Tobacco extract containing tobacco terpenes and method for producing the same

Abstract

This method for producing a tobacco extract containing tobacco terpenes comprises: step 1 for preparing a raw material derived from tobacco; step 2 for subjecting the raw material to solid-liquid extraction using an aprotic solvent; step 3 for collecting an organic phase from the aforementioned step; step 4 for adding a protic polar solvent or an aprotic neutral solvent to an extract, obtained by removing the solvent from the organic phase, to precipitate or disperse solid contents; and step 5 for removing the solid contents.

Description

[Technical Field]

[0001] The present invention relates to a tobacco extract containing tobacco terpenes and a method for producing the same, and more particularly to a tobacco extract containing sesquiterpenes or diterpenes and a method for producing the same. [Background technology]

[0002] The aroma components of tobacco leaves are primarily composed of pigment-derived decomposition products produced during the ripening or drying process, i.e., carotenoid decomposition products such as ionones and megastigmatotrienones, and leaf surface resin components such as sesquiterpenes and diterpenes. Most of these aroma components are hydrophobic. Various extraction methods have been investigated to utilize these aroma components. For example, many studies have explored the use of liquefied carbon dioxide or supercritical carbon dioxide to take advantage of the characteristics of the target components (Patent Documents 1 and 2). Meanwhile, raw materials expanded with liquefied carbon dioxide have been considered as a cigarette raw material, but this process is very similar to the extraction process using carbon dioxide described above. Therefore, methods that apply part of the expansion process to utilize these aroma components have been investigated (Patent Documents 3 and 4). For example, Patent Document 3 discloses an apparatus comprising: an extraction vessel that contacts tobacco raw materials with supercritical carbon dioxide and dissolves tobacco components in the carbon dioxide; a separation vessel connected to the extraction vessel that separates and recovers the fat-soluble portions of the tobacco components from the tobacco components dissolved in the carbon dioxide; a circulation path that circulates the supercritical carbon dioxide between the extraction vessel and an absorption vessel containing pure water while purifying it with an activated carbon purification layer, allowing the pure water to absorb the water-soluble portions of the tobacco components; and a recovery vessel that recovers the pure water that has absorbed the water-soluble portions of the tobacco components as absorbed water from the absorption vessel. The fat-soluble portions of the tobacco components and absorbed water obtained from the apparatus are used to produce flavor. Patent Document 4 also discloses a method for obtaining a heated aroma by impregnating tobacco raw materials with liquefied carbon dioxide, heating the resulting vaporized carbon dioxide, and then heating the tobacco components contained in the vaporized carbon dioxide to temperatures between 150°C and 400°C. This method is unique in that it produces reductones. However, it has been suggested that unwanted components derived from heating may also be produced, as shown in Patent Document 5 and other documents. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2007 / 029264 [Patent Document 2] British patent GB2173985 specification [Patent Document 3] International Publication No. 2007 / 119790 [Patent Document 4] International Publication No. 2016 / 051334A1 [Patent Document 5] Patent Publication No. 2016-526921 Summary of the Invention [Problem to be solved by the invention]

[0004] In conventional methods, it has not been easy to obtain flavor components from tobacco-derived raw materials in a simple and efficient manner. Therefore, an object of the present invention is to provide a method for producing components useful as flavoring agents from tobacco-derived raw materials in a simple and efficient manner. [Means for solving the problem]

[0005] The inventors have found that the above-mentioned problems can be solved by using waste materials containing tobacco leaf ribs and solid extracts that are discharged simultaneously with the separation of carbon dioxide gas during the tobacco expansion process as raw materials. That is, the above-mentioned problems are solved by the present invention described below. (1) Step 1: preparing a tobacco-derived raw material; Step 2: subjecting the raw material to solid-liquid extraction using an aprotic solvent; Step 3: recovering the organic phase from the previous step; Step 4: adding a protic polar solvent or an aprotic medium polar solvent to the extract obtained by removing the solvent from the organic phase to precipitate or disperse solids; and Step 5: removing the solids; A method for producing a tobacco extract containing tobacco terpenes, comprising: (2) The step 1 includes preparing a solid waste product obtained by an expansion process of a tobacco raw material; The step 2 includes subjecting the discharged solid to solid-liquid extraction using an aprotic solvent. (1) The manufacturing method described in (1). (3) The method according to (1) or (2), wherein the step 2 further comprises subjecting the organic phase obtained by the solid-liquid extraction to extraction with water or an aqueous acid solution. (4) The method according to any one of (1) to (3), wherein in step 4, the temperature of the extract to which the protic polar solvent or the aprotic medium polar solvent has been added is set to -10 to 10°C. (5) The manufacturing method according to any one of (1) to (4), wherein the tobacco extract contains a component having a retention index of 1600 to 2500 in gas chromatography. (6) The manufacturing method according to any one of (1) to (5), wherein the tobacco extract contains a component having a retention index of 1600 to 3500 in gas chromatography. (7) The method according to (5), wherein the solvent used in step 4 is a protic polar solvent. (8) The method according to (6), wherein the solvent used in step 4 is an aprotic medium-polarity solvent. (9) A tobacco extract obtained by the method described in (1) to (8) above. (10) A tobacco flavoring agent containing the tobacco extract described in (9) above. (11) The tobacco flavoring agent according to (10), further comprising ethanol, benzyl alcohol, or propylene glycol. (12) A tobacco material containing the tobacco flavoring agent according to (10) or (11). (13) The tobacco material according to (12), which is a tobacco sheet or tobacco shreds. (14) A tobacco rod portion comprising the tobacco material according to (12) or (13). (15) A tobacco flavor inhalation article comprising the tobacco rod portion of (14). (16) 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 (14). (17) A non-combustion heating tobacco flavor inhalation article according to (16), wherein the tobacco rod portion contains a tobacco extract produced by the method of (7) and is provided with a heating unit that heats the tobacco rod portion to 160 to 250°C. (18) A non-combustion heating tobacco flavor inhalation article according to (16), wherein the tobacco rod portion contains a tobacco extract produced by the method of (8) and is provided with a heating unit that heats the tobacco rod portion to 220 to 280°C. (19) Smokeless tobacco containing the tobacco material described in (12) or (13). [Brief explanation of the drawings]

