Smoking article comprising a flavourant

Abstract

The present invention relates to a smoking article including a novel flavorant, and more particularly, to a smoking article including a flavorant including a moiety derived from a flavor compound in a basic skeleton thereof, which is a novel compound decomposed into a lactone compound, a saccharide compound, and a flavor compound upon thermal decomposition.

Description

Technical Field

[0001] This invention relates to smoking articles comprising novel flavoring agents that release flavor components upon heating. Background Technology

[0002] Flavoring agents can be added to smoking products to further improve the taste. The smoke or aerosol produced in smoking products is delivered downstream to the smoker, thereby giving the smoker the satisfaction of smoking. Many factors determine the satisfaction of smoking, the most important of which is the taste of the cigarette perceived by the smoker. Smokers hope to enjoy a variety of tobacco flavors from a single smoking product; therefore, tobacco manufacturers add flavoring substances (such as flavoring agents) to meet smokers' needs, allowing them to experience different aromas or flavors.

[0003] Existing flavoring agents are prone to decomposition at room temperature during long-term storage of smoking media. This causes the flavor components to evaporate, resulting in insufficient aroma to enhance the taste of cigarettes during smoking, or a weakening of aroma persistence or changes in tobacco flavor over time. Therefore, it is necessary to develop a flavoring agent that can improve smoking satisfaction. Furthermore, flavoring agents often decompose during the manufacturing and / or storage of cigarettes, or the aroma disappears due to evaporation. Therefore, there is a need to develop a flavoring agent that can prevent or delay the release of volatile flavoring agents, thereby extending shelf life, and that can fully release the aroma when the user uses it (e.g., while smoking). Summary of the Invention

[0004] The problem the invention aims to solve

[0005] Existing flavoring compounds exhibit poor chemical stability at room temperature (rt) or near room temperature, leading to structural transformations or decomposition and the volatilization of flavor components. To address this issue, this invention provides a smoking product comprising a novel flavoring agent, which releases its flavor components through thermal decomposition upon heating.

[0006] However, the technical problems to be solved by the present invention are not limited to those mentioned above. Other technical problems not mentioned can be easily understood by those skilled in the art through the following description.

[0007] means for solving problems

[0008] According to one embodiment of the present invention, a smoking article comprising a flavoring agent is provided, said flavoring agent being a compound represented by the following chemical formula 1:

[0009] [Chemical Formula 1]

[0010]

[0011] In the chemical formula 1,

[0012] n is an integer of 1 or 2.

[0013] M is selected from alkali metals and transition metals.

[0014] R is a straight-chain or branched alkyl group having 1 to 30 carbon atoms.

[0015] Moiety A is a moiety derived from a fragrance compound comprising at least one of an aromatic ring having a hydroxyl group, an aliphatic ring, and an aliphatic chain, wherein the hydroxyl group participates in a carbonate bond. A' is equivalent to a fragrance compound other than a hydroxyl group.

[0016] Invention Effects

[0017] According to one embodiment of the present invention, the flavoring agent of the smoking article of the present invention can improve the pungent taste in the sideflow smoke by producing a flavoring component when smoking, and the flavoring agent releases the flavoring component through thermal decomposition during heating, thereby improving the taste of the cigarette and maintaining a constant taste.

[0018] According to one embodiment of the present invention, smoking articles including the flavoring agent of the present invention can be applied in various ways, in various locations, and / or with various modifications, thereby controlling and improving the tobacco flavor, atmosphere, etc. Attached Figure Description

[0019] Figure 1 The results are NMR analysis of ethyl 4-hydroxyheptanate (2a) prepared in the example according to an embodiment of the present invention.

[0020] Figure 2 The results are NMR analysis of ethyl 4-(mentholylcarbonyloxy)heptanate (3a) prepared in an embodiment of the present invention.

[0021] Figure 3 The results are NMR analysis of 4-(mentholylcarbonyloxy)heptanoic acid (4a) prepared in an embodiment of the present invention.

[0022] Figure 4 The results are NMR analysis of 4-(mentholylcarbonyloxy)nonanoic acid (4b) prepared in an embodiment of the present invention.

[0023] Figure 5 The results are NMR analysis of 5-(mentholylcarbonyloxy)decanoate (3c) prepared in an embodiment of the present invention.

[0024] Figure 6The results are NMR analysis of 5-(mentholylcarbonyloxy)decanoate (3c) prepared in an embodiment of the present invention.

[0025] Figure 7 The results are NMR analysis of 5-(mentholylcarbonyloxy)decanoic acid (4c) prepared in an embodiment of the present invention.

[0026] Figure 8 The results are NMR analysis of 5-(mentholylcarbonyloxy)decanoic acid (4c) prepared in an embodiment of the present invention.

[0027] Figure 9 The results are NMR analysis of ethyl 4-hydroxyundecanoate (2d) prepared in an embodiment of the present invention.

[0028] Figure 10 The results are NMR analysis of ethyl 4-hydroxyundecanoate (2d) prepared in an embodiment of the present invention.

[0029] Figure 11 The results are NMR analysis of ethyl 4-(mentholylcarbonyloxy)undecanoate (3d) prepared in an embodiment of the present invention.

[0030] Figure 12 The results are NMR analysis of 4-(mentholylcarbonyloxy)undecanoic acid (4d) prepared in an embodiment according to an embodiment of the present invention.

[0031] Figure 13 The results are NMR analysis of 4-(mentholylcarbonyloxy)undecanoic acid (4d) prepared in an embodiment according to an embodiment of the present invention.

[0032] Figure 14 The results are NMR analysis of ethyl 4-(benzyloxycarbonyloxy)undecanoate (3e) prepared in an embodiment according to an embodiment of the present invention.

[0033] Figure 15 The results are thermal analysis results of sodium (4-menthylcarbonyloxy)undecanoate (5d) prepared in an embodiment according to an embodiment of the present invention.

[0034] Figure 16 This is the compositional distribution of sodium (4-menthylcarbonyloxy)undecanoate (5d) prepared in an embodiment of the present invention as a function of thermal decomposition temperature.

[0035] Figure 17 This is the compositional distribution of sodium (4-menthylcarbonyloxy)undecanoate (5d) prepared in an embodiment of the present invention as a function of thermal decomposition temperature.

[0036] Figure 18 The accompanying drawings illustrate the decomposition and migration process of aroma components in a smoking article according to an embodiment of the present invention during combustion and smoking. Detailed Implementation

[0037] Embodiments of the present invention will now be described in detail with reference to the accompanying drawings. In describing the present invention, detailed descriptions of well-known functions or structures will be omitted where it would unnecessarily obscure the spirit of the invention. Furthermore, the terminology used in this specification to accurately describe embodiments may vary depending on the intent of the user or operator, or the conventions of the technical field to which this invention pertains. Therefore, the definitions of terms should be based on the overall content of this specification. The same reference numerals in each figure denote the same components.

[0038] Throughout the specification, when it is stated that a component is "on" another component, this includes not only the case where one component is in contact with another component, but also the case where another component exists between the two components.

[0039] Throughout the specification, when a section “includes” a component, it means that other components may be included, rather than excluding other components.

[0040] The following detailed description of the smoking article including the novel flavoring agent of the present invention is provided with reference to the embodiments and accompanying drawings. However, the present invention is not limited to these embodiments and drawings.

[0041] This invention relates to smoking articles comprising novel flavoring agents. According to one embodiment of the invention, the flavoring agent releases flavor components through thermal decomposition when heated, thereby improving the flavor and persistence of cigarettes.

