JP2017500002A - Composition for smoking containing flavor precursor - Google Patents

Abstract

The smoking composition includes an aerosol-forming substrate and a flavor precursor compound. When heated, the precursor compound releases a thiol-containing flavor compound or intermediate that enhances the flavor experience of the aerosol-forming substrate when used in a smoking article. The smoking article can include tobacco and can be configured to heat the tobacco but not to burn it.
[Selection] Figure 1

Description

  The present disclosure relates to smoking compositions having improved sensory components, and articles and methods associated with such smoking compositions.

  Smoking articles have been proposed that heat tobacco or other nicotine sources without burning the tobacco or nicotine source. Such articles generate an aerosol that can deliver nicotine and other tobacco components to the user. However, users may perceive flavor notes that are significantly different from those experienced with conventional smoking articles such as cigarettes.

  Accordingly, it is desirable to incorporate flavor compounds into tobacco or other nicotine sources used in non-combustible smoking articles so as to approximate the experience associated with smoking conventional cigarettes. Various flavor compounds are well known for addition to tobacco products. However, the volatility of such compounds presents challenges for incorporating the compounds into tobacco or smoking articles. For example, loss during production or storage can occur due to the volatility of the compound.

  As described herein, a smoking article in which a cigarette or other nicotine source is heated but does not burn will deliver a flavored aerosol to the user and experience the same as smoking a traditional cigarette. Provide to users. The article includes a flavor component that includes a flavor precursor that does not have a significant odor. The flavor precursor, upon heating, converts to one or more flavor compounds or intermediates for flavor compounds to produce a flavor note that provides a composition with a profile closer to that of a conventional cigarette.

  The smoking articles described herein may provide one or more advantages. For example, the smoking articles described herein provide an improved flavor experience as compared to smoking articles that do not include a flavor precursor. Upon heating, the flavor precursors described herein release a flavor compound or flavor compound intermediate containing a thiol group. Flavor compounds or intermediates containing thiols, such as hydrogen sulfide, methanethiol, and furfuryl thiol, have higher volatility than flavor precursor compounds. Because flavor precursors are not volatile or less volatile than flavor compounds, manufacturing losses can be reduced and the shelf life of the article can be longer. Furthermore, since the flavor precursor compound has a weaker aroma than the flavor compound, the article does not give a strong sulfur-based note when not in use.

  As used herein, “thiol” means a compound of formula RSH, where R is H or an organic group.

  As used herein, “thiol-containing flavor compounds” and “flavor compounds” are either thiol-containing flavor compounds that are released from a flavor precursor compound or formed by reaction of a thiol-containing intermediate with an aerosol-forming substrate. Means.

  As used herein, “thiol-containing intermediate” and “intermediate” are released from a flavor precursor compound and react with an aerosol-forming substrate such as tobacco or other nicotine source to produce a thiol-containing flavor. By any thiol-containing compound capable of producing a compound is meant.

  A thiol-containing flavor compound or intermediate is a compound that is more volatile than a flavor precursor compound. The flavor compound preferably has a flavor attribute that enhances the experience of the non-flammable smoking article and provides, for example, a more similar experience to that resulting from smoking of the burning smoking article. For example, flavor compounds can enhance flavor attributes such as complexity and mouthfulness. Complexity is commonly known as a single sensory attribute is not dominant and the overall flavor balance is richer. Mouthfulness is described as a perception of the richness and amount of smoke entering the mouth and throat. The released or generated thiol-containing flavor compound may provide one or more of these flavor attributes or other flavor attributes. In embodiments, the thiol-containing flavor compound that is released or generated is selected from the group consisting of hydrogen sulfide, methanethiol, 3-methyl-2-butene-1-thiol and furfurylthiol. Hydrogen sulfide and methanethiol are particularly preferred because of the flavor notes that are particularly associated with cigarette smoke.

  Any suitable test may be employed to determine whether the thiol-containing flavor compound produces a flavor component generally perceivable with cigarette smoking. For example, a compound reminiscent of the subjective flavor note perception associated with cigarette smoking is considered to have or produce a flavor for the purposes of this disclosure. In an embodiment, a trained flavorist determines whether a flavor compound has been released or produced upon heating of a flavor precursor compound, such as during smoking of a non-flammable smoking article in the presence of an aerosol-forming compound. May be. In embodiments, a randomly or non-randomly selected person may be selected to determine whether a compound that produces a flavor has been perceived. By way of example, a compound is determined to produce a flavor if more than 25%, eg, 50%, 60%, 70%, or 80% or more of the selected person perceive the flavor.

