RU2816933C2 - Nicotine-based composition, method for preparation thereof and aerosol-generating products containing thereof - Google Patents

Abstract

FIELD: smoking accessories.

SUBSTANCE: invention relates to a nicotine composition. Nicotine-based composition contains a non-aqueous solvent, at least 0.2 percent by weight of nicotine in terms of the weight of the nicotine-based composition, provides a first weight ratio of (β-ionone β-Damascenone) and (phenol) of more than 0.25, and a second weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine) * 100)) to (nicotine) of more than 5×10^-4.

EFFECT: invention enables to obtain a nicotine composition with reduced content of undesirable compounds.

15 cl, 12 ex, 3 tbl

Description

The present invention relates to nicotine-based compositions.

Aerosol generating systems for delivering an aerosol to a user are known that comprise a nebulizer configured to generate a respirable aerosol from a liquid composition, such as a nicotine-based liquid composition. Some known aerosol generating systems include a thermal nebulizer, such as an electric heater, configured to heat and vaporize a liquid composition to generate an aerosol. One popular type of electrically heated aerosol generating system is the electronic cigarette. Other known aerosol generating systems comprise a non-thermal atomizer configured to generate an aerosol from a liquid composition using, for example, impingement, ultrasonic or vibrating mesh technologies.

Nicotine-based compositions can be prepared by an 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 liquid tobacco extract.

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

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

By way of example, methods are known in which tobacco material is essentially boiled in water for a period of several hours or even days to form a vapor phase, and the distillate obtained by condensing the vapor phase is collected in a vessel. Over time, an oily, waxy layer containing a large proportion of apolar compounds accumulates on the surface of the distillate.

The water portion, over which the waxy layer accumulates and which contains nicotine and other water-soluble compounds, is returned by recycling to the water heater. The apolar co-solvent may optionally be supplied to the aqueous water heater to increase the yield of the extraction product. On the other hand, the waxy phase is collected and eventually forms the primary product of one such hydrodistillation process. Such a product is often called "tobacco essential oil" and contains a large proportion of apolar compounds found in tobacco, such as fatty acids, neophytadiene, etc. Tobacco essential oil obtained by this method alone generally does not contain nicotine.

It is also known to subject tobacco material to an extraction method involving the use of a volatile apolar solvent. Examples of suitable solvents are cyclic or acyclic short alkanes, as well as chlorinated solvents such as dichloromethane. In one such method, excess solvent can be evaporated by controlled heating under vacuum. Typically this is done in the presence of ethanol, which has a higher boiling point than the extraction solvent, so that even very small quantities of the extraction solvent can be detected.

The primary product of one such solvent extraction process is often called "tobacco absolute" and may contain trace amounts of ethanol. It is a waxy product and contains a highly concentrated mixture of most apolar compounds that can be extracted with a specific solvent, usually including nicotine, which is usually present in relatively high concentrations.

An alternative extraction method involves contacting the tobacco material with a solvent under supercritical conditions, such as supercritical carbon dioxide. One such method is disclosed in US 2013/160777, and its operating principle is based on the fact that volatiles in a feed material that is in contact with a supercritical fluid can be separated into the supercritical phase. After dissolving any soluble material, the supercritical fluid containing the solutes can be removed, and the dissolved components of the feed material can be separated from the supercritical fluid. The primary product of the supercritical extraction process is essentially similar to the "tobacco absolute" from the lower temperature and lower pressure solvent extraction process, contains no residual solvent and typically has a high level of waxy apolar compounds and includes nicotine, which typically present in relatively high concentrations.

In another type of extraction method, the tobacco material is soaked in a suitable solvent, such as an aerosolizing agent, at room temperature or below for a period of several weeks to extract the tobacco constituents into the solvent. In one such process, often referred to as a cold maceration process, the tobacco material is held in suspension in an extraction liquid for a period of up to several weeks or even months. The resulting slurry is then filtered and the liquid phase thus collected can be used to prepare a liquid composition for use in an aerosol generating system. However, in one such method it is usually difficult to control the extraction conditions (eg temperature and pressure). In addition, the liquid phase collected from the filtration of the slurry, which is the primary product of the cold maceration process, is highly dilute and tends to have low levels of apolar tobacco flavor compounds. Additionally, the liquid phase typically contains little or no nicotine. As such, liquid extracts produced by the cold maceration process typically require the addition of additional ingredients, such as nicotine salts and glycerin, before use in an aerosol generating system.

Liquid tobacco extracts and nicotine-based compositions obtained through such known extraction methods may have low nicotine levels. In addition, nicotine-based compositions obtained through such extraction methods may have low levels and low diversity of flavor compounds, particularly compounds associated with heated tobacco aroma such as furaneol. Nicotine-based compositions obtained through such extraction methods may also have high levels of undesirable compounds. In general, the concentration of nicotine, flavor compounds and undesirable compounds obtained through such extraction methods can be significantly influenced by the type or types of tobacco used as the starting material.

The purpose of the present invention is to eliminate one or more disadvantages of nicotine-based compositions obtained by known methods. It would be especially desirable to provide new and improved nicotine-based compositions.

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

The present invention further relates to a cartridge containing a nicotine-based composition. The present invention also relates to a nicotine-based composition obtained by a process comprising the step of heating the tobacco starting material at an extraction temperature of from 100 degrees Celsius to 160 degrees Celsius for at least 90 minutes.

The present invention provides a nicotine-based composition containing a non-aqueous solvent of at least 0.2 percent by weight of nicotine, based on the weight of the nicotine-based composition, comprising a first weight ratio of (β-ionone+β-damascenone) to (phenol) , being more than 0.25, and a second weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine)*100)) and (nicotine) being more than 5 x 10 ^-4 .

A nicotine-based composition containing a non-aqueous solvent, nicotine, comprising a first weight ratio of (β-ionone+β-damascenone) to (phenol) of greater than 0.25 and a second weight ratio of (furaneol + (2,3-diethyl-5 -methylpyrazine)*100) and (nicotine) amounting to more than 5 × 10 ^-4 can be obtained through a method including the steps of heating the starting tobacco material at an extraction temperature of from 100 degrees Celsius to 160 degrees Celsius for at least 90 minutes; collecting volatile compounds released from the starting tobacco material during the heating step; forming a liquid tobacco extract containing the collected volatile compounds; optionally dehydrating and concentrating the liquid tobacco extract to form a concentrated tobacco extract and forming a nicotine-based composition from the liquid tobacco extract or concentrated tobacco extract.

The nicotine-based composition may be a liquid nicotine-based composition or a gel-like nicotine-based composition.

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

As used herein, the term “aerosol generating device” refers to a device comprising a heating element that interacts with the nicotine composition of the present invention to produce an aerosol. During use, volatile compounds are released from the nicotine-based composition by heat transfer and are captured by air drawn through the aerosol generating device. As the released compounds cool, they condense to form an aerosol that is inhaled by the consumer.

When the nicotine composition is heated, an aerosol is released containing volatile compounds that were collected from the original tobacco material during the extraction process.

The nicotine-based composition may contain a non-aqueous solvent, water, nicotine and flavoring compounds.

The present inventors have discovered that, unlike the products of existing extraction methods that have been discussed above, the liquid tobacco extracts of the present invention have a significantly higher content of compounds associated with the aroma of heated tobacco. These flavoring compounds are virtually absent or present in trace amounts in tobacco extract obtained through the maceration process, which also typically contains little or no nicotine. These flavoring compounds are also usually absent or present in trace amounts in tobacco extract obtained using a solvent, including under supercritical conditions. Likewise, tobacco essential oil obtained by the distillation process also typically has very low levels, if any, of such flavoring compounds associated with the aroma of heated tobacco.

The nicotine-based composition may comprise a total non-aqueous solvent content of from about 10 percent to about 95 percent by weight. The nicotine-based composition preferably comprises a total non-aqueous solvent content of from about 50 percent to about 95 percent by weight, such as from about 65 percent to about 95 percent by weight, more preferably from about 70 percent to about 90 percent by weight, most preferably from approximately 80 percent to approximately 90 percent by weight. The non-aqueous solvent is preferably triacetin, glycerol, propylene glycol, 1,3-propanediol, or a mixture thereof.

One skilled in the art will understand that herein, when the percentage by weight of a particular component is described with reference to a nicotine composition, liquid tobacco extract, or concentrated tobacco extract, the percentage by weight is given based on the weight of the specific component relative to the total weight a corresponding composition based on nicotine, liquid tobacco extract or concentrated tobacco extract.

The nicotine-based composition may have a total propylene glycol content of from about 10 percent to about 95 percent by weight. The nicotine-based composition may have a total propylene glycol content of from about 20 percent to about 95 percent by weight, such as from about 50 percent to about 95 percent by weight, or from about 65 percent to about 95 percent by weight, from about 70 percent to about 90 percent by weight, or from about 80 percent to about 90 percent by weight.

The nicotine-based composition may have a total triacetin content of from about 10 percent to about 95 percent by weight. The nicotine-based composition may have a total triacetin content of from about 20 percent to about 95 percent by weight, such as from about 50 percent to about 95 percent by weight, from about 70 percent to about 90 percent by weight, or from about 65 percent to about 95 percent by weight, or from about 80 percent to about 90 percent by weight.

The nicotine-based composition may have a total glycerol content of from about 10 percent to about 95 percent by weight. The nicotine-based composition may have a total glycerol content of from about 20 percent to about 95 percent by weight, such as from about 50 percent to about 95 percent by weight, or from about 65 percent to about 95 percent by weight, from about 70 percent to about 90 percent by weight, or from about 80 percent to about 90 percent by weight.

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

The nicotine composition of the present invention contains at least 0.2 percent by weight nicotine. More preferably, the nicotine content of the nicotine-based composition is at least about 0.4 percent by weight. The nicotine composition may have a nicotine content of about 12 percent by weight or less, such as about 10 percent by weight or less, preferably about 8 percent by weight or less, more preferably about 5 percent by weight or less, preferably about 3.6 percent by weight or less. Most preferably, the nicotine-based composition contains from about 0.4 percent by weight to 3.6 percent by weight nicotine, based on the weight of the nicotine-based composition.

The nicotine-based composition may contain from 1 percent to 85 percent by weight water. The nicotine-based composition may contain from 2 percent to 50 percent by weight water. The nicotine-based composition may contain from 3 percent to 30 percent by weight water. The nicotine-based composition may contain from 5 percent to 25 percent by weight water. The nicotine-based composition may contain from 8 percent to 20 percent by weight water. The nicotine-based composition preferably contains from 10 percent to 15 percent by weight water.

In some embodiments, the nicotine-based composition may contain 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 having a solubility in water at 20°C that is greater than or equal to about 500 mg/ml.

One or more water-soluble organic acids may advantageously bind nicotine in a nicotine-based liquid tobacco extract by forming one of the nicotine salts. One or more nicotine salts may advantageously be dissolved and stabilized in the water present in the liquid tobacco extract or in a non-aqueous solvent. This may advantageously reduce nicotine absorption in the upper respiratory tract and improve nicotine delivery to and retention in the lungs.

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

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

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

If acetic acid is added to the liquid tobacco extract to form a nicotine-based composition, the total acetic acid content of the nicotine-based composition, including both acetic acid obtained by the extraction process and additional acetic acid, is preferably from about 0.01 percent to about 8 percent by weight, for example, from about 0.03 percent to about 8 percent by weight, from about 0.3 percent to about 8 percent by weight, from about 2 percent to about 8 percent by weight, or from about 3 percent percent to approximately 8 percent by weight. More preferably, the total acetic acid content is from about 0.01 percent to about 6 percent by weight, such as from about 0.03 percent to about 6 percent by weight, from about 0.3 percent to about 6 percent by weight, from about about 2 percent to about 6 percent by weight, or about 3 percent to about 6 percent by weight.

Preferably, the nicotine-based composition has a water-soluble organic acid content that is less than or equal to about 8 percent by weight. More preferably, the nicotine-based composition has a water-soluble organic acid content that is less than or equal to about 6 percent by weight.

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

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

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

Preferably, the nicotine-based composition has a non-tobacco flavoring content that is less than or equal to about 4 percent by weight. More preferably, the nicotine-based composition has a non-tobacco flavoring content that is less than or equal to about 3 percent by weight.

The nicotine composition is analyzed using gas chromatography to determine the liquid content. The weight of each compound in the nicotine-based composition may be expressed in micrograms per gram of nicotine-based composition. The weight ratios of the compounds in the nicotine composition can then be calculated as described herein.

In the nicotine-based composition of the present invention, the first weight ratio of (β-ionone+β-damascenone) to (phenol) is greater than 0.25. The above ratio is higher when the amount of desired 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-damascenone) to (phenol) is greater than 0.5 by weight, 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 the required flavor compounds contained in the nicotine composition of the present invention. Furaneol, for example, is a desired compound obtained by heat treating the intrinsic reducing sugar content of the tobacco plant material with other constituents of the tobacco plant. Light tobacco varieties typically have a much higher reducing sugar content (up to 25% by weight) than burley tobacco varieties.

In the nicotine-based composition of the present invention, the second weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine)*100) and (nicotine) is more than 5×10 ^-4 . Such ratios provide a good organoleptic profile. Preferably, the second weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine)*100)) and (nicotine) is from 8×10 ^-4 to 9×10 ^-3 or from 1×10 ^-3 to 5×10 ^-3 .

The nicotine composition of the present invention may include a weight ratio of (β-ionone + β-damascenone) and (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R, S)-N-nitrosoanatabine + (R, S)-N-nitrosoanabasine + N-nitrosonornicotine + ((2-furanmethanol)/600)), which is more than 1.5.

