Fragrances, fragrance compositions, and products comprising the same

Abstract

A kind of the present application relates to new flavor and the product including it. More specifically, it is related to a kind of flavor, the composition and product including it, the flavor includes the part derived from flavor compound represented by chemical formula 1, and is the compound that is decomposed into lactone compound and flavor compound when thermal decomposition.

Description

TECHNICAL FIELD

[0001] The present invention relates to a new flavorant, a flavorant composition, and a product including the same, which can release a flavor component by heating. BACKGROUND

[0002] Flavorants can be added to food and smoking articles to further improve the taste. Smoke or aerosol generated in a smoking article is transferred from upstream to downstream to a smoker, thereby allowing the smoker to achieve satisfaction of smoking. There are many factors that determine the satisfaction of smoking, among which the most important is the cigarette taste that the smoker feels. Smokers want to enjoy a variety of tobacco flavors from one smoking article, and thus, tobacco manufacturers add flavoring substances (e.g., flavorants) to allow smokers to experience different flavors or tastes in order to meet the needs of smokers.

[0003] With the existing flavorants, decomposition easily occurs at room temperature conditions during long-term storage of smoking media, which will cause the flavor component to volatilize, resulting in difficulty in generating sufficient flavor to enhance the taste of a cigarette during smoking, or the flavor persistence will be weakened or the tobacco taste will change as the smoking time elapses. Therefore, it is necessary to develop a flavorant that can improve the satisfaction of smoking during smoking. In food, flavorants are also used to add various flavors, but when food is processed and / or stored for a long time, the flavor often disappears due to volatilization and release. Therefore, it is necessary to develop a flavorant that can prevent or delay the release of a volatile flavorant, thereby extending the shelf life and fully releasing the flavor at the time of use by a consumer. SUMMARY

[0004] Problems to be Solved by the Invention

[0005] The existing compounds having a flavorant function have poor stability of chemical structure at room temperature (rt) or a temperature close to room temperature, and thus, structural transformation or decomposition occurs, resulting in volatilization of the flavor component. To solve this problem, the present invention provides a new flavorant, in which the flavor component is released by thermal decomposition when heated.

[0006] The present invention relates to a flavorant composition including the new flavorant of the present invention.

[0007] The present invention relates to a product including the new flavorant of the present invention.

[0008] However, the technical problems to be solved by the present invention are not limited to the above-mentioned technical problems, and other technical problems not mentioned can be easily understood by those skilled in the art through the following description.

[0009] Means for Solving the Problems

[0010] According to an embodiment of the present application, there is provided a flavoring agent, which is a compound represented by Chemical Formula 1 below:

[0011] [Chemical Formula 1]

[0012]

[0013] In the Chemical Formula 1,

[0014] n is an integer of 1 or 2,

[0015] M is selected from alkali metals and transition metals,

[0016] R is a linear or branched alkyl group having 1 to 30 carbon atoms,

[0017] a moiety A is a moiety derived from a flavor compound including at least one of an aromatic ring, an aliphatic ring, and an aliphatic chain having a hydroxyl group participating in a carbonic acid ester bond , and A' corresponds to the flavor compound except for the hydroxyl group.

[0018] According to an embodiment of the present application, the flavor compound can be selected from a cyclic monoterpene compound having a hydroxyl group, an acyclic monoterpene compound having a hydroxyl group, an aromatic compound having 6 to 10 carbon atoms having a hydroxyl group, and a non-aromatic ring having 5 to 6 carbon atoms having a hydroxyl group.

[0019] According to an embodiment of the present application, 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, and the alkali metal can be selected from Li, Na, K, Rb, and Cs.

[0020] According to an embodiment of the present application, the flavoring agent can be a flavoring agent compound generating a flavor upon thermal decomposition.

[0021] According to an embodiment of the present application, the flavoring agent can be decomposed into the flavor compound, a lactone compound, and carbon dioxide upon thermal decomposition.

[0022] According to an embodiment of the present application, the compound can be thermally decomposed at a temperature of 80°C or more.

[0023] According to an embodiment of the present application, the flavoring agent can be a flavoring agent for food or a smoking article.

[0024] According to an embodiment of the present application, there is provided a composition including the flavoring agent of the present application.

[0025] According to an embodiment of the present application, the composition can be a solid, a slurry, a paste, a gel, a liquid, an emulsion, or an aerosol.

[0026] According to an embodiment of the present application, the composition can further include a carrier, an additive, or both for a food or a smoking article.

[0027] According to an embodiment of the present application, there is provided a smoking article including the flavorant of the present application.

[0028] According to an embodiment of the present application, the smoking article can include a slurry, a paste, a liquid, a gel, a powder, a microbead, a flake, a film, a fiber, or a shaped body containing the flavorant.

[0029] According to an embodiment of the present application, the smoking article can be a cigarette or an electronic cigarette.

[0030] According to an embodiment of the present application, there is provided a food including the flavorant of the present application.

[0031] According to an embodiment of the present application, the food can be mixed with the flavorant of the present application or cooked by heating.

[0032] Inventive Effects

[0033] According to an embodiment of the present application, when the flavorant of the present application is used in a smoking article, the flavoring components generated during smoking can improve the pungent taste in sidestream smoke, and the flavorant is released by thermal decomposition upon heating, so that the taste of the cigarette can be improved and maintained constant.

[0034] According to an embodiment of the present application, the flavorant of the present application is released by thermal decomposition upon heating, so that when used in a food, it can provide rich flavor during cooking and extend the storage life of the flavorant during storage of the food. BRIEF DESCRIPTION OF DRAWINGS

[0035] Figure 1 is an NMR analysis result of ethyl 4-hydroxyheptanoate (2a) prepared in an example according to an embodiment of the present application.

[0036] Figure 2 is an NMR analysis result of ethyl 4-(menthylcarbonyloxy)heptanoate (3a) prepared in an example according to an embodiment of the present application.

[0037] Figure 3 is an NMR analysis result of 4-(menthylcarbonyloxy)heptanoic acid (4a) prepared in an example according to an embodiment of the present application.

[0038] Figure 4is the NMR analysis result of 4-(menthylcarbonyloxy)nonanoic acid (4b) prepared in the example according to an embodiment of the present application.

[0039] Figure 5 is the NMR analysis result of 5-(menthylcarbonyloxy)decanoate (3c) prepared in the example according to an embodiment of the present application.