（Ｉ）、
式中、
Ｒ¹はＯＨまたはアミノ酸残基であり、
Ｒ²はＨ、Ｃ（Ｏ）ＣＨ₃、またはアミノ酸残基であり、
Ｒ³はＨまたはＣ１−Ｃ３非置換型アルキルであり、
Ｒ⁴は随意で、存在する場合にはＣ１−Ｃ３非置換型アルキルであり、
ｘは１〜３の整数である。 Any suitable sulfur-containing flavor precursor compound may be employed to release the thiol-containing flavor compound or intermediate. In embodiments, the flavor precursor compound has the structure of Formula I as follows:

(I),
Where
R ¹ is OH or an amino acid residue;
R ² is H, C (O) CH ₃ , or an amino acid residue;
R ³ is H or C1-C3 unsubstituted alkyl;
R ⁴ is optional and, when present, is C1-C3 unsubstituted alkyl;
x is an integer of 1 to 3.

R ¹ is preferably an OH or glycine residue. R ² is preferably H, C (O) CH ₃ , or a glutamic acid residue. R ³ is preferably H or CH ₃ . R ⁴ is preferably CH _3, but when present, produces a positively charged sulfur species. R ⁴ is preferably absent. X is preferably 1 or 2.

（ＩＩ）
式中、
Ｒ¹はＯＨまたはアミノ酸残基であり、
Ｒ²はＨ、Ｃ（Ｏ）ＣＨ₃、またはアミノ酸残基であり、
Ｒ³はＨ、Ｃ１−Ｃ３非置換型アルキルまたはアミノ酸残基であり、
ｘは１〜３の整数である。 In embodiments, the flavor precursor compound has the structure of Formula II as follows:

(II)
Where
R ¹ is OH or an amino acid residue;
R ² is H, C (O) CH ₃ , or an amino acid residue;
R ³ is H, C1-C3 unsubstituted alkyl or an amino acid residue,
x is an integer of 1 to 3.

R ¹ is preferably an OH or glycine residue. R ² is preferably H, C (O) CH ₃ , or a glutamic acid residue. R ² is preferably H, C (O) CH ₃ , or a cysteine residue. X is preferably 1 or 2.

（ＩＩＩ）
式中、
Ｒ¹はＯＨまたはアミノ酸残基であり、
Ｒ²はＨ、Ｃ（Ｏ）ＣＨ₃、またはアミノ酸残基であり、
ｘは１〜３の整数である。 In embodiments, the flavor precursor compound has the structure of Formula III as follows:

(III)
Where
R ¹ is OH or an amino acid residue;
R ² is H, C (O) CH ₃ , or an amino acid residue;
x is an integer of 1 to 3.

R ¹ is preferably an OH or glycine residue. R ² is preferably H, C (O) CH ₃ , or a glutamic acid residue. X is preferably 1 or 2.

（ＩＶ）
式中、
Ｒ¹はＯＨまたはアミノ酸残基であり、
Ｒ²はＨ、Ｃ（Ｏ）ＣＨ₃、またはアミノ酸残基である。 In embodiments, the flavor precursor compound has the structure of Formula IV as follows:

(IV)
Where
R ¹ is OH or an amino acid residue;
R ² is H, C (O) CH ₃ , or an amino acid residue.

R ¹ is preferably an OH or glycine residue. R ² is preferably H, C (O) CH ₃ , or a glutamic acid residue.

  Of course, in connection with Formulas I-IV listed above, amino acid residues can be linked to the core structure via a peptide bond or via a suitable side chain (such as a carboxylic acid group).

  In embodiments, the flavor precursor compounds are cysteine (CAS number 3374-33-9), cysteine (CAS number 56-89-3), glutathione (CAS number 70-18-8), methionine (CAS number 59-51). -8), DL methionine methylsulfonium (CAS number 582174), N-acetylcysteine (CAS number 616-91-1), S-methylcysteine (CAS number 1187-84-4), DL-homocysteine (CAS number 454) -29-5), N-acetylmethionine (CAS number 65-82-7), farnesyl-Met-Ome (CAS number 218962-72-2), albumin (CAS number 9006-59-1) and 2-hydroxy- Consists of 4- (methylthio) butyric acid (CAS number 922-50-9) That is a compound selected from the group.

  Disclosure of a compound herein refers to the particular compound disclosed, as well as its appropriate salts, polymorphs, isomers, etc., whether by name, structure, reference number or the like. To do.

  In embodiments, the flavor precursor compound is a compound comprising a cysteine residue. Examples of such compounds include cysteine, glutathione, N-acetylcysteine, S-methylcysteine, and cysteine.

  The flavor precursor compound is preferably cysteine or glutathione. More preferably, the flavor precursor compound is cysteine.

  As used herein, a flavor component is a component that includes a flavor precursor compound, for example, additional compounds commonly used in flavor components. In particular, the ingredients may include one or more flavor compounds well known in the art, including menthol, Dutch peppermint, peppermint, eucalyptus, vanilla, cocoa, chocolate, coffee, tea, spices (cinnamon, cloves and ginger, etc. ), Fruit extracts, and combinations thereof. In embodiments, the flavor component further comprises menthol or eugenol. Such flavoring agents are generally used to provide a refreshing flavor to the smoke of smoking articles. Ingredients can also include adjuvants that allow the ingredients to meet technical requirements such as stability and tonality persistence.

