WO2019026201A1 - Method for producing tobacco flavor liquid, and tobacco flavor liquid - Google Patents

Method for producing tobacco flavor liquid, and tobacco flavor liquid Download PDF

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Publication number
WO2019026201A1
WO2019026201A1 PCT/JP2017/028041 JP2017028041W WO2019026201A1 WO 2019026201 A1 WO2019026201 A1 WO 2019026201A1 JP 2017028041 W JP2017028041 W JP 2017028041W WO 2019026201 A1 WO2019026201 A1 WO 2019026201A1
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Prior art keywords
tobacco
heating step
flavor
heating
liquid
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PCT/JP2017/028041
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French (fr)
Japanese (ja)
Inventor
茜 荻野
研児 伊藤
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日本たばこ産業株式会社
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Application filed by 日本たばこ産業株式会社 filed Critical 日本たばこ産業株式会社
Priority to PCT/JP2017/028041 priority Critical patent/WO2019026201A1/en
Priority to EP17920081.1A priority patent/EP3643184A4/en
Publication of WO2019026201A1 publication Critical patent/WO2019026201A1/en

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    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/10—Chemical features of tobacco products or tobacco substitutes
    • A24B15/16—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B13/00—Tobacco for pipes, for cigars, e.g. cigar inserts, or for cigarettes; Chewing tobacco; Snuff
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/10—Chemical features of tobacco products or tobacco substitutes
    • A24B15/16—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes
    • A24B15/167—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes in liquid or vaporisable form, e.g. liquid compositions for electronic cigarettes
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • A24B15/241—Extraction of specific substances

Definitions

  • the present invention relates to a method for producing a tobacco flavor liquid, and a tobacco flavor liquid produced by the method.
  • Flavor components are extracted from tobacco materials such as leaf tobacco to prepare a tobacco extract, which is applied to cut tobacco and tobacco paper, or incorporated into a raw material slurry of recycled tobacco, thereby providing a flavor source of tobacco products. It is reported that it is used as a raw material of (WO2007 / 052159).
  • the tobacco extract may be used as a raw material for a tobacco flavor source to be contained in the liquid storage portion of the non-heating type flavor suction device, or may be added to the liquid of the heating type flavor suction device aerosol source It is used as a raw material for flavor sources (Japanese Patent Application Laid-Open No. 2013-13394).
  • tobacco extract is prepared by extracting fragrant ingredients such as vanillin, syringaldehyde and pyrazine from tobacco stems or tobacco roots and that this is used as a raw material of tobacco product flavor source (WO 2012/103435).
  • the tobacco extract exhibit storage stability during the storage period of the tobacco product so that it can provide the user with an excellent flavor when used as a raw material of a flavor source of the tobacco product.
  • the present inventors examined heating the tobacco material in an aqueous alkaline solution to increase pyrazines contained in the tobacco extract, thereby increasing the flavor component of the tobacco extract.
  • the present inventors heated the tobacco material in an aqueous alkaline solution, it was possible to increase the pyrazines contained in the tobacco extract, and then, if the tobacco extract was exposed to the heating and drying process as in the prior art, pyrazine Species have disappeared (see Example 3 in Table 2 below). Therefore, when the present inventors heated the tobacco material in an aqueous alkaline solution and used the obtained tobacco extract as a raw material of the flavor source of the tobacco product without heating and drying it, after the storage of the tobacco product, the flavor and taste were observed. Has encountered a problem (see sample 2-2 in Table 3 below).
  • an object of the present invention is to provide a tobacco flavor liquid containing a large amount of pyrazines as a flavor component and containing only a small amount of an unstable component which causes a change in flavor during storage.
  • the present inventors considered that the above-mentioned change in flavor and taste was caused by instability of the flavor components cycloten, maltol and vanillin contained in the tobacco extract under alkaline conditions.
  • the present inventors heated the tobacco material in an aqueous alkaline solution to increase pyrazines contained in the tobacco extract, and then heated again at a relatively low temperature to substantially reduce the increased pyrazines content. It has been found that the content of cyclotene, maltol and vanillin can be significantly reduced without The present inventors confirmed that the tobacco extract produced based on such findings does not involve a large change in aroma taste even after storage for a certain period, and came to complete the present invention.
  • a tobacco flavor liquid produced by the above method, wherein a total content of pyrazines contained in the tobacco flavor liquid is 0.4 mg or more relative to 1 g of the tobacco material.
  • a tobacco flavor containing pyrazines such that the total content of cyclotene, maltol and vanillin contained in the tobacco flavor liquid is 0.05 mg or less per 1 g of the tobacco material A liquid is provided.
  • a tobacco flavor liquid containing a large amount of pyrazines as a flavor component and containing only a small amount of an unstable component which causes a change in flavor during storage.
  • FIG. 1 is a flow chart showing a preferred embodiment of the method of the present invention.
  • FIG. 2 is a graph showing the relationship between the number of days of the second heating step and the total content of pyrazines.
  • FIG. 3 is a graph showing the relationship between the number of days of the second heating step and the total content of cyclotene, maltol and vanillin.
  • a method of producing a tobacco flavor liquid is A first heating step of heating a mixture comprising tobacco material and an aqueous alkaline solution and having a pH of 11 to 13 at a temperature of 80 to 240 ° C .; And a second heating step of heating the mixture at a temperature of 25 to 60 ° C. after the first heating step.
  • the process for producing a tobacco flavor liquid is A first heating step of heating a mixture comprising tobacco material and an aqueous alkaline solution and having a pH of 11 to 13 at a temperature of 80 to 240 ° C .; Separating the liquid portion from the mixture to obtain a tobacco extract after the first heating step; And C. heating the separated tobacco extract at a temperature of 25 to 60 ° C.
  • FIG. 1 A preferred embodiment is shown in FIG. 1
  • the first heating step when the mixture containing the tobacco material and the aqueous alkali solution is heated, a mixture containing the tobacco extract and the tobacco residue is obtained, and pyrazines are extracted in the tobacco extract.
  • the pH of the mixture drops during the first heating step.
  • the second heating step when the mixture containing the tobacco extract and the tobacco residue or the separated tobacco extract is heated, a mixture containing the tobacco flavor liquid and the tobacco residue is obtained, and pyrazines in the tobacco flavor liquid
  • the total content is hardly reduced compared to that in the tobacco extract, but the total content of cycloten, maltol and vanillin in the tobacco flavor liquid is significantly reduced as compared to that in the tobacco extract.
  • the liquid obtained after the first heating step is referred to as "cigarette extract”, and the liquid obtained after the second heating step is referred to as "cigarette flavor liquid”.
  • the tobacco material used in the method of the present invention can use tobacco cut ready to be formulated into tobacco products such as smoking articles and flavored aspirators.
  • Prepared tobacco cut into tobacco products refers to the drying process at the farm, the long-term ripening process for one to several years at the raw material plant, and the blending and cutting at the subsequent manufacturing plant. Etc. refers to cut tobacco ready to be blended into tobacco products.
  • the tobacco mincing may be of any variety, such as yellow, burley, or orient.
  • the tobacco mincing may use a single variety or a mixture of different varieties.
  • Cutting of tobacco consists of deboned leaves, middle bones, and regenerated tobacco composed of these raw materials (that is, leaves, scraps, inside bones, flour, etc. produced in the working process of the factory are processed into reusable forms) Cut pieces of tobacco material).
  • the tobacco engraving is preferably cut tobacco.
  • a mixture comprising tobacco material and an aqueous alkaline solution and having a pH of 11 to 13 is heated at a temperature of 80 to 240.degree.
  • the pH of the mixture can be determined by measuring the pH of the liquid portion of the mixture of tobacco material and aqueous alkaline solution.
  • the mixture preferably has a pH of 11.5 to 12.5.
  • a 0.1 to 0.5 mol / L aqueous potassium hydroxide solution or a 0.1 to 0.5 mol / L aqueous sodium hydroxide solution can be used.
  • the ratio of the mass (g) of the tobacco material to the volume (mL) of the aqueous alkali solution is preferably 1: 5 to 1:20, and more preferably 1: 7 to 1:15.
  • the first heating step can be performed at 80 to 240 ° C., preferably 120 to 200 ° C.
  • the first heating step can be performed, for example, for one or more hours and less than 10 hours.
  • the first heating step is preferably Heating step A, comprising heating a mixture containing tobacco material and an aqueous alkali solution and having a pH of 11 to 13 at a temperature of 80 ° C. or more and less than 160 ° C. until the pH of the mixture becomes 10 or less;
  • the heating step B comprises heating the mixture at a temperature of 160 ° C. or more and 240 ° C. or less for at least 30 minutes after the heating step A.
  • the heating step A can be performed at a temperature of 120 to 150 ° C.
  • the heating step B can be performed at a temperature of 160 to 200 ° C.
  • the heating step A can be performed for 30 minutes to 2 hours, and the heating step B can be performed for 30 minutes to 2 hours.
  • the first heating step can generally be performed for less than 10 hours, preferably for 1 hour or more and less than 10 hours, more preferably for 1 to 4 hours. That is, the total time of the heating step A and the heating step B can be generally less than 10 hours, preferably 1 hour or more and less than 10 hours, more preferably 1 to 4 hours. Even if the first heating step is carried out for 10 hours or more, many pyrazines substrates (sugars, amino acids, proteins, etc.) are used up, and pyrazines are less likely to increase further, and pyrazines which are rather increased are It may be reduced by heating.
  • heating step A the pH drops.
  • the heating step A is performed until the pH of the mixture is 10 or less, preferably 8 to 10.
  • the first heating step is preferably performed in a closed container.
  • the liquid amount of the mixture can be maintained after the heating step.
  • pyrazines refers to aromatic alkylpyrazines in which at least one of the four hydrogen atoms of pyrazine is substituted with an ethyl group or a methyl group, and more specifically, 2-methylpyrazine, 2 , 5-dimethylpyrazine, 2,6-dimethylpyrazine, 2-ethylpyrazine, 2,3-dimethylpyrazine, 2-ethyl-5-methylpyrazine, 2-ethyl-6-methylpyrazine, 2,3,5-trimethyl Pyrazine, tetramethylpyrazine, 2-ethyl-3,6-dimethylpyrazine, and 2-ethyl-3,5-dimethylpyrazine.
  • Pyrazines are components that contribute to tobacco taste (specifically, fragrant taste).
  • the mixture may be cooled to room temperature and then subjected to the subsequent steps.
  • the liquid portion is separated from the mixture containing the tobacco extract and the tobacco residue to obtain a tobacco extract.
  • This separation step is preferably performed but may not be performed.
  • the tobacco extract is subjected to the second heating step, and when the separation step is not performed, the mixture including the tobacco extract and the tobacco residue is subjected to the second heating step.
  • the mixture containing the tobacco extract and the tobacco residue, or the separated tobacco extract is heated at a temperature of 25 to 60.degree.
  • the second heating step is performed at a temperature of less than 25 ° C., it is difficult to sufficiently reduce unstable components that cause a change in flavor during storage.
  • pyrazines increased in the first heating step tend to be reduced.
  • the second heating step can be carried out preferably at a temperature of 30 to 50.degree.
  • the second heating step can be performed preferably for 24 hours or more, more preferably for 24 to 720 hours, further preferably for 24 to 72 hours.
  • the second heating step is preferably performed in a closed vessel.
  • the liquid amount of the mixture can be maintained after the heating step.
  • the total content of cyclothene, maltol and vanillin in the tobacco extract can be significantly reduced without substantially reducing the total content of pyrazines in the tobacco extract.
  • the pyrazines are contained so that the total content of pyrazines contained in the finally produced tobacco flavor liquid is 0.4 mg or more per 1 g of the tobacco material as the starting material, A cigarette containing cycloten, maltol and vanillin so that the total content of cycloten, maltol and vanillin contained in the finally produced tobacco flavor liquid is 0.05 mg or less per 1 g of the tobacco material as a starting material A flavor liquid can be obtained.
