Aroma imparting method

Abstract

The present invention provides a method for imparting aroma to food or beverage, which comprises heating a specific precursor compound of sulfides in edible oil.The present invention also provides a method for imparting aroma to food or beverage, which comprises mixing a specific decomposition enhancer and a specific precursor compound of sulfides in a solution, followed by heating the mixture.

Description

Technical Field

[0001] The present invention relates to a method for imparting aroma to food and drink products, and more particularly, to a method for imparting aroma (especially garlic aroma) to food and drink products, which includes heating a specific compound that exhibits sulfides by thermal decomposition in edible oil. The present invention also relates to a method for imparting aroma (especially garlic aroma) to food and drink products, which includes heating at least one selected from the group consisting of a pyridine derivative having a specific structure and a Lewis acidic metal compound and a specific compound that exhibits sulfides by thermal decomposition in a solvent.

Background Art

[0002] Garlic contains about 1% of S-allyl-L-cysteine sulfoxide, which is a cysteine derivative and a precursor of aroma, and its common name is alliin (hereinafter sometimes referred to as "ALCSO"). Alliin is present in the cytoplasm. When garlic is cut with a knife or the like, alliinase, an alliin-degrading enzyme localized in the vacuole of the cell, comes into contact with ALCSO, and ALCSO is enzymatically decomposed. As a result, alliin is converted via allicin into sulfur-containing compounds typified by sulfides and thiophenes, and these become the characteristic aroma components of garlic (Non-Patent Document 1).

[0003] Regarding the method of decomposing ALCSO itself, there have already been reports. For example, it is known that ALCSO is decomposed by irradiating an aqueous solution of ALCSO with γ-rays (Non-Patent Documents 2 to 4). In these reports, it is presumed that ALCSO is decomposed through a reaction caused by hydroxyl radicals generated by γ-ray irradiation. However, even when ALCSO is decomposed by such a method, compounds of sulfides, which are the main components of garlic aroma, are not detected, and the aroma characteristic of garlic cannot be confirmed sensorially.

Prior Art Documents

Patent Documents

[0004] [Non-Patent Document 1] Rose, P. et al. Nat. Prod. Rep., 2005, 22, 351-368 [Non-Patent Document 2] Nishimura, H. et al. Agric. Biol. Chem. 1970, 34, 609-616 [Non-Patent Document 3] Nishimura, H. et al. Agric. Biol. Chem. 1973, 37(2), 213-217 [Non-Patent Document 4] Nishimura, H. et al. Agric. Biol. Chem. 1973, 37(7), 1749-1750 [Summary of the Invention] [Problems to be Solved by the Invention]

[0005] Garlic is a very important raw material that affects the flavor quality of various seasonings and processed foods, and the demand is increasing globally. As a result, the price of garlic is soaring and procurement is becoming difficult. Therefore, in order to overcome such problems, the development of alternative materials for garlic and an efficient method for imparting garlic flavor are strongly demanded. [Means for Solving the Problems]

[0006] As a result of intensive studies on the above problems, the present inventors have found that by heating a specific compound (e.g., ALCSO) that can generate sulfides, which are the main components of garlic aroma, by pyrolysis, in edible oil, aroma components can be efficiently expressed even without using garlic as a raw material. Further, the present inventors have found that by mixing and heating in a solution a specific compound (e.g., ALCSO) that can generate sulfides, which are the main components of garlic aroma, by pyrolysis, and a specific compound having the property of promoting the decomposition of the said compound (which may be referred to as "decomposition enhancer" etc. in the present specification), the decomposition of the specific compound that can generate the said sulfides is promoted, and aroma components can be efficiently expressed. Based on such findings, the present inventors have further advanced research and completed the present invention.

[0007] In one aspect, the present invention is as follows. [1] A method for imparting aroma to food and drink, comprising heating at least one sulfide precursor compound selected from the group consisting of S-allyl-L-cysteine sulfoxide (ALCSO), S-methyl-L-cysteine sulfoxide (MCSO), S-propyl-L-cysteine sulfoxide (PCSO), S-1-propenyl-L-cysteine sulfoxide (PeCSO), S-allyl-L-cysteine (ALC), S-methyl-L-cysteine (MC), S-propyl-L-cysteine (PC), and S-1-propenyl L-cysteine (PeC) in edible oil. [2] The method according to [1], wherein the sulfide precursor compound is ALCSO. [3] The method according to [1] or [2], characterized in that the heating temperature is 110°C to 250°C. [4]A method for producing a flavored food or drink, comprising heating at least one sulfide precursor compound selected from the group consisting of S-allyl-L-cysteine sulfoxide (ALCSO), S-methyl-L-cysteine sulfoxide (MCSO), S-propyl-L-cysteine sulfoxide (PCSO), S-1-propenyl-L-cysteine sulfoxide (PeCSO), S-allyl-L-cysteine (ALC), S-methyl-L-cysteine (MC), S-propyl-L-cysteine (PC), and S-1-propenyl L-cysteine (PeC) in edible oil. [5]The production method according to [4], wherein the sulfide precursor compound is ALCSO. [6]The production method according to [4] or [5], characterized in that the heating temperature is 110°C to 250°C. [7]A flavoring agent comprising at least one sulfide precursor compound selected from the group consisting of S-allyl-L-cysteine sulfoxide (ALCSO), S-methyl-L-cysteine sulfoxide (MCSO), S-propyl-L-cysteine sulfoxide (PCSO), S-1-propenyl-L-cysteine sulfoxide (PeCSO), S-allyl-L-cysteine (ALC), S-methyl-L-cysteine (MC), S-propyl-L-cysteine (PC), and S-1-propenyl L-cysteine (PeC). [8]The agent according to [7], wherein the sulfide precursor compound is ALCSO. A flavoring agent comprising a thermal decomposition product of at least one sulfide precursor compound selected from the group consisting of S-allyl-L-cysteine sulfoxide (ALCSO), S-methyl-L-cysteine sulfoxide (MCSO), S-propyl-L-cysteine sulfoxide (PCSO), S-1-propenyl-L-cysteine sulfoxide (PeCSO), S-allyl-L-cysteine (ALC), S-methyl-L-cysteine (MC), S-propyl-L-cysteine (PC), and S-1-propenyl L-cysteine (PeC) in edible oil.

[10] The agent according to [9], wherein the sulfide precursor compound is ALCSO.

[11] A food or drink comprising the agent according to any one of [7] to

[10] .

[0008] In another aspect, the present invention is as follows.

[12] (1) A pyridine derivative represented by the following general formula (I);

[0009] [Chemical formula]

[0010] (In the formula, R 1 is hydrogen or an optionally substituted C 1~5 alkyl group, R 2 is hydrogen, an optionally substituted C 1~5 alkyl group, or a phosphate group, and n is 0, 1, or 2), and at least one selected from the group consisting of Lewis acidic metal compounds, (2)At least one sulfide precursor compound selected from the group consisting of S-allyl-L-cysteine sulfoxide (ALCSO), S-methyl-L-cysteine sulfoxide (MCSO), S-propyl-L-cysteine sulfoxide (PCSO), S-1-propenyl-L-cysteine sulfoxide (PeCSO), S-allyl-L-cysteine (ALC), S-methyl-L-cysteine (MC), S-propyl-L-cysteine (PC), and S-1-propenyl L-cysteine (PeC), A method for imparting aroma to food and drink, which comprises mixing and heating the above in a solution.

[13] The method according to

[12] , wherein the pyridine derivative is at least one selected from the group consisting of pyridoxal-5'-phosphate and pyridoxal.

[14] The method according to

[12] or

[13] , wherein the Lewis acidic metal compound is at least one selected from the group consisting of iron(III) chloride and aluminum chloride.

[15] The method according to any one of

[12] to

[14] , wherein the sulfide precursor compound is ALCSO.

[16] The method according to any one of

[12] to

[15] , wherein the heating temperature is 40°C to 250°C.

[17] The method according to any one of

[12] to

[16] , wherein the heating time is 30 seconds to 48 hours.

[18] (1) A pyridine derivative represented by the following general formula (I);

[0011]

Chemical formula

[0012] (In the formula, R 1 is hydrogen or an optionally substituted C 1~5 alkyl group, and R 2 is hydrogen, an optionally substituted C 1~5is an alkyl group or a phosphate group, and n is 0, 1, or 2), and, at least one selected from the group consisting of Lewis acidic metal compounds, and (2) at least one sulfide precursor compound selected from the group consisting of S-allyl-L-cysteine sulfoxide (ALCSO), S-methyl-L-cysteine sulfoxide (MCSO), S-propyl-L-cysteine sulfoxide (PCSO), S-1-propenyl-L-cysteine sulfoxide (PeCSO), S-allyl-L-cysteine (ALC), S-methyl-L-cysteine (MC), S-propyl-L-cysteine (PC), and S-1-propenyl L-cysteine (PeC), A method for producing a food or beverage product imparted with aroma, which includes mixing and heating the above in a solution.

[19] The production method according to

[18] , wherein the pyridine derivative is at least one selected from the group consisting of pyridoxal-5'-phosphate and pyridoxal.

