Fragrance, fragrance composition and product containing the fragrance composition

Abstract

The present invention relates to a flavorant, a flavorant composition, and a product containing the flavorant composition. More specifically, the present invention relates to a flavorant, a composition containing the flavorant, and a product, wherein the basic skeleton of the flavorant includes a part derived from a sugar compound and a part derived from a fragrance compound, and the compound decomposes into a lactone compound, a sugar compound, and a fragrance compound upon thermal decomposition.

Description

Technical Field

[0001] The present invention relates to a flavorant, a flavorant composition, and a product containing the flavorant composition, which can release flavor components by heat. Background Art

[0002] Flavorants can be added to food and smoking articles to further improve the taste. The smoke or aerosol generated in a smoking article is transmitted from upstream to downstream to the smoker, thereby achieving the satisfaction of smoking. There are many factors that determine the satisfaction of smoking, and the most important of which is the cigarette taste felt by the smoker. Smokers hope to enjoy a variety of tobacco flavors from a smoking article. Therefore, in order to meet the needs of smokers, tobacco manufacturers add flavoring substances (e.g., flavorants) to enable smokers to experience different scents or tastes.

[0003] For existing flavorants, it is easy to decompose at room temperature during long-term storage of the smoking medium, resulting in the volatilization of flavor components. This makes it difficult to generate sufficient flavor during smoking to enhance the taste of cigarettes, or the flavor persistence weakens or the tobacco taste changes over time. Therefore, it is necessary to develop a flavorant that can improve the smoking satisfaction during smoking. In food, flavorants are used to add various flavors, but during long-term processing and / or storage of food, the flavors often volatilize and disappear. Therefore, it is necessary to develop a flavorant that can prevent or delay the release of volatile flavorants, thereby extending the shelf life and fully releasing the flavor when used by consumers. Summary of the Invention

[0004] Problems to be Solved by the Invention

[0005] Existing compounds with flavorant functions have poor chemical structure stability at room temperature (rt) or temperatures close to room temperature, so structural transformation or decomposition occurs, resulting in the volatilization of flavor components. To solve this problem, the present invention provides a flavorant in which flavor components are released by thermal decomposition when heated.

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

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

[0008] However, the technical problems to be solved by the present invention are not limited to the above-mentioned problems, and other problems not mentioned will be clearly understood by those of ordinary skill in the art from the following description.

[0009] Means for Solving the Problems

[0010] According to an embodiment of the present invention, there is provided a flavorant which is a compound represented by the following Chemical Formula 1:

[0011] [Chemical Formula 1]

[0012]

[0013] In the Chemical Formula 1,

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

[0015] R is a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms,

[0016] Moiety A' is a moiety derived from a fragrance compound containing at least one of an aromatic ring, an alicyclic ring, and an aliphatic chain having a hydroxyl group (-OH), and the hydroxyl group participates in a carbonate bond Moiety A' is a fragrance compound other than the hydroxyl group participating in the carbonate bond,

[0017] Moiety G' is a moiety derived from a sugar compound, and at least one of the hydroxyl groups (-OH) in the sugar compound ring participates in an ester bond G' is a sugar compound other than the hydroxyl group participating in the ester bond, and m is bonded to moiety G' through the ester bond The number of which is an integer from 1 to 8.

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

[0019] According to an embodiment of the present invention, the sugar compound is selected from tagatose, trehalose, galactose, rhamnose, cyclodextrin, maltodextrin, glucan, sucrose, glucose, ribulose, fructose, threose, arabinose, xylose, lyxose, allose, altrose, mannose, idose, lactose, maltose, invert sugar, isotrehalose, neotrehalose, palatinose or isomaltulose, erythrose, deoxyribose, glucose, idose, talose, erythritol, xylulose, allulose, turanose, cellobiose, amylopectin, glucosamine, mannosamine, fucose, glucuronic acid, gluconic acid, gluconolactone, abequose, galactosamine, isomaltooligosaccharide, xylooligosaccharide, gentiobioligosaccharide, sorbose, aspergillus oligosaccharide, oligopalatinose, fructooligosaccharide, maltotetritol, maltotriitol, maltooligosaccharide, lactulose, melibiose, raffinose, rhamnose, and ribose.

[0020] According to an embodiment of the present invention, the flavoring agent releases fragrance upon thermal decomposition.

[0021] According to an embodiment of the present invention, when the flavorant is thermally decomposed, it decomposes into the sugar compound, the fragrance compound, the lactone compound, and carbon dioxide.

[0022] According to an embodiment of the present invention, the flavorant is thermally decomposed at a temperature above 80°C.

[0023] According to an embodiment of the present invention, the flavorant is a flavorant for food or smoking products.

[0024] According to an embodiment of the present invention, there is provided a composition comprising the flavorant of the present invention.

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

[0026] According to an embodiment of the present invention, the composition further comprises a carrier, an additive, or both, which are permitted for use in food or smoking products.

[0027] According to an embodiment of the present invention, there is provided a smoking product comprising the flavorant of the present invention.

[0028] According to an embodiment of the present invention, the smoking product comprises a slurry, paste, liquid, gel, powder, microbead, flake, film, fiber or molded body containing the flavorant.

[0029] According to an embodiment of the present invention, the smoking product is a cigarette or an electronic cigarette.

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

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

[0032] Advantages of the Invention

[0033] According to an embodiment of the present invention, when the flavorant of the present invention is used in a smoking product, the flavor components generated during smoking can improve the pungent taste in the sidestream smoke, and since the flavorant emits flavor components through thermal decomposition during heating, the taste of the cigarette can be improved and a constant taste can be maintained.

[0034] According to an embodiment of the present invention, since the flavor components are emitted through thermal decomposition during heating, when used in food, it can provide rich flavors during the cooking process and extend the shelf life of the flavorant during the storage of the food. Brief Description of the Drawings

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

[0036] Figure 2 NMR analysis results of ethyl 4-(menthylcarbonyloxy)heptanoate (3a) according to an embodiment of the present invention.

[0037] Figure 3 NMR analysis results of 4-(menthylcarbonyloxy)heptanoic acid (4a).

[0038] Figure 4 NMR analysis results of glucosyl-(4-menthylcarbonyloxy)heptanoate (5a) prepared in an example according to an embodiment of the present invention.

[0039] Figure 5 NMR analysis results of glucosyl-(4-menthylcarbonyloxy)heptanoate (5a) prepared in an example according to an embodiment of the present invention.

[0040] Figure 6 NMR analysis results of 4-(menthylcarbonyloxy)nonanoic acid (4b) prepared in an example according to an embodiment of the present invention.

[0041] Figure 7 NMR analysis results of glucosyl-(4-menthylcarbonyloxy)nonanoate (5b) prepared in an example according to an embodiment of the present invention.

[0042] Figure 8 NMR analysis results of glucosyl-(4-menthylcarbonyloxy)nonanoate (5b) prepared in an example according to an embodiment of the present invention.

[0043] Figure 9 NMR analysis results of ethyl 5-(menthylcarbonyloxy)decanoate (3c) prepared in an example according to an embodiment of the present invention.

[0044] Figure 10 NMR analysis results of ethyl 5-(menthylcarbonyloxy)decanoate (3c) prepared in an example according to an embodiment of the present invention.

[0045] Figure 11 NMR analysis results of 5-(menthylcarbonyloxy)decanoic acid (4c) prepared in an example according to an embodiment of the present invention.

[0046] Figure 12 NMR analysis results of 5-(menthylcarbonyloxy)decanoic acid (4c) prepared in an example according to an embodiment of the present invention.

[0047] Figure 13NMR analysis results of 5-isopropyl-2-methylcyclohexyl-(1-oxo-1-(2-thioxothiazolin-3-yl)decyl-5-yl) carbonate (5c) prepared in an example according to an embodiment of the present invention.

