Tobacco extract containing cembratrienediol and method for producing same

Abstract

Provided is a production method for a tobacco extract containing cembratriendiol, the method comprising: a step 1 for preparing a discharged solid substance obtained from a tobacco raw material puffing process; a step 2 for subjecting the discharged solid substance to extraction using an aprotic solvent and water; and a step 3 for recovering an organic phase from the product of step 2.

Description

[Technical field]

[0001] The present invention relates to a tobacco extract containing cembratrienediol and a method for producing the same. [Background technology]

[0002] Cembranoids are secondary metabolites secreted from glandular trichomes in the epidermis of tobacco plants, and are components that exhibit various physiological activities for bioregulation. The main component of cembranoids is cembratrienediol (CBT), which has been noted as an important component in the expression of aroma quality because it correlates with the characteristic aroma of tobacco plants. Its content is the highest among 89 so-called cembranoid compounds reported in leaf surface resin components of other tobacco plants (Non-Patent Document 1). CBT is a monocyclic diterpenoid found in trichome exudates. Isomers exist, and α-CBT and β-CBT are known. This CBT, like other cembranoids, has attracted attention as a carcinogenic inhibitor (Patent Documents 1 and 2, Non-Patent Document 2), and for example, cembratrienediol (CBT) isolated from tobacco leaves has attracted attention as a high antitumor agent (Patent Document 5).

[0003] It is generally known that CBT is obtained as follows. For example, leaf surface resin components are immersed and extracted from fresh or dried tobacco leaves of tobacco plants using organic solvents such as hexane, ether, chloroform, dichloromethane, methanol, and ethanol. After concentrating the leaf surface resin components, they are isolated and purified by, for example, chromatography using silica gel (Patent Documents 3 and 4, Non-Patent Document 3). Various extraction methods have also been reported (Non-Patent Document 4, Patent Document 5). However, considering the expansion of effective use of CBT, the total amount of refined products obtained from tobacco leaves is very small. For example, Patent Document 5 describes that 6 g of α-CBT and 2 g of β-CBT were obtained from 10 kg of dried tobacco leaves.

[0004] In addition, many methods using liquefied carbon dioxide or supercritical carbon dioxide have been considered to take advantage of the characteristics of the target components (Patent Documents 6 and 7). On the other hand, raw materials expanded with liquefied carbon dioxide have been considered as one of the raw materials for cigarettes, but the process is very similar to the above-mentioned extraction process using carbon dioxide. Therefore, a method that applies a part of the expansion process has been considered (Patent Document 8). Patent Document 8 discloses a method for obtaining tobacco aroma components such as CBT, in which supercritical carbon dioxide is brought into contact with tobacco raw materials, the tobacco components are dissolved in the carbon dioxide, and the fat-soluble portion is separated and recovered from the tobacco components dissolved in the carbon dioxide. In these methods, attention is focused on the components that dissolve in vaporized carbon dioxide, and a separate gas-liquid separator is required to separate the gas and the tobacco components. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] U.S. Patent No. 7,977,384 [Patent Document 2] U.S. Patent Application No. 2005 / 025075 [Patent Document 3] U.S. Pat. No. 4,701,570 [Patent Document 4] US Patent Application No. 2013 / 0014771 [Patent Document 5] China Patent Publication No. 104000302A [Patent Document 6] International Publication No. 2007 / 029264 [Patent Document 7] British Patent No. GB2173985 [Patent Document 8] International Publication No. 2007 / 119790 [Non-patent literature]

[0006] [Non-Patent Document 1] Yan, N.; Du, Y.; Liu, X.; Zhang, H.; Liu, Y.; Zhang, P.; Gong, D.; Zhang, Z. Chemical structures, biosynthesis, bioactivities, biocatalysis and semisynthesis of tobacco cembranoids: An overview. Ind. Crop. Prod. 2016, 83, pp66-80. [Non-Patent Document 2] Hisao Takayanagi, Total synthesis of sarcophytol A, a cembranoid with antitumor activity, 1995, Vol. 53, No. 8, p. 724-736 [Non-Patent Document 3] Y. Saito et. al., Identification of cembratriene-4,6-diol as antitumor-promoting agent from cigarette smoke condensate. Carcinogenesis 6:1189-1194 (1985) [Non-Patent Document 4] I. Weini,et. al.. Application of response surface method to optimize purification of tobacco stem extract by molecular distillation[J]. Tobacco Science & Technology, 2019 , 52(2): 79-87. Summary of the Invention [Problem to be solved by the invention]

[0007] In conventional methods, it has not been easy to obtain an extract containing cembratrienediol (CBT) from tobacco raw materials in a simple and efficient manner. Therefore, an object of the present invention is to provide a method for producing an extract containing CBT from solid matter discharged during the expansion process of tobacco raw materials in a simple and efficient manner. [Means for solving the problem]

[0008] The inventors have found that the above-mentioned problems can be solved by using waste materials containing tobacco leaf midribs and solid extracts that are discharged simultaneously with the separation of carbon dioxide gas during the expansion process of tobacco raw materials as raw materials. (1) Step 1: preparing a solid waste product obtained by expanding tobacco raw material; A step 2 of subjecting the discharged solid matter to solid-liquid extraction using an aprotic solvent; and step 3, recovering the organic phase from step 2; A method for producing a tobacco extract containing cembratrienediol, comprising: (2) The method according to (1), wherein the step 2 further comprises subjecting the aprotic solvent phase obtained by the solid-liquid extraction to extraction with water or an aqueous acid solution. (3) The method according to (1) or (2), wherein the aprotic solvent is a non-water-soluble organic solvent. (4) The method according to (3), wherein the non-water-soluble organic solvent is a hydrocarbon having 5 or 6 carbon atoms. (5) a step P1 of subjecting the organic phase obtained in the step 2 or the tobacco extract obtained by removing the solvent from the organic phase to normal phase chromatography using a mixed solvent of n-hexane / ethyl acetate as a mobile phase to obtain an n-hexane / ethyl acetate=50:50 fraction and an n-hexane / ethyl acetate=40:60 fraction; The manufacturing method according to any one of (1) to (4), further comprising: (6) A process P2 of adding methanol or ethanol to the organic phase obtained in the process 2 or to the tobacco extract obtained by removing the solvent from the organic phase to generate a precipitate and then removing the precipitate to obtain a solution. The manufacturing method according to any one of (1) to (4), further comprising: (7) a step P3 of subjecting the fraction obtained in the step P1 or P2 to reverse phase chromatography using water / methanol as a mobile phase; The method for producing a semiconductor device according to claim 5 or 6, further comprising: (8) The method according to any one of (2) to (7), wherein the aqueous acid solution is an aqueous solution of sulfuric acid, citric acid, or oxalic acid. (9) The method according to any one of (2) to (8), wherein the acidic aqueous solution has a pH of 3 or less. (10) A tobacco extract containing cembratrienediol, produced by the method according to any one of (1) to (9) above. (11) The tobacco extract according to (10), containing 90% by weight or more of the cembratrienediol. (12) A tobacco flavoring agent comprising the tobacco extract according to (10) or (11). (13) A tobacco material comprising the tobacco flavoring agent according to (12) above. (14) The tobacco material according to (13), which is a tobacco sheet or tobacco shreds. (15) A tobacco rod portion comprising the tobacco material according to (13) or (14). (16) A tobacco flavor inhalation article comprising the tobacco rod portion of (15). (17) A non-combustion, non-heating tobacco flavor inhalation article or a non-combustion, non-heating tobacco flavor inhalation article, comprising the tobacco rod portion of (15). (18) A smokeless tobacco comprising the tobacco material according to (13) or (14). Effect of the Invention

