1.00 micrograms β-ionone per gram of nicotine composition, more preferably at least at least 1.00 micrograms β-ionone per gram of nicotine composition. 1.10 micrograms β-ionone, even more preferably at least 1.20 micrograms β-ionone per gram of nicotine composition, most preferably at least 1.30 micrograms β-ionone per gram of nicotine composition. The weight ratio of (β-ionone) to (phenol) may be greater than 0.150, such as greater than 0.200, preferably greater than 0.400, more preferably greater than 0.600, most preferably greater than 0.800, such as greater than 1.20. (β-ionone) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R,S)- The weight ratio of N-nitrosoanabasin + N-nitrosonornicotine + ((2-furanmethanol)/600) is greater than 0.300, for example greater than 0.500, preferably greater than 0.750, more preferably greater than 1.00, most preferably greater than 1.00. Preferably it may be greater than 1.20, such as greater than 1.80.

The nicotine composition includes β-damascenone. The nicotine composition contains at least 0.100 micrograms β-damascenone per gram of nicotine composition, preferably at least 0.350 micrograms β-damascenone per gram of nicotine composition, more preferably at least 0.600 micrograms β per gram of nicotine composition. -damascenone, most preferably at least 0.850 micrograms of β-damascenone per gram of the nicotine composition. In a preferred embodiment, the nicotine composition contains at least 1.10 micrograms β-damascenone per gram of nicotine composition, more preferably at least 1.35 micrograms β-damascenone per gram of nicotine composition, even more preferably At least 1.60 micrograms of β-damascenone per gram, most preferably at least 1.85 micrograms of β-damascenone per gram of the nicotine composition. In a particularly preferred embodiment, the nicotine composition contains at least 2.10 micrograms of β-damascenone per gram of nicotine composition, preferably at least 2.35 micrograms of β-damascenone per gram of nicotine composition, more preferably at least 2.35 micrograms of β-damascenone per gram of nicotine composition. at least 2.60 micrograms β-damascenone per gram, even more preferably at least 2.75 micrograms β-damasenone per gram of nicotine composition, most preferably at least 2.90 micrograms β-damasenone per gram of nicotine composition. Includes. The weight ratio of (β-damascenone) to (phenol) may be greater than 0.250, such as greater than 0.300, preferably greater than 0.700, more preferably greater than 1.00, most preferably greater than 1.30, such as greater than 1.60. (β-Damacenone) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R,S) The weight ratio of -N-nitrosoanabasin + N-nitrosonornicotine + ((2-furanmethanol)/600) is greater than 0.300, for example greater than 0.700, preferably greater than 1.00, more preferably greater than 1.50, Most preferably it may be greater than 2.20, such as greater than 2.70.

The weight ratio of (β-ionone + β-damacenone) to (nicotine) is greater than 5.00 x 10 ^-5 , for example greater than 1.00 x 10 ^-4 , preferably greater than 2.00 x 10 ^-4 , more preferably. It may be greater than 4.00 x 10 ^-4 , most preferably greater than 6.00 x 10 ^-4 , such as greater than 7.00 x 10 ^-4 .

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

The nicotine composition includes 2,3-diethyl-5-methylpyrazine. The nicotine composition may contain ^at least ^3.00 -5-methylpyrazine, more preferably at least 9.00 x 10 ^-3 micrograms per gram of nicotine composition 2,3-diethyl-5-methylpyrazine, most preferably at least 1.50 x 10 ^-2 per gram of nicotine composition It may contain micrograms of 2,3-diethyl-5-methylpyrazine. In a preferred embodiment, the nicotine composition contains at least 2.50 x 10 ^-2 micrograms 2,3-diethyl-5-methylpyrazine per gram of nicotine composition, more preferably at least 3.50 x 10 ^-2 micrograms per gram of nicotine composition. 2,3-diethyl-5-methylpyrazine, even more preferably at least 5.00 x 10 ^-2 micrograms per gram of nicotine composition. and at least 7.50 x 10 ^-2 micrograms of 2,3-diethyl-5-methylpyrazine per liter. In a particularly preferred embodiment, the nicotine composition contains at least 9.00 x 10 ^-2 micrograms 2,3-diethyl-5-methylpyrazine per gram of nicotine composition, preferably at least 0.100 micrograms 2,3- per gram of nicotine composition. Diethyl-5-methylpyrazine, more preferably at least 0.200 micrograms per gram of nicotine composition 2,3-diethyl-5-methylpyrazine, even more preferably at least 0.300 micrograms per gram of nicotine composition 2,3 -diethyl-5-methylpyrazine, most preferably at least 0.400 micrograms 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, such as It may be greater than 0.600. (2,3-diethyl-5-methylpyrazine) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine The weight ratio of + (R,S)-N-nitrosoanabasin + N-nitrosonornicotine + ((2-furanmethanol)/600) is greater than 0.0300, for example greater than 0.0400, preferably greater than 0.100, more Preferably it may be greater than 0.500, most preferably greater than 0.800, such as greater than 0.900.

The nicotine composition may include acetic acid. Preferably, the acetic acid is derived from the extraction process, but as previously discussed herein, additional acetic acid may be added after the extraction process. Acetic acid is a preferred compound for smoothing and reducing the harshness of the generated aerosol.

The nicotine composition has at least 300 micrograms acetic acid per gram of nicotine composition, preferably at least 500 micrograms acetic acid per gram of nicotine composition, more preferably at least 700 micrograms acetic acid per gram of nicotine composition, most preferably at least 700 micrograms acetic acid per gram of nicotine composition. May contain at least 900 micrograms acetic acid per gram. In a preferred embodiment, the nicotine composition contains at least 1200 micrograms acetic acid per gram of nicotine composition, more preferably at least 1500 micrograms acetic acid per gram of nicotine composition, even more preferably at least 2000 micrograms acetic acid per gram of nicotine composition, Most preferably it contains at least 2500 micrograms of acetic acid per gram of nicotine composition. In a particularly preferred embodiment, the nicotine composition contains at least 3000 micrograms acetic acid per gram of nicotine composition, preferably at least 3500 micrograms acetic acid per gram of nicotine composition, more preferably at least 4000 micrograms acetic acid per gram of nicotine composition. More preferably it comprises at least 4500 micrograms acetic acid per gram of nicotine composition, and most preferably at least 5000 micrograms 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-nitro The weight ratio of sonabacin + N-nitrosonornicotine + ((2-furanmethanol)/600) is greater than 2100, for example greater than 2800, preferably greater than 3000, more preferably greater than 4000, most preferably It may be greater than 5500, such as greater than 7500.

The nicotine composition may include vanillin. The nicotine composition contains at least 3.00 x 10 ^-2 micrograms vanillin per gram of nicotine composition, preferably at least 5.00 x 10 ^-2 micrograms vanillin per gram of nicotine composition, more preferably at least 7.00 x 10 ^{- 2} micrograms vanillin, most preferably at least 9.00 x 10 ^-2 micrograms vanillin per gram of nicotine composition. In a preferred embodiment, the nicotine composition contains at least 0.100 micrograms vanillin per gram of nicotine composition, more preferably at least 0.200 micrograms vanillin per gram of nicotine composition, even more preferably at least 0.300 micrograms vanillin per gram of nicotine composition, Most preferably it contains at least 0.400 micrograms vanillin per gram of nicotine composition. In a particularly preferred embodiment, the nicotine composition contains at least 0.500 micrograms vanillin per gram of nicotine composition, preferably at least 0.600 micrograms vanillin per gram of nicotine composition, more preferably at least 0.700 micrograms vanillin per gram of nicotine composition. More preferably it comprises at least 0.800 micrograms vanillin per gram of nicotine composition, most preferably at least 0.900 micrograms vanillin per gram of 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-nitro The weight ratio of sonabacin + N-nitrosonornicotine + ((2-furanmethanol)/600) is greater than 0.110, for example greater than 0.150, preferably greater than 0.160, more preferably greater than 0.200, most preferably It may be greater than 0.300, such as greater than 0.500.

The nicotine composition may include 2-ethyl-3,5-dimethylpyrazine. The nicotine composition contains at least 0.0800 micrograms 2-ethyl-3,5-dimethylpyrazine per gram of nicotine composition, preferably at least 0.100 micrograms 2-ethyl-3,5-dimethylpyrazine per gram of nicotine composition, more preferably The nicotine composition may comprise at least 0.200 micrograms 2-ethyl-3,5-dimethylpyrazine per gram, most preferably at least 0.300 micrograms 2-ethyl-3,5-dimethylpyrazine per gram of nicotine composition. In a preferred embodiment, the nicotine composition contains at least 0.500 micrograms 2-ethyl-3,5-dimethylpyrazine per gram of nicotine composition, more preferably at least 0.700 micrograms 2-ethyl-3,5-dimethyl per gram of nicotine composition. pyrazine, even more preferably at least 0.900 micrograms 2-ethyl-3,5-dimethylpyrazine per gram of nicotine composition, most preferably at least micrograms 2-ethyl-3,5-dimethylpyrazine per gram of nicotine composition. Includes. In a particularly preferred embodiment, the nicotine composition contains at least 1.10 micrograms 2-ethyl-3,5-dimethylpyrazine per gram of nicotine composition, preferably at least 1.30 micrograms 2-ethyl-3,5-dimethyl per gram of nicotine composition. pyrazine, more preferably at least 1.50 micrograms 2-ethyl-3,5-dimethylpyrazine per gram of nicotine composition, even more preferably at least 1.70 micrograms 2-ethyl-3,5-dimethylpyrazine per gram of nicotine composition , most preferably comprising at least 1.90 micrograms 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, such as 2.50. It may be excessive. (2-ethyl-3,5-dimethylpyrazine) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + The weight ratio of (R,S)-N-nitrosoanabasin + N-nitrosonornicotine + ((2-furanmethanol)/600) is greater than 0.500, for example greater than 0.750, preferably greater than 1.00, more preferably Typically it may be greater than 2.00, most preferably greater than 3.00, such as greater than 3.50.

