WO2024247150A1 - Purified labdanum extract, method for producing same, tobacco material, tobacco rod, and flavor inhaler - Google Patents

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

Purified labdanum extract and its manufacturing method, tobacco material, tobacco rod, and flavor inhaler

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.

Labdanum products are made from the raw leaves, dried leaves and twigs of Cistus Ladaniferous L., and are obtained by steam distillation (Labdanum oil), solvent extraction (Concrete or Absolute), and alcohol extraction of gum resin (Resinoid). Labdanum products are characterized by a long-lasting scent of amber animal, balsam, zetterwood, etc. Concrete, Absolute, and Resinoid are dark brown viscous substances. It is said that the scent of labdanum products is composed of more than 300 components. Known characteristic aroma components include 2,2,6-trimethylcyclohexanone, ethyl dihydrocinnamate, and other monoterpenes (Non-Patent Document 1).

Furthermore, the acid isolated as the main component of the gum of labdanum has been named labdanolic acid and has been reported to be a bicyclic diterpene derivative (Non-Patent Documents 2 and 3). Analogues of this bicyclic compound are collectively called labdanoids and are found in large quantities in Orient tobacco and other tobacco products (Non-Patent Document 4).

A known method for refining labdanum extract is to use labdanum oil as the starting material, extract acidic components as salts using an alkaline aqueous solution, add an acidic substance to the extract, and separate and obtain the liberated acidic components of labdanum oil, which are then heat-treated (Patent Document 1). This method can emphasize the amber animal-like scent of labdanum oil.

Japanese Patent Application Publication No. 07-018288

Central Customs Laboratory Report No. 22 1981 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. 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. Iwao Fujimori, "Terpene Compounds in Tobacco", Chemistry and Biology, vol. 22, No. 6, 358-368, 1984

Orient tobacco contains labdanoids and hydrocarbons as flavor components (Non-Patent Document 4). However, Orient tobacco also contains other unpleasant odor components, such as isovaleric acid, known as off-flavors. Therefore, it is difficult to bring out the characteristics of desirable flavor components by simply changing the blend ratio of Orient tobacco.

On the other hand, labdanum is an example of a plant other than tobacco that contains labdanoids and hydrocarbons. Therefore, labdanum extracts may be used as a flavor enhancer that reinforces the flavor of tobacco. However, if labdanum extract is added as is, it also gives off an amber animal-like odor derived from monoterpene hydrocarbons with relatively low boiling points, making it difficult to use as a tobacco flavor enhancer.

The present invention aims to provide a purified labdanum extract that is effective as a flavor enhancer for tobacco, as well as a tobacco material, a tobacco rod, and a flavor inhaler that contain the purified labdanum extract.

The present invention includes the following embodiments:

[1] A purified labdanum extract in which, when analyzed by GC/MS using a column whose stationary phase is 95% dimethylpolysiloxane, the sum of the peak areas of components having a retention index (RI) of 1399 or less is 20% or less of the sum of the entire peak area.

[2] The purified labdanum extract according to [1], in which the sum of the peak areas of the component groups having a retention index (RI) of 2500 or more is 30% or more of the sum of the entire peak area.

[3] The purified labdanum extract according to [1] or [2], in which the sum of the peak areas of the component groups having a retention index (RI) of 1700 or more is 90% or more of the sum of the entire peak area.

[4] A purified labdanum extract according to any one of [1] to [3], in which the sum of the peak areas of the component group having a retention index (RI) of 1800 to 1900 is 4% or less of the sum of the entire peak area.

[5] A method for producing a purified labdanum extract according to any one of [1] to [4], comprising the steps of:
Step 1 of preparing a labdanum extract;
Step 2: separating the labdanum extract into a fraction and a residue using distillation;
The method includes:

[6] The method according to [5], wherein the distillation is reduced pressure distillation.

[7] The method according to [5] or [6], wherein the labdanum extract is a steam distillate (oil), a solvent extract (concrete or absolute), or an alcohol extract of gum resin (resinoid).

[8] A purified labdanum extract according to any one of [1] to [4], which is used in a flavor inhaler.

[9] The purified labdanum extract described in [8], which is used in a non-combustion, non-heating flavor inhaler or a non-combustion, non-heating flavor inhaler.

[10] The purified labdanum extract described in [8], which is used in a combustion-type flavor inhaler.

[11] A tobacco material containing a purified labdanum extract according to any one of [1] to [4] and [8] to [10].

[12] A tobacco rod comprising the tobacco material described in [11].

[13] A flavor inhaler comprising the tobacco rod described in [12].

[14] The flavor inhaler described in [13], which is a non-combustion heating type flavor inhaler or a non-combustion non-heating type flavor inhaler.

[15] The flavor inhaler described in [13], which is a combustion type flavor inhaler.

The present invention provides a purified labdanum extract that is effective as a tobacco flavor enhancer, as well as a tobacco material, a tobacco rod, and a flavor inhaler that contain the purified labdanum extract.

1 is a flowchart showing an example of a method for producing a purified labdanum extract according to the present embodiment. FIG. 2 is a schematic diagram showing an example of a non-combustion heating type flavor inhaler according to the present embodiment. 1 is a schematic diagram showing an example of a non-combustion heating type flavor inhalation system according to an embodiment of the present invention. FIG. 2 is a schematic diagram showing an example of a non-combustion and non-heating type flavor inhaler according to the present embodiment. FIG. 2 is a schematic diagram showing an example of a tobacco capsule of a non-combustion, non-heating type flavor inhaler according to the present embodiment. FIG. 2 is a schematic diagram showing an example of a power supply unit of a non-combustion and non-heating type flavor inhaler according to the present embodiment. FIG. 2 is a schematic diagram showing an example of a cartridge of a non-combustion and non-heating type flavor inhaler according to the present embodiment. FIG. 2 is a schematic diagram showing an example of a cartridge of a non-combustion and non-heating type flavor inhaler according to the present embodiment. FIG. 2 is a schematic diagram showing an example of a combustion type flavor inhaler according to the present embodiment. 1 is a chromatogram of GC/MS analysis of the unpurified labdanum extract (Resinoid) of Example 1. 1 is a chromatogram of GC/MS analysis of purified labdanum extract 1 of Example 1. 1 is a chromatogram of GC/MS analysis of purified labdanum extract 2 of Example 1.

