Agent for imparting or enhancing oil / fat cooking aroma

Abstract

The present invention provides an agent which is for imparting or enhancing an oil / fat cooking aroma, which can be used for foods, drinks, or seasonings in general, and which comprises: 2,4-dienal and / or one or more of n-saturated aldehydes as an active component; one or more of α-amino acids, proline, lysine hydrochloride, cysteine, and glutathione as a key component (component A); and, as a sub component, a component B that is constituted by one or more components from among unsaturated aldehydes, 1-octen-3-ol, and (Z)-6-dodecen-4-olide and / or a component C that is constituted by one or more components (component C-1) from among sulfur compounds and 3-mercaptopropionic acid and one or more hydroxyketones (component C-2).　When the active component is an n-saturated aldehyde, the agent for imparting or enhancing an oil / fat cooking aroma comprises one or more of dicarbonyl compounds as a second key component (component D).

Description

Fat cooking aroma enhancer

[0001] The present invention relates to an agent for imparting or enhancing an oil / fat cooking aroma to a food, drink, or seasoning.

[0002] In recent years, excessive intake of calories and fat has become a problem due to the Westernization of dietary habits and the diversification of processed and prepared foods. In response, progress has been made in the development of low-calorie and low-fat foods, but fat plays a major role in making food and drink more delicious, and satisfying consumer preferences with low-fat foods is a challenge.

[0003] Against this background, techniques for enhancing the cooking aroma of oils and fats include adding aroma components specific to the oily feel and cooking aroma to cooked foods as flavorings, and adding precursors of components that contribute to the cooking aroma before the heating process.

[0004] For example, Patent Document 1 proposes a method for improving the flavor of low-fat foods by simply adding a trace amount of (E)-6-octenal, which is an active ingredient, in combination with a flavor-improving composition to low-fat foods or non-oil foods. However, problems with this technology include limited applications due to the limited variety of aroma notes and the difficulty of imparting a more complex cooked feel. Furthermore, the aroma cannot be enhanced when heated during consumption.

[0005] Furthermore, Patent Document 2 proposes a method for imparting a burnt oil flavor or cooking aroma, enhancing the oily and fatty feel, and masking unpleasant odors by combining phenols, unsaturated aldehydes, etc. However, with this technology, the flavor is in its final form immediately after adding the above-mentioned components, and it is inevitable that the aroma (effect) will fade or change over time (during processing, distribution, and storage).

[0006] On the other hand, Patent Document 3 proposes an agent for imparting or enhancing a freshly cooked aroma, which contains as active ingredients a component A consisting of one or more compounds selected from the group consisting of α-amino acids, cystine, and glutathione, and a component B consisting of one or more compounds selected from the group consisting of dicarbonyl compounds, mercaptocarbonyl compounds, and 3-mercaptopropionic acid. However, no consideration is given to enhancing the cooking aroma of fats and oils.

[0007] Japanese Patent Publication No. 2018-000022 Japanese Patent No. 7156270 Japanese Patent Publication No. 2021-106518

[0008] As mentioned above, there is a need for a technology for enhancing or imparting an oily cooking aroma to cooked foods that can be used universally for all foods and beverages, that allows for adjustment of the aroma tone and concentration on an aroma component-by-aroma component basis, that has a simple manufacturing process, that imparts a desirable oily cooking aroma when heated, and that is strongest when eaten; however, such a technology does not exist to date.

[0009] The term "cooked aroma of oil and fat" as used herein refers to the aroma that is produced by heating food, drink, or seasonings, and is a combination of the oil and fat aroma that gives the richness and fullness of fat and the cooked aroma.

[0010] The present invention has been made in consideration of the above circumstances, and aims to provide an agent for imparting or enhancing an oil / fat cooking aroma that can be used in foods, beverages, or seasonings in general, is highly effective in contributing to the aroma of oil / fat cooking, and can satisfy consumer preferences.

[0011] As a result of intensive research conducted by the inventors to solve the above-mentioned problems, they have found that when a composition containing a specific active ingredient, a specific group of key ingredients (ingredient A), and specific sub-ingredients (ingredient B and / or ingredient C), or a further specific second key ingredient (ingredient D), is heated, at least one type of ingredient in group I, which consists of long-chain alkylpyridines and long-chain alkylpyrazines that contribute to the oily aroma that brings about a rich feeling and a thick body, increases, and at least one type of ingredient in group II, which consists of pyrazines, pyrroles, thiazoles, thiophenes, furans, and pyridines that contribute to the cooked aroma, is produced, and that when this composition is added to a food, drink, or seasoning and heated, the cooked aroma of oily ingredients can be imparted or enhanced.

[0012] That is, the inventors have discovered that the specific active ingredient and the specific key ingredient contained in the composition, or further the second key ingredient, are precursors capable of producing components belonging to Group I consisting of long-chain alkylpyridines and long-chain alkylpyrazines that contribute to the aroma of fats and oils, and components belonging to Group II consisting of pyrazines, pyrroles, thiazoles, thiophenes, furans, and pyridines that contribute to the aroma of cooked fats and oils, and that when a composition containing these components and a specific sub-ingredient is heated, it is possible to produce a more desirable aroma of cooked fats and oils that contains at least one component belonging to each of Group I and Group II, has a unified flavor, and has an enhanced desired aroma.

