UA117836C2 - Smoking composition comprising flavour precursor - Google Patents

Abstract

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.

Description

The present disclosure relates to smoking compositions with enhanced sensory components, as well as articles and methods relating to such smoking compositions.

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

Accordingly, it may be desirable to include flavoring compounds in tobacco or other nicotine sources used in non-combustible smoking products to more closely approximate the sensation associated with smoking a conventional cigarette. A variety of flavoring compounds are known for addition to tobacco products. However, the volatility of such compounds presents a problem when incorporating the compounds into tobacco or smoking products.

For example, losses may occur during production or storage due to the volatility of compounds.

As used herein, smoking products in which the tobacco or other nicotine source is heated, but not burned, deliver an aerosol that contains a flavoring agent to the user to provide the user with a sensation similar to that of smoking a regular cigarette. The products contain a flavoring composition, which includes a flavoring substance precursor that does not have a pronounced smell. The flavoring precursor is converted to one or more flavoring compounds or flavoring intermediates upon heating to produce flavoring notes that provide a composition with a profile that more closely resembles that of conventional cigarettes.

The smoking products described herein provide one or more advantages.

For example, the smoking products described herein provide an improved flavoring experience compared to smoking products that do not contain a flavoring precursor. When heated, the flavoring precursors described herein release flavoring compounds or flavoring intermediates that contain a thiol group. Thiol-containing aromatic compounds or

Intermediates such as hydrogen sulfide, methanethiol, and furfurylthiol are more volatile than the precursor aromatic compounds. Since flavoring precursors are non-volatile or less volatile than flavoring compounds, manufacturing losses can be reduced and products can have a longer shelf life. In addition, because the flavoring precursor compounds are less odorous than the flavoring compounds, the product does not give off noticeable sulfur notes when not in use.

As used herein, "thiol" means a compound of the formula KZN, where K is H or an organic group.

As used herein, "thiol-containing flavoring compound" and "flavoring compound" mean a thiol-containing flavoring compound that is released from a precursor flavoring compound or that is formed by the reaction of a thiol-containing intermediate with an aerosol-forming substrate.

As used herein, "thiol-containing intermediate" and "intermediate" refer to any thiol-containing compound that is released from a precursor flavoring compound and that can react with an aerosol-forming substrate, such as tobacco or another nicotine source, to formation of a thiol-containing aromatic compound.

A thiol-containing flavoring compound or intermediate is a compound that is more volatile than the precursor flavoring compound. Preferably, the flavoring compound has flavoring properties that enhance the sensation of non-combustible smoking products to provide, for example, a sensation more similar to that obtained from smoking a combustible smoking product. For example, a flavoring compound can improve flavoring properties such as richness and mouthfeel.

Multifacetedness in the general sense is known as the overall balance of the aroma, being more "rich" without the dominance of individual sensory features. The degree of mouth filling is described as the perception of the thickness and volume of smoke in the mouth and throat. The released or formed thiol-containing flavoring compounds may provide one or more of these or other flavoring properties. In embodiments, the released or formed thiol-containing flavoring 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 for their creation of flavoring notes, particularly those associated with

Gs10) with tobacco smoke.

Any suitable test can be used to determine whether a thiol-containing flavoring compound can form the flavoring component typically experienced in cigarette smoking. For example, a compound that initiates the subjective perception of a flavoring note associated with cigarette smoking will be considered to have or constitute a flavoring for the purposes of this disclosure. In embodiments, skilled flavor tasters can determine whether a flavoring compound is released or formed by heating a precursor flavoring compound, such as in the presence of an aerosol-forming compound, during the smoking process of a non-combustible smoking product. In embodiments, individuals may be selected randomly or non-randomly to determine their ability to perceive a compound to form a flavoring substance. As an example, if 25 95 or more, such as 50 95 or more, 60 95 or more, 70 95 or more, or 80 95 or more of the selected people perceive the flavoring substance, the compound is defined as producing the flavoring substance.

Any suitable sulfur-containing aromatic precursor compound can be used to release the thiol-containing aromatic compound or intermediate. In embodiments, the aromatization precursor compound has the structure of formula I as shown below:

NM

IS! (zn) x

Z ud Me v v (), where:

B' is OH or an amino acid residue,

IN? is H, C(O)CH3 or an amino acid residue,

BZ is H or unsubstituted C1-C3-alkyl,

B" is optional and, if present, is unsubstituted C1-C3-alkyl, and x is an integer from 1 to 3.

B' is preferably OH or a glycine residue. K? is preferably H, C(O)CH3 or a glutamate residue. KZ is preferably H or CH3. ФВ", if present, is mainly CH3 for the formation of positively charged sulfur particles. Mostly EK" is absent.

X is preferably equal to 1 or 2.

In embodiments, the flavoring precursor compound has the structure of formula I,

From the following: i

NM

IS!

Her" Them

In (1), where:

AW! is OH or an amino acid residue,

B2 is H, C(O)CH3 or an amino acid residue,

BZ is H, unsubstituted C1-C3 alkyl, or an amino acid residue, and x is an integer from 1 to 3.

