TW201429415A - Flavor precursors - Google Patents

Abstract

A smoking composition comprises an aerosol-generating substrate and a phenolic glycoside. Cleavage of the glycosidic bond releases a phenolic compound having a smoky note. The smoking composition may be incorporated into a smoking article that is configured to cause the glycosidic bond to be cleaved during use. The smoking article may include tobacco and may be configured to heat, but does not combust, tobacco. Such articles typically are lacking in smoky flavor relative to smoking articles in which tobacco is combusted. Inclusion of the phenolic glycoside helps bridge the flavor gap.

Description

Spice precursor

This invention relates to perfume precursors useful in cigarette compositions, as well as articles and methods relating to such cigarette compositions.

Smoking articles that heat tobacco rather than burn tobacco have been proposed. Such articles can produce an aerosol capable of delivering nicotine and other tobacco components to a user. However, since tobacco is not burned during the use of such articles, the smoky note that the user may feel is significantly less than that of conventional smoking articles such as cigarettes.

Therefore, it may be desirable to incorporate the compound into the tobacco used in non-combustible smoking articles to bring it closer to the experience associated with smoking conventional cigarettes. There are many compounds known to produce a scent of smoke. However, the volatility of such compounds can present challenges when incorporating such compounds into tobacco or smoking articles. For example, losses may occur due to the volatility of the compound during production or storage. In addition, articles incorporating such compounds but not yet used may result in an unpleasant burnt or smoke odor.

As described herein, wherein tobacco or other materials are heated The non-combustible smoking article provides the user with an aerosol containing the compound of the invention, allowing the user to feel a feeling similar to smoking a conventional cigarette. Such articles contain a composition of cigarettes including phenol glycosides that do not produce significant odors. The glycosidic linkage of the phenol glycoside breaks upon heating to produce a phenolic compound that provides a scent of smoke. Therefore, users of tobacco products can feel a similar feeling of smoking a conventional cigarette.

The smoking articles described herein can provide one or more advantages over smoking articles of the old non-combustible tobacco. For example, as previously described, the smoking articles described herein provide an enhanced aroma or sensory experience relative to smoking articles that do not include a chemically immobilized phenolic compound having a scent of smoke. Because the phenolic compound is capable of dissociating from the glycoside, and because the glycoside does not volatilize or is less volatile than the phenolic compound, it can slow the loss in the production process, and the article can have a longer shelf life. Further, since the glycoside has a lower odor than the phenolic compound, the product does not produce a burnt smell or a smoke smell when not used.

For the purposes of the present invention, the term "fragrance compound" can be used interchangeably with "a phenolic compound having a scent of smoke".

The term "smoky" as used herein is readily understood by an experienced perfumer, meaning the aroma associated with wood burning. This term is used in many reference books, including "Flavor, Chemistry and Technology" by Gary Reineccius, Second Edition, and "Perfume and Fragrance Chemicals by Steffen Arctander" (Perfume and Flavor Chemicals", 1969.

Any suitable perfume compound can be combined with a reducing sugar to produce A phenol glucoside, which can be added to tobacco or other materials to produce the cigarette composition described herein. When the glycosidic bond is cleaved, the phenolic compound having a scent of smoke is released.

In a particular embodiment, the perfume compound has the structure of:

Wherein R ¹ , R ² , R ³ , R ⁴ and R ⁵ are each independently selected from the group consisting of (i)H and (ii) a C1-C5 linear or branched alkyl or alkoxy group, wherein the alkane The base or alkoxy group is unsubstituted or substituted by halogen or hydroxy. One or more of R ¹ , R ² , R ³ , R ⁴ and R ⁵ are a C1-C5 linear or branched alkyl or alkoxy group. The substituted or unsubstituted alkyl or alkoxy group is preferably a C1-C3 alkyl group or an alkoxy group. The alkyl or alkoxy group is preferably unsubstituted.

In a particular embodiment, one or more of R ¹ , R ² , R ³ , R ⁴ and R ⁵ are selected from the group consisting of methyl, ethyl, propyl (eg isopropyl), methoxy and ethoxy. The group that is formed. One or more of R ¹ , R ² , R ³ , R ⁴ and R ^{5 are} preferably selected from the group consisting of methyl, ethyl, isopropyl and methoxy. In some embodiments, R ¹ , R ² , R ³ , R ⁴ and R ⁵ of the non-methyl, ethyl, propyl, methoxy or ethoxy group are H.

In a particular embodiment, one or both of R ¹ and R ⁵ are methoxy.

In some embodiments, R ³ is isopropyl.

In a particular embodiment, one or more of R ¹ , R ² and R ³ are methyl.

In a particular embodiment, R ² is ethyl.

Preferred perfume compounds include those selected from the group consisting of 2-methoxyphenol (or guaiacol wherein R ^{1 in} formula I is methoxy and R ² , R ³ , R ⁴ and R ⁵ are H), 2 , 6-dimethoxyphenol (wherein R ¹ and R ^{5 in} formula I are methoxy, and R ² , R ³ and R ⁴ are H), o-cresol (wherein R ^{1 in} formula I is A) And R ² , R ³ , R ⁴ and R ⁵ are H), m-cresol (wherein R ^{2 in} formula I is methyl, and R ¹ , R ³ , R ⁴ and R ⁵ are H), Cresol (wherein R ^{3 in} formula I is methyl, and R ¹ , R ² , R ⁴ and R ⁵ are H), 3-ethylphenol (wherein R ^{2 in} formula I is ethyl, and R ¹ And R ³ , R ⁴ and R ⁵ are H), 4-isopropylphenol (wherein R ³ in the formula I is isopropyl, and R ¹ , R ² , R ⁴ and R ⁵ are H) and 2, a group consisting of 3-dimethylphenol (wherein R ¹ and R ^{2 in} formula I are methyl groups, and R ³ , R ⁴ and R ⁵ are H). More preferably, the perfume compound is guaiacol (2-methoxyphenol).

