EP4721586A1

EP4721586A1 - Purified labdanum extract, method for producing same, tobacco material, tobacco rod, and flavor inhaler

Info

Publication number: EP4721586A1
Application number: EP23939627.8A
Authority: EP
Inventors: Yoshinobu SHIRAHASHI; Masahiro Chida
Original assignee: Japan Tobacco Inc
Current assignee: Japan Tobacco Inc
Priority date: 2023-05-31
Filing date: 2023-05-31
Publication date: 2026-04-08
Also published as: CN120857875A; KR20250168567A; WO2024247150A1; JPWO2024247150A1

Abstract

Provided is a purified labdanum extract that is effective as a flavor promoter for tobacco. A purified labdanum extract in which, when analysis is performed by GC/MS using a column in which the stationary phase is 95% dimethylpolysiloxane, the sum of peak areas of component groups in which the retention index (RI) is equal to or less than 1399 is 20% or less of the sum of all peak areas.

Description

TECHNICAL FIELD

The present invention relates to a purified labdanum extract and a method for producing the same, a tobacco material, a tobacco rod, and a flavor inhaler.

BACKGROUND ART

Labdanum products are obtained by steam distillation (a labdanum oil), solvent extraction (a concrete or absolute), or alcohol extraction from a gum resin (a resinoid), etc., with fresh leaves, dried leaves, and twigs of Cistus ladaniferus L. as the raw material. Labdanum products have the feature of exhibiting a persistent odor of amber/animal, balsam, cedar wood, etc. As concretes, absolutes, or resinoids, they are dark brown viscous materials. The aroma of a labdanum product is said to comprise 300 or more components. 2,2,6-Trimethylcyclohexanone, ethyl dihydrocinnamate, and other monoterpenes are known characteristic aroma constituents (NPL 1).
It has also been reported that an acid isolated as the main component of a gum-like labdanum has been named labdanolic acid, and is a bicyclic diterpene derivative (NPL 2 and 3). Analogs of this bicyclic compound are collectively referred to as labdanoids, and are widely found in oriental tobacco, etc. (NPL 4).
A known method for purifying labdanum extract is to extract the acidic components as salts, using an alkaline aqueous solution, with labdanum oil as a starting material, and heat treating the extract thereof after separating out the acidic components of labdanum oil that are released by adding an acidic substance thereto (PTL 1). Said method may accentuate the amber/animalic odor of labdanum oil.

CITATION LIST

PATENT LITERATURE

PTL 1: JP H7-018288 A

NON-PATENT LITERATURE

NPL 1: Report of the Japan Central Customs Laboratory, No. 22, 1981
NPL 2: Cocker, J.D., Halsall, T.G., Bowers, A. (1956) The chemistry of gum labdanum, I. Some acidic constituents. Journal of the Chemical Society: 4259-62.
NPL 3: Cocker, J.D., Halsall, T.G., (1956) The chemistry of gum labdanum, II. The structure of labdanolic acid. Journal of the Chemical Society: 4262-71.
NPL 4: Fujimori, Iwao. Terpene compounds in tobacco. Chemistry and Biology, Vol. 22, No. 6, 358-368, 1984

SUMMARY OF INVENTION

TECHNICAL PROBLEM

Oriental tobacco contains labdanoids and hydrocarbons as flavor components (NPL 4). However, in addition to the above, oriental tobacco also contains unpleasantly odorous components such as isovaleric acid that are referred to as off-flavors. Therefore, it is difficult to accentuate the characteristics of the preferred flavor component simply by changing the blending ratio of oriental tobacco.
Meanwhile, an example of a plant other than tobacco containing labdanoids and hydrocarbons is labdanum. It is therefore possible that an extract of labdanum could be used as a flavor promoter to strengthen the flavor of tobacco. However, it is difficult to use a labdanum extract as a flavor promoter for tobacco if added without modification, since an amber/animalic odor, derived from monoterpene hydrocarbons, etc., with relatively low boiling points, is imparted at the same time.
The purpose of the present invention is to provide a purified labdanum extract that is effective as a flavor promoter for tobacco, as well as a tobacco material, a tobacco rod, and a flavor inhaler comprising the purified labdanum extract.

SOLUTION TO PROBLEM

The present invention includes the following embodiments.

[1] A purified labdanum extract wherein the sum of peak areas of a component group with a retention index (RI) of 1399 or less is less than or equal to 20% of the sum of all peak areas when analyzed by GC/MS using a column in which the stationary phase is 95% dimethylpolysiloxane.
[2] The purified labdanum extract set forth in [1], wherein the sum of peak areas of a component group with a retention index (RI) of 2500 or higher is greater than or equal to 30% of the sum of all peak areas.
[3] The purified labdanum extract set forth in [1] or [2], wherein the sum of peak areas of a component group with a retention index (RI) of 1700 or higher is greater than or equal to 90% of the sum of all peak areas.
[4] The purified labdanum extract set forth in any of [1]-[3], wherein the sum of peak areas of a component group with a retention index (RI) of 1800-1900 is less than or equal to 4% of the sum of all peak areas.
[5] A method for producing the tobacco filler set forth in any of [1]-[4], comprising:
- a Step 1 for preparing a labdanum extract; and
- a Step 2 for separating the labdanum extract by distillation into a distillate and a residue.
[6] The method set forth in [5], wherein the distillation is vacuum distillation.
[7] The method set forth in [5] or [6], wherein the labdanum extract is a steam distillate (an oil), a solvent extract (a concrete or absolute), or an alcohol extract of a gum resin (a resinoid).
[8] The purified labdanum extract set forth in any of [1]-[4], for use in a flavor inhaler.
[9] The purified labdanum extract set forth in [8], for use in a heat-not-burn flavor inhaler or a non-burning/non-heating flavor inhaler.
[10] The purified labdanum extract set forth in [8], for use in a burning-type flavor inhaler.
[11] A tobacco material comprising the purified labdanum extract set forth in any of [1]-[4] or [8]-[10].
[12] A tobacco rod comprising the tobacco material set forth in [11].
[13] A flavor inhaler comprising the tobacco rod set forth in [12].
[14] The flavor inhaler set forth in [13], which is a heat-not-burn flavor inhaler or a non-burning/non-heating flavor inhaler.
[15] The flavor inhaler set forth in [13], which is a burning-type flavor inhaler.

