Pungency enhancer, method for enhancing spiciness, food composition, and method for producing a food composition.

Abstract

The objectives are to provide novel spiciness enhancers for chili peppers, ginger, or black pepper, and to provide novel spiciness enhancers for capsaicinoids, gingerol, shogaol, or piperine. [Solution] Compound represented by the following formula (1): JPEG0007869392000026.jpg38170 The above problem can be solved by a spice, spice extract, or spice flavor enhancer in a food containing the following, comprising (wherein R is a hydroxy(C1-6) alkyl group, a formyl group (-CHO), a (C1-6) alkylformyl group, a formyloxymethyl group (-CH2OC(O)H), a (C1-6) aliphatic acyloxymethyl group, a carboxyl group (-COOH), or a (C1-6) alkylcarboxyl group), wherein the spice is chili pepper, ginger, or black pepper.

Description

Technical Field

[0001] The present invention relates to a pungency enhancer and a method for enhancing pungency. The present invention also relates to a food composition and a method for producing the food composition.

Background Art

[0002] In recent years, globalization has advanced, and a variety of people have come to eat a variety of spices. Among them, there are people who prefer the strong flavor of spices, but if a large amount of spices or components derived from spices are blended, it may lead to an increase in the cost of the product.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] Patent Document 1 discloses a compound that can enhance the salty taste effect by adding a small amount. Regarding the pungency of spices, there has also been a desire for such an enhancing component.

Means for Solving the Problems

[0005] The present inventor has intensively studied a novel pungency enhancer for spices. As a result, surprisingly, it has been found that the compound represented by the formula (1) has an effect of enhancing the pungency of various spices. Further, from the evaluation results by trained panelists in the examples described later, the compound represented by the formula (1) is considered to have an action of enhancing the pungency exhibited by capsinoids, gingerols, shogaols, or piperine, which are pungent components. The present invention is based on such findings. Therefore, the present invention includes the following embodiments. [1] Compounds represented by the following formula (1): [ka] (In the formula, R is a hydroxy(C1-6)alkyl group, a formyl group (-CHO), a (C1-6)alkylformyl group, a formyloxymethyl group (-CH2OC(O)H), a (C1-6)aliphatic acyloxymethyl group, a carboxyl group (-COOH), or a (C1-6)alkylcarboxyl group.) A spice, a spice extract, or a spiciness enhancer in a food containing these, The aforementioned spice is a spice enhancer, which is chili pepper, ginger, or black pepper. [2] The pungent flavor enhancer according to [1], wherein R is selected from a hydroxymethyl group (-CH2OH), a formyl group (-CHO), a formyloxymethyl group (-CH2OC(O)H), and an acetyloxymethyl group (-CH2OC(O)CH3). [3] The pungent flavor enhancer according to [1] or [2], wherein the compound represented by formula (1) is administered in an amount of 0.001 ppb to 1.0% by mass in the spice, spice extract, or food standard containing these after addition. [4] Compounds represented by the following formula (1): [ka] (wherein R is a hydroxy(C1-6)alkyl group, a formyl group (-CHO), a (C1-6)alkylformyl group, a formyloxymethyl group (-CH2OC(O)H), a (C1-6)aliphatic acyloxymethyl group, a carboxyl group (-COOH), or a (C1-6)alkylcarboxyl group), and Spices or spice extracts A food composition containing, A food composition in which the spice is chili pepper, ginger, or black pepper. [5] The compound represented by formula (1) is present in a concentration of 0.001 ppb to 1.0% by mass based on the total amount of the composition. The food composition described in [4], which includes the following: [6] The food composition according to [4] or [5], wherein R is selected from a hydroxymethyl group (-CH2OH), a formyl group (-CHO), a formyloxymethyl group (-CH2OC(O)H), and an acetyloxymethyl group (-CH2OC(O)CH3). [7] The food composition according to any one of [4] to [6], comprising 0.1 to 99% by mass of the spice or spice extract based on the total amount of the composition. [8] Compounds represented by the following formula (1): [ka] (wherein R is a hydroxy(C1-6)alkyl group, a formyl group (-CHO), a (C1-6)alkylformyl group, a formyloxymethyl group (-CH2OC(O)H), a (C1-6)aliphatic acyloxymethyl group, a carboxyl group (-COOH), or a (C1-6)alkylcarboxyl group) Contact with spices, spice extracts, or foods containing them. A method for enhancing the spiciness of spices, spice extracts, or foods containing the same, A method for enhancing spiciness, wherein the spice is chili pepper, ginger, or black pepper. [9] The method for enhancing spiciness according to [8], wherein R is selected from a hydroxymethyl group (-CH2OH), a formyl group (-CHO), a formyloxymethyl group (-CH2OC(O)H), and an acetyloxymethyl group (-CH2OC(O)CH3).