Any perfume compound may be released from the glycoside, as taught herein. The perfume compound referred to herein is an aromatic six member carbon ring structure in which at least one carbon atom in the ring has a hydroxy substituent. Other cyclic components may be substituted or unsubstituted as long as the compound produces a scent of smoke.

Any suitable test method can be used to determine if the fragrance compound will produce a scent of smoke. For example, a compound which induces a subjective feeling of odor, odour, smell, flavor, etc. can be considered to have or produce a scent of smoke. rhyme. In a particular embodiment, a person trained in odor can be used to confirm whether the phenolic compound has a scent of smoke. In particular embodiments, random or non-randomly selected persons may also be used to confirm whether they are aware that the compound produces a scent of smoke. For example, if 25% or more (for example, 50% or more, 60% or more, 70% or more, or 80% or more), the selected person feels the smell of smoke, or a panel uses the relevant smoke. For the description of the flavor (such as smoke), the compound will be considered to have a scent of smoke. The perfume compound, or a derivative thereof, can be joined to any suitable reducing sugar (also known as a glycone) via a glycosidic linkage to produce a glycoside which will liberate the phenolic compound upon cleavage of the glycosidic linkage. The glycosyl group can be any suitable monosaccharide or polysaccharide or a derivative thereof. For example, the polysaccharide can be a cellulose, a trisaccharide or a disaccharide. Examples of the trisaccharide which can be used as the glycosyl group include isomaltotriose, Aspergillus trisaccharide, maltotriose, melezitose, maltotrione, raffinose, canetriose, and the like. Examples of the disaccharide which can be used as a glycosyl group include sucrose, maltose, lactose, cellobiose, lactulose, trehalose, bismuthose, avermose, isomaltose, β, β-trehalose, α, β- Trehalose, bismuth saccharide, kelp disaccharide, gentiobiose, pine disaccharide, maltulose, palatinose, gentiobiulose, mannose, melibiose, melibet Sugar (melibiulose), chewing gum, rutinulose, xylobiose, and the like.

If the monosaccharide is a glycosyl group, the monosaccharide is preferably a C5-C7 monosaccharide. The monosaccharide is more preferably a C6 monosaccharide. Examples of the monosaccharide which can be used as a glyco group include glucose, galactose, glucuronic acid, fructose, xylose, ribose, mannose, gum sugar, maltose, tagatose s and the like. The monosaccharide is preferably glucose.

The glycoside can be synthesized in any suitable manner. An example of a saccharification reaction is the Koenigs-Knorr reaction, which is a substitution reaction of a glycoside halide with an alcohol, which is carried out in the presence of a heavy metal or a silver salt to produce a glycoside. Other saccharification methods that can be used are Helferich saccharification, in which the catalyst is a mercury salt such as mercury cyanide; Fischer saccharification reaction; utilization of glycoside glycosyl ester; glycosyltrichloroethylene imidate; glycosyl fluoride; Internal glycosyl transfer; and so on.

In particular embodiments, for example, (i) Dignum et al. (2004), Food Science 85: 199-205; (ii) Hayasaka et al. (2010), Journal of Agro-Food Chemistry 58: 10989-10998; Iii) The saccharification reaction described in Cai et al. (2010), Asian Chemical Journal (2010) 22(9): 6647-6651; or (iv) WO 88/09133 to produce phenol glycosides.

The saccharification reaction generally involves reacting a glycosyl donor with a glycosyl acceptor in the presence of a catalyst to produce a phenolic glycoside, which in the present invention is a phenolic compound or a derivative thereof. The free alcohol of the phenolic compound or its derivative will react with the glycosyl donor to produce an O-glycosidic linkage. Any suitable glycosyl donor can be used. Typically, the glycosyl donor is a glycosyl halide such as a glycosyl bromide, a glycosyl chloride, and the like.

2,3,4,6-Tetradecyl-α-D-glucopyranosyl bromide ("Ethyl bromide") is commonly used to prepare glycosides derived from glucose. The preparation method of acetaminophen bromoglucose usually comprises using glucose in a solvent (such as dichloromethane) in the presence of a catalyst such as pyridine, triethylamine and dimethylaminopyridine or sodium acetate and zinc chloride. Acetic anhydride is subjected to a full oximation reaction. The obtained 1,2,3,4,6-pentaethyl-α-β-D-glucopyranoside can be treated with HBr-acetic acid in, for example, dichloromethane to produce ethyl bromide, which can be Obtained by crystallization. The chlorine derivative can be obtained by using HCl vapor, SOCl ₂ in dimethylformamide ("DMF"), or the like.

If the sugar contains an acid-sensitive group (such as an azide) or an acid-sensitive protecting group (such as acetal or benzylidene), a milder halogenation reaction condition (such as phosgene in DMF or trimethyl) can be used. In bromodecane) to produce a glycosyl halide.

Ethyl bromide (CAS No. 572-09-8) can be synthesized as described above or purchased by a supplier such as Sigma-Aldrich. The above reaction for acetamidine bromide can be easily modified to produce trimethyl ethane bromide (CAS number 81058-27-7). Alternatively, it is purchased by a supplier to purchase trimethyl ethane bromide from a supplier such as Sigma-Aldrich.