ADVANTAGEOUS EFFECTS OF INVENTION

The present invention enables provision of a purified labdanum extract that is effective as a flavor promoter for tobacco, as well as a tobacco material, a tobacco rod, and a flavor inhaler comprising the purified labdanum extract.

BRIEF DESCRIPTION OF DRAWINGS

Fig. 1 is a flowchart showing an example of a method for producing a purified labdanum extract of the present embodiment.
Fig. 2 is a schematic diagram showing an example of a heat-not-burn flavor inhaler of the present embodiment.
Fig. 3 is a schematic diagram showing an example of a heat-not-burn flavor inhalation system of the present embodiment.
Fig. 4 is a schematic diagram showing an example of a non-burning/non-heating flavor inhaler of the present embodiment.
Fig. 5 is a schematic diagram showing an example of a capsule for the non-burning/non-heating flavor inhaler of the present embodiment.
Fig. 6 is a schematic diagram showing an example of a power supply unit for the non-burning/non-heating flavor inhaler of the present embodiment.
Fig. 7 is a schematic diagram showing an example of a cartridge for the non-burning/non-heating flavor inhaler of the present embodiment.
Fig. 8 is a schematic diagram showing an example of a cartridge for the non-burning/non-heating flavor inhaler of the present embodiment.
Fig. 9 is a schematic diagram showing an example of a burning-type flavor inhaler of the present embodiment.
Fig. 10 is a chromatogram from a GC/MS analysis of a pre-purification labdanum extract (a resinoid) in example 1.
Fig. 11 is a chromatogram from a GC/MS analysis of the purified labdanum extract 1 in example 1.
Fig. 12 is a chromatogram from a GC/MS analysis of the purified labdanum extract 2 in example 1.

DESCRIPTION OF EMBODIMENTS

[Purified labdanum extract]

The purified labdanum extract of the present embodiment is such that the sum of peak areas of a component group with a retention index (RI) of 1399 or lower is less than or equal to 20% of the sum of all peak areas when analyzed by GC/MS (a gas chromatograph-mass spectrometer) using a column in which the stationary phase is 95% dimethylpolysiloxane.
Since the sum of peak areas of the component group with an RI of 1399 or lower is less than or equal to 20% when the GC/MS analysis is performed, the purified labdanum extract of the present embodiment has a low content of low boiling-point components such as ethyl dihydrocinnamate and monoterpene hydrocarbons. The amber/animalic odor is thus inhibited, indicating the effectiveness thereof as a flavor promoter for tobacco. The purified labdanum extract of the present embodiment has a low content of low boiling point components, and therefore has a relatively high content of high boiling point components, which is thought to reduce irritation, and in this respect too the purified labdanum extract of the present embodiment is effective as a flavor promoter for tobacco. The sum of peak areas of the component group of the purified labdanum extract of the present embodiment with an RI of 1399 or less is preferably 15% or less, more preferably 10% or less, and still more preferably 7% or less. It should be noted that the sum of peak areas of the component group with an RI of 1399 or lower is preferably small, and there is no particular restriction as to the lower limit of the range thereof, which may be, for example, 0.1% or greater.
GC/MS analysis of purified labdanum extract can be performed by the following method. For example, the purified labdanum extract can be dissolved in ethyl acetate, and analyzed under the following conditions.

Apparatus: 7890A GC, manufactured by Agilent Technologies
Oven: From 40°C (for 3 minutes) to 280°C (for 20 minutes) at 4°C/minute
Runtime: 83 minutes
Injection volume: 1 µL
Injection mode: Split (10:1)
Injection port temperature: 270°C
Septum purge flow: 5 ml/minute
Gas saver: Off
Transfer line temperature: 280°C
Column: HP-5MS (30 m × 0.25 mm × 0.25 µm)
Column flow rate: 1 ml/minute (constant flow mode)
Solvent wait time: 4 minutes
Gain factor: 1
Measurement mode: Scan
Mass range: 26-450
Threshold: 50
Sampling rate: 2
MS ion source temperature: 230°C
MS Quadrupole temperature: 150°C

In the present embodiment, the "retention index (RI)" denotes an index that represents in relative terms the retention ratio of n-alkanes to the compound being analyzed by gas chromatography analysis, taking the number of carbon atoms in a straight-chain hydrocarbon (n-alkane) as a standard. When a column having a predetermined stationary phase is used, the retention index (RI) of the same compound will theoretically be the same value, even if the length of the column, the carrier gas flow rate, etc. are changed. The retention index (RI) is specifically calculated on the basis of the following formula. $RI = 100 n + 100 (t_{x} - t_{n}) / (t_{n + 1} - t_{n})$

n: Number of carbon atoms in n-alkane appearing as a peak immediately before the analyte compound peak
t_x: Retention time of the analyte compound peak
t_n: Retention time of n-alkane appearing as a peak immediately before the analyte compound peak
t_n+1: Retention time of n-alkane appearing as a peak immediately after the analyte compound peak