The above ratio is higher when the amount of desired flavor compounds β-ionone and β-damascenone is higher or when the amount of TCHA and 2-furanmethanol is lower.

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

The nicotine-based composition may contain other desired compounds derived directly from natural tobacco, many of which are flavoring agents. The nicotine-based composition may contain one or more of acetic acid, vanillin, 2-ethyl-3,5-dimethylpyrazine, 2-methylbutanoic acid, 3-methylbutanoic acid, 3-methyl-2,4-nonanedione, 2-methoxyphenol, 2 -phenylethanol, eugenol and sotolon.

The nicotine-based composition contains β-ionone. The nicotine-based composition may contain at least 0.100 micrograms of β-ionone per gram of nicotine-based composition, preferably at least 0.200 micrograms of β-ionone per gram of nicotine-based composition, more preferably at least 0.300 micrograms of β-ionone per gram of composition nicotine-based, most preferably at least 0.400 micrograms of β-ionone per gram of nicotine-based composition. In preferred embodiments, the nicotine-based composition contains at least 0.500 micrograms of β-ionone per gram of nicotine-based composition, more preferably at least 0.600 micrograms of β-ionone per gram of nicotine-based composition, even more preferably at least 0.700 micrograms of β -ionone per gram of nicotine-based composition, most preferably at least 0.800 micrograms of β-ionone per gram of nicotine-based composition. In particularly preferred embodiments, the nicotine-based composition contains at least 0.9 micrograms of β-ionone per gram of nicotine-based composition, preferably at least 1.00 micrograms of β-ionone per gram of nicotine-based composition, more preferably at least 1.10 micrograms of β-ionone per gram of nicotine-based composition, even more preferably at least 1.20 micrograms of β-ionone per gram of nicotine-based composition, most preferably at least 1.30 micrograms of β-ionone per gram of composition per nicotine based. 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. Weight ratio of (β-ionone) and (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R, S)-N-nitrosoanatabine + (R, S)-N-nitrosoanabasine + N-nitrosonornicotine + ((2-furanmethanol)/600) may be greater than 0.300, eg greater than 0.500, preferably greater than 0.750, more preferably greater than 1.00, most preferably greater than 1.20, eg greater than 1.80.

The nicotine-based composition contains β-damascenone. The nicotine-based composition may contain at least 0.100 micrograms of β-damascenone per gram of nicotine-based composition, preferably at least 0.350 micrograms of β-damascenone per gram of nicotine-based composition, more preferably at least 0.600 micrograms of β-damascenone per gram of composition nicotine-based, most preferably at least 0.850 micrograms of β-damascenone per gram of nicotine-based composition. In preferred embodiments, the nicotine-based composition contains at least 1.10 micrograms of β-damascenone per gram of nicotine-based composition, more preferably at least 1.35 micrograms of β-damascenone per gram of nicotine-based composition, even more preferably at least at least 1.60 micrograms of β-damascenone per gram of nicotine-based composition, most preferably at least 1.85 micrograms of β-damascenone per gram of nicotine-based composition. In especially preferred embodiments, the nicotine-based composition contains at least 2.10 micrograms of β-damascenone per gram of nicotine-based composition, preferably at least 2.35 micrograms of β-damascenone per gram of nicotine-based composition, more preferably at least 2.60 micrograms of β-damascenone per gram of nicotine-based composition, even more preferably at least 2.75 micrograms of β-damascenone per gram of nicotine-based composition, most preferably at least 2.90 micrograms of β-damascenone per gram of composition per nicotine based. 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. Weight ratio of (β-damascenone) and (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R, S)-N-nitrosoanatabine + (R, S)-N-nitrosoanabasine + N-nitrosonornicotine + ((2-furanmethanol)/600) may be greater than 0.300, eg greater than 0.700, preferably greater than 1.00, more preferably greater than 1.50, most preferably greater than 2.20, eg greater than 2.70.

The weight ratio of (β-ionone+β-damascenone) to (nicotine) may be greater than 5.00×10 ^-5 , for example greater than 1.00×10 ^-4 , preferably greater than 2.00×10 ^-4 , more preferably greater than 4 .00×10 ^-4 , most preferably more than 6.00×10 ^-4 , for example more than 7.00×10 ^-4 .

The nicotine-based composition contains furaneol. The nicotine-based composition may contain at least 0.0100 microgram furaneol per gram of nicotine-based composition, preferably at least 0.100 microgram furaneol per gram of nicotine-based composition, more preferably at least 0.300 microgram furaneol per gram of nicotine-based composition, most preferably at least 0.500 micrograms of furaneol per gram of nicotine composition. In preferred embodiments, the nicotine-based composition contains at least 0.700 micrograms of furaneol per gram of nicotine-based composition, more preferably at least 0.900 micrograms of furaneol per gram of nicotine-based composition, even more preferably at least 1.10 micrograms of furaneol per gram nicotine-based compositions, most preferably at least 1.30 micrograms of furaneol per gram of nicotine-based composition. In especially preferred embodiments, the nicotine-based composition contains at least 1.50 micrograms of furaneol per gram of nicotine-based composition, preferably at least 1.80 micrograms of furaneol per gram of nicotine-based composition, more preferably at least 2.00 micrograms furaneol per gram of nicotine-based composition, even more preferably at least 2.20 micrograms of furaneol per gram of nicotine-based composition, most preferably at least 2.40 micrograms of furaneol per gram of nicotine-based 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. Weight ratio of (furaneol) and (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R, S)-N-nitrosoanatabine + (R, S)-N-nitrosoanabasine + N-nitrosonornicotine + ( (2-furanmethanol)/600) may be greater than 0.600, eg greater than 0.800, preferably greater than 1.00, more preferably greater than 1.50, most preferably greater than 2.00, eg greater than 2.10.

The nicotine-based composition contains 2,3-diethyl-5-methylpyrazine. The nicotine composition may contain at least 3.00 x 10 ^-3 micrograms of 2,3-diethyl-5-methylpyrazine per gram of nicotine composition, preferably at least 5.00 x 10 ^-3 micrograms 2,3-diethyl -5-methylpyrazine per gram of nicotine-based composition, more preferably at least 9.00 x 10 ^-3 micrograms of 2,3-diethyl-5-methylpyrazine per gram of nicotine-based composition, most preferably at least 1.50 x 10 ^-2 micrograms of 2,3-diethyl-5-methylpyrazine per gram of nicotine composition. In preferred embodiments, the nicotine composition contains at least 2.50 x 10 ^-2 micrograms of 2,3-diethyl-5-methylpyrazine per gram of nicotine composition, more preferably at least 3.50 x 10 ^-2 micrograms ,3-diethyl-5-methylpyrazine per gram of nicotine-based composition, even more preferably at least 5.00 x 10 ^-2 micrograms of 2,3-diethyl-5-methylpyrazine per gram of nicotine-based composition, most preferably at least 7.50 x 10 ^-2 micrograms of 2,3-diethyl-5-methylpyrazine per gram of nicotine composition. In particularly preferred embodiments, the nicotine-based composition contains at least 9.00×10 ^-2 micrograms of 2,3-diethyl-5-methylpyrazine per gram of nicotine-based composition, preferably at least 0.100 micrograms of 2,3-diethyl-5 -methylpyrazine per gram of nicotine-based composition, more preferably at least 0.200 micrograms of 2,3-diethyl-5-methylpyrazine per gram of nicotine-based composition, even more preferably at least 0.300 micrograms of 2,3-diethyl-5-methylpyrazine per gram of nicotine-based composition, most preferably at least 0.400 microgram of 2,3-diethyl-5-methylpyrazine per gram of nicotine-based composition. The weight ratio of (2,3-diethyl-5-methylpyrazine) to (phenol) may be 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 greater than 0.600. Weight ratio of (2,3-diethyl-5-methylpyrazine) and (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R, S)-N-nitrosoanatabine + (R, S)-N -nitrosoanabasine + N-nitrosonornicotine + ((2-furanmethanol)/600) may be greater than 0.0300, for example greater than 0.0400, preferably greater than 0.100, more preferably greater than 0.500, most preferably greater than 0.800, for example greater than 0.900.

The nicotine-based composition may contain acetic acid. Preferably, the acetic acid was obtained using an extraction method, however, additional acetic acid may be added after the extraction method, as described previously herein. Acetic acid is the required compound that smoothes and reduces the astringency of the generated aerosol.

The nicotine-based composition may contain at least 300 micrograms of acetic acid per gram of nicotine-based composition, preferably at least 500 micrograms of acetic acid per gram of nicotine-based composition, more preferably at least 700 micrograms of acetic acid per gram of nicotine-based composition most preferably at least 900 micrograms of acetic acid per gram of nicotine composition. In preferred embodiments, the nicotine-based composition contains at least 1200 micrograms of acetic acid per gram of nicotine-based composition, more preferably at least 1500 micrograms of acetic acid per gram of nicotine-based composition, even more preferably at least 2000 micrograms of acetic acid per gram of nicotine-based composition, most preferably at least 2500 micrograms of acetic acid per gram of nicotine-based composition. In particularly preferred embodiments, the nicotine-based composition contains at least 3,000 micrograms of acetic acid per gram of nicotine-based composition, preferably at least 3,500 micrograms of acetic acid per gram of nicotine-based composition, more preferably at least 4,000 micrograms of acetic acid per gram nicotine-based composition, even more preferably at least 4500 micrograms of acetic acid per gram of nicotine-based composition, most preferably at least 5000 micrograms of acetic acid per gram of nicotine-based 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. The weight ratio of (acetic acid) to (4-(methylnitrosamino) -1-(3-pyridyl)-1-butanone + (R, S)-N-nitrosoanatabine + (R, S)-N-nitrosoanabasine + N-nitrosonornicotine + ((2-furanmethanol)/600) can be more than 2100 , for example more than 2800, preferably more than 3000, more preferably more than 4000, most preferably more than 5500, for example more than 7500.

The nicotine-based composition may contain vanillin. The nicotine-based composition may contain at least 3.00 x 10 ^-2 micrograms of vanillin per gram of nicotine-based composition, preferably at least 5.00 x 10 ^-2 micrograms of vanillin per gram of nicotine-based composition, more preferably at least 7.00 x 10 ^-2 micrograms of vanillin per gram of nicotine-based composition, most preferably at least 9.00 x 10 ^-2 micrograms of vanillin per gram of nicotine-based composition. In preferred embodiments, the nicotine-based composition contains at least 0.100 micrograms of vanillin per gram of nicotine-based composition, more preferably at least 0.200 micrograms of vanillin per gram of nicotine-based composition, even more preferably at least 0.300 micrograms of vanillin per gram of composition per nicotine base, most preferably at least 0.400 micrograms of vanillin per gram of nicotine base composition. In particularly preferred embodiments, the nicotine-based composition contains at least 0.500 micrograms of vanillin per gram of nicotine-based composition, preferably at least 0.600 micrograms of vanillin per gram of nicotine-based composition, more preferably at least 0.700 micrograms of vanillin per gram of nicotine-based composition nicotine, even more preferably at least 0.800 micrograms of vanillin per gram of nicotine-based composition, most preferably at least 0.900 micrograms of vanillin per gram of nicotine-based 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. The weight ratio of (vanillin) to (4-(methylnitrosamino)-1 -(3-pyridyl)-1-butanone + (R, S)-N-nitrosoanatabine + (R, S)-N-nitrosoanabasine + N-nitrosonornicotine + ((2-furanmethanol)/600) may be more than 0.110, e.g. greater than 0.150, preferably greater than 0.160, more preferably greater than 0.200, most preferably greater than 0.300, for example greater than 0.500.

The nicotine-based composition may contain 2-ethyl-3,5-dimethylpyrazine. The nicotine composition may contain at least 0.0800 microgram of 2-ethyl-3,5-dimethylpyrazine per gram of nicotine composition, preferably at least 0.100 microgram of 2-ethyl-3,5-dimethylpyrazine per gram of nicotine composition more preferably at least 0.200 micrograms of 2-ethyl-3,5-dimethylpyrazine per gram of nicotine-based composition, most preferably at least 0.300 micrograms of 2-ethyl-3,5-dimethylpyrazine per gram of nicotine-based composition. In preferred embodiments, the nicotine-based composition contains at least 0.500 micrograms of 2-ethyl-3,5-dimethylpyrazine per gram of nicotine-based composition, more preferably at least 0.700 micrograms of 2-ethyl-3,5-dimethylpyrazine per gram of composition per nicotine base, even more preferably at least 0.900 micrograms of 2-ethyl-3,5-dimethylpyrazine per gram of nicotine-based composition, most preferably at least micrograms of 2-ethyl-3,5-dimethylpyrazine per gram of nicotine-based composition. In particularly preferred embodiments, the nicotine-based composition contains at least 1.10 micrograms of 2-ethyl-3,5-dimethylpyrazine per gram of nicotine-based composition, preferably at least 1.30 micrograms of 2-ethyl-3,5-dimethylpyrazine per gram of nicotine-based composition, more preferably at least 1.50 micrograms of 2-ethyl-3,5-dimethylpyrazine per gram of nicotine-based composition, even more preferably at least 1.70 micrograms of 2-ethyl-3,5- dimethylpyrazine per gram of nicotine-based composition, most preferably at least 1.90 micrograms of 2-ethyl-3,5-dimethylpyrazine per gram of nicotine-based composition. The weight ratio of (2-ethyl-3,5-dimethylpyrazine) to (phenol) may be greater than 0.100, for example greater than 0.400, preferably greater than 1.00, more preferably greater than 1.50, most preferably greater than 2.00, such as greater than 2, 50. Weight ratio of (2-ethyl-3,5-dimethylpyrazine) and (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R, S)-N-nitrosoanatabine + (R, S)-N -nitrosoanabasine + N-nitrosonornicotine + ((2-furanmethanol)/600) may be more than 0.500, for example more than 0.750, preferably more than 1.00, more preferably more than 2.00, most preferably more than 3.00, for example more than 3.50 .