[0009] The present invention provides a method for producing a tobacco extract containing CBT in a simple and efficient manner. [Brief description of the drawings]

[0010] [Figure 1] 1 is a total ion chromatogram by GC / MS of the n-hexane solution obtained in Example 2. [Diagram 2] 1 is a total ion chromatogram by GC / MS of the chloroform solution obtained in Example 2. [Diagram 3] 1 is a total ion chromatogram by GC / MS of the ethyl acetate solution obtained in Example 2. [Figure 4]1 is a total ion chromatogram by GC / MS of the acetone solution obtained in Comparative Example 2. [Diagram 5] 1 is a total ion chromatogram by GC / MS of the methanol solution obtained in Comparative Example 2. [Figure 6] 1 is a total ion chromatogram by GC / MS of the n-hexane solution obtained in Example 3. [Figure 7] 1 is a total ion chromatogram by GC / MS of an ethyl acetate solution (concentration: 4% by weight) of the dried product obtained from the n-hexane / ethyl acetate 50:50 eluate fractionated by column chromatography in Example 4. [Figure 8] 1 is a total ion chromatogram by GC / MS of an ethyl acetate solution (concentration: 4% by weight) of the dried product obtained from the elution product with n-hexane / ethyl acetate 40:60 fractionated by column chromatography in Example 4. [Figure 9] 1 is a total ion chromatogram by GC / MS of an ethyl acetate solution (concentration: 4% by weight) of the dried product obtained from the eluate with n-hexane as a single solvent fractionated by column chromatography in Example 4. [Figure 10] 1 is a chromatogram showing fractionation of α-CBT and β-CBT by preparative high performance liquid column chromatography in Example 5. [Figure 11] FIG. 1 is a diagram showing one embodiment of a non-combustion heating type tobacco flavor inhalation article. [Figure 12] FIG. 1 is a diagram showing one embodiment of a non-combustion heating type tobacco flavor inhalation system. [Figure 13] FIG. 1 is a diagram showing one embodiment of a non-combustion, non-heating type tobacco flavor inhalation article. [Figure 14] FIG. 1 shows an embodiment of a tobacco capsule. [Figure 15] FIG. 1 illustrates an example of a power supply unit. [Figure 16] FIG. 2 is a cross-sectional view of one embodiment of a cartridge. [Figure 17] FIG. 2 shows the internal structure of one embodiment of the cartridge. [Figure 18]FIG. 2 is a diagram for explaining an outline of the expansion treatment process. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0011] The present invention will be described in detail below. In the present invention, "X to Y" includes the extreme values ​​X and Y. 1. Manufacturing method The manufacturing method of the present invention includes step 1 of preparing an excreted solid obtained in an expansion process of tobacco raw material, step 2 of subjecting the excreted solid to extraction using an aprotic solvent, and step 3 of recovering an organic phase from step 2.

[0012] (1) Process 1 In this step, the solid matter discharged from the tobacco raw material expansion process is prepared. The expansion process refers to a process in which the tobacco raw material is impregnated with a liquid and the liquid is rapidly vaporized to increase the volume of the tobacco material (see FIG. 18). In the present invention, the solid matter discharged from a known expansion process can be used. The tobacco raw material is tobacco leaves, aged tobacco leaves, tobacco shreds, tobacco powder, or the like. Tobacco leaves are a general term for harvested tobacco leaves before they are aged. One form of aging includes curing. Tobacco shreds are aged tobacco leaves or the like that are shredded to a predetermined size. In the present invention, it is preferable to use a solid fat-soluble component obtained when the expansion process is performed using supercritical carbon dioxide as described in Patent Document 8 and carbon dioxide is separated from the supercritical carbon dioxide containing the tobacco components as the discharged solid matter. This is because the discharged solid matter from the expansion process using supercritical carbon dioxide contains a large amount of CBT. In addition, the expansion process includes a step of threshing and chopping the raw tobacco leaves at the beginning, during which a small amount of cut pieces of tobacco fine powder and midribs are mixed into the tobacco raw material. When the raw material is subjected to the expansion process, after expansion, the light expanded midribs and the heavy midribs are discharged together with carbon dioxide gas, becoming discharged solids. Therefore, the discharged solids are the solid fat-soluble components described above, or solids of the expanded midribs and the unexpanded midribs, or a mixture of these.

[0013] (2) Process 2 In this step, the discharged solid matter is subjected to solid-liquid extraction using an aprotic solvent. An aprotic solvent is a solvent that does not dissolve in water because it does not have a dissociated proton. Examples of aprotic solvents include hydrocarbons; halogenated hydrocarbons such as dichloromethane and chloroform; esters such as ethyl acetate and propylene carbonate; ketones such as acetone; and nitriles such as acetonitrile. Among them, from the viewpoint of easy removal in the subsequent step, those having a boiling point of 70°C or less are preferable, and specifically, water-insoluble organic solvents, such as hydrocarbons having 5 or 6 carbon atoms (heptane, hexane, etc.), are more preferable. The target CBT is transferred to the aprotic solvent (organic phase). The aprotic solvent can be classified into low polarity solvents and medium polarity solvents according to their polarity. In one embodiment, the aprotic medium polarity solvent is defined as a solvent that exhibits a positive value of log Kow of 2 or less using the octanol / water partition ratio (Kow), and the aprotic low polarity solvent is defined as a solvent that exhibits a value of log Kow of more than 2 and 4 or less. In the present invention, aprotic low polarity solvents are preferred. Hydrocarbons with 5 or 6 carbon atoms are aprotic low polarity solvents. Kow is defined as the ratio of the concentration of the target compound (solvent) dissolved in the octanol phase to the concentration dissolved in water in a two-phase system of octanol and water. Kow is measured at room temperature. Kow = concentration in octanol phase / concentration in water phase

[0014] In one embodiment, the solvents used in the present invention are classified as exemplified below.

[0015] [Table 1]

[0016] In this step, the discharged solid may be subjected to extraction using an aprotic solvent and water or an acid aqueous solution. This is because nicotine in the discharged solid can be transferred to the aqueous phase by water. Since nicotine in the discharged solid can be transferred to the aqueous phase in the form of a salt by acid, it is preferable that the water contains an acid, that is, that the water is an acid aqueous solution. As the acid, an inorganic acid or an organic acid can be used, but from the viewpoint of the stability of the nicotine salt, it is preferable that the acid is sulfuric acid, citric acid, or oxalic acid. The pH of the acid aqueous solution is preferably 4 or less, more preferably 3 or less. If the pH exceeds 4, nicotine may not be sufficiently extracted. The lower limit of the pH is not limited, but is preferably 2 or more. The temperature at which this step is carried out is not limited, but is preferably 10 to 35°C, more preferably 20 to 30°C. In this step, it is preferable that the discharged solid is subjected to solid-liquid extraction using an aprotic solvent, and the organic phase obtained by the solid-liquid extraction is subjected to liquid-liquid extraction using water or an acid aqueous solution. After the solid-liquid extraction, the insoluble solids may be removed by filtration or the like.