For example, a glycoside having glucose or a derivative thereof as a glycosyl group and a perfume compound as an aglycone is depicted by the following formula II:

Wherein R ¹ , R ² , R ³ , R ⁴ and R ^{5 are} as defined in the above formula I, and R ⁶ , R ⁷ , R ⁸ and R ⁹ are each independently H or a protecting group such as ethyl hydrazino. [-C(O)CH ₃ ], trimethylethenyl [-C(O)(CH ₃ ) ₃ , also known as trimethylethenyl or 2,2-dimethylpropanyl]; and many more. In a particular embodiment, R ⁶ , R ⁷ , R ⁸ and R ⁹ are the same. R ⁶ , R ⁷ , R ⁸ and R ^{9 are} preferably H. If R ⁶ , R ⁷ , R ⁸ or R ⁹ is a protecting group, the protecting group can be cleaved to produce a phenolic glycoside having an unsubstituted sugar group. For example, an ethenyl or trimethylethenyl group can be readily cleaved in sodium methoxide-methanol (NaOMe-MeOH). Other protecting groups can be readily removed via any suitable deprotection reaction, many of which are known techniques. It will be understood that the glycosyl group may be derived from any suitable monosaccharide other than the glucose depicted in Formula II or a polysaccharide as previously described.

In a preferred embodiment, the glycoside is guaiacol glucoside ((2R,3S,4S,5R,6S)-2-hydroxymethyl)-6-(2-methoxyphenoxy)tetrahydrogen -2H-pyran-3,4,5-triol), which has the structure of the formula:

The perfume composition referred to herein contains a composition of a phenol glycoside. In this article, the word "phenolic glycoside" is used interchangeably with the word "perfume precursor compound". The perfume delivery composition of the present invention comprises a perfume precursor compound and which facilitates the release of the perfume precursor compound in a controlled manner Put it in the surrounding environment. In various embodiments, the phenolic glycoside is synthesized or purified prior to its addition to the perfume composition or perfume delivery composition.

As stated previously, the phenol glycoside can be contained in the cigarette composition in any suitable manner and in any suitable amount. The term "cigarette composition" is used to describe a composition that produces smoke when it is burned or heated and is used to make a smoking article. The term "smoking articles" includes cigarettes, cigars, cigarillos and other products in which cigarette constituents (such as tobacco constituents) are ignited and burnt to produce smoke. The term "smoking article" also includes articles in which the composition of the cigarette is not burned, such as, but not limited to, a smoking article that directly or indirectly heats the composition of the cigarette but does not burn or burn the composition of the cigarette, or neither burns nor heats. A cigarette composition is a smoking article that uses a gas stream or chemical reaction to deliver nicotine, a fragrance compound, or other material from tobacco. As used herein, the term "smoke" is used to describe an aerosol produced by burning a smoking article. The aerosol produced by the smoking article may be, for example, smoke produced by a flammable smoking article (such as a cigarette) or by a non-combustible smoking article (such as a heated smoking article or a non-heated smoking article). Aerosol.

In addition to the perfume precursor compound, the perfume composition of the present invention may comprise one or more flavoring agents known in the art including, but not limited to, menthol, spearmint, mint, eucalyptus, vanilla, cocoa, chocolate, coffee, tea. , spices (such as cinnamon, cloves and ginger), fruit extracts, and combinations thereof. In a particular embodiment, the perfume composition further contains menthol or eugenol. Such fragrances are often used to impart a cool, aromatic scent to the smoke of smoking articles.

The perfume delivery composition can be controlled to release the perfume precursor compound to the surrounding environment by any suitable means, such as by modifying the perfume delivery composition or by changing the temperature. The amount of fragrance precursor compound released over time intervals, as well as the beginning or end of the interval, is controllable. The amount of perfume precursor compound released during each time interval, as well as the length of the time interval, need not be equal.

In a particular embodiment, the perfume delivery composition can be in any suitable form so long as it is capable of maintaining the fragrance composition in the structure of the composition until it needs to be released. Preferably, the perfume delivery composition comprises a closed matrix or network structure that locks the perfume precursor compound in the closed structure. For example, the perfume composition can be locked in a region within the matrix structure. When the material is compressed or deformed, the perfume precursor composition will be extruded from the matrix structure, for example, via a fracture of the surrounding structure. In a particular embodiment, the perfume delivery composition comprises a polymeric matrix comprising one or more matrix forming polymers. For example, the polymer matrix gradually disintegrates as the compressive strength, temperature, or both increase, such that the perfume precursor compound is controlled to be released from the perfume delivery composition. Thus, the release of the perfume precursor compound can be varied as a function of temperature or deformation caused by compression or shear forces applied to the perfume delivery composition. The perfume delivery composition can advantageously be disposed in the smoking article in a variety of different forms, thereby providing considerable flexibility in the manner in which the composition is incorporated into the smoking article. In a particular embodiment, the flavor delivery composition can be in the form of granules, beads or capsules. These granules, beads or capsules can be formed into any suitable shape, but are preferably substantially cylindrical or spherical.

The cigarette composition of the present invention comprises a fragrance precursor compound, a fragrance composition or a fragrance delivery composition. The cigarette composition may comprise, for example, vanilla leaves, tobacco leaves, tobacco stems, stem fragments, homogenized tobacco, reconstituted tobacco, one or more of one or more forms such as powder, granules, pellets, chips, thin strips or flakes, Processing tobacco, extruded tobacco and expanded tobacco. The cigarette composition can be in a loose form or can be placed in a suitable container or cartridge. For example, the cigarette composition can be contained in paper or roll paper and have the form of a plug.