[10] The method according to [8] or [9], wherein the compound represented by formula (1) is brought into contact with the spice, spice extract, or food standard containing these in an amount of 0.001 ppb to 1.0% by mass.

[11] Compounds represented by the following formula (1): [ka] (In the formula, R is a hydroxy(C1-6)alkyl group, a formyl group (-CHO), a (C1-6)alkylformyl group, a formyloxymethyl group (-CH2OC(O)H), a (C1-6)aliphatic acyloxymethyl group, a carboxyl group (-COOH), or a (C1-6)alkylcarboxyl group.) and contact with spices, spice extracts, or foods containing them. A method for producing a food composition, including, A method for producing a food composition, wherein the spice is chili pepper, ginger, or black pepper.

[12] A method for producing a food composition according to

[11] , wherein R is selected from a hydroxymethyl group (-CH2OH), a formyl group (-CHO), a formyloxymethyl group (-CH2OC(O)H), and an acetyloxymethyl group (-CH2OC(O)CH3).

[13] The method according to

[11] or

[12] , wherein the compound represented by formula (1) is brought into contact with the composition at a concentration of 0.001 ppb to 1.0% by mass on a basis of the total amount of the composition.

[14] Compounds represented by the following formula (1): [ka] (wherein R is a hydroxy(C1-6)alkyl group, a formyl group (-CHO), a (C1-6)alkylformyl group, a formyloxymethyl group (-CH2OC(O)H), a (C1-6)aliphatic acyloxymethyl group, a carboxyl group (-COOH), or a (C1-6)alkylcarboxyl group), and Capsaicinoids, gingerol, shogaol, or piperine, in an amount of 0.5 ppm to 10.0% by mass based on the total weight of the composition. Includes food composition.

[15] The food composition according to

[14] , comprising 0.001 ppb to 1.0% by mass of the compound represented by formula (1) on a basis of the total amount of the composition.

[16] In the formula, R is selected from a hydroxymethyl group (-CH2OH), a formyl group (-CHO), a formyloxymethyl group (-CH2OC(O)H), and an acetyloxymethyl group (-CH2OC(O)CH3), and is the food composition according to

[14] or

[15] .

[17] The compound represented by formula (1) is 0.01 ppb to 0.1% by mass based on the total amount of the composition, and capsaicinoid, gingerol, shogaol, or piperine is 0.5 ppm to 1.0% by mass based on the total amount of the composition The food composition according to any one of

[14] to

[16] .

[18] The content of the compound represented by formula (1) based on the total amount of the composition is a mass ratio of 0.000001 to 10 with respect to the content of capsaicinoid, gingerol, shogaol, or piperine based on the total amount of the composition (content of the compound represented by formula (1) based on the total amount of the composition / content of capsaicinoid, gingerol, shogaol, or piperine based on the total amount of the composition), and is the food composition according to any one of

[14] to

[17] .

[19] A compound represented by the following formula (1):

Chemical formula

[19] , the compound represented by formula (1) may be martenol or martenal. [1] to

[19] , the compound represented by formula (1) may be isolated martenol or isolated martenal.