[20] The production method according to

[18] or

[19] , wherein the Lewis acidic metal compound is at least one selected from the group consisting of iron(III) chloride and aluminum chloride.

[21] The production method according to any one of

[18] to

[20] , wherein the sulfide precursor compound is ALCSO.

[22] The production method according to any one of

[18] to

[21] , characterized in that the heating temperature is 40°C to 250°C.

[23] The production method according to any one of

[18] to

[22] , characterized in that the heating time is 30 seconds to 48 hours.

[24] (1) A pyridine derivative represented by the following general formula (I);

[0013]

Chemical formula

[0014] (In the formula, R 1is hydrogen, or an optionally substituted C 1~5 alkyl group, and R 2 is hydrogen, an optionally substituted C 1~5 alkyl group, or a phosphate group, and n is 0, 1 or 2), and, at least one selected from the group consisting of Lewis acidic metal compounds, and (2) at least one sulfide precursor compound selected from the group consisting of S-allyl-L-cysteine sulfoxide (ALCSO), S-methyl-L-cysteine sulfoxide (MCSO), S-propyl-L-cysteine sulfoxide (PCSO), S-1-propenyl-L-cysteine sulfoxide (PeCSO), S-allyl-L-cysteine (ALC), S-methyl-L-cysteine (MC), S-propyl-L-cysteine (PC), and S-1-propenyl L-cysteine (PeC), and a flavoring agent comprising the same.

[25] The agent according to

[24] , wherein the pyridine derivative is at least one selected from the group consisting of pyridoxal-5'-phosphate and pyridoxal.

[26] The agent according to

[24] or

[25] , wherein the Lewis acidic metal compound is at least one selected from the group consisting of iron(III) chloride and aluminum chloride.

[27] The agent according to any one of

[24] to

[26] , wherein the sulfide precursor compound is ALCSO.

[28] (1) A pyridine derivative represented by the following general formula (I);

[0015] [Chemical formula]

[0016] (In the formula, R 1 is hydrogen, or an optionally substituted C 1~5 alkyl group, and R 2 is hydrogen, an optionally substituted C1~5 an alkyl group or a phosphate group, where n is 0, 1, or 2), and using at least one selected from the group consisting of Lewis acidic metal compounds (2) A flavoring agent comprising a thermal decomposition product of at least one sulfide precursor compound selected from the group consisting of S-allyl-L-cysteine sulfoxide (ALCSO), S-methyl-L-cysteine sulfoxide (MCSO), S-propyl-L-cysteine sulfoxide (PCSO), S-1-propenyl-L-cysteine sulfoxide (PeCSO), S-allyl-L-cysteine (ALC), S-methyl-L-cysteine (MC), S-propyl-L-cysteine (PC), and S-1-propenyl L-cysteine (PeC).

[29] The agent according to

[28] , wherein the pyridine derivative is at least one selected from the group consisting of pyridoxal-5'-phosphate and pyridoxal.

[30] The agent according to

[28] or

[29] , wherein the Lewis acidic metal compound is at least one selected from the group consisting of iron(III) chloride and aluminum chloride.

[31] The agent according to any one of

[28] to

[30] , wherein the sulfide precursor compound is ALCSO.

[32] A food or drink comprising the agent according to any one of

[24] to

[31] .

Advantages of the Invention

[0017] According to the present invention, it is possible to efficiently impart an aroma (e.g., garlic aroma) to foods and drinks. In particular, since the present invention does not use an enzyme such as alliinase to decompose alliin, there is no problem of enzyme inactivation during high-temperature heating, which is a problem in enzymatic conversion. Therefore, it is also possible to achieve aroma imparting during high-temperature heating.

Modes for Carrying Out the Invention

[0018] Hereinafter, the present invention will be described in detail.

[0019] In this specification, a specific compound that can generate sulfides (e.g., diallyl disulfide, diallyl sulfide, etc.), which are the main components of garlic aroma, by thermal decomposition, will be referred to as a "sulfide precursor compound".

[0020] As a first aspect of the present invention, aroma imparting to food and drink by heating a sulfide precursor compound in edible oil will be described.

[0021] 1. Method for imparting aroma to food and drink 1 The present invention provides a method for imparting aroma to food and drink (hereinafter sometimes referred to as "Method 1 of the present invention"), which includes heating at least one sulfide precursor compound selected from the group consisting of S-allyl-L-cysteine sulfoxide (ALCSO), S-methyl-L-cysteine sulfoxide (MCSO), S-propyl-L-cysteine sulfoxide (PCSO), S-1-propenyl-L-cysteine sulfoxide (PeCSO), S-allyl-L-cysteine (ALC), S-methyl-L-cysteine (MC), S-propyl-L-cysteine (PC), and S-1-propenyl L-cysteine (PeC) in edible oil.

[0022] Examples of the sulfide precursor compound that can be used in Method 1 of the present invention include the following compounds: (1) S-allyl-L-cysteine sulfoxide (ALCSO, CAS number: 556-27-4); (2) S-methyl-L-cysteine sulfoxide (MCSO, CAS number: 6853-87-8); (3) S-propyl-L-cysteine sulfoxide (PCSO, CAS number: 17795-24-3); (4) S-1-propenyl-L-cysteine sulfoxide (PeCSO, CAS No.: 3836-24-6); (5) S-allyl-L-cysteine (ALC, CAS No.: 21593-77-1); (6) S-methyl-L-cysteine (MC, CAS No.: 7728-98-5); (7) S-propyl-L-cysteine (PC, CAS No.: 1115-93-1); and (8) S-1-propenyl L-cysteine (PeC, CAS No.: 49621-03-6). All of the above compounds can be produced or extracted by methods known per se, and can also be produced by chemical synthesis or the like. Further, these compounds may be commercially available products.

[0023] The amount of the sulfide precursor compound used in Method 1 of the present invention can be appropriately set according to the intensity of the aroma to be imparted, the balance with the flavor and taste inherent in the food or drink, or the preferences of consumers, etc. Usually, it is usually 0.001% by weight or more, preferably 0.01% by weight or more, more preferably 0.05% by weight or more, still more preferably 1% by weight or more, particularly preferably 1.5% by weight or more, based on the amount of the edible oil used. Also, the upper limit is not particularly limited, but usually 10% by weight or less, preferably 9% by weight or less, more preferably 8% by weight or less, still more preferably 7% by weight or less, particularly preferably 5% by weight or less. In one embodiment, the amount of the sulfide precursor compound (e.g., ALCSO) used is usually 0.001% by weight to 10% by weight, preferably 0.01% by weight to 9% by weight, more preferably 0.05% by weight to 8% by weight, still more preferably 1% by weight to 7% by weight, particularly preferably 1.5% by weight to 5% by weight.

[0024] The edible oil in Method 1 of the present invention is not particularly limited as long as it is an edible oil, and either animal or vegetable oil may be used, but vegetable oil can be preferably used. Examples of vegetable oils include, but are not limited to, olive oil, wheat germ oil, rice bran oil, safflower oil, soybean oil, camellia oil, corn oil, rapeseed oil, sunflower oil, cottonseed oil, peanut oil, and castor oil. Examples of animal oils include, but are not limited to, lard, fish oil, squalane, and beeswax. Also, a combination of two or more of these may be used as the edible oil.

[0025] The edible oil in the present invention may be not only an edible oil that does not contain components other than oil, but also may contain components other than oil (e.g., moisture). For example, when preparing oil-based products (e.g., deep-fried foods, tempura, etc.) using Method 1 of the present invention, it is assumed that moisture derived from food ingredients flows into the edible oil. In this case, the disulfide precursor compound will be heated in a mixture of the edible oil and moisture. However, in the said mixture, if the proportion of the edible oil is sufficiently large relative to the proportion of the moisture, and thus the disulfide precursor compound can be sufficiently thermally decomposed in the said mixture, the desired effect of the present invention can be obtained. The proportion of the oil content in the mixture capable of obtaining the desired effect of the present invention can be at least 90% by weight or more, preferably 93% by weight or more, more preferably 95% by weight or more, still more preferably 96% by weight or more, and particularly preferably 97% by weight or more.

[0026] Targets to which aroma can be imparted using Method 1 of the present invention include all food and drink products (including pharmaceuticals, etc.), and are not particularly limited. However, from the viewpoint that aroma imparting can be easily achieved only by performing normal cooking steps, food and drink products that go through a process of heating and cooking food ingredients in edible oil during cooking are preferred. Examples of food and drink products to which aroma can be imparted by Method 1 of the present invention include, but are not limited to, fried foods (e.g., deep-fried chicken, tempura, etc.), stir-fried dishes (e.g., fried rice, etc.), and retort foods, etc.