[0013] The present invention has been completed based on these findings and provides the following invention: [1] An agent for imparting or enhancing cooking aroma to fats and oils, comprising, as active ingredients, one or more 2,4-dienals represented by the following general formula (1) and / or n-saturated aldehydes represented by the following general formula (2), and, as key components (component A), one or more of an α-amino acid represented by the following general formula (3), proline, lysine hydrochloride, cystine, and glutathione, and, as subcomponents, component B consisting of one or more of an unsaturated aldehyde represented by the following general formula (4), 1-octen-3-ol, and (Z)-6-dodecen-4-olide, and / or component C consisting of one or more of a sulfur compound represented by the following general formula (5) and 3-mercaptopropionic acid (component C-1), and one or more hydroxyketones represented by the following general formula (6) (component C-2). However, when the active ingredient is the n-saturated aldehyde, the composition contains, as the second key ingredient (ingredient D), one or more dicarbonyl compounds represented by the following general formula (7). (In the formula, R １ represents a linear saturated alkyl group having 4 or more carbon atoms. (In the formula, R ２ represents a linear saturated alkyl group having 4 or more carbon atoms. (In the formula, R ３ indicates an amino acid side chain.) (In the formula, R ４ represents a linear saturated alkyl group having 3 to 6 carbon atoms.) (In the formula, R ５ and R ６ each independently represents any one of an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, a hydroxyl group, and a hydrogen atom. (In the formula, R ７ and R ８each independently represents any one of an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, a hydroxyl group, and a hydrogen atom. (In the formula, R ９ and R １０each independently represent an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, an aralkyl group which may have a substituent, a hydroxyl group, or a hydrogen atom.) [2] The agent for imparting or enhancing a cooking aroma of fats and oils according to [1] above, wherein the active ingredient, the key ingredient, and the sub-ingredient, or further the second key ingredient, upon a heating reaction, produce at least one component belonging to Group I consisting of long-chain alkylpyridines and long-chain alkylpyrazines, and at least one component belonging to Group II consisting of pyrazines, pyrroles, thiazoles, thiophenes, furans, and pyridines. [3] The agent for imparting or enhancing a cooking aroma of fats and oils according to [1] or [2] above, wherein the 2,4-dienal represented by the general formula (1) is one or more selected from the group consisting of 2,4-nonadienal, 2,4-decadienal, and 2,4-undecadienal. [4] The cooking aroma imparting or enhancing agent for fats and oils according to any one of [1] to [3], wherein the n-saturated aldehyde represented by the general formula (2) is one or more selected from the group consisting of pentanal, hexanal, heptanal, octanal, and nonanal. [5] The cooking aroma imparting or enhancing agent for fats and oils according to any one of [1] to [4], wherein the α-amino acid represented by the general formula (3) is one or more selected from the group consisting of glycine, alanine, leucine, valine, phenylalanine, glutamine, glutamic acid, methionine, and histidine. [6] The cooking aroma imparting or enhancing agent for fats and oils according to any one of [1] to [5], wherein the unsaturated aldehyde represented by the general formula (4) is one or more selected from the group consisting of (E)-2-hexenal, (E)-2-heptenal, (E)-2-octenal, and (E)-2-nonenal. [7] The cooking aroma imparting or enhancing agent for fats and oils according to any one of [1] to [6], wherein the sulfur compound represented by the general formula (5) is one or more selected from the group consisting of 2-mercaptosuccinic acid, 2-mercaptopropionic acid, and 3-mercapto-2-butanone.[8] The cooking aroma imparting or enhancing agent for fats and oils according to any one of [1] to [7] above, wherein the hydroxyketone represented by the general formula (6) is one or more selected from the group consisting of acetoin, acetol, and dihydroxyacetone. [9] The cooking aroma imparting or enhancing agent for fats and oils according to any one of [1] to [8] above, wherein the dicarbonyl compound represented by the general formula (7) is one or more selected from the group consisting of glyoxal, pyruvaldehyde, pyruvic acid, diacetyl, acetylpropionyl, acetylbutyryl, acetylvaleryl, and acetylbenzoyl.

[10] The cooking aroma imparting or enhancing agent for fats and oils according to any one of [1] to [9] above, further comprising one or more selected from the group consisting of synthetic flavors, natural flavors, spice extracts, and solvents.

[0014] The active ingredient, the key ingredient, the sub-ingredient, and / or the second key ingredient in the fat / oil cooking aroma imparting or enhancing agent of the present invention are precursors of aromas that contribute to the fat / oil aroma or the cooked aroma, and heating these precursors newly generates aroma components that contribute to the rich fat / oil aroma and the cooked aroma. Therefore, according to the present invention, by heating a food or drink or seasoning to which an effective amount of the fat / oil cooking aroma imparting or enhancing agent has been added, new components that contribute to the fat / oil cooking aroma are generated, and the mixture of these components produces a synergistic effect, thereby imparting or enhancing the fat / oil cooking aroma.

[0015] Hereinafter, embodiments of the present invention will be described in detail, but the present invention is not limited to these embodiments. Note that when a numerical range is stated (two numerical values ​​connected by "to"), it means that the numerical values ​​stated as the lower limit and upper limit are also included.

[0016] The agent for imparting or enhancing cooking aroma to fats and oils of the present invention is characterized by containing, as active ingredients, one or more 2,4-dienals represented by the following general formula (1) and / or n-saturated aldehydes represented by the following general formula (2): as key components (component A), one or more selected from α-amino acids represented by the following general formula (3), proline, lysine hydrochloride, cystine, and glutathione; and as sub-components, one or more selected from unsaturated aldehydes represented by the following general formula (4), 1-octen-3-ol, and (Z)-6-dodecen-4-olide (component B), and / or one or more selected from sulfur compounds represented by the following general formula (5) and 3-mercaptopropionic acid (component C-1), and a hydroxyketone represented by the following general formula (6) (component C-2), each at effective concentrations. However, when the active ingredient is the n-saturated aldehyde, the second key ingredient (component D) contains one or more dicarbonyl compounds represented by the following general formula (7).

[0017] In the present invention, the term "effective concentration" means a sufficient amount to exhibit the desired aroma (cooking aroma of fats and oils). Therefore, the cooking aroma imparting or enhancing agent of this embodiment may contain only the active ingredient, the key ingredient, and the sub-ingredient, or the second key ingredient, but may also contain other flavoring ingredients, food ingredients, and additives such as solvents, as long as the desired aroma is not impaired.

[0018] The active ingredient, key ingredient, and sub-ingredient, or even the second key ingredient, of the present invention, can serve as precursors of aromas that contribute to the aroma of fats and oils or cooking aroma. When these ingredients are heated, a composition that imparts or enhances the aroma of fats and oils cooking is obtained, which contains at least one component belonging to Group I, consisting of long-chain alkylpyridines and long-chain alkylpyrazines, which contribute to a thick, rich body and rich flavor, and at least one component belonging to Group II, consisting of pyrazines, pyrroles, thiazoles, thiophenes, furans, and pyridines, which contribute to the aroma of cooking. The composition has a unified flavor and a desired enhanced aroma. Therefore, by heating a food, drink, or seasoning to which the fat and oil cooking aroma imparting or enhancing agent of the present invention has been added, the desired fat and oil cooking aroma can be imparted or enhanced to the food, drink, or seasoning. The fat and oil cooking aroma imparting or enhancing agent of the present invention will be described in more detail below.

[0019] <Active ingredient> In the present invention, one or more active ingredients selected from the group consisting of 2,4-dienals represented by the following general formula (1) (hereinafter also referred to as "active ingredient 1") and n-saturated aldehydes represented by the following general formula (2) (hereinafter also referred to as "active ingredient 2") are used as the active ingredient.

[0020] (In the formula, R １ represents a linear saturated alkyl group having 4 or more carbon atoms.

[0021] (In the formula, R ２ represents a linear saturated alkyl group having 4 or more carbon atoms.

[0022] The 2,4-dienal represented by the general formula (1) is not particularly limited, but for example, those approved as food additives such as 2,4-nonadienal, 2,4-decadienal, and 2,4-undecadienal can be suitably used, with 2,4-decadienal being most suitably used. The n-saturated aldehyde represented by the general formula (2) is not particularly limited, but for example, those approved as food additives such as pentanal, hexanal, heptanal, octanal, nonanal, and decanal can be suitably used, with pentanal, hexanal, heptanal, octanal, and nonanal being most suitably used.

