ES2645338T3 - Composition for smoking comprising a flavor precursor - Google Patents

Abstract

A smoking article (101, 102) comprising: an aerosol forming substrate (106, 111); a heating element (104, 113) configured to heat, but not combustion, the aerosol forming substrate; a flavor precursor compound added to the aerosol forming substrate, wherein the flavor precursor compound releases a thiol-containing flavoring compound after heating of the aerosol forming substrate by the heating element.

Description

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DESCRIPTION

Composition for smoking comprising a precursor of flavor

This description refers to smoking compositions having improved sensory components, and articles and methods related to such smoking compositions.

US 4,941,486 describes a cigarette comprising smoking material contained in a surrounding wrapping material. The wrapping material has intimate contact with a flavor precursor in an amount sufficient to provide the smoke aroma alteration of the sidestream of the cigarette after it is burned during use. The flavor precursor provides essentially less perceptible characteristics of the smoke aroma of the mainstream of the cigarette than the smoke of the sidestream during use. The flavor precursor essentially does not provide perceivable characteristics of cigarette aroma before use.

Smoking articles that heat tobacco or other sources of nicotine have been proposed, without the combustion of tobacco or the source of nicotine. Such items generate aerosols that can supply nicotine and other tobacco constituents to a user. However, a user can perceive significantly different flavor notes from experiences with conventional smoking articles such as cigarettes.

Consequently, it would be convenient to incorporate flavoring compounds into tobacco or other sources of nicotine that are used in non-combustible smoking articles to better approximate the experience associated with the action of smoking a conventional cigarette. A variety of flavoring compounds are known for addiction to tobacco products. However, the volatility of such compounds presents challenges for the incorporation of the compounds into tobacco or smoking articles. For example, losses may occur during production or storage due to the volatility of the compounds.

As described herein, smoking articles, in which tobacco or other nicotine source is heated but not burned, provide a user with an aerosol containing a flavor to provide the user with an experience similar to of smoking a conventional cigarette. The articles contain a flavoring composition that includes a precursor of flavor, which does not have a significant odor. The flavor precursor becomes one or more flavoring compounds or intermediate compounds for flavoring compounds after heating to produce flavor notes that provide the composition with a profile that looks more like conventional cigarettes.

The smoking articles described in the present description may provide one or more advantages. For example, the smoking articles described in the present description provide an improved flavoring experience relative to smoking articles that do not include a flavor precursor. After heating, the flavor precursors described in the present disclosure release flavoring compounds or intermediate compounds of flavoring compounds comprising a thiol group. Flavoring compounds or thiol-containing intermediates, such as hydrogen sulfide, methanethiol, and furfurylthiol, are more volatile than flavor precursor compounds. Because flavor precursors are not volatile or less volatile than the flavoring compound, losses during production can be mitigated and items can have a longer shelf life. In addition, because flavor precursor compounds have less odor than flavor compounds, the article does not impart essential sulfur notes when not in use.

As used herein, "thiol" refers to a compound of the formula RSH, where R is H or an organic group.

As used herein, "thiol-containing flavoring compound" and "flavoring compound" refer to a thiol-containing flavoring compound that is released from the flavor precursor compound or that is generated from the reaction of an intermediate compound It contains thiol with an aerosol forming substrate.

As used herein, "thiol-containing intermediate compound" and "intermediate compound" refer to any thiol-containing compound that is released from the flavor precursor compound and which can react with an aerosol-forming substrate, such as tobacco. or other sources of nicotine to generate a flavoring compound that contains thiol.

The flavoring compound containing thiol or the intermediate compound is a compound that is more volatile than the flavor precursor compound. Preferably, the flavoring compound has flavoring properties that enhance the experience of non-combustible smoking articles to, for example, provide an experience more similar to that resulting from the action of smoking a fuel-smoking article. For example, the flavoring compound may improve the flavoring properties such as complexity and fullness in the mouth. Complexity is generally known as the total balance of flavor that is richer without dominating unique sensory attributes. Fullness in the mouth is described as the perception of richness and volume of smoke in the mouth and throat. Flavoring compounds containing thiol released or generated may provide

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one or more of these or other flavoring properties. In embodiments, the flavoring compound containing released or generated thiol 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 generation of flavor notes particularly associated with tobacco smoke.

Any suitable test can be used to determine if the thiol-containing flavoring compound produces a flavoring component that is typically perceptible by the action of cigarette smoking. For example, a compound that invokes a subjective perception of a taste note, associated with the action of cigarette smoking would be considered to have or produce a flavor for the purposes of the present description. In embodiments, experts trained in flavors can determine if a flavoring compound is released or generated by heating a flavor precursor compound, such as in the presence of an aerosol forming compound during the smoking action of a non-smoking article fuel. In modalities, randomly or non-randomly selected persons may be chosen to determine whether they perceive the compound to produce a flavor. As an example, if 25% or more, for example, 50% or more, 60% or more, 70% or more, or 80% or more of the selected people perceive a taste, the compound will be determined to produce the flavoring

Any suitable sulfur-containing flavor precursor compound can be used to release a flavoring compound containing thiol or an intermediate compound. In embodiments, the flavor precursor compound has a Formula I structure, as follows:

R2 O

image 1

R1

(I),

where:

R1 is OH or an amino acid residue,

R2 is H, C (O) CH3, or an amino acid residue,

R3 is H or unsubstituted C1-C3 alkyl,

R4 is optional and, if present, is unsubstituted C1-C3 alkyl, and x is an integer from 1 to 3.

