JP2020058390A - Smoking composition comprising flavour precursor - Google Patents

Abstract

To provide smoking compositions having enhanced sensory components.SOLUTION: A smoking composition comprises an aerosol-forming substrate and a flavour precursor compound. Upon heating, the precursor compound releases a thiol-containing flavour compound or intermediate that enhances the flavour experience of the aerosol-forming substrate when used in a smoking article. The smoking article may include tobacco and may be configured to heat, but not combust, the tobacco.SELECTED DRAWING: 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 for heating tobacco or other nicotine sources without burning the tobacco or nicotine source. Such articles generate aerosols that can deliver nicotine and other tobacco ingredients to the user. However, the user may perceive flavor notes that are significantly different from those experienced with conventional smoking articles such as cigarettes.

  Therefore, it is desirable to incorporate flavor compounds into tobacco or other sources of nicotine used in non-combustible smoking articles to more closely approximate the experience associated with conventional cigarette smoking. 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, losses may occur during manufacture or storage due to the volatility of the compound.

  As described herein, a smoking article in which a tobacco or other source of nicotine is heated but not burned delivers a flavor-containing aerosol to the user, providing a similar experience to smoking a conventional cigarette. Provide to users. The article comprises a flavor component that includes a flavor precursor that has no significant odor. The flavor precursors upon heating convert to one or more flavor compounds or intermediates for flavor compounds to produce flavor notes that provide a composition with a profile that is closer to that of conventional cigarettes.

  The smoking articles described herein may provide one or more benefits. For example, 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 containing a thiol group or a flavor compound intermediate. Flavor compounds or intermediates containing thiols, such as hydrogen sulfide, methanethiol, and furfurylthiol, are more volatile than flavor precursor compounds. Flavor precursors are either less volatile or less volatile than flavor compounds, which can reduce manufacturing losses and extend the shelf life of the article. In addition, the flavor precursor compounds have a weaker aroma than the flavor compounds so that the article does not give a strong sulfur 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 compound" and "flavor compound" refer to a thiol-containing flavor compound released from a flavor precursor compound or resulting from the reaction of a thiol-containing intermediate with an aerosol-forming substrate. Means

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

  A thiol-containing flavor compound or intermediate is a compound that is more volatile than the flavor precursor compound. The flavor compound preferably has a flavor attribute that enhances the experience of the non-combustible smoking article, for example, providing a more similar experience to that resulting from smoking of a burning smoking article. For example, flavor compounds can enhance flavor attributes such as complexity and mouthfeel. Complexity is commonly known as the fact that no single sensory attribute is dominant and the overall flavor balance is richer. Mouth filling 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 or other flavor attributes. In embodiments, the released or generated thiol-containing flavor compound 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 they produce flavor notes that are particularly associated with cigarette smoke.

  Any suitable test may be employed to determine whether a thiol-containing flavor compound produces a generally perceptible flavor component in cigarette smoking. For example, compounds that are reminiscent of the subjective perception of flavor notes associated with cigarette smoking are considered to have or produce a flavor for the purposes of this disclosure. In embodiments, a trained flavorist determines whether a flavor compound is released or produced upon heating a flavor precursor compound, such as during smoking of a non-combustible smoking article in the presence of an aerosol-forming compound. You may. In embodiments, randomly or non-randomly selected persons may be selected to determine whether they perceive a flavor producing compound. As an example, a compound is determined to produce a flavor if 25% or more, eg 50% or more, 60% or more, 70% or more, or 80% or more of the selected individuals perceive a flavor.

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 optionally C1-C3 unsubstituted alkyl, if present,
x is an integer of 1 to 3.

R ¹ is preferably OH or a 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 positively charged sulfur species. R ⁴ is preferably absent. X is preferably 1 or 2.

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, a C1-C3 unsubstituted alkyl or amino acid residue,
x is an integer of 1 to 3.

R ¹ is preferably OH or a 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.

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

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 OH or a 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, the amino acid residue may be attached 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 compound is 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-acetyl cysteine (CAS number 616-91-1), S-methyl cysteine (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.

  The disclosure of compounds herein, whether by name, structure, reference number or the like, means the particular compound disclosed, as well as the appropriate salts, polymorphs, isomers, etc. thereof. To do.

