IMPROVED TOBACCO FLAVOURED DRY POWDER FORMULATION

Abstract

There is provided a tobacco flavoured dry powder formulation comprising a plurality of particles comprising a base material and a tobacco flavouring composition, wherein a first ratio by weight of (β-ionone+β-damascenone) to (phenol) in the tobacco flavoured dry powder formulation is greater than 0.25. Further, there is provided a method of producing one such tobacco flavoured powder formulation. The method comprises the steps of: preparing a tobacco starting material; heating the tobacco starting material at an extraction temperature of between 100 degrees Celsius and 160 degrees Celsius for at least 90 minutes; collecting the volatile compounds released from the tobacco starting material during the heating step; forming a liquid tobacco flavouring composition comprising the collected volatile compounds; combining a base material and the liquid tobacco flavouring composition to form tobacco flavoured particles.

Claims

1-15. (canceled)

16. A tobacco flavoured dry powder formulation comprising a plurality of particles comprising a base material and a tobacco flavouring composition, wherein a first ratio by weight of (β-ionone+β-damascenone) to (phenol) in the tobacco flavoured dry powder formulation is greater than 0.25.

17. The tobacco flavoured powder formulation according to claim 16, wherein the ratio by weight of (β-ionone+β-damascenone) to (phenol) in the tobacco flavoured dry powder formulation is greater than 0.5.

18. The tobacco flavoured powder formulation according to claim 16, wherein a ratio by weight of (β-ionone+β-damascenone) to (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone+(R,S)—N-nitrosoanatabine+(R,S)—N-nitrosoanabasine+N-nitrosonornicotine+((2-furanemethanol)/600)) is greater than 1.5.

19. The tobacco flavoured powder formulation according to claim 16, further comprising one or more of furaneol, 2,3-diethyl-5-methylpyrazine, acetic acid, vanillin, 2-ethyl-3,5-dimethylpyrazine, 2-methylbutanoic acid, 3-methylbutanoic acid, 3-methyl-2,4-nonanedione, 2-methoxyphenol, 2-phenylethanol, eugenol and sotolone.

20. A method of producing a tobacco flavoured powder formulation, the method comprising the steps of: preparing a tobacco starting material; heating the tobacco starting material at an extraction temperature of between 100 degrees Celsius and 160 degrees Celsius for at least 90 minutes; collecting the volatile compounds released from the tobacco starting material during the heating step; forming a liquid tobacco flavouring composition comprising the collected volatile compounds; combining a base material and the liquid tobacco flavouring composition to form tobacco flavoured particles, wherein in the step of preparing the tobacco starting material, the tobacco starting material is not subjected to any treatment adapted to alter the pH of the tobacco.

21. The method according to claim 20, wherein the tobacco starting material is heated at an extraction temperature of between 120 degrees Celsius and 140 degrees Celsius.

22. The method according to claim 20, wherein the tobacco starting material is heated at the extraction temperature for at least 120 minutes.

23. The method according to claim 20, wherein the extraction temperature is selected to provide a ratio by weight of (β-ionone+β-damascenone) to (phenol) in the tobacco flavouring composition of at least about 0.25.

24. The method according to claim 20, wherein the extraction temperature is selected to provide a ratio by weight of (β-ionone+β-damascenone) to (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone+(R,S)—N-nitrosoanatabine+(R,S)—N-nitrosoanabasine+N-nitrosonornicotine+((2-furanemethanol)/600)) in the tobacco flavouring composition of at least about 1.5.

25. The method according to claim 20, wherein the extraction temperature is selected to provide a ratio by weight of (furaneol+(2,3-diethyl-5-methylpyrazine)*100)) to (nicotine) in the tobacco flavouring composition of at least about 5×10-4.

26. The method according to claim 20, wherein the base material comprises one or more of a gum, a starch, a hydrolysed starch, a chemically modified starch, carboxymethyl cellulose, a monosaccharide, a disaccharide.

27. The method according to claim 20, wherein the step of collecting the volatile compounds released from the tobacco starting material during the heating step comprises causing the volatile compounds to condensate by refrigeration.

28. The method according to claim 20, wherein the step of combining the base material and the liquid tobacco flavouring composition to form tobacco flavoured particles comprises: forming a mixture of the base material and the liquid tobacco flavouring composition; freezing the mixture; drying the frozen mixture; and grinding the dried mixture to form the tobacco flavoured particles; or wherein the step of combining the base material and the liquid tobacco flavouring composition to form tobacco flavoured particles comprises: forming a mixture of the base material and the liquid tobacco flavouring composition; spray-drying the mixture to form the tobacco flavoured particles.

29. A powder system comprising: a first plurality of particles according to claim 16 and having a particle size of at least about 20 micrometres; and a second plurality of particles having a particle size of about 10 micrometres or less and comprising nicotine.

30. A powder system comprising: a first plurality of tobacco flavoured particles having a particle size of at least about 20 micrometres and a second plurality of particles having a particle size of less than about 20 micrometres, wherein a first ratio by weight of (β-ionone+β-damascenone) to (phenol) in the tobacco flavoured of the first plurality is greater than 0.25.