[0048] Figure 14 NMR analysis results of glucosyl-(5-menthylcarbonyloxy)decanoate (6c) prepared in an example according to an embodiment of the present invention.

[0049] Figure 15 NMR analysis results of glucosyl-(5-menthylcarbonyloxy)decanoate (6c) prepared in an example according to an embodiment of the present invention.

[0050] Figure 16 NMR analysis results of ethyl 4-hydroxyundecanoate (2d) prepared in an example according to an embodiment of the present invention.

[0051] Figure 17 NMR analysis results of ethyl 4-hydroxyundecanoate (2d) prepared in an example according to an embodiment of the present invention.

[0052] Figure 18 NMR analysis results of ethyl 4-(menthylcarbonyloxy)undecanoate (3d) prepared in an example according to an embodiment of the present invention.

[0053] Figure 19 NMR analysis results of 4-(menthylcarbonyloxy)undecanoic acid (4d) prepared in an example according to an embodiment of the present invention.

[0054] Figure 20 NMR analysis results of 4-(menthylcarbonyloxy)undecanoic acid (4d) prepared in an example according to an embodiment of the present invention.

[0055] Figure 21 NMR analysis results of glucosyl-(4-menthylcarbonyloxy)undecanoate (6d) prepared in an example according to an embodiment of the present invention.

[0056] Figure 22 NMR analysis results of glucosyl-(4-menthylcarbonyloxy)undecanoate (6d) prepared in an example according to an embodiment of the present invention.

[0057] Figure 23 NMR analysis results of ethyl 4-(benzyloxycarbonyloxy)undecanoate (3e) prepared in an example according to an embodiment of the present invention.

[0058] Figure 24NMR analysis results of glucosyl-(4-benzyloxycarbonyloxy) nonanoate (5e) prepared in an example according to an embodiment of the present invention.

[0059] Figure 25 Thermal analysis results of the compound prepared in an example according to an embodiment of the present invention.

[0060] Figure 26 Component distribution of the compound prepared in an example according to an embodiment of the present invention with the change of the thermal decomposition temperature. Detailed Description of the Invention

[0061] Embodiments of the present invention will be described in detail below with reference to the accompanying drawings. When explaining the present invention, when it is considered that a detailed description of related well-known functions or structures will unnecessarily obscure the gist of the present invention, the detailed description thereof will be omitted. Also, the terms in this specification are used to accurately describe the embodiments and may vary according to the intention of the user, operator, or the convention in the technical field to which the present invention belongs. Therefore, the definition of the terms should be based on the entire content of the specification. The same reference numerals in each figure represent the same components.

[0062] Throughout the specification, when it is stated that one 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.

[0063] Throughout the specification, when a part "comprises" a certain component, it means that other components may be further included, rather than excluding other components.

[0064] Hereinafter, the flavoring agent of the present invention and the method of using the flavoring agent will be specifically described with reference to the embodiments and the accompanying drawings. However, the present invention is not limited to the embodiments and the accompanying drawings.

[0065] The present invention relates to a flavoring agent. According to an embodiment of the present invention, when the flavoring agent is heated, flavor components are expressed through thermal decomposition.

[0066] According to an embodiment of the present invention, the flavoring agent may be a compound represented by the following Chemical Formula 1.

[0067] [Chemical Formula 1]

[0068]

[0069] In an example of the present invention, the Chemical Formula 1 includes a part (G') derived from a sugar compound and a part (A') derived from a fragrance compound. In the Chemical Formula 1, the fragrance compound is covalently bonded through a carbonate bond, and the sugar compound is bonded through an ester bond Bonding. When the compound of Chemical Formula 1 is heated, it thermally decomposes and decomposes into flavor components of a sugar compound, a fragrance compound, and a lactone compound and then emits. For example, the compound of Chemical Formula 1 reacts with the hydroxyl group (-OH) of the sugar compound through the ring-opening mechanism of the lactone compound to bond through an ester bond, and reacts with the hydroxyl group of the fragrance compound to bond through a carbonate bond Bonding, thereby achieving synthesis. That is, the compound of Chemical Formula 1 has a stable structure and low volatility at about normal temperature or a similar temperature. When heated, the carbonate bond and the ester bond are broken through a ring-closure mechanism and decomposed into a sugar compound (G), a lactone compound, and a fragrance compound (A), so that the fragrance is released, and carbon dioxide harmless to the human body is generated during the decomposition process. During the heating process, the carbonate bond is broken and decomposed into a fragrance compound, and carbon dioxide is generated, and then the ester bond is broken through ring closure, thereby decomposing into a sugar compound and a lactone compound, thereby releasing the fragrance.

[0070] According to an embodiment of the present invention, the moiety A' in Chemical Formula 1 may be a moiety derived from a fragrance compound including at least one of an aromatic ring having a hydroxyl group, an alicyclic ring having a hydroxyl group, and an aliphatic chain having a hydroxyl group. The hydroxyl group includes at least one (for example, one or two) of a ring, a chain, or both, which may correspond to a substituent having a hydroxyl group, a basic skeleton, and / or a moiety. The hydroxyl group participates in the covalent bonding of the carbonate bond in Chemical Formula 1, and the moiety A' corresponds to the fragrance compound except for the hydroxyl group. That is, the hydroxyl group of the fragrance compound in the moiety A' is protected by the carbonate bond, and the decomposition reaction based on ring closure at normal temperature can be prevented.

[0071] According to an embodiment of the present invention, the fragrance compound may be selected from a cyclic monoterpenoid compound having a hydroxyl group, a monoterpenoid acyclic compound having a hydroxyl group, an aromatic compound having 6 to 10 carbon atoms and having a hydroxyl group, and a non-aromatic ring having 5 to 10 carbon atoms or 5 to 6 carbon atoms and their isomers. For example, the fragrance compound may be selected from the following compounds, which are compounds generated due to the breakage of the carbonate bond when the Chemical Formula 1 undergoes thermal decomposition:

[0072]

[0073]

[0074] According to an embodiment of the present invention, the moiety A' may be selected from the following chemical formulas. Wherein, * is the oxygen site in the carbonate bond:

[0075]

[0076]

[0077] According to an embodiment of the present invention, a part of G' is a part derived from a sugar compound, and is formed by participating in an ester bond through bonding to a hydroxyl group of the sugar compound ring The compound of Formula 1 can reduce volatility at room temperature, maintain structural stability, and improve solubility in organic solvents by bonding of the sugar compound. This can improve compatibility and / or processability in various substrates (or matrices) of the compound of Formula 1, and expand the scope of application as food and smoking products.

[0078] According to an embodiment of the present invention, the sugar compound may include a six-membered ring, a five-membered ring, or both, and at least one, at least two, at least three, or all of the hydroxyl groups bonded to the sugar compound ring may participate in the ester bond of Formula 1. For example, an ester bond is formed through a single or multiple hydroxyl groups, such that in the [] part in Formula 1, i.e., a single or multiple can be bonded to part G'.

[0079] According to an embodiment of the present invention, m refers to the [] part that can be bonded to part G' through the ester bond, i.e., the number of which can be an integer from 1 to 8, 1 to 7, 1 to 6, 1 to 5, 1 to 4, 1 to 3, or 1 to 2.

[0080] According to an embodiment of the present invention, the sugar compound can be selected from tagatose, trehalose, galactose, rhamnose, cyclodextrin, maltodextrin, glucan, sucrose, glucose, ribulose, fructose, threose, arabinose, xylose, lyxose, allose, altrose, mannose, idose, lactose, maltose, invert sugar, isotrehalose, neotrehalose, palatinose, or isomaltulose, erythrose, deoxyribose, glucose, idose, talose, erythritol, xylulose, allulose, turanose, cellobiose, amylopectin, glucosamine, mannosamine, fucose, glucuronic acid, gluconic acid, gluconolactone, abequose, galactosamine, isomaltooligosaccharide, xylooligosaccharide, gentiobioligosaccharide, sorbose, aspergillus oligosaccharide, oligopalatinose, fructooligosaccharide, maltotetritol, maltotriitol, maltooligosaccharide, lactulose, melibiose, raffinose, rhamnose, and ribose. Preferably, it can be glucose, lactose, maltose, galactose, sucrose, D-fructose, gulose, talose, and idose.