  • the pyrazines are contained so that the total content of pyrazines contained in the finally produced tobacco flavor liquid is 0.4 to 4 mg per 1 g of the tobacco material as the starting material, Does it contain cyclotene, maltol and vanillin so that the total content of cyclotene, maltol and vanillin contained in the finally produced tobacco flavor liquid is 0.05 mg or less per 1 g of the starting tobacco material? It is possible to obtain a tobacco flavor liquid free of, or cyclotene, maltol and vanillin.
  • the tobacco flavor liquid obtained by the method of the present invention contains a large amount of pyrazines and contains only a small amount or none of cyclotene, maltol and vanillin. Therefore, when used as a raw material of a flavor source of tobacco products, such a tobacco flavor liquid can provide rich flavor and taste to users by containing a large amount of pyrazines, and a small amount of cycloten, maltol and vanillin. By containing only or not containing at all, these components can be prevented from changing during storage of the tobacco product to cause a change in flavor and taste.
  • a source of flavor source for tobacco products eg flavor suckers
  • a tobacco flavor liquid when incorporated into a tobacco product such as smokeless tobacco (snus) or cigarette, it is added to the tobacco residue and exposed to a heat drying process at, for example, 80 to 120 ° C. before being incorporated into the tobacco product.
  • a heat drying process at, for example, 80 to 120 ° C.
  • the tobacco flavor liquid should not be exposed to such a heating and drying step.
  • the tobacco extract is subjected to a second heating step to become a tobacco flavor liquid, and then placed under temperature conditions exceeding 60 ° C. until it is used in the tobacco product as a raw material of the tobacco product flavor source and used by the user. If not, the tobacco flavor liquid can be stably contained even after storage without reducing pyrazines, and a tobacco product containing such tobacco flavor liquid as a raw material of a flavor source has an excellent flavor and taste for the user at the time of use Can be provided.
  • the tobacco extract or tobacco flavor liquid may be subjected to temperature conditions above 60 ° C.
  • the manufactured tobacco flavor liquid may be neutralized before being applied to the tobacco product .
  • the tobacco flavor liquid manufactured according to the method of this invention can be used as a raw material for manufacturing the flavor source applied, for example to a non-heating type flavor suction device or a heating type flavor suction device.
  • the “non-heated type flavor suction device” is a suction device which allows the user to taste the flavor of the tobacco flavor source by suction without heating the tobacco flavor source (eg, tobacco cut and tobacco flavor liquid), for example, a suction holder And a flavor suction device including a tobacco flavor source filled in the air flow passage of the suction holder (see, for example, WO 2010/095659).
  • tobacco flavor source eg, tobacco cut and tobacco flavor liquid
  • the "heated flavor suction device” is a suction device which heats the tobacco flavor source without burning it and tastes the flavor of the heated tobacco flavor source by suction, and for example, the tobacco flavor source is heated by combustion heat of a carbon heat source
  • a carbon heat source type aspirator see, for example, WO2006 / 073065
  • an electrically heated aspirator for example, see WO2010 / 110226) comprising an aspirator and a heating device for electrically heating the aspirator
  • a cigarette A liquid atomization type aspirator see, for example, WO 2015/046385 which atomizes a liquid aerosol source containing a flavor source by heating.
  • the tobacco flavor liquid produced according to the method of the present invention may be used as a raw material for producing a liquid flavor source which is independently incorporated into the liquid storage in the "non-heated flavor suction device", or other materials And may be used as a raw material to produce a flavor source that can be mixed with and placed in a pod.
  • the tobacco flavor liquid produced according to the method of the present invention may be used as a raw material for producing a liquid flavor source which is independently incorporated into the liquid storage unit in the "heating type flavor suction device", or the like It may be used as a raw material to produce a flavor source that is mixed with ingredients and placed in a pod, or used as a raw material to produce a flavor source that is used mixed with an aerosol source liquid (eg, glycerin) It may be done.
  • an aerosol source liquid eg, glycerin
  • the method for producing a tobacco flavor liquid A first heating step of heating a mixture comprising tobacco material and an aqueous alkaline solution and having a pH of 11 to 13 at a temperature of 80 to 240 ° C .; And a second heating step of heating the mixture at a temperature of 25 to 60 ° C. after the first heating step.
  • the method for producing a tobacco flavor liquid is: A first heating step of heating a mixture comprising tobacco material and an aqueous alkaline solution and having a pH of 11 to 13 at a temperature of 80 to 240 ° C .; Separating the liquid portion from the mixture to obtain a tobacco extract after the first heating step; And C. heating the separated tobacco extract at a temperature of 25 to 60 ° C.
  • the first heating step is Heating step A, comprising heating a mixture containing tobacco material and an aqueous alkaline solution and having a pH of 11 to 13 at a temperature of 80 ° C. or more and less than 160 ° C. until the pH of the mixture becomes 10 or less;
  • the heating step B comprises heating the mixture at a temperature of 160 ° C. or more and 240 ° C. or less for at least 30 minutes after the heating step A.
  • the heating step A is performed at a temperature of 120 to 150 ° C. in any one of the above embodiments.
  • the heating step B is performed at a temperature of 160 to 200 ° C. in any one of the above embodiments.
  • the heating step A is performed for 30 minutes to 2 hours in any one of the above embodiments.
  • the heating step B is performed for 30 minutes to 2 hours in any one of the above embodiments.
  • the first heating step is performed for less than 10 hours.
  • the first heating step is performed for 1 hour or more and less than 10 hours, preferably for 1 to 4 hours.
  • the tobacco material is tobacco cut, preferably cut tobacco.
  • the mixture has a pH of 11.5 to 12.5.
  • the aqueous alkali solution is a 0.1-0.5 mol / L aqueous potassium hydroxide solution, or a 0.1-0.5 mol / L aqueous hydroxide. It is an aqueous solution of sodium.
  • the ratio of the mass (g) of the tobacco material to the volume (mL) of the aqueous alkaline solution is 1: 5 to 1:20, preferably Is 1: 7 to 1:15.
  • the heating step A is performed until the pH of the mixture is 8-10.
  • the first heating step is performed in a closed container.
  • the second heating step is performed for 24 hours or more.
  • the second heating step is performed for 24 to 720 hours, preferably for 24 to 72 hours.
  • the second heating step is performed at a temperature of 30 to 50.degree.
  • the second heating step is performed in a closed container.
  • the tobacco extract obtained after the first heating step becomes a tobacco flavor liquid through the second heating step, and then the tobacco product It is not subjected to temperature conditions exceeding 60 ° C. until it is used in tobacco products as a raw material for flavor sources of and used by users.
  • the tobacco extract obtained after the first heating step becomes a tobacco flavor liquid through the second heating step, and then the tobacco product It is subjected to temperature conditions of minus 30 ° C. to plus 60 ° C. until it is used in tobacco products as a raw material of flavor sources of and used by users.
  • the tobacco flavor liquid which concerns on preferable embodiment is manufactured by the method as described in any one of the said embodiment, and the total content of the pyrazines contained in the said tobacco flavor liquid with respect to 1 g of said tobacco materials is 0. It contains pyrazines to be 4 mg or more, and the total content of cycloten, maltol and vanillin contained in the tobacco flavor liquid is 0.05 mg or less with respect to 1 g of the tobacco material Including.
  • the tobacco flavor liquid which concerns on a more preferable embodiment is manufactured by the method as described in any one of the said embodiment, and the total content of the pyrazines contained in the said tobacco flavor liquid with respect to 1 g of said tobacco materials is 0 .Containing pyrazines to 4 to 4 mg, and cyclotene, maltol and martol such that the total content of cyclotene, maltol and vanillin contained in the tobacco flavor liquid is 0.05 mg or less per 1 g of the tobacco material Contains vanillin or does not contain cyclotene, maltol and vanillin.
  • Example 1 Production of Tobacco Flavor Liquid ⁇ Example 1> As tobacco material, cut leaf tobacco (a mixture of American Burley leaves and domestic yellow leaves (weight ratio of 9: 1)) was used.
  • the tobacco material was heated by sequentially performing the following heating step A and heating step B (first heating step).
  • Heating step A In a stainless steel pressure container, 10 mL (pH 12) of a 0.25 mol / L aqueous potassium hydroxide solution was added to 1 g of the tobacco material to obtain a mixture. The pH of the mixture immediately after the addition of potassium hydroxide was 12. The resulting mixture was heated at 120 ° C. for 1 hour using a jacket heater. That is, the resulting mixture was heated at 120 ° C. until pH 10 or less.
  • Heating step B After heating step A, the mixture was heated at 180 ° C. for 1 hour.
  • the heating steps A and B were performed in a closed vessel (volume: 100 mL) in order to keep the liquid volume of the mixture.
  • the residue was removed from the mixture by suction filtration to obtain a tobacco extract.
  • the tobacco extract was placed in a lidded glass bottle and heated at 40 ° C. in a thermostat (second heating step).
  • the second heating step was performed for 1 day, 3 days, 7 days, 14 days, or 28 days.
  • the second heating step was also performed in a closed vessel (volume: 10 mL) in order to maintain the liquid volume of the tobacco extract.
  • a tobacco flavor liquid was obtained.
  • Example 2 (comparative example)>
  • the second heating step was performed by placing the tobacco extract in a glass bottle with a lid and heating at 80 ° C. in a thermostat, and the second heating step was performed for 1 day, 3 days, or 7 days
  • a tobacco flavor liquid was obtained in the same manner as in Example 1 except for the following.
  • Example 3 (comparative example)> The tobacco flavor liquid was obtained according to the same method as Example 1 except that the second heating step was performed by filtering the tobacco extract through filter paper and then heating and drying in a thermostat at 80 ° C. for 1 hour. .
  • the heating and drying was performed in an open container, not in a glass bottle with a lid (ie, a closed container), so the liquid amount of the tobacco flavor liquid obtained in Example 3 was smaller than the liquid amount of the tobacco extract.
  • Example 1 the content of the flavor component in the tobacco flavor liquid was measured 1 day, 3 days, 7 days, 14 days, and 28 days after the second heating step was started.
  • Example 2 the content of the flavor component in the tobacco flavor liquid was measured one day, three days, and seven days after the second heating step was started.
  • Example 3 after heat drying at 80 ° C. for 1 hour, the content of the flavor component in the tobacco flavor liquid was measured.
  • the measurement was performed as follows.
  • a 50 ⁇ L internal standard (4-bromophenethyl alcohol) and 80 mL water were added to 1.0 mL tobacco flavor liquid to prepare a measurement solution.
  • the measurement solution was adjusted to pH 2 or 9 using hydrochloric acid or sodium hydroxide aqueous solution. Thereafter, each of the pH 2 measurement solution and the pH 9 measurement solution was applied to a WATERS Corporation Oasis HLB cartridge. The cartridge was then washed with 20 mL of water and the support was eluted with diethyl ether. The supernatant of the eluate was subjected to GC / MS analysis. The column was heated to 60-240 ° C. using DB-FFAP manufactured by Agilent. MS detected in SIM mode.
  • Example 1 The results of Example 1 are shown in Table 1 and FIGS. 2 and 3 and the results of Examples 2 and 3 are shown in Table 2.
  • the content of the flavor component is represented by the content (mg) per 1 g of the tobacco material.
  • Example 1 28 days after the start of the second heating step (40 ° C. heating), the total content of pyrazines in the tobacco flavor liquid maintains about 88% by mass of the initial content, Although not reduced, the total content of cycloten, maltol and vanillin in the tobacco flavor liquid was reduced to about 3% by weight of the initial content (see Table 1 and Figures 2 and 3).
  • Example 2 seven days after the start of the second heating step (heating at 80 ° C.), the total content of pyrazines in the tobacco flavor liquid decreases to about 36% by mass of the initial content, The total content of cycloten, maltol and vanillin in the flavor liquid decreased to about 3% by weight of the initial content (see Table 2).
  • Example 3 when the tobacco extract is dried by heating at 80 ° C. for 1 hour, pyrazines in the tobacco flavor liquid disappear, and the total content of cyclotene, maltol and vanillin in the tobacco flavor liquid is the initial content It has decreased to about 41% by weight (see Table 2).
