Patent Docment: Method for Producing a Flavor Composition (for Beef, Pork, and Chicken)

Here is the English translation of the Japanese patent document (JP5495366B2).

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(19) Japan Patent Office (JP) (12) Patent Publication (B2) (11) Patent Number

Patent No. 5495366
(45) Date of Issuance: May 21, 2014 (2014.5.21) (24) Date of Registration: March 14, 2014 (2014.3.14)

(51) Int. Cl. F I

A23L 1/22 (2006.01) A23L 1/22 C
A23L 1/226 (2006.01) A23L 1/22 A
A23L 1/318 (2006.01) A23L 1/22 D
A23L 1/226 G
A23L 1/318

Number of Claims: 6 (Total 23 pages)

(54) Title of Invention: METHOD FOR PRODUCING A FLAVOR COMPOSITION

(57) [Claims]

[Claim 1]
A flavor composition for use in cooking beef, pork, or chicken, said composition obtained by heating a formulation comprising amino acids, wherein the molar ratio of sodium L-aspartate to L-glutamic acid or its sodium salt is from 1.0:0.25 to 0.25:0.75, and the molar ratio of said amino acids to sugar is from 1.0:1.5 to 1.0:0.19, in the presence of beef tallow for beef, lard for pork, or palm oil for chicken, wherein said composition imparts a roasted flavor and richness (kokumi) to meats via aromatic components containing pyrazines and furans.

[Claim 2]
The flavor composition according to Claim 1, characterized in that the L-glutamic acid or its sodium salt is L-glutamic acid.

[Claim 3]
A powdered seasoning, liquid seasoning, or paste-like seasoning characterized by having a roasted and rich (kokumi) taste, obtained by adding the flavor composition according to Claim 1 or 2 to a seasoning.

[Claim 4]
A method for producing flavored meat, characterized by heating a formulation comprising amino acids, wherein the molar ratio of sodium L-aspartate to L-glutamic acid or its sodium salt is from 1.0:0.25 to 0.25:0.75, and the molar ratio of said amino acids to sugar is from 1.0:1.5 to 1.0:0.19, in the presence of beef and beef tallow, pork and lard, or chicken and palm oil, thereby imparting a roasted flavor and richness (kokumi) via aromatic components containing pyrazines and furans to the meat which is beef, pork, or chicken.

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[Claim 5]
A kit for producing a flavor composition for use in cooking beef, pork, or chicken, said kit comprising amino acids, wherein the molar ratio of sodium L-aspartate to L-glutamic acid or its sodium salt is from 1.0:0.25 to 0.25:0.75, and sugar, wherein the molar ratio of said amino acids to sugar is from 1.0:1.5 to 1.0:0.19, and further comprising beef tallow for beef, lard for pork, or palm oil for chicken, said kit for imparting a roasted flavor and richness (kokumi) to meats via aromatic components containing pyrazines and furans.

[Claim 6]
The kit according to Claim 5, characterized in that the amino acids and sugar are included in a mixed state.

Detailed Description of the Invention

[Technical Field]
[0001]
The present invention relates to a method for producing a flavor composition, and more specifically, to a flavor composition containing aromatic components such as pyrazines obtained by heating a specific mixture of amino acids and sugar, and a method for producing the same.

[Background Art]
[0002]
In the field of food manufacturing, aroma and taste are important factors. For improving flavor, for example, the Maillard reaction (also called the aminocarbonyl reaction) is sometimes utilized. The Maillard reaction is a reaction that starts with the reaction between an amino group and a carbonyl group, producing a compound with a carbon-nitrogen double bond called a Schiff base. Subsequently, if hydroxyl groups of sugars are nearby, it undergoes an Amadori rearrangement and then various reactions such as dehydration, generating a diverse array of products. Heating food generates aromas completely different from its raw state. This occurs because components in the food are broken down into low-molecular-weight compounds upon heating, and a chain of reactions produces aromas. This is an aminocarbonyl reaction between amino acids and reducing sugars upon heating, playing a crucial role in generating aromas in food. This aminocarbonyl reaction varies greatly depending on the types of reducing sugars (carbohydrates) and amino acids (proteins) used, as well as reaction temperature, time, moisture content, pH, etc., resulting in significantly different aromas. Meanwhile, many aromatic components have been isolated from the heated reaction products of reducing sugars and amino acids, and their chemical structures have been elucidated. For example, many are known, including furans, furanones, pyranones, aldehydes, pyrroles, pyrazines, thiazoles, thiophenes, thiols, sulfides, and others.