[Refined Labdanum Extract]
When the purified labdanum extract of this embodiment is analyzed by GC/MS (gas chromatograph mass spectrometer) using a column whose stationary phase is 95% dimethylpolysiloxane, the sum of the peak areas of the component groups having a retention index (RI) of 1399 or less is 20% or less of the sum of the entire peak area.

In the purified labdanum extract according to this embodiment, the total peak area of the component group having an RI of 1399 or less is 20% or less when the GC/MS analysis is performed, and therefore the content of low-boiling point components such as ethyl dihydrocinnamate and monoterpene hydrocarbons is low. Therefore, the amber animal-like odor is suppressed, and the purified labdanum extract according to this embodiment is effective as a tobacco flavor enhancer. In addition, since the purified labdanum extract according to this embodiment has a low content of low-boiling point components, the content of high-boiling point components is relatively high, and it is considered that irritation is reduced, and in this respect, the purified labdanum extract according to this embodiment is effective as a tobacco flavor enhancer. In the purified labdanum extract according to this embodiment, the total peak area of the component group having an RI of 1399 or less is preferably 15% or less, more preferably 10% or less, and even more preferably 7% or less. It is preferable that the total peak area of the component group having an RI of 1399 or less is small, and the lower limit of the range is not particularly limited, but it can be, for example, 0.1% or more.

The GC/MS analysis of the purified labdanum extract can be carried out by the following method. For example, the purified labdanum extract can be dissolved in ethyl acetate and analyzed under the following conditions.
Equipment: Agilent Technologies 7890A GC
Oven 40℃ (3 min) → 4℃/min → 280℃ (20 min)
Run time: 83 minutes Injection volume: 1 μl
Injection mode Split (10:1)
Inlet temperature 270℃
Septum purge flow rate: 5 ml/min Gas saver: off Transfer line temperature: 280°C
Column: HP-5MS (30m x 0.25mm x 0.25μm)
Column flow rate: 1 ml/min (constant flow mode)
Solvent waiting 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℃

In this embodiment, the term "retention index (RI)" refers to an index that, in gas chromatography analysis, represents the relative retention ratio between n-alkanes and the compound being analyzed, based on the carbon number of straight-chain hydrocarbons (n-alkanes). When a column with a specified stationary phase is used, the retention index (RI) will theoretically be the same for the same compound, even if the column length, carrier gas flow rate, etc. are changed. Specifically, the retention index (RI) is calculated based on the following formula:

n: carbon number of n-alkane appearing as a peak immediately before the peak of the analyte compound t _x : retention time of the peak of the analyte compound t _n : retention time of n-alkane appearing as a peak immediately before the peak of the analyte compound t _n+1 : retention time of n-alkane appearing as a peak immediately after the peak of the analyte compound

In the purified labdanum extract of this embodiment, the sum of the peak areas of the component group having an RI of 2500 or more is preferably 30% or more of the total peak area. When the sum of the peak areas of the component group having an RI of 2500 or more is 30% or more, the content of hydrocarbons, which are effective flavor components, is high, and when used as a tobacco flavor enhancer, the persistence of tobacco flavor is further improved. In the purified labdanum extract of this embodiment, the sum of the peak areas of the component group having an RI of 2500 or more is more preferably 40% or more and 100% or less, and even more preferably 50% or more and 100% or less.

In the purified labdanum extract of this embodiment, the sum of the peak areas of the component group having an RI of 1700 or more is preferably 90% or more of the total peak area. When the sum of the peak areas of the component group having an RI of 1700 or more is 90% or more, the content of labdanoids such as cembranoids and hydrocarbons, which are effective flavor components, is high, and the persistence of tobacco flavor is further improved when used as a tobacco flavor enhancer. In the purified labdanum extract of this embodiment, the sum of the peak areas of the component group having an RI of 1700 or more is more preferably 92% or more and 100% or less, and even more preferably 94% or more and 100% or less.

The purified labdanum extract of this embodiment may have a total peak area of components with an RI of 1800-1900 that is 4% or less of the total peak area. The components with an RI of 1800-1900 include neophytadiene (RI: approximately 1840). Extracts of Orient tobacco usually contain a lot of neophytadiene, but the purified labdanum extract of this embodiment has a low neophytadiene content. The purified labdanum extract of this embodiment may have a total peak area of components with an RI of 1800-1900 that is 0.01% or more and 3% or less, or 0.1% or more and 2% or less.

The purified labdanum extract according to this embodiment is useful as a tobacco flavor enhancer, and is therefore suitable for use in a flavor inhaler capable of inhaling the flavor of tobacco components and the like. Examples of flavor inhalers include non-combustion heating type flavor inhalers, non-combustion non-heating type flavor inhalers, and combustion type flavor inhalers, which will be described later. The purified labdanum extract according to this embodiment can be contained, for example, in the tobacco material filled in the tobacco rod of the flavor inhaler.

[Method of producing purified labdanum extract]
The method for producing the purified labdanum extract according to the present embodiment includes the following steps: Step 1: preparing a labdanum extract; Step 2: separating the labdanum extract into a fraction and a residue by distillation. The present inventors have confirmed that the purified product obtained by distillation of the labdanum extract contains labdanoids and hydrocarbons, and have found that the purified product has less of the odor specific to labdanum when used in tobacco, and is effective as a tobacco flavor enhancer. This is presumably because distillation can remove low-boiling components such as ethyl dihydrocinnamate and monoterpene hydrocarbons, while sufficiently maintaining the effective flavor components of labdanoids and hydrocarbons. According to the method for producing the purified labdanum extract according to the present embodiment, the purified labdanum extract according to the present embodiment described above can be produced simply and efficiently.