  A delivery system may be provided, which encapsulates the flavor component or flavor precursor compound. The delivery system protects the flavor component or flavor precursor compound during manufacture and storage.

  In embodiments, the delivery system can take any suitable form that can retain the flavor component or flavor precursor compound within the structure of the system until release is desired.

  The delivery system preferably has a closed matrix or network structure, which encloses the flavor precursor compound within the closed structure. For example, the flavor component or precursor may be confined within a region inside the matrix structure. As the material is compressed or deformed, flavor components or precursors are forced out of the matrix structure, for example through breakage of the surrounding structure. In embodiments, the delivery system includes a polymeric matrix that includes one or more substrate-forming polymers. For example, the gradual collapse of the polymer matrix with compressive force, temperature, or both results in controlled release of the flavor precursor compound from the delivery system. The release of the flavor precursor compound can vary as a function of deformation due to temperature or pressure or shear forces applied to the delivery system.

  The delivery system can be advantageously provided in a variety of different forms within the smoking article so that the method or the precursor can be incorporated into the smoking article is flexible. In embodiments, the delivery system is provided in the form of particles, beads or capsules. The particles, beads or capsules can be formed in any suitable shape, but are preferably substantially cylindrical or spherical.

  In various embodiments, the flavor precursor is synthesized or purified before being added to the flavor component or flavor delivery component.

  As noted above, the flavor precursor compound may be included in any suitable manner and in any suitable amount within the smoking composition. The term “smoking composition” is used to describe an ingredient that, when heated, produces an aerosol and is used to make a smoking article. The term “smoking article” refers to an article that directly or indirectly heats a smoking composition, or does not burn or heat a smoking composition, but rather uses an air stream or chemical reaction to produce tobacco or other Smoking articles that deliver nicotine, flavor compounds, or other materials from any nicotine source. As used herein, the term “smoke” is used to describe an aerosol produced by a smoking article. The aerosol produced by the smoking article can be produced by a non-combustible smoking article such as, for example, a heated smoking article or a non-heated smoking article.

  The flavor delivery system can controllably release the flavor precursor compound to its surrounding environment by any suitable method, for example, by deformation of the flavor delivery system or by a change in temperature. The amount of flavor precursor compound released at regular intervals, as well as the start or end of the interval, can be controlled. The amount of flavor precursor compound released during each interval and the length of the time interval need not be the same.

  The smoking composition of the present invention includes a flavor precursor compound or flavor component, which is optionally provided as part of a delivery system. Smoking compositions include, for example, one or more of herbal leaves, tobacco leaves, tobacco stems, tobacco stem fragments, homogenized tobacco, reconstituted tobacco, processed tobacco, extruded tobacco, and expanded tobacco. It may contain one or more of powders, granules, pellets, pieces, strips or sheets. The smoking composition may be in a non-contained form or provided in a suitable container or cartridge. For example, the smoking composition may be placed in paper or wrap to have the form of a plug.

  Smoking articles that include aerosol generators generally include an aerosol-forming substrate that is often assembled in the form of a rod with other ingredients. In general, such rods are configured in a shape and size that is inserted into an aerosol generator that includes a heating element for heating the aerosol-forming substrate.

  As used herein, an “aerosol-forming substrate” is a type of smoking composition that can be used in an aerosol generator to produce an aerosol. The aerosol-forming substrate can release a flavor compound upon heating. The aerosol-forming substrate can be in solid form or in liquid form. The substrate can include both liquid and solid components. The aerosol-forming substrate can include tobacco and flavor components, where the flavor precursor compound or separated flavor compound is released from the substrate upon heating. In embodiments, the aerosol-forming substrate does not include tobacco but includes a flavor component, wherein the flavor precursor compound or separate flavor compound described herein is released from the substrate upon heating and optionally from nicotine. The The aerosol-forming substrate can further include an aerosol former. Examples of suitable aerosol formers are glycerin and propylene glycol. Optionally, the aerosol-forming substrate can be provided on or embedded in a carrier, which can take the form of a powder, granules, pellets, pieces, spaghetti strands, strips or sheets. The aerosol-forming substrate may be deposited on the surface of the carrier, for example in the form of a sheet, foam, gel or slurry. The aerosol-forming substrate can be deposited over the entire surface of the carrier, or alternatively in a fixed pattern to provide non-uniform flavor delivery in use.

  The smoking article may include a filter, which may be a single segment filter or a multi-component filter including two or more connected or unconnected filter segments. Any suitable filter or filter segment may be included in the smoking article described herein. Each of the one or more filter segments may comprise a flavor precursor compound or flavor component, but the precursor or component is optionally provided within the delivery system. Smoking articles can be packaged for sale in containers (eg, in soft packs or hinge-lid packs), with inner liners coated or impregnated with flavor compounds, flavor components or delivery systems.