[0003]
Techniques for improving aroma and flavor include roasted oils containing abundant aroma and flavor, obtained by heating amino acids and monosaccharides, or amino acids and oligosaccharides or oligopeptides and monosaccharides, with vegetable or animal fats and oils, optionally adding dried vegetable powder (see, e.g., Patent Document 1); methods for producing a seasoning liquid by adding glutathione and/or cysteine within a soluble range to a seasoning liquid containing sugar, amino acids, and also soy sauce and/or broth, and heating at 60-120°C for 5-300 minutes (see, e.g., Patent Document 2); flavor-active compounds obtainable by subjecting a peptide selected from the group consisting of Tyr-Val, Val-Tyr, Leu-Leu, Pro-Val, Val-Phe, and Lys-Glu to a Maillard reaction with a reducing sugar (see, e.g., Patent Document 3); and methods for improving the flavor of foods and drinks by adding an aminocarbonyl reaction product of a peptide with a molecular weight of 1000-5000 and a carbonyl compound to the food or drink (see, e.g., Patent Document 4).

[0004]
Regarding taste, there are the five basic tastes (sweetness, saltiness, sourness, bitterness, and umami), and additionally, there is richness (kokumi), which cannot be expressed by the five basic tastes. Richness (kokumi) is said to be not a basic taste itself but a taste that enhances aspects like thickness, breadth, continuity, and unity, which surround the basic tastes. Known techniques and improvement methods for primarily imparting or enhancing richness (kokumi) in seasonings include: methods for producing foods with enhanced richness (kokumi) by combining sodium glutamate with glutathione (see, e.g., Patent Document 5); richness (kokumi) seasoning materials containing gelatin, tropomyosin, and sugars and/or amino acids (see, e.g., Patent Document 6); richness (kokumi) imparting agents using imidazole dipeptides, sulfonic group-containing compounds, organic acids, etc. (see, e.g., Patent Document 7); seasonings containing pyrazine compounds, capable of imparting richness (kokumi) in particular (see, e.g., Patent Document 8); peptides consisting of specific amino acid sequences, having a taste-improving, particularly richness (kokumi)-enhancing, effect (see, e.g., Patent Document 9); methods for imparting richness (kokumi) to foods or seasonings by adding a specific amount of a glycopeptide with a specific structural formula to the food (see, e.g., Patent Document 10); and methods for imparting richness (kokumi) to foods and drinks by adding specific amounts of glutamic acid and/or its salt, and aspartic acid and/or its salt, having a specific molar ratio, to the food or drink (see, e.g., Patent Document 11).

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(3) JP 5495366 B2 2014.5.21

[0005]
Furthermore, known methods for producing or accelerating roasted flavors, chicken flavors, etc., similar to those generated when heating meats, and techniques for improving these flavors include: methods for producing chicken flavor by heating a β-alanine derivative and an amino acid in a solvent (see, e.g., Patent Document 12); mixtures of precursors for flavor-imparting agents that generate aromatic notes through the formation of thiols during roasting or grilling of foods such as meat (see, e.g., Patent Document 13); methods for producing cooked flavors comprising the steps of: (1) physically and/or enzymatically (using proteolytic enzymes) pulverizing meat of animals, birds, and/or seafood to an average particle size of 10 μm to 2000 μm; (2) heating the pulverized meat at 100°C to 180°C; (3) cooling the heat-treated product, then adding one or a mixture of two or more selected from amino acids, saccharides, animal/plant extracts, yeast extracts, and hydrolyzed animal/plant proteins, and heating again at 100°C to 180°C (see, e.g., Patent Document 14); and methods for producing a composition with chicken flavor comprising steps of: (a) preparing a mixture containing at least one reducing carbohydrate and at least one amino acid; (b) maintaining the mixture at a temperature sufficient for the reducing carbohydrate and amino acid to react with each other; (c) adding to the mixture a composition comprising arachidonic acid, wherein said arachidonic acid is esterified to the glycerol component of triglycerides at least 50% (w/w), preferably at least 65% (w/w), more preferably at least 80% (w/w), and most preferably at least 90% (w/w); and (d) maintaining the mixture at a temperature sufficient to develop a chicken flavor (see, e.g., Patent Document 15).