[0040] Figure 6 is the NMR analysis result of 5-(menthylcarbonyloxy)decanoate (3c) prepared in the example according to an embodiment of the present application.

[0041] Figure 7 is the NMR analysis result of 5-(menthylcarbonyloxy)decanoic acid (4c) prepared in the example according to an embodiment of the present application.

[0042] Figure 8 is the NMR analysis result of 5-(menthylcarbonyloxy)decanoic acid (4c) prepared in the example according to an embodiment of the present application.

[0043] Figure 9 is the NMR analysis result of 4-hydroxyundecanoic acid ethyl ester (2d) prepared in the example according to an embodiment of the present application.

[0044] Figure 10 is the NMR analysis result of 4-hydroxyundecanoic acid ethyl ester (2d) prepared in the example according to an embodiment of the present application.

[0045] Figure 11 is the NMR analysis result of 4-(menthylcarbonyloxy)undecanoic acid ethyl ester (3d) prepared in the example according to an embodiment of the present application.

[0046] Figure 12 is the NMR analysis result of 4-(menthylcarbonyloxy)undecanoic acid (4d) prepared in the example according to an embodiment of the present application.

[0047] Figure 13 is the NMR analysis result of 4-(menthylcarbonyloxy)undecanoic acid (4d) prepared in the example according to an embodiment of the present application.

[0048] Figure 14 is the NMR analysis result of 4-(benzyloxy carbonyloxy)undecanoic acid ethyl ester (3e) prepared in the example according to an embodiment of the present application.

[0049] Figure 15 is the thermal analysis result of sodium (4-menthylcarbonyloxy)undecanoate (5d) prepared in the example according to an embodiment of the present application.

[0050] Figure 16 The component distribution of sodium (4-menthylcarbonyloxy)undecanoate (5d) prepared in the Example according to an embodiment of the present application as a function of thermal decomposition temperature. DETAILED DESCRIPTION

[0051] Embodiments of the present application will be described in detail with reference to the accompanying drawings. In describing the present application, when it is considered that a detailed description of related known functions or constructions will unnecessarily obscure the gist of the present application, a detailed description thereof will be omitted. Also, the terms used in the specification are used to accurately describe the embodiments, and can be changed according to the intention of the user, operator, or the custom in the technical field to which the present application pertains. Therefore, the definition of the terms should be made based on the overall content of the specification. The same reference numerals are used throughout the drawings to refer to the same components.

[0052] Throughout the specification, when it is stated that a member is "on" another member, it includes not only the case where the one member is in contact with the other member, but also the case where a further member is present between the two members.

[0053] Throughout the specification, when a part "comprises" a certain member, it means that other members can be further included, rather than excluding other members.

[0054] Hereinafter, the novel flavor and the method for using the same according to the present application will be described in detail with reference to the embodiments and the accompanying drawings. However, the present application is not limited to only these embodiments and the accompanying drawings.

[0055] One of the present application relates to a novel flavor, according to an embodiment of the present application, the flavor when heated will release flavor components by thermal decomposition.

[0056] According to an embodiment of the present application, the flavor can be a compound represented by the following Chemical Formula 1.

[0057] [Chemical Formula 1]

[0058]

[0059] As an example of the present application, the flavor compound in Chemical Formula 1 is a compound represented by the following Chemical Formula 2, which is a compound having a carbonic acid ester bond (— O— CO— O— ) in the molecule. ) covalently bonded, the compound of Chemical Formula 1 is decomposed into a perfume compound and a lactone compound upon heating, thereby releasing a fragrance. For example, the compound of Chemical Formula 1 reacts with a hydroxyl group of a perfume compound through a ring-opening mechanism of a lactone compound, thereby covalently bonding the perfume compound through a carbonate bond. It can function as a protecting group at room temperature and / or a temperature close thereto, preventing conversion into a lactone compound due to ring closure. The compound of Chemical Formula 1 is structurally stable at about room temperature or a temperature close thereto, and has low volatility, and upon heating, the carbonate bond is broken through a ring closure mechanism, thereby decomposing into a lactone compound and a perfume compound, allowing a fragrance to be released, and carbon dioxide harmless to the human body is generated in the process of decomposition. That is, the carbonate bond is broken and decomposed into a perfume compound and generates carbon dioxide during heating. Then, it is decomposed into a lactone compound through ring closure, thereby releasing a fragrance.

[0060] According to an embodiment of the present application, n in Chemical Formula 1 can be an integer of 1 or 2. R is a linear or branched alkyl group having a carbon atom number of 1 to 30; preferably, it can be a linear or branched alkyl group having a carbon atom number of 2 to 10.

[0061] According to an embodiment of the present application, the moiety A in Chemical Formula 1 can be a moiety derived from a perfume compound including 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 can include at least one (e.g., one or both) of a ring, a chain, or both. This can correspond to a substituent, a basic skeleton, and / or a moiety having a hydroxyl group. The hydroxyl group can participate in a carbonate bond in Chemical Formula 1, and A' can correspond to a perfume compound other than a hydroxyl group. That is, the hydroxyl group of the perfume compound in the moiety A is protected by a carbonate bond, and decomposition reaction based on ring closure at room temperature can be prevented.

[0062] According to an embodiment of the present application, the perfume compound can be selected from a cyclic monoterpene compound having a hydroxyl group, an acyclic monoterpene compound having a hydroxyl group, an aromatic compound having a carbon atom number of 6 to 10 having a hydroxyl group, and an aliphatic compound having a carbon atom number of 5 to 10 having a hydroxyl group; or a non-aromatic ring having a carbon atom number of 5 to 6 and an isomer thereof. For example, the perfume compound can be selected from the following compounds, which are generated due to the breaking of a carbonate bond upon thermal decomposition of Chemical Formula 1:

[0063] , , , , , , 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 and .

[0064] According to an embodiment of the present application, A' in the moiety A can be selected from the following formulae. Wherein * is the oxygen site within the carbonate linkage:

[0065] 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、

[0066] and .

[0067] According to an embodiment of the present application, the M can be selected from alkali metals and transition metals, the M can form a salt with the oxygen of the ester group to increase the solubility in water-soluble solvents, and facilitate application to food and smoking articles. 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, the M can be a metal forming a monovalent cation, which can be selected from Li, Na, and K.