The sum of peak areas of the component group of the purified labdanum extract of the present embodiment with an RI of 2500 or higher is preferably 30% or more of the total of all peak areas. As a result of the sum of peak areas of the component group with an RI of 2500 or higher being 30% or more, there is a high content of hydrocarbons that are effective flavor components, which means that the flavor persistence of tobacco is further improved when the purified labdanum extract of the present embodiment is used as a flavor promoter for tobacco. The sum of peak areas of the component group in the purified labdanum extract of the present embodiment with an RI of 2500 or higher is more preferably 40-100%, and still more preferably 50-100%.
The sum of peak areas of the component group of the purified labdanum extract of the present embodiment with an RI of 1700 or higher is preferably 90% or more of the total of all peak areas. As a result of the sum of peak areas of the component group with an RI of 1700 or higher being 90% or higher, there is a high content of hydrocarbons and labdanoids such as cembranoids that are effective flavor components, which means that the flavor persistence of tobacco is further improved when the purified labdanum extract of the present embodiment is used as a flavor promoter for tobacco. The sum of peak areas of the component group in the purified labdanum extract of the present embodiment with an RI of 1700 or higher is more preferably 92-100%, and still more preferably 94-100%.
The sum of peak areas of the component group of the purified labdanum extract of the present embodiment with an RI of 1800-1900 may be 4% or less of the sum of all peak areas. The component group with an RI of 1800-1900 includes neophytadiene (RI: approximately 1840). While extracts of oriental tobacco usually contain large amounts of neophytadiene, the purified labdanum extract of the present embodiment has a low neophytadiene content. The sum of peak areas of the component group of the purified labdanum extract in the present embodiment with an RI of 1800-1900 may be 0.01-3%, or may be 0.1-2%.
Since the purified labdanum extract of the present embodiment is useful as a flavor promoter for tobacco, it is preferably used in a flavor inhaler that enables inhalation of the flavor of tobacco components, etc. Flavor inhalers include, for example, the heat-not-burn flavor inhaler, non-burning/non-heating flavor inhaler, and burning-type flavor inhaler described below. The purified labdanum extract of the present embodiment can for example be contained in the tobacco material with which the tobacco rod of the flavor inhaler is filled.

[Method for producing purified labdanum extract]

The method for producing the purified labdanum extract of the present embodiment comprises the following steps: a Step 1 for preparing a labdanum extract; and a Step 2 for separating the labdanum extract by distillation into a distillate and residue. The present inventors confirmed that the purified product obtained by distillation of labdanum extract contains labdanoids and hydrocarbons, and found that the purified product has little of the distinctive odor of labdanum when used in tobacco, and is effective as a flavor promoter for tobacco. It is speculated that distillation can remove low boiling point components such as ethyl dihydrocinnamate and monoterpene hydrocarbons, and meanwhile can sufficiently preserve labdanoids and hydrocarbons which are effective flavor components. The purified labdanum extract of the present embodiment, described above, can be produced simply and efficiently by the purified labdanum extract production method of the present embodiment.

(Step 1)

In the present step, a labdanum extract is prepared. There are no particular limitations as to the labdanum extract, which can for example be a steam distillate (an oil), a solvent extract (a concrete or absolute), or an alcohol extract of a gum resin (a resinoid).

(Step 2)

In this step, the labdanum extract of Step 1 is separated by distillation into a distillate and a residue. In order to make the components contained therein less susceptible to chemical changes due to heat, the distillation is preferably vacuum distillation. The distillation may be carried out continuously or in batches. There are no particular limitations as to the apparatus used for distillation, and for example a short path distiller can be used in a continuous manner, or a glass tube oven for batches.
Distillation may be performed once in the present step, but twice or more is preferred to enable more precise removal of low boiling point components. For example, in the case of a single distillation, labdanum extract may be separated into a distillate and a residue by distillation, and the residue may be used as a purified labdanum extract. On the other hand, in the case of e.g. two distillations, the first distillation separates the labdanum extract into a distillate 1 (low boiling point components) and a residue 1 (Step 2-1), as shown in Fig. 1. The residue 1 is then separated into a distillate 2 and a residue 2 by the second distillation (Step 2-2). Both the distillate 2 and the residue 2 can be used as purified labdanum extracts (purified labdanum extracts 1 and 2), since the main low boiling components are removed as the distillate 1 in Step 2-1. However, the residue 2 (purified labdanum extract 2) contains less of the low boiling point components and more of the high boiling point components, such as labdanoids and hydrocarbons, that are useful as flavor components, and is therefore more preferable as a purified labdanum extract for a tobacco flavor promoter.
For a single distillation, the pressure during distillation is preferably 10-60 Pa in terms of absolute pressure, and more preferably 10-40 Pa. The temperature during distillation depends on the pressure during distillation but is preferably 120-170°C, and more preferably 130-160°C. The distillation time depends on the pressure and temperature during distillation, and for short path distillation with an input flow rate of 50-300 g/hour, for example, the passage time through the heating evaporation section may be from 30 seconds to 5 minutes; whereas in the case of a glass tube oven, the heating time may be 60-240 minutes. There are no particular limitations as to the mass ratios of the distillate and residue, and the ratio of the mass of the distillate to the sum of the mass of the distillate and the residue may for example be 1-20 mass%.
For two distillations, the pressure during the first distillation is preferably 40-3000 Pa in terms of absolute pressure, and more preferably 40-1800 Pa. The temperature during the first distillation depends on the pressure during the first distillation, but is preferably 50-150°C, and more preferably 90-130°C. The first distillation time depends on the pressure and temperature during the first distillation, and for short path distillation with an input flow rate of 100-400 g/hour, for example, the passage time through the heating evaporation section may be from 15 seconds to 3 minutes; whereas in the case of a glass tube oven, the heating time may be 30-180 minutes. There are no particular limitations as to the mass ratios of the distillate 1 and the residue 1, and the mass ratio of the distillate 1 to the sum of the mass of the distillate 1 and the residue 1 may for example be 1-10 mass%.
The pressure during the second distillation is preferably 10-60 Pa in terms of absolute pressure, and more preferably 10-40 Pa. The temperature during the second distillation depends on the pressure during the second distillation, but is preferably 120-170°C, and more preferably 130-160°C. The second distillation time depends on the pressure and temperature during the second distillation, and for short path distillation with an input flow rate of 100-400 g/hour, for example, the passage time through the heating evaporation section may be from 15 seconds to 3 minutes; whereas in the case of a glass tube oven, the heating time may be 30-180 minutes. There are no particular limitations as to the mass ratios of the distillate 2 and the residue 2, and the ratio of the mass of the distillate 2 to the sum of the mass of the fraction 2 and the residue 2 may for example be 1-20 mass%.