[0027] As described above, the method 1 of the present invention can be applied to various food and drink products. In other words, the heating temperature and heating time in the method 1 of the present invention can be changed according to the type of food and drink products and their cooking processes. Therefore, the heating temperature is not particularly limited. However, as one embodiment, it is usually 110°C or higher, preferably 115°C or higher, more preferably 120°C or higher, still more preferably 125°C or higher, and particularly preferably 135°C or higher. The upper limit can be usually 250°C or lower, preferably 230°C or lower, more preferably 210°C or lower, still more preferably 200°C or lower, and particularly preferably 190°C or lower. In one aspect, the heating temperature can be usually 110°C to 250°C, preferably 115°C to 230°C, more preferably 120°C to 210°C, still more preferably 125°C to 200°C, and particularly preferably 135°C to 190°C. Also, the heating time is likewise not particularly limited. However, as one embodiment, it is usually 30 seconds or longer, preferably 1 minute or longer, more preferably 5 minutes or longer, still more preferably 7 minutes or longer, and particularly preferably 10 minutes or longer. The upper limit can be usually 60 minutes or shorter, preferably 50 minutes or shorter, more preferably 40 minutes or shorter, still more preferably 30 minutes or shorter, and particularly preferably 20 minutes or shorter. In one aspect, the heating time can be usually 30 seconds to 60 minutes, preferably 1 minute to 50 minutes, more preferably 5 minutes to 40 minutes, still more preferably 7 minutes to 30 minutes, and particularly preferably 10 minutes to 20 minutes.

[0028] In addition, even for food and drink products that do not undergo heat treatment in cooking oil, the aroma can be imparted by Method 1 of the present invention. Briefly explained, first, sulfide precursor compounds are heated in cooking oil to generate sulfides, which are the main components of the garlic aroma. Sulfide precursor compounds such as ALCSO are generally water-soluble before decomposition, but sulfides after decomposition are generally oil-soluble. Therefore, the sulfides generated by decomposition dissolve and exist in the oil liquid. Accordingly, after collecting the oil liquid and diluting it as necessary, the oil liquid can be mixed, applied, sprayed, etc. to the food and drink products to be aromatized before cooking, during cooking, after cooking, or immediately before eating, thereby aromatizing the food and drink products. Alternatively, sulfides that bring about the garlic aroma can be isolated and purified from the oil liquid rich in such sulfides by a method known per se. Then, the purified product of the sulfides that bring about the garlic aroma can also be used to impart the garlic aroma to food and drink products by mixing, applying, adding, etc. to the food and drink products before cooking, during cooking, after cooking, or immediately before eating.

[0029] In one aspect, Method 1 of the present invention may be implemented in combination with other aroma and / or flavor imparting methods. Therefore, in such an embodiment, the food and drink products to which the aroma is imparted by Method 1 of the present invention may have other aromas and / or flavors in addition to the aroma derived from the present invention, or may exhibit a synergistic flavor.

[0030] 2. Method for producing food and drink with imparted aroma 1 The present invention also provides a method for producing a flavored food or drink (hereinafter sometimes referred to as "Production Method 1 of the present invention") including heating at least one sulfide precursor compound selected from the group consisting of S-allyl-L-cysteine sulfoxide (ALCSO), S-methyl-L-cysteine sulfoxide (MCSO), S-propyl-L-cysteine sulfoxide (PCSO), S-1-propenyl-L-cysteine sulfoxide (PeCSO), S-allyl-L-cysteine (ALC), S-methyl-L-cysteine (MC), S-propyl-L-cysteine (PC), and S-1-propenyl L-cysteine (PeC) in edible oil.

[0031] The sulfide precursor compound, edible oil, heating temperature, heating time, etc. used in Production Method 1 of the present invention are the same as those in the above-described "1. Method for imparting aroma to food and drink 1".

[0032] As one embodiment of Production Method 1 of the present invention, a food or beverage intended to be imparted with an aroma is produced by heating a raw material of the food or beverage and a sulfide precursor compound in edible oil. Further, even for a food or beverage that does not undergo heat treatment in edible oil during cooking, the aroma can be imparted by Method 1 of the present invention. Briefly explained, first, the sulfide precursor compound is heated in edible oil to generate sulfides, which are the main components of the garlic aroma. Sulfide precursor compounds such as ALCSO are generally water-soluble before decomposition, but the sulfides after decomposition are generally oil-soluble. Therefore, the sulfides generated by decomposition will dissolve and exist in the oil. Accordingly, after collecting the oil and diluting it as necessary, the oil can be mixed, applied, sprayed, etc. to the food or beverage intended to be imparted with an aroma before cooking, during cooking, after cooking, or immediately before eating to impart an aroma to the food or beverage. Alternatively, the sulfides that bring about the garlic aroma may be isolated and purified from the oil rich in such sulfides by a method known per se. Then, the purified product of the sulfides that bring about the garlic aroma can also be used to impart the garlic aroma to the food or beverage by mixing, applying, adding, etc. to the food or beverage before cooking, during cooking, after cooking, or immediately before eating.

[0033] In one aspect, Production Method 1 of the present invention can also be implemented in combination with other aroma and / or flavor imparting methods. Accordingly, in such an embodiment, the food or beverage produced by Production Method 1 of the present invention may have other aromas and / or flavors in addition to the aroma derived from the present invention, or may exhibit a synergistic flavor.

[0034] 3. Aroma imparting agent 1 The present invention also provides a flavoring agent (hereinafter sometimes simply referred to as "Agent 1 of the present invention") containing at least one sulfide precursor compound selected from the group consisting of S-allyl-L-cysteine sulfoxide (ALCSO), S-methyl-L-cysteine sulfoxide (MCSO), S-propyl-L-cysteine sulfoxide (PCSO), S-1-propenyl-L-cysteine sulfoxide (PeCSO), S-allyl-L-cysteine (ALC), S-methyl-L-cysteine (MC), S-propyl-L-cysteine (PC), and S-1-propenyl L-cysteine (PeC).

[0035] The sulfide precursor compound and the like used in Agent 1 of the present invention are the same as those described in the above-mentioned "1. Method for imparting flavor to food and drink 1".

[0036] The blending amount of the sulfide precursor compound in Agent 1 of the present invention is not particularly limited as long as the desired effect can be obtained, but is usually 0.01% by weight to 100% by weight, preferably 1% by weight to 100% by weight, more preferably 10% by weight to 100% by weight, still more preferably 50% by weight to 100% by weight, and particularly preferably 70% by weight to 100% by weight based on the total weight of the agent.

[0037] In addition to the sulfide precursor compound, Agent 1 of the present invention may further contain other components that can be added to food and drink. Such other components include, for example, pH adjusters, antioxidants, preservatives, sweeteners, fragrances, seasonings, nutrient enhancers, colorants, thickeners, stabilizers, and emulsifiers, etc., but are not limited thereto. In one embodiment, Agent 1 of the present invention may be formulated in the form of a "flavor seasoning" or the like in combination with these other components.

[0038] The form of Agent 1 of the present invention can be prepared in any form such as solid forms like powder or granules, liquid forms, gel forms, slurry forms, etc. However, from the viewpoints of transportation and storage, solid forms are preferred.

[0039] When the food or beverage intended to be imparted with aroma is a food or beverage involving heat treatment in edible oil in the cooking process, Agent 1 of the present invention is added before or during the heat treatment of the edible oil of the food or beverage, and by heating the mixture, a food or beverage imparted with aroma can be produced. Also, when imparting a garlic aroma to a food or beverage that does not undergo heat treatment in edible oil in a normal cooking process using Agent 1 of the present invention, first, Agent 1 of the present invention is added to edible oil and heated to obtain a solution rich in sulfides which are the main components of the garlic aroma. Although sulfide precursor compounds such as ALCSO are generally water-soluble before decomposition, the sulfides generated by decomposition are generally oil-soluble, so the sulfides generated by decomposition dissolve in the edible oil. Therefore, the heated edible oil is recovered, diluted if necessary, and then mixed, applied, sprayed, etc. to the food or beverage before cooking, during cooking, after cooking, or immediately before eating to impart the garlic aroma to the food or beverage. Alternatively, the sulfides that bring about the garlic aroma may be isolated and purified from the heated edible oil rich in sulfides by a method known per se. And by mixing, applying, spraying, etc. the purified product of the sulfides that bring about the garlic aroma to the food or beverage before cooking, during cooking, after cooking, or immediately before eating to perfume it, a food or beverage can also be imparted with the garlic aroma. Incidentally, the addition amount of Agent 1 of the present invention to the food or beverage may be appropriately set according to the intensity of the aroma to be imparted, the balance with the inherent aroma, flavor, and taste of the food or beverage, or the preference of consumers, etc.

[0040] As described above, Agent 1 of the present invention may contain various other seasonings. Therefore, when formulated as a flavor seasoning, it is possible to impart an aroma and flavor in which various flavors are complexly combined, and at least a garlic aroma can be imparted. Accordingly, in one aspect, it can be said that the aroma-imparting agent of the present invention is for imparting a garlic aroma.