[0068] According to an embodiment of the present application, the lactone compound can be a γ-lactone of the following Chemical Formula 2 or a δ-lactone of the following Chemical Formula 3.

[0069] [Chemical Formula 2]

[0070]

[0071] [Chemical Formula 3]

[0072]

[0073] In an example of the present application, R of the Chemical Formula 1 and the Chemical Formula 2 is a linear or branched alkyl group having 1 to 30 carbon atoms, preferably a linear or branched alkyl group having 2 to 10 carbon atoms.

[0074] According to an embodiment of the present application, the lactone can be selected from the following Chemical Formulae:

[0075] 、 、 、 、 、 、 、 、 、 、 、 and .

[0076] According to an embodiment of the present application, the compound can be selected from the following Chemical Formulae 1-1 to 1-26.

[0077] [Chemical Formula 1-1]

[0078]

[0079] [Chemical Formula 1-2]

[0080]

[0081] [Chemical Formula 1-3]

[0082]

[0083] [Chemical Formula 1-4]

[0084]

[0085] [Chemical Formula 1-5]

[0086]

[0087] [Chemical Formula 1-6]

[0088]

[0089] [Chemical Formula 1-7]

[0090]

[0091] [Chemical Formula 1-8]

[0092]

[0093] [Chemical Formula 1-9]

[0094]

[0095] [Chemical Formula 1-10]

[0096]

[0097] [Chemical Formula 1-11]

[0098]

[0099] [Chemical Formula 1-12]

[0100]

[0101] [Chemical Formula 1-13]

[0102]

[0103] [Chemical Formula 1-14]

[0104]

[0105] [Chemical Formula 1-15]

[0106]

[0107] [Chemical Formula 1-16]

[0108]

[0109] [Chemical Formula 1-17]

[0110]

[0111] [Chemical Formula 1-18]

[0112]

[0113] [Chemical Formula 1-19]

[0114]

[0115] [Chemical Formula 1-20]

[0116]

[0117] [Chemical Formula 1-21]

[0118]

[0119] [Chemical Formula 1-22]

[0120]

[0121] [Chemical Formula 1-23]

[0122]

[0123] [Chemical Formula 1-24]

[0124]

[0125] [Chemical Formula 1-25]

[0126]

[0127] [Chemical Formula 1-26]

[0128]

[0129] wherein M and R are as defined in the Chemical Formula 1.

[0130] According to an embodiment of the present application, 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. Also, the thermal decomposition can be performed in an environment including oxygen and / or moisture.

[0131] According to an embodiment of the present application, the flavoring agent can be used as a flavoring agent for food and smoking articles. That is, it can be used as an additive allowed for food and smoking articles.

[0132] The present application relates to a composition including the flavoring agent of the present application.

[0133] According to an embodiment of the present application, the composition includes the flavoring agent of the present application (i.e., the flavoring agent compound represented by Chemical Formula 1), and according to the use, can further include a carrier, an additive, or both. The carrier and the additive are carriers and additives allowed for food or smoking articles, and for example, can include a solvent, an adhesive, a diluent, a disintegrant, a lubricant, a flavoring agent, a coloring agent, a preservative, an antioxidant, an emulsifier, a stabilizer, an enhancer, a sweetener, etc., but are not limited thereto.

[0134] According to an embodiment of the present application, the composition can further include a base material (or a base) ingredient according to the use, and for example, can include paper, pulp, wood, a polymer resin (e.g., cellulose), a fiber, a vegetable oil, a petroleum-derived oil (e.g., paraffin), an animal oil, a wax, a fatty acid (e.g., an animal fat, a vegetable fat, a saturated fatty acid, an unsaturated fatty acid (e.g., a monounsaturated fatty acid or a polyunsaturated fatty acid) having 1 to 50 carbon atoms), etc. The base material ingredient can further include an organic and / or inorganic or ceramic powder (e.g., chalk, perlite, vermiculite, diatomaceous earth, colloidal silica, magnesium oxide, magnesium sulfate, magnesium carbonate), a wetting agent (e.g., glycerol or propylene glycol), and an acetate compound, etc.

[0135] According to an embodiment of the present application, the composition can further include a tobacco ingredient according to the use. When used for a smoking article, the composition can generate a flavor in a mainstream smoke and a sidestream smoke under a smoking condition. The tobacco ingredient can be a solid material based on a reconstituted tobacco, a cut tobacco, a recombined tobacco, etc., and can be selected from a tobacco leaf, an extruded tobacco, and a bandcast tobacco. Also, the composition can further include an aerosol generator as a cigarette medium, and non-limiting examples of the aerosol generator include sorbitol, glycerol, propylene glycol, triethylene glycol, lactic acid, diacetin, triacetin, triethylene glycol diacetate, triethyl citrate, ethyl myristate, isopropyl myristate, methyl stearate, dimethyl dodecanedioate, dimethyl tetradecanedioate, etc.

[0136] According to an embodiment of the present application, the flavoring agent can be 0.0001% by weight or more; 0.001% by weight or more; 0.01% by weight or more; 0.0001% to 100% by weight (or less than 100% 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; 5% to 10% by weight in the composition. When included in the range, the flavoring agent can release a flavor by thermal decomposition, and can improve the taste of a cigarette when used in a smoking article.

[0137] According to an embodiment of the present application, the composition can be prepared in various phases, for example, can be prepared as a solid (e.g., powder, crystal, flake, pulverization), slurry, paste, gel, liquid, emulsion, or aerosol. For example, the composition can be molded, or can be mixed with a desired product, or used in a manner of printing, impregnation, spraying, and / or coating, etc. as publicly known in the art, which is not specifically described herein.

[0138] The present application relates to a food including the flavoring agent of the present application. According to an embodiment of the present application, the food can include at least one of the flavoring agent compounds represented by Chemical Formula 1 of the present application. The flavoring agent can provide a flavor by thermal decomposition when the food is heated and / or baked.

[0139] According to an embodiment of the present application, the food can be made of a food raw material and the flavoring agent or a composition including the flavoring agent, and the composition can further include a food additive, such as a solvent (e.g., water, alcohol, liquid extract), adhesive, diluent (e.g., oil), disintegrant, lubricant, coloring agent, preservative, antioxidant, emulsifier, stabilizer, flavor enhancer, sweetener, etc., according to a desired food, but is not limited thereto. For example, the flavoring agent can be directly mixed with the food, or a composition including the flavoring agent can be used by mixing, impregnation, spraying, and / or coating.