The nicotine-based composition may contain 2-methylbutanoic acid. The nicotine composition may contain at least 1.00 micrograms of 2-methylbutanoic acid per gram of nicotine composition, preferably at least 2.00 micrograms of 2-methylbutanoic acid per gram of nicotine composition, more preferably at least 3. 00 micrograms of 2-methylbutanoic acid per gram of nicotine-based composition, most preferably at least 5.00 micrograms of 2-methylbutanoic acid per gram of nicotine-based composition. In preferred embodiments, the nicotine composition contains at least 6.00 micrograms of 2-methylbutanoic acid per gram of nicotine composition, more preferably at least 7.00 micrograms of 2-methylbutanoic acid per gram of nicotine composition, even more preferably at least 8.00 micrograms of 2-methylbutanoic acid per gram of nicotine-based composition, most preferably at least micrograms of 2-methylbutanoic acid per gram of nicotine-based composition. In especially preferred embodiments, the nicotine composition contains at least 9.00 micrograms of 2-methylbutanoic acid per gram of nicotine composition, preferably at least 10.0 micrograms of 2-methylbutanoic acid per gram of nicotine composition, more preferably at least 12.0 micrograms of 2-methylbutanoic acid per gram of nicotine-based composition, even more preferably at least 14.0 micrograms of 2-methylbutanoic acid per gram of nicotine-based composition, most preferably at least 15.0 micrograms of 2-methylbutanoic acid acid per gram of nicotine-based composition. The weight ratio of (2-methylbutanoic acid) to (phenol) may be greater than 7.00, for example 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 . Weight ratio of (2-methylbutanoic acid) and (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R, S)-N-nitrosoanatabine + (R, S)-N-nitrosoanabasine + N- nitrosonornicotine + ((2-furanmethanol)/600) may be greater than 12.0, eg greater than 17.0, preferably greater than 20.0, more preferably greater than 25.0, most preferably greater than 30.0, eg greater than 32.0.

The nicotine-based composition may contain 3-methylbutanoic acid. The nicotine composition may contain at least 2.00 micrograms of 3-methylbutanoic acid per gram of nicotine composition, preferably at least 3.00 micrograms of 3-methylbutanoic acid per gram of nicotine composition, more preferably at least 4. 00 micrograms of 3-methylbutanoic acid per gram of nicotine-based composition, most preferably at least 5.00 micrograms of 3-methylbutanoic acid per gram of nicotine-based composition. In preferred embodiments, the nicotine composition contains at least 6.00 micrograms of 3-methylbutanoic acid per gram of nicotine composition, more preferably at least 8.00 micrograms of 3-methylbutanoic acid per gram of nicotine composition, even more preferably at least 10.0 micrograms of 3-methylbutanoic acid per gram of nicotine-based composition, most preferably at least micrograms of 3-methylbutanoic acid per gram of nicotine-based composition. In especially preferred embodiments, the nicotine composition contains at least 15.0 micrograms of 3-methylbutanoic acid per gram of nicotine composition, preferably at least 20.0 micrograms of 3-methylbutanoic acid per gram of nicotine composition, more preferably at least 25.0 micrograms of 3-methylbutanoic acid per gram of nicotine-based composition, even more preferably at least 30.0 micrograms of 3-methylbutanoic acid per gram of nicotine-based composition, most preferably at least 35.0 micrograms of 3-methylbutanoic acid acid per gram of nicotine-based composition. The weight ratio of (3-methylbutanoic acid) to (phenol) may be greater than 11.0, for example greater than 15.0, preferably greater than 20.0, more preferably greater than 30.0, most preferably greater than 50.0, such as greater than 51.0 . Weight ratio of (3-methylbutanoic acid) and (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R, S)-N-nitrosoanatabine + (R, S)-N-nitrosoanabasine + N- nitrosonornicotine + ((2-furanmethanol)/600) may be greater than 18.0, eg greater than 40.0, preferably greater than 50.0, more preferably greater than 60.0, most preferably greater than 65.0, eg greater than 70.0.

The nicotine-based composition may contain 3-methyl-2,4-nonanedione. The nicotine composition may contain at least 6.00 x 10 ^-3 micrograms of 3-methyl-2,4-nonanedione per gram of nicotine composition, preferably at least 8.00 x 10 ^-3 micrograms 3-methyl-2 ,4-nonanedione per gram of nicotine-based composition, more preferably at least 9.00 x 10 ^-3 micrograms of 3-methyl-2,4-nonanedione per gram of nicotine-based composition, most preferably at least 0.0100 microgram 3 -methyl-2,4-nonanedione per gram of nicotine composition. In preferred embodiments, the nicotine-based composition contains at least 0.0300 micrograms of 3-methyl-2,4-nonanedione per gram of nicotine-based composition, more preferably at least 0.0500 micrograms of 3-methyl-2,4-nonanedione per gram of nicotine-based composition, even more preferably at least 0.0700 micrograms of 3-methyl-2,4-nonanedione per gram of nicotine-based composition, most preferably at least micrograms of 3-methyl-2,4-nonanedione per gram nicotine-based compositions. In especially preferred embodiments, the nicotine-based composition contains at least 0.0900 micrograms of 3-methyl-2,4-nonanedione per gram of nicotine-based composition, preferably at least 0.100 micrograms of 3-methyl-2,4-nonanedione per gram nicotine-based composition, more preferably at least 0.150 microgram of 3-methyl-2,4-nonanedione per gram of nicotine-based composition, even more preferably at least 0.200 microgram of 3-methyl-2,4-nonanedione per gram of nicotine-based composition nicotine, most preferably at least 0.250 micrograms of 3-methyl-2,4-nonanedione per gram of nicotine composition. The weight ratio of (3-methyl-2,4-nonanedione) to (phenol) may be 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 greater than 0.250. Weight ratio of (3-methyl-2,4-nonanedione) and (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R, S)-N-nitrosoanatabine + (R, S)-N -nitrosoanabasine + N-nitrosonornicotine + ((2-furanmethanol)/600) may be greater than 0.035, for example greater than 0.040, preferably greater than 0.080, more preferably greater than 0.090, most preferably greater than 0.100, for example greater than 0.130.

The nicotine-based composition may contain 2-methoxyphenol. The nicotine-based composition may contain at least 0.150 micrograms of 2-methoxyphenol per gram of nicotine-based composition, preferably at least 0.300 micrograms of 2-methoxyphenol per gram of nicotine-based composition, more preferably at least 0.500 micrograms of 2-methoxyphenol per gram of composition nicotine-based, most preferably at least 0.600 micrograms of 2-methoxyphenol per gram of nicotine-based composition. In preferred embodiments, the nicotine-based composition contains at least 0.700 micrograms of 2-methoxyphenol per gram of nicotine-based composition, more preferably at least 0.800 micrograms of 2-methoxyphenol per gram of nicotine-based composition, even more preferably at least 0.900 micrograms -methoxyphenol per gram of nicotine composition, most preferably at least micrograms of 2-methoxyphenol per gram of nicotine composition. In especially preferred embodiments, the nicotine-based composition contains at least 1.00 micrograms of 2-methoxyphenol per gram of nicotine-based composition, preferably at least 1.50 micrograms of 2-methoxyphenol per gram of nicotine-based composition, more preferably at least 2.00 micrograms of 2-methoxyphenol per gram of nicotine-based composition, even more preferably at least 2.50 micrograms of 2-methoxyphenol per gram of nicotine-based composition, most preferably at least 3.00 micrograms of 2-methoxyphenol per gram of composition per nicotine based. 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. Weight ratio of (2-methoxyphenol) and (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R, S)-N-nitrosoanatabine + (R, S)-N-nitrosoanabasine + N-nitrosonornicotine + ((2-furanmethanol)/600) may be greater than 1.40, eg greater than, preferably greater than 1.80, more preferably greater than 2.00, most preferably greater than 3.00, eg greater than 6.00.

The nicotine-based composition may contain 2-phenylethanol. The nicotine-based composition may contain at least 1.50 micrograms of 2-phenylethanol per gram of nicotine-based composition, preferably at least 3.00 micrograms of 2-phenylethanol per gram of nicotine-based composition, more preferably at least 5.00 micrograms 2-phenylethanol per gram of nicotine-based composition, most preferably at least 7.00 micrograms of 2-phenylethanol per gram of nicotine-based composition. In preferred embodiments, the nicotine-based composition contains at least 9.00 micrograms of 2-phenylethanol per gram of nicotine-based composition, more preferably at least 10.0 micrograms of 2-phenylethanol per gram of nicotine-based composition, even more preferably at least at least 11.0 micrograms of 2-phenylethanol per gram of nicotine-based composition, most preferably at least micrograms of 2-phenylethanol per gram of nicotine-based composition. In particularly preferred embodiments, the nicotine-based composition contains at least 13.0 micrograms of 2-phenylethanol per gram of nicotine-based composition, preferably at least 15.0 micrograms of 2-phenylethanol per gram of nicotine-based composition, more preferably at least 16.0 micrograms of 2-phenylethanol per gram of nicotine-based composition, even more preferably at least 17.0 micrograms of 2-phenylethanol per gram of nicotine-based composition, most preferably at least 18.0 micrograms of 2-phenylethanol per gram of composition per nicotine based. 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. Weight ratio of (2-phenylethanol) and (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R, S)-N-nitrosoanatabine + (R, S)-N-nitrosoanabasine + N-nitrosonornicotine + ((2-furanmethanol)/600) may be greater than 10.0, eg greater than 13.0, preferably greater than 14.0, more preferably greater than 15.0, most preferably greater than 17.0, eg greater than 35.0.

The nicotine-based composition may contain eugenol. The nicotine-based composition may contain at least 0.0600 microgram of eugenol per gram of nicotine-based composition, preferably at least 0.0650 microgram of eugenol per gram of nicotine-based composition, more preferably at least 0.0700 microgram of eugenol per gram of composition nicotine-based, most preferably at least 0.0800 microgram of eugenol per gram of nicotine-based composition. In preferred embodiments, the nicotine-based composition contains at least 0.0900 micrograms of eugenol per gram of nicotine-based composition, more preferably at least 0.100 micrograms of eugenol per gram of nicotine-based composition, even more preferably at least 0.200 micrograms of eugenol per gram nicotine-based compositions, most preferably at least micrograms of eugenol per gram of nicotine-based composition. In especially preferred embodiments, the nicotine-based composition contains at least 0.300 micrograms of eugenol per gram of nicotine-based composition, preferably at least 0.400 micrograms of eugenol per gram of nicotine-based composition, more preferably at least 0.500 micrograms of eugenol per gram of nicotine-based composition nicotine, even more preferably at least 0.600 micrograms of eugenol per gram of nicotine-based composition, most preferably at least 0.700 micrograms of eugenol per gram of nicotine-based 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. Weight ratio (eugenol) and (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R, S)-N-nitrosoanatabine + (R, S)-N-nitrosoanabasine + N-nitrosonornicotine + ( (2-furanmethanol)/600) may be greater than 0.0200, eg greater than 0.0250, preferably greater than 0.0300, more preferably greater than 0.500, most preferably greater than 0.550, eg greater than 1.50.

The nicotine-based composition may contain sotolon. The nicotine-based composition may contain at least 3.00 x 10 ^-3 micrograms of sotolon per gram of nicotine-based composition, preferably at least 5.00 x 10 ^-3 micrograms of sotolon per gram of nicotine-based composition, more preferably at least 7.00 x 10 ^-3 micrograms of sotolon per gram of nicotine-based composition, most preferably at least 9.00 x 10 ^-3 micrograms of sotolon per gram of nicotine-based composition. In preferred embodiments, the nicotine-based composition contains at least 0.0100 micrograms of sotolon per gram of nicotine-based composition, more preferably at least 0.0200 micrograms of sotolon per gram of nicotine-based composition, even more preferably at least 0.0300 microgram of sotolon per gram of nicotine-based composition, most preferably at least micrograms of sotolon per gram of nicotine-based composition. In especially preferred embodiments, the nicotine-based composition contains at least 0.0400 microgram of sotolon per gram of nicotine-based composition, preferably at least 0.0500 microgram of sotolon per gram of nicotine-based composition, more preferably at least 0.0600 microgram sotolon per gram of nicotine-based composition, even more preferably at least 0.0700 microgram of sotolon per gram of nicotine-based composition, most preferably at least 0.0800 microgram of sotolon per gram of nicotine-based composition. The weight ratio of (sotolon) 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, most preferably greater than 0.0500, such as greater than 0.0510. Weight ratio of (sotolone) and (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R, S)-N-nitrosoanatabine + (R, S)-N-nitrosoanabasine + N-nitrosonornicotine + ( (2-furanmethanol)/600) may be greater than 0.0300, eg greater than 0.0400, preferably greater than 0.0500, more preferably greater than 0.0600, most preferably greater than 0.0700, eg greater than 0.0750.

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

The nicotine-based composition may contain no more than 12.0 micrograms of phenol per gram of nicotine-based composition, such as no more than 10.0 micrograms of phenol per gram of nicotine-based composition, preferably no more than 8.00 micrograms of phenol per gram of nicotine-based composition, more preferably, no more than 6.00 micrograms of phenol per gram of nicotine-based composition, even more preferably, no more than 4.00 micrograms of phenol per gram of nicotine-based composition, most preferably, no more than 2.00 micrograms of phenol per gram of nicotine-based composition.