[Tobacco material]

The tobacco material of the present embodiment comprises the purified labdanum extract of the present embodiment. There are no particular limitations as to the tobacco material of the present embodiment, provided that the purified labdanum extract of the present embodiment is included therein, and examples include flavor agents for tobacco, such as liquid flavors, as well as tobacco sheets and cut tobacco.
Tobacco sheets are obtained by molding a composition containing e.g. aged leaf tobacco into the form of a sheet. There are no particular limitations as to the aged leaf tobacco used in the tobacco sheet, and examples that have been de-stemmed and separated into laminae and midribs may be cited. Aged leaf tobacco is leaf tobacco that has been treated, e.g. by curing, and stored for a long period in warehouses. A "sheet" in the present embodiment denotes a material having substantially parallel paired main faces and side faces. The tobacco sheet may be formed by a well-known method such as papermaking, casting, or rolling. Details on various types of tobacco sheets molded by such methods are disclosed in the Dictionary of Tobacco, Tobacco Academic Studies Center, March 31, 2009. There is no limitation as to the mode in which the purified labdanum extract is added to the tobacco sheet in the present embodiment.
For example, the purified labdanum extract of the present embodiment may be dissolved in a solvent to prepare a tobacco flavor agent as a solution, which may be sprayed onto or impregnated into the finished tobacco sheet, or the purified labdanum extract of the present embodiment may be added when the tobacco sheet is formed. Papermaking may for example involve a process in which water-soluble components are extracted from aged tobacco leaf and separated into an aqueous extract and a residue, a mixture of the fibrillated residue and pulp is made into paper, and a concentrate of the aqueous extract is added to the sheet thus produced, and the purified labdanum extract of the present embodiment can be added to the aqueous extract. Casting may involve a process in which a mixture is produced by mixing water, pulp, a binder, and ground aged tobacco, and the mixture is cast, and the purified labdanum extract of the present embodiment can be added to the mixture. Rolling may involve a process in which a mixture is produced by mixing water, pulp, a binder, and ground aged tobacco, and the mixture is rolled between a plurality of rollers, and the purified labdanum extract of the present embodiment can be added to the mixture.
Furthermore, as indicated in WO 2014/104078 A1 , ground aged tobacco may be mixed with a binder, the resulting mixture may be interposed between nonwovens, and the resulting laminate may be formed into a given shape by heat sealing to obtain a nonwoven fabric tobacco sheet. In this method, the purified labdanum extract of the present embodiment can be added to the mixture.
The tobacco sheet may comprise an aerosol-generating substrate (i.e. an aerosol source). There are no particular limitations as to the type of aerosol-generating substrate, and extracts, or constituents thereof, may be selected from among various natural substances, depending on the intended use. Specific examples of aerosol-generating substrates include polyhydric alcohols such as glycerin, propylene glycol, sorbitol, xylitol, and erythritol, as well as triacetin, 1,3-butanediol, and mixtures thereof. The aerosol generating-substrate content may be adjusted to varying degrees, depending on the mode of use in a tobacco product. For example, when the tobacco sheet contains an aerosol-generating substrate, the content thereof of is usually 5% by weight or more, preferably 10% by weight or more, and more preferably 15% by weight or more, and is usually 50% by weight or less, preferably 40% by weight or less, and more preferably 25% by weight or less of the total weight of the tobacco sheet, for the sake of obtaining a good flavor.
Examples of cut tobacco include aged leaf tobacco that has been cut to a predetermined size, as well as the abovementioned tobacco sheets cut to a predetermined size, and mixtures thereof. The size is not limited, and may be for example be 0.5-2 mm in width and 3-10 mm in length. Cut tobacco of such a size is preferable for filling the filled articles described below. Other examples of cut tobacco include strand-cut tobacco, which is processed tobacco leaf cut to a width of 0.5-2.0 mm and a length greater than that of the abovementioned cut tobacco, and preferably approximating the length of the wrapping paper. The purified labdanum extract of the present embodiment may be added to the cut tobacco or may be added to the uncut raw material.
The aerosol-generating substrate may also be included in cut tobacco. When the cut tobacco contains an aerosol-generating substrate, the content of the aerosol generating-substrate is usually 5% by weight or more, preferably 10% by weight or more, and more preferably 15% by weight or more, and is usually 50% by weight or less, preferably 40% by weight or less, and more preferably 25% by weight or less of the total weight of the cut tobacco, in order to generate sufficient aerosol and obtain a good flavor.

[Tobacco rod, flavor inhaler]

The tobacco rod of the present embodiment comprises the tobacco material of the present embodiment. The flavor inhaler of the present embodiment comprises the tobacco rod of the present embodiment. The flavor inhaler of the present embodiment is a heat-not-burn flavor inhaler, a non-burning/non-heating flavor inhaler, or a burning-type flavor inhaler.
A "flavor inhaler" in the present embodiment denotes an article with which a user inhales a flavor. Flavor inhalers are broadly divided into "burning-type flavor inhalers," in which flavor is produced by combustion, and "non-burning-type flavor inhalers," in which flavor is produced without burning. Non-burning-type flavor inhalers are further divided broadly into "heat-not-burn flavor inhalers" in which flavor is produced by heating and "non-burning/non-heating flavor inhalers" in which flavor is produced without heating. A combination of a device for generating an aerosol (such as a heating device or an atomizing device) and a heat-not-burn flavor inhaler is specifically referred to as a heat-not-burn flavor inhalation system.

(Heat-not-burn flavor inhaler)

Fig. 2 shows an embodiment of a heat-not-burn flavor inhaler of the present embodiment. As shown in Fig. 2, the heat-not-burn flavor inhaler 20 comprises a tobacco rod 20A, a cylindrical cooling portion 20B having perforations in the perimeter thereof, and a filter portion 20C. The heat-not-burn flavor inhaler 20 may have other members. The axial length of the heat-not-burn flavor inhaler 20 is not particularly limited, but is preferably 40-90 mm, more preferably 50-75 mm, and still more preferably 50-60 mm. The length of circumference of the heat-not-burn flavor inhaler is preferably 16-25 mm, more preferably 20-24 mm, and still more preferably 21-23 mm. Examples include a mode with a tobacco rod 20A length of 20 mm, a cooling portion 20B length of 20 mm, and a filter portion 20C length of 7 mm. The lengths of the individual members can be modified as appropriate, depending on e.g. manufacturability and required quality. A mode in which a first segment 25 is arranged is shown in Fig. 2, but arrangement thereof may be omitted, with only a second segment 26 arranged downstream of the cooling portion 20B.