[0140] According to an embodiment of the present application, the food can be a food to which the flavoring agent is added, or a semi-finished product or finished product that is cooked by heating. When the flavoring agent is added, the food can be additionally heated to function the flavoring agent. In addition, the flavoring agent can be heated together with the semi-finished product or finished product to function, or the flavoring agent can be added to the semi-finished product or finished product and additionally heated to function.

[0141] According to an embodiment of the present application, the flavoring agent can be 0.0001% by weight or more to 99% by weight; 0.01% by weight or more; 0.1% by weight or more; 1% to 50% by weight; 1% to 30% by weight; or 1% to 20% by weight in the food. When included in the range, the flavoring agent can produce a flavor and maintain the inherent properties of the food material.

[0142] According to an embodiment of the present application, the "food" can be a food material, a sauce, an additive, a seasoning, a food and drink, a snack, a processed food, a frozen food, a refrigerated food, a stored food, a pickled food, a functional food, a fermented food. Also, it can be in a state of being added without cooking (for example, a state of surface coating, a state of filling, a state of seasoning, a state of pickling, a state of drying, a state of mixing), or a semi-finished or finished food (for example, a food cooked by heating such as baking, steaming, grilling, frying, boiling, heating, etc.). Non-limiting examples are cereal products, rice products, cassava products, sago products, bread products, rice cake products, biscuit products, pastry products, candy products, dessert products, chewing gum, bubble gum, chocolate, ice cream, honey products, molasses products, yeast products, baking powder, salt and seasoning products, condiments, sweeteners, savory products, mustard products, vinegar products, sauces (condiments), cooked fruits and vegetable products, and meat products, jelly, jam, fruit flavoring, egg products, milk and dairy products, cheese products, butter and butter substitutes, milk substitutes, bean products, edible oil and fat products, beverages, alcoholic beverages, beer, carbonated beverages, soda water and other non-alcoholic beverages, fruit beverages, fruit juice, coffee, artificial coffee, tea, cocoa, chocolate, candy, extract foods, plant extracts, meat extracts, gelatin, pharmaceuticals, elixirs, syrups, and other preparations for making beverages.

[0143] The present application relates to a smoking article including the flavoring agent of the present application. According to an embodiment of the present application, the smoking article can include at least one of the flavoring agent compounds represented by Chemical Formula 1 of the present application. The flavoring agent provides a flavor by thermal decomposition when the smoking article is heated and / or combusted. That is, the flavor can be released to the mainstream smoke and / or the sidestream smoke when the smoking article is heated and / or combusted.

[0144] According to an embodiment of the present application, the "smoking article" can refer to tobacco, tobacco derivatives, expanded tobacco, reconstituted tobacco, or any product that can be inhaled like a cigarette 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 a cigarette, a cigar, a cigarillo, an electronic cigarette, or the like aerosol-generating smoking article. The smoking article can include an aerosol-generating material or an aerosol-generating substrate. Alternatively, the smoking article can include a solid material based on a tobacco raw material such as reconstituted tobacco, tobacco shreds, reconstituted tobacco, or the like.

[0145] According to an embodiment of the present application, the flavoring agent can be 0.0001 parts by weight or more; 0.001 parts by weight or more; 0.1 parts by weight or more; 1 parts by weight or more; 1 parts by weight to 20 parts by weight, in the smoking article, with respect to 100 parts by weight of a smoking medium.

[0146] According to an embodiment of the present application, the amount of the flavoring component such as lactones, etc. emitted from the flavoring agent in the smoking article can 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 parts by weight or more; 1 parts by weight to 20 parts by weight, with respect to 100 parts by weight of a smoking medium, when the smoking article is smoked.

[0147] According to an embodiment of the present application, the smoking article can be a cigarette-type cigarette, a liquid-type cigarette, or a hybrid-type cigarette, and can be a combustion-type cigarette or a heating-type cigarette. Alternatively, it can also be an electronic cigarette (e.g., an electronic heating cigarette).

[0148] According to an embodiment of the present application, when the flavoring agent is applied to the cigarette paper of a cigarette and the cigarette is heated and / or combusted, particularly smouldered, the flavoring component (e.g., lactones and / or flavoring components) is released by heat, thereby improving the pungent odor in the sidestream smoke.

[0149] According to an embodiment of the present application, when applied to a medium of a heating-type tobacco rod, the flavoring component can be left for a long time. For a heating-type cigarette, static heating can cause the flavoring component contained in the medium to be consumed at the first puff, but the flavoring agent is released only when it is thermally decomposed, so even if the puffing is continued, the flavoring component is generated at the last puff, thereby maintaining a constant tobacco taste.

[0150] According to an embodiment of the present application, the smoking article can include the flavoring agent or the flavoring agent composition. For example, it can be a constituent element and / or a fitting of the smoking article. Preferably, it can be a constituent element and / or a fitting of a region heated in the smoking article. For example, it can be a smoking medium (e.g., liquid, gel, solid, slurry, paste), a paper tube, a smoke tube, a filter (e.g., a tubular filter, a fiber filter, a woven filter, a paper filter, a capsule filter), a rolling paper, a cigarette paper, a tipping paper, a wrapping paper, a cartridge (e.g., a heating cartridge), etc., and can include a well-known element in the technical field of the present application without departing from the object of the present application, and thus will not be described in detail herein.

[0151] According to an embodiment of the present application, in manufacturing the smoking article, the flavoring agent itself can be mixed with a substrate or a base material, or a composition including the flavoring agent can be mixed, printed, impregnated (or soaked), coated, and / or sprayed with a substrate or a base material.

[0152] According to an embodiment of the present application, the smoking medium can further include a flavoring agent and a tobacco raw material (e.g., a medium raw material, a tobacco leaf), or can further include an additive. As another example, in manufacturing a constituent element and / or a member of the smoking article, the flavoring agent can be added as a flavoring agent, thereby being mixed with a base material, a solvent, a flavoring material, a smoking medium material, etc. suitable for the smoking article. Also, the smoking medium can be a liquid, a gel, or a solid.

[0153] Hereinafter, the present application will be described in more detail through examples and comparative examples, but the following examples are only for illustrating the present application, and the content of the present application is not limited only to the following examples.

