US20200359672A1 - Tobacco extract, method for producing tobacco extract, and non-combustion flavor inhaler including tobacco extract - Google Patents

Tobacco extract, method for producing tobacco extract, and non-combustion flavor inhaler including tobacco extract Download PDF

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US20200359672A1
US20200359672A1 US16/913,934 US202016913934A US2020359672A1 US 20200359672 A1 US20200359672 A1 US 20200359672A1 US 202016913934 A US202016913934 A US 202016913934A US 2020359672 A1 US2020359672 A1 US 2020359672A1
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Prior art keywords
tobacco extract
tobacco
fraction
extract according
extraction
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Inventor
Masahiro Chida
Masashi Mizutani
Shohei MIYAGO
Akane YOSHIZAKI
Kei Kobayashi
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Japan Tobacco Inc
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Japan Tobacco Inc
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Assigned to JAPAN TOBACCO INC. reassignment JAPAN TOBACCO INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: YOSHIZAKI, AKANE, KOBAYASHI, KEI, MIYAGO, Shohei, CHIDA, MASAHIRO, MIZUTANI, MASASHI
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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
    • A24B15/12—Chemical features of tobacco products or tobacco substitutes of reconstituted tobacco
    • 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
    • A24B15/243—Nicotine
    • 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
    • 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
    • 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
    • A24B15/26—Use of organic solvents for extraction

Definitions

  • the present invention relates to a tobacco extract, a method for producing the tobacco extract, and a non-combustion type flavor inhaler using the tobacco extract.
  • a tobacco extract or a method for extracting the tobacco extract is used for the purpose of ameliorating the flavor of a tobacco raw material or for the purpose of lowering the contents of components in a tobacco raw material.
  • a method for obtaining a tobacco raw material having satisfactory flavor by subjecting a leaf tobacco material to extraction with a low-polar solvent, further subjecting a residue after the extraction to extraction with a highly polar solvent, and pouring an extract extracted with the low-polar solvent back into a resultant residue (PTL1) a method for preparing a tobacco product containing a lowered amount of a phenol-based compound by subjecting a tobacco material to extraction with a solvent to provide an extract and a residue, treating the extract with phenol oxidase to lower the amount of the phenol-based compound, and combining a resultant with a tobacco residue (PTL2), a method of using as refined oil a fraction obtained by subjecting leaf tobacco to steam distillation and mixing the fraction with the other materials (PTL3), and the like are reported.
  • a tobacco extract When a tobacco extract is utilized for a non-combustion type flavor inhaler, there exist, as means of extraction, methods such as extraction with a solvent containing an organic solvent, water, or the like, which is a general tobacco-extracting method, high-pressure carbonic acid gas extraction, and steam distillation.
  • methods such as extraction with a solvent containing an organic solvent, water, or the like, which is a general tobacco-extracting method, high-pressure carbonic acid gas extraction, and steam distillation.
  • a tobacco extract obtained by any of these methods is applied to a non-combustion type flavor inhaler using propylene glycol, glycerin, or the like as a solvent, insoluble particles are generated and quality abnormality such as precipitation brings about a problem in the case where a component insoluble in, for example, propylene glycol or glycerin exists.
  • insoluble particles contain a large amount of a hydrophobic component containing some glucosides and higher fatty acids, and polymer compounds each having a different cyclic structure and substituent in the case where extraction means is solvent extraction and a volatile organic solvent or a halogen-based organic solvent is used as an extraction solvent.
  • insoluble particles are also generated in a tobacco extract obtained by water extraction when the tobacco extract is applied to a non-combustion type flavor inhaler using propylene glycol, glycerin, or the like as a solvent. This is because a component insoluble in propylene glycol or glycerin, such as a protein or an inorganic salt, is contained in the water-extracted product.
  • hydrophobic components such as refined oil are contained in a resultant water-insoluble fraction in the case where extraction means is steam distillation.
  • hydrophobic components are considered to be a main cause for the insoluble particles to be generated when propylene glycol, glycerin, a mixture thereof, or the like is applied as a solvent.
  • a mixed liquid is heated at a heat source section to be vaporized at a boiling point of a polyol (such as propylene glycol or glycerin) which is a solvent for the mixed liquid or at a temperature close to the boiling point of the mixed product of the polyols, and a hardly volatile component, which is not gasified at this temperature, retains at the heat source section and scorches to be a cause for a change in flavor.