Description

EXAMPLE 1

[0193] A tobacco starting material is prepared from a flue-cured Bright tobacco material. The tobacco material is cut to form tobacco shreds having dimensions of 2.5 millimetres by 2.5 millimetres and the tobacco shreds are loaded into an extraction chamber, without compression. The tobacco starting material is heated within the extraction chamber to a temperature of 130 degrees Celsius for a period of 3 hours. During heating, a flow of nitrogen is passed through the extraction chamber at a flow rate of about 40 litres per minute.

[0194] The volatile compounds released from the tobacco starting material during the heating step are collected by absorption into a liquid solvent formed of propylene glycol at minus 10 degrees Celsius and with agitation of 750 rpm.

[0195] Thus a liquid tobacco flavouring composition is obtained directly from an extraction process at a temperature of 130 degrees Celsius for a period of 3 hours. The liquid tobacco flavouring composition provides an optimised level of desirable flavour compounds such as β-damascenone and β-ionone 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-furanemethanol. The liquid tobacco flavouring composition further provides a level of desirable flavour compounds such as furaneol and 2,3-diethyl-5-methylpyrazine to nicotine.

[0196] The solution of propylene glycol with the collected volatile compounds is concentrated in a desiccation process to reduce the moisture level of the liquid tobacco extract to approximately 15 percent.

EXAMPLE 2

[0197] This example provides two liquid tobacco flavouring compositions, both of which are obtained directly from an extraction process at a temperature of 130 degrees Celsius for a period of 3 hours.

EXAMPLE 2a

[0198] Example 2a relates to a liquid tobacco flavouring composition derived from flue-cured Bright tobacco material. The content of the concentrated liquid tobacco flavouring composition of Example 2a is as follows: [0199] Nicotine: 0.53% w/w [0200] Propylene Glycol: 91.8% w/w [0201] Water: 6.3% w/w [0202] Balance (including flavourants as detailed in Table 1 below): 1.57% w/w

EXAMPLE 2b

[0203] Example 2b relates to a liquid tobacco flavouring composition derived from Burley tobacco material. The content of the concentrated liquid tobacco flavouring composition of Example 2b is as follows: [0204] Nicotine: 1.82% w/w [0205] Propylene Glycol: 89.6% w/w [0206] Water: 5.7% w/w [0207] Balance (including flavourants as detailed in Table 1 below): 2.88% w/w

TABLE-US-00001 TABLE 1 Content of selected flavour compounds in liquid tobacco flavouring composition (all values given in micrograms per kilogram of liquid tobacco flavouring composition) 2- 3- 2,3- ethyl- 2- 3- methyl- 2- β- diethyl- 3,5- methyl- methyl- 2,4- meth- 2- Exam- Acetic β- damas- fur- 5-methyl- Van- dimethyl- butanoic butanoic nonane- oxy- phenyl- Eu- soto- ple acid ionone cenone aneol pyrazine illin pyrazine acid acid dione phenol ethanol genol lone 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 liquid tobacco flavour compositions of Examples 2a and 2b in accordance with the 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-furanemethanol.

EXAMPLE 3

[0208] This example provides three liquid tobacco flavouring compositions in accordance with the invention, each of which is a liquid tobacco flavouring composition obtained directly from an extraction process at a temperature of 130 degrees Celsius for a period of 3 hours.

EXAMPLE 3a

[0209] Example 3a relates to a liquid tobacco flavouring composition derived from oriental Bright tobacco material. The content of the liquid tobacco flavouring composition of Example 3a is as follows: [0210] Nicotine: 0.4% w/w [0211] Propylene glycol: 84% w/w [0212] Acetic Acid: 1.0% w/w [0213] Water: 12.5% w/w [0214] Balance (including flavourants): 2.1% w/w

EXAMPLE 3b

[0215] Example 3b relates to a liquid tobacco flavouring composition derived from flue-cured Bright tobacco material. The content of the liquid tobacco flavouring composition of Example 3b is as follows: [0216] Nicotine: 1.2% w/w [0217] Propylene Glycol: 84% w/w [0218] Acetic acid: 1.0% w/w [0219] Water: 12.5% w/w [0220] Balance (including flavourants): 1.3% w/w

EXAMPLE 3c

[0221] Example 3c relates to a liquid tobacco flavouring composition derived from Burley tobacco material. The content of the liquid tobacco flavouring composition of Example 3c is as follows: [0222] Nicotine: 2.6% w/w [0223] Propylene Glycol: 84% w/w [0224] Acetic acid: 0.5% w/w [0225] Water: 12.5% w/w [0226] Balance (including flavourants): 0.4% w/w
The liquid tobacco flavouring compositions of Example 3 provide an optimised level of desirable flavour compounds such as β-damascenone and β-ionone 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-furanemethanol. The liquid tobacco flavouring compositions further provide a level of desirable flavour compounds such as furaneol and 2,3-diethyl-5-methylpyrazine to nicotine.

EXAMPLE 4

[0227] The liquid tobacco flavouring composition of Example 1 was concentrated in a desiccation process to reduce the moisture level of the liquid tobacco extract to approximately 15 percent.