[0006] [Figure 1] 1 to 6 show total ion chromatograms by GC / MS of the hexane solution obtained in Experimental Example 1. In Figures 1 to 6, the vertical lines indicate retention times where the RI is 1600 to 2500, and the arrows indicate the peak of CBT (cembratrienediol). [Figure 2] 1 is a total ion chromatogram by GC / MS of the chloroform solution obtained in Experimental Example 1. [Figure 3] 1 is a total ion chromatogram by GC / MS of the ethyl acetate solution obtained in Experimental Example 1. [Figure 4] 1 is a total ion chromatogram by GC / MS of the acetone solution obtained in Comparative Example 1. [Figure 5] 1 is a total ion chromatogram by GC / MS of the methanol solution obtained in Comparative Example 1. [Figure 6] 1 shows total ion chromatograms by GC / MS of the alcoholic preparation obtained in Example 4 (top row) and the alcoholic preparation immediately before swelling obtained by the same method as in Example 4 (bottom row). [Figure 7] 1 shows a total ion chromatogram by GC / MS of the alcohol preparation obtained in Example 5. The vertical lines indicate the retention times at which the RI is 800, 1600, 2500, and 3500. [Figure 8] 1 shows a total ion chromatogram by GC / MS of the benzyl alcohol preparation obtained in Example 10. The vertical lines indicate the retention times at which the RI is 800, 1600, 2500, and 3500. [Figure 9] 1A and 1B are diagrams showing an embodiment of a non-combustion heating type tobacco flavor inhalation article. [Figure 10] 1 is a diagram showing one embodiment of a non-combustion heating type tobacco flavor inhalation system. [Figure 11] 1A and 1B are diagrams showing an embodiment of a non-combustion, non-heating tobacco flavor inhalation article. [Figure 12] FIG. 1 shows an embodiment of a tobacco capsule. [Figure 13] FIG. 1 illustrates an example of a power supply unit. [Figure 14] FIG. 1 is a cross-sectional view of one embodiment of a cartridge. [Figure 15] FIG. 2 shows the internal structure of one embodiment of the cartridge. [Figure 16] FIG. 1 is a diagram illustrating an outline of the expansion treatment process. [Figure 17] 1 is a total ion chromatogram by GC / MS of the preparation (yellow seed raw material) obtained in Example 12. [Figure 18] 1 is a total ion chromatogram by GC / MS of the preparation (burley seed raw material) obtained in Example 12. DETAILED DESCRIPTION OF THE INVENTION

[0007] 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 comprises the following steps. Step 1: Prepare a tobacco-derived raw material. Step 2: The raw material is subjected to solid-liquid extraction using an aprotic solvent. Step 3: Recover the organic phase from the previous step. Step 4: A protic polar solvent or an aprotic medium polar solvent is added to the extract obtained by removing the solvent from the organic phase to precipitate or disperse solids. Step 5: Removing the solids.

[0008] (1) Process 1 In this process, a tobacco-derived raw material is prepared. The tobacco-derived raw material is a raw material derived from a Nicotiana plant, and examples thereof include tobacco raw materials such as tobacco leaves, aged tobacco leaves, tobacco shreds, or tobacco powder, as well as processed products or waste products obtained by subjecting tobacco raw materials to processing. Tobacco leaves are a general term for harvested tobacco leaves before they undergo aging. One form of aging includes curing. Tobacco shreds are aged tobacco leaves or the like that have been shredded to a predetermined size. Tobacco powder is obtained by pulverizing tobacco leaves or the like.

[0009] In the present invention, it is preferable to prepare a discharged solid obtained from a tobacco raw material expansion process. 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 Figure 16). In the present invention, a discharged solid obtained from a known expansion process can be used. As described above, the tobacco raw material is tobacco leaves, tobacco shreds, or tobacco powder. In the present invention, it is preferable to use, as the discharged solid, solid fat-soluble components obtained by performing an expansion process using supercritical carbon dioxide as described in Patent Document 3 and separating carbon dioxide from the supercritical carbon dioxide containing tobacco components. This is because the discharged solid from an expansion process using supercritical carbon dioxide contains a large amount of tobacco terpenes. Tobacco terpenes are preferably sesquiterpenes or diterpenes (hereinafter simply referred to as "terpenes"). Furthermore, the expansion process initially includes a process of threshing and chopping the raw tobacco leaves, which results in a small amount of tobacco powder and midribs being mixed into the tobacco raw material as shredded tobacco. When the raw material is subjected to a puffing process, the light puffed minced meat and the heavy backbone and unpuffed minced meat are discharged together with carbon dioxide gas after puffing to form excreted solids. Therefore, the excreted solids are the solid fat-soluble components described above, or solids of puffed minced meat, backbone, and unpuffed minced meat, or a mixture thereof. Below, an embodiment in which the excreted solids are used as a tobacco-derived raw material will be described as an example.

[0010] (2) Process 2 In this step, the discharged solids are subjected to solid-liquid extraction using an aprotic solvent. An aprotic solvent is a solvent that lacks a dissociable proton and is therefore poorly soluble in water, forming an organic phase separate from the aqueous phase. Examples of aprotic solvents include esters such as ethyl acetate, butyl butyrate, and ethyl butyrate; halogenated hydrocarbons such as dichloromethane and chloroform; ketones such as acetone; nitriles such as acetonitrile; and hydrocarbons such as hexane. Among these, aprotic medium-polar solvents containing heteroatoms, such as esters and halogenated hydrocarbons, are preferred from the viewpoint of efficient extraction of the target terpenes. Furthermore, solvents with a boiling point of 80°C or less are preferred from the viewpoint of ease of removal in subsequent steps. Therefore, the solvent is preferably ethyl acetate, butyl butyrate, ethyl butyrate, dichloromethane, or chloroform; more preferably ethyl acetate, butyl butyrate, or ethyl butyrate; and even more preferably ethyl acetate. In this step, the target terpenes are transferred to the aprotic solvent (organic phase).

[0011] Aprotic solvents can be classified into low-polarity solvents and medium-polarity solvents based on their polarity. In one aspect, aprotic medium-polarity solvents are defined as solvents that exhibit a positive log Kow of 2 or less using the octanol / water partition coefficient (Kow), and aprotic low-polarity solvents are defined as solvents that exhibit a log Kow of more than 2 but not more than 4. In the present invention, aprotic medium-polarity solvents are preferred. 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 aqueous phase

[0012] In one embodiment, the solvents used in the present invention are classified as exemplified below.

[0013] [Table 1]

[0014] In this step, the discharged solid may be subjected to extraction using an aprotic solvent and water or an acidic aqueous solution. This is because water can transfer nicotine in the discharged solid to the aqueous phase. Because acid can transfer nicotine in the discharged solid to the aqueous phase in the form of a salt, the water preferably contains an acid, i.e., is an acidic aqueous solution. The acid can be an inorganic or organic acid, but sulfuric acid, citric acid, or oxalic acid is preferred from the viewpoint of the stability of the nicotine salt. The pH of the acidic aqueous solution is preferably 4 or less, more preferably 3 or less. If the pH exceeds 4, nicotine extraction may be insufficient. The lower limit of the pH is not limited, but is preferably 2 or higher. The temperature at which this step is performed is not limited, but is preferably 10 to 35°C, more preferably 20 to 30°C. In this step, the discharged solid is preferably subjected to solid-liquid extraction using an aprotic solvent, and then the organic phase is preferably subjected to liquid-liquid extraction using water or an acidic aqueous solution. In the solid-liquid extraction, insoluble solids may be removed by filtration or the like.

[0015] (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 recovery method is not limited, and can be carried out using, for example, a separatory funnel. If necessary, the aqueous phase can be washed with an aprotic solvent, and the solvent after washing can be added to the organic phase. In this way, a tobacco extract solution containing terpenes can be obtained.