  • the tobacco material is heated in an alkaline aqueous solution to increase pyrazines contained in the tobacco extract, and then heated again at a relatively low temperature to increase the pyrazines It can be seen that the contents of cyclotene, maltol and vanillin can be significantly reduced without a substantial reduction of the content.
  • the tobacco flavor liquid was produced by performing the first heating step according to the method described in Example 1, and then performing the second heating step at 40 ° C. for 3 days. Immediately after production, 2 mL of the tobacco flavor liquid was placed in a lidded glass bottle (volume: 10 mL) to prepare sample 1-1 for sensory evaluation. The sample 1-1 was stored at room temperature (22 ° C.) for 24 hours to obtain a sample 1-2 for sensory evaluation.
  • a tobacco extract was prepared by performing the first heating step according to the method described in Example 1. Immediately after production, 2 mL of the tobacco extract was placed in a lidded glass bottle (volume: 10 mL) to prepare a sample for sensory evaluation 2-1. The sample 2-1 was stored at room temperature (22 ° C.) for 24 hours to obtain a sample 2-2 for sensory evaluation.
  • the first heating step is performed according to the method described in Example 3 to obtain a tobacco extract, and then the tobacco extract (2 mL) is filtered through filter paper and then dried by heating at 80 ° C. for 1 hour to obtain a tobacco flavor liquid Manufactured.
  • the tobacco flavor liquid ie, the tobacco flavor liquid obtained from 2 mL of the tobacco extract
  • sample 1-2 was evaluated as to whether or not there was a change in aroma compared to sample 1-1.
  • sample 2-2 it was evaluated whether or not there was a change in aroma compared to sample 2-1.
  • the tobacco flavor liquid of Sample 1-1 had excellent aroma.
  • Sample 1-1 was stored to prepare Sample 1-2, Sample 1-2 maintained the excellent aroma of Sample 1-1.
  • sample 2-1 had a fruity aroma, but compared with sample 1-1, it lacked the complexity of the aroma.
  • Sample 2-2 had a reduced fruity aroma and did not maintain the aroma of Sample 2-1.
  • the tobacco flavor liquid of sample 3-1 had a weak aroma.
  • a flavor liquid can be produced.
  • such a tobacco flavor liquid When used as a raw material of a flavor source of tobacco products, such a tobacco flavor liquid can provide rich flavor by containing a large amount of pyrazines, and contains only a small amount of cyclotene, maltol and vanillin Thus, these components can be prevented from being changed during storage of the tobacco product to cause a change in flavor and taste.

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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Manufacture Of Tobacco Products (AREA)

Abstract

A method for producing a tobacco flavor liquid, said method comprising: a first heating step for heating a mixture, which contains a tobacco material and an aqueous alkali solution and has a pH value of 11-13, at a temperature of 80-240oC; and a second heating step for, after the first heating step, heating the mixture at a temperature of 25-60oC.

Description

たばこ香味液の製造方法およびたばこ香味液Method for producing tobacco flavor liquid and tobacco flavor liquid
　本発明は、たばこ香味液の製造方法、および前記方法により製造されたたばこ香味液に関する。 The present invention relates to a method for producing a tobacco flavor liquid, and a tobacco flavor liquid produced by the method.
　葉たばこなどのたばこ材料から香喫味成分を抽出してたばこ抽出液を調製し、これを、たばこ刻やたばこ巻紙に塗布したり、再生たばこの原料スラリーに組み込んだりすることにより、たばこ製品の香味源の原材料として使用することが報告されている（ＷＯ２００７／０５２１５９号公報）。あるいは、たばこ抽出液は、非加熱タイプの香味吸引器の液体収容部に収容するためのたばこ香味源の原材料として使用されたり、加熱タイプの香味吸引器のエアロゾル源の液体に添加するためのたばこ香味源の原材料として使用されたりしている（日本国特開２０１３－１３３９４号公報）。 Flavor components are extracted from tobacco materials such as leaf tobacco to prepare a tobacco extract, which is applied to cut tobacco and tobacco paper, or incorporated into a raw material slurry of recycled tobacco, thereby providing a flavor source of tobacco products. It is reported that it is used as a raw material of (WO2007 / 052159). Alternatively, the tobacco extract may be used as a raw material for a tobacco flavor source to be contained in the liquid storage portion of the non-heating type flavor suction device, or may be added to the liquid of the heating type flavor suction device aerosol source It is used as a raw material for flavor sources (Japanese Patent Application Laid-Open No. 2013-13394).
　例えば、バニリン、シリンガアルデヒド、およびピラジンなどの香喫味成分をたばこの茎またはたばこの根から抽出してたばこ抽出液を調製し、これをたばこ製品の香味源の原材料として用いることが報告されている（ＷＯ２０１２／１０３４３５号公報）。 For example, it is reported that tobacco extract is prepared by extracting fragrant ingredients such as vanillin, syringaldehyde and pyrazine from tobacco stems or tobacco roots and that this is used as a raw material of tobacco product flavor source (WO 2012/103435).
　たばこ抽出液は、たばこ製品の香味源の原材料として用いられた際にユーザーに優れた香喫味を提供することができるように、たばこ製品の蔵置期間中に保存安定性を示すことが望まれる。 It is desirable that the tobacco extract exhibit storage stability during the storage period of the tobacco product so that it can provide the user with an excellent flavor when used as a raw material of a flavor source of the tobacco product.
　本発明者らは、たばこ材料をアルカリ水溶液中で加熱して、たばこ抽出液中に含まれるピラジン類を増加させて、これにより、たばこ抽出液の香喫味成分を増加させることを検討した。本発明者らが、たばこ材料をアルカリ水溶液中で加熱したところ、たばこ抽出液に含まれるピラジン類を増加させることができたが、その後、たばこ抽出液を従来どおり加熱乾燥工程に晒すと、ピラジン類が消失してしまった（後述の表２の例３を参照）。そこで、本発明者らは、たばこ材料をアルカリ水溶液中で加熱し、得られたたばこ抽出液を加熱乾燥させることなくたばこ製品の香味源の原材料として用いたところ、たばこ製品の蔵置後に、香喫味が変化するという問題に遭遇した（後述の表３のサンプル２－２を参照）。 The present inventors examined heating the tobacco material in an aqueous alkaline solution to increase pyrazines contained in the tobacco extract, thereby increasing the flavor component of the tobacco extract. When the present inventors heated the tobacco material in an aqueous alkaline solution, it was possible to increase the pyrazines contained in the tobacco extract, and then, if the tobacco extract was exposed to the heating and drying process as in the prior art, pyrazine Species have disappeared (see Example 3 in Table 2 below). Therefore, when the present inventors heated the tobacco material in an aqueous alkaline solution and used the obtained tobacco extract as a raw material of the flavor source of the tobacco product without heating and drying it, after the storage of the tobacco product, the flavor and taste were observed. Has encountered a problem (see sample 2-2 in Table 3 below).
　したがって、本発明は、香喫味成分としてピラジン類を多量に含み、かつ、蔵置期間中に香喫味の変化を引き起こす不安定な成分を少量しか含まないたばこ香味液を提供することを目的とする。 Therefore, an object of the present invention is to provide a tobacco flavor liquid containing a large amount of pyrazines as a flavor component and containing only a small amount of an unstable component which causes a change in flavor during storage.
　本発明者らは、上述の香喫味の変化は、たばこ抽出液中に含まれる香喫味成分であるシクロテン、マルトールおよびバニリンが、アルカリ性条件下で不安定であることに起因すると考えた。本発明者らは、たばこ材料をアルカリ水溶液中で加熱して、たばこ抽出液に含まれるピラジン類を増加させた後、比較的低い温度で再度加熱すると、増加したピラジン類の含有量をほとんど減少させることなく、シクロテン、マルトールおよびバニリンの含有量を顕著に減少させることができることを見出した。本発明者らは、このような知見に基づいて製造されたたばこ抽出液が、一定期間の蔵置後も香喫味の大きな変化を伴わないことを確認し、本発明を完成させるに至った。 The present inventors considered that the above-mentioned change in flavor and taste was caused by instability of the flavor components cycloten, maltol and vanillin contained in the tobacco extract under alkaline conditions. The present inventors heated the tobacco material in an aqueous alkaline solution to increase pyrazines contained in the tobacco extract, and then heated again at a relatively low temperature to substantially reduce the increased pyrazines content. It has been found that the content of cyclotene, maltol and vanillin can be significantly reduced without The present inventors confirmed that the tobacco extract produced based on such findings does not involve a large change in aroma taste even after storage for a certain period, and came to complete the present invention.
　すなわち、本発明の一つの側面によれば、
　たばこ材料とアルカリ水溶液とを含み、１１～１３のｐＨを有する混合物を、８０～２４０℃の温度で加熱する第１の加熱工程と、
　前記第１の加熱工程の後に、前記混合物を２５～６０℃の温度で加熱する第２の加熱工程と
を含む、たばこ香味液の製造方法が提供される。 That is, according to one aspect of the present invention,
A first heating step of heating a mixture comprising tobacco material and an aqueous alkaline solution and having a pH of 11 to 13 at a temperature of 80 to 240 ° C .;
And a second heating step of heating the mixture at a temperature of 25 to 60 ° C. after the first heating step.
　本発明の別の側面によれば、前記方法により製造されるたばこ香味液であって、前記たばこ材料１ｇに対して前記たばこ香味液中に含まれるピラジン類の合計含有量が０．４ｍｇ以上となるようにピラジン類を含み、前記たばこ材料１ｇに対して前記たばこ香味液中に含まれるシクロテン、マルトールおよびバニリンの合計含有量が０．０５ｍｇ以下となるようにシクロテン、マルトールおよびバニリンを含むたばこ香味液が提供される。 According to another aspect of the present invention, there is provided a tobacco flavor liquid produced by the above method, wherein a total content of pyrazines contained in the tobacco flavor liquid is 0.4 mg or more relative to 1 g of the tobacco material. A tobacco flavor containing pyrazines such that the total content of cyclotene, maltol and vanillin contained in the tobacco flavor liquid is 0.05 mg or less per 1 g of the tobacco material A liquid is provided.
　本発明によれば、香喫味成分としてピラジン類を多量に含み、かつ、蔵置期間中に香喫味の変化を引き起こす不安定な成分を少量しか含まないたばこ香味液を提供することができる。 According to the present invention, it is possible to provide a tobacco flavor liquid containing a large amount of pyrazines as a flavor component and containing only a small amount of an unstable component which causes a change in flavor during storage.
図１は、本発明の方法の好ましい実施形態を示すフローチャートである。FIG. 1 is a flow chart showing a preferred embodiment of the method of the present invention. 図２は、第２の加熱工程の日数とピラジン類の合計含有量との関係を示すグラフである。FIG. 2 is a graph showing the relationship between the number of days of the second heating step and the total content of pyrazines. 図３は、第２の加熱工程の日数とシクロテン、マルトールおよびバニリンの合計含有量との関係を示すグラフである。FIG. 3 is a graph showing the relationship between the number of days of the second heating step and the total content of cyclotene, maltol and vanillin.
　以下、本発明を詳細に説明するが、以下の説明は、本発明を説明することを目的とし、本発明を限定することを意図しない。 The present invention will be described in detail below, but the following description is for the purpose of describing the present invention and is not intended to limit the present invention.
　＜１．たばこ香味液の製造方法＞
　一実施形態によれば、たばこ香味液の製造方法は、
　たばこ材料とアルカリ水溶液とを含み、１１～１３のｐＨを有する混合物を、８０～２４０℃の温度で加熱する第１の加熱工程と、
　前記第１の加熱工程の後に、前記混合物を２５～６０℃の温度で加熱する第２の加熱工程と
を含む。 <1. Method for producing a tobacco flavor liquid>
According to one embodiment, a method of producing a tobacco flavor liquid is
A first heating step of heating a mixture comprising tobacco material and an aqueous alkaline solution and having a pH of 11 to 13 at a temperature of 80 to 240 ° C .;
And a second heating step of heating the mixture at a temperature of 25 to 60 ° C. after the first heating step.
