EP4643668A1

EP4643668A1 - Constituent member perfumed by flavor raw material and smoking article

Info

Publication number: EP4643668A1
Application number: EP22969943.4A
Authority: EP
Inventors: Toru Ishii; Kojiro TOKUNAGA; Yasuhiro Nakagawa; Naoya TSURUOKA; Haruna HIRAKAWA; Kenichi Kudo; Katsunori MURAKOSHI
Original assignee: Japan Tobacco Inc
Current assignee: Japan Tobacco Inc
Priority date: 2022-12-26
Filing date: 2022-12-26
Publication date: 2025-11-05
Also published as: KR20250100785A; JPWO2024142149A1; WO2024142149A1; CN120769707A

Abstract

The purpose of the present invention is to provide a constituent member perfumed by a flavor raw material, the constituent member providing strong cool feeling, being excellent in storage resistance and having less bitterness.

This constituent member perfumed by a flavor raw material comprises a smoking article constituent member, and
a flavor raw material, wherein the flavor raw material includes a cooling sensation agent (A) with a retention index (RI) of 1300 or more in a chromatogram obtained through analysis with gas chromatography with a mass spectrometer (GC/MS) using a column in which the stationary phase is 95% dimethylpolysiloxane/5% phenyl-methyl polysiloxane,
and the flavor raw material perfumes the smoking article constituent member.

Description

TECHNICAL FIELD

The present invention pertains to flavoring ingredient-scented constituent members and smoking articles.

BACKGROUND ART

A cooling sensation component (i.e., a type of flavoring ingredient) such as menthol is added to a constituent member of a smoking article, such as a tobacco filler, so that a cooling sensation is obtained in a combustion smoking article, a heated smoking article (i.e., a heat-not-burn smoking article), a smokeless smoking article, or an electronic cigarette. Thereby a constituent member that is scented with a flavoring ingredient (i.e., a flavoring ingredient-scented constituent member) is formed.

SUMMARY OF INVENTION

TECHNICAL PROBLEM

Smoking articles may also have requirements as to the cooling sensation intensity, storage resistance, and bitter flavor properties, as follows.

The stronger the cooling sensation intensity of a cooling sensation component, the less of the cooling sensation component needs to be admixed to achieve a predetermined cooling sensation intensity, thus increasing the degree of freedom in blending components other than the cooling sensation component into the flavoring ingredient. The level of scenting with the flavoring ingredient can also be reduced if the cooling sensation intensity of the cooling sensation component is stronger. Since there are thus advantages from a manufacturing perspective, there is a need for a cooling sensation component of greater cooling sensation intensity.

Smoking articles may be used after being stored for long periods of time. Therefore, the flavoring ingredient-scented constituent member must retain cooling sensation intensity after storage (i.e., must have excellent storage resistance in terms of cooling sensation intensity).
However, cooling sensation components, of which menthol is representative, are often highly volatile Commercially available smoking articles are usually stored in closed systems that are covered with a film packaging, of which polypropylene is representative, but cooling sensation components such as menthol evaporate inside the packaging, and end up being absorbed into different sites from those to which they were originally added. There is thus a problem that when smoked after opening the film packaging, the product has a different cooling intensity from that at the site to which they were originally added.
Further, after the film packaging is opened, the film packaging becomes an open storage system, and the added cooling sensation components evaporate into the air. In that case, there is also a problem when smoked in that the amount that actually functions as a cooling sensation component is less than the amount originally added, resulting in a product with a weak cooling sensation intensity.

It is known that if the amount of a cooling sensation component is increased to achieve a required cooling sensation intensity, the cooling sensation is imparted together with a bitter flavor. Accordingly, there is a need for a cooling sensation component that increases cooling sensation intensity without increasing the bitter flavor.
In view of these circumstances, the problem addressed by the present invention is to provide a flavoring ingredient-scented constituent member that has powerful cooling sensation intensity, excellent storage resistance, and little bitter flavor.

SOLUTION TO PROBLEM

As a result of intensive research for the purpose of solving the abovementioned problems, the inventors found that the problems can be solved by using a cooling sensation agent showing a specific retention index (RI) as a cooling sensation component, and perfected the present invention. Specific aspects of the present invention are as follows.

[1] A flavoring ingredient-scented constituent member, comprising a constituent member of a smoking article and a flavoring ingredient that contains a cooling sensation agent (A) having a retention index (RI) of 1300 or greater in a chromatogram obtained through analysis thereof by gas chromatography with a mass spectrometer (GC/MS), using a column having a stationary phase of 95% dimethylpolysiloxane/5% phenyl-methylpolysiloxane,
wherein the constituent member of the smoking article is scented with the flavoring ingredient.
[2] The flavoring ingredient-scented constituent member set forth in [1], wherein the retention index (RI) of the cooling sensation agent (A) is 2,000 or greater.
[3] The flavoring ingredient-scented constituent member set forth in [1] or [2], wherein the retention index (RI) of the cooling sensation agent (A) is 2,400-2,600.
[4] The flavoring ingredient-scented constituent member set forth in any one of [1]-[3], wherein the cooling sensation agent (A) contains a methyl menthol derivative represented by the following General Formula (1):
- (in Formula (1), the asterisks are asymmetric carbon atoms, X represents a hydrogen atom or substituent, and Y is an aryl group with 6-20 carbon atoms that may have a substituent)
- or a salt thereof.
[5] The flavoring ingredient-scented constituent member set forth in any one of [1]-[4], wherein the content of the cooling sensation agent (A) is 1 ppm or more of the flavoring ingredient-scented constituent member.
[6] The flavoring ingredient-scented constituent member set forth in any one of [1]-[5], wherein the flavoring ingredient contains a flavor, a cooling sensation component, or a combination thereof.
[7] The flavoring ingredient-scented constituent member set forth in [6], wherein the cooling sensation component contains a cooling sensation agent, a cooling sensation flavor component, or a combination thereof.
[8] The flavoring ingredient-scented constituent member set forth in [7], wherein the cooling sensation agent comprises the cooling sensation agent (A) and a cooling sensation agent other than the cooling sensation agent (A).
[9] The flavoring ingredient-scented constituent member set forth in [7] or [8], wherein the cooling sensation flavor component comprises menthol, menthone, peppermint oil, or a mixture thereof.
[10] The flavoring ingredient-scented constituent member set forth in any one of [7]-[9], wherein the content of the cooling sensation flavor component is 0.0001-99 wt% of the flavoring ingredient-scented constituent member.
[11] The flavoring ingredient-scented constituent member set forth in any one of [6]-[10], wherein the flavor comprises a natural flavor, a synthetic flavor, or a mixture thereof.
[12] The flavoring ingredient-scented constituent member set forth in any one of [1]-[11], wherein the flavoring ingredient further contains a carrier.
[13] The flavoring ingredient-scented constituent member set forth in [12], wherein the carrier contains a carbohydrate, cellulose derivative, non-pulp fiber, lipid, polyvinylpyrrolidone, polyvinyl alcohol, or a mixture thereof.
[14] The flavoring ingredient-scented constituent member set forth in any one of [1]-[13], wherein the flavoring ingredient further contains an emulsifier.
[15] The flavoring ingredient-scented constituent member set forth in any one of [1]-[14], wherein the flavoring ingredient is liquid, semi-solid, or solid.
[16] The flavoring ingredient-scented constituent member set forth in any one of [1]-[15], wherein the flavoring ingredient-scented constituent member further contains an aerosol source.
[17] The flavoring ingredient-scented constituent member set forth in [16], wherein the aerosol source contains a polyhydric alcohol, triethyl citrate, triacetin, or a mixture thereof.
[18] The flavoring ingredient-scented constituent member set forth in any one of [1]-[17], wherein the constituent member of the smoking article contains a nicotine source.
[19] The flavoring ingredient-scented constituent member set forth in any one of [1]-[18], wherein the flavoring ingredient-scented constituent member further contains an adsorbent.
[20] The flavoring ingredient-scented constituent member set forth in any one of [1]-[19], wherein the constituent member of the smoking article is a tobacco filler, filter, tube, rolling paper, tipping paper, plug, pouch, or liquid.
[21] The flavoring ingredient-scented constituent member set forth in any one of [1]-[20], wherein the constituent member of the smoking article is a non-woven fabric.
[22] A smoking article, comprising the flavoring ingredient-scented constituent member set forth in any one of [1]-[21].
[23] The smoking article set forth in [22], which is a heated smoking article.
[24] The smoking article set forth in [22], which is a combustion smoking article.
[25] The smoking article set forth in [22], which is a non-combustion smoking article.
[26] The smoking article set forth in [22], which is an electronic cigarette.

ADVANTAGEOUS EFFECTS OF INVENTION

The flavoring ingredient-scented constituent member of the present invention imparts a strong cooling sensation, and has excellent storage resistance and little bitter flavor.

BRIEF DESCRIPTION OF DRAWINGS

Fig. 1 is a cross-sectional schematic view showing an example of a heat-not-burn smoking article.
Fig. 2 is a cross-sectional schematic view showing an example of a heat-not-burn smoking system.
Fig. 3 is a perspective view showing an example of the exterior of a heat-not-burn smoking article.
Fig. 4 is an exploded view showing an example of a heat-not-burn smoking article.
Fig. 5 is a schematic view showing an example of the interior of a smoking article 30.
Fig. 6 is a chromatogram of menthol and other cooling sensation agents obtained by GC/MS.
Fig. 7 is a total ion chromatogram, obtained by GC 'MS, of a tobacco stick sample prior to storage with 2,500 ppm of a methyl menthol derivative added.
Fig. 8 is a total ion chromatogram, obtained by GC 'MS, of a tobacco stick sample prior to storage with 5,000 ppm of a methyl menthol derivative added.
Fig. 9 is a total ion chromatogram, obtained by GC 'MS, of a tobacco stick sample prior to storage with 10,000 ppm of a methyl menthol derivative added.
Fig. 10 is a total ion chromatogram, obtained by GC/MS, of a tobacco stick sample after storage with 2,500 ppm of a methyl menthol derivative added.
Fig. 11 is a total ion chromatogram, obtained by GC/MS, of a tobacco stick sample after storage with 5,000 ppm of a methyl menthol derivative added.
Fig. 12 is a total ion chromatogram, obtained by GC/MS, of a tobacco stick sample after storage with 10,000 ppm of a methyl menthol derivative added.

DESCRIPTION OF EMBODIMENTS

In the present description, the unit "ppm" indicates "ppm by weight." In addition, "X-Y," indicating a numerical range, is used in the sense that the numerical values stated first and last are each included as the lower and upper limits thereof.
The flavoring ingredient-scented constituent member and smoking article of the present invention are described below.

1. Flavoring ingredient-scented constituent member

The flavoring ingredient-scented constituent member of the present invention is:

a flavoring ingredient-scented constituent member, comprising a constituent member of a smoking article and
a flavoring ingredient that contains a cooling sensation agent (A) having a retention index (RI) of 1300 or greater in a chromatogram obtained through analysis thereof by gas chromatography with a mass spectrometer (GC/MS), using a column having a stationary phase of 95% dimethylpolysiloxane/5% phenyl-methylpolysiloxane,
wherein the constituent member of the smoking article is scented with the flavoring ingredient.

1-1. Flavoring ingredient

The constituent member of the smoking article is scented with the flavoring ingredient. In the present description, "scenting" means adding a specific ingredient. There are no particular limitations as to the scenting of the constituent member of the smoking article with a flavoring ingredient, which can be accomplished by application, admixture, insertion, or processing that combines two or more thereof. Either the constituent member of the smoking article or a precursor (raw material) of the constituent member may be scented with the flavoring ingredient.

The cooling sensation agent (A) has a retention index (RI) of 1300 or greater in a chromatogram obtained through analysis thereof by gas chromatography with a mass spectrometer (GC/MS), using a column having a stationary phase of 95% dimethylpolysiloxane/5% phenyl-methylpolysiloxane, with 2,000 or greater being preferable, 2,400-2,600 more preferable, and 2,300-2,600 most preferable. As a result of having an RI within the abovementioned numerical range, storage resistance is excellent, and a compound can be efficiently volatilized and inhaled during smoking.

In the present description, 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 carbon number of straight-chain hydrocarbons (n-alkanes) as a standard. When a column having a predetermined stationary phase is used, the 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 RI is specifically calculated by the following equation. $RI = 100 n + 100 (t_{x} - t_{n}) / (t_{n + 1} - t_{n})$

n: Carbon number of n-alkane appearing as a peak immediately before analyte compound peakt_x: Analyte compound peak retention time
t_n: Retention time of n-alkane appearing as a peak immediately before analyte compound peak
t_n+1: Retention time of n-alkane appearing as a peak immediately after analyte compound peak

The RI used in the present description is a value calculated using a mixture of n-alkanes ranging from n-hexane (C6, RI: 600) to n-pentatriacontane (C35, RI: 3500), but the n-alkane mixture used in calculating RI is not limited thereto.
In the present description, the column used in gas chromatography has, for example, a non-polar or low-polar stationary phase, and preferably a non-polar stationary phase. In gas chromatography using these columns, it is believed that the lower the numeric value of RI, the more likely the compound is to volatilize, and conversely, the higher the numeric value of RI, the less likely the compound is to volatilize.
A column with a stationary phase of 95% dimethylpolysiloxane/5% phenyl-methylpolysiloxane, for example, can be used as the column with a low-polar stationary phase.
HP-5MS (manufactured by Agilent Technologies), for example, can be used as a column with a stationary phase of 95% dimethylpolysiloxane/5% phenyl-methylpolysiloxane, but this is not limited thereto.
A column with a stationary phase of 100% dimethylpolysiloxane, for example, can be used as a column with a non-polar stationary phase.
DB-1 (manufactured by Agilent Technologies), for example, can be used as a column with a stationary phase of 100% dimethylpolysiloxane, but this is not limited thereto.
There are no particular limitations as to the apparatus and conditions used for gas chromatography with a mass spectrometer (GC/MS), but the apparatus and conditions mentioned in the Examples below can be used.