B' is preferably OH or a glycine residue. K- is preferably H, C(O)CH3 or a glutamate residue. KZ is preferably H, CH3 or a cysteine residue. X is preferably equal to 1 or 2.

In embodiments, the flavoring precursor compound has the structure of formula I, shown below: i

NM

Ge

І" They know (1), where:

AW! is OH or an amino acid residue,

B2 is H, C(O)CH3 or an amino acid residue, and x is an integer from 1 to 3.

B' is preferably OH or a glycine residue. K2 is preferably H, C(O)CH3 or a glutamate residue. X is preferably equal to 1 or 2.

In embodiments, the flavor precursor compound has the structure of formula IM shown below: its

NM in! zn (M), where:

B' represents OH or an amino acid residue, and

IN? is H, C(O)CH3 or an amino acid residue.

B" preferably represents OH or a glycine residue. K? preferably represents H, C(O)CH3 or a glutamate residue.

It will be understood that, with respect to the formulas I-IM presented above, the amino acid residue can be linked to the core structure by a peptide bond or by a suitable side chain, such as a carboxylic acid group.

In embodiments, the flavor precursor compound is a compound selected from the group consisting of cysteine (Me according to CA5 3374-33-9), cysteine (Mo according to CA5 56-89-3), glutathione (Me according to SAB 70-18-8), methionine (Me according to SAB 59-51-8), 0I-methionine methylsulfonium (Me according to SAZ 582174), M-acetylcysteine (Mo according to SAB 616-91-1), 5-methylcysteine (Me according to SAB 1187-84-4), OI -homocysteine (Mo according to SAB 454-29-5). M-

From acetylmethionine (Me according to CA5 65-82-7), farnesyl-Mei-OMe (Mo according to SAB 218962-72-2), albumin (Mo according to SAZ 9006-59-1) and 2-hydroxy-4- (methylthio)butyric acid (Mo according to

CA5 922-50-9).

The disclosure of a compound herein either by name, structure, registration number, or similar characteristics refers to the specific disclosed compound, as well as to its suitable salts, polymorphs, isomers, etc.

In embodiments, the flavor precursor compound is a compound that contains a cysteine residue. Examples of such compounds include cysteine, glutathione, M-acetylcysteine, 5-methylcysteine, and cysteine.

Preferably, the flavoring precursor compound is cysteine or glutathione. More preferably, the aromatic precursor compound is cysteine.

For example, a flavoring composition as used herein is a composition that contains a flavoring precursor compound and an additional compound typically used in flavoring compositions. In particular, the composition may contain one or more flavoring compounds known in the art, including but not limited to menthol, peppermint, peppermint, eucalyptus, vanilla, cocoa, chocolate, coffee, tea, spices (such as cinnamon, clove and ginger), fruit extracts and their combinations. In embodiments, the flavoring composition additionally contains menthol or eugenol. Such flavoring agents are widely used to provide a refreshing flavoring agent for the smoke of a smoking product. The composition may also contain auxiliaries that ensure compliance of the composition with technical requirements, such as stability or constancy of tonality.

A delivery system that encapsulates the flavoring composition or flavoring precursor compound may be provided. The delivery system protects the flavor composition or flavor precursor compound during manufacture and storage.

In embodiments, the delivery system may take any suitable form that is capable of retaining the flavoring composition or flavoring precursor compound within the structure of the system until release is required.

Preferably, the delivery system comprises a closed matrix or mesh structure that holds the aroma precursor compound within the closed structure. For example, the flavoring composition or precursor can be contained in areas within the matrix structure. When the material is compressed or deformed, the flavoring composition or precursor is squeezed out of the matrix structure, for example, through a break in the structure surrounding it. In embodiments, the delivery system comprises a polymer matrix that contains one or more matrix-forming polymers. For example, the gradual destruction of the polymer matrix with increasing compression force, temperature, or both, provides a controlled release of the flavoring precursor compound from the delivery system.

The release of the flavoring precursor compound can thus vary depending on the temperature or deformation resulting from the compressive or shear force applied to the delivery system.

The delivery system may preferably be provided within the smoking article in a plurality of different forms, such that there is variability in the manner in which the composition or precursor may be introduced into the smoking article. In embodiments, the delivery system is provided in the form of particles, droplets, or capsules. The particles, droplets or capsules may take any suitable shape, but are preferably actually cylindrical or spherical.

In various embodiments, the flavoring precursor is synthesized or purified prior to its addition to the flavoring or flavoring delivery composition.

The flavor precursor compound described above may be incorporated into the smoking composition in any suitable manner and in any suitable amount. The term "smoking composition" is used to describe a composition that, when heated, produces an aerosol and is used to make a smoking product. The term "smoking product" also includes products that heat the smoking composition directly or indirectly, or smoking products in which the smoking composition is not burned or heated, but uses air flow or a chemical reaction to deliver nicotine, flavoring compounds, or other materials from tobacco or other sources of nicotine. As used herein, the term "smoke" is used to describe the aerosol produced by a smoking product. Aerosol produced by a smoking product can be produced, for example, by non-combustible smoking products such as heated smoking products or non-heated smoking products.