　好ましい実施形態によれば、たばこ香味液の製造方法は、
　たばこ材料とアルカリ水溶液とを含み、１１～１３のｐＨを有する混合物を、８０～２４０℃の温度で加熱する第１の加熱工程と、
　前記第１の加熱工程の後に、前記混合物から液体部分を分離してたばこ抽出液を得る工程と、
　分離された前記たばこ抽出液を２５～６０℃の温度で加熱する第２の加熱工程と
を含む。 According to a preferred embodiment, the process for producing a tobacco flavor liquid is
A first heating step of heating a mixture comprising tobacco material and an aqueous alkaline solution and having a pH of 11 to 13 at a temperature of 80 to 240 ° C .;
Separating the liquid portion from the mixture to obtain a tobacco extract after the first heating step;
And C. heating the separated tobacco extract at a temperature of 25 to 60 ° C.
　好ましい実施形態を図１に示す。 A preferred embodiment is shown in FIG.
　第１の加熱工程で、たばこ材料とアルカリ水溶液とを含む混合物を加熱すると、たばこ抽出液とたばこ残渣とを含む混合物が得られ、たばこ抽出液中にピラジン類が抽出される。第１の加熱工程の間に混合物のｐＨは低下する。 In the first heating step, when the mixture containing the tobacco material and the aqueous alkali solution is heated, a mixture containing the tobacco extract and the tobacco residue is obtained, and pyrazines are extracted in the tobacco extract. The pH of the mixture drops during the first heating step.
　第２の加熱工程で、たばこ抽出液とたばこ残渣とを含む混合物または分離されたたばこ抽出液を加熱すると、たばこ香味液とたばこ残渣とを含む混合物が得られ、たばこ香味液中のピラジン類の合計含有量は、たばこ抽出液中のものと比べてほとんど低下しないが、たばこ香味液中のシクロテン、マルトールおよびバニリンの合計含有量は、たばこ抽出液中のものと比べて著しく低下する。 In the second heating step, when the mixture containing the tobacco extract and the tobacco residue or the separated tobacco extract is heated, a mixture containing the tobacco flavor liquid and the tobacco residue is obtained, and pyrazines in the tobacco flavor liquid The total content is hardly reduced compared to that in the tobacco extract, but the total content of cycloten, maltol and vanillin in the tobacco flavor liquid is significantly reduced as compared to that in the tobacco extract.
　これにより、香喫味成分としてピラジン類を多量に含み、かつ、蔵置期間中に香喫味の変化を引き起こす不安定な成分を少量しか含まないたばこ香味液を得ることができる。 As a result, it is possible to obtain a tobacco flavor liquid containing a large amount of pyrazines as a flavor component and containing only a small amount of an unstable component that causes a change in flavor during storage.
　本明細書において、第１の加熱工程後に得られる液体を「たばこ抽出液」と呼び、第２の加熱工程後に得られる液体を「たばこ香味液」と呼ぶ。 In the present specification, the liquid obtained after the first heating step is referred to as "cigarette extract", and the liquid obtained after the second heating step is referred to as "cigarette flavor liquid".
　以下、「第１の加熱工程」、「分離工程」、「第２の加熱工程」の順に説明する。 Hereinafter, the “first heating process”, the “separation process”, and the “second heating process” will be described in this order.
　［第１の加熱工程］
　本発明の方法で使用されるたばこ材料は、喫煙物品や香味吸引器などのたばこ製品に配合される準備が整ったたばこ刻を使用することができる。「たばこ製品に配合される準備が整ったたばこ刻」とは、農家での乾燥工程、その後の原料工場での１年ないし数年の長期熟成工程、およびその後の製造工場でのブレンドおよび裁刻など種々の加工処理を経て、たばこ製品に配合される準備が整ったたばこ刻を指す。 [First heating step]
The tobacco material used in the method of the present invention can use tobacco cut ready to be formulated into tobacco products such as smoking articles and flavored aspirators. “Prepared tobacco cut into tobacco products” refers to the drying process at the farm, the long-term ripening process for one to several years at the raw material plant, and the blending and cutting at the subsequent manufacturing plant. Etc. refers to cut tobacco ready to be blended into tobacco products.
　たばこ刻は、任意の品種のものを使用することができ、たとえば黄色種、バーレー種、オリエント種などのものを使用することができる。たばこ刻は、単一品種のものを使用してもよいし、異なる品種の混合物を使用してもよい。 The tobacco mincing may be of any variety, such as yellow, burley, or orient. The tobacco mincing may use a single variety or a mixture of different varieties.
　たばこ刻は、除骨葉、中骨、及びこれら原料から構成される再生たばこ（すなわち、工場の作業工程で生じる葉屑、刻み屑、中骨屑、細粉などを再使用可能な形状に加工したたばこ材料）の切断片を含むことができる。たばこ刻は、好ましくは、裁刻された葉たばこである。 Cutting of tobacco consists of deboned leaves, middle bones, and regenerated tobacco composed of these raw materials (that is, leaves, scraps, inside bones, flour, etc. produced in the working process of the factory are processed into reusable forms) Cut pieces of tobacco material). The tobacco engraving is preferably cut tobacco.
　第１の加熱工程において、たばこ材料とアルカリ水溶液とを含み、１１～１３のｐＨを有する混合物が、８０～２４０℃の温度で加熱される。混合物のｐＨ は、たばこ材料とアルカリ水溶液との混合物の液体部分のｐＨを測定することにより求めることができる。 In a first heating step, a mixture comprising tobacco material and an aqueous alkaline solution and having a pH of 11 to 13 is heated at a temperature of 80 to 240.degree. The pH of the mixture can be determined by measuring the pH of the liquid portion of the mixture of tobacco material and aqueous alkaline solution.
　混合物は、好ましくは１１．５～１２．５のｐＨを有する。アルカリ水溶液は、例えば、０．１～０．５ｍｏｌ／Ｌの水酸化カリウム水溶液、または０．１～０．５ｍｏｌ／Ｌの水酸化ナトリウム水溶液を使用することができる。 The mixture preferably has a pH of 11.5 to 12.5. As the alkaline aqueous solution, for example, a 0.1 to 0.5 mol / L aqueous potassium hydroxide solution or a 0.1 to 0.5 mol / L aqueous sodium hydroxide solution can be used.
　たばこ材料の質量（ｇ）とアルカリ水溶液の体積（ｍＬ）との比は、１：５～１：２０であることが好ましく、１：７～１：１５であることがより好ましい。 The ratio of the mass (g) of the tobacco material to the volume (mL) of the aqueous alkali solution is preferably 1: 5 to 1:20, and more preferably 1: 7 to 1:15.
　第１の加熱工程は、８０～２４０℃、好ましくは１２０～２００℃で行うことができる。第１の加熱工程は、例えば、１時間以上、１０時間未満にわたって行うことができる。 The first heating step can be performed at 80 to 240 ° C., preferably 120 to 200 ° C. The first heating step can be performed, for example, for one or more hours and less than 10 hours.
　第１の加熱工程は、好ましくは、
　たばこ材料とアルカリ水溶液とを含み、１１～１３のｐＨを有する混合物を、８０℃以上１６０℃未満の温度で 、前記混合物のｐＨが１０以下になるまで加熱する加熱工程Ａと、
　加熱工程Ａの後に、混合物を、１６０℃以上２４０℃以下の温度で少なくとも３０分間加熱する加熱工程Ｂと
から構成される。 The first heating step is preferably
Heating step A, comprising heating a mixture containing tobacco material and an aqueous alkali solution and having a pH of 11 to 13 at a temperature of 80 ° C. or more and less than 160 ° C. until the pH of the mixture becomes 10 or less;
The heating step B comprises heating the mixture at a temperature of 160 ° C. or more and 240 ° C. or less for at least 30 minutes after the heating step A.
　このように第１の加熱工程を加熱工程Ａおよび加熱工程Ｂの２段階で行うことにより、ピラジン類を効率的に合成することができる。 By thus performing the first heating step in two steps of the heating step A and the heating step B, pyrazines can be efficiently synthesized.
　好ましくは、加熱工程Ａは１２０～１５０℃の温度で行うことができ、加熱工程Ｂは１６０～２００℃の温度で行うことができる。 Preferably, the heating step A can be performed at a temperature of 120 to 150 ° C., and the heating step B can be performed at a temperature of 160 to 200 ° C.
　例えば、加熱工程Ａは３０分～２時間にわたって行うことができ、加熱工程Ｂは３０分～２時間にわたって行うことができる。 For example, the heating step A can be performed for 30 minutes to 2 hours, and the heating step B can be performed for 30 minutes to 2 hours.
　第１の加熱工程は、一般的には１０時間未満にわたって行うことができ、好ましくは１時間以上、１０時間未満、より好ましくは１～４時間 にわたって行うことができる。すなわち、加熱工程Ａおよび加熱工程Ｂの合計時間は、一般的には１０時間未満、好ましくは１時間以上、１０時間未満、より好ましくは１～４時間とすることができる。第１の加熱工程を１０時間以上行っても、ピラジン類の基質（糖、アミノ酸、タンパク質など）の多くが使い果たされており、ピラジン類が更に増加しにくく、むしろ増大したピラジン類が、加熱により減少する可能性がある。 The first heating step can generally be performed for less than 10 hours, preferably for 1 hour or more and less than 10 hours, more preferably for 1 to 4 hours. That is, the total time of the heating step A and the heating step B can be generally less than 10 hours, preferably 1 hour or more and less than 10 hours, more preferably 1 to 4 hours. Even if the first heating step is carried out for 10 hours or more, many pyrazines substrates (sugars, amino acids, proteins, etc.) are used up, and pyrazines are less likely to increase further, and pyrazines which are rather increased are It may be reduced by heating.
　加熱工程Ａの間にｐＨは低下する。加熱工程Ａは、混合物のｐＨが１０以下、好ましくは８～１０になるまで行う。加熱工程Ａの間に起こるｐＨの低下は、混合物のｐＨが１０以下になると頭打ちになることを本発明者らは実験により実証している。このような頭打ちの状態は、ピラジン類の基質のほとんどが使い尽くされたために起こると考えられる。したがって、加熱工程Ａは、混合物のｐＨが１０以下になるまで、すなわちピラジン類の基質のほとんどが使い尽くされるまで行うことが好ましい。その後、反応温度を上昇させて加熱工程Ｂを行うことにより、ピラジン類の合成反応を促進することができる。 During the heating step A, the pH drops. The heating step A is performed until the pH of the mixture is 10 or less, preferably 8 to 10. We have experimentally demonstrated that the drop in pH that occurs during heating step A plateaus when the pH of the mixture goes below 10. Such a peak condition is believed to occur because most of the pyrazines substrate is exhausted. Therefore, heating step A is preferably performed until the pH of the mixture is 10 or less, that is, until most of the pyrazines substrate is used up. Thereafter, by raising the reaction temperature and performing the heating step B, the synthesis reaction of pyrazines can be promoted.
　第１の加熱工程は、密閉容器内で行うことが望ましい。第１の加熱工程を密閉容器内で行った場合、加熱工程後に混合物の液体量を維持することができる。 The first heating step is preferably performed in a closed container. When the first heating step is performed in a closed vessel, the liquid amount of the mixture can be maintained after the heating step.
