JP6027680B2 - Tobacco products containing purified natural (L) -menthol - Google Patents

Description

  The present invention relates to a tobacco product containing a natural (L) -purified product of menthol, and more specifically, by adding activated carbon to crude menthol, the miscellaneous taste is removed and the natural (L)-for smoking articles having a refreshing feeling. The present invention relates to a tobacco product containing purified menthol.

  Menthol is a cyclic monoterpene, an organic compound of alcohol, and is a volatile colorless crystal with a mint smell. Menthol has several diastereomers and enantiomers. Among them, natural (L) -menthol is frequently used for toothpaste, confectionery, mouth freshener, etc. Because it has, it is also used for pharmaceuticals.

  In addition, menthol has been used as a fragrance for tobacco. When the raw leaf tobacco is burned, it emits its own unique savory taste, and at the same time has its own irritation, off-flavor such as blue or raw odor, astringency and bitterness. On the other hand, licorice, sugar, honey, rum, fruit juice, vanilla, etc. are empirically used to relieve off-flavors and bad taste.

  In recent years, tobacco preferences have shown a tendency to diversify, and products with an exhilarating and rich flavor have come to be preferred. Of the components contained in the so-called tobacco flavor improver that improves the flavor as a fragrance, natural (L) -menthol contributes greatly.

  Most cigarette products currently on the market are cigarettes (cigarettes), but other cigarettes that are wrapped around tobacco leaves instead of paper, snuff products that enjoy the scent without igniting, and direct tobacco leaves Chewed tobacco products are known that enjoy a flavor by chewing a mixture containing. For example, in North Europe, a snuff product called snooze that sniffs a sachet containing tobacco powder between the gums and upper lip is widely used, and chewing tobacco products are popular among baseball players. Natural (L) -menthol is also used as a flavor improver in these tobacco products.

  As menthol, natural (L) -menthol and synthetic (L) -menthol are used. Synthetic (L) -menthol has a higher (L) -menthol purity than natural (L) -menthol, but does not contain fragrance component impurities derived from raw mint oil. And inferior to natural (L) -menthol. Since natural (L) -menthol is extracted from plants such as mint leaves, impurities are contained, and the content of these impurities affects the quality and flavor of natural (L) -menthol. For this reason, various investigations have been made on methods for purifying natural (L) -menthol. As one of them, there is a method in which crude menthol is brought into contact with supercritical carbon dioxide, and impurities are extracted by fractionation (see, for example, Patent Document 1). By this method, components such as an unpleasant odor (flavor), a bitter component, a weed-like aroma, a heavy miscellaneous substance, a resinous substance and the like can be removed. However, since this method uses supercritical carbon dioxide, an expensive apparatus is required, and it is difficult to industrialize easily.

  As another method, there is a method of crystallizing menthol by dissolving the crude menthol in acetonitrile and then cooling the solution (see, for example, Patent Document 2). As a result, natural (L) -menthol having a chemical purity of 99% or more and an optical purity of 99% ee or more can be obtained. However, since menthol is dissolved in an organic solvent (acetonitrile), the working environment that can be implemented is limited.

  As described above, even if the technique disclosed in Patent Document 1 or Patent Document 2 is used, a natural (L) -menthol purified product having a refreshing sensation and a mint-like fragrance and this natural (L) -menthol purified product It has been difficult to easily and inexpensively supply tobacco products containing sucrose.

Japanese Patent No. 3935987 Japanese Patent No. 5014846

  The present invention has been made to solve the above-described problems of the prior art, and is a natural (L) -menthol purified product that removes miscellaneous taste and has a refreshing feeling and a mint-like aroma derived from a natural product. To provide tobacco products.

The invention according to claim 1 contains a purified natural (L) -menthol product having a saturation of 1 or less as measured by the following methods (1) to (3) and having a refreshing feeling and a mint-like aroma. Tobacco products characterized by
(1) A step of distilling a purified natural (L) -menthol purified product under reduced pressure in a heat-melted state to obtain a vacuum distillation residue.
(2) A step of adding ethanol to the residue obtained in the step (1) to prepare an ethanol solution.
(3) A step of obtaining chroma using a color difference meter according to ISO 7724 (JIS Z8722) using the ethanol solution obtained in the step (2) as a color difference measurement sample.

  The invention according to claim 2 relates to the tobacco product according to claim 1, wherein the saturation is in a range of 0.4 to 0.6.

  According to a third aspect of the present invention, there are provided a cigarette engraver and a winding portion made of a wrapping paper surrounding the cigarette engraving, a filter portion made of a filter and a wrapping paper enclosing the periphery of the filter, at least a part of the winding portion and the filter portion It is a cigarette provided with the chip paper which connects the said winding part and the said filter part by wrapping the circumference | surroundings, The tobacco product of Claim 1 or 2 characterized by the above-mentioned.