[0081] In an embodiment of the present invention, the flavoring agent can be selected from the following Formulas 1-1 to 1-9.

[0082] [Formula 1-1]

[0083]

[0084] [Chemical Formula 1-2]

[0085]

[0086] [Chemical Formula 1-3]

[0087]

[0088] [Chemical Formula 1-4]

[0089]

[0090] [Chemical Formula 1-5]

[0091]

[0092] In one example of the present invention, R in Chemical Formulas 1-1 to 1-5 1 to R 5 can be selected from hydroxyl (-OH) and

[0093] (n, R, and A' are as defined in Chemical Formula 1).

[0094] Preferably, can be at least one, at least two, at least three, at least four, or all of R 1 to R 5 , more preferably, can be at least one of R 1 and R 5 , at least one of R 1 and R 4 , and / or at least one of R 3 and R 4 .

[0095] [Chemical Formula 1-6]

[0096]

[0097] In one example of the present invention, R in Chemical Formula 1-6 1 to R 4 can be selected from hydroxyl (-OH) and (n, R, and A' are as defined in Chemical Formula 1).

[0098] Preferably, can be at least one, at least two, at least three, or all of R 1 to R 4 , more preferably, can be R 1and R 4 at least one of R 2 and R 3 at least one of, and / or R 1 and R 3 at least one of.

[0099] [Chemical Formula 1-7]

[0100]

[0101] [Chemical Formula 1-8]

[0102]

[0103] [Chemical Formula 1-9]

[0104]

[0105] In one example of the present invention, R in the Chemical Formulas 1-7 to 1-9 1 to R 8 can be selected from hydroxy (-OH) and (n, R and A' are defined as in the Chemical Formula 1).

[0106] Preferably, can be at least one of R 1 to R 8 at least two, at least three; at least four, or all, more preferably, can be at least one of R 1 to R 3 at least one of, and / or R 5 and R 8 at least one of, most preferably, can be at least one of R 1 to R 2 at least one of R 1 and R 3 at least one of R 6 and R 8 at least one of, and / or R 7 and R 5 at least one of.

[0107] According to an embodiment of the present invention, the flavoring agent can be selected from the following Chemical Formulas 1-1-a to 1-9-a.

[0108] [Chemical Formula 1-1-a]

[0109]

[0110] [Chemical Formula 1-2-a]

[0111]

[0112] [Chemical Formula 1-3-a]

[0113]

[0114] [Chemical Formula 1-4-a]

[0115]

[0116] [Chemical Formula 1-5-a]

[0117]

[0118] [Chemical Formula 1-6-a]

[0119]

[0120] [Chemical Formula 1-7-a]

[0121]

[0122] [Chemical Formula 1-8-a]

[0123]

[0124] [Chemical Formula 1-9-a]

[0125]

[0126] Among them, n, R, and A' are defined as in the said Chemical Formula 1.

[0127] According to an embodiment of the present invention, n in the said Chemical Formula 1 is an integer of 1 or 2. R can be a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; preferably, it can be a straight-chain or branched-chain alkyl group having 2 to 10 carbon atoms.

[0128] According to an embodiment of the present invention, the lactone compound can be a γ-lactone of the following Chemical Formula 2 or a δ-lactone of Chemical Formula 3.

[0129] [Chemical Formula 2]

[0130]

[0131] [Chemical Formula 3]

[0132]

[0133] In an example of the present invention, R in the said Chemical Formula 1 and Chemical Formula 2 can be a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, preferably a straight-chain or branched-chain alkyl group having 2 to 10 carbon atoms.

[0134] For example, the lactone compound can be selected from the following chemical formulas:

[0135] and

[0136] According to an 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, it can be 120 °C or higher, 150 °C or higher, 200 °C or higher, or more preferably, it can be 200 °C to 300 °C. And it can be thermally decomposed in an environment containing oxygen and / or moisture.

[0137] According to an embodiment of the present invention, the flavoring agent can be used as a flavoring agent for foods and smoking articles. That is, it can be used as an additive permitted for foods and smoking articles.

[0138] The present invention relates to a composition containing the flavoring agent of the present invention.

[0139] According to an embodiment of the present invention, the composition contains the flavoring agent of the present invention (i.e., the flavoring agent compound represented by Chemical Formula 1), and according to the use, it may further include a carrier, an additive, or both. The carrier and the additive are carriers and additives permitted for foods or smoking articles. For example, it may include a solvent, a binder, a diluent, a disintegrant, a lubricant, a flavoring agent, a colorant, a preservative, an antioxidant, an emulsifier, a stabilizer, a flavor enhancer, a sweetening agent, etc., but is not limited thereto.

[0140] According to an embodiment of the present invention, the composition may further include a substrate (or matrix) component according to the use. For example, it can be paper, pulp, wood, a polymer resin (such as cellulose), a fiber, a vegetable oil, a petroleum (such as paraffin), an animal oil, a wax, a fatty acid (such as an animal fat, a vegetable fat, a saturated fatty acid, an unsaturated fatty acid (such as a monounsaturated fatty acid or a polyunsaturated fatty acid) having 1 to 50 carbon atoms), etc. Organic substances and / or inorganic substances or ceramic powders (such as chalk, perlite, vermiculite, diatomaceous earth, colloidal silica, magnesium oxide, magnesium sulfate, magnesium carbonate), a wetting agent (such as glycerol or propylene glycol), and an acetate compound, etc. can be further added to the substrate component.

[0141] According to an embodiment of the present invention, the composition may further comprise a tobacco component according to its use. When the composition is used in a smoking article, it can generate a fragrance in the mainstream smoke and / or sidestream smoke under smoking conditions. The tobacco component may be a solid substance based on tobacco raw materials such as recombinant tobacco, cut tobacco, and reconstituted tobacco, and may be selected from tobacco leaves, extruded tobacco, and bandcast tobacco. In addition, the composition may further comprise an aerosol generating agent as a cigarette medium. Non-limiting examples of the aerosol generating agent 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.

[0142] According to an embodiment of the present invention, the flavoring agent may be 0.0001% by weight or more, 0.001% by weight or more, 0.01% by weight or more, 0.1% 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 it is included within this range, the fragrance can be expressed through the thermal decomposition of the flavoring agent, and the taste of the cigarette can be improved when used in a smoking article.

[0143] According to an embodiment of the present invention, the composition can be prepared into various phases. For example, it can be prepared into a solid (such as powder, crystal, flake, crushed material), slurry, paste, gel, liquid, emulsion, or aerosol. For example, the composition can be molded, mixed with the desired product, or used in ways such as printing, impregnation, spraying, and / or coating, which are well known in the art and will not be specifically described herein.

[0144] The present invention relates to a food containing the flavoring agent of the present invention. According to an embodiment of the present invention, the food may comprise at least one of the flavoring agent compounds represented by Chemical Formula 1 of the present invention. When the food is heated and / or roasted, the flavoring agent can provide a fragrance through thermal decomposition.

[0145] According to an embodiment of the present invention, the food may be made from food raw materials and the flavorant or a composition containing the flavorant, and, depending on the desired food, the composition may further contain food additives such as solvents (e.g., water, alcohol, liquid extracts), binders, diluents (e.g., oils), disintegrants, lubricants, colorants, preservatives, antioxidants, emulsifiers, stabilizers, flavor enhancers, sweeteners, etc., but not limited thereto. For example, the flavorant itself may be mixed with the food, or a composition containing the flavorant may be used by mixing, impregnating, spraying, and / or coating.

