Taste-enhancing composition, method for producing same, food product, and method for enhancing taste of food product

Abstract

The present invention provides a taste-enhancing composition capable of enhancing a taste of a food product when mixed into the food product, and a method for producing the taste-enhancing composition, and a food product having an enhanced taste and a method for enhancing a taste of a food product. A first embodiment pertains to a taste-enhancing composition comprising a cyclic dipeptide. A second embodiment pertains to a method that is for producing the taste-enhancing composition and that comprises increasing the cyclic dipeptide in a spice such as coriander by heating the spice. A third embodiment pertains to a food product comprising the taste-enhancing composition. A fourth embodiment pertains to a method that is for enhancing a taste of a food product, and that comprises mixing the taste-enhancing composition into the food product.

Description

Flavor enhancing composition, method for producing the same, food, and method for enhancing the flavor of food

[0001] The present invention relates to a composition for enhancing flavor, a method for producing the same, a food, and a method for enhancing the flavor of a food.

[0002] Salt (sodium chloride) is used in foods to impart a pleasant taste and as a source of chlorine and sodium, elements essential for maintaining life. However, excessive salt intake is known to cause many diseases, including hypertension, and therefore reducing salt intake is desirable.

[0003] Patent Document 1 discloses a spice mix for enhancing saltiness, which contains paprika, yuzu peel and / or dried mandarin orange peel, ginger, and allspice in a predetermined ratio, and may further contain at least one spice selected from red chili pepper, cumin, coriander, and celery seed. Patent Document 1 describes that the saltiness enhancing effect can be further enhanced by including smoked spices in the spice mix for enhancing saltiness. Smoked paprika is described as a specific example of a smoked spice. According to Patent Document 1, the spice mix for enhancing saltiness, when added to food together with salt, has the effect of enhancing the saltiness of the food.

[0004] Patent Document 2 discloses a salty taste enhancer containing a mixture of pepper, ginger, cloves and cinnamon, and a salty taste enhancer containing a mixture of pepper, ginger, cloves, cinnamon and capsicum.

[0005] Patent Document 3 discloses a method for producing a spice with enhanced caramel aroma, which includes a step of heating at least one spice selected from the group consisting of coriander, cumin, dried orange peel, anise, celery, turmeric, fenugreek, garlic, chili pepper, paprika, fennel, black pepper, ginger, and asafoetida under a gauge pressure of 0.05 MPa or more under conditions such that the heating value becomes 15 to 170; and a method for producing a spice with enhanced almond aroma, which includes a step of heating at least one spice selected from the group consisting of turmeric, chili pepper, fenugreek, cumin, coriander, dried orange peel, garlic, paprika, fennel, anise, celery, black pepper, ginger, fenugreek leaves, and cinnamon under conditions such that the heating value becomes 50 to 180 under a gauge pressure of less than 0.05 MPa. Patent Document 3 further discloses that a spice with enhanced charcoal aroma can be obtained by heating coriander under conditions that result in a heating value of 800 or higher.

[0006] JP 2018-102142 A JP 2012-239398 A JP 2020-103257 A

[0007] The present invention provides a taste enhancing composition that can enhance the taste of food by adding it to the food, and a method for producing the same. The present invention also provides a method for enhancing the taste of food.

[0008] The present inventors have discovered the following means as a taste enhancing composition that can enhance the taste of food, a method for producing a taste enhancing composition, a food with enhanced taste, and a method for enhancing the taste of food.

[0009] [1] A taste enhancing composition containing a cyclic dipeptide. The taste enhancing composition may be, for example, a salty taste enhancing composition.

[0010] [2] The taste enhancing composition according to [1], wherein the cyclic dipeptide contains one or more selected from the group consisting of proline, leucine, isoleucine, glycine, phenylalanine, glutamic acid, tyrosine, valine, aspartic acid, histidine, and alanine.

[0011] [3] The cyclic dipeptide is cyclic (Pro-Asn), cyclic (Pro-His), cyclic (Pro-Asp), cyclic (Pro-Pro), cyclic (Pro-Val), cyclic (Pro-Tyr), cyclic (Pro-Leu), cyclic (Pro-Ile), cyclic (Pro-Glu), cyclic (Pro-Gly), cyclic (Pro-Met), cyclic (Arg-Pro), cyclic (Thr-Pro), cyclic (hyPro-Pro), cyclic (Leu-Leu), cyclic (Ile-Leu), cyclic (Ile-Ile), cyclic (Leu-Asp), cyclic (Ile-Asp), cyclic (Leu-Ser), cyclic (Ile-Ser), cyclic (Leu-Val), cyclic (Ile-Val), cyclic (Leu-His), cyclic (Ile-His), cyclic (Leu-Met), cyclic (Ile-Met), cyclic (Arg-Leu), cyclic (Arg-Ile), cyclic (hyPro-Leu), cyclic (hyPro-Ile), cyclic (Thr-Leu), cyclic (Thr-Ile), cyclic (Gly-His), cyclic (Gly-Ser), cyclic (Gly-Arg), cyclic (Gly-Val), cyclic (Gly-Leu), cyclic (Gly-Ile), cyclic (Gl cyclic (Gly-Phe), cyclic (Gly-Tyr), cyclic (Gly-Thr), cyclic (Gly-Gly), cyclic (Gly-Ala), cyclic (Phe-Leu), cyclic (Phe-Ile), cyclic (Phe-Ser), cyclic (Phe-Ala), cyclic (Phe-Asp), cyclic (Phe-Thr), cyclic (Phe-Pro), cyclic (Phe-Tyr), cyclic (Phe-Phe), cyclic (Glu-His), cyclic (Glu-Glu), cyclic (Glu-Arg), cyclic (Glu-Gly), cyclic (Glu-Asp), cyclic (Glu-Tyr), cyclic (Glu-Phe), one or more selected from the group consisting of cyclic (Glu-Leu), cyclic (Glu-Ile), cyclic (Tyr-Asp), cyclic (Tyr-His), cyclic (Tyr-Ser), cyclic (Val-Arg), cyclic (Val-Tyr), cyclic (Val-Val), cyclic (Val-Phe), cyclic (Val-Ser), cyclic (Ala-His), cyclic (Ala-Arg), cyclic (Ala-Pro), cyclic (Ala-Tyr), cyclic (Ala-Val), cyclic (Ala-Leu), cyclic (Ala-Ile), cyclic (Ala-Asp) and cyclic (Ala-Asn);The taste enhancing composition according to [1] or [2].

[0012] [4] The taste enhancing composition according to [3], wherein the cyclic dipeptide is one or more selected from the group consisting of cyclic (Ala-Leu), cyclic (Ala-Ile), cyclic (Thr-Pro), cyclic (Pro-His), cyclic (Ala-Pro), cyclic (Arg-Pro), cyclic (Phe-Pro), cyclic (Phe-Ala), cyclic (Pro-Pro), cyclic (hyPro-Pro), cyclic (Leu-Val), cyclic (Ile-Val), cyclic (Gly-Val), cyclic (Ala-Val), cyclic (Pro-Met), cyclic (hyPro-Leu), cyclic (hyPro-Ile), cyclic (Pro-Leu), cyclic (Pro-Ile), and cyclic (Pro-Val).

[0013] [5] The taste enhancing composition according to [3], wherein the cyclic dipeptide is one or more selected from the group consisting of cyclic (Pro-Met), cyclic (Glu-His), cyclic (Ala-His), cyclic (Gly-His), cyclic (Tyr-His), cyclic (Leu-His), cyclic (Ile-His), cyclic (Leu-Val), cyclic (Ile-Val), cyclic (Glu-Gly), cyclic (Pro-His), and cyclic (Glu-Phe).

[0014] [6] The taste enhancing composition according to any one of [1] to [4], further comprising one or more selected from the group consisting of sulfurol (4-methyl-5-thiazoleethanol), sulfurol acetate, carveol, nerolidol, α-terpinen-7-al, and organic acids.

[0015] [7] The taste enhancing composition according to [6], wherein the organic acid is one or more selected from the group consisting of cis-aconitic acid, trans-aconitic acid, tartaric acid, malic acid, and citric acid.

[0016] [8] A method for producing the composition for enhancing flavor according to any one of [1] to [7], comprising heating one or more spices selected from the group consisting of coriander, paprika, cumin, and asafoetida to increase the cyclic dipeptide in the spice.

[0017] [9] A food product containing the taste enhancing composition according to any one of [1] to [7].

[0018]

[10] A method for enhancing the taste of food, comprising blending the taste enhancing composition according to any one of [1] to [7] into food. The taste enhancing composition may be, for example, a salty taste enhancing composition.

[0019]

[11] Use of a cyclic dipeptide to enhance the taste of food.

[0020]

[12] The use according to

[11] , wherein the cyclic dipeptide is a cyclic dipeptide defined in any one of [1] to [5].

[0021]

[13] The use according to

[11] or

[12] , wherein the cyclic dipeptide is a combination of the cyclic dipeptide with one or more selected from the group consisting of sulfurol (4-methyl-5-thiazoleethanol), sulfurol acetate, carveol, nerolidol, α-terpinen-7-al, and organic acids.

[0022]

[14] The use according to

[13] , wherein the organic acid is one or more selected from the group consisting of cis-aconitic acid, trans-aconitic acid, tartaric acid, malic acid, and citric acid.

[0023]

[15] The use according to any one of

[11] to

[14] , wherein the cyclic dipeptide is contained in one or more heat-treated spices selected from the group consisting of coriander, paprika, cumin, and asafoetida.

[0024]

[16] A method for enhancing the taste of food, comprising adding a cyclic dipeptide to the food.

[0025]

[17] The method according to

[16] , wherein the cyclic dipeptide is a cyclic dipeptide defined in any one of [1] to [5].

[0026]

[18] The method according to

[16] or

[17] , wherein the cyclic dipeptide is a combination of the cyclic dipeptide with one or more selected from the group consisting of sulfurol (4-methyl-5-thiazoleethanol), sulfurol acetate, carveol, nerolidol, α-terpinen-7-al, and organic acids.

[0027]

[19] The method according to

[18] , wherein the organic acid is one or more selected from the group consisting of cis-aconitic acid, trans-aconitic acid, tartaric acid, malic acid, and citric acid.

[0028]

[20] The method according to any one of

[16] to

[19] , wherein the cyclic dipeptide is contained in one or more heat-treated spices selected from the group consisting of coriander, paprika, cumin, and asafoetida.

[0029]

[21] Cyclic dipeptides for use in enhancing the taste of food.

[0030]

[22] The cyclic dipeptide according to

[21] , wherein the cyclic dipeptide is a cyclic dipeptide defined in any one of [1] to [5].

[0031]

[23] The cyclic dipeptide according to

[21] or

[22] , wherein the cyclic dipeptide is a combination of the cyclic dipeptide with one or more selected from the group consisting of sulfurol (4-methyl-5-thiazoleethanol), sulfurol acetate, carveol, nerolidol, α-terpinen-7-al, and organic acids.

[0032]

[24] The cyclic dipeptide according to

[23] , wherein the organic acid is one or more selected from the group consisting of cis-aconitic acid, trans-aconitic acid, tartaric acid, malic acid, and citric acid.

[0033]

[25] The cyclic dipeptide according to any one of

[21] to

[24] , wherein the cyclic dipeptide is contained in one or more heat-treated spices selected from the group consisting of coriander, paprika, cumin, and asafoetida.

[0034]

[26] Use of a cyclic dipeptide in the manufacture of an additive for enhancing the taste of food.

[0035]

[27] The use according to

[26] , wherein the cyclic dipeptide is a cyclic dipeptide defined in any one of [1] to [5].

[0036]

[28] The use according to

[26] or

[27] , wherein the cyclic dipeptide is a combination of the cyclic dipeptide with one or more selected from the group consisting of sulfurol (4-methyl-5-thiazoleethanol), sulfurol acetate, carveol, nerolidol, α-terpinen-7-al, and organic acids.

[0037]

[29] The use according to

[28] , wherein the organic acid is one or more selected from the group consisting of cis-aconitic acid, trans-aconitic acid, tartaric acid, malic acid, and citric acid.

[0038]

[30] The use according to any one of

[26] to

[29] , wherein the cyclic dipeptide is contained in one or more heat-treated spices selected from the group consisting of coriander, paprika, cumin, and asafoetida.

[0039] This specification includes the disclosure of Japanese Patent Application No. 2023-013624, from which the present application claims priority. All publications, patents, and patent applications cited in this specification are incorporated herein by reference in their entirety.

[0040] The taste enhancing composition according to one or more embodiments of the present invention can enhance the taste of food by being added to the food.

[0041] According to the method for producing a composition for taste enhancement according to one or more embodiments of the present invention, the composition for taste enhancement can be produced.

[0042] In one or more embodiments of the present invention, the food product is a food product with enhanced flavor.

[0043] According to the method for enhancing the taste of food according to one or more embodiments of the present invention, the taste of the food can be enhanced by blending the composition for taste enhancement into the food.

