WO2014203581A1 - Produit de tabac contenant un produit purifié de (l)-menthol naturel - Google Patents

Produit de tabac contenant un produit purifié de (l)-menthol naturel Download PDF

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Publication number
WO2014203581A1
WO2014203581A1 PCT/JP2014/058642 JP2014058642W WO2014203581A1 WO 2014203581 A1 WO2014203581 A1 WO 2014203581A1 JP 2014058642 W JP2014058642 W JP 2014058642W WO 2014203581 A1 WO2014203581 A1 WO 2014203581A1
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WIPO (PCT)
Prior art keywords
menthol
tobacco
natural
product
filter
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2014/058642
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English (en)
Japanese (ja)
Inventor
慎太郎 秋山
百合 吉岡
耕司 安田
晋一 松村
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Japan Tobacco Inc
Original Assignee
Japan Tobacco Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Japan Tobacco Inc filed Critical Japan Tobacco Inc
Priority to CN201480034871.3A priority Critical patent/CN105324041B/zh
Priority to HK16103479.6A priority patent/HK1215359B/zh
Priority to SG11201510174TA priority patent/SG11201510174TA/en
Priority to JP2015522602A priority patent/JP6027680B2/ja
Publication of WO2014203581A1 publication Critical patent/WO2014203581A1/fr
Priority to PH12015502810A priority patent/PH12015502810B1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES OF CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00—Tobacco smoke filters, e.g. filter tips or filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces of cigars or cigarettes
    • A24D3/06—Use of materials for tobacco smoke filters
    • A24D3/14—Use of materials for tobacco smoke filters of organic materials as additive
    • 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
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • A24B15/301—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by aromatic compounds
    • 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
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • A24B15/302—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by natural substances obtained from animals or plants
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES OF CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D1/00—Cigars; Cigarettes
    • A24D1/002—Cigars; Cigarettes with additives, e.g. for flavouring
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES OF CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00—Tobacco smoke filters, e.g. filter tips or filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces of cigars or cigarettes
    • A24D3/04—Tobacco smoke filters characterised by their shape or structure
    • A24D3/048—Tobacco smoke filters characterised by their shape or structure containing additives
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES OF CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00—Tobacco smoke filters, e.g. filter tips or filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces of cigars or cigarettes
    • A24D3/06—Use of materials for tobacco smoke filters
    • A24D3/061—Use of materials for tobacco smoke filters containing additives entrapped within capsules, sponge-like material or the like, for further release upon smoking

Definitions

  • the present invention relates to a tobacco product containing purified natural (L) -menthol, and more specifically, natural (L)-for smoking articles which remove miscellaneous taste and have a refreshing feeling by adding activated carbon to crude menthol.
  • the present invention relates to a tobacco product containing menthol refined product.
  • Menthol is a kind of cyclic monoterpene, an organic compound of alcohol, and is a colorless, colorless crystal with a minty odor. Menthol has several diastereomers and enantiomers. Among them, natural (L) -menthol is often used for toothpaste, confectionery, mouth freshener, etc., as well as topical vasodilator action, skin irritation action, etc. Because it has, it is used also for medicine.
  • menthol has been used as a tobacco perfume since before.
  • the raw material tobacco is burned, it exudes its own distinctive flavor and taste, and it also has peculiar irritation, off-flavor such as bluish or fresh odor, astringent taste and bitter taste.
  • off-flavor such as bluish or fresh odor, astringent taste and bitter taste.
  • licorice, sugar, honey, rum, fruit juice, vanilla and the like are used empirically, and offensive odors and unpleasant tastes are alleviated.
  • cigarette products currently in circulation are cigarettes (cigarette cigarettes), cigars wrapped around with tobacco leaves instead of paper, other cigarette products that enjoy the smell without ignition, snuff products, and direct tobacco leaves
  • Chew tobacco products are known which enjoy the flavor by chewing a mixture comprising
  • snuff products called snus which are used to sandwich tobacco powder sachets between gums and upper lip, are widely used, and chewing tobacco products are popular among baseball players.
  • Natural (L) -menthol is also used as a flavor and taste improver in these tobacco products.