The flavoring delivery system can release the flavoring compound (precursor) into the environment in a controlled manner by any suitable means, for example by deforming the flavoring delivery system or by changing the temperature. The amount of flavoring precursor compound released over a period of time can be controlled , and the beginning or end of the interval(s).The amount of flavor precursor compound released during each interval and the duration of the time intervals need not be equal.

The smoking composition of the present invention comprises a flavoring precursor compound or flavoring composition, wherein the composition or precursor is optionally provided as part of a delivery system. The smoking composition may contain, 60 for example, one or more of a powder, granules, pellets, pieces, strips, or layers that contain one or more of a herbaceous plant leaf, tobacco leaf, tobacco stems, tobacco vein fragments, homogenized tobacco, reconstituted tobacco, processed tobacco, extruded tobacco and expanded tobacco. The smoking composition may be in loose form or may be provided in a suitable container or cartridge. For example, the smoking composition may be contained in paper or wrapping and be in the form of a rod.

Smoking products that include aerosol generating devices typically contain an aerosol generating substrate that is assembled, often with other components, in the form of a rod. As a rule, such a rod is made in a shape and size that provides for insertion into an aerosol generating device containing a heating element for heating the aerosol generating substrate. An "aerosol generating substrate" as used herein 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 the flavoring compound when heated. The substrate that forms the aerosol can be in solid form or in liquid form. The substrate that forms the aerosol can contain both liquid and solid components. The substrate that forms the aerosol may contain tobacco and a flavoring composition where the flavoring precursor compound or dissociated flavoring compound is released from the substrate upon heating. In embodiments, the substrate that forms the aerosol does not contain tobacco, but contains a flavoring composition where a flavoring precursor compound described herein or a dissociated flavoring compound is released from the substrate upon heating, and optionally nicotine.

The aerosol-forming substrate may additionally contain an aerosol-forming substance.

Examples of suitable substances for aerosol formation are glycerol and propylene glycol.

Optionally, the aerosol-forming substrate may be provided on or included in the carrier, which may take the form of powder, granules, pellets, pieces, spaghetti, strips, or layers. The substrate that forms the aerosol can be applied to the surface of the carrier in the form of, for example, a layer, a foam, a gel or a suspension. The aerosol-forming substrate may be applied to the entire surface of the support or, alternatively, may be applied in a pattern to provide non-uniform delivery of the flavoring agent during

From use.

Smoking products can contain a filter, which can be a single-segment filter or a multi-component filter that contains two or more connected or unconnected filter segments. Any suitable filter or filter segment may be incorporated into the smoking product described herein. Each of the one or more segments of the filter may contain a flavoring compound-precursor or a flavoring composition, while the precursor or composition is not necessarily provided in the delivery system. The smoking products may be packaged in a container for sale, for example, in soft packs or packs with a hinged lid, with an inner layer lining, coated or saturated with a flavoring compound, flavoring composition or delivery system.

A composition for smoking that contains a flavoring compound-precursor or flavoring composition, and the precursor or composition is not necessarily provided in the delivery system, can be made using any suitable technique.

For example, a flavoring composition that contains a flavoring precursor compound can be applied to the tobacco by spraying. To facilitate spraying, the flavoring precursor compound can be added to a liquid carrier to form a mixture such as a solution, suspension or suspension, and the suspension can be applied to the tobacco. Slurries that contain a flavoring precursor compound may include any liquid or liquid mixture suitable for distributing and dispensing (eg, spraying) particles that contain a flavoring precursor compound. The preferred liquid is water (eg, deionized water), although other liquids such as alcohols can be used.

In some embodiments, the tobacco may be immersed in a solution, suspension, or dispersion that contains a flavoring precursor. A solid, such as a powder or crystals, that contains a flavoring precursor can be added to the tobacco. The smoking composition can then be processed for use in a smoking product.

In some embodiments, the flavoring compound (precursor) can be added to the raw cut tobacco filler fed to the cigarette machine, or applied to a preformed column of tobacco prior to wrapping the cigarette wrapper around the column of tobacco.

The concentration of the flavoring compound-precursor in the suspension can be any amount suitable for distributing the suspension over the tobacco. Slurries that contain a dispersion of flavor precursor compound in liquid may contain from about 0.01 to about 2 95 by weight of flavor precursor compound. The precursor flavoring compound can be presented in the form of a dry powder and applied to the tobacco as such.

If dry powder is used, it can be sprinkled on the tobacco. Another technique for incorporating a flavoring precursor compound into a smoking tobacco composition involves adding the flavoring precursor compound to a suspension of ingredients useful in the manufacture of reconstituted tobacco. The slurry comprising the precursor flavoring compound may be formed as a layer of reconstituted tobacco, and the layer may be cut into pieces for inclusion as a cut filler in a smoking composition rod or other forms of smoking article.