　第１の加熱工程後に、たばこ抽出液とたばこ残渣とを含む混合物が得られ、たばこ抽出液中のピラジン類の含有量が増加する。本明細書において、「ピラジン類」は、ピラジンの４つの水素原子の少なくとも一つがエチル基またはメチル基で置換された、芳香を有するアルキルピラジンを指し、具体的には、２－メチルピラジン、２，５－ジメチルピラジン、２，６－ジメチルピラジン、２－エチルピラジン、２，３－ジメチルピラジン、２－エチル－５－メチルピラジン、２－エチル－６－メチルピラジン、２，３，５－トリメチルピラジン、テトラメチルピラジン、２－エチル－３，６－ジメチルピラジン、および２－エチル－３，５－ジメチルピラジンを指す。ピラジン類は、たばこ香喫味（具体的には香ばしい香喫味）に寄与する成分である。 After the first heating step, a mixture comprising a tobacco extract and a tobacco residue is obtained, and the content of pyrazines in the tobacco extract is increased. As used herein, “pyrazines” refers to aromatic alkylpyrazines in which at least one of the four hydrogen atoms of pyrazine is substituted with an ethyl group or a methyl group, and more specifically, 2-methylpyrazine, 2 , 5-dimethylpyrazine, 2,6-dimethylpyrazine, 2-ethylpyrazine, 2,3-dimethylpyrazine, 2-ethyl-5-methylpyrazine, 2-ethyl-6-methylpyrazine, 2,3,5-trimethyl Pyrazine, tetramethylpyrazine, 2-ethyl-3,6-dimethylpyrazine, and 2-ethyl-3,5-dimethylpyrazine. Pyrazines are components that contribute to tobacco taste (specifically, fragrant taste).
　第１の加熱工程の後、混合物を室温まで冷ましてから、その後の工程に供してもよい。 After the first heating step, the mixture may be cooled to room temperature and then subjected to the subsequent steps.
　［分離工程］
　第１の加熱工程の後に、たばこ抽出液とたばこ残渣とを含む混合物から液体部分を分離してたばこ抽出液を得る。この分離工程は行うことが好ましいが、行わなくてもよい。 [Separation process]
After the first heating step, the liquid portion is separated from the mixture containing the tobacco extract and the tobacco residue to obtain a tobacco extract. This separation step is preferably performed but may not be performed.
　分離工程を行った場合、たばこ抽出液を第２の加熱工程に供し、分離工程を行わなかった場合、たばこ抽出液とたばこ残渣とを含む混合物を第２の加熱工程に供する。 When the separation step is performed, the tobacco extract is subjected to the second heating step, and when the separation step is not performed, the mixture including the tobacco extract and the tobacco residue is subjected to the second heating step.
　［第２の加熱工程］
　第２の加熱工程において、たばこ抽出液とたばこ残渣とを含む混合物、または分離されたたばこ抽出液を２５～６０℃の温度で加熱する。第２の加熱工程が、２５℃未満の温度で行われると、蔵置期間中に香喫味の変化を引き起こす不安定な成分を十分に減少させることが難しい。また、第２の加熱工程が、６０℃を超える温度で行われると、第１の加熱工程で増加したピラジン類が減少し易くなる。 [Second heating step]
In the second heating step, the mixture containing the tobacco extract and the tobacco residue, or the separated tobacco extract is heated at a temperature of 25 to 60.degree. When the second heating step is performed at a temperature of less than 25 ° C., it is difficult to sufficiently reduce unstable components that cause a change in flavor during storage. In addition, when the second heating step is performed at a temperature higher than 60 ° C., pyrazines increased in the first heating step tend to be reduced.
　第２の加熱工程は、好ましくは３０～５０℃の温度で行うことができる。 The second heating step can be carried out preferably at a temperature of 30 to 50.degree.
　第２の加熱工程は、好ましくは２４時間以上、より好ましくは２４～７２０時間、更に好ましくは２４～７２時間にわたって行うことができる。 The second heating step can be performed preferably for 24 hours or more, more preferably for 24 to 720 hours, further preferably for 24 to 72 hours.
　第２の加熱工程は、密閉容器内で行われることが望ましい。第２の加熱工程を密閉容器内で行った場合、加熱工程後に混合物の液体量を維持することができる。 The second heating step is preferably performed in a closed vessel. When the second heating step is performed in a closed vessel, the liquid amount of the mixture can be maintained after the heating step.
　第２の加熱工程後に、たばこ抽出液中のピラジン類の合計含有量をほとんど減少させることなく、たばこ抽出液中のシクロテン、マルトールおよびバニリンの合計含有量を顕著に減少させることができる。 After the second heating step, the total content of cyclothene, maltol and vanillin in the tobacco extract can be significantly reduced without substantially reducing the total content of pyrazines in the tobacco extract.
　これにより、好ましくは、
　出発原料となるたばこ材料１ｇに対して、最終的に製造されるたばこ香味液中に含まれるピラジン類の合計含有量が０．４ｍｇ以上となるようにピラジン類を含み、
　出発原料となるたばこ材料１ｇに対して、最終的に製造されるたばこ香味液中に含まれるシクロテン、マルトールおよびバニリンの合計含有量が０．０５ｍｇ以下となるようにシクロテン、マルトールおよびバニリンを含む
たばこ香味液を得ることができる。 Thereby, preferably
The pyrazines are contained so that the total content of pyrazines contained in the finally produced tobacco flavor liquid is 0.4 mg or more per 1 g of the tobacco material as the starting material,
A cigarette containing cycloten, maltol and vanillin so that the total content of cycloten, maltol and vanillin contained in the finally produced tobacco flavor liquid is 0.05 mg or less per 1 g of the tobacco material as a starting material A flavor liquid can be obtained.
　より好ましくは、
　出発原料となるたばこ材料１ｇに対して、最終的に製造されるたばこ香味液中に含まれるピラジン類の合計含有量が０．４～４ｍｇとなるようにピラジン類を含み、
　出発原料となるたばこ材料１ｇに対して、最終的に製造されるたばこ香味液中に含まれるシクロテン、マルトールおよびバニリンの合計含有量が０．０５ｍｇ以下となるようにシクロテン、マルトールおよびバニリンを含むか、またはシクロテン、マルトールおよびバニリンを含まない
たばこ香味液を得ることができる。 More preferably,
The pyrazines are contained so that the total content of pyrazines contained in the finally produced tobacco flavor liquid is 0.4 to 4 mg per 1 g of the tobacco material as the starting material,
Does it contain cyclotene, maltol and vanillin so that the total content of cyclotene, maltol and vanillin contained in the finally produced tobacco flavor liquid is 0.05 mg or less per 1 g of the starting tobacco material? It is possible to obtain a tobacco flavor liquid free of, or cyclotene, maltol and vanillin.
　このように、本発明の方法により得られるたばこ香味液は、ピラジン類を多量に含み、シクロテン、マルトールおよびバニリンを少量しか含まないか、または全く含まない。したがって、かかるたばこ香味液は、たばこ製品の香味源の原材料として用いられた際に、ピラジン類を多量に含むことにより、豊かな香喫味をユーザーに与えることができ、シクロテン、マルトールおよびバニリンを少量しか含まないか、または全く含まないことにより、これら成分がたばこ製品の蔵置中に変化して香喫味の変化を起こすことを防ぐことができる。 Thus, the tobacco flavor liquid obtained by the method of the present invention contains a large amount of pyrazines and contains only a small amount or none of cyclotene, maltol and vanillin. Therefore, when used as a raw material of a flavor source of tobacco products, such a tobacco flavor liquid can provide rich flavor and taste to users by containing a large amount of pyrazines, and a small amount of cycloten, maltol and vanillin. By containing only or not containing at all, these components can be prevented from changing during storage of the tobacco product to cause a change in flavor and taste.
　＜２．たばこ製品＞
　後述の実施例で示されるとおり、第１の加熱工程で得られたたばこ抽出液を、４０℃の加熱工程に晒しても、増大したピラジン類は減少しなかったが、８０℃の加熱乾燥工程に晒すと、増大したピラジン類が減少してしまった（後述の表１の例１および表２の例３を参照）。従って、本発明の方法に従って製造されたたばこ香味液は、ピラジン類の減少を引き起こす高温に晒されることなく、たばこ製品（例えば香味吸引器）の香味源の原材料としてたばこ製品で用いられる必要がある。従来、たばこ香味液は、無煙たばこ（スヌース）やシガレットなどのたばこ製品に組み込まれる際、たばこ残渣にかけ戻して、これを例えば８０～１２０℃の加熱乾燥工程に晒してからたばこ製品に組み込まれていたが、本発明では、たばこ香味液が、かかる加熱乾燥工程に晒されるべきではない。 <2. Tobacco products>
As shown in the examples described below, even if the tobacco extract obtained in the first heating step was subjected to the heating step at 40 ° C., the increased pyrazines did not decrease, but the heating and drying step at 80 ° C. When the exposure to (1), the pyrazines increased (see Example 1 in Table 1 and Example 3 in Table 2 below). Thus, the tobacco flavoring liquid produced according to the method of the present invention needs to be used in the tobacco product as a source of flavor source for tobacco products (eg flavor suckers) without being exposed to high temperatures causing reduction of pyrazines . Conventionally, when a tobacco flavor liquid is incorporated into a tobacco product such as smokeless tobacco (snus) or cigarette, it is added to the tobacco residue and exposed to a heat drying process at, for example, 80 to 120 ° C. before being incorporated into the tobacco product. However, in the present invention, the tobacco flavor liquid should not be exposed to such a heating and drying step.
　具体的にいうと、第１の加熱工程後にピラジン類を多量に含むように調製されたたばこ抽出液は、第２の加熱工程を経てたばこ香味液になり、その後、たばこ製品の香味源の原材料としてたばこ製品で用いられてユーザーに使用されるまで、６０℃を超える温度条件下に置かれないことが好ましい。より具体的には、第１の加熱工程後にピラジン類を多量に含むように調製されたたばこ抽出液は、第２の加熱工程を経てたばこ香味液になり、その後、たばこ製品の香味源の原材料としてたばこ製品で用いられてユーザーに使用されるまで、６０℃以下、具体的にはマイナス３０℃～プラス６０℃の温度条件下に置かれることが好ましい。 Specifically, the tobacco extract prepared so as to contain a large amount of pyrazines after the first heating step passes through the second heating step to become a tobacco flavor liquid, and thereafter, the raw material of the flavor source of the tobacco product It is preferred not to be subjected to temperature conditions exceeding 60 ° C. until it is used as a tobacco product and used by the user. More specifically, the tobacco extract prepared so as to contain a large amount of pyrazines after the first heating step is converted to a tobacco flavor liquid through the second heating step, and thereafter, the raw material of the flavor source of the tobacco product It is preferable to be subjected to temperature conditions of 60 ° C. or less, specifically, minus 30 ° C. to plus 60 ° C., until it is used as a tobacco product and used by a user.
　たばこ抽出液が、第２の加熱工程を経てたばこ香味液になり、その後、たばこ製品の香味源の原材料としてたばこ製品で用いられてユーザーに使用されるまで、６０℃を超える温度条件下に置かれないと、たばこ香味液は、蔵置後も、ピラジン類を減少させることなく安定に含むことができ、かかるたばこ香味液を香味源の原材料として含むたばこ製品は、使用時にユーザーに優れた香喫味を提供することができる。 The tobacco extract is subjected to a second heating step to become a tobacco flavor liquid, and then placed under temperature conditions exceeding 60 ° C. until it is used in the tobacco product as a raw material of the tobacco product flavor source and used by the user. If not, the tobacco flavor liquid can be stably contained even after storage without reducing pyrazines, and a tobacco product containing such tobacco flavor liquid as a raw material of a flavor source has an excellent flavor and taste for the user at the time of use Can be provided.
　このように、たばこ抽出液やたばこ香味液は、６０℃を超える温度条件下に置かれないことが好ましいが、製造されたばこ香味液は、たばこ製品に適用される前に中和されてもよい。 Thus, although it is preferred that the tobacco extract or tobacco flavor liquid not be subjected to temperature conditions above 60 ° C., the manufactured tobacco flavor liquid may be neutralized before being applied to the tobacco product .
　本発明の方法に従って製造されたたばこ香味液は、例えば、非加熱型香味吸引器や加熱型香味吸引器に適用される香味源を製造するための原材料として用いることができる。 The tobacco flavor liquid manufactured according to the method of this invention can be used as a raw material for manufacturing the flavor source applied, for example to a non-heating type flavor suction device or a heating type flavor suction device.