(1) Tobacco rod 20A

Cut tobacco or a tobacco sheet containing the purified labdanum extract of the present embodiment may be used as a tobacco filler 21 in the tobacco rod 20A. There are no particular limitations as to the method of filling the inside of the wrapping paper 22 with the tobacco filler 21, and the tobacco filler 21 may for example be enclosed inside the wrapping paper 22, or the inside of a cylindrically shaped wrapping paper 22 may be filled with the tobacco filler 21. When the tobacco has a longitudinal direction, so as to be rectangularly shaped, said tobacco may be filled inside of the wrapping paper 22 such that the longitudinal direction of the tobacco is randomly oriented therein, or may be filled such that said longitudinal direction is oriented in the axial direction of the tobacco rod 20A, or in a direction perpendicular thereto. The tobacco rod 20A is heated so that the tobacco component, aerosol-generating substrate, and water contained in the tobacco filler 21 are vaporized and are ready to be inhaled.

(2) Cooling portion 20B

The cooling portion 20B preferably comprises a cylindrical member. The cylindrical member may be, for example, a paper tube 23 of cardboard processed into a cylindrical shape. The cooling portion 20B may also be formed by a sheet of a thin material that is creased and then pleated, gathered, or folded to form channels. Examples of such materials that can be used include sheet materials selected from the group consisting of polyethylene, polypropylene, polyvinyl chloride, polyethylene terephthalate, polylactic acid, cellulose acetate, and aluminum foil. The total surface area of the cooling portion 20B is prepared, as appropriate, taking cooling efficiency into account, and may for example be 300-1000 mm²/mm. The cooling portion 20B is preferably provided with perforations 24. The perforation 24 allows external air to be introduced into the cooling portion 20B during inhalation. As a result, the vaporized aerosol components that are generated by heating the tobacco rod 20A come into contact with the external air, the temperature thereof is lowered and said vaporized aerosol components liquefy as a result to form an aerosol. There are no particular limitations as to the diameter (length across) of the perforations 24, which may for example be 0.5-1.5 mm. There are no particular limitations as to the number of perforations 24, of which there may be one or more. Multiple perforations 24 may be provided on the circumference of the cooling portion 20B, for example.
The cooling portion 20B may be formed into a rod shape having an axial length of 7-28 mm, for example. The axial length of the cooling portion 20B may be 18 mm, for example. The cooling portion 20B has a substantially circular axial cross-sectional shape, which can be 5-10 mm in diameter. The cooling portion can be approximately 7 mm in diameter, for example.

(3) Filter portion 20C

There are no particular limitations as to the configuration of the filter portion 20C, which may comprise one or more filling layers. The outside of the filling layer may be wrapped with a single or multiple wrapping papers. The airflow resistance of the filter portion 20 may be modified, as appropriate, depending on e.g. the amount and material of the filler with which the filter portion 20C is filled. For example, when the filler is cellulose acetate fibers, the airflow resistance can be increased by increasing the amount of cellulose acetate fibers with which the filter portion 20C is filled. When the filler is cellulose acetate fibers, the packing density of cellulose acetate fibers may be 0.13-0.18 g/cm³. The airflow resistance is the value determined using an airflow resistance measurement device (brand name: Sodimax, produced by Sodim).
There are no particular limitations as to the length of the circumference of the filter portion 20C, but it is preferably 16-25 mm, more preferably 20-24 mm, and still more preferably 21-23 mm. The filter portion 20C may have an axial length (in the horizontal direction in Fig. 2) of 4-10 mm, which can be selected so as to result in an airflow resistance of 15-60 mm H₂O per segment. The axial length of the filter portion 20C is preferably 5-9 mm, and more preferably 6-8 mm. There are no particular limitations as to the cross-sectional shape of the filter portion 20C, which may for example be circular, elliptical, or polygonal. Flavor-containing destructible capsules, flavor beads, and flavors can also be directly added to the filter portion 20C.
The filter portion 20C may comprise a center hole portion as the first segment 25. The center hole portion may comprise a first filling layer 25a having one or more hollow portions, and an inner plug wrapper (i.e., inside wrapping paper) 25b that covers the filling layer. The center hole portion has the function of strengthening the mouthpiece portion. The shape of the center hole portion may be retained by means of thermoforming, without an inner plug wrapper 25b being provided. The first filling layer 25a may be, for example, a rod having an inside diameter of φ1.0-5.0 mm, that has been filled to a high density with cellulose acetate fibers that have been cured by adding a triacetin-containing plasticizer thereto in an amount of 6-20 mass% of the mass of cellulose acetate. Since the first filling layer 25a has a high fiber packing density, air or an aerosol will flow only through the hollow portion during inhalation, with virtually none flowing through the first filling layer 25a. The first filling layer 25a of the center hole portion is a fiber filling layer, and the user will therefore experience little discomfort when touching the outside during use. The filter portion 20C may comprise a second segment 26. The second segment 26 comprises a second filling layer 26a and an inner plug wrapper (i.e., inside wrapping paper) 26b that covers the filling layer.
The first segment 25 and the second segment 26 are connected by an outer plug wrapper (i.e., outside wrapping paper) 27. The outer plug wrapper 27 may be cylindrical paper, for example. The tobacco rod 20A, cooling portion 20B, and the connected first segment 25 and second segment 26 can be connected by a mouthpiece lining paper 28. These connections may be formed, for example, by coating an inside surface of the mouthpiece lining paper 28 with a glue such as a vinyl acetate-based glue, and wrapping the abovementioned three members. The members may also be connected by multiple separate connections with a plurality of lining papers.

(Heat-not-burn flavor inhalation system)

Fig. 3 shows an example of the heat-not-burn flavor inhalation system of the present embodiment. In Fig. 3, the heat-not-burn flavor inhalation system comprises a heat-not-burn flavor inhaler 20 and a heating device 10 that heats the tobacco rod 20A from the outside.
The heating device 10 comprises a body 11, a heater 12, a metal tube 13, a battery unit 14, and a control unit 15. The body 11 has a cylindrical recess 16, in which the heater 12 and the metal tube 13 are positioned to accommodate the tobacco rod 20A inserted therein. The heater 12 can be a heater employing electrical resistance, such that heating by the heater 12 is effected by supplying electrical power from the battery unit 14 in accordance with commands from the control unit 15, which controls temperature. Heat emitted from the heater 12 is transferred through the highly thermally conductive metal tube 13 to the tobacco rod 20A. Fig. 3 shows a mode in which the heating device 10 heats the tobacco rod 20A from the outside, but the rod may also be heated from the inside. There are no particular limitations as to the heating temperature of the heating device 10, but 400°C or lower is preferable, 150-400°C is more preferable, and 200-350°C is still more preferable. The heating temperature refers to the temperature of the heater 12 of the heating device 10.