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

The nicotine composition may include 3-methylbutanoic acid. The nicotine composition contains at least 2.00 micrograms 3-methylbutanoic acid per gram of nicotine composition, preferably at least 3.00 micrograms 3-methylbutanoic acid per gram of nicotine composition, more preferably at least 4.00 micrograms per gram of nicotine composition. -methylbutanoic acid, most preferably at least 5.00 micrograms 3-methylbutanoic acid per gram of nicotine composition. In a preferred embodiment, the nicotine composition contains at least 6.00 micrograms 3-methylbutanoic acid per gram of nicotine composition, more preferably at least 8.00 micrograms 3-methylbutanoic acid per gram of nicotine composition, even more preferably and at least 10.0 micrograms 3-methylbutanoic acid per gram, most preferably at least micrograms 3-methylbutanoic acid per gram of the nicotine composition. In a particularly preferred embodiment, the nicotine composition contains at least 15.0 micrograms 3-methylbutanoic acid per gram of nicotine composition, preferably at least 20.0 micrograms 3-methylbutanoic acid per gram of nicotine composition, more preferably gram of nicotine composition. at least 25.0 micrograms 3-methylbutanoic acid per gram, even more preferably at least 30.0 micrograms 3-methylbutanoic acid per gram of nicotine composition, and most preferably at least 35.0 micrograms 3-methylbutanoic acid per gram of nicotine composition. Includes. The weight ratio of (3-methylbutanoic acid) to (phenol) may be 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, such as greater than 51.0. (3-methylbutanoic acid) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R,S) -The weight ratio of N-nitrosoanabasin + N-nitrosonornicotine + ((2-furanmethanol)/600) is greater than 18.0, for example greater than 40.0, preferably greater than 50.0, more preferably greater than 60.0, Most preferably it may be greater than 65.0, such as greater than 70.0.

The nicotine composition may include 3-methyl-2,4-nonanedione. The nicotine composition contains at least 6.00 x 10 ^-3 micrograms 3-methyl-2,4-nonanedione per gram of nicotine composition, preferably at least 8.00 x 10 ^-3 micrograms 3-methyl-2,4 per gram of nicotine composition. -nonanedione, more preferably at least 9.00 x 10 ^-3 micrograms 3-methyl-2,4-nonanedione, most preferably at least 0.0100 micrograms 3-methyl-2 per gram of nicotine composition. , 4-nonanedione may be included. In a preferred embodiment, the nicotine composition contains at least 0.0300 micrograms 3-methyl-2,4-nonanedione per gram of nicotine composition, more preferably at least 0.0500 micrograms 3-methyl-2,4-nonane per gram of nicotine composition. dione, even more preferably at least 0.0700 micrograms 3-methyl-2,4-nonanedione per gram of nicotine composition, most preferably at least micrograms 3-methyl-2,4-nonanedione per gram of nicotine composition. do. In a particularly preferred embodiment, the nicotine composition contains at least 0.0900 micrograms 3-methyl-2,4-nonanedione per gram of nicotine composition, preferably at least 0.100 micrograms 3-methyl-2,4-nonane per gram of nicotine composition. dione, more preferably at least 0.150 micrograms 3-methyl-2,4-nonanedione per gram of nicotine composition, even more preferably at least 0.200 micrograms 3-methyl-2,4-nonanedione per gram of nicotine composition , most preferably comprising 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) de (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, such as 0.250. It may be excessive. (3-methyl-2,4-nonanedione) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + The weight ratio of (R,S)-N-nitrosoanabasin + N-nitrosonornicotine + ((2-furanmethanol)/600) is greater than 0.035, for example greater than 0.040, preferably greater than 0.080, more preferably Typically it may be greater than 0.090, most preferably greater than 0.100, such as greater than 0.130.

The nicotine composition may include 2-methoxyphenol. The nicotine composition contains at least 0.150 micrograms 2-methoxyphenol per gram of nicotine composition, preferably at least 0.300 micrograms 2-methoxyphenol per gram of nicotine composition, more preferably at least 0.500 micrograms per gram of nicotine composition. -methoxyphenol, most preferably at least 0.600 micrograms 2-methoxyphenol per gram of the nicotine composition. In a preferred embodiment, the nicotine composition contains at least 0.700 micrograms 2-methoxyphenol per gram of nicotine composition, more preferably at least 0.800 micrograms 2-methoxyphenol per gram of nicotine composition, even more preferably and at least 0.900 micrograms 2-methoxyphenol per gram, most preferably at least at least micrograms 2-methoxyphenol per gram of the nicotine composition. In a particularly preferred embodiment, the nicotine composition contains at least 1.00 micrograms 2-methoxyphenol per gram of nicotine composition, preferably at least 1.50 micrograms 2-methoxyphenol per gram of nicotine composition, more preferably at least 1.50 micrograms 2-methoxyphenol per gram of nicotine composition. at least 2.00 micrograms 2-methoxyphenol per gram, even more preferably at least 2.50 micrograms 2-methoxyphenol per gram of nicotine composition, and most preferably at least 3.00 micrograms 2-methoxyphenol per gram of nicotine composition. Includes. The weight ratio of (2-methoxyphenol) to (phenol) may be greater than 0.0900, such as greater than 1.00, preferably greater than 1.50, more preferably greater than 2.00, most preferably greater than 3.00, such as greater than 4.50. (2-methoxyphenol) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R,S) The weight ratio of -N-nitrosoanabasin + N-nitrosonornicotine + ((2-furanmethanol)/600) is greater than 1.40, for example greater than 1.80, more preferably greater than 2.00, most preferably greater than 2.00. Preferably it may be greater than 3.00, such as greater than 6.00.

The nicotine composition may include 2-phenylethanol. The nicotine composition contains at least 1.50 micrograms 2-phenylethanol per gram of nicotine composition, preferably at least 3.00 micrograms 2-phenylethanol per gram of nicotine composition, more preferably at least 5.00 micrograms 2-phenyl per gram of nicotine composition. Ethanol, most preferably at least 7.00 micrograms 2-phenylethanol per gram of nicotine composition. In a preferred embodiment, the nicotine composition contains at least 9.00 micrograms 2-phenylethanol per gram of nicotine composition, more preferably at least 10.0 micrograms 2-phenylethanol per gram of nicotine composition, even more preferably per gram of nicotine composition. and at least 11.0 micrograms 2-phenylethanol, most preferably at least micrograms 2-phenylethanol per gram of nicotine composition. In a particularly preferred embodiment, the nicotine composition contains at least 13.0 micrograms 2-phenylethanol per gram of nicotine composition, preferably at least 15.0 micrograms 2-phenylethanol per gram of nicotine composition, more preferably at least per gram of nicotine composition. 16.0 micrograms 2-phenylethanol, even more preferably at least 17.0 micrograms 2-phenylethanol per gram of nicotine composition, and most preferably at least 18.0 micrograms 2-phenylethanol per gram of nicotine composition. The weight ratio of (2-phenylethanol) to (phenol) may be greater than 3.00, such as greater than 5.00, preferably greater than 8.00, more preferably greater than 9.00, most preferably greater than 10.0, such as greater than 25.0. (2-phenylethanol) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R,S)- The weight ratio of N-nitrosoanabasin + N-nitrosonornicotine + ((2-furanmethanol)/600) is greater than 10.0, for example greater than 13.0, preferably greater than 14.0, more preferably greater than 15.0, most preferably greater than 15.0. Preferably it may be greater than 17.0, such as greater than 35.0.

The nicotine composition may include eugenol. The nicotine composition may contain at least 0.0600 microgram eugenol per gram of nicotine composition, preferably at least 0.0650 microgram eugenol per gram of nicotine composition, more preferably at least 0.0700 microgram eugenol per gram of nicotine composition, most preferably The nicotine composition may contain at least 0.0800 micrograms of eugenol per gram. In a preferred embodiment, the nicotine composition contains at least 0.0900 micrograms eugenol per gram of nicotine composition, more preferably at least 0.100 micrograms eugenol per gram of nicotine composition, and even more preferably at least 0.200 micrograms per gram of nicotine composition. Eugenol, most preferably at least micrograms eugenol per gram of nicotine composition. In a particularly preferred embodiment, the nicotine composition contains an emulsion of at least 0.300 microgram eugenol per gram of nicotine composition, preferably at least 0.400 microgram eugenol per gram of nicotine composition, more preferably at least 0.500 microgram eugenol per gram of nicotine composition. nicotine composition, more preferably at least 0.600 microgram eugenol per gram of nicotine composition, and most preferably at least 0.700 microgram eugenol per gram of nicotine composition. The weight ratio of (eugenol) to (phenol) may be 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, such as greater than 1.20. (Eugenol) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R,S)-N- The weight ratio of nitrosoanabasin + N-nitrosonornicotine + ((2-furanmethanol)/600) is greater than 0.0200, for example greater than 0.0250, preferably greater than 0.0300, more preferably greater than 0.500, most preferably may be greater than 0.550, such as greater than 1.50.

The nicotine composition may include sotolone. The nicotine composition has at least 3.00 x 10 ^-3 micrograms sotolone per gram of nicotine composition, preferably at least 5.00 x 10 ^-3 micrograms sotolone per gram of nicotine composition, more preferably at least 7.00 x 10 -3 micrograms sotolone per gram of nicotine composition. 10 ^-3 micrograms sotolone, most preferably at least 9.00 x 10 ^-3 micrograms sotolone per gram of nicotine composition. In a preferred embodiment, the nicotine composition contains at least 0.0100 micrograms sotolone per gram of nicotine composition, more preferably at least 0.0200 micrograms sotolone per gram of nicotine composition, and even more preferably at least 0.0300 micrograms per gram of nicotine composition. sotolone, most preferably at least micrograms sotolone per gram of nicotine composition. In a particularly preferred embodiment, the nicotine composition contains at least 0.0400 microgram sotolone per gram of nicotine composition, preferably at least 0.0500 microgram sotolone per gram of nicotine composition, more preferably at least 0.0600 microgram sotolone per gram of nicotine composition. Tolon, even more preferably at least 0.0700 micrograms sotolone per gram of nicotine composition, most preferably at least 0.0800 micrograms sotolone per gram of nicotine composition. The weight ratio of (sotolone) to (phenol) may be greater than 0.0200, such as greater than 0.0400, preferably greater than 0.150, more preferably greater than 0.0450 and most preferably greater than 0.0500, such as greater than 0.0510. (sotolone) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R,S)-N- The weight ratio of nitrosoanabasin + N-nitrosonornicotine + ((2-furanmethanol)/600) is greater than 0.0300, for example greater than 0.0400, preferably greater than 0.0500, more preferably greater than 0.0600, most preferably may be greater than 0.0700, such as greater than 0.0750.

