JP2024141414A - Flavor-imparting composition - Google Patents

Abstract

[Problem] An object of the present invention is to provide a composition that can improve the flavor of plant-based foods without using beef extract. [Solution] The above object is achieved by a flavor-imparting composition containing methyl 5-hexenoate; a flavor-imparting composition containing methyl 5-hexenoate and 2-vinylpyrazine; and a method for imparting flavor to plant-based foods, comprising a step of cooking using methyl 5-hexenoate or methyl 5-hexenoate and 2-vinylpyrazine with a plant-derived ingredient. [Selected Figures] None

Description

The present invention relates to a flavor-imparting composition. More specifically, the present invention relates to a flavor-imparting composition used to impart flavor to a plant-based food product obtained using a plant-derived food ingredient.

Meat and fish dishes are generally enjoyed as main dishes at meals. However, in recent years, in addition to vegetarians, the number of strict vegetarians known as vegans, who do not eat any animal-derived food, including meat, fish, dairy products and eggs, has been increasing. Vegans eat plant-based foods that use plant-derived ingredients and no animal-derived ingredients.

The proteins, polyunsaturated fatty acids and other nutrients contained in animal-derived ingredients give food a rich, distinctive flavor. Meat in particular has a rich texture and a distinctive fat aroma, giving it a unique taste. In contrast, plant-based foods are often perceived as lacking in texture and flavor when compared to foods made with animal-derived ingredients.

When it comes to foods that use meat, meat extracts, which are meat extracts, are sometimes used instead of meat itself. Among meat extracts, beef extract can impart the distinctive richness and flavor of beef to foods. Beef extract is made from the broth that is a by-product produced during the manufacturing process of beef-based processed meat products such as corned beef and boiled beef. By cooking plant-derived ingredients with beef extract, the resulting foods can be imparted with richness and beef flavor.

Known substitutes for beef extract include a flavoring agent with a pH of 5.8 obtained by suspending a plant such as onion in a caustic soda solution, heating and refluxing the filtrate, adding dried wheat gluten hydrolysate, hydrochloric acid, ribose, and beef or beef tallow to the filtrate, and then heating and refluxing the resulting mixture (see, for example, Patent Document 1), and a meat flavoring agent for vegetable protein-containing foods that contains (E)-6-nonenal (see, for example, Patent Document 2).

Publication No. 56-5141 Patent No. 7011095

However, although beef extract is not meat itself, vegans dislike foods made using beef extract. In addition, the flavoring agent described in Patent Document 1 also uses beef or beef fat, so vegans cannot eat foods made using the flavoring agent described in Patent Document 1.

On the other hand, the flavor enhancer described in Patent Document 2 contains (E)-6-nonenal as an active ingredient. However, (E)-6-nonenal has a grassy odor similar to that of melon, and is not suitable for use in lightly flavored plant-based foods.

The problem that the present invention aims to solve is to provide a composition that can improve the flavor of plant-based foods without using beef extract.

The inventors of the present invention have conducted extensive research to solve the above problems, and have tried and tested numerous ingredients, either alone or in suitable combinations, to enhance the flavor of plant-based foods.

And, after much research, it was finally discovered that methyl 5-hexenoate can impart richness to plant-based foods obtained by processing plant-derived ingredients, making the flavor of the plant-based foods richer. Furthermore, it was surprisingly discovered that by combining methyl 5-hexenoate with 2-vinylpyrazine, it is possible to impart a beef flavor to the plant-based foods in addition to richness, more significantly than when each component is used alone. The flavor-imparting effect of the combination of methyl 5-hexenoate and 2-vinylpyrazine is not an additive effect based on each component, but a synergistic effect that is only manifested by the combination. The discovery that the flavor of plant-based foods can be improved by methyl 5-hexenoate or methyl 5-hexenoate and 2-vinylpyrazine is a surprising and unexpected discovery made for the first time by the present inventors.

Based on this knowledge, the inventors have succeeded in creating a composition that can improve the flavor of plant-based foods without using beef extract, in order to solve the problems of the present invention. The present invention was completed based on the knowledge and success stories first obtained by the inventors.