Homogenized tobacco can also be used to make an aerosol generating substrate for use in smoking products that can be heated in an aerosol generating device. In this context, the term "homogenized tobacco" means a material formed by agglomeration of tobacco in the form of particles. Tobacco dust generated by grinding tobacco during transportation and manufacturing, leaf blade, stalks and other tobacco waste that is very finely ground can be mixed with a binder to agglomerate the tobacco in the form of particles. Homogenized tobacco may contain other additives in addition to the flavoring precursor or flavoring composition, including without limitation aerosolizing agents, plasticizers, hygroscopic substances and non-tobacco fibers, fillers, aqueous and nonaqueous solvents, and combinations thereof.

Homogenized tobacco can be molded, extruded or rolled. Several recovery methods are known from the prior art for the production of homogenized tobacco materials. They include, without limitation, methods of paper production belonging to the type described, for example, in OZ 5724998; casting methods of the type described, for example, in 05 5724998; methods of restoring the pasty mass, belonging to the type described, for example, in 5 3894544; and extrusion methods of the type described, for example, in OV 983928.

It will be understood that the aerosol-forming substrates may have different shapes and sizes depending, for example, on the type of smoking product in which they are intended to be used.

The substrate that forms the aerosol can be essentially three-dimensional. For example, the substrate that forms the aerosol can be blocks or rods that contain many bundles of homogenized tobacco material. Alternatively, the aerosol-generating substrates may be essentially two-dimensional. For example, aerosol-generating substrates may be layers or layers that contain many bundles of homogenized tobacco.

The amount of precursor flavor compound required in the smoking composition may vary depending on the end product into which the composition is to be incorporated. For example, a flavoring precursor compound can be added to tobacco to enhance the flavoring or flavor of conventional smoking products such as cigarettes, cigars, and the like. As such, the products may already produce a similar flavoring substance or flavor when smoked, while flavoring precursor compounds that release flavoring compounds with similar flavoring properties may be added at relatively low concentrations or amounts. In contrast, it may be desirable to add higher concentrations or amounts of flavoring precursor compounds to smoking compositions, such as tobacco-containing aerosol-forming substrates to be used in smoking products in which the components are in the form of a non-burning aerosol. Smoking products with tobacco-containing aerosol-forming substrates for use in an aerosol-generating device generally provide flavoring characteristics that differ from those of combustible smoking products. It may also be desirable to include higher concentrations or amounts of flavoring compounds in non-tobacco smoking compositions, such as non-tobacco aerosol forming substrates. Preferably, the flavor precursor compounds are included in smoking compositions for use in smoking products in amounts that provide a user perception of a note similar to that of a combustible smoking product such as a cigarette.

For example, a flavoring precursor can be incorporated into a non-combustible smoking product or a smoking product that does not include tobacco in an amount that results in the release or delivery of the flavoring compound in a concentration or amount similar to that delivered to the user of a conventional smoking product such as a cigarette .

In embodiments, the amount of flavoring compound delivered to the user can be determined based on puffs. Any suitable method may be used to determine the amount of flavoring compound delivered per puff. For example, ISO (International Organization for Standardization), Health Canada Smoking Intensity, or other standard or automated procedures can be used or modified to determine puff content.

Examples of I5O methods that can be applied or modified include: (i) I5BO 4387:1991, Cigarettes - Determination of total dry matter and dry matter not containing nicotine using a conventional analytical smoking machine, 1991-10-15; (its) ISO 8454:1995, cigarettes - Determination of carbon monoxide in the vapor phase of cigarette smoke -

Method MOIIIK, 11-15-1991; (its) IBO 10315:1991, cigarettes - Determination of nicotine in smoke condensates - Gas chromatographic method, 1991-08-01; and (im) ISO 10362-1:1991, cigarettes -

Determination of water in smoke condensates - Part 1: Gas chromatographic method, 1991-09-15.

Health Canada's method of determining intensity refers to the following: Health Canada - Official Method T-115, Determination of "Tar", Nicotine and Carbon Monoxide in Inhaled Tobacco Smoke, December 1999.

Regardless of the method used, it may be desirable to determine the amount of flavoring compound delivered per puff of a conventional cigarette and to develop a non-conventional smoking product that aerosolizes the tobacco or other ingredients without burning so that it delivers similar amounts of flavoring compound per puff .

The amount of flavoring precursor compound added to the smoking composition for such products can be varied and tested to determine the amount of flavoring precursor required to deliver a similar amount of flavoring compound.

Of course, the required amount of flavoring compound delivered per puff will depend on the flavoring compound itself. In embodiments, the smoking article is designed to deliver approximately 5 nanograms or more of a flavoring compound per puff. In embodiments, the smoking article is configured to deliver from about 10 nanograms of flavoring compound per puff to 1 milligram of flavoring compound per puff, such as from about 50 nanograms per puff to about 750 nanograms per puff or from about 75 nanograms per puff up to about 500 nanograms per puff.

The amount of precursor flavor compound added to the smoking composition to deliver the required amount of dissociated flavor compound to the user will depend on the components and configuration of the products and the precursor flavor compound.