  • a polyol such as propylene glycol or glycerin
  • a problem to be solved by the present invention is to provide a tobacco extract that, when utilized for a non-combustion type flavor inhaler, does not generate insoluble particles in a mixed liquid or the like, and can thereby suppress scorching at the heat source section and also suppress the change in flavor.
  • the present inventors have advanced diligent studies in order to solve the problems to find that a tobacco extract produced by subjecting all or a portion of a tobacco plant body to steam distillation to obtain a fraction, subjecting the fraction to solvent extraction with a suitable organic solvent, and removing the organic solvent has low contents of a hydrophobic component and a hardly volatile component; and that the tobacco extract does not generate insoluble particles in a mixed liquid or the like when utilized for a non-combustion type flavor inhaler, and that the tobacco extract can suppress scorching at a heat source section and also suppress a change in flavor particularly when utilized for a mixed liquid to be used for a heating type flavor inhaler which is one embodiment of the non-combustion type flavor inhaler; and have thereby completed the present invention.
  • the present invention includes, but not limited to, the following embodiments and aspects.
  • a tobacco extract wherein, when analysis by gas chromatography (a hydrogen flame ionization detector) is performed using a column comprising a stationary phase of 100% of dimethyl polysiloxane, a total peak area of a component group having a retention index (RI) of less than 2100 is 78% or more of a total peak area of the whole.
  • gas chromatography a hydrogen flame ionization detector
  • a non-combustion type flavor inhaler comprising the tobacco extract according to any one of [1] to [11].
  • a heating type flavor inhaler comprising the tobacco extract according to any one of [1] to [12].
  • a mixed liquid for a heating type flavor inhaler comprising the tobacco extract according to any one of [1] to [12].
  • a heating type flavor inhaler comprising the mixed liquid for a heating type flavor inhaler according to [15].
  • a tobacco extract of the present invention enables providing a non-combustion type flavor inhaler that does not cause a problem such as precipitation by a solvent-insoluble component, suppresses scorching at a heat source section, and also suppresses a change in flavor when the tobacco extract is utilized for the non-combustion type flavor inhaler.
  • liquid-to-liquid transfer of a fraction with a solvent, the fraction obtained by steam distillation in an extraction step, while keeping the fraction acidic enables further providing a tobacco extract in which an alkaloid content is reduced or an alkaloid is removed.
  • FIG. 1 is a chromatogram of a tobacco extract solution by gas chromatography (GC/FID), wherein the tobacco extract solution obtained in such a way that: a fraction obtained by subjecting a tobacco leaf to steam distillation is subjected to liquid-to-liquid transfer using ethyl acetate; an ethyl acetate layer at an upper portion is separated and extracted; ethyl acetate is then removed under reduced pressure; and further, a resultant dried and solidified product (tobacco extract component) is dissolved in ethyl acetate in a weight of 100 times the weight of the dried and solidified product.
  • a vertical line in the chromatogram shows a retention time when a retention index (RI) is 2100.
  • RI retention index
  • a peak of linolenic acid is shown by an arrow.
  • FIG. 2 is a chromatogram of a tobacco extract solution by GC/FID, wherein the tobacco extract solution obtained in such a way that: a fraction obtained by subjecting a tobacco leaf to steam distillation is subjected to liquid-to-liquid transfer using diethyl ether; a diethyl ether layer at an upper portion is separated and extracted; diethyl ether is then removed under reduced pressure; and further, a resultant dried and solidified product (tobacco extract component) is dissolved in diethyl ether in a weight of 100 times the weight of the dried and solidified product.
  • a vertical line in the chromatogram shows a retention time when RI is 2100.
  • a peak of linolenic acid is shown by an arrow.
  • FIG. 3 is a chromatogram of a tobacco extract solution by GC/FID, wherein the tobacco extract solution obtained in such a way that: a fraction obtained by subjecting a tobacco leaf to steam distillation is subjected to liquid-to-liquid transfer using chloroform; a chloroform layer at a lower portion is separated and extracted; chloroform is then removed under reduced pressure; and further, a resultant dried and solidified product (tobacco extract component) is dissolved in chloroform in a weight of 100 times the weight of the dried and solidified product.