[0006] Furthermore, the present invention also includes the following embodiments. [A1] The use of a compound represented by the following formula (1) for enhancing the spiciness of a spice, a spice extract, or a food containing the same, wherein the spice is chili pepper, ginger, or black pepper: [ka] (wherein R is a hydroxy(C1-6)alkyl group, a formyl group (-CHO), a (C1-6)alkylformyl group, a formyloxymethyl group (-CH2OC(O)H), a (C1-6)aliphatic acyloxymethyl group, a carboxyl group (-COOH), or a (C1-6)alkylcarboxyl group). [A2] In the formula, R is selected from a hydroxymethyl group (-CH2OH), a formyl group (-CHO), a formyloxymethyl group (-CH2OC(O)H), and an acetyloxymethyl group (-CH2OC(O)CH3), as described in [A1]. [A3] The use described in [A1] or [A2], wherein the compound represented by formula (1) is administered in a concentration of 0.001 ppb to 1.0% by mass in the spice, spice extract, or food standard containing these after addition. [B1] Use of compounds represented by the following formula (1) for enhancing spiciness in foods containing capsaicinoids, gingerol, shogaol, or piperine: [ka] (wherein R is a hydroxy(C1-6)alkyl group, a formyl group (-CHO), a (C1-6)alkylformyl group, a formyloxymethyl group (-CH2OC(O)H), a (C1-6)aliphatic acyloxymethyl group, a carboxyl group (-COOH), or a (C1-6)alkylcarboxyl group). [B2] In the formula, R is selected from a hydroxymethyl group (-CH2OH), a formyl group (-CHO), a formyloxymethyl group (-CH2OC(O)H), and an acetyloxymethyl group (-CH2OC(O)CH3), as described in [B1]. [B3] The use described in [B1] or [B2], wherein the compound represented by formula (1) is administered in a manner that results in a concentration of 0.001 ppb to 1.0% by mass in a spice, spice extract, or food standard containing these after addition. In [A1] to [B3], the compound represented by formula (1) may be myrtenol or myrtenal. In [A1] to [B3], the compound represented by formula (1) may be isolated myrtenol or isolated myrtenal. [Effects of the Invention]

[0007] According to the present invention, novel spiciness enhancers for various spices can be provided. Furthermore, according to the present invention, novel spiciness enhancers such as capsaicinoids, gingerols, shogaols, or piperine can be provided. [Modes for carrying out the invention]

[0008] The spiciness enhancer of the present invention is a compound represented by the following formula (1): [ka] (In the formula, R is a hydroxy(C1-6)alkyl group, a formyl group (-CHO), a (C1-6)alkylformyl group, a formyloxymethyl group (-CH2OC(O)H), a (C1-6)aliphatic acyloxymethyl group, a carboxyl group (-COOH), or a (C1-6)alkylcarboxyl group.) It includes. In the pungent flavor enhancer of the present invention, the compound represented by formula (1) may be in the form of a salt, insofar as it has the effect of the present invention.

[0009] A hydroxy(C1-6)alkyl group refers to a substituent having a structure in which one or more hydroxyl groups (-OH) are bonded to a linear or branched aliphatic alkyl chain having 1 to 6 carbon atoms. While having one hydroxyl group is preferred, it may have two or three or more. Specific examples include hydroxymethyl group (-CH2OH), 2-hydroxyethyl group (-CH2CH2OH), and 1,3-dihydroxypropyl group (-CH2CH(OH)CH2OH). The hydroxy(C1-6)alkyl group is preferably a hydroxy(C1-3)alkyl group, and more preferably a hydroxymethyl group (-CH2OH).

[0010] A (C1-6) alkylformyl group refers to a substituent having a structure in which one or more formyl groups (-CHO) are bonded to a linear or branched aliphatic alkyl chain having 1 to 6 carbon atoms. It is preferable to have one formyl group, but it may have two or more. Specific examples include formylmethyl group (-CH2CHO) and formylethyl group (-CH2CH2CHO). The (C1-6) alkylformyl group is preferably a (C1-3) alkylformyl group.

[0011] A (C1-6) aliphatic acyloxymethyl group refers to a substituent having a structure in which an acyl group (R'-CO-) derived from a linear or branched aliphatic carboxylic acid with 1 to 6 carbon atoms is bonded to a methyl group (-CH2-) via an oxy group (-O-). Specific examples include acetyloxymethyl group (-CH2OC(O)CH3), propionyloxymethyl group (-CH2OC(O)CH2CH3), and butyryloxymethyl group (-CH2OC(O)CH2CH2CH3). A (C1-6) aliphatic acyloxymethyl group is preferably a (C1-3) aliphatic acyloxymethyl group.

[0012] A (C1-6) alkylcarboxyl group refers to a substituent having a structure in which a carboxyl group (-COOH) is bonded to the end of a linear or branched aliphatic alkyl chain having 1 to 6 carbon atoms. It is preferable to have one carboxyl group, but it may have two or more. Specifically, examples include a carboxymethyl group (-CH2COOH), a carboxyethyl group (-CH2CH2COOH), and a carboxypropyl group (-CH2CH2CH2COOH). The (C1-6) alkylcarboxyl group is preferably a (C1-3) alkylcarboxymethyl group.