[0023] <Key Component (Component A)> In the present invention, the key component (Component A) is at least one selected from the group consisting of an α-amino acid represented by the following general formula (3), proline, lysine hydrochloride, cystine, and glutathione.

[0024] (In the formula, R ３ indicates an amino acid side chain.)

[0025] The α-amino acid represented by the general formula (3) is not particularly limited, and for example, those approved as food additives such as glycine, alanine, leucine, valine, phenylalanine, glutamine, glutamic acid, methionine, histidine, arginine, asparagine, tyrosine, and threonine can be suitably used, with glycine, alanine, leucine, valine, phenylalanine, glutamine, glutamic acid, methionine, and histidine being particularly suitable. The key component is an essential component for producing at least one of long-chain alkylpyridines and long-chain alkylpyrazines, which are components belonging to Group I, and at least one of pyrazines, pyrroles, thiazoles, thiophenes, furans, and pyridines, which are components belonging to Group II, by heating together with Active Ingredient 1, or by heating together with Active Ingredient 2 and a second key component described below.

[0026] <Sub-components> In the present invention, the sub-components include the following component B, and / or a component C consisting of the following component C-1 and component C-2. The sub-components are not essential for producing the above-mentioned group I and group II, but are essential for unifying the flavor and enhancing the desired aroma when heated together with the above-mentioned active ingredient, the above-mentioned key component, and / or the above-mentioned second key component.

[0027] (Component B) In the present invention, one or more members selected from the group consisting of unsaturated aldehydes represented by the following general formula (4), 1-octen-3-ol, and (Z)-6-dodecen-4-olide are used as component B.

[0028] (In the formula, R ４ represents a linear saturated alkyl group having 3 to 6 carbon atoms.)

[0029] The unsaturated aldehyde represented by the general formula (4) is not particularly limited, but for example, those approved as food additives such as (E)-2-hexenal, (E)-2-heptenal, (E)-2-octenal, and (E)-2-nonenal can be suitably used, and in particular, (E)-2-heptenal, (E)-2-octenal, and (E)-2-nonenal can be most suitably used.

[0030] (Component C-1) In the present invention, one or more compounds selected from the group consisting of sulfur compounds represented by the following general formula (5) and 3-mercaptopropionic acid are used as component C-1.

[0031] (In the formula, R ５ and R ６ each independently represents any one of an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, a hydroxyl group, and a hydrogen atom.

[0032] The sulfur compound represented by the general formula (5) is not particularly limited, but for example, those approved as food additives such as 3-mercapto-2-butanone, 3-mercapto-2-pentanone, 2-mercaptopropionic acid, and 2-mercaptosuccinic acid can be suitably used, and in particular, 2-mercaptopropionic acid, 2-mercaptosuccinic acid, and 3-mercapto-2-butanone can be most suitably used.

[0033] (Component C-2) In the present invention, one or more hydroxyketones selected from the group consisting of hydroxyketones represented by the following general formula (6) are used as component C-2.

[0034] (In the formula, R ７ and R ８ each independently represents any one of an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, a hydroxyl group, and a hydrogen atom.

[0035] The hydroxyketone represented by the general formula (6) is not particularly limited, but for example, acetoin, acetol, dihydroxyacetone, and other hydroxyketones approved as food additives can be suitably used, with acetoin and acetol being particularly suitable.

[0036] <Second Key Component (Component D)> In the present invention, when the active ingredient is the n-saturated aldehyde, one or more compounds selected from the group consisting of dicarbonyl compounds represented by the following general formula (7) are used as the second key component (Component D):

[0037] (In the formula, R ９ and R １０ each independently represents any one of an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, a hydroxyl group, and a hydrogen atom.

[0038] The dicarbonyl compound represented by the general formula (7) is not particularly limited, but for example, pyruvaldehyde, pyruvic acid, diacetyl, acetylpropionyl, acetylbutyryl, acetylvaleryl, acetylisovaleryl, acetylbenzoyl, and other compounds approved as food additives can be suitably used, and in particular, pyruvaldehyde, diacetyl, acetylpropionyl, and acetylbutyryl can be most suitably used.

[0039] In the fat / oil cooking aroma imparting or enhancing agent according to this embodiment, the contents of the active ingredient, the key ingredient, the sub-ingredient, and / or the second key ingredient are not particularly limited and vary depending on the type of food or beverage and the type of aroma composition used, but are preferably within the range of 0.0001 to 60% by mass, more preferably 0.0005 to 30% by mass, and most preferably 0.0008 to 15% by mass.

[0040] (Components Belonging to Groups I and II) The active ingredient and the key component, or the second key component, are precursors capable of producing at least one component belonging to Group I, consisting of long-chain alkylpyridines and long-chain alkylpyrazines, which contribute to the thickness and richness of the body, and at least one component belonging to Group II, consisting of pyrazines, pyrroles, thiazoles, thiophenes, furans, and pyridines, which contribute to the cooked aroma. The respective components react upon heating to produce a desirable cooked aroma of fats and oils containing at least one component from each of Groups I and II. The subcomponents are not essential components for producing the components from Groups I and II, but are necessary for unifying the flavor and enhancing the desired aroma.

[0041] (Components Belonging to Group I) Specific examples of components belonging to Group I (oil and fat aromas that contribute to the thickness and richness of the body) include long-chain alkylpyridines such as 2-butylpyridine, 2-pentylpyridine, 2-hexylpyridine, and 2-heptylpyridine, and long-chain alkylpyrazines such as 2-methyl-3-pentylpyrazine, 2-methyl-5-pentylpyrazine, 2-methyl-6-pentylpyrazine, 2,5-dimethyl-3-pentylpyrazine, 2,6-dimethyl-3-pentylpyrazine, 2,5-dimethyl-3,6-dipentylpyrazine, and 2,6 -dimethyl-3,5-dipentylpyrazine, 2,3,5-trimethyl-6-pentylpyrazine, 2-hexyl-3-methylpyrazine, 2-hexyl-5-methylpyrazine, 2-hexyl-6-methylpyrazine, 2-hexyl-3,5-dimethylpyrazine, 2-hexyl-3,6-dimethylpyrazine, 2,5-dihexyl-3,6-dimethylpyrazine, 2,6-dihexyl-3,5-dimethylpyrazine, 2-hexyl-3,5,6-trimethylpyrazine, 2-heptyl-3-methylpyrazine, 2-heptyl-5-methylpyrazine ethylpyrazine, 2-heptyl-6-methylpyrazine, 2-heptyl-3,5-dimethylpyrazine, 2-heptyl-3,6-dimethylpyrazine, 2,5-diheptyl-3,6-dimethylpyrazine, 2,6-diheptyl-3,5-dimethylpyrazine, 2-heptyl-3,5,6-trimethylpyrazine, 2-methyl-3-octylpyrazine, 2-methyl-5-octylpyrazine, 2-methyl-6-octylpyrazine, 2,5-dimethyl-3-octylpyrazine, 2,6-dimethyl-3-octylpyrazine, 2,5-dimethyl Examples include 2,6-dimethyl-3,6-dioctylpyrazine, 2,6-dimethyl-3,5-dioctylpyrazine, 2,3,5-trimethyl-6-octylpyrazine, 2-methyl-3-nonanylpyrazine, 2-methyl-5-nonanylpyrazine, 2-methyl-6-nonanylpyrazine, 2,5-dimethyl-3-nonanylpyrazine, 2,6-dimethyl-3-nonanylpyrazine, 2,5-dimethyl-3,6-dinonanylpyrazine, 2,6-dimethyl-3,5-dinonanylpyrazine, and 2,3,5-trimethyl-6-nonanylpyrazine.