Thus, according to one aspect of the present invention, there is provided:
[1] A flavor-imparting composition comprising methyl 5-hexenoate.
[2] A flavor-imparting composition comprising methyl 5-hexenoate and 2-vinylpyrazine.
[3] The flavor-imparting composition according to [1] or [2], wherein the flavor-imparting composition is a packaged flavor-imparting composition.
[4] The flavor-imparting composition according to [1] or [2], which is used as a seasoning.
[5] The flavor-imparting composition according to [1] or [2], which is used for plant-based foods.
[6] The flavor-imparting composition according to [1] or [2], wherein the content of the methyl 5-hexenoate is an amount such that the content is 0.001 ppm to 5 ppm in the plant-based food used.
[7] The flavor-imparting composition according to [2], wherein the content of 2-vinylpyrazine is an amount such that the content is 0.001 ppm to 5 ppm in the plant-based food used.
[8] The flavor-imparting composition according to [2], wherein the content of the methyl 5-hexenoate is an amount such that the plant food used is 0.001 ppm to 5 ppm, and the content of the 2-vinylpyrazine is an amount such that the plant food used is 0.01 ppm to 5 ppm, or the content of the methyl 5-hexenoate is an amount such that the plant food used is 0.01 ppm to 5 ppm, and the content of the 2-vinylpyrazine is an amount such that the plant food used is 0.001 ppm to 5 ppm.
[9] A method for imparting flavor to a plant-based food, comprising a step of cooking using methyl 5-hexenoate or methyl 5-hexenoate and 2-vinylpyrazine with a plant-derived food ingredient.

According to the present invention, it is possible to impart a rich, beefy flavor to a plant-based food without using beef extract, thereby improving the flavor of the plant-based food. Furthermore, since the flavor-imparting composition of one embodiment of the present invention contains methyl 5-hexenoate or methyl 5-hexenoate and 2-vinylpyrazine as active ingredients, a plant-based food using the flavor-imparting composition of one embodiment of the present invention can still be a plant-based food. Thus, according to the present invention, it is possible to produce a highly palatable plant-based food for use in vegetarian and vegan meals.

The flavor-imparting composition of one embodiment of the present invention can be obtained by a simple manufacturing method, and therefore can be mass-produced on an industrial scale.

Each aspect of the present invention will be described in detail below, but the present invention is not limited to the items in this section, and various aspects may be adopted as long as the object of the present invention is achieved.

Unless otherwise specified, each term in this specification is used in the sense commonly used by those skilled in the art of food and should not be construed as having an unduly restrictive meaning. Furthermore, the speculations and theories made in this specification are based on the inventors' knowledge and experience to date, and therefore the present invention is not limited solely to such speculations and theories.

The term "composition" is not particularly limited to the commonly used meaning, but may be, for example, a combination of two or more ingredients. "Foodstuff" and "(raw) material" refer to a substance used (added) in producing a composition, and are synonymous with "ingredient.""Foodstuff" and "(raw) material" may exist in a composition in a qualitatively and/or quantitatively maintained or altered state compared to before use.
"Content" is synonymous with concentration and amount added (amount used), and refers to the ratio of the amount of a component to the total amount of a composition. However, the total amount of the content of the components does not exceed 100%. "w/v%" represents a mass volume percent concentration synonymous with "% (w/v)", "vol%" represents a volume percent concentration synonymous with "% (v/v)", and "wt%" represents a mass percent concentration synonymous with "% (w/w)". In addition, when a commercially available product is used, the content of the component is preferably the amount of the component contained in the commercially available product, but may be the amount of the commercially available product itself.
"Flavor" refers to the aroma (retronasal) that escapes from the oral cavity to the nose when held in the mouth, the taste (taste) that is felt on the tongue when held in the mouth, or both.
"Food" means foodstuffs, beverages or both. "Processed food" means food obtained by cooking ingredients. "Plant-based food" means processed food that contains mainly plant-derived ingredients and no animal-derived ingredients.
"Containerized" means filled or contained in a sealable airtight or sealed container. An airtight container is a container that prevents the intrusion of solid or liquid foreign matter and the loss or evaporation of the contents under normal handling, transportation, or storage conditions. A sealed container is a container that prevents the intrusion of gas under normal handling, transportation, or storage conditions.
"Comprising" means that elements other than the elements explicitly stated as being included can be added (same meaning as "comprising at least"), but also encompasses "consisting of" and "consisting essentially of." That is, "comprising" can mean including the elements explicitly stated and any one or more elements, consisting of the elements explicitly stated, or consisting essentially of the elements explicitly stated. Elements include limitations such as ingredients, steps, conditions, and parameters.
The term "and/or" means any one or any or all combinations of two or more of the associated listed items.
"ppm" is a unit as commonly known, specifically, 1 ppm is ^1/106 , which is 1 μg/g in mass conversion, and approximately 1 mg/L in mass/volume conversion.
The word "to" in a numerical range includes the numerical values before and after it, for example, "0% to 100%" means a range that is equal to or greater than 0% and equal to or less than 100%. "More than" and "less than" refer to the lower and upper limits, respectively, without including the numerical value before it, for example, "more than 1" means a number greater than 1, and "less than 100" means a number less than 100. "About" refers to an amount within ±10% of the quantity that follows the term, for example, "about 100" means 100 ±10%, i.e., 90 to 110.
The number of digits in an integer value is the same as the number of significant digits. For example, 1 has one significant digit, and 10 has two significant digits. Also, the number of digits after the decimal point in a decimal value is the same as the number of significant digits. For example, 0.1 has one significant digit, and 0.10 has two significant digits.