[0146] According to an embodiment of the present invention, the flavorant may be added to the food or heated to cook it into a semi-finished or finished product. When adding the flavorant, the food may be additionally heated to enable the flavorant to function. In addition, heating together with the flavorant in the form of a semi-finished or finished product to function, or adding the flavorant to the semi-finished or finished food and additionally heating to function, is also possible.

[0147] According to an embodiment of the present invention, the flavorant in the food may 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. When included within this range, the flavorant may produce a fragrance and maintain the inherent characteristics of the food raw materials.

[0148] According to an embodiment of the present invention, the "food" may be food materials, sauces, additives, seasonings, beverages, favorite foods, processed foods, frozen foods, refrigerated foods, stored foods, pickled foods, functional foods, fermented foods. And it may be added when uncooked (such as surface coating, filling, seasoning, pickling, drying, mixing), or semi-finished or finished foods (such as cooked finished foods through baking, steaming, roasting, frying, boiling, heating, etc.). Non-limiting examples include cereal products, rice products, cassava products, sago products, baked products, rice cake products, biscuit products, pastry products, confectionery products, dessert products, chewing gum, bubble gum, chocolate, ice cream, honey products, molasses products, yeast products, baking powder, salt and marinade products, seasonings, sweeteners, savory products, mustard products, vinegar products, sauces (seasonings), cooked fruit and vegetable products, and meat products, jellies, jams, fruit condiments, egg products, milk and dairy products, cheese products, butter and butter substitutes, milk substitutes, soybean products, edible oil and fat products, beverages, alcoholic beverages, beer, carbonated beverages, soda water and other non-alcoholic beverages, fruit beverages, fruit juices, coffee, artificial coffee, tea, cocoa, chocolate, candies, extract foods, plant extracts, meat extracts, gelatin, pharmaceuticals, elixirs, syrups and other preparations for manufacturing beverages.

[0149] The present invention relates to a smoking article comprising the flavorant of the present invention. According to an embodiment of the present invention, the smoking article may comprise at least one of the flavorant compounds represented by Chemical Formula 1 of the present invention. When the smoking article is heated and / or burned, the flavorant provides a flavor through thermal decomposition. That is, when the smoking article is heated and / or burned, the mainstream smoke and / or sidestream smoke emits a flavor.

[0150] According to an embodiment of the present invention, the "smoking article" may 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, whether it is based on a tobacco substitute or not. For example, the smoking article may refer to smoking articles that generate aerosols such as cigarettes, cigars, cigarillos, e-cigarettes, etc. 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, cut tobacco, and reconstituted tobacco.

[0151] According to an embodiment of the present invention, in the smoking article, the flavorant 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, and 1 to 20 parts by weight relative to 100 parts by weight of the smoking medium.

[0152] According to an embodiment of the present invention, during smoking, the amount of flavor components such as lactones emitted by the flavorant in the smoking article 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, and 1 to 20 parts by weight relative to 100 parts by weight of the smoking medium.

[0153] According to an embodiment of the present invention, the smoking article may be a cigarette-type cigarette, a liquid-type cigarette or a mixed-type cigarette, and may be a combustion-type cigarette or a heating-type cigarette. Or it may be an electronic cigarette (such as an electronic heated cigarette).

[0154] According to an embodiment of the present invention, when the flavorant is applied to the cigarette paper of a cigarette and the cigarette is heated and / or burned, especially when smouldering occurs, it can improve the pungent smell in the sidestream smoke by thermally expressing flavor components (such as lactones and / or flavor components).

[0155] According to an embodiment of the present invention, when applied to the medium of a heated cigarette rod, it can make the flavor components last. That is, for a heated cigarette, static heating will consume the flavor components contained in the medium during the initial puff, but the flavorant is only expressed when thermally decomposed. Therefore, even if puffing continues, flavor components can be produced until the last puff, thus maintaining a constant tobacco flavor.

[0156] According to an embodiment of the present invention, the smoking article may contain the flavorant or the flavorant composition, or be made of them. 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 (such as a liquid, gel, solid, slurry, paste), a paper tube, a tube, a filter (such as a tubular filter, a fiber filter, a woven filter, a paper filter, a capsule filter), rolling paper, cigarette paper, mouthpiece paper, packaging paper, a cartridge (such as a heated cartridge), etc. Without departing from the purpose of the present invention, it may include well-known components in the technical field of the present invention, which will not be specifically described herein.

[0157] According to an embodiment of the present invention, when manufacturing the smoking article, the flavorant itself may be mixed with a matrix or a substrate, or a composition containing the flavorant may be used to be mixed, printed, impregnated (or soaked), coated and / or sprayed with the matrix or the substrate.

[0158] According to an embodiment of the present invention, the smoking medium may further contain a flavorant and tobacco raw materials (e.g., medium raw materials, tobacco leaves), or may further contain additives. As another example, when manufacturing the components and / or members of a smoking article, the flavorant may be added as a flavorant and mixed with a substrate, a solvent, a flavor material, a smoking medium material, etc. suitable for the smoking article. And the smoking medium may be a liquid, a gel, or a solid.

[0159] The present invention will be described in more detail below through examples and comparative examples. However, the following examples are only for illustrating the present invention, and the content of the present invention is not limited to the following examples.

[0160] Example 1

[0161] [Scheme 1]

[0162]

[0163] (1-1) Synthesis of Ethyl 4-hydroxyheptanoate (2a)

[0164] Dissolve 20 g of γ-Heptalactone (0.15 mol) in 100 mL of methanol, and slowly add 11.17 g of KOH (0.16 mol, 1.05 eq.) while stirring, and then react at room temperature for 12 hours. After concentrating the reaction solution under reduced pressure, add 80 mL of DMF, and add 17 g of bromoethane (0.15 mol, 1 eq.) while stirring and react for 12 hours. Add 100 mL of water to the reaction solution and extract with ethyl acetate, and then wash with water and brine. Dry the organic layer and concentrate under reduced pressure to obtain 18.1 g of the target product 2a (66.7%, 2 steps). 4 1H NMR (CDCl3, 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-CH2), 1.81~0.92 (m, 12H, alkyl)

[0165] 1 1H NMR(CDCl3 3 , 400.13 MHz); δ8.01(s, 1H, -OH), 4.12(q, 2H, J=8Hz, COO-CH2-), 3.63(m, 1H, CH-O), 2.42(m, 2H, CO-CH2 2 ),1.81~0.92(m, 12H, alkyl)

[0166] (1-2) Synthesis of Ethyl 4-(mentylcarbonyloxy)heptanoate [[Ethyl 4-(mentylcarbonyloxy)heptanoate, 3a]]

[0167] Dissolve 18 g of ethyl 4-hydroxyheptanoate (2a, 0.1 mol) in 120 mL of THF, then add 16 g of pyridine (0.2 mol, 2 eq.) and stir while cooling with ice water. At the same time, slowly dropwise add a solution of 23 g of mentyl chloroformate (0.1 mol, 1 eq.) and 20 mL of THF. After one hour, warm the reaction solution to room temperature and react overnight, then add water and extract with ethyl acetate. Wash the organic layer with dilute hydrochloric acid, saturated sodium bicarbonate solution, and brine respectively, and then dry with MgSO 4 After drying and concentrating under reduced pressure, 30 g of the target product 3a (yield 81%) in the form of a yellow liquid was obtained.