  • a vertical line in the chromatogram shows a retention time when RI is 2100.
  • a peak of linolenic acid is shown by an arrow.
  • FIG. 4 is a chromatogram of a tobacco extract solution by GC/FID, wherein the tobacco extract solution obtained in such a way that: a fraction obtained by subjecting a tobacco leaf to steam distillation is subjected to liquid-to-liquid transfer using n-hexane; a n-hexane layer at an upper portion is separated and extracted; n-hexane is then removed under reduced pressure; and further, a resultant dried and solidified product (tobacco extract component) is dissolved in n-hexane in a weight of 100 times the weight of the dried and solidified product.
  • a vertical line in the chromatogram shows a retention time when RI is 2100.
  • a peak of linolenic acid is shown by an arrow.
  • FIG. 5 is a chromatogram of a tobacco extract by GC/FID, wherein the tobacco extract obtained by subjecting a tobacco leaf to solvent immersion extraction with ethyl acetate.
  • a vertical line in the chromatogram shows a retention time when RI is 2100.
  • FIG. 6 is a chromatogram of a tobacco extract by GC/FID, wherein the tobacco extract obtained by subjecting a tobacco leaf to solvent immersion extraction with diethyl ether.
  • a vertical line in the chromatogram shows a retention time when RI is 2100.
  • FIG. 7 is a chromatogram of a tobacco extract by GC/FID, wherein the tobacco extract obtained by subjecting a tobacco leaf to solvent immersion extraction with chloroform.
  • a vertical line in the chromatogram shows a retention time when RI is 2100.
  • FIG. 8 is a chromatogram of a tobacco extract by GC/FID, wherein the tobacco extract obtained by subjecting a tobacco leaf to solvent immersion extraction with n-hexane.
  • a vertical line in the chromatogram shows a retention time when RI is 2100.
  • FIG. 9 is a chromatogram of a tobacco extract by GC/FID, wherein the tobacco extract obtained by subjecting a tobacco leaf to solvent immersion extraction with acetone.
  • a vertical line in the chromatogram shows a retention time when RI is 2100.
  • FIG. 10 is a chromatogram of a tobacco extract by GC/FID, wherein the tobacco extract obtained by subjecting a tobacco leaf to solvent immersion extraction with ethanol.
  • a vertical line in the chromatogram shows a retention time when RI is 2100.
  • FIG. 11 is a chromatogram of a tobacco extract by GC/FID, wherein the tobacco extract obtained by subjecting a tobacco leaf to solvent immersion extraction with methanol.
  • a vertical line in the chromatogram shows a retention time when RI is 2100.
  • FIG. 12 is a chromatogram of a tobacco extract by GC/FID, wherein the tobacco extract obtained by subjecting a tobacco leaf to warm water extraction to the warm water extraction solution, and then subjecting subjecting the warm water extraction solution to solvent extraction with ethyl acetate,.
  • a vertical line in the chromatogram shows a retention time when RI is 2100.
  • FIG. 13 is a chromatogram of a tobacco extract by GC/FID, wherein the tobacco extract obtained by subjecting a tobacco leaf to warm water extraction to the warm water extraction solution, and then subjecting the warm water extraction solution to solvent extraction with diethyl ether.
  • a vertical line in the chromatogram shows a retention time when RI is 2100.
  • FIG. 14 is a chromatogram of a tobacco extract by GC/FID, wherein the tobacco extract obtained by subjecting a tobacco leaf to warm water extraction to the warm water extraction solution, and then subjecting the warm water extraction solution to solvent extraction with chloroform.
  • a vertical line in the chromatogram shows a retention time when RI is 2100.
  • FIG. 15 is a chromatogram of a tobacco extract by GC/FID, wherein the tobacco extract obtained by subjecting a tobacco leaf to warm water extraction to the warm water extraction solution, and then subjecting the warm water extraction solution to solvent extraction with n-hexane.
  • a vertical line in the chromatogram shows a retention time when RI is 2100.
  • the present invention provides a tobacco extract, wherein, when analysis by gas chromatography is performed using a column having a stationary phase of 100% of dimethyl polysiloxane, a total peak area of a component group having a retention index (RI) of less than 2100 is 78% or more of a total peak area of the whole.