  A smoking composition comprising a flavor precursor compound or flavor component (precursor or component is optionally provided within the delivery system) can be manufactured using any suitable technique. For example, a flavor component containing a flavor precursor compound may be sprayed on the tobacco. To facilitate spraying, the flavor precursor compound can be added to the liquid carrier to form a mixture such as a solution, suspension or slurry, and the slurry can be applied to tobacco. The slurry comprising the flavor precursor compound can comprise any liquid or liquid mixture suitable for dispersion and distribution (eg, spraying) of the particles comprising the flavor precursor compound. A preferred liquid is water (eg, deionized water), although other liquids such as alcohols can be used.

  In some embodiments, the tobacco can be immersed in a solution, suspension or dispersion containing a flavor precursor. Solids such as powders or crystals containing flavor precursors may be added to the tobacco. The smoking composition can then be processed for use in a smoking article.

  In some embodiments, the flavor precursor compound may be added to the cut filler tobacco stock supplied to the cigarette making machine, or in a pre-formed tobacco column before the cigarette wrapper is wrapped around the tobacco column. It may be applied.

  The concentration of the flavor precursor compound in the slurry can be any amount suitable for the distribution of the slurry onto the tobacco. A slurry comprising a flavor precursor compound dispersed in a liquid can comprise from about 0.01 to about 2 weight percent of a flavor precursor compound. The flavor precursor compound is provided in the form of a dry powder and can be applied to tobacco as is. If dry powder is used, it can be dusted onto tobacco. Another technique for incorporating a flavor precursor compound into a tobacco smoking composition involves adding the flavor precursor compound to a slurry of the ingredients used to make the reconstituted tobacco. The slurry, including the flavor precursor compound, can be formed into a reconstituted tobacco sheet, and the sheet can be cut into pieces for incorporation as a cut filler in a smoking composition or other form of smoking article rod. Can do.

  Homogenized tobacco can also be used to make an aerosol-forming substrate for use in smoking articles that are heated with an aerosol generator. The term “homogenized tobacco” as used herein means a material formed by agglomerating tobacco particles. Tobacco dust can be agglomerated by smoking during shipping and production, and leaf lamina, petiole and other finely pulverized tobacco by-products can be mixed with a binder to agglomerate particulate tobacco. Homogenized tobacco includes, in addition to flavor precursors or flavor components, aerosol forming agents, plasticizers, wetting agents, and non-tobacco fibers, excipients, water-soluble and water-insoluble solvents and combinations thereof. Other additives that are not limited thereto may be provided. Homogenized tobacco can be molded, extruded or rolled. Numerous reconstruction processes for producing homogenized tobacco materials are well known in the art. These include, for example, papermaking processes of the type described in US 5,724,998, for example molding processes of the type described in US 5,724,998, such as US 3,894,544. Includes, but is not limited to, types of soft mass reconstitution processes and extrusion processes of the type described, for example, in GB 983,928.

  Of course, the aerosol-forming substrate may have different shapes and sizes, for example, depending on the type of smoking article intended for use. The aerosol-forming substrate can be substantially three-dimensional. For example, the aerosol-forming substrate may be a brick or plug that includes a plurality of strands of homogenized tobacco material. Alternatively, the aerosol generating substrate may be substantially two-dimensional. For example, the aerosol generating substrate may be a mat or sheet comprising a plurality of homogenized tobacco strands.

  The amount of flavor precursor compound desired in the smoking composition can vary depending on the final product intended to include the smoking composition. For example, flavor precursor compounds can be added to tobacco to enhance the flavor or aroma of conventional smoking articles such as cigarettes, cigarettes, and the like. Because such articles already produce a similar flavor or fragrance upon smoking, flavor precursor compounds that release flavor compounds with similar flavor qualities may be added in relatively low concentrations or amounts. In contrast, higher concentrations or higher amounts of flavor precursor compounds are added to smoking compositions (such as tobacco-containing aerosol-forming substrates) that are to be used in smoking articles whose components are aerosolized without burning. It may be desirable to add. Smoking articles having tobacco-containing aerosol-forming substrates for use with aerosol generators generally provide flavor characteristics that are different from those of combustion-type smoking articles. It may also be desirable to include higher concentrations or higher amounts of flavor compounds in tobacco-free smoking compositions, such as non-tobacco-containing aerosol-forming substrates. Preferably, the smoking composition for use in a smoking article includes a flavor precursor compound in an amount that provides the user with a perceived notebook similar to a burning smoking article such as a cigarette. For example, a flavor precursor is included in a non-combustible smoking article or a tobacco-free smoking article in an amount that results in the release or delivery of a flavor compound similar to that delivered to a user of a conventional smoking article such as a cigarette. Also good.