In addition to phenol, TSNA NNK, NAT, NAB and NNNN, and 2-furanmethanol, other undesirable compounds that may be present in the nicotine composition but are minimized by the extraction method described herein include formaldehyde (from sugars) and acetaldehyde; Phenolic compounds such as catechol, hydroquinone, m-cresol and p-cresol, and nitrogen containing compounds such as ammonia, acetamide, pyridine, 3-aminobiphenyl, 4-aminobiphenyl and o-toludine.

The nicotine composition may contain at most 12.0 micrograms phenol per gram of nicotine composition, for example at most 10.0 micrograms phenol per gram of nicotine composition, preferably at most 8.00 micrograms phenol per gram of nicotine composition, more preferably at most 8.00 micrograms phenol per gram of nicotine composition. It may comprise up to 6.00 micrograms phenol per gram, more preferably up to 4.00 micrograms phenol per gram of nicotine composition, and most preferably up to 2.00 micrograms phenol per gram of nicotine composition.

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

The nicotine composition may contain at most 2.00 micrograms (R,S)-N-nitrosoanatabine (NAT) per gram of nicotine composition, for example at most micrograms NAT per gram of nicotine composition, preferably at most per gram of nicotine composition. 1.50 micrograms NAT, more preferably at most 1.00 micrograms NAT per gram of nicotine composition, even more preferably at most 0.500 micrograms NAT per gram of nicotine composition, most preferably at most 0.300 micrograms NAT per gram of nicotine composition. may include.

The nicotine composition may contain at most 1.60 micrograms (R,S)-N-nitrosoanabasin (NAB) per gram of nicotine composition, for example at most micrograms NAB per gram of nicotine composition, preferably at most per gram of nicotine composition. 1.20 micrograms NAB, more preferably at most 0.500 micrograms NAB per gram of nicotine composition, even more preferably at most 0.300 micrograms NAB per gram of nicotine composition, most preferably at most 0.200 micrograms NAB per gram of nicotine composition. may include.

The nicotine composition may contain at most 1.60 micrograms N-nitrosonornicotine (NNN) per gram of nicotine composition, for example at most micrograms NNN per gram of nicotine composition, preferably at most 1.20 micrograms NNN per gram of nicotine composition, more Preferably at most 0.500 micrograms NNN per gram of nicotine composition, even more preferably at most 0.300 micrograms NNN per gram of nicotine composition, and most preferably at most 0.200 micrograms NNN per gram of nicotine composition.

The nicotine composition may contain up to 1500 micrograms 2-furanmethanol per gram of nicotine composition, for example up to micrograms 2-furanmethanol per gram of nicotine composition, preferably at most 1200 micrograms 2-furanmethanol per gram of nicotine composition, More preferably at most 1000 micrograms 2-furanmethanol per gram of nicotine composition, even more preferably at most 900 micrograms 2-furanmethanol per gram of nicotine composition, most preferably at most 700 micrograms per gram of nicotine composition. It may contain 2-furanmethanol.

The nicotine composition may contain at most 60 micrograms formaldehyde per gram of nicotine composition, for example at most micrograms formaldehyde per gram of nicotine composition, preferably at most 50 micrograms formaldehyde per gram of nicotine composition, more preferably at most 50 micrograms formaldehyde per gram of nicotine composition. may comprise at most 40 micrograms formaldehyde per gram, even more preferably at most 30 micrograms formaldehyde per gram of nicotine composition, and most preferably at most 20 micrograms formaldehyde per gram of nicotine composition.

The nicotine composition may contain at most 60 micrograms acetaldehyde per gram of nicotine composition, for example at most micrograms acetaldehyde per gram of nicotine composition, preferably at most 55 micrograms acetaldehyde per gram of nicotine composition, more preferably at most 55 micrograms acetaldehyde per gram of nicotine composition. may comprise at most 45 micrograms acetaldehyde per gram, even more preferably at most 35 micrograms acetaldehyde per gram of nicotine composition, and most preferably at most 30 micrograms acetaldehyde per gram of nicotine composition.

The nicotine composition may contain at most 5.00 micrograms catechol per gram of nicotine composition, for example at most microgram catechol per gram of nicotine composition, preferably at most 4.00 microgram catechol per gram of nicotine composition, more preferably at most 4.00 microgram catechol per gram of nicotine composition. may comprise at most 3.00 micrograms catechol per gram, more preferably at most 2.00 micrograms catechol per gram of nicotine composition, and most preferably at most 1.00 micrograms catechol per gram of nicotine composition.

The nicotine composition may contain at most 1.00 micrograms hydroquinone per gram of nicotine composition, for example at most 0.950 microgram hydroquinone per gram of nicotine composition, preferably at most 0.900 microgram hydroquinone per gram of nicotine composition, more preferably nicotine. The composition may comprise up to 0.850 micrograms hydroquinone per gram of nicotine composition, even more preferably up to 0.800 microgram hydroquinone per gram of nicotine composition, and most preferably up to 0.700 microgram hydroquinone per gram of nicotine composition.

The nicotine composition may contain at most 1.30 micrograms m-cresol per gram of nicotine composition, for example at most 1.20 micrograms m-cresol per gram of nicotine composition, preferably at most 1.00 micrograms m-cresol per gram of nicotine composition, more preferably preferably at most 0.800 micrograms m-cresol per gram of nicotine composition, more preferably at most 0.600 micrograms m-cresol per gram of nicotine composition, most preferably at most 0.500 micrograms m-cresol per gram of nicotine composition. It can be included.

The nicotine composition may contain at most 1.60 micrograms o-cresol per gram of nicotine composition, for example at most 1.30 micrograms o-cresol per gram of nicotine composition, preferably at most 1.10 micrograms o-cresol per gram of nicotine composition, more preferably preferably at most 0.800 micrograms o-cresol per gram of nicotine composition, more preferably at most 0.600 micrograms o-cresol per gram of nicotine composition, most preferably at most 0.400 micrograms o-cresol per gram of nicotine composition. It can be included.

The nicotine composition may contain at most 2.10 micrograms p-cresol per gram of nicotine composition, for example at most 1.50 micrograms p-cresol per gram of nicotine composition, preferably at most 1.20 micrograms p-cresol per gram of nicotine composition, more preferably Preferably at most 1.00 micrograms p-cresol per gram of nicotine composition, more preferably at most 0.900 micrograms p-cresol per gram of nicotine composition, most preferably at most 0.700 micrograms p-cresol per gram of nicotine composition. It can be included.

The nicotine composition may contain at most 350 micrograms ammonia per gram of nicotine composition, for example at most 300 micrograms ammonia per gram of nicotine composition, preferably at most 275 micrograms ammonia per gram of nicotine composition, more preferably at most 275 micrograms ammonia per gram of nicotine composition. It may comprise up to 250 micrograms ammonia per gram, even more preferably up to 200 micrograms ammonia per gram of nicotine composition, and most preferably up to 175 micrograms ammonia per gram of nicotine composition.

The nicotine composition may contain at most 250 micrograms acetamide per gram of nicotine composition, for example at most 225 micrograms acetamide per gram of nicotine composition, preferably at most 200 micrograms acetamide per gram of nicotine composition, more preferably nicotine. The composition may comprise up to 150 micrograms acetamide per gram of the nicotine composition, even more preferably up to 100 micrograms acetamide per gram of the nicotine composition, and most preferably up to 70 micrograms acetamide per gram of the nicotine composition.

The nicotine composition may contain at most 45 micrograms pyridine per gram of nicotine composition, for example at most 35 micrograms pyridine per gram of nicotine composition, preferably at most 25 micrograms pyridine per gram of nicotine composition, more preferably at most grams of nicotine composition. It may comprise up to 20 micrograms pyridine per gram, more preferably up to 15 micrograms pyridine per gram of nicotine composition, and most preferably up to 10 micrograms pyridine per gram of nicotine composition.

The nicotine composition can be produced as a liquid tobacco extract from tobacco starting material consisting of a single type of natural tobacco. Tobacco starting materials may include a blend of two or more types of natural tobacco. Alternatively, the nicotine composition may comprise a first tobacco starting material consisting of a first single type of natural tobacco from which the first extract is extracted, a first single type of natural tobacco from which the second extract is extracted. 2 A liquid tobacco extract from a blend produced from a second tobacco starting material consisting of a single type of natural tobacco, wherein the first extract and the second extract are blended to form the liquid tobacco extract. Two or more extracts can be blended in this manner to form a liquid tobacco extract. The proportion of different tobacco types can be adapted depending on the desired properties of the aerosol generated from the nicotine composition. For example, if it is desirable to provide relatively high levels of nicotine, the proportion of Burley type cigarettes may be increased.

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

For example, liquid tobacco extract produced by an extraction process can be used to prepare a nicotine composition comprising 10 to 20 mg of nicotine per milliliter, without the need for adding nicotine. The term “liquid tobacco extract” describes the direct product of the extraction process from tobacco material. Accordingly, liquid tobacco extracts typically include a mixture of natural components that are isolated from, removed from, or derived from natural tobacco material using tobacco extraction processing conditions and techniques. Accordingly, in one such process, the extracted tobacco components are removed from the natural tobacco material and separated from the unextracted tobacco components. Accordingly, a liquid tobacco extract typically consists of a mixture of natural tobacco components derived from the tobacco starting material and extracted or formed during the extraction process, in combination with one or more materials other than the tobacco starting material, such as the extraction solvent used during the extraction process. The extraction solvent is preferably an aerosol former.