[0016] (4) Process 4 In this step, an extract is first obtained by removing the aprotic solvent from the organic phase. The solvent removal method is not limited, and an evaporator, for example, can be used. Next, a protic polar solvent or an aprotic mid-polar solvent is added to the extract to precipitate or disperse the solids. Protic solvents are organic solvents with dissociable protons, such as aliphatic alcohols (e.g., methanol, ethanol, and propanol), glycols (e.g., propylene glycol), and ketones (e.g., acetone). Examples of aprotic mid-polar solvents used in this step include aromatic alcohols (e.g., benzyl alcohol, phenylethyl alcohol, and cumyl alcohol), esters (e.g., ethyl acetate), ethers (e.g., diethyl ether), and chlorinated hydrocarbons (e.g., chloroform). In one embodiment, a protic polar solvent is defined as a solvent exhibiting a negative log Kow value. The aprotic mid-polar solvent used in step 4 may be the same as the aprotic solvent used in step 2, but it is preferable that they are different. The aprotic mid-polar solvent used in step 4 is preferably an aromatic alcohol.

[0017] The protic polar solvent (preferably an aliphatic alcohol) phase obtained in this step contains the target terpenes. These terpenes have a retention index (hereinafter simply referred to as "RI") in gas chromatography of 1600 to 2500, and therefore the protic polar solvent phase contains components with an RI of 1600 to 2500. However, the protic polar solvent phase preferably does not contain components with an RI of more than 2500 and not more than 3500. This is because components with an RI of more than 2500 and not more than 3500 are primarily higher hydrocarbons, which produce undesirable flavors and aromas when heated to 160 to 250°C. Therefore, the components contained in the protic polar solvent phase are suitable for tobacco flavor inhalation products heated to 160 to 250°C, and are even more suitable for tobacco flavor inhalation products heated to 160 to 220°C. RI is an index obtained by standardizing the retention time in gas chromatography using a standard substance. In the present invention, it refers to an index obtained by a linear method using the retention time of n-paraffin as a scale.

[0018] The aprotic medium-polar solvent (preferably aromatic alcohol) phase obtained in this step contains the target terpenes. These terpenes exist at an RI of 1600 to 2500, and therefore the aprotic medium-polar solvent phase contains components with an RI of 1600 to 2500. Furthermore, the aprotic medium-polar solvent phase preferably contains components with an RI of greater than 2500 and less than 3500, i.e., components with an RI of 1600 to 3500. Components with an RI of greater than 2500 and less than 3500 are nonpolar and function as retainers, dissolving aroma components more effectively. When heated to 220 to 280°C, these components are vaporized, resulting in a soft, smooth, and fragrant smoking experience. Therefore, tobacco extracts obtained using this solvent are suitable for tobacco flavor inhalation products heated to 220 to 280°C, and are even more suitable for tobacco flavor inhalation products heated to greater than 250°C and less than 280°C.

[0019] From the viewpoint of imparting an excellent flavor and taste and from the viewpoint of safety, the protic polar solvent is preferably ethanol, and the aprotic medium polar solvent is preferably benzyl alcohol.

[0020] In this step, the solvent is added to precipitate or disperse solids. This step specifically includes two modes: adding the solvent to the extract to form a solution, followed by precipitation of solids; and adding the solvent to the extract to quickly obtain a dispersion in which the solids are dispersed. In the latter mode, it is preferable to further promote precipitation of solids. The method for precipitation or promoting precipitation is not limited, and examples include leaving the system to stand or centrifuging. In this case, it is preferable to keep the system at a temperature of -10 to 10°C. This prevents degradation of the target terpenes. The amount of the solvent is not limited, but from the viewpoint of efficiently obtaining a precipitate, it is preferably an amount such that the extract concentration in the liquid is preferably 5 to 20% by weight, more preferably 8 to 15% by weight.

[0021] (5) Process 5 In this step, the solid matter is removed. The removal method is not limited, and the removal can be performed by filtration or decantation.

[0022] 2. Tobacco extract The tobacco extract obtained by the above production method (hereinafter also referred to as "tobacco extract of the present invention") contains the terpenes. Because the terpenes impart tobacco aroma and flavor, the tobacco extract of the present invention is useful as a tobacco flavoring agent. In one embodiment, the tobacco flavoring agent is a tobacco extract, and in another embodiment, it contains a tobacco extract and other components. As described above, the tobacco extract obtained using an aprotic medium-polar solvent in step 4 is suitable for tobacco flavor inhalation products heated to 220 to 280°C, while the tobacco extract obtained using a protic polar solvent is suitable for tobacco flavor inhalation products heated to 160 to 250°C. The tobacco extract obtained using an acid aqueous solution in step 2 contains no alkaloids such as nicotine, or contains only trace amounts of these alkaloids. The tobacco extract of the present invention can also be dissolved in ethanol, benzyl alcohol, or propylene glycol to form a tobacco flavoring agent (preparation). The concentration of the tobacco extract of the present invention in the preparation can be approximately 10 to 30% by weight. Tobacco flavor preparations are easy to handle because they can be sprayed or impregnated onto objects. The amount of the preparation added is preferably 50 to 200 weight ppm relative to the tobacco material in the case of combustible tobacco, 0.2 to 0.75 weight % relative to the tobacco material in the case of non-combustible tobacco, and 50 to 200 weight ppm relative to the base liquid in the case of liquid-heated tobacco.

[0023] 3. Tobacco materials A 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, and the like. A 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 and the like. The aged tobacco leaves used for the tobacco sheet are not particularly limited, but examples include those that have been deboned and separated into lamina and midrib. Aged tobacco leaves refer to tobacco leaves that have undergone processes such as curing and long-term storage in a warehouse or the like. In the present invention, a "sheet" refers to a material having a pair of approximately parallel main and side surfaces. Tobacco sheets can be molded by known methods such as papermaking, casting, and rolling. Details of various tobacco sheets molded by these 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 a tobacco sheet is not limited.

[0024] For example, a solution of the tobacco flavoring agent of the present invention may be prepared and sprayed or impregnated onto a finished tobacco sheet, or the tobacco flavoring agent of the present invention may be added when the tobacco sheet is molded. For example, in a paper-making method, water-soluble components are extracted from aged tobacco leaves and 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. The tobacco flavoring agent of the present invention can be added to the aqueous extract. In a casting method, water, pulp, a binder, and ground aged tobacco are mixed to form a mixture, which is then cast. The tobacco flavoring agent of the present invention can be added to this mixture. In a rolling method, water, pulp, a binder, and ground aged tobacco are mixed to form a mixture, which is then fed into multiple rolling rollers and rolled. The tobacco flavoring agent of the present invention can be added to this mixture.

[0025] 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 specific shape by heat welding. In this method, the tobacco flavoring agent of the present invention can be added to the mixture.

[0026] The tobacco sheet may contain an aerosol-generating substrate. The type of aerosol-generating substrate is not particularly limited, and extracts from various natural products or their components can be selected depending on the application. Specific examples of aerosol-generating substrates 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 thereof is typically 5% by weight or more, preferably 10% by weight or more, and more preferably 15% by weight or more, and typically 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 perspective of achieving a good flavor.