  In embodiments, the flavor precursor compound is a compound that includes a cysteine residue. Examples of such compounds include cysteine, glutathione, N-acetyl cysteine, S-methyl cysteine, 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 comprises a flavor precursor compound, eg, a further compound commonly used in flavor components. In particular, the ingredients may include one or more flavoring compounds known in the art, including menthol, Dutch peppermint, peppermint, eucalyptus, vanilla, cocoa, chocolate, coffee, tea, spices such as cinnamon, cloves and ginger. ), Fruit extracts, and combinations thereof. In embodiments, the flavor component further comprises menthol or eugenol. Such flavorants are commonly used to provide a refreshing flavor to the smoke of smoking articles. Ingredients may also include adjuvants, which allow the ingredients to meet technical requirements such as stability and duration of tonality.

  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 capable of retaining 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 confines the flavor precursor compound within the closed structure. For example, the flavor component or precursor may be trapped within the region within the matrix structure. As the material is compressed or deformed, the flavoring ingredients or precursors are forced out of the matrix structure, for example through breakage of the surrounding structure. In embodiments, the delivery system comprises a polymeric matrix that includes one or more substrate-forming polymers. For example, gradual collapse of the polymeric matrix with compressive force, temperature, or both results in controlled release of the flavor precursor compound from the delivery system. The release of flavor precursor compounds can change as a function of temperature or deformation due to pressure or shear applied to the delivery system.

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

  In various embodiments, the flavor precursor is synthesized or purified prior to addition to the flavor component or flavor delivery component.

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

  The flavor delivery system can controllably release the flavor precursor compound into its surrounding environment by any suitable method, such as by modification of the flavor delivery system or by changes in temperature. The amount of flavor precursor compound released over time, as well as the beginning 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 compositions of the present invention include a flavor precursor compound or flavor ingredient, which ingredient or precursor is optionally provided as part of a delivery system. The smoking composition may include, for example, one or more of medicinal leaves, tobacco leaves, tobacco stems, tobacco stem debris, homogenized tobacco, reconstituted tobacco, processed tobacco, extruded tobacco and expanded tobacco. May include one or more of powders, granules, pellets, pieces, strips or sheets. The smoking composition may be in uncontained form or may be provided in a suitable container or cartridge. For example, the smoking composition may be placed in a paper or wrap and have the form of a plug.

  Smoking articles, including aerosol generators, generally include an aerosol-forming substrate that is often assembled with other components in the form of a rod. Generally, such rods are configured and sized to be inserted into an aerosol generating device that includes a heating element for heating an aerosol-forming substrate.

  As used herein, an "aerosol forming substrate" is a type of smoking composition that can be used in an aerosol generating device to produce an aerosol. The aerosol-forming substrate can release a flavor compound upon heating. The aerosol-forming substrate can be in solid or liquid form. The substrate can include both liquid and solid components. The aerosol-forming substrate may include tobacco and flavor components, where the flavor precursor compound or the separated flavor compound is released from the substrate upon heating. In embodiments, the aerosol-forming substrate does not include tobacco but does include a flavor component, and the flavor precursor compound or separated flavor compound described herein is released from the substrate upon heating and optionally from nicotine. It The aerosol-forming substrate may further include an aerosol-forming body. 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 powders, granules, pellets, fragments, 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 surface of the carrier or, in the alternative, in a pattern to provide a 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 that includes two or more connected or unconnected filter segments. Any suitable filter or filter segment may be included within the smoking articles described herein. Each of the one or more filter segments may comprise a flavor precursor compound or flavor component, with the precursor or component optionally being provided within the delivery system. The smoking article may be packaged for sale in a container (eg, in a soft pack or hinge-lid pack) with an inner liner coated or impregnated with a flavor compound, flavor component or delivery system.

  Smoking compositions comprising a flavor precursor compound or a flavor component (the precursor or component optionally being provided within the delivery system) can be manufactured using any suitable technique. For example, a flavor component including a flavor precursor compound may be sprayed onto the tobacco. Flavor precursor compounds can be added to liquid carriers to form mixtures such as solutions, suspensions, or slurries, and the slurries can be applied to tobacco to facilitate spraying. The slurry containing the flavor precursor compound can include any liquid or liquid mixture suitable for the dispersion and distribution (eg, spraying) of particles containing the flavor precursor compound. The preferred liquid is water (eg, deionized water), but other liquids such as alcohols can be used.

  In some embodiments, the tobacco may be dipped into a solution, suspension or dispersant containing the 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 smoking articles.