  • Synthetic (L) -menthol has a higher (L) -menthol purity than natural (L) -menthol, but it does not contain aroma component contaminants derived from the raw material mint oil, so it has a flavor point It is inferior to natural (L) -menthol.
  • Natural (L) -menthol contains contaminants because it is extracted from plants such as mint leaves, and the content of the contaminants affects the quality and flavor of natural (L) -menthol. For this reason, various studies have been made on the purification method of natural (L) -menthol.
  • Another method is to dissolve crude menthol in acetonitrile and then cool the solution to crystallize menthol (see, for example, Patent Document 2).
  • natural (L) -menthol having a chemical purity of 99% or more and an optical purity of 99% ee or more can be obtained.
  • organic solvent acetonitrile
  • purified natural (L) -menthol having both coolness and mint-like aroma even when using the technology disclosed in Patent Document 1 or Patent Document 2, and purified natural (L) menthol product It has been difficult to easily and inexpensively supply tobacco products containing
  • the present invention has been made to solve the above-mentioned problems of the prior art, and is a purified natural (L) -menthol product which removes miscellaneous taste and combines a refreshing sensation and a mint-like aroma derived from a natural product. It provides a tobacco product containing.
  • L purified natural
  • the invention according to claim 1 contains a purified natural (L) -menthol product having a saturation of 1 or less and having both a cool feeling and a mint-like odor as measured by the following methods (1) to (3).
  • a tobacco product characterized by (1) A step of vacuum distillation of the purified natural (L) -menthol purified product under heating and melting conditions to obtain a vacuum distillation residue. (2) A step of adding ethanol to the residue obtained in the above step (1) to prepare an ethanol solution. (3) A step of obtaining saturation by using the ethanol solution obtained in the step (2) as a color difference measurement sample and using a color difference meter according to ISO 7724 (JIS Z 8722).
  • the invention according to claim 2 relates to the tobacco product according to claim 1, wherein the color saturation is in the range of 0.4 to 0.6.
  • the invention according to claim 3 is a winding unit comprising a tobacco cut and a wrapping paper wrapping the periphery of the tobacco cutting, a filter and a filter unit comprising a winding paper wrapping the periphery of the filter, at least a part of the winding unit and the filter unit It is a cigarette provided with the tip paper which connects the said winding part and the said filter part by wrapping the circumference
  • the tobacco products of Claim 1 or 2 characterized by the above-mentioned.
  • the invention according to claim 4 relates to the tobacco product according to claim 3, characterized in that the purified natural (L) -menthol is contained in the cut tobacco.
  • the invention according to claim 5 relates to the tobacco product according to claim 1, wherein the reduced-pressure distillation residue of the purified natural (L) -menthol product is less than 0.1% by weight.
  • the palatability is measured 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. It is possible to confirm the presence of a large impacting contaminant.
  • the purified natural (L) -menthol having a saturation of 1 or less can be made into a purified natural (L) -menthol having both a cool feeling and a mint-like aroma.
  • the purified natural (L) -menthol By incorporating the purified natural (L) -menthol into a tobacco product, it is possible to obtain a tobacco product having a cool feeling and a mint-like aroma.
  • the saturation is within the range of 0.4 to 0.6.
  • a tobacco product containing purified natural (L) -menthol is purified from natural (L) -menthol having a stronger refreshing feeling and mint-like aroma than a tobacco product containing the purified natural (L) -menthol according to claim 1
  • Products can be tobacco products (see Table 1).
  • the purified natural (L) menthol according to claim 1 by containing the purified natural (L) -menthol according to claim 1 in tobacco cutting, the purified natural (L) menthol can be easily transferred to smoke when smoking. It is possible to obtain a cigarette having a cool feeling and a mint-like aroma.
  • the reduced-pressure distillation residue of the purified natural (L) -menthol product when the reduced-pressure distillation residue of the purified natural (L) -menthol product is less than 0.1% by weight, there is less contamination by relatively easy process of contacting activated carbon. It is possible to obtain a purified natural (L) -menthol compound having a refreshing feeling and a mint-like aroma, and by including this, it is possible to obtain a tobacco product having a refreshing feeling and a mint-like aroma.