While not specifically limited thereto, the cooling sensation agent (A) may contain or consist of a methyl menthol derivative represented by the following General Formula (1).

(in Formula (1), the asterisks are asymmetric carbon atoms, X represents a hydrogen atom or substituent, and Y is an aryl group with 6-20 carbon atoms that may have substituent)
or a salt thereof.

Specifically, methyl menthol derivatives represented by General Formula (1) that are included in the cooling sensation agent (A) have a cyclohexane ring structure and have asymmetric carbons at positions 1 and 2, and therefore, four types of diastereomer represented by the following formula (1-a) to (1-d), respectively, are present.
The methyl menthol derivative represented by the General Formula (1) is preferably a trans form.
There is no particular limitation as to the salt of the methyl menthol derivative represented by General Formula (1), and specific examples include a sodium salt, potassium salt, magnesium salt, calcium salt, and aluminum salt.
In General Formula (1), X represents a hydrogen atom or substituent.
Examples of substituents include a hydroxyl group, acetoxy group, oxo group, alkyl group having 1-10 carbon atoms, hydroxymethyl group, hydroxyethyl group, methoxy group, ethoxy group, and phenoxy group. Examples of an alkyl group having 1-10 carbon atoms include a methyl group, ethyl group, n-propyl group, isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, and decyl group.
Among these, X is preferably a hydrogen atom, hydroxyl group, acetoxy group, oxo group, or methyl group, as regards persistence of cooling sensation, cooling sensation intensity, minimality of bitter flavor, and ease of manufacture.
In General Formula (1), Y is an aryl group having 6-20 carbon atoms that may have a substituent.
Examples of aryl groups having 6-20 carbon atoms include aromatic monocyclic groups, aromatic polycyclic groups, and aromatic fused cyclic groups having 6-20 carbon atoms. Specific examples include a phenyl group, naphthyl group, anthryl group, phenanthryl group, and indenyl group.
The aryl group having 6-20 carbon atoms may have as a substituent, for example: a hydroxy group; a hydroxy alkyl group having 1-4 carbon atoms, such as a hydroxymethyl group, hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, or 1-hydroxybutyl group; an alkoxy group having 1-6 carbon atoms, such as a methoxy group, ethoxy group, n-propoxyl group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, methylenedioxy group, ethylenedioxy group, tert-butoxy group, or phenoxy group; a mercapto group; a thioalkoxy group having 1 to 4 carbon atoms, such as a thiomethoxy group, thioethoxy group, n-thiopropoxy group, thioisopropoxy group, n-thiobutoxy group, thioisobutoxy group, sec-thiobutoxy group, methylenedithio group, or tert-thiobutoxy group; an alkyl group having 1-6 carbon atoms, such as a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, or hexyl group; a cycloalkyl group having 5-8 carbon atoms, such as a cyclopentyl group, a cyclohexyl group, or a cycloheptyl group; a halogen atom, such as a fluorine atom, chlorine atom, bromine atom, or iodine atom; a phenyl group; an aralkyl group having 7-12 carbon atoms, such as a benzyl group, a phenylethyl group, or a naphthylmethyl group; a carboxyl group; an alkoxycarbonyl group having 2-8 carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, or a benzyloxycarbonyl group; an acyl group having 1-7 carbon atoms, such as a formyl group, an acetyl group, a propionyl group, or a benzoyl group; a carboxamide group; a dialkylamino group having 2-8 carbon atoms, such as a dimethylamino group, a diethylamino group, or a dibutylamino group; a nitrile group; a cyanoalkyl group (wherein the alkyl group has 1 to 4 carbon atoms), such as a cyanomethyl group, a cyanoethyl group, a cyanopropyl group, or a cyanobutyl group; an aliphatic heterocyclic group such as an oxiranyl group, an aziridinyl group, 2-oxopyrrolidyl group, piperidyl group, piperazinyl group, morpholino group, tetrahydrofuryl group, tetrahydropyranyl group, or tetrahydrothienyl group; or an aromatic heterocyclic group such as a tetrazinyl group, furyl group, thienyl group, pyridyl group, pyridinyl group, pyrazinyl group, pyradazinyl group, imidazoyl group, oxazoyl group, thiazoyl group, benzofuryl group, benzothienyl group, quinolyl group, isoquinolyl group, quinoxanoyl group, phthalazinyl group, quinazolinyl group, naphthyldinyl group, cinnolinyl group, benzimidazoline group, benzoxazolyl group, or benzothiazolyl groups.
In the present invention, Y is preferably a phenyl group which may have a substituent, as regards persistence of cooling sensation, cooling sensation intensity, minimality of bitter flavor, and ease of manufacture.
In the abovementioned Formula (1), X is preferably a hydrogen atom, hydroxyl group, acetoxy group, oxo group, or methyl group, and Y is preferably a phenyl group which may have a substituent.
The abovementioned Formula (1) is also preferably represented by Structural Formula 2 below: (In Formula 2, the asterisks are asymmetric carbon atoms.)
The following compounds may be cited as examples of methyl menthol derivatives of the invention that are represented by the Formula (1), which are not however limited thereto.
In the following compounds, Me represents a methyl group, Et represents an ethyl group, and Ac represents an acetyl group.
While not specifically limited thereto, the methyl menthol derivative of the invention, represented by Formula (1), may contain or consist of N-(2-hydroxy-2-phenylethyl)-2-isopropyl-5,5-dimethylcyclohexane-1-carboxamide. COOLACT^® 370 (manufactured by Takasago International Corporation) can be used as the N-(2-hydroxy-2-phenylethyl)-2-isopropyl-5,5-dimethylcyclohexane-1-carboxamide.
The methyl menthol derivative of the invention represented by the abovementioned Formula (1) can be synthesized on the basis of a well-known conventional method such as that disclosed in WO 2018/131575 .
The methyl menthol derivative represented by General Formula (1) of the present invention has a powerful cooling sensation intensity, provides a sustained cooling sensation to the back of the throat, and can as such be used alone, as a cooling sensation agent or sensation imparting agent. It is also known that many cooling sensation components impart a bitter flavor together with a cooling sensation, but a cooling sensation experience with little bitter flavor can be obtained during smoking through use of a methyl menthol derivative represented by General Formula (1) of the present invention.
While not specifically limited thereto, the content of the cooling sensation agent (A) may be 1 ppm or more, 100 ppm or more, 200 ppm or more, or 300 ppm or more of the flavoring ingredient-scented constituent member. Alternatively, the content of the cooling sensation agent (A) may be 500,000 ppm or less, 50,000 ppm or less, or 5,000 ppm or less of the flavoring ingredient-scented constituent member. The abovementioned numerical ranges of the content of the cooling sensation agent (A) can be combined as desired. As a result of having the content of the cooling sensation agent (A) within the abovementioned numerical ranges, an effect is obtained such that a cooling sensation is felt at the back of the throat, with little bitter flavor.

The flavoring ingredient may contain a cooling sensation component.
The cooling sensation component may contain or consist of a cooling sensation agent, a cooling sensation flavor component, or a mixture thereof.
In the present description, a cooling sensation agent means a compound that only has the function of imparting a refreshing sensation (or refreshing feeling) and/or a cold sensation (or cool feeling), and the abovementioned cooling sensation agent (A) (for example, a methyl menthol derivative or a salt thereof) is included among cooling sensation agents.
Moreover, in the present description, a cooling sensation flavor component means a compound other than the cooling sensation agent, which has a function of providing a refreshing sensation (or refreshing feeling), a cold sensation (or cool feeling), and/or other similar sensation.
The cooling sensation agent can contain or consist of the cooling sensation agent (A) and a cooling sensation agent other than the cooling sensation agent (A).
While not specifically limited thereto, the cooling sensation agent other than the cooling sensation agent (A) may contain or consist of isopulegol, cineol, mint oil, eucalyptus oil, 2-L-menthoxyethanol (COOLACT^® 5, manufactured by Takasago International Corporation), 3-L-menthoxypropane-1,2-diol (COOLACT^® 10, manufactured by Takasago International Corporation), L-menthyl-3-hydroxybutyrate (COOLACT^® 20, manufactured by Takasago International Corporation), p-menthane-3,8-diol (COOLACT^® 38D, manufactured by Takasago International Corporation), N-(4-(cyanomethyl)phenyl)-2-isopropyl-5,5-dimethylcyclohexanecarboxamide (COOLACT^® 400, manufactured by Takasago International Corporation), N-(3-hydroxy-4-methoxyphenyl)-2-isopropyl-5,5-dimethylcyclohexanecarboxamide, N-ethyl-p-menthane-3-carboxamide (Symcool^® WS-3, manufactured by Symrise AG), ethyl-2-(p-menthane-3-carboxamido)acetate (Symcool^® WS-5, manufactured by Symrise AG), N-(4-methoxyphenyl)-p-menthanecarboxamide (Symcool^® WS-12, manufactured by Symrise AG), 2-isopropyl-N,2,3-trimethylbutyramide (Symcool^® WS-23, manufactured by Symrise AG), 3-L-menthoxy-2-methylpropane-1,2-diol, 2-L-menthoxyethane-1-ol, 3-L-menthoxypropane-1-ol, 4-L-menthoxybutane-1-ol, menthyl lactate (FEMA 3748), menthone glycerol acetal (Frescolat MGA, FEMA 3807, or FEMA 3808), 2-(2-L-menthyloxyethyl)ethanol, menthyl glyoxylate, menthyl 2-pyrrolidone-5-carboxylate, menthyl succinate (FEMA 3810), N-(2-(pyridin-2-yl)-ethyl)-3-p-menthanecarboxamide (FEMA 4549), N-(ethoxycarbonylmethyl)-p-menthane-3-carboxamide, N-(4-cyanomethylphenyl)-p-menthanecarboxamide, or N-(4-aminocarbonylphenyl)-p-menthane, or a combination of two or more of these.
While not specifically limited thereto, the content of the cooling sensation agent other than the cooling sensation agent (A) may be 1 ppm or more, 100 ppm or more, 200 ppm or more, or 300 ppm or more relative to the entire flavoring ingredient-scented constituent member. Alternatively, the content of the cooling sensation agent other than the cooling sensation agent (A) may be 500,000 ppm or less, 50,000 ppm or less, or 5,000 ppm or less relative to the entire flavoring ingredient-scented constituent member. The abovementioned numerical ranges of the content of the cooling sensation agent other than the cooling sensation agent (A) may also be combined as desired. A cooling sensation that is free of bitter flavor is obtained by setting the content of the cooling sensation agent other than the cooling sensation agent (A) within the abovementioned numerical range.
While not specifically limited thereto, the cooling sensation flavor component may contain or comprise menthol, menthone, peppermint oil, or a mixture of two or more of these. Among these, menthol is preferred. The use of menthol provides a strong characteristic flavor that is reminiscent of a refreshing sensation (or refreshing feeling) and/or a cold sensation (or cool feeling).
While not specifically limited thereto, the content of the cooling sensation flavor component may be 1 ppm or more, 10 ppm or more, or 100 ppm or more relative to the entire flavoring ingredient-scented constituent member. Alternatively, the content of the cooling sensation flavor component may be 990,000 ppm or less, 500,000 ppm or less, or 40,000 ppm or less relative to the entire flavoring ingredient-scented constituent member. The content of the cooling sensation flavor component may be 0.0001-99 wt% relative to the entire flavoring ingredient-scented constituent member. The abovementioned numerical ranges of the content of the cooling sensation flavor component can be combined as desired.

The flavoring ingredient may contain a flavor.
In the present description, a flavor means a compound that does not impart a refreshing sensation (or refreshing feeling) and/or a cold sensation (or cool feeling), and has the function of providing various other sensations.
While not specifically limited thereto, the flavor may contain or consist of a natural flavor, a synthetic flavor, or a mixture thereof. While not specifically limited thereto, natural flavors may comprise or consist of lemon oil, lime oil, orange oil, ginger oil, dill oil, or a mixture of two or more thereof. While not specifically limited thereto, synthetic flavors may comprise or consist of isoamyl acetate, ethyl butyrate, linalyl acetate, linalool, ethyl acetate, or a mixture of two or more thereof.
While not specifically limited thereto, the content of the flavor may be 1 ppm or more, 10 ppm or more, or 100 ppm or more relative to the entire flavoring ingredient-scented constituent member. Alternatively, the content of the flavor may be 990,000 ppm or less, 50,000 ppm or less, or 40,000 ppm or less relative to the entire flavoring ingredient-scented constituent member. The numerical value ranges of the content of the abovementioned flavor may be combined as desired.

The flavoring ingredient can further comprise a carrier.
While not specifically limited thereto, the carrier may comprise or consist of a flavor-containing sheet, a carbohydrate, a cellulose derivative, a non-pulp fiber, a lipid, a polyvinyl pyrrolidone, a polyvinyl alcohol, or a mixture of two or more thereof, as described in e.g. WO 202020/235007 , WO 2018/100688 , WO 2012/18034A1 , and WO 2012/11833A1 . Since the carrier has a property of stabilizing and covering a flavor and/or cooling sensation component that is dispersed in the flavoring ingredient, evaporation and dissipation of the flavor and/or cooling sensation component during storage can be suppressed, and storage resistance can be improved. The carrier can also protect against escape of the flavor and/or cooling sensation component from the flavoring ingredient as a result physical damage from impact, rubbing, etc.