The nicotine composition may contain no more than 0.045 microgram of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) per gram of nicotine composition, for example, no more than 0.040 microgram of NNK per gram of nicotine composition , preferably no more than 0.035 microgram of NNK per gram of nicotine-based composition, more preferably no more than 0.030 microgram of NNK per gram of nicotine-based composition, even more preferably no more than 0.025 microgram of NNK per gram of nicotine-based composition, most preferably no more than 0.020 microgram of NNK per gram of nicotine-based composition.

The nicotine-based composition may contain no more than 2.00 micrograms of (R, S)-N-nitrosoanatabine (NAT) per gram of nicotine-based composition, for example no more than micrograms of NAT per gram of nicotine-based composition, preferably no more than 1.50 micrograms NAT per gram of nicotine-based composition, more preferably not more than 1.00 microgram NAT per gram of nicotine-based composition, even more preferably not more than 0.500 microgram NAT per gram of nicotine-based composition, most preferably not more than 0.300 microgram NAT per gram of composition per nicotine based.

The nicotine-based composition may contain no more than 1.60 micrograms of (R, S)-N-nitrosoanabasine (NAB) per gram of nicotine-based composition, for example no more than micrograms of NAB per gram of nicotine-based composition, preferably no more than 1.20 micrograms NAB per gram of nicotine-based composition, more preferably not more than 0.500 microgram NAB per gram of nicotine-based composition, even more preferably not more than 0.300 microgram NAB per gram of nicotine-based composition, most preferably not more than 0.200 microgram NAB per gram of nicotine-based composition .

The nicotine-based composition may contain no more than 1.60 micrograms of N-nitrosonornicotine (NNN) per gram of nicotine-based composition, for example, no more than micrograms of NNN per gram of nicotine-based composition, preferably no more than 1.20 micrograms of NNN per gram of composition per nicotine-based composition, more preferably no more than 0.500 microgram NNN per gram of nicotine-based composition, even more preferably no more than 0.300 microgram NNN per gram of nicotine-based composition, most preferably no more than 0.200 microgram NNN per gram of nicotine-based composition.

The nicotine-based composition may contain no more than 1500 micrograms of 2-furanmethanol per gram of nicotine-based composition, for example no more than micrograms of 2-furanmethanol per gram of nicotine-based composition, preferably no more than 1200 micrograms of 2-furanmethanol per gram of nicotine-based composition, more preferably no more than 1000 micrograms of 2-furanmethanol per gram of nicotine-based composition, even more preferably no more than 900 micrograms of 2-furanmethanol per gram of nicotine-based composition, most preferably no more than 700 micrograms of 2-furanmethanol per gram of nicotine-based composition.

The nicotine-based composition may contain no more than 60 micrograms of formaldehyde per gram of nicotine-based composition, such as no more than micrograms of formaldehyde per gram of nicotine-based composition, preferably no more than 50 micrograms of formaldehyde per gram of nicotine-based composition, more preferably no more than 40 micrograms of formaldehyde per gram of nicotine-based composition, even more preferably no more than 30 micrograms of formaldehyde per gram of nicotine-based composition, most preferably no more than 20 micrograms of formaldehyde per gram of nicotine-based composition.

The nicotine-based composition may contain no more than 60 micrograms of acetaldehyde per gram of nicotine-based composition, such as no more than micrograms of acetaldehyde per gram of nicotine-based composition, preferably no more than 55 micrograms of acetaldehyde per gram of nicotine-based composition, more preferably no more than 45 micrograms of acetaldehyde per gram of nicotine-based composition, even more preferably no more than 35 micrograms of acetaldehyde per gram of nicotine-based composition, most preferably no more than 30 micrograms of acetaldehyde per gram of nicotine-based composition.

The nicotine-based composition may contain no more than 5.00 micrograms of catechol per gram of nicotine-based composition, such as no more than micrograms of catechol per gram of nicotine-based composition, preferably no more than 4.00 micrograms of catechol per gram of nicotine-based composition, more preferably no more than 3.00 micrograms of catechol per gram of nicotine-based composition, even more preferably no more than 2.00 micrograms of catechol per gram of nicotine-based composition, most preferably no more than 1.00 micrograms of catechol per gram of nicotine-based composition.

The nicotine-based composition may contain no more than 1.00 micrograms of hydroquinone per gram of nicotine-based composition, such as no more than 0.950 micrograms of hydroquinone per gram of nicotine-based composition, preferably no more than 0.900 micrograms of hydroquinone per gram of nicotine-based composition, more preferably no more 0.850 micrograms of hydroquinone per gram of nicotine-based composition, even more preferably not more than 0.800 micrograms of hydroquinone per gram of nicotine-based composition, most preferably not more than 0.700 micrograms of hydroquinone per gram of nicotine-based composition.

The nicotine-based composition may contain no more than 1.30 micrograms of m-cresol per gram of nicotine-based composition, for example no more than 1.20 micrograms of m-cresol per gram of nicotine-based composition, preferably no more than 1.00 micrograms of m-cresol per gram of nicotine-based composition, more preferably no more than 0.800 microgram of m-cresol per gram of nicotine-based composition, even more preferably no more than 0.600 microgram of m-cresol per gram of nicotine-based composition, most preferably no more than 0.500 microgram of m-cresol per gram nicotine-based compositions.

The nicotine-based composition may contain no more than 1.60 micrograms of o-cresol per gram of nicotine-based composition, for example no more than 1.30 micrograms of o-cresol per gram of nicotine-based composition, preferably no more than 1.10 micrograms of o-cresol per gram of nicotine-based composition, more preferably no more than 0.800 microgram o-cresol per gram of nicotine-based composition, even more preferably no more than 0.600 microgram of o-cresol per gram of nicotine-based composition, most preferably no more than 0.400 microgram of o-cresol per gram nicotine-based compositions.

The nicotine-based composition may contain no more than 2.10 micrograms of p-cresol per gram of nicotine-based composition, for example no more than 1.50 micrograms of p-cresol per gram of nicotine-based composition, preferably no more than 1.20 micrograms of p-cresol per gram of nicotine-based composition, more preferably no more than 1.00 microgram of p-cresol per gram of nicotine-based composition, even more preferably no more than 0.900 microgram of p-cresol per gram of nicotine-based composition, most preferably no more than 0.700 microgram of p-cresol per gram of nicotine-based composition.

The nicotine-based composition may contain no more than 350 micrograms of ammonia per gram of nicotine-based composition, such as no more than 300 micrograms of ammonia per gram of nicotine-based composition, preferably no more than 275 micrograms of ammonia per gram of nicotine-based composition, more preferably no more than 250 micrograms of ammonia per gram of nicotine-based composition, even more preferably no more than 200 micrograms of ammonia per gram of nicotine-based composition, most preferably no more than 175 micrograms of ammonia per gram of nicotine-based composition.

The nicotine-based composition may contain no more than 250 micrograms of acetamide per gram of nicotine-based composition, such as no more than 225 micrograms of acetamide per gram of nicotine-based composition, preferably no more than 200 micrograms of acetamide per gram of nicotine-based composition, more preferably no more than 150 micrograms acetamide per gram of nicotine-based composition, even more preferably no more than 100 micrograms of acetamide per gram of nicotine-based composition, most preferably no more than 70 micrograms of acetamide per gram of nicotine-based composition.

The nicotine-based composition may contain no more than 45 micrograms of pyridine per gram of nicotine-based composition, such as no more than 35 micrograms of pyridine per gram of nicotine-based composition, preferably no more than 25 micrograms of pyridine per gram of nicotine-based composition, more preferably no more than 20 micrograms pyridine per gram of nicotine-based composition, even more preferably no more than 15 micrograms of pyridine per gram of nicotine-based composition, most preferably no more than 10 micrograms of pyridine per gram of nicotine-based composition.

The nicotine-based composition may be prepared from a liquid tobacco extract from a tobacco starting material consisting of one type of natural tobacco. The tobacco starting material may contain a mixture of two or more types of natural tobacco. Alternatively, the nicotine composition may be prepared from a liquid tobacco extract from a mixture obtained from a first tobacco starting material consisting of a first one type of natural tobacco, which is subjected to extraction to form a first extract, a second tobacco starting material consisting of a second one type of natural tobacco , which is subjected to extraction to form a second extract, where the first extract and the second extract are mixed to form a liquid tobacco extract. In this way, two or more extracts can be mixed to form a liquid tobacco extract. The ratio of different types of tobacco can be adapted depending on the desired characteristics of the aerosol generated from the nicotine-based composition. For example, if it is desired to provide a relatively high level of nicotine, the proportion of burley tobacco may be increased.

The nicotine-based composition may be a liquid tobacco extract obtained by an extraction process, wherein the liquid tobacco extract contains a non-aqueous solvent, water, nicotine and flavoring compounds. The liquid tobacco extract may advantageously be used directly to provide a nicotine-based composition for use in an electronic cigarette or other aerosol generating system. The nicotine-based composition may be a liquid tobacco extract obtained by an extraction process without adding additional nicotine. The nicotine-based composition may be a liquid tobacco extract obtained by an extraction process without the addition of additional aromatic compounds. The nicotine-based composition may be a liquid tobacco extract obtained by an extraction process without adding additional non-aqueous solvent. The nicotine-based composition may be a liquid tobacco extract obtained by an extraction process without adding additional water.

For example, liquid tobacco extract obtained by the extraction method can be used to obtain a nicotine-based composition containing 10 to 20 mg of nicotine per milliliter, without the need for added nicotine. The term "liquid tobacco extract" describes the direct product of the extraction process from tobacco material. Thus, liquid tobacco extract typically includes a mixture of natural components isolated from, extracted from, or obtained from natural tobacco material using tobacco extraction conditions and techniques. Thus, in one such method, extracted tobacco components are removed from natural tobacco material and separated from unextracted tobacco components. Therefore, liquid tobacco extract consists of a mixture of natural tobacco components that have been obtained from the parent tobacco material and have been extracted or formed during the extraction process, typically in combination with one or more materials other than the parent tobacco material, such as an extraction solvent, used during the extraction process. The extraction solvent is preferably an aerosol forming agent.

As used herein, the term “aerosol generating agent” refers to a compound or mixture of compounds that, when used, facilitates the formation of an aerosol and that is preferably substantially resistant to thermal degradation at the operating temperature of the aerosol generating article or device. Examples of suitable aerosol-forming substances include polyhydric alcohols such as propylene glycol, triethylene glycol, 1,3-propanediol, 1,3-butanediol and glycerin; polyhydric alcohol esters 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-based composition may contain liquid tobacco extract obtained by an extraction process with the addition of additional nicotine. In the nicotine-based composition of the present invention, at least 50 percent by weight, based on the total weight of the nicotine-based composition, of the nicotine content of the nicotine-based composition may come from the liquid tobacco extract rather than being added after extraction. In preferred embodiments, at least 80 percent by weight, based on the total weight of the nicotine-based composition, of the nicotine content of the nicotine-based composition comes from the liquid tobacco extract rather than being added after extraction. Even more preferably, at least 90 percent by weight, based on the total weight of the nicotine-based composition, of the nicotine content of the nicotine-based composition comes from the liquid tobacco extract rather than being added after extraction.

The nicotine-based composition may comprise liquid tobacco extract obtained by an extraction method with the addition of an additional amount of a non-aqueous solvent. In the nicotine-based composition of the present invention, at least 50 percent by weight, based on the total weight of the nicotine-based composition, of the non-aqueous solvent content of the nicotine-based composition may come from the liquid tobacco extract rather than being added after extraction. In preferred embodiments, at least 80 percent by weight, based on the total weight of the nicotine-based composition, of the non-aqueous solvent content of the nicotine-based composition comes from the liquid tobacco extract rather than being added after extraction. Even more preferably, at least 90 percent by weight, based on the total weight of the nicotine-based composition, of the non-aqueous solvent content of the nicotine-based composition comes from the liquid tobacco extract rather than being added after extraction.

The nicotine-based composition may contain liquid tobacco extract obtained by an extraction method with the addition of additional water. In the nicotine-based composition of the present invention, at least 50 percent by weight, based on the total weight of the nicotine-based composition, of the water content of the nicotine-based composition may come from the liquid tobacco extract rather than being added after extraction. In preferred embodiments, at least 80 percent by weight, based on the total weight of the nicotine-based composition, of the water content of the nicotine-based composition comes from the liquid tobacco extract rather than being added after extraction. Even more preferably, at least 90 percent by weight, based on the total weight of the nicotine-based composition, of the water content of the nicotine-based composition comes from the liquid tobacco extract rather than being added after extraction. Even more preferably, 100 percent by weight, based on the total weight of the nicotine-based composition, of the nicotine content of the nicotine-based composition comes from the liquid tobacco extract and is not added after extraction.

The nicotine-based composition may contain liquid tobacco extract obtained by an extraction process with the addition of additional flavoring compounds. In the nicotine-based composition of the present invention, at least 50 percent by weight, based on the total weight of the nicotine-based composition, of the desired types of tobacco flavorings in the nicotine-based composition may come from the liquid tobacco extract rather than being added after extraction. In preferred embodiments, at least 80 percent by weight, based on the total weight of the nicotine-based composition, of the desired tobacco flavorings in the nicotine-based composition comes from the liquid tobacco extract rather than being added after extraction. More preferably, at least 90 percent by weight, based on the total weight of the nicotine-based composition, of the desired types of tobacco flavor compounds in the nicotine-based composition comes from the liquid tobacco extract rather than being added after extraction. Even more preferably, 100 percent by weight, based on the total weight of the nicotine-based composition, of the desired types of tobacco flavor compounds in the nicotine-based composition comes from the liquid tobacco extract rather than being added after extraction.