  • A is a cross-sectional view of a cigarette provided with a string containing purified natural (L) -menthol in the center of the filter, and (B) is its AA cross-sectional view.
  • A) is a cross-sectional view of a cigarette provided with a destructible capsule containing a purified natural (L) -menthol in the interstice in the filter, and (B) the cigarette of the cigarette provided with the destructive capsule in the interstice in the filter It is a cross-sectional view when a capsule is destroyed.
  • A Schematic of cigar and
  • B Transverse view of cigar.
  • FIG. 1 illustrates the use of chewing tobacco products.
  • 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. Contains a refined natural (L) -menthol compound with a mint-like odor. Cigarettes suitable for containing the purified natural (L) -menthol of the present invention will be described with reference to FIGS. 1 to 4.
  • FIG. 1 is a schematic view of a cigarette having one type of filter.
  • the cigarette comprises a winding portion (2) consisting of a cigarette paper (6) and a wrapping paper (5) wrapping the periphery of the cigarette cutting (6), and a filter (7) and a winding paper (3) wrapping around the filter (7).
  • a filter section (1), and chip paper (4) for connecting the winding section (2) and the filter section (1) by wrapping at least a part of the winding section (2) and the periphery of the filter section (1) Prepare.
  • the tobacco engraving (6) is a combination of tobacco leaf (yellow species, burley type, etc.) engraving, incising of the inside, sheet tobacco engraving and relaxation engraving.
  • Wrapping paper (5) contains flax and wood pulp as raw materials, may contain calcium carbonate to suppress burning odor of paper and match burning rate with tobacco cutting, and may contain citrate as a combustion improver. good. Further, as the paper roll (5), a fine holed one may be used to control the air inflow.
  • the filter (7) is generally an acetate filter made of acetate fiber, but neo-sheet, rayon, paper or the like may be used. Although a plain paper is generally used as a material of a paper roll (3), it is not specifically limited. Although wood pulp, calcium carbonate and titanium oxide are generally used as the material of the chip paper (4), fine holes may be used in order to control the inflow of air. In this case, the purified natural (L) -menthol can be contained in the cut tobacco (6) and / or the filter (7).
  • FIG. 2 is a schematic view of a cigarette having two types of filters.
  • the filter section (1) has almost the same structure as the cigarette having one type of filter in FIG. 1, but the filter section (1) is composed of two types of filters, an acetate filter (9) and a charcoal filter (10). Also, a base paper (8) wrapping around the acetate filter (9) and the charcoal filter (10), and a paper roll (3) connecting the acetate filter (9) and the charcoal filter (10) are provided.
  • the charcoal filter (10) is a dual or triple structure in which activated carbon is incorporated by combining acetate fiber, neosheet, rayon and paper.
  • the material paper (8) is generally similar to the paper (3), although plain paper is used as a material, but it is not particularly limited. In this case, as in the case of cigarettes having one type of filter, purified natural (L) -menthol may be contained in tobacco cut (6) and / or acetate filter (9) and / or charcoal filter (10). it can.
  • FIG. 3 is (A) a cross-sectional view of a cigarette provided with a string containing purified natural (L) -menthol at the center of the filter and (B) its AA cross-sectional view.
  • the structure is substantially the same as that of the cigarette having one type of filter in FIG. 1, but it has a string (11) located approximately at the center of the filter.
  • the cord (11) is generally made of cotton, but is not particularly limited, and a natural (L) menthol refined product is applied and used.
  • the purified natural (L) -menthol can be contained in the filter (7) and / or the tobacco cut (6) in addition to the string (11).
  • FIG. 4 shows (A) a cross-sectional view of a cigarette provided with a destructible capsule containing natural (L) -menthol purified material in the interstice in the filter and (B) a cigarette provided with the destructible capsule in the interstice in the filter
  • FIG. 6 is a cross-sectional view of the capsule of FIG. It is similar in construction to the cigarette with one type of filter in FIG. 1, but with a frangible capsule (12) in the gap in the filter.