[Summary of flavor-imparting composition]
A first aspect of the present invention is a flavor-imparting composition comprising methyl 5-hexenoate. A second aspect of the present invention is a flavor-imparting composition comprising methyl 5-hexenoate and 2-vinylpyrazine. In this specification, methyl 5-hexenoate or methyl 5-hexenoate and 2-vinylpyrazine may be collectively referred to as "active ingredients".

The flavor-imparting composition of one embodiment of the present invention can impart richness, beef flavor, or both to a plant-based food obtained using a plant-derived food ingredient. In other words, a plant-based food using the flavor-imparting composition of one embodiment of the present invention has a richness and/or beef flavor superior to a plant-based food not using the flavor-imparting composition of one embodiment of the present invention. Such an effect of the flavor-imparting composition of one embodiment of the present invention, which imparts richness and/or beef flavor to a plant-based food, is also referred to as a "flavor-imparting effect."

[Active ingredient]
Methyl 5-hexenoate has a CAS registration number of 2396-80-7 and is represented by the following formula (I):
(I)
It is a compound having the structure represented by the following formula:

The content of methyl 5-hexenoate may be an amount that can exert a flavor-imparting effect. As shown in Table 1 in the examples described later, according to the investigations conducted by the present inventors, when a plant-based food contains 0.01 ppm or more of methyl 5-hexenoate, or when a plant-based food contains 0.001 ppm or more of methyl 5-hexenoate together with 2-vinylpyrazine, the richness of the plant-based food is felt strongly. On the other hand, when the content of methyl 5-hexenoate is high, the plant-based food may have a flavor (off-flavor) that is not normally felt. For example, when a plant-based food contains 10 ppm of methyl 5-hexenoate, the plant-based food may emit an off-flavor similar to kerosene.

Therefore, the content of methyl 5-hexenoate in the plant-based food is preferably 0.001 ppm or more and less than 10 ppm, and in order to exert a more excellent flavor-imparting effect, the content is more preferably 0.001 ppm to 5 ppm in the plant-based food, even more preferably 0.01 ppm to 5 ppm, and even more preferably 0.1 ppm to 3 ppm. Note that "an amount that results in 0.001 ppm to 5 ppm of methyl 5-hexenoate" means, for example, an amount such that 100 g of the plant-based food contains 0.1 μg to 500 μg of methyl 5-hexenoate.

For example, when the flavor-imparting composition of one embodiment of the present invention is used at 1 wt % in a plant-based food, and the flavor-imparting composition of one embodiment of the present invention contains 0.1 ppm to 500 ppm of methyl 5-hexenoate, the content of methyl 5-hexenoate in the plant-based food will be 0.001 ppm to 5 ppm.

2-Vinylpyrazine has a CAS registration number of 4177-16-6 and is represented by the following formula (II):
(II)
It is a compound having the structure represented by the following formula:

The amount of 2-vinylpyrazine contained may be any amount that can exert a flavor-imparting effect. As shown in Table 1 in the examples described below, according to research by the present inventors, when a plant-based food contains methyl 5-hexenoate and further contains 0.001 ppm or more of 2-vinylpyrazine, the plant-based food has a strong richness and beefy flavor. On the other hand, when the amount of 2-vinylpyrazine is high, the plant-based food may have a flavor (an unusual flavor) that is not normally felt. For example, when a plant-based food contains 10 ppm of 2-vinylpyrazine, the plant-based food may emit an unusual flavor that makes the tongue numb.

Therefore, the content of 2-vinylpyrazine in the plant-based food is preferably 0.001 ppm or more and less than 10 ppm, and in order to exert a more excellent flavor-imparting effect, the content is more preferably 0.001 ppm to 5 ppm, even more preferably 0.01 ppm to 5 ppm, and even more preferably 0.1 ppm to 3 ppm in the plant-based food.