As an example, at least 50 percent by weight, based on the total weight of the nicotine-based composition, of the furaneol content of the nicotine-based composition may come from the liquid tobacco extract rather than being added after extraction. In preferred embodiments, at least 80 percent by weight, based on the total weight of the nicotine-based composition, of the furaneol content of the nicotine-based composition comes from the liquid tobacco extract rather than being added after extraction. More preferably, at least 90 percent by weight, based on the total weight of the nicotine composition, of the furaneol content of the nicotine composition comes from the liquid tobacco extract rather than being added after extraction. Even more preferably, 100 percent by weight, based on the total weight of the nicotine composition, of the furaneol content of the nicotine composition comes from the liquid tobacco extract and is not added after extraction.

As another example, at least 50 percent by weight, based on the total weight of the nicotine composition, of the 2,3-diethyl-5-methylpyrazine content of the nicotine composition may come from the liquid tobacco extract rather than being added after extraction. In preferred embodiments, at least 80 percent by weight, based on the total weight of the nicotine composition, of the 2,3-diethyl-5-methylpyrazine content of the nicotine composition comes from the liquid tobacco extract rather than being added after extraction. More preferably, at least 90 percent by weight, based on the total weight of the nicotine composition, of the 2,3-diethyl-5-methylpyrazine content in the nicotine composition comes from the liquid tobacco extract rather than being added after extraction. Even more preferably, 100 percent by weight, based on the total weight of the nicotine composition, of the 2,3-diethyl-5-methylpyrazine content of the nicotine composition comes from the liquid tobacco extract and is not added after extraction.

The nicotine-based composition may contain further processed, in particular concentrated liquid tobacco extract. Preferably, the nicotine-based composition is a concentrated liquid tobacco extract obtained by dehydrating the liquid tobacco extract in a dehydration step, such as the dehydration step described herein. Additional non-aqueous solvent, water, nicotine and flavoring compounds, as previously described, can be added to the liquid tobacco extract or concentrated tobacco extract to form a nicotine-based composition.

As an example, in the nicotine-based composition of the present invention, at least 50 percent by weight, based on the total weight of the nicotine-based composition, of the furaneol content of the nicotine-based composition may come from the tobacco extract rather than being added after extraction. In preferred embodiments, at least 80 percent by weight, based on the total weight of the nicotine composition, of the furaneol content of the nicotine composition comes from the tobacco extract rather than being added after extraction. Even more preferably, at least 90 percent by weight, based on the total weight of the nicotine-based composition, of the furaneol content of the nicotine-based composition comes from the tobacco extract rather than being added after extraction.

As another example, in the nicotine composition of the present invention, at least 50 percent by weight, based on the total weight of the nicotine composition, of the 2,3-diethyl-5-methylpyrazine content in the nicotine composition may come from tobacco extract rather than added after extraction. In preferred embodiments, at least 80 percent by weight, based on the total weight of the nicotine composition, of the 2,3-diethyl-5-methylpyrazine content of the nicotine composition comes from the tobacco extract rather than being added after extraction. Even more preferably, at least 90 percent by weight, based on the total weight of the nicotine composition, of the 2,3-diethyl-5-methylpyrazine content in the nicotine composition comes from the tobacco extract rather than being added after extraction.

The nicotine-based composition is preferably prepared from liquid tobacco extract. The liquid tobacco extract is preferably prepared using an extraction process with an extraction temperature within a certain range in combination with a specifically defined heating duration which advantageously provides an improved liquid tobacco extract and therefore an improved nicotine composition having a significantly improved ratio of desired compounds to undesired compounds . In particular, the extraction method provides a liquid tobacco extract and nicotine composition having the maximum ratio of desired compounds to undesired compounds for the tobacco starting material. For example, the use of a specific combination of extraction temperature and time has been determined to optimize levels of nicotine and flavor compounds while also minimizing levels of undesirable compounds such as furans, phenol and phenolic compounds, and tobacco-specific nitrosamines (TSNAs).

Thus, liquid tobacco extracts and nicotine-based compositions obtained using one of these methods have significant differences in composition compared to tobacco extracts and nicotine-based compositions obtained using existing extraction methods, and can be used as a liquid for e-cigarette or to produce an e-liquid that, when heated, generates an aerosol that has a different composition and flavor profile than currently available e-liquids. In particular, liquid tobacco extracts and nicotine-based compositions obtained using the method of the present invention can be used to generate an aerosol that provides a heated tobacco flavor that is more similar to the aerosol generated by conventional cigarettes or when tobacco is heated in a heating device no combustion compared to available aerosols derived from existing nicotine-based liquid formulations.

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

The nicotine-based composition may contain liquid tobacco extract.

The nicotine-based composition may contain at least about 10 percent by weight of liquid tobacco extract. Preferably, the nicotine-based composition contains at least about 20 percent by weight of liquid tobacco extract. More preferably, the nicotine-based composition contains at least about 30 percent by weight of liquid tobacco extract. In preferred embodiments, the nicotine-based composition contains at least about 40 percent by weight liquid tobacco extract, more preferably at least about 50 percent by weight liquid tobacco extract, even more preferably at least about 60 percent by weight liquid tobacco extract. In especially preferred embodiments, the nicotine-based composition comprises at least about 65 percent by weight liquid tobacco extract, more preferably at least about 70 percent by weight liquid tobacco extract, even more preferably at least about 75 percent by weight liquid tobacco extract , most preferably at least about 80 percent by weight of liquid tobacco extract.

In some embodiments, the nicotine-based composition may comprise liquid tobacco extract, wherein the liquid tobacco extract is a concentrated tobacco extract. Concentrated tobacco extract is liquid tobacco extract that has been concentrated in a dehydration step, such as the dehydration step described herein. The nicotine-based composition may contain at least about 10 percent by weight of concentrated tobacco extract, at least about 20 percent by weight of concentrated tobacco extract, at least about 30 percent by weight of concentrated tobacco extract, at least about 40 percent by weight of concentrated tobacco extract concentrated tobacco extract, at least about 50 percent by weight of the concentrated tobacco extract, at least about 60 percent by weight of the concentrated tobacco extract, more preferably at least about 70 percent by weight of the concentrated tobacco extract, even more preferably at least about 75 percent by weight of the concentrated tobacco extract, and most preferably at least about 80 percent by weight of the concentrated tobacco extract.

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

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

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

The nicotine-based composition may contain up to about 100 percent by weight of liquid tobacco extract. In some embodiments, the nicotine-based composition may be formed directly from the liquid tobacco extract without the need to add additional non-aqueous solvent, flavorings, or nicotine. That is, the nicotine-based composition may contain 100 percent by weight of liquid tobacco extract. In some embodiments, the liquid tobacco extract is a concentrated tobacco extract, such that the nicotine-based composition may contain 100 percent by weight concentrated tobacco extract. In embodiments in which the nicotine-based composition contains 100 percent by weight liquid tobacco extract or 100 percent by weight concentrated tobacco extract, no additional non-aqueous solvent is present.

Alternatively, in some embodiments, the nicotine-based composition containing liquid tobacco extract may contain an additional non-aqueous solvent. The additional non-aqueous solvent is the non-aqueous solvent that was added after the extraction step. The additional non-aqueous solvent is a solvent that is auxiliary to the non-aqueous extraction solvent present in the liquid tobacco extract. In embodiments in which the liquid tobacco extract is a concentrated tobacco extract, the nicotine-based composition containing the concentrated tobacco extract may contain an additional non-aqueous solvent. The total non-aqueous solvent content of the nicotine-based composition as described above includes the non-aqueous extraction solvent and additional non-aqueous solvent, if present.

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

In embodiments in which the nicotine-based composition contains an additional non-aqueous solvent, the nicotine-based composition may contain 90 percent by weight or less of the additional non-aqueous solvent. Preferably, the nicotine-based composition contains 80 percent by weight or less of additional non-aqueous solvent. More preferably, the nicotine-based composition contains 70 percent by weight or less of additional non-aqueous solvent. In preferred embodiments, the nicotine-based composition contains about 60 percent by weight or less of additional non-aqueous solvent, more preferably about 50 percent by weight or less of additional non-aqueous solvent, even more preferably about 40 percent by weight or less of additional non-aqueous solvent. In especially preferred embodiments, the nicotine-based composition contains about 35 weight percent or less of an additional non-aqueous solvent, more preferably about 30 weight percent or less of an additional non-aqueous solvent, even more preferably about 25 weight percent or less of an additional non-aqueous solvent, most preferably approximately 20 percent by weight or less of liquid tobacco extract.

In one illustrative embodiment, the nicotine composition is a concentrated tobacco extract containing 84 percent by weight propylene glycol, 12.5 percent by weight water, 1.2 percent by weight nicotine, 0.5 percent by weight acetic acid and 1.8 percent by weight of the remainder of the other components, including the desired flavor compounds, obtained using the extraction method as described herein.

In one illustrative embodiment, the nicotine-based composition contains 80 percent by weight of concentrated tobacco extract and 20 percent by weight of an additional non-aqueous solvent. In this illustrative embodiment, the nicotine-based composition contains 20 percent by weight glycerin as an additional non-aqueous solvent and 80 percent by weight concentrated tobacco extract, the concentrated tobacco extract contains 84 percent by weight propylene glycol, 12.5 percent by weight water, 1.2 percent by weight of nicotine, 0.5 percent by weight of total acetic acid, and 1.8 percent by weight of the remainder of the other components, including the desired flavor compounds obtained by the extraction method as described herein. Thus, the nicotine composition of this illustrative embodiment contains 20 percent by weight glycerin, 67.2 percent by weight propylene glycol, 10 percent by weight water, 0.96 percent nicotine, 0.4 percent by weight total acetic acid, and 1 .44 percent by weight of the remainder of the remaining components, including the desired flavor compounds obtained by the extraction method as described herein. This composition contains 87.2 percent by weight of a non-aqueous solvent, the non-aqueous solvent comprising glycerin and propylene glycol.

The nicotine-based composition may be a gel-type nicotine-based composition. Since nicotine can cause skin irritation, it is advisable to prevent possible nicotine leakage by fixing the nicotine in a gel at room temperature. Such gels are described, for example, in document WO 2018/019543 A1.

Advantageously, the nicotine-based gel composition contains a thermoreversible gel. This means that the gel will become fluid when heated to the melting temperature and will set to become a gel again at the gelation temperature. The gelation temperature occurs preferably at room temperature and atmospheric pressure or higher. Atmospheric pressure means pressure equal to 1 atmosphere. The melting temperature is preferably higher than the gelation temperature. Preferably, the melting point of the gel is above 50 degrees Celsius, or 60 degrees Celsius, or 70 degrees Celsius, and more preferably, above 80 degrees Celsius. Melting point in this context means the temperature at which the gel is no longer solid and begins to flow.

The nicotine-based gel composition may contain a suitable gelling agent. Preferably, the nicotine-based gel composition contains agar, agarose, sodium alginate or gellan gum. Most preferably, the nicotine-based gel composition contains agar. The nicotine-based gel composition preferably contains from about 0.5 percent to about 5 percent by weight of a gelling agent, more preferably from about 0.8 percent to about 1 percent by weight of a gelling agent.

The nicotine-based gel composition may contain liquid tobacco extract. Preferably, the nicotine-based gel composition contains from about 50 percent to about 99.5 percent liquid tobacco extract, more preferably from about 60 percent to about 99.5 percent liquid tobacco extract, even more preferably from about 70 percent to about 99.5 percent liquid tobacco extract. most preferably from about 80 percent to about 99.5 percent liquid tobacco extract.

The liquid tobacco extract may be a concentrated tobacco extract, so that the nicotine-based gel composition may contain a concentrated tobacco extract. Preferably, the nicotine gel composition contains from about 50 percent to about 99.5 percent concentrated tobacco extract, more preferably from about 60 percent to about 99.5 percent concentrated tobacco extract, even more preferably from about 70 percent to about 99.5 percent concentrated tobacco extract, most preferably from about 80 percent to about 99.5 percent concentrated tobacco extract.

The nicotine-based gel composition may contain an additional non-aqueous solvent. Preferably, the nicotine gel composition contains from about 5 percent to about 49.5 percent, more preferably from about 10 percent to about 40 percent, even more preferably from about 15 percent to about 30 percent, most preferably from about 20 percent to about 30 percent additional non-aqueous solvent. The additional non-aqueous solvent is preferably glycerol, propylene glycol, triacetin, 1,3-propanediol, or a mixture thereof.

The total non-aqueous solvent content of the nicotine-based gel composition includes the non-aqueous extraction solvent and additional non-aqueous solvent, if present. The nicotine-based gel composition may comprise a total non-aqueous solvent content of from about 10 percent to about 95 percent by weight. The nicotine-based gel composition preferably comprises a total non-aqueous solvent content of from about 50 percent to about 95 percent by weight, such as from about 65 percent to about 95 percent by weight, more preferably from about 70 percent to about 90 percent by weight, most preferably from approximately 80 percent to approximately 90 percent by weight. The non-aqueous solvent is preferably triacetin, glycerol, propylene glycol, 1,3-propanediol, or a mixture thereof.

The nicotine-based gel composition may contain from 1 percent to 85 percent by weight water. The nicotine-based gel composition may contain from 2 percent to 50 percent by weight water. The nicotine-based gel composition may preferably contain from 3 percent to 30 percent by weight water. The nicotine-based gel composition may contain from 8 percent to 20 percent by weight water. The nicotine-based gel composition may contain from 10 percent to 15 percent by weight water.