Smoking articles comprising an aerosol generating device typically comprise an aerosol generating substrate which is often assembled into a rod-like form with other ingredients. In general, such a rod will be shaped and sized to be inserted into an aerosol generating device comprising a heating element for heating the aerosol generating substrate. As used herein, "aerosol-generating substrate" is a type of cigarette composition that can be used in an aerosol generating device to produce an aerosol. The aerosol-generating substrate can release the fragrance compound upon burning or heating. The aerosol-generating substrate can be in solid form or in liquid form. The substrate can include both liquid and solid components. The aerosol-generating substrate can include a tobacco and perfume composition wherein the perfume precursor compound or the dissociated perfume compound is released from the substrate upon heating. In a particular embodiment, the aerosol-generating substrate does not include tobacco, but includes a perfume composition and selected nicotine in which the phenolic glycoside or dissociated perfume compound as described herein is heated by the substrate. Released in the middle. The aerosol-generating substrate may further comprise an aerosol former. Examples of suitable aerosol formers are glycerin and propylene glycol. Optionally, the aerosol generating substrate can be mounted or embedded in a carrier, It may be in the form of powder, granules, pellets, chips, pasta, thin strips or flakes. The aerosol-generating substrate can be deposited on the surface of the carrier in the form of, for example, a sheet, foam, gel or slurry. The aerosol-generating substrate can be deposited on the entire surface of the carrier or, alternatively, in a pattern for providing non-uniform perfume delivery during use.

The smoking article can include a filter that can be a single-stage filter or a multi-component filter that includes two or more connected or unconnected filter segments. Those skilled in the art will recognize that there are many suitable filter segments. The one or more filter segments can each comprise a perfume precursor compound, a perfume composition, or a perfume delivery composition. The smoking article can be packaged and sold in a container, such as a soft box or a flip-top box, the liner being coated or impregnated with a fragrance compound, a fragrance composition or a fragrance delivery composition.

Any suitable technique can be used to make a cigarette composition comprising a flavor precursor compound, a perfume composition, or a perfume delivery composition. For example, the flavor precursor compound can be added to the cigarette tobacco stock fed to the cigarette maker, or it can be applied to the preformed tobacco column before the cigarette paper is wrapped around the tobacco column. In a particular embodiment, a method for making a cigarette composition includes the step of spraying tobacco with a flavor precursor compound. To facilitate spraying, the perfume precursor compound can be added to a liquid carrier to form a solution or suspension, and the solution or suspension applied to the tobacco. The cigarette composition can then be processed for use in cigarettes or other smoking articles. The solution or suspension containing the perfume precursor compound can include any liquid or liquid mixture suitable for dispersing or dispensing (spraying) the particles of the fragrance-containing precursor compound. The preferred liquid is water (eg, deionized water), but other liquids may also be used, such as Such as alcohols.

The concentration of the perfume precursor compound in the slurry can be any amount suitable for dispensing the solution or suspension onto the tobacco. Such solutions or suspensions comprising a dispersion of a perfume precursor compound in a liquid may contain from about 0.1% by weight and up to about 0.5% by weight, or from about 0.2% by weight and up to about 1% by weight of the perfume precursor compound. The perfume precursor compound can be in the form of a dry powder and applied to the tobacco itself. If you are using a dry powder, you can sprinkle it on the tobacco. Another technique for incorporating a flavor precursor compound into a tobacco cigarette composition relates to the addition of a perfume precursor compound to a slurry used to make the ingredients of the reconstituted tobacco. The slurry containing the perfume precursor compound can form a reconstituted tobacco sheet, and the sheet can be cut into pieces to incorporate a cigarette composition rod or other form of smoking article as a face filler.

Homogenized tobacco can also be used to make an aerosol-generating substrate for use in smoking articles that can be heated in an aerosol generating device. As used herein, the term "homogenized tobacco" means a material formed by cohesive particulate tobacco. Tobacco ash, leaves, stems and other tobacco by-products resulting from tobacco breakage during shipping and manufacturing may be mixed with the binder after fine grinding to cause the tobacco particles to coagulate. Homogenized tobacco may contain, in addition to the perfume composition or perfume delivery composition, other additives including, but not limited to, aerosol formers, plasticizers, humectants, and non-tobacco fibers, fillers, aqueous and non-aqueous solvents. And their combinations. Homogenized tobacco can be cast, extruded or rolled. Several methods of reconstituting tobacco for making homogenized tobacco are known in the art. These methods include, but are not limited to, those described in, for example, US 5,724,998 A paper process; a casting process as described in, for example, US 5,724,998; a dough reconstitution process as described, for example, in US Pat. No. 3,894,544; and an extrusion process as described, for example, in GB 983,928.

It should be understood that the aerosol-generating substrate can have different shapes and sizes depending on, for example, the type of smoking article to be used. The aerosol-generating substrate can be substantially three-dimensional. For example, the aerosol-generating substrate can be a brick or plug comprising a plurality of bundles of homogenized tobacco material of the present invention. Alternatively, the aerosol-generating substrate can be substantially two-dimensional. For example, the aerosol-generating substrate of the present invention may be a mesh or sheet comprising a plurality of homogenized tobacco bundles.

The amount of perfume precursor compound required in the composition of the cigarette may vary depending on the final product containing the composition of the cigarette. For example, phenol glycosides can be added to tobacco to enhance the smoke or aroma of traditional smoking articles such as cigarettes, cigars, and the like. Since such articles may have produced a smoke or aroma when smoking, the phenolic compounds described herein may be added in relatively low concentrations or amounts. Conversely, it may be desirable to add a higher concentration or amount of phenol glycoside to a cigarette composition, such as a tobacco-containing aerosol-generating substrate, which will be used to make up a smoking article that is aerosolized or heated to be unburned. Smoking articles having an aerosol-generating substrate (which contains tobacco and are used with an aerosol generating device) generally provide a less intense smoke or aroma to the user than conventional cigarettes. It may also be desirable to include a higher concentration or amount of phenol glycoside in a cigarette composition that does not include tobacco, such as an aerosol-generating substrate comprising non-tobacco. The phenol glycoside is preferably contained in a cigarette composition for smoking articles in an amount that provides a user with a similar smoking article (such as a cigarette). The intensity of the feeling. For example, a phenolic glycoside may be contained in a non-combustible smoking article or a tobacco-free smoking article in an amount that results in a perceived concentration of the phenolic compound being delivered to the user in a manner similar to conventional smoking articles (eg, cigarettes). Or release or deliver.