(Step 1)
In this step, a labdanum extract is prepared. The labdanum extract is not particularly limited, but may be, for example, a steam distillate (oil), a solvent extract (concrete or absolute), or an alcohol extract of gum resin (resinoid).

(Step 2)
In this step, the labdanum extract of step 1 is separated into fraction and residue by distillation.In order to prevent the content components from being affected by chemical changes caused by heat, the distillation is preferably vacuum distillation.The distillation may be performed in a continuous manner or in a batch manner.The apparatus used for distillation is not particularly limited, but for example, a short-path distiller can be used in a continuous manner, and a glass tube oven can be used in a batch manner.

In this step, distillation may be performed once, but it is preferable to perform it twice or more, since low boiling point components can be removed more accurately. For example, when distillation is performed once, the labdanum extract is separated into a fraction and a residue by distillation, and the residue can be used as a purified labdanum extract. On the other hand, when distillation is performed twice, as shown in FIG. 1, the labdanum extract is first separated into fraction 1 (low boiling point components) and residue 1 by the first distillation (step 2-1). Next, the residue 1 is subjected to a second distillation to separate it into fraction 2 and residue 2 (step 2-2). Since the main low boiling point components have been removed as fraction 1 by step 2-1, both fraction 2 and residue 2 can be used as purified labdanum extract (purified labdanum extracts 1 and 2). However, Residue 2 (Purified Labdanum Extract 2) contains less low-boiling components and more high-boiling components such as labdanoids and hydrocarbons that are useful as flavor components, making it more preferable as a purified labdanum extract for use as a flavor enhancer in tobacco.

When distillation is performed once, the pressure in the distillation is preferably 10 to 60 Pa, and more preferably 10 to 40 Pa, in absolute pressure. The temperature in the distillation depends on the pressure in the distillation, but is preferably 120 to 170°C, and more preferably 130 to 160°C. The distillation time depends on the pressure and temperature in the distillation, but for example, in the case of short-path distillation, the input flow rate is 50 to 300 g/hour and the passing time through the heating evaporation section is 30 seconds to 5 minutes, and in the case of a glass tube oven, the heating time can be 60 to 240 minutes. The mass ratio of the fraction and the residue is not particularly limited, but the ratio of the mass of the fraction to the total mass of the fraction and the residue can be, for example, 1 to 20 mass%.

When distillation is performed twice, the pressure in the first distillation is preferably 40 to 3000 Pa, more preferably 40 to 1800 Pa, in absolute pressure. The temperature in the first distillation depends on the pressure in the first distillation, but is preferably 50 to 150°C, more preferably 90 to 130°C. The time of the first distillation depends on the pressure and temperature in the first distillation, but for example, in the case of short path distillation, the input flow rate is 100 to 400 g/hour and the passing time through the heating evaporation section is 15 seconds to 3 minutes, and in the case of a glass tube oven, the heating time can be 30 to 180 minutes. The mass ratio of fraction 1 and residue 1 is not particularly limited, but the ratio of the mass of fraction 1 to the total mass of fraction 1 and residue 1 can be, for example, 1 to 10 mass%.

The pressure in the second distillation is preferably 10 to 60 Pa, and more preferably 10 to 40 Pa, in absolute pressure. The temperature in the second distillation depends on the pressure in the second distillation, but is preferably 120 to 170°C, and more preferably 130 to 160°C. The time of the second distillation depends on the pressure and temperature in the second distillation, but for example, in the case of short path distillation, the input flow rate is 100 to 400 g/hour and the passing time through the heating evaporation section is 15 seconds to 3 minutes, and in the case of a glass tube oven, the heating time can be 30 to 180 minutes. The mass ratio of fraction 2 and residue 2 is not particularly limited, but the ratio of the mass of fraction 2 to the total mass of fraction 2 and residue 2 can be, for example, 1 to 20 mass%.

[Tobacco materials]
The tobacco material according to the present embodiment includes the purified labdanum extract according to the present embodiment. The tobacco material according to the present embodiment is not particularly limited as long as it includes the purified labdanum extract according to the present embodiment, and examples thereof include tobacco flavorings such as liquid flavorings, tobacco sheets, and tobacco shreds.

A tobacco sheet is a sheet obtained by molding a composition containing aged tobacco leaves. The aged tobacco leaves used for the tobacco sheet are not particularly limited, but may be, for example, those that have been deboned and separated into lamina and midrib. Aged tobacco leaves refer to tobacco leaves that have been subjected to processes such as curing and long-term storage in a warehouse or the like. In this embodiment, a "sheet" refers to a material that has a pair of approximately parallel main and side surfaces. A tobacco sheet can be molded by known methods such as a papermaking method, a casting method, or a rolling method. Details of various tobacco sheets molded by such methods are disclosed in "Encyclopedia of Tobacco, Tobacco Research Center, March 31, 2009." The manner in which the purified labdanum extract according to this embodiment is added to the tobacco sheet is not limited.

For example, the purified labdanum extract according to the present embodiment may be dissolved in a solvent to prepare a liquid tobacco flavoring agent, which may then be sprayed or impregnated into a completed tobacco sheet, or the purified labdanum extract according to the present embodiment may be added when the tobacco sheet is molded. For example, in the papermaking method, water-soluble components are extracted from aged tobacco leaves and separated into an aqueous extract and a residue, a mixture of the fibrous residue and pulp is made into paper, and a concentrated solution of the aqueous extract is added to the paper-made sheet, and the purified labdanum extract according to the present embodiment may be added to the aqueous extract. In the casting method, water, pulp, binder, and ground aged tobacco are mixed to form a mixture, which is then cast, and the purified labdanum extract according to the present embodiment may be added to the mixture. In the rolling method, water, pulp, binder, and ground aged tobacco are mixed to form a mixture, which is then fed into a plurality of rolling rollers for rolling, and the purified labdanum extract according to the present embodiment may be added to the mixture.