  In embodiments, the amount of flavor compound delivered to the user can be determined per smoke absorption. Any suitable method may be used to determine the amount of flavor compound delivered per smoke. For example, ISO, Health Canada Intense Law, or other standard or automated procedures may be employed or modified to determine the per-smoke content. Examples of ISO methods that may be employed or modified include: (i) ISO 4387: 1991 Cigarettes-Determination of total and nicotine-free dry matter using routine analytical smoking machines (1991-10-15), (Ii) ISO 8454: 1995 Cigarette-Determination of carbon monoxide in the vapor phase of cigarette smoke-NDIR method (1991-11-15), (iii) ISO 10315: 1991 Cigarette-Nicotine in smoke condensate -Gas chromatographic method (1991-08-01) and (IV) ISO 10362-1: 1991 Cigarette-Determination of water in smoke condensate-Part 1: Gas chromatographic method (1991-09-15), etc. Is included. Health Canada Intense Act means Health Canada-official method T-115, determination of “tar”, nicotine and carbon monoxide in mainstream cigarette smoke (December 1999). Regardless of the method employed, the amount of flavor compound delivered per smoked conventional cigarette is determined so as to deliver a similar amount of flavored compound per smoked, and the cigarette or It may be desirable to formulate non-conventional smoking articles that aerosolize other ingredients. The amount of flavor precursor compound added to the smoking composition for such articles can vary, and how much flavor precursor is required to deliver a similar amount of flavor compound. You may test to determine.

  Of course, the desired amount of flavor compound delivered per smoke will depend on the flavor compound itself. In embodiments, the smoking article is configured to deliver more than about 5 nanograms of flavor compound per smoke. In embodiments, the smoking article is from about 10 nanograms of flavor compound per smoke to 1 milligram of flavor compound per smoke, eg, from about 50 nanograms per smoke to about 750 nanograms per smoke, or 1 smoke. It is configured to deliver from about 75 nanograms per minute to about 500 nanograms per smoke absorption.

  The amount of flavor precursor compound added to the smoking composition to deliver the desired amount of separated flavor compound to the user will depend on the components and components of the article and flavor precursor compound.

  Of course, the flavor precursor may be added in any amount or concentration appropriate to the smoking composition. In an embodiment, the smoking composition comprises 0.001% by weight or more of the flavor precursor compound based on the total weight of the tobacco. In embodiments, the smoking composition comprises 0.005% by weight or more of the flavor precursor compound. In embodiments, the smoking composition comprises 0.01% by weight or less of a flavor precursor compound. In embodiments, the smoking composition comprises from about 0.001% to about 2% by weight flavor precursor compound, such as from about 0.005% to about 1% by weight flavor precursor compound, or about 0.01%. % By weight to about 0.25% by weight of a flavor precursor compound.

  The flavor precursor compound may be added to the tobacco at any suitable time, such as before or during processing, for incorporation into a smoking article or the like. It is preferred that the flavor precursor compound is stable under such treatment (ie, no flavor compound is released or produced).

  In embodiments, one or more flavor precursor compounds are dissolved in a food solvent and then applied to a tobacco substrate or other suitable substrate at a concentration of up to 1000 ppm. The substrate can then be equilibrated for at least 48 hours at room temperature and approximately 60% humidity. For application during substrate generation (eg, cast leaf process, extrusion), the compound can be added directly as a solid material to any available food solvent system required in the process. If application as a solid is not feasible, the compound can be applied as a solution, suspension, etc. produced as described above. The concentration on the substrate during production can reach 1% of the total dry weight%.

  In an embodiment, tobacco reconstitution is performed by drying and shaping a homogeneous slurry of tobacco powder, water, glycerin, binder and cellulose fibers. This type of process, known as the cast leaf process, is widely used by the tobacco industry to produce reconstituted or homogenized tobacco in conventional cigarette applications. The cast leaf process may involve the application of temperatures up to about 140 ° C, such as from about 90 ° C to about 140 ° C. Therefore, when a smoking composition containing a flavor precursor compound is produced in a cast leaf process, the flavor precursor compound is preferably stable at such temperatures.

  The flavor precursor compound preferably releases the flavor compound or intermediate under the general use conditions of the article in which the flavor precursor compound is incorporated. As an example, a smoking article that heats tobacco without burning it to aerosolize tobacco components typically heats the tobacco to about 200 ° C to about 450 ° C. Accordingly, the flavor precursor compound preferably releases the flavor compound at a temperature of about 200 ° C. to about 450 ° C. when a smoking composition comprising the flavor precursor compound is included in such an article. As another example, tobacco burning typically occurs at a temperature of about 450 ° C. Accordingly, the flavor precursor compound preferably releases the flavor compound at a temperature below about 450 ° C. when a tobacco component comprising the flavor precursor compound is included in a combustible smoking article such as a cigarette or cigarette.

  In embodiments, the flavor precursor compound releases the flavor compound at a temperature of about 150 ° C. or higher. In embodiments, the flavor precursor compound releases the flavor compound at a temperature of about 450 ° C. or less. In embodiments, the flavor precursor compound releases the flavor compound at a temperature of about 100 ° C. to about 450 ° C., such as about 150 ° C. to about 450 ° C. or about 200 ° C. to about 450 ° C.