[0042] This invention relates to smoking articles comprising novel flavoring agents that release flavor components upon thermal decomposition. According to one embodiment of the invention, the flavoring agent releases volatile flavor components through thermal decomposition when heated. Specifically, by applying this synthetic compound that releases flavor components upon thermal decomposition to the constituent elements of cigarettes (such as cigarette paper), the flavor components (e.g., lactones and / or menthol) are released due to heat when the cigarette is heated, particularly during smoking, thereby improving the pungent odor in sidestream smoke. Furthermore, when applied to the medium of a heated tobacco stick, the flavor components can be made to last longer. For heated cigarettes, static heating causes the flavor components contained in the medium to be consumed during the initial puff, but the flavoring agent is only released upon thermal decomposition; therefore, even with continuous smoking, flavor components are produced on the last puff, thus maintaining a constant tobacco flavor.

[0043] According to one embodiment of the present invention, the fragrance agent may be a compound represented by the following chemical formula 1.

[0044] [Chemical Formula 1]

[0045]

[0046] As an example of the present invention, the fragrance compound in Formula 1 is obtained through a carbonate bond ( The compound of Formula 1 is covalently bonded, and upon heating, it decomposes into fragrance compounds and lactone compounds, thereby releasing fragrance. For example, the compound of Formula 1 reacts with the hydroxyl group of the fragrance compound through a ring-opening mechanism of lactone compounds, thereby covalently bonding the fragrance compound through carbonate bonds. It can act as a protecting group at room temperature and / or near-room temperature, preventing conversion to lactone compounds due to ring closure. The compound of Formula 1 is structurally stable and has low volatility at approximately room temperature or near-room temperature. Upon heating, the carbonate bonds break through a ring-closure mechanism, thereby decomposing into lactone compounds and fragrance compounds, releasing fragrance, and producing harmless carbon dioxide during the decomposition process. In other words, during heating, the carbonate bonds break and decompose into fragrance compounds, generating carbon dioxide. Then, through ring closure, it decomposes into lactone compounds, thereby releasing fragrance.

[0047] According to one embodiment of the present invention, n in the chemical formula 1 can be an integer of 1 or 2. R is a straight-chain or branched alkyl group having 1 to 30 carbon atoms; preferably, it can be a straight-chain or branched alkyl group having 2 to 10 carbon atoms.

[0048] According to an embodiment of the present invention, moiety A in Formula 1 may be a moiety derived from a fragrance compound comprising at least one of an aromatic ring having a hydroxyl group, an aliphatic ring having a hydroxyl group, and an aliphatic chain having a hydroxyl group. The hydroxyl group may comprise at least one of a ring, a chain, or both (e.g., one or both). This may correspond to a substituent having a hydroxyl group, a basic skeleton, and / or a moiety. The hydroxyl group in Formula 1 may participate in a carbonate bond, and A' may correspond to a fragrance compound other than the hydroxyl group. That is, the hydroxyl group of the fragrance compound in moiety A is protected by a carbonate bond, preventing ring-closure-based decomposition reactions at room temperature.

[0049] According to an embodiment of the present invention, the fragrance compound may be selected from cyclic monoterpenoids having hydroxyl groups, acyclic monoterpenoids having hydroxyl groups, aromatic compounds having 6 to 10 carbon atoms having hydroxyl groups, and compounds having 5 to 10 carbon atoms having hydroxyl groups; or non-aromatic rings having 5 to 6 carbon atoms and their isomers. For example, the fragrance compound may be selected from the following compounds, which are compounds produced by the breaking of carbonate bonds during the thermal decomposition of the chemical formula 1:

[0050] , , , , , , , , , , , , , , , , , , , , , , , , , as well as .

[0051] According to an embodiment of the present invention, A' in moiety A can be selected from the following chemical formulas. Wherein, * represents an oxygen site within the carbonate bond:

[0052] , , , , , , , , , , , , , , , , , , , , , , , , , as well as .

[0053] According to one embodiment of the present invention, M can be selected from alkali metals and transition metals. M can form a salt with the oxygen of the ester group to improve its solubility in water-soluble solvents and facilitate its application in food and smoking products. For example, the transition metal can be selected from Zr, Mg, Ca, Co, Rh, Ir, Nb, Pd, Pt, Fe, Ru, Os, Cr, Mo, W, Mn, Tc, Re, Cu, Ag, and Au; the alkali metal can be selected from Li, Na, K, Rb, and Cs. For example, M can be a metal that forms a monovalent cation, and it can be selected from Li, Na, and K.

[0054] According to one embodiment of the present invention, the lactone compound may be a γ-lactone of chemical formula 2 or a δ-lactone of chemical formula 3.

[0055] [Chemical Formula 2]

[0056]

[0057] [Chemical Formula 3]

[0058]

[0059] In one example of the present invention, R in both Formula 1 and Formula 2 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms, preferably a straight-chain or branched alkyl group having 2 to 10 carbon atoms.

[0060] According to one embodiment of the present invention, lactones may be selected from those described by the following chemical formulas:

[0061] , , , , , , , , , , , as well as .

[0062] According to one embodiment of the present invention, the compound may be selected from the following chemical formulas 1-1 to 1-26.

[0063] [Chemical Formula 1-1]

[0064]

[0065] [Chemical Formula 1-2]

[0066]

[0067] [Chemical Formulas 1-3]

[0068]

[0069] [Chemical Formulas 1-4]

[0070]

[0071] [Chemical Formulas 1-5]

[0072]

[0073] [Chemical Formulas 1-6]

[0074]

[0075] [Chemical Formulas 1-7]

[0076]

[0077] [Chemical Formulas 1-8]

[0078]

[0079] [Chemical Formulas 1-9]

[0080]

[0081] [Chemical Formulas 1-10]

[0082]

[0083] [Chemical Formula 1-11]

[0084]

[0085] [Chemical Formula 1-12]

[0086]

[0087] [Chemical Formula 1-13]

[0088]

[0089] [Chemical Formula 1-14]

[0090]

[0091] [Chemical Formula 1-15]

[0092]

[0093] [Chemical Formula 1-16]

[0094]

[0095] [Chemical Formula 1-17]

[0096]

[0097] [Chemical Formula 1-18]

[0098]

[0099] [Chemical Formula 1-19]

[0100]

[0101] [Chemical Formula 1-20]

[0102]

[0103] [Chemical Formula 1-21]

[0104]

[0105] [Chemical Formula 1-22]

[0106]

[0107] [Chemical Formula 1-23]

[0108]

[0109] [Chemical Formula 1-24]

[0110]

[0111] [Chemical Formula 1-25]

[0112]

[0113] [Chemical Formula 1-26]

[0114]

[0115] Wherein, M and R are as defined in the chemical formula 1.

[0116] According to one embodiment of the present invention, the thermal decomposition temperature of the compound can be 70°C or higher; 80°C or higher; 90°C or higher; or 100°C or higher, preferably 120°C or higher; 150°C or higher; 200°C or higher; or more preferably 200°C to 300°C. Furthermore, it can be thermally decomposed in an environment including oxygen and / or moisture.

[0117] According to one embodiment of the present invention, the smoking article may include at least one flavoring compound represented by Chemical Formula 1 of the present invention. When the smoking article is heated and / or burned, the flavoring compound provides flavor through thermal decomposition. For example, when the smoking article is heated and / or burned, flavor may be released into the mainstream smoke and / or sidestream smoke, thereby providing an effect that improves the mainstream smoke and / or sidestream smoke. For example, Figure 18 The migration process of the aroma components of the present invention is illustrated, which can be achieved in... Figure 18 The flavoring compound is applied to the heated and / or burned portion and / or the portion near and / or affected by heat of the smoking article. When the flavoring compound is applied, it can improve the sidestream smoke as the flavoring components migrate through the sidestream / mainstream smoke.