Of course, the flavor precursor can be added to the smoking composition in any suitable amount or concentration. In embodiments, the smoking composition contains 0.001 wt. 95 or more, based on the total weight of the tobacco, flavoring precursor compound. In embodiments, the smoking composition includes 0.005 wt. 96 or more flavor precursor compound. In embodiments, the smoking composition includes 0.01 wt. 95% or less of the flavor precursor compound. In embodiments, the smoking composition comprises from about 0.001 wt.95 to about 2 wt. 95 flavoring compound precursor, for example, from about 0.005 wt. 95 to about 1 wt. 96 flavoring precursor compounds or from about 0.01 wt. 95 to about 0.25 wt. 96 flavoring precursor compound.

The flavoring compound-(precursor) may be added to the tobacco at any convenient time, such as before or during the processing of the tobacco, for inclusion in a smoking product, or the like. Preferably, the flavoring precursor compound is stable (in other words, the flavoring compound does not released or not formed) during such processing.

In embodiments, one or more flavoring precursor compounds are dissolved in a food solvent and then applied to a tobacco substrate or other suitable substrate at concentrations up to 1000 ppm. The substrate can then be equilibrated at room temperature to a humidity of about 60 96 for at least 48 hours. For use in a substrate formation method (e.g. sheet forming method, extrusion) the compounds can be added directly as a solid material to any available food solvent system required for the method. In the event that application in the form of a solid substance is not possible, the compound can be used in the form of a solution, suspension, etc., formed as described above. The concentration of the substrate in the process of formation can reach 1 95 of the total dry weight.

In variants of implementation, tobacco recovery is performed by drying and forming a homogeneous suspension from tobacco powder, water, glycerin, binder and cellulose fibers. This type of process is known as a sheet forming process and is widely used in the tobacco industry to produce reconstituted or homogenized tobacco for use in a regular cigarette. The sheet forming method may include the application of temperatures up to about 140°C, for example, from about 907°C to about 140°C.

Accordingly, if a smoking composition that includes a precursor flavoring compound is to be manufactured using a sheet-forming method, the precursor flavoring compound will preferably be stable at such temperatures.

Preferably, the flavoring precursor compound releases the flavoring compound or intermediate under conditions of general use of the product incorporating the flavoring precursor compound. By way of example, in smoking products in which the tobacco is heated but not burned to aerosolize the tobacco components, the tobacco is typically heated at a temperature of from about 200°C to about 450°C. Accordingly, the flavoring precursor compound preferably releases flavoring compound at a temperature of from about 200°C to about 450°C, if a smoking composition with a precursor flavoring compound is included in such products. As another example, tobacco combustion 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 the flavor precursor compound tobacco composition is incorporated into a combustible smoking product such as a cigarette or cigar.

In embodiments, the flavoring precursor compound releases the flavoring compound at a temperature of about 150°C or greater. 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 from about 1007°C to about 450°C, such as from about 1507°C to about 450°C or from about 2007C to about 45076.

Tobacco compositions as used herein refer to smoking compositions that include tobacco and a flavoring precursor. For example, the tobacco composition can be used in combustible smoking products or non-combustible smoking products that use an aerosol-forming substrate. The tobacco composition can be reconstituted tobacco, which contains different types of tobacco of various origins, as well as binders and hygroscopic substances. Hygroscopic substances make it easier to obtain an aerosol. When heated, hygroscopic substances evaporate and re-condense into small droplets with the formation of a visible aerosol. Preferably, the flavoring precursor composition releases the flavoring compound under conditions of use, but not under conditions of storage, processing, or manufacture.

In the case of combustible smoking products, such as cigarettes, the smoking composition can be used in any part of the smoking product with a tobacco substrate, for example, in the tobacco rod of a conventional cigarette or in one or more filter segments of a conventional cigarette. In the case of smoking products in which the smoking composition or component thereof does not burn, the smoking composition may be applied to any portion of the smoking product with an aerosol-forming substrate.

By way of example and with reference to FIG. 1, a schematic representation of a smoking article 102 is shown in which the smoking composition does not burn. As shown in fig. 1, the smoking article 102 includes a combustible heat source 104, an aerosol-forming substrate 106, an elongated expansion chamber 108, and a mouthpiece 110, which are adjacent to each other in coaxial alignment, and which are wrapped on top by an outer wrapper of cigarette paper 112 with low air permeability.

Combustible heat source 104 is a pyrolyzed porous carbon-based heat source. Combustible heat source 104 is cylindrical and includes a central channel 116 for air flow that passes through heat source 104 in a longitudinal direction. A substantially airtight, heat-resistant coating 114 of iron oxide is located on the inner surface of the central channel 116 for air flow. The aerosol-forming substrate 106 is located immediately downstream of the combustible heat source 104 and includes a cylindrical insert of homogenized tobacco material 118 that contains a flavoring precursor compound and glycerol as an aerosol-forming substance and is surrounded by a filter wick 120 . Homogenized tobacco material!!8 consists of longitudinally aligned strands of extruded tobacco material.