While not specifically limited thereto, the carbohydrate may comprise or consist of a polysaccharide, sugar, sugar alcohol, or a mixture of two or more thereof.
While not specifically limited thereto, polysaccharides may comprise or consist of a single-component system of one component selected from the group comprising dextrin, oligosaccharides, starches, carrageenan, locust bean gum, guar gum, agar, gellan gum, tamarind gum, xanthan gum, tara gum, konjac glucomannan, cassia gum, or psyllium seed gum; or a composite system in which two or more components selected from the abovementioned group are combined.
While not specifically limited thereto, sugars may comprise or consist of a single-component system of one component selected from the group comprising cane sugar, trehalose, maltose, lactose, glucose, and fructose; or a composite system in which two or more components selected from the abovementioned group are combined.
While not specifically limited thereto, sugar alcohols may comprise or consist of a single-component system of one component selected from the group comprising reduced maltose syrup, sorbitol, mannitol, xylitol, erythritol, and maltitol; or a composite system in which two or more components selected from the abovementioned group are combined.

While not specifically limited thereto, the cellulose derivative is preferably an organic solvent-soluble cellulose derivative. A cellulose derivative herein refers to a derivative obtained by introducing a substituent for an OH group into cellulose, and examples include ethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methylcellulose (e.g., hydrophobic hydroxypropyl methylcellulose), and hydroxypropyl methylcellulose phthalate. Due to the complex effects brought about by the characteristic functional groups of cellulose derivatives, they are in general widely used as binders, film-forming agents, and gelling agents. The organic solvent in the expression "organic solvent-soluble..." herein is, for example, ethanol.
The cellulose derivative is preferably an amphiphilic cellulose derivative, and more preferably hydroxypropyl cellulose. The degree of substitution in hydroxypropyl cellulose is, for example, 0.1-4.5, and preferably 2.0-4.5. In the present description, the degree of substitution in hydroxypropyl cellulose represents the number of hydroxypropyl groups per glucose. A hydroxypropyl cellulose that may be used is, for example, commercially available from Nippon Soda Co., Ltd. under the brand name Celny.
The advantages of using hydroxypropyl cellulose as a cellulose derivative are described below. Hydroxypropyl cellulose is a derivative of cellulose, and is a substance obtained by substituting hydroxypropyl groups for OH groups in cellulose. Hydroxypropyl cellulose is widely used as a binder, film-forming agent, or gelling agent. Cellulose is a hydrophobic substance, since OH groups are hydrogen bonded to each other such that intermolecular crystallization occurs. Hydroxypropyl cellulose, on the other hand, has hydroxypropyl groups, meaning that hydrogen bonds are therefore less likely to form between molecules therein, and thus is a substance that is both hydrophilic and hydrophobic (i.e., an amphiphilic agent).
It has also been reported that in a system comprising glycerol, a network-structured complex is formed through interaction (i.e., hydrogen bonding) between hydroxypropyl groups of hydroxypropyl cellulose and OH groups of glycerol. It is believed that hydroxypropyl cellulose can form a network-structured complex by interaction with a flavor, such as the hydrogen bond and hydrophobic interaction with the flavor, even when a flavor other than glycerol is used. It is also believed that since hydroxypropyl cellulose is amphiphilic, it can incorporate hydrophilic and hydrophobic flavors into a network structure without the use of an emulsifier or the like. It is believed that the flavor is stably retained by this network complex, without evaporation thereof, when a tobacco product is stored, and is stably released when the tobacco product is used (especially when a smoking article is heated).
Furthermore, hydroxypropyl cellulose is soluble in organic solvents, particularly ethanol. Thus, when a liquid composition containing hydroxypropyl cellulose, a flavor, and a solvent is used in the form of an ethanol solution, the ethanol solution is more advantageous than an aqueous solution in terms of such manufacturing processes as conveyance and coating, since the viscosity thereof can reduced to a greater degree than with an aqueous solution. Also, when an ethanol solution is dried and the flavor composition (a film of hydroxypropyl cellulose, etc.) is formed, the evaporation of the solvent is faster than in the case of an aqueous solution, and there are thus advantages such as shortened manufacturing time and reduced cost of energy during drying.

<Non-pulp fiber>

Non-pulp fiber is fiber other than pulp fiber. Pulp fiber is an aggregate of cellulose fiber extracted from plants such as wood, and is ordinarily used as a raw material for paper. Examples of pulp fiber include waste paper pulp, chemical pulp, and mechanical pulp. In the present application, the non-pulp fiber is preferably plant-derived. Because plant-derived fiber is biodegradable, there is little environmental impact.
Components such as conventional tobacco sheets are based on pulp fiber such as wood pulp, i.e. plant fiber bundles (as in e.g. the specification of US Patent No. 5,322,076 ). Wood pulp ordinarily consists of bundles of multiple monofilaments with a diameter of 20 µm, and wood pulp has a fiber diameter of about 100-200 µm, and a fiber length of about 1,000-2,000 µm. When a tobacco sheet having a practical tensile strength is manufactured using wood pulp, the sheet has a thickness of 100-300 µm, and thus the thermal conductivity thereof is reduced. However, since non-pulp fibers are used in the present application, a thin sheet having excellent mechanical strength can be formed, and excellent thermal conductivity can be achieved. From this perspective, the average fiber diameter of the non-pulp fibers is preferably 25 µm or less, more preferably 20 µm or less, and still more preferably 15 µm or less. There is no restriction as to the lower limit of the average fiber diameter, which may be 2 nm or greater, 10 nm or greater, 100 nm or greater, 1 µm or greater, or 5 µm or greater.
The average fiber diameter of non-pulp fibers can be determined by obtaining an image of the fibers, measuring the widths (i.e., short axes) of a plurality of fibers, and averaging these values. When the fibers are columnar in shape (and rectangular in cross-section), the width of the fiber, from between the width of the main surface and the width of a side surface, is taken to be the width of the main surface (i.e., the longer of the two). The number of fibers measured is preferably 100 or more.
The non-pulp fiber is preferably monofilament cellulose. Monofilament cellulose is a fine fiber obtained by subjecting a pulp fiber to processing such as defibration. The monofilament cellulose may be chemically modified, e.g. by oxidation. The average fiber diameter of the monofilament cellulose is as indicated above. While not limited thereto, the upper limit of the average fiber length of the monofilament cellulose is preferably 2,000 µm or less, and more preferably 1,500 µm or less. The lower limit thereof is preferably 100 µm or greater, and more preferably 500 µm or greater.
The non-pulp fiber is also preferably dietary fiber. Dietary fiber is a dietary component that is not digested by human digestive enzymes, and in the present application is more preferably an insoluble dietary fiber that is insoluble in water. The dietary fiber may be porous, i.e. sponge-like. Porous fibers can increase the surface area of a sheet for a smoking article, and improve the thermal conductivity of the sheet. In terms of availability, etc., the abovementioned fiber is preferably citrus fiber. Citrus fiber is a fiber having citrus albedo as the main raw material. The average fiber diameter of the citrus fiber is as indicated above. Moreover, the dietary fiber may be a short fiber or columnar particle with a low aspect ratio.
In one aspect, monofilament cellulose and dietary fiber are used in combination. Using both improves the strength and water dispersibility of the tobacco sheet, as well as the amount of smoke therefrom. The upper limit of the weight of the monofilament cellulose relative to 1 part by weight of the dietary fiber is preferably 1.5 parts by weight or less, more preferably 1.2 parts by weight or less, and the lower limit is preferably 0.1 or greater, and more preferably 0.3 or greater.

<Lipid>

While not specifically limited thereto, the lipid may be a solid wax, ceramide, derived fat such as a fatty acid, complex lipid such as a phospholipid, or a mixture of two or more thereof.
The flavoring ingredient containing the abovementioned carrier may be a flavor-carrying ingredient. In the present case, while not specifically limited thereto, the content of the carrier may be 1 ppm or more, 1,000 ppm or more, or 10,000 ppm or more of the entire flavoring ingredient including the carrier (i.e., the flavor-carrying ingredient). Alternatively, the content of the carrier may be 500,000 ppm or less, 400,000 ppm or less, or 300,000 ppm or less of the entire flavor-carrying ingredient. The numerical ranges of the content of the abovementioned carrier may be combined as desired. As a result of having the content of the carrier within the abovementioned numerical range, an effective flavor-carrying ingredient with a good balance between support and release of the flavoring ingredient is obtained.

The flavoring ingredient may further contain an emulsifier.
There are no particular limitations as to the type of emulsifier, and for example sorbitan monolaurate such as SPAN^® 20 (available from Uniqema of Wilmington, DE, USA); poly(ethylene oxide) sorbitan monolaurate such as TWEEN^® 20 (available from Uniqema of Wilmington, DE, USA); glycerol fatty acid ester such as glycerol monostearate, decaglycerol monolaurate, or decaglycerol pentastearate; a sugar ester such as sucrose monostearate or sucrose monopalmitate; a propylene glycol fatty acid ester such as propylene glycol monostearate; lecithin; or a combination of two or more thereof can be used.
While not specifically limited thereto, the content of the emulsifier may be 1 ppm or more, 100 ppm or more, or 1,000 ppm or more of the entire flavoring ingredient including the emulsifying agent. Alternatively, the content of the emulsifier may be 500,000 ppm or less, 400,000 ppm or less, or 300,000 ppm or less of the entire flavoring ingredient including the emulsifier. The numerical ranges of the content of the abovementioned emulsifier may be combined as desired. Having the content of the emulsifier within the abovementioned numerical range allows the water-soluble component and oil-soluble component of the flavoring ingredient to be efficiently emulsified and dispersed.
While not specifically limited thereto, the flavoring ingredient may be in a liquid, semi-solid, or solid state. If the flavoring ingredient is solid, it can be in the form of a powder, a capsule such as a seamless capsule form, or a sheet.

The flavoring ingredient-scented constituent member may further comprise an aerosol source.
While not specifically limited thereto, the aerosol source may be a polyhydric alcohol such as glycerol or propylene glycol, or e.g. a triethylamine citrate or triacetin, or a mixture of two or more thereof. Of these, glycerol is preferable. The use of glycerol can effectively increase the amount of visible smoke.
While not specifically limited thereto, the content of the aerosol source may be 1 ppm or more, 10,000 ppm or more, 50,000 ppm or more, or 200,000 ppm or more relative to the entire flavoring ingredient-scented constituent member. Alternatively, the content of the aerosol source may be 990,000 ppm or less, 500,000 ppm or less, or 200,000 ppm or less relative to the entire flavoring ingredient-scented constituent member. The numerical ranges of the content of the abovementioned aerosol source may be combined as desired. Having an aerosol-generating substrate content within the abovementioned numerical ranges can effectively increase the amount of visible smoke.

The abovementioned flavoring ingredient-scented constituent member may further comprise an adsorbing agent.
While not specifically limited thereto, the adsorbing agent may comprise or consist of e.g. activated carbon, zeolite, or silica, or a combination of two or more thereof. Of these, activated carbon is preferred. By using activated carbon, an effect of decreasing the flavor-inhibiting substance is obtained.
The content of the adsorbing agent relative to the entire flavoring ingredient-scented constituent member may be set as desired, and while not specifically limited thereto, may be 1 mg or more thereof. Alternatively, the content of the adsorbing agent may be 300 mg or less or 100 mg or less relative to the entire flavoring ingredient-scented constituent member. The numerical ranges of the content of the abovementioned adsorbing agent may be combined as desired.

1-2. Constituent member of a smoking article

While not specifically limited thereto, the constituent member of a smoking article may be a tobacco filler, filter, tube, rolling paper, tipping paper, plug, pouch, liquid, or a combination of two or more thereof. Of these, a tobacco filler is preferable. As a result of using a tobacco filler, an effective cooling sensation is obtained through efficient heating and evaporation of the cooling sensation agent.

A tobacco filler denotes a fillable object filled with processed tobacco leaves in a predetermined aspect. A "fillable object" is an object to be filled with processed tobacco leaves, and is part of a tobacco product. Examples of a fillable object include, but are not limited to, a rolling paper formed into a cylinder, and a receptacle having an air inlet and an air outlet.
Examples of aspects of a fillable object filled with processed tobacco leaves include an aspect in which the processed tobacco leaves are rolled in a rolling paper so as to be on the inside thereof (referred to below as a "tobacco rod"), and an aspect in which a receptacle for processed tobacco leaves has an air inlet and an air outlet (referred to below as a "tobacco cartridge").
In the present description, "tobacco leaf" is a generic term for harvested tobacco leaves before they have been aged. One aspect of aging includes curing.
Meanwhile, tobacco leaves that have been aged and have not yet been processed into various modes for use in tobacco products (such as cut tobacco, tobacco sheets, or tobacco granules) are referred to as "aged tobacco leaves." In addition, aged tobacco leaves that are processed into various forms utilized in tobacco products are referred to as "processed tobacco leaves."
Aged tobacco leaves are processed into various modes utilized in tobacco products to form processed tobacco leaves. The modes used in tobacco products can include, for example, "cut tobacco," which is aged tobacco leaves cut to a predetermined size. Other examples include "tobacco sheets" and "tobacco granules" obtained by forming a composition containing aged tobacco leaves ground to a predetermined particle size (referred to below as "fine tobacco powder") into a specific shape. Note that the aforementioned "fine tobacco powder" is also a mode of processed tobacco leaves.
Processed tobacco leaves are not limited to the abovementioned "cut tobacco," "tobacco sheet," "tobacco granules," and "fine tobacco powder," and can include various processed modes of aged tobacco leaves.
Aspects in which the fillable object is filled with processed tobacco leaves differ in accordance with whether the mode of processed tobacco leaves is the abovementioned cut tobacco, a tobacco sheet, or tobacco granules.
Examples of tobacco filler include a tobacco filler comprising cut tobacco wherewith a fillable object is filled (referred to below as a "first tobacco filler"), a tobacco filler comprising a tobacco sheet wherewith a fillable object is filled (referred to below as a "second tobacco filler"), and a tobacco filler comprising tobacco granules wherewith a fillable object is filled (referred to below as a "third tobacco filler").