[0154] Example 1

[0155] 1. Synthesis of Sodium (4-mentylcarbonyloxy) heptanoate [5a]

[0156] [Scheme 1]

[0157]

[0158] (1-1) Synthesis of Ethyl 4-hydroxyheptanoate [2a]

[0159] To 20 g of γ-Heptalactone (0.15 mol) dissolved in 100 mL of methanol, 11.17 g of KOH (0.16 mol, 1.05 eq.) was slowly added while stirring, and then reacted for 12 hours at room temperature. After the reaction solution was concentrated under reduced pressure, 80 mL of DMF was added, 17 g of bromoethane (0.15 mol, 1 eq.) was added while stirring, and then reacted for 12 hours. After 100 mL of water was added to the reaction solution and extracted with ethyl acetate, it was washed with water and brine. After the organic layer was dried with MgSO4, it was concentrated under reduced pressure, thereby obtaining 18.1 g of the target product 2a (66.7%, 2 steps).

[0160] 1 H NMR (CDC13, 400.13 MHz); 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).

[0161] (1-2) Synthesis of Ethyl 4-(mentylcarbonyloxy)heptanoate [3a]

[0162] To 18 g of Ethyl 4-hydroxyheptanoate (2a, 0.1 mol) dissolved in 120 mL of THF, 16 g of pyridine (0.2 mol, 2 eq.) was added and stirred while cooling with ice water, and then 23 g of mentyl chloroformate (0.1 mol, 1 eq.) dissolved in 20 mL of THF was slowly dropped. After one hour, the reaction solution was warmed to room temperature and reacted overnight, and then water was added and extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, a saturated sodium bicarbonate solution, and brine, respectively, and then dried with MgSO4, and after concentration under reduced pressure, 30 g (yield 81%) of the target product 3a was obtained as a yellow liquid.

[0163] 1H NMR (CDC13, 400.13 MHz); 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).

[0164] (1-3) Synthesis of 4-(mentylcarbonyloxy)heptanoic acid [4-(mentylcarbonyloxy)heptanoic acid, 4a]

[0165] Ethyl 4-(mentylcarbonyloxy)heptanoate (3a, 68.5 mmol) was dissolved in 100 mL of THF and 30 mL of distilled water, and 4.2 g of lithium hydroxide monohydrate (102.4 mmol, 1.5 eq.) was added, and the reaction was allowed to proceed at room temperature for 12 hours. 50 mL of distilled water was added and extracted with ether. After adjusting the aqueous layer to pH 3 by adding concentrated hydrochloric acid, it was extracted with ethyl acetate. The organic layer was washed with brine, dried with MgSO4, and concentrated under reduced pressure to obtain 21.8 g (yield 81%) of the target product 4a as a yellow liquid.

[0166] 1 H NMR (CDC13, 400.13 MHz); 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).

[0167] (1-4) Synthesis of sodium (4-mentylcarbonyloxy)heptanoate [Sodium (4-mentylcarbonyloxy)heptanoate, 5a]

[0168] Dissolve 2.5 g of 4-(mentylcarbonyloxy)hepanoic acid (7.5 mmol) in 20 mL of 95% ethanol, add 0.29 g of 98% NaOH (0.95 eq) and stir at room temperature for two hours. Evaporate the water and ethanol using the azotrope phenomenon, then add toluene to remove the water, then add hexane, ethyl acetate and filter to obtain a white solid.

[0169] 2. Synthesis of sodium 4-(mentylcarbonyloxy)nonanoate [5b]

[0170] [Scheme 2]

[0171]

[0172] (2-1) Synthesis of ethyl 4-hydroxynonanoate [2b]

[0173] Dissolve 20 g of γ-Nonalactone (0.13 mol) in 100 mL of methanol, slowly add 9.18 g of KOH (0.14 mol, 1.05 eq.) while stirring, and react at room temperature for 12 hours. Concentrate the reaction solution under reduced pressure, add 80 mL of DMF and stir, add 14 g of bromoethane (0.13 mol, 1 eq.) while stirring, and react for 12 hours. Add 100 mL of water to the reaction solution and extract with ethyl acetate, then wash with water and brine. Dry the organic layer with MgS04, then concentrate under reduced pressure to obtain 24 g (93%, 2 steps) of the target product 2b.

[0174] (2-2) Synthesis of ethyl 4-(mentylcarbonyloxy)nonanoate [3b]

[0175] To 24 g of ethyl 4-hydroxynonanoate (2b, 0.12 mol) dissolved in 120 mL of THF, 18 g of pyridine (0.42 mol, 2 eq.) was added and cooled with ice water while stirring, and a solution of 26 g of menthyl chloroformate (0.12 mol, 1 eq.) dissolved in 30 mL of THF was slowly dropped. After one hour, the reaction was warmed to room temperature and left overnight, and then water was added and 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 34 g (yield 74.5%) of the target product 3b as a yellow liquid.

[0176] 1 H NMR (CDC13, 400.13 MHz); 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).

[0177] (2-3) Synthesis of 4-(mentylcarbonyloxy)nonanoic acid [4-(mentylcarbonyloxy)nonanoic acid, 4b]

[0178] To 11.5 g of ethyl 4-(mentylcarbonyloxy)nonanoate (3, 29.9 mmol) 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 reacted at room temperature for 12 hours. 50 mL of distilled water was added and extracted with ether. After adjusting the water layer to pH 3 by adding concentrated hydrochloric acid, it was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and after concentration under reduced pressure, 8.6 g (yield 80%) of the target product 4b was obtained as a yellow liquid.

[0179] 1 H NMR (CDC13, 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).

[0180] (2-4) Synthesis of sodium 4-(mentylcarbonyloxy)nonanoate [4-(mentylcarbonyloxy) nonanoate, 5b]

[0181] To 2.5 g of 4-(mentylcarbonyloxy)nonanoic acid (4b, 7.5 mmol) dissolved in 20 mL of 95% ethanol, 0.29 g of 98% NaOH (0.95 eq) was added and stirred at room temperature for two hours. Water and ethanol were evaporated using the azotrope phenomenon, and then toluene was added to remove water, followed by the addition of hexane, ethyl acetate, and filtration to obtain a white solid.