  In some embodiments, the flavor precursor compound may be added to the cut filler tobacco stock supplied to the cigarette making machine, or to a preformed tobacco column prior to wrapping the cigarette wrapper around the tobacco column. You may apply.

  The concentration of the flavor precursor compound in the slurry can be any amount suitable for distribution of the slurry on tobacco. Slurries containing the flavor precursor compound dispersed in a liquid may include from about 0.01 to about 2 weight percent flavor precursor compound. The flavor precursor compound is provided in the form of a dry powder and can be applied as it is to tobacco. If dry powder is used, it can be dusted on the 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. Slurries, including flavor precursor compounds, can be formed into reconstituted tobacco sheets and the sheets can be cut into pieces for incorporation as cut fillers in rods of smoking compositions or other forms of smoking articles. You can

  The homogenized tobacco can also be used to make an aerosol-forming substrate for use in smoking articles heated in an aerosol generator. The term "homogenized tobacco" as used herein means a material formed by agglomerating tobacco particles. It is also possible to mix tobacco dust from shipping and manufacturing tobacco breaks, leaf lamina, petiole and other finely chopped tobacco byproducts with a binder to agglomerate particulate tobacco. Homogenized tobacco includes aerosol forming agents, plasticizers, wetting agents, and non-tobacco fibers, excipients, water-soluble and water-insoluble solvents and combinations thereof in addition to the flavor precursors or components. Other additives including, but not limited to, may be included. The homogenized tobacco can be shaped, extruded or rolled. Numerous reconstitution processes for producing homogenized tobacco material are well known in the art. These include, for example, papermaking processes of the type described in US Pat. No. 5,724,998, for example molding processes of the type described in US Pat. No. 5,724,998, for example US Pat. No. 3,894,544. Includes, but is not limited to, types of soft-bulk reconstitution processes and extrusion processes of the type described, for example, in GB 983,928.

  Of course, the aerosol-forming substrate can have different shapes and sizes depending, for example, on the type of smoking article for which it is intended. The aerosol-forming substrate can be substantially three-dimensional. For example, the aerosol-forming substrate may be a brick or plug containing 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 containing a plurality of homogenized tobacco strands.

  The desired amount of flavor precursor compound in the smoking composition may vary depending on the final product in which the smoking composition is intended to be included. For example, a flavor precursor compound may be added to the tobacco to enhance the flavor or aroma of conventional smoking articles such as cigarettes, cigars and the like. Since such articles already produce a similar flavor or aroma upon smoking, a relatively low concentration or amount of flavor precursor compound that releases a flavor compound with a similar flavor quality may be added. In contrast, higher concentrations or higher amounts of flavor precursor compounds are used in smoking compositions such as tobacco-containing aerosol-forming substrates to be used in smoking articles where the components are aerosolized without combustion. It may be desirable to add. Smoking articles having a tobacco-containing aerosol-forming substrate for use with an aerosol generator generally provide flavor characteristics that differ from those of combustion-type smoking articles. It may also be desirable to include higher concentrations or higher amounts of flavoring compounds in tobacco-free smoking compositions, such as non-tobacco-containing aerosol-forming substrates. It is preferred that smoking compositions for use in smoking articles include a flavor precursor compound in an amount that provides the user with a perceived note that is similar to burning smoking articles such as cigarettes. For example, a flavor precursor may be included in a non-combustible smoking article or smoking article that does not include a tobacco 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. Good.

  In embodiments, the amount of flavor compound delivered to the user may be determined per puff. Any suitable method may be used to determine the amount of flavor compound delivered per puff. For example, ISO, Health Canada Intense Act, or other standard or automated procedure may be employed or modified to determine puff content. Examples of ISO methods that may be adopted 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 Nicotine in smoke-smoke condensate Determination-Gas Chromatography (1991-08-01), and (IV) ISO 10362-1: 1991 Cigarettes-Determination of Water in Smoke Condensates-Part 1: Gas Chromatography (1991-09-15), etc. Is included. Health Canada Intense Act refers to Health Canada-Official Method T-115, determination of "tar", nicotine and carbon monoxide in mainstream tobacco smoke (December 1999). Regardless of the method employed, the amount of flavor compound delivered per puff of conventional cigarettes is determined to deliver a similar amount of flavor compound per puff, and tobacco or smoke without combustion It may be desirable to formulate a non-conventional smoking article that aerosolizes other ingredients. The amount of flavor precursor compound added to the smoking composition for such articles can vary, and one may wonder how much flavor precursor is needed to deliver a similar amount of flavor compound. It may be tested to determine.