R1 is preferably OH or a glycerin residue. R2 is preferably H, C (O) CH3, or a glutamate residue. R3 is preferably H or CH3. R4 is preferably CH3, if present, to produce a positively charged sulfur species. Preferably, R4 is not present. X is preferably 1 or 2.

In embodiments, the flavor precursor compound has a Formula II structure, as follows:

R2 O

image2

R1

where:

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R1 is OH or an amino acid residue,

R2 is H, C (O) CH3, or an amino acid residue,

R3 is H, unsubstituted C1-C3 alkyl or an amino acid residue, and x is an integer from 1 to 3.

R1 is preferably OH or a glycerin residue. R2 is preferably H, C (O) CH3, or a glutamate residue. R3 is preferably H, CH3 or a cysteine residue. X is preferably 1 or 2.

In embodiments, the flavor precursor compound has a Formula III structure, as follows:

R2 O

image3

(III)

where:

R1 is OH or an amino acid residue,

R2 is H, C (O) CH3, or an amino acid residue, and x is an integer from 1 to 3.

R1 is preferably OH or a glycerin residue. R2 is preferably H, C (O) CH3 or a glutamate residue. X is preferably 1 or 2.

In embodiments, the flavor precursor compound has a Formula IV structure, as follows:

R2 O

R1

image4

where:

R1 is OH or an amino acid residue, and R is H, C (O) CH3, or an amino acid residue.

R1 is preferably OH or a glycerin residue. R2 is preferably H, C (O) CH3, or a glutamate residue.

It will be understood that, with respect to Formulas I-IV presented above, an 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 (CAS No. 3374-22-9), cystine (CAS No. 56-89-3), glutathione (CAS No. 70-18- 8), methionine (CAS No. 59-51-8), DL-methionine methylsulfonium (CAS No. 582174), N-acetyl cystephine (CAS No. 616-91-1), S-methyl cystephine (CAS No. 1187-84-4), DL-homocysteine (CAS No. 454-29-5), N-acetyl methionine (CAS No. 65-82-7), Farnesyl-Met-Ome (CAS No. 218962-72-2 ), albumin (CAS No. 9006-59-1) and 2-hydroxy-4- (methylthio) butyric acid (CAS No. 922-50-9).

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The description of a compound of the present description, whether by name, structure, reference number or the like, refers to the particular compound described, as well as suitable salts, polymorphs, isomers, etc. of the same.

In embodiments, the flavor precursor compound is a compound comprising a cystem residue. Examples of such compounds include cystem, glutathione, N-acetyl cystem, S-methyl cystem, and cystine.

Preferably, the flavor precursor compound is cystem or glutathione. More preferably, the flavor precursor compound is cystem.

As used herein, a flavoring composition is a composition comprising a flavor precursor compound and an additional compound typically used in flavoring compositions, for example. In particular, the composition may comprise one or more flavoring compounds known in the art, including but not limited to, menthol, spearmint, mint, eucalyptus, vanilla, cocoa, chocolate, coffee, tea, spices (such as cinnamon, clove and ginger), fruit extracts, and combinations thereof. In embodiments, the flavoring composition further comprises menthol or eugenol. Such flavorings are commonly used to provide a refreshing taste to the smoke of a smoking article. The composition may also comprise adjuvants that allow the composition to meet technical requirements, such as stability or persistence of hue.

A delivery system can be provided, which encapsulates a flavoring composition or flavor precursor compound. The delivery system protects the flavoring composition or precursor flavor compound during manufacturing and storage.

In embodiments, a delivery system can take any suitable form that is capable of retaining the flavor composition or flavor precursor compound within the structure of the system until the release is convenient.

Preferably, the delivery system comprises a closed network or matrix structure, which traps the flavor precursor compound within the closed structure. For example, the flavoring or precursor composition can be trapped in the domains within a matrix structure. After compression or deformation of the material, the flavoring or precursor composition is forced out of the matrix structure, for example, through breaks in the surrounding structure. In embodiments, the delivery system comprises a polymer matrix comprising one or more matrix forming polymers. For example, the gradual rupture of the polymer matrix with temperature, increasing compressive force, or both provides controlled release of the precursor compound from the flavor of the delivery system. The release of the flavor precursor compound may therefore vary as a function of the temperature or deformation that results from the compressive or shear force that is applied to the delivery system.

The delivery system can be advantageously provided within the smoking articles in a variety of different ways so that there is flexibility in the manner in which the composition or precursor can be incorporated into the smoking article. In modalities the delivery system is provided in the form of particles, beads or capsules. The particles, beads or capsules can be formed in any suitable form, but preferably they are essentially cylindrical or spherical.

In several embodiments, the flavor precursor is synthesized or purified before its addition to the flavoring composition or flavor delivery composition.