  • the destructible capsule (12) is filled with purified natural (L) -menthol, and by applying pressure with a finger to break before or during smoking, the destructive capsule (12) is The purified natural (L) -menthol is released to the filter (7).
  • the membrane 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.
  • the purified natural (L) -menthol can be contained in the filter (7) and / or the cut tobacco (6) in addition to the destructible capsule (12).
  • purified natural (L) -menthol may be applied to the inside of a cigarette packaging container.
  • an aluminum laminated paper coated with a purified natural (L) -menthol product may be inserted into a cigarette packaging container, and the purified natural (L) -menthol product directly inside the packaging container May be applied.
  • purified natural (L) -menthol By applying purified natural (L) -menthol to the inside of the cigarette packaging container, the natural (L) -menthol purified product is transferred to cigarette tobacco cut (6) and / or filter (7) during storage. It can be done.
  • FIG. 5 shows (A) a schematic view and (B) a cross-sectional view of a cigar.
  • the cigar comprises a filler (13) comprising tobacco leaf or cut tobacco, a binder (14) optionally wrapping around the filler with tobacco leaf, and a wrapper (15) wrapping around the filler or binder with tobacco leaf.
  • purified natural (L) -menthol can be contained in tobacco leaf or tobacco mincing.
  • a snuff product suitable for containing the purified natural (L) -menthol of the present invention is described with reference to FIGS. 6 and 7.
  • Snuff products include snuff, flavor suction pipes, moist smokeless tobacco products and the like.
  • FIG. 6 shows the structure and use of the moist suction pipe and
  • FIG. 7 the moist smokeless tobacco product.
  • Snuff is a dry or moist tobacco powder. The dry tobacco powder is placed on the thumb of the back of the hand, a pinch of the base of the forefinger, and sucked from the nose.
  • moist tobacco powder is generally applied to the gums as a method of using snuff.
  • the purified natural (L) -menthol can be contained in the tobacco powder.
  • FIG. 6 is (A) a schematic view and (B) a cross-sectional view of a flavor suction pipe which is a snuff product.
  • the flavor suction pipe has 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), a pipe body (16 And a tobacco cut (6) filled in the replaceable flavor generation cartridge (19) and the flavor generation cartridge (19).
  • the purified natural (L) -menthol can be contained in the tobacco cut (6) in the cartridge (19).
  • FIG. 7 shows (A) schematic, (B) AA cross section of the moist smokeless tobacco product, which is a snuff product, and (C) a usage of the moist smokeless tobacco product (22).
  • the moist smokeless tobacco product (22) comprises a cut water containing tobacco (6), a water permeable packaging material (21) for wrapping the cut tobacco (6), and a seal (20) for sealing the water permeable packaging material (21) ).
  • the water content of the cut tobacco (6) may be 20 to 70%, and a nonwoven fleece is generally used as a packaging material, but it is not particularly limited as long as it is a material that is permeable to water.
  • the material of the seal is also not particularly limited.
  • the moist smokeless tobacco product (22) is used by being sandwiched between the upper lip and the gums, as shown in FIG. 7 (C). In this case, purified natural (L) -menthol can be contained in water-containing tobacco shreds (6).
  • a chewing tobacco product suitable for containing the purified natural (L) -menthol of the present invention is described with reference to FIG.
  • FIG. 8 is a diagram showing how to use the chewing tobacco product (23).
  • Chew tobacco products (23) include plugs, twists, scraps, chewing gum and the like.
  • the chewing tobacco product (23) is used by being put directly in the mouth for chewing as shown in FIG.
  • the plug is obtained by wrapping the tobacco leaf or tobacco cut into a sheet and wrapping it with the upper rolled leaf and compressing it again.
  • the sheet of tobacco cut is generally square, but the shape is not particularly limited.
  • the purified natural (L) -menthol can be contained in the tobacco leaf, cut tobacco and / or upper rolled leaf. Twist twists tobacco leaf, wraps it in upper roll leaf, twists it again and applies pressure.
  • the purified natural (L) -menthol can be contained in the tobacco leaf and / or the top roll leaf.
  • the scrap is one that directly bites the tobacco cut into the mouth.
  • purified natural (L) -menthol can be contained in the tobacco cut.