[0013] In formula (1), R is preferably selected from a hydroxy(C1-6) alkyl group, a formyl group (-CHO), a (C1-6) alkylformyl group, a formyloxymethyl group (-CH2OC(O)H), and a (C1-6) aliphatic acyloxymethyl group, more preferably selected from a hydroxy(C1-6) alkyl group, a formyl group (-CHO), a formyloxymethyl group (-CH2OC(O)H), and a (C1-6) aliphatic acyloxymethyl group, even more preferably selected from a hydroxymethyl group (-CH2OH), a formyl group (-CHO), a formyloxymethyl group (-CH2OC(O)H), and an acetyloxymethyl group (-CH2OC(O)CH3), even more preferably selected from a hydroxymethyl group (-CH2OH) and a formyl group (-CHO), and most preferably R is a hydroxymethyl group (-CH2OH).

[0014] (Myrtenol and Myrtenal) In formula (1), the compound in which R is a hydroxymethyl group is called myrtenol [(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methanol].

[0015] Compounds in formula (1) in which R is a formyl group (-CHO) or a (C1-6) alkylformyl group can be obtained by oxidizing the hydroxyl group of myrtenol. An example of such a compound is myrtenal (where R is -CHO).

[0016] Furthermore, compounds in formula (1) where R is a formyloxymethyl group (-CH2OC(O)H) or a (C1-6) aliphatic acyloxymethyl group can be obtained by reacting the hydroxyl group of myrtenol with a carboxylic acid (dehydration condensation) to esterify it. Examples of such compounds include myrtel acetate (R is -CH2OC(O)CH3), myrtel formate (R is -CH2OC(O)H), and myrtel butyrate (R is -CH2OC(O)CH2CH2CH3).

[0017] The structures of myrtenol and myrtenal are shown below. [ka] Myrtenol. [ka] Myrtenall.

[0018] The compound represented by formula (1) has the following characteristic ring structure: 6,6-dimethylbicyclo[3.1.1]hepta-2-ene-2 ​​structure. The 6,6-dimethylbicyclo[3.1.1]hepta-2-ene-2 ​​structure is also called α-pinene. [ka] α-pinene itself does not have a pungent-enhancing effect. It is surprising that α-pinene does not have a pungent-enhancing effect, while its analogues, myrtenol, and its oxides and esters do.

[0019] If the compound represented by formula (1) contains multiple isomers, the spiciness enhancer of the present invention may contain any of the isomers or multiple isomers.

[0020] The compound represented by formula (1) may be commercially available or prepared in-house. Preparation methods may include known methods (e.g., chemical synthesis, enzymatic methods, fermentation, extraction, etc.) or similar methods. For example, myrtenol can be purchased commercially from Nippon Terpene Chemical Co., Ltd. or Sigma-Aldrich Co. LLC. The spiciness enhancer of the present invention may be in the form of a food ingredient containing the compound represented by formula (1), or in the form of a formulation containing an isolated compound represented by formula (1). Examples of food ingredients containing the compound represented by formula (1) include animal and plant-derived raw materials (extracts, purified products, etc.) that contain a large amount of the compound represented by formula (1). The isolated compound represented by formula (1) can be prepared by known methods, such as synthesis, microbial culture, or extraction and purification. The isolated compound represented by formula (1) may include a compound of the compound represented by formula (1), or an extract obtained from a composition containing the compound represented by formula (1) (e.g., myrtenol or myrtenal), which contains the compound represented by formula (1) (e.g., myrtenol or myrtenal). The isolated compound represented by formula (1) may or may not be purified. If the pungent flavor enhancer of the present invention contains the isolated compound represented by formula (1), it may be provided in a state containing a solvent for dissolution and other additives. Other additives include excipients, binders, disintegrants, emulsifiers, lubricants, flow enhancers, diluents, preservatives, colorants, flavorings, flavorings, stabilizers, humectants, preservatives, antioxidants, or suspending agents. The above description of the isolated compound represented by formula (1) also applies to capsaicinoids, gingerols, shogaols, or piperines, as described later. The isolated compound represented by formula (1) is preferably isolated myrtenol, isolated myrtenal, isolated myrtelacetate, or isolated myrtelformate, and more preferably isolated myrtenol or isolated myrtenal. Myrtenol and its oxide, myrtenal, have a characteristic mild aroma but lack a strong taste and spiciness. Similarly, myrtel acetate and myrtel formate, which are esters of myrtenol, also have a characteristic mild aroma but lack a strong taste and spiciness. The spiciness enhancer of the present invention is thought to be able to enhance the spiciness of chili peppers, ginger, or black pepper (hereinafter sometimes referred to as the three spices) or foods to which these are added, without impairing the flavor of the three spices. The compound represented by formula (1) is preferably myrtenol, myrtenal, myrtel acetate, or myrtel formate, more preferably myrtenol or myrtenal, and most preferably myrtenol.