As used herein, the term “aerosol former” refers to a compound or mixture of compounds that, when used, promotes the formation of an aerosol and is preferably substantially resistant to thermal degradation at the operating temperature of the aerosol-generating article or device. refers to 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 mono-, di- or triacetate; and aliphatic esters of mono-, di- or polycarboxylic acids such as dimethyl dodecanedioate and dimethyl tetradecanedioate.

The nicotine composition may include liquid tobacco extract resulting from an extraction process to which additional nicotine is added. In the nicotine composition according to the invention, at least 50% by weight of the nicotine content in the nicotine composition, based on the total weight of the nicotine composition, may come from liquid tobacco extract as opposed to being added after extraction. In a preferred embodiment, at least 80% by weight of the nicotine content in the nicotine composition, based on the total weight of the nicotine composition, comes from liquid tobacco extract as opposed to being added after extraction. Even more preferably, at least 90% by weight of the nicotine content in the nicotine composition, based on the total weight of the nicotine composition, comes from liquid tobacco extract as opposed to being added after extraction.

The nicotine composition may include liquid tobacco extract resulting from an extraction process in which additional non-aqueous solvents are added. In the nicotine composition according to the invention, at least 50% by weight, based on the total weight of the nicotine composition, of the non-aqueous extraction solvent content in the nicotine composition may come from liquid tobacco extract as opposed to being added after extraction. In a preferred embodiment, at least 80% by weight of the non-aqueous extraction solvent content in the nicotine composition, based on the total weight of the nicotine composition, comes from the liquid tobacco extract as opposed to being added after extraction. Even more preferably, at least 90% by weight of the non-aqueous extraction solvent content in the nicotine composition, based on the total weight of the nicotine composition, comes from liquid tobacco extract as opposed to being added after extraction.

The nicotine composition may include liquid tobacco extract resulting from an extraction process to which additional water is added. In the nicotine composition according to the invention, at least 50% by weight of the water content in the nicotine composition, based on the total weight of the nicotine composition, may come from the liquid tobacco extract as opposed to being added after extraction. In a preferred embodiment, at least 80% by weight of the water content in the nicotine composition, based on the total weight of the nicotine composition, comes from the liquid tobacco extract as opposed to being added after extraction. Even more preferably, at least 90% by weight of the water content in the nicotine composition, based on the total weight of the nicotine composition, comes from the liquid tobacco extract as opposed to being added after extraction. Even more preferably, 100% by weight of the nicotine content in the nicotine composition, based on the total weight of the nicotine composition, comes from liquid tobacco extract as opposed to being added after extraction.

The nicotine composition may include liquid tobacco extract resulting from an extraction process to which additional flavor compounds are added. In the nicotine composition according to the invention, at least 50% by weight, based on the total weight of the nicotine composition, of the desired tobacco flavor species content in the nicotine composition may come from liquid tobacco extract as opposed to being added after extraction. In a preferred embodiment, at least 80% by weight, based on the total weight of the nicotine composition, of the desired tobacco flavor species content in the nicotine composition comes from the liquid tobacco extract as opposed to being added after extraction. More preferably, at least 90% by weight, based on the total weight of the nicotine composition, of the desired tobacco flavor species content in the nicotine composition comes from liquid tobacco extract as opposed to being added after extraction. Even more preferably, 100% by weight, based on the total weight of the nicotine composition, of the desired tobacco flavor species content in the nicotine composition comes from liquid tobacco extract as opposed to being added after extraction.

By way of example, at least 50% by weight of the furaneol content in the nicotine composition, based on the total weight of the nicotine composition, may come from liquid tobacco extract as opposed to being added after extraction. In a preferred embodiment, at least 80% by weight of the furaneol content in the nicotine composition, based on the total weight of the nicotine composition, comes from the liquid tobacco extract as opposed to being added after extraction. More preferably, at least 90% by weight of the furaneol content in the nicotine composition, based on the total weight of the nicotine composition, comes from liquid tobacco extract as opposed to being added after extraction. Even more preferably, 100% by weight of the furaneol content in the nicotine composition, based on the total weight of the nicotine composition, comes from liquid tobacco extract as opposed to being added after extraction.

As another example, at least 50% by weight of the 2,3-diethyl-5-methylpyrazine content in the nicotine composition, based on the total weight of the nicotine composition, may come from liquid tobacco extract as opposed to being added after extraction. In a preferred embodiment, at least 80% by weight of the 2,3-diethyl-5-methylpyrazine content in the nicotine composition, based on the total weight of the nicotine composition, comes from liquid tobacco extract as opposed to being added after extraction. More preferably, at least 90% by weight of the 2,3-diethyl-5-methylpyrazine content in the nicotine composition, based on the total weight of the nicotine composition, comes from liquid tobacco extract as opposed to being added after extraction. Even more preferably, 100% by weight of the 2,3-diethyl-5-methylpyrazine content in the nicotine composition, based on the total weight of the nicotine composition, comes from liquid tobacco extract as opposed to being added after extraction.

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

By way of example, in a nicotine composition according to the invention, at least 50% by weight of the furaneol content in the nicotine composition, based on the total weight of the nicotine composition, may come from tobacco extract as opposed to being added after extraction. In a preferred embodiment, at least 80% by weight of the furaneol content in the nicotine composition, based on the total weight of the nicotine composition, comes from tobacco extract as opposed to being added after extraction. Even more preferably, at least 90% by weight of the furaneol content in the nicotine composition, based on the total weight of the nicotine composition, comes from tobacco extract as opposed to being added after extraction.

As another example, in the nicotine composition according to the present invention, at least 50% by weight, based on the total weight of the nicotine composition, of the 2,3-diethyl-5-methylpyrazine content in the nicotine composition is obtained from the tobacco extract as opposed to being added after extraction. It can come out. In a preferred embodiment, at least 80% by weight of the 2,3-diethyl-5-methylpyrazine content in the nicotine composition, based on the total weight of the nicotine composition, comes from tobacco extract as opposed to being added after extraction. Even more preferably, at least 90% by weight of the 2,3-diethyl-5-methylpyrazine content in the nicotine composition, based on the total weight of the nicotine composition, comes from tobacco extract as opposed to being added after extraction.

The nicotine composition is preferably produced from liquid tobacco extract. The liquid tobacco extract is preferably prepared in combination with a specifically defined heating duration that advantageously provides an improved liquid tobacco extract, and thus an improved nicotine composition, with a significantly improved balance of desirable versus undesirable compounds. It is produced using an extraction method at extraction temperatures within the range. In particular, the extraction process provides liquid tobacco extracts and nicotine compositions with maximized ratios of desirable to undesirable compounds for tobacco starting materials. For example, the use of specific combinations of defined extraction temperatures and times allows the levels of nicotine and flavor compounds to be optimized while removing undesirable substances such as furans, phenols and phenolic compounds, and tobacco-specific nitrosamines (TSNA). Minimize levels of compounds.

Accordingly, the liquid tobacco extracts and nicotine compositions obtained by one such method exhibit significant compositional differences with respect to the tobacco extracts and nicotine compositions obtained by conventional extraction processes and, when heated or used as e-liquids, are significantly different from those currently available. It can be used in the preparation of e-liquids to generate aerosols with distinct composition and flavor characteristics compared to e-liquids. In particular, the liquid tobacco extracts and nicotine compositions obtained by the process according to the invention are more effective than the available aerosols generated from conventional liquid nicotine compositions, such as those generated by conventional cigarettes or upon heating the tobacco with a non-combustion-heating device. It can be used to generate an aerosol that provides a heated tobacco taste that more closely resembles the generated aerosol.

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% by weight liquid tobacco extract. Preferably, the nicotine composition comprises at least about 20% by weight liquid tobacco extract. More preferably, the nicotine composition includes at least about 30% by weight liquid tobacco extract. In a preferred embodiment, the nicotine composition comprises at least about 40% by weight liquid tobacco extract, more preferably at least about 50% by weight liquid tobacco extract, and even more preferably at least about 60% by weight liquid tobacco extract. In a particularly preferred embodiment, the nicotine composition comprises at least about 65% by weight liquid tobacco extract, more preferably at least about 70% by weight liquid tobacco extract, even more preferably at least about 75% by weight liquid tobacco extract, most preferably Preferably it includes at least about 80% by weight 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 step, such as the drying step described herein. The nicotine composition may comprise at least about 10% by weight concentrated tobacco extract, at least about 20% by weight concentrated tobacco extract, at least about 30% by weight concentrated tobacco extract, at least about 40% by weight concentrated tobacco extract, at least about 50% by weight concentrate. Tobacco extract, preferably at least about 60% by weight concentrated tobacco extract, more preferably at least about 70% by weight concentrated tobacco extract, even more preferably at least about 75% by weight concentrated tobacco extract, and most preferably It may comprise at least about 80% by weight of concentrated tobacco extract.

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

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

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

The nicotine composition may include up to about 100% liquid tobacco extract by weight. In some embodiments, nicotine compositions can be formed directly from liquid tobacco extract without the need to add additional non-aqueous solvents, flavoring agents, or nicotine. That is, the nicotine composition may include 100% by weight of liquid tobacco extract. In some embodiments, the liquid tobacco extract is a concentrated tobacco extract, such that the nicotine composition may include 100% by weight of the concentrated tobacco extract. In embodiments where the nicotine composition comprises 100% liquid tobacco extract by weight or 100% concentrated tobacco extract by weight, 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. As noted above, the total content of non-aqueous solvents in the nicotine composition includes the non-aqueous extraction solvent and additional non-aqueous solvents, if present.