In a particular embodiment, the amount of phenolic perfume compound delivered to the user can be determined on a per smoke basis. Any suitable method can be used to determine the amount of perfume compound delivered per puff. For example, the ISO, Health Canada Intense, or other standard or automated procedures can be used or modified to determine the internal content of each puff. Examples of ISO methods that can be used or modified include: (i) ISO 4387: 1991 cigarettes - determination of all and no nicotine dry matter using conventional analytical smoking machines, 1991-10-15; (ii) ISO 8454: 1995 cigarettes - determination One of the carbon oxides in the gas phase of cigarette smoke - NDIR method, 1991-11-15; (iii) ISO 10315: 1991 cigarette - determination of nicotine in gas condensate - gas chromatography, 1991-08-01; (iv) ISO 10362-1:1991 - Determination of moisture in flue gas condensate - Part 1: Gas chromatographic analysis, 1991-09-15. Health Canada's deep pumping method refers to: Health Canada - Official Method T-115, measuring "tar", nicotine and carbon monoxide in tobacco mainstream smoke, December 1999. Regardless of the method used, it may be desirable to determine the amount of perfume compound delivered by each cigarette in a conventional cigarette, and then formulate a non-traditional smoking article that aerosolizes tobacco or other ingredients in the unburned condition. A similar amount of perfume compound can be delivered at each puff. The amount of phenol glycoside added to the cigarette composition used in such articles can be varied and tested to determine how much phenol glycoside is needed A similar amount of perfume compound is delivered.

By way of example and more detailed discussion below, it has been found that when measured by the Canadian Department of Health's deep aspiration method, the amount of guaiacol that a conventional cigarette can deliver to a smoker is about 100 ng per squirt per spurt. About 300 Nike. Therefore, for non-traditional smoking articles, such as aerosolized tobacco constituents or other ingredients that are not burned, it is desirable to have a phenolic glycoside amount capable of achieving 50 ng or more of guaiacol per squirt, for example Each smog is about 50 ng guaiacol to about 500 ng guaiacol, or about 100 ng per gram of guaiacol to about 300 ng guaiacol.

Of course, the amount of perfume compound required to deliver each puff will depend on the perfume compound itself. In a particular embodiment, the smoking article is designed to deliver about 5 nanograms or more of perfume compound per puff. In a particular embodiment, the smoking article is designed to deliver from about 10 ng to 1 mg of perfume compound per puff, such as from about 50 Ng/smoke to about 750 Ng/smoke, or about 75 Ng/smoke to About 500 ng / puff.

The amount of the perfume precursor compound added to the cigarette composition to deliver the desired amount of the dissociated perfume compound to the user is determined by the composition and design of the article and the phenol glycoside.

Of course, the phenol glycoside can be added to the cigarette composition in any suitable amount or concentration. In a particular embodiment, the cigarette composition comprises about 0.001% by weight, more preferably about 0.005% by weight, still more preferably about 0.01% by weight phenol glycoside. In a particular embodiment, the cigarette composition can include up to about 2% by weight phenol glycoside, still more preferably up to about 1% by weight phenol glycoside, still more preferably up to about 0.5% by weight phenol glycoside, And still more preferably up to about 0.02% by weight of phenol glycoside (all % by weight refers to dry weight).

One or more added phenol glycosides may be naturally present in matured or unripened tobacco. For example, guaiacol glucoside [((2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(2-methoxyphenoxy)tetrahydro-2H-pyridyl has been discovered Anthracene-3,4,5-triol)] is present in tobacco. Thus, the addition or purification of a synthetic or purified phenol glycoside to tobacco will increase the concentration of phenolic glycoside in the tobacco-containing cigarette composition relative to the tobacco itself. In a particular embodiment, the synthetic or purified phenol glycoside is added to the tobacco to form a cigarette composition having a concentration of phenol glycoside that is 1.5 times or more the concentration in the tobacco itself. For example, the concentration of the phenolic glycoside of the cigarette composition may be 2 times or more, 2.5 times or more, 3 times or more, 3.5 times or more, 4 times or more, 4.5 times or more, 5 times of the concentration in the tobacco itself. Or more, 7.5 times or more, or 10 times or more.

One or more flavor precursors can be added to the cigarette composition in any suitable manner. For example, the perfume composition containing the perfume precursor compound may be sprayed onto the tobacco in the form of a solution, suspension or dispersion; the tobacco may be impregnated in a solution, suspension or dispersion of the phenol glycoside; the powder of the phenol glycoside may be Or crystals added to tobacco; and so on. The flavor precursor compound can be added to the tobacco at any suitable time, such as before or during the processing of the tobacco to incorporate the smoking article or the like. The glycoside is preferably capable of being stable during processing (i.e., the glycosidic linkage does not break).

For example, tobacco can be reconstituted by drying a homogeneous slurry of tobacco powder, water, glycerin, gum beans and cellulose fibers. And the way of casting. This type of process is known as the cast leaf process and is widely used in the tobacco industry to make reconstituted or homogenized tobacco for use in conventional cigarettes. The cast leaf process may involve application of temperatures below 200 °C, below 150 °C, or in the range of from about 100 to 150 °C, or from 100 to 200 °C. Therefore, if a cigarette composition containing a flavor precursor compound is to be produced in the cast leaf method, the flavor precursor compound is preferably stable at this temperature.

Preferably, the glycosidic linkage of the perfume precursor compound is cleaved under the general conditions of use of the article incorporating the composition of the cigarette. For example, a smoking article that heats rather than combusts tobacco to aerosolize the tobacco component typically heats the tobacco at a temperature of from about 200 °C to about 300 °C. Thus, when such an article contains a cigarette composition having a glycoside, the glycosidic linkage of the perfume precursor compound is preferably cleaved at a temperature below about 200 ° C to about 300 ° C. As another example, the burning of tobacco typically occurs at a temperature of about 400 °C. Thus, when a conventional smoking article (such as a cigarette or cigar) contains a tobacco composition having a glycoside, the glycosidic linkage of the flavor precursor compound is preferably cleaved at a temperature below about 400 °C.