[0027] (2) Tobacco cuttings Examples of tobacco shreds include aged tobacco leaves shredded to a predetermined size, the aforementioned tobacco sheets shredded to a predetermined size, and mixtures thereof. The size is not limited, and examples include shreds of 0.5 to 2.0 mm in width and 3 to 10 mm in length. Tobacco shreds of this size are preferred in the embodiment of filling a filler, which will be described later. Other examples of tobacco shreds include strand-type shreds, which are processed tobacco leaves shredded to a width of 0.5 to 2.0 mm and a length longer than the aforementioned tobacco shreds, preferably approximately 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 shredding.

[0028] The tobacco shreds may contain the aerosol-forming base material. When the aerosol-forming base material is contained in the tobacco shreds, the content thereof is usually 5% by weight or more, preferably 10% by weight or more, and more preferably 15% by weight or more, relative to 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, and more preferably 25% by weight or less.

[0029] (3) Rolling paper Cigarette paper containing the tobacco flavoring agent of the present invention can be prepared by spraying or impregnating the cigarette paper. Cigarette paper containing the tobacco flavoring agent can be used, for example, as a cigarette paper containing pulp as its main component. Pulp may be made from wood pulp such as softwood pulp or hardwood pulp, or may be made by blending non-wood pulp commonly used in cigarette paper for tobacco articles, such as flax pulp, hemp pulp, sisal pulp, or esparto. These pulps may be used alone or in combination of multiple types in any ratio. The cigarette paper may be composed of one sheet or multiple sheets. The cigarette paper may be used to wrap tobacco raw materials such as tobacco shreds, and may also be used as a material (e.g., tipping paper) for wrapping the wrapped material together with other components such as a cooling element or a filter element. Pulp that can be used includes chemical pulp produced by kraft cooking, acidic, neutral or alkaline sulfite cooking, soda cooking, etc., ground pulp, chemi-ground pulp, thermomechanical pulp, etc.

[0030] (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.

[0031] The polysaccharide sheet containing the tobacco flavoring agent of the present invention can be used in both combustible and non-combustible tobacco flavor inhalation articles. In the former embodiment, a polysaccharide sheet such as that disclosed in Patent No. 5,481,574 can be used. In this embodiment, the content of the tobacco flavoring agent of the present invention is 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 weight of the sheet. The polysaccharide sheet can be prepared by mixing and heating a polysaccharide with water to prepare an aqueous solution of the polysaccharide, adding a flavoring and an emulsifier to the aqueous solution, and kneading and emulsifying the mixture. Known emulsifiers can be used.

[0032] In the latter embodiment, a polysaccharide sheet such as that 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 relative to the sheet is preferably 10 to 50% by weight, more preferably 15 to 45% by weight. Furthermore, the content of the tobacco flavoring agent of the present invention in the polysaccharide sheet can be 35 to 80% by weight relative to the sheet.

[0033] In this embodiment, it is preferable to use a sugar 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, relative to 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, relative to the weight of the agar.

[0034] The polysaccharide sheet in this embodiment can be produced by kneading raw materials including agar, a sugar compound, a flavoring, and an emulsifier in water to prepare a raw material slurry, spreading the raw material slurry on a substrate, and drying it.

[0035] 4. Tobacco-flavored inhalers In the present invention, a "flavor inhalation article" refers to an article through which a user inhales flavor. Among flavor inhalation articles, those containing tobacco or components derived from tobacco are referred to as "tobacco flavor inhalation articles." Tobacco flavor inhalation articles are broadly classified into "combustion-type tobacco flavor inhalation articles" (also simply referred to as "smoking articles") that generate flavor through combustion, and "non-combustion-type tobacco flavor inhalation articles" that generate flavor without combustion. Non-combustion-type tobacco flavor inhalation articles are further broadly classified into "non-combustion-heated tobacco flavor inhalation articles" that generate flavor through heating, and "non-combustion-non-heated tobacco flavor inhalation articles" that generate flavor without heating. The tobacco flavoring agent of the present invention is suitable for non-combustion-heated tobacco flavor inhalation articles or non-combustion-non-heated tobacco flavor inhalation articles. Furthermore, a combination of a device for generating aerosol (such as a heating device or an atomizing device) and a non-combustion-heated tobacco flavor inhalation article is also referred to as a non-combustion-heated tobacco flavor inhalation system.

[0036] (1) Non-combustion heated tobacco flavor inhalation products FIG. 9 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 its circumference, and a filter portion 20C. The non-combustion heating tobacco flavor inhalation article 20 may include other components. 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. 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, the tobacco rod portion 20A may be 20 mm long, the cooling portion 20B may be 20 mm long, and the filter portion 20C may be 7 mm long. The lengths of these individual components may be appropriately changed depending on manufacturing suitability, required quality, and the like. FIG. 9 shows an embodiment in which the first segment 25 is arranged, but it is also possible to arrange only the second segment 26 downstream of the cooling section 20B without the first segment 25 being arranged.

[0037] 1) Tobacco rod part 20A The tobacco rod portion 20A can use tobacco shreds or a tobacco sheet containing the tobacco flavoring agent of the present invention as the tobacco filler 21. The method for filling the tobacco filler 21 into the cigarette paper 22 is not particularly limited. For example, the tobacco filler 21 may be wrapped in the cigarette paper 22, or the tobacco filler 21 may be filled into a tubular 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 within the cigarette paper 22, or may be aligned in the axial direction of the tobacco rod portion 20A or in a direction perpendicular to the axial direction. Furthermore, the cigarette paper 22 can also be made of cigarette paper containing the tobacco flavoring agent of the present invention. When the tobacco rod portion 20A is heated, the tobacco components, aerosol-generating substrate, and water contained in the tobacco filler 21 vaporize and are available for inhalation.

[0038] 2) Cooling section 20B The cooling section 20B is preferably configured as a tubular member. The tubular 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 from a sheet of thin material that is wrinkled and then pleated, gathered, or folded to form channels. Examples of such materials include sheet materials selected from the group consisting of polyethylene, polypropylene, polyvinyl chloride, polyethylene terephthalate, polylactic acid, cellulose acetate, and aluminum foil. The total surface area of ​​the cooling section 20B is appropriately adjusted taking into account cooling efficiency, and may be, for example, 300 to 1000 mm2 / mm2. 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 puffing. This allows the tobacco rod section 20 The vaporized aerosol components generated by heating A come into contact with the outside air, and as their temperature drops, they are liquefied, forming an aerosol. The diameter (distance across) of perforations 24 is not particularly limited, but 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 cooling section 20B.

[0039] 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 section with a diameter of 5 to 10 mm. For example, the diameter of the cooling section may be approximately 7 mm.

[0040] 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 layer may be wrapped with one or more sheets of wrapping paper. The airflow resistance of the filter part 20C can be appropriately changed depending on the amount, material, etc. 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 using an airflow resistance measuring device (product name: SODIMAX, manufactured by SODIM).