[0041] In another aspect of Agent 1 of the present invention, as also exemplified in the case of imparting garlic aroma to food and drink products that are not heat-treated in the normal cooking process using Agent 1 of the present invention, an aroma component obtained by thermally decomposing a sulfide precursor compound in edible oil in advance (that is, a compound group containing sulfides or a purified product of the compound group containing the sulfides, etc.) may be used as an active ingredient. That is, the present invention may be an aroma-imparting agent containing a thermal decomposition product of at least one sulfide precursor compound selected from the group consisting of S-allyl-L-cysteine sulfoxide (ALCSO), S-methyl-L-cysteine sulfoxide (MCSO), S-propyl-L-cysteine sulfoxide (PCSO), S-1-propenyl-L-cysteine sulfoxide (PeCSO), S-allyl-L-cysteine (ALC), S-methyl-L-cysteine (MC), S-propyl-L-cysteine (PC), and S-1-propenyl L-cysteine (PeC) in edible oil.

[0042] In this aspect, the sulfide precursor compound, edible oil, heating temperature, heating time, etc. are the same as those described above in "1. Method for imparting aroma to food and drink product 1". Also, regarding the usage amount of the sulfide precursor compound and other components that may be contained, etc., appropriate settings may be made while referring to the respective conditions described in the above "1. Method for imparting aroma to food and drink product 1" and "3. Aroma-imparting agent 1". Since this agent uses the aroma component itself as an active ingredient, aroma can be easily imparted by appropriately adding it to food and drink products. In addition, this agent may also contain various other seasonings, similar to Agent 1 of the present invention. Therefore, when formulated as a flavor seasoning, it is possible to impart an aroma and flavor in which various flavors are complexly combined, but at least garlic aroma can be imparted. Therefore, in one aspect, it can be said that this agent is for imparting garlic aroma.

[0043] In the present specification, although the description has been made in detail from the perspective of imparting aroma (e.g., garlic aroma), originally, when applying the method 1 or agent 1 of the present invention to food and drink products that originally have even a slight aroma (e.g., garlic aroma), the method 1 of the present invention, the production method 1 of the present invention, or agent 1 can respectively be also referred to as a method for enhancing aroma (e.g., garlic aroma), a production method of food and drink products with enhanced aroma (e.g., garlic aroma), or an agent for enhancing aroma (e.g., garlic aroma). Needless to say. Further, when applying the present invention to food and drink products that originally contain a certain amount of sulfide precursor compounds, it can be added so that the total amount of the sulfide precursor compounds contained in the food and drink products and the amount of sulfide precursor compounds added from the outside is within the above range.

[0044] As a second aspect of the present invention, aroma imparting to food and drink products by heating a sulfide precursor compound together with a decomposition enhancer will be described.

[0045] The "halogeno group" means fluoro, chloro, bromo, or iodo.

[0046] "C 1~5 alkyl group" means a linear or branched alkyl group, and specifically includes groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, neopentyl, 2-pentyl, 3-pentyl, etc.

[0047] "C 1~5 alkyl group" may have a substituent, and examples of such substituents include the following. (1) halogeno group, (2) hydroxyl group, (3) cyano group, (4) nitro group, (5) carboxyl group, (6) phosphoric acid group, (7) alkenyl group (C 2-10Alkenyl group; examples include vinyl, allyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, butadienyl, hexatrieneyl, and their respective isomers), (8) Alkynyl group (C 2-10 Alkynyl group; examples include ethynyl, propynyl, butynyl, pentynyl, hexynyl, and their respective isomers), (9) Halogenoalkyl group (examples include monofluoromethyl, difluoromethyl, trifluoromethyl, monofluoroethyl, difluoroethyl, trifluoroethyl, chloromethyl, chloroethyl, dichloroethyl, and their respective isomers), (10) Cyclic alkyl group (which may contain a heteroatom in the ring) (examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, tetrahydrofuranyl, tetrahydropyranyl, aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl), (11) Aryl group (examples include phenyl, naphthyl).

[0048] When two or more substituents are present, they may be the same or different.

[0049] 4. Method for imparting aroma to food and drink 2 The present invention relates to (1) a pyridine derivative represented by the following general formula (I);

[0050]

Chemical formula

[0051] (In the formula, R 1 is hydrogen or an optionally substituted C 1~5 alkyl group, and R 2 is hydrogen or an optionally substituted C 1~5It is an alkyl group or a phosphate group, n is 0, 1 or 2 (hereinafter, it may be referred to as "pyridine derivative used in the present invention" or simply "pyridine derivative" in this specification)), and at least one selected from the group consisting of Lewis acidic metal compounds, and (2) S-allyl-L-cysteine sulfoxide (ALCSO), S-methyl-L-cysteine sulfoxide (MCSO), S-propyl-L-cysteine sulfoxide (PCSO), S-1-propenyl-L-cysteine sulfoxide (PeCSO), S-allyl-L-cysteine (ALC), S-methyl-L-cysteine (MC), S-propyl-L-cysteine (PC), and S-1-propenyl L-cysteine (PeC) A method for imparting aroma to food and drink (hereinafter, may be simply referred to as "Method 2 of the present invention") is provided, which includes mixing and heating at least one sulfide precursor compound selected from the group consisting of

[0052] The pyridine derivative used in the present invention is represented by the above general formula (I) and is not particularly limited as long as it is a compound that can be added to food and drink. For example, pyridoxal (in the general formula (I), R 1 is a methyl group, R 2 is a methyl group substituted with a hydroxyl group, and n = 0, CAS number: 66-72-8) and pyridoxal-5'-phosphate (in the general formula (I), R 1 is a methyl group, R 2 is a methyl group substituted with a phosphate group, n = 0, CAS number: 41468-25-1), etc. are mentioned.

[0053] [Pyridoxal]

[0054] [Chemical formula]

[0055] [Pyridoxal-5'-phosphate]

[0056] [Chemical formula]

[0057] The above pyridine derivative can be produced by a method known per se, and commercially available products can also be used.

[0058] In addition, the "Lewis acidic metal compound" used in Method 2 of the present invention can also be added to food and drink, and is not particularly limited as long as the desired effects of the present invention can be obtained. Examples include aluminum chloride and iron(III) chloride. These Lewis acidic metal compounds can also be produced by methods known per se, and commercially available products may also be used. In this specification, "Lewis acid" includes an atom having an empty orbital capable of accommodating an electron pair, and particularly includes substances that act as Lewis acids with respect to ALCSO.

[0059] Examples of the sulfide precursor compound that can be used in Method 2 of the present invention include the following compounds: (1) S-allyl-L-cysteine sulfoxide (ALCSO, CAS No.: 556-27-4); (2) S-methyl-L-cysteine sulfoxide (MCSO, CAS No.: 6853-87-8); (3) S-propyl-L-cysteine sulfoxide (PCSO, CAS No.: 17795-24-3); (4) S-1-propenyl-L-cysteine sulfoxide (PeCSO, CAS No.: 3836-24-6); (5) S-allyl-L-cysteine (ALC, CAS No.: 21593-77-1); (6) S-methyl-L-cysteine (MC, CAS No.: 7728-98-5); (7) S-propyl-L-cysteine (PC, CAS No.: 1115-93-1); and (8) S-1-propenyl L-cysteine (PeC, CAS No.: 49621-03-6). All of the above compounds can be produced or extracted by methods known per se, and can also be produced by chemical synthesis or the like. Further, these compounds may be commercially available products.

[0060] The amount of the sulfide precursor compound used in Method 2 of the present invention is not particularly limited as long as the desired effect of the present invention can be obtained, and can be set as appropriate. For example, when the purpose is to efficiently convert the sulfide precursor compound into an aroma component, the amount of the sulfide precursor compound used is usually 500 weight ppm or more, preferably 1,000 weight ppm or more, more preferably 4,000 weight ppm or more, still more preferably 10,000 weight ppm or more, and particularly preferably 30,000 weight ppm or more, based on the solvent. Further, the upper limit is not particularly limited, but is usually 100,000 weight ppm or less, preferably 80,000 weight ppm or less, more preferably 60,000 weight ppm or less, still more preferably 50,000 weight ppm or less, and particularly preferably 35,000 weight ppm or less. In one aspect, the amount of the sulfide precursor compound (e.g., ALCSO) used can be 500 weight ppm to 100,000 weight ppm, preferably 1,000 weight ppm to 80,000 weight ppm, more preferably 4,000 weight ppm to 60,000 weight ppm, still more preferably 10,000 weight ppm to 50,000 weight ppm, and particularly preferably 30,000 weight ppm to 35,000 weight ppm.

[0061] In addition, the amount (mol) of the pyridine derivative and / or the Lewis acidic metal compound used in the present invention is not particularly limited as long as the desired effect of the present invention can be obtained. For example, relative to the amount (mol) of the sulfide precursor compound, it is usually 0.15 equivalent or more, preferably 0.2 equivalent or more, more preferably 0.5 equivalent or more, still more preferably 0.6 equivalent or more, and particularly preferably 0.75 equivalent or more. Also, the upper limit is not particularly limited, but is usually 100 equivalents or less, preferably 50 equivalents or less, more preferably 30 equivalents or less, still more preferably 10 equivalents or less, and particularly preferably 5 equivalents or less. When using a plurality of types of pyridine derivatives and / or Lewis acidic metal compounds, for example, the amount used can be determined such that the sum of each component is within the above range. In one aspect, the amount (mol) of the pyridine derivative and / or the Lewis acidic metal compound used in the present invention is usually 0.15 equivalent to 100 equivalents, preferably 0.2 equivalent to 50 equivalents, more preferably 0.5 equivalent to 30 equivalents, still more preferably 0.6 equivalent to 10 equivalents, and particularly preferably 0.75 equivalent to 5 equivalents relative to the amount (mol) of the sulfide precursor compound (e.g., ALCSO).