[0044] Internal standard (47 μg / g L-lysine-) of several cyclic dipeptides in unheated and heat-treated coriander １３ C ６The peak area ratios in the extracted ion chromatograms obtained by LC-MS / MS are shown for the internal standard (47 μg / g L-lysine-monohydrochloride) of several cyclic dipeptides in unheated coriander and heat-treated coriander. １３ C ６ The peak area ratios in the extracted ion chromatograms obtained by LC-MS / MS are shown for the internal standard (47 μg / g L-lysine-monohydrochloride) of sulfurol and sulfurol acetate in unheated coriander and heat-treated (roasted) coriander. １３ C ６ The peak area ratios of tartaric acid, malic acid, and trans-aconitic acid to the internal standard (99 μg / g ribitol) in the extracted ion chromatogram obtained by LC-MS / MS are shown. The peak area ratios of cyclic (Phe-Leu / Ile) (1), cyclic (Pro-Asn) (2), cyclic (Leu / Ile-Leu / Ile) (3), and cyclic (Thr-Leu / Ile) (4) in the extracted ion chromatogram obtained by LC-MS / MS are shown. The peak area ratios of cyclic (Phe-Leu / Ile) (1), cyclic (Pro-Asn) (2), cyclic (Leu / Ile-Leu / Ile) (3), and cyclic (Thr-Leu / Ile) (4) in the extracted ion chromatogram obtained by LC-MS / MS are shown. １３ C ６ The peak area ratios in the extracted ion chromatograms obtained by LC-MS / MS are shown relative to the peak area ratios of the internal standard (47 μg / g L-lysine-monohydrochloride) of cyclic (Phe-Ser) (5), cyclic (Gly-His) (6), cyclic (Gly-Ser) (7), and cyclic (Gly-Arg) (8) in unheated paprika (Comparative Examples 201 and 202) and paprika heat-treated under specified conditions (Examples 201 to 216). １３ C ６ The peak area ratios in the extracted ion chromatograms obtained by LC-MS / MS are shown relative to the peak area ratios of the internal standard (47 μg / g L-lysine-monohydrochloride) of cyclic (Ala-His) (9), cyclic (Glu-His) (10), cyclic (Glu-Arg) (11), and cyclic (Ala-Arg) (12) in unheated paprika (Comparative Examples 201 and 202) and paprika heat-treated under specified conditions (Examples 201 to 216). １３ C ６The peak area ratios in the extracted ion chromatograms obtained by LC-MS / MS are shown relative to the peak area ratios of the internal standard (47 μg / g L-lysine-monohydrochloride) of cyclic (Glu-Glu) (13), cyclic (Glu-Gly) (14), cyclic (Glu-Asp) (15), and cyclic (Pro-His) (16) in unheated paprika (Comparative Examples 201 and 202) and paprika heat-treated under specified conditions (Examples 201 to 216). １３ C ６ The peak area ratios in the extracted ion chromatograms obtained by LC-MS / MS are shown relative to the peak area ratios of the internal standard (47 μg / g L-lysine-monohydrochloride) of cyclic (Glu-Tyr) (17), cyclic (Leu / Ile-Asp) (18), cyclic (Pro-Asp) (19), and cyclic (Val-Arg) (20) in unheated paprika (Comparative Examples 201 and 202) and paprika heat-treated under specified conditions (Examples 201 to 216). １３ C ６ The peak area ratios in the extracted ion chromatograms obtained by LC-MS / MS are shown relative to the peak area ratios of the internal standard (47 μg / g L-lysine-monohydrochloride) of cyclic (Thr-Pro) (21), cyclic (HyPro-Pro) (22), cyclic (Gly-Val) (23), and cyclic (Ala-Pro) (24) in unheated paprika (Comparative Examples 201 and 202) and paprika heat-treated under specified conditions (Examples 201 to 216). １３ C ６ The peak area ratios in the extracted ion chromatograms obtained by LC-MS / MS are shown relative to the peak area ratios of the internal standard (47 μg / g L-lysine-monohydrochloride) of cyclic (Ala-Tyr) (25), cyclic (Arg-Leu / Ile) (26), cyclic (Leu / Ile-Ser) (27), and cyclic (Ala-Val) (28) in unheated paprika (Comparative Examples 201 and 202) and paprika heat-treated under specified conditions (Examples 201 to 216). １３ C ６The peak area ratios in the extracted ion chromatograms obtained by LC-MS / MS are shown relative to the peak area ratios of the internal standard (47 μg / g L-lysine-monohydrochloride) of cyclic (Pro-Pro) (29), cyclic (Gly-Leu / Ile) (30), cyclic (Gly-Phe) (31), and cyclic (Pro-Tyr) (32) in unheated paprika (Comparative Examples 201 and 202) and paprika heat-treated under specified conditions (Examples 201 to 216). １３ C ６ The peak area ratios in the extracted ion chromatograms obtained by LC-MS / MS are shown relative to the peak area ratios of the internal standard (47 μg / g L-lysine-monohydrochloride) of cyclic (Phe-Asp) (33), cyclic (Pro-Val) (34), cyclic (Ala-Leu / Ile) (35), and cyclic (Val-Tyr) (36) in unheated paprika (Comparative Examples 201 and 202) and paprika heat-treated under specified conditions (Examples 201 to 216). １３ C ６ The peak area ratios in the extracted ion chromatograms obtained by LC-MS / MS are shown relative to the peak area ratios of the internal standard (47 μg / g L-lysine-monohydrochloride) of cyclic (Tyr-Ser) (37), cyclic (Phe-Ala) (38), cyclic (Val-Val) (39), and cyclic (Pro-Leu / Ile) (40) in unheated paprika (Comparative Examples 201 and 202) and paprika heat-treated under specified conditions (Examples 201 to 216). １３ C ６ The peak area ratios in the extracted ion chromatograms obtained by LC-MS / MS are shown relative to the peak area ratios of the internal standard (47 μg / g L-lysine-monohydrochloride) of cyclic (Phe-Tyr) (41), cyclic (Phe-Thr) (42), cyclic (Phe-Pro) (43), and cyclic (Leu / Ile-Val) (44) in unheated paprika (Comparative Examples 201 and 202) and paprika heat-treated under specified conditions (Examples 201 to 216). １３ C ６The peak area ratios in the extracted ion chromatograms obtained by LC-MS / MS are shown relative to the peak area ratios of the internal standard (47 μg / g L-lysine-monohydrochloride) of cyclic (Val-Phe) (45), cyclic (Tyr-Asp) (46), cyclic (Ala-Asp) (47), and cyclic (Val-Ser) (48) in unheated paprika (Comparative Examples 201 and 202) and paprika heat-treated under specified conditions (Examples 201 to 216). １３ C ６ The peak area ratios in the extracted ion chromatograms obtained by LC-MS / MS are shown for sulfurol and sulfurol acetate in unheated paprika (Comparative Examples 201 and 202) and in paprika heat-treated under specified conditions (Examples 201 to 216). １３ C ６ The peak area ratios of cyclic (Phe-Phe) (1), cyclic (Phe-Leu / Ile) (2), and cyclic (Leu / Ile-Val) (3) in unheated cumin (Comparative Example 301) and cumin (Examples 301 to 319) heated under specified conditions were compared to the internal standard (47 μg / g L-lysine- １３ C ６The figures show the peak area ratios in extracted ion chromatograms obtained by LC-MS / MS relative to the internal standard for cyclic (Phe-Pro) (4), cyclic (Phe-Tyr) (5), and cyclic (Pro-Leu / Ile) (6) in unheated cumin (Comparative Example 301) and cumin heat-treated under specified conditions (Examples 301 to 319). The figures show the peak area ratios in extracted ion chromatograms obtained by LC-MS / MS relative to the internal standard for cyclic (Val-Val) (7), cyclic (Phe-Ala) (8), and cyclic (Tyr-Ser) (9) in unheated cumin (Comparative Example 301) and cumin heat-treated under specified conditions (Examples 301 to 319). The extracted ion chromatograms obtained by LC-MS / MS show the peak area ratios of cyclic (Pro-Val) (10), cyclic (Pro-Tyr) (11), and cyclic (Pro-Pro) (12) relative to the internal standard in unheated cumin (Comparative Example 301) and cumin heat-treated under specified conditions (Examples 301 to 319). The extracted ion chromatograms obtained by LC-MS / MS show the peak area ratios of cyclic (Leu / Ile-Ser) (13), cyclic (Arg-Leu / Ile) (14), and cyclic (Ala-Tyr) (15) relative to the internal standard in unheated cumin (Comparative Example 301) and cumin heat-treated under specified conditions (Examples 301 to 319). Figure 1 shows the peak area ratios of cyclic (Gly-Tyr) (16), cyclic (Ala-Pro) (17), and cyclic (Gly-Val) (18) in extracted ion chromatograms obtained by LC-MS / MS relative to the internal standard in unheated cumin (Comparative Example 301) and cumin heat-treated under specified conditions (Examples 301 to 319). Figure 1 shows the peak area ratios of cyclic (hyPro-Pro) (19), cyclic (Thr-Pro) (20), and cyclic (Val-Arg) (21) in unheated cumin (Comparative Example 301) and cumin heat-treated under specified conditions (Examples 301 to 319) relative to the internal standard in extracted ion chromatograms obtained by LC-MS / MS.The extracted ion chromatograms obtained by LC-MS / MS show the peak area ratios of cyclic (Pro-Asp) (22), cyclic (Arg-Pro) (23), and cyclic (Glu-Tyr) (24) relative to the internal standard in unheated cumin (Comparative Example 301) and cumin heat-treated under specified conditions (Examples 301 to 319). The extracted ion chromatograms obtained by LC-MS / MS show the peak area ratios of cyclic (Pro-His) (25), cyclic (Glu-Asp) (26), and cyclic (Gly-Arg) (27) relative to the internal standard in unheated cumin (Comparative Example 301) and cumin heat-treated under specified conditions (Examples 301 to 319). The extracted ion chromatograms obtained by LC-MS / MS show the peak area ratios of cyclic (Gly-His) (28), cyclic (Leu / Ile-Leu / Ile) (29), and cyclic (Glu-Glu) (30) relative to the internal standard in unheated cumin (Comparative Example 301) and cumin heat-treated under specified conditions (Examples 301 to 319). The extracted ion chromatograms obtained by LC-MS / MS show the peak area ratios of cyclic (Leu / Ile-Asp) (31) and cyclic (Phe-Asp) (32) relative to the internal standard in unheated cumin (Comparative Example 301) and cumin heat-treated under specified conditions (Examples 301 to 319). The internal standard (47 μg / g L-lysine-) of sulfurol (top) and sulfurol acetate (middle) in unheated cumin (Comparative Example 301) and cumin heated under specified conditions (Examples 301 to 319). １３ C ６The figures show the peak area ratios of trans-aconitic acid (top), tartaric acid (middle), and malic acid (bottom) in extracted ion chromatograms obtained by LC-MS / MS to the internal standard (99 μg / g ribitol) in unheated cumin (Comparative Example 301) and cumin heat-treated under specified conditions (Examples 301 to 319). The figures show the peak area ratios of citric acid in unheated cumin (Comparative Example 301) and cumin heat-treated under specified conditions (Examples 301 to 319) to the internal standard (99 μg / g ribitol) in extracted ion chromatograms obtained by LC-MS / MS. The figure shows the peak area ratios of carveol (top), nerolidol (middle), and α-terpinen-7-al (bottom) in unheated cumin (Comparative Example 301) and cumin heat-treated under specified conditions (Examples 301 to 319) to the internal standard (625 μg / g 4-methylthiazole) in extracted ion chromatograms obtained by GC-MS. The figure shows the peak area ratios of cyclic (Gly-Thr) (1), cyclic (Gly-His) (2), cyclic (Ala-Asp) (3), and cyclic (Val-Ser) (4) in unheated asafoetida (Comparative Example 401) and asafoetida heat-treated under specified conditions (Examples 401 to 404) to the internal standard (47 μg / g L-lysine- １３ C ６ The peak area ratios in the extracted ion chromatograms obtained by LC-MS / MS are shown relative to the peak area ratios of the internal standard substances (47 μg / g L-lysine-monohydrochloride) of cyclic (Gly-Arg) (5), cyclic (Ala-His) (6), cyclic (Glu-Asp) (7), and cyclic (Phe-Phe) (8) in unheated asafoetida (Comparative Example 401) and asafoetida heated under specified conditions (Examples 401 to 404). １３ C ６The peak area ratios in the extracted ion chromatograms obtained by LC-MS / MS are shown relative to the peak area ratios of the internal standard (47 μg / g L-lysine-monohydrochloride) of cyclic (Leu / Ile-Leu / Ile) (9), cyclic (Ala-Arg) (10), cyclic (Leu / Ile-Val) (11), and cyclic (Phe-Pro) (12) in unheated asafoetida (Comparative Example 401) and asafoetida heated under specified conditions (Examples 401 to 404). １３ C ６ The peak area ratios in the extracted ion chromatograms obtained by LC-MS / MS are shown relative to the peak area ratios of the internal standard (47 μg / g L-lysine-) of cyclic (Phe-Leu / Ile) (13), cyclic (Pro-Pro) (14), cyclic (Glu-Phe) (15), and cyclic (Arg-Leu / Ile) (16) in unheated asafoetida (Comparative Example 401) and asafoetida heated under specified conditions (Examples 401 to 404). １３ C ６ The peak area ratios in the extracted ion chromatograms obtained by LC-MS / MS are shown relative to the peak area ratios of the internal standard (47 μg / g L-lysine-monohydrochloride) of cyclic (Pro-Leu / Ile) (17), cyclic (Pro-Glu) (18), cyclic (Glu-Leu / Ile) (19), and cyclic (Ala-Pro) (20) in unheated asafoetida (Comparative Example 401) and asafoetida heated under specified conditions (Examples 401 to 404). １３ C ６ The peak area ratios in the extracted ion chromatograms obtained by LC-MS / MS were compared with the peak area ratios of the internal standard (47 μg / g L-lysine-) of cyclic (Pro-Val) (21) and cyclic (Pro-His) (22) in unheated asafoetida (Comparative Example 401) and in asafoetida heated under specified conditions (Examples 401 to 404). １３ C ６ The peak area ratios in the extracted ion chromatograms obtained by LC-MS / MS are shown for sulfurol in unheated asafoetida (Comparative Example 401) and asafoetida heated under predetermined conditions (Examples 401 to 404), relative to the internal standard (47 μg / g L-lysine- １３ C６ The peak area ratios of tartaric acid, malic acid, and citric acid to the internal standard (99 μg / g ribitol) in the extracted ion chromatogram obtained by LC-MS / MS are shown.

[0045] <Taste Enhancement> In this specification, "taste" refers to the taste of a food, and can be, for example, one or more tastes selected from salty, sweet, sour, bitter, umami, rich, sweet-umami, spicy, astringent, full-flavored taste, and fragrant. "Enhancement" of taste refers to enhancing the taste felt when eating a food, and refers to, for example, enhancing the weak taste felt when eating a food containing a reduced amount of taste components than usual (e.g., a reduced-salt food).

[0046] In this specification, the taste felt when eating a food product can be divided into three stages: the "top" taste felt first, the "middle" taste felt next, and the "last" taste felt last. In this specification, "enhancing the taste" refers to enhancing at least one of these tastes.

[0047] As used herein, the term "salty taste" refers to the taste felt when consuming salt (sodium chloride). Salty taste encompasses the taste of salt itself and the taste felt when salt is combined with ingredients other than salt. For example, the top taste of a food containing salt can be the "salty edge," which is the pungent taste of salt; middle tastes can include "fullness" and "fragrantness"; and final tastes can include a "complex metallic taste" and "aftertaste." Salty taste can also include the taste resulting from "taste boost," in which the taste of ingredients other than salt is enhanced by salt. In this specification, "enhancing saltiness" refers to enhancing at least one of these salty tastes (tastes).

[0048] As used herein, "enhanced flavor" more preferably refers to flavor enhancement derived from one or more flavor components selected from salt, sucrose, citric acid, tartaric acid, naringin, glutamic acid or a salt thereof, aspartic acid or a salt thereof, succinic acid or a salt thereof, inosinic acid or a salt thereof, guanylic acid or a salt thereof, glycine or a salt thereof, alanine or a salt thereof, chili pepper, black pepper, animal- or plant-derived extracts, and seasonings. Examples of the salts in the one or more flavor components include sodium salts. Examples of the animal- or plant-derived extracts include one or more extracts selected from beef extract, chicken extract, pork extract, seafood extract, garlic extract, and onion extract. Examples of the seasonings include one or more selected from tomato paste, banana paste, apple paste, honey, soy sauce, miso, ketchup, Worcestershire sauce, mayonnaise, cheese, noodle soup base, defatted soybeans, skim milk powder, yeast extract, protein hydrolysate, and curry powder. In this specification, enhanced taste more preferably refers to enhanced taste resulting from one or more taste components in a food product containing the one or more taste components, particularly in a food product containing the one or more taste components in a smaller amount than usual.