Provided that the filter has the typical functions of a filter, there are no particular limitations thereto, and for example tow comprising a synthetic fiber (also referred simply as "tow"), a tubular filter such a center hole filter, or a material such as paper processed into a cylindrical shape can be used. Examples of typical functions of a filter include adjusting the amount of air that is admixed when e.g. an aerosol is drawn in, lightening the flavor, and reducing nicotine and tar, but the filter need not have all of these functions. Furthermore, in electrically heated tobacco products, which tend to generate less flavoring component and to have a lower tobacco filler filling rate than a cigarette product, an important function of the filter is to reduce the filtering function while preventing the tobacco filler from falling out.
Note that the filter may be produced by a manufacturing method that is well known in the relevant technical field, or may be a commercial product.
There is no particular limitation as to the mode of filter, and examples include plain filters comprising a single filter segment and multi-segment filters, such as dual filters and triple filters, comprising multiple filter segments.
There is no particular limitation as to the shape of the filter, and a well-known shape can be employed; a cylindrical shape can typically be adopted, and the aspect below may be used.
Also, the filter may be provided with a section such as a cavity or recess whereof the circumferential cross-section is an empty space (i.e., hollow).
The filter may be ventilated by a well-known method, for example by using a pre-perforated or air-permeable packaging material, or implementing laser perforation of the packaging material and the tip overlap (if present). A full tip overlap for ventilation may likewise be inherently air-permeable, or may be provided with vent holes. In an air-permeable product in which both a packaging material and a tip overlap are present, the ventilation section of the overlap is preferably aligned with the position of the ventilation section of the packaging material (for example, a plug wrap). Vent holes through the filter packaging material, vent holes through the tip overlap, or vent holes through both at once may be formed by laser drilling during filter manufacture.

<Tube>

The tube (i.e., cooling segment) may be an aspect comprising a cylindrical member. The cylindrical member may be a paper tube obtained by processing cardboard into a cylindrical shape, for example.
The internal structure of the cooling segment preferably has a large total surface area. Accordingly, in a preferred embodiment, the cooling segment may be formed by a sheet which is a thin material that is crimped and then pleated, gathered, and folded to form channels. The more folds or pleats within a given volume of the element, the greater the total surface area of the cooling segment.
The cylindrical member is provided with perforations.
Having perforations allows external air to be introduced into the cooling segment during inhalation. The vaporized component of the aerosol generated by heating a tobacco-containing segment thereby comes into contact with the external air, declines in temperature, and therefore liquefies to form an aerosol.
While not specifically limited thereto, the diameter of (or length across) the perforations may be, for example, 0.5-1.5 mm.
There is no particular limitation as to the number of perforations, and there may be one, two, or more. Multiple perforations may be provided on the circumference of the cooling segment, for example.
In some embodiments, the temperature of the aerosol generated may decrease by 10°C or more when the aerosol passes through the cooling segment to be inhaled by the user. In some embodiments, the temperature of the aerosol generated may decrease by 15°C or more in another aspect, and by 20°C or more in still another aspect, when the aerosol passes through the cooling segment to be inhaled by the user.
The cooling segment may comprise a sheet material selected from the group consisting of a metal foil, a polymer sheet, and a substantially pore-free paper or cardboard. In one embodiment, the cooling segment may comprise a sheet material selected from the group consisting of polyethylene, polypropylene, polyvinyl chloride, polyethylene terephthalate, polylactic acid, cellulose acetate and aluminum foil.
The constituent materials of the cooling segment may be a biodegradable material, e.g. a biodegradable polymer, such as a non-perforated paper or polylactic acid, or a starch copolymer.
Airflow through the interior of the cooling segment is preferably not significantly deflected between adjacent segments. In other words, the airflow through the interior of the cooling segment preferably flows along the longitudinal segment without significant radial deflection. In some embodiments, the cooling segment is formed from a material of low porosity or virtually without pores, except for the longitudinally extending channels. The material used to define or form the longitudinally extending channels, for example, a crimped or gathered sheet, has low porosity or virtually no pores.
As mentioned above, the cooling segment may comprise a crimped, pleated, gathered, or folded sheet of an appropriate constituent material. Cross-sectional profiles of such elements may show randomly oriented channels. The cooling segment can be formed by other means. For example, the cooling segment can be formed from a bundle of longitudinally extending tubes. The cooling segment may be formed by extrusion, molding, lamination, injection, or shredding.
The cooling segment may be formed, for example, by wrapping a pleated, gathered, or folded sheet material with a rolling paper. In some embodiments, the cooling segment is gathered into a rod shape, and may comprise a wrapper, e.g. a filter paper sheet of a crimped material bound by a rolling paper.

There is no particular limitation as to the constitution of the rolling paper, and a typical aspect thereof may be adopted, having for example pulp as the main component. The pulp may be made of wood pulp such as conifer wood pulp and/or deciduous wood pulp, or produced with admixture of non-wood pulp that is typically used in rolling paper for smoking products, such as flax pulp, hemp pulp, sisal pulp, or esparto. A single type of such pulp may be used, or multiple types of pulp may be combined for use in any desired proportions.
The rolled paper may also comprise a single sheet or may comprise a plurality of sheets.
The paper may be used in an aspect for wrapping a tobacco raw material, such as cut tobacco.
Pulp modes that may be used include chemical pulp, ground pulp, chemiground pulp, and thermomechanical pulp, etc. that are obtained by e.g. kraft cooking, acid/neutral/alkaline sulfite cooking, or soda cooking.
Note that the rolling paper may be manufactured by a manufacturing method described below or may be a commercially available product.
There is no particular limitation as to the rolling paper manufacturing method, which may be a known method, and the rolling paper may for example be manufactured from beaten pulp in a paper machine to achieve uniformity through adjustment of texture.
There is no particular limitation as to the type of paper machine, and for example, a Fourdrinier paper machine, a cylinder paper machine, or a combined cylinder-short wire paper machine can be used.
Moreover, water resistance may be imparted to the rolling paper by adding a wet strength agent, as required, and the print quality on the rolling paper may be adjusted by adding a sizing agent. Internal additives for papermaking such as aluminum sulfate and various anionic, cationic, nonionic, or amphoteric yield improving agents, drainage improving agents, and paper strengthening agents; and papermaking additives such as dyes, pH adjusters, antifoaming agents, pitch control agents, and slime control agents, can also be added.
Rolling paper produced as described above may also undergo calendering in which calender rollers are used to press the rolling paper. There are no particular limitations as to the methods and conditions for calendar processing, which may be performed, for example, by the methods and conditions described in WO 2008/072523 . Since the rolling paper is beaten in the course of calender processing, the degree to which the rolling paper is beaten can be increased and air permeability reduced.

Tipping paper refers to paper used to connect two or more of the tobacco rod, the cooling segment, and the filter segment. On the other hand, the abovementioned rolling paper is paper for wrapping individual members constituting the tobacco rod, the cooling segment, or the filter segment. For example, if the filter segment comprises a center hole filter and an acetate filter, the paper wrapped around the center hole filter and the paper wrapped around the acetate filter are both rolling papers. The filter is usually arranged on the mouth side, so that the tipping paper with which it is wrapped is necessarily a part that comes into contact with the mouth.
There is no particular limitation as to the constitution of the tipping paper, and a typical aspect thereof, for example one constituted similarly to the abovementioned rolling paper, may be adopted.

<Plug>

A plug is used, for example, to prevent the aerosol-forming substrate from being released from the tobacco rod during shipping, etc. of a heat-not-burn smoking article. In this case, a front plug (i.e., cap member) is provided at the distal end of the tobacco rod.
The plug may comprise a sheet. The plug may also comprise a wrapper, said wrapper being filled with the sheet, or may be shaped e.g. by bonding sheets together without using a wrapper. The former aspect is preferable in terms of being easy to manufacture.
The axial length of the plug is preferably 6-20 mm, more preferably 6-10 mm. The perimeter (i.e. circumference) thereof may be 15-30 mm. An axial length in this range enables mass production of the plug. If the axial length is less than the lower limit, the device may also become defective in that it becomes dirty from components that evaporate from a flavor source filler not being trapped, and leaking to the outside. If the axial length is excessive, the ventilation resistance of the plug as such increases, and thus the ventilation resistance of the entire heat-not-burn smoking article increases, making inhalation difficult during use.
In addition to the upstream end of the tobacco rod, a plug may also be arranged at the downstream end of the tobacco rod. The axial direction of the plug is the direction parallel to the longitudinal direction (i.e., axial direction) of the tobacco rod when incorporated as a tobacco rod. Additional arrangement of a plug at the downstream end of the tobacco rod can prevent the flavor source filler from spilling toward the mouthpiece segment when shipping. In the case of the internal heating type, the flavor source filler can also be prevented from spilling toward the mouthpiece segment when the heater is inserted into the rod.

A liquid means a liquid composition for use in an electronic cigarette. In an electronic cigarette, the liquid is evaporated to generate an aerosol. The liquid may contain propylene glycol (PG), glycerol (GL), nicotine, and a flavor.

<Pouch>

Any well-known pouch that is capable of packaging the filler, is not soluble in water, and is permeable to liquids (water, saliva, etc.) and water-soluble components of the filler, may be used without limitation, and for example, a non-woven fabric pouch may be used. Materials for the pouch include, for example, cellulose-based non-woven fabrics, and commercially available non-woven fabrics may be used. A pouch product can be produced by shaping a sheet comprising such a material into a bag shape, and filling with a filler and sealing the same by a means such as heat sealing.
While there is no particular limitation thereto, the basis weight of the abovementioned sheet is ordinarily 12-54 gsm, and preferably 24-30 gsm. While there is no particular limitation thereto, the thickness of the sheet is ordinarily 100-300 µm, and preferably 175-215 µm.
The inner surface and/or the outer surface of the pouch may be partially coated with a water-repellent material. A water-repellent fluororesin is suitable as the water-repellent material. A specific example of this type of water-repellent fluororesin is Asahi Guard^®, manufactured by Asahi Glass Co., Ltd. The water-repellent fluororesin is, for example, coated onto a packaging material for foodstuffs and other products such as confectioneries, milk products, prepared food, fast food, and pet food, that contain lipids. Thus, this type of water-repellent fluororesin is safe even when applied to a pouch to be placed inside the oral cavity. The water-repellent material is not limited to a fluororesin, and may be a material having a water-repellent effect, such as a paraffin resin, silicon resin, or epoxy resin.

(Mode of constituent member of smoking article)

While not specifically limited thereto, the mode of the constituent member of a smoking article may be a non-woven fabric.

While not specifically limited thereto, the constituent member of a smoking article may comprise or consist of a nicotine source.
While not specifically limited thereto, the nicotine source may contain or consist of nicotine or a salt thereof, derived from a tobacco raw material, non-tobacco raw material, or mixture thereof. Of these, nicotine or a salt thereof derived from a tobacco raw material is preferable. Through use of nicotine or a salt thereof derived from a tobacco raw material, the flavor unique to tobacco is inhaled simultaneously with nicotine, so that more satisfying sensations of smoking are obtained.
There is no particular limitation as to the nicotine source content relative to the entire constituent member of a smoking article.
The abovementioned tobacco leaves, aged tobacco leaves, processed tobacco leaves, or a combination of two or more of these can be used as the tobacco-derived raw material for the nicotine source.
Examples of non-tobacco-derived raw materials used as nicotine sources include coffee and tea. The parts of plants used may also include roots (including scaly roots (i.e. scaly bulbs), tuberous roots (i.e. potatoes), and bulbs), stems, tubers, bark (including bark of stems and trunks), leaves, flowers (including petals, pistils, and stamens), seeds, nuts, or tree trunks or branches.

In some embodiments of the present invention, the flavoring ingredient-scented constituent article is obtained by scenting a tobacco filler in which a tobacco-derived raw material is formed into an aspect such as a sheet or cut tobacco, or else a filter, tipping paper, tube, rolling paper, plug, pouch, or liquid, with a flavoring ingredient containing the abovementioned methyl menthol derivative or salt thereof.