[0168] 1 H NMR(CDCl 3 , 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)

[0169] (1-3) Synthesis of 4-(mentylcarbonyloxy)heptanoic acid [[4-(mentylcarbonyloxy)heptanoic acid, 4a]]

[0170] Dissolve 25 g of ethyl 4-(mentylcarbonyloxy)heptanoate (3a, 68.5 mmol) in 100 mL of THF and 30 mL of distilled water, add 4.2 g of lithium hydroxide monohydrate (102.4 mmol, 1.5 eq.) and react at room temperature for 12 hours. Add 50 mL of distilled water and extract with ether. Adjust the pH of the aqueous layer to 3 by adding concentrated hydrochloric acid and then extract with ethyl acetate. After washing the organic layer with brine, dry with MgSO 4 After drying and concentrating under reduced pressure, 21.8 g of the target product 4a (yield 81%) in the form of a yellow liquid was obtained.

[0171] 1 H NMR(CDCl 3, 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)

[0172] (1 - 4) Synthesis of Glucosyl-(4-mentylcarbonyloxy)heptanoate, 5a

[0173] Dissolve 3 g of 4-(mentylcarbonyloxy)heptanoic acid (4a, 9.1 mmol) in 20 mL of DMF, and then add 3.7 g of glucose (20.5 mmol, 2.2 eq.). While stirring at room temperature, add 1.7 g of diisopropylcarbodiimide (13.4 mmol, 1.5 eq.) and 0.05 g of DMAP (cat.) successively, and then react at room temperature for 12 hours. Add distilled water to the reaction mixture and extract with ethyl acetate. Wash the organic layer with dilute hydrochloric acid, saturated sodium bicarbonate solution, and brine successively, and then dry over MgSO 4 Dry and then concentrate under reduced pressure. Perform silica gel column chromatography on the mixture using a mixed solvent of methylene chloride and methanol (6:1) to obtain 0.6 g (yield 13%) of the target product 5a.

[0174] 1 1H NMR (CDCl 3 , 400.13 MHz); δ 5.30 - 3.54 (m, 13H, glucose, -COOCH, -COOCH), 2.45 (m, 2H, CO-CH2-), 2.03 - 0.78 (m, 27H, alkyl)

[0175] 2. Synthesis of Glucosyl-(4-mentylcarbonyloxy)nonanoate, 5b

[0176] [Scheme 2]

[0177]

[0178] (2 - 1) Synthesis of Ethyl 4-hydroxynonanoate, 2b

[0179] Dissolve 20 g of γ-Nonalactone (0.13 mol) in 100 mL of methanol. While stirring, slowly add 9.18 g of KOH (0.14 mol, 1.05 eq.) and react at room temperature for 12 hours. After concentrating the reaction solution under reduced pressure, add 80 mL of DMF and stir. While stirring, add 14 g of ethyl bromide (0.13 mol, 1 eq.) 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 MgSO 4 After drying, concentrate under reduced pressure to obtain 24 g (93%, 2 steps) of the target product 2b.

[0180] (2-2) Synthesis of Ethyl 4-(mentylcarbonyloxy)nonanoate [3b]

[0181] Dissolve 24 g of ethyl 4-hydroxynonanoate (2b, 0.12 mol) in 120 mL of THF. Add 18 g of pyridine (0.42 mol, 2 eq.) and cool with ice water. While stirring, slowly dropwise add a solution of 26 g of menthyl chloroformate (0.12 mol, 1 eq.) and 30 mL of THF. After one hour, warm the reaction solution to room temperature, react overnight, add water and extract with ethyl acetate. Wash the organic layer with dilute hydrochloric acid, saturated sodium bicarbonate solution and brine respectively, and then dry with MgSO 4 After drying, concentrate under reduced pressure to obtain 34 g (yield 74.5%) of the target product 3b as a yellow liquid.

[0182] 1 H NMR (CDCl 3 , 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)

[0183] (2-3) Synthesis of 4-(Mentylcarbonyloxy)nonanoic acid [4b]

[0184] Dissolve 11.5 g of ethyl 4-(mentylcarbonyloxy)nonanoate (3b, 29.9 mmol) in 50 mL of THF and 20 mL of distilled water. Add 2 g of lithium hydroxide monohydrate (48.7 mmol, 1.6 eq.) and react at room temperature for 12 hours. Add 50 mL of distilled water and extract with ether. Adjust the pH of the aqueous layer to 3 with concentrated hydrochloric acid and then extract with ethyl acetate. Wash the organic layer with brine and then dry with MgSO 4 After concentration under reduced pressure, 8.6 g (yield 80%) of the target product 4b as a yellow liquid was obtained.

[0185] 1 H NMR (CDCl 3 , 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)

[0186] (2 - 4) Synthesis of Glucosyl-(4-mentylcarbonyloxy)nonanoate, 5b

[0187] Dissolve 6.6 g of 4-(mentylcarbonyloxy)nonanoic acid (4b, 24.1 mmol) in 30 mL of DMF and add 13 g of glucose (72.1 mmol, 3 eq.). While stirring at room temperature, add 3.4 g of diisopropylcarbodiimide (26.9 mmol, 1.2 eq.) and 0.05 g of DMAP (cat.) in sequence, and then react at room temperature for 12 hours. Add distilled water to the reaction mixture and extract with ethyl acetate. Wash the organic layer with dilute hydrochloric acid, saturated sodium bicarbonate solution, and brine respectively and then dry with MgSO 4 After drying, concentrate under reduced pressure. Use a mixed solvent of dichloromethane and methanol (8:1) for silica gel column chromatography of the mixture to obtain 2 g (yield 16%) of the target product 5b.

[0188] 1 H NMR (CDCl 3 , 400.13 MHz); δ 5.57 - 3.35 (m, 13H, glucose, -COOCH, -COOCH), 2.43 (m, 2H, CO-CH 2 -), 2.03 - 0.78 (m, 31H, alkyl)

[0189] 3. Synthesis of Glucosyl-(5-mentylcarbonyloxy)decanoate (6c)

[0190] [Scheme 3]

[0191]

[0192] (3-1) Synthesis of Ethyl 5-hydroxydecanoate (2c)

[0193] Dissolve 10 g of δ-Decalactone (58.7 mmol) in 50 mL of methanol, and slowly add 4.2 g of KOH (64.7 mmol, 1.05 eq.) while stirring, then react at room temperature for 12 hours. After concentrating the reaction solution under reduced pressure, add 40 mL of DMF, add 6.4 g of ethyl bromide (58.7 mmol, 1 eq.) while stirring and react for 12 hours.

[0194] 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 MgSO 4 and concentrate under reduced pressure to obtain 7.6 g (60%, 2 steps) of the target product 2c.

[0195] (3-2) Synthesis of Ethyl 5-(mentylcarbonyloxy)decanoate (3c)

[0196] Dissolve 7.5 g of ethyl 5-hydroxydecanoate (2c, 34.6 mmol) in 50 mL of THF, add 5.3 g of pyridine (69.2 mmol, 2 eq.), cool with ice water, and then slowly dropwise add 8.3 g of menthyl chloroformate (37.9 mmol, 1.1 eq.) and 20 mL of THF solution while stirring. After one hour, warm the reaction solution to room temperature, react overnight, add water and extract with ethyl acetate. Wash the organic layer with dilute hydrochloric acid, saturated sodium bicarbonate solution and brine respectively, and then dry with MgSO 4 and concentrate under reduced pressure. Use a mixed solvent of n-hexane and ethyl acetate (7:1) for silica gel column chromatography of the mixture to obtain 4.5 g (yield 32.6%) of the target product 3c.

[0197] 1 H NMR(CDCl 3, 400.13 MHz); δ 4.72 (m, 1H, -COOCH-), 4.52 (m, 1H, COO-CH-), 4.12 (q, 2H, J = 8 Hz, COO-CH 2 -), 2.31 (t, 2H, J = 8 Hz, CO-CH 2 -), 2.08 - 0.86 (m, 27H, alkyl), 0.79 (d, 6H, J = 8 Hz, -CH 3 ).