A flavor precursor compound, as described above, may be included in a smoking composition in any suitable manner and in any suitable amount. The term "smoking composition" is used to describe a composition that produces an aerosol when heated, and is used to make an article for smoking. The term "smoking article" also includes items that heat the smoking composition directly or indirectly, or smoking items that neither combustion nor heat the smoking composition, but instead use an air flow or a chemical reaction to deliver nicotine, a flavoring compound or other materials from tobacco or other sources of nicotine. As used herein, the term "smoke" is used to describe an aerosol produced by a smoking article. An aerosol produced by a smoking article may be produced, for example, by non-combustible smoking articles, such as heated smoking articles or unheated smoking articles.

A flavoring delivery system can controlly release a flavor precursor compound to its surrounding environment by any of the suitable methods, for example by deformation of the flavoring delivery system or by changing the temperature. The amount of flavor precursor compound released over a time interval can be controlled, as well as the start or end of the intervals. The amount of flavor precursor compound released during each interval and the length of the time intervals need not be the same.

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A smoking composition of the invention comprises a flavor precursor compound or a flavoring composition, the composition or precursor that is optionally provided as part of a delivery system. A smoking composition may comprise, for example, one or more of: powder, granules, pfldoras, fragments, strips or sheets comprising one or more of: grass leaf, tobacco leaf, tobacco stalks, tobacco rib fragments , homogenized tobacco, reconstituted tobacco, processed tobacco, extruded tobacco and expanded tobacco. The smoking composition may be in loose form, or it may be provided in a suitable container or cartridge. For example, the smoking composition may be contained within a paper or wrap and be in the form of a plug.

Smoking articles that include aerosol generating devices typically comprise an aerosol forming substrate that is assembled, often with other components, in the form of a bar. Typically, such a rod is shaped and sized to be inserted into an aerosol generating device comprising a heating element for heating the aerosol forming substrate.

The "aerosol forming 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 a flavoring compound after heating. The aerosol forming substrate may be in solid or liquid form. The substrate may comprise both liquid and solid components. The aerosol forming substrate may comprise tobacco and a flavoring composition wherein a flavor precursor compound or a dissociated flavoring compound is released from the substrate after heating. In embodiments, the aerosol forming substrate does not include tobacco, but does include a flavoring composition wherein a flavor precursor compound as described herein or a dissociated flavoring compound is released from the substrate after heating, and optionally nicotine. The aerosol forming substrate may further comprise an aerosol forming. Examples of suitable aerosol formers are glycerin and propylene glycol. Optionally, the aerosol-forming substrate can be provided on or incorporated into a carrier that can take the form of powder, granules, pfldoras, fragments, spaghetti bands, strips or sheets. The aerosol forming substrate can be deposited on the surface of the carrier in the form of, for example, a sheet, foam, gel or suspension. The aerosol-forming substrate may be deposited on the entire surface of the carrier, or alternatively, may be deposited in a pattern to provide a non-uniform supply of the flavor during use.

The smoking articles may comprise a filter, which may be a single segment filter or a multi-component filter comprising two or more filter segments connected or disconnected. Any suitable filter or filter segment may be included in a smoking article described in the present description. One or more of the filter segments may each comprise a flavor precursor compound or a flavor composition, the precursor or composition that is optionally provided in a delivery system. Smoking articles can be packaged in containers for sale, for example in soft packages or flip-top packages, with an inner lining coated or impregnated with a flavoring compound, a flavoring composition or a delivery system.

A smoking composition comprising a flavor precursor compound or a flavoring composition, the precursor or composition that is optionally provided in a delivery system, can be manufactured using any suitable technique. For example, a flavoring composition comprising a flavor precursor compound can be atomized on tobacco. To facilitate atomization, the flavor 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 tobacco. The suspensions comprising the flavor precursor compound may include any liquid or liquid mixture suitable for dispersing and dispensing (eg, by atomizing) the particles comprising the flavor precursor compound. A preferred liquid is water (eg, deionized water), although other liquids, such as alcohols, can be used.

In some embodiments, tobacco can be banded in a solution, suspension or dispersion comprising the precursor of flavor. A solid such as a powder or crystals comprising the flavor precursor can be added to tobacco. The smoking composition can then be processed for use in a smoking article.

In some embodiments, the flavor precursor compound may be added to the volume of tobacco bite supplied to a cigarette maker or applied to a preformed tobacco column before wrapping a cigarette wrap around the tobacco column.

The concentration of a flavor precursor compound in the suspension may be any amount suitable for dispensing the suspension on tobacco. Suspensions comprising a dispersion of a flavor precursor compound in a liquid may comprise from about 0.01 to about 2% by weight of a flavor precursor compound. The flavor precursor compound may be provided in the form of a dry powder and applied to tobacco as such. If dry powder is used, it can spread over tobacco. Another technique for incorporating the flavor precursor compound into a smoking tobacco composition involves adding the flavor precursor compound to a suspension of ingredients used to make reconstituted tobacco. The suspension, which includes the flavor precursor compound, can be formed within a tobacco lamina

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reconstituted and the sheet can be cut into fragments for incorporation as a sting of a composition bar for smoking or other forms of the smoking article.