  The invention according to claim 4 relates to a tobacco product according to claim 3, characterized in that the purified natural (L) -menthol is contained in the tobacco.

  The invention according to claim 5 relates to the tobacco product according to claim 1, wherein a vacuum distillation residue of the purified natural (L) -menthol is less than 0.1% by weight.

  According to the invention according to claim 1, by measuring an ethanol solution obtained by adding ethanol to the residue after vacuum distillation of a purified natural (L) -menthol product with a color difference meter according to ISO 7742, the palatability is improved. It is possible to confirm the presence of impurities that have a large impact. At this time, a natural (L) -menthol purified product having a saturation of 1 or less can be a natural (L) -menthol purified product having both a refreshing feeling and a mint-like aroma. By including the purified product of natural (L) -menthol in a tobacco product, a tobacco product having both a refreshing feeling and a mint-like aroma can be obtained.

  According to the invention of claim 2, when the natural (L) -menthol purified product is evaluated by a color difference meter in the same manner as in claim 1, the saturation is in the range of 0.4 to 0.6. Tobacco products containing purified natural (L) -menthol have a stronger refreshing feeling and mint-like fragrance than tobacco products containing purified natural (L) -menthol according to claim 1. Tobacco products containing products (see Table 1).

  According to the invention which concerns on Claim 3, the cigarette which has a refreshing feeling and a mint-like aroma can be obtained by containing the natural (L) -menthol refinement | purification thing of Claim 1 in a part of cigarette. .

  According to the invention which concerns on Claim 4, natural (L) -menthol refinement | purification thing of Claim 1 is included in a tobacco engraving, and natural (L) menthol refinement | purification product is easy to transfer to smoke at the time of smoking. A cigarette having a refreshing feeling and a mint-like aroma can be obtained.

  According to the invention which concerns on Claim 5, there are few impurities by the comparatively easy process of making it contact with activated carbon because the vacuum distillation residue of the said natural (L) -menthol refined product is less than 0.1 weight%. A purified natural (L) -menthol product having both a refreshing sensation and a mint-like fragrance can be obtained, and a tobacco product having both a refreshing sensation and a mint-like fragrance can be obtained by containing this.

It is the schematic of the cigarette which has one type of filter. It is the schematic of the cigarette which has two types of filters. (A) It is a cross-sectional view of a cigarette provided with a string containing a purified natural (L) -menthol at the center of the filter, and (B) is a cross-sectional view taken along the line AA. (A) It is a cross-sectional view of a cigarette provided with a destructible capsule containing natural (L) -menthol purified product in the gap in the filter, and (B) the cigarette provided with a destructible capsule in the gap in the filter. It is a cross-sectional view when the capsule is broken. (A) Cigarette schematic, (B) Cigarette cross-sectional view. (A) It is the schematic of a flavor suction pipe, (B) It is a cross-sectional view of a flavor suction pipe. (A) It is the schematic of a wet smokeless tobacco product, (B) It is the AA sectional drawing, (C) It is the figure which showed the usage method of the wet smokeless tobacco product. It is the figure which showed the usage method of a chewing tobacco product.

  Hereinafter, the tobacco product containing the natural (L) -menthol purified product according to the present invention, its production method and evaluation method will be described in detail.

  First, a tobacco product containing the purified natural (L) -menthol of the present invention will be described below with reference to the drawings.

1. Tobacco product containing purified natural (L) -menthol The tobacco product of the present invention has a saturation of 1 or less, preferably in the range of 0.4 to 0.6 as measured by the following evaluation method. And a natural (L) -menthol refined product that combines a mint-like aroma. A cigarette suitable for containing the purified natural (L) -menthol of the present invention will be described with reference to FIGS.

FIG. 1 is a schematic view of a cigarette having one type of filter.
The cigarette is composed of a cigarette engraver (6) and a winding part (2) composed of a wrapping paper (5) enclosing the cigarette engraver (6), and a filter (7) and a winding paper (3) wrapping around the filter (7). Filter part (1) and chip paper (4) for connecting winding part (2) and filter part (1) by wrapping around at least part of winding part (2) and filter part (1) Prepare.
Tobacco stamp (6) is a blend of tobacco leaf (yellow, Burley, etc.), medium bone, sheet tobacco, and relaxation. The wrapping paper (5) contains flax and wood pulp as raw materials, may contain calcium carbonate to suppress the burning odor of the paper and match the burning rate with cigarette engraving, and may contain citrate as a combustion aid good. Further, the wrapping paper (5) may be used with fine holes in order to adjust the air inflow amount. The filter (7) is generally an acetate filter made of acetate fiber, but neo sheet, rayon, paper, etc. may be used. Although plain paper is generally used as a material for the web (3), it is not particularly limited. Wood pulp, calcium carbonate, and titanium oxide are generally used as the material of the chip paper (4), but a material having fine holes may be used to adjust the air inflow amount.
In this case, the purified natural (L) -menthol can be contained in the tobacco (6) and / or the filter (7).