　「非加熱型香味吸引器」は、たばこ香味源（例えば、たばこ刻やたばこ香味液）を加熱することなく、ユーザーが吸引によりたばこ香味源の香味を味わう吸引器であり、例えば、吸引ホルダと吸引ホルダの空気流通路に充填されたたばこ香味源とを含む香味吸引器が挙げられる（例えば、ＷＯ２０１０／０９５６５９を参照）。 The “non-heated type flavor suction device” is a suction device which allows the user to taste the flavor of the tobacco flavor source by suction without heating the tobacco flavor source (eg, tobacco cut and tobacco flavor liquid), for example, a suction holder And a flavor suction device including a tobacco flavor source filled in the air flow passage of the suction holder (see, for example, WO 2010/095659).
　「加熱型香味吸引器」は、たばこ香味源を燃焼させることなく加熱し、加熱されたたばこ香味源の香味をユーザーが吸引により味わう吸引器であり、例えば、炭素熱源の燃焼熱でたばこ香味源を加熱する炭素熱源型吸引器（例えばＷＯ２００６／０７３０６５を参照）；吸引器と吸引器を電気加熱するための加熱デバイスとを備えた電気加熱型吸引器（例えばＷＯ２０１０／１１０２２６を参照）；またはたばこ香味源を含有する液状のエアロゾル源を加熱により霧化する液体霧化型吸引器（例えばＷＯ２０１５／０４６３８５を参照）が挙げられる。 The "heated flavor suction device" is a suction device which heats the tobacco flavor source without burning it and tastes the flavor of the heated tobacco flavor source by suction, and for example, the tobacco flavor source is heated by combustion heat of a carbon heat source A carbon heat source type aspirator (see, for example, WO2006 / 073065); an electrically heated aspirator (for example, see WO2010 / 110226) comprising an aspirator and a heating device for electrically heating the aspirator; or a cigarette A liquid atomization type aspirator (see, for example, WO 2015/046385) which atomizes a liquid aerosol source containing a flavor source by heating.
　本発明の方法に従って製造されたたばこ香味液は、「非加熱型香味吸引器」において、単独で液体収容部に組み込まれる液体香味源を製造するための原材料として使用されてもよいし、その他材料と混合してポッド（pod）内に入れられる香味源を製造するための原材料として使用されてもよい。あるいは、本発明の方法に従って製造されたたばこ香味液は、「加熱型香味吸引器」において、単独で液体収容部に組み込まれる液体香味源を製造するための原材料として使用されてもよいし、その他材料と混合してポッド内に入れられる香味源を製造するための原材料として使用されてもよいし、エアロゾル源の液体（例えばグリセリン）と混合して用いられる香味源を製造するための原材料として使用されてもよい。 The tobacco flavor liquid produced according to the method of the present invention may be used as a raw material for producing a liquid flavor source which is independently incorporated into the liquid storage in the "non-heated flavor suction device", or other materials And may be used as a raw material to produce a flavor source that can be mixed with and placed in a pod. Alternatively, the tobacco flavor liquid produced according to the method of the present invention may be used as a raw material for producing a liquid flavor source which is independently incorporated into the liquid storage unit in the "heating type flavor suction device", or the like It may be used as a raw material to produce a flavor source that is mixed with ingredients and placed in a pod, or used as a raw material to produce a flavor source that is used mixed with an aerosol source liquid (eg, glycerin) It may be done.
　＜３．好ましい実施形態＞
　以下に、本発明の好ましい実施形態をまとめて示す。 <3. Preferred embodiment>
Hereinafter, preferred embodiments of the present invention will be summarized.
　上述のとおり、実施形態に係るたばこ香味液の製造方法は、
　たばこ材料とアルカリ水溶液とを含み、１１～１３のｐＨを有する混合物を、８０～２４０℃の温度で加熱する第１の加熱工程と、
　前記第１の加熱工程の後に、前記混合物を２５～６０℃の温度で加熱する第２の加熱工程と
を含む。 As described above, the method for producing a tobacco flavor liquid according to the embodiment
A first heating step of heating a mixture comprising tobacco material and an aqueous alkaline solution and having a pH of 11 to 13 at a temperature of 80 to 240 ° C .;
And a second heating step of heating the mixture at a temperature of 25 to 60 ° C. after the first heating step.
　また、上述のとおり、好ましい実施形態に係るたばこ香味液の製造方法は、
　たばこ材料とアルカリ水溶液とを含み、１１～１３のｐＨを有する混合物を、８０～２４０℃の温度で加熱する第１の加熱工程と、
　前記第１の加熱工程の後に、前記混合物から液体部分を分離してたばこ抽出液を得る工程と、
　分離された前記たばこ抽出液を２５～６０℃の温度で加熱する第２の加熱工程と
を含む。 In addition, as described above, the method for producing a tobacco flavor liquid according to a preferred embodiment is:
A first heating step of heating a mixture comprising tobacco material and an aqueous alkaline solution and having a pH of 11 to 13 at a temperature of 80 to 240 ° C .;
Separating the liquid portion from the mixture to obtain a tobacco extract after the first heating step;
And C. heating the separated tobacco extract at a temperature of 25 to 60 ° C.
　より好ましい実施形態によると、上記実施形態の何れか１つにおいて、
　前記第１の加熱工程が、
　たばこ材料とアルカリ水溶液とを含み、１１～１３のｐＨを有する混合物を、８０℃以上１６０℃未満の温度で、前記混合物のｐＨが１０以下になるまで加熱する加熱工程Ａと、
　前記加熱工程Ａの後に、前記混合物を、１６０℃以上２４０℃以下の温度で少なくとも３０分間加熱する加熱工程Ｂと
から構成される。 According to a more preferred embodiment, in any one of the above embodiments:
The first heating step is
Heating step A, comprising heating a mixture containing tobacco material and an aqueous alkaline solution and having a pH of 11 to 13 at a temperature of 80 ° C. or more and less than 160 ° C. until the pH of the mixture becomes 10 or less;
The heating step B comprises heating the mixture at a temperature of 160 ° C. or more and 240 ° C. or less for at least 30 minutes after the heating step A.
　より好ましい実施形態によると、上記実施形態の何れか１つにおいて、前記加熱工程Ａが１２０～１５０℃の温度で行われる。 According to a more preferred embodiment, the heating step A is performed at a temperature of 120 to 150 ° C. in any one of the above embodiments.
　好ましい実施形態によると、上記実施形態の何れか１つにおいて、前記加熱工程Ｂが１６０～２００℃の温度で行われる。 According to a preferred embodiment, the heating step B is performed at a temperature of 160 to 200 ° C. in any one of the above embodiments.
　より好ましい実施形態によると、上記実施形態の何れか１つにおいて、前記加熱工程Ａが３０分～２時間にわたって行われる。 According to a more preferred embodiment, the heating step A is performed for 30 minutes to 2 hours in any one of the above embodiments.
　好ましい実施形態によると、上記実施形態の何れか１つにおいて、前記加熱工程Ｂが３０分～２時間にわたって行われる。 According to a preferred embodiment, the heating step B is performed for 30 minutes to 2 hours in any one of the above embodiments.
　より好ましい実施形態によると、上記実施形態の何れか１つにおいて、前記第１の加熱工程が、１０時間未満にわたって行われる。 According to a more preferred embodiment, in any one of the above embodiments, the first heating step is performed for less than 10 hours.
　より好ましい実施形態によると、上記実施形態の何れか１つにおいて、前記第１の加熱工程が、１時間以上、１０時間未満にわたって、好ましくは１～４時間にわたって行われる。 According to a more preferred embodiment, in any one of the above embodiments, the first heating step is performed for 1 hour or more and less than 10 hours, preferably for 1 to 4 hours.
　より好ましい実施形態によると、上記実施形態の何れか１つにおいて、前記たばこ材料が、たばこ刻であり、好ましくは、裁刻された葉たばこである。 According to a more preferred embodiment, in any one of the above embodiments, the tobacco material is tobacco cut, preferably cut tobacco.
　より好ましい実施形態によると、上記実施形態の何れか１つにおいて、前記混合物が、１１．５～１２．５のｐＨを有する。 According to a more preferred embodiment, in any one of the above embodiments, the mixture has a pH of 11.5 to 12.5.
　より好ましい実施形態によると、上記実施形態の何れか１つにおいて、前記アルカリ水溶液が、０．１～０．５ｍｏｌ／Ｌの水酸化カリウム水溶液、または０．１～０．５ｍｏｌ／Ｌの水酸化ナトリウム水溶液である。 According to a more preferred embodiment, in any one of the above embodiments, the aqueous alkali solution is a 0.1-0.5 mol / L aqueous potassium hydroxide solution, or a 0.1-0.5 mol / L aqueous hydroxide. It is an aqueous solution of sodium.
　より好ましい実施形態によると、上記実施形態の何れか１つにおいて、前記たばこ材料の質量（ｇ）と前記アルカリ水溶液の体積（ｍＬ）との比が、１：５～１：２０であり、好ましくは、１：７～１：１５である。 According to a more preferred embodiment, in any one of the above embodiments, the ratio of the mass (g) of the tobacco material to the volume (mL) of the aqueous alkaline solution is 1: 5 to 1:20, preferably Is 1: 7 to 1:15.
　より好ましい実施形態によると、上記実施形態の何れか１つにおいて、前記加熱工程Ａが、前記混合物のｐＨが８～１０になるまで行われる。 According to a more preferred embodiment, in any one of the above embodiments, the heating step A is performed until the pH of the mixture is 8-10.
　より好ましい実施形態によると、上記実施形態の何れか１つにおいて、前記第１の加熱工程は、密閉容器内で行われる。 According to a more preferred embodiment, in any one of the above embodiments, the first heating step is performed in a closed container.
　より好ましい実施形態によると、上記実施形態の何れか１つにおいて、前記第２の加熱工程が、２４時間以上にわたって行われる。 According to a more preferred embodiment, in any one of the above embodiments, the second heating step is performed for 24 hours or more.
　より好ましい実施形態によると、上記実施形態の何れか１つにおいて、前記第２の加熱工程が、２４～７２０時間、好ましくは２４～７２時間にわたって行われる。 According to a more preferred embodiment, in any one of the above embodiments, the second heating step is performed for 24 to 720 hours, preferably for 24 to 72 hours.
　より好ましい実施形態によると、上記実施形態の何れか１つにおいて、前記第２の加熱工程が、３０～５０℃の温度で行われる。 According to a more preferred embodiment, in any one of the above embodiments, the second heating step is performed at a temperature of 30 to 50.degree.
　より好ましい実施形態によると、上記実施形態の何れか１つにおいて、第２の加熱工程が、密閉容器内で行われる。 According to a more preferred embodiment, in any one of the above embodiments, the second heating step is performed in a closed container.
　より好ましい実施形態によると、上記実施形態の何れか１つにおいて、前記第１の加熱工程後に得られたたばこ抽出液が、前記第２の加熱工程を経てたばこ香味液になり、その後、たばこ製品の香味源の原材料としてたばこ製品で用いられてユーザーに使用されるまで、６０℃を超える温度条件下に置かれない。 According to a more preferred embodiment, in any one of the above embodiments, the tobacco extract obtained after the first heating step becomes a tobacco flavor liquid through the second heating step, and then the tobacco product It is not subjected to temperature conditions exceeding 60 ° C. until it is used in tobacco products as a raw material for flavor sources of and used by users.
　より好ましい実施形態によると、上記実施形態の何れか１つにおいて、前記第１の加熱工程後に得られたたばこ抽出液が、前記第２の加熱工程を経てたばこ香味液になり、その後、たばこ製品の香味源の原材料としてたばこ製品で用いられてユーザーに使用されるまで、マイナス３０℃～プラス６０℃の温度条件下に置かれる。 According to a more preferred embodiment, in any one of the above embodiments, the tobacco extract obtained after the first heating step becomes a tobacco flavor liquid through the second heating step, and then the tobacco product It is subjected to temperature conditions of minus 30 ° C. to plus 60 ° C. until it is used in tobacco products as a raw material of flavor sources of and used by users.