[0042] (Components Belonging to Group II) Specific examples of components belonging to Group II (components contributing to cooked aroma) include 2-methyl-3-furanthiol, furfural, 2-furyl methyl ketone, 5-methyl-2-furfural, 2-methylfuran, 2,5-dimethylfuran, 2,3,4-trimethylfuran, 2,3,5-trimethylfuran, tetramethylfuran, 2-butylfuran, 2-pentylfuran, 2-hexylfuran, 2-acetyl-5-methylfuran, 3-acetyl-2,5-dimethylfuran, furfuryl alcohol, furaneol, and sotolo. thiazole, 2,5-dimethyl-3(2H)-furanone, thiazole, 2-methylthiazole, 4-methylthiazole, 4,5-dimethylthiazole, 2,4-dimethylthiazole, 2,4,5-trimethylthiazole, 2,5-diethylthiazole, 2-acetylthiazole, 2,4-dimethyl-5-acetylthiazole, benzothiazole, 4,5-dimethyl-2-isopropylthiazole, thiophene, 2-methylthiophene, butenylthiophene, 2,5-dimethylthiophene, 2,4-dimethylthiophene, 3,4- Dimethylthiophene, 2,5-diethylthiophene, 2,3,5-trimethylthiophene, 2-acetyl-5-methylthiophene, 2,3,4,5-tetramethylthiophene, 5-methyl-2-thiophenecarboxaldehyde, 5-ethyl-2-thiophenecarboxaldehyde, 1-methylpyrrole, 1-ethylpyrrole, 2-acetylpyrrole, 2,3,4-trimethylpyrrole, pyridine, 2-methylpyridine, 3-methylpyridine, 5-ethyl-2-methylpyridine, 3,4-dimethylpyridine, 2,4,6 -trimethylpyridine, pyrazine, 2-methylpyrazine, 2-ethylpyrazine, 2,3-dimethylpyrazine, 2,5-dimethylpyrazine, 2,6-dimethylpyrazine, 2-ethyl-5-methylpyrazine, 2-ethyl-6-methylpyrazine, 2-ethyl-3,5(6)-dimethylpyrazine, 2,5-diethylpyrazine, 2,6-diethylpyrazine, 3,5-diethyl-2-methylpyrazine, 2,3,5-trimethylpyrazine, 2,3,5,6-tetramethylpyrazine, 2-acetyl-3-methylpyrazine, and the like.

[0043] <Other Additives> (Flavoring Components) The fat / oil cooking aroma imparting or enhancing agent according to this embodiment may contain a food additive for flavoring in addition to the active ingredient, the key ingredient, the sub-ingredient, and / or the second key ingredient, as long as the desired aroma is not impaired. Such food additives are not particularly limited, and known additives can be used, including, for example, various synthetic flavors, natural flavors, and spice extracts. Examples of such additives include the synthetic flavors, natural flavors, and spice extracts described in "Japan Patent Office, Collection of Well-Known and Commonly Used Techniques (Flavors), Part II: Food Flavors, p. 88-131, published January 14, 2000."

[0044] Specific examples of such fragrances include: aldehydes such as acetaldehyde, propanal, butanal, isobutanal, 2-methylbutanal, 3-methylbutanal, isovaleraldehyde, trans-2-decenal, trans-2-undecenal, trans-2-dodecenal, 2,4-hexadienal, 2,4-heptadienal, and benzaldehyde; and alcohols such as ethanol, propanol, butanol, 2-methylbutanol, amyl alcohol, isoamyl alcohol, hexanol, 2-ethylhexanol, heptanol, octanol, nonanol, decanol, dodecanol, 1-penten-3-ol, benzyl alcohol, and furfuryl alcohol. Ketones such as 1-penten-3-one, 3-penten-2-one, 1-octen-3-one, 3-octen-2-one, amyl methyl ketone, and heptyl methyl ketone. Sulfur-containing compounds such as dimethyl sulfide, dimethyl disulfide, methyl propyl trisulfide, bis(methylthio)methane, methionol, and methional. Heterocyclic compounds such as thiazole, benzothiazole, 4,5-dimethylthiazole, sulfurol, 2-methylpyrazine, 2,3-dimethylpyrazine, 2,5-dimethylpyrazine, 2,6-dimethylpyrazine, 2-ethylpyrazine, tetramethylpyrazine, indole, skatole, furfural, 5-methyl-2-furfural, furaneol, 5-hydroxy-3-methyl-2-cyclopenten-1-one, and sotolone. Natural fragrances such as violet, hay, and oakmoss. Spice extracts such as mace, nutmeg, sage, coriander, cumin, thyme, allspice, laurel, cardamom, celery, cloves, dill, ginger, fenugreek, parsley, oregano, white pepper, black pepper, rose, etc. The above ingredients may be used alone or in combination of two or more.

[0045] (Solvent) The fat / oil cooking aroma imparting or enhancing agent according to this embodiment may contain a solvent as an additive in addition to the active ingredient, key ingredient, sub-ingredient, or even the second key ingredient, as long as the desired aroma is not impaired. The type and concentration of such a solvent are not particularly limited as long as it can dissolve the above-mentioned flavoring. However, preferred solvents are those approved as food additives, such as water, ethanol, propylene glycol, glycerin, and triacetin, with water, ethanol, and propylene glycol being particularly preferred. The above solvents may be used alone or in combination of two or more.

[0046] When a food, drink, or seasoning to which the oil / fat cooking aroma imparting or enhancing agent of the present invention is added is a food, drink, or seasoning to be heated at the time of consumption, the flavor of the food, drink, or seasoning can be enhanced by heating it at the time of consumption. The heating method is not particularly limited and varies depending on the type of food, drink, or seasoning, but known methods such as a microwave oven, oven, toaster, fryer, steam, boiling, grilling, and baking can be used. In order to obtain a product containing at least one component from each of Groups I and II by thermal reaction of the active ingredient, the key ingredient, and the sub-component, or further the second key ingredient, it is preferable to heat the food, drink, or seasoning at least once at 60 to 500°C for 1 to 180 minutes at the time of consumption.