  • the analysis is performed by gas chromatography (hydrogen flame ionization detector).
  • the tobacco extract of the present invention is produced using all or a portion of a tobacco plant body as a raw material.
  • the “portion of a tobacco plant body” refers to a part of a tobacco plant body, includes, for example, a leaf (including an upper leaf, a true leaf, an upper middle leaf, a middle leaf, and a lower leaf), a pinched part, an axillary bud, a stem, a trunk, a flower, a root, and a seed, or mixtures thereof, and is preferably a leaf, an axillary bud, and a trunk.
  • All or a portion of a tobacco plant body may be used as it is, or all or a portion of a tobacco plant body cut, pulverized, or ground into a slender piece-like, slurry-like, or fine particle-like product may be used.
  • All or a portion of a tobacco plant body harvested from farmland or the like may be used as it is, all or a portion of a tobacco plant body obtained by being left to stand indoors or outdoors for a predetermined period of time to dissipate part of moisture may be used, or all or a portion of a tobacco plant body obtained by almost dissipating moisture with a drier (including a freeze drier) or the like may be used.
  • the “retention index (RI)” refers to an index relatively representing a retention ratio of a n-alkane to a compound as an object of analysis based on the numbers of carbon atoms of a linear hydrocarbon (n-alkane) in the analysis by gas chromatography.
  • the retention index (RI) when a column having a predetermined stationary phase is used, the same compound theoretically has the same value even if the length of the column, the flow rate of a carrier gas, and the like are changed.
  • the retention index (RI) is specifically calculated by the following formula.
  • n-alkane mixture in a range from n-hexane (C 6 , RI: 600) to n-pentatriacontane (C 35 , RI:3500) is used as the retention index (RI), but the n-alkane mixture which is used when the retention index (RI) is calculated is not limited to this.
  • the column which is used in gas chromatography has, for example, a non-polar or low-polar stationary phase, preferably a non-polar stationary phase.
  • a column having a non-polar stationary phase a column having a stationary phase of, for example, 100% of dimethyl polysiloxane can be used.
  • DB-1 manufactured by Agilent Technologies, Inc.
  • the column is not limited to this.
  • a column having a low-polar stationary phase a column having a stationary phase of, for example, 95% of dimethyl polysiloxane/5% of diphenyl siloxane can be used.
  • DB-5 manufactured by Agilent Technologies, Inc.
  • the column is not limited to this.
  • the “hardly volatile component” or the “hardly volatile compound” refers to a substance which dissolves in a polyol to be a solvent and has a boiling point higher than the temperature at which the solvent gasifies, or a tobacco component or a compound having a characteristic that it does not form an azeotropic mixture with solvent and the compound per se does not gasify.
  • the hardly volatile component or compound include glucosides, proteins, polymer compounds each having a different cyclic structure or substituent, long-chain fatty acids, and long-chain hydrocarbons.
  • the hardly volatile component or compound typically has a retention time equal to or longer than the retention time of n-henicosane (C 21 , retention index (RI): 2100), that is, exhibits a retention index (RI) of 2100 or more in the analysis by gas chromatography using a non-polar or low-polar column.
  • the “component group having a retention index (RI) of less than 2100” means a component group having a retention time shorter than the retention time of n-henicosane (C 21 , retention index (RI): 2100) and a component group which has a relatively low boiling point and gasifies at 200 to 240° C. or less.
  • the total peak area of the “component group having a retention index (RI) of less than 2100” is, for example, 78% or more of the total peak area of the whole.
  • the total peak area of the “component group having a retention index (RI) of less than 2100” is preferably 80% or more, more preferably 81% or more.
  • a “peak area” refers to an area of a part surrounded by a line segment obtained by connecting the spots where tangent lines at right and left inflection points with respect to the top of a waveform of a peak of a separated tobacco component or compound and a base line intersect on a chromatogram obtained by the analysis by gas chromatography.
  • the present invention provides as another embodiment the tobacco extract, wherein a content of linolenic acid is 0.02% by weight or less of the whole amount of the tobacco extract.