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

In embodiments where the nicotine composition includes an additional non-aqueous solvent, the nicotine composition may include up to 90% by weight of the additional non-aqueous solvent. Preferably, the nicotine composition comprises up to 80% by weight of additional non-aqueous solvent. More preferably, the nicotine composition comprises up to 70% by weight of additional non-aqueous solvent. In a preferred embodiment, the nicotine composition contains up to about 60% by weight of additional non-aqueous solvent, more preferably up to about 50% by weight of additional non-aqueous solvent, and even more preferably up to about 40% by weight of additional non-aqueous solvent. Includes. In a particularly preferred embodiment, the nicotine composition contains up to about 35% by weight of additional non-aqueous solvent, more preferably up to about 30% by weight of additional non-aqueous solvent, and even more preferably up to about 25% by weight of additional non-aqueous solvent. , most preferably comprising up to about 20% by weight of liquid tobacco extract.

In one exemplary embodiment, the nicotine composition comprises the desired flavor compounds derived from an extraction process as described herein: 84% propylene glycol, 12.5% water, 1.2% nicotine, 0.5% by weight. It is a concentrated tobacco extract containing weight percent acetic acid and 1.8 weight percent balance of other ingredients.

In one exemplary embodiment, the nicotine composition includes 80% by weight of concentrated tobacco extract and 20% by weight of an additional non-aqueous solvent. In this exemplary embodiment, the nicotine composition comprises 20% by weight glycerin as an additional non-aqueous solvent and 80% by weight concentrated tobacco extract, wherein the concentrated tobacco extract contains the desired flavor compounds derived from the extraction process described herein. Including 84% propylene glycol, 12.5% water, 1.2% nicotine, 0.5% total acetic acid, and 1.8% balance by weight other ingredients. Accordingly, the nicotine composition of this exemplary embodiment includes the preferred flavor compounds derived from the extraction process described herein, including 20% by weight glycerin, 67.2% propylene glycol, 10% water, 0.96% by weight. It contains nicotine, 0.4% by weight total acetic acid, and 1.44% by weight balance of other ingredients. This composition contains a total content of non-aqueous solvents of 87.2% by weight, where the non-aqueous solvents include glycerin and propylene glycol.

The nicotine composition may be a gel nicotine composition. As nicotine can be irritating to the skin, it is desirable to prevent any possible leakage of nicotine by fixing it in a gel at room temperature. Such gels are described, for example, in WO 2018/019543 A1.

Advantageously, the gel nicotine composition comprises a thermoreversible gel. This means that the gel becomes a fluid when heated to its melting temperature and sets back into a gel at its gelation temperature. The gelation temperature is preferably room temperature and atmospheric pressure or higher. Atmospheric pressure means a pressure of 1 atmosphere. The melting temperature is preferably higher than the gelation temperature. Preferably, the melting temperature of the gel is greater than 50°C, or 60°C, or 70°C, more preferably greater than 80°C. 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 a suitable gelling agent. Preferably, the gel nicotine composition comprises agar, agarose, sodium alginate or gellan gum. Most preferably, the gel nicotine composition comprises agar. The gel nicotine composition preferably comprises from about 0.5% to about 5% by weight of gelling agent, more preferably from about 0.8% to about 1% by weight of gelling agent.

The gel nicotine composition may include liquid tobacco extract. Preferably, the gel nicotine composition contains from about 50% to about 99.5% liquid tobacco extract, more preferably from about 60% to about 99.5% liquid tobacco extract, and even more preferably from about 70% to about 99.5% liquid tobacco extract. Tobacco extract, most preferably about 80% to about 99.5% liquid tobacco extract.

The liquid tobacco extract can be a concentrated tobacco extract, and the gel nicotine composition can include a concentrated tobacco extract. Preferably, the gel nicotine composition is about 50% to about 99.5% concentrated tobacco extract, more preferably about 60% to about 99.5% concentrated tobacco extract, even more preferably about 70% to about 99.5% concentrated tobacco extract. Tobacco extract, most preferably about 80% to about 99.5% concentrated tobacco extract.

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

The total content of non-aqueous solvents in the gel nicotine composition includes the non-aqueous extraction solvent and additional non-aqueous solvents, if present. The gel nicotine composition may include a total content of non-aqueous solvents from about 10% to about 95% by weight. The gel nicotine composition preferably has about 50% to about 95% by weight, for example about 65% to about 95% by weight, more preferably about 70% to about 90% by weight, most preferably about 80% by weight. and a total content of non-aqueous solvents of from % to about 90% by weight. The non-aqueous solvent is preferably triacetin, glycerin, propylene glycol, 1,3-propanediol, or mixtures thereof.

Gel nicotine compositions may include 1% to 85% water by weight. The gel nicotine composition may include 2% to 50% water by weight. The gel nicotine composition may preferably include 3% to 30% by weight of water. The gel nicotine composition may include 8% to 20% water by weight. The gel nicotine composition may include 10% to 15% water by weight.

The gel nicotine composition contains at least 0.2% nicotine by weight. More preferably, the nicotine content in the gel nicotine composition is at least about 0.4% by weight. The gel nicotine composition may have a nicotine content of less than about 12% by weight, such as less than about 10% by weight, preferably less than about 8% by weight, more preferably less than about 5% by weight, preferably less than about 3.6% by weight. You can. Most preferably, the gel nicotine composition comprises about 0.4% to 3.6% nicotine by weight.

In one exemplary embodiment, the gel nicotine composition includes 80% liquid tobacco extract, 19% additional non-aqueous solvent, and 1% agar by weight. In this exemplary embodiment, the nicotine composition comprises 19% by weight glycerin as an additional non-aqueous solvent and 80% by weight liquid tobacco extract, wherein the liquid tobacco extract is a preferred flavoring agent derived from an extraction process as described herein. Including the compound, it contains 59% by weight glycerin, 37.5% by weight water, 1.2% by weight nicotine, 0.5% total acetic acid by weight, and 1.8% by weight balance of other ingredients. Accordingly, the nicotine composition of this exemplary embodiment comprises the preferred flavor compounds derived from the extraction process as described herein, including 66.2% glycerin, 30% water, 0.96% nicotine, 0.4% wt. of total acetic acid, 1% agar and 1.44% by weight balance of other ingredients.

Nicotine compositions according to the invention may be provided in cartridges for use in aerosol-generating systems. The cartridge may include a nebulizer configured to generate an aerosol from the nicotine composition. The nebulizer may be a thermal nebulizer configured to heat the nicotine composition to generate an aerosol. The thermal nebulizer may include, for example, a heater and a liquid transfer element configured to transfer the nicotine composition to the heater. The liquid transport element may include a capillary wick. Alternatively, the nebulizer may be a non-thermal nebulizer configured to generate an aerosol from the nicotine composition by means other than heating. Non-thermal nebulizers can be, for example, impinging jet nebulizers, ultrasonic nebulizers or vibrating mesh nebulizers.

Cartridges containing nicotine compositions may be used with any suitable aerosol-generating device that includes a housing configured to receive at least a portion of the cartridge. The aerosol-generating device may include a battery and control electronics.

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

Through control of the parameters of the extraction process, it is possible to adjust the properties of the nicotine composition, as well as the resulting aerosol produced from the nicotine composition and delivered to the consumer.

According to the present invention, there is provided a nicotine composition, which is prepared by a method comprising the following steps: a non-aqueous solvent, nicotine, more than 0.25 (β-ionone + β-damascenone) ) to (phenol), and a second weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine)*100) to (nicotine) of greater than 5 x 10 ^-4 . , the method comprises heating the tobacco starting material at an extraction temperature of 100° C. to 160° C. for at least 90 minutes; collecting volatile compounds released from the tobacco starting material during the heating step; forming a liquid tobacco extract comprising the collected volatile compounds; and forming a nicotine composition from the liquid tobacco extract.

As discussed above, nicotine compositions can be produced from liquid tobacco extracts from tobacco starting materials consisting of a single type of natural tobacco. Tobacco starting materials may include a blend of two or more types of natural tobacco. Alternatively, the nicotine composition may comprise a first tobacco starting material consisting of a first single type of natural tobacco from which the first extract is extracted, a first single type of natural tobacco from which the second extract is extracted. 2 A liquid tobacco extract from a blend produced from a second tobacco starting material consisting of a single type of natural tobacco, wherein the first extract and the second extract are blended to form the liquid tobacco extract. Two or more extracts can be blended in this manner to form a liquid tobacco extract. The proportion of different tobacco types can be adapted depending on the desired properties of the aerosol generated from the nicotine composition. For example, if it is desirable to provide relatively high levels of nicotine, the proportion of Burley type cigarettes may be increased.

The term “natural tobacco” is used herein, with reference to the present invention, to describe any part of any plant component of the genus Nicotiana , including but not limited to leaves, midribs, stems and stalks. It is used in In particular, natural tobacco includes flue-cured tobacco material, Burley tobacco material, Oriental tobacco material, Maryland tobacco material, and dark tobacco material. ), dark-fired tobacco material, Rustica tobacco material as well as material from other rare or specialty tobaccos, or blends thereof. As described in more detail below, the tobacco material may be whole (e.g., whole tobacco leaves), shredded, cut, or ground.

When it is desirable to produce a nicotine composition from a combination of two or more different tobacco types, the tobacco types can be heated separately at different extraction temperatures within a defined range of 100°C to 160°C to form a liquid tobacco extract, or the tobacco A mixture of types can be heated together at a single extraction temperature within a range.

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

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

Preferably, in the step of preparing the tobacco starting material, the tobacco is crushed or cut to reduce the size of the tobacco particles in the tobacco starting material. This can advantageously improve the heating homogeneity and extraction efficiency of the tobacco starting material.

The tobacco starting material may optionally be dried prior to the heating step to reduce the water content of the tobacco starting material. Drying of the tobacco starting material may be carried out 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 water content of the tobacco starting material.