FIG. 2 is a schematic view of a cigarette having two types of filters.
Although the structure is almost the same as that of the cigarette having one type of filter in FIG. 1, the filter portion (1) is composed of two types of filters: an acetate filter (9) and a charcoal filter (10). Moreover, the raw material paper (8) which wraps the circumference | surroundings of an acetate filter (9) and a charcoal filter (10), and the winding paper (3) which connects an acetate filter (9) and a charcoal filter (10) are provided.
The charcoal filter (10) is obtained by incorporating activated carbon into a double or triple structure in which acetate fibers, neo-sheets, rayon, paper, and the like are combined. As the material paper (8), plain paper is generally used as a material in the same manner as the web (3), but is not particularly limited.
In this case, the purified natural (L) -menthol product can be contained in the tobacco (6) and / or acetate filter (9) and / or the charcoal filter (10) as in the case of the cigarette having one type of filter. it can.

FIG. 3A is a cross-sectional view of a cigarette provided with a string containing a natural (L) -menthol purified product at the center of the filter, and FIG. The structure is almost the same as that of the cigarette having one type of filter shown in FIG. 1, but a string (11) located substantially at the center of the filter is provided.
The string (11) is generally made of cotton, but is not particularly limited, and a natural (L) menthol purified product is applied to the string (11).
In this case, the purified natural (L) -menthol product can be contained in the filter (7) and / or the tobacco (6) in addition to the string (11).

4A is a cross-sectional view of a cigarette with a destructible capsule containing a natural (L) -menthol purified product in the gap in the filter, and FIG. 4B is a cigarette with a destructible capsule in the gap in the filter. It is a cross-sectional view when destroying the capsule. The structure is almost the same as that of a cigarette having one type of filter in FIG. 1, but a destructible capsule (12) is provided in the gap in the filter.
The destructible capsule (12) is filled with purified natural (L) -menthol, and is broken by applying pressure with a finger before or during smoking to destroy the destructible capsule (12). The natural (L) -menthol purified product is released to the filter (7). The film of the destructible capsule (12) is made of gelatin or the like, and contains 1 to 10 mg of purified natural (L) -menthol in the capsule.
In this case, the purified natural (L) -menthol can be contained in the filter (7) and / or the tobacco (6) in addition to the destructible capsule (12). Although not shown in FIG. 4, a string may be provided at the center of the filter as shown in FIG. 3, and the string may contain a purified natural (L) -menthol product.

Moreover, in the case of a cigarette, you may apply | coat natural (L) -menthol refined | purified material to the inner side of a cigarette packaging container. Although the method of applying is not particularly limited, an aluminum laminated paper coated with natural (L) -menthol purified product may be inserted into a cigarette packaging container, and natural (L) -menthol purified product directly inside the packaging container May be applied.
The natural (L) -menthol purified product is applied to the inside of the cigarette packaging container so that the natural (L) -menthol purified product is transferred to the cigarette tobacco (6) and / or filter (7) during storage. Can be made.

  A cigar tobacco suitable for containing the purified natural (L) -menthol of the present invention will be described with reference to FIG.

5A is a schematic view of a cigarette and FIG. 5B is a cross-sectional view thereof. The cigarette includes a filler (13) containing tobacco leaves or tobacco cuts, a binder (14) optionally wrapped around the filler with tobacco leaves, and a wrapper (15) wrapped around the filler or binder with tobacco leaves.
In this case, a purified natural (L) -menthol product can be contained in tobacco leaves or tobacco.

  A snuff product suitable for containing the purified natural (L) -menthol product of the present invention will be described with reference to FIGS.

Snuff products include snuffs, flavor suction pipes, wet smokeless tobacco products, and the like. FIG. 6 shows the structure of the flavor suction pipe, and FIG. 7 shows the structure and method of use of the wet smokeless tobacco product.
Snuff refers to dry or moist tobacco powder. The dry tobacco powder is placed on the thumb of the back of the hand and the indentation at the base of the index finger and sucked from the nose. In addition, it is common practice to use snuff tobacco to apply wet tobacco powder to the gums.
In this case, the purified natural (L) -menthol can be contained in the tobacco powder.