Furthermore, as described in WO 2014/104078, a nonwoven tobacco sheet can be obtained by mixing ground aged tobacco with a binder to form a mixture, sandwiching the mixture between nonwoven fabrics, and forming the laminate into a certain shape by thermal welding. In this method, the purified labdanum extract according to this embodiment can be added to the mixture.

The tobacco sheet may contain an aerosol-generating substrate (aerosol source). The type of aerosol-generating substrate is not particularly limited, and extracts from various natural products or their components can be selected according to the application. Specific examples of aerosol-generating substrates include polyhydric alcohols such as glycerin, propylene glycol, sorbitol, xylitol, and erythritol, triacetin, 1,3-butanediol, and mixtures thereof. The content of the aerosol-generating substrate can be adjusted to various amounts depending on the form in which it is used in the tobacco product. For example, when the tobacco sheet contains an aerosol-generating substrate, the content is usually 5% by mass or more, preferably 10% by mass or more, and more preferably 15% by mass or more, and usually 50% by mass or less, preferably 40% by mass or less, and more preferably 25% by mass or less, based on the total mass of the tobacco sheet, from the viewpoint of obtaining a good flavor.

Tobacco shreds may be aged tobacco leaves shredded to a specified size, the tobacco sheets described above shredded to a specified size, or a mixture of these. The size is not limited, and an example is a shredded tobacco sheet with a width of 0.5 to 2.0 mm and a length of 3 to 10 mm. Tobacco shreds of this size are preferred in the aspect of filling a filling material described below. Other examples of tobacco shreds include strand-type shredded tobacco leaves shredded to a width of 0.5 to 2.0 mm and a length longer than the tobacco shreds described above, preferably about the same length as cigarette paper. The purified labdanum extract according to this embodiment may be added to the tobacco shreds or to the raw material before cutting.

The tobacco shreds may contain the aerosol-generating substrate. When the tobacco shreds contain the aerosol-generating substrate, the content thereof is usually 5% by mass or more, preferably 10% by mass or more, and more preferably 15% by mass or more, relative to the mass of the tobacco shreds, from the viewpoint of generating a sufficient amount of aerosol and obtaining a good flavor, and is usually 50% by mass or less, preferably 40% by mass or less, and more preferably 25% by mass or less.

[Tobacco rods, flavor inhalers]
The tobacco rod according to the present embodiment includes the tobacco material according to the present embodiment. The flavor inhaler according to the present embodiment includes the tobacco rod according to the present embodiment. The flavor inhaler according to the present embodiment can be a non-combustion heating type flavor inhaler, a non-combustion non-heating type flavor inhaler, or a combustion type flavor inhaler.

In this embodiment, a "flavor inhaler" refers to an item that allows a user to inhale flavors. Flavor inhalers are broadly divided into "combustion-type flavor inhalers" that generate flavors through combustion, and "non-combustion-type flavor inhalers" that generate flavors without combustion. Non-combustion-type flavor inhalers are further broadly divided into "non-combustion heating-type flavor inhalers" that generate flavors through heating, and "non-combustion non-heating-type flavor inhalers" that generate flavors without heating. The combination of a device for generating aerosols (such as a heating device or atomizing device) and a non-combustion heating-type flavor inhaler is also referred to as a non-combustion heating-type flavor inhalation system.

(Non-combustion heating type flavor inhaler)
FIG. 2 shows one embodiment of the non-combustion heating type flavor inhaler according to the present embodiment. As shown in FIG. 2, the non-combustion heating type flavor inhaler 20 includes a tobacco rod 20A, a cylindrical cooling part 20B having perforations on the circumference, and a filter part 20C. The non-combustion heating type flavor inhaler 20 may include other members. The axial length of the non-combustion heating type flavor inhaler 20 is not limited, but is preferably 40 to 90 mm, more preferably 50 to 75 mm, and even more preferably 50 to 60 mm or less. The circumferential length of the non-combustion heating type flavor inhaler 20 is preferably 16 to 25 mm, more preferably 20 to 24 mm, and even more preferably 21 to 23 mm. For example, the tobacco rod 20A may have a length of 20 mm, the cooling part 20B may have a length of 20 mm, and the filter part 20C may have a length of 7 mm. The lengths of these individual members may be changed as appropriate depending on the manufacturing suitability, the required quality, and the like. FIG. 2 shows an embodiment in which the first segment 25 is disposed, but it is also possible to dispose the first segment 25 and to dispose only the second segment 26 downstream of the cooling section 20B.

(1) Tobacco rod 20A
In the tobacco rod 20A, tobacco shreds or tobacco sheets containing the purified labdanum extract according to the present embodiment can be used as the tobacco filler 21. The method of filling the tobacco filler 21 into the cigarette paper 22 is not particularly limited, but for example, the tobacco filler 21 may be wrapped in the cigarette paper 22, or the tobacco filler 21 may be filled into a cylindrical cigarette paper 22. When the tobacco has a longitudinal direction such as a rectangular shape, the tobacco may be filled so that the longitudinal direction is in an unspecified direction within the cigarette paper 22, or may be filled so that the tobacco is aligned in the axial direction of the tobacco rod 20A or aligned in a direction perpendicular to the axial direction. When the tobacco rod 20A is heated, the tobacco components, aerosol-generating substrate, and water contained in the tobacco filler 21 are vaporized and are available for inhalation.