In a particular embodiment, the glycosidic linkage of the perfume precursor compound is cleaved at a temperature of about 150 ° C or higher to liberate the perfume compound of the present invention. In a particular embodiment, the glycosidic linkage of the perfume precursor compound is cleaved at a temperature of about 400 ° C or less. In a particular embodiment, the glycosidic linkage of the perfume precursor compound is cleaved at a temperature of from about 100 ° C to about 400 ° C, such as between about 150 ° C to about 300 ° C, or between about 200 ° C to about 300 ° C.

The tobacco composition used herein refers to tobacco And a cigarette composition of a flavor precursor compound, and which can be used to make any suitable smoking article that is desired to have a strong smoke flavor. For example, the tobacco composition can be used in a conventional smoking article or in a smoking article that uses an aerosol-generating substrate. The tobacco composition can be a reconstituted tobacco containing a variety of different types of tobacco types and binders and humectants. Humectants are good for aerosol production. When heated, the humectant evaporates and recondenses into small droplets to produce a visible aerosol. The glycosidic linkage of the perfume precursor composition is preferably cleavable in the case of use, rather than cleavage in the case of storage, processing or manufacture.

In the case of a flammable smoking article, such as a cigarette, the cigarette composition can be used in any part of a smoking article having a tobacco substrate, such as a tobacco rod of a conventional cigarette, or one or more filters of a conventional cigarette. If it is a smoking article in which the cigarette composition or component thereof is not burned, the cigarette composition can be applied to any portion of the smoking article having the aerosol-generating substrate.

101‧‧‧Smoking products

102‧‧‧Smoking products

103‧‧‧ front end embolization

104‧‧‧heat source

105‧‧‧ mouthpiece filter

106‧‧‧Aerosol generating substrate

107‧‧‧Transport

108‧‧‧Expansion room

109‧‧‧ hollow cellulose acetate tube

110‧‧‧ mouthpieces

111‧‧‧Aerosol generating substrate

112‧‧‧cigarette paper

113‧‧‧ heating elements

114‧‧‧heat resistant coating

115‧‧‧cigarette paper

116‧‧‧Central airflow channel

117‧‧‧Insulation casing

118‧‧‧Homogeneous tobacco materials

119‧‧‧Aerosol generating device

120‧‧‧ Embossed roll paper

121‧‧‧sheath

122‧‧‧thermal element

124‧‧‧Open cardboard tube

126‧‧‧cellulose acetate tow

128‧‧‧Filter plug paper

Figure 1 shows a schematic view of a smoking article in which the composition of the cigarette is not burned; Figure 2 shows a smoking article which is heated by an electric heat source when engaged with the smoking device; Figure 3 shows that the guaiacol glucoside is in heat The ion detection results of heating in the desorber; Figure 4 shows the results of the guaiacol concentration determined by the stable isotope dilution analysis (SIDA) method for the trapped aerosol.

By way of example with reference to Figure 1, it shows a schematic representation of a non-limiting smoking article 102 in which the cigarette composition is not burned. As shown in FIG. 1, the smoking article 102 includes a combustible heat source 104, an aerosol generating substrate 106, an elongated expansion chamber 108, and a coaxially butted mouthpiece 110, both of which are covered by an outer package of the low permeability cigarette paper 112. .

The combustible heat source 104 is a pyrolyzed porous carbon-based heat source. The combustible heat source 104 is cylindrical and includes a central airflow passage 116 that extends longitudinally through the combustible heat source 104. A substantially gas impermeable iron oxide heat resistant coating 114 is disposed on the inner surface of the central gas flow passage 116. The aerosol-generating substrate 106 is located immediately downstream of the combustible heat source 104 and includes a cylindrical plug of homogenized tobacco material 118 surrounded by a plug wrap 120 that contains a flavor precursor compound and Aerosol forming agent glycerin. The homogenized tobacco material 118 is comprised of longitudinally aligned extruded tobacco material filaments.

The thermally conductive element 122 is comprised of a circumferential aluminum foil tube and is in contact with the anterior segment of the combustor heat source 104 and the aerosol generating substrate 106. As shown in FIG. 1, the rear section of the aerosol-generating substrate 106 is not surrounded by the heat-conducting element 122.

The elongated expansion chamber 108 is located downstream of the aerosol-generating substrate 106 and includes an open cardboard tube 124. The mouthpiece 110 of the smoking article 102 is located downstream of the expansion chamber 108 and contains a cylindrical plug of cellulose acetate tow 126 having a very low filtration efficiency, which is surrounded by the filter plug wrap 128. The mouthpiece 110 can be surrounded by a tipping paper (not shown). The size of the smoking article 102 can be compared to the traditional The cigarettes are similar.

In use, the user ignites the combustible carbon-based heat source 104 and then draws air through the central airflow passage 116 to the downstream mouthpiece 110. The front section of the aerosol-generating substrate 106 is primarily heated via conduction adjacent the unburned rear section of the combustible heat source 104 and the thermally conductive element 122. The inhaled air will be heated as it passes through the central airflow passage 116, and then the aerosol-generating substrate 106 is heated via convection. Heating of the aerosol-generating substrate 106 will release volatile and semi-volatile compounds, including dissociated perfume compounds and glycerol from the aerosol-forming substrate 118, as the heated inhaled air flows through the aerosol-generating substrate. Being taken in it.