A heat-conducting element 122 consisting of a tube of aluminum foil surrounds and is in contact with the back of the combustible heat source 104 and abuts the front of the aerosol-generating substrate 106. As shown in fig. 1, the rear 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 contains a cylindrical cardboard tube 124 with open ends.

The mouthpiece 110 of the smoking product 102 is located downstream of the expansion chamber 108 and includes a cylindrical rod of very low filtration efficiency cellulose acetate fiber tow 126 surrounded by a filter wick 128. Mouthpiece 110 may be surrounded by rim paper (not shown). The dimensions of the smoking product 102 may be similar to a conventional cigarette.

In use, the user ignites a combustible carbon-based heat source 4 and then draws air through the central channel 116 to flow air downward toward the mouthpiece 110. The front of the aerosol-generating substrate 106 is heated primarily by conduction through the non-combustible rear a portion of the adjacent combustible heat source 104 and heat conducting element 122. The entrained air is heated as it passes through the central air flow channel 116 and then heats the aerosol forming substrate 106 by convection. Heating of the aerosol-forming substrate 106 causes the release of volatile and semi-volatile compounds, including dissociated flavoring compound and glycerol from the substrate 118, which are drawn into the heated entrained air as it flows through the aerosol-forming substrate.

The heated air and inhaled compounds pass downstream through the expansion chamber 108, cool and condense to form an aerosol that passes through the mouthpiece into the user's oral cavity (at approximately ambient temperature).

To manufacture the smoking product 102, a rectangular section of the heat-conducting element 122 is glued to the cigarette paper 112. The heat source 104, the substrate rod 106, which forms the aerosol, and the expansion chamber 108 are appropriately aligned and positioned on the cigarette paper 112 with the heat-conducting element 122 attached. The cigarette paper 112 with attached thermal element 122 is wrapped around the back of heat source 104, aerosol generating substrate 106, and expansion chamber 108 and bonded. The mouthpiece 110 is attached to the open end of the expansion chamber with

With the use of known technology of connection with a filter.

In another example of a heated smoking article, the smoking composition containing the flavor precursor compound is brought into direct contact with a non-burning heat source, such as an electric heat source. In fig. 2 shows a smoking product that is heated by an electric heat source when connected to a device for use. The smoking product 101 includes a front rod 103, an aerosol forming substrate 111, an empty cellulose acetate tube 109, a transfer section 107 and a mouthpiece filter 105. These four elements are arranged in series and adjacent to each other in coaxial alignment, and are joined by cigarette paper 115 to form a core.

The rod has an oral end that the user inserts into their mouth during use and a distal end located at the opposite end of the rod relative to the oral end. In the assembled state, the length of the rod is 52 mm, and the diameter is 7.2 mm. The front rod 103 is a cylindrical part made of cellulose acetate fiber.

The substrate 111, which forms an aerosol, is located downstream of the front rod 103 and contains a bundle of corrugated molded leaf tobacco wrapped in filter paper. Molded leaf tobacco contains additives, including glycerin as an aerosol forming agent. Tube 109 is located immediately downstream of substrate 111, which forms an aerosol, and is made of cellulose acetate.

The transmission section 107 allows the volatile substances, including the flavoring compound released from the substrate 111, which forms an aerosol, to pass along the rod towards the end to be brought to the mouth. Volatile substances can be cooled in the transfer section 107 to form an aerosol. Mouthpiece filter 105 is a traditional mouthpiece filter made of cellulose acetate fiber. The elements indicated above are connected by dense wrapping with cigarette paper 115.

The aerosol generating device 19 includes a shell 121 for receiving a smoking article 101 for consumption. The heating element 113 is located in the shell 121 and is connected to the far end of the smoking product 101. The heating element 113 has the shape of a blade that ends in a point. As the smoking product 101 is pushed into the shell, the tip of the heating element 113 first connects with the front rod 103, and then penetrates the substrate 111, which forms an aerosol. When the smoking product 101 is properly connected to the device 119 that generates the aerosol, the heating element 113 is located in the substrate 111 that generates the aerosol. The heat generated by the heating element 113 is transferred by conduction and convection to the substrate 111, which forms an aerosol containing the flavor precursor compound.

The insulating ring 117 can surround the part of the heating element 113 with which it is in contact and protect the front rod 103 from ignition or melting. Of course, it should be understood that the smoking products described with respect to FIG. 1 and fig. 2, are only two examples of a smoking product in which a smoking composition containing a flavoring precursor compound described herein can be used. It should also be understood that other methods can be used to make a smoking article with a smoking composition that contains a flavoring precursor compound other than those described in connection with FIG. 1 and fig. 2.

Any suitable method of manufacturing a smoking article with a smoking composition that includes a precursor flavoring compound may be used. In general, a method of making a smoking product with a smoking composition comprising a flavoring compound (precursor) includes adding or incorporating a flavoring precursor compound or composition to deliver a flavoring substance to a smoking composition, such as tobacco or other substrate; and including a composition for smoking in a smoking product.