[0118] exist Figure 18 A burning con is formed in (a) and (b), and then sidestream smoke is generated during combustion, producing flavor components that will be added to the sidestream smoke. This is because the heat from the burning con causes the synthetic flavorings coated on the cigarette paper to thermally decompose, thereby releasing flavor components (e.g., undecalactone).

[0119] exist Figure 18 In (c), as outside air flows in during smoking, some of the thermally decomposed aroma components can be inhaled into the mainstream smoke.

[0120] According to one embodiment of the present invention, the compound represented by the chemical formula 1, in the smoking article, may be 0.0001 parts by weight or more; 0.001 parts by weight or more; 0.1 parts by weight or more; 1 part by weight or more; 1 to 5 parts by weight; 1 to 10 parts by weight; or 1 to 20 parts by weight, relative to 100 parts by weight of the smoking medium. Thus, the flavor, atmosphere, etc. of the sidestream smoke and / or mainstream smoke during smoking can be controlled and improved.

[0121] According to one embodiment of the present invention, when smoking, the amount of flavor components such as lactones emitted by the compound represented by Chemical Formula 1 in the smoking product may be 0.00001 parts by weight or more; 0.0001 parts by weight or more; 0.001 parts by weight or more; 0.1 parts by weight or more; 1 part by weight or more; 1 to 5 parts by weight; 1 to 10 parts by weight; or 1 to 20 parts by weight relative to 100 parts by weight of the smoking medium. Therefore, the flavor, atmosphere, etc. of the sidestream smoke and / or mainstream smoke during smoking can be controlled and improved.

[0122] According to one embodiment of the present invention, the smoking article may include a slurry, paste, liquid, gel, powder, bead, sheet, film, fiber or molded body containing a compound represented by the chemical formula 1.

[0123] According to one embodiment of the present invention, the smoking article may be made by applying a compound represented by the chemical formula 1 or a composition comprising thereof, or by manufacturing thereof. For example, it may be a component and / or accessory of the smoking article. Preferably, it may be a component and / or accessory of the heated area in the smoking article. For example, it may be a smoking medium (e.g., liquid, gel, solid, slurry, paste), paper tube, cigarette tube, filter tip (e.g., tubular filter tip, fiber filter tip, woven filter tip, paper filter tip, capsule filter tip), rolling paper, cigarette paper, tipping paper, packaging paper, cartridge (e.g., heated cartridge), etc., and may include components known in the technical field of the present invention without departing from the purpose of the present invention, which will not be specifically described here.

[0124] According to one embodiment of the present invention, the composition includes the flavoring agent of the present invention (i.e., the flavoring compound represented by the chemical formula 1), and may also include a carrier, an additive, or both, depending on the intended use. The carrier and additive are carriers and additives permitted for use in food or smoking articles, and may include, for example, solvents, adhesives, diluents, disintegrants, lubricants, flavoring agents, coloring agents, preservatives, antioxidants, emulsifiers, stabilizers, flavor enhancers, sweeteners, etc., but are not limited thereto.

[0125] According to one embodiment of the present invention, the composition may further include a substrate (or matrix) component, depending on the intended use. For example, it may include paper, pulp, wood, polymer resin (e.g., cellulose), fiber, vegetable oil, petroleum-derived oil (e.g., paraffin), animal oil, wax, fatty acids (e.g., animal fats, vegetable fats, saturated fatty acids, unsaturated fatty acids (e.g., monounsaturated or polyunsaturated fatty acids) having 1 to 50 carbon atoms). The substrate component may further contain organic and / or inorganic substances or ceramic powders (e.g., chalk, perlite, vermiculite, diatomaceous earth, colloidal silica, magnesium oxide, magnesium sulfate, magnesium carbonate), wetting agents (e.g., glycerol or propylene glycol), and acetate compounds.

[0126] According to one embodiment of the present invention, the composition may further include a tobacco component, depending on its intended use. When used in a smoking article, the composition can generate aroma in mainstream smoke and / or sidestream smoke under smoking conditions. The tobacco component may be a solid substance based on tobacco raw materials such as reconstituted tobacco, shredded tobacco, or reconstituted tobacco, and may be selected from tobacco leaves, extruded tobacco, and bandcast tobacco. Furthermore, the composition may also include an aerosol generator as a cigarette medium, non-limiting examples of which include sorbitol, glycerin, propylene glycol, triethylene glycol, lactic acid, diacetate, triacetate, triethylene glycol diacetate, triethyl citrate, ethyl myristate, isopropyl myristate, methyl stearate, dimethyl dodecanoate, and dimethyl tetradecanoate.

[0127] According to one embodiment of the present invention, the flavoring agent may be 0.0001% to 100% by weight (or less than 100% by weight); more than 0.001% by weight; more than 0.01% by weight; 0.1% to 80% by weight; 0.0001% to 60% by weight; 0.001% to 50% by weight; 0.1% to 30% by weight; 1% to 20% by weight; 5% to 20% by weight; or 5% to 10% by weight. When included within the ranges described, the flavor can be released through thermal decomposition of the flavoring agent, and when used in smoking articles, it can improve the flavor of cigarettes.

[0128] According to one embodiment of the present invention, the composition can be prepared into various phases, such as solids (e.g., powders, crystals, flakes, pulverized material), suspensions, slurries, pastes, gels, liquids, emulsions, or aerosols. For example, the composition can be molded, mixed with a desired product, or used by methods known in the art such as printing, dipping, spraying, and / or coating, which will not be specifically described here.

[0129] According to one embodiment of the present invention, the "smoking article" can refer to tobacco, tobacco derivatives, expanded tobacco, reconstituted tobacco, or any product that can be inhaled like smoking, or any product that provides a smoking experience, regardless of whether it is based on a tobacco substitute. For example, the smoking article can refer to aerosol-generating smoking articles such as cigarettes, cigars, cigarillos, and e-cigarettes. The smoking article may include aerosol-generating substances or aerosol-generating matrices. Alternatively, the smoking article may include solid materials based on tobacco raw materials such as reconstituted tobacco, shredded tobacco, or reconstituted tobacco. The smoking article may include volatile compounds.

[0130] According to one embodiment of the present invention, the smoking product may be a cigarette, a liquid cigarette, or a blended cigarette, and may be a combustible cigarette or a heated cigarette. Alternatively, it may be an electronic cigarette (e.g., an electronic heated cigarette).

[0131] According to one embodiment of the present invention, the smoking article may include at least one of a sheet, a film, and a filter tip that has a compound represented by Chemical Formula 1 partially printed or coated on all or at least a portion of its surface. Furthermore, the compound represented by Chemical Formula 1 may be printed or coated on one or both surfaces.

[0132] According to one embodiment of the present invention, the compound represented by Chemical Formula 1 is printed as a pattern along the axial, transverse, or two other directions of a smoking article. The pattern can be printed on all or part of at least one side of the smoking article, or on at least a portion thereof. For example, the smoking article may include one or more patterned areas along the axial, transverse, or two other directions, which can control the flavor and atmosphere of the sidestream smoke and / or mainstream smoke during smoking. For example, the pattern can be arranged in at least one shape selected from straight lines, dashed lines, grids, polygons, dots, circles, and ellipses. For example, the size of the pattern can be 0.01 mm or more; 0.1 mm or more; 1 mm to 10 mm; or 1 mm to 5 mm. The size can refer to thickness, length, diameter, etc., and in dotted patterns, it can be spacing, intervals, etc. For example, the spacing can be 0.01 mm to 1 mm.