[0021] The concentration of the compound represented by formula (1) in the spiciness enhancer of the present invention is not particularly limited, as long as it is a concentration that can enhance the spiciness of the three spices, extracts of the three spices, or foods containing these (hereinafter sometimes referred to as "three spices, etc.") when added to the three spices, extracts of the three spices, or foods containing these (hereinafter sometimes referred to as "three spices, etc."). It may contain 1% by mass or more, 10% by mass or more, 30% by mass or more, 50% by mass or more, 80% by mass or more, or 99% by mass or more, based on the total amount of the spiciness enhancer. The spiciness enhancer of the present invention may consist of the compound represented by formula (1). The above content is the total amount if two types of compounds represented by formula (1) are included.

[0022] The spiciness enhancer of the present invention may be in the form of a solid or powder formulation such as fine granules, granules, tablets, capsules, or pills, or a liquid formulation such as a suspension, paste, emulsion, syrup, or extract. The spiciness enhancer of the present invention may be, for example, in the form of a dissolved water containing a compound represented by formula (1), intended for addition to three spices in powder form.

[0023] The amount of the spiciness enhancer of the present invention added can be appropriately determined considering the types of the three spices, etc. Specifically, the spiciness enhancer of the present invention can be added such that the concentration of the compound represented by formula (1) in the three spices, etc. after addition is 0.001 ppb to 1.0% by mass, preferably 0.001 ppb to 8000 ppm, more preferably 0.01 ppb to 5000 ppm, more preferably 0.05 ppb to 1000 ppm, even more preferably 0.1 ppb to 800 ppm, even more preferably 0.1 ppb to 500 ppm, even more preferably 0.1 ppb to 100 ppm, even more preferably 1 ppb to 100 ppm, even more preferably 10 ppb to 100 ppm, and most preferably 100 ppb to 100 ppm. The above concentration is the total amount if two types of the compound represented by formula (1) are included. The above concentration is the final concentration in the three spices, etc. after addition. In this specification, "ppm" and "ppb" mean mass ratio. By increasing the concentration of the compound represented by formula (1) to 0.1 ppb or higher, the spiciness can be significantly enhanced. Furthermore, by increasing the concentration of the compound represented by formula (1) to 100 ppb or higher, the spiciness can be more significantly enhanced. The spiciness enhancer of the present invention contains a compound represented by formula (1) as an active ingredient, and by adding only a very small amount, it is possible to enhance the spiciness of three types of spices.

[0024] (Chili pepper) In this specification, "chili pepper" means the plant body (including roots, stems, leaves, flowers, fruits, and seeds) of a plant belonging to the genus Capsicum, preferably a seasoning prepared from the fruit. There are various species in the genus Capsicum. In this specification, however, the genus Capsicum includes, but is not limited to, C. annuum, C. baccatum, C. chinense, C. frutescens, and C. pubescens. In this specification, “chili pepper” includes packaged products containing chili peppers or chili pepper extracts, intended to be added to other foods to impart a chili pepper flavor to those foods (hereinafter sometimes referred to as “chili pepper products”). Chili pepper products are preferably dried chili pepper products, chili pepper powder products, grated chili pepper products, chili pepper sauce products, or chili pepper dressing products.

[0025] (Ginger) In this specification, "ginger" means the plant body of Zingiber officinale (including rhizomes, stems, leaves, flowers, fruits, and seeds), preferably a seasoning prepared from the rhizome. In this specification, "ginger" includes packaged products containing ginger or ginger extract, intended for addition to other foods to impart a ginger flavor to those foods (hereinafter sometimes referred to as "ginger products"). Ginger products are preferably dried ginger products, powdered ginger products, grated ginger products, ginger sauce products, ginger syrup products, and ginger dressing products.