[0041] The circumferential length of the filter portion 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 portion 20C (the horizontal direction in FIG. 9) can be selected from the range of 4 to 10 mm, and is selected so that the airflow resistance is 15 to 60 mmH2O / seg. The axial length of the filter portion 20C is preferably 5 to 9 mm, more preferably 6 to 8 mm. The cross-sectional shape of the filter portion 20C is not particularly limited, but may be, for example, circular, elliptical, polygonal, etc. In addition, a flavor-containing breakable capsule, flavor beads, or flavor may be directly added to the filter portion 20C.

[0042] The filter portion 20C may have a center hole portion as the first segment 25. The center hole portion is composed of a first packed layer 25a having one or more hollow portions and an inner plug wrapper (inner wrapping paper) 25b that covers the packed layer. The center hole portion functions to increase the strength of the mouthpiece portion. The center hole portion may not have an inner plug wrapper 25b and its shape may be maintained by thermoforming. The filter portion 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 may be, for example, a rod with an inner diameter of 5.0 to 1.0 mm, densely packed with cellulose acetate fibers and hardened with 6 to 20 wt. % of a plasticizer containing triacetin added to the cellulose acetate. Because the second packed layer has a high fiber packing density, air and aerosol flow only through the hollow portions during inhalation, with almost no flow within 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.

[0043] 1st packed layer 25 a The tobacco rod portion 20A, the cooling portion 20B, and the first packed layer 25a are connected by an outer plug wrapper (outer wrapping paper) 27. The outer plug wrapper 27 can be, for example, a cylindrical piece of paper. a and the second filling layer 26a are connected by mouthpiece lining paper 28. These connections can be made by, for example, applying glue such as vinyl acetate glue to the inside surface of mouthpiece lining paper 28 and wrapping the three components around it. These components may also be connected in multiple places using multiple lining papers.

[0044] 5) Non-combustion heating 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 such a system is shown in Fig. 10. 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.

[0045] The heating device 10 comprises 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 electrical resistance, and power is supplied from a battery unit 14 in response to instructions from a control unit 15 that controls temperature, causing the heater 12 to heat. The heat generated by the heater 12 is transferred to the tobacco rod portion 20A through a metal tube 13 with high thermal conductivity. While the figure shows an embodiment in which the heating device 10 heats the tobacco rod portion 20A from the outside, it may also heat 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 heater temperature of the heating device 10. In particular, when the tobacco rod portion contains a tobacco extract obtained using a protic polar solvent in step 4, the heating device 10 is preferably capable of heating the tobacco rod portion to 160 to 250°C. Furthermore, when the tobacco rod portion contains a tobacco extract obtained using an aprotic medium polar solvent in step 4, the heating device 10 can heat the tobacco rod portion to 160 to 250°C. In this case, it is preferable that the tobacco rod portion can be heated to 220 to 280°C.

[0046] (3) Non-combustible, non-heated tobacco-flavored inhalers 11 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-mouth 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.

[0047] 1) Tobacco capsules Fig. 12 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 the tobacco material of the present invention. The tobacco capsule 30F is connected to a cartridge 30E. Specifically, a portion of the tobacco capsule 30F is housed within the cartridge 30E.

[0048] The tobacco capsule 30F has a housing 310 that houses the flavor source 300, a mesh body 320, a nonwoven fabric 330, and a cap 340. Aerosol atomized by the atomization unit 220 (described later) is introduced into the housing 310 through the mesh body 320, and is imparted with flavor by coming into contact with the flavor source 300. The aerosol is then inhaled by the user through the nonwoven fabric 330. In this way, the non-combustion and non-heating 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.

[0049] In the direction of aerosol flow, the length of the tobacco capsule 30F (container 310) is preferably 40 mm or less, more preferably 25 mm or less. Furthermore, in the direction of aerosol flow, the length is preferably 1 mm or more, more preferably 5 mm or more. In a direction perpendicular to the direction of 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. Furthermore, in a direction perpendicular to the direction of aerosol flow, the maximum length of the tobacco capsule 30F (container 310) is preferably 1 mm or more, more preferably 3 mm or more.

[0050] The flavor source 300, which includes 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 make up the flavor source 300, the greater the specific surface area, thereby facilitating the release of flavor and flavor components. The raw material pieces that make up the flavor source 300 can be, for example, tobacco shreds, which are the tobacco material of the present invention, or molded bodies obtained by molding the tobacco material of the present invention into granules. The flavor source 300 may contain natural flavors such as plants other than tobacco (e.g., mint, herbs, etc.) and menthol, synthetic flavors, fruit juice, flavorings, and plant powders. Examples of flavorings include materials that impart sweetness, sourness, saltiness, umami, bitterness, astringency, richness, spiciness, harshness, and astringency. Examples of materials that impart sweetness include sugars, sugar alcohols, and sweeteners. Examples of sugars include monosaccharides, disaccharides, oligosaccharides, polysaccharides, etc. Examples of sweeteners include natural sweeteners, synthetic sweeteners, etc.

[0051] 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 using a stainless steel sieve with 0.71 mm openings for 20 minutes by dry mechanical shaking to obtain raw material pieces that pass through the stainless steel sieve with 0.71 mm openings. Next, the raw material pieces are sieved using a stainless steel sieve with 0.212 mm openings for 20 minutes by dry mechanical shaking to remove the raw material pieces that pass through the stainless steel sieve with 0.212 mm openings. In other words, the raw material pieces that make up the flavor source 300 are raw material pieces that pass through the stainless steel sieve (mesh opening = 0.71 mm) that defines the upper limit but do not pass through the stainless steel sieve (mesh opening = 0.212 mm) that defines 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 size 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 size of the stainless steel sieve that defines the upper limit.

[0052] 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 volatilized during smoking.

[0053] 2) The power supply unit An example of a power supply unit 30D is shown in FIG. 13. The power supply unit 30D has a battery 110. The battery 110 may be a disposable battery or a rechargeable battery. The initial 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.

[0054] 3) The cartridge An example of a cartridge 30E is shown in Figures 14 and 15. Figure 14 is a cross-sectional view of an example of the cartridge 30E, and Figure 15 is a diagram 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.

[0055] 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 aerosol flow direction (direction from the non-suction end to the suction end (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, for example, from a porous body such as a resin web or cotton. The reservoir 210 may also be formed from a tank that stores the liquid aerosol source 200. Examples of the aerosol source 200 include glycerin and propylene glycol.

[0056] The atomization unit 220 atomizes the aerosol source 200 using power supplied from the battery 110 without combustion. The atomization unit 220 is composed of a heating wire (coil) wound at a predetermined pitch. The atomization 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 equal to or greater than the value at which the heating wires do not touch each other, and is preferably smaller than that. 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.

[0057] The flow path forming body 230 has a cylindrical shape that forms a first flow path 200X extending along the aerosol flow direction. The outer frame body 240 has a cylindrical shape that houses the flow path forming body 230. The outer frame body 240 extends downstream of 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 into the tobacco capsule 30F. F This prevents leakage to the side.