For example, when the flavor-imparting composition of one embodiment of the present invention is used at 1 wt % in a plant-based food, and the flavor-imparting composition of one embodiment of the present invention contains 0.1 ppm to 500 ppm of 2-vinylpyrazine, the content of 2-vinylpyrazine in the plant-based food will be 0.001 ppm to 5 ppm.

The total amount of the active ingredient is not particularly limited, but in order to exert an effective effect on the plant-based food and to avoid a strong unpleasant flavor, it is preferable that the amount in the plant-based food is 0.01 ppm or more and less than 10 ppm, and in order to exert a more excellent flavor-imparting effect, it is more preferable that the amount in the plant-based food is 0.1 ppm to 5 ppm, and even more preferable that the amount is 0.5 ppm to 4 ppm.

For example, when the flavor-imparting composition of one embodiment of the present invention is used at 1 wt % in a plant-based food, and the flavor-imparting composition of one embodiment of the present invention contains 50 ppm to 100 ppm of methyl 5-hexenoate and 50 ppm to 100 ppm of 2-vinylpyrazine, the contents of methyl 5-hexenoate and 2-vinylpyrazine in the plant-based food are each 0.5 ppm to 1 ppm, and the total amount is 1.0 ppm to 2 ppm.

The active ingredient may be the active ingredient itself, or an active ingredient-containing product that contains the active ingredient. When using the active ingredient itself, commercially available products can be used.

[Flavor-imparting composition]
The flavor-imparting composition of one embodiment of the present invention can contain other ingredients in addition to the active ingredient. The other ingredients are not particularly limited, but include, for example, ingredients used in foods and seasonings, and specifically, liquid ingredients include water, soy sauce, alcohol, sweet ingredients (mirin, liquid sugar, starch syrup, etc.), sour ingredients (vinegar, apple, yuzu, lemon, and other citrus fruits), oil and fat ingredients (sesame oil, olive oil, salad oil, soybean oil, chili oil, etc.), alcoholic beverage ingredients (wine, sake, etc.), fruit juice (apple juice, etc.); solid ingredients include salt, sugars (sugar, Examples of food additives include glucose, fructose, starch syrup, isomerized liquid sugar, etc.), grain ingredients (bread crumbs, wheat flour, oatmeal, etc.), spices (ginger, chili pepper, pepper, basil, oregano, ginger, mixed spices, etc.), thickeners (thickening polysaccharides such as carrageenan, starch, modified starch, gums, etc.), chemical seasonings (glutamic acid, sodium glutamate, glycine, sodium inosinate, sodium guanylate, etc.), flavors, miso, curry powder, and plant-derived ingredients.

The plant-derived foodstuff is not particularly limited as long as it is derived from a plant that is generally used as a foodstuff, but examples include vegetables such as radish, onion, leek, carrot, burdock, lotus root, ginger, garlic, cabbage, bell pepper, tomato, corn, and bamboo shoots; spicy vegetables such as shiso, parsley, celery, Chinese chives, and mitsuba; mushrooms such as shiitake, mushrooms, enoki, and shimeji; fruits such as apples, pears, kiwi, pineapple, and plums; nuts and seeds such as sesame, nuts, and chestnuts; and seaweed such as hijiki, kelp, and wakame. The plant-derived foodstuff may be a processed plant food such as tofu, fried tofu, konjac, soy protein, and the like. In other words, the plant-derived foodstuff may be one that has been subjected to processing such as grating a plant, making it into a paste, crushing, slicing, cutting into dices, strips, or the like, baking, or frying.

However, when the flavor-imparting composition of one embodiment of the present invention is applied to plant-based foods, it is preferable that it does not contain animal-derived ingredients such as meat, eggs, or dairy products.

The other components may be one of the above alone or a combination of two or more. The content of the other components may be set appropriately as long as the problem of the present invention can be solved.

The flavor-imparting composition of one embodiment of the present invention is not particularly limited in its form, but it is preferably a liquid composition such as a liquid, suspension, or paste, since it mixes well with food ingredients.

The flavor-imparting composition of one embodiment of the present invention may be a packaged composition filled in a sealable airtight or sealed container. The container is not particularly limited as long as it is an airtight or sealed container, and examples of the container include packaging containers such as single-layer or laminated film bags, retort pouches, vacuum packs, molded containers, bottles, and cans made of metals such as aluminum and steel, paper, plastics such as PET, and glass. The packaged composition can be sold independently and commercially available in the market. Note that a container with a lid used for the purpose of storing food at home is a sealed container, and is strictly distinguished from an airtight container and a sealed container, especially a sealed container.