　好ましい実施形態に係るたばこ香味液は、上記実施形態の何れか１つに記載の方法により製造され、前記たばこ材料１ｇに対して前記たばこ香味液中に含まれるピラジン類の合計含有量が０．４ｍｇ以上となるようにピラジン類を含み、前記たばこ材料１ｇに対して前記たばこ香味液中に含まれるシクロテン、マルトールおよびバニリンの合計含有量が０．０５ｍｇ以下となるようにシクロテン、マルトールおよびバニリンを含む。 The tobacco flavor liquid which concerns on preferable embodiment is manufactured by the method as described in any one of the said embodiment, and the total content of the pyrazines contained in the said tobacco flavor liquid with respect to 1 g of said tobacco materials is 0. It contains pyrazines to be 4 mg or more, and the total content of cycloten, maltol and vanillin contained in the tobacco flavor liquid is 0.05 mg or less with respect to 1 g of the tobacco material Including.
　より好ましい実施形態に係るたばこ香味液は、上記実施形態の何れか１つに記載の方法により製造され、前記たばこ材料１ｇに対して前記たばこ香味液中に含まれるピラジン類の合計含有量が０．４～４ｍｇとなるようにピラジン類を含み、前記たばこ材料１ｇに対して前記たばこ香味液中に含まれるシクロテン、マルトールおよびバニリンの合計含有量が０．０５ｍｇ以下となるようにシクロテン、マルトールおよびバニリンを含むか、またはシクロテン、マルトールおよびバニリンを含まない。 The tobacco flavor liquid which concerns on a more preferable embodiment is manufactured by the method as described in any one of the said embodiment, and the total content of the pyrazines contained in the said tobacco flavor liquid with respect to 1 g of said tobacco materials is 0 .Containing pyrazines to 4 to 4 mg, and cyclotene, maltol and martol such that the total content of cyclotene, maltol and vanillin contained in the tobacco flavor liquid is 0.05 mg or less per 1 g of the tobacco material Contains vanillin or does not contain cyclotene, maltol and vanillin.
　１．たばこ香味液の製造
　＜例１＞
　たばこ材料として、裁刻された葉たばこ（米国産バーレー葉および国産黄色葉（９：１の質量比）の混合物）を使用した。 1. Production of Tobacco Flavor Liquid <Example 1>
As tobacco material, cut leaf tobacco (a mixture of American Burley leaves and domestic yellow leaves (weight ratio of 9: 1)) was used.
　たばこ材料を、以下の加熱工程Ａおよび加熱工程Ｂを順次行うことにより加熱した（第１の加熱工程）。 The tobacco material was heated by sequentially performing the following heating step A and heating step B (first heating step).
　加熱工程Ａ：ステンレス製の耐圧容器内で、たばこ材料１ｇに０．２５ｍｏｌ／Ｌの水酸化カリウム水溶液１０ｍＬ（ｐＨ１２）を加え、混合物を得た。水酸化カリウム添加直後の混合物のｐＨは１２であった。得られた混合物を、ジャケットヒーターを用いて１２０℃で１時間加熱した。すなわち、得られた混合物を１２０℃でｐＨ１０以下になるまで加熱した。 Heating step A: In a stainless steel pressure container, 10 mL (pH 12) of a 0.25 mol / L aqueous potassium hydroxide solution was added to 1 g of the tobacco material to obtain a mixture. The pH of the mixture immediately after the addition of potassium hydroxide was 12. The resulting mixture was heated at 120 ° C. for 1 hour using a jacket heater. That is, the resulting mixture was heated at 120 ° C. until pH 10 or less.
　加熱工程Ｂ：加熱工程Ａの後、混合物を１８０℃で１時間加熱した。 Heating step B: After heating step A, the mixture was heated at 180 ° C. for 1 hour.
　加熱工程ＡおよびＢは、混合物の液体量を保つために密閉容器（容量：１００ｍＬ）内で行った。 The heating steps A and B were performed in a closed vessel (volume: 100 mL) in order to keep the liquid volume of the mixture.
　加熱工程Ｂの後、混合物から吸引濾過により残渣を除去して、たばこ抽出液を得た。 After the heating step B, the residue was removed from the mixture by suction filtration to obtain a tobacco extract.
　たばこ抽出液を、蓋付きガラス瓶に入れ、恒温槽において４０℃で加熱した（第２の加熱工程）。第２の加熱工程は、１日間、３日間、７日間、１４日間、または２８日間行った。第２の加熱工程も、たばこ抽出液の液体量を保つために密閉容器（容量：１０ｍＬ）内で行った。これによりたばこ香味液を得た。 The tobacco extract was placed in a lidded glass bottle and heated at 40 ° C. in a thermostat (second heating step). The second heating step was performed for 1 day, 3 days, 7 days, 14 days, or 28 days. The second heating step was also performed in a closed vessel (volume: 10 mL) in order to maintain the liquid volume of the tobacco extract. Thus, a tobacco flavor liquid was obtained.
　＜例２（比較例）＞
　第２の加熱工程を、たばこ抽出液を、蓋付きガラス瓶に入れ、恒温槽において８０℃で加熱することにより行ったこと、第２の加熱工程を、１日間、３日間、または７日間行ったこと以外は、例１と同様の方法に従ってたばこ香味液を得た。 <Example 2 (comparative example)>
The second heating step was performed by placing the tobacco extract in a glass bottle with a lid and heating at 80 ° C. in a thermostat, and the second heating step was performed for 1 day, 3 days, or 7 days A tobacco flavor liquid was obtained in the same manner as in Example 1 except for the following.
　＜例３（比較例）＞
　第２の加熱工程を、たばこ抽出液を、濾紙で濾過した後に、恒温槽において８０℃で１時間加熱乾燥することにより行ったこと以外は、例１と同様の方法に従ってたばこ香味液を得た。例３において加熱乾燥は、蓋付きガラス瓶（すなわち密閉容器）ではなく、開放容器内で行ったため、例３で得られたたばこ香味液の液体量は、たばこ抽出液の液体量より減少した。 <Example 3 (comparative example)>
The tobacco flavor liquid was obtained according to the same method as Example 1 except that the second heating step was performed by filtering the tobacco extract through filter paper and then heating and drying in a thermostat at 80 ° C. for 1 hour. . In Example 3, the heating and drying was performed in an open container, not in a glass bottle with a lid (ie, a closed container), so the liquid amount of the tobacco flavor liquid obtained in Example 3 was smaller than the liquid amount of the tobacco extract.
　２．香味成分の含有量の評価
　＜方法＞
　第２の加熱工程の開始時（０日目）に、たばこ抽出液中の香味成分の含有量を測定した。 2. Evaluation of content of flavor component <Method>
At the start of the second heating step (day 0), the content of the flavor component in the tobacco extract was measured.
　例１では、第２の加熱工程を開始してから１日後、３日後、７日後、１４日後、および２８日後に、たばこ香味液中の香味成分の含有量を測定した。例２では、第２の加熱工程を開始してから１日後、３日後、および７日後に、たばこ香味液中の香味成分の含有量を測定した。例３では、８０℃で１時間の加熱乾燥後に、たばこ香味液中の香味成分の含有量を測定した。 In Example 1, the content of the flavor component in the tobacco flavor liquid was measured 1 day, 3 days, 7 days, 14 days, and 28 days after the second heating step was started. In Example 2, the content of the flavor component in the tobacco flavor liquid was measured one day, three days, and seven days after the second heating step was started. In Example 3, after heat drying at 80 ° C. for 1 hour, the content of the flavor component in the tobacco flavor liquid was measured.
　測定は、以下のとおり行った。 The measurement was performed as follows.
　１．０ｍＬのたばこ香味液に内部標準（４－ブロモフェネチルアルコール）５０μＬと水８０ｍＬを加え、測定液を調製した。測定液を、塩酸、または水酸化ナトリウム水溶液を用いｐＨ２または９に調整した。その後、ｐＨ２の測定液およびｐＨ９の測定液のそれぞれを、WATERS社製Oasis HLBカートリッジに供した。その後、水２０ｍＬでカートリッジを洗浄し、ジエチルエーテルを用いて担持物を溶出した。その溶出液の上清を、GC/MS分析に供した。カラムはAgilent社製DB-FFAPを用い、オーブンは６０～２４０℃まで昇温した。MSはSIMモードで検出した。 A 50 μL internal standard (4-bromophenethyl alcohol) and 80 mL water were added to 1.0 mL tobacco flavor liquid to prepare a measurement solution. The measurement solution was adjusted to pH 2 or 9 using hydrochloric acid or sodium hydroxide aqueous solution. Thereafter, each of the pH 2 measurement solution and the pH 9 measurement solution was applied to a WATERS Corporation Oasis HLB cartridge. The cartridge was then washed with 20 mL of water and the support was eluted with diethyl ether. The supernatant of the eluate was subjected to GC / MS analysis. The column was heated to 60-240 ° C. using DB-FFAP manufactured by Agilent. MS detected in SIM mode.
　＜結果＞
　例１の結果を表１、並びに図２および３に示し、例２および３の結果を表２に示す。 <Result>
The results of Example 1 are shown in Table 1 and FIGS. 2 and 3 and the results of Examples 2 and 3 are shown in Table 2.
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-T000002
Figure JPOXMLDOC01-appb-T000002
　表１および２、並びに図２および３において、香味成分の含有量は、たばこ材料１ｇあたりの含有量（ｍｇ）で表す。 In Tables 1 and 2 and FIGS. 2 and 3, the content of the flavor component is represented by the content (mg) per 1 g of the tobacco material.
　例１では、第２の加熱工程（４０℃加熱）を開始してから２８日後に、たばこ香味液中のピラジン類の合計含有量は、初期の含有量の約８８質量％を維持し、ほとんど減少しなかったが、たばこ香味液中のシクロテン、マルトールおよびバニリンの合計含有量は、初期の含有量の約３質量％まで減少した（表１、並びに図２および３を参照）。 In Example 1, 28 days after the start of the second heating step (40 ° C. heating), the total content of pyrazines in the tobacco flavor liquid maintains about 88% by mass of the initial content, Although not reduced, the total content of cycloten, maltol and vanillin in the tobacco flavor liquid was reduced to about 3% by weight of the initial content (see Table 1 and Figures 2 and 3).
　例２では、第２の加熱工程（８０℃加熱）を開始してから７日後に、たばこ香味液中のピラジン類の合計含有量は、初期の含有量の約３６質量％まで減少し、たばこ香味液中のシクロテン、マルトールおよびバニリンの合計含有量は、初期の含有量の約３質量％まで減少した（表２を参照）。 In Example 2, seven days after the start of the second heating step (heating at 80 ° C.), the total content of pyrazines in the tobacco flavor liquid decreases to about 36% by mass of the initial content, The total content of cycloten, maltol and vanillin in the flavor liquid decreased to about 3% by weight of the initial content (see Table 2).
　例３では、たばこ抽出液を８０℃で１時間加熱乾燥させると、たばこ香味液中のピラジン類は消失し、たばこ香味液中のシクロテン、マルトールおよびバニリンの合計含有量は、初期の含有量の約４１質量％まで減少した（表２を参照）。 In Example 3, when the tobacco extract is dried by heating at 80 ° C. for 1 hour, pyrazines in the tobacco flavor liquid disappear, and the total content of cyclotene, maltol and vanillin in the tobacco flavor liquid is the initial content It has decreased to about 41% by weight (see Table 2).
　なお、たばこ抽出液を、第２の加熱工程に晒すことなく室温（約２２℃）に２８日間静置したところ、ピラジン類の合計含有量を維持することはできたが、シクロテン、マルトールおよびバニリンの合計含有量を十分に減少させることができなかった。 When the tobacco extract was allowed to stand at room temperature (about 22 ° C.) for 28 days without exposure to the second heating step, the total content of pyrazines could be maintained, but cyclotene, maltol and vanillin Could not be reduced sufficiently.