2. Smoking article

The smoking article of the present invention comprises the flavoring ingredient-scented constituent member described above in 1.
There may be one, two, or more flavoring ingredient-scented constituent members included in the smoking article, with no particular limitation as to the number thereof.
In addition to the flavoring ingredient-scented constituent member, the smoking article may include or not include a constituent member that is not scented with a flavoring ingredient. The constituent member that is not scented with a flavoring ingredient may be the abovementioned tobacco filler, filter, tube, rolling paper, tipping paper, plug, pouch, or liquid.
In the smoking article of the present embodiment, the cooling sensation agent (A) included in the flavoring ingredient-scented constituent member can remain at the site to which it was originally added both before and after storage. Thus, the smoking article of the present embodiment can exhibit excellent cooling sensation intensity, as originally intended, both before and after storage.
The smoking article may be a heated smoking article, a combustion smoking article, a smokeless smoking article, or an electronic cigarette.
Smoking articles include flavor inhalation articles with which a user savors a flavor by inhalation, and smokeless tobacco (i.e., smokeless smoking articles) with which a user savors a flavor by inserting the article directly into the nasal cavity or oral cavity. Flavor inhalation articles can be broadly divided into combustion smoking articles such as conventional cigarettes, electronic cigarettes, and heat-not-burn smoking articles.
Smokeless smoking articles include, for example, articles inserted into the oral cavity, such as snus and nicotine pouches, as well as snuff, etc.
Well-known methods can be used for the production of snus. In this case, the abovementioned flavoring ingredient-scented constituent article is obtained by employing a well-known method to fill a packaging material, for which a raw material such as a non-woven fabric is used. For example, snus is obtained by filling the packaging material with an adjusted amount of a flavoring ingredient-scented constituent member, and sealing the same by a means such as heat sealing.
Although the packaging material can be used without any particular limitation, a cellulose-based non-woven fabric or the like is preferably used.
Examples of combustion smoking articles include cigarettes, pipes, kiseru (Japanese smoking pipes), cigars, and cigarillos.
Electronic cigarettes includes, for example, open tank types, closed tank types, and cigarette-like types.
Heat-not-burn smoking articles (i.e., heated smoking articles) may be heated by a heating device that is separate from the product, or by a heating device that is integrated with the product. In the former type of smoking product (i.e. the separate type), the heat-not-burn smoking article and the heating device are collectively referred to as a "heat-not-burn smoking system." An example of a heat-not-burn smoking system is described below with reference to Figures 1 and 2.
Figure 1 is a cross-sectional view of a heat-not-burn smoking article 20. As shown in Figure 1, the heat-not-burn smoking article 20 (referred to below simply as the "smoking article 20") has a cylindrical shape. The length of the circumference of the smoking article 20 is preferably 16-27 mm, more preferably 20-26 mm, and still more preferably 21-25 mm While not specifically limited thereto, the total length (i.e., horizontal length) of the smoking article 20 is preferably 40-90 mm, more preferably 50-75 mm, and still more preferably 50-60 mm.
The smoking article 20 comprises a smoking segment 20A, a filter portion 20C constituting the mouthpiece, and a connecting portion 20B that connects these.
The smoking segment 20A is cylindrical, and the total length (i.e., the axial length) thereof is, for example, preferably 5-100 mm, more preferably 10-50 mm, and still more preferably 10-25 mm. While not specifically limited thereto, the cross-sectional shape of the smoking segment 20A may be for example circular, elliptical, or polygonal.
The smoking segment 20A has a smoking composition sheet or material derived therefrom 21, around which is wrapped a wrapper 22. A flavor may be included in the smoking composition sheet or material derived therefrom 21.
The filter portion 20C is cylindrical. The filter portion 20C has a rod-shaped first segment 25 that is constituted by being filled with cellulose acetate fibers, and a rod-shaped second segment 26 that is similarly constituted by being filled with cellulose acetate fibers. The first segment 25 is located on the smoking segment 20A side. The first segment 25 may have a hollow portion. The second segment 26 is located on the mouthpiece side. The second segment 26 is solid. The first segment 25 comprises a first filling layer 25a (of cellulose acetate fibers) and an inner plug wrapper 25b that is wrapped around the first filling layer 25a. The second segment 26 comprises a second filling layer 26a (of cellulose acetate fibers) and an inner plug wrapper 26b that is wrapped around the second filling layer 26a. The first and second segments 25 and 26 are connected by an outer plug wrapper 27. The outer plug wrapper 27 is bonded to the first segment 25 and second segment 26 by a vinyl acetate emulsion adhesive, for example.
The length of the filter portion 20C may be 10-30 mm, for example, the length of the connecting portion 20B may be 10-30 mm, for example, the length of the first segment 25 may be 5-15 mm, for example, and the length of the second segment 26 may be 5-15 mm, for example. The lengths of these individual segments are examples, and may be modified as appropriate, in accordance with e.g. the manufacturability, the required quality, and the length of the smoking segment 20A.
For example, the first segment 25 (i.e., a center hole segment) comprises the first filling layer 25a, which has one or multiple hollow portions, and the inner plug wrapper 25b that covers the first filling layer 25a. The first segment 25 has the function of increasing the strength of the second segment 26. The first filling layer 25a of the first segment 25 is, for example, densely filled with cellulose acetate fibers. The cellulose acetate fibers are cured by adding for example 6-20% by mass of a triacetin-containing plasticizer to the mass of cellulose acetate. The hollow portion of the first segment 25 may, for example, have an inner diameter of φ 1.0-5.0 mm.
The first filling layer 25a of the first segment 25 may, for example, be constituted with a relatively high fiber filling density, or may have a fiber filling density similar to that of the second filling layer 26a of the second segment 26 described below. Thus, during inhalation, air or aerosol will flow only through the hollow portion, and virtually no air or aerosol will flow through the first filling layer 25a. If, for example, a lesser reduction of the aerosol component by filtration is desired in the second segment 26, the second segment 26 may be shortened, for example, so that the first segment 25 can be lengthened to an equal degree.
Replacing the shortened second segment 26 with the first segment 25 effectively increases aerosol delivery. Being a fiber filling layer, the texture of the first filling layer 25a of the first segment 25 therefore causes the user no discomfort when touched from the outside during use.
The second segment 26 is composed of the second filling layer 26a and an inner plug wrapper 26b that covers the second filling layer 26a. The second segment 26 (filter segment) is filled with cellulose acetate fibers at a typical density, and has typical aerosol filtration performance.
The filtration performance of the first segment 25 in filtering an aerosol (i.e., mainstream smoke) released from the smoking segment 20A may differ from that of the second segment 26. The first segment 25 and/or the second segment 26 may contain a flavor. The structure of the filter portion 20C is discretionary, and may be a structure having a plurality of segments as described above, or may consist of a single segment. The filter portion 20C may consist of one segment. In such cases, the filter portion 20C may consist of either the first segment or the second segment.
The connecting portion 20B is cylindrical. The connecting portion 20B has a paper tube 23 that is formed into a cylinder, using cardboard, for example. The connecting portion 20B may be filled with a cooling member for cooling the aerosol. Examples of cooling members include a sheet of a polymer such as polylactic acid, which can be folded for filling. A support that prevents the smoking segment 20A from shifting position may be additionally provided between the smoking segment 20A and the connecting portion 20B. The support may comprise known materials such as a center hole filter as in the first segment 25.
The smoking segment 20A, connecting portion 20B, and filter portion 20C are integrally joined by a wrapper 28 that is cylindrically wrapped around the outsides thereof. On one side (the inner side) of the wrapper 28, the entire surface or nearly the entire surface, except for the vicinity of the ventilation holes 24, is coated with a vinyl acetate emulsion adhesive. A plurality of ventilation holes 24 are externally formed by a laser process after the smoking segment 20A, connecting portion 20B, and filter portion 20C have been integrated by the wrapper 28.
The ventilation holes 24 comprise two or more through-holes that pass through the connecting portion 20B in the thickness direction. The two or more through-holes are formed so as to be arranged radially when viewed from an extension of the central axis of the smoking article 20. The ventilation holes 24 are provided in the connecting portion 20B in the present embodiment, but may be provided in the filter portion 20C. Moreover, the two or more through-holes among the ventilation holes 24 are provided in a single row at a constant interval and in a single ring in the present embodiment, but may be provided in two rows at a constant interval in two rings, or one or two rows of the ventilation holes 24 may be provided discontinuously or irregularly. When a user inhales with the mouthpiece held in the mouth, outside air is entrained in the mainstream smoke via the ventilation holes 24. However, ventilation holes 24 need not be provided.
Figure 2 shows an example of a heat-not-burn smoking system. The heat-not-burn smoking system in the drawing comprises a heat-not-burn smoking article 20 and a heating device 10 that heats the smoking segment 20A from the outside.
The heating device 10 shown in Figure 2 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, and the heater 12 and metal tube 13 are positioned to accommodate the smoking segment 20A that is to be inserted thereinto. The heater 12 may be a heater employing electrical resistance, and electrical power is supplied by the battery unit 14 in accordance with a command from the control unit 15, which controls the temperature, such that heating is provided by the heater 12. The heat emitted from the heater 12 is transferred to the aerosol source-containing smoking segment 20A via the metal tube 13, which has high thermal conductivity. The drawing shows an aspect in which the heating device 10 heats the smoking segment 20A from the outside, but the latter may be heated from the inside. While not specifically limited thereto, the heating temperature provided by the heating device 10 is preferably 400°C or lower, more preferably 150-400°C, and still more preferably 200-350°C. The heating temperature refers to the heater temperature of the heating device 10.
Another example of a heat-not-burn smoking article is described below with reference to Figures 3-5.
Figure 3 is a perspective view showing an example of the exterior of a heat-not-burn smoking article. Figure 4 is an exploded view showing an example of a heat-not-burn smoking article. The heat-not-burn smoking article 30 (referred to below simply as the smoking article 30) is e.g. an electronic cigarette or nebulizer that generates and provides an aerosol to a user in response to inhalation by the user. Note that a single continuous inhalation by the user will be called a "puff." The smoking article 30 also adds a component such as a flavor to the generated aerosol, and releases the same into the oral cavity of the user.
As shown in Figures 3 and 4, the smoking article 30 comprises a body 30A, an aerosol source holding part 30B, and an additive component holding portion 30C. The body 30Aa supplies electric power and controls the operation of the entire device. The aerosol source holding part 30B holds an aerosol source for atomizing to generate aerosol. The additive component holding part 30C holds a tobacco filler 38. The tobacco filler 38 may comprise the flavor-carrying component member (i.e., flavoring ingredient-scented constituent member) of the present invention, for example a flavor-carrying cut tobacco, a flavor-carrying sheet tobacco, flavor-carrying tobacco granules, a flavor-carrying granule substrate or a flavor-carrying metal foil. A user holds a mouthpiece in the mouth, at the end on the additive component holding part 30C side, and inhales an aerosol to which the flavor, etc. has been added.
A user, for example, assembles the body 30A, the aerosol source holding part 30B, and the additive component holding portion 30C to form the smoking article 30. The body 30A, aerosol source holding part 30B, and additive component holding part 30C are e.g. of a cylindrical or truncated cone shape that have diameters of a predetermined magnitude, and the body 30A, aerosol source holding part 30B, and additive component holding part 30C may be joined together in that order. The body 30A and the aerosol source holding part 30B are coupled by, for example, engaging male and female screw segments provided at the respective ends thereof. The aerosol source holding part 30B and the additive component holding part 30C are coupled, for example, by fitting the additive component holding part 30C, whereof the side surface is tapered, into a cylindrical portion provided at one end of the aerosol source holding part 30B. The aerosol source holding part 30B and the additive component holding part 30C may also be disposable replacement parts.
Figure 5 is a schematic view showing an example of the interior of the smoking article 30. The body 30A includes a power source 31, a control unit 32, and a inhalation sensor 33. The control unit 32 is electrically connected to the power source 31 and the inhalation sensor 33, respectively. The power source 31 is e.g. a secondary battery, and supplies power to an electrical circuit included in the smoking article 30. The control unit 32 is a processor such as a microcontroller (i.e. microcontroller unit (MCU)), and controls the operation of an electrical circuit included in the smoking article 30. The inhalation sensor 33 is e.g. an atmospheric pressure sensor or flow rate sensor. When the user inhales from the mouthpiece of the smoking article 30, the inhalation sensor 33 outputs a value corresponding to the negative pressure or the gas flow rate generated inside the smoking article 30. That is, the control unit 32 can detect inhalation on the basis of the output value of the inhalation sensor 33.
The aerosol source holding part 30B of the smoking article 30 includes a storage part 34, a supply unit 35, a load 36, and a residual amount sensor 37. The storage part 34 is a container for storing a liquid aerosol source to be atomized by heating. Note that the aerosol source is a polyol material, such as glycerol or propylene glycol. Note that the aerosol source may be a mixed solution containing a nicotinic liquid, water, flavor, and the like. Such an aerosol source is stored in advance in the storage part 34. Note that the aerosol source may be a solid that does not require the storage part 34.
The supply unit 35 includes a wick formed for example by twisting a fiber material such as glass fiber. The supply unit 35 is connected to the storage part 34. The supply unit 35 is connected to the load 36, or at least a part of the supply unit 35 is arranged near the load 36. The aerosol source penetrates the wick by capillary action, and moves to a portion in which the aerosol source can be atomized through heating by the load 36. In other words, the supply unit 35 draws the aerosol source from the storage part 34, and carries it to the load 36 or near thereto. A porous ceramic may be used in place of a glass fiber for the wick.
The load 36 is for example a coil-shaped heater, and generates heat when an electric current flows. Moreover, the load 36 has a positive temperature coefficient (PTC) property, and the resistance is almost directly proportional to the heating temperature thereof. Note that it is not necessary for the load 36 to have a positive temperature coefficient property, and the resistance may be correlated with the heating temperature. As an example, the load 36 may have a negative temperature coefficient (NTC) property. Note that the load 36 may be wound around the exterior of the wick, or conversely may be configured such that the wick covers the circumference of the load 36. The power supply to the load 36 is controlled by the control unit 32. When the supply unit 35 supplies the aerosol source from the storage part 34 to the load 36, the aerosol source is evaporated by the heat of the load 36, and thus aerosol is generated. The control unit 32 supplies power to the load 36 to generate aerosol when inhalation activity of a user is detected on the basis of an output value of the inhalation sensor 33. Also, when the remaining amount of the aerosol source stored in the storage part 34 is sufficient, a sufficient amount of the aerosol source is supplied to the load 36 as well, and since the heat generated at the load 36 is transported to the aerosol source, i.e., since the heat generated at the load 36 is used for temperature elevation and vaporization of the aerosol source, the temperature of the load 36 almost never exceeds a pre-planned, predetermined temperature. On the other hand, when the aerosol source stored in the storage part 34 is depleted, the amount of aerosol source supplied per hour to the load 36 decreases. Since, as a result, the heat generated at the load 36 is not transported to the aerosol source, i.e., since the heat generated at the load 36 is not used for temperature elevation and evaporation of the aerosol source, the load 36 is overheated, and the resistance of the load 36 is increased accordingly.
The residual amount sensor 37 outputs sensing data for estimating the residual amount of the aerosol source stored in the storage part 34 on the basis of the temperature of the load 36. For example, the residual amount sensor 37 includes a current-measuring resistor (i.e., a shunt resistor) that is connected in series with the load 36, and a measuring device that is connected in parallel with the resistor and measures the voltage level of the resistor. Note that the resistance of the resistor is a pre-planned, predetermined value that hardly changes with temperature. Thus, the level of electrical current flowing to the resistor is determined on the basis of a known resistance and the measured voltage.
The additive component holding part 30C of the smoking article 30 holds inside thereof the tobacco filler 38. As mentioned above, the tobacco filler 38 may comprise the flavor-carrying constituent member (i.e., flavoring ingredient-scented constituent member) of the present invention, for example, a flavor-carrying cut tobacco, a flavor-carrying sheet tobacco, flavor-carrying tobacco granules, a flavor-carrying granule substrate or a flavor-carrying metal foil. The tobacco filler 38 may comprise ordinary tobacco fillers, in addition to the "flavor-carrying constituent member" of the present invention. Ordinary tobacco fillers may comprise cut tobacco and/or sheet tobacco cut to a predetermined width (i.e., sheet tobacco cuttings). The additive component holding part 30C has ventilation holes on the mouthpiece side and in a portion coupled to the aerosol source holding part 30B, so that when a user inhales from the mouthpiece, negative pressure is generated inside the additive component holding part 30C, aerosol generated in the aerosol source holding part 30B is inhaled, and components such as nicotine and flavor are added to the aerosol inside the additive component holding part 30C and released into the oral cavity of the user.