(2) Cooling section 20B
The cooling section 20B is preferably constructed of a cylindrical member. The cylindrical member may be, for example, a cardboard tube 23 formed by processing cardboard into a cylindrical shape. The cooling section 20B may also be formed by a sheet of thin material that is wrinkled and then pleated, gathered, or folded to form a channel. For example, a sheet material selected from the group consisting of polyethylene, polypropylene, polyvinyl chloride, polyethylene terephthalate, polylactic acid, cellulose acetate, and aluminum foil may be used as such a material. The total surface area of the cooling section 20B is appropriately adjusted in consideration of the cooling efficiency, and may be, for example, 300 to 1000 mm ² /mm. The cooling section 20B is preferably provided with perforations 24. Due to the presence of the perforations 24, outside air is introduced into the cooling section 20B during inhalation. As a result, the aerosol vaporized components generated by heating the tobacco rod 20A come into contact with the outside air, and the temperature is lowered, so that the components are liquefied, and an aerosol is formed. The diameter (distance across) of the perforations 24 is not particularly limited, and may be, for example, 0.5 to 1.5 mm. The number of perforations 24 is not particularly limited, and may be one or two or more. For example, a plurality of perforations 24 may be provided on the circumference of the cooling portion 20B.

The cooling section 20B may be rod-shaped with an axial length of, for example, 7 to 28 mm. For example, the axial length of the cooling section 20B may be 18 mm. The cooling section 20B may have a substantially circular axial cross-sectional shape with a diameter of 5 to 10 mm. For example, the diameter of the cooling section may be approximately 7 mm.

(3) Filter section 20C
The configuration of the filter part 20C is not particularly limited, and may be composed of one or more filling layers. The outside of the filling layer may be wrapped with one or more wrapping papers. The airflow resistance of the filter part 20C can be appropriately changed depending on the amount and material of the filling filled in the filter part 20C. For example, when the filling is cellulose acetate fiber, the airflow resistance can be increased by increasing the amount of cellulose acetate fiber filled in the filter part 20C. When the filling is cellulose acetate fiber, the packing density of the cellulose acetate fiber can be 0.13 to 0.18 g/cm ^3. The airflow resistance is a value measured by an airflow resistance measuring device (product name: SODIMAX, manufactured by SODIM).

The circumferential length of the filter part 20C is not particularly limited, but is preferably 16 to 25 mm, more preferably 20 to 24 mm, and even more preferably 21 to 23 mm. The axial length of the filter part 20C (horizontal direction in FIG. 2) can be selected from 4 to 10 mm, and is selected so that the airflow resistance is 15 to 60 mmH ₂ O/seg. The axial length of the filter part 20C is preferably 5 to 9 mm, and more preferably 6 to 8 mm. The cross-sectional shape of the filter part 20C is not particularly limited, but can be, for example, a circle, an ellipse, a polygon, or the like. In addition, a destructible capsule containing a fragrance, fragrance beads, or a fragrance may be directly added to the filter part 20C.

The filter section 20C may have a center hole section as the first segment 25. The center hole section is composed of a first filling layer 25a having one or more hollow sections and an inner plug wrapper (inner wrapping paper) 25b that covers the filling layer. The center hole section has the function of increasing the strength of the mouthpiece section. The center hole section may not have an inner plug wrapper 25b and may maintain its shape by thermoforming. The first filling layer 25a may be, for example, a rod with an inner diameter of φ5.0 to φ1.0 mm, in which cellulose acetate fibers are densely packed and a plasticizer containing triacetin is added at 6 to 20 mass% relative to the mass of cellulose acetate and hardened. Since the first filling layer 25a has a high fiber packing density, air and aerosol flow only through the hollow section during inhalation and hardly flow inside the first filling layer 25a. Since the first filling layer 25a of the center hole section is a fiber packing layer, the feel from the outside during use is less likely to cause discomfort to the user. The filter section 20C may include a second segment 26. The second segment 26 is composed of a second packed layer 26a and an inner plug wrapper (inner wrapping paper) 26b that covers the packed layer.

The first segment 25 and the second segment 26 are connected by an outer plug wrapper (outer wrapping paper) 27. The outer plug wrapper 27 can be, for example, a cylindrical piece of paper. The tobacco rod 20A, the cooling section 20B, and the first segment 25 and the second segment 26 that have already been connected are connected by a mouthpiece lining paper 28. These connections can be made, for example, by applying a vinyl acetate glue or other adhesive to the inner surface of the mouthpiece lining paper 28 and wrapping the three components. These components may be connected in multiple layers using multiple lining papers.

(Non-combustion heating type flavor inhalation system)
An example of the non-combustion heating type flavor inhalation system according to the present embodiment is shown in Fig. 3. In Fig. 3, the non-combustion heating type flavor inhalation system includes a non-combustion heating type flavor inhaler 20 and a heating device 10 that heats a tobacco rod 20A from the outside.

The heating device 10 includes 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, and the heater 12 and the metal tube 13 are disposed at a position corresponding to the tobacco rod 20A inserted therein. The heater 13 can be an electric resistance heater, and the battery unit 14 supplies power to the heater 12 in response to an instruction from the control unit 15 that controls the temperature, thereby heating the heater 12. The heat generated by the heater 12 is transferred to the tobacco rod 20A through the metal tube 13, which has high thermal conductivity. FIG. 3 shows an embodiment in which the heating device 10 heats the tobacco rod 20A from the outside, but it may also heat the tobacco rod 20A from the inside. The heating temperature by the heating device 10 is not particularly limited, but is preferably 400°C or less, more preferably 150 to 400°C, and even more preferably 200 to 350°C. The heating temperature refers to the temperature of the heater 12 of the heating device 10.