[0198] (3 - 3) Synthesis of 5-(Mentylcarbonyloxy)decanoic acid [5-(Mentylcarbonyloxy)decanoic acid, 4c]

[0199] Dissolve 2.7 g of ethyl 5-(mentylcarbonyloxy)nonanoate (3c, 6.8 mmol) in 20 mL of THF and 10 mL of distilled water, add 0.42 g of lithium hydroxide monohydrate (10.2 mmol, 1.5 eq.), and react at room temperature for 12 hours. Add 10 mL of distilled water and extract with ether. Add concentrated hydrochloric acid to adjust the pH of the aqueous layer to 3, and then extract with ethyl acetate. Wash the organic layer with brine and then dry over MgSO 4 and concentrate under reduced pressure to obtain 2.1 g (yield 78%) of the target product 4c as a yellow liquid.

[0200] 1 H NMR (CDCl 3 , 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-CH 2 -), 2.38 (m, 2H, CO-CH 2 -), 2.06 - 0.78 (m, 33H, alkyl)

[0201] (3 - 4) Synthesis of 5-Isopropyl-2-methylcyclohexyl(1-oxo-1-(2-thioxothiazolidin-3-yl)decan-5-yl)carbonate [5-Isopropyl-2-methylcyclohexyl(1-oxo-1-(2-thioxothiazolidin-3-yl)decan-5-yl)carbonate, 5c]

[0202] Dissolve 1.9 g of 5-(mentylcarbonyloxy)decanoic acid (4c, 5.1 mmol) in 20 mL of dried dichloromethane. After adding 0.73 g of 2-mercaptothiazoline (6.1 mmol, 1.2 eq.), cool it with ice water, and then slowly add 1.2 g of EDC·HCl (6.1 mmol, 1.2 eq.) and 50 mg of DMAP respectively while stirring to carry out the reaction. After one hour, warm the reaction solution to room temperature. After reacting overnight, add water and extract with dichloromethane. Wash the organic layer with dilute hydrochloric acid, saturated sodium bicarbonate solution and brine respectively, and then dry with MgSO 4 Dry, and then concentrate under reduced pressure. Use a mixed solvent of n-hexane and ethyl acetate (3:1) for silica gel column chromatography of the mixture to obtain 2.1 g (yield 87.5%) of the target product 5c.

[0203] 1 H NMR (CDCl 3 , 400.13 MHz); δ 4.71 (m, 1H, -COOCH-), 4.57 (t, 2H, J = 8 Hz, N-CH 2 ), 4.51 (m, 1H, COO-CH-), 4.11 (q, 2H, J = 8 Hz, COO-CH 2 -), 3.28 (t, 2H, J = 8 Hz, S-CH 2 ), 3.21 (m, 2H, CO-CH 2 -), 2.04 - 0.79 (m, 33H, alkyl)

[0204] (3 - 5) Synthesis of glucosyl-(5-mentylcarbonyloxy)decanoate [Glucosyl-(5-mentylcarbonyloxy)decanoate, 6c]

[0205] Dissolve 2.2 g of 5-isopropyl-2-methylcyclohexyl (1-oxo-1-(2-thioxothiazolin-3-yl)decyl-5-yl) carbonate (5c, 4.7 mmol) in 20 mL of pyridine, and then add 2.5 g of glucose (14.1 mmol, 3 eq.). While stirring at room temperature, add 93 mg of sodium hydride (60%, 2.4 mmol, 0.5 eq.) and 0.03 g of DMAP (cat.) in sequence, and then react at room temperature for 12 hours. Add 0.5 mL of acetic acid to the reactant, then add saturated brine and extract with ethyl acetate. Use MgSO 4After drying the organic layer, it was concentrated under reduced pressure. The mixture was subjected to silica gel column chromatography using a dichloromethane / methanol mixed solvent (8:1) to obtain 0.55 g (yield 22%) of the target product 6c.

[0206] 1 H NMR(CDCl 3 , 400.13 MHz); δ 5.57~3.15 (m, 13H, glucose, -COOCH, -COOCH), 2.36 (m, 2H, CO-CH 2 -), 2.05~0.80 (m, 33H, alkyl)

[0207] 4. Synthesis of Glucosyl-(4-mentylcarbonyloxy)undecanoate (6d)

[0208] [Scheme 4]

[0209]

[0210] (4-1) Synthesis of Ethyl 4-hydroxyundecanoate (2d)

[0211] 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. After concentrating the reaction solution under reduced pressure, 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.

[0212] 80 mL of water was added to the reaction solution and it was extracted with ethyl acetate, then washed with water and brine. After drying the organic layer with MgSO 4 , it was concentrated under reduced pressure to obtain 10.7 g (85.6%, 2 steps) of the target product 2d.

[0213] 1 H NMR(CDCl 3 , 400.13 MHz); δ 4.12 (q, 2H, J = 8 Hz, COO-CH 2 -), 3.59 (m, 1H, CH-O), 2.43 (m, 2H, CO-CH 2 ), 1.81~0.92 (m, 20H, alkyl)

[0214] (4-2) Synthesis of Ethyl 4-(mentylcarbonyloxy)undecanoate (3d)

[0215] Dissolve 11 g of ethyl 4-hydroxyundecanoate (2d, 47.7 mmol) in 60 mL of THF, add 6.8 g of pyridine (95.5 mmol, 2 eq.), cool with ice water, and then slowly dropwise add (dropping) 10.5 g of menthyl chloroformate (47.7 mmol, 1 eq.) and 20 mL of THF solution while stirring. After one hour, warm the reaction solution to room temperature, add water after reacting overnight, and extract with ethyl acetate. Wash the organic layer successively with dilute hydrochloric acid, saturated sodium bicarbonate solution, and brine, and then dry with MgSO 4 After drying and concentrating under reduced pressure, 8.3 g (yield 42.1%) of the target product 3d as a yellow liquid was obtained.

[0216] 1 1H NMR (CDCl 3 , 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)

[0217] (4-3) Synthesis of 4-(Mentylcarbonyloxy)undecanoic acid (4d)

[0218] Dissolve 8.3 g of ethyl 4-(mentylcarbonyloxy)undecanoate (3d, 19.4 mmol) in 30 mL of THF and 20 mL of distilled water, add 1.2 g of lithium hydroxide monohydrate (29.1 mmol, 1.5 eq.), and react at room temperature for 12 hours. Add 20 mL of distilled water and extract with ether. Adjust the pH of the aqueous layer to 3 by adding concentrated hydrochloric acid, and then extract with ethyl acetate. Wash the organic layer with brine and then dry with MgSO 4 After drying, concentrate under reduced pressure. Perform silica gel column chromatography 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.

[0219] 1 1H NMR (CDCl 3, 400.13 MHz); δ 4.75 (m, 1H, -COOCH-), 4.51 (m, 1H, COO-CH-), 2.43 (m, 2H, CO-CH 2 -), 2.17 - 0.78 (m, 35H, alkyl)

[0220] (4-4) Synthesis of 5-Isopropyl-2-methylcyclohexyl(1-oxo-1-(2-thioxothiazolidin-3-yl)dodecan-5-yl)carbonate [5-Isopropyl-2-methylcyclohexyl(1-oxo-1-(2-thioxothiazolidin-3-yl)dodecan-5-yl)carbonate, 5d]

[0221] Dissolve 9.1 g of 4-(menthylcarbonyloxy)undecanoic acid (4d, 23.6 mmol) in 50 mL of dried dichloromethane, add 3 g of 2-mercapto-thiazoline (24.8 mmol, 1.05 eq.), cool with ice water, and then slowly add 5 g of EDC·HCl (25.9 mmol, 1.1 eq.) and 20 mg of DMAP while stirring for reaction. After one hour, warm the reaction solution to room temperature, react overnight, add water, and extract with dichloromethane. Wash the organic layer with dilute hydrochloric acid, saturated sodium bicarbonate solution, and brine respectively, and then dry with MgSO 4 to obtain 10.9 g (yield 92%) of the target product 5d after concentration under reduced pressure.