Homogenized tobacco can also be used to make the aerosol forming substrate for use in smoking articles that are heated in an aerosol generating device. As used herein, the term "homogenized tobacco" denotes a material formed by agglomeration of particulate tobacco. Tobacco dust created by the breakdown of tobacco during shipping and manufacturing, sheet foil, stems and other tobacco by-products that are finely ground can be mixed with a binder to agglomerate particulate tobacco. The homogenized tobacco may comprise other additives in addition to a flavor precursor or flavor composition, which includes but is not limited to aerosolizers, plasticizers, humectants, and non-tobacco fibers, fillers, aqueous and non-aqueous solvents and their combinations Homogenized tobacco can be molded, extruded, or rolled. A number of reconstitution processes to produce homogenized tobacco materials are known in the art. These include, but are not limited to: papermaking processes of the type described in, for example, US 5,724,998; molding processes of the type described in, for example, US 5,724,998; processes of reconstitution of a mass of the type described in, for example, US 3,894,544; and extrusion processes of the type described in, for example, GB983,928.

It will be appreciated that the aerosol forming substrates may have different shapes and sizes depending on, for example, the type of smoking article in which it is intended to be used. The aerosol forming substrates can be essentially three-dimensional. For example, the aerosol-forming substrates may be blocks or plugs comprising a plurality of strands of homogenized tobacco material. Alternatively, the aerosol generating substrates can be essentially two-dimensional. For example, aerosol generating substrates may be mats or sheets comprising a plurality of homogenized tobacco strands.

The amount of convenient flavor precursor compound in a smoking composition may vary depending on the final product in which the smoking composition is to be included. For example, the flavor precursor compound may be added to tobacco to improve the taste or aroma of conventional smoking articles, such as cigarettes, tobacco, and the like. As such, the articles can already produce a similar flavor or aroma when they are smoked, the flavor precursor compounds that release the flavoring compounds having similar taste qualities can be added in relatively low concentrations or amounts. On the contrary, it will be convenient to add higher concentrations or amounts of flavor precursor compounds to smoking compositions, such as tobacco-forming aerosol substrates, which will be used in smoking articles in which the constituents form aerosols without combustion. Smoking articles that have aerosol forming substrates containing tobacco for use with an aerosol generating device typically provide flavor characteristics that differ from fuel smoking articles. It is also convenient to include higher concentrations or amounts of flavoring compounds in smoking compositions that do not include tobacco, such as aerosol-forming substrates that do not contain tobacco. Preferably, the flavor precursor compounds are included in the smoking composition for use in smoking articles in amounts that provide a user with a perceived note similar to an article for smoking fuel, such as a cigarette. For example, the flavor precursor may be included in a non-combustible smoking article or a smoking article that does not include tobacco in an amount that results in the release or supply of the flavoring compound in a concentration or amount similar to that supplied to a user of a conventional smoking article such as a cigarette.

In embodiments, the amount of flavoring compound supplied to a user can be determined by draft. Any suitable method can be used to determine the amount of flavoring compound supplied per puff. For example, ISO, Health Canada Intense, or other automated or standard processes can be used or modified to determine the content per draft. Examples of ISO methods that can be used or modified include: (i) ISO 4387: 1991 Cigarettes - Determination of dry matter free of nicotine and total using an analytical routine smoking machine, 1991-10-15; (ii) ISO 8454: 1995 Cigarettes - Determination of carbon monoxide in the vapor phase of cigarette smoke - NDIR Method, 1991-11-15; (iii) ISO 10315: 1991 Cigarettes - Determination of nicotine in smoke condensates - Gas-chromatography method, 1991-08-01; and (iv) ISO 10362-1: 1991 cigarettes - Determination of water in smoke condensates - Part 1: Gas-chromatography method, 1991-09-15. The Health Canada Intensive Method refers to: Health Canada - Official Method T-115, Determination of "Alquitran", nicotine and carbon monoxide in the mainstream tobacco smoke, December 1999. With regard to the method used, senna It is convenient to determine the amount of a flavoring compound that is supplied by the shedding of a conventional cigarette and to formulate an unconventional smoking article that aerosolizes tobacco or other constituents without combustion so that it supplies similar amounts of the flavoring compound per draft. The amount of flavor precursor compound added to a smoking composition for such articles may vary and can be tested to determine how much flavor precursor is needed to deliver a similar amount of the flavoring compound.

Of course, the amount of flavoring compound supplied conveniently per puff will depend on the flavoring compound itself. In embodiments, a smoking article is configured to deliver approximately 5 nanograms or more of the flavoring compound per puff. In embodiments, a smoking article is configured to deliver approximately 10 nanograms of the flavoring compound per puff to 1 milligram of the

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Flavoring compound per draft, such as from about 50 nanograms per draft to approximately 750 nanograms per draft or from approximately 75 nanograms per draft to approximately 500 nanograms per draft.

The amount of flavor precursor compound added to a smoking composition to provide a convenient amount of dissociated flavoring compound to a user will depend on the components and the configuration of the article and the flavor precursor compound.