(Non-burning/non-heating flavor inhaler)

Fig. 4 shows one aspect of a non-burning/non-heating flavor inhaler of the present embodiment. The non-burning/non-heating flavor inhaler 30 has a power supply unit 30D, a cartridge 30E, and a tobacco capsule 30F. The non-burning/non-heating flavor inhaler 30 has a shape extending from the non-inhalation end u (upstream) towards the inhalation end d (downstream). The cartridge 30E is attachable to and detachable from the power supply unit 30D. The tobacco capsule 30F is also attachable to and detachable from the cartridge 30E.

(1) Tobacco capsule

Fig. 5 shows an example of a tobacco capsule 30F. As shown in Fig. 5, the tobacco capsule 30F is a tobacco rod that has a flavor source 300 inside. The flavor source 300 comprises the tobacco material of the present embodiment. The tobacco capsule 30F is connected to the cartridge 30E. Specifically, a part of the tobacco capsule 30F is housed within the cartridge 30E.
The tobacco capsule 30F has a housing 310 in which the flavor source 300 is housed, a mesh 320, a nonwoven fabric 330, and a cap 340. The aerosol atomized by the atomization unit 220 described below is introduced through the mesh 320 into the housing 310 and comes into contact with the flavor source 300, and thereby a flavor is imparted to the aerosol. The aerosol is then inhaled by the user via the nonwoven fabric 330. Thus, a flavor can be imparted to the aerosol in the non-burning/non-heating flavor inhaler 30, without heating the flavor source 300. Nor is aerosol substantially generated from the flavor source 300.
The length of the tobacco capsule 30F (housing 310) is preferably 40 mm or less, and more preferably 25 mm or less, in the direction in which the aerosol flows. The length thereof is also preferably 1 mm or more, and more preferably 5 mm or more, in the aerosol flow direction. The maximum length of the housing 310 of the tobacco capsule 30F (housing 310) is preferably 20 mm or less, and more preferably 10 mm or less, in the direction perpendicular to the aerosol flow direction. The maximum length of the tobacco capsule 30F (housing 310) is also preferably 1 mm or less, and more preferably 3 mm or less, in the direction perpendicular to the aerosol flow direction.
The tobacco-containing flavor source 300 comprises raw material pieces for imparting a flavor to the aerosol. The lower limit of the size of the raw material pieces is preferably 0.2-1.2 mm, and more preferably 0.2-0.7 mm. The smaller in size the raw material pieces constituting the flavor source 300, the greater the specific surface area thereof, and thus the more easily the flavor component is released. Examples of raw material pieces that may be used for constituting the flavor source 300 include cut tobacco containing the purified labdanum extract of the present embodiment, and a molded body of a tobacco material of the present embodiment that has been formed into granules. The flavor source 300 may include a flavor of e.g. a plant other than tobacco (such as a mint or herb) or menthol. The tobacco-containing flavor source 300 may also contain gustatory materials. Ingredients exhibiting sweetness, sourness, saltiness, an umami taste, bitterness, acerbity, body, spiciness, harshness, astringency, etc. may be cited as examples of gustatory materials. Saccharides, sugar alcohols, and sweeteners, etc. may be cited as examples of ingredients exhibiting sweetness. Monosaccharides, disaccharides, oligosaccharides, and polysaccharides, etc. may be cited as examples of saccharides. Natural sweeteners and synthetic sweeteners, etc. may be cited as examples of sweeteners.
The raw material pieces are for example obtained by sifting in compliance with JIS Z 8815, using a stainless steel sieve that is compliant with JIS Z 8801. For example, raw material pieces are sifted over a 20-minute period by drying and mechanical shaking, using a stainless steel sieve having 0.71 mm openings, to obtain raw material pieces that pass through the stainless sieve having 0.71 mm openings. The raw material pieces are then sifted over a 20-minute period by drying and mechanical shaking, using a stainless steel sieve having 0.212 mm openings, to remove raw material pieces that pass through the stainless sieve having 0.212 mm openings. That is, raw material pieces constituting the flavor source 300 are raw material pieces that pass through a stainless steel sieve of a specified upper limit (0.71 mm openings) and that do not pass through a stainless steel sieve of a specified lower limit (0.212 mm openings). The lower limit of the size of the raw material pieces constituting the flavor source 300 is thus defined by the openings of the stainless sieve of a specified lower limit. Moreover, the upper limit of the size of the raw material pieces constituting the flavor source 300 is defined by the openings of the stainless sieve of the specified upper limit.
The filling amount of the flavor source 300 housed in the housing 310 is preferably 300 mg or more, and more preferably 350 mg or more, in the interests of good flavor.

(2) Power supply unit

An example of a power supply unit 30D is shown in Fig. 6. The power supply unit 30D has a battery 110. The battery 110 may be a disposable type battery or a rechargeable type battery. The initial output voltage of the battery 110 is preferably in the range of 1.2-4.2 V. The battery 110 capacity is preferably in the range of 100-1000 mAh.