[0062] The solvent in Method 2 of the present invention is usually water, but is not particularly limited as long as the desired effect can be obtained. In one aspect, the water serving as the solvent may contain various components derived from seasonings and ingredients, etc., may be a soup, etc., or may be a mixture with cooking oil, etc.

[0063] Examples of the objects to which the aroma can be imparted using Method 2 of the present invention include all food and drink products (including pharmaceuticals, etc.), and are not particularly limited. However, from the viewpoint that the aroma can be easily imparted only by performing normal cooking steps, the food and drink products contain a relatively large amount of moisture during cooking (for example, 20% or more, 30% or more, 40% or more, 50% or more, 60% or more, 70% or more, 80% or more, 90% or more, or 95% or more moisture based on the weight of all ingredients) and undergo a heating process during cooking are preferred. In addition, examples of the heating process in this specification include processes such as baking, frying, stir-frying, stewing (cooking), steaming, boiling, etc., and further, two or more of these processes may be performed. Examples of food and drink products to which the aroma can be imparted by Method 2 of the present invention include grilled foods (e.g., aqua pizza), fried foods (e.g., tempura, etc.), stir-fried foods (e.g., stir-fried vegetables), boiled foods (e.g., meat and potato stew, cooked rice), steamed foods (e.g., shumai), boiled foods (e.g., spaghetti), etc. In addition, various soups, fried foods (e.g., fried chicken), retort foods, etc. can also be cited as examples to which Method 2 of the present invention can be applied. In particular, soups, stir-fried vegetables, etc. can be cited as preferred examples.

[0064] As described above, the method 2 of the present invention can be applied to various food and drink products. In other words, the heating temperature and heating time in the method 2 of the present invention can be changed according to the type of food and drink products and their cooking processes. Therefore, the heating temperature is not particularly limited. However, as one embodiment, it is usually 40°C or higher, preferably 50°C or higher, more preferably 60°C or higher, still more preferably 70°C or higher, and particularly preferably 80°C or higher. The upper limit can be usually 250°C or lower, preferably 230°C or lower, more preferably 200°C or lower, still more preferably 190°C or lower, and particularly preferably 180°C or lower. In one aspect, the heating temperature can be usually 40°C to 250°C, preferably 50°C to 230°C, more preferably 60°C to 200°C, still more preferably 70°C to 190°C, and particularly preferably 80°C to 180°C. Also, the heating time is likewise not particularly limited. However, as one embodiment, it is usually 30 seconds or longer, preferably 1 minute or longer, more preferably 5 minutes or longer, still more preferably 7 minutes or longer, and particularly preferably 10 minutes or longer. The upper limit can be usually 48 hours or shorter, preferably 24 hours or shorter, more preferably 6 hours or shorter, still more preferably 3 hours or shorter, and particularly preferably 1 hour or shorter. In one aspect, the heating time can be usually 30 seconds to 48 hours, preferably 1 minute to 24 hours, more preferably 5 minutes to 6 hours, still more preferably 7 minutes to 3 hours, and particularly preferably 10 minutes to 1 hour.

[0065] As a specific embodiment of Method 2 of the present invention, for food and drink intended to be imparted with aroma, the above various components are added and blended, and further, by heating this mixture, the food and drink can be imparted with aroma. Specifically, for example, when imparting garlic aroma to a beverage (such as soup, etc.), the above components can be directly added to the beverage and heated to impart garlic aroma to the beverage. Alternatively, when imparting garlic aroma to stir-fried vegetables, when stir-frying the vegetables on a cooking utensil such as a frying pan, the above components are added and, through normal cooking steps, rich garlic aroma is imparted to the stir-fried vegetables. Also, when imparting garlic aroma to food and drink that do not undergo heat treatment in normal cooking steps or food and drink with relatively little moisture, first, the above components are added to a solvent in which water and oil are mixed, and this is heated to obtain a solution rich in sulfides, which are the main components of garlic aroma. Although sulfide precursor compounds such as ALCSO are generally water-soluble before decomposition, sulfides after decomposition are generally oil-soluble, so the sulfides generated by decomposition will be richly contained in the oil component of the solution. Therefore, the oil component is recovered, and after diluting the recovered oil component as necessary, it is mixed, applied, sprayed, etc. to food and drink before cooking, during cooking, after cooking, or immediately before eating to impart the scent of garlic aroma to the food and drink. Alternatively, the sulfides that bring about the garlic aroma may be isolated and purified from the oil component rich in sulfides by a method known per se. And by imparting the purified product of the sulfides that bring about the garlic aroma by mixing, applying, spraying, etc. to food and drink before cooking, during cooking, after cooking, or immediately before eating, the food and drink can also be imparted with garlic aroma. Incidentally, the concentration of sulfides in food and drink at the time of eating obtained by Method 2 of the present invention is not particularly limited, and it may be appropriately set according to the strength of the aroma to be imparted, the balance with the flavor and taste originally possessed by the food and drink, or the preferences of consumers, etc.

[0066] In one aspect, the method 2 of the present invention may be carried out in combination with other aroma and / or flavor imparting methods. Thus, in such embodiments, the food or beverage to which aroma is imparted in the method 2 of the present invention may have other aromas and / or flavors in addition to the aroma derived from the present invention, or may exhibit a synergistic flavor.

[0067] 5. Method for producing food and drink with imparted aroma 2 The present invention also provides a method for producing a flavored food or beverage (hereinafter sometimes simply referred to as "production method 2 of the present invention"), which comprises mixing and heating at least one selected from the group consisting of (1) a pyridine derivative represented by the following general formula (I);

[0068]

Chemical formula

[0069] (wherein R 1 is hydrogen or an optionally substituted C 1~5 alkyl group, R 2 is hydrogen, an optionally substituted C 1~5 alkyl group or a phosphate group, and n is 0, 1 or 2), and at least one sulfide precursor compound selected from the group consisting of (2) S-allyl-L-cysteine sulfoxide (ALCSO), S-methyl-L-cysteine sulfoxide (MCSO), S-propyl-L-cysteine sulfoxide (PCSO), S-1-propenyl-L-cysteine sulfoxide (PeCSO), S-allyl-L-cysteine (ALC), S-methyl-L-cysteine (MC), S-propyl-L-cysteine (PC), and S-1-propenyl L-cysteine (PeC) in a solution.

[0070] The pyridine derivative, Lewis acidic metal compound, sulfide precursor compound, solvent, heating temperature, heating time, food and drink, etc. used in Production Method 2 of the present invention are the same as those described above in "4. Method for imparting aroma to food and drink 2".

[0071] As a specific embodiment of Production Method 2 of the present invention, for a food or drink intended to be imparted with an aroma, the above various components are added and blended, and then this is heated to produce a food or drink imparted with an aroma. Further, when imparting a garlic aroma to a food or drink that does not undergo heat treatment in a normal cooking process or a food or drink with relatively little moisture, first, the above components are added to a solvent in which water and oil are mixed, and this is heated to obtain a solution rich in sulfides, which are the main components of the garlic aroma. Sulfide precursor compounds such as ALCSO are generally water-soluble before decomposition, but the sulfides generated by decomposition are generally oil-soluble. Therefore, the sulfides generated by decomposition will be richly contained in the oil component of the solution. Thus, the oil component is recovered, and after diluting the recovered oil component as necessary, it is mixed, applied, sprayed, etc. to the food or drink before cooking, during cooking, after cooking, or immediately before eating, whereby the food or drink can be scented with the garlic aroma. Alternatively, the sulfides that bring about the garlic aroma may be isolated and purified from the oil component rich in the sulfides by a method known per se. Then, by scenting the purified product of the sulfides that bring about the garlic aroma by mixing, applying, spraying, etc. to the food or drink before cooking, during cooking, after cooking, or immediately before eating, the food or drink can also be imparted with the garlic aroma.

[0072] In one aspect, Production Method 2 of the present invention can also be carried out in combination with other aroma and / or flavor imparting methods. Therefore, in such an embodiment, the food or drink produced by Production Method 2 of the present invention may have other aromas and / or flavors in addition to the aroma derived from the present invention, or may exhibit a synergistic flavor.