Of course, a flavor precursor can be added to a smoking composition in any suitable amount or concentration. In embodiments, a smoking composition comprises 0.001% by weight or more, based on the total weight of tobacco, of the flavor precursor compound. In embodiments, a smoking composition includes 0.005% by weight or more of the precursor flavor compound. In embodiments, a smoking composition includes 0.01% by weight or less of the precursor flavor compound. In embodiments, a smoking composition includes from about 0.001% by weight to about 2% by weight of the flavor precursor compound, such as from about 0.005% by weight to about 1% by weight of the flavor precursor compound or from about 0, 01% by weight to about 0.25% by weight of the flavor precursor compound.

The flavor precursor compound may be added to tobacco at any suitable time, such as before or during tobacco processing for incorporation into a smoking article or the like. Preferably the flavor precursor compound is stable (that is, the flavoring compound is not released or generated) under such processing.

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

In embodiments, the reconstitution of tobacco is carried out by drying and molding a homogeneous suspension of tobacco powder, water, glycerin, binder and cellulose fibers. This type of process is known as a molded sheet process and is widely used by the tobacco industry for the manufacture of homogenized or reconstituted tobacco for use in a conventional cigarette. A molded sheet process may involve applying temperatures of up to about 140 ° C, such as between about 90 ° C and about 140 ° C. Accordingly, if the smoking composition that includes the flavor precursor compound is manufactured in a molded sheet process, the flavor precursor compound is preferably stable at such temperatures.

Preferably, the flavor precursor compound releases the flavor compound or intermediate compound under general conditions of use of the article in which the flavor precursor compound is incorporated. As an example, smoking articles that heat, but not combustion tobacco to aerosolize tobacco constituents, typically heat tobacco from about 200 ° C to about 450 ° C. Accordingly, the flavor precursor compound preferably releases the flavor compound at a temperature of about 200 ° C to about 450 ° C when a smoking composition having the flavor precursor compound is included in such articles. As another example, combustion of tobacco typically occurs at a temperature of approximately 450 ° C. Accordingly, the flavor precursor compound preferably releases the flavoring compound at a temperature below about 450 ° C when a tobacco composition having the flavor precursor compound is included in fuel smoking articles such as cigarettes or tobacco.

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

Tobacco compositions, as used herein, refer to smoking compositions that include tobacco and a flavor precursor. For example, the tobacco composition can be used in combustible smoking articles or non-combustible smoking articles in which an aerosol forming substrate is used. The tobacco composition may be reconstituted tobacco that contains various types of tobacco of different origins, as well as binders and humectants. Moisturizers facilitate the production of an aerosol. When heated, the humectants evaporate and condense again into small droplets to generate a visible aerosol. Preferably, the precursor of the flavor composition releases the flavoring compound under conditions of use, but not under conditions of storage, processing, or manufacturing.

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In the case of fuel smoking articles such as cigarettes, the smoking composition may be used in any portion of the smoking article having a tobacco substrate, for example in the tobacco bar of a conventional cigarette, or in one or more segments of the filter of a conventional cigarette. In the case of smoking articles in which the smoking composition, or a component thereof, does not combustion, the smoking composition may be used in any portion of the smoking article having an aerosol forming substrate.

By way of example and with reference to Fig. 1, a schematic drawing of a smoking article 102 is shown in which the smoking composition does not combustion. 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 nozzle 110 in adjacent coaxial alignment, which is enveloped in an outer wrapping of cigarette paper 112 of low air permeability.

The combustible heat source 104 is a pyrolized porous heat source based on carbon. The combustible heat source 104 is cylindrical and comprises a central air flow channel 116 which extends longitudinally through the combustible heat source 104. A heat-resistant coating essentially impermeable to air 114 of iron oxide is provided on the inner surface of the central air flow channel 116. The aerosol forming substrate 106 is located immediately downstream of the combustible heat source 104 and comprises a cylindrical plug of homogenized tobacco material 118 comprising a flavor precursor compound and glycerin as an aerosol former and circumscribed by the wrapper of the filter plug 120. The homogenized tobacco material 118 consists of longitudinally aligned filaments of extruded tobacco material.

A heat conducting element 122, consisting of an aluminum foil tube, surrounds and is in contact with a rear portion of the combustible heat source 104 and an adjacent front portion of the aerosol generating substrate 106. As shown in Fig. 1, a rear portion of the aerosol forming substrate 106 is not surrounded by the heat conducting element 122.

The elongate expansion chamber 108 is located downstream of the aerosol generating substrate 106 and comprises a cylindrical open-ended cardboard tube 124. The nozzle 110 of the smoking article 102 is located downstream of the expansion chamber 108 and comprises a plug cylindrical cellulose acetate tow 126 of very low filtration efficiency circumscribed by a filter plug wrap 128. The nozzle 110 may be circumscribed by a nozzle paper (not shown). The dimensions of the smoking article 102 may be similar to a conventional cigarette.

During use, a user turns on the carbon-based fuel heat source 4 and then draws air through the central air flow channel 116 downstream to the nozzle 110. The front portion of the aerosol generating substrate 106 is mainly heated by conduction through the non-combustible rear portion adjacent to the fuel heat source 104 and the heat conducting element 122. The aspirated air is heated when it passes through the central air flow channel 116 and then the forming substrate is heated of spray 106 by convection. Heating of the aerosol forming substrate 106 releases volatile and semi-volatile compounds, including the dissociated flavoring compound, and glycerin from the aerosol forming substrate 118, which are drawn into the hot sucked air as it flows through the aerosol forming substrate .

