JP2012029616A - Flavor enhancer - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a flavor enhancer enabling increase in deliciousness of food and drink, addition of rich taste to the food and drink and favorable meltability of palatability of the food and drink which are not sufficiently achieved by addition of conventional seasoning, natural extract and/or the like; and to provide a method for enhancing flavor.SOLUTION: The flavor enhancer comprises pyroglutamyl dipeptide or its salt represented by formula (1) (wherein R is a residue of an amino acid selected from among serine, glycine, histidine, arginine, alanine, an aspartic acid, a glutamic acid, a pyroglutamic acid, phenylalanine, threonine, cysteine, cystine, glutamine, asparagine, methionine, tyrosine, tryptophan, valine, isoleucine, lysine or leucine, which is combined with an adjacent carbonyl group via an amino group in molecules).

Description

  The present invention relates to a flavor enhancer comprising pyroglutamyl dipeptide or a salt thereof, a seasoning containing pyroglutamyl dipeptide or a salt thereof, a food or drink containing them, and a pyroglutamyl dipeptide or a salt thereof. The present invention relates to a flavor enhancing method characterized by adding salt.

  In many foods and drinks, umami shows an important taste, and methods for enhancing umami have been developed. For example, as a method for enhancing the flavor of food, a method using ammonium L-glutamate (Patent Document 1), and as a method for enhancing taste, a method using Trehalose (Patent Document 2), gluconic acid A method of using a salt of (Patent Document 3) has been proposed

  In addition, kokumi is known as a taste that gives a mellowness and depth to the taste of food and drink. Natural flavors such as livestock meat extracts, seafood extracts, and vegetable extracts are widely used for imparting richness, as well as glutathione (patent document 4), acidic insoluble fractions of livestock meat and seafood extracts (patent document 5), and amino acid derivatives. Utilization of a component imparting a rich taste such as (Patent Document 6) is proposed. However, since natural extracts have an unpleasant odor, bitterness, and savory taste derived from raw materials, there are problems that the amount of use is limited depending on the use, and a sufficient richness cannot be imparted.

  In addition, the components imparting rich taste such as peptides have problems that separation and purification are complicated and expensive, and also have undesirable tastes and off-flavors, and further technical development has been demanded. On the other hand, as an example of pyroglutamyl dipeptide, it has been reported that a novel pyroglutamyl proline is effective for bitterness masking (Patent Document 7), but the flavor enhancing effect has not been known.

Japanese Patent Application Laid-Open No. 2004-261098 Japanese Patent Laid-Open No. 10-66540 WO01 / 060178 JP-A-60-9465 Japanese Patent Laid-Open No. 9-94076 JP-A-8-143551 Japanese Patent Laid-Open No. 9-100297

  The problem to be solved by the present invention is that the addition of conventional seasonings, natural extracts, etc. is not sufficient, mellow enhancement of food and drink, imparting rich taste and taste of food and drink are more mellow It is to provide a flavor enhancing agent and a flavor enhancing method.

As a result of searching for a compound having a flavor enhancing effect to solve the above problems, the present inventors have found that pyroglutamyl dipeptide or a salt thereof enhances the umami of food and drink and imparts a rich taste. Furthermore, these components have the property of enhancing the umami of foods and beverages when added to foods and beverages, imparting a rich taste, and enhancing the flavor as a whole, even though they themselves have astringency. The present invention was found and the invention was completed.

（式中、Ｒは隣接するカルボニル基と分子中のアミノ基を介して結合する、セリン、グリシン、ヒスチジン、アルギニン、アラニン、アスパラギン酸、グルタミン酸、ピログルタミン酸、フェニルアラニン、トレオニン、システイン、シスチン、グルタミン、アスパラギン、メチオニン、チロシン、トリプトファン、バリン、イソロイシン、リシンまたはロイシンから選ばれるアミノ酸の残基を表す）で表されるピログルタミルジペプチド又はその塩からなることを特徴とする風味増強剤であり、アミノ酸がＬ形アミノ酸であること、さらに、アミノ酸がＬ−グルタミン又はＬ−グリシンであることを特徴とする。 That is, the present invention
Formula (1)