[0058] 5. Smokeless tobacco Smokeless tobacco is a product that contains a flavor source, and the user tastes the flavor derived from the flavor source by inhaling the product directly 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 examples of smokeless tobacco. [Example]

[0059] [Experimental Example 1] Selection of solvent for extracting active ingredients from solids We prepared solid waste obtained from the expansion process of tobacco raw materials using supercritical carbon dioxide. Specifically, we performed the process shown in Figure 16, impregnating the tobacco raw materials with supercritical carbon dioxide, extracting the dry ice-like tobacco raw materials, and then rapidly air-drying them to remove the carbon dioxide. The solid waste obtained consisted of the high-temperature carbon dioxide gas (tail gas) emitted during this process, and a solid waste consisting of tar-like components separated from the carbon dioxide and solidified shredded powder (dust).

[0060] Approximately 5 g of the solids were weighed into a 100 ml screw tube, 50 ml of organic solvent was added, and the mixture was mixed thoroughly and left to stand overnight at room temperature. The organic solvents used were n-hexane, chloroform, and ethyl acetate. The mixture was filtered through filter paper, and a small amount of anhydrous sodium sulfate was added to the filtrate (extract) to dehydrate it. The mixture was then filtered again through filter paper, and the organic solvent was removed under reduced pressure. The resulting dry product (yield: n-hexane 3.4%, chloroform 7.8%, ethyl acetate 15.6%) was dissolved in the same solvent used for extraction, yielding a solution with a dry product concentration of 4 wt%. This solution was analyzed by GC / MS under the following conditions. Gas chromatography with mass spectrometry (GC / MS) Instrument: 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: 5 ml / min Carrier gas: Helium (He) Column flow rate: 1 ml / min (constant flow mode) Oven temperature: 40°C (3 min), increase to 280°C at 4°C / min, 280°C (20 min) Transfer line temperature: 280℃ MS conditions Solvent waiting time: 4 minutes Ionization method: Electron impact ionization (EI), 70 eV Ion source temperature: 230℃ Quadrupole temperature: 150℃ Measurement mode: Scan MS scan range: m / z 26-450 Threshold: 50 Sampling rate: 2

[0061] [Comparative Example 1] Except for using acetone and methanol as the solvent, extraction was carried out in the same manner as in Experimental Example 1. The yield was 24.7% when acetone was used and 28.9% when methanol was used.

[0062] Figures 1–5 show the total ion chromatograms obtained by GC / MS analysis of n-hexane, chloroform, ethyl acetate, acetone, and methanol solutions. The chromatograms in Figures 1–5 reveal that when solvent extraction was performed with n-hexane, chloroform, or ethyl acetate (Figures 1–3), the peak areas of components with retention indices (RI) of 1600–2500 (sesquiterpenes and diterpenes) were large. On the other hand, when solvent extraction was performed with acetone or methanol (Figures 4 and 5), the peak areas of the same components were small. Of the three solvents capable of efficiently extracting the desired components, ethyl acetate, which yielded the highest yield from the solid, was found to be the preferred extraction solvent. It was suggested that chloroform may leave trace amounts of halogens remaining in the extract.

[0063] [Experimental Example 2] Nicotine removal 150 g of the discharged solids were weighed and placed in a 2500 ml sealed stainless steel container. Next, 1500 ml of ethyl acetate (Fujifilm Wako Pure Chemical Industries, high-performance liquid chromatograph grade) was added, and extraction was performed for 3 hours in a sealed, stirring bath at 40 °C. After extraction, the ethyl acetate solution and the extraction residue were separated using a 250 μm mesh stainless steel mesh to obtain approximately 1400 ml of ethyl acetate solution. 300 ml of the resulting ethyl acetate solution and 500 ml of dilute sulfuric acid solution adjusted to approximately pH 5.0, pH 4.0, pH 3.0, and pH 2.0 were placed in a 1000 ml separatory funnel for liquid-liquid extraction, and the organic phase was recovered. The solvent was removed from the organic phase under reduced pressure using a rotary evaporator. Ethyl acetate was added to this concentrated solution to a dry matter concentration of 4 wt %, and GC / MS analysis was performed under the conditions described in Experimental Example 1 to quantify alkaloids such as nicotine. The table below shows the peak area ratio of each peak to all peaks displayed on the total ion chromatogram. The peaks of each alkaloid were separately confirmed by their characteristic single ions (for example, nicotine has an m / z of 84). As a result, it was confirmed that alkaloids, mainly nicotine, were removed by performing extraction in the acidic range of pH 4.0 or below.

[0064] [Table 2]

[0065] [Example 3] Removal of higher hydrocarbons 150 g of the discharged solids were weighed and placed in a 2500 ml sealed stainless steel container. Next, 1500 ml of ethyl acetate (Fujifilm Wako Pure Chemical Industries, high-performance liquid chromatograph grade) was added, and extraction was carried out for 3 hours in a sealed, stirring-filled hot bath at 40°C. After extraction, the ethyl acetate solution and extraction residue were separated using a 250 μm mesh stainless steel mesh to obtain approximately 1400 ml of ethyl acetate solution. For dehydration, 50 g of anhydrous sodium sulfate was added to the solution, stirred for 5 minutes, allowed to stand for a sufficient period of time, and then filtered using filter paper to remove the anhydrous sodium sulfate. The resulting ethyl acetate solution was divided into 300 ml portions in 500 ml eggplant flasks, and the solvent was removed under reduced pressure using a rotary evaporator.

[0066] Next, 99% ethanol was added to the dried material to achieve concentrations of 50%, 10%, 5%, and 1% V / V, respectively, and the mixture was dispersed and dissolved. Each solution was subjected to a 3-minute dispersion treatment in an ultrasonic cleaner (SHARP SILENTSONIC UT-304) to confirm that all solids on the bottom of the recovery flask had been dispersed. Next, 40 ml of each dispersion was placed in four approximately 50 ml polypropylene centrifuge tubes and stored overnight in a refrigerator. The solution was then centrifuged at 3,000 rpm for 10 minutes in a Kubota 3700. As shown in the table below, the results demonstrated that higher hydrocarbons could be efficiently removed by diluting the solution to a high concentration of 10 wt% or more and subjecting it to cold precipitation.

[0067] [Table 3]

[0068] Example 4 Preparation of Tobacco Flavor Formulation 150 g of the 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, high-performance liquid chromatograph grade) was added, and extraction was performed for 3 hours in a sealed, stirring bath at 40 °C. After extraction, the ethyl acetate solution and the extraction residue were separated using a 250 μm mesh stainless steel mesh to obtain approximately 1400 ml of ethyl acetate solution. A 0.1% aqueous sulfuric acid solution was prepared in advance, and this solution and the previously obtained ethyl acetate solution were mixed in a separatory funnel at a 5:3 ratio to obtain an 800 ml mixture. 50 g of salt was then added, and the mixture was thoroughly shaken in the separatory funnel to perform liquid-liquid extraction. During this process, alkaloids, primarily nicotine, migrated to the lower sulfuric acid aqueous solution, while the hydrophobic active ingredients of the tobacco leaf migrated to the upper ethyl acetate solution. After allowing to stand for a sufficient period, the ethyl acetate solution was removed, and approximately 50 g of anhydrous sodium sulfate was added and stirred for dehydration. The ethyl acetate solution was filtered using filter paper, and then the ethyl acetate was removed under reduced pressure using a rotary evaporator (manufactured by Nippon Buchi Co., Ltd.), yielding 7.7 g of a dry product (yield: 5.2%). Next, 99% ethanol was added to the dry product so that the content was 10%, and the mixture was stirred and dissolved at room temperature. The resulting solution was then sealed and left to stand overnight in a refrigerator at approximately 5°C, resulting in the formation of an insoluble precipitate (equivalent to approximately 0.3% by weight). The precipitate was removed by filtration using filter paper, yielding the desired tobacco flavoring agent (a clear, brown alcoholic preparation).