  Of course, the desired amount of flavor compound delivered per puff will depend on the flavor compound itself. In embodiments, the smoking article is configured to deliver about 5 nanograms or more of the flavor compound per puff. In an embodiment, the smoking article has from about 10 nanograms of flavor compound per puff to 1 milligram of flavor compound per puff, such as about 50 nanograms per puff to about 750 nanograms per puff, or one puff. Configured to deliver from about 75 nanograms per minute to about 500 nanograms per puff.

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

  Of course, the flavor precursor may be added to the smoking composition in any suitable amount or concentration. In embodiments, the smoking composition comprises 0.001% by weight or more of the flavor precursor compound, based on the total weight of the cigarette. In embodiments, the smoking composition comprises 0.005% by weight or more of a flavor precursor compound. In embodiments, the smoking composition comprises 0.01 wt% or less of the flavor precursor compound. In embodiments, the smoking composition has 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%. % To about 0.25% by weight flavor precursor compound.

  The flavor precursor compound may be added to the tobacco at any suitable time, such as before or during tobacco treatment, for incorporation into smoking articles or the like. The flavor precursor compound is preferably stable under these treatments (ie, no flavor compound is released or produced).

  In an embodiment, one or more flavor precursor compounds are dissolved in a food grade 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 at room temperature and humidity of approximately 60% for at least 48 hours. For application during substrate formation (eg, cast leaf process, extrusion), the compound can be added directly as a solid material to any available food grade solvent system required by the process. If application as a solid is not feasible, the compound can be applied as a solution, suspension, etc., formed as described above. Concentrations on the substrate during production can reach 1% of the total dry weight percent.

  In embodiments, tobacco reconstitution is performed by drying and shaping a homogenous slurry of tobacco powder, water, glycerin, binder and cellulose fibers. This type of process is known as the cast leaf process and is widely used by the tobacco industry to produce reconstituted or homogenized tobacco for conventional cigarette applications. The cast leaf process may involve application of temperatures up to about 140 ° C, such as about 90 ° C to about 140 ° C. Therefore, when a smoking composition comprising 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 conditions of normal use of the article in which the flavor precursor compound is incorporated. As an example, smoking articles that heat tobacco without burning it to aerosolize tobacco components generally heat the tobacco to about 200 ° C to about 450 ° C. Thus, the flavor precursor compound preferably releases the flavor compound at a temperature of from about 200 ° C. to about 450 ° C. when a smoking composition containing the flavor precursor compound is included in such an article. As another example, tobacco combustion generally occurs at temperatures of about 450 ° C. Thus, the flavor precursor compound preferably releases the flavor compound at a temperature below about 450 ° C. when the tobacco component containing the flavor precursor compound is included in a combustible smoking article, such as a cigarette or cigar.

  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 flammable smoking articles or non-combustible smoking articles in which an aerosol-forming substrate is used. The tobacco component may be tobacco types of varying origin, as well as reconstituted tobacco containing binders and wetting agents. Wetting agents accelerate the formation of aerosols. 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 may comprise any portion of the smoking article having a tobacco substrate (eg, with a conventional cigarette tobacco rod) or a conventional cigarette filter. Can be used in one or more segments of In the case of smoking articles where the smoking composition, or components thereof, is not burned, the smoking composition may be used in any part of the smoking article that has an aerosol-forming substrate.

FIG. 1 is a schematic diagram of a smoking article in which the smoking composition is not burned. FIG. 2 is a schematic diagram of a smoking article heated by an electrical heat source when engaged with a consumer device.

  By way of 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 an adjacent and coaxially arranged flammable heat source 104, an aerosol-forming substrate 106, an elongated expansion chamber 108, and a mouthpiece 110, which are low air permeable cigarette paper. Wrapped in outer wrapper 112.

  Combustion heat source 104 is a pyrolyzed porous carbon-based heat source. The combustible heat source 104 is cylindrical and comprises a central airflow channel 116 extending longitudinally through the combustible heat source 104. A substantially impervious 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 combustible heat source 104 and comprises a flavor precursor compound and glycerin as an aerosol former, and comprises a cylindrical plug of homogenized tobacco material 118 surrounded by a filter plug wrap 120. Prepare The homogenized tobacco material 118 is composed of filaments of extruded tobacco material that are longitudinally aligned.

  A thermally conductive element 122, which comprises a tube of aluminum foil, surrounds and contacts the rear portion of the flammable 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.