[0222] 1 H NMR (CDCl 3 , 400.13 MHz); δ 4.71 (m, 1H, -COOCH-), 4.57 (t, 2H, J = 8 Hz, N-CH 2 ), 4.51 (m, 1H, COO-CH-), 4.11 (q, 2H, J = 8 Hz, COO-CH 2 -), 3.28 (t, 2H, J = 8 Hz, S-CH 2 ), 3.21 (m, 2H, CO-CH 2 -), 2.04 - 0.79 (m, 33H, alkyl)

[0223] (4-5) Synthesis of Glucosyl-(4-mentylcarbonyloxy)undecanoate [Glucosyl-(4-mentylcarbonyloxy)undecanoate, 6d]

[0224] Dissolve 4.9 g of 4-(menthylcarbonyloxy)undecanoic acid (12.7 mmol) in 30 mL of dichloromethane, then add 3 g of thionyl chloride (25.2 mmol, 2 eq) and reflux for two hours. Then, in another flask, add 6.9 g of glucose (3 eq) and 4.9 g of pyridine (5 eq) in DMF solvent, stir at room temperature, and slowly dropwise add the above reaction solution and react for 12 hours. Add water to the reaction solution and extract with dichloromethane. Wash the organic layer with dilute hydrochloric acid, saturated sodium bicarbonate solution, and brine respectively, and then dry with MgSO 4 Dry, concentrate under reduced pressure, and use silica gel column chromatography (MC / MeOH, 10:1) to obtain 2.6 g of the target product (6d) (yield 37.7%).

[0225] 1 H NMR (CDCl 3 , 400.13 MHz); δ 5.23 - 3.35 (m, 13H, glucose, -COOCH, -COOCH), 2.43 (m, 2H, CO-CH 2 -), 2.03 - 0.78 (m, 35H, alkyl)

[0226] 5. Synthesis of Glucosyl-(4-benzyloxycarbonyloxy)undecanoate (5e)

[0227] [Scheme 5]

[0228]

[0229] (5-1) Synthesis of Ethyl 4-hydroxyundecanoate (2d)

[0230] Dissolve 10 g of γ-undecalactone (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 at room temperature for 12 hours. Concentrate 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.

[0231] Add 80 mL of water to the reaction solution and extract with ethyl acetate, then wash with water and brine. Dry the organic layer with MgSO 4 Dry the organic layer, concentrate under reduced pressure to obtain 10.7 g (85.6%, 2 steps) of the target product 2d.

[0232] 1 H NMR (CDCl 3 , 400.13 MHz); δ 4.12 (q, 2H, J = 8 Hz, COO-CH 2 -), 3.59 (m, 1H, CH-O), 2.43 (m, 2H, CO-CH 2 ), 1.81~0.92 (m, 20H, alkyl)

[0233] (5-2) Synthesis of Ethyl 4-(benzyloxycarbonyloxy)undecanoate, 3e

[0234] Dissolve 8.3 g of ethyl 4-hydroxyundecanoate (2d, 36 mmol) in 50 mL of THF. After adding 5.5 g of pyridine (72.3 mmol, 2 eq.) and cooling with ice water, 6.1 g of benzyl chloroformate (35.3 mmol, 1 eq.) and 20 mL of THF solution are slowly dropped in while stirring. After one hour, the reaction solution is warmed to room temperature, and after reacting overnight, water is added and extraction is carried out with ethyl acetate. The organic layer is washed with dilute hydrochloric acid, saturated sodium bicarbonate solution, and brine respectively, and then dried with MgSO 4 After concentration under reduced pressure, 9.9 g (yield 75.6%) of the target product 3e in the form of a yellow liquid is obtained.

[0235] 1 H NMR (CDCl 3 , 400.13 MHz); δ 7.37~7.34 (m, 5H, ph), 5.14 (m, 2H, O-CH 2 -Ph), 4.12 (brs, 1H, O-CH-), 2.42 (m, 2H, CO-CH2-), 1.90~0.79 (m, 21H, alkyl)( Figure 24 )

[0236] (5-3) Synthesis of 4-(Benzyloxycarbonyloxy)undecanoic acid, 4e

[0237] Dissolve 10 g of ethyl 4-(benzyloxycarbonyloxy)undecanoate (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. Add concentrated hydrochloric acid to adjust the pH of the aqueous layer to 3, and then extract with ethyl acetate. Wash the organic layer with brine and then dry with MgSO 4 After drying and concentrating under reduced pressure, 8.2 g (yield 89%) of the target product 4e was obtained.

[0238] 1 H NMR (CDCl 3 , 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)

[0239] (5-4) Synthesis of Glucosyl-(4-benzyloxycarbonyloxy)nonanoate, 5e

[0240] Dissolve 8 g of 4-(benzyloxycarbonyloxy)undecanoic acid (4e, 23.8 mmol) in 30 mL of DMF, and then add 13 g of glucose (72.1 mmol, 3 eq.). While stirring at room temperature, sequentially add 3.4 g of diisopropylcarbodiimide (26.9 mmol, 1.1 eq.) and 0.05 g of DMAP (cat.), and then react at room temperature for 12 hours. Add distilled water to the reaction mixture and extract with ethyl acetate. Wash the organic layer with dilute hydrochloric acid, saturated sodium bicarbonate solution, and brine respectively, and then dry with MgSO 4 After drying, concentrate under reduced pressure. Perform silica gel column chromatography on the mixture using a mixed solvent of dichloromethane and methanol (8:1) to obtain 0.3 g (yield 2.5%) of the target product 5e.

[0241] 1 H NMR (CDCl 3 , 400.13 MHz); δ 7.37 - 7.34 (m, 5H, ph), 5.30 - 3.37 (m, 13H, glucose, -COOCH, -COOCH), 2.39 (m, 2H, CO-CH 2 -), 1.92 - 0.84 (m, 17H, alkyl)

[0242] Experimental Example

[0243] A pyrolysis test was conducted to confirm the pyrolytic behavior of the 6d compound (2C) when exposed to heat. This test utilized the well-known Pyrolysis-Gas Chromatography / Mass Spectrometry [Py-GC / MS] method. The pyrolyzer was operated in a system where the "Double-Shot Pyrolyzer 2020iD" (Frontier Lab, Japan) was connected to GC / MS equipment (Agilent 6890 GC, USA / Agilent 7890 MSD, USA). After diluting 2C to a concentration of 2.5% in an ethyl alcohol solution, 10 μl was loaded into 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. The initial pyrolysis temperature was 80 °C, and the sample cup containing the sample was exposed to the furnace at 80 °C for 30 seconds, causing the target compound (2C) in the sample cup to pyrolyze. 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 being affected by the pyrolysis temperature. After the GC / MS analysis of the first pyrolysis, the originally used sample cup was pyrolyzed again without injecting a new compound. This time, the pyrolysis temperature was 90 °C, which was 10 °C higher, and it lasted for 30 seconds. Similarly, after the thermal decomposition ended, the sample cup was removed from the furnace to avoid being affected by the pyrolysis temperature. In this way, the initial sample was loaded into the sample cup, and the thermal decomposition experiment was carried out with the pyrolysis temperature increasing from 80 °C, 90 °C, 100 °C to 320 °C. Thus, the pyrolysis characteristics of the compound changing with the increase in the pyrolysis temperature at different temperatures could be observed. The results are as Figure 25 and Figure 26 shown.