The nicotine-based gel composition contains at least 0.2 percent by weight nicotine. More preferably, the nicotine content of the nicotine gel composition is at least about 0.4 percent by weight. The nicotine gel composition may have a nicotine content of about 12 percent by weight or less, such as about 10 percent by weight or less, preferably about 8 percent by weight or less, more preferably about 5 percent by weight or less, preferably about 3.6 percent by weight or less. Most preferably, the nicotine gel composition contains from about 0.4 percent by weight to 3.6 percent by weight nicotine.

In one illustrative embodiment, the nicotine-based gel composition contains 80 percent by weight liquid tobacco extract, 19 percent by weight additional non-aqueous solvent, and 1 percent agar. In this illustrative embodiment, the nicotine composition contains 19 percent by weight glycerin as an additional non-aqueous solvent and 80 percent by weight liquid tobacco extract, the liquid tobacco extract contains 59 percent by weight glycerin, 37.5 percent by weight water, 1.2 percent by weight of nicotine, 0.5 percent by weight of total acetic acid and 1.8 percent by weight of the remainder of the other components, including the desired flavor compounds obtained by the extraction method as described herein. Thus, the nicotine composition of this illustrative embodiment contains 66.2 percent by weight glycerin, 30 percent by weight water, 0.96 percent by weight nicotine, 0.4 percent by weight total acetic acid, 1 percent agar, and 1 .44 percent by weight of the remaining other components, including the desired flavor compounds obtained using the extraction method as described herein.

The nicotine-based composition of the present invention may be provided in a cartridge for use in an aerosol generating system. The cartridge may include an atomizer configured to generate an aerosol from the nicotine-based composition. The atomizer may be a thermal atomizer configured to heat the nicotine-based composition to generate an aerosol. The thermal atomizer may include, for example, a heater and a liquid moving element configured to move the nicotine-based composition toward the heater. The fluid transfer element may include a capillary wick. Alternatively, the atomizer may be a non-thermal atomizer configured to generate an aerosol from the nicotine-based composition in a manner other than heating. The non-thermal nebulizer may be, for example, an impinging jet nebulizer, an ultrasonic nebulizer, or a vibrating mesh nebulizer.

The cartridge containing the nicotine-based composition may be used in combination with any suitable aerosol generating device comprising a housing configured to receive at least a portion of the cartridge. The aerosol generating device may include a battery and an electronic control circuit.

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

It is possible to control the nicotine-based composition as well as the characteristics of the resulting aerosol produced from the nicotine-based composition and delivered to the consumer by controlling the parameters of the extraction method.

According to the present invention, there is provided a nicotine-based composition containing a non-aqueous solvent, nicotine, having a first weight ratio of (β-ionone+β-damascenone) to (phenol) of greater than 0.25 and a second weight ratio of (furaneol + (2.3 -diethyl-5-methylpyrazine)*100) and (nicotine) comprising more than 5 x 10 ^-4 , obtained by a process comprising the steps of heating the starting tobacco material at an extraction temperature of from 100 degrees Celsius to 160 degrees Celsius for at least 90 minutes; collecting volatile compounds released from the starting tobacco material during the heating step; forming a liquid tobacco extract containing the collected volatile compounds; forming a nicotine-based composition from liquid tobacco extract.

As discussed above, a nicotine-based composition can be prepared from a liquid tobacco extract from a tobacco starting material consisting of one type of natural tobacco. The tobacco starting material may contain a mixture of two or more types of natural tobacco. Alternatively, the nicotine composition may be prepared from a liquid tobacco extract from a mixture obtained from a first tobacco starting material consisting of a first one type of natural tobacco, which is subjected to extraction to form a first extract, a second tobacco starting material consisting of a second one type of natural tobacco , which is subjected to extraction to form a second extract, where the first extract and the second extract are mixed to form a liquid tobacco extract. In this way, two or more extracts can be mixed to form a liquid tobacco extract. The ratio of different types of tobacco can be adapted depending on the desired characteristics of the aerosol generated from the nicotine-based composition. For example, if it is desired to provide a relatively high level of nicotine, the proportion of burley tobacco may be increased.

The term "natural tobacco" is used herein with reference to the present invention to describe any part of any plant belonging to the genus Nicotiana , including, without limitation, leaves, leaf midribs, stems and petioles. In particular, the natural tobacco may include fire-cured tobacco material, burley tobacco material, oriental tobacco material, Maryland tobacco material, dark tobacco material, dark fire-cured tobacco material, shag tobacco material, as well as material from other rare or specialty tobaccos or mixtures of them. As will be described in more detail below, the tobacco material may be whole leaf (eg, whole tobacco leaves), shredded, cut, or ground.

If it is desired to produce a nicotine composition from a combination of two or more different types of tobacco, the tobacco types may be heated separately at different extraction temperatures within a specific range of 100 degrees Celsius to 160 degrees Celsius to form a liquid tobacco extract, or a mixture of tobacco types may be heated together at the same extraction temperature within the specified range.

The tobacco starting material may be solid tobacco material, such as powder, tobacco pharmaceuticals, pieces of tobacco leaves, or intact leaves. Alternatively, the tobacco starting material may be a liquid tobacco material such as a paste, gel, slurry or suspension.

The tobacco starting material may be derived from any suitable tobacco material, including, without limitation, tobacco leaf, tobacco stem, reconstituted tobacco, molded tobacco, extruded tobacco, or tobacco-derived pellets.

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

The tobacco starting material may optionally be dried before the heating step to reduce the water content of the tobacco starting material. Drying of the tobacco starting material can be accomplished by any suitable chemical or physical drying method. 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.

The step of producing the tobacco starting material may include the step of impregnating the tobacco starting material with an aerosol-forming substance. When this impregnation of the tobacco starting material is carried out before the heating step, it can advantageously increase the amount of certain desired tobacco compounds released from the tobacco starting material upon heating. For example, it has been found that impregnating a tobacco starting material with glycerin advantageously increases the amount of nicotine extracted from the tobacco starting material. In another example, it has been found that impregnation of the tobacco starting material with a non-aqueous extraction solvent that is also an aerosol forming agent, such as propylene glycol, glycerin, 1,3-propanediol, triacetin, or mixtures thereof, advantageously increases the amount of flavor compounds extracted from source tobacco material.

Preferably, during the production step of the natural tobacco material, the tobacco is not subjected to any treatment designed to alter the pH of the tobacco. In particular, during the production stage of natural tobacco material, the tobacco is not subjected to any processing designed to significantly increase the pH of the tobacco. For example, natural tobacco material does not come into contact with an aqueous solution containing an alkali or alkaline earth metal salt. Advantageously, it has been found that maintaining 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. In addition, the present inventors have discovered that performing a treatment on the natural tobacco material to increase the pH of the tobacco, such as an alkali treatment, prior to heating the tobacco material during the extraction process results in lower levels of desired heated tobacco flavor compounds in the liquid tobacco extract. As an example, it has been found that avoiding alkali treatment of natural tobacco material is associated with a significant increase in the weight ratio of (β-ionone+β-damascenone) to (phenol) in the liquid tobacco extract compared to equivalent alkali-treated natural tobacco material.

In preferred embodiments, the tobacco starting material consists of natural tobacco. Thus, the water content of the original tobacco material may be approximately 11 percent by weight (the water content typically present in natural tobacco material).

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

The starting tobacco material may thus comprise at least about 40 percent by weight natural tobacco material, or at least about 60 percent by weight natural tobacco material, or at least about 80 percent by weight natural tobacco material, or at least about 90 percent by weight of natural tobacco material, or at least about 95 percent by weight of natural tobacco material.

In some embodiments, the water content of the tobacco starting material may be from about 3 percent by weight to about 60 percent by weight, more preferably from about 3 percent by weight to about 20 percent by weight, even more preferably from about 3 percent by weight to approximately 12 percent by weight. In other embodiments, the water content of the tobacco starting material may be from about 5 percent by weight to about 60 percent by weight, more preferably from about 5 percent by weight to about 20 percent by weight, even more preferably from about 5 percent by weight. to approximately 12 percent by weight. In further embodiments, the water content of the tobacco starting material may be from about 8 percent by weight to about 60 percent by weight, more preferably from about 8 percent by weight to about 20 percent by weight, even more preferably from about 8 percent by weight. to approximately 12 percent by weight.

In some embodiments, the nonaqueous solvent content may be at least about 5 percent by weight, or at least about 10 percent by weight, or at least about 15 percent by weight, or at least about 20 percent by weight, or at least about 25 percent by weight, or at least about 30 percent by weight, or at least about 35 percent by weight, or at least about 40 percent by weight.

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

The tobacco starting material may optionally be analyzed prior to the heating step to determine composition, for example, reducing sugar or alkaloid content. This composition information can be helpful in selecting an appropriate extraction temperature.

The extraction temperature and heating duration may be selected within ranges determined depending on factors such as the type of tobacco, possible other components of the tobacco starting material, the desired level of nicotine, or the desired nicotine composition formed from the liquid tobacco extract. By controlling the combination of temperature and extraction time, the liquid tobacco extract can be adjusted depending on the desired characteristics of the aerosol generated from the nicotine-based composition. In particular, the proportion of specific tobacco compounds in the nicotine-based composition can be adjusted to a certain extent by selecting extraction parameters to maximize the ratio of desired and undesired tobacco compounds in the liquid tobacco extract and nicotine-based composition.

For a particular tobacco compound, the variation in release level of the compound as a function of extraction temperature in the extraction process for any given tobacco starting material can be readily determined. For example, it has been found that the level of nicotine released from the tobacco starting material will generally increase as the extraction temperature increases. The magnitude of the increase was found to vary among different types of tobacco.

It has also been found that the level of desired tobacco flavor compounds, such as β-damascenone and β-ionone, released from the tobacco material will increase as the extraction temperature is increased to a certain peak extraction temperature, after which the level will begin to decrease. The peak extraction temperature for such flavor compounds is typically in the range of 100 degrees Celsius to 160 degrees Celsius so that the level of desired flavor compounds can be effectively optimized in the extraction method.

In methods in which the tobacco material is soaked in a suitable liquid solvent, such as an aerosol forming agent, at room temperature or below for a period of several weeks to extract the tobacco constituents into the solvent, much lower constituent contents are typically obtained than in compositions according to the present invention. Extraction methods in which the tobacco material is soaked in a suitable solvent, such as an aerosolizing agent, at room temperature or below, do not generate compounds that are not present in the tobacco, but are formed by heat following the Maillard reaction. One such compound formed by heat after the Maillard reaction is furaneol. Furaneol is obtained by heat treating the tobacco plant's own reducing sugar with other constituents of the tobacco plant.

Light tobacco varieties typically have much higher reducing sugar content (up to 25% by weight) than Burley tobacco, and the amount of furaneol released by heating light tobacco varieties has been found to vary significantly with extraction temperature, with a direct correlation between extraction temperature and the level of released furaneol. As described herein, the peak extraction temperature for such flavor compounds is typically in the range of 100 degrees Celsius to 160 degrees Celsius so that the level of such desired flavor compounds can be effectively optimized in the extraction process.

The level of many undesirable tobacco compounds has been found to increase slowly with increasing extraction temperature up to a certain threshold temperature, above which a rapid increase is observed. This applies, for example, to the levels of phenol, other phenolic compounds and TCNA, and in the case of light tobacco types, to the level of furans and formaldehyde. In many cases, the threshold temperature is within the range of 100 degrees Celsius to 160 degrees Celsius and thus the level of undesirable compounds can be effectively controlled in the extraction method.

The present inventors have discovered that for certain types of tobacco, the level of certain undesirable nitrogenous compounds, such as TCNA, released during extraction depends on the extraction temperature. For light tobacco varieties, the nitrogen content is usually very low, and increasing the extraction temperature has very little effect on the level of TCNA released during the extraction process. On the other hand, Burley tobacco typically has a much higher content of nitrogenous compounds, and the amount of TCNA released by heating has been found to vary significantly with extraction temperature, with a direct correlation between extraction temperature and the levels of TCNA released.

It has also been discovered by the present inventors that for certain types of tobacco, the level of specific undesirable furan compounds, 2-furylmethanol, released during extraction depends on the extraction temperature. For Burley tobacco varieties, the reducing sugar content is typically very low (less than 2% by weight) and increasing the extraction temperature has very little effect on the level of 2-furylmethanol released during the extraction process. On the other hand, light tobacco varieties typically have much higher reducing sugar content (up to 25% by weight), and the amount of 2-furylmethanol released upon heating has been found to vary significantly with extraction temperature, with a direct correlation between extraction temperature and level released 2-furylmethanol. The degree to which the level of 2-furylmethanol released from light tobacco increases with increasing extraction temperature may differ for each type of tobacco.

As described herein, during the heating step of the extraction process, the tobacco starting material is heated to an extraction temperature of about 100 degrees Celsius to 160 degrees Celsius. It has been found that if the tobacco starting material is heated to a temperature above this range, the resulting compositions have a much greater weight of phenol relative to the weight of β-ionone and β-damascenone, resulting in a lower weight ratio of β-ionone to β-damascenone to phenol.

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), (R,S)-N-nitrosoanatabine (NAT), (R,S)-N-nitrosoanabasine (NAB) and N-nitrosonornicotine (NNN) represent TSNA. As described herein, such undesirable compounds are produced in relatively large quantities from tobacco species that have a higher content of nitrogenous compounds, such as Burley tobacco, and the amount of TCNA released upon heating has been found to vary significantly depending on the extraction temperature with direct correlation between extraction temperature and levels of TCNA released.

As described herein, 2-furanmethanol is produced in relatively large quantities from tobacco species that have higher reducing sugar content, such as light tobacco, and the amount of 2-furylmethanol released upon heating has been found to vary significantly with temperature extraction with a direct correlation between extraction temperature and the level of 2-furylmethanol released.