[0182] 3. Sodium 5-(mentylcarbonyloxy)decanoate 5c

[0183] [Scheme 3]

[0184]

[0185] (3-1) Synthesis of Ethyl 5-hydroxydecanoate (2c)

[0186] To 10 g of δ-decalactone (58.7 mmol) dissolved in 50 mL of methanol, 4.2 g of KOH (64.7 mmol, 1.05 eq.) was slowly added while stirring, and reacted at room temperature for 12 hours. After the reaction solution was concentrated under reduced pressure, 40 mL of DMF was added, 6.4 g of bromoethane (58.7 mmol, 1 eq.) was added while stirring, and reacted for 12 hours.

[0187] 100 mL of water was added to the reaction solution and extracted with ethyl acetate, and then washed with water and brine. After the organic layer was dried with MgSO4, it was concentrated under reduced pressure to obtain 7.6 g (60%, 2 steps) of the target product 2c.

[0188] (3-2) Synthesis of Ethyl 5-(mentylcarbonyloxy)decanoate (3c)

[0189] To a solution of 7.5 g of ethyl 4-hydroxynonanoate (2c, 34.6 mmol) in 50 mL of THF, 5.3 g of pyridine (69.2 mmol, 2 eq.) was added and cooled with ice water, and then a solution of 8.3 g of menthyl chloroformate (37.9 mmol, 1.1 eq.) in 20 mL of THF was slowly dropped while stirring. After one hour, the reaction was warmed to room temperature and reacted overnight, after which water was added and 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 mixed solvent of n-hexane and ethyl acetate (7:1) to obtain 4.5 g (yield 32.6%) of the target product 3c.

[0190] 1 H NMR (CDCI3, 400.13 MHz); 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).

[0191] (3-3) Synthesis of 5-(menthylcarbonyloxy)decanoic acid [4c]

[0192] To a solution of 2.7 g of ethyl 4-(menthylcarbonyloxy)nonanoate (3c, 6.8 mmol) 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 reacted at room temperature for 12 hours. 10 mL of distilled water was added and extracted with ether. After adjusting the aqueous layer to pH 3 by adding concentrated hydrochloric acid, it was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure to obtain 2.1 g (yield 78%) of the target product 4b as a yellow liquid.

[0193] 1 H NMR (CDCI3, 400.13 MHz); 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).

[0194] (3-4) Synthesis of 5-(mentylcarbonyloxy) decanoate 5c]

[0195] Dissolve 5-(mentylcarbonyloxy) decanoic acid (4c, 7.5 mmol) in 20 mL of 95% ethanol, and stir for two hours at room temperature after adding 0.29 g of 98% NaOH (0.95 eq). Evaporate water and ethanol using the azotrope phenomenon, and then add toluene to remove water, and then add hexane, ethyl acetate, and filter to obtain a white solid.

[0196] 4. Synthesis of Sodium (4-mentylcarbonyloxy) undecanoate 5d

[0197] [Scheme 4]

[0198]

[0199] (4-1) Synthesis of Ethyl 4-hydroxyundecanoate 2d

[0200] Dissolve 10 g of γ-undecalactone (54.2 mmol) in 50 mL of methanol, and slowly add 3.9 g of KOH (56.9 mmol, 1.05 eq.) while stirring, and react for 12 hours at room temperature. Add 50 mL of DMF to the reaction solution, and add 5.9 g of bromoethane (54.2 mmol, 1 eq.) while stirring, and react for 12 hours. Add 80 mL of water to the reaction solution, and extract using ethyl acetate, and then wash with water and brine. Dry the organic layer using MgSO4, and concentrate under reduced pressure to obtain 10.7 g (85.6%, 2 steps) of the target product 2d.

[0201] 1 H NMR (CDC13, 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).

[0202] (4-2) Synthesis of Ethyl 4-(mentylcarbonyloxy)undecanoate]Ethyl 4-(mentylcarbonyloxy)undecanoate, 3d]

[0203] Ethyl 4-hydroxyundecanoate (2d, 47.7 mmol) was dissolved in 60 mL of THF, 6.8 g of pyridine (95.5 mmol, 2 eq.) was added and cooled with ice water, then a solution of 10.5 g of mentyl chloroformate (47.7 mmol, 1 eq.) in 20 mL of THF was slowly dropped while stirring. After one hour the reaction was warmed to room temperature and left overnight, then water was added and extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, sodium bicarbonate saturated solution and brine, then dried over MgS04, and after concentration under reduced pressure the target product 3d was obtained as a yellow liquid (8.3 g, 42.1% yield).

[0204] 1 H NMR (CDC13, 400.13 MHz); 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).

[0205] (4-3) Synthesis of 4-(mentylcarbonyloxy)undecanoic acid [4-(mentylcarbonyloxy) undecanoic acid, 4d]

[0206] Ethyl 4-(mentylcarbonyloxy)undecanoate (3d, 19.4 mmol) was dissolved in 30 mL of THF and 20 mL of distilled water, 1.2 g of lithium hydroxide monohydrate (29.1 mmol, 1.5 eq.) was added, and reacted at room temperature for 12 hours. 20 mL of distilled water was added and extracted with ether. After adjusting the water layer to pH 3 with concentrated hydrochloric acid, it was extracted with ethyl acetate. After washing the organic layer with brine, it was dried with MgSO4, and then concentrated under reduced pressure. Silica gel column chromatography was performed on the mixture using a mixed solvent of n-hexane and ethyl acetate (8:1) to obtain 6.8 g (yield 91.8%) of the target product 4d.

[0207] 1 H NMR (CDCI3, 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).

[0208] (4-4) Synthesis of Sodium 4-(mentylcarbonyloxy)undecanoate [5d]

[0209] 2.5 g of 4-(mentylcarbonyloxy)undecanoic acid (4d, 7.5 mmol) was dissolved in 20 mL of 95% ethanol, and after adding 0.29 g of 98% NaOH (0.95 eq.), it was stirred at room temperature for two hours. Water and ethanol were volatilized using the azotrope phenomenon, and then toluene was added to remove water, and after that, hexane, ethyl acetate were added and filtered to obtain a white solid.