[0228] Glycerine was added to the resultant concentrated liquid tobacco extract, such that the liquid tobacco flavouring composition ultimately contained 20 percent by weight glycerine and 80 percent by weight liquid tobacco extract, based on the weight of the liquid tobacco flavouring composition.

EXAMPLE 5

[0229] The liquid tobacco flavouring compositions of Examples 1 to 4 are combined with a base material consisting of maltodextrin. A weight ratio of liquid tobacco flavour composition to base material is 30:70.

[0230] In more detail, 3 grams of each one of the liquid tobacco flavouring compositions of Examples 1 to 4 are weighed into respective beakers, after 7 grams of maltodextrin are weighed into each one of the beakers.

[0231] The two ingredients are stirred to obtain a homogeneous dough-like mixture. The dough-like mixture is spread on a Petri dish, covered with aluminium foil and stored in a freezer for at least 2 hours. Subsequently, the frozen dough-like mixture is introduced into a lyophilisation chamber (freeze-dryer) in order to dehydrate the dough-like mixture. This is done in a two-step process. In a first step of primary drying the dough-like mixture is dried for about 12 hours to allow the ice to sublimate. In a second set of secondary drying the dough-like mixture is dried for a further 2 hours to allow the unfrozen water molecules to be removed.

[0232] Prior to start of the drying process the aluminium foil on top of the Petri dish is perforated in order to favour the elimination of water from the dough-like mixture.

[0233] The dehydrated dough-like mixture is subsequently transferred into an alumina mortar and ground to form tobacco flavoured particles. A tobacco flavoured dry powder formulation is thus obtained that has a particle size distribution mean of about 50 micrometres to about 60 micrometres.

EXAMPLE 6

[0234] Examples 6 provides particles of a tobacco flavoured dry powder formulation similar to the particles of Example 5. In contrast to the particles of Example 5, a weight ratio of liquid tobacco flavour composition to base material in the particles of Example 6 is 50:50 (Example 6a) and 20:80 (Example 6b).

EXAMPLE 7

[0235] Example 7 provides particles of a tobacco flavoured dry powder formulation similar to the particles of Example 5. In contrast to the particles of Example 5 the extract of Example 7 was produced by condensation without the addition of propylene glycol or other solvent. Accordingly, the concentration of the flavour compounds within liquid tobacco flavour composition is significantly high and in light of this a weight ratio of liquid tobacco flavour composition to base material in the particles of Example 7 is 10:90 (Example 7a) and 15:85 (Example 7b).

EXAMPLE 8

[0236] Three tobacco starting materials are prepared from a flue-cured Bright tobacco material (2A), a Burley tobacco material (2B), and an Oriental tobacco material (2C), respectively.

[0237] Each one of the three tobacco materials is cut to form tobacco shreds having dimensions of 2.5 millimetres by 2.5 millimetres, and the tobacco shreds are loaded into an extraction chamber, without compression.

[0238] Each one of the tobacco starting materials is heated within the extraction chamber to a temperature of 130 degrees Celsius for a period of 120 minutes. During heating, a flow of nitrogen is passed through the extraction chamber at a flow rate of 2 litres per minute.

[0239] The volatile compounds released from each tobacco starting material during the heating step are collected by absorption into a liquid solvent formed of polypropylene glycol at 0 degrees Celsius.

[0240] A liquid tobacco extract is obtained directly from such extraction process. Each liquid extract obtained from each one of the three tobacco starting materials is then concentrated under vacuum (50 mbar) at 55 degrees Celsius until a moisture content of 12 percent±2 percent is reached.

TABLE-US-00002 TABLE 2 Value of selected ratios by weight of desirable to undesirable tobacco compounds within the liquid tobacco extracts (β-ionone+ β-damascenone) to (4-(methylnitrosamino)- 1-(3-pyridyl)-1 -butanone + (R,S)-N- nitrosoanatabine + (furaneol + (R,S)-N- (2,3-diethyl- nitrosoanabasine + N- (β-ionone + 5-methylpyrazine) * nitrosonornicotine + β-damascenone) 100)) ((2-furanemethanol)/ Example to (phenol) to (nicotine) 600)) 2A 2.27 1.35 × 10.sup.−3 5.25 2B 2.96 1.71 × 10.sup.−3 3.50 2C 4.12 2.75 × 10.sup.−3 7.83

[0241] In all three liquid extracts in accordance with the invention 2A, 2B, and 2C the ratio by weight of (β-ionone+β-damascenone) to (phenol) is consistently and significantly above 2.0. Further, in all three liquid extracts in accordance with the invention 2A, 2B, and 2C the ratio by weight of (furaneol+(2,3-diethyl-5-methylpyrazine)*100)) to (nicotine) is consistently and significantly above 1×10.sup.−3. Additionally, in all three liquid extracts in accordance with the invention 2A, 2B, and 2C the ratio by weight of (β-ionone+β-damascenone) to (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone+(R,S)—N-nitrosoanatabine+(R,S)—N-nitrosoanabasine+N-nitrosonornicotine+((2-furanemethanol)/600)) is consistently and significantly above 3.