As described herein, during the heating step of the extraction process, the tobacco starting material is heated to an extraction temperature of about 100 degrees Celsius to 160 degrees Celsius. It has been found that if the tobacco starting material is heated to a temperature above this range, the resulting compositions have much greater weights of TCNA and 2-furanmethanol relative to the weights of β-ionone and β-damascenone, resulting in a lower weight ratio (β-ionone+β -damascenone) and (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R, S)-N-nitrosoanatabine + (R, S)-N-nitrosoanabasine (NAB) and N-nitrosonornicotine ( NNN) + (2-furanmethanol/600).

Nicotine is usually present in higher percentages by weight in extracts obtained from burley tobacco compared to light tobacco, but some undesirable nitrogenous compounds, such as TCNA, are usually obtained in higher amounts from burley tobacco compared to light tobacco varieties. Certain desirable flavoring compounds, such as furaneol, are derived from reducing sugars and are usually present in higher quantities in light tobacco varieties compared to burley tobacco varieties due to the higher level of reducing sugar in the former, but some undesirable compounds such as 2- furanmethanol, also derived from reducing sugars, is typically present in higher amounts in light tobaccos compared to burley tobaccos. Therefore, the nicotine-based composition of the present invention is preferably prepared from a mixture of different types of tobacco. Preferably, the nicotine-based composition is derived from burley tobacco and light tobacco. The light tobacco may be one or more of oriental tobacco and fire-cured tobacco.

During the heating step, the tobacco starting material is heated to an extraction temperature of about 100 degrees Celsius to about 160 degrees Celsius. It has been found that below this range, insufficient levels of nicotine and certain flavor compounds are released from the tobacco starting material such that the resulting liquid tobacco extract lacks the desired flavor properties. On the other hand, if the tobacco starting material is heated to a temperature above this specific range, unacceptably high levels of certain undesirable tobacco compounds such as phenol, TCHA and 2-furanmethanol may be released.

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

Preferably, the extraction temperature is no more than about 150 degrees Celsius, more preferably no more than about 145 degrees Celsius, more preferably no more than about 140 degrees Celsius, most preferably no more than about 135 degrees Celsius.

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

The tobacco starting material is heated at the extraction temperature for at least about 30 minutes, or for at least about 60 minutes, or for at least about 90 minutes, more preferably for at least about 120 minutes. This extraction time is long enough so that the desired tobacco flavor compounds can be efficiently extracted to produce a nicotine-based composition that can produce 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 may be heated for from about 90 minutes to about 270 minutes, or from about 120 minutes to about 180 minutes.

The heating time specified above corresponds to the length of time that the starting tobacco material is heated at the extraction temperature and does not include the time required to raise the temperature of the starting tobacco material to the extraction temperature.

Typically, when natural tobacco material is heated, any moisture present in the natural tobacco material is also released with volatile compounds in the form of steam.

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

The inventors have discovered that heating natural tobacco material in an inert atmosphere is advantageous because volatile tobacco compounds are released into the inert gas stream during the heating step so that the inert gas acts as a carrier for the volatile components. The flow of inert gas helps remove vapors generated by the evaporation of moisture contained in the natural tobacco material and volatile compounds, including, but not limited to, nicotine or aroma-related compounds or both, from the extraction equipment.

In addition, using a flow of an inert gas such as nitrogen at a slight elevated pressure in the extraction equipment has the advantage of preventing oxygen from entering the extraction equipment. This can also be achieved by performing the heating step under vacuum. This advantage is desirable because it prevents the risk of any, even partial combustion of the natural tobacco material during the heating step. Uncontrolled combustion of natural tobacco material would obviously be undesirable as it would pose a major safety hazard in an industrial environment. However, the present inventors have discovered that even limited partial combustion of natural tobacco material may result in deterioration in the quality of the tobacco extract produced by the process, which would be undesirable.

Without being limited by theory, it should be understood that by preventing the natural tobacco material from igniting, the formation of any unwanted combustion by-products is also prevented. In addition, since conditions conducive to ignition of the natural tobacco material are prevented, the natural tobacco material is effectively heated under conditions somewhat simulating the conditions under which the tobacco-containing substrate (eg, homogenized tobacco material) is typically heated in heat-not-burn products. As a result, selective extraction of the aromatic volatile compounds responsible for the taste consumers associate with heated tobacco is advantageously promoted.

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

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

It has been found that adding water or steam to tobacco during extraction increases the yield of extracted components. However, excessive addition of water or steam complicates processing, for example causing the tobacco material to become sticky.

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

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

The tobacco starting material may optionally be analyzed prior to the heating step to determine composition, for example, reducing sugar or alkaloid content. This composition information can be helpful in selecting 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. If the tobacco starting material is heated in an inert gas stream as described above, volatile compounds are collected from the inert gas stream. Various collection methods are well known to those skilled in the art.

Preferably, the volatile compounds collection step uses an absorption technique in which the volatile compounds are captured in a non-aqueous solvent. For example, an inert gas stream containing volatile compounds may be directed into a container containing a non-aqueous extraction solvent. The non-aqueous extraction solvent is preferably an aerosol forming agent. The non-aqueous solvent is preferably triacetin, glycerol, propylene glycol (PG), 1,3-propanediol, or a mixture thereof. The non-aqueous extraction solvent may be a polyhydric alcohol. The use of the aerosolizing agent as a non-aqueous extraction solvent is potentially advantageous because the aerosolizing agent can be retained as a diluent in the final liquid tobacco extract and nicotine composition. This means that the additional step of removing the non-aqueous extraction solvent is not necessary.

In preferred embodiments, the volatile compounds are collected by condensation and the resulting condensate is added to a liquid substance to form an aerosol, preferably PG.

The addition of a liquid aerosol agent, and in particular the addition of PG, can advantageously prevent the volatile compounds from separating into two phases or forming an emulsion, as some tobacco constituents tend to do. Without wishing to be bound by theory, the present inventors have discovered that the solubility of tobacco constituents in the hydrolate (i.e., the aqueous fraction of a naturally sourced liquid tobacco extract) is primarily dependent on their polarity, their concentration, and the pH of the hydrolate, which may vary depending on the type of tobacco. As a result, if the amount of substance to form an aerosol is insufficient, an oily layer usually forms on the surface of the natural liquid tobacco extract. Such oily material may accumulate in various areas of the collection equipment in which the collection step is carried out. The addition of a liquid aerosolizing agent, such as PG, helps prevent the formation of such a layer and helps homogenize the naturally sourced liquid tobacco extract. In turn, this helps prevent any loss of desired aroma-related compounds during the fourth stage (dewatering), during which such compounds may be deposited undesirably on equipment surfaces.

In addition, the liquid aerosol forming agent advantageously helps to capture aroma-related compounds regardless of their polarity and volatility. Additionally, during the fourth stage (dehydration), the liquid aerosol agent helps prevent loss of the most volatile fraction and also helps selectively remove excess water from the naturally sourced liquid tobacco extract to produce a concentrated tobacco extract.

The use of PG as an aerosol forming agent for the condensation and collection step has the additional advantage that by reducing the activity of water in aqueous solutions, PG exerts an antimicrobial effect. Therefore, by adjusting the PG content of a naturally sourced liquid tobacco extract, it is also possible to ensure that the extract is substantially free of any microbial activity.

The naturally occurring liquid tobacco extract obtained at the end of the picking stage is usually a homogeneous liquid. Such a homogeneous liquid can be stored for a limited holding time (up to approximately 4 weeks) before being subjected to an optional dehydration step. The composition of a naturally occurring liquid tobacco extract depends on several variables, including the nature of the natural tobacco material; moisture content of natural tobacco material; the amount of aerosol-forming substance used to produce natural tobacco material, if such a substance was used.

Preferably, the non-aqueous extraction solvent is maintained at a temperature less than 0 degrees Celsius to optimize the transfer of volatile compounds into the non-aqueous extraction solvent. The non-aqueous extraction solvent is preferably maintained at a temperature of at least -10 degrees Celsius. Temperatures below these values may lead to undesirable freezing processes.

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

Additionally, as an alternative, the volatile compound collection step can be carried out 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, the step of forming the liquid tobacco extract includes a filtration step.

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

The next stage of this method is to obtain a liquid tobacco extract from the collected volatile compounds. The nature of this stage may depend on the method of collection. "Collected volatile compounds" typically include a solution of tobacco-derived volatile compounds in a non-aqueous extraction solvent.

The extraction method provides a liquid tobacco extract that contains more than 20 percent by weight of water, based on the weight of the liquid tobacco extract. Typically, liquid tobacco extract may contain at least about 40 percent by weight water. The liquid tobacco extract may contain from about 40 percent by weight to about 70 percent by weight water.

The extraction method described herein provides a liquid tobacco extract with a nicotine content of at least 0.2 percent by weight. More preferably, the nicotine content of the liquid tobacco extract is at least about 0.4 percent by weight. The liquid tobacco extract may have a nicotine content of no more than about 10 percent by weight, more preferably no more than about 8 percent by weight, more preferably no more than about 5 percent by weight, most preferably no more than about 3.6 percent by weight. Most preferably, the liquid tobacco extract contains from about 0.4 percent by weight to 3.6 percent by weight nicotine, based on the weight of the liquid tobacco extract.

The extraction method described herein provides a liquid tobacco extract that may have a non-aqueous extraction solvent content of from about 25 percent to about 65 percent by weight, preferably from about 30 percent to 60 percent by weight, most preferably from about 35 percent to about 55 percent by weight. The non-aqueous extraction solvent is preferably triacetin, glycerol, propylene glycol, 1,3-propanediol, or a mixture thereof.

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

The nicotine-based composition may advantageously be formed directly from the liquid tobacco extract obtained by the extraction process, without the need to add additional nicotine. The nicotine-based composition may advantageously be formed directly from the liquid tobacco extract obtained by the extraction process, without the need to add additional aromatic compounds. The nicotine-based composition may advantageously be formed directly from the liquid tobacco extract without the need to add an additional non-aqueous solvent. For example, liquid tobacco extract obtained by the extraction method can be used to obtain a nicotine-based composition containing 10 to 20 mg of nicotine per milliliter, without the need for added nicotine.

Alternatively, the liquid tobacco extract may be subjected to additional processing steps to form the nicotine-based composition. Even with these additional steps, a nicotine-based composition can be formed without the need to add additional nicotine or flavor compounds. Preferably, the liquid tobacco extract can be concentrated in a dehydration step as described herein to form a concentrated tobacco extract, and the concentrated tobacco extract can be used to form a nicotine-based composition. Preferably, an additional non-aqueous solvent may be added to the liquid tobacco extract or concentrated tobacco extract to form a nicotine-based composition.

If the volatile compounds are collected by absorption in a non-aqueous extraction solvent as described above, the solution of the volatile compounds in a liquid solvent forming a liquid tobacco extract is preferably dried to concentrate the solution since the liquid solvent may include both a non-aqueous extraction solvent and water. This can be done, for example, to achieve the desired concentration of nicotine or flavor compounds. Drying can be accomplished using any suitable means, including, without limitation, dehydration, molecular sieves, freeze drying, phase separation, distillation, membrane permeation, controlled water crystallization and filtration, reverse hygroscopicity, ultracentrifugation, liquid chromatography, reverse osmosis, or chemical drying.

A solution of volatile compounds in a liquid solvent forming a liquid tobacco extract is preferably concentrated by dehydration in a dehydration step to form a concentrated tobacco extract. Concentrated tobacco extract can be used to form a nicotine-based composition.

In the dehydration step, a solution of volatile compounds in a liquid solvent is heated to evaporate at least some of the water and produce a concentrated tobacco extract. To this end, a solution of volatile compounds in a liquid solvent can be heated to a certain temperature and for a certain time to reduce the water content of the tobacco extract by at least about 60 percent.

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

In the dehydration step, the liquid tobacco extract may be heated from about 35 degrees Celsius to about 95 degrees Celsius, more preferably from about 35 degrees Celsius to about 90 degrees Celsius, even more preferably from about 35 degrees Celsius to about 85 degrees Celsius, most preferably from approximately 35 degrees Celsius to approximately 80 degrees Celsius.

During the dehydration step, the liquid tobacco extract may be heated under reduced pressure. The liquid tobacco extract can be heated at a pressure that is less than or equal to approximately 200 mbar. In the dehydration step, the liquid tobacco extract may be heated to a pressure of at least about 20 mbar.

Alternatively, during the drying step, the liquid tobacco extract may be heated in an air stream. The liquid tobacco extract may be heated in a flow of air at a rate of at least about 10 kg/hour. The liquid tobacco extract may be heated in a flow of air at a rate of at least about 15 kg/hour. The relative humidity of the air stream may be less than or equal to about 50 percent, preferably less than or equal to about 25 percent.

After the dehydration stage, the liquid tobacco extract is called concentrated tobacco extract. Concentrated tobacco extract contains approximately 20 percent by weight water or less. Preferably, the concentrated tobacco extract contains from 8 percent to 15 percent water, based on the weight of the concentrated tobacco extract.

The dehydration step provides a concentrated tobacco extract that may have a non-aqueous extraction solvent content of from about 65 percent to about 95 percent by weight, preferably from about 65 percent to 85 percent by weight, most preferably from about 75 percent to about 85 percent by weight. The non-aqueous extraction solvent is preferably triacetin, glycerol, propylene glycol, 1,3-propanediol, or a mixture thereof.

The dehydration step provides a concentrated tobacco extract that may have a nicotine content of at least about 0.2 weight percent nicotine, preferably from about 0.5 weight percent to about 12 weight percent nicotine, most preferably from about 2 weight percent to approximately 8 percent by weight nicotine.