(Wherein R binds to an adjacent carbonyl group via an amino group in the molecule, serine, glycine, histidine, arginine, alanine, aspartic acid, glutamic acid, pyroglutamic acid, phenylalanine, threonine, cysteine, cystine, glutamine, A flavor enhancer characterized by comprising a pyroglutamyl dipeptide represented by asparagine, methionine, tyrosine, tryptophan, valine, isoleucine, lysine or leucine) or a salt thereof. It is an L-form amino acid, and the amino acid is L-glutamine or L-glycine.

Moreover, this invention is a seasoning characterized by adding said flavor enhancer, It is 1-10 < ⁶ > ppm of said flavor enhancer as an active ingredient, It is a seasoning characterized by the above-mentioned. .

Moreover, this invention is the food / beverage characterized by adding the said seasoning, It contains 0.1-10 < ⁵ > ppm said flavor enhancer as an active ingredient.
Furthermore, this invention is 0.001-1 mass part of said flavor enhancer with respect to 1 mass part of glutamic acid or its salt, It is a flavor enhancement method characterized by the above-mentioned.

  The flavor enhancer of the present invention can enhance the umami of food and drink, impart a rich taste, and enhance the flavor as a whole. Furthermore, the flavor enhancer of the present invention can synergistically enhance the umami by combining it with an amino acid seasoning or a nucleic acid seasoning.

（式中、Ｒは隣接するカルボニル基と分子中のアミノ基を介して結合する、セリン、グリシン、ヒスチジン、アルギニン、アラニン、アスパラギン酸、グルタミン酸、ピログルタミン酸、フェニルアラニン、トレオニン、システイン、シスチン、グルタミン、アスパラギン、メチオニン、チロシン、トリプトファン、バリン、イソロイシン、リシンまたはロイシンから選ばれるアミノ酸の残基を表す）で表されるピログルタミルジペプチドであり、アミノ酸がＬ形アミノ酸であるものが好ましい。特に、アミノ酸がＬ−グルタミン又は
Ｌ−グリシンである下記化学式のピログルタミルグルタミンとピログルタミルグリシンが好ましい。

本発明で使用するピログルタミルジペプチドは、合成あるいは天然物から分離・精製したものを用いて添加することができる。 (1) Flavor enhancer The pyroglutamyl dipeptide used in the present invention has the formula (1)

(Wherein R binds to an adjacent carbonyl group via an amino group in the molecule, serine, glycine, histidine, arginine, alanine, aspartic acid, glutamic acid, pyroglutamic acid, phenylalanine, threonine, cysteine, cystine, glutamine, It is preferably a pyroglutamyl dipeptide represented by asparagine, methionine, tyrosine, tryptophan, valine, isoleucine, lysine or leucine), wherein the amino acid is an L-form amino acid. Particularly preferred are pyroglutamylglutamine and pyroglutamylglycine having the following chemical formula, wherein the amino acid is L-glutamine or L-glycine.

The pyroglutamyl dipeptide used in the present invention can be added using a synthesized or separated and purified product from a natural product.

  Further, commercially available pyroglutamyl dipeptide can be used as it is. For example, pyroglutamyl glutamine and pyroglutamylglycine are manufactured and sold by BACHEM in the United States, and thus can be easily obtained by those skilled in the art.

The flavor enhancer of this invention can be suitably added in the processing stage of food and drink. The amount added varies somewhat depending on the degree of purification of the flavor enhancer, but generally 0.1 to 10 ⁵ ppm (as an active ingredient) is appropriate for food and drink. preferably 0.1 to 10 ⁴ ppm from the viewpoint of adding to the extent that the flavor does not affect, particularly preferably 1 to 10 ⁴ ppm in terms of its effectiveness, the use aspect 10 to 10 ⁴ ppm Is most preferred.