[0069] The pre-expanded syrup, which was used as the raw material for the discharged solids, was evaluated using the target component group with an RI of 1600 to 2500 as an index. Specifically, a tobacco flavoring agent (alcohol preparation) was prepared in the same manner as in Example 4, except that the pre-expanded syrup was used as the raw material. Small amounts of this product were then separated, and the ethanol was removed under reduced pressure. Ethanol was added to the resulting dried product to a concentration of 4 wt% to completely dissolve it, and the resulting solution was subjected to GC / MS analysis under the conditions described in Example 1. The results are shown in Figure 6. The lower panel shows a chromatogram of the extract from the pre-expanded syrup, while the upper panel shows a chromatogram of the extract from the discharged solids (prepared in Example 4). In both cases, the components with an RI of 1600 to 2500 were extracted. However, the upper panel showed a larger peak area containing cembratrienediol (CBT), excluding the unsaturated hydrocarbon neophytadiene. This demonstrated that effective aroma components are selectively concentrated in the discharged solids during the expansion process. Furthermore, from the viewpoint of yield (5.2% solid matter, 3.6% before expansion), extraction from the discharged solid matter can be said to be effective. The tobacco flavoring agent obtained in Example 4 had a tobacco-specific aroma.

[0070] [Example 5] Confirmation of selective extraction of effective aroma components A small amount of the tobacco flavoring agent (alcohol preparation) obtained in Example 4, which was extracted using ethyl acetate as an extraction solvent, was taken and the ethanol was removed under reduced pressure. Ethanol was added to the resulting dried product so that the concentration was 4% by weight, and the resulting solution was completely dissolved. GC / MS analysis was performed under the conditions described in Experimental Example 1. The peak area ratios were calculated based on the chromatogram in Figure 7, and the results were as follows: components with an RI of less than 1600 accounted for 8.2%, components with an RI of 1600 to 2500 accounted for 79.1%, and components with an RI of over 2500 accounted for 12.7%. This confirmed that the desired group of components with an RI of 1600 to 2500, i.e., the active aroma components sesquiterpenes and diterpenes, were selectively extracted.

[0071] [Example 6] Dissolution in propylene glycol An alcohol preparation containing approximately 10% by weight of tobacco extract (dried matter) was obtained using the same method as in Example 4. The solvent, ethanol, was then removed from the preparation using a rotary evaporator. Propylene glycol was then added to the preparation so that the dry matter concentration was 1% by weight, and the mixture was stirred and dissolved at room temperature. Insoluble matter was removed by filtration, yielding a clear brown liquid (propylene glycol preparation). The flavoring agent obtained in this example had a tobacco aroma equivalent to that of the flavoring agent prepared in Example 4.

[0072] [Example 7] Confirmation of effect on cigarettes The tobacco flavoring agent (alcohol preparation) obtained in Example 4 was added to tobacco shreds in amounts of 50 and 100 ppm. The resulting flavored shreds were dried to obtain flavored shreds suitable for smoking evaluation. Cigarettes were prepared using these flavored shreds, and smoking evaluation was performed. The smoking evaluation was performed by five well-trained panelists with an average age of 48 years. The evaluation method used tobacco aroma intensity as an indicator, with unflavored tobacco being scored as 1 point (no change), 2 points (strong), and 3 points (very strong). Differences in the mean scores were tested using a two-tailed test. The results confirmed that flavored shreds better expressed the original tobacco aroma.

[0073] [Table 4]

[0074] [Example 8] Confirmation of the effect on non-combustible tobacco The tobacco flavoring agent (alcohol preparation) obtained in Example 4 was added to the tobacco base sheet shreds at 2000 ppm. The obtained aromatized sheet shreds were dried to obtain aromatized sheet shreds suitable for smoking evaluation. These aromatized sheet shreds were used to prepare non-combustion heating type flavor inhalation articles. The articles were heated externally using a heating device preset to 230-240°C, and the same smoking evaluation as in Example 7 was carried out. As a result, it was confirmed that the aromatized sheet shreds better expressed the original tobacco aroma than the unaromatized sheet shreds.

[0075] [Example 9] Confirmation of the effect of heated liquid tobacco The tobacco flavoring agent (propylene glycol preparation) obtained in Example 6 was added at 100 ppm to a base liquid consisting of 50% glycerin and 50% propylene glycol. TM The tobacco flavoring agent was filled into a container. Smoking evaluation was carried out using the article in the same manner as in Example 7. As a result, it was confirmed that the original tobacco aroma was better expressed.

[0076] [Example 10] Preparation of tobacco-flavored benzyl alcohol preparation 150 g of the solid waste was weighed and placed in a 2500 ml sealed stainless steel container. Next, 1500 ml of ethyl acetate (Fujifilm Wako Pure Chemical Industries, high-performance liquid chromatograph grade) was added, and extraction was performed for 3 hours in a sealed, stirring bath at 40 °C. After extraction, the ethyl acetate solution and the extraction residue were separated using a 250 μm mesh stainless steel mesh to obtain approximately 1400 ml of ethyl acetate solution. A 0.1% aqueous sulfuric acid solution was prepared in advance, and this solution and the previously obtained ethyl acetate solution were mixed in a separatory funnel at a 5:3 ratio to obtain an 800 ml mixture. 50 g of salt was then added, and the mixture was thoroughly shaken in the separatory funnel to perform liquid-liquid extraction. During this process, alkaloids, primarily nicotine, migrated to the lower sulfuric acid aqueous solution phase, while the hydrophobic active ingredients of the tobacco leaf migrated to the upper ethyl acetate solution phase. After allowing to stand for a sufficient period, the ethyl acetate solution was removed, and approximately 50 g of anhydrous sodium sulfate was added and stirred for dehydration. The ethyl acetate solution was filtered using filter paper, and then the ethyl acetate was removed under reduced pressure using a rotary evaporator (manufactured by Nippon Buchi Co., Ltd.), yielding 7.7 g of a dry product (yield: 5.2%). Next, benzyl alcohol was added to the dry product so that the content was 20% by weight, and the mixture was stirred and dissolved at room temperature. The resulting solution was sealed and left to stand overnight in a refrigerator at approximately 5°C, resulting in the formation of an insoluble precipitate (equivalent to approximately 0.01% by weight). The precipitate was removed by filtration using filter paper, yielding the desired tobacco flavoring agent (a clear, brown benzyl alcohol preparation).