FIG. 6: is the (A) schematic and (B) cross-sectional view of the flavor suction pipe which is a snuff tobacco product. The flavor suction pipe includes a tube-shaped pipe body (16), a mouthpiece (18) removably inserted into one end of the pipe body (16), a cap (17) covering the mouthpiece (18), and a pipe body (16 And a replaceable flavor generating cartridge (19) and a tobacco stamp (6) filled in the flavor generating cartridge (19).
In this case, the purified natural (L) -menthol can be contained in the tobacco (6) in the cartridge (19).

FIG. 7 is a diagram showing a method of using the wet smokeless tobacco product (A), (B) AA sectional view, and (C) wet smokeless tobacco product (22), which are snuff products. The wet smokeless tobacco product (22) includes a tobacco engraved moisture (6), a water permeable packaging material (21) for wrapping the tobacco engraving (6), and a seal portion (20) for sealing the water permeable packaging material (21). ).
The moisture content of the tobacco stamp (6) may be between 20-70%, and a nonwoven fleece is generally used as a packaging material, but is not particularly limited as long as the material transmits moisture. The material of the seal is not particularly limited. The wet smokeless tobacco product (22) is used by being sandwiched between the upper lip and the gum as shown in FIG. 7 (C).
In this case, the purified natural (L) -menthol can be contained in the tobacco (6) containing moisture.

  A chewing tobacco product suitable for containing the purified natural (L) -menthol product of the present invention will be described with reference to FIG.

FIG. 8 is a view showing a method of using the chewing tobacco product (23).
Chewing tobacco products (23) include plugs, twists, scraps, chewing gums and the like. The chewing tobacco product (23) is used by being put directly into the mouth as shown in FIG.
The plug is a cigarette leaf or cigarette stamp that has been compressed into a sheet shape, wrapped around the upper winding leaf, and compressed again. The tobacco sheet is generally rectangular, but the shape is not particularly limited. In this case, the purified natural (L) -menthol can be contained in the tobacco leaf, tobacco cut and / or upper roll leaf.
Twist is a twisted cigarette leaf wrapped with an upper roll, twisted again, and pressure is applied. In this case, the natural (L) -menthol purified product can be contained in the tobacco leaf and / or the upper roll leaf.
Scrap is a bite of cigarettes that are put directly into the mouth. In this case, the purified natural (L) -menthol product can be contained in the tobacco.
Chewing gum is obtained by processing tobacco components into chewing gum without using tobacco leaves or tobacco cuts. In this case, the purified natural (L) -menthol product can be contained in the chewing gum together with the tobacco component.

2. Method for Producing Natural (L) -Menthol Purified Product Next, a method for producing a purified natural (L) -menthol product will be described.
The crude menthol according to the present invention is obtained by extraction by steam distillation or the like from Mentha aquatica, Mentha arvensis, Mentha longifolia, Mentha pulegium, Mentha spicata, Mentha piperita and the like belonging to the genus Labiatae. These production areas and varieties are not particularly limited. Crude menthol obtained from mint hay leaves and essential oils extracted from the ground by steam distillation or the like is used in the present invention.

  The larger the (L) -menthol content, the better the crude menthol, desirably 90% or more, and the extraction method is not particularly limited. For example, crude menthol may be natural (L) -menthol obtained by crystallizing essential oil and centrifuging, or may be further purified by distillation, column chromatography or the like.

<Heat-melting process>
The extracted crude menthol is heated and melted before adding activated carbon to form liquid crude menthol. Since the melting point of menthol is around 42 ° C., the heating temperature may be 45 to 100 ° C., preferably 55 to 60 ° C., but is not particularly limited.

<Activated carbon addition process>
Activated carbon is added to the liquid crude menthol. At this time, an amount of 0.1 to 10% by weight of the crude menthol may be added, preferably 1 to 4% by weight. If the amount of activated carbon added is less than 0.1% by weight, the impurities in the crude menthol cannot be sufficiently removed, and as a result, the miscellaneous taste cannot be removed. On the other hand, if the amount of activated carbon added exceeds 10% by weight, impurities in the crude menthol are removed more than necessary, and the mint-like aroma is impaired. Mint-like aroma refers to the natural mint scent.

<Stirring step>
Thereafter, in order to prevent the crude menthol from solidifying, it is stirred while warming to adsorb impurities on the activated carbon. At this time, the temperature for warming the crude menthol may be in the range of 50 ° C. to 80 ° C., preferably 55 ° C. to 65 ° C., and the stirring time is in the range of 30 minutes to 24 hours, preferably 2 to 5 hours. If it is good. The heat retaining means and the stirring means are not particularly limited.