Preparing the tobacco starting material may include impregnating the tobacco starting material with an aerosol former. When this impregnation of the tobacco starting material is carried out before the heating step, this can advantageously increase the amount of certain desirable tobacco compounds released from the tobacco starting material upon heating. For example, impregnating tobacco starting material with glycerin has been found to beneficially increase the amount of nicotine extracted from the tobacco starting material. In another example, impregnating 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, can be used to remove the flavor compounds extracted from the tobacco starting material. It has been found to favorably increase the amount.

Preferably, in the step of preparing the natural tobacco material, the tobacco is not subjected to any treatment adapted to change the pH of the tobacco. In particular, at the stage of producing natural tobacco material, the tobacco is not subjected to any treatment adapted to significantly increase the pH of the tobacco. For example, natural tobacco materials are not contacted with aqueous solutions containing salts of alkali or alkaline earth metals. Advantageously, it has been discovered that keeping the tobacco material in a less modified state can provide a more authentic or more natural flavor profile that can be appreciated by the consumer. Additionally, the inventors have found that it is desirable to subject 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. was found to result in lower levels of As an example, not subjecting the natural tobacco material to alkali treatment results in a significant increase in the weight ratio of (β-ionone + β-damascenone) to (phenol) in the liquid tobacco extract compared to the equivalent alkali-treated natural tobacco material. was found to be associated with an increase.

In a preferred embodiment, the tobacco starting material consists of natural tobacco. As such, the water content in the tobacco starting material may be about 11% by weight (water 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, non-aqueous solvents or added water or both. One example of a suitable solvent is propylene glycol.

Accordingly, the tobacco starting material is at least about 40% by weight natural tobacco material, or at least about 60% by weight natural tobacco material, or at least about 80% by weight natural tobacco material, or at least about 90% by weight natural tobacco material, or at least about 95% by weight. % of natural tobacco ingredients.

In some embodiments, the water content in the tobacco starting material is from about 3% to about 60% by weight, more preferably from about 3% to about 20% by weight, and even more preferably from about 3% to about 12% by weight. It can be. In other embodiments, the water content in the tobacco starting material is from about 5% to about 60% by weight, more preferably from about 5% to about 20% by weight, and even more preferably from about 5% to about 12% by weight. It can be. In a further embodiment, the water content in the tobacco starting material is from about 8% to about 60% by weight, more preferably from about 8% to about 20% by weight, even more preferably from about 8% to about 12% by weight. It can be.

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

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

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

The extraction temperature and duration of heating may be selected within defined ranges depending on factors such as the type of tobacco, possible other components of the tobacco starting material, desired nicotine level, or desired composition of the nicotine composition formed from the liquid tobacco extract. 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 proportion of specific tobacco compounds in the nicotine composition can be adjusted to some extent through selection of extraction parameters to maximize the ratio of desirable to undesirable tobacco compounds in the liquid tobacco extract and nicotine composition.

For a particular tobacco compound, the change in the release level of the compound at extraction temperature during the extraction process can be easily determined for any given tobacco starting material. For example, the level of nicotine released from tobacco starting material has been found to typically increase with increasing extraction temperature. The rate of increase was found to vary for different cigarette types.

Additionally, it has been found that the levels of desirable tobacco flavor compounds such as -damacenon and -ionone released from the tobacco material will increase as the extraction temperature is increased up to a certain peak extraction temperature, after which the levels will begin to decrease. . Peak extraction temperatures for these flavor compounds are typically in the range of 100°C to 160°C so that levels of the desired flavor compounds can be effectively optimized in the extraction method.

In processes where the tobacco material is immersed in a suitable liquid solvent, such as an aerosol former, for a period of several weeks, at or below room temperature, to extract the tobacco components into the solvent, ingredient contents much lower than the compositions of the invention are typically obtained. The extraction process, in which the tobacco material is immersed in a suitable solvent, such as an aerosol former, below room temperature, does not generate compounds that are not present in the tobacco but are generated by heat after the Maillard reaction has occurred. One such compound generated by heat after the Maillard reaction occurs is furaneol. Furaneol, another tobacco plant component, is derived from heat treatment of the inherent reducing sugar content of the tobacco plant material.

Bright tobacco typically has a much higher reducing sugar content (up to 25% by weight) than Burley tobacco, and the amount of furaneol released when heating bright tobacco is a direct result of the difference between extraction temperature and the level of furaneol released. It was found to vary significantly depending on the extraction temperature, with a correlation. As described herein, peak extraction temperatures for these flavor compounds are typically in the range of 100°C to 160°C so that levels of these desirable flavor compounds can be effectively optimized in the extraction process.

Many undesirable tobacco compounds are found to increase slowly with increasing extraction temperature up to a critical temperature, beyond which a rapid increase is observed. This applies, for example, to the levels of phenols, other phenolic compounds and TSNA, and in the case of Bright tobacco, to the levels of furans and formaldehyde. In many cases, the critical temperature is in the range of 100°C to 160°C, so that the levels of undesirable compounds can be effectively controlled in the extraction method.

It has been discovered by the inventors that for a particular tobacco type, the levels of certain undesirable nitrogen compounds, such as TSNA, released during extraction depend 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 level of TSNA released during the extraction process. On the other hand, Burley tobacco typically has a much higher content of nitrogen compounds and the amount of TSNA released upon heating was found to vary significantly with extraction temperature, with a direct correlation between extraction temperature and the level of TSNA released.

Additionally, it has been discovered by the inventors that for a particular tobacco type, the level of certain undesirable furans released during extraction, 2-furanmethanol, is dependent 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 has a direct correlation between the extraction temperature and the level of 2-furanmethanol released. It was found to vary considerably depending on the The degree of increase in the level of 2-furanmethanol released from bright tobacco with increasing extraction temperature may be different for each tobacco type.

As described herein, during the heating step of the extraction process, the tobacco starting material is heated to an extraction temperature of about 100°C to 160°C. If the tobacco starting material is heated to a temperature exceeding this range, in the resulting composition the weight of phenol relative to the weight of β-ionone and β-damacenon will be much higher, resulting in lower β-ionone and β-damacene. was found to result in a weight ratio of paddy to phenol.

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 explained herein, these undesirable compounds are derived in relatively higher amounts from tobacco higher in nitrogen compounds, such as Burley tobacco, and the amount of TSNA released upon heating varies between the extraction temperature and the level of TSNA released. was found to vary significantly with extraction temperature, with a direct correlation of .

As explained herein, 2-furanmethanol is derived in relatively higher amounts from sweet pears that are higher in reducing sugar content, such as bright tobacco, and the amount of 2-furanmethanol released upon heating is a function of the extraction temperature and the amount of 2-furan released. It was found to vary significantly with extraction temperature, with a direct correlation between the levels of methanol.

As described herein, during the heating step of the extraction process, the tobacco starting material is heated to an extraction temperature of about 100°C to 160°C. If the tobacco starting material is heated to a temperature exceeding this range, in the resulting composition the weight of TSNA and 2-furanmethanol relative to the weight of β-ionone and β-damacenone will be much higher, resulting in a lower (β-ion paddy field + β-damasenone) vs. (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R,S)-N-nitrosoanatabine + (R,S )-N-nitrosonabacin (NAB) and N-nitrosonornicotine (NNN) + (2-furanmethanol/600).

Nicotine is typically present in higher weight percent in extracts produced from Burley tobacco compared to Bright tobacco, but certain undesirable nitrogen compounds, such as TSNA, are typically present in higher amounts from Burley tobacco compared to Bright tobacco. It is induced. Certain preferred flavor compounds, such as furaneol, are derived from reducing sugars and are typically present in higher amounts in Bright tobacco compared to Burley tobacco due to the higher reducing sugars in the former, but certain preferred flavor compounds, such as 2-furanemethanol, Non-compounds are also derived from reducing sugars and are typically present in higher amounts in Bright tobacco compared to Burley tobacco. Accordingly, the nicotine compositions of the present invention are preferably produced from a blend of different tobacco types. Preferably, the nicotine composition is derived from Burley tobacco and Bright tobacco. Bright tobacco may be one or more of Orient tobacco and Yellow tobacco.

During the heating step, the tobacco starting material is heated to an extraction temperature of about 100° C. to about 160° C. Below this range, insufficient levels of nicotine and certain flavor compounds have been found to be 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 exceeding these defined ranges, unacceptably high levels of certain undesirable tobacco compounds such as phenol, TSNA and 2-furanmethanol may be released.

Preferably, the extraction temperature is at least about 110°C, more preferably at least about 115°C, more preferably at least about 120°C, and more preferably at least about 125°C.

Preferably, the extraction temperature is about 150°C or less, more preferably about 145°C or less, more preferably about 140°C or less, and most preferably about 135°C or less.

For example, the extraction temperature may be about 110°C to 150°C, or about 120°C to about 140°C, or about 125°C to about 135°C, or about 130°C. An extraction temperature of approximately 130° C. was found to provide a particularly optimized ratio of desirable to undesirable compounds in the liquid tobacco extract.

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

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

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

The heating times indicated above correspond to the duration for which the tobacco starting material is heated at the extraction temperature and do not include the time taken to increase the temperature of the tobacco starting material to the extraction temperature.

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

The heating step is preferably carried out in an inert atmosphere. For example, natural tobacco material can be heated with a flow of inert gas or with a flow of water or a combination of steam and inert gas. Preferably, a flow of inert gas, such as nitrogen, is passed through the starting tobacco material during the heating step. As an alternative, the heating step can be performed under vacuum.

The inventors have discovered that it is advantageous to heat natural tobacco materials in an inert atmosphere because the volatile tobacco compounds are released into the stream of inert gases during the heating step so that the inert gases act as a carrier for the volatile components. The flow of inert gas helps to convey the vapor generated by the moisture content of the natural tobacco material and the evaporation of volatile species, especially nicotine or flavor-related compounds, or both, from the extraction equipment.