The flavor-imparting effect of the flavoring composition of one embodiment of the present invention may be an effect of imparting a stronger richness, beef flavor, or both to a plant-based food using the composition compared to a plant-based food (control) not using the composition under the same conditions. The flavor-imparting effect includes the effect of imparting a beef flavor to a plant-based food that is not normally felt in plant-based foods, as well as the effect of imparting a richness to the plant-based food so that the plant-based food has a richness that it does not normally have, or so that the richness that the plant-based food originally has is made richer.

The flavor-imparting action can be confirmed by the method described in the Examples below. For example, a sensory evaluation of sukiyaki warishita using a flavor-imparting composition according to one embodiment of the present invention is performed on the evaluation items "richness" and "beef flavor," and at least one evaluation result selected from the group consisting of a stronger sense of "richness" and a stronger sense of "beef flavor" compared to a control, and preferably all two evaluation results, are obtained. By increasing the flavor-imparting action, the plant-based food used becomes more palatable. From this perspective, the flavor-imparting action is preferably an action that results in an overall evaluation of "◎," "○," or "△" when a similar sensory evaluation is performed, more preferably an action that results in an overall evaluation of "◎" or "○," and even more preferably an action that results in an overall evaluation of "◎."

The food to be used with the flavor-imparting composition of one embodiment of the present invention is not particularly limited, and may be either a plant-based food or an animal-based food, but in order to strongly express the flavor-imparting effect, a plant-based food is preferable. The plant-based food is not particularly limited, but examples include sukiyaki-wari, plant-based bouillon, dressing, salad, soy sauce, sauce, ketchup, dipping sauce, broth, ponzu sauce, Chinese soy sauce, soup, noodles, noodle broth, plant-based pate, plant-based milk, cooking sake, seasoning oil, etc.

The amount of the flavor-imparting composition of one embodiment of the present invention used is not particularly limited and can be appropriately set depending on the content of the active ingredient in the flavor-imparting composition of one embodiment of the present invention, the food material to which the flavor-imparting composition of one embodiment of the present invention is to be applied, and the type and amount of the processed food to be produced. For example, the amount of the flavor-imparting composition of one embodiment of the present invention used is preferably 0.001% to 50% by mass, more preferably 0.01% to 10% by mass, and even more preferably 0.1% to 5% by mass, relative to the plant-based food.

The method for producing the flavor-imparting composition of one embodiment of the present invention is not particularly limited, and examples thereof include a method for producing a seasoning by mixing each component as is commonly known, specifically a method including mixing the active ingredient with other components such as water, alcohol, and seasoning components by a mixing means such as stirring at room temperature or under heating. The other components may be pre-treated by being subjected to a process such as chopping, crushing, swelling, or heating.

The flavor-imparting composition of one embodiment of the present invention is preferably a heated composition. In addition, in consideration of storage stability, the flavor-imparting composition of one embodiment of the present invention is preferably one that has been subjected to anti-spoilage treatment, such as sterilization treatment by heating or filtration. The flavor-imparting composition of one embodiment of the present invention is preferably a composition that has been subjected to sterilization treatment under conditions that are normally used when sterilizing foods such as seasonings, and is preferably a composition that has been heat-sterilized at 100°C or less for several seconds to several minutes. The flavor-imparting composition of one embodiment of the present invention may be subjected to retort sterilization. Retort sterilization may be performed at a temperature, pressure, and time that allows sterilization to a state that allows long-term storage, and is not particularly limited. For example, retort sterilization is performed under normal pressure or pressure, at 100°C to 130°C, preferably about 120°C, for 1 minute to 30 minutes, preferably about 10 minutes.