[0077] A small amount of the benzyl alcohol preparation was taken and completely dissolved with ethyl acetate to a dry matter concentration of 4% by weight. The solution was then analyzed by GC / MS under the conditions described in Experimental Example 1. Figure 8 shows the chromatogram. Compared to the ethanol preparation shown in Figure 7, the benzyl alcohol preparation expanded to include components with an RI of 1600 to 3500, and the content of saturated higher hydrocarbons was significantly higher. Calculation of the peak area ratio excluding benzyl alcohol revealed that, using the retention index (RI) as an index, components with an RI below 1600 accounted for 1.3%, components with an RI of 1600 to 2500 accounted for 87.5%, components with an RI greater than 2500 and up to 3500 accounted for 8.8%, and components with an RI greater than 3500 accounted for 2.4%. This confirmed that the desired component group with an RI of 1600 to 3500, i.e., the active aroma components sesquiterpenes and diterpenes, as well as saturated higher hydrocarbons important for flavor, were selectively extracted.

[0078] Using the tobacco flavoring agent obtained in this example, a non-combustion heating type flavor inhalation article was prepared in the same manner as in Example 8. The article was heated externally using a heating device set at a heating temperature of 270 to 280°C, and smoking evaluation was carried out by the same panel as in Example 7. The evaluation method used the intensity of tobacco aroma as an index, with no added aroma being given a score of 1 (no change), 2 points (strong), and 3 points (very strong). Differences in the mean scores were tested using a two-sided test. As a result, it was confirmed that the article had a soft and smooth flavor characteristic in addition to the aroma unique to tobacco.

[0079] [Table 5]

[0080] [Example 11] Removal of insoluble components 150 g of the discharged solids were weighed and placed in a 2500 ml sealed stainless steel container. Next, 1500 ml of ethyl acetate (Fujifilm Wako Pure Chemical Industries, high-performance liquid chromatograph grade) was added, and extraction was carried out for 3 hours with stirring in a sealed hot bath at 40 °C. After extraction, the ethyl acetate solution and extraction residue were separated using a 250 μm mesh stainless steel mesh to obtain approximately 1400 ml of ethyl acetate solution. Further dehydration treatment was carried out by adding 50 g of anhydrous sodium sulfate and stirring for 5 minutes, then allowing to stand for a sufficient time and filtering using filter paper to remove the anhydrous sodium sulfate. The resulting ethyl acetate solution was divided into 300 ml portions in 500 ml eggplant flasks, and the solvent was removed under reduced pressure using a rotary evaporator.

[0081] Next, benzyl alcohol was added to the dried material to achieve dry matter concentrations of 40% V / V, 20% V / V, 10% V / V, and 5% V / V, and the mixture was dispersed and dissolved. Each solution was dispersed in an ultrasonic cleaner (SHARP SILENTSONIC UT-304) for 3 minutes to confirm that all solids on the bottom of the recovery flask had been dispersed. 40 ml of each solution was placed in four approximately 50 ml polypropylene centrifuge tubes and stored overnight in a refrigerator. The solution was then centrifuged at 10,000 rpm for 1 hour using a Kubota 3700. As shown in the table below, the insoluble components could be efficiently removed by diluting the solution to a concentration of 10 to 40 wt% and then cold precipitating it.

[0082] [Table 6]

[0083] [Example 12] Confirmation of the effect on fine powder from raw material factory Flue-cured and burley-cured raw materials were prepared in the form of small lamina discarded from the processing of tobacco leaf raw materials and tobacco leaf powder collected in a dust collector. 150 g of each of the yellow seed and burley seed raw materials was weighed and placed in a 2500 ml sealed stainless steel container. Next, 1500 ml of ethyl acetate (Fujifilm Wako Pure Chemical Industries, high-performance liquid chromatograph grade) was added, and extraction was performed for 3 hours in a sealed, stirring bath at 40 °C. After extraction, the ethyl acetate solution and the extraction residue were separated using a 250 μm mesh stainless steel mesh to obtain approximately 1400 ml of ethyl acetate solution. 300 ml of the resulting ethyl acetate solution and 500 ml of dilute sulfuric acid solution adjusted to pH 2.0 were placed in a 1000 ml separatory funnel for liquid-liquid extraction, and the organic phase was recovered. The solvent was removed from the organic phase under reduced pressure using a rotary evaporator. Ethyl acetate was added to the concentrated solution to a dry matter concentration of 4 wt %, and GC / MS analysis was performed under the conditions described in Experimental Example 1. Figures 17 and 18 show the charts for the yellow seed and burley seed raw materials, respectively. The results obtained were very similar to those in Figure 8. Furthermore, each of the dried products obtained above was dissolved in benzyl alcohol to a content of 20% by weight, and the solid content was precipitated and removed in the same manner as in Example 11 to prepare a benzyl alcohol preparation. This preparation was compared with the preparation derived from the expansion process obtained in Example 10 by sensory evaluation. Samples for evaluation were prepared according to Example 10, and smoking evaluation was performed using the same panel as in Example 7 at a set heating temperature of 270 to 280°C.

[0084] [Table 7]

[0085] As shown in the table, it was revealed that the preparations derived from flue-cured and burley raw materials respectively had very similar flavor characteristics. [Explanation of symbols]

[0086] 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 product 20A Tobacco rod part 20B Cooling section 20C filter section 21 Tobacco filler 22 Rolling 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-combustion, 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 First 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 tobacco raw material; Step 2: subjecting the discharged solid matter to solid-liquid extraction using ethyl acetate; Step 3: recovering the organic phase obtained in step 2; Step 4: adding benzyl alcohol to the extract obtained by removing the solvent from the organic phase to precipitate or disperse a solid; and Step 5: removing the solids; A method for producing a tobacco extract containing tobacco terpenes, comprising:

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

3. The method according to claim 1 or 2, wherein in step 4, the temperature of the extract to which benzyl alcohol has been added is set to -10 to 10°C.

4. The method according to any one of claims 1 to 3, wherein the tobacco extract contains a component having a retention index of 1600 to 2500 in gas chromatography.

5. The method according to any one of claims 1 to 4, wherein the tobacco extract contains a component having a retention index of 1600 to 3500 in gas chromatography.

6. A tobacco extract obtained by the method of claims 1 to 5.

7. A tobacco flavoring agent comprising the tobacco extract of claim 6.

8. 8. The tobacco flavoring agent of claim 7, further comprising ethanol, benzyl alcohol, or propylene glycol.

9. A tobacco material comprising the tobacco flavoring agent according to claim 7 or 8.

10. The tobacco material according to claim 9, which is a tobacco sheet or tobacco shreds.

11. A tobacco rod portion comprising the tobacco material according to claim 9 or 10.

12. A tobacco flavor inhalation article comprising the tobacco rod portion of claim 11.

13. A non-combustion and non-heating tobacco flavor inhalation article or a non-combustion and non-heating tobacco flavor inhalation article, comprising the tobacco rod portion of claim 11.

14. A non-combustion heating tobacco flavor inhalation system comprising: a non-combustion heating tobacco flavor inhalation article, the tobacco rod portion of which contains the tobacco extract produced by the method of claim 5; and a heating device that heats the tobacco rod portion to 220 to 280°C.

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