[0017] (3) Process 3 In this step, the organic phase obtained in step 2 is recovered. The organic phase is the organic phase obtained by the solid-liquid extraction or the organic phase obtained by the liquid-liquid extraction. The method of recovery is not limited, and can be carried out, for example, using a separatory funnel. If necessary, the aqueous phase may be washed with an aprotic solvent, and the solvent after washing may be added to the organic phase. In this way, a solution of tobacco extract containing CBT can be obtained. The aprotic solvent may be removed from the solution to obtain a concentrated solution, or the tobacco extract may be isolated. The method of removing the solvent is not limited, and for example, an evaporator may be used.

[0018] (4) Purification process The production method of the present invention may include a step of purifying the organic phase. The purification can be performed by subjecting the organic phase or the tobacco extract obtained by removing the solvent from the organic phase to normal phase chromatography using a mixed solvent of n-hexane / ethyl acetate as the mobile phase to obtain an n-hexane / ethyl acetate=50:50 fraction and an n-hexane / ethyl acetate=40:60 fraction (step P1). Alternatively, the purification can be performed by adding methanol or ethanol to the organic phase or the tobacco extract obtained by removing the solvent from the organic phase to generate a precipitate, and then obtaining a solution from which the precipitate has been removed (step P2). Furthermore, the fraction obtained in step P1 or the solution obtained in step P2 may be subjected to reverse phase chromatography using water / methanol as the mobile phase to obtain the n-hexane / ethyl acetate=50:50 fraction and the 40:60 fraction. By passing through these steps, the content of CBT in the tobacco extract can be increased. In the present invention, CBT refers to α-CBT, β-CBT, or a combination thereof.

[0019] 2. Tobacco extract The tobacco extract obtained by the above-mentioned production method (hereinafter also referred to as "tobacco extract of the present invention") contains CBT. Since CBT imparts tobacco aroma and taste, the tobacco extract of the present invention is useful as a tobacco flavoring agent. Furthermore, the tobacco extract obtained through the above-mentioned purification step has a CBT content of preferably 90% or more, more preferably 95% or more, and even more preferably 99% or more, and has a high purity. In one embodiment, the tobacco flavoring agent is a tobacco extract, and in another embodiment, it contains tobacco extract and other components.

[0020] 3.Tobacco materials The tobacco flavoring agent containing the tobacco extract of the present invention (hereinafter also referred to as "the tobacco flavoring agent of the present invention") is useful as an additive to tobacco materials. Examples of tobacco materials include tobacco sheets, tobacco shreds, cigarette papers, polysaccharide sheets, etc. The tobacco material to which the tobacco flavoring agent of the present invention has been added is also referred to as "the tobacco material of the present invention". (1) Tobacco sheets A tobacco sheet is a sheet obtained by molding a composition containing aged tobacco leaves. The aged tobacco leaves used for the tobacco sheet are not particularly limited, but may be, for example, those that have been deboned and separated into lamina and midrib. The aged tobacco leaves refer to tobacco leaves that have been subjected to treatment such as curing and long-term storage in a warehouse or the like. In the present invention, the term "sheet" refers to a material having a pair of approximately parallel main and side surfaces. The tobacco sheet can be molded by known methods such as a papermaking method, a casting method, and a rolling method. Details of various tobacco sheets molded by such methods are disclosed in "Encyclopedia of Tobacco, Tobacco Research Center, March 31, 2009". The manner in which the tobacco flavoring agent of the present invention is added to the tobacco sheet is not limited.

[0021] For example, the tobacco extract of the present invention may be dissolved in a solvent to prepare a tobacco flavoring agent in a solution form, which may then be sprayed or impregnated into a completed tobacco sheet, or the tobacco flavoring agent of the present invention may be added when the tobacco sheet is molded. For example, in the papermaking method, a water-soluble component is extracted from aged tobacco leaves, separated into an aqueous extract and a residue, a mixture of the fibrous residue and pulp is made into paper, and a concentrated solution of the aqueous extract is added to the paper-made sheet, and the tobacco flavoring agent of the present invention may be added to the aqueous extract. In the casting method, water, pulp, binder, and aged tobacco pulverized material are mixed to form a mixture, which is then cast, and the tobacco flavoring agent of the present invention may be added to the mixture. In the rolling method, water, pulp, binder, and aged tobacco pulverized material are mixed to form a mixture, which is then fed into a plurality of rolling rollers for rolling, and the tobacco flavoring agent of the present invention may be added to the mixture.

[0022] Furthermore, as described in WO 2014 / 104078, a nonwoven tobacco sheet can be obtained by mixing ground aged tobacco with a binder to form a mixture, sandwiching the mixture between nonwoven fabrics, and molding the laminate into a certain shape by heat welding. In this method, the tobacco flavoring agent of the present invention can be added to the mixture.

[0023] The tobacco sheet may contain an aerosol-generating substrate. The type of the aerosol-generating substrate is not particularly limited, and various extracts from natural products or their components can be selected according to the application. Specific examples of the aerosol-generating substrate include polyhydric alcohols such as glycerin, propylene glycol, sorbitol, xylitol, and erythritol, triacetin, 1,3-butanediol, and mixtures thereof. The content of the aerosol-generating substrate can be adjusted to various amounts depending on the form in which it is used in the tobacco product. For example, when the tobacco sheet contains an aerosol-generating substrate, the content is usually 5% by weight or more, preferably 10% by weight or more, and more preferably 15% by weight or more, and usually 50% by weight or less, preferably 40% by weight or less, and more preferably 25% by weight or less, based on the total weight of the tobacco sheet, from the viewpoint of obtaining a good flavor.

[0024] (2) Tobacco Shreds Examples of tobacco shreds include aged tobacco leaves shredded to a predetermined size, the above-mentioned tobacco sheets shredded to a predetermined size, or a mixture of these. The size is not limited, and an example is a shredded tobacco sheet with a width of 0.5 to 2.0 mm and a length of 3 to 10 mm. Tobacco shreds of such a size are preferable in the embodiment of filling a filling material described below. In addition, examples of tobacco shreds include strand-type shreds obtained by shredding processed tobacco leaves to a width of 0.5 to 2.0 mm and a length longer than the above-mentioned tobacco shreds, preferably about the same length as cigarette paper. The tobacco flavoring agent of the present invention may be added to tobacco shreds or to the raw material before cutting.

[0025] The tobacco shreds may contain the aerosol-generating substrate. When the tobacco shreds contain the aerosol-generating substrate, the content of the aerosol-generating substrate is usually 5% by weight or more, preferably 10% by weight or more, more preferably 15% by weight or more, based on the weight of the tobacco shreds, from the viewpoints of generating a sufficient amount of aerosol and obtaining a good flavor, and is usually 50% by weight or less, preferably 40% by weight or less, more preferably 25% by weight or less.