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

To make the smoking article 102, a rectangular thermally conductive element 122 is adhered to the cigarette paper 112. The heat source 104, the plug of the aerosol-generating substrate 106, and the expansion chamber 108 are properly aligned and positioned on the cigarette paper 112 that has been adhered to the thermally conductive element 122. The cigarette paper 112 to which the heat conductive member 122 has been attached surrounds the rear portion of the heat source 104, the aerosol generating substrate 106, and the expansion chamber 108, and is glued. The mouthpiece 110 is attached to the open end of the expansion chamber using known filter joining techniques.

In another embodiment of heating a smoking article, the cigarette composition comprising the flavor precursor compound is in direct contact with an unburned heat source such as an electric heat source. Figure 2 shows a smoking article that is heated by an electric heat source when engaged with a smoking device. Smoking article 101 includes a front end The plug 103, the aerosol generating substrate 111, the hollow cellulose acetate tube 109, the transfer section 107, and the mouthpiece filter 105. The five components are sequentially and coaxially aligned and assembled by cigarette paper 115 to form a tobacco rod. The tobacco rod has a mouth end and a distal end, the user inserts the mouth end into his or her mouth when in use, and the distal end is located at the other end of the mouth end of the tobacco rod. When assembled, the tobacco rod 15 is 52 mm long and has a diameter of 7.2 mm. The front end plug 103 is a cylindrical cellulose acetate tow. The aerosol-generating substrate 111 is located downstream of the front end plug 103 and includes a bundle of crimped cast tobacco that is wrapped within the filter paper. Cast leaf tobacco includes an additive comprising glycerin as an aerosol former. The tube 109 is located immediately downstream of the aerosol-generating substrate 111 and is formed of cellulose acetate. The transfer section 107 allows the volatile substance including the fragrance compound released from the aerosol-generating substrate 111 to pass through the tobacco rod toward the mouth end. The volatile material can be cooled in the transfer section 107 to form an aerosol. The mouthpiece filter 105 is a conventional mouthpiece filter formed of cellulose acetate tow. The above-specified elements are combined by being tightly wrapped in the cigarette paper 115.

The aerosol generating device 119 includes a sheath 121 for receiving the smoking article 101 for ingestion. The heating element 113 is located within the sheath 121 and is positioned in a position engageable with the distal end of the smoking article 101. The shape of the heating element 113 is a blade shape having a pointed end. When the smoking article 101 is pressed into the sheath, the sharp point of the heating element 113 will first engage the front end plug 103 and then penetrate into the aerosol generating substrate 111. When the smoking article 101 is properly engaged with the aerosol generating device 119, the heating element 113 is located within the aerosol generating substrate 111. The heat generated by the heating element 113 is transferred via conduction and convection to an aerosol generating base containing a perfume precursor compound. Inside the material 111. The insulating sleeve 117 can surround a portion of the heating element 113 that is in contact with the front end plug 103 and protects it from burning or burning. Of course, it should be understood that the smoking articles described in Figures 1 and 2 are merely examples of two smoking articles in which a cigarette composition comprising a flavor precursor compound described herein can be used. It will be further appreciated that smoking articles comprising a cigarette composition having a flavor precursor compound can also be made using methods other than those described in Figures 1 and 2.

Any suitable method can be used to make a smoking article comprising a cigarette composition having a flavor precursor compound. In general, a method for making a smoking article comprising a cigarette composition having a flavor precursor compound comprises: adding or incorporating a flavor precursor compound or a perfume delivery composition into a cigarette composition, such as tobacco or other substrate; The cigarette composition is incorporated into a smoking article.

In general and as described herein, a method for enhancing the odor or aroma of a cigarette of a cigarette composition comprises adding a flavor precursor compound or a perfume delivery composition to the composition of the cigarette. The glycosidic bond of the perfume precursor compound is hydrolyzed upon heating to cause dissociation of the perfume compound. When a smoker uses (burns or heats) a smoking article, the flavor precursor compound is heated.

Unless otherwise indicated, all scientific and technical terms used herein have the meaning commonly employed in the art. The definitions provided in this article are intended to facilitate the understanding of certain terms used frequently in this article.

The singular forms "a", "the", and "the"

The word "or" used in the scope of the present application and the accompanying patent application generally includes the meaning of "and/or" unless the context clearly dictates otherwise.

The terms "having", "including" and "including" as used herein mean an open-ended meaning and generally mean "including, but not limited to". It should be understood that terms such as "consisting essentially of" and "consisting of" are all included in the category of "including".

Provided below are non-limiting examples illustrating certain aspects of the compounds, compositions, methods, and articles of manufacture disclosed herein.

Example

Example 1: Evaluation of Compounds with Smoke Flavor

Forty-five compounds described in the literature and other sources are listed as candidate materials with smoke flavor characteristics. Certain compounds were tested by a panel of sensory experts and compared to the scent of guaiacol, guaiacol has been determined to best trigger the scent of smoke. Although some compounds can also cause aromas of smoke, they present additional scent that interferes with or weakens the scent of smoke. For example, 2-methoxythiophenol has some smoke odor characteristics, but at the same time has a heavier meat flavor. Many other compounds have been tested and do not give a feeling of smoke.

Although guaiacol is used as an example of leading testing, other phenolic compounds having similar desirable flavor characteristics can also be specified. These compounds include 2,6-dimethoxyphenol (CAS 91-10-1); o-cresol, m-cresol or p-cresol; 3-ethylphenol (CAS 123-07-9); 4-isopropylphenol (CAS 99-89-8); and 2,3-dimethylphenol (CAS 526-75-0).

Example 2: Release of guaiacol from guaiacol glucoside in smoking articles

Synthesis of guaiacol ((2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(2-methoxyphenoxy)tetrahydro-2H-pyran-3,4,5 - Triol) glycoside, and as a result of initial testing with a thermal desorber, it shows that guaiacol is released upon heating. As shown in Figure 3, it shows the initial temperature at which guaiacol is released from glycosides when guaiacol glycoside is heated in a thermal desorber (especially) for the detection of guaiacol ions. It is about 222 °C. This release temperature is well suited for smoking, rather than smoking, smoking articles to increase the smell of smoke in the aerosols produced by such products.