(Non-burning, non-heating flavor inhaler)
4 shows one aspect of the non-combustion non-heating flavor inhaler according to the present embodiment. The non-combustion non-heating flavor inhaler 30 has a power supply unit 30D, a cartridge 30E, and a tobacco capsule 30F. The non-combustion non-heating flavor inhaler 30 has a shape extending from a non-suction end u (upstream) to a mouth end d (downstream). The cartridge 30E is detachable from the power supply unit 30D. The tobacco capsule 30F is 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 and has a flavor source 300 therein. The flavor source 300 includes the tobacco material according to this embodiment. The tobacco capsule 30F is connected to a cartridge 30E. Specifically, a portion of the tobacco capsule 30F is accommodated in the cartridge 30E.

The tobacco capsule 30F has a container 310 that contains the flavor source 300, a mesh body 320, a nonwoven fabric 330, and a cap 340. The aerosol atomized by the atomization section 220 described below is introduced into the container 310 through the mesh body 320, and is flavored by contacting the flavor source 300. The aerosol is then inhaled by the user through the nonwoven fabric 330. In this way, the non-combustion, non-heating type flavor inhaler 30 can impart flavor to the aerosol without heating the flavor source 300. Furthermore, substantially no aerosol is generated from the flavor source 300.

In the direction of the aerosol flow, the length of the tobacco capsule 30F (container 310) is preferably 40 mm or less, and more preferably 25 mm or less. In addition, in the direction of the aerosol flow, the length is preferably 1 mm or more, and more preferably 5 mm or more. In the direction perpendicular to the direction of the aerosol flow, the maximum length of the container 310 of the tobacco capsule 30F (container 310) is preferably 20 mm or less, and more preferably 10 mm or less. In addition, in the direction perpendicular to the direction of the aerosol flow, the maximum length of the tobacco capsule 30F (container 310) is preferably 1 mm or more, and more preferably 3 mm or more.

The flavor source 300 containing tobacco is composed of raw material pieces that impart flavor to the aerosol. The lower limit of the size of the raw material pieces is preferably 0.2 to 1.2 mm, and more preferably 0.2 to 0.7 mm. The smaller the size of the raw material pieces that constitute the flavor source 300, the greater the specific surface area, and therefore the easier it is to release the flavor components. As the raw material pieces that constitute the flavor source 300, shredded tobacco containing the purified labdanum extract of this embodiment, or a molded product obtained by molding the tobacco material of this embodiment into a granular form, etc., can be used. The flavor source 300 may contain flavorings such as plants other than tobacco (e.g., mint, herbs, etc.) and menthol. Furthermore, the flavor source 300 containing tobacco may contain a flavoring agent. Examples of flavoring agents include materials that exhibit sweetness, sourness, saltiness, umami, bitterness, astringency, richness, spiciness, harshness, and astringency. Examples of materials that exhibit sweetness include sugars, sugar alcohols, and sweeteners. Examples of sugars include monosaccharides, disaccharides, oligosaccharides, polysaccharides, etc. Examples of sweeteners include natural sweeteners, synthetic sweeteners, etc.

The raw material pieces are obtained, for example, by sieving in accordance with JIS Z 8815 using a stainless steel sieve conforming to JIS Z 8801. For example, a stainless steel sieve having a mesh size of 0.71 mm is used to sieve the raw material pieces for 20 minutes by a dry mechanical shaking method to obtain raw material pieces that pass through the stainless steel sieve having a mesh size of 0.71 mm. Next, a stainless steel sieve having a mesh size of 0.212 mm is used to sieve the raw material pieces for 20 minutes by a dry mechanical shaking method to remove the raw material pieces that pass through the stainless steel sieve having a mesh size of 0.212 mm. In other words, the raw material pieces that make up the flavor source 300 are raw material pieces that pass through the stainless steel sieve (mesh size = 0.71 mm) that specifies the upper limit, but do not pass through the stainless steel sieve (mesh size = 0.212 mm) that specifies the lower limit. Therefore, the lower limit of the size of the raw material pieces that make up the flavor source 300 is defined by the opening of the stainless steel sieve that defines the lower limit. Also, the upper limit of the size of the raw material pieces that make up the flavor source 300 is defined by the opening of the stainless steel sieve that defines the upper limit.

From the viewpoint of good flavor, the amount of flavor source 300 contained in the container 310 is preferably 300 mg or more, and more preferably 350 mg or more.

(2) Power Supply Unit An example of the 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 battery or a rechargeable battery. The initial value of the output voltage of the battery 110 is preferably in the range of 1.2 V to 4.2 V. The battery capacity of the battery 110 is preferably in the range of 100 mAh to 1000 mAh.

(3) Cartridge An example of a cartridge 30E is shown in Figures 7 and 8. Figure 7 is a cross-sectional view of an example of the cartridge 30E, and Figure 8 is a diagram showing its internal structure. The cartridge 30E has a reservoir 210, an atomizing section 220, a flow path forming body 230, an outer frame 240, and an end cap 250. The cartridge 30E has a first flow path 200X, which is disposed downstream of the atomizing section 220, as an aerosol flow path.

The reservoir 210 stores the aerosol source 200. The reservoir 210 is located around the flow path forming body 230 in a cross section perpendicular to the flow direction of the aerosol (direction from the non-suction end to the suction end (upstream to downstream)). The reservoir 210 is located in the gap between the flow path forming body 230 and the outer frame body 240. The reservoir 210 is formed of a porous body such as a resin web or cotton, for example. The reservoir 210 may also be formed of a tank that contains the liquid aerosol source 200. Examples of the aerosol source 200 include glycerin, propylene glycol, etc.

The atomization unit 220 atomizes the aerosol source 200 without combustion using power supplied from the battery 110. The atomization unit 220 is composed of a heating wire (coil) wound at a predetermined pitch. The atomization unit 220 is preferably composed of a heating wire having a resistance value in the range of 1.0 to 3.0 Ω. The predetermined pitch is equal to or greater than the value at which the heating wires do not come into contact, and is preferably smaller than that. The predetermined pitch is preferably, for example, 0.40 mm or less. The predetermined pitch is preferably constant to stabilize the atomization of the aerosol source 200. The predetermined pitch is the distance between the centers of adjacent heating wires.