[0026] (3) Rolling paper The cigarette paper containing the tobacco flavoring agent of the present invention can be prepared by spraying or impregnating the cigarette paper. Examples of the cigarette paper include those containing pulp as a main component. Pulp may be made from wood pulp such as softwood pulp or hardwood pulp, or may be made by mixing non-wood pulp such as flax pulp, hemp pulp, sisal pulp, and esparto, which are generally used for cigarette paper for tobacco articles. These pulps may be used alone or in combination of multiple types in any ratio. The cigarette paper may be made of one sheet or multiple sheets or more. The cigarette paper may be used in a form in which tobacco raw material such as tobacco shreds is wrapped, and may also be used as a material (e.g., tip paper) for wrapping the wrapped member together with other members such as a cooling member or a filter member. As the pulp, chemical pulp produced by the kraft cooking method, acidic / neutral / alkaline sulfite cooking method, soda salt cooking method, etc., ground pulp, chemi-ground pulp, thermomechanical pulp, etc. can be used.

[0027] (4) Polysaccharide sheet A polysaccharide sheet is a sheet whose main component is polysaccharide, and the tobacco flavoring agent of the present invention can be contained in the polysaccharide sheet. A flavor inhalation article using a polysaccharide sheet containing the tobacco flavoring agent of the present invention can release a sufficient flavor. Examples of polysaccharides include carrageenan, agar, gellan gum, tamarind gum, psyllium seed gum, konjac glucomannan, carrageenan, locust bean gum, guar gum, agar, xanthan gum, gellan gum, tamarind gum, tara gum, konjac glucomannan, starch, cassia gum, and psyllium seed gum.

[0028] The polysaccharide sheet containing the tobacco flavoring agent of the present invention can be used in a burnable tobacco flavor inhalation article and a non-burnable tobacco flavor inhalation article. In the former embodiment, for example, a polysaccharide sheet as disclosed in Patent No. 5481574 can be used. In this embodiment, the content of the tobacco flavoring agent of the present invention can be preferably 10% by weight or more, more preferably 18% by weight or more, even more preferably 60% by weight or more, and particularly preferably 70% by weight or more, based on the sheet. The polysaccharide sheet can be prepared by mixing polysaccharide and water, heating to prepare an aqueous solution of the polysaccharide, adding a flavoring and an emulsifier to the aqueous solution, and kneading and emulsifying the mixture. A known emulsifier can be used as the emulsifier.

[0029] In the latter embodiment, a polysaccharide sheet as described in PCT / JP2019 / 20136 can be used. In this embodiment, it is particularly preferable to use agar as the polysaccharide. The content of agar is preferably 10 to 50% by weight, more preferably 15 to 45% by weight, based on the sheet. The content of the tobacco flavoring agent of the present invention in the polysaccharide sheet can be 35 to 80% by weight based on the sheet.

[0030] In this embodiment, it is preferable to use a saccharide compound selected from the group consisting of sugars and sugar alcohols. Examples of "sugars" include glucose, sucrose, fructose, xylose, galactose, mannose, maltose, trehalose, lactose, and raffinose. Examples of "sugar alcohols" include sorbitol, an alcohol obtained by reducing the carbonyl group of a sugar to a hydroxyl group. The content of this compound is preferably 10% by weight or more, more preferably 10 to 500% by weight, even more preferably 10 to 300% by weight, and even more preferably 10 to 200% by weight, based on the weight of the agar. In addition, it is preferable to use an emulsifier in this embodiment. Known emulsifiers can be used, and the content is preferably 0.5 to 10% by weight, more preferably 1.0 to 8.0% by weight, based on the weight of the agar.

[0031] The polysaccharide sheet in this embodiment can be produced by kneading raw materials including agar, a saccharide compound, a flavoring, and an emulsifier in water to prepare a raw material slurry, spreading the raw material slurry on a substrate, and drying.

[0032] 4. Tobacco-flavored inhalation products In the present invention, the term "flavor inhalation article" refers to an article for a user to inhale flavor. Among flavor inhalation articles, those containing tobacco or components derived from tobacco are referred to as "tobacco flavor inhalation article". Tobacco flavor inhalation articles are broadly classified into "combustion type tobacco flavor inhalation article" (also simply referred to as "smoking article") that generates flavor by combustion, and "non-combustion type tobacco flavor inhalation article" that generates flavor without combustion. Furthermore, non-combustion type tobacco flavor inhalation articles are broadly classified into "non-combustion heating type tobacco flavor inhalation article" that generates flavor by heating, and "non-combustion non-heating type tobacco flavor inhalation article" that generates flavor without heating. The tobacco flavoring agent of the present invention is suitable for non-combustion heating type tobacco flavor inhalation article or non-combustion non-heating type tobacco flavor inhalation article. In addition, a combination of a device for generating aerosol (such as a heating device or an atomizing device) and a non-combustion heating type tobacco flavor inhalation article is particularly referred to as a non-combustion heating type tobacco flavor inhalation system.

[0033] (1) Non-combustion heating tobacco flavor inhalation products FIG. 11 shows one embodiment of a non-combustion heating tobacco flavor inhalation article. As shown in the figure, the non-combustion heating tobacco flavor inhalation article 20 includes a tobacco rod portion 20A, a cylindrical cooling portion 20B having perforations on the circumference, and a filter portion 20C. The non-combustion heating tobacco flavor inhalation article 20 may include other members. The axial length of the non-combustion heating tobacco flavor inhalation article 20 is not limited, but is preferably 40 to 90 mm, more preferably 50 to 75 mm, and even more preferably 50 to 60 mm or less. The circumferential length of the non-combustion heating tobacco flavor inhalation article 20 is preferably 16 to 25 mm, more preferably 20 to 24 mm, and even more preferably 21 to 23 mm. For example, an embodiment in which the length of the tobacco rod portion 20A is 20 mm, the length of the cooling portion 20B is 20 mm, and the length of the filter portion 20C is 7 mm can be mentioned. The length of each of these members can be appropriately changed according to the manufacturing suitability, the required quality, and the like. FIG. 11 shows an embodiment in which the first segment 25 is disposed, but it is also possible to dispose the first segment 25 and to dispose only the second segment 26 downstream of the cooling section 20B.

[0034] 1) Tobacco rod section 20A In the tobacco rod portion 20A, tobacco shreds or tobacco sheets containing the tobacco flavoring agent of the present invention can be used as the tobacco filler 21. The method of filling the tobacco filler 21 into the cigarette paper 22 is not particularly limited, but for example, the tobacco filler 21 may be wrapped in the cigarette paper 22, or the tobacco filler 21 may be filled into a cylindrical cigarette paper 22. When the tobacco has a longitudinal direction such as a rectangular shape, the tobacco may be filled so that the longitudinal direction is in an unspecified direction in the cigarette paper 22, or may be filled so that the tobacco is aligned in the axial direction of the tobacco rod portion 20A or aligned in a direction perpendicular to the axial direction. In addition, the cigarette paper 22 may be a cigarette paper containing the tobacco flavoring agent of the present invention described above. When the tobacco rod portion 20A is heated, the tobacco components, aerosol-generating base material, and water contained in the tobacco filler 21 are vaporized and are available for inhalation.