  • the chewing gum is one obtained by processing tobacco components into chewing gum without using tobacco leaf or tobacco cutting.
  • purified natural (L) -menthol can be contained in chewing gum together with the tobacco component.
  • the crude menthol according to the present invention can be obtained by steam distillation or the like from Mentha aquatica, Mentha arvensis, Mentha longifolia, Mentha pulegium, Mentha spicata, Mentha piperita or the like belonging to the genus Laminaceae.
  • these production areas, varieties, etc. are not particularly limited.
  • crude menthol obtained from essential oils extracted from the leaf and above-ground parts of these mints by means of steam distillation and the like is used in the present invention.
  • the crude menthol content is preferably as high as possible, preferably 90% or more, as the content of (L) -menthol is as high as possible.
  • the method of extraction is not particularly limited.
  • crude menthol may be natural (L) -menthol obtained by crystallizing an essential oil and centrifuging it, or it may be further purified by distillation, column chromatography or the like.
  • the extracted crude menthol is heated and melted before adding activated carbon to give 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 it is not particularly limited.
  • Activated carbon is added to the liquid crude menthol. At this time, an amount of 0.1 to 10% by weight of coarse 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 contaminants in the crude menthol can not be sufficiently removed, and as a result, the unwanted taste can not be removed, which is not preferable. On the other hand, if the amount of activated carbon added exceeds 10% by weight, the crude menthol impurities are removed more than necessary, and the mint-like aroma is impaired, which is not preferable. Mint-like aroma refers to the smell of natural mint.
  • 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. That's fine.
  • the heat retention means and the stirring means are not particularly limited.
  • the activated carbon is removed by filtering the liquid menthol after stirring.
  • the method of filtration and the device to be used are not particularly limited, and a pressure filter or a suction filter can be used. In the present example, a pressure filter was used.
  • the obtained filtrate is recrystallized to cool.
  • the cooling rate is not particularly limited, gradual cooling is preferable, and the temperature of the menthol melting solution may be lowered by, for example, leaving the melting vessel at room temperature, for example, if the temperature drop is about 1 to 5 ° C / min. good.
  • the purified menthol purified product is heated and thawed and distilled under reduced pressure.
  • the heating temperature is 80 ° C., and distillation is performed at 2 kPa or less.
  • the heating temperature may be in the range of 75 to 95 ° C. 10 to 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 the color difference measurement sample using a color difference meter in accordance with ISO 7742 (JIS Z8722) to determine the saturation.
  • the taste and saturation are correlated, and the higher the taste evaluation, the lower the saturation.
  • the tobacco products of the present invention use natural (L) -menthol purified products having a chroma of 1 or less.
  • L natural
  • the menthol purified product which has been purified is distilled under reduced pressure in a heating and melting state to obtain a vacuum distillation residue. After that, by using an ethanol solution obtained by adding ethanol to a vacuum distillation residue as a color difference measurement sample, it was found that there is a correlation between taste and saturation.
  • the purified natural (L) -menthol contained in the tobacco product of the present invention is characterized in that the color saturation as measured by the above evaluation method is 1 or less.
  • a purified natural (L) -menthol product having a saturation of 1 or less can be a purified natural (L) -menthol compound having a cool feeling and a mint-like aroma, and this purified natural (L) -menthol product is a tobacco product. When blended into products, it becomes menthol tobacco products with high palatability.
  • the purified natural (L) -menthol contained in the tobacco product of the present invention is not influenced by the (L) -menthol content, it is preferable to contact activated carbon with crude menthol at 90% or more and filter it efficiently. Can be obtained. By removing an appropriate amount of contaminants with activated carbon, it is possible to easily purify a purified natural (L) -menthol having both a refreshing feeling and a mint-like aroma. After removal of the activated carbon by filtration, recrystallization can finally obtain a purified natural (L) -menthol product.
  • the (L) -menthol content is preferably 97% or more, and the (L) -menthol content is more preferably 99% or more.
  • the reduced-pressure distillation residue of the purified natural (L) -menthol is preferably less than 0.1% by weight. As a result, it is possible to obtain a purified natural (L) -menthol compound which has both a refreshing feeling and a mint-like odor with less impurities by the relatively easy process of contacting with activated carbon.