[0047] Furthermore, as described above, in the case of foods, beverages, or seasonings that are heated only during production, such as in a sterilization step, but not when eaten, the flavor of the foods and beverages when eaten can be enhanced by utilizing only the heating during production. However, in order to obtain a food or beverage that contains at least one component of each of Groups I and II, it is preferable to heat the food or beverage at least once during the production process at 60 to 500°C for 1 to 180 minutes.

[0048] The present invention will be described below using examples and comparative examples, but the present invention is not limited to these examples.

[0049] (Example 1) In this example, the products formed by heating were examined for the invention product and comparative products described below. [Preparation of Invention Product 1] For invention product 1, a fragrance composition was prepared using 2,4-decadienal as the active ingredient, DL-alanine as component A, (E)-2-heptenal as component B, and water as the solvent. The composition is shown in Table 1.

[0050]

[0051] [Preparation of Comparative Product 1A] A fragrance composition consisting of the active ingredient, ingredient B, and solvent, but not containing ingredient A in Invention Product 1, was prepared and designated "Comparative Product 1A." The composition is shown in Table 2.

[0052]

[0053] [Preparation of Comparative Product 1B] A fragrance composition consisting of Component A, Component B, and a solvent was prepared without the active ingredient of Invention Product 1, and designated "Comparative Product 1B." The composition is shown in Table 3.

[0054]

[0055] [Preparation of Comparative Product 1C] A fragrance composition consisting of the active ingredient, component A, and solvent was prepared without the sub-components (component B and component C) of Invention Product 1, and named "Comparative Product 1C." The composition is shown in Table 4.

[0056]

[0057] [Preparation of Invention Product 2] For Invention Product 2, a fragrance composition was prepared using hexanal as the active ingredient, L-valine as component A, 3-mercaptopropionic acid as component C-1, acetol as component C-2, pyruvaldehyde as component D, and propylene glycol as the solvent. The composition is shown in Table 5.

[0058]

[0059] [Preparation of Comparative Product 2A] A fragrance composition consisting of the active ingredient, ingredients C-1, C-2, D, and a solvent, but not containing ingredient A in Invention Product 2, was prepared and designated "Comparative Product 2A." The composition is shown in Table 6.

[0060]

[0061] [Preparation of Comparative Product 2B] A fragrance composition consisting of Component A, Component C-1, Component C-2, Component D, and a solvent was prepared without the active ingredient of Invention Product 2, and designated "Comparative Product 2B." The composition is shown in Table 7.

[0062]

[0063] [Preparation of Comparative Product 2C] A fragrance composition was prepared that did not contain Component D in Invention Product 2 and consisted of the active ingredient, Component A, Component C-1, Component C-2, and a solvent, and was designated "Comparative Product 2C." The composition is shown in Table 8.

[0064]

[0065] [Preparation of Comparative Product 2D] A fragrance composition consisting of the active ingredient, component A, component D, and solvent was prepared without the components C-1 and C-2 of Invention Product 2, and designated "Comparative Product 2D." The composition is shown in Table 9.

[0066]

[0067] [Analysis of the present invention and comparative products] The present invention and comparative products were subjected to instrumental analysis to investigate how the presence or absence of the active ingredient, component A, component B, component C, and component D affects the amount of components that contribute to the newly generated cooking aroma of fats and oils. The analytical results (amounts of components that contribute to the cooking aroma of fats and oils: relative mass ppm) are shown in Tables 10 and 11. Heating was performed at 120°C for 30 minutes in an aluminum block reactor (Shibata Scientific CP-400), and the known SPME method was used for analysis.

[0068]

[0069]

[0070] As shown in Tables 10 and 11, the coexistence and heating of the active ingredient and component A (or component D in addition to component A when an n-saturated aldehyde is selected as the active ingredient) resulted in the expression of at least one of the long-chain alkylpyridines and long-chain alkylpyrazines belonging to Group I, and at least one of the pyrazines, pyrroles, thiazoles, thiophenes, furans, and pyridines belonging to Group II. Therefore, the coexistence and heating of the active ingredient and component A (or component D in addition to component A when an n-saturated aldehyde is selected as the active ingredient) are necessary as a means of producing and enhancing components that contribute to richness and increased volume, and components that contribute to the cooked aroma. Furthermore, the presence of the sub-components (components B and C) is not essential for producing Group I and Group II, but is necessary for unifying the flavor and enhancing the desired aroma, as determined by the sensory evaluation described below.

[0071] [Preparation of Invention Product 3] For Invention Product 3, a fragrance composition was prepared in the same manner as Invention Product 1, except that propylene glycol was used as the solvent. The composition is shown in Table 12.

[0072]

[0073] [Preparation of Invention Product 4] Invention Product 4 was prepared in the same manner as Invention Product 1, except that triacetin was used as the solvent. The composition is shown in Table 13.

[0074]

[0075] [Analysis of the Products of the Present Invention] The Products 1, 3, and 4 of the present invention were subjected to instrumental analysis to investigate how the type of solvent affects the generation of components that contribute to the cooking aroma of fats and oils. The analytical results (amounts of components that contribute to the cooking aroma of fats and oils: relative mass ppm) are shown in Table 14. Heating was carried out at 120°C for 30 minutes in an aluminum block reactor (Shibata Scientific CP-400), and the known SPME method was used for analysis.

[0076]

[0077] As shown in Table 14, even when propylene glycol or triacetin was used as the solvent, it was found that at least one component belonging to group I and at least one component belonging to group II were expressed.

[0078] In the following examples, the products of the present invention and comparative products were added to various foods and drinks, and sensory evaluations were carried out by a panel. The evaluation criteria and definitions of each evaluation item were as follows:

[0079] (Evaluation criteria) -: No significant difference from additive-free product +: Slightly noticeable ++: Strongly noticeable In the tables showing the results, the most frequent value among these is listed.

[0080] (Definition of evaluation items) Cooked oil aroma: Richness and fat of oil, appetizing flavor that can be felt immediately after cooking, roasting or baking. Flavor enhancement effect: Three-dimensional effect with depth, breadth and thickness. Flavor sustaining effect: An effect that clings to the mouth for a long time. Flavor balance improvement effect: Good cohesion, good balance of flavor in the food and drink as a whole. The comments column in the table listing the results is an extract of the most common opinions from the panel.

[0081] (Example 2) [Preparation of White Sauce for Evaluation] White sauce for evaluation was prepared according to the formulation in Table 15 below.

[0082]

[0083] [Addition to White Sauce] Invention Product 1 and Comparative Product 1B were each added to 100 g of the above-mentioned white sauce for evaluation in an amount of 0.00005% by mass relative to the total amount, sterilized in a retort pouch at 120°C for 20 minutes, boiled for 10 minutes before consumption, and then subjected to a sensory evaluation by four well-trained panelists. The results are shown in Table 16.

[0084]

[0085] As shown in Table 16, the white sauce containing invention product 1 exhibited enhanced flavor in all of the evaluation items compared to the white sauce containing comparative product 1B, and was particularly excellent in enhancing the thickness and richness of the milk fat and improving the balance of flavor. It was found that the addition of an active ingredient provided significant benefits.