EXAMPLES

The present invention is described experimentally through the following examples, and is not intended to be construed as limiting the scope of the present invention to the examples.

Menthol (L-Menthol, manufactured by Takasago International Corporation) and cooling sensation agents (the abovementioned COOLACT^® 370, COOLACT^® 5, COOLACT^® 10, COOLACT^® 20, Symcool^® WS-5, and Symcool^® WS-23) were respectively diluted by adding ethanol to obtain diluted solutions of menthol and each cooling sensation agent diluted to 1000 ppm in ethanol.
Gas chromatography with a mass spectrometer (GC/MS) was then performed on the abovementioned diluted solutions thus obtained.
The conditions for GC/MS analysis were as follows.

· GC/MS
Apparatus: 7890B/5977B GC/MSD, manufactured by Agilent Technologies
· GC conditions
Column: HP-5MS (manufactured by Agilent Technologies)
Inner diameter 0.25 mm x length 30 m, film thickness 0.25 µm
Injection volume: 1 µL
Injection mode: Split (10:1)
Injection port temperature: 270°C
Septum purge flow: 5 ml/minute
Carrier gas: Helium (He)
Column flow rate: 1 mL/minute (constant flow mode)
Oven temperature: From 40°C (3 minutes) to 280°C (20 minutes) at a rate of 4°C/minute
Transfer line temperature: 280°C
· MS conditions
Solvent wait time: 4 minutes
Ionization method: Electron impact ionization (EI), 70 eV
Ion source temperature: 230°C
Quadrupole temperature: 150°C
Measurement mode: Scan
MS scan range: m/z 26-450
Threshold: 50
Sampling rate: 2

The chromatogram retention index (RI) obtained by the abovementioned GC/MS analysis was calculated by the following method.
The RI of menthol or respective cooling agent was calculated by a linear method on the basis of an n-alkane mixture ranging from n-hexane (C6, RI: 600) to n-pentatriacontane (C35, RI: 3500) Note that the n-alkane mixture used in calculating the RI is not limited thereto.
The RIs of the resulting menthol and cooling sensation agents were as follows.

Menthol: 1173
COOLACT^® 370: 2477
COOLACT^® 5: 1414
COOLACT^® 10: 1674
COOLACT^® 20: 1611
Symcool^® WS-5: 1942
Symcool^® WS-23: 1287

The chromatogram obtained is shown in Figure 6.
The column used in this study: HP-5MS (95% dimethylpolysiloxane/5% phenyl-methylpolysiloxane) is a low polarity column, and it appears that the lower the value of RI, the easier a compound is to evaporate, and conversely, the higher the value of RI is, the more difficult a compound is to evaporate. The results in Figure 6 suggest that the COOLACT^® 370 is the most difficult to evaporate among menthol and the cooling sensation agents measured at this time.

(Preparation of heat-not-burn smoking articles (Example 1, Comparative Examples 1 and 2))

Tobacco sticks (glycerol content relative to tobacco filler: 7.5 wt%) manufactured from tobacco leaves were prepared on the basis of a well-known papermaking method.
Moreover, 20 g of a methyl menthol derivative (N-(2-hydroxy-2-phenylethyl)-2-isopropyl-5,5-dimethylcyclohexane-1-carboxamide, COOLACT^® 370, manufactured by Takasago International Corporation), 80 g of menthol (manufactured by Takasago International Corporation) as a cooling sensation flavor component, or 20 g of 2-isopropyl-N,2,3-trimethylbutyramide (Symcool^® WS-23, manufactured by Symrise) as a cooling sensation agent other than a methyl menthol derivative or a salt thereof were each added to and mixed with 80 g of ethanol to obtain a methyl menthol derivative solution, a menthol solution, and a solution of the cooling sensation agent other than a methyl menthol derivative, respectively.
The abovementioned methyl menthol derivative solution, menthol solution, or solution of the cooling sensation agent other than a methyl menthol derivative was then added, using a syringe, so as to spread throughout the entire tobacco filler in the prepared tobacco sticks, and thus were obtained the tobacco stick containing the cooling sensation component of Example 1, in which the methyl menthol derivative content was 2,000 ppm relative to the flavoring ingredient-scented tobacco filler (i.e., the total of the tobacco filler and the flavoring ingredient); the tobacco stick containing a cooling sensation component of Comparative Example 1, in which the menthol content was 5,000 ppm relative to the flavoring ingredient-scented tobacco filler, and the tobacco stick containing the cooling sensation component of Comparative Example 2, in which the content of the cooling sensation agent other than a methyl menthol derivative was 2,000 ppm relative to the flavoring ingredient-scented tobacco filler.

(Preparation of a heat-not-burn smoking article (Example 2))

A flavoring ingredient containing a carrier (hydroxypropyl cellulose) was obtained by mixing 0.5 g of a methyl menthol derivative (the abovementioned COOLACT^® 370), 1.5 g of hydroxypropyl cellulose (Celny SSL, manufactured by Nippon Soda Co., Ltd.), and 8.0 g of propylene glycol. The heated smoking article of Example 2, in which the content of the methyl menthol derivative was 2,000 ppm relative to the flavoring ingredient-scented tobacco filler (i.e., the total of the tobacco filler and the flavoring ingredient), was prepared by injecting 10.8 mg of the flavoring ingredient thus obtained into 260 mg of tobacco filler (containing tobacco leaves). The contents of components in the cooling sensation component-containing heated smoking article of Example 2 thus obtained were: tobacco leaves 96.0 mass%, methyl menthol derivative 0.2 mass%, hydroxypropyl cellulose 0.6 mass%, and propylene glycol 3.2 mass%.

(Preparation of combustion smoking articles (Example 3, Comparative Examples 3 and 4))

A combustion smoking article manufactured from tobacco leaves was prepared.
A solution of a methyl menthol derivative, a solution of menthol, and a solution of a cooling sensation agent other than a methyl menthol derivative were each obtained by a similar procedure and using menthol or other cooling sensation agents similar to that in the preparation of the abovementioned heat-not-burn smoking articles (Example 1, and Comparative Examples 1 and 2).
The abovementioned methyl menthol derivative solution, menthol solution, or solution of the cooling sensation agent other than a methyl menthol derivative was then added, using a syringe, so as to spread throughout the entire tobacco filler in the prepared combustion smoking articles, and thus were obtained the cooling sensation component-containing combustion smoking article of Example 3 in which the methyl menthol derivative content was 2,000 ppm relative to the flavoring ingredient-scented tobacco filler (i.e., the total of the tobacco filler and the flavoring ingredient), the cooling sensation component-containing combustion smoking article of Comparative Example 3 in which the menthol content was 5,000 ppm relative to the flavoring ingredient-scented tobacco filler, and the cooling sensation component-containing combustion smoking article of Example 4 in which the content of the cooling sensation agent other than a methyl menthol derivative was 2,000 ppm relative to the flavoring ingredient-scented tobacco filler.
The inventors conducted a preliminary study, and found that since menthol has a weaker cooling sensation intensity than the abovementioned methyl menthol derivatives and cooling agents other than methyl menthol derivatives, it is difficult to compare cooling sensation intensities thereof at similar contents. Whereas the content of the methyl menthol derivative or cooling agent other than a methyl menthol derivative as a cooling ingredient was 2000 ppm in the abovementioned Examples 1-3 and in Comparative Examples 2 and 4, the content of the cooling ingredient menthol in the abovementioned Comparative Examples 1 and 3 was set to 5,000 ppm, thus adjusting the cooling sensation intensity as much as possible to facilitate comparison, in order to assess cooling sensation intensity in the present sensory evaluation.

(Preparation of a pre-storage smoking article)

The heat-not-burn smoking articles of Examples 1 and 2 and Comparative Examples 1 and 2 (within 5 days after manufacture, at 25°C; referred to below as "pre-storage heat-not-burn smoking articles"), produced as described above, were placed in the non-combustion smoking system with external heating shown in Figure 2. Also prepared were combustion smoking articles of Example 3 and Comparative Examples 3 and 4 (within 5 days after manufacture, at 25°C; referred to below as "pre-storage heat-not-burn smoking articles") that had been produced as described above. Each smoking article thus prepared was used to perform the following sensory assessments.

(1) Cooling sensation intensity

The cooling sensation associated with each pre-storage heat-not-burn smoking article in Examples 1 and 2 and Comparative Examples 1 and 2, and each pre-storage combustion smoking article in Example 3 and Comparative Examples 3 and 4, was evaluated by five well trained panelists. In the present description, "cooling sensation" means a refreshing feeling (or refreshing sensation) and/or a cold sensation (or cool sensation).
The panelists evaluated the cooling sensations of smoking test rolls according to the six-level scale in Table 1 below. In the scale shown in Table 1 below, a score of 3 is equivalent to that of a menthol-containing smoking article (Comparative Example 1 for heat-not-burn smoking articles and Comparative Example 3 for combustion smoking articles). The evaluators all recognized in advance that Comparative Example 1 would be scored as 3 in Table 1 when evaluating Examples 1 and 2 and Comparative Example 2, and that Comparative Example 3 would be scored as 3 in Table 1 when evaluating Example 3 and Comparative Example 4. The evaluation results were obtained by calculating the average of the five panelists, and when the average was a value to two decimal places, the score computed was rounded to the nearest tenth. The evaluation results are shown in Table 2.

[Table 1]

Table 1

Cooling sensation
0	Not felt
1	Very weak
2	Weak
3	Moderate
4	Intense
5	Very intense

[Table 2]

Table 2

Heat-not-burn smoking articles
	Example 1	3.0
	Example 2	2.8
	Comparative Example 1	3.0
	Comparative Example 2	2.6

Combustion smoking articles
	Example 3	3.6
	Comparative Example 3	3.0
	Comparative Example 4	2.8

As indicated above, the menthol (Comparative Examples 1 and 3) content was 5,000 ppm, while the methyl menthol derivative (Examples 1-3) content and the content of the cooling sensation agent other than a methyl menthol derivative (Comparative Examples 2 and 4) were adjusted to 2,000 ppm, in order to facilitate comparison of cooling sensation intensities in the present evaluation.
From the results in Table 2, the cooling sensation intensity of the methyl menthol derivative-containing smoking article (Example 1) was similar to the cooling sensation intensity of the menthol-containing smoking article (Comparative Example 1), among tobacco stick aspects of a heat-not-burn smoking article (Example 1 and Comparative Examples 1 and 2). Among combustion smoking articles (Example 3 and Comparative Examples 3 and 4), the cooling sensation intensity of the methyl menthol derivative-containing smoking article (Example 3) was greater than that of the menthol-containing smoking article (Comparative Example 3).
Thus, when the menthol content was reduced to 2000 ppm, the same as the methyl menthol derivative, the cooling sensation intensity appears to have been insufficient. Consequently, it was found that the methyl menthol derivative-containing smoking article had a greater cooling sensation intensity than the menthol-containing smoking article.
It was also found that a methyl menthol derivative-containing smoking article (Example 1 or Example 3) had a cooling sensation intensity equal to or greater than that of a smoking article containing a cooling sensation agent other than a methyl menthol derivative (Comparative Example 2 or 4), regardless of whether it was a combustion smoking article or heat-not-burn smoking article,.
A methyl menthol derivative-containing smoking article with added carrier hydroxypropyl cellulose (Example 2) also had a cooling sensation intensity approximately equivalent to that of a methyl menthol derivative-containing smoking article (Example 1) without added hydroxypropyl cellulose. This confirmed that the characteristics of methyl menthol derivative-containing smoking articles confirmed from the abovementioned sensory evaluation results were expressed regardless of the presence or absence of additional hydroxypropyl cellulose. The carrier has a property of stabilizing and covering a flavor or a cooling sensation component that is dispersed in a flavoring ingredient. Therefore, in addition to suppressing evaporation and dissipation of the flavor and/or cooling sensation component, and improving storage resistance, addition of the abovementioned carrier can be expected to have the effect of protecting a flavor and/or cooling sensation component from physical damage.