  • the naturally occurring crude menthol was heated and melted, 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. At this time, sensory evaluation of the obtained purified product was performed. Also, the menthol purified product was distilled, and ethanol was added to the residue. The L * a * b * value was measured using this as a color difference measurement sample to determine the saturation.
  • the obtained purified natural (L) -menthol product is dissolved in a solvent solution to prepare an additive solution.
  • Ethanol was used as a solvent solution.
  • the additive liquid may contain other flavors in addition to natural (L) -menthol, and the solvent liquid is not limited to ethanol.
  • the blending ratio of natural (L) -menthol to the solvent liquid may be 9: 1 to 5: 5.
  • 10,000 ppm of the additive solution thus prepared was added to cut tobacco (American Blend, 2 unflavored) by a method such as spray spraying or nozzle addition, and wound up into a cigarette with a filter.
  • menthol addition location in a cigarette it may be a filter other than tobacco cutting, and is not specifically limited.
  • Cigarettes were produced in the same manner for Production Examples 2 and 3. Next, sensory evaluation by taste will be described. The evaluation was conducted by smoking a cigarette by 14 trained professional evaluators. In the evaluation of taste, two items of strength of refreshing feeling and strength of mint-like aroma were used as evaluation items. When a natural (L) -menthol purified product having a refreshing feeling and a mint-like aroma is blended in a tobacco product, it can be said that the tobacco product is highly palatable. Further, 250 g of purified natural (L) -menthol was distilled at 80 ° C. and 2 kPa or less.
  • the saturation can be determined by calculating L * a * b * measured by the measurement color difference meter according to the following equation.
  • the resulting natural (L) -menthol purified product was added in an amount of 10,000 ppm to tobacco shredded in the same manner as in Production Example 1 and rolled up into a cigarette with a filter (American blend, 2 unflavored). Then, sensory evaluation by taste was performed. In the evaluation of taste, two items of strength of refreshing feeling and strength of mint-like aroma were used as evaluation items. Natural (L) -menthol, which has a refreshing feeling and a mint-like aroma, can be considered as a highly palatable tobacco product when it is incorporated into tobacco. Further, 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.
  • the purified purified natural (L) -menthol product was added to the cut tobacco in an amount of 10,000 ppm in the same manner as in Production Examples 1 and 2 and rolled up into a cigarette with a filter (American blend, 2 unflavored). After that, sensory evaluation was performed by taste. In the evaluation of taste, two items of strength of refreshing feeling and strength of mint-like aroma were used as evaluation items. Natural (L) -menthol, which has a refreshing feeling and a mint-like aroma, can be considered as a highly palatable tobacco product when it is incorporated into tobacco. Further, 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.
  • the “stirring time” in Table 1 indicates the time after heating and thawing the natural (L) -menthol purified product and then adding activated carbon and stirring under a 60 ° C. water bath.
  • the saturation the higher the taste evaluation.
  • the saturation 0.31 or less (see Example 11)
  • the mint-like aroma is impaired.
  • the saturation is 1 or less
  • the evaluation of coolness and mint-like aroma is relatively high
  • the saturation is in the range of 0.4 to 0.6
  • the evaluation of coolness and mint-like aroma is Both were A and very high.
  • the saturation is correlated with the taste evaluation, it can be said that the taste can be evaluated not only by the sensory evaluation but also numerically if the saturation is used as an index by using this evaluation method.
  • natural (L) -menthol purified products with high evaluation of taste can be obtained by adding more activated carbon.
  • the more refined natural (L) -menthol purified product can be said as the smaller the amount of impurities, the contrary the evaluation of taste, particularly the mint-like aroma is impaired if the amount of impurities is too small. Therefore, it is considered that the purified natural (L) -menthol having both a refreshing feeling and a mint-like odor requires the presence of a trace amount of contaminants.
  • the tobacco product according to the present invention containing the purified natural (L) -menthol is a tobacco product which can taste both a refreshing sensation and a mint-like aroma.