[0049] <Taste Enhancement Composition> A first embodiment of the present invention relates to a taste enhancement composition containing a cyclic dipeptide.

[0050] The taste enhancing composition according to this embodiment can be incorporated into food to enhance the taste of the food. For example, a food containing one or more of the above-mentioned taste components in a reduced amount compared to normal (e.g., a reduced-salt food containing less salt than normal) that contains the taste enhancing composition according to this embodiment can have a taste closer to that of a food containing one or more taste components in normal amounts than a food that does not contain the composition, and more preferably, can have a taste equivalent to that of a food containing one or more taste components in normal amounts.

[0051] The cyclic dipeptide in the taste enhancing composition according to this embodiment preferably contains, as constituent amino acids, one or more selected from the group consisting of proline, leucine, isoleucine, glycine, phenylalanine, glutamic acid, tyrosine, valine, aspartic acid, histidine, alanine, serine, arginine, threonine, asparagine, and methionine, and particularly preferably contains one or more selected from the group consisting of proline, leucine, isoleucine, glycine, phenylalanine, glutamic acid, tyrosine, valine, aspartic acid, histidine, and alanine. Cyclic dipeptides containing one or more amino acids selected from the above group are preferred because they have a particularly high taste enhancing effect. Specific examples of cyclic dipeptides containing one or more amino acids selected from the above group include cyclic (Pro-Asn), cyclic (Pro-His), cyclic (Pro-Asp), cyclic (Pro-Pro), cyclic (Pro-Val), cyclic (Pro-Tyr), cyclic (Pro-Leu), cyclic (Pro-Ile), cyclic (Pro-Glu), cyclic (Pro-Gly), cyclic (Pro-Me), and cyclic (Pro-Me-Me). t), cyclic (Arg-Pro), cyclic (Thr-Pro), cyclic (hyPro-Pro), cyclic (Leu-Leu), cyclic (Ile-Leu), cyclic (Ile-Ile), cyclic (Leu-A sp), cyclic (Ile-Asp), cyclic (Leu-Ser), cyclic (Ile-Ser), cyclic (Leu-Val), cyclic (Ile-Val), cyclic (Leu-His), cyclic (Ile-His) ), cyclic (Leu-Met), cyclic (Ile-Met), cyclic (Arg-Leu), cyclic (Arg-Ile), cyclic (hyPro-Leu), cyclic (hyPro-Ile), cyclic (Thr-Leu), cyclic (Thr-Ile), cyclic (Gly-His), cyclic (Gly-Ser), cyclic (Gly-Arg), cyclic (Gly-Val), cyclic (Gly-Leu), cyclic (Gly-Ile e), cyclic (Gly-Phe), cyclic (Gly-Tyr), cyclic (Gly-Thr), cyclic (Gly-Gly), cyclic (Gly-Ala), cyclic (Phe-Leu), cyclic (Phe-Ile), cyclic (Phe-Ser), cyclic (Phe-Ala), cyclic (Phe-Asp), cyclic (Phe-Thr), cyclic (Phe-Pro), cyclic (Phe-Tyr), cyclic (Phe-Phe),cyclic (Glu-His), cyclic (Glu-Glu), cyclic (Glu-Arg), cyclic (Glu-Gly), cyclic (Glu-Asp), cyclic (Glu-Tyr), cyclic (Glu-Phe), cyclic (Glu-Leu), cyclic (Glu-Ile), cyclic (Tyr-Asp), cyclic (Tyr-His), cyclic (Tyr-Ser), cyclic (Val-Arg), cyclic (Val-Tyr), cyclic (Val-Val), cyclic (Val-Phe), cyclic (Val-Ser), cyclic (Ala-His), cyclic (Ala-Arg), cyclic (Ala-Pro), cyclic (Ala-Tyr), cyclic (Ala-Val), cyclic (Ala-Leu), cyclic (Ala-Ile), cyclic (Ala-Asp) and cyclic and cyclic (Ala-Asn), more preferably cyclic (Ala-Leu), cyclic (Ala-Ile), cyclic (Thr-Pro), cyclic (Pro-His), cyclic (Ala-Pro), cyclic (Arg-Pro), cyclic (Phe-Pro), cyclic (Phe-Ala), cyclic (Pro-Pro), cyclic (hyPro-Pro), cyclic (Leu-Val), cyclic (Ile-Val), cyclic (Gly-Val), cyclic (Ala-Val), cyclic (Pro-Met), cyclic (hyPro-Leu), cyclic (hyPro-Ile), cyclic (Pro-Leu), cyclic (Pro-Ile), and cyclic (Pro-Val). These specific examples of cyclic dipeptides have particularly high taste enhancing effects. Another preferred example of the cyclic dipeptide having a particularly high taste enhancing effect is one or more selected from the group consisting of cyclic (Pro-Met), cyclic (Glu-His), cyclic (Ala-His), cyclic (Gly-His), cyclic (Tyr-His), cyclic (Leu-His), cyclic (Ile-His), cyclic (Leu-Val), cyclic (Ile-Val), cyclic (Glu-Gly), cyclic (Pro-His), and cyclic (Glu-Phe), more preferably a mixture of five or more cyclic dipeptides selected from the group, and particularly preferably a mixture of all cyclic dipeptides in the group (wherein cyclic (Leu-His) and cyclic (Ile-His) include at least one of these, and cyclic (Leu-Val) and cyclic (Ile-Val) include at least one of these). In the present specification,Cyclic (Phe-Phe) and the like represent cyclic dipeptides consisting of two amino acids. In this specification, "Leu / Ile" represents a mixture of one or both of leucine (Leu) and isoleucine (Ile). For example, "cyclic (Leu / Ile-Val)" means a mixture of one or both of cyclic (Leu-Val) and cyclic (Ile-Val). In this specification, "hyPro" refers to γ-hydroxy-proline. In this specification, all of the amino acids constituting the cyclic dipeptide may be in the L-form, the D-form, or a mixture of the L- and D-forms.

[0052] As described above, enhancing the salty taste refers to enhancing one or more of the top, middle, and last tastes. Meanwhile, cyclic dipeptides may have different taste enhancement profiles depending on the constituent amino acids. To impart the taste enhancing composition of this embodiment with an effect of enhancing the top taste, one or more cyclic dipeptides having the effect of enhancing the top taste can be blended. Similarly, to impart the taste enhancing composition of this embodiment with an effect of enhancing the middle taste, one or more cyclic dipeptides having the effect of enhancing the middle taste can be blended, and to impart the effect of enhancing the last taste, one or more cyclic dipeptides having the effect of enhancing the last taste can be blended. Furthermore, to impart the taste enhancing composition of this embodiment with an effect of enhancing multiple stages of taste, namely the top, middle, and last, multiple cyclic dipeptides can be blended in combination depending on the taste to be enhanced.

[0053] The taste enhancing composition according to the present embodiment contains at least a cyclic dipeptide. The taste enhancing composition according to the present embodiment preferably further contains, in addition to the cyclic dipeptide, one or more selected from the group consisting of sulfurol, sulfurol acetate, carveol, nerolidol, α-terpinen-7-al, and an organic acid. The taste enhancing effect is further enhanced by combining the cyclic dipeptide with one or more selected from the group consisting of sulfurol, sulfurol acetate, carveol, nerolidol, α-terpinen-7-al, and an organic acid. The organic acid in the taste enhancing composition according to the present embodiment is preferably one or more selected from the group consisting of cis-aconitic acid, trans-aconitic acid, tartaric acid, malic acid, and citric acid.

[0054] In the taste enhancing composition according to this embodiment, the cyclic peptide may be blended as a purified product of the artificially produced or naturally derived cyclic dipeptide, or as a naturally derived material containing the cyclic dipeptide. The purified cyclic dipeptide may be in a form containing the cyclic dipeptide at a high concentration, for example, 30% to 100% by mass, preferably 50% to 100% by mass, and more preferably 75% to 100% by mass. Examples of naturally derived materials containing the cyclic dipeptide include spices and extracts thereof obtained by heating one or more spices selected from the group consisting of coriander, paprika, cumin, and asafoetida, which have an increased content of the cyclic dipeptide. A preferred embodiment of the spice will be described in relation to the second embodiment of the present invention. Heating the spice increases the content of the cyclic dipeptide as well as one or more compounds selected from the group consisting of sulfurol, sulfurol acetate, carveol, nerolidol, α-terpinen-7-al, and organic acids.

[0055] The taste enhancing composition according to this embodiment may consist solely of the cyclic dipeptide or a naturally occurring material containing the cyclic peptide, or may contain the cyclic dipeptide or a naturally occurring material containing the cyclic peptide and other ingredients. Examples of other ingredients include one or more ingredients that have a taste enhancing effect and one or more ingredients that are acceptable as food. The taste enhancing composition according to this embodiment may be in the form of a powder, granules, paste, liquid, or the like, and may contain one or more ingredients that are acceptable as food, such as excipients or carriers, as needed to obtain the desired form.

[0056] The taste enhancing composition of this embodiment can contain the cyclic dipeptide in a proportion of preferably 0.1% by mass or more and 100% by mass or less, more preferably 1% by mass or more and 100% by mass or less, even more preferably 5% by mass or more and 100% by mass or less, and particularly preferably 10% by mass or more and 100% by mass or less.

[0057] In an aspect in which the taste enhancing composition of this embodiment contains the naturally-derived material including the cyclic dipeptide, the naturally-derived material can be contained in an amount of preferably 30% by mass or more and 100% by mass or less, more preferably 50% by mass or more and 100% by mass or less, even more preferably 80% by mass or more and 100% by mass or less, and most preferably 95% by mass or more and 100% by mass or less.

[0058] The naturally occurring material containing the cyclic dipeptide in the flavor enhancing composition according to this embodiment is preferably in powder form, with a particle size of, for example, 1000 μm or less. The particle size can be determined from the mesh size of a standard sieve specified in JIS. The naturally occurring material containing the cyclic dipeptide may further contain an oil or fat.

[0059] <Method for producing a composition for enhancing a taste> A second embodiment of the present invention relates to a method for producing a composition for enhancing a taste according to the first embodiment of the present invention, the method comprising: increasing the cyclic dipeptide in one or more spices selected from the group consisting of coriander, paprika, cumin, and asafoetida by heating the spices.

[0060] The present inventors have found that heating the spice increases the amount of cyclic dipeptides in the spice. The present inventors have also found that heating the spice increases not only the amount of cyclic dipeptides but also one or more compounds selected from the group consisting of sulfurol, sulfurol acetate, carveol, nerolidol, α-terpinen-7-al, and organic acids.

[0061] Coriander refers to the seeds of Coriander (Coriandrum sativum), an annual plant of the Apiaceae family. The coriander to be heated may be whole coriander seeds or a pulverized product obtained by pulverizing whole seeds, but whole seeds are preferred.

[0062] Paprika refers to a spice (paprika powder) made by drying and powdering the skin and flesh of the fruit of Capsicum annuum var. grossum, a perennial plant of the Solanaceae family. Hereinafter, unless otherwise specified, paprika refers to paprika powder that can be used as a spice. Paprika powder can be heated.

[0063] Cumin refers to the seeds of Cuminum cyminum, an annual plant of the Apiaceae family. The cumin to be heated may be whole cumin seeds or a pulverized product obtained by pulverizing whole seeds, but whole seeds are preferred.

[0064] As used herein, asafoetida refers to dried resin extracted from asafoetida (Ferula assa-foetida), a plant in the Umbelliferae family, which is used as a spice. Asafoetida used as a spice may further contain additives such as gum arabic and rice flour in addition to asafoetida resin. For example, powdered asafoetida containing asafoetida resin and additives is commercially available as a spice. Unless otherwise specified, asafoetida used herein refers to asafoetida used as a spice, which may contain the additives. The mass of asafoetida used in each embodiment described below is expressed as a mass converted based on an asafoetida resin content of 12% by mass. For example, when the asafoetida resin content of the used asafoetida is 6% by mass, "200 mg of heat-treated asafoetida" is 400 mg in mass when the asafoetida resin content is assumed to be 12% by mass.

[0065] Next, a process for heating one or more spices selected from the group consisting of coriander, paprika, and cumin will be described.

[0066] The treatment of heating one or more selected from the group consisting of coriander, paprika, and cumin is preferably a heat treatment including heating one or more selected from the group consisting of coriander, paprika, and cumin without adding oil or fat (hereinafter may be referred to as a "first heat treatment"), or a heat treatment including heating one or more selected from the group consisting of coriander, paprika, and cumin together with oil or fat (hereinafter may be referred to as a "second heat treatment").

[0067] A preferred embodiment of the first heat treatment of one or more selected from the group consisting of coriander, paprika, and cumin will be described below.

[0068] In the first heating treatment in which one or more selected from the group consisting of coriander, paprika, and cumin are heated without adding oil or fat, only one or more selected from the group consisting of coriander, paprika, and cumin may be heated, or a mixture of water and one or more selected from the group consisting of coriander, paprika, and cumin may be heated. When a mixture of water and one or more selected from the group consisting of coriander, paprika, and cumin is heat-treated, the amount of water to be added is not particularly limited, but preferably, the amount of water to be added can be appropriately set so that the water activity after heating falls within the range described below.

[0069] In the case of heating coriander, the temperature and time of the first heat treatment are preferably set so that the heating value is preferably 100 or more, more preferably 1000 or more, even more preferably 5000 or more, and further so that the heating value is preferably 100 or more and 20000 or less. In the case of heating paprika and cumin, the temperature and time of the first heat treatment are preferably set so that the heating value is preferably 15 or more, preferably 50 or more, preferably 60 or more, preferably 100 or more, preferably 130 or more, even more preferably 190 or more, and most preferably 200 or more, and further so that the heating value is preferably 15 or more and 1000 or less, preferably 15 or more and 600 or less, more preferably 60 or more and 500 or less, even more preferably 100 or more and 410 or less, and particularly preferably 190 or more and 410 or less. One or more selected from the group consisting of coriander, paprika, and cumin that have been heat-treated under conditions such that the heating value falls within the above ranges are particularly preferred because they contain a large amount of cyclic dipeptides. The heating conditions under which the heating value falls within the above range may preferably include heating at the temperature and for the time period described below.

[0070] Here, the heating value is determined by integrating the value expressed by the formula (hereinafter referred to as "CV value") over the heating time (minutes).

[0071] (Formula): CV value=10[(product temperature−reference temperature) / Z value] In this specification, the “reference temperature” is 110° C., and the “Z value” is 30 (° C.).