<Activated carbon removal process>
Next, the activated carbon is removed by filtering the liquid menthol after stirring. At this time, the filtration method and the apparatus to be used are not particularly limited, and a pressure filter or a suction filter can be used. In this example, a pressure filter was used.

<Recrystallization process>
The filtrate obtained is recrystallized by cooling. Although the cooling rate is not particularly limited, it is preferable to gradually cool, and if the temperature of the menthol melt solution is lowered by leaving the melting container at room temperature, for example, a temperature drop of about 1 to 5 ° C./min. good.

3. Evaluation Method for Purified Natural (L) -Menthol Next, a method for evaluating the purified natural (L) -menthol will be described.
In order to evaluate the taste of the recrystallized natural (L) -menthol purified product, the natural (L) -menthol purified product is added to tobacco. A fixed amount of purified menthol was added to each sample for comparison between samples. In the taste evaluation, two evaluation items are a refreshing feeling and a mint-like aroma. The refreshing sensation refers to the cool feeling that remains in the mouth after smoking, and as described above, the mint-like fragrance refers to the scent of natural mint. When this natural (L) -menthol purified product having both a refreshing sensation and a mint-like fragrance is added to tobacco, menthol tobacco with high palatability is obtained.

  In order to measure the amount of contaminants contained in the natural (L) -menthol purified product, the purified menthol purified product is heated and melted and distilled under reduced pressure. The heating temperature is 80 ° C. and distillation is performed at 2 kPa or less. In addition, the heating temperature should just be the range of 75-95 degreeC. 10-30 ml of ethanol is added to the residue thus obtained. More preferably, it is 20 ml. This ethanol solution is used as a color difference measurement sample.

The degree of purification is evaluated by measuring the L ^* a ^* b ^* value of a color difference measurement sample using a color difference meter according to ISO 7742 (JIS Z8722) and obtaining the saturation. The taste and saturation are correlated, and the higher the taste evaluation, the lower the saturation. In the tobacco product of the present invention, a natural (L) -menthol purified product having a saturation of 1 or less is used.
When the menthol purified product was used as a color difference measurement sample, it was difficult to find a correlation between taste and saturation because there was almost no difference. As a result of extensive studies by the inventors, the purified menthol product is distilled under reduced pressure in a heated and melted state to obtain a vacuum distillation residue. Thereafter, an ethanol solution obtained by adding ethanol to the vacuum distillation residue was used as a color difference measurement sample, and it was found that there is a correlation between taste and saturation.

4). Natural (L) -menthol purified product Finally, the natural (L) -menthol purified product of the present invention will be described.
The natural (L) -menthol purified product contained in the tobacco product of the present invention has a saturation of 1 or less as measured by the above evaluation method. A natural (L) -menthol purified product having a saturation of 1 or less can be a natural (L) -menthol purified product having both a refreshing sensation and a mint-like fragrance. When combined with the product, it becomes a highly-preferred menthol tobacco product.

  The purified natural (L) -menthol contained in the tobacco product of the present invention is not affected by the (L) -menthol content, but is preferably efficient by contacting activated carbon with 90% or more of crude menthol and filtering. Can get to. By removing an appropriate amount of impurities with activated carbon, a purified natural (L) -menthol product having both a refreshing feeling and a mint-like fragrance can be easily purified. After removal of the activated carbon by filtration, a purified natural (L) -menthol can be finally obtained by recrystallization. The (L) -menthol content is preferably 97% or more, and the (L) -menthol content is more preferably 99% or more.

  Moreover, it is preferable that the vacuum distillation residue of the said natural (L) -menthol refined product is less than 0.1 weight%. This makes it possible to obtain a purified natural (L) -menthol product that has both a refreshing sensation with little impurities and a mint-like aroma by a relatively easy process of contacting with activated carbon.

  Hereinafter, the effect of the present invention will be made clearer by showing examples related to tobacco products containing the purified natural (L) -menthol according to the present invention. However, the present invention is not limited to the following examples.

Naturally-derived crude menthol was melted by heating, and activated carbon was added and stirred. Thereafter, the activated carbon was removed, and menthol was recrystallized from the filtrate to obtain a purified natural (L) -menthol product. At this time, sensory evaluation of the obtained purified product was performed. Moreover, the purified menthol product was distilled and ethanol was added to the residue. Using this as a color difference measurement sample, the L ^* a ^* b ^* value was measured to determine the saturation.