[0133] According to one embodiment of the present invention, the smoking article may include a smoking medium portion and a filter portion. The smoking medium portion may include cigarette paper containing a compound represented by Chemical Formula 1, a smoking medium, or both.

[0134] According to one embodiment of the present invention, when the flavoring agent is applied to the cigarette paper of a cigarette and the cigarette is heated and / or burned, especially when smoke is generated, the heat releases flavoring components (e.g., lactones and / or flavoring components), thereby improving the pungent odor in the sideflow smoke.

[0135] According to one embodiment of the present invention, when used in a medium for heated tobacco sticks, the aroma components can be made to retain their aroma for a longer period of time. For heated cigarettes, static heating causes the aroma components contained in the medium to be consumed during the initial puff, but the aroma agent is only released when it is decomposed by heat. Therefore, even with continuous puffing, aroma components will be produced on the last puff, thereby maintaining a constant tobacco flavor.

[0136] According to one embodiment of the present invention, in manufacturing the smoking article, the flavoring agent itself may be mixed with a matrix or substrate, or a composition including the flavoring agent may be mixed with, printed, impregnated (or impregnated), coated and / or sprayed with a matrix or substrate.

[0137] According to one embodiment of the present invention, the compound represented by the chemical formula 1 can be coated on cigarette paper or added to a smoking medium (e.g., tobacco medium).

[0138] As an example of the present invention, the method of adding the compound represented by Chemical Formula 1 to a smoking medium (e.g., tobacco medium) is the same as the method of adding other flavorings during the tobacco manufacturing process. The compound represented by Chemical Formula 1 is dissolved in a solvent for dilution and then added to the tobacco medium (e.g., tobacco shreds) by spraying. Furthermore, it is water-soluble in the reconstituted tobacco manufacturing process, thereby being added through various methods during the manufacture of reconstituted tobacco.

[0139] As an example of the present invention, there are many methods for coating the cigarette paper. It can be coated on the entire cigarette stem or partially coated on at least a portion of the cigarette stem. Furthermore, it can be coated onto the cigarette paper of a cigarette, or added during the manufacturing process of the cigarette paper. For example, the entire surface of the cigarette paper can be distributed with patterned areas of compounds represented by Chemical Formula 1, or patterned areas of compounds represented by Chemical Formula 1 can be partially distributed based on the transverse and / or axial direction of the cigarette stem. The position of the patterned areas can control the flavor and atmosphere of the side-flow smoke. For example, the cigarette paper can have one or more patterned areas, and these areas can be formed at different locations on the cigarette paper stem, such as near the distal side of the cigarette stem (e.g., the cigarette tip or lighting position), near the filter tip, or in the middle portion. For example, the pattern can be formed as a line (or transverse), a band (or axial), or based on both in the cigarette stem.

[0140] For example, in the cigarette paper, the patterned area can be 5%, 10%, 20%, 30%, 50%, 70%, 90%, and 95% of the length of the cigarette paper (or the bar, i.e., from the far side).

[0141] As an example of the present invention, when applied to cigarette paper, in the process of manufacturing cigarette paper, such as raw material peeling → removal of black skin → screening → soaking → cooking → washing / screening → bleaching → pulping → pulp preparation → stirring → papermaking → pressing → drying → finished product, a compound represented by chemical formula 1 may be added during the soaking or papermaking stage.

[0142] As an example of the present invention, the compound represented by the chemical formula 1 can be mixed or dissolved in a solvent, which may include an organic solvent and / or water that can disperse and / or dissolve the compound. By having solubility, it can be easily added in the papermaking process with water or alcohol when manufacturing cigarette paper.

[0143] For example, when cigarettes are being produced at a cigarette manufacturing plant (high speed), ink can be added to the cigarette stem, much like stamping ink.

[0144] For example, during cigarette manufacturing, it can be added by spraying it onto the cigarette rod.

[0145] For example, the amount of the compound relative to 100 parts by weight of the smoking medium (or tobacco portion) is 0.0001 parts by weight or more; 1 part by weight or more; 5 parts by weight or more; or 1 to 20 parts by weight.

[0146] According to one embodiment of the present invention, the smoking medium may further include flavoring agents and tobacco raw materials (e.g., medium raw materials, tobacco leaves), or may further include additives. As another example, the flavoring agent may be added as a flavoring agent when manufacturing the components and / or parts of a smoking article, thereby mixing with a base material, solvent, flavoring material, smoking medium material, etc., suitable for the smoking article. Furthermore, the smoking medium may be a liquid, gel, or solid.

[0147] The present invention will be described in more detail below through embodiments and comparative examples, but the following embodiments are only used to illustrate the present invention, and the content of the present invention is not limited to the following embodiments.

[0148] Example 1

[0149] 1. Synthesis of sodium (4-mentylcarbonyloxy)heptanoate, 5a

[0150]

[0151] (1-1) Synthesis of ethyl 4-hydroxyheptanoate [2a]

[0152] 20 g of γ-heptalactone (0.15 mol) was dissolved in 100 mL of methanol. While stirring, 11.17 g of KOH (0.16 mol, 1.05 eq.) was slowly added, and the reaction was carried out at room temperature for 12 hours. After concentrating the reaction solution under reduced pressure, 80 mL of DMF was added, followed by the addition of 17 g of bromoethane (0.15 mol, 1 eq.) while stirring, and the reaction was carried out for another 12 hours. 100 mL of water was added to the reaction solution, and the mixture was extracted with ethyl acetate, followed by washing with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain 18.1 g of the target product 2a (66.7%, two steps).

[0153] 1H NMR (CDCl3, 400.13MHz); δ 8.01 (s, 1H, -OH), 4.12 (q, 2H, J = 8 Hz, COO-CH2-), 3.63 (m, 1H, CH-O), 2.42 (m, 2H, CO-C H 2), 1.81 ~ 0.92 (m, 12H, alkyl).

[0154] (1-2) Synthesis of ethyl 4-(mentylcarbonyloxy)heptanoate [3a]

[0155] 18 g of ethyl 4-hydroxyheptanoate (2a, 0.1 mol) was dissolved in 120 mL of THF, then 16 g of pyridine (0.2 mol, 2 eq.) was added, and the mixture was cooled with ice water while stirring. Simultaneously, 20 mL of THF solution containing 23 g of mentyl chloroformate (0.1 mol, 1 eq.) was slowly dropped in. After one hour, the reaction mixture was heated to room temperature and reacted overnight. Water was then added, and the mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, a saturated sodium bicarbonate solution, and brine, respectively, then dried over MgSO4, and concentrated under reduced pressure to obtain 30 g (81% yield) of the target product 3a as a yellow liquid.

[0156] 1 H NMR (CDCl3, 400.13MHz); δ 4.74 (7tet, 1H, J = 4 Hz, -COOCH-), 4.51 (td, 1H, J = 9, 4 Hz, COO-CH-), 4.12 (q, 2H, J = 8 Hz, COO-CH2-), 2.36 (m, 2H, CO-CH2-), 1.93 ~ 0.79 (m, 30H, alkyl).