[0072] In the first heat treatment, heating of one or more selected from the group consisting of coriander, paprika, and cumin can be carried out at a temperature of, for example, 110° C. or higher, preferably 120° C. or higher, more preferably 125° C. or higher, and particularly preferably 128° C. or higher, for example, 110° C. or higher and 300° C. or lower, preferably 120° C. or higher and 250° C. or lower, preferably 125° C. or higher and 200° C. or lower, preferably 128° C. or higher and 180° C. or lower, preferably 128° C. or higher and 160° C. or lower, and more preferably 128° C. or higher and 150° C. Heating of one or more selected from the group consisting of coriander, paprika, and cumin can be carried out for a heating time within the above temperature range of, for example, 5 minutes or longer, preferably 10 minutes or longer, preferably 20 minutes or longer, more preferably 30 minutes or longer, for example, 5 minutes or longer and 120 minutes or shorter, preferably 10 minutes or longer and 90 minutes or shorter, more preferably 20 minutes or longer and 75 minutes or shorter.

[0073] The first heat treatment of coriander may be a heat treatment in an open system without sealing, or a heat treatment under pressurized sealed conditions, but is preferably a heat treatment in an open system without sealing. Heat treatment of coriander in an open system can be performed by heating using superheated steam or heating using an oven. Examples of heating devices used for heat treatment of coriander include a superheated steam vortex mixer, an oven, a flat roaster, a vertical heating mixer, a microwave heating device, etc.

[0074] The first heat treatment of one or more selected from the group consisting of paprika and cumin can be carried out under a pressure condition in which the gauge pressure is preferably 0.05 MPa or more, more preferably 0.2 MPa or more. There is no particular upper limit to the pressure during heating, but in terms of the apparatus, a gauge pressure of 0.6 MPa or less is preferred.

[0075] The first heating treatment of one or more selected from the group consisting of paprika and cumin can be performed using various means such as pressurized sealed heating, superheated steam heating, oven heating, etc., but pressurized sealed heating is preferably used. Examples of heating devices used for pressurized sealed heating include pressurized sealed kettles and retort sterilizers. When using heating other than pressurized sealed heating, ovens, flat roasters, vertical heating mixers, microwave heating devices, superheated steam vortex mixers, superheated steam sterilizers, etc. can be used as appropriate.

[0076] Next, a preferred embodiment of the second heat treatment for one or more selected from the group consisting of coriander, paprika, and cumin will be described below.

[0077] In the second heat treatment, one or more spices selected from the group consisting of coriander, paprika, and cumin are heated together with fats and oils. The heat-treated spices obtained by the second heat treatment are preferred because they have a particularly strong effect of enhancing flavor. The amount of fats and oils used in the second heat treatment is not particularly limited, but for example, 10 parts by mass or more and 500 parts by mass or less, preferably 50 parts by mass or more and 200 parts by mass or less, per 100 parts by mass of the spices can be used. The fats and oils are not particularly limited as long as they are edible fats and oils derived from plants, animals, etc. that are acceptable as foods. The melting point of the fats and oils may be adjusted by techniques such as fatty acid transesterification or hydrogenation.

[0078] The temperature and time of the second heat treatment are preferably set so that the heating value, as defined above, is preferably 0.3 or more, more preferably 0.3 or more and 6000 or less. The heating value range for paprika in the second heat treatment is, for example, 0.3 or more and 6000 or less, preferably 2.5 or more and 450 or less, more preferably 30 or more and 110 or less. The heating value range for coriander or cumin in the second heat treatment is, for example, 1 or more and 6000 or less, preferably 20 or more and 4000 or less, more preferably 100 or more and 1000 or less, and particularly preferably 200 or more and 600 or less. Spices heat-treated under conditions that result in a heating value within the above range are particularly preferred because they contain a large amount of cyclic dipeptides. Heating conditions that result in a heating value within the above range preferably include heating at the temperature and time described below.

[0079] In the second heat treatment, a mixture of one or more spices selected from the group consisting of coriander, paprika, and cumin and fats and oils can be heated at a temperature of, for example, 90°C or higher, preferably 100°C or higher, more preferably 120°C or higher, more preferably 130°C or higher, more preferably 140°C or higher, more preferably 150°C or higher, and for example, 90°C or higher and 230°C or lower, preferably 100°C or higher and 220°C or lower, more preferably 120°C or higher and 220°C or lower, more preferably 130°C or higher and 210°C or lower, more preferably 150°C or higher and 210°C or lower, and particularly preferably 160°C or higher and 210°C or lower. The second heat treatment can be performed for a heating time within the above temperature range of, for example, 1 minute or longer, preferably 2 minutes or longer, preferably 3 minutes or longer, for example, 1 minute or longer and 10 minutes or shorter, preferably 2 minutes or longer and 7 minutes or shorter, more preferably 3 minutes or longer and 7 minutes or shorter. The spices obtained by the second heat treatment under these conditions are preferred because they contain a particularly large amount of cyclic dipeptides.

[0080] The second heat treatment of one or more spices selected from the group consisting of coriander, paprika, and cumin can be carried out in an open system or a closed system.

[0081] The second heat treatment of one or more spices selected from the group consisting of coriander, paprika, and cumin can be performed by heating using superheated steam or an oven. Examples of heating devices used for the second heat treatment include an oven, a pan roaster, a vertical heating mixer, and a microwave heating device.

[0082] The one or more spices selected from the group consisting of coriander, paprika, and cumin heated by the first heat treatment or the second heat treatment may be further subjected to an aging treatment after the heat treatment. The aging treatment is a treatment of storing the spices in an air atmosphere at a temperature higher than room temperature, for example, in an airtight container sealed with air, at 30°C to 50°C, preferably 35°C to 45°C, for 5 days to 15 days, preferably 7 days to 10 days.

[0083] The one or more spices selected from the group consisting of coriander, paprika, and cumin heated by the first heat treatment or the second heat treatment preferably have a water activity measured at 25°C of 0.85 or less, more preferably 0.81 or less, and particularly preferably 0.80 or less.

[0084] Next, the heating treatment of asafoetida, one of the spices, will be described.

[0085] The treatment for heating asafoetida is also preferably a treatment including heating asafoetida without adding fats or oils (hereinafter may be referred to as the "first heating treatment"), or a treatment including heating asafoetida together with fats or oils (hereinafter may be referred to as the "second heating treatment").

[0086] A preferred embodiment of the first heat treatment of Asafoetida will be described below.

[0087] The temperature and time of the first heat treatment of asafoetida are preferably set so that the heating value as defined above is preferably 15 or more, more preferably 50 or more, even more preferably 100 or more, and further so that the heating value is preferably 15 or more and 1,000 or less, more preferably 50 or more and 500 or less, even more preferably 100 or more and 410 or less, and most preferably 100 or more and 300 or less. A preferred range of the heating value is, for example, 50 or more and 300 or less. Asafoetida heat-treated under conditions such that the heating value falls within the above range is particularly preferred because it contains a large amount of cyclic dipeptides. Heating conditions such that the heating value falls within the above range can preferably include heating at the temperature and time described below.

[0088] In the first heat treatment of asafoetida, heating can be performed at a temperature of, for example, 110°C or higher, preferably 120°C or higher, more preferably 125°C or higher, and particularly preferably 128°C or higher, and for example, 100°C to 180°C, preferably 120°C to 160°C, more preferably 125°C to 150°C, and particularly preferably 128°C to 150°C. The first heat treatment can be performed for a heating time within the above temperature range of, for example, 20 minutes or longer, preferably 30 minutes or longer, for example, 20 minutes to 120 minutes, preferably 30 minutes to 90 minutes, and more preferably 30 minutes to 60 minutes. Asafoetida obtained by the first heat treatment under these conditions is preferred because it contains a large amount of cyclic dipeptides.

[0089] The first heat treatment can be carried out under a pressure condition in which the gauge pressure is preferably 0.05 MPa or more, more preferably 0.2 MPa or more. There is no particular upper limit to the pressure during heating, but in terms of the apparatus, a gauge pressure of 0.6 MPa or less is preferred.

[0090] The first heat treatment may be performed using asafoetida alone or a mixture of asafoetida and water. The amount of water in the mixture of asafoetida and water is not particularly limited, but preferably, the amount of water can be appropriately set so that the water activity after heating falls within the range described below.

[0091] For the first heating treatment, various means such as pressurized sealed heating, superheated steam heating, oven heating, etc. can be used, but pressurized sealed heating is preferably used. Examples of heating devices used for pressurized sealed heating include pressurized sealed kettles and retort sterilizers. When using heating other than pressurized sealed heating, ovens, flat-pan roasters, vertical heating mixers, microwave heating devices, superheated steam vortex mixers, superheated steam sterilizers, etc. can be used as appropriate.

[0092] Next, a preferred embodiment of the second heat treatment for Asafoetida will be described below.

[0093] In the second heating treatment, asafoetida is heated together with a fat or oil. The heat-treated asafoetida obtained by the second heating treatment is preferable because it has a particularly strong effect of enhancing flavor. The amount of fat or oil used in the second heating treatment is not particularly limited, but for example, 10 parts by mass or more and 500 parts by mass or less, preferably 50 parts by mass or more and 200 parts by mass or less of fat or oil can be used per 100 parts by mass of asafoetida. The fat or oil is not particularly limited as long as it is an edible fat or oil derived from a plant, animal, or the like that is acceptable as a food. The melting point of the fat or oil may be adjusted by techniques such as fatty acid transesterification or hydrogenation.

[0094] The temperature and time of the second heat treatment are preferably set so that the heating value as defined above is preferably 5 or more, more preferably 10 or more, and even more preferably 20 or more. The upper limit of the heating value in the second heat treatment is, for example, 100 or less, preferably 50 or less, and more preferably 40 or less. That is, the heating value is preferably 5 or more and 100 or less, more preferably 10 or more and 50 or less, and even more preferably 20 or more and 40 or less. Asafoetida heat-treated under conditions such that the heating value falls within the above range is particularly preferred because it contains a large amount of cyclic dipeptides. The heating conditions such that the heating value falls within the above range can preferably include heating at the temperature and time described below.

[0095] In the second heat treatment, the mixture of asafoetida and fats and oils can be heated at a temperature of, for example, 90°C or higher, preferably 100°C or higher, more preferably 110°C or higher, more preferably 120°C or higher, and particularly preferably 125°C or higher, for example, for 30 minutes or longer and 180°C or lower, preferably 100°C or higher and 160°C or lower, more preferably 110°C or higher and 150°C or lower. The second heat treatment can be carried out so that the heating time within the above temperature range is, for example, 2 minutes or longer, preferably 3 minutes or longer, for example, 2 minutes or longer and 10 minutes or shorter, preferably 3 minutes or longer and 7 minutes or shorter. Asafoetida obtained by the second heat treatment under these conditions is preferred because it contains a particularly large amount of cyclic dipeptides.

[0096] The second heat treatment can be carried out in an open system or a closed system.

[0097] The second heating treatment can be performed by heating using superheated steam or heating using an oven. Examples of heating devices used in the second heating treatment include an oven, a flat-pan roaster, a vertical heating mixer, and a microwave heating device.

[0098] The water activity of the asafoetida obtained by the heat treatment, measured at 25°C, is preferably 0.70 or less, more preferably 0.60 or less, and particularly preferably 0.50 or less.

[0099] Next, in this embodiment, one or more compounds selected from the group consisting of cyclic dipeptides, sulfurol, sulfurol acetate, carveol, nerolidol, α-terpinen-7-al, and organic acids that are increased by heating one or more spices selected from the group consisting of coriander, paprika, cumin, and asafoetida will be described.

[0100] Heating one or more spices selected from the group consisting of coriander, paprika, cumin, and asafoetida increases one or more selected from the group consisting of the cyclic dipeptide, sulfurol, sulfurol acetate, carveol, nerolidol, α-terpinen-7-al, and organic acid described in relation to the taste enhancing composition according to the first embodiment of the present invention. The cyclic dipeptide is preferably a cyclic dipeptide containing, as constituent amino acids, one or more selected from the group consisting of proline, leucine, isoleucine, glycine, phenylalanine, glutamic acid, tyrosine, valine, aspartic acid, histidine, alanine, serine, arginine, threonine, asparagine, and methionine, and particularly preferably a cyclic dipeptide containing one or more selected from the group consisting of proline, leucine, isoleucine, glycine, phenylalanine, glutamic acid, tyrosine, valine, aspartic acid, histidine, and alanine, and preferred specific examples thereof are as described above.

[0101] Examples of cyclic dipeptides that increase when coriander is heated include one or more selected from the cyclic dipeptides assigned coriander IDs 1 to 60 shown in the table at the end of the examples. Furthermore, heating coriander increases one or more selected from sulfurol, sulfurol acetate, and organic acids, and in particular, increases one or more selected from sulfurol, sulfurol acetate, tartaric acid, malic acid, and trans-aconitic acid.

[0102] Cyclic dipeptides that increase when paprika is heated typically include one or more selected from the cyclic dipeptides assigned paprika IDs 1 to 48 in the table at the end of the examples. Furthermore, heating paprika increases one or more selected from sulfurol, sulfurol acetate, and organic acids, and in particular increases one or more selected from sulfurol (4-methyl-5-thiazoleethanol), sulfurol acetate, trans-aconitic acid, and tartaric acid.

[0103] Examples of cyclic dipeptides that increase upon heating cumin include one or more selected from the cyclic dipeptides assigned Cumin IDs 1 to 32 listed in the table at the end of the Examples. Furthermore, heating cumin increases one or more selected from sulfurol, sulfurol acetate, carveol, nerolidol, α-terpinen-7-al, and organic acids, and in particular, increases one or more selected from sulfurol, sulfurol acetate, cis-aconitic acid, trans-aconitic acid, tartaric acid, malic acid, and citric acid.

[0104] Examples of cyclic dipeptides that increase upon heating asafoetida include typically one or more selected from the cyclic dipeptides assigned Asafoetida IDs 1 to 22 listed in the table at the end of the Examples. Furthermore, heating asafoetida increases one or more selected from sulfurol, sulfurol acetate, and organic acids, and in particular, increases one or more selected from sulfurol, tartaric acid, malic acid, and citric acid.

[0105] The method for producing a flavor enhancing composition according to this embodiment may use the spice itself after heating as the flavor enhancing composition, or may further include a step of extracting, concentrating or purifying the cyclic dipeptide from the spice after heating, or may further include a step of processing the spice itself after heating, or the cyclic dipeptide extracted, concentrated or purified from the spice after heating, into a form such as powder, granules, paste or liquid.

[0106] <Food with Enhanced Flavor> A third embodiment of the present invention relates to a food containing the flavor enhancing composition according to the first embodiment of the present invention.

[0107] The food product according to this embodiment is a food product with enhanced flavor. The food product according to this embodiment is preferably a food product containing one or more of the above-mentioned flavor components in amounts lower than usual (for example, a reduced-salt food product containing less salt than usual). The food product according to this embodiment can preferably contain one or more flavor components, and more preferably can contain salt.