(Production Example 1)
500 g of crude menthol was heated and melted, and activated carbon (0 wt%, 1 wt%, 2 wt%, 4 wt%) was added. Subsequently, impurities were adsorbed by stirring for 0, 2.5, 5 and 15 hours in a 60 ° C. warm bath. Thereafter, suction filtration was performed with a 0.5 μm membrane filter to remove the activated carbon. The resulting filtrate was allowed to cool at room temperature and recrystallized. In addition, as the activated carbon in this example, purified white lees (for brewing) manufactured by Nippon Enviro Chemicals was used.
Next, the production procedure of a cigarette with a filter using a natural (L) -menthol purified product will be described. First, the obtained natural (L) -menthol purified product is dissolved in a solvent solution to prepare an additive solution. Ethanol was used as the solvent liquid. The additive solution may contain other fragrance in addition to natural (L) -menthol, and the solvent solution is not limited to ethanol. Moreover, although it does not specifically limit, the compounding ratio of natural (L) -menthol and a solvent liquid should just be 9: 1-5: 5. Thereafter, 10,000 ppm of the prepared additive solution was added to tobacco (American blend, 2 incense) by a method such as spraying or nozzle addition, and the resultant was wound up on a cigarette with a filter. Moreover, about the menthol addition location in a cigarette, it may be a filter other than a tobacco cut, and it is not specifically limited. For Production Examples 2 and 3, cigarettes were produced in the same procedure.
Next, sensory evaluation based on taste will be described. Evaluation was performed by smoking cigarettes by 14 trained professional evaluators. In the taste evaluation, the evaluation items were the strength of the refreshing feeling and the strength of the mint-like aroma. When a natural (L) -menthol purified product having both a refreshing sensation and a mint-like fragrance is blended in a tobacco product, it can be said that the tobacco product has high palatability.
Moreover, 250 g of purified natural (L) -menthol was distilled at 80 ° C. and 2 kPa or less. To the resulting residue was added 20 ml of 95% ethanol. In addition, although 95% ethanol was used as ethanol, it is not restricted to this. Using this as a color difference measurement sample, the L ^* a ^* b ^* value was measured using a color difference meter ZE-2000 (manufactured by Nippon Denshoku Industries Co., Ltd.) in accordance with ISO 7742 (JIS Z8722) to determine the saturation. As a measuring method, a transmission method was used. The results are shown in Table 1. The samples with saturation exceeding 1 were designated as Comparative Examples 1 and 2, respectively, and those below 1 were designated as Examples 1, 2, 3, and 4, respectively.
The saturation can be obtained by calculating L ^* a ^* b ^* measured by a measurement color difference meter according to the following equation. L *, a *, b * (these three values together are called L ^* a ^* b ^* values) are the lightness of the color (L = 0 is black, L = 100 is white diffused color), red and Corresponds to positions between green (a negative value is closer to green, positive values are closer to red), and positions between yellow and blue (b negative values are closer to blue, positive values are closer to yellow) doing.

(Production Example 2)
6,000 g of crude menthol was distilled at 80 ° C. and 2 kPa or less. The product concentrated to a weight of 3,000 g was designated as a double concentrated product. A part of the distillate is used in Production Example 3.
500 g of this two-fold concentrated contaminant was heated and melted, and activated carbon (0 wt%, 1 wt%, 2 wt%, 4 wt%) was added. Subsequently, impurities were adsorbed by stirring for 0, 2.5, 5 and 15 hours in a 60 ° C. warm bath. Thereafter, suction filtration was performed with a 0.5 μm membrane filter to remove the activated carbon. The resulting filtrate was allowed to cool at room temperature and recrystallized.
In the same manner as in Production Example 1 of the obtained purified natural (L) -menthol product, 10,000 ppm was added to the cigarette, and it was rolled up into a cigarette with a filter (American blend, 2 incense). Then, sensory evaluation by taste was performed. In the taste evaluation, the evaluation items were the strength of the refreshing feeling and the strength of the mint-like aroma. When natural (L) -menthol, which has both a refreshing sensation and a mint-like fragrance, is mixed with tobacco, it can be said to be a highly-preference tobacco product.
Moreover, 250 g of purified natural (L) -menthol was distilled at 80 ° C. and 2 kPa or less. To the resulting residue was added 20 ml of 95% ethanol. Using this as a color difference measurement sample, the L ^* a ^* b ^* value was measured using a color difference meter ZE2000 (manufactured by Nippon Denshoku Industries Co., Ltd.) in accordance with ISO 7742 (JIS Z8722) to determine the saturation. The results are shown in Table 1. Comparative examples 3, 4, 5, 6, and 7 were those with saturation exceeding 1, and Example 5 was those with 1 or less.