A non-limiting specific embodiment of the present invention is a flavor-imparting composition comprising the following component (A) in an amount of 1 wt %:
Component (A) 1 ppm or more and less than 1,000 ppm of methyl 5-hexenoate (0.01 ppm or more and less than 10 ppm in plant-based foods)

A non-limiting specific embodiment of the present invention is a flavoring composition comprising the following components (A) and (B) in an amount of 1 wt %.
Component (A): 5-hexenoic acid methyl, 0.1 ppm or more and less than 1,000 ppm (0.001 ppm or more and less than 10 ppm in plant-based foods)
Component (B) 2-vinylpyrazine at 1 ppm or more and less than 1,000 ppm (at 0.01 ppm or more and less than 10 ppm in plant foods)

A non-limiting specific embodiment of the present invention is a flavoring composition comprising the following components (A) and (B) in an amount of 1 wt %.
Component (A): 0.1 ppm to 500 ppm of methyl 5-hexenoate (0.001 ppm to 5 ppm for plant foods)
Component (B) 0.1 ppm to 500 ppm of 2-vinylpyrazine (0.001 ppm to 5 ppm for plant foods)

A non-limiting specific embodiment of the present invention is a flavoring composition comprising the following components (A) and (B) in an amount of 1 wt %.
Component (A): 1 ppm to 500 ppm of methyl 5-hexenoate (0.01 ppm to 5 ppm for plant foods)
Component (B) 1 ppm to 500 ppm of 2-vinylpyrazine (0.01 ppm to 5 ppm for plant foods)

A non-limiting specific embodiment of the present invention is a flavoring composition comprising the following components (A) and (B) in an amount of 1 wt %.
Component (A): 10 ppm to 300 ppm of methyl 5-hexenoate (0.1 ppm to 3 ppm for plant foods)
Component (B) 10 ppm to 300 ppm of 2-vinylpyrazine (0.1 ppm to 3 ppm for plant foods)

A non-limiting specific embodiment of the present invention is a flavoring composition comprising the following components (A) and (B) in an amount of 1 wt %.
Component (A): 1 ppm to 500 ppm of methyl 5-hexenoate (0.01 ppm to 5 ppm for plant foods)
Component (B) 0.1 ppm to 500 ppm of 2-vinylpyrazine (0.001 ppm to 5 ppm for plant foods)

By using the flavor-imparting composition of one embodiment of the present invention and a plant-derived food material and cooking them at room temperature or by heating, a highly palatable plant-based food product with improved flavor, such as richness and beef flavor, can be obtained. The flavor-imparting composition of one embodiment of the present invention can be used as a seasoning.

The method of cooking a plant-derived food using the flavor-imparting composition of one embodiment of the present invention as a seasoning is not particularly limited, and can be appropriately set depending on the type and amount of plant-derived ingredients used, the type of plant-derived food to be obtained, etc. For example, cooking methods include ordinary heating and cooking methods such as stir-frying, deep-frying, baking, steaming, heating using a microwave oven, heating with hot air, and heating in hot water.

[Another aspect of the present invention]
By using the active ingredient, it is possible to impart richness, beef flavor, or both to a plant-based food. Thus, another aspect of the present invention is a method for imparting flavor to a plant-based food, comprising a step of cooking the plant-based food using methyl 5-hexenoate or methyl 5-hexenoate and 2-vinylpyrazine, and a plant-derived food ingredient.

The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples, and the present invention can take various forms as long as the object of the present invention can be solved.

Example 1: Evaluation of the effect of a flavor-imparting composition on a plant-based food [1-1. Preparation of a flavor-imparting composition]
0.1 g of methyl 5-hexenoate (purity over 98.0% manufactured by Tokyo Chemical Industry Co., Ltd.) was placed in a 10 ml volumetric flask and diluted with 95% ethanol to prepare a methyl 5-hexenoate stock solution (1 g/100 ml). Next, the methyl 5-hexenoate solution to be added to each test food described below was standardized to 100 μl when the methyl 5-hexenoate solution was used alone, or to 50 μl when used in combination with a 2-vinylpyrazine solution, and the methyl 5-hexenoate stock solution was diluted with water so that the content of methyl 5-hexenoate in each test food was a predetermined amount, to prepare each methyl 5-hexenoate solution.

0.1 g of 2-vinylpyrazine (Sigma-Aldrich) with a purity of over 97% was placed in a 10 ml measuring flask and diluted with 95% ethanol to prepare a 2-vinylpyrazine stock solution (1 g/100 ml). Next, the amount of 2-vinylpyrazine solution added to each test food (described below) was standardized to 100 μl when the 2-vinylpyrazine solution was used alone, or 50 μl when used in combination with a 5-methyl hexenoate solution, and the 2-vinylpyrazine stock solution was diluted with water to prepare each 2-vinylpyrazine solution so that the content of 2-vinylpyrazine in each test food was the specified amount.