[0035] 2) Cooling section 20B The cooling section 20B is preferably constructed of a cylindrical member. The cylindrical member may be, for example, a cardboard tube 23 formed by processing cardboard into a cylindrical shape. The cooling section 20B may also be formed by a sheet of thin material that is wrinkled and then pleated, gathered, or folded to form a channel. For example, a sheet material selected from the group consisting of polyethylene, polypropylene, polyvinyl chloride, polyethylene terephthalate, polylactic acid, cellulose acetate, and aluminum foil may be used as such a material. The total surface area of ​​the cooling section 20B is appropriately adjusted in consideration of the cooling efficiency, and may be, for example, 300 to 1000 mm2 / mm. The cooling section 20B is preferably provided with perforations 24. The presence of the perforations 24 allows outside air to be introduced into the cooling section 20B during inhalation. This allows the tobacco rod section 20 The vaporized aerosol components generated by heating A come into contact with the outside air, and the temperature drops, so that the components are liquefied, forming an aerosol. The diameter (diameter) of the perforations 24 is not particularly limited, and may be, for example, 0.5 to 1.5 mm. The number of perforations 24 is not particularly limited, and may be one or two or more. For example, a plurality of perforations 24 may be provided on the circumference of the cooling section 20B.

[0036] The cooling section 20B may be rod-shaped with an axial length of, for example, 7 to 28 mm. For example, the axial length of the cooling section 20B may be 18 mm. The cooling section 20B may have a substantially circular axial cross-sectional shape with a diameter of 5 to 10 mm. For example, the diameter of the cooling section may be about 7 mm.

[0037] 3) The filter part 20C The configuration of the filter part 20C is not particularly limited, and may be composed of one or more packed layers. The outside of the packed layers may be wrapped with one or more wrapping papers. The airflow resistance of the filter part 20C can be appropriately changed depending on the amount and material of the packing filled in the filter part 20C. For example, when the packing is cellulose acetate fiber, the airflow resistance can be increased by increasing the amount of cellulose acetate fiber filled in the filter part 20C. When the packing is cellulose acetate fiber, the packing density of the cellulose acetate fiber is 0.13 to 0.18 g / cm. 3 The airflow resistance is a value measured by an airflow resistance measuring device (product name: SODIMAX, manufactured by SODIM).

[0038] The circumferential length of the filter part 20C is not particularly limited, but is preferably 16 to 25 mm, more preferably 20 to 24 mm, and even more preferably 21 to 23 mm. The axial length of the filter part 20C (horizontal direction in FIG. 11) can be selected from 4 to 10 mm, and is selected so that the airflow resistance is 15 to 60 mmH2O / seg. The axial length of the filter part 20C is preferably 5 to 9 mm, more preferably 6 to 8 mm. The cross-sectional shape of the filter part 20C is not particularly limited, but can be, for example, a circle, an ellipse, a polygon, etc. In addition, a destructible capsule containing a fragrance, fragrance beads, or a fragrance may be directly added to the filter part 20C.

[0039] The filter part 20C may have a center hole part as the first segment 25. The center hole part is composed of a first packed layer 25a having one or more hollow parts and an inner plug wrapper (inner wrapping paper) 25b that covers the packed layer. The center hole part has a function of increasing the strength of the mouthpiece part. The center hole part may not have an inner plug wrapper 25b and may maintain its shape by thermoforming. The filter part 20C may have a second segment 26. The second segment 26 is composed of a second packed layer 26a and an inner plug wrapper (inner wrapping paper) 26b that covers the packed layer. The second packed layer 26a can be, for example, a rod with an inner diameter of φ5.0 to φ1.0 mm, which is packed with cellulose acetate fibers at a high density and hardened by adding 6 to 20% by weight of a plasticizer containing triacetin to the weight of the cellulose acetate. Since the second packed layer has a high fiber packing density, air and aerosol flow only through the hollow parts during inhalation, and hardly flow through the second packed layer. Since the second filling layer inside the center hole segment is a fiber filling layer, the feel from the outside during use is less likely to cause discomfort to the user.

[0040] 1st packed layer 25 a The first and second packed layers 26a and 26b are connected to each other by an outer plug wrapper (outer wrapping paper) 27. The outer plug wrapper 27 may be, for example, a cylindrical paper. The tobacco rod portion 20A, the cooling portion 20B, and the first packed layer 25 that has already been connected to each other are connected to each other by an outer plug wrapper (outer wrapping paper) 27. a and the second filling layer 26a are connected by mouthpiece lining paper 28. These connections can be made, for example, by applying glue such as vinyl acetate glue to the inside surface of the mouthpiece lining paper 28 and wrapping the three components. These components may be connected in multiple places with multiple lining papers.

[0041] 4) Non-combustion heating type tobacco flavor inhalation system A combination of a non-combustion heating type tobacco flavor inhalation article and a heating device for generating an aerosol is also referred to as a non-combustion heating type tobacco flavor inhalation system. An example of the system is shown in Fig. 12. In the figure, the non-combustion heating type tobacco flavor inhalation system includes a non-combustion heating type tobacco flavor inhalation article 20 and a heating device 10 that heats a tobacco rod portion 20A from the outside.

[0042] The heating device 10 includes a body 11, a heater 12, a metal tube 13, a battery unit 14, and a control unit 15. The body 11 has a cylindrical recess 16, and the heater 12 and the metal tube 13 are disposed at positions corresponding to the tobacco rod portion 20A to be inserted therein. 12 The heater 12 can be a heater using electric resistance, and power is supplied from a battery unit 14 in response to an instruction from a control unit 15 that controls temperature, to heat the heater 12. The heat generated by the heater 12 is transferred to the tobacco rod portion 20A through a metal tube 13 with high thermal conductivity. In the figure, the heating device 10 is shown as heating the tobacco rod portion 20A from the outside, but it may be heating from the inside. The heating temperature by the heating device 10 is not particularly limited, but is preferably 400°C or less, more preferably 150 to 400°C, and even more preferably 200 to 350°C. The heating temperature refers to the temperature of the heater of the heating device 10.

[0043] (3) Non-combustion, non-heating tobacco flavor inhalation products 13 shows one embodiment of a non-combustion, non-heating tobacco flavor inhalation article. The non-combustion, non-heating tobacco flavor inhalation article 30 includes a power supply unit 30D, a cartridge 30E, and a tobacco capsule 30F. The non-combustion, non-heating tobacco flavor inhalation article 30 has a shape extending from a non-suction end u (upstream) to a mouth end d (downstream). The cartridge 30E is detachable from the power supply unit 30D. The tobacco capsule 30F is detachable from the cartridge 30E.

[0044] 1) Tobacco capsules Fig. 14 shows an example of a tobacco capsule 30F. As shown in the figure, the tobacco capsule 30F is a tobacco rod portion and has a flavor source 300 therein. The flavor source 300 contains a tobacco material (the tobacco material of the present invention) containing a tobacco flavoring agent of the present invention. The tobacco capsule 30F is connected to a cartridge 30E. Specifically, a part of the tobacco capsule 30F is housed in the cartridge 30E.