(3) Cartridge

An example of a cartridge 30E is shown in Fig. 7 and 8. Fig. 7 shows a cross-sectional view of an example of a cartridge 30E, and Fig. 8 shows the internal structure thereof. The cartridge 30E comprises a reservoir 210, an atomization unit 220, a flow path-forming element 230, an outer frame 240, and an end cap 250. The cartridge 30E has a first flow path 200X, arranged downstream of the atomization unit 220, as an aerosol flow path.
An aerosol source 200 is stored in the reservoir 210. The reservoir 210 is positioned around the flow path-forming element 230 in a cross section perpendicular to the direction in which the aerosol flows (i.e. the direction from the non-inhalation end to the inhalation end (upstream to downstream)). The reservoir 210 is located in a void space between the flow path-forming element 230 and the outer frame 240. The reservoir 210 comprises, for example, a porous material such as a resin web or cotton. The reservoir 210 may also comprise a tank that houses a liquid aerosol source 200. Examples of the aerosol source 200 include glycerol and propylene glycol.
The atomization unit 220 atomizes the aerosol source 200, without combustion, using power supplied by the battery 110. The atomization unit 220 comprises a heating wire (coil) wound at a predetermined pitch. The atomization unit 220 preferably comprises a heating wire having a resistance in the range of 1.0-3.0 Ω. The predetermined pitch is preferably at least a value at which the heating wire is not in contact with itself, and lower values are preferred. The predetermined pitch is preferably no more than e.g. 0.40 mm. The predetermined pitch is preferably constant to stabilize atomization of the aerosol source 200. The predetermined pitch is the spacing between adjacent heating wire centers.
The flow path-forming element 230 has a cylindrical shape forming the first flow path 200X extending along the aerosol flow direction. The outer frame 240 has a cylindrical shape in which the flow channel-forming element 230 is housed. The outer frame 240 extends further downstream than the end cap 250 and houses a portion of the tobacco capsule 30F. The end cap 250 is a cap that blocks, from the downstream side, the void space between the flow path-forming element 230 and the outer frame 240. The end cap 250 prevents the aerosol source 200 that is stored in the reservoir 210 from leaking into the tobacco capsule 30F side.

(Burning-type flavor inhaler)

Fig. 9 shows an example of a burning-type flavor inhaler of the present embodiment. As shown in Fig. 9, the burning-type flavor inhaler 40 comprises a tobacco rod 41 and a filter 42 provided adjacent to the tobacco rod 41. The tobacco rod 41 comprises a tobacco filler 43, containing the purified labdanum extract of the present embodiment, and a wrapper 44 wrapped around the tobacco filler 43. The tobacco rod 41 is connected to the filter 42 by a tipping paper member 45 wrapped around the tobacco rod 41 and filter 42. The tipping paper member 45 may have ventilation holes in part of the outer circumference thereof. There may be one or multiple ventilation holes, and for example 10-40 thereof may be formed. If there are multiple ventilation holes, the ventilation holes may for example be arranged in a row circling the outer circumference of the tipping paper member 45. The multiple ventilation holes can be arranged at roughly regular intervals. Provision of ventilation holes allows air to be drawn from the ventilation holes into the filter 42 upon inhalation. Diluting the mainstream smoke with external air from the ventilation holes enables implementation of a product design with a desired tar level. Such burning-type flavor inhalers are generally typified by cigarettes. A user can enjoy the tobacco flavor by igniting the tip of the tobacco rod 41 and inhaling, with the inhalation end of the filter 42 placed in the mouth.

EXAMPLES

Specific examples of the present embodiment will be described below, but the present embodiment is not limited to these examples.

EXAMPLE 1

(Production of purified labdanum extract)

The labdanum extract was purified using the method shown in Fig. 1 to obtain a purified labdanum extract. Specifically, 500 g of labdanum extract (resinoid) were first prepared (Step 1). Next, the labdanum extract was heated in advance to 130°C to impart fluidity, then 496.1 g of the labdanum extract were fed continuously into a short-path distiller (brand name: DN-60, produced by Asahi Seisakusho) at a speed of 250 g/hour, and fractionated under conditions of 1700 Pa as the absolute pressure and 130°C as the jacket temperature (Step 2-1). As a result, 15.2 g of a distillate 1 and 464.9 g of a residue 1 were obtained. The residue 1 was reheated to 130°C, after which the residue 1 was fed into the aforementioned device and fractionated under conditions of 20 Pa as the absolute pressure and 150°C as the jacket temperature (Step 2-2). As a result, 78.6 g of a distillate 2 (purified labdanum extract 1) and 362.1 g of a residue 2 (purified labdanum extract 2) were obtained.
The pre-purification labdanum extract (resinoid), the purified labdanum extract 1, and the purified labdanum extract 2 were respectively dissolved in ethanol and analyzed by GC/MS under the following conditions.Fig. 10 shows a chromatogram from a GC/MS analysis of a pre-purification labdanum extract (a resinoid), Fig. 11 shows a chromatogram of the purified labdanum extract 1, and Fig. 12 shows a chromatogram from a GC/MS analysis of the purified labdanum extract 2, respectively.

Table 1 shows the peak area percentage in the retention index (RI) range of each of the chromatograms obtained by GC/MS analysis.

[Table 1]

GC/MS peak area percentage (Units: %)
	Pre-purification labdanum extract (resinoid)	Purified labdanum extract 1	Purified labdanum extract 2
RI: 1399 or less	29.4	16.4	6.0
RI: 1700 or greater	62.9	78.9	94.1
Internal RI: 1800-1900	0.8	1.8	0.6
RI: 2500 or greater	14.5	3.4	58.9

The chemical structures of compounds (labdanoids or analogs thereof) represented by peaks a) to d) in the chromatograms presented in Fig. 11 and 12 are shown below.

[Chem. 1]

a)	Norambreinolid	b)	(+)-Labda-8(17),13(E)-diene-15-ol
	RI:2069		RI:2315


c)	(+)-Copaiferic acid	d)	Sclareoloxide
	RI : 2563		RI : 2696

(Evaluation as a flavor promoter for tobacco)

A tobacco material was prepared by adding 500 ppm by mass of a pre-purification labdanum extract (resinoid), a purified labdanum extract 1, or a purified labdanum extract 2 to cut tobacco. Tobacco rods of a heat-not-burn flavor inhaler were filled with the tobacco material, and the amber/animalic odor intensity, irritation-reducing effect, and flavor persistence thereof were sensorially evaluated by panelists, using the heat-not-burn flavor inhalers. The sensory evaluations were conducted by three panelists, with assessments made on the basis of consensus of the three panelists. In evaluating irritation-reducing effect and improvement of flavor persistence, a determination was made as to whether an irritation-reducing effect was obtained, and whether flavor persistence had improved, for purified labdanum extract 1 and a purified labdanum extract 2, with a pre-purification labdanum extract (resinoid) as a control. Note that the three panelists had been thoroughly trained in sensory evaluation, using a plurality of types of samples, and it had been confirmed that the evaluation thresholds were equal, and were uniform among the panelists. The results are shown in Table 2.