[0210] 5. Synthesis of Sodium 4-(Benzyloxycarbonyloxy)undecanoate [5e]

[0211] [Scheme 5]

[0212]

[0213] (5-1) Synthesis of Ethyl 4-hydroxyundecanoate [2d]

[0214] Dissolve 10 g of undecanolide (54.2 mmol) in 50 mL of methanol, slowly add 3.9 g of KOH (56.9 mmol, 1.05 eq.) while stirring, and react for 12 hours at room temperature. After concentrating the reaction solution under reduced pressure, add 50 mL of DMF, add 5.9 g of bromoethane (54.2 mmol, 1 eq.) while stirring, and react for 12 hours.

[0215] Add 80 mL of water to the reaction solution and extract with ethyl acetate, and then wash with water and brine. Dry the organic layer with MgS04, and concentrate under reduced pressure to obtain 10.7 g (85.6%, 2 steps) of the target product 2d.

[0216] 1 H NMR (CDC13, 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).

[0217] (5-2) Synthesis of Ethyl 4-(Benzyloxycarbonyloxy)undecanoate [3e]

[0218] Dissolve 8.3 g of ethyl 4-hydroxyundecanoate (2d, 36 mmol) in 50 mL of THF, add 5.5 g of pyridine (72.3 mmol, 2 eq.) after cooling with ice water, and then slowly drop (dropping) a solution of 6.1 g of benzyl chloroformate (35.3 mmol, 1 eq.) in 20 mL of THF while stirring. After one hour, warm the reaction solution to room temperature, react overnight, and then add water and extract with ethyl acetate. Dry the organic layer with MgS04after washing with dilute hydrochloric acid, a saturated sodium bicarbonate solution, and brine, and concentrate under reduced pressure to obtain 9.9 g (yield 75.6%) of the target product 3e as a yellow liquid.

[0219] 1H NMR (CDC13, 400.13 MHz); δ 7.37 ~ 7.34 (m, 5H, ph), 5.14 (m, 2H, O-CH2-Ph), 4.12 (br s, 1H, O-CH-), 2.42 (m, 2H, CO-CH2-), 1.90 ~ 0.79 (m, 21H, alkyl). Figure 14 ).

[0220] (5-3) Synthesis of 4-(Benzyloxycarbonyloxy)undecanoic acid [4-(Benzyloxycarbonyloxy)undecanoic acid, 4e]

[0221] Dissolve 10 g of 4-(Benzyloxycarbonyloxy)undecanoic acid ethyl ester (3e, 27.5 mmol) in 30 mL of THF and 20 mL of distilled water, add 1.7 g of lithium hydroxide monohydrate (41.4 mmol, 1.5 eq.), and react at room temperature for 12 hours. Add 20 mL of distilled water and extract with ether. After adjusting the water layer to pH 3 with concentrated hydrochloric acid, extract with ethyl acetate. Wash the organic layer with brine, dry with MgS04, and concentrate under reduced pressure to obtain 8.2 g (yield 89%) of the target product 4e.

[0222] 1 H NMR (CDC13, 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).

[0223] (5-4) Synthesis of sodium 4-(Benzyloxycarbonyloxy)undecanoate [sodium 4-(Benzyloxycarbonyloxy)undecanoate, 5e]

[0224] Dissolve 2.5 g of 4-(Benzyloxycarbonyloxy)undecanoic acid [4-(Benzyloxycarbonyloxy)undecanoic acid, 4e, (7.5 mmol) in 20 mL of 95% ethanol, and after adding 0.29 g of 98% NaOH (0.95 eq.), stir at room temperature for two hours. Evaporate water and ethanol using the azotrope phenomenon, then add toluene to remove water, and then add hexane, ethyl acetate, and filter to obtain a white solid.

[0225] Experimental Example

[0226] Pyrolysis test was performed to confirm the thermal characteristics (pyrolytic behavior) of the 5d compound (2B) upon exposure to heat, using a known Pyrolysis-Gas Chromatography / Mass Spectrometry [Py-GC / MS] method. The pyrolyzer was performed in a system in which a "Double-Shot Pyrolyzer 2020iD" (Frontier Lab, Japan) was connected to a GC / MS (Agilent 6890gC, USA / Aginelt 7890 MSD, USA) device. After diluting 2B to a concentration of 2.5% in an Ethyl alcohol solution, 10 ul was loaded into a pyrolyzer sample cup and pyrolysis was performed. The pyrolysis temperature experienced by the sample was controlled by specifying the Furnace temperature of the Double-Shot Pyrolyzer, and the initial pyrolysis temperature was 80°C, and the sample cup containing the sample was exposed to the Furnace for 30 seconds, thereby pyrolyzing the target compound (2B) in the sample cup. The components generated or volatilized by heat were immediately injected into the GC / MS injector and separated. During the GC / MS analysis after pyrolysis, the sample cup was removed from the furnace to avoid the influence of the pyrolysis temperature, and after completing the GC / MS analysis for the first pyrolysis, the sample cup initially used was again subjected to pyrolysis without injecting a new compound, and the pyrolysis temperature was 90°C, which was 10°C higher than the initial pyrolysis temperature, and was continued for 30 seconds. Also, the sample cup was removed from the furnace after the thermal decomposition was completed to avoid the influence of the pyrolysis temperature. In this way, after loading the initial sample into the sample cup, the thermal decomposition experiment was performed such that the thermal decomposition temperature was increased to 80°C, 90°C, 100°C, and finally to 320°C. Thus, the pyrolysis characteristics of the compound changed as the thermal decomposition temperature increased could be observed separately based on different temperatures. The results are shown in Figure 15 and Figure 16

[0227] [Decomposition mechanism]

[0228]

[0229] Referring to Figure 15 and Figure 16 , it can be seen from the results of the thermal decomposition experiment that the [2B] compound decomposes into menthol and γ-undecalactone at a temperature of about 120°C.