[0157] (1-3) Synthesis of 4-(mentylcarbonyloxy)heptanoic acid [4a]

[0158] 25 g of ethyl 4-(mentylcarbonyloxy)heptanoate (3a, 68.5 mmol) was dissolved in 100 mL of THF and 30 mL of distilled water. 4.2 g of lithium hydroxide monohydrate (102.4 mmol, 1.5 eq.) was added, and the mixture was reacted at room temperature for 12 hours. 50 mL of distilled water was added, and extraction was performed using ether. The aqueous layer was adjusted to pH 3 with concentrated hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure to obtain 21.8 g (81% yield) of the target product 4a as a yellow liquid.

[0159] 1 H NMR (CDCl3, 400.13MHz); δ 4.76 (m, 1H, -COOCH-), 4.52 (td, 1H, J = 9, 4 Hz, COO-CH-), 4.11 (q, 2H, J = 8 Hz, COO-CH2-), 2.42 (m, 2H, CO-CH2-), 1.99 ~ 0.82 (m, 27H, alkyl).

[0160] (1-4) Synthesis of sodium (4-mentylcarbonyloxy)heptanoate [5a]

[0161] 2.5 g of 4-(mentylcarbonyloxy)hepanoic acid (7.5 mmol) was dissolved in 20 mL of 95% ethanol, and 0.29 g of 98% NaOH (0.95 eq) was added. The mixture was stirred at room temperature for two hours. The water and ethanol were evaporated using the azeotropic effect. Toluene was then added to remove the water, followed by the addition of hexane and ethyl acetate. The mixture was then filtered to obtain a white solid.

[0162] 2. Synthesis of sodium 4-(mentylcarbonyloxy)nonanoate, 5b

[0163] [Option 2]

[0164]

[0165] (2-1) Synthesis of ethyl 4-hydroxynonanoate [2b]

[0166] 20 g of γ-nonalactone (0.13 mol) was dissolved in 100 mL of methanol. While stirring, 9.18 g of KOH (0.14 mol, 1.05 eq.) was slowly added, and the reaction was carried out at room temperature for 12 hours. The reaction solution was concentrated under reduced pressure, and 80 mL of DMF was added with stirring. While stirring, 14 g of bromoethane (0.13 mol, 1 eq.) was added, and the reaction was carried out for 12 hours. 100 mL of water was added to the reaction solution, and the mixture was extracted with ethyl acetate, followed by washing with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain 24 g (93%, two steps) of the target product 2b.

[0167] (2-2) Synthesis of ethyl 4-(mentylcarbonyloxy)nonanoate [3b]

[0168] 24 g of ethyl 4-hydroxynonanoate (2b, 0.12 mol) was dissolved in 120 mL of THF. 18 g of pyridine (0.42 mol, 2 eq.) was added, and the mixture was cooled with ice water. While stirring, 30 mL of THF solution containing 26 g of menthyl chloroformate (0.12 mol, 1 eq.) was slowly dropped in. After one hour, the reaction mixture was heated to room temperature and reacted overnight. Water was then added, and the mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, saturated sodium bicarbonate solution, and brine, respectively, and dried over MgSO4. The solution was then concentrated under reduced pressure to obtain 34 g (74.5% yield) of the target product 3b as a yellow liquid.

[0169] 1 H NMR (CDCl3, 400.13MHz); δ 4.74 (7tet, 1H, J = 4 Hz, -COOCH-), 4.51 (td, 1H, J = 9, 4 Hz, COO-CH-), 4.12 (q, 2H, J = 8 Hz, COO-CH2-), 2.36 (m, 2H, CO-CH2-), 1.93 ~ 0.79 (m, 23H, alkyl).

[0170] (2-3) Synthesis of 4-(mentylcarbonyloxy)nonanoic acid [4b]

[0171] 11.5 g of ethyl 4-(mentholylcarbonyloxy)nonanoate (3, 29.9 mmol) was dissolved in 50 mL of THF and 20 mL of distilled water. 2 g of lithium hydroxide monohydrate (48.7 mmol, 1.6 eq.) was added, and the mixture was reacted at room temperature for 12 hours. 50 mL of distilled water was added, and extraction was performed using ether. The aqueous layer was adjusted to pH 3 with concentrated hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure to give 8.6 g (80% yield) of the target product 4b as a yellow liquid.

[0172] 1 ¹H NMR (CDCl₃, 400.13 MHz); δ 4.75 (m, 1H, -COOCH-), 4.49 (m, 1H, COO-CH-), 2.04 (m, 2H, CO-CH₂-), 1.93 ~ 0.79 (m, 31H, alkyl).

[0173] (2-4) Synthesis of sodium 4-(mentylcarbonyloxy)nonanoate [5b]

[0174] 2.5 g of 4-(mentylcarbonyloxy)nonanoic acid (4b, 7.5 mmol) was dissolved in 20 mL of 95% ethanol, and 0.29 g of 98% NaOH (0.95 eq) was added. The mixture was stirred at room temperature for two hours. The water and ethanol were evaporated using the azeotropic effect. Toluene was then added to remove the water, followed by the addition of hexane and ethyl acetate, and the mixture was filtered to obtain a white solid.

[0175] 3. Sodium 5-(mentylcarbonyloxy)decanoate, 5c]

[0176] [Option 3]

[0177]

[0178] (3-1) Synthesis of ethyl 5-hydroxydecanoate (2c)

[0179] 10 g of δ-Decalactone (58.7 mmol) was dissolved in 50 mL of methanol. While stirring, 4.2 g of KOH (64.7 mmol, 1.05 eq.) was slowly added, and the reaction was carried out at room temperature for 12 hours. The reaction solution was concentrated under reduced pressure, and 40 mL of DMF was added. While stirring, 6.4 g of bromoethane (58.7 mmol, 1 eq.) was added, and the reaction was carried out for 12 hours.

[0180] 100 mL of water was added to the reaction solution and the mixture was extracted with ethyl acetate, followed by washing with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain 7.6 g (60%, two steps) of the target product 2c.

[0181] (3-2) Synthesis of ethyl 5-(mentylcarbonyloxy)decanoate [3c]

[0182] 7.5 g of ethyl 4-hydroxynonanoate (2c, 34.6 mmol) was dissolved in 50 mL of THF. 5.3 g of pyridine (69.2 mmol, 2 eq.) was added, and the mixture was cooled with ice water. Then, while stirring, 20 mL of THF solution containing 8.3 g of menthyl chloroformate (37.9 mmol, 1.1 eq.) was slowly dropped in. After one hour, the reaction mixture was heated to room temperature and reacted overnight. Water was then added, and the mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, saturated sodium bicarbonate solution, and brine, respectively, dried over MgSO4, and concentrated under reduced pressure. The mixture was subjected to silica gel column chromatography using a 7:1 mixture of hexane and ethyl acetate to obtain 4.5 g (32.6% yield) of the target product 3c.

[0183] 1 H NMR (CDCl3, 400.13MHz); δ 4.72 (m, 1H, -COOCH-), 4.52 (m, 1H, COO-CH-), 4.12 (q, 2H, J = 8 Hz, COO-CH2-), 2.31 (t, 2H, J = 8 Hz, CO-CH2-), 2.08 ~ 0.86 (m, 27H, alkyl), 0.79 (d, 6H, J = 8 Hz, -CH3).

[0184] (3-3) Synthesis of 5-(mentylcarbonyloxy)decanoic acid [4c]

[0185] 2.7 g of ethyl 4-(mentholylcarbonyloxy)nonanoate (3c, 6.8 mmol) was dissolved in 20 mL of THF and 10 mL of distilled water. 0.42 g of lithium hydroxide monohydrate (10.2 mmol, 1.5 eq.) was added, and the mixture was reacted at room temperature for 12 hours. 10 mL of distilled water was added, and extraction was performed using ether. The aqueous layer was adjusted to pH 3 with concentrated hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure to obtain 2.1 g (78% yield) of the target product 4b as a yellow liquid.