  Tobacco component as used herein means a smoking composition comprising tobacco and a flavor precursor. For example, the tobacco component may be used in combustion smoking articles or non-combustible smoking articles in which an aerosol-forming substrate is used. The tobacco component may be a reconstituted tobacco including tobacco types with different origins, as well as binders and wetting agents. The wetting agent promotes aerosol formation. Upon heating, the wetting agent evaporates and recondenses into small droplets, producing a visible aerosol. The flavor precursor component releases the flavor compound under the conditions of use, but preferably does not release under the conditions of storage, processing, or manufacture.

  In the case of a combustible smoking article such as a cigarette, the smoking composition can be in any part of the smoking article having a tobacco substrate (eg, with a conventional cigarette tobacco rod) or with a conventional cigarette filter. Can be used in one or more segments. In the case of a smoking composition, or a smoking article whose components are not burned, the smoking composition can be used in any part of a smoking article having an aerosol-forming substrate.

  As an example, and with reference to FIG. 1, a schematic diagram of a smoking article 102 in which the smoking composition is not burned is shown. As shown in FIG. 1, a smoking article 102 includes a combustible heat source 104, an aerosol-forming substrate 106, an elongated expansion chamber 108, and a mouthpiece 110 that are adjacently and coaxially arranged, and these are low air permeable cigarette papers. Wrapped in 112 outer wrappers.

  The combustion heat source 104 is a pyrolytic porous carbon-based heat source. The combustible heat source 104 is cylindrical and includes a central airflow channel 116 extending longitudinally through the combustible heat source 104. A substantially air-impermeable and heat-resistant iron oxide coating 114 is provided on the inner surface of the central airflow channel 116. The aerosol-forming substrate 106 is located immediately downstream of the flammable heat source 104 and includes a cylindrical plug of homogenized tobacco material 118 that includes a flavor precursor compound and glycerin as an aerosol former and is surrounded by a filter plug wrap 120. Prepare. Homogenized tobacco material 118 is composed of filaments of extruded tobacco material aligned in the longitudinal direction.

  A thermally conductive element 122 comprising an aluminum foil tube surrounds and contacts the rear portion of the combustible heat source 104 and the adjacent front portion of the aerosol generating substrate 106. As shown in FIG. 1, the rear portion of the aerosol generating substrate 106 is not surrounded by the thermally conductive element 122.

  The elongated expansion chamber 108 is located downstream of the aerosol generating substrate 106 and comprises an open tube at the end of a cylindrical cardboard 124. The mouthpiece 110 of the smoking article 102 includes a cylindrical plug of cellulose acetate tow 126 located downstream of the expansion chamber 108 and surrounded by a filter plug wrap 128 with very low filtration efficiency. The mouthpiece 110 can be surrounded by chipping paper (not shown). The dimensions of the smoking article 102 may be similar to conventional cigarettes.

  In use, the user ignites the combustible carbon-based heat source 4 and then draws air toward the mouthpiece 110 through the downstream central airflow channel 116. The front portion of the aerosol generating substrate 106 is heated primarily by conduction through the combustible heat source 104 and the adjacent non-combustible rear portion of the thermally conductive element 122. The inhaled air is heated as it passes through the central airflow channel 116 and then heats the aerosol-forming substrate 106 by convection. Heating of the aerosol-forming substrate 106 releases volatile and semi-volatile compounds, including separated flavor compounds, and glycerin from the aerosol-forming substrate 118, which was inhaled as it flowed through the aerosol-forming substrate. It is mixed in the heated air.

  The heated air and entrained compounds flow downstream through the expansion chamber 108, cool and condense, forming an aerosol that enters the user's mouth through the mouthpiece (at approximately ambient temperature).

  To manufacture the smoking article 102, a rectangular part of the thermally conductive element 122 is glued to the cigarette paper 112. The heat source 104, the plug of the aerosol-forming substrate 106 and the expansion chamber 108 are properly aligned and arranged with the attached thermally conductive element 122 on the cigarette paper 112. The cigarette paper 112 and attached thermal conductive element 122 are wrapped and adhered around the heat source 104, the aerosol generating substrate 106 and the rear portion of the expansion chamber 108. The mouthpiece 110 is attached to the open end of the expansion chamber using well-known filter coupling techniques.

  In another example of a heated smoking article, a smoking composition comprising a flavor precursor compound is in direct contact with a non-combustible heat source, such as an electrical heat source. FIG. 2 shows a smoking article that is heated by an electrical heat source when engaged with a consumer device. The smoking article 101 includes a front plug 103, an aerosol forming substrate 111, a hollow cellulose acetate tube 109, a moving section 107, and a mouthpiece filter 105. These five elements are arranged in turn in a coaxial arrangement and are assembled by cigarette paper 115 to form a rod. The rod has a mouth end, the user inserts it into the mouth during use, and the distal end is located at the opposite end of the rod with respect to the mouth end. When assembled, the rod has a length of 52 mm and a diameter of 7.2 mm. The front plug 103 is a cylindrical portion of cellulose acetate tow. The aerosol-forming substrate 111 is located downstream of the front plug 103 and includes a bundle of crimped cast leaf cigarettes wrapped in filter paper. Cast leaf tobacco contains an additive containing glycerin as an aerosol former. The tube 109 is located immediately downstream of the aerosol-forming substrate 111 and is formed from cellulose acetate. The moving section 107 allows volatile substances, including flavor compounds, to be emitted from the aerosol-forming substrate 111 and pass along the rod toward the mouth end. Volatile materials can be cooled in the moving section 107 to form an aerosol. The mouthpiece filter 105 is a conventional mouthpiece filter formed from cellulose acetate tow. The elements specified above are assembled by tightly wrapping in cigarette paper 115.