In general and as described herein, a method of improving the flavoring of a smoking composition involves adding a precursor flavoring compound, optionally encapsulated in a delivery system, to the smoking composition.

The flavor precursor compound releases or dissociates the flavor compound or intermediate upon heating. As used in this document, "release" and "dissociate" are used interchangeably. The heating of the flavoring compound-precursor occurs when the smoker uses the smoking product (when burning or heating).

All scientific and technical terms used in this application have the meanings commonly used in the art, unless otherwise indicated. The following definitions are intended to facilitate understanding of certain terms frequently used in this application.

The singular forms used in this description and claims include variants

From implementation with these objects in the plural, unless the content clearly indicates otherwise.

The conjunction "or" used in this description and claims is usually used in a meaning that includes "and/or", unless the context clearly indicates otherwise.

As used in this application, the terms "have", "which has", "include", "which includes", "contain", "containing" or the like are used in their broad sense and generally mean "including but not limited to ". It should be understood that the terms "consisting essentially of", "which consists of", etc. belong to the "containing" category, etc.

Non-limiting examples that illustrate certain aspects of the compounds, compositions, methods, and articles of manufacture described in this disclosure are provided below.

Examples

Example 1

A number of non-volatile sulfur compounds shown in Table 1 were screened using (ATO) 240-M5 on a cellulose filter to determine whether and how much they release hydrogen sulfide and methanethiol upon heating.

The compounds were also added to non-combustible smoking products to evaluate the change in sensory properties provided by such compounds during aerosol formation by such products in the presence and absence of these compounds.

Some of the non-volatile sulfur compounds have also been applied to blended tobacco by syringe injection and used to produce non-combustible smoking substrates. Tobacco with non-volatile sulfur compounds was formed into sticks and equilibrated for at least 12 hours before evaluation.

The orthonasal effect of the selected compounds was evaluated at different concentrations of the general aroma when using a smoke simulator in push mode. Selected compounds were then selected for sensory testing.

Table 1.

Non-volatile sulfur compounds

Mezhydnoz SAB category: 374-33-9

Shchystino/////7777777771717171717171711111111111111111111Bb-893 cells

Methionine //////777717171717171111111111111111111111111111B9-51-8

Oi--methionine methylsulfonium chloride 582174

M-acetyl-i-cysteine 616-91-1 o3-methyliii-cysteine 77777771 187-844

Oi-homocysteine 77777771 5-25 oM-acetyl-y-methioninde 77777711 BB-82-7

Farnesyl-MeiOMe 18962-72-2

Egg albumin. 77777171 B006-59-1 sulfur-rich protein

Ca-salt of 2-hydroxy-4-(methylthio)butyric acid9d22-50-9

Aqueous solutions were prepared according to Table 2. Additionally, 1:10 and 1:100 dilutions were prepared for testing.

Table 2.

Preparation of the basic solution of the tested compounds

Oi--methionine methylsulfonium chloride

M-acetyl-i--cysteine

Farnesyl-MeiOMe

Ca-salt of 2-hydroxy-4-(methylthio)butyric acid

Analyzes of ATO-S40-M5 were performed using the following set of devices.

Table 3.

Used devices ATO-S40-M5

detailed information

Reikip EITeg Tpegta! Oezogbeg Tigbo Mayigih 350

Gas chromatograph Adiyepi 7890A SS 60 m x 0.25 μm, EPAR

Mass chromatograph Adiepi 59750

Table 4.

Parameters of ATO-C40-M5 20 μl of a solution of each compound (initial, 1:10, 1:100) was injected into a pre-equilibrated Satbgidde pad, which was then inserted into a glass tube. The contents of the tubes were assessed orthonasally after thermal desorption and certain aroma notes were detected. The results are shown in Table 5.

Table 5.

Roast flavor rating with a faint sulfur, meaty roast-like note

Sa-salt 2-tihydroxy-4- new tubes (heated to 2507С) had an odor similar to cooked (methylthio)buttered potatoes with a hint of sulfur and fried acid methylsulfonium chloride

The results indicate that there are mainly two families of compounds, one that forms mainly hydrogen sulfide (H5) and the second that forms mainly methanethiol (M5H). The exception is egg albumin, for which the formation is apparently similar.

Tubes with these candidates, which produce mainly No5, were orthonasally rated after heating as having a sulphurous, fried or burnt smell. Ne5 could not be directly detected. In contrast, all compounds that form methanethiol were rated as having a potato-like aroma, indicating the presence of methional as a byproduct.

Example 2

Orthonasal assessment and smoking assessment of selected non-volatile sulfur compounds were performed using a smoke simulator in push mode. The following experimental samples were tested.

Table 6.

Test samples that tested (approach A) (approach B) (methylthio)butyric acid chloride

Testing was performed as follows. The smoking regime met the norms of the Ministry of Health of Canada. The installed power of the smoke simulator was 54 W. Assessment while smoking was performed for approaches that demonstrated superiority in orthonasal assessment. The smoking assessment was performed by comparing the untreated mixture and the treated approach

Only cysteine and glutathione were selected for consideration through sensory testing by a group of experts. Approach B was chosen for glutathione and approach B was chosen for cysteine.