[0186] 1 ¹H NMR (CDCl₃, 400.13 MHz); δ 4.72 (m, 1H, -COOCH-), 4.51 (td, 1H, J = 8, 4 Hz, COO-CH-), 4.11 (q, 2H, J = 8 Hz, COO-CH₂-), 2.38 (m, 2H, CO-CH₂-), 2.06 ~ 0.78 (m, 33H, alkyl).

[0187] (3-4) Synthesis of sodium 5-(mentylcarbonyloxy)decanoate, 5c]

[0188] 5-(mentylcarbonyloxy)decanoic acid (4c, 7.5 mmol) was dissolved in 20 mL of 95% ethanol. After adding 0.29 g of 98% NaOH (0.95 eq), the mixture was stirred at room temperature for two hours. The water and ethanol were evaporated using an azeotropic reaction. Toluene was then added to remove the water, followed by the addition of hexane and ethyl acetate, and the mixture was filtered to obtain a white solid.

[0189] 4. Synthesis of sodium (4-mentylcarbonyloxy)undecanoate, 5d

[0190] [Option 4]

[0191]

[0192] (4-1) Synthesis of ethyl 4-hydroxyundecanoate [2d]

[0193] 10 g of γ-Undecalactone (54.2 mmol) was dissolved in 50 mL of methanol. While stirring, 3.9 g of KOH (56.9 mmol, 1.05 eq.) was slowly added, and the reaction was carried out at room temperature for 12 hours. The reaction solution was concentrated under reduced pressure, and 50 mL of DMF was added. While stirring, 5.9 g of bromoethane (54.2 mmol, 1 eq.) was added, and the reaction was carried out for 12 hours. 80 mL of water was added to the reaction solution, and the mixture was extracted with ethyl acetate, followed by washing with water and brine. The organic layer was dried with MgSO4 and concentrated under reduced pressure to obtain 10.7 g (85.6%, two steps) of the target product 2d.

[0194] 1 ¹H NMR (CDCl₃, 400.13 MHz); δ 4.12 (q, 2H, J = 8 Hz, COO-CH₂-), 3.59 (m, 1H, CH-O), 2.43 (m, 2H, CO-CH₂), 1.81 ~ 0.92 (m, 20H, alkyl)).

[0195] (4-2) Synthesis of ethyl 4-(mentylcarbonyloxy)undecanoate, 3d

[0196] 11 g of ethyl 4-hydroxyundecanoate (2d, 47.7 mmol) was dissolved in 60 mL of THF, and 6.8 g of pyridine (95.5 mmol, 2 eq.) was added. The mixture was cooled with ice water, and then, while stirring, 20 mL of THF solution containing 10.5 g of mentyl chloroformate (47.7 mmol, 1 eq.) was slowly dropped in. After one hour, the reaction mixture was heated to room temperature and reacted overnight. Water was then added and the mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, saturated sodium bicarbonate solution, and brine, respectively, dried over MgSO4, and concentrated under reduced pressure to obtain 8.3 g (yield 42.1%) of the target product 3d as a yellow liquid.

[0197] 1H NMR (CDCl3, 400.13MHz); δ 4.74 (7tet, 1H, J = 4 Hz, -COOCH-), 4.51 (td, 1H, J = 9, 4 Hz, COO-CH-), 4.12 (q, 2H, J = 8 Hz, COO-CH2-), 2.36 (m, 2H, CO-CH2-), 1.93 ~ 0.79 (m, 23H, alkyl).

[0198] (4-3) Synthesis of 4-(mentylcarbonyloxy)undecanoic acid [4-(mentylcarbonyloxy)undecanoic acid, 4d]

[0199] 8.3 g of ethyl 4-(mentylcarbonyloxy)undecanoate (3d, 19.4 mmol) was dissolved in 30 mL of THF and 20 mL of distilled water, and 1.2 g of lithium hydroxide monohydrate (29.1 mmol, 1.5 eq.) was added. The mixture was reacted at room temperature for 12 hours. 20 mL of distilled water was added, and extraction was performed using ether. The aqueous layer was adjusted to pH 3 with concentrated hydrochloric acid, and then extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The mixture was subjected to silica gel column chromatography in a mixture of n-hexane and ethyl acetate (8:1) to obtain 6.8 g (91.8% yield) of the target product 4d.

[0200] 1 1H NMR (CDCl3, 400.13 MHz); δ 4.75 (m, 1H, -COOCH-), 4.51 (m, 1H, COO-CH-), 2.43 (m, 2H, CO-CH2-), 2.17 ~ 0.78 (m, 35H, alkyl).

[0201] (4-4) Synthesis of sodium 4-(mentylcarbonyloxy)undecanoate, 5d

[0202] 2.5 g of 4-(mentylcarbonyloxy)undecanoic acid (4d, 7.5 mmol) was dissolved in 20 mL of 95% ethanol. After adding 0.29 g of 98% NaOH (0.95 eq), the mixture was stirred at room temperature for two hours. The water and ethanol were evaporated using the azeotropic effect. Toluene was then added to remove the water, followed by the addition of hexane and ethyl acetate, and the mixture was filtered to obtain a white solid.

[0203] 5. Synthesis of sodium 4-(Benzyloxycarbonyloxy)undecanoate, 5e

[0204] [Option 5]

[0205]

[0206] (5-1) Synthesis of ethyl 4-hydroxyundecanoate [2d]

[0207] 10 g of gamma-undecyl lactone (54.2 mmol) was dissolved in 50 mL of methanol. While stirring, 3.9 g of KOH (56.9 mmol, 1.05 eq.) was slowly added, and the reaction was carried out at room temperature for 12 hours. The reaction solution was concentrated under reduced pressure, and 50 mL of LDM was added. While stirring, 5.9 g of bromoethane (54.2 mmol, 1 eq.) was added, and the reaction was carried out for 12 hours.

[0208] 80 mL of water was added to the reaction solution and extracted with ethyl acetate, followed by washing with water and brine. The organic layer was dried with MgSO4 and concentrated under reduced pressure to obtain 10.7 g (85.6%, two steps) of the target product 2d.

[0209] 1 ¹H NMR (CDCl₃, 400.13 MHz); δ 4.12 (q, 2H, J = 8 Hz, COO-CH₂-), 3.59 (m, 1H, CH-O), 2.43 (m, 2H, CO-CH₂), 1.81 ~ 0.92 (m, 20H, alkyl).

[0210] (5-2) Synthesis of ethyl 4-(Benzyloxycarbonyloxy)undecanoate [Ethyl 4-(Benzyloxycarbonyloxy)undecanoate, 3e]

[0211] 8.3 g of ethyl 4-hydroxyundecanoate (2d, 36 mmol) was dissolved in 50 mL of THF. 5.5 g of pyridine (72.3 mmol, 2 eq.) was added, and the mixture was cooled with ice water. Then, while stirring, 20 mL of THF solution containing 6.1 g of benzylchloroformate (35.3 mmol, 1 eq.) was slowly dropped in. After one hour, the reaction mixture was heated to room temperature and reacted overnight. Water was then added, and the mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, saturated sodium bicarbonate solution, and brine, respectively, dried over MgSO4, and concentrated under reduced pressure to obtain 9.9 g (75.6% yield) of the target product 3e, a yellow liquid.