[0006]
However, a method for producing a flavor composition containing aromatic components such as pyrazines by heating specific amino acids including sodium L-aspartate with sugar is not known.

[Prior Art Documents]
[Patent Documents]
[0007]
[Patent Document 1] JP S60-30663 A
[Patent Document 2] JP Patent No. 3458514 B2
[Patent Document 3] JP Patent No. 4288164 B2
[Patent Document 4] JP Patent No. 3623753 B2
[Patent Document 5] JP S63-13661 B2
[Patent Document 6] JP H10-276709 A
[Patent Document 7] JP H8-289760 A
[Patent Document 8] JP H11-313635 A
[Patent Document 9] JP 2002-255994 A
[Patent Document 10] WO 2004-096836 A (Republication)
[Patent Document 11] WO 2006-062181 A (Republication)
[Patent Document 12] JP H11-215967 A

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[Patent Document 13] JP 2002-503763 A (National Publication of Translated Version)
[Patent Document 14] JP H11-25822 A
[Patent Document 15] JP 2004-532906 A (National Publication of Translated Version)

Summary of the Invention
Problem to be Solved by the Invention
[0008]
The problem to be solved by the present invention is to provide a flavor composition for use in cooking beef, pork, or chicken. Specifically, the invention aims to provide a flavor composition that, depending on the type of meat being cooked, uses fats and oils obtained from that meat to heat-react specific amino acids and sugar, thereby imparting a roasted flavor and richness (kokumi) to the meat via aromatic components containing pyrazines and furans.

Means for Solving the Problem
[0009]
As a result of intensive research to solve the above problem, the present inventors discovered that a flavor composition capable of imparting a roasted flavor and richness (kokumi) to meats via aromatic components containing pyrazines and furans can be obtained by heating a formulation in the presence of beef tallow for beef, lard for pork, or palm oil for chicken. The formulation comprises amino acids, where the molar ratio of sodium L-aspartate to L-glutamic acid or its sodium salt is from 1.0:0.25 to 0.25:0.75, and the molar ratio of said amino acids to sugar is from 1.0:1.5 to 1.0:0.19. This discovery led to the completion of the present invention.

[0010]
That is, the present invention relates to:
(1) A flavor composition for use in cooking beef, pork, or chicken, said composition obtained by heating a formulation comprising amino acids, wherein the molar ratio of sodium L-aspartate to L-glutamic acid or its sodium salt is from 1.0:0.25 to 0.25:0.75, and the molar ratio of said amino acids to sugar is from 1.0:1.5 to 1.0:0.19, in the presence of beef tallow for beef, lard for pork, or palm oil for chicken, wherein said composition imparts a roasted flavor and richness (kokumi) to meats via aromatic components containing pyrazines and furans.
(2) The flavor composition according to (1) above, characterized in that the L-glutamic acid or its sodium salt is L-glutamic acid.
(3) A powdered seasoning, liquid seasoning, or paste-like seasoning characterized by having a roasted and rich (kokumi) taste, obtained by adding the flavor composition according to (1) or (2) above to a seasoning.
(4) A method for producing flavored meat, characterized by heating a formulation comprising amino acids, wherein the molar ratio of sodium L-aspartate to L-glutamic acid or its sodium salt is from 1.0:0.25 to 0.25:0.75, and the molar ratio of said amino acids to sugar is from 1.0:1.5 to 1.0:0.19, in the presence of beef and beef tallow, pork and lard, or chicken and palm oil, thereby imparting a roasted flavor and richness (kokumi) via aromatic components containing pyrazines and furans to the meat which is beef, pork, or chicken.
(5) A kit for producing a flavor composition for use in cooking beef, pork, or chicken, said kit comprising amino acids, wherein the molar ratio of sodium L-aspartate to L-glutamic acid or its sodium salt is from 1.0:0.25 to 0.25:0.75, and sugar, wherein the molar ratio of said amino acids to sugar is from 1.0:1.5 to 1.0:0.19, and further comprising beef tallow for beef, lard for pork, or palm oil for chicken, said kit for imparting a roasted flavor and richness (kokumi) to meats via aromatic components containing pyrazines and furans.
(6) The kit according to (5) above, characterized in that the amino acids and sugar are included in a mixed state.