[0108] The amount of the taste enhancing composition according to the first embodiment of the present invention in the food according to this embodiment is not particularly limited and can be appropriately adjusted according to the form of the food. For example, when the food according to this embodiment is a food containing salt, the taste enhancing composition according to the first embodiment of the present invention can be blended so that the cyclic dipeptide is preferably 0.005 g or more, more preferably 0.010 g or more, particularly preferably 0.020 g or more, preferably 0.005 g or more and 50.0 g or less, more preferably 0.010 g or more and 20.0 g or less, particularly preferably 0.020 g or more and 10.0 g or less, per 100,000 g of salt equivalent of the food.

[0109] The type of food according to this embodiment is not limited, but examples include curry sauce, stew sauce, meat products, prepared foods, confectioneries, etc. <Method for enhancing taste> A fourth embodiment of the present invention relates to a method for enhancing the taste of food, which comprises blending the taste enhancing composition according to the first embodiment of the present invention into the food.

[0110] The method according to this embodiment can enhance the flavor of food, and can therefore be suitably used to enhance the flavor of food that contains one or more of the flavor components described above in amounts that are reduced compared to normal (e.g., low-salt foods that contain less salt than normal).

[0111] The amount of the taste enhancing composition according to the first embodiment of the present invention is not particularly limited and can be adjusted appropriately depending on the type of food. For example, for the purpose of enhancing saltiness, the taste enhancing composition according to the first embodiment of the present invention can be blended so that the cyclic dipeptide is preferably 0.005 g or more, more preferably 0.010 g or more, particularly preferably 0.020 g or more, preferably 0.020 g or more and 50.0 g or less, more preferably 0.010 g or more and 20.0 g or less, particularly preferably 0.020 g or more and 10.0 g or less, relative to 100,000 g of salt equivalent of food.

[0112] The type of food is not limited, but examples include curry sauce, stew sauce, meat products, prepared foods, confectioneries, etc. The food may contain one or more of the above-mentioned taste components in amounts lower than usual. The food may also contain one or more taste components, such as salt.

[0113] <One or more further embodiments> One or more further embodiments of the present invention relate to: use of a cyclic dipeptide for enhancing the taste of food; a method for enhancing the taste of food, comprising blending a cyclic dipeptide into food; a cyclic dipeptide for use in enhancing the taste of food; or use of a cyclic dipeptide in the manufacture of an additive for use in enhancing the taste of food.

[0114] In this embodiment, the cyclic dipeptide can preferably have the characteristics described for the cyclic dipeptide contained in the composition for taste enhancement according to the first embodiment of the present invention.

[0115] In this embodiment, the cyclic dipeptide may be a combination of the cyclic dipeptide and one or more selected from the group consisting of sulfurol, sulfurol acetate, carveol, nerolidol, α-terpinen-7-al, and an organic acid.

[0116] In this embodiment, the cyclic dipeptide may be contained in one or more heat-treated spices selected from the group consisting of coriander, paprika, cumin, and asafoetida. The heat-treated spices may preferably have the characteristics described for the heat-treated spices that may be contained in the flavor enhancing composition according to the first embodiment of the present invention.

[0117] In this embodiment, the food product may preferably comprise the features described in relation to the third and fourth embodiments of the present invention.

[0118] In this embodiment, the cyclic dipeptide is preferably blended with food so that the amount of cyclic dipeptide is preferably 0.005 g or more, more preferably 0.010 g or more, particularly preferably 0.020 g or more, preferably 0.005 g or more and 50.0 g or less, more preferably 0.010 g or more and 20.0 g or less, particularly preferably 0.020 g or more and 10.0 g or less per 100,000 g of salt equivalent of the food, and can be used to enhance the taste of the food.

[0119] 1. Experiment 1: Flavor Enhancement Effect of Heat-Treated Coriander and Cyclic Dipeptides Contained Therein 1.1. Preparation of Heat-Treated Coriander Coriander was prepared by heat-treating it under the conditions shown in the table below. As mentioned above, the heating value is the value obtained by integrating the CV value obtained from the above formula ("reference temperature" is 110°C, "Z value" is 30 (°C)) over the heating time (minutes). The temperature and time listed in the heating conditions column are the maximum temperature reached and the time it was maintained at, while the calculation of the heating value also took into account changes in temperature over time, including the temperature and time during temperature rise and fall.

[0120]

[0121] The control was coriander that had not been heat-treated, including heat sterilization.

[0122] The heat treatment of coriander was carried out by placing 100 g of whole coriander seeds in an open container (oven) under the heating conditions and heating values ​​shown in Table 1.

[0123] The water activity (Aw) of unheated (control) and heat-treated coriander was measured under the temperature conditions shown in the table above.

[0124] 1.2. Component Analysis The components contained in the above-mentioned unheated coriander (control) and the heat-treated coriander were analyzed by the following procedure.

[0125] (1) Preparation of LC-MS / MS test solution 200 mg of unheated coriander (control) or heat-treated coriander was placed in a 10 mL test tube, and 5 mL of ultrapure water was added. The test tube was heated in a thermostatic water bath set at 80°C for 30 minutes, and then allowed to cool to room temperature. 5 mL of acetonitrile (Fujifilm Wako Pure Chemical Industries) was added to the test tube, and L-lysine- １３ C ６ The L-lysine monohydrochloride (Fujifilm Wako Pure Chemical Industries, Ltd.) and ribitol (Fujifilm Wako Pure Chemical Industries, Ltd.) were added as an internal standard in the negative mode. １３ C ６ The monohydrochloride and ribitol were added at concentrations of 47 μg / g and 99 μg / g, respectively. The test tubes were agitated at 1,800 rpm at room temperature for 30 minutes in a high-speed shaker (CM-1000, Tokyo Rikakikai), and after centrifugation, 0.5 mL of the solution in the test tube was transferred to an ultrafiltration filter (Nanosep Centrifugal Filtration Device 3K, Nippon Pall). The ultrafiltration filter was centrifuged at 15,000 rpm for 20 minutes at room temperature, after which 0.5 mL of ultrapure water was added to the filtrate and vortexed for 10 seconds. The solution loaded onto the 0.2 μm filter was used as the LC-MS / MS sample (n=2).

[0126] (2) LC-MS / MS Analysis Conditions The analysis conditions for LC-orbitrap-MS are shown below. Analytical equipment: LC: Vanquish Flex (Thermo Fisher Scientific) MS: ID-X (Thermo Fisher Scientific) Analytical column: Unison UK-C18, 3 μm [particle size], 250 mm [length] × 4.6 mm [inner diameter] (Imtakt) LC conditions: Column temperature: 40°C Injection volume: 5 μL Mode: ESI positive, ESI negative Flow rate: 0.3 mL / min Mobile phase: Solution A: 0.1% formic acid aqueous solution (formic acid: LCMS grade, Fujifilm Wako Pure Chemical Industries) Solution B: acetonitrile (LCMS grade, Fujifilm Wako Pure Chemical Industries) Mobile phase composition - analysis time: 70 minutes

[0127]

[0128] MS conditions: Ion source temperature: 230° C., collision energy: 30 eV Monitoring ions: shown in the table below.

[0129] (3) Data Analysis: The exact mass of the precursor ion > product ion of each component was extracted from the LC-MS / MS chromatogram, and the peak area was obtained. The components in each sample were compared by calculating the product ion peak area ratio (= peak area of ​​the product ion of each component / peak area of ​​the product ion of the internal standard). In the table below, "Compound ID" is a number identifying 64 cyclic dipeptides confirmed to be increased in heat-treated coriander, as well as in heat-treated paprika, cumin, and asafoetida (described below) compared to unheated coriander. In the table below, "Coriander ID" is a number identifying 60 cyclic dipeptides confirmed to be increased in heat-treated coriander compared to unheated coriander. In the table below, A1 and A2 represent the two amino acids that make up each cyclic dipeptide identified by "Compound ID" and "Coriander ID."

[0130]

[0131]

[0132]

[0133] The peak area ratios of the cyclic peptides detected in the LC-MS / MS samples prepared from each sample relative to the internal standard are shown in Figures 1 and 2 and in the table below. The peak area ratios of sulfurol, sulfurol acetate, and organic acids (tartaric acid, malic acid, and trans-aconitic acid) detected in the LC-MS / MS samples prepared from each sample relative to the internal standard are shown in Figure 3. It was confirmed that heating coriander significantly increased the contents of the 60 cyclic dipeptides shown in the table above, as well as sulfurol, sulfurol acetate, and organic acids (tartaric acid, malic acid, and trans-aconitic acid).

[0134]

[0135] In the table, "nd" indicates that the specified compound was not detected. Also, in the table, "*" indicates that the factor could not be calculated because the specified compound was not detected (nd) in the unheated coriander.

[0136] 1.3 Flavor Enhancement Effect of Cyclic Dipeptides (1) Preparation of Conventional Curry Roux 20 g of wheat flour and 30 g of beef fat were placed in a pot and heated and stirred at 120° C. to prepare a wheat flour roux. 10 g of salt, 10 g of sugar, 10 g of cornstarch, 5 g of curry powder, and 15 g of other seasoning ingredients (vegetable and fruit extracts, yeast extract, seafood extract) were added to this wheat flour roux, heated to 105° C., and then cooled and solidified to prepare a block of conventional curry roux.

[0137] The salt equivalent amount per 100 g of this curry roux was 10.6 g.

[0138] (2) Preparation of reduced-salt curry roux A reduced-salt curry roux was prepared using the same procedure as in (1) above, except that the amount of salt was increased to 7 g.

[0139] The salt equivalent amount per 100 g of this reduced-salt curry roux was 7.7 g.

[0140] (3) Preparation of aqueous cyclic dipeptide solutions for sensory evaluation Among the cyclic dipeptides contained in the heat-treated coriander prepared in 1.1 above and confirmed to increase in concentration in 1.2 above, aqueous solutions of the 14 cyclic dipeptides shown in the table below were prepared. The concentration of the cyclic dipeptide in each aqueous solution was determined by the concentration of the internal standard (47 μg / g L-lysine-) of the cyclic dipeptide confirmed in 1.2 above. １３ C ６ The concentration was set to be equivalent to the concentration in the heat-treated coriander prepared in 1.1 above, estimated from the peak area ratio to the monohydrochloride salt.

[0141] (4) Sensory Evaluation Two samples were prepared by dissolving 44 g of the reduced-salt curry roux (2) in 300 g of boiling water.

[0142] To one of the samples, powdered heated or unheated coriander prepared in 1.1 above, or the aqueous solution of cyclic dipeptides prepared in (3) (corresponding to heated coriander) was added to a final concentration of 0.2% (w / w), and a sensory evaluation was performed.

[0143] (1) 44 g of regular curry roux was dissolved in 300 g of hot water.

[0144] A comparison was made between a reduced-salt curry roux dissolved in hot water and a regular curry roux dissolved in hot water, and four evaluators evaluated the intensity of the flavor from the perspective of "flavor enhancement" using the following evaluation criteria. In this experiment, "flavor enhancement" is the effect achieved by combining salt with other ingredients in the curry roux, and is one aspect of "saltiness." Therefore, the "flavor" in this experiment can also be expressed as "salty."

[0145] The "enhanced flavor" scores of 1, 2, 3, 4, and 5 were determined as follows, and three evaluators evaluated the flavor of each sample in increments of 0.1 to calculate the average score. 1 point: flavor similar to reduced-salt curry roux 2 points: flavor slightly stronger than reduced-salt curry roux 3 points: flavor stronger than reduced-salt curry roux 4 points: flavor significantly stronger than reduced-salt curry roux 5 points: flavor strength similar to regular curry roux

[0146] An average evaluation score of 1.0 or less was given an "F", 1.1 to 1.9 was given a "C", 2.0 to 2.5 was given a "B", 2.6 to 2.9 was given an "A", and 3.0 or more was given an "AA".

[0147] The evaluation results are shown in the table below. The hot water-dissolved reduced-salt curry roux to which the cyclic dipeptide of Examples 1 to 14 was added gave a stronger "enhanced flavor" impression than the reduced-salt curry roux to which no cyclic dipeptide was added, and in particular the hot water-dissolved reduced-salt curry roux to which the cyclic dipeptide of Examples 2, 3, 7, 11, 13, and 14 was added gave a flavor impression similar to that of the hot water-dissolved normal curry roux. Furthermore, the hot water-dissolved reduced-salt curry roux to which heat-treated coriander was added gave a stronger "enhanced flavor" impression than the reduced-salt curry roux to which unheated coriander (control) was added.

[0148]

[0149]

[0150] 2. Experiment 2: Flavor Enhancement by Heat-Treated Paprika 2.1. Preparation of Heat-Treated Paprika Paprika was prepared by heat-treating paprika powder under the conditions shown in the table below. As previously mentioned, the heating value is the value obtained by integrating the CV value obtained from the above formula ("reference temperature" is 110°C, "Z value" is 30 (°C)) over the heating time (minutes). The temperature and time listed in the heating conditions column are the maximum temperature reached and the time it was maintained, while the heating value was calculated based on the change in temperature over time, including the temperature and time during temperature rise and fall.

[0151]

[0152] Comparative Example 201 is paprika powder that has not been subjected to any heat treatment, including heat sterilization.

[0153] In Comparative Example 202, the paprika powder of Comparative Example 201 was aged at 40°C for 8 days in the same manner as in Examples 207 to 210 below.

[0154] Heating of paprika powder at a specified temperature and time without adding water was performed as follows: 100 g of paprika powder was filled into an aluminum foil pouch and sealed. The sealed pouch was heat-treated in a retort sterilizer at a specified temperature and time, and then cooled with water. The heat treatment in the retort sterilizer was performed under a gauge pressure of 0.2 MPa.

[0155] Heating of paprika powder "with water" at a specified temperature and time was performed as follows: 100 g of paprika powder and 10 g of water were filled into an aluminum foil pouch and sealed. The sealed pouch was heat-treated in a retort sterilizer at a specified temperature and time, and then cooled with water. The heat treatment in the retort sterilizer was performed under a gauge pressure of 0.2 MPa.

[0156] For the paprika powders of Examples 207 to 210, paprika powder was heated under specified conditions, filled into aluminum foil pouches, and sealed so as to contain air. The sealed pouches were stored at 40°C for 8 days to mature.

[0157] The paprika powder in Examples 211 to 216 was heated in oil according to the following procedure: 100 g of palm oil (melting point 45°C) was heated, and when it reached 80°C, 100 g of paprika powder was mixed in. The resulting mixture was heated to the specified temperature shown in the table above while stirring, and then held at that temperature for a specified time, after which the mixture was cooled. Cooling was carried out while stirring until the paprika powder was about 60°C, to the extent that it did not separate in the mixture, and then the mixture was cooled in a refrigerator until it solidified. Note that "reached temperature" in Examples 211 to 213 means that heating was stopped and cooling was started immediately when the mixture reached the specified temperature.