  • Linolenic acid is a linear unsaturated fatty acid having three double bonds and having a molecular formula represented by C 18 H 30 O 2 , is a hardly volatile component having high hydrophobicity, and is insoluble in a relatively high-polar organic solvent, such as propylene glycol, which is used as a solvent for a mixed liquid for a non-combustion type flavor inhaler.
  • a relatively high-polar organic solvent such as propylene glycol
  • the content of linolenic acid is, for example, 0.02% by weight or less, preferably 0.01% by weight or less, and more preferably 0.006% by weight or less of the whole amount of the tobacco extract.
  • the present invention provides as another embodiment the tobacco extract wherein a total peak area of at least one alkaloid selected from the group consisting of nicotine, nornicotine, myosmine, nicotyrine, nicotine-N-oxide, anabasine, anatabine, and cotinine decreases to 5% or less of the total the peak area of the whole.
  • the total peak area of the alkaloid is, for example, 5% or less, preferably 3.5% or less, and more preferably 2.5% or less of the total peak area of the whole, and most preferably, a peak of the alkaloid is not detected.
  • the present invention provides as another embodiment the tobacco extract to be used for a non-combustion type flavor inhaler.
  • non-combustion type flavor inhaler refers to a tobacco product that generates aerosol by means such as heating an aerosol-generating article held at an aerosol-generating-article-holding part with a heat source without combusting the aerosol-generating article, or atomizing an aerosol-generating article held at an aerosol-generating-article-holding part by ultrasonic waves, thereby delivering the aerosol through a mouthpiece member.
  • the aerosol-generating article include, but not limited to, a liquid or solid aerosol source containing a flavor component contained in a tobacco raw material, and tobacco materials such as a compressed tobacco pellet and a tobacco powder.
  • the non-combustion type flavor inhaler may be a tobacco product that produces aerosol (may be flavor-imparted aerosol) which a user inhales, and examples thereof include a heating type flavor inhaler of a type that uses a liquid aerosol source, a heating type flavor inhaler of a type that uses aerosol which is generated by heating tobacco as an aerosol source, and a non-heating type flavor inhaler for inhaling flavor of tobacco without heating the tobacco.
  • the non-combustion type flavor inhaler is not particularly limited, but preferably, a heating type flavor inhaler of a type that uses a liquid aerosol source can be used.
  • a mixed liquid for a non-combustion type flavor inhaler the mixed liquid containing a flavor component in a polyol such as glycerin or propylene glycol, the flavor component contained in a tobacco raw material.
  • the mixed liquid for a non-combustion type flavor inhaler can also contain the tobacco extract of the present invention as a material that provides a flavor component contained in a tobacco raw material.
  • the present invention provides as another aspect a method for producing the tobacco extract, the method comprising: 1) a step of subjecting all or a portion of a tobacco plant body to steam distillation, thereby obtaining a fraction; 2) a step of subjecting the obtained fraction to extraction with an organic solvent; and 3) a step of removing the organic solvent from an organic phase obtained by the extraction.
  • the variety of a tobacco (a plant of the genus Nicotiana) plant body which is used in steam distillation is not particularly limited.
  • flue-cured, burley, and orient can be used.
  • all of a tobacco plant body which is used in steam distillation can be used without choosing a site, or a portion of the tobacco plant body can be used by choosing only a desired site.
  • all or a portion of a tobacco plant body which is used in steam distillation may be utilized for steam distillation without being cut, or may be utilized for steam distillation after being cut appropriately into a desired size, for example, cut into a 2 cm square or so.
  • All or a portion of a tobacco plant body pulverized or ground by an ordinary method into a slender piece-like, slurry-like, or fine particle-like product may be utilized for steam distillation.
  • All or a portion of a tobacco plant body, which is used in steam distillation, harvested from farmland or the like may be used as it is, all or a portion of a tobacco plant body obtained by being left to stand indoors or outdoors for a predetermined period of time to dissipate part of moisture may be used, or all or a portion of a tobacco plant body obtained by almost dissipating moisture with a drier (including a freeze drier) or the like may be used.
  • a drier including a freeze drier
  • the “steam distillation” is a method of distilling a compound having a low vapor pressure and a high boiling point at a temperature equal to or lower than the boiling point.
  • the “liquid-to-liquid transfer” or “liquid-to-liquid extraction” refers to organic solvent extraction of a target compound from a sample in a liquid phase.