(2) Bitter flavor

The bitter flavor of pre-storage heat-not-burn smoking articles of Examples 1 and 2 and Comparative Examples 1 and 2, and of pre-storage combustion smoking articles of Example 3 and Comparative Examples 3 and 4, which had been prepared as described above, was evaluated by five well-trained panelists. It is known that if the amount of a cooling sensation component is increased to achieve a required cooling sensation intensity, the cooling sensation is imparted together with a bitter flavor. Therefore, the bitter flavor of the cooling sensation component is preferably weak.
The cooling sensation associated with each smoking test roll was assessed by the panelists according to the four-level scale in Table 3 below. In the scale used in Table 3 below, a score of 2 is equivalent to that of a menthol-containing smoking article (Comparative Example 1 for heat-not-burn smoking articles, and Comparative Example 3 for combustion smoking articles). The evaluators all recognized in advance that, among the smoking articles, Comparative Example 1 would be scored as 2 in Table 3 when evaluating Examples 1 and 2 and Comparative Example 2, and that Comparative Example 3 would be scored as 2 in Table 3 when evaluating Example 3 and Comparative Example 4. The evaluation results were obtained by calculating the average of the five panelists, and when the average was a value to two decimal places, the score computed was rounded to the nearest tenth. The evaluation results are shown in Table 4.

[Table 3]

Table 3

Bitter flavor
0	Not sensed
1	Weak
2	Moderate
3	Intense

[Table 4]

Table 4

Heat-not-burn smoking articles
	Example 1	0.4
	Example 2	0.4
	Comparative Example 1	2.0
	Comparative Example 2	0.4

Combustion smoking articles
	Example 3	0.6
	Comparative Example 3	2.0
	Comparative Example 4	0.6

In view of the results in Table 4, it was found that a methyl menthol derivative-containing smoking article (Example 1 or Example 3) had a weaker bitter flavor than a menthol-containing smoking article, regardless of whether it was a combustion smoking article or heat-not-burn smoking article, and was thus preferable (Comparative Example 2 or 4).
Results as in Example 1, which was without added hydroxypropyl cellulose, were also obtained with a methyl menthol derivative-containing smoking article to which the carrier hydroxypropyl cellulose had been added (Example 2). This confirmed that the preferred characteristic of weak bitter flavor of the methyl menthol derivative, confirmed from the abovementioned sensory evaluation results, was expressed regardless of the presence or absence of additional hydroxypropyl cellulose. As indicated above, in addition to suppressing evaporation and dissipation of the flavor and/or cooling sensation component, and improving storage resistance, the abovementioned carrier can be expected to have the effect of protecting a flavor and/or cooling sensation component from physical damage.

(3) Cooling sensation (site effect)

Cooling sensation site effects of pre-storage heat-not-burn smoking articles of Examples 1 and 2 and Comparative Examples 1 and 2, and of pre-storage combustion smoking articles of Example 3 and Comparative Examples 3 and 4, which had been prepared as described above, were assessed by five well-trained panelists. The effect on sites (site effect) was evaluated by having the five panelists select multiple sites, from among the upper jaw, tongue, cheek, and throat, as sites in the oral cavity at which the cooling sensation was felt when evaluating each Example and Comparative Example. The tallied results are shown in Table 5. For example, the notation "5" in Table 5 means that five panelists experienced a cooling sensation at a specific site.

[Table 5]

Table 5

Site effect - sites at which sensed (multiple selection)
		Upper jaw	Tongue	Cheek	Throat
Heat-not-burn smoking articles
	Example 1	2	1	0	4
	Example 2	2	1	0	4
	Comparative Example 1	5	5	3	0
	Comparative Example 2	5	3	1	1

Combustion smoking articles
	Example 3	2	1	1	3
	Comparative Example 3	5	4	3	0
	Comparative Example 4	5	2	1	1

As shown in Table 5, fewer evaluators reported feeling a cooling sensation on the tongue with a smoking article containing a methyl menthol derivative (Example 1 or Example 3) or a smoking article containing a cooling agent other than a methyl menthol derivative (Comparative Example 2 or Comparative Example 4) than with a menthol-containing smoking article (Comparative Example 1 or Comparative Example 3), regardless of whether it was a combustion smoking article or heat-not-burn smoking article.
The abovementioned evaluation results regarding the bitter flavor imparted to the tongue suggested a possible relationship thereof to differences as to the site at which the cooling sensation was felt. That is, the bitter flavor is thought to be lessened when the tongue is less likely to feel a cooling sensation.
In addition to the abovementioned site effect evaluation by multiple selection, participants were also asked to select only the one site in the oral cavity at which the cooling sensation was felt most from among the upper jaw, tongue, cheek, and throat. The tallied results are shown in Table 6.

[Table 6]

Table 6

Site effect - sites at which sensed (one selection only)
		Upper jaw	Tongue	Cheek	Throat
Heat-not-burn smoking articles
	Example 1	1	0	0	4
	Example 2	1	0	0	4
	Comparative Example 1	4	1	0	0
	Comparative Example 2	4	0	0	1

Combustion smoking articles
	Example 3	1	0	0	4
	Comparative Example 3	4	0	1	0
	Comparative Example 4	4	0	0	1

As shown in Table 6, more evaluators felt the cold sensation most in the throat with a methyl menthol derivative-containing smoking article (Example 1 or Example 3) than with a menthol-containing smoking article (Comparative Example 1 or Comparative Example 3) or a smoking article containing a cooling agent other than a methyl menthol derivative (Comparative Example 2 or Comparative Example 4), regardless of whether it was a combustion smoking article or heat-not-burn smoking article. Use of a cooling sensation agent having the pronounced characteristic that the cooling sensation is felt in the throat allows a smoker to enjoy an unprecedented cooling sensation.
More evaluators also felt the cooling sensation most in the throat with a methyl menthol derivative-containing smoking article to which the carrier hydroxypropyl cellulose had been added (Example 2), similarly to Example 1, which was without added hydroxypropyl cellulose. This confirmed that the characteristic of the methyl menthol derivative such that the cooling sensation is felt in the throat, confirmed from the abovementioned sensory evaluation results, was expressed regardless of the presence or absence of additional hydroxypropyl cellulose. As indicated above, in addition to suppressing evaporation and dissipation of the flavor and/or cooling sensation component, and improving storage resistance, the abovementioned carrier can be expected to have the effect of protecting a flavor and/or cooling sensation component from physical damage.

(4) Storage resistance

Pre-storage heat-not-burn smoking articles of Examples 1 and 2 and Comparative Examples 1 and 2, prepared as described above, were stored exposed to the air at 30°C for 5 days. Each heat-not-burn smoking article after storage was then installed in a non-combustion smoking system with external heating shown in Figure 2.
Pre-storage combustion smoking articles of Example 3 and Comparative Examples 3 and 4 were also prepared as described above, and stored exposed to the air at 30°C for 5 days.
Ordinary products are stored under nearly sealed condition in e.g. polypropylene films to suppress the evaporation of menthol or the like. The abovementioned storage exposed to the air at 30°C, on the other hand, could be considered as comparatively more severe storage conditions.
The cooling sensations imparted by the smoking articles thus prepared were evaluated after storage on the basis of the procedure and evaluation criteria described above in "(1) Cooling sensation intensity." The evaluation results are shown in Table 7. The "Post-storage" column in Table 7 shows the evaluation results for the smoking articles after storage. Meanwhile, the "Pre-storage" column in Table 7 shows the evaluation results for smoking articles before storage from Table 2.

[Table 7]

Table 7

		Pre-storage	Post-storage
Heat-not-burn smoking articles
	Example 1	3.0	4.0
	Example 2	2.8	3.4
	Comparative Example 1	3.0	1.6
	Comparative Example 2	2.6	1.8

Combustion smoking articles
	Example 3	3.6	3.8
	Comparative Example 3	3.0	1.6
	Comparative Example 4	2.8	2.0

As shown in Table 7, menthol-containing smoking articles (Comparative Example 1 and Comparative Example 3) and smoking articles containing a cooling agent other than a methyl menthol derivative (Comparative Example 2 and Comparative Example 4) had decreased cooling sensation intensity after storage as compared to the cooling sensation intensity before storage, regardless of whether they were combustion smoking articles or heat-not-burn smoking articles. Meanwhile, the cooling sensation intensity of the methyl menthol derivative-containing smoking articles (Example 1 and Comparative Example 3) after storage was equal to or greater than that before storage.
The cooling sensation intensity after storage of a methyl menthol derivative-containing smoking article to which the carrier hydroxypropyl cellulose had been added (Example 2), was equal to or greater than the cooling sensation intensity before storage, similarly to Example 1, which was without added hydroxypropyl cellulose. This confirmed that the characteristic of the methyl menthol derivative-containing smoking articles such that the cooling sensation intensity after storage is equal to or greater than that before storage, confirmed from the abovementioned sensory evaluation results, was expressed regardless of the presence or absence of additional hydroxypropyl cellulose. As indicated above, in addition to suppressing evaporation and dissipation of the flavor and/or cooling sensation components, and improving storage resistance, the abovementioned carrier can be expected to have the effect of protecting a flavor and/or cooling sensation component from physical damage.
Without over-theorizing, it may be surmised that the reason for a methyl menthol derivative-containing smoking article having, after storage, a cooling sensation intensity at least equal to that before storage is assumed to be as follows. It is surmised that moisture contained in tobacco, and volatile components derived from tobacco, evaporate and dwindle during storage, whereas the methyl menthol derivative remained unevaporated. It is inferred that, for that reason, the cooling sensation of the methyl menthol derivative was more readily felt in general.

(1) Measurement of menthol and other cooling sensation agents in tobacco filler in an open system

Solutions were prepared by dissolving menthol and other cooling agents (the abovementioned COOLACT^® 370 and Symcool^® WS-23) respectively through addition of ethanol thereto. Each solution thus obtained was added to the tobacco filler portion of a combustion smoking article, using a microsyringe (MS-50, Ito Microsyringe, manufactured by Ito Seisakusho), such that that the content of menthol or other cooling sensation agent was 5,000 ppm relative to the weight of the tobacco, and the samples immediately after addition were considered to be "pre-storage cigarette samples." Each solution thus obtained was also added to the tobacco filler portion of a heat-not-burn smoking article (a tobacco stick comprising a tobacco filler portion and a filter portion), using the abovementioned microsyringe, such that that the menthol or other cooling sensation agent content was 5,000 ppm relative to the weight of the tobacco therein, and the samples immediately after addition were considered to be "pre-storage tobacco stick samples." The cigarettes and tobacco sticks injected with menthol or other cooling sensation agent were then placed on a tray (DT-1 disposable tray, manufactured by As One), stored for 5 days in an incubator (SCI-13 compact incubator, manufactured by Shibata), and were respectively considered to be "post-storage cigarette samples" and "post-storage tobacco stick samples."
In addition, 1.0 g of quinoline was precisely weighed out as an internal standard, and diluted to 1 L with methanol to serve as an extraction solvent.
The pre-storage cigarette samples, pre-storage tobacco stick samples, post-storage cigarette samples, and post-storage tobacco stick samples obtained as described above then underwent the following treatment.

· The tobacco filler portion was removed from each sample and placed in a screw tube, and 10 mL of the extraction solvent, prepared as described above, was added. The screw tubes were then shaken at 200 rpm for 20 minutes, and, after having been left to stand overnight, shaken again at 200 rpm for 20 minutes to obtain tobacco filler portion extract samples. The extract samples obtained from the pre-storage cigarette samples, pre-storage tobacco stick samples, post-storage cigarette samples, and post-storage tobacco stick samples were respectively considered to be "pre-storage cigarette extract samples," "pre-storage tobacco stick extract samples," "post-storage cigarette extract samples," and "post-storage tobacco stick extract samples."

The extract samples thus obtained were each collected using a syringe (25 mL, SS-02SZ, manufactured by Terumo Corporation) and filtered through a filter (0.45 µm, Prem Syringe Filter, RC, manufactured by Agilent Technologies), and the liquids obtained after filtration were respectively considered to be extract samples for pre-storage cigarette analysis, extract samples for pre-storage tobacco stick analysis, extract samples for post-storage cigarette analysis, and extract samples for post-storage tobacco stick analysis.
The target ions and qualifier ions shown below were selected for the respective cooling sensation agents. A target ion and qualifier ion were also selected for quinoline, used as the internal standard.