[0045] The tobacco capsule 30F has a housing 310 housing the flavor source 300, a mesh body 320, a nonwoven fabric 330, and a cap 340. The aerosol atomized by the atomizing section 220 described later is introduced into the housing 310 through the mesh body 320, and is brought into contact with the flavor source 300 to impart flavor to the aerosol. The aerosol is then inhaled by the user through the nonwoven fabric 330. In this manner, the non-combustion, non-heating type tobacco flavor inhalation article 30 can impart flavor to the aerosol without heating the flavor source 300. Furthermore, substantially no aerosol is generated from the flavor source 300.

[0046] In the direction of the aerosol flow, the length of the tobacco capsule 30F (container 310) is preferably 40 mm or less, more preferably 25 mm or less. In addition, in the direction of the aerosol flow, the length is preferably 1 mm or more, more preferably 5 mm or more. In the direction perpendicular to the direction of the aerosol flow, the maximum length of the container 310 of the tobacco capsule 30F (container 310) is preferably 20 mm or less, more preferably 10 mm or less. In addition, in the direction perpendicular to the direction of the aerosol flow, the maximum length of the tobacco capsule 30F (container 310) is preferably 1 mm or more, more preferably 3 mm or more.

[0047] The flavor source 300 containing tobacco is composed of raw material pieces that impart flavor to the aerosol. The lower limit of the size of the raw material pieces is preferably 0.2 to 1.2 mm, and more preferably 0.2 to 0.7 mm. The smaller the size of the raw material pieces that constitute the flavor source 300, the greater the specific surface area, and therefore the easier it is to release flavor components. As the raw material pieces that constitute the flavor source 300, cut tobacco, which is the tobacco material of the present invention, or a molded product obtained by molding the tobacco raw material of the present invention into a granular form can be used. The flavor source 300 may contain flavors such as plants other than tobacco (e.g., mint, herbs, etc.) and menthol. Furthermore, the flavor source 300 containing tobacco may contain a flavoring agent. Examples of the flavoring agent include materials that exhibit sweetness, sourness, saltiness, umami, bitterness, astringency, richness, spiciness, harshness, astringency, and the like. Examples of materials that exhibit sweetness include sugars, sugar alcohols, and sweeteners. Examples of the sugars include monosaccharides, disaccharides, oligosaccharides, polysaccharides, etc. Examples of the sweeteners include natural sweeteners, synthetic sweeteners, etc.

[0048] The raw material pieces are obtained, for example, by sieving in accordance with JIS Z 8815 using a stainless steel sieve conforming to JIS Z 8801. For example, the raw material pieces are sieved for 20 minutes using a stainless steel sieve having an opening of 0.71 mm by a dry mechanical shaking method to obtain raw material pieces that pass through the stainless steel sieve having an opening of 0.71 mm. Next, the raw material pieces are sieved for 20 minutes using a stainless steel sieve having an opening of 0.212 mm by a dry mechanical shaking method to remove the raw material pieces that pass through the stainless steel sieve having an opening of 0.212 mm. In other words, the raw material pieces that constitute the flavor source 300 are raw material pieces that pass through the stainless steel sieve (opening = 0.71 mm) that specifies the upper limit and do not pass through the stainless steel sieve (opening = 0.212 mm) that specifies the lower limit. Therefore, the lower limit of the size of the raw material pieces constituting the flavor source 300 is defined by the opening of the stainless steel sieve that defines the lower limit, and the upper limit of the size of the raw material pieces constituting the flavor source 300 is defined by the opening of the stainless steel sieve that defines the upper limit.

[0049] The amount of flavor source 300 contained in the container 310 is preferably 300 mg or more, and more preferably 350 mg or more, from the viewpoint of increasing the amount of nicotine released during smoking.

[0050] 2) Power supply unit An example of a power supply unit 30D is shown in FIG. 15. The power supply unit 30D has a battery 110. The battery 110 may be a disposable battery or a rechargeable battery. The initial value of the output voltage of the battery 110 is preferably in the range of 1.2 V to 4.2 V. The battery capacity of the battery 110 is preferably in the range of 100 mAh to 1000 mAh.

[0051] 3) The cartridge An example of a cartridge 30E is shown in Figures 16 and 17. Figure 16 is a cross-sectional view of an example of the cartridge 30E, and Figure 17 is a view showing its internal structure. The cartridge 30E has a reservoir 210, an atomizing section 220, a flow path forming body 230, an outer frame body 240, and an end cap 250. E has a first flow path 200X disposed downstream of the atomizing section 220 as an aerosol flow path.

[0052] The reservoir 210 stores the aerosol source 200. The reservoir 210 is located around the flow path forming body 230 in a cross section perpendicular to the flow direction of the aerosol (direction from the non-suction end to the suction end (from upstream to downstream)). The reservoir 210 is located in the gap between the flow path forming body 230 and the outer frame body 240. The reservoir 210 is formed of, for example, a porous body such as a resin web or cotton. The reservoir 210 may also be formed of a tank that contains the liquid aerosol source 200. Examples of the aerosol source 200 include glycerin and propylene glycol.

[0053] The atomizing unit 220 atomizes the aerosol source 200 by the power supplied from the battery 110 without combustion. The atomizing unit 220 is composed of a heating wire (coil) wound at a predetermined pitch. The atomizing unit 220 is preferably composed of a heating wire having a resistance value in the range of 1.0 to 3.0 Ω. The predetermined pitch is preferably equal to or greater than a value at which the heating wires do not come into contact with each other, and is preferably smaller than that value. The predetermined pitch is preferably, for example, 0.40 mm or less. The predetermined pitch is preferably constant to stabilize the atomization of the aerosol source 200. The predetermined pitch is the distance between the centers of adjacent heating wires.

[0054] The flow path forming body 230 has a cylindrical shape that forms a first flow path 200X extending along the flow direction of the aerosol. The outer frame body 240 has a cylindrical shape that houses the flow path forming body 230. The outer frame body 240 extends downstream beyond the end cap 250 and houses a part of the tobacco capsule 30F. The end cap 250 is a cap that closes the gap between the flow path forming body 230 and the outer frame body 240 from the downstream side. The end cap 250 prevents the aerosol source 200 stored in the reservoir 210 from flowing downstream of the tobacco capsule 30F. F This prevents leakage to the side.