Effects of the Invention
[0011]
According to the present invention, it is possible to provide a flavor composition for use in cooking beef, pork, or chicken. By using fats and oils obtained from the specific type of meat being cooked to heat-react specific amino acids and sugar, the composition can effectively impart a roasted flavor and richness (kokumi) to the meat via aromatic components containing pyrazines and furans.

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Brief Description of the Drawings
[0012]
[Fig. 1] Figure 1 shows gas chromatograms of the flavor compositions obtained in Example 1 and Comparative Examples 1 to 3.
[Fig. 2] Figure 2 is an enlarged view of the gas chromatogram of the aromatic components of the flavor composition obtained in Example 1.

Mode for Carrying Out the Invention
[0013]
The flavor composition of the present invention is obtained by heating a formulation in the presence of beef tallow for beef, lard for pork, or palm oil for chicken. The formulation comprises amino acids, wherein the molar ratio of sodium L-aspartate to L-glutamic acid or its sodium salt is from 1.0:0.25 to 0.25:0.75, and the molar ratio of said amino acids to sugar is from 1.0:1.5 to 1.0:0.19.
[0014]
The amino acids used in the present invention include sodium L-aspartate and L-glutamic acid or its sodium salt. The molar ratio of these is sodium L-aspartate : L-glutamic acid or its sodium salt = 1.0 : 0.25 to 0.25 : 0.75, preferably 1.0 : 0.33 to 0.3 : 0.67, and more preferably 1.0 : 0.4 to 0.4 : 0.6. When the molar ratio of the amino acids is within the above range, the effects of the present invention, namely imparting a roasted flavor and richness (kokumi), can be effectively achieved. Furthermore, the molar ratio of amino acids to sugar is 1.0 : 1.5 to 1.0 : 0.19, preferably 1.0 : 1.2 to 1.0 : 0.23, and more preferably 1.0 : 1.0 to 1.0 : 0.25. When the molar ratio of amino acids to sugar is within the above range, the effects of the present invention can be effectively exhibited.
[0015]
The sugar used in the present invention is not particularly limited and includes, for example, sucrose, lactose, maltose, and the like; any sugar can be used. Among these, sucrose is preferred. The amount of sugar used is appropriately selected depending on the intended use of the target flavor composition, but for example, the molar ratio relative to the total amount of amino acids is 1.0 : 1.5 to 1.0 : 0.19.
[0016]
The heating reaction of the present invention is carried out in the presence of beef tallow for beef, lard for pork, or palm oil for chicken. This makes it possible to obtain a flavor composition tailored to the type of meat being cooked. The amount of fat or oil used is not particularly limited, but it is, for example, 0.1 to 50% by mass, preferably 0.5 to 30% by mass, and more preferably 1 to 20% by mass, relative to the total amount of amino acids and sugar.
[0017]
In the heating reaction of the present invention, preferably, the amino acids and sugar are mixed, then the fat or oil is added and the mixture is heated, or the amino acids and sugar are mixed and heated in the presence of the fat or oil. The heating temperature is preferably 100 to 180°C, more preferably 120 to 160°C. The heating time is preferably 1 to 180 minutes, more preferably 5 to 120 minutes. The heating reaction can be carried out under normal pressure or under pressure.
[0018]
The flavor composition of the present invention contains aromatic components including pyrazines and furans. Examples of pyrazines include methylpyrazine, 2,5-dimethylpyrazine, 2,6-dimethylpyrazine, ethylpyrazine, 2-ethyl-6-methylpyrazine, 2-ethyl-5-methylpyrazine, trimethylpyrazine, 2-ethyl-3-methylpyrazine, tetramethylpyrazine, 2-ethyl-3,5-dimethylpyrazine, and the like. Examples of furans include furfuryl alcohol, 2-furaldehyde (furfural), 2-acetylfuran, 5-methyl-2-furaldehyde (5-methylfurfural), and the like. By containing the above aromatic components, the flavor composition of the present invention can impart a roasted flavor and richness (kokumi) to meats. In the present invention, "richness (kokumi)" refers to a taste that imparts or enhances thickness, breadth, continuity, unity, and the like.
[0019]
The flavor composition of the present invention can be used as is in seasonings, etc. Furthermore, if necessary, it can be processed into a powdered form, for example, by adding excipients such as dextrin, and then drying using methods such as spray drying or freeze drying. The form of the flavor composition is not particularly limited and can be, for example, a paste, liquid, or powder.
[0020]
The flavor composition of the present invention can be added to various seasonings. Examples of seasonings include concentrated seasonings, mixed seasonings, seasoning powders, sauce seasonings, seasoning bases, and the like. By adding the flavor composition of the present invention, it is possible to produce seasonings with an excellent roasted flavor and richness (kokumi). Furthermore, by using the flavor composition of the present invention in combination with meats and fats/oils, it is possible to produce cooked meat products with an excellent roasted flavor and richness (kokumi). For example, when producing cooked meat products such as roast beef, roasted pork, or roasted chicken, by adding the flavor composition of the present invention, a more flavorful product can be obtained.
[0021]
The present invention also provides a kit for easily producing the above-mentioned flavor composition. The kit comprises specific amino acids and sugar, and further comprises specific fats or oils depending on the target meat type (beef tallow for beef, lard for pork, or palm oil for chicken). The amino acids and sugar may be included in the kit separately or in a pre-mixed state. The kit may also include instructions for use explaining, for example, the mixing ratios and heating conditions.