(2) Seasoning The seasoning containing the flavor enhancer of the present invention is suitable for seasonings used as food additives in addition to seasonings used in general cooking such as sugar, salt, vinegar, soy sauce, and miso. Used for.
The term “food additive seasoning” as used herein refers to amino acid-based seasonings such as L-aspartic acid, DL-alanine, glycine, and sodium L-glutamate, and nucleic acids such as sodium 5′-inosinate and 5′-ribonucleotide disodium. -Based seasonings, organic acid seasonings such as tripotassium citrate and succinic acid, and inorganic salt seasonings such as potassium chloride and tripotassium phosphate, preferably used for amino acid seasonings and nucleic acid seasonings In particular, it is preferably used for sodium L-glutamate and sodium 5'-inosinate.

The amount used when the flavor enhancer of the present invention is used in these seasonings depends on the mode of use, but generally it is sufficient if it contains 1 to 10 ⁶ ppm of the flavor enhancer of the present invention. 1 to 10 ⁵ ppm is preferable from the viewpoint of adding within the range that does not affect the original flavor, and 10 to 10 ⁵ ppm is particularly preferable from the viewpoint of its effectiveness. The usage form is 10 ² to 10 ^5. ppm is most preferred.
In particular, it is preferable to add 0.001 to 1 part by mass of the flavor enhancer of the present invention to 1 part by mass of glutamic acid or a salt thereof.

(3) Food and drink The flavor enhancer of the present invention can be used for various foods and drinks without any particular limitation.
For example, fruits or processed products thereof, vegetables or processed products thereof, seafood or processed products thereof, paste products, cooked foods, prepared vegetables, snacks, delicacies, processed foods, nutritional foods, tea drinks, coffee drinks, etc. Taste drinks, fruit juice drinks, carbonated drinks, soft drinks, functional drinks, alcoholic drinks, ice cream, confectionery such as sherbet, desserts such as jelly, pudding, sheep cane, cookies, cakes, chocolate, chewing gum, buns, etc. , Breads such as confectionery bread and bread, jams, ramune confectionery, tablets and tablet confectionery.

  Furthermore, Japanese soup stock, such as bonito, seafood, kelp, shiitake mushrooms, chicken, vegetables, etc., or soup stock of Western dishes, beef, chicken, pork, seafood, vegetables And soup, and Chinese-style tang (hot water) such as beef, chicken, pork, seafood, vegetables, and so on. Moreover, a flavor enhancer can also enhance a flavor and a color tone by suitably blending a flavor component or a pigment. There is no restriction | limiting in particular in the flavor component or pigment | dye used for preparation, A well-known flavor component or pigment | dye is suitably mix | blended and used according to the objective.

  EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited to the description of the examples.

[Example 1]
Pyroglutamyl glutamine (manufactured by BACHEM, Pry-Gln-OH) was added to the sodium glutamate solution for sensory evaluation.
L-sodium glutamate monohydrate 100.0 mg was dissolved in 200 mL of water as a control, and a sodium glutamate solution to which 80 mg of pyroglutamyl glutamine was added. This was evaluated by a panel of 10 people. The evaluation criteria were a 5-level relative evaluation where the taste of the control product was 2, the very strong taste was 5, and the very weak taste was 1. The results are shown in Table 1.

  From the above results, pyroglutamyl glutamine enhanced the umami and richness of sodium glutamate, and further provided an effect of imparting a mellow taste like food and drink.

[Example 2]
Pyroglutamyl glutamine was added to sodium inosinate for sensory evaluation.
Dissolve 200.0 mg of sodium inosinate in 200 mL of water and use it as a control product. In addition, the sodium inosinate solution with 80 mg of pyroglutamylglutamine has 10 people who have the umami, richness, and mildness of food The panel was evaluated. The evaluation criteria were a 5-level relative evaluation where the taste of the control product was 2, the very strong taste was 5, and the very weak taste was 1. The results are shown in Table 2.

  From the above results, pyroglutamyl glutamine enhanced the umami and richness of sodium inosinate, and further provided an effect of giving a mild taste like food and drink.