  The aerosol generator 119 includes an outer cylinder 121 for receiving the smoking article 101 for consumption. The heating element 113 is located in the outer cylinder 121 and is arranged to mesh with the distal end of the smoking article 101. The heating element 113 is formed in the form of a blade ending at the tip. When the smoking article 101 is pushed into the outer cylinder, the tip of the heating element 113 is first engaged with the front plug 103 and then penetrates into the aerosol forming substrate 111. When the smoking article 101 is properly engaged with the aerosol generating device 119, the heating element 113 is positioned in the aerosol-forming base 111. The heat generated by the heating element 113 is transferred to the aerosol-forming substrate 111 containing the flavor precursor compound by conduction and convection. The insulating collar 117 surrounds the portion of the heating element 113 that comes into contact with the front plug 103 and can protect it from burning and melting. Of course, the smoking articles described in connection with FIGS. 1 and 2 are only two examples of smoking articles that may employ a smoking composition comprising a flavor precursor compound as described herein. Further, it will be appreciated that a method for making a smoking article having a smoking composition comprising a flavor precursor compound in addition to those described in connection with FIGS. 1 and 2 may be employed.

  Any suitable method for making a smoking article having a smoking composition comprising a flavor precursor compound may be employed. In general, a method for making a smoking article having a smoking composition comprising a flavor precursor compound includes adding or incorporating the flavor precursor compound or flavor delivery composition into a smoking composition such as a cigarette or other substrate. And incorporating the smoking composition into the smoking article.

  In general, and as described herein, a method for improving the flavor of a smoking composition adds a flavor precursor compound (optionally encapsulated within a delivery system) to the smoking composition. Process. The flavor precursor compound releases or separates the flavor compound or intermediate upon heating. As used herein, “release” and “separation” are used interchangeably. Heating of the flavor precursor compound occurs when the smoker uses the smoking article (when burning or heating).

  All academic and technical terms as used herein have meanings commonly used in the art unless otherwise specified. The definitions provided herein are provided to facilitate the understanding of certain terms frequently used herein.

  As used in this specification and the appended claims, the singular forms ("a" and "the") include embodiments that have the plural subject matter, but are clearly defined by their content. That is not the case.

  As used herein or in the appended claims, the term “or” is generally used in its sense including “and / or” unless the content clearly dictates otherwise.

  The expressions “having”, “including”, “comprising” or the like as used herein are used in an unrestricted sense and generally mean “including but not limited to”. It is understood that expressions “substantially composed”, “configured” and the like are encompassed by expressions “including” and the like.

  Non-limiting examples illustrating certain aspects of the compounds, components, processes and articles described in this disclosure are provided below.

  As shown in Table 1, various non-volatile sulfur compounds are screened by (ATD) GC-MS on a cellulose filter to determine whether and how much hydrogen sulfide and methanethiol are released upon heating. .

  A compound is also added to a non-combustible smoking article to evaluate changes in the sensory attributes of the compound during aerosolization of the article in the presence or absence of the compound.

  In addition, a certain non-volatile sulfur compound is applied to tobacco mixed by syringe injection and used for a non-combustion smoking substrate. Cigarettes with non-volatile sulfur compounds are formed into rods and allowed to equilibrate for at least 12 hours prior to evaluation.

Using a smoke simulator in the push method, the orthorusal effect of the selected compound is evaluated at different concentrations for the overall aroma. The selected compound is then selected for sensory testing.

The aqueous solution is prepared according to Table 2. In addition, 1:10 and 1: 100 dilutions are prepared for verification.

ATD-GC-MS analysis is performed using the following instrument settings:

For each compound solution (stock solution, 1:10, 1: 100), 20 μL is spiked into a pre-equilibrated Cambridge pad piece, which is then inserted into a glass tube. After thermal desorption, the tube is evaluated for orthonasal and the detected aroma note is determined. The results are shown in Table 5.

The results showed that there are two main types of compounds, the first mainly generating hydrogen sulfide (H ₂ S) and the second mainly generating methanethiol (MSH). It is. The exception was egg albumin, but the occurrence appears to be similar.

These candidate tubes, which primarily generate H ₂ S, were orthosesal rated as sulfur-based, roasty or burnt after heating. H ₂ S could not be detected directly. In contrast, all compounds that generate methanethiol were determined to have a potato-like fragrance, indicating the presence of methional as a secondary product.