[0055] 5. Smokeless tobacco Smokeless tobacco is a product that contains a flavor source, and a user can taste the flavor derived from the flavor source by directly inhaling the product into the nasal cavity or oral cavity. The tobacco material of the present invention can be used as the flavor source contained in the smokeless tobacco. Snuff and chewing tobacco are known as smokeless tobacco. EXAMPLES

[0056] [Example 1] A solid discharged material obtained from the expansion process of tobacco raw materials using supercritical carbon dioxide was prepared. Specifically, the process shown in FIG. 18 was performed, the tobacco raw materials were impregnated with carbon dioxide in a supercritical state, the tobacco raw materials in a dry ice state were taken out, and then the carbon dioxide was removed by rapid air drying. The high-temperature carbon dioxide gas (tail gas) discharged at that time and the discharged solid material (dust) consisting of the tar-like components and finely chopped powder separated from the carbon dioxide were obtained as the discharged solid material. 150 g of the discharged solid material was weighed and placed in a 2500 ml sealed stainless steel container. Next, 1500 ml of ethyl acetate (Fujifilm Wako Pure Chemical Industries, for high-performance liquid chromatography) was added, and the mixture was extracted for 3 hours in a 40°C warm bath while being sealed and stirred. After extraction, the ethyl acetate solution and the extraction residue were separated using a stainless steel mesh with a mesh size of 250 μm, and about 1300 ml of ethyl acetate solution was obtained. A 0.1% aqueous sulfuric acid solution (pH=3) was prepared in advance, and the 0.1% aqueous sulfuric acid solution and the previously obtained ethyl acetate solution were mixed in a solution ratio of 5:3 to obtain a mixed solution of 800 ml. 50 g of salt was further added, and the mixture was thoroughly shaken in a separating funnel to perform liquid-liquid extraction. At this time, tobacco alkaloid components, mainly nicotine, were transferred to the lower sulfuric acid aqueous solution, and the hydrophobic active ingredients of tobacco leaves were transferred to the upper organic phase. After sufficient standing, the organic phase was removed, and about 50 g of anhydrous sodium sulfate was added and stirred to perform a dehydration operation within the organic phase. Insoluble matter was removed by paper filtration. Ethyl acetate was further removed under reduced pressure using a rotary evaporator (manufactured by Nippon Buchi Co., Ltd.), and 6.8 g (yield 4.5%) of dried matter was obtained. The dried matter was dissolved in the same solvent as that used in the extraction to prepare a solution with a dried matter concentration of 4 wt%. This solution was analyzed by GC / MS under the following conditions.

[0057] Gas Chromatography with Mass Spectrometer (GC / MS) Equipment: Agilent Technologies 7890A / 5975C GC / MSD GC conditions Column: HP-5MS (Agilent Technologies) Inner diameter 0.25mm x length 30m, film thickness 0.25μm Injection volume: 1μl Injection mode: Split (10:1) Inlet temperature: 270℃ Septum purge flow rate: 5ml / min Carrier gas: Helium (He) Column flow rate: 1 ml / min (constant flow mode) Oven temperature: 40℃ (3 min) - 4℃ / min - 280℃ (20 min) Transfer line temperature: 280℃ MS conditions Solvent waiting time: 4 minutes Ionization method: Electron impact ionization method (EI method), 70 eV Ion source temperature: 230℃ Quadrupole temperature: 150℃ Measurement mode: Scan MS scan range: m / z 26-450 Threshold: 50 Sampling rate: 2

[0058] [Comparative Example 1] A dry product (5.4 g, yield 3.6%) was obtained in the same manner as in Example 1, except that the pre-puffed solid was used instead of the discharged solid.

[0059] From the total ion chromatogram obtained by GC / MS analysis of the solid and the product before expansion, a single ion (m / z 83) contained in the MS pattern of CBT was extracted, and the peak area values ​​of each were compared. It was confirmed that the CBT peak area value of the solid product was approximately 8 times larger than that of the product before expansion. Furthermore, the solid product (unwanted material discharged from the expansion process) can be said to be suitable as a sample for extracting the effective utilization of CBT.

[0060] [Example 2, Comparative Example 2] Examination of organic solvents The following organic solvents were prepared for use in the extraction process. Example 2: n-Hexane, chloroform, ethyl acetate Comparative Example 2: Acetone, Methanol Five 100 ml screw tubes were prepared, and about 5 g of the same discharged solids as those used in Example 1 were weighed out into each screw tube, and 50 ml of each organic solvent was added and mixed well, and then the mixture was left to stand at room temperature for a day and night. The mixture was filtered through a filter paper, and a small amount of anhydrous sodium sulfate was added to the filtrate to dehydrate it, and then the mixture was filtered through a filter paper again, and the organic solvent was removed under reduced pressure. The obtained dried matter was dissolved in the same solvent as that used for extraction to obtain a solution with a dry matter concentration of 4 wt%. These solutions were analyzed by GC / MS under the conditions shown in Example 1.

[0061] The total ion chromatograms obtained by GC / MS analysis of n-hexane, chloroform, ethyl acetate, acetone, and methanol solutions are shown in Figures 1 to 5. From the chromatograms in Figures 1 to 5, it was found that CBT (retention time 48.6 minutes) was extracted from the solid matter when solvent extraction was performed with n-hexane, chloroform, or ethyl acetate. It was confirmed that peaks of other components (retention time 24 minutes or earlier) were present in the extraction with chloroform or ethyl acetate. It was revealed that, among the three solvents capable of extracting the desired CBT, n-hexane, which contains as few peaks of unnecessary components as possible, is preferable as the extraction solvent. It was found that when the extraction process was performed using a polar solvent such as acetone or methanol, CBT was hardly extracted from the solid matter.

[0062] [Example 3] 300 g of the discharged solid material used in Example 1 was weighed and placed in a 2500 ml sealed stainless steel container. Next, 1500 ml of n-hexane (Fujifilm Wako Pure Chemical Industries, for high performance liquid chromatography) was added, and the mixture was extracted for 3 hours in a 40°C warm bath while being sealed and stirred. After the extraction, the n-hexane solution and the extraction residue were separated using a stainless steel mesh with a mesh size of 250 μm, and about 1200 ml of n-hexane solution was obtained. A 0.1% aqueous sulfuric acid solution was prepared in advance, and the 0.1% aqueous sulfuric acid solution and the previously obtained n-hexane solution were mixed in a solution ratio of 5:3 to obtain a mixed solution of 800 ml. Furthermore, 50 g of salt was added, and the mixture was thoroughly shaken in a separating funnel to perform a liquid-liquid extraction operation. At this time, alkaloid components represented by nicotine were transferred to the lower layer of the aqueous sulfuric acid solution, and hydrophobic active ingredients of the tobacco leaves were transferred to the upper layer of the organic phase. After sufficient standing, the organic phase was removed, and about 50 g of anhydrous sodium sulfate was added and stirred to perform a dehydration operation within the organic phase. Insoluble matter was removed by paper filtration. Furthermore, n-hexane was removed under reduced pressure using a rotary evaporator (manufactured by Nippon Buchi Co., Ltd.), and 6.9 g of a dry solid (yield 2.3%) was obtained. The dry solid was dissolved in the same solvent as that used in the extraction to prepare a solution with a dry solid concentration of 4 wt.%. This was analyzed by GC / MS under the same conditions as in Example 1 (Figure 6). From the chromatogram in Figure 6, it was confirmed that CBT (retention time 48.6 minutes) was present and that alkaloids, such as nicotine (retention time 24.6 minutes), could be removed by the liquid-liquid extraction operation.

[0063] [Example 4] The dried product containing CBT from which alkaloids were removed obtained in Example 3 was fractionated using normal phase column chromatography. 3.3 g of the solid dissolved in n-hexane was added to a glass chromatographic column packed with 60 g of Wakosil C-300 (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) mixed with n-hexane, and the mixture was developed sequentially using a mixed solvent of n-hexane and ethyl acetate (including n-hexane and ethyl acetate alone). The eluate obtained was analyzed by GC / MS under the conditions shown in Example 1, and n-hexane / ethyl acetate 50:50 (Figure 7) and 40:60 (Figure 8) were confirmed as fractions containing CBT. It was found that higher hydrocarbons other than CBT (retention time 57.4 to 68.4 minutes) were eluted with the initial n-hexane single solvent (Figure 9).