[Table 2]

	Amber/animalic odor intensity	Irritation-reducing effect	Improvement of aroma persistence
Pre-purification labdanum extract (resinoid)	Intense	-	-
(Control)	Intense	-	-
Purified labdanum extract 1	Somewhat intense	None	Somewhat
Purified labdanum extract 2	Weak	Yes	Yes

As shown in Table 2, the purified labdanum extract 1 and purified labdanum extract 2 of the present embodiment had a less intense amber/animalic odor and improved aroma persistence than the pre-purification labdanum extract (resinoid). Thus it was found that the purified labdanum extract 1 and the purified labdanum extract 2 of the present embodiment are effective as flavor promoters for tobacco. In particular, it was found that the purified labdanum extract 2 performed similarly to oriental tobacco in providing an irritation-reducing effect, imparting a persistent weighty impression, and improving ease of inhalation.

EXAMPLE 2

The labdanum extract was purified using the method shown in Fig. 1 to obtain a purified labdanum extract. Specifically, 1.6 g of a labdanum extract (resinoid) were first prepared (Step 1). Next, the labdanum extract was placed in a glass tube oven (brand name: GTO-1000, manufactured by Sibata Scientific Technology) and continuously distilled under conditions of 60°C as the heating temperature at an absolute pressure of 55 Pa, 90°C as the heating temperature at an absolute pressure of 40 Pa, and 130°C as the heating temperature at an absolute pressure of 40 Pa (Step 2-1). As a result, 0.06 g of a distillate 1 and 1.54 g of a residue 1 were obtained. The residue 1 was further fractionated at an absolute pressure of 40 Pa and a heating temperature of 160°C (Step 2-2). As a result, 0.03 g of a distillate 2 (purified labdanum extract 1) and 1.48 g of a residue 2 (purified labdanum extract 2) were obtained.

The pre-purification labdanum extract (resinoid), the purified labdanum extract 1, and the purified labdanum extract 2 were respectively dissolved in ethanol, and underwent GC/MS analysis under the same conditions as in example 1.Table 3 shows the peak area percentage in the retention index (RI) range of each of the chromatograms obtained by GC/MS analysis.

[Table 3]

GC/MS peak area percentage (Units: %)
	Pre-purification labdanum extract (resinoid)	Purified labdanum extract 1	Purified labdanum extract 2
RI: 1399 or less	29.4	0.3	3.5
RI: 1700 or greater	62.9	89.5	95.5
Internal RI: 1800-1900	0.8	1.6	0.2
RI: 2500 or greater	14.5	7.4	32.0

The present embodiment includes the following aspects.

REFERENCE SIGNS LIST

10: Heating device
11: Body
12: Heater
13: Metal tube
14: Battery unit
15: Control unit
16: Recess
17: Vent hole
20: Heat-not-burn flavor inhaler
20A: Tobacco rod portion
20B: Cooling portion
20C: Filter portion
21: Tobacco filler
22: Wrapping paper
23: Paper tube
24: Perforation
25: First segment
25a: First filling layer
25b: Inner plug wrapper
26: Second segment
26a: Second filling layer
26b: Inner plug wrapper
27: Outer plug wrapper
28: Lining paper
30: Non-burning/non-heating flavor inhaler
30D: Power supply unit
30E: Cartridge
30F: Tobacco capsule
u: Non-inhalation end
d: Inhalation end
40: Burning-type flavor inhaler
41: Tobacco rod
42: Filter
43: Tobacco filler
44: Wrapper
45: Tipping paper member
110: Battery
200: Aerosol source
210: Reservoir
220: Atomization unit
230: Flow path-forming element
240: Outer frame
250: End cap
200X: First flow path
300: Flavor source
310: Housing
320: Mesh
330: Nonwoven fabric
340: Cap

Claims

A purified labdanum extract wherein the sum of peak areas of a component group with a retention index (RI) of 1399 or less is less than or equal to 20% of the sum of all peak areas when analyzed by GC/MS using a column in which the stationary phase is 95% dimethylpolysiloxane.
The purified labdanum extract set forth in Claim 1, wherein the sum of peak areas of a component group with a retention index (RI) of 2500 or higher is greater than or equal to 30% of the sum of all peak areas.
The purified labdanum extract set forth in Claim 1 or 2, wherein the sum of peak areas of a component group with a retention index (RI) of 1700 or higher is greater than or equal to 90% of the sum of all peak areas.
The purified labdanum extract set forth in any one of Claims 1-3, wherein the sum of peak areas of a component group with a retention index (RI) of 1800-1900 is less than or equal to 4% of the sum of all peak areas.
A method for producing the purified labdanum extract set forth in any one of Claims 1-4, comprising:
a Step 1 for preparing a labdanum extract; and

a Step 2 for separating the labdanum extract by distillation into a distillate and a residue.
The method set forth in Claim 5, wherein the distillation is vacuum distillation.
The method set forth in Claim 5 or 6, wherein the labdanum extract is a steam distillate (an oil), a solvent extract (a concrete or absolute), or an alcohol extract of a gum resin (a resinoid).
The purified labdanum extract set forth in any one of Claims 1-4, for use in a flavor inhaler.
The purified labdanum extract set forth in Claim 8, for use in a heat-not-burn or a non-burning/non-heating flavor inhaler.
The purified labdanum extract set forth in Claim 8, for use in a burning-type flavor inhaler.
A tobacco material comprising the purified labdanum extract set forth in any one of Claims 1-4 or 8-10.
A tobacco rod comprising the tobacco material set forth in Claim 11.
A flavor inhaler comprising the tobacco rod set forth in Claim 12.
The flavor inhaler set forth in Claim 13, which is a heat-not-burning flavor inhaler or a non-burning/non-heating flavor inhaler.
The flavor inhaler set forth in Claim 13, which is a burning-type flavor inhaler.