[0158] The water activity (Aw) of the paprika powders of Comparative Example 201 and Examples 201 to 210 was measured under the temperature conditions shown in the table above. 2.2. Flavor Enhancement Effect Regular curry roux and reduced-salt curry roux were prepared according to the procedures described in 1.3. (1) and (2) above. Two solutions were prepared by dissolving 44 g of the reduced-salt curry roux described in 1.3. (2) above in 300 g of boiling water.

[0159] To one of the mixtures, the paprika powder of the comparative example or example was added so as to give a final concentration of 0.0464% by mass.

[0160] 44 g of the regular curry roux described in 1.3.(1) above was dissolved in 300 g of boiling water.

[0161] A hot water-dissolved reduced-salt curry roux and a hot water-dissolved regular curry roux were compared, and the flavor intensity was evaluated by three evaluators (Evaluators 1, 2, and 3) from the perspective of "middle flavor expansion" using the following evaluation criteria. In this experiment, "flavor (middle flavor expansion)" is the flavor of the middle flavor achieved by combining salt with other ingredients in the curry roux, and is one aspect of "saltiness." Therefore, the "flavor (middle flavor expansion)" in this experiment can also be expressed as "salty flavor (middle flavor expansion)."

[0162] The taste (middle fullness) was scored as follows: 1, 2, 3, 4, and 5 points. Three evaluators evaluated the taste of each sample in 0.1 point increments and calculated the average score. 1 point: taste similar to reduced-salt curry roux; 2 points: taste slightly stronger than reduced-salt curry roux; 3 points: taste stronger than reduced-salt curry roux; 4 points: taste significantly stronger than reduced-salt curry roux; 5 points: taste similar to regular curry roux.

[0163] The average evaluation score was rated as "C" if it was higher than those of Comparative Examples 201 and 202 and was 2.0 or less, "B" if it was 2.1 or more and 2.5 or less, "A" if it was 2.6 or more and 3.0 or less, and "AA" if it was 3.1 or more and 5.0 or less.

[0164] The evaluation results are shown in the table below. It was confirmed that the heat-treated paprikas of Examples 201 to 216 had a greater effect of enhancing the "middle fullness" of flavor than the paprikas of Comparative Examples 201 and 202.

[0165]

[0166] 2.3. Component Analysis The components contained in the paprika samples of Comparative Examples 201-202 and Examples 201-216 were analyzed by the following procedure.

[0167] (1) Preparation of LC-MS / MS test solution 200 mg of paprika sample (when the paprika sample is a paprika sample that has been heat-treated with oil or fat, the mass is calculated as the paprika sample without oil or fat) was collected in a 10 mL test tube, and 5 mL of ultrapure water was added. The test tube was heated in a thermostatic water bath set at 80°C for 30 minutes and then allowed to cool to room temperature. 5 mL of acetonitrile (Fujifilm Wako Pure Chemical Industries) was added to the test tube, and L-lysine- １３ C ６ The paprika sample (if the paprika sample is a paprika sample that has been heat-treated with oil or fat, the mass is calculated as the paprika sample excluding the oil or fat) was added with L-lysine- １３ C ６The monohydrochloride and ribitol were added at concentrations of 47 μg / g and 99 μg / g, respectively. The test tubes were agitated at 1,800 rpm at room temperature for 30 minutes in a high-speed shaker (CM-1000, Tokyo Rikakikai), and after centrifugation, 0.5 mL of the solution in the test tube was transferred to an ultrafiltration filter (Nanosep Centrifugal Filtration Device 3K, Nippon Pall). The ultrafiltration filter was centrifuged at 15,000 rpm for 20 minutes at room temperature, after which 0.5 mL of ultrapure water was added to the filtrate and vortexed for 10 seconds. The solution loaded onto the 0.2 μm filter was used as the LC-MS / MS sample (n=2). The above 200 mg of paprika sample refers to the mass converted into a paprika sample excluding fats and oils, and refers to 200 mg as the mass of the heat-treated paprika samples of Examples 201 to 210 in which only paprika or a mixture of paprika and water was heat-treated, and refers to 400 mg as the mass of the heat-treated paprika samples of Examples 211 to 216 in which a mixture of paprika and fats and oils was heat-treated.

[0168] (2) LC-MS / MS Analysis Conditions The analysis conditions for LC-orbitrap-MS are shown below. Analytical equipment: LC: Vanquish Flex (Thermo Fisher Scientific) MS: ID-X (Thermo Fisher Scientific) Analytical column: Unison UK-C18, 3 μm [particle size], 250 mm [length] × 4.6 mm [inner diameter] (Imtakt) LC conditions: Column temperature: 40°C Injection volume: 5 μL Mode: ESI positive, ESI negative Flow rate: 0.3 mL / min Mobile phase: Solution A: 0.1% formic acid aqueous solution (formic acid: LCMS grade, Fujifilm Wako Pure Chemical Industries) Solution B: acetonitrile (LCMS grade, Fujifilm Wako Pure Chemical Industries) Mobile phase composition - analysis time: 70 minutes

[0169]

[0170] MS conditions: Ion source temperature: 230° C., collision energy: 30 eV Monitoring ions: shown in the table below.

[0171] (3) Data Analysis: From the LC-MS / MS chromatogram, the exact mass of the precursor ion > product ion of each component (see the table below) was extracted and the peak area was obtained. The components in each sample were compared by calculating the peak area ratio of the product ions (= peak area of ​​the product ion of each component / peak area of ​​the product ion of the internal standard). In the table below, A1 and A2 represent the two amino acids that make up each cyclic dipeptide.

[0172]

[0173]

[0174]

[0175] The peak area ratios of cyclic peptides, organic acids (tartaric acid and trans-aconitic acid), sulfurol, and sulfurol acetate detected in the LC-MS / MS samples prepared from each sample relative to the internal standard are shown in Figures 4 to 16. The bars in the figures represent standard deviations.

[0176] The results shown in Figures 4 to 16 show that the heat-treated paprika of Examples 201 to 216 had higher concentrations of cyclic (Phe-Leu / Ile), cyclic (Pro-Asn), cyclic (Leu / Ile-Leu / Ile), cyclic (Thr-Leu / Ile), cyclic (Phe-Ser), cyclic (Gly-His), cyclic (Gly-Ser), cyclic (Gly-Arg), and cyclic (Al a-His), cyclic (Glu-His), cyclic (Glu-Arg), cyclic (Ala-Arg), cyclic (Glu-Glu), cyclic (Glu-Gly), cyclic (Glu-Asp), cyclic (Pro-His), cyclic (Glu-Tyr), cyclic (Leu / Ile-Asp), cyclic (Pro-Asp), cyclic (Val-Arg), cyclic (Thr-Pro), cyclic (hyPro-Pro), cyclic (Gly-Val), cyclic ( Ala-Pro), cyclic (Ala-Tyr), cyclic (Arg-Leu / Ile), cyclic (Leu / Ile-Ser), cyclic (Ala-Val), cyclic (Pro-Pro), cyclic (Gly-Leu / Ile), cyclic (Gly-Phe), cyclic (Pro-Tyr), cyclic (Phe-Asp), cyclic (Pro-Val), cyclic (Ala-Leu / Ile), cyclic (Val-Tyr), cyclic (Tyr-Ser), cyclic ( The results show that the paprika contained high amounts of trans-aconitic acid, including cyclic (Phe-Ala), cyclic (Val-Val), cyclic (Pro-Leu / Ile), cyclic (Phe-Tyr), cyclic (Phe-Thr), cyclic (Phe-Pro), cyclic (Leu / Ile-Val), cyclic (Val-Phe), cyclic (Tyr-Asp), cyclic (Ala-Asp), cyclic (Val-Ser), sulfurol, sulfurol acetate, tartaric acid, and trans-aconitic acid. The amounts of these components tended to correlate with the strength of the flavor enhancement effect. In particular, cyclic (Gly-His), cyclic (Gly-Ser), cyclic (hyPro-Pro), cyclic (Gly-Val), cyclic (Tyr-Asp), and cyclic (Ala-Asp) are components specific to heat-treated paprika and are not found in unheated paprika (below the detection limit).

[0177] 2.4. Flavor Enhancement Effect on Various Food Materials (1) Sample Preparation The food materials listed in the "Basic Flavor," "Dashi Ingredients," "Seasoning," and "Ingredients" columns in the table below were each diluted with water to the concentrations (% (w / w)) shown in the table below to prepare food material dilutions. Each of the food material dilutions was mixed with the heat-treated paprika powder of Example 203 to a final concentration of 0.05% (w / w) to prepare a sample. The food material dilution without added paprika powder served as a negative control sample. Additionally, a food material dilution with a concentration approximately 1.2 times that shown in the table below was prepared as a positive control sample for each food material.

[0178] The foods, such as curry, shown in the "Food" column of the table below were prepared using a commercially available instant food kit. To facilitate evaluation of flavor enhancement, each food was prepared using approximately 1.2 times the amount of water specified in the kit. Each of the prepared foods was mixed with the heated paprika powder of Example 203 to a final concentration ranging from 0.03 to 0.07% (w / w) to prepare a sample. Each of the above foods without added paprika powder served as a negative control. Additionally, each food was prepared as a positive control using the amount of water specified in the kit.

[0179] (2) Sensory Evaluation The taste intensity of the samples prepared from each food material was evaluated by three evaluators (evaluators 1, 2, and 3).

[0180] The following scores were assigned: 1, 2, 3, 4, and 5. Three evaluators evaluated the taste intensity of each sample in increments of 0.5, and the average score was calculated. 1 point: Taste similar to the negative control sample. 2 points: Taste slightly stronger than the negative control sample. 3 points: Taste slightly stronger than the negative control sample. 4 points: Taste slightly stronger than the negative control sample. 5 points: Taste similar to the positive control sample.

[0181] The average evaluation score was rated as "C" if it was greater than 1.0 (negative control sample) and less than 2.0, "B" if it was 2.1 or more and less than 2.5, "A" if it was 2.6 or more and less than 3.0, and "AA" if it was 3.1 or more and less than 5.0.

[0182] The evaluation results are shown in the table below. It was confirmed that the heat-treated paprika powder of Example 203 has a high effect of enhancing the flavor of various food ingredients.

[0183]

[0184] 3. Experiment 3: Flavor Enhancement Effect of Heat-Treated Cumin 3.1. Preparation of Heat-Treated Cumin Whole cumin seeds (cumin seeds) were heat-treated under the conditions shown in the table below. As previously mentioned, the heating value is the value obtained by integrating the CV value obtained from the above formula ("reference temperature" is 110°C, "Z value" is 30 (°C)) over the heating time (minutes). The temperature and time listed in the heating conditions column are the maximum temperature reached and the time it was maintained at, while the calculation of the heating value also took into account changes in temperature over time, including the temperature and time during temperature rise and fall.

[0185]

[0186] Comparative Example 301 is cumin seeds that have not been subjected to any heat treatment including heat sterilization.

[0187] Cumin seeds were heated "without adding water" at a specified temperature and time as follows: 100 g of cumin seeds were packed into an aluminum foil pouch and sealed. The sealed pouch was heat-treated in a retort sterilizer at a specified temperature and time, and then cooled with water. The heat treatment in the retort sterilizer was carried out under a gauge pressure of 0.2 MPa.

[0188] Cumin seeds were heated "with added water" at a specified temperature and time as follows: 100 g of cumin seeds and 10 g of water were packed into an aluminum foil pouch and sealed. The sealed pouch was heat-treated in a retort sterilizer at a specified temperature and time, and then cooled with water. The heat treatment in the retort sterilizer was carried out under a gauge pressure of 0.2 MPa.

[0189] The cumin seeds of Examples 307, 308, 313, and 314 were heated and then crushed and aged according to the following procedure. The heated cumin seeds were crushed into powder using a stamp mill for 3 minutes per 20 g. The powder was then packed into an aluminum foil pouch and sealed to contain air. The sealed pouch was then stored at 40°C for 8 days to age.

[0190] The cumin in the comparative examples and examples other than Examples 307, 308, 313, and 314 was also pulverized under the same conditions to form powder, and used as samples for the following water activity measurement, confirmation of the flavor enhancing effect, and component analysis. The cumin in Examples 307, 308, 313, and 314 was used as a sample as it was after aging.

[0191] In Examples 315 to 319, ground cumin seeds were heated in oil according to the following procedure.

[0192] Unheated cumin seeds were ground into powder using a stamp mill for 5 minutes per 75g.

[0193] 100 g of palm oil (melting point 45°C) was heated, and when the temperature reached 80°C, 100 g of ground cumin seeds was mixed in. The resulting mixture was heated to the specified temperature shown in the table while stirring, and after maintaining that temperature for a specified time, the mixture was cooled. Cooling was carried out to about 60°C while stirring to a degree that prevented the ground cumin seeds from separating in the mixture, and then the mixture was cooled in a refrigerator until solidification occurred. Note that "reached temperature" in Example 315 means that heating was stopped and cooling was started immediately when the mixture reached the specified temperature.

[0194] The water activity (Aw) of the cumin samples of Comparative Example 301 and Examples 301 to 314 was measured under the temperature conditions shown in the table above.

[0195] 3.2. Flavor Enhancement Effect Regular curry roux and reduced-salt curry roux were prepared according to the procedures described in 1.3. (1) and (2) above. Two solutions were prepared by dissolving 44 g of the reduced-salt curry roux described in 1.3. (2) above in 300 g of boiling water.

[0196] To one of the samples, cumin from the comparative example or example was added to a final concentration of 0.0619% by mass.

[0197] (1) 44 g of regular curry roux was dissolved in 300 g of hot water.

[0198] A hot water-dissolved reduced-salt curry roux was compared with a hot water-dissolved regular curry roux, and the flavor intensity was evaluated by three evaluators (Evaluators 1, 2, and 3) from the perspectives of "top salt angle" and "middle fullness" using the following evaluation criteria. In this experiment, "taste (top salt angle)" and "taste (middle fullness)" are the top and middle flavors, respectively, achieved by combining salt with other ingredients in the curry roux, and are one aspect of "salty taste." Therefore, in this experiment, "taste (top salt angle)" and "taste (middle fullness)" can also be expressed as "salty taste (top salt angle)" and "salty taste (middle fullness)," respectively.

[0199] The taste ("saltiness at the top" and "fullness in the middle") was scored as follows: 1, 2, 3, 4, and 5 points. Three evaluators evaluated the taste of each sample in increments of 0.1 points, and the average score was calculated. 1 point: taste similar to reduced-salt curry roux 2 points: taste slightly stronger than reduced-salt curry roux 3 points: taste stronger than reduced-salt curry roux 4 points: taste significantly stronger than reduced-salt curry roux 5 points: taste strength similar to regular curry roux

[0200] For both the evaluation items of "top salt angle" and "middle fullness", the average score was rated as "C" if it was higher than that of Comparative Example 301 and was 2.0 or less, "B" if it was 2.1 or more and 2.5 or less, and "A" if it was 2.6 or more.