  • 0.1 g to 0.2 g was transferred to a Teflon container, and 5 ml of a nitric acid solution was added. Another 1 ml of H 2 O 2 was added and the vessel was sealed. The vessel was placed in a microwave sample decomposition apparatus and decomposed at 150 ° C. for 20 minutes. The vessel was then cooled and removed from the microwave sampler. The residue in the vessel 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.
  • Blanks to which no residue was added were also prepared by the above method.
  • a standard solution for preparing a calibration curve was prepared using a multielement standard solution XVI and a nitric acid solution. Specifically, a 0.2% nitric acid solution was first added to 1 ml of a multi-element standard solution to make up to 100 ml, and a standard stock solution of 1000 ppb was prepared. 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 tobacco product containing the purified natural (L) -menthol which is the present invention is suitably used for cigarettes, cigars, snuff products and chewing tobacco products.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Botany (AREA)
  • Manufacture Of Tobacco Products (AREA)
  • Cigarettes, Filters, And Manufacturing Of Filters (AREA)
  • Fats And Perfumes (AREA)
  • Spectrometry And Color Measurement (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

[Problème] Produire un produit de tabac caractérisé en ce qu'il contient un produit purifié de (L)-menthol naturel qui élimine les goûts déplaisants et combine une sensation de fraîcheur et un arôme similaire à la menthe. [Solution] La présente invention concerne un produit de tabac caractérisé en ce qu'il contient un produit purifié de (L)-menthol naturel qui combine une sensation de fraîcheur et un arôme similaire à la menthe et qui a une saturation de couleur de 1 ou moins telle que mesurée par le procédé de (1) à (3) ci-dessous. (1) Étape de distillation sous vide du produit purifié de (L)-menthol naturel tandis que le produit purifié est dans un état thermiquement fondu et d'obtention d'un résidu de distillation sous vide. (2) Étape d'ajout d'éthanol au résidu de distillation sous vide obtenu dans l'étape (1) et d'obtention d'une solution éthanolique. (3) Étape de préparation d'un échantillon de mesure de différence de couleur de la solution éthanolique obtenue dans l'étape (2) et d'évaluation de la saturation de couleur au moyen d'un dispositif de mesure de différence de couleur conforme à l'ISO 7742 (JIS Z 8722).
PCT/JP2014/058642 2013-06-18 2014-03-26 Produit de tabac contenant un produit purifié de (l)-menthol naturel Ceased WO2014203581A1 (fr)

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CN201480034871.3A CN105324041B (zh) 2013-06-18 2014-03-26 含有天然(l)-薄荷醇精制物的烟草制品
HK16103479.6A HK1215359B (zh) 2013-06-18 2014-03-26 含有天然(l)-薄荷醇精制物的烟草制品
SG11201510174TA SG11201510174TA (en) 2013-06-18 2014-03-26 Tobacco product containing purified natural (l)-menthol
JP2015522602A JP6027680B2 (ja) 2013-06-18 2014-03-26 天然（ｌ）−メントール精製物を含有するたばこ製品
PH12015502810A PH12015502810B1 (en) 2013-06-18 2015-12-17 Tobacco product containing purified natural (l)-menthol

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JP2013-127965 2013-06-18

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CN106868926A (zh) * 2017-03-09 2017-06-20 广东中烟工业有限责任公司 一种中药组合物在制备卷烟纸中的应用以及卷烟纸与制备方法
CN107328718A (zh) * 2017-05-31 2017-11-07 广东中烟工业有限责任公司 一种以三乙酸甘油酯为溶剂的烟用香精的质量快速判别方法
JP2018531623A (ja) * 2015-09-08 2018-11-01 アール・ジエイ・レイノルズ・タバコ・カンパニー タバコ材料の高圧低温殺菌
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CN105324041A (zh) 2016-02-10
SG11201510174TA (en) 2016-01-28
CN105324041B (zh) 2018-12-04
PH12015502810A1 (en) 2016-03-14
JPWO2014203581A1 (ja) 2017-02-23
MY173599A (en) 2020-02-07
PH12015502810B1 (en) 2018-11-28
HK1215359A1 (zh) 2016-08-26

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