[0073] 6. Aroma imparting agent 2 The present invention also provides a flavoring agent (hereinafter sometimes simply referred to as "Agent 2 of the present invention") comprising: (1) a pyridine derivative represented by the following general formula (I);

[0074] [Chemical formula]

[0075] (wherein R 1 is hydrogen or an optionally substituted C 1~5 alkyl group, R 2 is hydrogen, an optionally substituted C 1~5 alkyl group or a phosphate group, and n is 0, 1 or 2), and at least one selected from the group consisting of Lewis acidic metal compounds, and (2) at least one sulfide precursor compound selected from the group consisting of S-allyl-L-cysteine sulfoxide (ALCSO), S-methyl-L-cysteine sulfoxide (MCSO), S-propyl-L-cysteine sulfoxide (PCSO), S-1-propenyl-L-cysteine sulfoxide (PeCSO), S-allyl-L-cysteine (ALC), S-methyl-L-cysteine (MC), S-propyl-L-cysteine (PC), and S-1-propenyl L-cysteine (PeC).

[0076] The pyridine derivative, Lewis acidic metal compound, sulfide precursor compound, etc. used in Agent 2 of the present invention are the same as those described in the above-mentioned "4. Method for imparting flavor to food and drink 2".

[0077] The compounding amounts of the sulfide precursor compound, pyridine derivative, and / or Lewis acidic metal compound in Agent 2 of the present invention are not particularly limited as long as the desired effects can be obtained. For example, the compounding amount (mol) of the sulfide precursor compound and the compounding amount (mol) of the pyridine derivative and / or Lewis acidic metal compound used in the present invention are usually 1:0.3 to 10, preferably 1:0.5 to 5, more preferably 1:0.6 to 3, even more preferably 1:0.7 to 2, and particularly preferably 1:0.75 to 1.5. When using a plurality of pyridine derivatives and / or Lewis acidic metal compounds used in the present invention, for example, the compounding amounts can be determined such that the total of each component is within the above range.

[0078] In addition to the above components, Agent 2 of the present invention may further contain other components that can be added to foods and drinks. Examples of such other components include, but are not limited to, pH adjusters, antioxidants, preservatives, sweeteners, flavors, seasonings, nutritional fortifiers, colorants, thickeners, stabilizers, and emulsifiers. In one embodiment, Agent 2 of the present invention may be formulated in the form of a "flavor seasoning" or the like in combination with these other components.

[0079] Agent 2 of the present invention can be prepared in any form such as solid forms like powder or granules, liquid form, gel form, slurry form, etc. From the viewpoints of transportation and storage, a solid form is preferred.

[0080] When the food or drink intended to be imparted with aroma has a relatively high water content and is a food or drink that involves heat treatment in the cooking process, the agent 2 of the present invention is added before or during the heat treatment of the food or drink, and the mixture is heated, whereby a food or drink imparted with aroma can be produced. Further, when imparting a garlic aroma to a food or drink that does not undergo heat treatment in a normal cooking process or a food or drink with relatively little moisture using the agent 2 of the present invention, first, the agent 2 of the present invention is added to a solvent in which water and oil are mixed, and this is heated to obtain a solution rich in sulfides, which are the main components of the garlic aroma. Sulfide precursor compounds such as ALCSO are generally water-soluble before decomposition, but the sulfides generated by decomposition are generally oil-soluble. Therefore, the sulfides generated by decomposition will be richly contained in the oil component of the solvent. Therefore, the oil component is recovered, and after diluting the recovered oil component as necessary, it is mixed, applied, sprayed, etc. to the food or drink before cooking, during cooking, after cooking, or immediately before eating, whereby the food or drink can be scented with the garlic aroma. Alternatively, the sulfides that bring about the garlic aroma may be isolated and purified from the oil component rich in the sulfides by a method known per se. Then, the purified product of the sulfides that bring about the garlic aroma can also be used to impart the garlic aroma to the food or drink by mixing, applying, spraying, etc. to the food or drink before cooking, during cooking, after cooking, or immediately before eating. Incidentally, the amount of the agent 2 of the present invention added to the food or drink may be appropriately set according to the intensity of the aroma to be imparted, the aroma, flavor, and taste originally possessed by the food or drink, or the preference of the consumer, etc.

[0081] As described above, the agent 2 of the present invention may contain various other seasonings. Therefore, when formulated as a flavor seasoning, it is possible to impart an aroma and flavor in which various flavors are complexly combined, but at least a garlic aroma can be imparted. Therefore, in one aspect, it can be said that the aroma-imparting agent 2 of the present invention is for imparting a garlic aroma.

[0082] In another aspect of the agent 2 of the present invention, as also exemplified in the case of imparting garlic aroma to foods and beverages that are not heat-treated in the normal cooking process or foods and beverages with relatively low moisture content using the agent 2 of the present invention, an aroma component obtained by thermally decomposing a sulfide precursor compound using a decomposition enhancer in advance (that is, a compound group containing sulfides or a purified product of a compound group containing sulfides, etc.) may be used as an active ingredient. That is, the present invention relates to (1) a pyridine derivative represented by the following general formula (I);

[0083]

Chemical formula

[0084] (In the formula, R 1 is hydrogen or an optionally substituted C 1~5 alkyl group, R 2 is hydrogen, an optionally substituted C 1~5 alkyl group, or a phosphate group, and n is 0, 1, or 2), and an aroma-imparting agent comprising a thermal decomposition product of at least one sulfide precursor compound selected from the group consisting of (2) S-allyl-L-cysteine sulfoxide (ALCSO), S-methyl-L-cysteine sulfoxide (MCSO), S-propyl-L-cysteine sulfoxide (PCSO), S-1-propenyl-L-cysteine sulfoxide (PeCSO), S-allyl-L-cysteine (ALC), S-methyl-L-cysteine (MC), S-propyl-L-cysteine (PC), and S-1-propenyl L-cysteine (PeC) may also be used.

[0085] In this embodiment, the pyridine derivative, Lewis acidic metal compound, sulfide precursor compound, etc. are the same as those in the above-mentioned "4. Method for imparting aroma to food and drink 2". Also, regarding the usage amounts of the respective components, heating conditions, and other components that may be included, appropriate settings may be made while referring to the respective conditions described in the above-mentioned "4. Method for imparting aroma to food and drink 2" and "6. Aroma imparting agent 2". Since this agent uses the aroma component itself as an active ingredient, aroma can be easily imparted by appropriately adding it to food and drink. In addition, since this agent may also contain various other seasonings, similar to agent 2 of the present invention, when formulated as a flavor seasoning, flavoring with a complex combination of various flavors becomes possible, and at least garlic aroma can be imparted. Therefore, in one aspect, it can be said that this agent is for imparting garlic aroma.

[0086] In this specification, although specifically described from the perspective of imparting aroma (e.g., garlic aroma), originally, when applying method 2 or agent 2 of the present invention to food and drink that already has a certain amount of aroma (e.g., garlic aroma), method 2 of the present invention, manufacturing method 2 of the present invention, or agent 2 can respectively be rephrased as a method for enhancing aroma (e.g., garlic aroma), a manufacturing method for food and drink with enhanced aroma (e.g., garlic aroma), or an agent for enhancing aroma (e.g., garlic aroma), etc. Needless to say. Also, when applying the present invention to food and drink that originally contains a certain amount of sulfide precursor compound and / or pyridine derivative and / or Lewis acidic metal compound used in the present invention, the amount of sulfide precursor compound and / or pyridine derivative and / or Lewis acidic metal compound contained in the food and drink, and the total amount of sulfide precursor compound and / or pyridine derivative and / or Lewis acidic metal compound added from the outside can be added so that the total is within the above range.

[0087] The present invention will be described more specifically in the following examples, but the present invention is not limited by these examples.

Examples

[0088] [Example 1: Examination of Conditions for Promoting the Decomposition of ALCSO 1] To screen for conditions that can promote the decomposition of ALCSO in a manner capable of efficiently imparting garlic aroma, ALCSO was heated in edible oil under various conditions shown in Table 2 below to check whether aroma components were generated. Specifically, ALCSO and edible oil ("crispy canola oil", manufactured by J-Oil Mills, Inc.) or a mixture of ALCSO, edible oil, and water were mixed in a vial (ICHEM vial), and this was set on a heating stirrer and heated. At that time, in order to carry out the reaction in an open system close to actual cooking conditions, only the inner lid of the vial was removed and covered with aluminum foil from above. The time taken to reach a predetermined temperature was taken as the heating time of 0 minutes, and after the elapse of a predetermined heating time, the vial was cooled with ice water to stop the reaction.

[0089] [Pretreatment for Analysis of Heating Test] To each reaction solution reacted according to the above-described experimental conditions, MilliQ water and edible oil were added to the vial so that it became 4 mL of water and 4 mL of oil, and it was sufficiently stirred with a vortex. The total volume of the solution (8 mL) was put into a 50 mL Falcon tube and centrifuged at 9,000 rpm for 10 minutes. The reaction solution separated into an upper layer (oil layer) and a lower layer (water layer).

[0090] [Examination of the Decomposition Rate of ALCSO] 10 μL was sampled from the lower layer (i.e., the water layer) of the centrifuged aqueous solution, and the aqueous solution diluted 10,000-fold with MilliQ water was filtered through a filter (manufactured by GL Sciences, model number 5040-28510). 200 μL of the filtered aqueous solution was put into an LC vial, and the decomposition rate of ALCSO was calculated using the analysis conditions (LC / MS) and calculation formula detailed in Table 1 below.