[0201] The evaluation results are shown in the table below. It was confirmed that the heat-treated cumin of Examples 301 to 319 had a higher effect of enhancing the flavor in terms of both the "salt angle of the top" and the "fullness of the middle" compared to the cumin of Comparative Example 301.

[0202]

[0203]

[0204] 3.3. Component Analysis The components contained in the cumin samples of Comparative Example 301 and Examples 301 to 319 were analyzed by the following procedure.

[0205] 3.3.1. Component analysis by LC-MS / MS (1) Preparation of LC-MS / MS test solution 200 mg of cumin sample (when the cumin sample is a cumin sample that has been heat-treated with fats and oils, the mass is calculated as the cumin sample without fats and oils) was placed in a 10 mL test tube, and 5 mL of ultrapure water was added. The test tube was heated in a thermostatic water bath set to 80°C for 30 minutes and then allowed to cool to room temperature. 5 mL of acetonitrile (Fujifilm Wako Pure Chemical Industries) was added to the test tube, and L-lysine- １３ C ６ The cumin sample (if the cumin sample is a cumin sample heat-treated together with fat or oil, the mass is calculated as the mass of the cumin sample excluding fat or oil) was added with L-lysine- １３ C ６ The monohydrochloride and ribitol were added at concentrations of 47 μg / g and 99 μg / g, respectively. The test tubes were agitated at 1,800 rpm at room temperature for 30 minutes in a high-speed shaker (CM-1000, Tokyo Rikakikai), and after centrifugation, 0.5 mL of the solution in the test tube was transferred to an ultrafiltration filter (Nanosep Centrifugal Filtration Device 3K, Nippon Pall). The ultrafiltration filter was centrifuged at 15,000 rpm for 20 minutes at room temperature, after which 0.5 mL of ultrapure water was added to the filtrate and vortexed for 10 seconds. The solution loaded onto the 0.2 μm filter was used as the LC-MS / MS sample (n=2). The above 200 mg of cumin sample refers to the mass converted into a cumin sample excluding fats and oils, and refers to 200 mg as the mass of the heat-treated cumin samples of Examples 301 to 314 in which only cumin or a mixture of cumin and water was heat-treated, and refers to 400 mg as the mass of the heat-treated cumin samples of Examples 315 to 319 in which a mixture of cumin and fats and oils was heat-treated.

[0206] (2) LC-MS / MS Analysis Conditions LC-MS / MS analysis was carried out under the conditions described in 1.2.(2) above.

[0207] (3) Data Analysis: From the LC-MS / MS ion chromatogram, the exact mass of the precursor ion > product ion of each component (see table below) was extracted and the peak area was obtained. The components in each sample were compared by calculating the peak area ratio of the product ions (= peak area of ​​the product ion of each component / peak area of ​​the product ion of the internal standard). In the table below, A1 and A2 represent the two amino acids that make up each cyclic dipeptide.

[0208]

[0209]

[0210]

[0211] 3.3.2. Component Analysis by GC-MS (1) Preparation of GC-MS Test Solution 15 mg of cumin sample (if the cumin sample was heat-treated with oil or fat, this refers to the mass converted to the cumin sample excluding the oil or fat) was placed in a 10 mL test tube, to which 5 mL of acetone (Fujifilm Wako Pure Chemical Industries, Ltd.) and 5 mL of methanol (Fujifilm Wako Pure Chemical Industries, Ltd.) were added. 4-Methylthiazole (Tokyo Chemical Industry Co., Ltd.) was added as an internal standard to a concentration of 625 μg / g of the cumin sample (mass converted to cumin). The test tube was stirred at 1,800 rpm at room temperature for 30 minutes in a high-speed shaker (CM-1000, Tokyo Rikakikai Co., Ltd.). After stirring, the mixture was centrifuged. 0.1 mL of the solution in the test tube was transferred to a GC-MS vial, and 1 mL of acetone was added to prepare a GC-MS sample (n=2). The above 15 mg of cumin sample means the mass converted into the cumin sample excluding fats and oils, and means 15 mg as the mass of the heat-treated cumin samples of Examples 301 to 314 in which only cumin or a mixture of cumin and water was heat-treated, and means 30 mg as the mass of the heat-treated cumin samples of Examples 315 to 319 in which a mixture of cumin and fats and oils was heat-treated.

[0212] (2) GC-MS Analysis Conditions The analysis conditions for GC-orbitrap-MS are as follows: Analytical equipment: GC: TRACE1310 (Thermo Fisher Scientific) MS: QExactiveGC (Thermo Fisher Scientific) Analytical column: TG-WAXMS [length] 60 m [inner diameter] 0.25 mm [film thickness] 0.25 μm (Thermo Fisher Scientific) Autosampler: TRIPLUS RSH (Thermo Fisher Scientific) GC conditions: Injection method: liquid injection Injection volume: 1 μL Gas: helium, 130 kPa (pressure) Injection port temperature: 240°C Oven temperature: 40°C (hold for 1 minute) -10°C / min -110°C -2°C / min -180°C -3°C / min -240°C -10°C / min -250°C (hold for 6 minutes), total 70 minutes MS conditions: Transfer temperature: 240°C Ion source temperature: 230°C Ionization method: EI positive MS scan: m / z 30-450 Monitoring ions: shown in the table below.

[0213] (3) Data Analysis: The exact mass of each component (see the table below) was extracted from the GC-MS chromatogram, and the peak area was obtained. The components in each sample were compared by calculating the peak area ratio (= peak area of ​​each component / peak area of ​​the internal standard).

[0214]

[0215] 3.3.3. Component analysis results

[0216] The peak area ratios of cyclic peptides, organic acids (tartaric acid, malic acid, citric acid, cis-aconitic acid, trans-aconitic acid), sulfurol, sulfurol acetate, carveol, nerolidol, and α-terpinen-7-al detected in specimens prepared from each sample relative to the internal standard are shown in Figures 17 to 31. The bars in the figures represent standard deviations.

[0217] The results shown in Figures 17 to 31 show that the heat-treated cumin of Examples 301 to 314 had higher concentrations of cyclic (Phe-Phe), cyclic (Phe-Leu / Ile), cyclic (Leu / Ile-Val), cyclic (Phe-Pro), cyclic (Phe-Tyr), cyclic (Pro-Leu / Ile), cyclic (Val-Val), cyclic (Phe-Ala), cyclic (Tyr-Ser), cyclic (Pro-Val), cyclic (Pro-Tyr), cyclic (Pro-Pro), cyclic (Leu / Ile-Ser), cyclic (Arg-Leu / Ile), cyclic (Ala-Tyr), cyclic (Gly-Tyr), cyclic (Ala-Pro), and cyclic (G The results show that the extract was rich in α-terpinen-7-al, cyclic (α-Val), cyclic (α-Pro-Pro), cyclic (Thr-Pro), cyclic (Val-Arg), cyclic (Pro-Asp), cyclic (Arg-Pro), cyclic (Glu-Tyr), cyclic (Pro-His), cyclic (Glu-Asp), cyclic (Gly-Arg), cyclic (Gly-His), cyclic (Leu / Ile-Leu / Ile), cyclic (Glu-Glu), cyclic (Leu / Ile-Asp), cyclic (Phe-Asp), tartaric acid, malic acid, citric acid, cis-aconitic acid, trans-aconitic acid, sulfurol, sulfurol acetate, carveol, nerolidol, and α-terpinen-7-al. Among these, the cumin of Examples 305 to 314, which were heat-treated at 130° C. or 140° C., showed particularly significant increases in the above components. In particular, cyclic (Phe-Tyr), cyclic (Phe-Ala), cyclic (Tyr-Ser), cyclic (Leu / Ile-Ser), cyclic (Ala-Tyr), cyclic (Gly-Tyr), cyclic (Ala-Pro), cyclic (Gly-Val), cyclic (hyPro-Pro), and cyclic (Glu-Glu) are components specific to heat-treated cumin and are not found in unheated cumin (below the detection limit).

[0218] 3.4. Flavor Enhancement Effect on Various Food Materials (1) Sample Preparation Samples in which the heat-treated cumin of Example 305 was added to the diluted food materials or foods shown in the table below, as well as their negative and positive control samples, were prepared by the method described in 2.4.(1) above, except that the heat-treated cumin of Example 305 was added instead of the heat-treated paprika powder of Example 203, so that the final concentration in the diluted food material sample was 0.05% (w / w) and the final concentration in the food sample was 0.03 to 0.07% (w / w).

[0219] (2) Sensory Evaluation Three evaluators tasted and evaluated the taste intensity of the samples prepared from each food material. The evaluation criteria and method were as described in 2.4. (2) above.

[0220] The evaluation results are shown in the table below. It was confirmed that the heat-treated cumin of Example 305 has a high effect of enhancing the flavor of various food ingredients.

[0221]

[0222] 4. Experiment 4: Flavor Enhancement by Heat-Treated Asafoetida 4.1. Preparation of Heat-Treated Asafoetida The asafoetida powder used in the following experiments contained 12% by mass of asafoetida (resin), 60% by mass of gum arabic, and 28% by mass of rice flour. The asafoetida powder was prepared by dissolving asafoetida, mixing it with gum arabic and rice flour, drying, and then powdering. The asafoetida powder was heat-treated under the conditions shown in the table below. As previously described, the heating value is the value obtained by integrating the CV value obtained by the above formula ("reference temperature" is 110°C, and "Z value" is 30°C) over the heating time (minutes). The temperature and time listed in the heating conditions column are the maximum temperature reached and the time it was maintained at, while the calculation of the heating value also took into account changes in temperature over time, including the temperature and time during temperature rise and fall.

[0223]

[0224] Comparative Example 401 is asafoetida powder that has not been subjected to any heat treatment, including heat sterilization.

[0225] The heating of asafoetida powder in Example 401 (130°C for 30 minutes, without adding water) was carried out as follows: 100 g of asafoetida powder was filled into an aluminum foil pouch and sealed. The sealed pouch was heat-treated in a retort sterilizer at a predetermined temperature for a predetermined time, and then cooled with water. The heat treatment in the retort sterilizer was carried out under a gauge pressure of 0.2 MPa.

[0226] The asafoetida powder was heated in oil in Examples 402, 403, and 404 as follows: Asafoetida powder (12% by mass of asafoetida) and palm oil (melting point 45°C) were mixed in a mass ratio of 50:50, heated at a predetermined temperature for a predetermined time while stirring, and then cooled to obtain asafoetida heated in oil that was in the form of a solid curry roux at room temperature.

[0227] The water activity (Aw) of the Asafoetida powder of Comparative Example 401 was measured under the temperature conditions shown in the table above.

[0228] 4.2 Flavor Enhancement Effect Regular curry roux and reduced-salt curry roux were prepared according to the procedures described in 1.3. (1) and (2) above. Two solutions were prepared by dissolving 44 g of the reduced-salt curry roux described in 1.3. (2) above in 300 g of boiling water.

[0229] To one of them, asafoetida of the Comparative Example or Example was added so as to give a final concentration of 0.00077% by mass. The amount of asafoetida heated in oil added in Example 402, 403 or 404 is an amount including the amount of oil or fat added.

[0230] 44 g of the regular curry roux described in 1.3.(1) above was dissolved in 300 g of boiling water.

[0231] A hot water-dissolved reduced-salt curry roux and a hot water-dissolved regular curry roux were compared, and three evaluators (Evaluators 1, 2, and 3) evaluated the flavor intensity from the perspective of "flavor enhancement" using the following evaluation criteria. In this experiment, "flavor enhancement" is the effect achieved by combining salt with other ingredients in the curry roux, and is one aspect of "saltiness." Therefore, the "flavor" in this experiment can also be expressed as "salty."

[0232] The "enhanced flavor" scores of 1, 2, 3, 4, and 5 were determined as follows, and three evaluators evaluated the flavor of each sample in increments of 0.1 to calculate the average score. 1 point: flavor similar to reduced-salt curry roux 2 points: flavor slightly stronger than reduced-salt curry roux 3 points: flavor stronger than reduced-salt curry roux 4 points: flavor significantly stronger than reduced-salt curry roux 5 points: flavor strength similar to regular curry roux

[0233] The average evaluation score was rated as "C" if it was higher than that of Comparative Example 401 and 2.0 or less, "B" if it was 2.1 or more and 2.5 or less, "A" if it was 2.6 or more and 3.0 or less, and "AA" if it was 3.1 or more and 5.0 or less.

[0234] The evaluation results are shown in the table below. It was confirmed that the heat-treated asafoetida of Examples 401 to 404 had a higher effect of enhancing the "flavor enhancement" than the asafoetida of Comparative Example 401.

[0235]

[0236] 4.3. Component Analysis The components contained in the asafoetida of Comparative Example 401 and Examples 401 to 404 were analyzed by the following procedure.

[0237] (1) Preparation of LC-MS / MS test solution 200 mg of asafoetida from Comparative Example 401 or Example 401, or 400 mg of oil-heated asafoetida from Examples 402, 403, or 404 (200 mg as a mass calculated assuming an asafoetida resin content of 12% by mass) was placed in a 10 mL test tube, and 5 mL of ultrapure water was added. The test tube was heated in a thermostatic water bath set at 80°C for 30 minutes and then allowed to cool to room temperature. 5 mL of acetonitrile (Fujifilm Wako Pure Chemical Industries) was added to the test tube, and L-lysine- １３ C ６Asafoetida monohydrochloride (Fujifilm Wako Pure Chemical Industries, Ltd.) was added to the asafoetida sample at a concentration of 47 μg / g (for the asafoetida samples heated in oil in Examples 402, 403, and 404, calculated as an asafoetida resin content of 12% by mass), and ribitol (Fujifilm Wako Pure Chemical Industries, Ltd.) was added as an internal standard for negative mode at a concentration of 99 μg / g (for the asafoetida samples heated in oil in Examples 402, 403, and 404, calculated as an asafoetida resin content of 12% by mass). The test tube was stirred at room temperature at 1,800 rpm for 30 minutes in a high-speed shaker (CM-1000, Tokyo Rikakikai) and centrifuged. 0.5 mL of the solution in the test tube was transferred to an ultrafiltration filter (Nanosep Centrifugal Filtration Device 3K, Nippon Pall). The ultrafiltration filter was centrifuged at room temperature at 15,000 rpm for 20 minutes, and 0.3 mL of the filtrate was loaded onto a solid-phase extraction column, InertSep C18 (100 mg / 1 mL, GL Sciences), and the eluate was collected. Prior to loading the filtrate, the InertSep C18 was conditioned with 1 mL of 50% (w / w) acetonitrile water. An additional 0.5 mL of acetonitrile was loaded onto the InertSep C18, and the eluate was collected. 1.5 mL of ultrapure water was added to the eluate, and the mixture was vortexed for 10 seconds. The solution loaded onto the 0.2 μm filter was used as the LC-MS / MS sample (n=2).