(Production Example 3)
A mixture of 1500 g, which is a part of the distillate obtained in Production Example 2, and 1,500 g of crude menthol was used as a 1 / 2-fold concentrated product of impurities.
500 g of this contaminant ½-fold concentrated product was heated and melted, and activated carbon (0 wt%, 1 wt%, 2 wt%, 4 wt%) was added. Subsequently, impurities were adsorbed by stirring for 0, 2.5, 5 and 15 hours in a 60 ° C. warm bath. Thereafter, suction filtration was performed with a 0.5 μm membrane filter to remove the activated carbon. The resulting filtrate was allowed to cool at room temperature and recrystallized.
The obtained natural (L) -menthol purified product was added to tobacco at 10,000 ppm in the same manner as in Production Examples 1 and 2, and wound up on a cigarette with a filter (American blend, unscented). Thereafter, sensory evaluation by taste was performed. In the taste evaluation, the evaluation items were the strength of the refreshing feeling and the strength of the mint-like aroma. When natural (L) -menthol, which has both a refreshing sensation and a mint-like fragrance, is mixed with tobacco, it can be said to be a highly-preference tobacco product.
Moreover, 250 g of purified natural (L) -menthol was distilled at 80 ° C. and 2 kPa or less. To the resulting residue was added 20 ml of 95% ethanol. Using this as a color difference measurement sample, the L ^* a ^* b ^* value was measured using a color difference meter ZE2000 (manufactured by Nippon Denshoku Industries Co., Ltd.) in accordance with ISO 7724 (JIS Z8722) to determine the saturation. The results are shown in Table 1. Examples with a saturation of 1 or less were designated as Examples 6, 7, 8, 9, 10, and 11, respectively.

<Evaluation>
A sensory test of refreshing feeling and mint-like aroma was performed on cigarettes during smoking by 14 trained panelists, and they were evaluated on a 10-point scale, and the average was evaluated as follows.
・ Score 8.0 or higher: A rating (very cool or very strong mint-like aroma),
・ Score 7.0 or more and less than 8.0: B rating (strong refreshment or strong mint-like aroma),
・ Score 6.0 or more and less than 7.0: C rating (coolness or mint-like fragrance is slightly weak),
-Rating less than 6.0: D evaluation (a refreshing feeling or a mint-like fragrance is weak).

  The “stirring time” in Table 1 indicates the time of stirring in a 60 ° C. warm bath after adding activated carbon after heating and melting the purified natural (L) -menthol product.

  From Table 1, it was found that the taste evaluation is generally higher for the refreshing feeling and the mint-like aroma as the amount of activated carbon added is larger. However, it was shown that the mint-like aroma was lowered when the amount added was too large relative to the amount of impurities (see Example 11).

  In Production Example 1, the longer the stirring time, the greater the refreshing feeling. In Production Examples 2 and 3, the difference in taste evaluation due to the stirring time could not be confirmed.

  In all Examples, the taste evaluation tended to be higher as the saturation was lower. However, when the saturation is 0.31 or less (see Example 11), the mint-like aroma is impaired. If the saturation is 1 or less, the refreshing feeling and the mint-like fragrance are relatively high. If the saturation is in the range of 0.4 to 0.6, the refreshing feeling and the mint-like fragrance are evaluated. Both were A and very high.

In Production Examples 1 and 2, the L ^* value was higher as the amount of activated carbon added was larger, but the difference was very small. In Production Example 3, a correlation between the amount of activated carbon added and the L ^* value could not be found.

  The tendency similar to the saturation was shown, and in all the production examples, the lower the b value, the higher the taste evaluation. In other words, it was found that when the natural (L) -menthol purified product contains a large amount of impurities, the color difference meter exhibits a yellow color.

  From the above, since the saturation is correlated with the taste evaluation, it can be said that if the saturation is used as an index using this evaluation method, the taste can be evaluated not only by sensory evaluation but also by numerical values. Moreover, generally a natural (L) -menthol refinement | purification thing with high taste evaluation is obtained, so that activated carbon is added much. That is, it can be said that the smaller the amount of impurities, the more highly natural (L) -menthol purified product, but if the amount of impurities is too small, the taste evaluation, particularly the mint-like aroma, is impaired. Therefore, it is considered that the presence of a trace amount of impurities is necessary for the purified natural (L) -menthol having both a refreshing feeling and a mint-like fragrance. And it can be said that the tobacco product which concerns on this invention containing this natural (L) -menthol refined | purified product is a tobacco product which can taste both a refreshing feeling and a mint-like aroma.