　これらの結果から、本発明の方法に従って、たばこ材料をアルカリ水溶液中で加熱して、たばこ抽出液に含まれるピラジン類を増加させた後、比較的低い温度で再度加熱すると、増加したピラジン類の含有量をほとんど減少させることなく、シクロテン、マルトールおよびバニリンの含有量を顕著に減少させることができることが分かる。 From these results, according to the method of the present invention, the tobacco material is heated in an alkaline aqueous solution to increase pyrazines contained in the tobacco extract, and then heated again at a relatively low temperature to increase the pyrazines It can be seen that the contents of cyclotene, maltol and vanillin can be significantly reduced without a substantial reduction of the content.
　３．官能評価
　＜方法＞
　例１に記載される方法に従って、第１の加熱工程を行い、その後、第２の加熱工程を４０℃で３日間行うことにより、たばこ香味液を製造した。製造後速やかに、たばこ香味液２ｍＬを蓋付きガラス瓶（容量：１０ｍＬ）に入れて、官能評価用のサンプル１－１を調製した。サンプル１－１を、室温（２２℃）で２４時間蔵置して、これを官能評価用のサンプル１－２とした。 3. Sensory evaluation <Method>
The tobacco flavor liquid was produced by performing the first heating step according to the method described in Example 1, and then performing the second heating step at 40 ° C. for 3 days. Immediately after production, 2 mL of the tobacco flavor liquid was placed in a lidded glass bottle (volume: 10 mL) to prepare sample 1-1 for sensory evaluation. The sample 1-1 was stored at room temperature (22 ° C.) for 24 hours to obtain a sample 1-2 for sensory evaluation.
　例１に記載される方法に従って、第１の加熱工程を行うことにより、たばこ抽出液を製造した。製造後速やかに、たばこ抽出液２ｍＬを蓋付きガラス瓶（容量：１０ｍＬ）に入れて、官能評価用サンプル２－１を調製した。サンプル２－１を、室温（２２℃）で２４時間蔵置して、これを官能評価用のサンプル２－２とした。 A tobacco extract was prepared by performing the first heating step according to the method described in Example 1. Immediately after production, 2 mL of the tobacco extract was placed in a lidded glass bottle (volume: 10 mL) to prepare a sample for sensory evaluation 2-1. The sample 2-1 was stored at room temperature (22 ° C.) for 24 hours to obtain a sample 2-2 for sensory evaluation.
　例３に記載される方法に従って、第１の加熱工程を行ってたばこ抽出液を得、その後、たばこ抽出液（２ｍＬ）を濾紙で濾過した後に８０℃で１時間加熱乾燥することによりたばこ香味液を製造した。製造後速やかに、たばこ香味液（すなわち、２ｍＬのたばこ抽出液から得られたたばこ香味液）を蓋付きガラス瓶（容量：１０ｍＬ）に入れて、官能評価用のサンプル３－１を調製した。 The first heating step is performed according to the method described in Example 3 to obtain a tobacco extract, and then the tobacco extract (2 mL) is filtered through filter paper and then dried by heating at 80 ° C. for 1 hour to obtain a tobacco flavor liquid Manufactured. Immediately after production, the tobacco flavor liquid (ie, the tobacco flavor liquid obtained from 2 mL of the tobacco extract) was placed in a lidded glass bottle (volume: 10 mL) to prepare sample 3-1 for sensory evaluation.
　上記サンプルを調製後速やかに、専門パネラー５人による官能評価により評価した。パネラーは、ガラス瓶の蓋を外して香気を嗅ぐことにより各サンプルを評価した。 Immediately after preparation of the above samples, evaluation was made by sensory evaluation by five expert panelists. The panelists evaluated each sample by removing the lid of the glass bottle and smelling the aroma.
　サンプル１－１、２－１および３－１については、パネラーは香気の特徴をコメントすることにより評価した。サンプル１－２については、サンプル１－１と比較して香気に変化があったか否かを評価した。同様に、サンプル２－２については、サンプル２－１と比較して香気に変化があったか否かを評価した。 The panelists evaluated samples 1-1, 2-1 and 3-1 by commenting on the characteristics of the aroma. Sample 1-2 was evaluated as to whether or not there was a change in aroma compared to sample 1-1. Similarly, for sample 2-2, it was evaluated whether or not there was a change in aroma compared to sample 2-1.
　＜結果＞
　官能評価の結果を表３に示す。 <Result>
The results of sensory evaluation are shown in Table 3.
Figure JPOXMLDOC01-appb-T000003
Figure JPOXMLDOC01-appb-T000003
　サンプル１－１のたばこ香味液は、優れた香気を有していた。サンプル１－１を蔵置してサンプル１－２を調製した場合、サンプル１－２は、サンプル１－１の優れた香気を維持していた。 The tobacco flavor liquid of Sample 1-1 had excellent aroma. When Sample 1-1 was stored to prepare Sample 1-2, Sample 1-2 maintained the excellent aroma of Sample 1-1.
　一方、サンプル２－１のたばこ香味液は、フルーティーな香気を有していたが、サンプル１－１と比較すると、香気の複雑さに欠けていた。サンプル２－１を蔵置してサンプル２－２を調製した場合、サンプル２－２は、フルーティーな香気が減少し、サンプル２－１の香気を維持していなかった。 On the other hand, the tobacco flavor liquid of sample 2-1 had a fruity aroma, but compared with sample 1-1, it lacked the complexity of the aroma. When Sample 2-1 was stored to prepare Sample 2-2, Sample 2-2 had a reduced fruity aroma and did not maintain the aroma of Sample 2-1.
　サンプル３－１のたばこ香味液は、香気が薄かった。 The tobacco flavor liquid of sample 3-1 had a weak aroma.
　これらの結果から、本発明の方法に従って、たばこ材料をアルカリ水溶液中で加熱し、その後、比較的低い温度で再度加熱してたばこ香味液を製造すると、蔵置後も優れた香気を有するたばこ香味液が得られることが分かる。 From these results, according to the method of the present invention, when the tobacco material is heated in an aqueous alkaline solution and then heated again at a relatively low temperature to produce a tobacco flavor liquid, the tobacco flavor liquid having excellent aroma even after storage It can be seen that
　また、上述の「香味成分の含有量の評価」および「官能評価」の結果から、以下のことが分かる。本発明の方法によれば、香喫味成分としてピラジン類を多量に含み、かつ、シクロテン、マルトールおよびバニリン（すなわち、蔵置期間中に香喫味の変化を引き起こす不安定な成分）を少量しか含まないたばこ香味液を製造することができる。かかるたばこ香味液は、たばこ製品の香味源の原材料として用いられた際に、ピラジン類を多量に含むことにより、豊かな香喫味を与えることができ、シクロテン、マルトールおよびバニリンを少量しか含まないことにより、これら成分がたばこ製品の蔵置中に変化して香喫味の変化を起こすことを防ぐことができる。 Moreover, the following thing is known from the result of the above-mentioned "evaluation of content of a flavor component" and "sensory evaluation." According to the method of the present invention, a tobacco containing a large amount of pyrazines as a flavor and taste component and containing only a small amount of cyclotene, maltol and vanillin (that is, an unstable component which causes change in flavor and taste during storage) A flavor liquid can be produced. When used as a raw material of a flavor source of tobacco products, such a tobacco flavor liquid can provide rich flavor by containing a large amount of pyrazines, and contains only a small amount of cyclotene, maltol and vanillin Thus, these components can be prevented from being changed during storage of the tobacco product to cause a change in flavor and taste.

Claims (11)

  1. 　たばこ材料とアルカリ水溶液とを含み、１１～１３のｐＨを有する混合物を、８０～２４０℃の温度で加熱する第１の加熱工程と、
    　前記第１の加熱工程の後に、前記混合物を２５～６０℃の温度で加熱する第２の加熱工程と
    を含む、たばこ香味液の製造方法。     A first heating step of heating a mixture comprising tobacco material and an aqueous alkaline solution and having a pH of 11 to 13 at a temperature of 80 to 240 ° C .;
    A second heating step of heating the mixture at a temperature of 25 to 60 ° C. after the first heating step.
  2. 　前記第１の加熱工程が、
    　たばこ材料とアルカリ水溶液とを含み、１１～１３のｐＨを有する混合物を、８０℃以上１６０℃未満の温度で、前記混合物のｐＨが１０以下になるまで加熱する加熱工程Ａと、
    　前記加熱工程Ａの後に、前記混合物を、１６０℃以上２４０℃以下の温度で少なくとも３０分間加熱する加熱工程Ｂと
    から構成される、請求項１に記載の方法。     The first heating step is
    Heating step A, comprising heating a mixture containing tobacco material and an aqueous alkaline solution and having a pH of 11 to 13 at a temperature of 80 ° C. or more and less than 160 ° C. until the pH of the mixture becomes 10 or less;
    The method according to claim 1, wherein the heating step B comprises heating the mixture at a temperature of 160 ° C to 240 ° C for at least 30 minutes after the heating step A.
  3. 　前記加熱工程Ａが１２０～１５０℃の温度で行われ、前記加熱工程Ｂが１６０～２００℃の温度で行われる請求項２に記載の方法。 The method according to claim 2, wherein the heating step A is performed at a temperature of 120 to 150 属 C, and the heating step B is performed at a temperature of 160 to 200 属 C.
  4. 　前記加熱工程Ａが３０分～２時間にわたって行われ、前記加熱工程Ｂが３０分～２時間にわたって行われる請求項２または３に記載の方法。 The method according to claim 2 or 3, wherein the heating step A is performed for 30 minutes to 2 hours, and the heating step B is performed for 30 minutes to 2 hours.
  5. 　前記第１の加熱工程が、１０時間未満にわたって行われる請求項１～３の何れか１項に記載の方法。 The method according to any one of the preceding claims, wherein the first heating step is performed for less than 10 hours.
  6. 　前記第１の加熱工程が、１時間以上、１０時間未満にわたって行われる請求項１～３および５の何れか１項に記載の方法。 The method according to any one of claims 1 to 3, wherein the first heating step is performed for 1 hour or more and less than 10 hours.
  7. 　前記第２の加熱工程が、２４時間以上にわたって行われる請求項１～６の何れか１項に記載の方法。 The method according to any one of claims 1 to 6, wherein the second heating step is performed for 24 hours or more.
  8. 　前記第２の加熱工程が、２４～７２０時間にわたって行われる請求項１～７の何れか１項に記載の方法。 The method according to any one of the preceding claims, wherein the second heating step is performed for 24 to 720 hours.
  9. 　前記第１の加熱工程の後に、前記混合物から液体部分を分離してたばこ抽出液を得る工程を更に含み、
    　前記第２の加熱工程が、分離された前記たばこ抽出液を２５～６０℃の温度で加熱する工程である
    請求項１～８の何れか１項に記載の方法。     Separating the liquid portion from the mixture to obtain a tobacco extract after the first heating step;
    The method according to any one of claims 1 to 8, wherein the second heating step is a step of heating the separated tobacco extract at a temperature of 25 to 60 属 C.
  10. 　前記第２の加熱工程が、３０～５０℃の温度で行われる請求項１～９の何れか１項に記載の方法。 The method according to any one of the preceding claims, wherein the second heating step is performed at a temperature of 30 to 50 属 C.
  11. 　請求項１～１０の何れか１項に記載の方法により製造されるたばこ香味液であって、前記たばこ材料１ｇに対して前記たばこ香味液中に含まれるピラジン類の合計含有量が０．４ｍｇ以上となるようにピラジン類を含み、前記たばこ材料１ｇに対して前記たばこ香味液中に含まれるシクロテン、マルトールおよびバニリンの合計含有量が０．０５ｍｇ以下となるようにシクロテン、マルトールおよびバニリンを含むたばこ香味液。 It is a tobacco flavor liquid manufactured by the method in any one of Claims 1-10, Comprising: The total content of the pyrazines contained in the said tobacco flavor liquid with respect to 1 g of said tobacco materials is 0.4 mg As described above, it contains pyrazines, and contains 1 g of the tobacco material such that the total content of cycloten, maltol and vanillin contained in the tobacco flavor liquid is 0.05 mg or less. Tobacco flavor liquid.
PCT/JP2017/028041 2017-08-02 2017-08-02 Method for producing tobacco flavor liquid, and tobacco flavor liquid WO2019026201A1 (en)

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