As shown in Table 1, test foods 1 to 14 were prepared by adding 0.1 ml of 5-hexenoic acid methyl solution, 0.1 ml of 2-vinylpyrazine solution, or 0.1 ml of a mixture of 5-hexenoic acid methyl solution and 2-vinylpyrazine solution to diluted sukiyaki warishita obtained by diluting "Ningyocho Imahan Sukiyaki Warishita" (manufactured by Kinoene Shoyu Co., Ltd.), which does not contain animal ingredients, twice with water.

Reference food 1 was diluted sukiyaki wari with neither methyl 5-hexenoate solution nor 2-vinylpyrazine solution added, and reference foods 2 and 3 were diluted sukiyaki wari with 1 wt% and 2 wt% of "Beef Extract N" (Tsukasa Foods Co., Ltd.), respectively.

[1-2. Sensory evaluation method]
For the sensory evaluation, the test foods and reference foods at room temperature were placed on a spoon, eaten, and the intensity of the "richness" and "beef flavor" felt on the tongue when placed in the mouth was evaluated using a 6-point scoring system (0 being the weakest and 5 being the strongest).

"Body" refers to the taste felt on the tongue with persistence and breadth, and can also be described as the depth of flavor. "Beef flavor" refers to the distinctive meaty aroma of beef that can be felt in beef extract.

In the sensory evaluation, reference foods 1 to 3 were used as indices, and for both "richness" and "beef flavor," reference food 1 was given a score of 0, reference food 2 a score of 3, and reference food 3 a score of 5. Based on these indices, the panel assigned scores to the test foods according to the following criteria.
0: No difference from reference food 1 1: Slightly stronger than reference food 1 2: Stronger than reference food 1, but weaker than reference food 2 3: About the same as reference food 2 4: Stronger than reference food 2, but weaker than reference food 3 5: About the same as or stronger than reference food 3

In the overall evaluation, test foods with "richness" and "beef flavor" each rated 4 points or more were rated as foods with excellent palatability with a rating of "◎", test foods with "richness" and "beef flavor" each rated 3 points or more and 4 points or less were rated as foods with high palatability with a rating of "○", test foods with either "richness" or "beef flavor" rated 3 points or more and the other less than 3 points were rated as foods with good palatability with a rating of "△", and test foods with "richness" and "beef flavor" each rated less than 3 points were rated as foods with poor palatability with a rating of "×". In addition, test foods that had a strange flavor not normally felt in sukiyaki warishita were also rated as "×", regardless of the score for "richness" or "beef flavor".

[1-3. Sensory evaluation results]
The results of the sensory evaluation of test foods 1 to 14 are shown in Table 1. As shown in Table 1, test foods 1 to 4 containing 0.01 ppm to 10 ppm of methyl 5-hexenoate were perceived as having a stronger richness than reference food 1, which did not contain methyl 5-hexenoate. However, when the methyl 5-hexenoate content was 10 ppm, the flavor as a plant-based food was improved and the problem of the present invention could be solved, but an unusual flavor similar to kerosene was perceived.

These results show that methyl 5-hexenoate, especially methyl 5-hexenoate with a content of 0.01 ppm or more and less than 10 ppm, has the effect of imparting body and improving the flavor of plant-based foods.

Test foods 5 to 8, which contained 0.01 ppm to 10 ppm of 2-vinylpyrazine, had a slightly richer, beefier flavor than reference food 1, which did not contain 2-vinylpyrazine. However, when the 2-vinylpyrazine content was 10 ppm, an unusual flavor that caused a numbing sensation on the tongue was present. These results show that 2-vinylpyrazine itself has a weak effect of imparting richness and beefy flavor to plant-based foods.

In contrast, test foods 9 to 14, which contained 2-vinylpyrazine in addition to methyl 5-hexenoate, had a stronger richness than reference food 1, which did not contain methyl 5-hexenoate or 2-vinylpyrazine. Test foods 10 to 14 also had a stronger beef flavor that was not present or was barely present in test foods 1 to 7, which contained only methyl 5-hexenoate or only 2-vinylpyrazine. However, test food 14, which contained 10 ppm of 2-vinylpyrazine, had an improved flavor as a plant-based food and was able to solve the problem of the present invention, but it had a strange flavor that caused a numbing sensation on the tongue.

Test Foods 11 and 9 contained very small amounts of methyl 5-hexenoate and 2-vinylpyrazine, each at 0.001 ppm, but by containing both methyl 5-hexenoate and 2-vinylpyrazine, they not only had a rich flavor but also a beefy taste.