The flow path forming body 230 has a cylindrical shape that forms a first flow path 200X that extends along the flow direction of the aerosol. The outer frame body 240 has a cylindrical shape that houses the flow path forming body 230. The outer frame body 240 extends downstream beyond the end cap 250 and houses a part of the tobacco capsule 30F. The end cap 250 is a cap that closes the gap between the flow path forming body 230 and the outer frame body 240 from the downstream side. The end cap 250 prevents the aerosol source 200 stored in the reservoir 210 from leaking to the tobacco capsule 30F.

(Combustion-type flavor inhaler)
An example of a combustion type flavor inhaler according to the present embodiment is shown in FIG. 9. As shown in FIG. 9, the combustion type flavor inhaler 40 includes a tobacco rod 41 and a filter 42 provided adjacent to the tobacco rod 41. The tobacco rod 41 includes a tobacco filler 43 containing the purified labdanum extract according to the present embodiment, and a wrapper 44 wrapped around the tobacco filler 43. The tobacco rod 41 and the filter 42 are connected by a tipping paper member 45 wrapped around the tobacco rod 41 and the filter 42. The tipping paper member 45 may have an air hole in a part of its outer periphery. The number of the air holes may be one or more, and for example, 10 to 40 air holes may be formed. When the number of the air holes is more than one, the air holes may be arranged in a line in a ring shape on the outer periphery of the tipping paper member 45. The multiple air holes may be arranged at approximately regular intervals. By providing the air holes, air is taken into the filter 42 through the air holes during inhalation. By diluting the mainstream smoke with outside air from the ventilation hole, a product with a desired tar value can be designed. A typical example of such a combustion-type flavor inhaler is a cigarette. A user can enjoy the flavor of tobacco by lighting the tip of the tobacco rod 41 and holding the mouth end of the filter 42 in their mouth and inhaling.

　Below, this embodiment will be described in detail with reference to examples, but this embodiment is not limited to these examples.

[Example 1]
(Production of Purified Labdanum Extract)
Labdanum extract was purified by the method shown in FIG. 1 to obtain a purified labdanum extract. Specifically, 500 g of labdanum extract (Resinoid) was first prepared (Step 1). Next, in order to give fluidity, the labdanum extract was heated to 130° C. in advance, and 496.1 g of the labdanum extract was continuously charged into a short-path distiller (trade name: DN-60, manufactured by Asahi Seisakusho) at a rate of 250 g/hour, and fractionated under conditions of an absolute pressure of 1700 Pa and a jacket temperature of 130° C. (Step 2-1). As a result, 15.2 g of fraction 1 and 464.9 g of residue 1 were obtained. The residue 1 was heated again to 130° C., and then charged into the apparatus, and fractionated under conditions of an absolute pressure of 20 Pa and a jacket temperature of 150° C. (Step 2-2). As a result, 78.6 g of fraction 2 (purified labdanum extract 1) and 362.1 g of residue 2 (purified labdanum extract 2) were obtained.

　The unpurified labdanum extract (Resinoid), purified labdanum extract 1, and purified labdanum extract 2 were each dissolved in ethanol and subjected to GC/MS analysis under the following conditions. The chromatogram of the unpurified labdanum extract (Resinoid) is shown in Figure 10, the chromatogram of purified labdanum extract 1 in Figure 11, and the chromatogram of purified labdanum extract 2 in Figure 12.

Equipment: Agilent Technologies 7890A GC
Oven 40℃ (3 min) → 4℃/min → 280℃ (20 min)
Run time: 83 minutes Injection volume: 1 μl
Injection mode Split (10:1)
Inlet temperature 270℃
Septum purge flow rate: 5 ml/min Gas saver: off Transfer line temperature: 280°C
Column: HP-5MS (30m x 0.25mm x 0.25μm)
Column flow rate: 1 ml/min (constant flow mode)
Solvent waiting 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℃

In addition, the peak area ratios in each retention index (RI) range in the chromatogram obtained by the GC/MS analysis are shown in Table 1.

The chemical structures of the compounds (labdanoids or their analogues) represented by peaks a) to d) in the chromatograms shown in Figures 11 and 12 are shown below.

(Evaluation as a tobacco flavor enhancer)
Tobacco materials were prepared by adding 500 ppm by mass of unrefined labdanum extract (Resinoid), purified labdanum extract 1, or purified labdanum extract 2 to tobacco shreds. The tobacco materials were filled into the tobacco rod of a non-combustion heating type flavor inhaler, and panelists used the non-combustion heating type flavor inhaler to perform sensory evaluation of the intensity of amber animal aroma, irritation reduction effect, and flavor persistence. The sensory evaluation was performed by three panelists, and the evaluation was based on the consensus of the three panelists. Regarding the evaluation of the irritation reduction effect and the improvement of flavor persistence, the unrefined labdanum extract (Resinoid) was used as a control, and it was judged whether the purified labdanum extract 1 and the purified labdanum extract 2 had an irritation reduction effect and whether the flavor persistence was improved. The three panelists had been thoroughly trained in these sensory evaluations using multiple types of samples, and it was confirmed that the evaluation thresholds were equal and unified among the panelists. The results are shown in Table 2.

As shown in Table 2, the refined labdanum extract 1 and refined labdanum extract 2 according to this embodiment had a weaker amber animal scent and improved scent persistence compared to the unrefined labdanum extract (Resinoid). Therefore, it was found that the refined labdanum extract 1 and refined labdanum extract 2 according to this embodiment are effective as tobacco flavor enhancers. In particular, the refined labdanum extract 2 provided an irritation-reducing effect, which is a function similar to that of Orient tobacco, and also imparted a persistent heavy feeling, making it easier to smoke.