Concentrated tobacco extract can be used directly to form a nicotine composition without the need to add additional nicotine. The concentrated tobacco extract can be used directly to form a nicotine-based composition without the need to add an additional non-aqueous solvent. The concentrated tobacco extract can be used directly to form a nicotine composition without the need to add additional water. Concentrated tobacco extract can be used directly to form a nicotine-based composition without the need for additional flavoring.

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

The nicotine-based composition may have optional and preferred characteristics as previously described herein.

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

Examples

Example 1

The starting tobacco material is prepared from fire-cured light tobacco material. The tobacco material is cut to form tobacco pieces measuring 2.5 millimeters by 2.5 millimeters and the tobacco pieces are loaded into the extraction chamber without compression. The starting tobacco material is heated in the extraction chamber to a temperature of 130 degrees Celsius for a period of 3 hours. During heating, a stream of nitrogen is passed 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 absorption into a liquid solvent formed by propylene glycol at a temperature of minus 10 degrees Celsius and with stirring at a speed of 750 rpm.

The nicotine composition of Example 1 is a liquid tobacco extract obtained directly through an extraction method at a temperature of 130 degrees Celsius for a period of 3 hours. The nicotine based formulation provides optimized levels of desired aromatic compounds such as β-damascenone and β-ionone, relative to undesirable compounds such as phenol, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, (R, S) N-nitrosoanatabine, (R, S)-N-nitrosoanabasine, N-nitrosonornicotine and 2-furanmethanol. The nicotine-based composition further provides the level of desired aromatic compounds, such as furaneol and 2,3-diethyl-5-methylpyrazine, to nicotine. Particularly, in the nicotine-based composition, the weight ratio of (β-ionone+β-damascenone) to (phenol) is more than 0.25, and the weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine)*100)) and (nicotine) is more than 5×10-4.

Example 2

This example presents two nicotine compositions according to the present invention, both of which are concentrated tobacco extracts obtained using an extraction method at a temperature of 130 degrees Celsius for a period of 3 hours followed by a dehydration step to reduce the level of moisture content in the liquid tobacco extract to approximately 6 percent. The concentrated tobacco extract is then directly used to form nicotine-based compositions. In both nicotine-based compositions, the weight ratio of (β-ionone+β-damascenone) to (phenol) is greater than 0.25, and the weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine)*100)) to ( nicotine) is more than 5×10-4.

Example 2a

Example 2a relates to a concentrated tobacco extract obtained from fire-cured light tobacco material. The content of components in the liquid tobacco extract of Example 2a is as follows:

nicotine: 0.53% w/w,

polypolene glycol: 91.8% w/w,

water: 6.3% w/w,

rest (including flavorings as shown in Table 1 below): 1.57% w/w.

Example 2b

Example 2b relates to a concentrated tobacco extract obtained from Burley tobacco material. The content of components in the liquid tobacco extract from example 2b is as follows:

nicotine: 1.82% w/w,

polypolene glycol: 89.6% w/w,

water: 5.7% w/w,

rest (including flavors as shown in Table 1 below): 2.88% w/w.

Table 1 . Content of selected flavor compounds in concentrated tobacco extract (all values are given in micrograms per kilogram of liquid tobacco extract)

Example Acetic acid β-Ionone β-Damascenone Furaneol 2,3-Diethyl-5-methylpyrazine Vanillin 2-Ethyl-3,5-dimethylpyrazine 2-Methylbutanoic acid 3-Methylbutanoic acid 3-Methyl-2,4-nonandione 2-Methoxyphenol 2-Phenylethanol Eugenol Sotolon 2a 6193580 1352 2995 2420 39 1040 838 14081 20114 273 1649 19875 619 85 2b 3868247 939 1139 154 478 340 1980 16209 36356 69 3169 18196 845 36

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

Example 3

This example presents three nicotine compositions according to the present invention, each of which is a concentrated tobacco extract obtained using an extraction method at a temperature of 130 degrees Celsius for a period of 3 hours, followed by a dehydration step to reduce the level of moisture content in the liquid tobacco extract to approximately 12.5 percent. The concentrated tobacco extract is then directly used to form nicotine-based compositions. In these nicotine-based compositions, the weight ratio of (β-ionone+β-damascenone) and (phenol) is more than 0.25, and the weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine)*100)) and ( nicotine) is more than 5×10-4.

Example 3a

Example 3a relates to a concentrated tobacco extract obtained from light oriental tobacco material. The content of components in the concentrated tobacco extract from example 3a is as follows:

nicotine: 0.4% w/w,

polypolene glycol: 84% w/w,

acetic acid: 1.0% w/w,

water: 12.5% w/w,

rest (including flavors): 2.1% w/w.

Example 3b

Example 3b relates to a concentrated tobacco extract obtained from fire-cured light tobacco material. The content of components in the concentrated tobacco extract from example 3b is as follows:

nicotine: 1.2% w/w,

polypolene glycol: 84% w/w,

acetic acid: 1.0% w/w,

water: 12.5% w/w,

rest (including flavors): 1.3% w/w.

Example 3c

Example 3c relates to a concentrated tobacco extract obtained from Burley tobacco material. The contents of the concentrated tobacco extract from Example 3c are as follows:

nicotine: 2.6% w/w,

polypolene glycol: 84% w/w,

acetic acid: 0.5% w/w,

water: 12.5% w/w,

rest (including flavors): 0.4% w/w.

The nicotine compositions of Example 3 provide optimized levels of desired aromatic compounds such as β-damascenone and β-ionone, relative to undesirable compounds such as phenol, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, (R, S)-N-nitrosoanatabine, (R, S)-N-nitrosoanabasine, N-nitrosonornicotine and 2-furanmethanol. Nicotine-based compositions additionally provide levels of desired aromatic compounds, such as furaneol and 2,3-diethyl-5-methylpyrazine, relative to nicotine.

Example 4

The liquid tobacco extract from Example 1 was concentrated using a dehydration process to reduce the moisture level of the liquid tobacco extract to about 15 percent.

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

Example 5

Example 5 relates to a nicotine-based composition in gel form according to the present invention. The nicotine gel composition is formed from the liquid tobacco extract of Example 1. The content of the components in the nicotine gel composition is as follows:

liquid tobacco extract from example 1: 99.0% w/w,

agar: 1.0% w/w.

Example 6

The three starting tobacco materials of the present invention were respectively prepared from light fire-cured tobacco material (6A), burley tobacco material (6B) and oriental tobacco material (6C).

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

Each of the starting tobacco materials is heated in an extraction chamber to a temperature of 130 degrees Celsius for a period of 120 minutes. During heating, a stream of nitrogen is passed 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 absorption into a liquid solvent formed from polypropylene glycol at a temperature of 0 degrees Celsius.

Liquid tobacco extract is directly obtained from this extraction method. Each liquid extract obtained from each of the three starting tobacco materials is then concentrated under vacuum (50 mbar) at 55 degrees Celsius to achieve a moisture content of 12 percent ± 2 percent.

Table 2 . Significance of selected weight ratios of desired and undesired tobacco compounds in liquid tobacco extracts

Example (β-ionone+ β-damascenone) and (phenol) (furaneol + (2,3-diethyl-5-methylpyrazine)*100)) and (nicotine) (β-ionone+β-damascenone) and (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R, S)-N-nitrosoanatabine + (R, S)-N-nitrosoanabasine+N -nitrosonornicotine + ((2-furanmethanol)/600)) 6A 2.27 1.35×10 ^-3 5.25 6B 2.96 1.71×10 ^-3 3.50 6C 4.12 2.75×10 ^-3 7.83

In all three liquid extracts of the present invention 6A, 6B and 6C, the weight ratio of (β-ionone+β-damascenone) to (phenol) is consistently and significantly greater than 2.0. In addition, in all three liquid extracts of the present invention 6A, 6B and 6C, the weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine)*100)) and (nicotine) is constantly and significantly greater than 1×10 ^-3 . Additionally, in all three liquid extracts of the present invention 6A, 6B and 6C, the weight ratio of (β-ionone + β-damascenone) and (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R, S )-N-nitrosoanatabine + (R, S)-N-nitrosoanabasine + N-nitrosonornicotine + ((2-furanmethanol)/600)) is constantly and significantly greater than 3.

Comparative example

The two tobacco starting materials are derived from fire-cured light tobacco material (CE1, CE2). Two additional tobacco starting materials are derived from Burley tobacco material (CE3, CE4). Each of the four starting tobacco materials is cut to form tobacco pieces measuring 2.5 millimeters by 2.5 millimeters.

Tobacco pieces are mixed with an alkaline solution of potassium carbonate in water to achieve the desired pH value for each tobacco material. One such alkali treatment of tobacco starting material is described in US 2016/360780.

In more detail, tobacco starting materials CE1 and CE3 are mixed with an alkaline solution of potassium carbonate in water to achieve a pH value of 8, while tobacco starting materials CE2 and C4 are mixed with an alkaline solution of potassium carbonate in water to achieve a pH value of 9.5.

After this alkaline treatment, the tobacco pieces of each starting tobacco material are loaded into the extraction chamber without compression. Each tobacco starting material is heated in an extraction chamber to a temperature of 130 degrees Celsius for a period of 120 minutes. During heating, a stream of nitrogen is passed 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 absorption into a liquid solvent formed from polypropylene glycol at a temperature of 0 degrees Celsius.

Liquid tobacco extract is directly obtained from this extraction method. Each liquid extract obtained from each of the four tobacco starting materials is then concentrated under vacuum (50 mbar) at 55 degrees Celsius until a moisture content of 12 percent ± 2 percent is achieved.

Table 3 . Significance of selected weight ratios of desired and undesired tobacco compounds in liquid tobacco extracts

Example (β-ionone+ β-damascenone) and (phenol) (furaneol + (2,3-diethyl-5-methylpyrazine)*100)) and (nicotine) (β-ionone+β-damascenone) and (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + (R, S)-N-nitrosoanatabine + (R, S)-N-nitrosoanabasine+N -nitrosonornicotine + ((2-furanmethanol)/600)) CE1 0.10 4.53×10 ^-4 0.32 CE2 0.14 2.98×10 ^-4 2.25 CE3 0.12 1.17×10 ^-4 0.39 CE4 0.10 4.30×10 ^-4 0.35

In all four liquid extracts according to comparative example CE1, CE2, CE3 and CE4, the weight ratio of (β-ionone+β-damascenone) and (phenol) is constant and significantly less than 0.25. In addition, in all four liquid extracts according to comparative example CE1, CE2, CE3 and CE4, the weight ratio of (furaneol + (2,3-diethyl-5-methylpyrazine)*100)) and (nicotine) is constantly and significantly less than 5×10 ^{- 4} .

Claims (19)

1. A nicotine composition containing a non-aqueous solvent of at least 0.2 percent by weight of nicotine based on the weight of the nicotine composition, providing a first weight ratio of (β-ionone+β-damascenone) to (phenol) of greater than 0.25, and a second weight ratio of (furaneol+(2,3-diethyl-5-methylpyrazine)*100)) to (nicotine) of more than 5×10 ^-4 . 2. The composition according to claim 1, wherein the first weight ratio is more than 0.5, more preferably more than 1, even more preferably more than 1.5, most preferably more than 2, in particular from 2 to 10 or from 2 to 5. 3. Composition according to any one of paragraphs. 1 or 2, in which the second weight ratio is from 8×10 ^-4 to 9×10 ^-3 . 4. A composition according to any of the preceding claims, containing from 0.4 percent by weight to 3.6 percent by weight nicotine, based on the weight of the nicotine composition. 5. The composition according to any of the preceding claims, further comprising a third weight ratio, wherein the third weight ratio is a weight ratio of (β-ionone+β-damascenone) to (4-(methylnitrosamino)-1-(3-pyridyl)-1- butanone+(R,S)-N-nitrosoanatabine+(R,S)-N-nitrosoanabasine+N-nitrosonornicotine+((2-furanmethanol)/600)), and the third weight ratio is more than 1.5. 6. A composition according to any of the previous paragraphs, obtained from burley tobacco and light tobacco. 7. The composition of claim 6, wherein the light tobacco is one or more of oriental tobacco and fire-cured tobacco. 8. A composition as claimed in any one of the preceding claims, wherein the non-aqueous solvent is glycerol, propylene glycol, triacetin, 1,3-propanediol, or a mixture thereof. 9. The composition according to any of the previous claims, further containing one or more of acetic acid, vanillin, 2-ethyl-3,5-dimethylpyrazine, 2-methylbutanoic acid, 3-methylbutanoic acid, 3-methyl-2,4-nonanedione, 2-methoxyphenol, 2-phenylethanol, eugenol and sotolon. 10. A composition according to any of the preceding claims, containing at least 300 micrograms of acetic acid per gram of nicotine composition. 11. The composition according to claim 8, containing from 80 percent by weight to 90 percent by weight of a non-aqueous solvent and from 10 percent by weight to 15 percent by weight of water, based on the weight of the nicotine composition. 12. The composition according to any of the previous paragraphs, which is a liquid nicotine composition. 13. The composition according to any of the previous paragraphs, which is a gel-like nicotine composition. 14. A cartridge containing a nicotine composition according to any of the previous paragraphs. 15. The composition according to claim 1, obtained using a method including the stages heating the tobacco starting material at an extraction temperature from 100 degrees Celsius to 160 degrees Celsius for at least 90 minutes; collecting volatile compounds released from the starting tobacco material during the heating step; forming a liquid tobacco extract containing the collected volatile compounds; formation of a nicotine composition from liquid tobacco extract.