[0086] (Example 3) [Preparation of Invention Product 5] For Invention Product 5, a fragrance composition was prepared using "octanal" as the active ingredient, "L-valine" as component A, "(E)-2-octenal" as component B, "pyruvaldehyde" as component D, and water as the solvent. The composition is shown in Table 17.

[0087]

[0088] [Preparation of Comparative Product 5] A fragrance composition consisting of the active ingredient, components A and B, and a solvent, but excluding component D from invention product 5, was prepared and designated "Comparative Product 5." The composition is shown in Table 18.

[0089]

[0090] [Addition to White Sauce] Invention Product 5 and Comparative Product 5 were each added to 100 g of the above-mentioned white sauce for evaluation at a concentration of 0.05% by mass relative to the total amount, sterilized in a retort pouch at 120°C for 20 minutes, boiled for 10 minutes before consumption, and then subjected to a sensory evaluation by four well-trained panelists. The results are shown in Table 19.

[0091]

[0092] As shown in Table 19, the white sauce containing invention product 5 exhibited enhanced results in most of the evaluation items compared to the white sauce containing comparison product 5, and was particularly excellent in improving the balance of flavor. It was found that when the active ingredient is an n-saturated aldehyde, adding a second key ingredient provides a significant effect.

[0093] Example 4 Preparation of Comparative Product 2E A fragrance composition was prepared that did not contain Component C-1 of Invention Product 2, but consisted of the active ingredient, Component A, Component C-2, Component D, and a solvent, and was designated "Comparative Product 2E." The composition is shown in Table 20.

[0094]

[0095] [Preparation of Comparative Product 2F] A fragrance composition consisting of the active ingredient, Component A, Component C-1, Component D, and a solvent was prepared without the component C-2 of Invention Product 2, and designated "Comparative Product 2F." The composition is shown in Table 21.

[0096]

[0097] [Addition to White Sauce] Invention Product 2, Comparative Product 2E, and Comparative Product 2F were each added to 100 g of the above-mentioned white sauce for evaluation at 0.000005% by mass, and the mixture was sterilized in a retort pouch at 120°C for 20 minutes. After boiling for 10 minutes before eating, the mixture was subjected to a sensory evaluation by four well-trained panelists. The results are shown in Table 22.

[0098]

[0099] As shown in Table 22, the white sauce containing invention product 2 was characterized by being stronger in almost all evaluation items compared to the white sauce containing comparison products 2E and 2F, and was particularly excellent in improving the balance of cheese-like richness and thickness, and flavor. It was found that the coexistence of components C-1 and C-2 provided a significant effect.

[0100] (Example 5) [Preparation of Invention Product 6] For Invention Product 6, a fragrance composition was prepared using 2,4-undecadienal as the active ingredient, L-proline and L-methionine as component A, 3-mercapto-2-butanone as component C-1, acetoin as component C-2, and water as the solvent. The composition is shown in Table 23.

[0101]

[0102] [Preparation of Comparative Product 6A] A fragrance composition consisting of the active ingredient, Component A, Component C-1, and a solvent was prepared without the component C-2 in Invention Product 6, and designated "Comparative Product 6A." The composition is shown in Table 24.

[0103]

[0104] [Preparation of Comparative Product 6B] A fragrance composition consisting of the active ingredient, Component A, Component C-2, and a solvent was prepared without the component C-1 of Invention Product 6, and designated "Comparative Product 6B." The composition is shown in Table 25.

[0105]

[0106] [Addition to White Sauce] Invention Product 6, Comparative Product 6A, and Comparative Product 6B were each added to 100 g of the above white sauce for evaluation at 0.05% by mass, and the mixture was sterilized in a retort pouch at 120°C for 20 minutes. The mixture was then boiled for 10 minutes before consumption, and a sensory evaluation was performed by four well-trained panelists. The results are shown in Table 26.

[0107]

[0108] As shown in Table 26, the white sauce containing invention product 6 exhibited enhanced results in all evaluation items compared to the white sauces containing comparative products 6A and 6B, and was particularly excellent in the effects of sustaining flavor and improving flavor balance. It was found that the coexistence of components C-1 and C-2 provided significant effects.

[0109] (Example 6) [Preparation of Invention Product 7] For Invention Product 7, a fragrance composition was prepared using "hexanal" and "heptanal" as the active ingredients, "L-proline" and "L-leucine" as the A component, "2-mercaptosuccinic acid" as the C-1 component, "acetol" and "acetoin" as the C-2 component, "diacetyl" as the D component, and ethanol and water as the solvent. The composition is shown in Table 27.

[0110]

[0111] [Preparation of Comparative Product 7] A fragrance composition consisting of the active ingredient, component A, component D, and solvent was prepared without the components C-1 and C-2 of Invention Product 7, and designated "Comparative Product 7." The composition is shown in Table 28.

[0112]

[0113] [Addition to White Sauce] Invention Product 7 and Comparative Product 7 were each added to 100 g of the above white sauce for evaluation at 0.05% by mass, and the mixture was sterilized in a retort pouch at 120°C for 20 minutes. The mixture was then boiled for 10 minutes before consumption, and a sensory evaluation was performed by 11 well-trained panelists. The results are shown in Table 29.

[0114]

[0115] As shown in Table 29, the white sauce containing invention product 7 exhibited enhanced flavor in all of the evaluation items compared to the white sauce containing comparison product 7, and was particularly excellent in flavor-lasting effects and flavor-balance improving effects. It was found that significant effects were imparted by adding the sub-components C-1 and C-2 together.

[0116] (Example 7) [Preparation of Invention Product 8] For Invention Product 8, a fragrance composition was prepared using 2,4-nonadienal as the active ingredient, L-proline and L-leucine as component A, (Z)-6-dodecen-4-olide as component B, and ethanol and water as solvents. The composition is shown in Table 30.

[0117]

[0118] [Preparation of Comparative Product 8] A fragrance composition consisting of the active ingredient, Component A, and a solvent, but excluding Component B from Invention Product 8, was prepared and designated "Comparative Product 8." The composition is shown in Table 31.

[0119]

[0120] [Addition to White Sauce] Invention Product 8 and Comparative Product 8 were each added to 100 g of the above-mentioned white sauce for evaluation at 0.05% by mass, and the mixture was sterilized in a retort pouch at 120°C for 20 minutes. After boiling for 10 minutes before eating, a sensory evaluation was performed by four well-trained panelists. The results are shown in Table 32.

[0121]

[0122] As shown in Table 32, the white sauce containing invention product 8 exhibited enhanced flavor in all of the evaluation items compared to the white sauce containing comparison product 8, and was particularly excellent in enhancing the natural milk fat feel and flavor. It was found that the addition of component B, a sub-component group, also provided a significant effect.