<Analysis and measurement of metal elements contained in residue>
Next, in order to confirm whether or not impurities have been reduced and removed by the activated carbon treatment, analysis and measurement of metal elements contained in the residue of the crude menthol before the activated carbon treatment and the purified menthol product after the activated carbon treatment are performed by the following method. went.

  5,000 g of crude menthol before activated carbon treatment and purified menthol after activated carbon treatment prepared under the same conditions as in Example 4 of Production Example 1 were prepared and heated and melted at 60 ° C. Then, it distilled at 80 degreeC and 2 kPa or less, and obtained 0.396g and 0.829g of residues, respectively. This sample was subjected to elemental analysis by ICP MS using the following reagents and measuring instruments.

<Method for preparing analysis sample>
0.1 g to 0.2 g of the obtained residue was transferred to a Teflon (registered trademark) container, and 5 ml of nitric acid solution was added.
An additional 1 ml of H ₂ O ₂ was added and the vessel was sealed. This container was placed in a microwave sample decomposition apparatus and decomposed at 150 ° C. for 20 minutes.
The container was then cooled and removed from the microwave sample digester. The residue in the container was transferred to a 100 ml volumetric flask, made up to 100 ml with ultrapure water, and shaken well.
This sample solution was used for analysis and measurement of metal elements.

A blank with no residue added was also prepared by the above method.
In addition, a standard solution for preparing a calibration curve was prepared using a multi-element standard solution XVI and a nitric acid solution.
Specifically, first, a 0.2% nitric acid solution was added to 1 ml of a multi-element standard solution to make up to 100 ml, thereby preparing a standard stock solution of 1000 ppb.
Using this standard stock solution and 1.0% nitric acid solution, standard solutions of 1 ppb, 3 ppb, 5 ppb, 10 ppb, 15 ppb, and 20 ppb were prepared.

The measurement results were converted to concentration (ppm) using the following formula.
{(Sample lead-blank lead) × volume of sample solution} / (weight of residue g × 1000)
The results are shown in Table 4.

単位：ｐｐｍ

Unit: ppm

From Table 4, it was found that when activated carbon treatment was performed, the amount decreased to 1/29 to 1/118 when the amount of metal element was not performed.
That is, it was found that the amount of contaminants was significantly reduced by the activated carbon treatment.
From this, it can be said that most of impurities including metal elements such as iron, zinc, sodium, magnesium and aluminum can be removed from menthol by adding and purifying activated carbon.
Therefore, the tobacco product containing the purified natural (L) -menthol product of the present invention can be easily and inexpensively added to the tobacco product containing the purified natural (L) -menthol product with less impurities by adding activated carbon. It can be said that it can be supplied.

  The tobacco product containing the purified natural (L) -menthol product of the present invention is suitably used for cigarettes, cigar tobacco, snuff tobacco products, and chewing tobacco products.

DESCRIPTION OF SYMBOLS 1 Filter part 2 Winding part 3 Winding paper 4 Chip paper 5 Winding paper 6 Cigarette engraving 7 Filter 8 Material paper 9 Acetate filter 10 Charcoal filter 11 String 12 Destructible capsule 13 Filler 14 Binder 15 Wrapper 16 Pipe body 17 Cap 18 Mouthpiece 19 Flavor generation Cartridge 20 Sealing part 21 Water-permeable packaging material 22 Wet tobacco product 23 Chewing tobacco product

Claims (5)

A tobacco product characterized by containing a purified natural (L) -menthol product having a saturation of 1 or less as measured by the following methods (1) to (3) and having a refreshing feeling and a mint-like aroma.
(1) A step of distilling a purified natural (L) -menthol purified product under reduced pressure in a heat-melted state to obtain a vacuum distillation residue.
(2) A step of adding ethanol to the vacuum distillation residue obtained in the step (1) to obtain an ethanol solution.
(3) A step of obtaining chroma using a color difference meter according to ISO 7742 (JIS Z8722) using the ethanol solution obtained in the step (2) as a color difference measurement sample.   2. The tobacco product according to claim 1, wherein the saturation is in a range of 0.4 to 0.6.   A wrapping portion composed of a cigarette engraver and a wrapping paper surrounding the cigarette engraving, a filter portion composed of a filter and a wrapping paper enclosing the periphery of the filter, and wrapping at least a part of the wrapping portion and the periphery of the filter portion. The cigarette product according to claim 1, wherein the cigarette product includes a cigarette including a chip paper for connecting the filter section and the filter section.   The tobacco product according to claim 3, wherein the purified natural (L) -menthol is contained in the tobacco.   The tobacco product according to claim 1, wherein a vacuum distillation residue of the purified natural (L) -menthol is less than 0.1% by weight.

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