  • the “liquid-to-liquid transfer” or “liquid-to-liquid extraction” is a method of extracting a compound using an organic solvent as a solvent. By adding an organic solvent to a sample in a liquid phase, the sample containing a target compound, to form two separated phases, and shaking the two separated phases, the target compound is extracted into the added organic solvent utilizing the difference in distribution to the two phases.
  • solvent immersion extraction refers to organic solvent extraction of a target compound from a sample in a solid phase. By immersing a sample in a solid phase, the sample containing a target compound, the target compound is extracted into the organic solvent.
  • the organic solvent which is used in the extraction step with an organic solvent may be a solvent that is not miscible with water, for example, ethyl acetate, diethyl ether, propyl acetate, isopropyl acetate, and the like, and preferably ethyl acetate or diethyl ether can be used.
  • a method which is used in the step of removing the organic solvent from the organic phase obtained by extraction is not particularly limited. Methods such as solvent removal under reduced pressure with an evaporator or the like, solvent removal by heating with a heater, and solvent removal by blasting a purge gas can be used.
  • the present invention provides as another embodiment the method for producing the tobacco extract, the method further comprising a step of adjusting pH of the fraction in steam distillation to 3.0 to 6.0.
  • a step of adjusting pH of the fraction in steam distillation to 3.0 to 6.0.
  • the pH of the fraction in steam distillation is adjusted to, for example, 6.0 or less, preferably 5.0 or less, and more preferably 4.0 or less.
  • the pH of the fraction in steam distillation is adjusted to, for example, 1.0 or more, preferably 2.0 or more, and more preferably 3.0 or more.
  • the “warm water extraction” refers to solvent extraction using heated water as a solvent.
  • the condition is, for example, such that water is heated to 50 to 60° C. to make the temperature of water about 40° C. to 45° C. when a raw material is immersed therein.
  • the present invention provides as another aspect the tobacco extract produced by the above-described production method.
  • the tobacco extract is produced using all or a portion of a tobacco plant body as a raw material, the contents of respective components originally contained greatly vary in some cases depending on the seed, the part to be used, and the growth environment of the tobacco plant body which is used as a raw material, therefore it can be considered that the specification of the tobacco extract of the present invention using the contents of components in the extract as indexes is not practical in some cases, but when the above-described production method is used, it is expected that the tobacco extract of the present invention in which a hardly volatile component decreases and/or the alkaloid content is reduced or the alkaloid is removed, and which has constant quality to some extent is obtained, and this tobacco extract exhibits the effects of the present invention.
  • a tobacco product was produced using a United States flue-cured tobacco leaf according to the following procedure.
  • organic solvent ethyl acetate, diethyl ether, chloroform, and n-hexane were used.
  • the organic phase was transferred into a 300 mL Erlenmeyer flask, 20 g of anhydrous sodium sulfate was added, and a resultant mixture was shaken calmly and was then left to stand at room temperature for 30 minutes to perform dehydration.
  • the organic phase after dehydration was filtrated with a filter paper (manufactured by Advantec Toyo Kaisha, Ltd., No. 2, 150 mm) on which a small amount of anhydrous sodium sulfate was placed, and solvent removal under reduced pressure was performed in a 40° C. water bath until the filtrate was evaporated to dryness with a rotary evaporator. Further, 5 mL of ethanol having a purity of 99% (Wako Guaranteed Reagent) was added, and the residual organic solvent was completely removed under a reduced pressure condition with a rotary evaporator to obtain 17 mg of a tobacco extract as a dried and solidified product.
  • a filter paper manufactured by Advantec Toyo Kaisha, Ltd., No. 2, 150 mm
  • solvent removal under reduced pressure was performed in a 40° C. water bath until the filtrate was evaporated to dryness with a rotary evaporator.
  • 5 mL of ethanol having a purity of 99% (Wako Guarantee
  • the organic solvent (the same as used for extraction) in a weight of 100 times the weight of the extract was added to dissolve the extract.
  • a dissolved product was filtrated with a filter (PTFE) having a pore diameter of 0.45 ⁇ m to be used as a tobacco extract solution.
  • PTFE filter
  • FIGS. 1 to 4 Chromatograms obtained by the analysis of tobacco extracts by GC/FID in the cases where solvent extraction was performed with ethyl acetate, diethyl ether, chloroform, and n-hexane are shown in FIGS. 1 to 4 , respectively.