[0123] (Example 8) [Preparation of Invention Product 9] For Invention Product 9, a fragrance composition was prepared using "pentanal" as the active ingredient, "DL-alanine" and "L-valine" as component A, "1-octen-3-ol" as component B, "pyruvaldehyde" as component D, and ethanol and water as solvents. The composition is shown in Table 33.

[0124]

[0125] [Preparation of Comparative Product 9] A fragrance composition consisting of the active ingredient, components A and D, and a solvent, but excluding component B from Invention Product 9, was prepared and designated "Comparative Product 9." The composition is shown in Table 34.

[0126]

[0127] [Preparation of Beef Stew for Evaluation] Beef stew for evaluation was prepared according to the recipe in Table 35 below.

[0128]

[0129] [Addition to beef stew] Invention product 9 and comparative product 9 were each added to 100 g of the above-mentioned beef stew for evaluation at a concentration of 0.2% by mass relative to the total amount, sterilized in a retort pouch at 120°C for 20 minutes, boiled for 10 minutes before eating, and then subjected to a sensory evaluation by four well-trained panelists. The results are shown in Table 36.

[0130]

[0131] As shown in Table 36, the beef stew to which Invention Product 9 was added exhibited enhanced characteristics in most of the evaluation items compared to the beef stew to which Comparative Product 9 was added, and was particularly excellent in enhancing the cooking aroma of oil and fat and improving the balance of flavor. It was found that the addition of Component B, a sub-component group, also provided significant effects.

[0132] Example 9 Preparation of Invention Product 10 For invention product 10, a fragrance composition was prepared using 2,4-decadienal and hexanal as active ingredients, L-glutamic acid as component A, (E)-2-heptenal, 1-octen-3-ol, and (Z)-6-dodecen-4-olide as component B, pyruvaldehyde as component D, and ethanol and water as solvents. The composition is shown in Table 37.

[0133]

[0134] [Preparation of Comparative Product 10] A fragrance composition consisting of Components A, B, D, and a solvent, but not containing the active ingredient of Invention Product 10, was prepared and designated "Comparative Product 10." The composition is shown in Table 38.

[0135]

[0136] [Preparation of curry for evaluation] Curry for evaluation was prepared according to the recipe in Table 39 below.

[0137]

[0138] [Addition to curry] Invention product 10 and comparative product 10 were each added to 100 g of the above-mentioned evaluation curry at a concentration of 0.1% by mass relative to the total amount, and sterilized in a retort pouch at 120°C for 20 minutes. After sterilization, the mixture was boiled for 10 minutes before eating, and then a sensory evaluation was performed by four well-trained panelists. The results are shown in Table 40.

[0139]

[0140] As shown in Table 40, the curry containing invention product 10 had better results in all respects than the curry containing comparison product 10. In particular, the balance of flavor was dramatically improved. It was found that adding an active ingredient together provided a significant effect.

[0141] (Example 10) [Preparation of Invention Product 11] For Invention Product 11, a fragrance composition was prepared using 2,4-decadienal and 2,4-nonadienal as the active ingredients, L-glutamic acid and L-valine as the A component, 3-mercaptopropionic acid as the C-1 component, acetoin as the C-2 component, and ethanol and water as the solvent. The composition is shown in Table 41.

[0142]

[0143] [Preparation of Comparative Product 11] A fragrance composition consisting of the active ingredient, ingredients C-1 and C-2, and a solvent, but not containing ingredient A in invention product 11, was prepared and designated "Comparative Product 11." The composition is shown in Table 42.

[0144]

[0145] [Addition to frozen yakitori] Invention Product 11 and Comparative Product 11 were each added to approximately 30 g of commercially available microwave-thawable yakitori at 0.1% by mass, and the yakitori were microwaved at 500 W for 1 minute. After that, a sensory evaluation was performed by eight well-trained panelists. The results are shown in Table 43.

[0146]

[0147] As shown in Table 43, the frozen yakitori to which Invention Product 11 was added not only had an enhanced oily cooking aroma and flavor compared to the frozen yakitori to which Comparative Product 11 was added, but also had the characteristic of masking the chicken odor and improving the balance of flavor. It was found that adding the key ingredients together provided a significant effect.

[0148] Example 11 Preparation of Invention Product 12 A fragrance composition was prepared using hexanal and heptanal as active ingredients, L-proline and L-leucine as component A, (E)-2-heptenal, 1-octen-3-ol, and (Z)-6-dodecen-4-olide as component B, diacetyl as component D, and ethanol and water as solvents. The composition is shown in Table 44.

[0149]

[0150] [Preparation of Comparative Product 12] A fragrance composition consisting of Components A, B, D, and a solvent, but not containing the active ingredient of Invention Product 12, was prepared and designated "Comparative Product 12." The composition is shown in Table 45.

[0151]

[0152] [Preparation of Milk-Flavored Lactic Ice Cream for Evaluation] Milk-flavored lactic ice cream for evaluation was prepared according to the recipe in Table 46 below.

[0153]

[0154] [Addition to milk-flavored lacto ice cream] Invention product 12 and comparison product 12 were each added to 100 g of the above-mentioned milk-flavored lacto ice cream for evaluation at a concentration of 0.05% by mass relative to the total amount, and the mixture was heat-sterilized at 85°C for 5 minutes, after which a sensory evaluation was performed by 10 well-trained panelists.

[0155] The definitions for each evaluation item of the milk-flavored lacto ice cream are as follows: (Definition of evaluation items) Cooked oily aroma: A flavor that further accentuates the richness, fat, and milkiness of the oily flavorFlavor enhancing effect: A three-dimensional effect with depth, breadth, and thicknessFlavor sustaining effect: An effect that clings to the mouth for a long timeFlavor balance improving effect: Good cohesion, good balance of flavor in the food and drink as a wholeThe comments column contains an extract of the most common opinions of the panelists. The results are shown in Table 47.

[0156]

[0157] As shown in Table 47, the milk-flavored lacto ice cream containing invention product 12 was superior in enhancing the oily cooking aroma and flavor compared to the milk-flavored lacto ice cream containing comparison product 12. It was found that the effect was enhanced by adding an active ingredient.

[0158] (Example 12) [Preparation of chocolate-flavored lacto ice cream for evaluation] Chocolate-flavored lacto ice cream for evaluation was prepared according to the recipe in Table 48 below.

[0159]

[0160] [Addition to chocolate-flavored lacto ice cream] Invention product 12 and comparative product 12 were each added to 100 g of the chocolate-flavored lacto ice cream for evaluation in an amount of 0.05% by mass relative to the total amount, and the mixture was sterilized by heating at 85°C for 5 minutes. After that, a sensory evaluation was carried out in the same manner as for the milk-flavored lacto ice cream by 10 well-trained panelists. The results are shown in Table 49.

[0161]

[0162] As shown in Table 49, the results showed that the chocolate-flavored lacto ice cream to which invention product 12 was added had a dramatically enhanced oil and fat cooking aroma compared to the chocolate-flavored lacto ice cream to which comparison product 12 was added. It was found that the addition of an active ingredient in combination provided a significant effect.