Additionally, using a flow of inert gas such as nitrogen under slightly excessive pressure in the extraction equipment has the advantage of preventing the presence of oxygen within the extraction equipment. This can also be achieved by carrying out the heating step under vacuum. This advantage is desirable in that it avoids the risk of any, even partial combustion of the natural tobacco material during the heating step. Uncontrolled burning of natural tobacco materials would obviously be undesirable as it could represent a major safety hazard within the manufacturing environment. However, the inventors have discovered that even limited partial combustion of the natural tobacco material can lead to a reduction in the quality of the tobacco extract obtainable by the process, which would be undesirable.

Without wishing to be bound by theory, it is understood that by preventing combustion of the natural tobacco material, the formation of any undesirable combustion by-products is also prevented. Additionally, as conditions conducive to combustion of natural tobacco materials are prevented, natural tobacco materials are subject to conditions under which tobacco-containing substrates (e.g., homogenized tobacco materials) are typically heated in “non-combustion-heated” articles. It is heated effectively under conditions that mimic the degree of heat. As a result, selective extraction of flavor-bearing volatile species responsible for the flavor consumers associate with heated tobacco is advantageously favored.

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

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

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

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

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

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

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

Preferably, the step of collecting the volatile compounds uses an adsorption technique where the volatile compounds are captured in a non-aqueous solvent. For example, an inert gas stream containing volatile compounds can be directed into a vessel of non-aqueous extraction solvent. The non-aqueous extraction solvent is preferably an aerosol former. The non-aqueous solvent is preferably triacetin, glycerin, propylene glycol (PG), 1,3-propanediol, or mixtures thereof. The non-aqueous extraction solvent may be a polyhydric alcohol. The use of an aerosol former as a non-aqueous extraction solvent is potentially advantageous because the aerosol former can be retained as a diluent in the final liquid tobacco extract and nicotine composition. This means that an additional step to remove the non-aqueous extraction solvent is not necessarily necessary.

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

The addition of liquid aerosol formers, especially the addition of PG, can advantageously prevent the condensed volatile compounds from splitting into two phases or forming emulsions, as some tobacco components tend to do. Without being bound by theory, the inventors have observed that the solubility of tobacco components in hydroxide (i.e. liquid, aqueous fraction of naturally derived tobacco extract) depends primarily on its polarity, its concentration and the pH of the hydroxide, which It may change depending on the type. As a result, an oily layer tends to form on the surface of liquid, natural tobacco extract if the amount of aerosol former is insufficient. This oily material can be collected at different locations on the capture equipment, where collection steps are performed. The addition of a liquid aerosol former such as PG helps prevent the formation of these layers and favors the homogenization of the liquid, naturally derived tobacco extract. This, in turn, helps prevent any loss of the desired flavor-related compounds during the fourth (drying) step, during which these compounds may undesirably deposit on the equipment surfaces.

Additionally, liquid aerosol formers advantageously help capture flavor-related compounds regardless of their polarity and volatility. Additionally, during the fourth (drying) step, the liquid aerosol former not only helps prevent the loss of the most volatile fractions, but also selectively removes excess water from the liquid, naturally derived tobacco extract to obtain a concentrated tobacco extract. It helps to gain advantage.

The use of PG as an aerosol former for the condensation and collection steps has the additional advantage that PG exerts its microbial activity by reducing the water activity of the aqueous solution. Therefore, by adjusting the content of PG in the liquid, naturally derived tobacco extract, it is also possible to ensure that the extract does not substantially suffer from any microbial activity.

The liquid obtained at the end of the collection step, the naturally derived tobacco extract, is typically a homogeneous liquid. This homogeneous liquid can be stored for a limited holding time period (up to about 4 weeks) before undergoing an optional drying step. The composition of the liquid, naturally derived tobacco extract will depend on the nature of the natural tobacco material, if any; moisture content in natural tobacco materials; It depends on a number of variables, including the amount of aerosol former used to prepare natural tobacco materials.

Preferably, the non-aqueous extraction solvent is maintained at a temperature below 0° C. to optimize the transfer of volatile compounds to the non-aqueous extraction solvent. The non-aqueous extraction solvent is preferably maintained at a temperature of -10°C or higher. Temperatures below these values may result in undesirable freezing phenomena.

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

As a further alternative, the step of collecting volatile compounds can be performed using an adsorption technique in which the volatile compounds are adsorbed onto the surface of a solid adsorbent material, such as activated carbon. The adsorbed compounds are then transferred to 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 derived from different tobacco starting materials are combined.

In the method, the next step is the formation of a liquid tobacco extract from the collected volatile compounds. The nature of these steps may depend on the collection method. “Collected volatile compounds” will typically include a solution of tobacco derived volatile compounds in a non-aqueous extraction solvent.

The extraction method provides a liquid tobacco extract comprising greater than about 20% water by weight based on the weight of the liquid tobacco extract. Typically, liquid tobacco extract may contain at least about 40% water by weight. Liquid tobacco extract may contain from about 40% to about 70% water by weight.

The extraction method described herein provides a liquid tobacco extract with a nicotine content of at least 0.2% by weight. More preferably, the nicotine content in the liquid tobacco extract is at least about 0.4% by weight. The liquid tobacco extract may have a nicotine content of less than or equal to about 10% by weight, more preferably less than or equal to about 8% by weight, more preferably less than or equal to about 5% by weight, and most preferably less than or equal to about 3.6% by weight. Most preferably, the liquid tobacco extract comprises about 0.4% to 3.6% nicotine by weight, based on the weight of the liquid tobacco extract.

The extraction methods described herein include a non-aqueous extraction solvent content of from about 25% to about 65% by weight, preferably from about 30% to about 60% by weight, and most preferably from about 35% to about 55% by weight. Provides a liquid tobacco extract that can be had. The non-aqueous extraction solvent is preferably triacetin, glycerin, propylene glycol, 1,3-propanediol or mixtures thereof.

In the method, the next step involves forming the 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 adding additional nicotine. The nicotine composition can advantageously be formed directly from the liquid tobacco extract resulting from the extraction process, without the need for adding additional flavor compounds. The nicotine composition can advantageously be formed directly from the liquid tobacco extract without the need for adding additional non-aqueous solvents. For example, liquid tobacco extract produced by an extraction process can be used to prepare a nicotine composition comprising 10 to 20 mg of nicotine per milliliter, without the need for adding nicotine.

Alternatively, the liquid tobacco extract may be subjected to additional processing steps to form the nicotine composition. Even with these additional steps, the nicotine composition can be formed without the need for adding additional nicotine or flavor compounds. Preferably, the liquid tobacco extract can be concentrated in a drying step as described herein to form a concentrated tobacco extract, which can 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 described above, when the volatile compounds are collected by adsorption in a non-aqueous extraction solvent, the solution of the volatile compounds in the liquid solvent forming the liquid tobacco extract is preferably such that the liquid solvent contains both the non-aqueous extraction solvent and water. Because it can, the solution is dried to concentrate it. This can be done, for example, to reach a desired concentration of nicotine or flavor compound. Drying includes, but is not limited to, drying, molecular sieves, freeze-drying, phase separation, distillation, membrane permeation, controlled crystallization and filtration of water, reverse hygroscopicity, ultracentrifugation, liquid chromatography, reverse osmosis, or chemical drying. It can be carried out using suitable means.

The solution of the volatile compounds in the liquid solvent forming the liquid tobacco extract is preferably concentrated by drying in a drying step to form the concentrated tobacco extract. Concentrated tobacco extracts can 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 part of the water and obtain a concentrated tobacco extract. For this purpose, a solution of the volatile compound in a liquid solvent can be heated to a temperature and for a time such that the water content in the tobacco extract is reduced by at least about 60%.

In one embodiment, the solution of the volatile compound in the liquid solvent is heated under vacuum, preferably at a temperature of at least about 70°C. In another embodiment, a solution of the volatile compound in a liquid solvent is heated under a flow of air, preferably with a relatively low humidity, at a temperature of at least about 35°C. Therefore, a concentrated tobacco extract can be obtained. One such concentrated tobacco extract typically contains less than about 20% water by weight.

In the drying step, the liquid tobacco extract is heated to a temperature of about 35°C to about 95°C, more preferably from about 35°C to about 90°C, even more preferably from about 35°C to about 85°C, most preferably from about 35°C to about 85°C. Can be heated to 80℃.

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

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

After the drying step, the liquid tobacco extract is referred to as concentrated tobacco extract. Concentrated tobacco extract contains up to about 20% water by weight. Preferably, the concentrated tobacco extract comprises 8% to 15% by weight of water based on the weight of the concentrated tobacco extract.

The drying step is a concentration step that may have a non-aqueous extraction solvent content of about 65% to about 95% by weight, preferably about 65% to about 85% by weight, and most preferably about 75% to about 85% by weight. Provides tobacco extract. The non-aqueous extraction solvent is preferably triacetin, glycerin, propylene glycol, 1,3-propanediol or mixtures thereof.

The drying step can be performed to produce a concentrated tobacco product that can have a nicotine content of at least about 0.2% nicotine by weight, preferably about 0.5% to about 12% nicotine by weight, and most preferably about 2% to about 8% nicotine by weight. Extracts are provided.

Concentrated tobacco extracts can be used directly to form nicotine compositions, without the need to add additional nicotine. Concentrated tobacco extracts can be used directly to form nicotine compositions, without the need to add additional non-aqueous solvents. Concentrated tobacco extract can be used directly to form nicotine compositions, without the need to add water. Concentrated tobacco extracts can be used directly to form nicotine compositions, without the need to add 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.

Nicotine compositions may possess optional and desirable features as described above herein.

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

Tobacco starting material is prepared from xanthobright tobacco material. The tobacco material is cut to form tobacco shreds with dimensions of 2.5 mm x 2.5 mm, and the tobacco shreds are loaded into the extraction chamber without compression. The tobacco starting material is heated to a temperature of 130° C. for a period of 3 hours in the extraction chamber. During heating, a flow of nitrogen passes through the extraction chamber at a flow rate of approximately 40 liters per minute.

The volatile compounds released from the tobacco starting material during the heating step are collected by adsorption into a liquid solvent formed from propylene glycol with stirring at 750 rpm at -10°C.