The heated air and the entrained compounds pass downstream through the expansion chamber 108, cool and condense to form an aerosol that passes through the nozzle into the user's mouth (at approximately room temperature).

To make the smoking article 102, a rectangular piece of the heat conducting element 122 is glued to the cigarette paper 112. The heat source 104, the cap of the aerosol forming substrate 106 and the expansion chamber 108 are aligned and positioned suitably on the cigarette paper 112 with the heat conducting element attached 122. The cigarette paper 112 with the heat conducting element attached 122 is wrapped around the rear portion of the heat source 104, the aerosol generating substrate 106 and the expansion chamber 108 and sticks. The nozzle 110 is attached to the open end of the expansion chamber using a known filter combination technology.

In another example of a heated smoking article, the smoking composition comprising the flavor precursor compound is brought into direct contact with a non-combustion heat source, such as an electric heat source. Fig. 2 shows a smoking article that is heated by an electric heat source when coupled with a device for consumption. The smoking article 101 comprises a front cap 103, an aerosol forming substrate 111, a hollow cellulose acetate tube 109, a transfer section 107, and a nozzle filter 105. These five elements are arranged sequentially and in alignment. Coaxial and assembled using a cigarette paper 115 to form a bar. The bar has one end of the side of the mouth, which a user inserts into his mouth during use, and a distal end located at the opposite end of the bar to the end of the side of the mouth. When assembled, the bar is 52 mm long and has a diameter of 7.2 mm. The front cap 103 is a cylindrical portion of cellulose acetate bast. The aerosol forming substrate 111 is located downstream of the front plug 103 and comprises a set of molded tobacco curly sheets wrapped in a filter paper. Molded tobacco leaf includes additives, which include glycerin as a former

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Spray The tube 109 is located immediately downstream of the aerosol forming substrate 111 and is formed of cellulose acetate. Transfer section 107 allows volatile substances to include the flavoring compound released from aerosol-forming substrate 111 to pass along the bar toward the end of the mouth side. The volatile substances may be cooled within the transfer section 107 to form an aerosol. The nozzle filter 105 is a conventional nozzle filter formed of cellulose acetate bast. The elements identified above are assembled when wrapped tightly inside a cigarette paper 115.

The aerosol generating device 119 comprises a cover 121 for receiving the smoking article 101 for consumption. A heating element 113 is located within the sheath 121 and is positioned to engage with the distal end of the smoking article 101. The heating element 113 is in the form of a sheet that ends at a point. When the smoking article 101 is pushed into the sheath, the point of the heating element 113 is first coupled with the front cap 103 and then penetrates into the aerosol forming substrate 111. When the smoking article 101 is properly coupled with 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 by conduction and by convection to the aerosol forming substrate 111 comprising the flavor precursor compound . An insulating collar 117 may surround a portion of the heating element 113 that is to say in contact with and protecting the front cap 103 from burning or melting. Of course, it will be understood that the smoking articles described with respect to Fig. 1 and Fig. 2 are just two examples of a smoking article that can employ a smoking composition comprising a flavor precursor compound as described in the present description. It will also be understood that methods for making a smoking article having a smoking composition that includes a precursor compound of the flavor different from those described in relation to Fig. 1 and Fig. 2 can be employed.

Any suitable method can be used to make a smoking article having a smoking composition that includes a flavor precursor compound. In general, a method of making a smoking article having a smoking composition that includes a flavor precursor compound includes adding or incorporating the flavor precursor compound or a flavor delivery composition into a smoking composition, such as tobacco or other substrate; and incorporate the smoking composition into a smoking article.

In general and as described herein, a method for improving the taste of a smoking composition comprises adding a precursor flavor compound, optionally encapsulated in a delivery system, to the smoking composition. The flavor precursor compound releases or dissociates a flavoring compound or intermediate after heating. As used herein, "release" and "dissociate" are used interchangeably. The heating of the flavor precursor compound occurs when a smoking article (combustion or heating) is used by a smoker.

All the scientific and technical terms used in the present description have meanings that are commonly used in the art unless otherwise specified. The definitions provided in this description are to facilitate the understanding of certain terms frequently used in this description.

As used in this description and the appended claims, the singular forms "a", "a", and "the" encompass modalities having plural referents, unless the content clearly indicates otherwise.

As used in this description and the appended claims, the term "or" is generally used in a sense that includes "and / or" unless the content clearly indicates otherwise.

As used herein, "has", "has", "includes", "includes", "comprises", "comprising" or the like are used in their broad sense, and generally imply "including, but it is not limited to ”. It will be understood that the expression "consisting essentially of", "consists of" and the like are included in "comprising" and the like.

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

Examples

Example 1

A variety of non-volatile sulfur compounds, as shown in Table 1, are analyzed for mutations by (ATD) GC-MS on a cellulose filter to determine if and how much hydrogen sulfide and methanethiol released after heating.

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The compounds are also added to non-combustible smoking articles to evaluate the change in the sensory attributes of such compounds during the customization of such articles in the presence and absence of the compounds.