[0230] ​That is, in the decomposition mechanism, the lactone [1B, propylundecanolide] is ring-opened, and the hydroxyl group is covalently bonded as a linking group to L-menthol (L-Menthol) to produce the [2B] compound. After the [2B] compound is applied to a product substrate, L-menthol ([3B]) and CO2 are generated by heating, while forming the [4B] compound with an exposed hydroxyl group. The [4B] compound also undergoes ring-closing (intramoleculate esterification) by heat, thereby generating propylundecanolide [5B]. In the [2B] state, the hydroxyl group is protected by the menthyl carbonate group, thereby inhibiting ring-closing (intramoleculate esterification) at room temperature. The thermal decomposition pattern of the [2B] compound was observed, and menthol was thermally decomposed and released during the temperature rise from 120°C to 260°C, and the γ-lactone was released for the first time during the temperature rise from 120°C to 200°C, and then was released more abundantly for the second time during the temperature rise from 200°C to 300°C. This is because even menthol used as a protecting group is released by deprotection by heating, and also exists for a certain period of time in the form of the [4B] compound (i.e., an intermediate). Although, ultimately, the lactone will be produced by intramoleculate esterification, this ring-closing can be delayed in the salt form. In addition, it can be observed from the thermal decomposition experimental results that menthol is thermally decomposed and released as the temperature rises, and in the [4B] state of the salt form, intramoleculate esterification to generate the lactone [5B] occurs at a higher temperature. That is, it can be found that the remaining thermal decomposition (Ring-Closing) occurs in the high temperature region after a certain period of time from the temperature range in which menthol is thermally decomposed.

[0231] Example 2

[0232] The target product of the preparation example (synthetic sodium (4-menthylcarbonyloxy)heptanoate, 5a, 1 wt%), water (40 wt%), milk (10 wt%), and flour (49 wt%) were mixed and kneaded into a dough, and heated and baked in an electric oven at a temperature of 200°C for 1 hour. After it was taken out of the electric oven, the generation of an aroma (e.g., a lactone aroma and a menthol aroma used to synthesize the target product) was confirmed by smelling the odor.

[0233] Example 3

[0234] After mixing the target product of the preparation example (synthetic sodium 5-(menthylcarbonyloxy)decanoate, 5c, 0.01 to 5% by weight), a matrix (paper pulp, 95 to 99% by weight), and other additives (balance), a sheet (2 mm thick) was produced by a roll-to-roll method, and dried at room temperature. The sheet was smelled at room temperature, and no odor of the flavorant compound used in the synthesis of the target product was detected. Then, the sheet was used as a cigarette paper for a cigarette, and a conventional cigarette was produced and smoked, and it was confirmed that the flavor (e.g., the lactone flavor and the mint flavor used in the synthesis of the target product) was generated upon smoking.

[0235] Example 4

[0236] After mixing the target product of the preparation example (synthetic sodium (4-menthylcarbonyloxy)undecanoate, 5d, 0.003 to 0.02% by weight), a tobacco powder (90 to 99% by weight, 0.03 mm to about 0.12 mm in average particle size), and other additives (balance), a tobacco composition was produced in a conventional manner. After wrapping the tobacco composition as a smoking medium in a cigarette paper, a filter and a paper were formed to produce a conventional cigarette. The cigarette was smoked, and it was confirmed that the flavor was generated in the mainstream smoke and the sidestream smoke upon smoking.

[0237] In view of the foregoing description, the embodiments are illustrated by the limited drawings, and a person of ordinary skill in the art can make various modifications and variations based on the description. Even if the described techniques are performed in a different order, and / or if the described components are combined or integrated in a different form or by other components or equivalents, or are replaced or substituted by other components or equivalents, appropriate results can be obtained. Therefore, other embodiments, other examples, and the scope equivalent to the claims should be interpreted as included in the present application.

Claims

1. A fragrance agent, characterized in that, The flavoring agent is 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 straight-chain or branched alkyl group having 1 to 30 carbon atoms. Part A is a portion derived from a fragrance compound containing at least one of an aromatic ring, an aliphatic ring, and an aliphatic chain having a hydroxyl group, wherein the hydroxyl group participates in a carbonate bond ( A' is a fragrance compound other than the hydroxyl group.

2. The fragrance agent according to claim 1, characterized in that, The fragrance compound is selected from cyclic monoterpenoids with hydroxyl groups, acyclic monoterpenoids with hydroxyl groups, aromatic compounds with 6 to 10 carbon atoms having hydroxyl groups, and non-aromatic rings with 5 to 6 carbon atoms having hydroxyl groups.

3. The fragrance agent according to claim 1, characterized in that, The fragrance compound is selected from the following chemical formulas: , , , , , , , , , , , , , , , , , , , , , , , , , as well as .

4. The fragrance agent according to claim 1, characterized in that, The portion A' is selected from the following chemical formulas. Where * represents the oxygen bonding site within the carbonate: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 , , , , , , , , , , , as well as .

5. The fragrance agent according to claim 1, characterized in that, The transition metals are 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 is selected from Li, Na, K, Rb, and Cs.

6. The fragrance agent 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] [Chemical Formula 1-2] [Chemical Formulas 1-3] [Chemical Formulas 1-4] [Chemical Formulas 1-5] [Chemical Formulas 1-6] [Chemical Formulas 1-7] [Chemical Formulas 1-8] [Chemical Formulas 1-9] [Chemical Formulas 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 fragrance agent according to claim 1, characterized in that, The fragrance agent is a fragrance compound that releases fragrance upon thermal decomposition.

8. The fragrance agent according to claim 1, characterized in that, The flavoring agent decomposes into the flavoring compound, lactone compound, and carbon dioxide upon thermal decomposition.

9. The fragrance agent according to claim 1, characterized in that, The compound decomposes thermally at temperatures above 80°C.

10. The fragrance agent according to claim 8, characterized in that, The lactone compound decomposes into either γ-lactone of Formula 2 or δ-lactone of Formula 3: [Chemical Formula 2] [Chemical Formula 3] R is a straight-chain or branched alkyl group having 1 to 30 carbon atoms.

11. The fragrance agent according to claim 8, characterized in that, The lactone compound is selected from the following chemical formulas: , , , , , , , , , , , as well as .

12. The fragrance agent according to claim 1, characterized in that, The flavoring agent is a flavoring agent for food or tobacco products.

13. A composition comprising the fragrance agent of claim 1.

14. The composition according to claim 13, characterized in that, The composition is a solid, liquid, or aerosol.

15. The composition according to claim 13, characterized in that, The composition also includes a carrier, additive, or both that are permitted for use in food or tobacco products.

16. A smoking article comprising the flavoring agent of claim 1, characterized in that, The smoking product is either a cigarette or an electronic cigarette.

17. The smoking article according to claim 16, characterized in that, The smoking products include liquids, powders, films, and fibers containing the flavoring agent.

18. A food product comprising the flavoring agent of claim 1.

19. The food product according to claim 18, characterized in that, The food is mixed with the flavoring agent of claim 1 or cooked by heating.

Images