[0212] 1 ¹H NMR (CDCl₃, 400.13 MHz); δ 7.37 ~ 7.34 (m, 5H, ph), 5.14 (m, 2H, O-CH₂-Ph), 4.12 (brs, 1H, O-CH⁻), 2.42 (m, 2H, CO-CH₂-), 1.90 ~ 0.79 (m, 21H, alkyl) Figure 14 ).

[0213] (5-3) Synthesis of 4-(Benzyloxycarbonyloxy)undecanoic acid, 4e

[0214] 10 g of ethyl 4-(benzyloxycarbonyloxy)undecanoate (3e, 27.5 mmol) was dissolved in 30 mL of THF and 20 mL of distilled water. 1.7 g of lithium hydroxide monohydrate (41.4 mmol, 1.5 eq.) was added, and the mixture was reacted at room temperature for 12 hours. 20 mL of distilled water was added, and extraction was performed using ether. The aqueous layer was adjusted to pH 3 with concentrated hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure to obtain 8.2 g (89% yield) of the target product 4e.

[0215] 1 ¹H NMR (CDCl₃, 400.13 MHz); δ 7.37 ~ 7.35 (m, 5H, ph), 5.14 (m, 2H, O-CH₂-Ph), 4.48 (m, 1H, O-CH⁻), 2.47 (m, 2H, CO-CH₂-), 1.90 ~ 0.79 (m, 21H, alkyl).

[0216] (5-4) Synthesis of sodium 4-(Benzyloxycarbonyloxy)undecanoate, 5e

[0217] 2.5 g of 4-(Benzyloxycarbonyloxy)undecanoic acid, 4e, (7.5 mmol) was dissolved in 20 mL of 95% ethanol. After adding 0.29 g of 98% NaOH (0.95 eq), the mixture was stirred at room temperature for two hours. Water and ethanol were evaporated using the azeotropic effect. Toluene was then added to remove water, followed by the addition of hexane and ethyl acetate, and the mixture was filtered to obtain a white solid.

[0218] Experimental Example

[0219] Pyrolysis tests were performed to confirm the thermal properties (pyrolytic behavior) of compound 5d (2B) when exposed to heat. This test utilized a well-known pyrolysis-gas-chromatography / mass-spectroscopy (Py-GC / MS) method. The pyrolyzer was operated in a system connected to a Double-Shot Pyrolyzer 2020iD (Frontier Lab, Japan) and a GC / MS instrument (Agilent 6890gC, USA / Aginelt 7890 MSD, USA). 2B was diluted to a concentration of 2.5% in ethanol solution, and 10 μL was added to the pyrolyzer sample cup for pyrolysis. The pyrolysis temperature experienced by the sample was controlled by specifying the furnace temperature of the double-shot pyrolyzer, with an initial pyrolysis temperature of 80°C. The sample cup containing the sample was exposed to the furnace for 30 seconds to allow the target compound (2B) within the sample cup to pyrolyze. The thermally generated or volatilized components were immediately injected into the GC / MS injector for separation. During GC / MS analysis after pyrolysis, the sample cup was removed from the furnace to avoid exposure to the pyrolysis temperature. After completing the GC / MS analysis for the first pyrolysis, the initially used sample cup was pyrolyzed again at 90°C (10°C higher) for 30 seconds without injecting new compounds. Again, the sample cup was removed from the furnace after pyrolysis to avoid exposure to the pyrolysis temperature. In this manner, the initial sample was placed into a sample cup, and thermal decomposition experiments were performed by gradually increasing the thermal decomposition temperature to 320°C, starting at 80°C, then 90°C, then 100°C. This allows for the observation of the pyrolysis characteristics of the compound, which change with increasing decomposition temperature, at different temperature intervals. The results are as follows... Figures 15 to 17 As shown.

[0220] [Decomposition Mechanism]

[0221]

[0222] Reference Figures 15 to 17 The thermal decomposition experiment results show that the [2B] compound decomposes into menthol and γ-undecyl lactone at a temperature of about 120°C.

[0223] In the aforementioned decomposition mechanism, the lactone [1B, gamma-undecyl lactone] undergoes ring-opening, and the hydroxyl group is covalently bonded to L-menthol as a linking group to prepare compound [2B]. After applying compound [2B] to a product substrate, heating generates L-menthol ([3B]) and CO2, simultaneously forming compound [4B] with exposed hydroxyl groups. Compound [4B] also undergoes ring-closing (intramolecular esterification) via heat, thereby generating gamma-undecyl lactone [5B]. In the [2B] state, the hydroxyl group is protected by the menthyl carbonate group, thus inhibiting ring-closing (intramolecular esterification) at room temperature.

[0224] The compounds of the present invention that release thermally decomposed aroma components are as follows. Observing the thermal decomposition pattern of compound [2B], menthol is thermally decomposed and released during heating from 120°C to 260°C, and γ-lactone is released for the first time during heating from 120°C to 200°C, followed by a more abundant second release during heating from 200°C to 300°C. This may be because even when menthol, acting as a protecting group, is released due to deprotection upon heating, it exists for a period of time in the form of compound [4B] (i.e., intermediate state). Although the lactone will eventually be generated via intramolecular esterification, this ring-closing may be delayed in the salt form. Furthermore, it can be observed from the results of the thermal decomposition experiments that menthol is thermally decomposed and released with increasing temperature, and in the salt form of [4B], intramolecular esterification occurs at higher temperatures to generate lactone [5B]. In other words, it can be observed that after a certain time interval from the temperature range of menthol thermal decomposition, the remaining thermal decomposition (Ring-Closing) occurs in the higher temperature region.

[0225] Example 2

[0226] The target product of the preparation example (synthesized sodium 5-(mentholocarbonyloxy)decanoate, 5c, 0.01 wt% to 5 wt%), matrix (pulp, 95 wt% to 99 wt%), and other additives (balance) were mixed and formed into a sheet (2 mm thick) using a roll-to-roll method, and dried at room temperature. The sheet was smelled at room temperature and no odor of the flavoring compound used in the synthesis of the target product was observed. The sheet was then used as cigarette paper to manufacture ordinary cigarettes and smoked, confirming that a flavor (e.g., the lactone flavor and menthol flavor used in the synthesis of the target product) was produced upon smoking.

[0227] Example 3

[0228] A tobacco composition is manufactured by mixing the target product of the preparation example (synthesized sodium (4-menthylcarbonyloxy)undecanoate, 5d, 0.003 wt% to 0.02 wt%), tobacco powder (tobacco powder, 90 wt% to 99 wt%, average particle size of 0.03 mm to about 0.12 mm), and other additives (balance). The tobacco composition is then wrapped in rolling paper as a smoking medium to form a filter and rolling paper to prepare a conventional cigarette. Smoking the cigarette confirms the production of aroma in both the mainstream and sidestream smoke.

[0229] Example 4

[0230] An ink composition was prepared by mixing the target product (synthesized sodium (4-menthylcarbonyloxy)undecanoate, 5d) and solvents (water and ethanol). One or more dashed lines of 0.1 mm to 1 mm thickness (line thickness) of the ink composition were printed onto one side of cigarette paper using an embossing method. The coating amount of the synthetic flavoring in each sample was g of the target product per 100 kg of tobacco. As shown in Table 1, when applied to cigarette paper, different effects can be imparted depending on the application area, and it can be used on different parts depending on the cigarette rod.

[0231] [Table 1]

[0232]

[0233] Example 5

[0234] The ink composition (using compound 5d) was applied to multiple locations on cigarette paper in the same manner as in Example 4, and the effect of applying the synthetic flavoring for improving sideflow smoke to different coating locations on smoking articles was evaluated.