Using a smoke simulator in a pushing manner, orthosesal and smoking assessments of selected non-volatile sulfur compounds are performed. The following prototypes were tested:

  The test was conducted as follows. The smoking system is from the Canadian Health Service. The power setting of the smoke simulator is 54W. Smoking evaluation was carried out for each concept showing the palatability in orthonasal evaluation. A smoking assessment was performed by comparing the untreated mixture with the treated concept.

Only cysteine and glutathione were selected for submission to the expert panel sensory test. Concept B was selected for glutathione and Concept B for cysteine.

  The addition of sulfur-containing compounds, especially those with free thiol groups, improved the flavor perception of non-flammable products and addressed issues such as off-note, complexity and mouthfeel. In particular, the addition of the thiol-containing precursors cysteine and glutathione contributes positively by adding smokyness, mouthfeel, roughness, bitterness and complexity to the overall flavor of the aerosol formed upon heating.

  In summary, the addition of sulfur-containing precursors increases the overall prototype quality by increasing the smoky and dark attributes, reducing the off-notes of non-flammable products, and increasing mouth and throat sensations such as bitterness and mouthfulness. It has been shown to have a positive effect on sensitive perception.

Claims (19)

A smoking article,
An aerosol-forming substrate;
A heating element configured to heat but not burn the aerosol-forming substrate;
A smoking article comprising: a flavor precursor compound added to the aerosol-forming substrate, wherein the flavor precursor compound releases a thiol-containing flavor compound upon heating of the aerosol-forming substrate by the heating element. .   The smoking article according to claim 1, wherein the thiol-containing flavor compound is hydrogen sulfide or methanethiol. The smoking article according to claim 1 or 2, wherein the flavor precursor compound has the following structure.

(I),
Where
R ¹ is OH or an amino acid residue;
R ² is H, C (O) CH ₃ , or an amino acid residue;
R ³ is H or C1-C3 unsubstituted alkyl;
R ⁴ is optional and, when present, is C1-C3 unsubstituted alkyl;
x is an integer of 1 to 3. R ¹ is OH or glycine residue, R ² is H, C (O) CH ₃ , or glutamic acid residue, R ³ is H or CH ₃ , R ⁴ is not present, and x is 1 or 2. Item 6. A smoking article according to Item 3. The smoking article according to claim 1 or 2, wherein the flavor precursor compound has the following structure.

(II)
Where
R ¹ is OH or an amino acid residue;
R ² is H, C (O) CH ₃ , or an amino acid residue;
R ³ is H, C1-C3 unsubstituted alkyl or cysteine residue,
x is an integer of 1 to 3. The smoking article according to claim 5, wherein R ¹ is OH or glycine residue, R ² is H, C (O) CH ₃ , or glutamic acid residue, R ³ is H or CH ₃ , and x is 1 or 2. . The smoking article according to claim 1 or 2, wherein the flavor precursor compound has the following structure.

(III)
Where
R ¹ is OH or an amino acid residue;
R ² is H, C (O) CH ₃ , or an amino acid residue;
x is an integer of 1 to 3. The smoking article according to claim 7, wherein R ¹ is OH or glycine residue, R ² is H, C (O) CH ₃ , or glutamic acid residue, and x is 1 or 2. The smoking article according to claim 1 or 2, wherein the flavor precursor compound has the following structure.

(IV)
Where
R ¹ is OH or an amino acid residue;
R ² is H, C (O) CH ₃ , or an amino acid residue. The smoking article according to claim 9, wherein R ¹ is OH or a glycine residue, and R ² is H, C (O) CH ₃ , or a glutamic acid residue.   The smoking article according to claim 1 or 2, wherein the flavor precursor compound contains a cysteine residue.   The smoking article of claim 11, wherein the flavor precursor compound is selected from the group consisting of cysteine, glutathione, N-acetylcysteine, S-methylcysteine, and cystine.   The flavor precursor compounds are cysteine, cystine, glutathione, methionine, DL methionine methylsulfonium, N-acetylcysteine, S-methylcysteine, DL-homocysteine, N-acetylmethionine, farnesyl-Met-Ome, albumin and 2- The smoking article according to claim 1 or 2, selected from the group consisting of hydroxy-4- (methylthio) butyric acid.   14. A smoking article according to claim 13, wherein the flavor precursor compound is cysteine or glutathione.   The smoking article according to claim 1 or 2, wherein the flavor precursor compound is cysteine.   The smoking article according to any one of claims 1 to 15, wherein the aerosol-forming substrate comprises tobacco.   17. The smoking article of claim 16, wherein heating the tobacco and the flavor precursor compound produces furfuryl thiol.   18. A smoking article according to any one of the preceding claims, wherein the flavor precursor compound is configured to release hydrogen sulfide or methanethiol at a temperature of about 200C to about 450C.   The smoking article according to any one of claims 1 to 18, further comprising nicotine or a nicotine source.

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