· Menthol (target ion: m/z = 95.1, qualifier ion: m/z = 71.0, 81.1)
· Symcool^® WS-3 (target ion: m/z = 114.0, qualifier ion: m/z = 57.0, 102.0)
· COOLACT^® 370 (target ion: m/z = 211.2, qualifier ion: m/z = 97.0, 168.1)
· Quinoline (target ion: m/z = 129.1, qualifier ion: m/z = 76.0, 102.0)

The analytical extract samples obtained as described above then underwent GC/MS analysis under the following conditions.

(Measurement apparatus and conditions)
Apparatus: Manufactured by Agilent Technologies
Column: HP-5MS (manufactured by Agilent Technologies), inner diameter 0.25 mm x length 30 m, film thickness 0.25 µm Injection volume: 1 µL
Injection mode: Split (10:1)
Injection port temperature: 270°C
Septum purge flow rate: 5 mL/minute
Carrier gas: Helium (He)
Column flow rate: 1 ml/minute (constant flow mode)
Oven: 40°C (for 3 minutes) to 280°C (for 10 minutes) at 10°C/minute
MS conditions
Solvent wait time: 4 minutes
Ionization method: Electron impact ionization (EI), 70 eV
Ion source temperature: 230°C
Quadrupole temperature: 150°C
Measurement mode: SIM
Transfer line temperature: 280°C

The area of menthol or other cooling agent and the internal standard area from the chromatogram obtained for each analytical extract sample was used to calculate the ratio of the internal standard to menthol or other cooling sensation agent (i.e., the internal standard ratio) by the following equation. $Internal standard ratio = menthol or other cooling agent area / internal standard area$
Using the internal standard ratios thus obtained, the residual rate of menthol and each cooling agent added to a cigarette or tobacco stick was calculated to three significant digits on the basis of the equation below. The results for cigarettes (i.e., combustion smoking articles) are shown in Table 8, and the results for tobacco sticks (i.e., heat-not-burn smoking articles) are shown in Table 9, respectively.
Residual rate = (Internal standard ratio of menthol or other cooling agent in the extract samples for post-storage analysis) / (Internal standard ratio of menthol or other cooling agent in an extract sample for pre-storage analysis) x 100

[Table 8]

Table 8

	Residual rate (%)
COOLACT^® 370	98.5
Menthol	15.9
Symcool^® WS-23	33.5

[Table 9]

Table 9

	Residual rate (%)
COOLACT^® 370	100
Menthol	10.4
Symcool^® WS-23	50.2

In view of the results in Tables 8 and 9, it was found that less of the menthol or the cooling sensation agent (Symcool^® WS-23) other than the methyl menthol derivatives was contained in the tobacco after storage than before storage, regardless of whether it had been in a combustion smoking article or a heat-not-burn smoking article Meanwhile, it was found that the amount of a methyl menthol derivative (i.e., COOLACT^® 370) contained in the tobacco remained almost unchanged from before to after storage.
This suggested that a methyl menthol derivative-containing smoking article has storage resistance superior to that of a menthol-containing smoking article or a smoking article containing a cooling sensation agent other than the methyl menthol derivative, regardless of whether it is in combustion smoking articles or heat-not-burn smoking articles.

(2) Measurement of menthol and other cooling agent in tobacco filler and filter in a closed system

A solution was prepared by dissolving a methyl menthol derivative (the abovementioned COOLACT^® 370) through addition of methanol thereto. The solution thus obtained was added using the microsyringe described above to the tobacco filler of portion of an unheated smoking article (a tobacco stick comprising a tobacco filler portion and a filter portion), using the abovementioned microsyringe, such that the methyl menthol derivative content was 2,500 ppm, 5,000 ppm, or 10,000 ppm relative to the weight of tobacco therein, and the samples immediately after addition were considered to be "pre-storage tobacco stick samples." Each tobacco stick injected with the methyl menthol derivative was placed in a Lami-Zip bag (AL-5, manufactured by Seisannipponsha), and left in an incubator (an SCI-13 compact incubator, manufactured by Shibata) for 5 days to provide a "post-storage tobacco stick sample."
The pre-storage and post-storage tobacco stick samples obtained in the abovementioned manner underwent the following processing.

· The tobacco filler portion and filter portion were removed from each sample and placed in a separate screw tube, and 10 mL of methanol were added. The screw tubes were then shaken at 200 rpm for 20 minutes, and, after having been left to stand overnight, shaken again at 200 rpm for 20 minutes to obtain extract samples from the tobacco filler portions and filter portions, respectively. The extract samples obtained from the pre-storage tobacco stick samples and post-storage tobacco stick samples were respectively considered to be "pre-storage tobacco stick extract samples" and "post-storage tobacco stick extract samples."

The extract samples thus obtained were each collected using a syringe (25 mL, SS-02SZ, manufactured by Terumo Corporation) and filtered through a filter (0.45 µm, Prem Syringe Filter, RC, manufactured by Agilent Technologies), and the liquids obtained after filtration were respectively considered to be extract samples for analysis ("extract samples for pre-storage tobacco stick analysis" and "extract samples for post-storage tobacco stick analysis," respectively).
The extract samples for analysis obtained as described above then underwent GC/MS analysis under the following conditions.

(Measurement apparatus and conditions)
Gas chromatography (GC/MS)
Apparatus: Manufactured by Agilent Technologies
Column: HP-5MS (manufactured by Agilent Technologies), inner diameter 0.25 mm x length 30 m, film thickness 0.25 µm Injection volume: 1 µL
Injection mode: Split (10:1)
Injection port temperature: 270°C
Septum purge flow rate: 5 mL/minute
Carrier gas: Helium (He)
Column flow rate: 1 mL/minute (constant flow mode)
Oven: 40°C (for 3 minutes) to 280°C (for 20 minutes) at 4°C/minute
MS conditions
Solvent wait time: 4 minutes
Ionization method: Electron impact ionization (EI), 70 eV
Ion source temperature: 230°C
Quadrupole temperature: 150°C
Measurement mode: Scan
MS scan range: m/z 26-450
Threshold: 50
Sampling rate: 2, Transfer line temperature: 280°C

Figures 7-9 are total ion chromatograms, obtained by GC/MS, of pre-storage tobacco stick samples to which 2,500 ppm, 5,000 ppm, and 10,000 ppm of a methyl menthol derivative (COOLACT^® 370) had been respectively added. In Figures 7-9, the upper part is a total ion chromatogram of the extract from the tobacco filler portion, and the lower part is a total ion chromatogram of the extract from the filter portion. The peak of the methyl menthol derivative is near retention time (RT): 53.05 in Figure 7, and near RT: 53.07 in Figures 8 and 9.
In Figures 7-9, peaks derived from the abovementioned methyl menthol derivative were detected in extracts from the tobacco filler portions, but no peaks derived from the abovementioned methyl menthol derivative were detected in extracts from the filter portions. It was thus found that the abovementioned methyl menthol derivative did not migrate from the tobacco filler portion to the filter portion immediately after addition (and before storage).
Figures 10-12 are total ion chromatograms, obtained by GC/MS, of post-storage tobacco stick samples to which 2,500 ppm, 5,000 ppm, and 10,000 ppm of a methyl menthol derivative (COOLACT^® 370) were respectively added. In Figures 10-12, the upper part is a total ion chromatogram of the extract from the tobacco filler portion, and the lower part that of the extract from the filter portion. The peak of the methyl menthol derivative is near RT: 53.00 in Figure 10, near RT: 53.03 in Figure 11, and near RT: 53.06 in Figure 12.
In Figures 10-12, peaks derived from the abovementioned methyl menthol derivative were detected in extracts from the tobacco filler portions, but no peaks derived from the abovementioned methyl menthol derivative were detected in extracts from the filter portions. It was thus found after storage, similarly to before storage, that the methyl menthol derivative had not migrated from the tobacco filler portion to the filter portion.
This suggested that the methyl menthol derivative remained at the site to which it was originally added, and that smoking articles containing the methyl menthol derivative can be expected to have the same cooling sensation intensity after storage as before storage.
Consequently, it was found that the flavoring ingredient-scented constituent member of the present invention, containing the cooling sensation agent (A)and having a retention index (RI) of 1300 or higher has a cooling sensation intensity superior to that of menthol. It was also found that said flavoring ingredient-scented constituent member has the characteristic of less bitter flavor than menthol.
It was also found that the abovementioned flavoring ingredient-scented constituent member has storage resistance superior to that of a flavoring ingredient-scented constituent member that contains menthol or a cooling sensation agent other than the abovementioned cooling sensation agent (A).

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 smoking article
20A Smoking segment
20B Connecting portion
20C Filter portion
21 Smoking composition sheet or material derived therefrom
22 Wrapper
23 Paper tube
24 Ventilation holes
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 Wrapper
30 Heat-not-burn smoking article
30A Body
30B Aerosol source holder
30C Additive component holding part
31 Power source unit
32 Control unit
33 Inhalation sensor
34 Storage part
35 Supply unit
36 Load
37 Residual amount sensor
38 Tobacco filler

Claims

A flavoring ingredient-scented constituent member, comprising
a constituent member of a smoking article and

a flavoring ingredient that contains a cooling sensation agent (A) having a retention index (RI) of 1300 or greater in a chromatogram obtained through analysis thereof by gas chromatography with a mass spectrometer (GC/MS), using a column having a stationary phase of 95% dimethylpolysiloxane/5% phenyl-methylpolysiloxane,

wherein the constituent member of the smoking article is scented with the flavoring ingredient.
The flavoring ingredient-scented constituent member set forth in claim 1, wherein the retention index (RI) of the cooling sensation agent (A) is 2,000 or greater.
The flavoring ingredient-scented constituent member set forth in claim 1 or 2, wherein the retention index (RI) of the cooling sensation agent (A) is 2,400-2,600.
The flavoring ingredient-scented constituent member set forth in any one of claims 1-3, wherein the cooling sensation agent (A) contains a methyl menthol derivative represented by the following General Formula (1):
(in Formula (1), the asterisks are asymmetric carbon atoms, X represents a hydrogen atom or substituent, and Y is an aryl group with 6-20 carbon atoms that may have a substituent)

or a salt thereof.
The flavoring ingredient-scented constituent member set forth in any one of claims 1-4, wherein the content of the cooling sensation agent (A) is 1 ppm or more relative to the flavoring ingredient-scented constituent member.
The flavoring ingredient-scented constituent member set forth in any one of claims 1-5, wherein the flavoring ingredient contains a flavor, a cooling sensation component, or a combination thereof.
The flavoring ingredient-scented constituent member set forth in claim 6, wherein the cooling sensation component contains a cooling sensation agent, a cooling sensation flavor component, or a combination thereof.
The flavoring ingredient-scented constituent member set forth in claim 7, wherein the cooling sensation agent comprises the cooling sensation agent (A) and a cooling sensation agent other than the cooling sensation agent (A).
The flavoring ingredient-scented constituent member set forth in claim 7 or 8, wherein the cooling sensation flavor component comprises menthol, menthone, peppermint oil, or a mixture thereof.
The flavoring ingredient-scented constituent member set forth in any one of claims 7-9, wherein the content of the cooling sensation flavor component is 0.0001-99 wt% relative to the flavoring ingredient-scented constituent member.
The flavoring ingredient-scented constituent member set forth in any one of claims 6-10, wherein the flavor comprises a natural flavor, a synthetic flavor, or a mixture thereof.
The flavoring ingredient-scented constituent member set forth in any one of claims 1-11, wherein the flavoring ingredient further contains a carrier.
The flavoring ingredient-scented constituent member set forth in claim 12, wherein the carrier contains a carbohydrate, cellulose derivative, non-pulp fiber, lipid, polyvinylpyrrolidone, polyvinyl alcohol, or a mixture thereof.
The flavoring ingredient-scented constituent member set forth in any one of claims 1-13, wherein the flavoring ingredient further contains an emulsifier.
The flavoring ingredient-scented constituent member set forth in any one of claims 1-14, wherein the flavoring ingredient is a liquid, semi-solid, or solid.
The flavoring ingredient-scented constituent member set forth in any one of claims 1-15, wherein the flavoring ingredient-scented constituent member further contains an aerosol source.
The flavoring ingredient-scented constituent member set forth in claim 16, wherein the aerosol source contains a polyhydric alcohol, triethyl citrate, triacetin, or a mixture thereof.
The flavoring ingredient-scented constituent member set forth in any one of claims 1-17, wherein the constituent member of the smoking article contains a nicotine source.
The flavoring ingredient-scented constituent member set forth in any one of claims 1-18, wherein the flavoring ingredient-scented constituent member further contains an adsorbent.
The flavoring ingredient-scented constituent member set forth in any one of claims 1-19, wherein the constituent member of the smoking article is a tobacco filler, filter, tube, rolling paper, tipping paper, plug, pouch, or liquid.
The flavoring ingredient-scented constituent member set forth in any one of claims 1-20, wherein the constituent member of the smoking article is a non-woven fabric.
A smoking article comprising the flavoring ingredient-scented constituent member set forth in any one of claims 1-21.
The smoking article set forth in claim 22, which is a heated smoking article.
The smoking article set forth in claim 22, which is a combustion smoking article.
The smoking article set forth in claim 22, which is a smokeless smoking article.
The smoking article set forth in claim 22, which is an electronic cigarette.