Certain non-volatile sulfur compounds are applied to other tobacco mixed by syringe injection and used for non-combustible smoking substrates. Tobacco with non-volatile sulfur compounds are formed in branches and equilibrated at least 12 hours before the evaluation.

The orthonasal impact of the selected compounds is evaluated in different concentrations of the global aroma by the use of the smoke simulator in forced mode. The selected compounds are then selected for the sensory test.

Table 1: Non-volatile sulfur compounds

 Compounds containing non-volatile

 CAS No. category

 Cystefna

 3374-33-9 amino acid

 Cystine

 56-89-3 amino acid derivative

 Glutathione

 70-18-8 natural antioxidant in cells

 Methionine

 59-51-8 amino acid

 DL-Methionine Methylsulfonium Chloride

 582174 amino acid derivative

 N-Acetyl L-Cystephine

 616-91-1 amino acid derivative

 S-methyl L-cystephine

 1187-84-4 amino acid derivative

 DL-Homocysteine

 454-29-5 amino acid derivative

 N-Acetyl L-Methionine

 65-82-7 amino acid derivative

 Farnesil-Met-Ome

 218962-72-2 amino acid derivative

 egg albumin

 9006-59-1 sulfur rich proteins

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

 922-50-9 sulfur source without amino acid

Aqueous solutions are prepared in accordance with Table 2. In addition, solutions 1:10 and 1: 100 are prepared for validation.

Table 2: Preparation of the solution in the presence of the tested compounds

 Sulfur compounds not volatile

 Weight (g) ml H2O

 Cystefna

 1.00 10

 Cystine

 n / a n / a

 Glutathione

 1.00 10

 Methionine

 0.50 20

 DL-Methionine Methylsulfonium Chloride

 1.08 10

 N-Acetyl L-Cystephine

 1.50 10

 S-methyl L-cystephine

 0.98 20

 DL-Homocysteine

 0.50 10

 N-Acetyl L-Methionine

 1.91 10

 Farnesil-Met-Ome

 1 pl 20 pl

 egg albumin

 0.50 10

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

 1.00 20

The ATD-GC-MS analyzes were carried out using the following instrumental installation: Table 3: ATD-GC-MS Instrumentation

 Instrument

 Details

 Injector

 Thermos Extruder Turbo Matrix Perkin Elmer 350

 Gas chromatograph

 Agilent 7890A GC

 Column

 60 m x 0.25 pm, FFAP

 Mass chromatograph

 Agilent 5975C

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Table 4: ATD-GC-MS parameters

 ATD parameters

 Value

 tube temperature

 250 ° C

 trapdoor temperature

 O 0 O

 temperature gradient

 99 ° C per second at 275 ° C

 desorption time

 5 min

 N2 pressure

 170 kPa; constant

From each solution of the compound (1:10, 1: 100 in stock) 20pl is injected into a piece of Cambridge pre-balanced pad that is then inserted into the glass tube. The tubes are evaluated ortonasally after thermal desorption and the aroma notes detected are determined. The results are given in Table 5.

Table 5: Flavor evaluation

 Sulfur compounds not volatile

 Comments and orthonasal evaluation

 Cystefna

 New tubes (heated to 250 ° C) gave an impression of roasted and burned phenol with a weak note of sulfur meat

 Glutathione

 New tubes (heated to 350 ° C) gave only a weak roasted impression

 Methionine

 New tubes (heated to 350 ° C) olio with cooked potato and meat

 N-Acetyl L-Methionine

 Methanothiol Note Stronger than the Hydrogen Sulfide Note

 Farnesil-Met-Ome

 baked potato

 egg albumin

 balanced methanethiol and hydrogen sulfide

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

 New tubes (heated to 250 ° C) cooked potato olio with a sulfur roasted appearance

 DL-Methionine Methylsulfonium Chloride

 green, cabbage, fishy smell, sulfur green

 N-Acetyl-Cystephine

 popcorn, meat smell, toasted

 DL-Homocysteine

 very weak toast

 S-methyl-L-cysteine

 sulfur cabbage

The results indicate that there are mainly two families of compounds, the first one that predominantly generates hydrogen sulfide (H2S) and the second one that predominantly generates methanethiol (MSH). The exception is egg albumin for which the generation seems to be similar.

The tubes of these candidates that generate mainly H2S were evaluated ortonasally after heating that gave sulfur, toasting or burning. H2S could not be detected directly. In contrast, methanethiol generating compounds were judged to have a potato-like aroma, indicating the presence of metional as a secondary product.

Example 2

The orthonasal and smoking action evaluation of selected non-volatile sulfur compounds is carried out using a forced mode smoke simulator. The following prototypes are tested:

Table 6: Prototypes tested

 Sulfur compounds not volatile

 Concentration injected in mg (concept A) Concentration injected in mg (concept B)

 Cystefna

 1.82 0.182

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 Glutathione

 1.75 0.175

 Methionine

 0.47 0.047

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

 0.94 0.094

 DL-Methionine Methylsulfonium Chloride

 1.00 0.10

 S-methyl-L-cysteine

 2.07 0.20

The test is carried out as follows. The smoking regime is Health Canada. The established power of the smoke simulator is 54W. The smoking action evaluation is carried out for concepts that show the preferences in the orthonasal evaluation. The evaluation of the action of smoking is carried out by comparing an untreated mixture against a treated concept

For the sensory test submission in the panel of experts, only cystephine and glutathione were selected. For glutathione the concept B was chosen and for cystefna the concept B was chosen.