[0091]

Table 1

[0092] The ALCSO decomposition rate was calculated using the following calculation formula.

[0093] ALCSO decomposition rate = (1 - (ALCSO concentration after reaction [weight ppm]) / (ALCSO concentration before reaction [weight ppm])) × 100 [%]

[0094] [Examination of the presence and intensity of garlic aroma] The decomposition products of ALCSO using candidate compounds were evaluated by a sensory test for the presence of garlic aroma. Specifically, the sensory test was conducted as follows. The test samples after reaction were each diluted so as to be 300 weight ppm in terms of the equivalent amount of ALCSO before decomposition (for example, when the reaction was carried out with ALCSO at 30,000 weight ppm before decomposition, the test samples after reaction were diluted 100-fold using dilution with a water / oil = 50 / 50 solution). One professional panelist evaluated the presence and intensity of garlic aroma for the obtained diluted samples using the following criteria.

[0095] ++: With strong garlic aroma +: With garlic aroma -: Without garlic aroma

[0096] The results are shown in Table 2.

[0097]

Table 2

[0098] As shown in Table 2, it was confirmed that ALCSO was decomposed with the generation of sulfides, which are aroma components, if the heating temperature was above a certain level and the oil content in the solvent was above a certain ratio.

[0099] [Example 2: Examination of conditions for promoting the decomposition of ALCSO 2] In order to examine the optimal heating temperature and heating time, the following experiment was conducted. ALCSO (concentration 3% by weight (30,000 ppm by weight)) was added to edible oil ("Sarasara Canola Oil", manufactured by J-Oil Mills, Inc.), and heated at various temperatures (140 °C, 160 °C, 180 °C, and 200 °C) and times (5 minutes, 10 minutes, 15 minutes), and the decomposition rate of ALCSO was analyzed. Also, whether garlic aroma was actually felt was evaluated by a sensory test.

[0100] The method for analyzing the decomposition rate of ALCSO was the same as that used in Example 1. Also, the sensory test was specifically conducted as follows. The test sample after the reaction was diluted 100-fold using a water / oil = 50 / 50 solution (i.e., diluted so as to be 300 ppm by weight in terms of the equivalent amount of ALCSO before decomposition). Regarding the diluted sample, one professional panelist evaluated the presence and intensity of garlic aroma using the following criteria.

[0101] ++: There is a strong garlic aroma +: There is a garlic aroma -: There is no garlic aroma

[0102] The results are shown in Tables 3 and 4.

[0103]

Table 3

[0104]

Table 4

[0105] As shown in Table 3, it was confirmed that ALCSO was efficiently decomposed at any heating time and heating temperature. Also, as shown in Table 4, although another aroma (pungent odor) may be generated simultaneously (conditions marked with "※" in Table 4), the generation of garlic aroma was confirmed at any heating time and heating temperature.

[0106] [Example 3: Examination Using ACSO Analogs Other Than ALCSO] The following experiments were conducted using MCSO (S-Methyl-L-cysteine sulfoxide), PCSO (S-Propyl-L-cysteine sulfoxide), and PeCSO (S-1-Propenyl-L-cysteine sulfoxide), which are cysteine sulfoxides similar to ALCSO. MCSO, PCSO, or PeCSO (3% by weight) was added to a mixture of edible oil ("Sarasara Canola Oil", manufactured by J-Oil Mills, Inc.) and water (weight ratio 97:3), heated at 140°C for 10 minutes, and then their decomposition rates were analyzed. Also, the presence or absence of an onion-like aroma (such as garlic, shallot, onion, etc.) was evaluated by a sensory test.

[0107] The method for analyzing the decomposition rate was the same as that used in Example 1, but only the target ions for the analysis conditions were changed as shown in Table 5. Also, the sensory test was specifically conducted as follows. The test sample after the reaction was diluted 100-fold using a water / oil = 50 / 50 solution (i.e., diluted to 0.03% by weight as the equivalent amount of MCSO, PCSO, or PeCSO before decomposition). Regarding the diluted sample, one professional panelist evaluated the presence and intensity of an onion-like aroma using the following criteria.

[0108] ++: There is a strong onion-like aroma +: There is an onion-like aroma -: There is no onion-like aroma

[0109]

Table 5

[0110] The results are shown in Table 6.

[0111]

Table 6

[0112] As shown in Table 6, when MCSO and PeCSO were used, it was confirmed that they decomposed efficiently and a scallion-like aroma was generated. Also, when PCSO was used, although the decomposition rate was not very high, a scallion-like aroma was sufficiently confirmed to be generated.

[0113] [Example 4: Examination of Use in Cooking]

[0114] To confirm the effect of the invention in tempura, the following experiment was conducted. 15 g of chicken breast meat was well coated with the coating of the formulation in Table 7. As a control test group, chicken breast meat coated with a coating not containing ALCSO was prepared. Those cooked by deep-frying in edible oil ("Sarasara Canola Oil", manufactured by J-Oil Mills, Inc.) at 170 °C for 4 minutes were evaluated by a sensory test.

[0115]

Table 7

[0116] [Examination of the Presence and Intensity of Garlic Aroma] It was evaluated by a sensory test whether the tempura after cooking had a garlic aroma. In the sensory test, one professional panelist evaluated the presence and intensity of the garlic aroma using the following criteria.

[0117] ++: Having a strong garlic aroma +: Having a garlic aroma -: Having no garlic aroma

[0118] The results are shown in Table 8.

[0119]

Table 8

[0120] As shown in Table 8, it was confirmed that a strong garlic aroma was generated only in the test group with ALCSO formulated in the coating.

[0121] [Example 5: Screening of Candidate Compounds that Promote the Decomposition of ALCSO] In order to screen for compounds that can promote the decomposition of ALCSO in a manner that can efficiently impart the aroma of garlic, the following experiments were conducted. A vial (ICHEM vial) containing a sample prepared according to the formulation in Table 9 was set on a heating stirrer and heated. At that time, in order to make the reaction in an open system close to the actual cooking conditions, only the inner lid of the vial was removed and covered with aluminum foil from above. The time when the temperature reached the predetermined temperature was set as the heating time of 0 minutes, and after the specified time in Table 9 elapsed, the vial was cooled with ice water to stop the reaction. The candidate compounds are as follows: pyridoxal-5'-phosphate, pyridoxal, furfural, salicylaldehyde, pyridoxine, aluminum chloride, iron(III) chloride, copper(II) chloride, zinc chloride, zinc oxide, iron(III) chloride tetrahydrate. The added amount of each candidate compound was added so as to be 1 equivalent to the amount of substance [mol] of ALCSO.

[0122]

Table 9

[0123] In addition, the reagents, instruments, etc. used in this screening are shown in Table 10 below.

[0124]

Table 10

[0125] [Pretreatment for Analysis of Heating Test] For each reaction solution reacted according to the above-described experimental conditions, Milli-Q water and salad oil were added to the vial so that it became 4 mL of water and 4 mL of oil, and it was sufficiently stirred by vortexing. The total volume of the solution (8 mL) was put into a 50 mL Falcon tube and centrifuged at 9,000 rpm for 10 minutes. The reaction solution was separated into an upper layer (oil layer) and a lower layer (water layer).

[0126] [Examination of the Decomposition Rate of ALCSO] 10 μL was collected from the lower layer (i.e., the aqueous layer) of the centrifuged aqueous solution, and the aqueous solution diluted 10,000-fold with Milli-Q water was filtered through a filter (manufactured by GL Sciences Inc., model number 5040-28510). 200 μL of the filtered aqueous solution was placed in an LC vial, and the decomposition rate of ALCSO was calculated using the analysis conditions (LC / MS) and calculation formula detailed in Table 11 below.

[0127]

Table 11

[0128] [Regarding various calculation formulas] The decomposition rate of ALCSO was calculated using the following calculation formula.

[0129] ALCSO decomposition rate = (1 - (ALCSO concentration after reaction [weight ppm]) / (ALCSO concentration before reaction weight [ppm])) × 100 [%]

[0130] [Examination of the presence and intensity of garlic aroma] The decomposition product of ALCSO using the candidate compound was evaluated by a sensory test for the presence of garlic aroma. The sensory test was specifically conducted as follows. The test sample after the reaction was diluted so that it became 300 weight ppm as the equivalent amount of ALCSO before decomposition (for example, when the reaction was carried out at 30,000 weight ppm of ALCSO before decomposition, the test sample after the reaction was diluted 100-fold using dilution with a water / oil = 50 / 50 solution). One professional panelist evaluated the presence and intensity of garlic aroma for the obtained diluted sample using the following criteria.

[0131] ++: With strong garlic aroma +: With garlic aroma -: Without garlic aroma

[0132] [Results] The results of sensory tests regarding the decomposition rate of ALCSO, the presence and intensity of garlic aroma when promoting the decomposition of ALCSO using various candidate compounds are shown in Table 12 below. The meanings of "◎", "○", and "×" in the table are as follows.