[0026] (Pepper) In this specification, "pepper" means the plant body (including rhizomes, stems, leaves, flowers, fruits, and seeds) of plants belonging to the genus Piper, preferably a seasoning prepared from the fruit. There are various species in the genus Piper. In this specification, the genus Piper includes, but is not limited to, Piper longum, Piper retrofractum, and Piper cubeba. In this specification, "pepper" includes packaged products containing pepper or pepper extract, intended for addition to other foods to impart a peppery flavor to those foods (hereinafter sometimes referred to as pepper products). Pepper products are preferably dried pepper products, powdered pepper products, coarse-ground pepper products, pepper sauce products, pepper dressing products, and pepper salt products.

[0027] Furthermore, products that contain the three spices and the compound represented by formula (1) separately in a single product package are also included in chili pepper products, ginger products, or pepper products. For example, powdered ginger products include products that contain ginger syrup and dissolved water containing the compound represented by formula (1), and in which the ginger syrup and the dissolved water containing the compound represented by formula (1) are mixed after purchase. In the above case, ginger ale or ginger lemonade with enhanced ginger spiciness can be obtained.

[0028] (extract) In this specification, "extracts" of the three spices mean extracts obtained by extracting the pungent components from the plants of these spices using any extraction method. As for the extraction method, any known extraction method can be used without limitation. Examples of extraction methods for the pungent components contained in the three spices include solvent extraction, steam distillation, pressing, or supercritical fluid extraction. A combination of these extraction methods may also be used, for example, a method combining solvent extraction and steam distillation. When employing solvent extraction, the extraction solvent is preferably water, alcohol, hexane, acetone, or a mixture thereof, and more preferably water, ethanol, or a mixture thereof.

[0029] The components that give chili peppers their spiciness include, for example, capsaicinoids (capsaicin, dihydrocapsaicin, homocapsaicin, etc.) and capsiates. Examples of pungent components found in ginger include [6]-gingerol, [6]-shogaol, and zingerone. Examples of pungent components in pepper include piperine.

[0030] (Foods containing chili peppers, ginger, or black pepper, or extracts thereof) In this specification, “foods containing chili peppers, ginger, or pepper or extracts thereof” is not particularly limited as long as it contains the three spices or extracts thereof, and includes, for example, the following foods: • Cooked foods such as steaks, pizzas, and hamburgers; • Stir-fried dishes such as stir-fried vegetables; Processed foods made from vegetables such as tomatoes, bell peppers, celery, bitter melon, carrots, potatoes, and asparagus; Cookies, bread, biscuits, hardtack, cakes, rice crackers, sweet bean jelly, pudding, jelly, ice cream, chewing gum, crackers, chips, chocolate, and candy; • Noodles such as udon, pasta, and soba; • Fish paste products such as kamaboko (fish cake), ham, and fish sausage; • Dairy products such as cheese, cream, and butter; • Seasonings other than chili products, ginger products, or pepper products, such as miso, soy sauce, ketchup, mayonnaise, soup base, noodle soup base, curry powder, curry roux, mirin, furikake, instant ochazuke mix, oil, etc. • Soy products such as tofu; • Liquid foods and beverages such as juice and soup.

[0031] Foods containing chili peppers, ginger, or black pepper, or extracts thereof, may contain only one or two of these, or all of them. Foods containing chili peppers, ginger, or black pepper, or extracts thereof, may be mixed spices containing all of these, such as curry powder or curry roux.

[0032] Three types of spices to which the compound represented by formula (1) has been added, or three types of spices containing the compound represented by formula (1), may hereafter be referred to as the first food composition of the present invention. The first food composition of the present invention may optionally contain food additives and food materials, either individually or in combination of two or more, such as antioxidants, flavorings, acidulants, colorings, emulsifiers, preservatives, seasonings, sweeteners, other spices or their extracts, pH adjusters, stabilizers, vegetable oils, animal oils, sugars and sugar alcohols, vitamins, organic acids, fruit juice extracts, vegetable extracts, grains, legumes, vegetables, meats, and seafood. The amounts of these food materials and food additives can be appropriately determined within a range that does not impair the effects of the present invention.