[0235] [Table 2]

[0236]

[0237] The amount of gamma-undecyl lactone released during thermal decomposition in sample 5-1 was 2.56 g / 100 kg of tobacco. Its evaluation is as follows:

[0238] Appearance and aroma: No difference from the control group (no odor).

[0239] Mainstream smoke: The odor of lactone is faint but can be faintly detected. From the user's point of view, there is no obvious difference, giving people a soft feeling.

[0240] Sideflow smoke: The pungent smell of the cigarette smoke in the control group was slightly reduced, but there was no significant difference. It gave the user a slight sensation.

[0241] The amount of gamma-undecyl lactone released during thermal decomposition in sample 5-2 was 12.51 g / 100 kg of tobacco. Its evaluation is as follows:

[0242] Appearance and aroma: No difference from the control group (no odor).

[0243] Mainstream smoke: When smoking, it emits a faint lactone aroma, and the menthol aroma becomes stronger closer to the coated area (strip). When the coated area burns, it releases more aroma, without any nauseating or greasy feeling.

[0244] Sidestream smoke: Releases a large amount of aroma at the coating location, resulting in a strong but not unpleasant flavor. It's necessary to move the coating location from the end to the middle to provide a more rapid change in flavor. Sidestream smoke significantly increases aroma release and can also reduce finger smoke odor.

[0245] Example 6

[0246] The ink composition (using compound 6d) was applied to multiple locations on cigarette paper in the same manner as in Example 4, and the effect of applying the synthetic flavoring (flavoring agent) for improving sideflow smoke to different application locations in the cigarette product was evaluated. The application locations of the synthetic flavoring (flavoring agent) for improving sideflow smoke in the cigarette product are shown in Table 3 below.

[0247] [Table 3]

[0248]

[0249] In this invention, a novel compound that releases aroma components upon thermal decomposition is applied to the cigarette paper of a conventional cigarette. During cigarette combustion, particularly during smoke smoulding, the heat releases aroma components (e.g., lactones or menthol), thereby reducing the pungent odor in sidestream smoke. Furthermore, it can be applied to traditional cigarette tobacco media such as tobacco shreds to enhance the persistence of the aroma.

[0250] When applied to a medium for heated tobacco sticks (NGPs), this invention enables the flavor components to remain for a longer period. For heated cigarettes, static heating causes the flavor components contained in the medium to be consumed during the initial puff. However, the flavoring agents are only released when they decompose upon heating. Therefore, even with continuous puffing, flavor components are produced on the last puff, thus maintaining a constant tobacco flavor.

[0251] In summary, embodiments have been described with reference to the limited accompanying drawings. Those skilled in the art can make various modifications and variations based on the description. Suitable results can be obtained even if the described techniques are performed in a different order, and / or if the described constituent elements are combined or combined in different forms, or replaced or substituted by other constituent elements or equivalents. Therefore, other embodiments, other examples, and the scope of the claims should be interpreted as including in this invention.

Claims

1. A smoking article, characterized by comprising a flavoring agent, the flavoring agent being a compound represented by the following Chemical Formula 1: [Chemical Formula 1] In the Chemical Formula 1, n is an integer of 1 or 2, M is selected from alkali metals and transition metals, R is a linear or branched alkyl group having a carbon atom number of 1 to 30, 2.The smoking article according to claim 1, characterized in that the flavoring compound is selected from cyclic monoterpenes having a hydroxyl group, acyclic monoterpenes having a hydroxyl group, aromatic compounds having a hydroxyl group and having a carbon atom number of 6 to 10, and non-aromatic rings having a hydroxyl group and having a carbon atom number of 5 to 6. Part A is a moiety derived from a perfume compound comprising at least one of an aromatic ring, an aliphatic ring, and an aliphatic chain having a hydroxyl group that participates in the carbonate linkage ), A' is a perfume compound other than a hydroxyl group. 3.The smoking article according to claim 1, characterized in that the flavoring compound is selected from the following Chemical Formula: 4.The smoking article according to claim 1, characterized in that the moiety A' is selected from the following Chemical Formula, wherein * is an oxygen bonding site within a carbonate: 5.The smoking article according to claim 1, characterized in that the transition metal is selected from Zr, Mg, Ca, Co, Rh, Ir, Nb, Pd, Pt, Fe, Ru, Os, Cr, Mo, W, Mn, Tc, Re, Cu, Ag, and Au, 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 and . the alkali metal is selected from Li, Na, K, Rb, and Cs. 6.The smoking article according to claim 1, characterized in that the compound is selected from the following Chemical Formulas 1-1 to 1-26: [Chemical Formula 1-1] , , , , , , , , , , , , , , , , , , , , , , , , , and . [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-9] [Chemical Formula 1-10] [Chemical Formula 1-11] [Chemical Formula 1-12] [Chemical Formula 1-13] [Chemical Formula 1-14] [Chemical Formula 1-15] [Chemical Formula 1-16] [Chemical Formula 1-17] [Chemical Formula 1-18] [Chemical Formula 1-19] [Chemical Formula 1-20] [Chemical Formula 1-21] [Chemical Formula 1-22] [Chemical Formula 1-23] [Chemical Formula 1-24] [Chemical Formula 1-25] [Chemical Formula 1-26] wherein M and R are as defined in the Chemical Formula 1. 7.The smoking article according to claim 1, characterized in that the flavoring agent is a flavoring agent compound that generates a flavor upon thermal decomposition. 8.The smoking article according to claim 1, characterized in that the flavoring agent decomposes into the flavoring compound, a lactone compound, and carbon dioxide upon thermal decomposition. 9.The smoking article according to claim 1, characterized in that the compound thermally decomposes at a temperature of 80℃ or higher. 10.The smoking article according to claim 8, characterized in that the lactone compound decomposes into a γ-lactone of the following Chemical Formula 2 or a δ-lactone of Chemical Formula 3: [Chemical Formula 2] [Chemical Formula 3] wherein R is a linear or branched alkyl group having a carbon atom number of 1 to 30. 11.The smoking article according to claim 8, characterized in that ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ The lactone compound is selected from the following chemical formula: 、 、 、 、 、 、 、 、 、 、 、 and .

12. The smoking article according to claim 1, wherein The smoking article comprises a liquid, a powder, a film, or a fiber containing the compound represented by Chemical Formula 1.

13. The smoking article according to claim 1, wherein The smoking article comprises at least one of a film and a filter, and the compound represented by Chemical Formula 1 is printed or applied on the entire surface or at least a part of the film and the filter.

14. The smoking article according to claim 1, wherein The compound represented by Chemical Formula 1 is printed in a pattern in one or more directions of the smoking article rod, The pattern is arranged in at least one shape of a straight line, a broken line, a grid, a polygon, a dot, a circle, and an ellipse.

15. The smoking article according to claim 1, wherein The compound represented by Chemical Formula 1 is 0.0001 parts by weight or more with respect to 100 parts by weight of the smoking medium.

16. The smoking article according to claim 1, wherein The smoking article comprises a filter portion and a smoking medium portion, The smoking medium portion comprises a cigarette paper, a smoking medium, or both, containing the compound represented by Chemical Formula 1.

17. The smoking article according to claim 16, wherein The cigarette paper comprises a pattern area of the compound represented by Chemical Formula 1 distributed at least on the entire one side or partially distributed in one or more directions of the smoking article rod, and the cigarette taste and atmosphere contained in sidestream smoke are controlled according to the position of the pattern area.

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