[Example 3]
Pyroglutamylglycine (manufactured by BACHEM, Pry-Gly-OH) was added to commercially available consomme soup for sensory evaluation. To 10 g of commercially available consomme powder, 5 mg of pyroglutamylglycine was added, and hot water was added to prepare a consomme soup with a total volume of 600 mL, which was used as an evaluation sample.
As a control, 10 g of the above-mentioned commercially available consomme powder was added with hot water to make a total amount of 600 mL, and the two types of consomme soup had a umami, richness, and a mildness of consomme soup. Rated by name panel. The evaluation criteria was a five-step relative evaluation where the taste of the control product was 2, the very strong taste was 5, and the very weak taste was 1. The results are shown in Table 3.

  From the above results, pyroglutamylglycine was effective in enhancing the richness of consomme soup and making the taste more mellow and preferable than consomme soup.

[Example 4]
Pyroglutamylglycine was added to a commercially available coffee beverage and sensory evaluation was performed. 20 mg of pyroglutamylglycine was added to 1000 g of a commercially available coffee drink to prepare a sample for evaluation.
Using the above-mentioned commercially available coffee beverage as a control product, the umami, the strength of the rich taste, and the mildness of taste like a coffee beverage were evaluated for each coffee beverage using a panel of 10 people. The evaluation criteria were a 5-level relative evaluation where the taste of the control product was 2, the very strong taste was 5, and the very weak taste was 1. The results are shown in Table 4.

  From the above results, pyroglutamylglycine was found to have the effect of enhancing the richness of coffee beverages and making the taste more mellow and preferable like coffee.

[Example 5]
Pyroglutamyl glutamine was added to a commercially available green tea beverage for sensory evaluation. 30 mg of pyroglutamyl glutamine was added to 1000 g of a commercially available green tea beverage to prepare a sample for evaluation.
Using the above-mentioned commercially available green tea beverage as a control product, the umami, the strength of the rich taste, and the mildness of taste like a green tea beverage were evaluated for each green tea beverage using a panel of 10 people. The evaluation criteria were a 5-level relative evaluation where the taste of the control product was 2, the very strong taste was 5, and the very weak taste was 1. The results are shown in Table 5.

  From the above results, pyroglutamyl glutamine has the effect of enhancing the richness of green tea beverages and making the taste more mellow and preferable than green tea.

[Example 6]
When 0.1 part by mass of pyroglutamyl glutamine was added to commercially available concentrated soy sauce to prepare a Japanese-style seasoning, a rich, mellow and broad Japanese-style seasoning was obtained compared to the additive-free product.

[Example 7]
When 0.1 part by mass of pyroglutamylglycine was added to a commercial miso to prepare a miso, a rich and mellow miso was obtained compared to the additive-free product.

[Example 8]
10 parts by weight of milk, 80 parts by weight of water, 10 parts by weight of corn paste, 2 parts by weight of sugar and 0.5 parts by weight of sodium chloride were heated and stirred and emulsified at 10,000 rpm for 5 minutes. Furthermore, when 0.01 part by mass of pyroglutamyl glutamine was added to prepare a corn soup, a corn soup having a strong taste and broadness compared to the additive-free product was obtained.

[Example 9]
Add 50 parts by weight of weak flour to 50 parts by weight of palm oil, fry slowly over low heat, add 500 parts by weight of milk, 600 parts by weight of water, 3 parts by weight of chicken consomme powder, 6 parts by weight of salt, and mix well until viscosity rises After slowly heating on low heat, 1 part by mass of pyroglutamyl glutamine was added to prepare a white sauce. As a result, a corn soup with a strong taste and breadth was obtained compared to the additive-free product.

[Example 10]
40 parts by mass of raw yeast dissolved in water was added to 1400 parts by mass of strong powder and stirred well, followed by fermentation at 28 ° C. for 4 hours. To the obtained dough, 600 parts by weight of strong powder, 100 parts by weight of sugar, 100 parts by weight of milk, 40 parts by weight of salt, and 2 parts by weight of pyroglutamylglycine were added and kneaded well. After the fermentation for 30 minutes, the bread was baked at 220 ° C. for 40 minutes to prepare a bread. As a result, a bread with a strong taste and sweetness and a rich bread was obtained as compared with the additive-free product.