Table 7.

Observations were recorded during experimental work

Cysteine I:

In sulphurous notes of cold weather, there are fewer secondary notes /-://:/С/

In sulphurous notes, there are fewer secondary notes /-://:/С/ notes

ES ZSh iy iniiy

Ca-salt of 2-hydroxy-4-| And (methylthio)butter scallion - - - there is no significant difference in the secondary notes chloride chuttlyut (A oon nia

C-methyl-i-cysteine of pepper, and meaty notes

The IWs are close to matching the heightened, hay-like green notes

The addition of sulphur-containing compounds, especially those with free thiol groups, improves the perception of the flavoring of non-flammable products and solves the problems associated with secondary notes, multifacetedness and the degree of filling of the oral cavity. In particular, the addition of thiol-containing precursors of cysteine and glutathione makes a positive contribution to the overall aroma of heated aerosols by adding smokiness, degree of mouth filling, burning, bitterness and multifacetedness.

Thus, it was demonstrated that the addition of sulfur-containing precursors has a positive effect on the overall sensory perception of the test samples by enhancing the smoke intensity features, reducing the secondary notes of the non-combustible product, and increasing mouth and throat sensations, such as bitterness and mouth fullness.

Claims (19)

FORMULA OF THE INVENTION 1. A smoking product that contains: a substrate that forms an aerosol; a heating element made with the possibility of heating, but without burning the substrate, which forms an aerosol; a flavoring precursor compound added to the aerosol-forming substrate, wherein the flavoring precursor compound releases the thiol-containing flavoring compound when the aerosol-forming substrate is heated by a heating element. 2. The smoking product according to claim 1, where the thiol-containing flavoring compound is hydrogen sulfide or methanethiol. 3. Smoking product according to claim 1 or claim 2, where the flavoring precursor compound has the following structure: ISN.IX 5 "mk: where: AB! represents OH or an amino acid residue, B2 represents H, C(O)CH3 or an amino acid residue, BZ represents H or an unsubstituted C.1-C3-alkyl, B" is a neoob and, if present, is unsubstituted C:-C3-alkyl, and x is an integer from 1 to 3. 4. The smoking product according to claim 3, where KE" is OH or a glycine residue, B? is H, C(O)CH3 or a glutamate residue, EZ is H or CH", B" is absent, and x is 1 or 2. 5. Smoking product according to claim 1 or claim 2, where the flavoring precursor compound has the following structure: its ISN.I ZK with Kai Zo where: B' represents OH or an amino acid residue, B? is H, C(O)CH3 or an amino acid residue, BZ is H, unsubstituted C1-C3 alkyl or a cysteine residue, and x is an integer from 1 to 3. 6. The smoking product according to claim 5, where K' represents OH or a glycine residue, K2 represents H, C(O)CH3 or a glutamate residue, ECZ represents H or Snu", and x is 1 or 2. 7. Smoking product according to claim 1 or claim 2, where the flavoring precursor compound has the following structure: Ш их в' ISNI, known as (I) where: В' is OH or an amino acid residue, В? is H, C(O)CH3 or an amino acid residue, and x is an integer from 1 to 3. 8. Smoking product according to claim 7, where KE! is OH or a glycine residue, KE? is H, C(O)CH:z or a glutamate residue, and x is 1 or 2. 9. Smoking product according to claim 1 or claim 2, where the flavoring precursor compound has the following structure: its sha v' where: B' is OH or an amino acid residue, and B: is H, C(O)CH3 or an amino acid residue . 10. The smoking product according to claim 9, where K' is OH or a glycine residue, and K2 is H, C(O)CH: or a glutamate residue. 11. The smoking product according to claim 1 or claim 2, where the flavoring precursor compound contains a cysteine residue. 12. The smoking product according to claim 11, wherein the flavoring precursor compound is selected from the group consisting of cysteine, glutathione, M-acetylcysteine, 5-methylcysteine and cystine. 13. The smoking product according to claim 1 or claim 2, where the flavoring precursor compound is selected from the group consisting of cysteine, cystine, glutathione, methionine, OiI-methionine methylsulfonium, M-acetylcysteine, Z-methylcysteine, Oi-homocysteine, M- acetylmethionine, farnesyl-Mei-Ote, albumin and 2-hydroxy-4-(methylthio)butyric acid. 14. The smoking product according to claim 13, where the flavoring precursor compound is cysteine or glutathione. 15. Smoking product according to claim 1 or claim 2, where the flavoring compound-precursor is Zo cysteine. 16. The smoking product according to any of the previous items, where the substrate that forms the aerosol contains tobacco. 17. The smoking product according to claim 16, wherein heating the tobacco and the flavoring precursor compound leads to the formation of furfurylthiol. 18. The smoking product of any of the preceding claims, wherein the flavoring precursor compound is capable of releasing hydrogen sulfide or methanethiol at a temperature of from about 200°C to about 450°C. 19. A smoking product according to any of the previous items, which additionally contains nicotine or a source of nicotine.