Table 7: Observations recorded during experimental execution

 Thiol-containing compound

 Concept Panel description

 Cystefna

 A sulfur, cold smoke, less totally different notes

 B

 sulfur, cold smoke, less totally different notes

 Glutathione

 A sulfur, cold smoke, less totally different notes

 B

 sulfur, cold smoke, less totally different notes

 Methionine

 A cooked potato and sulfur vegetable are dominant

 B

 cooked potato, sulfur vegetable, less totally different notes

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

 At increased sulfur notes; sulfur green direction and smoked ham

 B

 Perception of smoked sulfur increased with less totally different notes

 DL-Methionine Methylsulfonium Chloride

 A cooked potato, cabbage notes, atypical aroma

 B

 insignificant difference

 S-methyl-L-cysteine

 A rise in sulfur notes; green, meat and paprika notes

 B

 close to the reference with augmented greenish hay-like notes

The addition of sulfur-containing compounds, especially with thiol-free groups, improves the perception of the taste of non-combustible products and faces problems, such as totally different notes, complexity and fullness in the mouth. In particular, the addition of precursors containing thiol, cysteine and glutathione contribute positively to the overall taste of aerosols formed after heating by the addition of smoke, fullness in the mouth, hardness, bitterness and complexity.

In summary, the addition of sulfur-containing precursors showed that it has a positive effect on the total sensory perception of the prototypes, increasing the attributes of black smoke, reducing the totally different notes of non-combustible products and increasing the sensations in the mouth and in the mouth. throat, like bitterness and fullness in the mouth.

Claims (7)

5 10 fifteen twenty 25 30 35 40 Four. Five fifty 55 60 65 A smoking article (101, 102) comprising: an aerosol forming substrate (106, 111); a heating element (104, 113) configured to heat, but not combustion, the aerosol forming substrate; a flavor precursor compound added to the aerosol forming substrate, wherein the flavor precursor compound releases a thiol-containing flavoring compound after heating of the aerosol forming substrate by the heating element. An article for smoking according to claim 1, wherein the flavoring compound containing thiol is hydrogen sulfide or methanethiol. A smoking article according to claim 1 or 2, wherein the flavor precursor compound has the following structure: R2 O image 1 R1 (I), where: R1 is OH or an amino acid residue, R2 is H, C (O) CH3, or an amino acid residue, R3 is H or unsubstituted C1-C3 alkyl, R4 is optional and, if present, is unsubstituted C1-C3 alkyl, and x is an integer from 1 to 3. A smoking article according to claim 1 or 2, wherein the flavor precursor compound has the following structure: R2 O image2 (II) where: R1 is OH or an amino acid residue, R2 is H, C (O) CH3, or an amino acid residue, R3 is H, unsubstituted C1-C3 alkyl or a cysteine residue, and x is an integer from 1 to 3. 5 10 fifteen twenty 25 30 35 40 Four. Five fifty 55 60 65 7. 8. 9. 10. 11. 12. An article for smoking according to claim 4, wherein R1 is OH or a glycerin residue, R2 is H, C (O) CH3, or a glutamate residue, R3 is H or CH3, and x is 1 or 2. A smoking article according to claim 1 or 2, wherein the flavor precursor compound has the following structure: R2 O image3 where: R1 is OH or an amino acid residue, R2 is H, C (O) CH3, or an amino acid residue, and x is an integer from 1 to 3. An article for smoking according to claim 6, wherein R1 is OH or a glycerin residue, R2 is H, C (O) CH3, or a glutamate residue, and x is 1 or 2. A smoking article according to claim 1 or 2, wherein the flavor precursor compound has the following structure: R2 O image4 where: R1 is OH or an amino acid residue, and R2 is H, C (O) CH3, or an amino acid residue. An article for smoking according to claim 8, wherein R1 is OH or a glycerin residue and R2 is H, C (O) CH3, or a glutamate residue. A smoking article according to claim 1 or 2, wherein the flavor precursor compound comprises a cysteine residue. An article for smoking according to claim 1 or 2, wherein the flavor precursor compound is selected from the group consisting of cysteine, cystine, glutathione, methionine, DL-methionine methylsulphonium, N-acetyl cystephine, S-methyl cysteine , DL-homocysteine, N-acetyl methionine, Farnesyl-Met-Ome, albumin and 2-hydroxy-4- (methylthio) butyric acid. An article for smoking in accordance with any preceding claim, wherein the aerosol forming substrate comprises tobacco. An article for smoking according to claim 12, wherein heating the tobacco and the flavor precursor compound results in the production of furfuriltiol. fifteen 14. A smoking article according to any preceding claim, wherein the flavor precursor compound is configured to release hydrogen sulfide or methanethiol at a temperature of about 200 ° C to about 450 ° C. 5 15. An article for smoking in accordance with any preceding claim, further comprising nicotine or a source of nicotine. image5 image6 Figure 1 image7 Figure 2