  An elongated expansion chamber 108 is located downstream of the aerosol-generating substrate 106 and comprises an open-ended tube of cylindrical cardboard 124. The mouthpiece 110 of the smoking article 102 comprises 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 may be surrounded by tipping paper (not shown). The dimensions of the smoking article 102 can be similar to conventional cigarettes.

  In use, the user ignites the combustible carbon-based heat source 4 and then draws air through the central airflow channel 116 downstream toward the mouthpiece 110. 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 convection heats the aerosol-forming substrate 106. 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 expansion chamber 108, cool and condense, forming an aerosol that enters the user's mouth through the mouthpiece (at about ambient temperature).

  To manufacture the smoking article 102, the rectangular pieces of the heat conductive element 122 are adhered 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 positioned on the cigarette paper 112 with the attached thermally conductive element 122. The cigarette paper 112 and the attached thermally 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. 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, the smoking composition comprising the flavor precursor compound is in direct contact with a non-combustion heat source, such as an electrical heat source. FIG. 2 shows a smoking article heated by an electrical heat source when engaged with a consumer device. The smoking article 101 comprises a front plug 103, an aerosol-forming substrate 111, a hollow cellulose acetate tube 109, a transfer section 107, and a mouthpiece filter 105. These five elements are sequentially arranged in a coaxial arrangement and assembled by a cigarette paper 115 to form a rod. The rod has a mouth end and the user inserts it into the mouth during use, with the distal end 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 tobacco wrapped in filter paper. Cast leaf tobacco includes an additive that includes glycerin as an aerosol former. The tube 109 is located immediately downstream of the aerosol forming substrate 111 and is made of cellulose acetate. The transfer section 107 allows volatile substances, including flavor compounds, to be released from the aerosol-forming substrate 111 and pass along the rod towards the mouth-side end. It is also possible to cool the volatile substances in the transfer section 107 to form an aerosol. Mouthpiece filter 105 is a conventional mouthpiece filter formed from cellulose acetate tow. The elements identified above are assembled by being tightly wrapped in a cigarette paper 115.

  The aerosol generator 119 comprises an outer barrel 121 for receiving the smoking article 101 for consumption. The heating element 113 is located inside the outer cylinder 121 and is arranged so as to mesh with the distal end of the smoking article 101. The heating element 113 is molded 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 first meshes with the front plug 103, and then penetrates into the aerosol forming substrate 111. When the smoking article 101 properly engages the aerosol generating device 119, the heating element 113 is located within the aerosol forming substrate 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 contacts the front plug 103 and may protect it from burning or melting. Of course, the smoking articles described in connection with FIGS. 1 and 2 are only two examples of smoking articles that may employ smoking compositions that include the flavor precursor compounds described herein. Furthermore, it should be understood that methods other than those described in connection with FIGS. 1 and 2 may be employed to make smoking articles having smoking compositions that include a flavor precursor compound.

  Any suitable method for making a smoking article having a smoking composition that includes a flavor precursor compound may be employed. Generally, a method for making a smoking article having a smoking composition that includes a flavor precursor compound includes adding or incorporating a flavor precursor compound or a flavor delivery composition to a smoking composition, such as a tobacco or other substrate. And a step of incorporating the smoking composition into a smoking article.

  Generally, and as described herein, a method for enhancing the flavor of a smoking composition adds a flavor precursor compound, optionally encapsulated within a delivery system, to the smoking composition. Including steps. The flavor precursor compound releases or separates the flavor compound or intermediate upon heating. As used herein, "release" and "separation" are used interchangeably. The heating of the flavor precursor compound occurs when the smoking article is used by the smoker (when burning or heating).

  As used herein, all scientific and technical terms have the meaning commonly used in the art unless otherwise specified. The definitions provided herein are provided to facilitate understanding of certain terms frequently used herein.

  As used in this specification and the appended claims, the singular forms ("a" and "an") imply an embodiment having the subject matter of the plural, unless expressly stated otherwise. If not, that is not the case.

  The term "or", when used in the present specification or the appended claims, is generally used in its sense including "and / or" unless the content clearly dictates otherwise.

  The terms “having”, “including”, “comprising”, and the like, as used herein are used in their open meaning, and generally mean “including but not limited to”. It is understood that "substantially composed", "consisting of" and like expressions are subsumed in "including" and like expressions.

  The following are non-limiting examples illustrating certain aspects of the compounds, ingredients, processes and articles described in this disclosure.