[Example 2]
Labdanum extract was purified by the method shown in FIG. 1 to obtain a purified labdanum extract. Specifically, 1.6 g of labdanum extract (Resinoid) was first prepared (Step 1). Next, the labdanum extract was subjected to continuous fractional distillation under conditions of absolute pressure of 55 Pa and heating temperature of 60° C., absolute pressure of 40 Pa and heating temperature of 90° C., and absolute pressure of 40 Pa and heating temperature of 130° C. (Step 2-1). As a result, 0.06 g of fraction 1 and 1.54 g of residue 1 were obtained. The residue 1 was further fractionally distilled under conditions of absolute pressure of 40 Pa and heating temperature of 160° C. (Step 2-2). As a result, 0.03 g of fraction 2 (purified labdanum extract 1) and 1.48 g of residue 2 (purified labdanum extract 2) were obtained.

　The labdanum extract before purification (Resinoid), purified labdanum extract 1, and purified labdanum extract 2 were each dissolved in ethanol, and GC/MS analysis was carried out under the same conditions as in Example 1. In the chromatogram obtained by the GC/MS analysis, the peak area ratios in each retention index (RI) range are shown in Table 3.

This embodiment includes the following aspects:

[1] A purified labdanum extract in which, when analyzed by GC/MS using a column whose stationary phase is 95% dimethylpolysiloxane, the sum of the peak areas of components having a retention index (RI) of 1399 or less is 20% or less of the sum of the entire peak area.

[2] The purified labdanum extract according to [1], in which the sum of the peak areas of the component groups having a retention index (RI) of 2500 or more is 30% or more of the sum of the entire peak area.

[3] The purified labdanum extract according to [1] or [2], in which the sum of the peak areas of the component groups having a retention index (RI) of 1700 or more is 90% or more of the sum of the entire peak area.

[4] A purified labdanum extract according to any one of [1] to [3], in which the sum of the peak areas of the component group having a retention index (RI) of 1800 to 1900 is 4% or less of the sum of the entire peak area.

[5] A method for producing a purified labdanum extract according to any one of [1] to [4], comprising the steps of:
Step 1 of preparing a labdanum extract;
Step 2: separating the labdanum extract into a fraction and a residue using distillation;
The method includes:

[6] The method according to [5], wherein the distillation is reduced pressure distillation.

[7] The method according to [5] or [6], wherein the labdanum extract is a steam distillate (oil), a solvent extract (concrete or absolute), or an alcohol extract of gum resin (resinoid).

[8] A purified labdanum extract according to any one of [1] to [4], which is used in a flavor inhaler.

[9] The purified labdanum extract described in [8], which is used in a non-combustion, non-heating flavor inhaler or a non-combustion, non-heating flavor inhaler.

[10] The purified labdanum extract described in [8], which is used in a combustion-type flavor inhaler.

[11] A tobacco material containing a purified labdanum extract according to any one of [1] to [4] and [8] to [10].

[12] A tobacco rod comprising the tobacco material described in [11].

[13] A flavor inhaler comprising the tobacco rod described in [12].

[14] The flavor inhaler described in [13], which is a non-combustion heating type flavor inhaler or a non-combustion non-heating type flavor inhaler.

[15] The flavor inhaler described in [13], which is a combustion type flavor inhaler.

10 Heating device 11 Body 12 Heater 13 Metal tube 14 Battery unit 15 Control unit 16 Recess 17 Vent 20 Non-combustion heating type flavor inhaler 20A Tobacco rod section 20B Cooling section 20C Filter section 21 Tobacco filler 22 Cigarette 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-combustion non-heating type flavor inhaler 30D Power supply unit 30E Cartridge 30F Tobacco capsule u Non-suction end d Suction end 40 Combustion 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 section 230 Flow passage forming body 240 Outer frame body 240
250 End cap 200X First flow path 300 Flavor source 310 Container 320 Mesh body 330 Nonwoven fabric 340 Cap

Claims (15)

A purified labdanum extract in which the sum of the peak areas of components with a retention index (RI) of 1399 or less is 20% or less of the sum of the entire peak area when analyzed by GC/MS using a column whose stationary phase is 95% dimethylpolysiloxane. The purified labdanum extract according to claim 1, wherein the sum of the peak areas of the component groups having a retention index (RI) of 2500 or more is 30% or more of the sum of the entire peak areas. The purified labdanum extract according to claim 1 or 2, wherein the sum of the peak areas of the component groups having a retention index (RI) of 1700 or more is 90% or more of the sum of the entire peak areas. The purified labdanum extract according to any one of claims 1 to 3, wherein the sum of the peak areas of the component group having a retention index (RI) of 1800 to 1900 is 4% or less of the sum of the entire peak area. A method for producing a purified labdanum extract according to any one of claims 1 to 4, comprising the steps of:
Step 1 of preparing a labdanum extract;
Step 2: separating the labdanum extract into a fraction and a residue using distillation;
The method includes: The method of claim 5, wherein the distillation is vacuum distillation. The method according to claim 5 or 6, wherein the labdanum extract is a steam distillate (Oil), a solvent extract (Concrete or Absolute), or an alcohol extract of gum resin (Resinoid). The purified labdanum extract according to any one of claims 1 to 4, which is used in a flavor inhaler. The purified labdanum extract according to claim 8, which is used in a non-combustion, non-heating flavor inhaler or a non-combustion, non-heating flavor inhaler. The purified labdanum extract according to claim 8, which is used in a combustion-type flavor inhaler. A tobacco material comprising the purified labdanum extract according to any one of claims 1 to 4 and 8 to 10. A tobacco rod comprising the tobacco material according to claim 11. A flavor inhaler comprising the tobacco rod according to claim 12. The flavor inhaler according to claim 13, which is a non-combustion heating type flavor inhaler or a non-combustion non-heating type flavor inhaler. The flavor inhaler according to claim 13, which is a combustion type flavor inhaler.