[0244] [Decomposition mechanism]

[0245]

[0246] Referring to Figure 25 and Figure 26 , from the results of the thermal decomposition experiment of the 2C compound, it can be seen that menthol and γ-undecalactone decompose at a temperature of approximately 120 °C.

[0247] That is, in the decomposition mechanism, the lactone [1C, γ-undecalactone] undergoes ring-opening, and after the hydroxyl group is bonded to L-menthol through a carbonate linkage, it is ester-bonded to a sugar (glucose) to prepare a [2C] compound. After applying the [2C] compound to the product substrate, L-menthol ([3C]) and CO are generated by heating 2 , and at the same time, a [4C] compound with an exposed hydroxyl group is formed. The [4C] compound also undergoes ring-closing (ring-closing, intramolecular esterification) through heat, thereby generating γ-undecalactone [5C]. In the [2C] state, the hydroxyl group is protected by a menthyl carbonate group, thus inhibiting ring-closing (intramolecular esterification) at room temperature. In addition, as a result of the thermal decomposition experiment, it was confirmed that a lactone ring was generated while decomposing menthol by heat.

[0248] Example 2

[0249] The target product of the preparation example (synthesized glucosyl-(4-menthylcarbonyloxy)heptanoate, 5a, 1% by weight), water (40% by weight), milk (10% by weight), and wheat flour (49% by weight) were mixed and kneaded into a dough, and baked in an electric oven at a temperature of about 200 °C for 1 hour. After taking it out of the electric oven, it was confirmed by smelling that a fragrance was generated (for example, the lactone fragrance and menthol fragrance used to synthesize the target product).

[0250] Example 3

[0251] The target product of the preparation example (synthesized glucosyl-(4-menthylcarbonyloxy)nonanoate, 5b, 0.01% to 5% by weight), a substrate (pulp, 95% to 99% by weight), and other additives (the balance) were mixed, and then made into a sheet (2 mm thick) by roll-to-roll (room temperature or low temperature), and dried at room temperature. When smelling the sheet at room temperature, there was no smell of the fragrance compound used in the synthesized target product. Then, this sheet was used as cigarette paper for cigarettes to make ordinary cigarettes and smoke, and it was confirmed that a fragrance was generated during smoking (for example, the lactone fragrance and mint fragrance used to synthesize the target product).

[0252] Example 4

[0253] The target product of the preparation example (synthesized glucosyl-(5-menthylcarbonyloxy)decanoate, 6c, 0.003 wt% to 0.02 wt%), tobacco powder (90 wt% to 99 wt%, average particle size of 0.03 mm to about 0.12 mm), and other additives (the balance) are mixed, and a tobacco composition is manufactured in a conventional manner. After wrapping the tobacco composition as a smoking medium with cigarette paper, a filter tip and cigarette paper are formed to prepare a conventional cigarette. When smoking the cigarette, it is confirmed that flavors (for example, the lactone flavor and mint flavor used for synthesizing the target product) are generated in the mainstream smoke and sidestream smoke during smoking.

[0254] In summary, the embodiments are illustrated by limited drawings, and those of ordinary skill in the art can make various changes and modifications based on the description. Appropriate results can also be obtained if the described techniques are performed in a different order, and / or if the described components are combined or assembled in a different form, or replaced or substituted by other components or equivalents. Therefore, other embodiments, other embodiments, and the scope of the claims and their equivalents should be construed as being included in the present invention.

Claims

1. A flavoring 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, R is a linear or branched alkyl group having 1 to 30 carbon atoms, Portion A' is a portion derived from a fragrance compound containing at least one of an aromatic ring, an alicyclic ring, and an aliphatic chain having a hydroxyl group (-OH), and the hydroxyl group participates in a carbonate bond Portion A' is a fragrance compound other than the hydroxyl group participating in the carbonate bond Moiety G' is a moiety derived from a saccharide compound, and at least one of the hydroxyl groups (-OH) in the saccharide compound ring is involved in an ester bond G' is a saccharide compound other than the hydroxyl group participating in the ester bond, and m is bonded to moiety G' through the ester bond The number of m is an integer from 1 to 8.

2. The flavoring agent according to claim 1, characterized in that, the perfume compound is selected from cyclic monoterpenoids having a hydroxyl group, acyclic monoterpenoids having a hydroxyl group, aromatic compounds having 6 to 10 carbon atoms and having a hydroxyl group, and non-aromatic ring compounds having 5 to 6 carbon atoms and having a hydroxyl group.

3. The flavoring agent according to claim 1, characterized in that, the perfume compound is selected from the following chemical formulas: and 4. The flavoring agent according to claim 1, characterized in that, the moiety A' is selected from the following chemical formulas, wherein, * is the oxygen bonding site in the carbonate bond in the Chemical Formula 1, and 5. The flavoring agent according to claim 1, characterized in that, the sugar compound is selected from tagatose, trehalose, galactose, cyclodextrin, maltodextrin, glucan, sucrose, glucose, ribulose, fructose, threose, arabinose, xylose, lyxose, allose, altrose, mannose, lactose, maltose, isotrehalose, neotrehalose, palatinose or isomaltulose, erythrose, deoxyribose, idose, talose, erythritol, xylulose, allulose, turanose, cellobiose, amylopectin, glucosamine, mannosamine, fucose, glucuronic acid, gluconic acid, gluconolactone, abequose, galactosamine, isomaltooligosaccharide, xylooligosaccharide, gentiobioligosaccharide, sorbose, aspergillus oligosaccharide, oligopalatinose, fructooligosaccharide, maltotetritol, maltotriitol, lactulose, melibiose, raffinose, rhamnose, and ribose.

6. The flavoring agent according to claim 1, characterized in that, the flavoring agent is selected from the following Chemical Formulas 1-1 to 1-9: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] Among them, R in Chemical Formulas 1-1 to 1-5 1 to R 5 are respectively selected from hydroxyl (-OH) and selected from, wherein n, R and A' are as defined in said Chemical Formula 1; [Chemical Formula 1-6] Among them, R 1 to R 4 are respectively selected from hydroxy (-OH) and ; n, R and A' are as defined in the said Chemical Formula 1; [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-9] Among them, R in Chemical Formulas 1-7 to 1-9 1 to R 8 are respectively selected from hydroxyl group (-OH) and n, R and A' are as defined in Chemical Formula 1 above.

7. The flavoring agent according to claim 1, characterized in that, the flavoring agent is selected from the following Chemical Formulas 1-1-a to 1-9-a: [Chemical Formula 1-1-a] [Chemical Formula 1-2-a] [Chemical Formula 1-3-a] [Chemical Formula 1-4-a] [Chemical Formula 1-5-a] [Chemical Formula 1-6-a] [Chemical Formula 1-7-a] [Chemical Formula 1-8-a] [Chemical Formula 1-9-a] 8. The flavoring agent according to claim 1, characterized in that, the flavoring agent releases fragrance during thermal decomposition, and decomposes into the sugar compound, the perfume compound, a lactone compound, and carbon dioxide during thermal decomposition.

9. The flavoring agent according to claim 1, characterized in that, the compound thermally decomposes at a temperature of 80 °C or higher.

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

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

12. The flavoring agent according to claim 1, characterized in that the flavoring agent is a food flavoring agent or a smoking article flavoring agent.

13. A composition comprising the flavoring agent according to claim 1.

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

15. The composition according to claim 13, characterized in that the composition further comprises a carrier, an additive or both that are permitted for use in food or smoking articles.

16. A smoking article comprising the flavoring agent according to claim 1.

17. The smoking article according to claim 16, characterized in that the smoking article includes a slurry, paste, liquid, gel, powder, microbead, flake, fiber containing the flavoring agent.

18. The smoking article according to claim 16, characterized in that the smoking article is a cigarette or an electronic cigarette.

19. A food comprising the flavoring agent according to claim 1.

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