[Example 11]
15 parts by weight of shortening, 30 parts by weight of sugar, 3 parts by weight of whole egg, 1 part by weight of sodium chloride and 0.1 parts by weight of pyroglutamylglycine were added, stirred for 30 minutes, and then aged for 30 minutes. The obtained dough was poured into a mold and baked at 220 ° C. for 5 minutes to prepare hard biscuits. As a result, hard biscuits with a strong taste and sweetness and a mellow spread were obtained as compared with the additive-free products.

[Example 12]
60 parts by weight of sugar, 40 parts by weight of candy and 35 parts by weight of water are combined and heated to 155 ° C., then cooled to 130 ° C., 5 parts by weight of coffee extract, 0.3 parts by weight of caramel, 0.01 g of pyroglutamyl glutamine When a mass part was added, mixed and molded to prepare a coffee hard candy, a coffee hard candy having a rich natural sweetness with enhanced richness and a rich taste was obtained.

[Example 13]
To the water was added 10 parts by mass of fructose-glucose liquid sugar, 5 parts by mass of sugar, and 1 part by mass of a gelling agent. Furthermore, 0.01 parts by mass of pyroglutamyl glutamine was added, and after correcting the total amount to 100 parts by mass, the orange jelly was prepared by sterilizing at 85 ° C. for 20 minutes. An orange jelly having a refreshing sweetness with reduced aftertaste was obtained.

[Example 14]
15 parts by weight of full fat sweetened condensed milk and 3 parts by weight of fructose-glucose liquid sugar are dissolved in distilled water, and 2 parts by weight of full fat milk powder and 1 part by weight of skim milk powder previously dispersed in distilled water are added and heated at around 40 ° C. Then, 3.5 parts by weight of super white sugar, 0.7 parts by weight of stabilizer and 0.02 parts by weight of emulsifier were added and heated to 80 ° C. After adding 0.3 part by mass of corn starch, the mixture was sterilized (80 ° C., 15 minutes). The mass was adjusted to 100 parts by mass with hot water and emulsified with a clear mix. After adding 0.01 parts by mass of pyroglutamyl glycine and stirring, the mixture was cooled in a glass container to prepare a milk pudding. As a result, milk pudding with enhanced natural sweetness and added umami taste was obtained. .

  The flavor enhancer of the present invention has the effect of improving the sweetness, saltiness, bitterness, sourness, umami and / or richness of foods and drinks to be more mellow and preferable by adding them to foods and drinks. It can be used widely.

Claims (8)

Formula (1)

(Wherein R binds to an adjacent carbonyl group via an amino group in the molecule, serine, glycine, histidine, arginine, alanine, aspartic acid, glutamic acid, pyroglutamic acid, phenylalanine, threonine, cysteine, cystine, glutamine, Represents an amino acid residue selected from asparagine, methionine, tyrosine, tryptophan, valine, isoleucine, lysine or leucine)
The flavor enhancer characterized by consisting of the pyroglutamyl dipeptide represented by these, or its salt.   The flavor enhancer according to claim 1, wherein the amino acid is an L-form amino acid.   The flavor enhancer according to claim 1, wherein the amino acid is L-glutamine or L-glycine.   A seasoning comprising the flavor enhancer according to any one of claims 1 to 3. The seasoning according to claim 4, comprising 1 to 10 ⁶ ppm of a flavor enhancer as an active ingredient.   A food or drink comprising the seasoning according to claim 5 added thereto. The food / beverage product according to claim 6, comprising 0.1 to 10 ⁵ ppm of a flavor enhancer as an active ingredient.   A flavor enhancing method comprising adding 0.001 to 1 part by mass of the flavor enhancer according to any one of claims 1 to 3 to 1 part by mass of glutamic acid or a salt thereof.