  • peaks on a chromatogram are classified by numerical ranges of retention indexes (RI) of 700 to 2099, 2100 to 2299, and 2300 or more
  • the proportion (%) of the total peak area of the component group in each range in the total peak area of the whole, and the number of peaks of the component group in each range, and the proportion (%) of the number of peaks of the component group in each range in the total number of peaks of the whole are shown in Table 1 below.
  • the contents (% by weight) of linolenic acid and of phytol, which are each a highly hydrophobic, hardly volatile compound, in the whole amount of tobacco extract are shown in Table 2 below.
  • the peaks of the component group having a RI of 2100 or more are smaller, and the peak of linolenic acid was smaller even as compared to the cases where solvent extraction was performed with chloroform or n-hexane.
  • Table 1 in the cases where solvent extraction was performed with ethyl acetate or diethyl ether, it was found that the proportion of the peak area of the component group which has a relatively low boiling point and easily volatilizes, the component group having a RI of less than 2100, exceeds 78%.
  • the content of linolenic acid is about 0.1% by weight or less in any of the cases where solvent extraction was performed with ethyl acetate, diethyl ether, chloroform, or n-hexane.
  • the content of linolenic acid was about 0.02% by weight or less, and was extremely lower even as compared to the cases where solvent extraction was performed with chloroform or n-hexane. Accordingly, it was demonstrated that a tobacco extract in which a hardly volatile component is significantly decreased is obtained by subjecting the fraction after steam distillation to solvent extraction with ethyl acetate or diethyl ether.
  • LV-950A manufactured by HORIBA, Ltd.
  • the tobacco extracts each produced by subjecting the fraction after steam distillation to liquid-to-liquid extraction with ethyl acetate or diethyl ether dissolved by adding propylene glycol in a weight of 4 times the weight of the extracts, and insoluble particles of 0.45 ⁇ m or larger were not recognized.
  • the tobacco extracts each produced by subjecting the fraction after steam distillation to solvent extraction with chloroform or n-hexane did not dissolve completely because insoluble particles having a diameter of 0.45 ⁇ m or larger were recognized when propylene glycol in a weight of 4 times the weight of the extracts was added.
  • a tobacco extract in which a hydrophobic component in the tobacco leaf is significantly decreased and which easily dissolves into propylene glycol is obtained by subjecting the fraction after steam distillation to solvent extraction with ethyl acetate or diethyl ether.
  • organic solvent ethyl acetate, diethyl ether, chloroform, n-hexane, acetone, ethanol, and methanol were used.
  • a filter paper manufactured by Advantec Toyo Kaisha, Ltd., No. 2, 150 mm
  • Chromatograms obtained by the analysis by GC/FID are shown in FIGS. 5 to 11 .
  • peaks on a chromatogram are classified by numerical ranges of retention indexes (RI) of 700 to 2099, 2100 to 2299, and 2300 or more
  • RI retention indexes
  • the proportion (%) of the total peak area of the component group in each range in the total peak area of the whole, and the number of peaks of the component group in each range, and the proportion (%) of the number of peaks of the component group in each range in the total number of peaks of the whole are shown in Table 3 below.
  • Distilled water was heated to prepare 500 mL of about 60° C. warm water, and a United States flue-cured tobacco leaf (50 g) cut into a 2 cm square or so was placed therein to perform extraction for 10 minutes while keeping the temperature in such a way as to be 40 to 45° C. under stirring with a stirrer.
  • the warm water after extraction was cooled to room temperature in a 6° C. refrigerator and was filtrated with a filter paper (ADVANTEC, No. 5A) to remove a solid, thereby obtaining 470 mL of a warm water extract solution.
  • organic solvent ethyl acetate, diethyl ether, chloroform, and n-hexane were used.
  • Chromatograms obtained by the analysis by GC/FID are shown in FIGS. 12 to 15 .
  • peaks on a chromatogram are classified by numerical ranges of retention indexes (RI) of 700 to 2099, 2100 to 2299, and 2300 or more
  • RI retention indexes
  • the proportion (%) of the total peak area of the component group in each range in the total peak area of the whole, and the number of peaks of the component group in each range, and the proportion (%) of the number of peaks of the component group in each range in the total number of peaks of the whole are shown in Table 4 below.