[0163] (Example 13) [Preparation of Invention Product 13] For Invention Product 13, a fragrance composition was prepared using 2,4-decadienal and pentanal as the active ingredients, L-leucine, L-phenylalanine, and L-glutamine as component A, (E)-2-nonenal as component B, diacetyl, acetylpropionyl, and acetylbenzoyl as component D, and ethanol and water as the solvent. The composition is shown in Table 50.

[0164]

[0165] [Preparation of Comparative Product 13] A fragrance composition consisting of the active ingredient, components A and D, and a solvent, but excluding component B in Invention Product 11, was prepared and designated "Comparative Product 13." The composition is shown in Table 51.

[0166]

[0167] [Preparation of butter cookies for evaluation] Baked confectioneries for evaluation were prepared according to the recipes in Table 52 below.

[0168]

[0169] [Addition to Butter Cookies] Invention Product 13 and Comparative Product 13 were each added to 100 g of the above-mentioned butter cookies for evaluation in an amount of 0.15% by mass relative to the total amount, and the cookies were baked at 180°C for 10 minutes, after which a sensory evaluation was performed by eight well-trained panelists. The results are shown in Table 53.

[0170]

[0171] As shown in Table 53, the butter cookies containing invention product 13 exhibited an enhanced oily texture without compromising the balance compared to the butter cookies containing comparison product 13. It was found that the addition of the sub-components simultaneously provided a significant effect.

[0172] Example 14 Preparation of Invention Product 14 A fragrance composition was prepared using nonanal as the active ingredient, L-lysine hydrochloride and L-histidine as component A, 3-mercapto-2-butanone as component C-1, dihydroxyacetone as component C-2, pyruvaldehyde and acetylvaleryl as component D, and ethanol and water as solvents. The composition is shown in Table 54.

[0173]

[0174] [Preparation of Comparative Product 14] A fragrance composition consisting of the active ingredient, Component A, Component C-1, Component C-2, and a solvent, but excluding Component D from Invention Product 14, was prepared and designated "Comparative Product 14." The composition is shown in Table 55.

[0175]

[0176] [Addition to frozen gyoza] Inventive product 14 and comparative product 14 were each added to approximately 30 g of commercially available frozen gyoza for thawing in a microwave oven at 0.05% by mass, and the gyoza were microwaved at 500 W for 1 minute. After that, a sensory evaluation was carried out by eight well-trained panelists. The results are shown in Table 56.

[0177]

[0178] As shown in Table 56, the frozen dumplings containing invention product 14 showed greater effects in all categories than the frozen dumplings containing comparison product 14, and were characterized by an increased juiciness due to the oily texture. It was found that the addition of the second key ingredient group also provided a significant effect.

[0179] The above results demonstrate that the flavor composition of the present invention can impart or enhance the aroma of cooking oils and fats to a wide range of foods.

Claims

1. An agent for imparting or enhancing cooking aroma to fats and oils, comprising as active ingredients 2,4-dienal represented by the following general formula (1) and / or one or more n-saturated aldehydes represented by the following general formula (2): as key components (component A) one or more of α-amino acids represented by the following general formula (3), proline, lysine hydrochloride, cystine, and glutathione; and as sub-components component B consisting of one or more of unsaturated aldehydes represented by the following general formula (4), 1-octen-3-ol, and (Z)-6-dodecen-4-olide, and / or component C consisting of one or more of sulfur compounds represented by the following general formula (5) and 3-mercaptopropionic acid (component C-1), and one or more hydroxyketones represented by the following general formula (6) (component C-2). However, when the active ingredient is the n-saturated aldehyde, the composition contains, as the second key ingredient (ingredient D), one or more dicarbonyl compounds represented by the following general formula (7). (In the formula, R １ represents a linear saturated alkyl group having 4 or more carbon atoms. (In the formula, R ２ represents a linear saturated alkyl group having 4 or more carbon atoms. (In the formula, R ３ indicates an amino acid side chain.) (In the formula, R ４ represents a linear saturated alkyl group having 3 to 6 carbon atoms.) (In the formula, R ５ and R ６ each independently represents any one of an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, a hydroxyl group, and a hydrogen atom. (In the formula, R ７ and R ８ each independently represents any one of an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, a hydroxyl group, and a hydrogen atom. (In the formula, R ９ and R １０ each independently represents any one of an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, a hydroxyl group, and a hydrogen atom.

2. The agent for imparting or enhancing cooking aroma to fats and oils according to claim 1, wherein the active ingredient, the key ingredient, and the sub-ingredient, or further the second key ingredient, when heated, produce at least one component belonging to Group I consisting of long-chain alkylpyridines and long-chain alkylpyrazines, and at least one component belonging to Group II consisting of pyrazines, pyrroles, thiazoles, thiophenes, furans, and pyridines.

3. The agent for imparting or enhancing cooking aroma to fats and oils according to claim 1, wherein the 2,4-dienal represented by general formula (1) is one or more selected from the group consisting of 2,4-nonadienal, 2,4-decadienal, and 2,4-undecadienal.

4. The agent for imparting or enhancing cooking aroma to fats and oils according to claim 1, wherein the n-saturated aldehyde represented by general formula (2) is one or more selected from the group consisting of pentanal, hexanal, heptanal, octanal, and nonanal.

5. The agent for imparting or enhancing cooking aroma to fats and oils according to claim 1, wherein the α-amino acid represented by the general formula (3) is one or more selected from the group consisting of glycine, alanine, leucine, valine, phenylalanine, glutamine, glutamic acid, methionine, and histidine.

6. The agent for imparting or enhancing cooking aroma to fats and oils according to claim 1, wherein the unsaturated aldehyde represented by general formula (4) is one or more selected from the group consisting of (E)-2-hexenal, (E)-2-heptenal, (E)-2-octenal, and (E)-2-nonenal.

7. The agent for imparting or enhancing cooking aroma to fats and oils according to claim 1, wherein the sulfur compound represented by general formula (5) is one or more compounds selected from the group consisting of 2-mercaptosuccinic acid, 2-mercaptopropionic acid, and 3-mercapto-2-butanone.

8. An agent for imparting or enhancing cooking aroma to fats and oils according to claim 1, wherein the hydroxyketone represented by general formula (6) is one or more selected from the group consisting of acetoin, acetol, and dihydroxyacetone.

9. The agent for imparting or enhancing cooking aroma to fats and oils according to claim 1, wherein the dicarbonyl compound represented by general formula (7) is one or more selected from the group consisting of glyoxal, pyruvaldehyde, pyruvic acid, diacetyl, acetylpropionyl, acetylbutyryl, acetylvaleryl, and acetylbenzoyl.

10. The cooking aroma imparting or enhancing agent for oils and fats according to any one of claims 1 to 9, further comprising one or more selected from the group consisting of synthetic flavors, natural flavors, spice extracts, and solvents.

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