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

  Also, compounds are added to non-combustible smoking articles to assess the change in sensory attributes of the compound during aerosolization of the article in the presence or absence of the compound.

  Also, certain non-volatile sulfur compounds are applied to mixed tobacco by syringe injection and used in non-combustible smoking substrates. Tobacco with non-volatile sulfur compounds is formed into rods and equilibrated for at least 12 hours before evaluation.

Using the push-method smoke simulator, the orthonasal effect of selected compounds is evaluated at different concentrations for 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 validation.

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

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

The results showed that there were two main types of compounds, the first mainly generating hydrogen sulfide (H ₂ S) and the second mainly generating methanethiol (MSH). Is. The exception was egg albumin, whose occurrences appear to be similar.

These candidate tubes, which primarily generate H ₂ S, were orthonally evaluated 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 aroma, indicating the presence of methional as a by-product.

Orthonasal and smoking assessments of selected non-volatile sulfur compounds are performed using the push-method smoke simulator. We tested the following prototypes:

  The test was conducted as follows. The smoking system belongs to the Canadian Health Service. The smoke simulator power setting is 54W. A smoking evaluation was conducted for each concept indicating the preference in the orthonasal evaluation. A smoking rating was performed by comparing the untreated mixture with the treated concept.

Only cysteine and glutathione were selected for submission to the sensory panel in the expert panel. 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-combustible products and addressed issues such as off-note, complexity and mouthfeel. In particular, the addition of the thiol-containing precursors cysteine and glutathione contribute positively by adding smoky, fullness, 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 prototyping of the prototype by increasing the smoky and dark attributes, reducing off-notes of non-combustible products, and increasing mouth and throat sensations such as bitterness and fullness. It was shown that it had a positive effect on various perceptions.

Claims (19)

A smoking article,
An aerosol-forming substrate,
A heating element configured to heat the aerosol-forming substrate but not burn it;
A flavor precursor compound added to the aerosol-forming substrate, wherein the flavor precursor compound releases a thiol-containing flavor compound with heating of the aerosol-forming substrate by the heating element. .   The smoking article of claim 1, wherein the thiol-containing flavor compound is hydrogen sulfide or methanethiol. The smoking article of claim 1 or 2, wherein the flavor precursor compound has the 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 optionally C1-C3 unsubstituted alkyl, if present,
x is an integer of 1 to 3. R ¹ is an OH or glycine residue, R ² is H, C (O) CH ₃ , or a glutamic acid residue, R ³ is H or CH ₃ , R ⁴ is absent, and x is 1 or 2. Item 3. The smoking article according to item 3. The smoking article of claim 1 or 2, wherein the flavor precursor compound has the 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, a 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 a glycine residue, R ² is H, C (O) CH ₃ , or a glutamic acid residue, R ³ is H or CH ₃ , and x is 1 or 2. . The smoking article of claim 1 or 2, wherein the flavor precursor compound has the 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 of claim 1 or 2, wherein the flavor precursor compound has the 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 an OH or glycine residue, and R ² is H, C (O) CH ₃ , or a glutamic acid residue.   The smoking article of claim 1 or 2, wherein the flavor precursor compound comprises a cysteine residue.   12. The smoking article of claim 11, wherein the flavor precursor compound is selected from the group consisting of cysteine, glutathione, N-acetyl cysteine, S-methyl cysteine, and cystine.   The flavor precursor compound is cysteine, cystine, glutathione, methionine, DL methionine methylsulfonium, N-acetyl cysteine, S-methyl cysteine, DL-homocysteine, N-acetyl methionine, farnesyl-Met-Ome, albumin and 2-. A smoking article according to claim 1 or 2, selected from the group consisting of hydroxy-4- (methylthio) butyric acid.   14. The smoking article of claim 13, wherein the flavor precursor compound is cysteine or glutathione.   The smoking article of claim 1 or 2, wherein the flavor precursor compound is cysteine.   16. The smoking article of any of claims 1-15, wherein the aerosol-forming substrate comprises tobacco.   17. The smoking article of claim 16, wherein the furfuryl thiol is produced as a result of heating the tobacco and the flavor precursor compound.   18. The smoking article of any of claims 1-17, wherein the flavor precursor compound is configured to release hydrogen sulfide or methanethiol at a temperature of about 200 <0> C to about 450 <0> C.   19. The smoking article of any of claims 1-18, further comprising nicotine or a nicotine source.