The nicotine composition of Example 1 is a liquid tobacco extract obtained directly from an extraction process at a temperature of 130° C. for a period of 3 hours. The nicotine composition combines optimized levels of desirable flavor compounds such as -damascenone and -ionone with undesirable compounds such as phenol, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, ( R,S)-N-nitrosoanatabine, (R,S)-N-nitrosoanabasine, N-nitrosonornicotine and 2-furan methanol. The nicotine composition further provides nicotine with levels of desirable flavor compounds such as furaneol and 2,3-diethyl-5-methylpyrazine. In particular, 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) The weight ratio of to (nicotine) is greater than 5 x 10-4.

This example provides two nicotine compositions according to the invention, both of which are prepared after an extraction process at a temperature of 130° C. for a period of 3 hours, followed by a drying step to reduce the moisture level of the liquid tobacco extract to approximately 6%. It is a concentrated tobacco extract obtained. The concentrated tobacco extract is then used directly to form the nicotine composition. In both nicotine compositions, the weight ratio of (β-ionone + β-damascenone) to (phenol) is greater than 0.25, and (furaneol + (2,3-diethyl-5-methylpyrazine)*100) The weight ratio of to (nicotine) is greater than 5 x 10-4.

Example 2a

Example 2a relates to concentrated tobacco extract derived from xanthoma bright tobacco material. The contents of the liquid tobacco extract of Example 2a were as follows:

- Nicotine: 0.53% w/w

- Propylene glycol: 91.8 % w/w

- Water: 6.3% w/w

- Balance (including flavors detailed in Table 1 below): 1.57% w/w

Example 2b

Example 2b relates to concentrated tobacco extract derived from Burley species tobacco material. The contents of the liquid tobacco extract of Example 2b were as follows:

- Nicotine: 1.82% w/w

- Propylene glycol: 89.6 % w/w

- Water: 5.7% w/w

- Balance (including flavors detailed in Table 1 below): 2.88 % w/w

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

This example provides three nicotine compositions according to the invention, each of which is prepared after an extraction process at a temperature of 130° C. for a period of 3 hours, followed by a drying step to reduce the moisture level of the liquid tobacco extract to approximately 12.5%. It is a concentrated tobacco extract obtained. The concentrated tobacco extract is then used directly to form the nicotine composition. In these nicotine compositions, the weight ratio of (β-ionone + β-damascenone) to (phenol) is greater than 0.25, and (furaneol + (2,3-diethyl-5-methylpyrazine)*100) to The weight ratio of (nicotine) is greater than 5 x 10-4.

Example 3a

Example 3a relates to concentrated tobacco extract derived from Oriental Bright tobacco material. The contents of the concentrated tobacco extract of Example 3a were 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 flavor): 2.1% w/w

Example 3b

Example 3b relates to concentrated tobacco extract derived from xanthobright tobacco material. The contents of the concentrated tobacco extract of Example 3b were 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 flavor): 1.3% w/w

Example 3c

Example 3c relates to concentrated tobacco extract derived from Burley species tobacco material. The contents of the concentrated tobacco extract of Example 3c were 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 flavor): 0.4% w/w

The nicotine composition of Example 3 combines optimized levels of desirable flavor compounds such as -damacenone and -ionone with undesirable compounds such as phenol, 4-(methylnitrosamino)-1-(3-pyridyl)-1- Butanone, (R,S)-N-nitrosoanatabine, (R,S)-N-nitrosoanabasin, N-nitrosonornicotine and 2-furanmethanol are provided. The nicotine composition further provides nicotine with levels of desirable flavor compounds such as furaneol and 2,3-diethyl-5-methylpyrazine.

The liquid tobacco extract of Example 1 was concentrated in a drying process to reduce the moisture level of the liquid tobacco extract to approximately 15%.

Glycerin was added to the resulting concentrated liquid tobacco extract to form the nicotine composition, so that the nicotine composition contained 20% glycerin and 80% liquid tobacco extract by weight, based on the weight of the nicotine composition.

Example 5 relates to a nicotine composition in gel form according to the present invention. A gel nicotine composition was formed from the liquid tobacco extract of Example 1. The contents of the gel nicotine composition are as follows:

- Liquid tobacco extract of Example 1: 99.0 % w/w

- Baby: 1.0 % w/w

The three tobacco starting materials according to the invention are produced respectively from yellow type bright tobacco material (6A), Burley type tobacco material (6B) and orient type tobacco material (6C).

Each of the three tobacco materials is cut to form a tobacco shred with dimensions of 2.5 mm x 2.5 mm, and the tobacco shred is loaded into the extraction chamber without compression.

Each of the tobacco starting materials is heated to a temperature of 130° C. for a period of 120 minutes in the extraction chamber. During heating, a flow of nitrogen passes through the extraction chamber at a flow rate of 2 liters per minute.

The volatile compounds released from each tobacco starting material during the heating step are collected by adsorption into a liquid solvent formed with polypropylene glycol at 0°C.

Liquid tobacco extract is obtained directly from this extraction process. The respective liquid extracts obtained from each of the three tobacco starting materials are then concentrated under vacuum (50 mbar) at 55° C. until a moisture content of 12% ± 2% is reached.

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. Additionally, in all three liquid extracts according to the invention 6A, 6B and 6C, the weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine)*100) to (nicotine) is consistently and significantly 1 x is greater than 10 ^-3 . Additionally, in all three liquid extracts according to inventions 6A, 6B and 6C, (β-ionone + β-damascenone) versus (4-(methylnitrosamino)-1-(3-pyridyl)- 1-butanone + (R,S)-N-nitrosoanatabine + (R,S)-N-nitrosoanabasin + N-nitrosonornicotine + ((2-furanmethanol)/600)) The weight ratio is consistently and significantly above 3.

Comparative example

Two tobacco starting materials are prepared from xanthobright tobacco materials (CE1, CE2). Two additional tobacco starting materials are made from Burley tobacco materials (CE3, CE4). Each of the four starting tobacco materials is cut to form a tobacco shred with dimensions of 2.5 mm x 2.5 mm.

Tobacco shreds are mixed with an alkaline solution of potassium carbonate in water to achieve a predetermined pH for each tobacco material. This 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 achieve a pH of 8, while tobacco starting materials CE2 and C4 are mixed with an alkaline solution of potassium carbonate in water to achieve a pH of 9.5. achieve

After this alkaline treatment, the tobacco shreds of each tobacco starting material are loaded into the extraction chamber without compression. Each tobacco starting material is heated to a temperature of 130° C. for a period of 120 minutes in the extraction chamber. During heating, a flow of nitrogen passes through the extraction chamber at a flow rate of approximately 2 liters per minute.

The volatile compounds released from each tobacco starting material during the heating step are collected by adsorption into a liquid solvent formed with polypropylene glycol at 0°C.

Liquid tobacco extract is obtained directly from this extraction process. Each liquid extract obtained from each of the four tobacco starting materials is then concentrated under vacuum (50 mbar) at 55° C. until a moisture content of 12% ± 2% is reached.

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. Moreover, in all four liquid extracts according to comparative examples CE1, CE2, CE3 and CE4, the weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine)*100) to (nicotine) was consistent. and is significantly less than 5 x 10 ^-4 .

Claims (15)

A non-aqueous solvent, at least 0.2% by weight 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 greater than 5 x 10 ^-4 A nicotine composition comprising a second weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine)*100) to (nicotine). The nicotine composition of claim 1, wherein the first weight ratio is greater than 0.5. The nicotine composition of claim 1, wherein the second weight ratio is 8 x 10 ^-4 to 9 x 10 ^-3 . The nicotine composition of claim 1, wherein the nicotine composition comprises 0.4% to 3.6% by weight of nicotine based on the weight of the nicotine composition. 2. The method of claim 1, further comprising a third weight ratio, wherein the third weight ratio is (β-ionone + β-damacenone) to (4-(methylnitrosamino)-1-(3-pyridyl)- 1-butanone + (R,S)-N-nitrosoanatabine + (R,S)-N-nitrosoanabasin + N-nitrosonornicotine + ((2-furanmethanol)/600)) weight ratio, and the third weight ratio is greater than 1.5. The nicotine composition of claim 1, wherein the nicotine composition is derived from Burley tobacco and bright tobacco. The nicotine composition of claim 6, wherein the bright tobacco is one or more of Oriental tobacco and flue-cured tobacco. The nicotine composition of claim 1, wherein the non-aqueous solvent is glycerin, propylene glycol, triacetin, 1,3-propanediol, or mixtures thereof. The method of claim 1, wherein acetic acid, vanillin, 2-ethyl-3,5-dimethylpyrazine, 2-methylbutanoic acid, 3-methylbutanoic acid, 3-methyl-2,4-nonanedione, 2-methoxyphenol, A nicotine composition further comprising one or more of 2-phenylethanol, eugenol, and sotolone. 2. The nicotine composition of claim 1, wherein the nicotine composition comprises at least 300 micrograms of acetic acid per gram of nicotine composition. 9. The nicotine composition of claim 8, comprising 80% to 90% by weight of the non-aqueous solvent and water, based on the weight of the nicotine composition. The nicotine composition of claim 1, wherein the nicotine composition is a liquid nicotine composition. The nicotine composition of claim 1, wherein the nicotine composition is a gel nicotine composition. A cartridge comprising the nicotine composition of any one of claims 1 to 13. A non-aqueous solvent, nicotine, a first weight ratio of (β-ionone + β-damascenone) to (phenol) of greater than 0.25, and a first weight ratio of greater than 5 x 10 ^-4 , prepared by a process comprising the following steps: A nicotine composition comprising a second weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine)*100) to (nicotine), the method comprising:
heating the tobacco starting material at an extraction temperature of 100° C. to 160° C. for at least 90 minutes;
collecting volatile compounds released from the tobacco starting material during the heating step;
forming a liquid tobacco extract comprising the collected volatile compounds;
A nicotine composition comprising; forming the nicotine composition from liquid tobacco extract.