[0238] (2) LC-MS / MS Analysis Conditions LC-MS / MS analysis was carried out under the conditions described in 1.2.(2) above.

[0239] (3) Data Analysis: From the LC-MS / MS chromatogram, the exact mass of the precursor ion > product ion of each component (see the table below) was extracted and the peak area was obtained. The components in each sample were compared by calculating the peak area ratio of the product ions (= peak area of ​​the product ion of each component / peak area of ​​the product ion of the internal standard). In the table below, A1 and A2 represent the two amino acids that make up each cyclic dipeptide.

[0240]

[0241]

[0242]

[0243] The peak area ratios of cyclic peptides, organic acids (tartaric acid, malic acid, citric acid), and sulfurol detected in the LC-MS / MS samples prepared from each sample relative to the internal standard are shown in Figures 32 to 38. The bars in the figures represent standard deviations.

[0244] The results shown in Figures 32 to 38 show that the heat-treated asafoetida of Examples 401 to 404 had higher cyclic (Gly-Thr), cyclic (Gly-His), cyclic (Ala-Asp), cyclic (Val-Ser), cyclic (Gly-Arg), cyclic (Ala-His), cyclic (Glu-Asp), cyclic (Phe-Phe), cyclic (Leu / Ile-Leu / Ile), cyclic (Ala-Arg), cyclic These results indicate that the asafoetida samples contained large amounts of cyclic (Leu / Ile-Val), cyclic (Phe-Pro), cyclic (Phe-Leu / Ile), cyclic (Pro-Pro), cyclic (Glu-Phe), cyclic (Arg-Leu / Ile), cyclic (Pro-Leu / Ile), cyclic (Pro-Glu), cyclic (Glu-Leu / Ile), cyclic (Ala-Pro), cyclic (Pro-Val), cyclic (Pro-His), tartaric acid, malic acid, citric acid, and sulfurol. In particular, the asafoetida samples of Examples 402 to 404 heated in oil, which has a strong flavor enhancing effect, showed a significant increase in the above components. The amounts of these components tended to correlate with the strength of the flavor enhancing effect. In particular, cyclic (Val-Ser), cyclic (Pro-Pro), and cyclic (Pro-Glu) are components specific to heat-treated asafoetida that are not contained in unheated asafoetida (below the detection limit).

[0245] 4.4. Flavor Enhancement Effect on Various Food Materials (1) Sample Preparation Samples in which the heat-treated asafoetida of Example 403 was added to the diluted solutions or foods of the food materials shown in the table below, as well as their negative and positive control samples, were prepared by the method described in 2.4.(1) above, except that the heat-treated asafoetida of Example 403 was added instead of the heat-treated paprika powder of Example 203 so that the final concentration in the diluted food material samples was 0.025% (w / w) and the final concentration in the food samples was 0.015 to 0.035% (w / w).

[0246] (2) Sensory Evaluation Three evaluators tasted and evaluated the taste intensity of the samples prepared from each food material. The evaluation criteria and method were as described in 2.4. (2) above.

[0247] The evaluation results are shown in the table below. It was confirmed that the heat-treated asafoetida of Example 403 has a high effect of enhancing the taste of various food ingredients.

[0248]

[0249] 5. Cyclic dipeptides correlated with the strength of flavor enhancing effect In Experiments 1 to 4 above, it was confirmed that heat-treated coriander, paprika, cumin, and asafoetida have a flavor enhancing effect compared to unheated ones. Furthermore, in Experiments 1 to 4 above, it was confirmed that heat-treated coriander, paprika, cumin, and asafoetida have an increased amount of multiple cyclic dipeptides compared to unheated ones.

[0250] The following table shows 64 cyclic dipeptides that were confirmed to be increased in heat-treated coriander, paprika, cumin, and asafoetida compared to unheated ones. As described in Experiment 1, each cyclic dipeptide was assigned a "compound ID," and cyclic dipeptides confirmed to be increased in heat-treated coriander were assigned a "coriander ID." Similarly, cyclic dipeptides confirmed to be increased in heat-treated paprika were assigned a "paprika ID," cyclic dipeptides confirmed to be increased in heat-treated cumin were assigned a "cumin ID," and cyclic dipeptides confirmed to be increased in heat-treated asafoetida were assigned an "asafoetida ID." In the table below, A1 and A2 represent the two amino acids that make up each cyclic dipeptide identified by the "compound ID."

[0251]

[0252] 6. Experiment 6: Taste enhancement effect of cyclic dipeptides (1) Preparation of aqueous cyclic dipeptide solutions for sensory evaluation For each of the cyclic dipeptides shown in the table below, an internal standard (47 μg / g L-lysine- １３ C ６ An aqueous solution was prepared so that the concentration of cyclohexanediamine in the heat-treated coriander prepared in 1.1 above (hereinafter referred to as "heat-treated coriander-equivalent aqueous solution") was the same as that in the heat-treated paprika prepared in Example 203 in 2.1 above, estimated from the peak area ratio to the cyclohexanediamine monohydrochloride salt (monohydrochloride). Cyclic dipeptides prepared by the applicant were used in this experiment. A mixture of equal amounts of a Leu-containing cyclic dipeptide and an Ile-containing cyclic dipeptide was used as the Leu / Ile-containing cyclic dipeptide.

[0253] (2) Preparation of Evaluation Samples Regular curry roux and reduced-salt curry roux were prepared according to the procedures described in 1.3. (1) and (2) above.

[0254] Two solutions were prepared by dissolving 44 g of the reduced-salt curry roux in 300 g of boiling water. To one of the solutions, an aqueous solution of a cyclic dipeptide shown in the table below equivalent to heat-treated coriander or heat-treated paprika was added to a final concentration of 0.5% (w / w) or 1.0% (w / w).

[0255] 44 g of the above-mentioned regular curry roux was dissolved in 300 g of hot water.

[0256] A comparison was made between a hot water-dissolved reduced-salt curry roux and a hot water-dissolved regular curry roux, and three evaluators evaluated the flavor intensity from the perspectives of "saltiness at the top," "fullness in the middle (enhanced flavor)," and "enhanced flavor at the end (extension)" using the following evaluation criteria.

[0257] The following scores were assigned to "top saltiness," "middle fullness (enhanced thickness)," and "final flavor boost (extension)," with three evaluators rating the taste of each sample in increments of 0.1 to calculate the average score. 1 point: Taste similar to reduced-salt curry roux 2 points: Taste slightly stronger than reduced-salt curry roux 3 points: Taste stronger than reduced-salt curry roux 4 points: Taste significantly stronger than reduced-salt curry roux 5 points: Taste strength similar to that of regular curry roux

[0258] An average evaluation score of 1.0 or less was given an "F", 1.1 to 1.9 was given a "C", 2.0 to 2.5 was given a "B", 2.6 to 2.9 was given an "A", and 3.0 or more was given an "AA".

[0259] The evaluation results are shown in the table below. In the table, "ID" refers to the compound ID. "Coriander 0.5%" and "Coriander 1.0%" refer to the addition of the aqueous solution of cyclic dipeptide equivalent to heat-treated coriander to final concentrations of 0.5% (w / w) and 1.0% (w / w), respectively. "Paprika 0.5%" and "Paprika 1.0%" refer to the addition of the aqueous solution of cyclic dipeptide equivalent to heat-treated paprika to final concentrations of 0.5% (w / w) and 1.0% (w / w), respectively.

[0260] Compared to the reduced-salt curry roux without added cyclic dipeptides, the hot water-dissolved reduced-salt curry roux with each cyclic dipeptide added had a stronger perceived "saltiness at the top," "fullness in the middle (enhanced thickness)," and "enhanced flavor at the end (extension)."

[0261]

[0262]

[0263] 7. Experiment 7: Taste-enhancing effect of cyclic dipeptides on various food ingredients (1) Sample preparation A mixture of cyclic (Pro-Met) (ID: 60), cyclic (Glu-His) (ID: 8), cyclic (Ala-His) (ID: 13), cyclic (Gly-His) (ID: 4), cyclic (Tyr-His) (ID: 57), cyclic (Leu / Ile-His) (ID: 59), cyclic (Leu / Ile-Val) (ID: 46), cyclic (Glu-Gly) (ID: 12), cyclic (Pro-His) (ID: 18), and cyclic (Glu-Phe) (ID: 53) was added to the internal standard (47 μg / g L-lysine- １３ C ６ An aqueous solution (hereinafter referred to as "mixed cyclic dipeptide aqueous solution") was prepared so that the concentration of the mixed cyclic dipeptide was the same as that in the heat-treated coriander prepared in 1.1 above, estimated from the peak area ratio to the monohydrochloride of the mixed cyclic dipeptide.

[0264] The cyclic dipeptides used were as described in Experiment 6.

[0265] Samples in which the mixed cyclic dipeptide aqueous solution was added to the food dilutions or foods shown in the table below, as well as their negative and positive control samples, were prepared by the method described in 2.4.(1) above, except that the mixed cyclic dipeptide aqueous solution was added in place of the heat-treated paprika powder of Example 203 so that the final concentration of the aqueous solution in the food dilution sample or food sample was 1.0% (w / w).

[0266] (2) Sensory Evaluation The taste intensity of the samples prepared from each food ingredient and food was evaluated by three evaluators (Evaluators 1, 2, and 3). The evaluation criteria are as described in 2.4.(2) above.

[0267] The average evaluation score was rated as "F" if it was 1 point (negative control sample) or less, "C" if it was more than 1 point (negative control sample) and 1.9 or less, "B" if it was 2.0 or more and 2.5 or less, "A" if it was 2.6 or more and 2.9 or less, and "AA" if it was 3.0 or more and 5.0 or less.

[0268] The evaluation results are shown in the table below. It was confirmed that the mixed cyclic dipeptide aqueous solution containing the above 10 types of cyclic dipeptides at the same concentrations as the heat-treated coriander had a strong effect of enhancing various flavors.

[0269]

Claims

1. A taste enhancing composition containing a cyclic dipeptide.

2. The composition for enhancing taste according to claim 1, wherein the cyclic dipeptide contains one or more selected from the group consisting of proline, leucine, isoleucine, glycine, phenylalanine, glutamic acid, tyrosine, valine, aspartic acid, histidine and alanine.

3. The cyclic dipeptide is cyclic (Pro-Asn), cyclic (Pro-His), cyclic (Pro-Asp), cyclic (Pro-Pro), cyclic (Pro-Val), cyclic (Pro-Tyr), cyclic (Pro-Leu), cyclic (Pro-Ile), cyclic (Pro-Glu), cyclic (Pro-Gly), cyclic (Pro-Met), cyclic (Arg-Pro), cyclic (Thr-Pro), cyclic (hyPro-Pro), cyclic (Leu-Leu), cyclic (Ile-Leu), cyclic (Ile-Ile), cyclic (Leu-Asp), cyclic (Ile-Asp), cyclic (Leu-Se). r), cyclic(Ile-Ser), cyclic(Leu-Val), cyclic(Ile-Val), cyclic(Leu-His), cyclic(Ile-His), cyclic(Leu-Met), cyclic(Ile-Met), cyclic(Arg-Leu), cyclic(Arg-Ile), cyclic(hyPro-Leu), cyclic(hyPro-Ile), cyclic(Thr-Leu), cyclic(Thr-Ile), cyclic(Gly-His), cyclic(Gly-Ser), cyclic(Gly-Arg), cyclic(Gly-Val), cyclic(Gly-Leu), cyclic(Gly-Ile), cyclic(Gly-Phe), cyclic( Gly-Tyr), cyclic (Gly-Thr), cyclic (Gly-Gly), cyclic (Gly-Ala), cyclic (Phe-Leu), cyclic (Phe-Ile), cyclic (Phe-Ser), cyclic (Phe-Ala), cyclic (Phe-Asp), cyclic (Phe-Thr), cyclic (Phe-Pro), cyclic (Phe-Tyr), cyclic (Phe-Phe), cyclic (Glu-His), cyclic (Glu-Glu), cyclic (Glu-Arg), cyclic (Glu-Gly), cyclic (Glu-Asp), cyclic (Glu-Tyr), cyclic (Glu-Phe), cyclic (Glu-Leu), cyclic 2. The taste enhancing composition according to claim 1, wherein the cyclic amine is one or more selected from the group consisting of cyclic (Glu-Ile), cyclic (Tyr-Asp), cyclic (Tyr-His), cyclic (Tyr-Ser), cyclic (Val-Arg), cyclic (Val-Tyr), cyclic (Val-Val), cyclic (Val-Phe), cyclic (Val-Ser), cyclic (Ala-His), cyclic (Ala-Arg), cyclic (Ala-Pro), cyclic (Ala-Tyr), cyclic (Ala-Val), cyclic (Ala-Leu), cyclic (Ala-Ile), cyclic (Ala-Asp) and cyclic (Ala-Asn).

4. The taste enhancing composition according to claim 3, wherein the cyclic dipeptide is one or more selected from the group consisting of cyclic (Ala-Leu), cyclic (Ala-Ile), cyclic (Thr-Pro), cyclic (Pro-His), cyclic (Ala-Pro), cyclic (Arg-Pro), cyclic (Phe-Pro), cyclic (Phe-Ala), cyclic (Pro-Pro), cyclic (hyPro-Pro), cyclic (Leu-Val), cyclic (Ile-Val), cyclic (Gly-Val), cyclic (Ala-Val), cyclic (Pro-Met), cyclic (hyPro-Leu), cyclic (hyPro-Ile), cyclic (Pro-Leu), cyclic (Pro-Ile) and cyclic (Pro-Val).

5. The taste enhancing composition according to claim 3, wherein the cyclic dipeptide is one or more selected from the group consisting of cyclic (Pro-Met), cyclic (Glu-His), cyclic (Ala-His), cyclic (Gly-His), cyclic (Tyr-His), cyclic (Leu-His), cyclic (Ile-His), cyclic (Leu-Val), cyclic (Ile-Val), cyclic (Glu-Gly), cyclic (Pro-His) and cyclic (Glu-Phe).

6. The taste enhancing composition according to claim 1, further comprising one or more selected from the group consisting of sulfurol (4-methyl-5-thiazoleethanol), sulfurol acetate, carveol, nerolidol, α-terpinen-7-al, and organic acids.

7. 7. The taste enhancing composition according to claim 6, wherein the organic acid is at least one selected from the group consisting of cis-aconitic acid, trans-aconitic acid, tartaric acid, malic acid and citric acid.

8. A method for producing the taste enhancing composition according to any one of claims 1 to 7, comprising the steps of: increasing the cyclic dipeptide in one or more spices selected from the group consisting of coriander, paprika, cumin and asafoetida; The method includes:

9. A food product comprising the flavor enhancing composition according to any one of claims 1 to 7.

10. The method includes blending the flavor enhancing composition according to any one of claims 1 to 7 into a food product. A method for enhancing the flavor of food.