These results show that a combination of methyl 5-hexenoate and 2-vinylpyrazine, particularly a combination in which the methyl 5-hexenoate content is 0.001 ppm or more and less than 10 ppm and the 2-vinylpyrazine content is 0.01 ppm or more and less than 10 ppm, or a combination in which the methyl 5-hexenoate content is 0.01 ppm or more and less than 10 ppm and the 2-vinylpyrazine content is 0.001 ppm or more and less than 10 ppm, has the effect of imparting body and a beefy flavor to plant-based foods.

Since 5-methyl hexenoate and 2-vinylpyrazine alone are unable to impart a beef flavor to plant-based foods, it was found that the effect of imparting a beef flavor to plant-based foods by combining these ingredients is a synergistic effect rather than an additive effect of each ingredient.

Example 2 Evaluation of flavor imparting to plant-based foods As an example of the flavor imparting effect of an active ingredient on plant-based foods , sukiyaki was prepared using soy protein instead of meat by using a sukiyaki warishita with 5-methyl hexenoate and 2-vinylpyrazine.

A test sample was prepared by adding the mixture of methyl 5-hexenoate and 2-vinylpyrazine prepared in Example 1 to sukiyaki warisukiyaki that does not contain animal ingredients so that the content of each component was 1 ppm. As a control, a reference sample was prepared by adding beef extract to the sample so that the content was 2 wt%.

100 g of rehydrated soy protein ("Fujinic-PT-FLH"; Fuji Oil Co., Ltd.), 25 g of onion, 25 g of green onion, 35 g of shiitake mushrooms, 50 g of tofu, and 60 g of Chinese cabbage were placed in a pot, and the test or reference ingredients were added and heated to cook sukiyaki.

A comparison of soy protein in sukiyaki cooked with the test material and the reference material showed that the sukiyaki cooked with the test material, which contained 1 ppm each of methyl 5-hexenoate and 2-vinylpyrazine, had a rich, beefy flavor, and a good overall flavor, and was comparable to the sukiyaki cooked with the reference material containing added beef extract.

As another example of the effect of active ingredients in imparting flavor to plant-based foods, a Japanese-style sesame dressing was prepared using 5-methyl hexenoate and 2-vinylpyrazine.

32.5g of granulated sugar, 15g of ground sesame, 15g of dark soy sauce, 15g of sesame oil, 30g of rapeseed salad oil, and 7.5g of vinegar were mixed together to prepare a Japanese-style sesame dressing.

A test dressing was prepared by adding the mixture of methyl 5-hexenoate and 2-vinylpyrazine prepared in Example 1 to Japanese sesame dressing so that the content of each component was 1 ppm. A reference dressing was also prepared by adding beef extract to Japanese sesame dressing so that the content was 2 wt%.

When the test dressing and the reference dressing were compared, the test dressing had a rich, beefy flavor, and a good overall flavor, and was comparable to the reference dressing.

The flavor-imparting composition of one embodiment of the present invention is capable of imparting a desirable flavor to plant-based foods, can be produced industrially, and can be used in restaurants and at home, making it useful as a seasoning for use in a variety of situations.

Claims (9)

A flavor-imparting composition containing methyl 5-hexenoate. A flavor-imparting composition comprising methyl 5-hexenoate and 2-vinylpyrazine. The flavor-imparting composition according to claim 1 or 2, wherein the flavor-imparting composition is a packaged flavor-imparting composition. The flavor-imparting composition according to claim 1 or 2, which is used as a seasoning. The flavor-imparting composition according to claim 1 or 2, which is used for plant-based foods. The flavor-imparting composition according to claim 1 or 2, wherein the content of the methyl 5-hexenoate is in an amount of 0.001 ppm to 5 ppm in the plant food in which it is used. The flavor-imparting composition according to claim 2, wherein the content of the 2-vinylpyrazine is in an amount such that the plant food to which it is applied has a content of 0.001 ppm to 5 ppm. The flavor-imparting composition according to claim 2, wherein the content of the methyl 5-hexenoate is an amount that is 0.001 ppm to 5 ppm in the plant food used, and the content of the 2-vinylpyrazine is an amount that is 0.01 ppm to 5 ppm in the plant food used, or the content of the methyl 5-hexenoate is an amount that is 0.01 ppm to 5 ppm in the plant food used, and the content of the 2-vinylpyrazine is an amount that is 0.001 ppm to 5 ppm in the plant food used. A method for imparting flavor to a plant-based food, comprising a step of cooking the food using methyl 5-hexenoate or methyl 5-hexenoate and 2-vinylpyrazine, and a plant-derived food ingredient.