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Examples
[0022]
Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples.
[0023]
Example 1
17.3 g (0.1 mol) of sodium L-aspartate (manufactured by Ajinomoto Co., Inc.) and 14.7 g (0.1 mol) of L-glutamic acid (manufactured by Ajinomoto Co., Inc.) (molar ratio 1.0:1.0) were mixed with 34.2 g (0.1 mol) of sucrose (manufactured by Wako Pure Chemical Industries, Ltd.) (amino acids:sucrose molar ratio 1.0:0.5). To this mixture, 10 g of beef tallow (manufactured by Prima Meat Packers, Ltd.) was added and heated at 140°C for 30 minutes with stirring, followed by cooling to obtain a paste-like flavor composition. The obtained flavor composition had a strong roasted beef-like flavor.
[0024]
Comparative Example 1
A flavor composition was obtained in the same manner as in Example 1, except that L-glutamic acid was not used and only 17.3 g (0.1 mol) of sodium L-aspartate was used as the amino acid. The obtained flavor composition had a weak roasted flavor.
[0025]
Comparative Example 2
A flavor composition was obtained in the same manner as in Example 1, except that sodium L-aspartate was not used and only 14.7 g (0.1 mol) of L-glutamic acid was used as the amino acid. The obtained flavor composition had a weak roasted flavor.
[0026]
Comparative Example 3
A flavor composition was obtained in the same manner as in Example 1, except that beef tallow was not added. The obtained flavor composition had a weak roasted flavor and lacked richness (kokumi).
[0027]
Analysis of Aromatic Components
The flavor compositions obtained in Example 1 and Comparative Examples 1 to 3 were analyzed for their aromatic components under the following conditions. The gas chromatograms obtained are shown in Figure 1. Figure 2 shows an enlarged view of the gas chromatogram for Example 1. The peaks identified as pyrazines and furans based on retention times of standards are indicated in Figure 2.

• Sample Preparation: 1 g of the flavor composition was extracted with 10 mL of diethyl ether. The extract was concentrated under a nitrogen stream and used as the analysis sample.
• GC Conditions:
  • Device: Agilent 6890N (Agilent Technologies)
  • Column: DB-WAX (60 m x 0.25 mm I.D., 0.25 μm film thickness, J&W Scientific)
  • Carrier Gas: Helium (1.0 mL/min, constant flow)
  • Injection Port Temperature: 250°C
  • Detector (FID) Temperature: 250°C
  • Oven Temperature: Held at 40°C for 5 minutes, increased to 240°C at a rate of 5°C/min, then held for 10 minutes.