[0064] [Example 5] In order to isolate and purify CBT from the fraction containing CBT obtained in Example 4 (a mixture of n-hexane / ethyl acetate 50:50 and 40:60 eluates), reversed-phase HPLC was performed as follows. The sample used for HPLC (Agilent Technologies 1260Infinity) was treated with Sep-Pak Vac C18 (Waters) to remove low polarity components such as dyes. 500 μL of the treated sample was injected. The HPLC flow rate was 5 mL / min, the mobile phase was Water / MeOH (20 / 80), and isocratic elution was performed using a YMC-Pack ODS-A / S-5 μm / 12 nm column (YMC). A diode array detector was used as the detector, and the detection wavelength was 214 nm. The signal detected at 214 nm was fractionated into a fraction collector. When the detection times were confirmed using standard samples of α-CBT and β-CBT, α-CBT was detected at 15.0 min and β-CBT was detected at 20.7 min. Therefore, each fraction (within the dashed line in FIG. 10) corresponding to the above detection times was collected, and the sample was concentrated and dried to obtain α-CBT and β-CBT as white powder. In addition, the peak area values ​​of the dried product obtained in Example 3 and each fraction containing CBT obtained above were compared from the total ion chromatogram obtained by GC / MS analysis, and the yield of CBT was 71.5% (α-CBT: 57.6%, β-CBT: 13.9%), confirming that CBT can be obtained with high efficiency from tobacco expansion process waste.

[0065] It is clear that the present invention makes it possible to efficiently produce an extract containing CBT in a simple manner from the solid waste obtained during the expansion process of tobacco raw material.

[0066] [Example 6] Confirmation of the effect on non-combustible cigarettes A dried product containing CBT from which alkaloids had been removed was produced according to the method of Example 3. The CBT concentration of the dried product was about 99%. About 100 ppm by weight of the dried product was added to the tobacco base sheet shreds. The resulting scented sheet shreds were dried to obtain scented sheet shreds that could be evaluated for smoking. A non-combustion heating type flavor inhalation article was prepared using the scented sheet shreds. The article was heated from the outside and evaluated for smoking. The smoking evaluation was carried out by five well-trained panelists with an average age of 48 years. The evaluation method used tobacco aroma intensity as an index, with no aroma being scored as 1 point (no change), 2 points (strong), and 3 points (very strong). The test of the difference in the average scores was performed using a two-sided test. As a result, it was confirmed that the aroma characteristic of tobacco was imparted.

[0067] [Example 7] Confirmation of the effect on cigarettes The dried product obtained in Example 3 was added to tobacco shreds in an amount of about 100 ppm by weight. The flavored shreds were dried to obtain flavored shreds that could be evaluated for smoking. Cigarettes using the flavored shreds were prepared by a standard method, and the smoking evaluation was carried out in the same manner as in Example 6. As a result, it was confirmed that the flavored shreds better expressed the original tobacco aroma. [Explanation of symbols]

[0068] 10 Heating device 11. Body 12 Heater 13 Metal tube 14 Battery unit 15 Control Unit 16 Recess 17 Ventilation holes 20 Non-combustion heating type flavor inhalation products 20A Tobacco rod part 20B Cooling section 20C Filter section 21 Tobacco filling 22 Scroll Paper 23 Paper tube 24 perforation 25 First Segment 25a 1st packed bed 25b Inner plug wrapper 26 Second Segment 26a 2nd packed bed 26b Inner plug wrapper 27 Outer plug wrapper 28 Lining Paper 30 Non-burning, non-heating flavor inhalation products 30D Power Supply Unit 30E Cartridge 30F Tobacco Capsule u Non-suction end d Mouth end 110 Batteries 200 Aerosol Sources 210 Reservoir 220 Atomization section 230 Flow path formation body 240 Outer frame 240 250 end cap 200X 1st flow path 300 Flavor source 310 Containment Unit 320 Mesh body 330 Nonwoven fabric 340 Cap

Claims

1. Step 1: preparing a solid waste product obtained by expanding a tobacco raw material; A step 2 of subjecting the discharged solid matter to solid-liquid extraction using an aprotic solvent; and Step 3 recovering the organic phase from step 2; A method for producing a tobacco extract containing cembratrienediol, comprising:

2. The method according to claim 1 , wherein the discharged solid material is a discharged solid material obtained when performing an expansion process using supercritical carbon dioxide and separating carbon dioxide from the supercritical carbon dioxide containing tobacco components.

3. The method according to claim 1 or 2, wherein the step 2 further comprises subjecting the aprotic solvent phase obtained by the solid-liquid extraction to extraction with water or an aqueous acid solution.

4. The method according to any one of claims 1 to 3, wherein the aprotic solvent is non-water soluble.

5. The method according to claim 4, wherein the aprotic solvent is a hydrocarbon having 5 or 6 carbon atoms.

6. A step P1 of subjecting the organic phase obtained in the step 2 or the tobacco extract obtained by removing the aprotic solvent from the organic phase to normal phase chromatography using a mixed solvent of n-hexane / ethyl acetate as a mobile phase to obtain an n-hexane / ethyl acetate=50:50 fraction and an n-hexane / ethyl acetate=40:60 fraction; The method according to any one of claims 1 to 5, further comprising:

7. A process P2 of adding methanol or ethanol to the organic phase obtained in the process 2 or to the tobacco extract obtained by removing the aprotic solvent from the organic phase to generate a precipitate and then obtaining a solution from which the precipitate has been removed. The method according to any one of claims 1 to 5, further comprising:

8. Step P3, which subjects the fraction obtained in step P1 or P2 to reverse phase chromatography using water / methanol as a mobile phase; The method of claim 6 or claim 7 which relies on claim 6, further comprising:

9. The method according to claim 3, or any one of claims 4 to 8 which cite claim 3, wherein the aqueous acid solution is an aqueous solution of sulfuric acid, citric acid, or oxalic acid.

10. The method according to claim 3, or any one of claims 4 to 9 which cite claim 3, wherein the pH of the aqueous acid solution is 3 or less.

11. A tobacco extract containing cembratrienediol, produced by the method according to any one of claims 1 to 10.

12. 12. The tobacco extract according to claim 11, comprising 90% by weight or more of said cembratrienediol.

13. A tobacco flavoring agent comprising the tobacco extract according to claim 11 or 12.

14. A tobacco material comprising the tobacco flavoring agent according to claim 13.

15. The tobacco material according to claim 14, which is a tobacco sheet or tobacco shreds.

16. A tobacco rod portion comprising the tobacco material according to claim 14 or 15.

17. A tobacco flavor inhalation article comprising the tobacco rod portion of claim 16.

18. A non-combustion, non-heating type tobacco flavor inhalation article or a non-combustion, non-heating type tobacco flavor inhalation article, comprising the tobacco rod portion of claim 16.

19. A smokeless tobacco comprising the tobacco material according to claim 14 or 15.

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