  • a tobacco extract in which the alkaloid content was reduced or the alkaloid was removed was produced using a United States flue-cured tobacco leaf according to the following procedure. That is, by adjusting the pH of the fraction in steam distillation, the fraction obtained in the same manner as in Example 1, the equilibrium between the molecular form and ionic form of the alkaloid is shifted to the ionic form to inhibit the extraction into the organic solvent, and thereby the alkaloid content was reduced or the alkaloid was removed.
  • a flue-cured tobacco leaf was subjected to steam distillation in the same manner as in Example 1 (1) to obtain 1000 mL of a fraction.
  • diethyl ether was used as an organic solvent.
  • Diethyl glycol was removed from the diethyl ether phase after dehydration according to the same procedure as in Example 1 (3) to obtain 18 mg of a tobacco extract as a solidified and dried product.
  • the tobacco extract was dissolved by adding diethyl ether in a weight of 100 times the weight of the extract.
  • a dissolved product was filtrated with a filter (PTFE) having a pore diameter of 0.45 ⁇ m to be used as a tobacco extract solution.
  • PTFE filter
  • a tobacco extract was produced using a French flue-cured tobacco according to the following procedure.
  • the French flue-cured tobacco (958.5 g) was subjected to steam distillation by heating (setting: 280° C., actual temperature: 126 to 128° C.) a steam distillation apparatus (Herb Oil Maker (for 3 kg) manufactured by TOKYOSEISAKUSHO Co., Ltd.) with 3 L of water to obtain 2.3 L of a fraction.
  • the dropping speed of the fraction was 9.5 to 10 ml/min.
  • the solubility of the above-described tobacco extracts in propylene glycol was tested. Specifically, the existence or non-existence of insoluble particles was checked visually by adding a predetermined amount of propylene glycol. In addition, the particle size distribution was measured with a wet type particle analyzer (LA-960 manufactured by HORIBA, Ltd.) to check the existence or non-existence of insoluble particles having a particle diameter of 0.45 ⁇ m or larger. The results are shown in Tables 6 and 7 below.
  • the flue-cured tobacco extract produced by subjecting the fraction after steam distillation to solvent extraction with chloroform did not dissolve and insoluble particles having a particle diameter of 0.45 ⁇ m or larger were recognized in the case where propylene glycol in a weight of 20 times the weight of the extract was added, and the flue-cured tobacco extract produced by subjecting the fraction after steam distillation to solvent extraction with chloroform dissolved finally by adding propylene glycol in a weight of 50 times the weight of the extract.
  • the flue-cured tobacco extract produced by subjecting the fraction after steam distillation to solvent extraction with n-hexane did not dissolve, and insoluble particles of 0.45 ⁇ m or larger were recognized even in the case where propylene glycol in a weight of 50 times the weight of the extract was added.
  • a tobacco extract in which a hydrophobic component in a tobacco leaf is significantly decreased and which easily dissolves in propylene glycol is obtained also from French flue-cured by subjecting the fraction after steam distillation to solvent extraction with ethyl acetate or diethyl ether.
  • the present invention can provide a tobacco extract in which the amount of a hardly volatile component in a tobacco leaf is significantly decreased, a method for producing the tobacco extract, a non-combustion type flavor inhaler comprising the tobacco extract, and further, a heating type flavor inhaler which is one embodiment of the non-combustion type flavor inhaler comprising the non-combustion type flavor inhaler.
  • the present invention can further provide a tobacco extract in which an alkaloid content is reduced or an alkaloid is removed, a method for producing the tobacco extract, a non-combustion type flavor inhaler comprising the tobacco extract, and, further, a heating type flavor inhaler which is one embodiment of the non-combustion type flavor inhaler comprising the tobacco extract.

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CN114788576A (zh) * 2022-04-07 2022-07-26 河南中烟工业有限责任公司 一种烤甜香突出的豫烟浸膏美拉德反应香料及其制备方法和应用
RU2782648C1 (ru) * 2022-04-07 2022-10-31 Индивидуальный Предприниматель Тихонов Евгений Эдуардович Газированная жидкость для электронных сигарет

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