[0028]
As is clear from Figure 1, many more peaks for aromatic components were detected in the flavor composition of Example 1 compared to those of Comparative Examples 1 to 3. Particularly, as shown in Figure 2, the peaks for pyrazines (e.g., methylpyrazine, 2,5-dimethylpyrazine, trimethylpyrazine) and furans (e.g., furfural, 5-methylfurfural, furfuryl alcohol) were prominent. This demonstrates that by using a specific combination of amino acids and heating in the presence of fat or oil, a flavor composition rich in aromatic components such as pyrazines and furans, which contribute to a roasted flavor, can be obtained.
[0029]
Sensory Evaluation
Seasoning liquids were prepared by adding 1% by mass of each of the flavor compositions obtained in Example 1 and Comparative Examples 1 to 3 to a 1% aqueous sodium chloride solution. These seasoning liquids were subjected to a sensory evaluation by a panel of 10 trained experts. The evaluation items were "roasted flavor (aroma)" and "richness (kokumi, taste)". Each item was evaluated on a 5-point scale (1: Very weak, 2: Weak, 3: Moderate, 4: Strong, 5: Very strong), and the average score was calculated. The results are shown in Table 1.
[0030]

[0031]
From the results in Table 1, it is clear that the flavor composition of Example 1 was evaluated as having a strong roasted flavor and richness (kokumi) compared to the compositions of Comparative Examples 1 to 3. In Comparative Example 1, where only sodium L-aspartate was used as the amino acid, both roasted flavor and richness were weak. In Comparative Example 2, where only L-glutamic acid was used, the effects were also insufficient. In Comparative Example 3, where heating was performed without fat or oil, the roasted flavor was weaker than in Example 1, and richness was particularly low. These results confirm that by using a specific mixture of amino acids and heating in the presence of a specific fat or oil, a flavor composition capable of effectively imparting a roasted flavor and richness (kokumi) can be obtained.

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Example 2
18.2 g (0.105 mol) of sodium L-aspartate and 7.0 g (0.0475 mol) of L-glutamic acid (molar ratio 1.0:0.45) were mixed with 45.9 g (0.134 mol) of sucrose (amino acids:sucrose molar ratio 1.0:0.88). To this mixture, 15 g of lard (manufactured by Prima Meat Packers, Ltd.) was added and heated at 150°C for 20 minutes with stirring, followed by cooling to obtain a paste-like flavor composition. The obtained flavor composition had a strong roasted pork-like flavor.
[0032]
Example 3
9.0 g (0.052 mol) of sodium L-aspartate and 11.5 g (0.078 mol) of L-glutamic acid (molar ratio 1.0:1.5) were mixed with 20.0 g (0.058 mol) of sucrose (amino acids:sucrose molar ratio 1.0:0.45). To this mixture, 8 g of palm oil (manufactured by Fuji Oil Co., Ltd.) was added and heated at 130°C for 60 minutes with stirring, followed by cooling to obtain a paste-like flavor composition. The obtained flavor composition had a strong roasted chicken-like flavor.
[0033]
Example 4 (Production of Seasoning)
0.5 parts by mass of the flavor composition obtained in Example 1 was added to 100 parts by mass of a commercially available concentrated Worcestershire sauce (manufactured by Company A) and mixed uniformly to obtain a seasoned sauce. This seasoned sauce had an enhanced roasted flavor and richness (kokumi) compared to the sauce before addition, resulting in a deep and rich flavor profile.
[0034]
Example 5 (Production of Cooked Meat Product)
0.2 parts by mass of the flavor composition obtained in Example 2, 2.0 parts by mass of salt, and 1.0 part by mass of sugar were mixed. This mixture was rubbed onto 100 parts by mass of pork loin, allowed to stand overnight, then roasted in an oven at 180°C. The obtained roasted pork had a strong roasted flavor and richness (kokumi), and was very delicious.
[0035]
Comparative Example 4
Roasted pork was prepared in the same manner as in Example 5, except that the flavor composition of Example 2 was not added. The obtained roasted pork had a weaker roasted flavor and lacked richness (kokumi) compared to the product of Example 5.

Industrial Applicability
[0036]
The flavor composition of the present invention can effectively impart a roasted flavor and richness (kokumi) to meats. Therefore, it is useful in the food industry, particularly in the field of processed meat products and seasonings.

Explanation of Reference Numerals
[0037]
None.

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