[0133] ◎: Decomposition rate of 80% or more ○: Decomposition rate of 60% or more and less than 80% ×: Decomposition rate of less than 60%

[0134]

Table 12

[0135] As shown in Table 12, when adding a pyridine derivative having an aldehyde group at the 4-position such as pyridoxal or pyridoxal-5'-phosphate and having a free hydroxyl group in the molecule, or a Lewis acidic metal compound, the decomposition of ALCSO accompanied by garlic aroma is promoted.

[0136] Although not intended to be bound by theory, a pyridine derivative having an aldehyde group at the 4-position and having a free hydroxyl group in the molecule may have its aldehyde group in the molecule condense with the amino group of ALCSO, thereby forming a Schiff base, and then promoting the decomposition of ALCSO accompanied by garlic aroma. In addition, a Lewis acidic metal compound may coordinate with the double bond or oxygen atom of ALCSO, thereby promoting the decomposition of ALCSO accompanied by garlic aroma.

[0137] [Example 6: Examination of the addition concentration of sulfide precursor compounds] To determine the addition concentration of sulfide precursor compounds capable of imparting a favorable aroma, using an apparatus similar to the experimental apparatus used in Example 5, sulfide precursor compounds at various concentrations were pyrolyzed in a solvent using a decomposition enhancer, and the aroma-imparting effect was verified. As the decomposition enhancer, pyridoxal-5'-phosphate (1 equivalent relative to the amount of ALCSO used) was used. As the sulfide precursor compound, ALCSO was used. ALCSO and pyridoxal-5'-phosphate were dissolved in a solvent (a mixture of MilliQ water (80 wt% (4000 mg)) and salad oil (20 wt% (1000 mg))), and heated at 100 °C for 10 minutes. For the obtained samples, one professional panel evaluated the aroma-imparting effect by a sensory test. The evaluation criteria were the same as those used in Example 5. The results are shown in Table 13.

[0138]

Table 13

[0139] As shown in Table 13, it was shown that an aroma-imparting effect can be obtained by using a certain amount or more of ALCSO.

[0140] [Example 7: Examination of the addition amount of the decomposition enhancer] To determine the preferred addition amount of the decomposition enhancer, using an apparatus similar to the experimental apparatus used in Example 5, with various addition amounts of the decomposition enhancer, the sulfide precursor compound was pyrolyzed in a solvent, and the aroma-imparting effect was verified. As the sulfide precursor compound, ALCSO (usage amount: 30000 weight ppm) was used. As the decomposition enhancer, pyridoxal-5'-phosphate was used. The composition of the solvent, heating temperature, and heating time were the same as in Example 6. Note that the addition amount of the decomposition enhancer indicates the amount relative to the usage amount (mol) of ALCSO. The results are shown in Table 14.

[0141]

Table 14

[0142] As shown in Table 14, it was shown that an aroma imparting effect can be obtained by using pyridoxal-5'-phosphate in an amount of a certain level or more with respect to the amount of use (mol) of ALCSO. Although the study at an addition amount exceeding 1 equivalent has not been conducted, since it is considered that the reaction between the sulfides precursor compound and the decomposition enhancer proceeds more easily as the addition amount of the decomposition enhancer increases, it is expected that a preferable aroma imparting effect can be obtained even in the case of an addition concentration exceeding 1 equivalent.

[0143] [Example 8: Examination of reaction temperature] In order to determine the temperature range capable of imparting a preferable aroma, using a device similar to the experimental device used in Example 5, the sulfides precursor compound was thermally decomposed in a solvent using a decomposition enhancer at various temperatures, and the aroma imparting effect was verified. ALCSO (usage amount: 30,000 weight ppm) was used as the sulfides precursor compound. Pyridoxal-5'-phosphate (0.75 equivalent with respect to the usage amount of ALCSO) was used as the decomposition enhancer. The composition of the solvent and the heating time were the same as in Example 6. The results are shown in Table 15.

[0144]

Table 15

[0145] As shown in Table 15, it was shown that an aroma imparting effect can be obtained by heating at a temperature of a certain level or more. Although the study at a temperature of 100 °C or higher has not been conducted, since it is considered that the sulfides precursor compound is more easily thermally decomposed as the heating temperature is higher, it is expected that a preferable aroma imparting effect can be obtained even when heating at a temperature exceeding 100 °C.

[0146] [Example 9: Examination of heating time] To determine the shortest heating time capable of imparting a favorable aroma, using an apparatus similar to the experimental apparatus used in Example 5, a sulfide precursor compound was heated in a solvent for 1 minute using a decomposition enhancer, and the aroma-imparting effect was verified. As the sulfide precursor compound, ALCSO (see Table 17 below for the usage amount) was used. As the decomposition enhancer, pyridoxal-5'-phosphate (0.75 equivalent relative to the usage amount of ALCSO) was used. The composition of the solvent and the heating temperature were the same as in Example 6. Under the conditions shown in Table 16 below, using a gas chromatograph (manufactured by Agilent technology), the abundance of diallyl disulfide contained in the sample 1 minute after the start of heating was shown as the peak area value. Specifically, in the sample spectrum analyzed under the conditions described in Table 16 below, when searching by molecular weight (Mw: 146), the peak that appears around a retention time of 5.4 min to 5.6 min was integrated, and the value was recorded. In the case where it was not detected by the above method, it was described as "N.D. (not detected)". Also, for the obtained sample, one professional panel evaluated the presence or absence of aroma by a sensory test. The evaluation criteria were the same as those used in Example 5. The results are shown in Table 17.

[0147]

Table 16

[0148]

Table 17

[0149] As shown in Table 17, the aroma component (i.e., diallyl disulfide) was detected 1 minute after the start of heating, and it was also confirmed that it had a garlic aroma in the sensory evaluation. Therefore, it was shown that the aroma-imparting effect of the present invention can be obtained immediately after the start of heating.

Industrial Applicability

[0150] According to the present invention, even if the amount of garlic used is reduced, the garlic flavor can be efficiently imparted to food and drink products, which is useful in the food and drink manufacturing industry.

[0151] This application is based on Japanese Patent Application No. 2018-211747 (filing date: November 9, 2018) and Japanese Patent Application No. 2018-211748 (filing date: November 9, 2018), the contents of which are all incorporated herein.

Claims

**Claim 1** A method for imparting aroma to a food or drink, comprising adding and heating: (1) at least one Lewis acidic metal compound selected from the group consisting of iron(III) chloride and aluminum chloride; and (2) S-allyl-L-cysteine sulfoxide (ALCSO). **Claim 2** A method for imparting aroma to a food or drink, comprising adding (1) at least one Lewis acidic metal compound selected from the group consisting of iron(III) chloride and aluminum chloride; and (2) S-allyl-L-cysteine sulfoxide (ALCSO) to a solvent in which water and oil are mixed, heating to obtain a solution containing sulfides as aroma components, recovering the oil component from the solution, and mixing, applying, or spraying the oil component to the food or drink. **Claim 3** The method according to claim 2, wherein the recovered oil component is diluted and then mixed, applied, or sprayed onto the food or drink. **Claim 4** The method according to any one of claims 1 to 3, wherein the heating temperature is 40°C to 250°C. **Claim 5** The method according to any one of claims 1 to 4, wherein the heating time is 30 seconds to 48 hours. **Claim 6** A method for producing a food or drink imparted with aroma, comprising adding and heating: (1) at least one Lewis acidic metal compound selected from the group consisting of iron(III) chloride and aluminum chloride; and (2) S-allyl-L-cysteine sulfoxide (ALCSO). **Claim 7** A method for producing a food or drink imparted with aroma, comprising adding (1) at least one Lewis acidic metal compound selected from the group consisting of iron(III) chloride and aluminum chloride; and (2) S-allyl-L-cysteine sulfoxide (ALCSO) to a solvent in which water and oil are mixed, heating to obtain a solution containing sulfides as aroma components, recovering the oil component from the solution, and mixing, applying, or spraying the oil component to the food or drink. **Claim 8** The production method according to claim 7, wherein the recovered oil component is diluted and then mixed, applied, or sprayed onto the food or drink. **Claim 9** The production method according to any one of claims 6 to 8, wherein the heating temperature is 40°C to 250°C. **Claim 10** The production method according to any one of claims 6 to 9, characterized in that the heating time is from 30 seconds to 48 hours.

11. (1) at least one Lewis acidic metal compound selected from the group consisting of iron(III) chloride and aluminum chloride, (2) S-allyl-L-cysteine sulfoxide (ALCSO), A method for producing a flavoring agent, comprising adding and heating the above to a solvent.

12. (1) at least one Lewis acidic metal compound selected from the group consisting of iron(III) chloride and aluminum chloride, (2) S-allyl-L-cysteine sulfoxide (ALCSO), A method for producing a flavoring agent, comprising adding the above to a solvent obtained by mixing water and oil and heating to obtain a solution containing sulfides as flavor components, and recovering the oil component from the solution.

13. The production method according to claim 12, further comprising diluting the recovered oil component.

14. The production method according to any one of claims 11 to 13, characterized in that the heating temperature is from 40°C to 250°C.

15. The production method according to any one of claims 11 to 14, characterized in that the heating time is from 30 seconds to 48 hours.

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