As also shown in Figure 3, a lower amount of acetate ions will be detected at an initial temperature of about 250 °C.

Second, various concentrations of guaiacols glycosides were incorporated into the tobacco. The plug incorporating tobacco is contained in a smoking article that is heated but not burned. The first smoking article comprises a first tobacco blend (blend A, no heat exchanger) and the second smoking article comprises a second tobacco blend (blend B, with a heat exchanger).

The article was aspirated according to the Canadian Department of Health's deep suction method and the aerosol produced by more than 12 soots was collected in a cold trap. The guaiacol concentration of the trapped aerosol has been determined by the stable isotope dilution analysis (SIDA) method. The result is presented in Figure 4.

As shown in Figure 4, guaiacol-glycoside delivers high guaiacol yield when heated by electrical means in the tobacco in the first smoking article (blend A, no heat exchanger) , HX), (the upper half of the curve in Figure 4). Add 1 mg of guaiacol glucoside to the first smoking article Can be caused to release more than 3000 ng/smoke of guaiacol, which is more than 10 times the guaiacol concentration (not shown in Figure 4) observed in conventional cigarettes of the commercial brand. In addition, the second smoking article (blend B, with heat exchanger, HX) (the lower half of the green curve in Figure 4) shows that the release of guaiacol is comparable to that of a commercial brand of traditional cigarettes. High, but significantly lower than smoking articles without heat exchangers. It has been known from previous experiments that compounds having a hydroxyl group (especially phenolic compounds such as guaiacol) are trapped by a heat exchanger.

Next, consider the amount of guaiacol delivered in 12 puffs under the Canadian Department of Health's deep pumping method, and calculate the conversion yield relative to the initial amount of precursor incorporated into each plug. % of the ear to indicate). Although the conversion yield of a smoking article without a heat exchanger is about 10 mol%, the smoking article with a heat exchanger is only 1 mol%. However, the addition of a relatively low amount of guaiacol glucoside can still achieve the target concentration of guaiacol (150-250 Ng/spray, which is observed in commercial brands of conventional cigarettes).

Since only a portion of the tobacco was heated and only a portion of the precursor was degraded during 12 puffs, the conversion yield was significantly less than 100%. The results are shown in Table 1 below.

* The relationship between the concentration in the aerosol (the sum of 12 puff/smoking articles) and the amount of each embedding, expressed in mole units. The plug contains 280 mg of tobacco.

102‧‧‧Smoking products

104‧‧‧heat source

106‧‧‧Aerosol generating substrate

108‧‧‧Expansion room

110‧‧‧ mouthpieces

112‧‧‧cigarette paper

114‧‧‧heat resistant coating

116‧‧‧Central airflow channel

118‧‧‧Homogeneous tobacco materials

120‧‧‧ Embossed roll paper

122‧‧‧thermal element

124‧‧‧Open cardboard tube

126‧‧‧cellulose acetate tow

128‧‧‧Filter plug paper

Claims (14)

A cigarette composition comprising: a chemically synthesized phenol glycoside compound, wherein the cleavage of the glucoside of the phenolic glycoside results in the release of a phenolic compound having the following structure: Wherein R ¹ , R ² , R ³ , R ⁴ and R ⁵ are each independently selected from the group consisting of (i)H and (ii) a C1-C5 linear or branched alkyl or alkoxy group, wherein Alkyl or alkoxy is unsubstituted or substituted by halogen or hydroxy, wherein one or more of R ¹ , R ² , R ³ , R ⁴ and R ⁵ are C1-C5 straight or branched alkyl or alkane An oxy group wherein the phenolic compound has a smoky flavor note. The cigarette composition of claim 1, wherein R ¹ , R ² , R ³ , R ⁴ and R ⁵ are each independently selected from (i) hydrogen and (ii) C1-C5 linear or branched alkyl or alkoxy A group consisting of a group in which the alkyl or alkoxy group is unsubstituted. The cigarette composition of claim 1, wherein the phenolic compound is guaiacol. The cigarette composition of claim 1, wherein the phenolic compound is selected from the group consisting of 2,6-dimethoxyphenol, 3-ethylphenol, o-cresol, m-cresol, p-cresol, 4-isopropyl A group consisting of phenol and 2,3-dimethylphenol. A cigarette composition according to any one of the preceding claims, wherein the glyco moiety of the phenol glycoside is a monosaccharide group, a disaccharide group, a trisaccharide group, or a derivative thereof, wherein one or more A protecting group is used to replace one or more of the one or more hydroxyl groups of the monosaccharide, disaccharide or trisaccharide group. A cigarette composition according to any of the preceding claims, wherein the monosaccharide group is a glucose group. The cigarette composition of claim 1, wherein the phenol glycoside is guaiacol glucoside. A cigarette composition according to any one of the preceding claims, wherein the glucoside linkage cleavage of the phenol glycoside occurs at a temperature above about 140 °C. A cigarette composition according to any of the preceding claims, wherein the glucoside linkage cleavage of the phenol glycoside occurs at a temperature below about 400 °C. A cigarette composition according to any of the preceding claims, wherein the glycosidic linkage cleavage of the phenolic glycoside occurs at a temperature of from about 200 °C to about 300 °C. A cigarette composition according to any of the preceding claims, which further comprises tobacco. A smoking article comprising the composition of any of the preceding claims. A smoking article according to claim 12, which comprises an aerosol-forming substrate, wherein the substrate comprises the cigarette composition. The smoking article of claim 13, wherein the article is designed to be delivered Approximately 10 ng of perfume compound per squirt to 1 mg of perfume compound per squirt.