[0033] (container packaging) The first food composition of the present invention can be consumed immediately after preparation, or it can be sealed and stored using packaging materials. Examples of packaging materials include highly airtight materials such as glass bottles, metal cans, bottles, tubes (e.g., plastic tubes), bags (e.g., aluminum pouches), etc.

[0034] (composition) The first food composition of the present invention may contain three spices, more specifically the plant bodies of the three spices (powder, dried powder, extract, grated paste, etc.) or extracts thereof, in amounts of 0.1 to 99% by mass, 0.5 to 90% by mass, 1 to 80% by mass, 2 to 70% by mass, 3 to 60% by mass, 5 to 50% by mass, or 10 to 40% by mass, based on the total amount of the composition. The lower limit may be 15% by mass, 20% by mass, 25% by mass, 30% by mass, 35% by mass, 40% by mass, or 50% by mass. The amount of water in the first food composition of the present invention is not limited to the following, but can be 10-90% by mass, 15-80% by mass, 18-70% by mass, 20-60% by mass, or 20-50% by mass based on the total amount of the composition. The amount of solids in the first food composition of the present invention is not limited to the following, but can be 10-90% by mass, 15-85% by mass, 30-80% by mass, or 50-80% by mass based on the total amount of the composition. Moisture and solids can be measured by methods such as the loss on drying method or the vacuum drying method. The content of the compound represented by formula (1) in the first food composition of the present invention can be the content described above.

[0035] (Form of food) The first food composition of the present invention can be in any suitable form. Examples of suitable forms include liquid, paste, solid, powder, and granular forms.

[0036] (Capsaicinoids, gingerol, shogaol, or piperine) Capsaicinoids are the pungent compounds found in chili peppers. In this specification, capsaicinoids refer not only to capsaicin but also to the total amount of its analogues. Gingerol and shogaol are pungent compounds found in ginger. Piperine is a pungent compound found in pepper. The compound represented by formula (1) is thought to enhance the spiciness derived from these capsaicinoids, gingerol, shogaol, or piperine. The first food composition of the present invention may contain, for example, 1 ppm to 10.0% by mass, preferably 5 ppm to 5.0% by mass, more preferably 10 ppm to 1.0% by mass, and even more preferably 20 ppm to 500 ppm, of capsaicinoids, gingerol, shogaol, or piperine. Isolated capsaicinoids, gingerols, shogaols, or piperines can be prepared by known methods, such as synthesis, microbial culture, or extraction and purification. The isolated capsaicinoids, gingerols, shogaols, or piperines may be provided in a state containing a solvent for dissolution and other additives. Other additives may include excipients, binders, disintegrants, emulsifiers, lubricants, flow enhancers, diluents, preservatives, colorants, flavorings, flavorings, stabilizers, humectants, antiseptics, antioxidants, or suspending agents.

[0037] (The ratio of the compound represented by formula (1) to capsaicinoids, gingerol, shogaol, or piperine) The mass ratio of the content of the compound represented by formula (1) to the content of capsaicinoids, gingerol, shogaol, or piperine (content of the compound represented by formula (1) / content of capsaicinoids, gingerol, shogaol, or piperine) may be, for example, 0.000001 to 10, 0.00001 to 10, 0.0001 to 10, 0.001 to 10, 0.001 to 10, 0.01 to 10, or 0.1 to 10.

[0038] (Increased spiciness) In this specification, "enhancing spiciness" or "enhancing spiciness" means that when the compound represented by formula (1) is consumed together with the three spices, it causes the eater to perceive spiciness beyond the original spiciness derived from the three spices, thereby making the eater feel that the spiciness from the three spices has been enhanced. Therefore, by using the compound represented by formula (1), the amount of the three spices in the three spices can be reduced.

[0039] In this specification, the content of the compound represented by formula (1) can be measured by LC-MS (liquid chromatography-mass spectrometry) or GC-MS (gas chromatography). Detailed measurement methods for myrtenol and myrtenal are shown below. The content can be measured by changing the following conditions depending on the compound being measured. (1)Analysis method An organic solvent is added to the sample, and osmosis extraction is performed for 20 minutes. The extract is centrifuged to obtain a filtrate. This process is repeated twice, and the combined extracts are filtered. This filtrate is measured using a liquid chromatograph-mass spectrometer. (2) Calibration curve creation for the substance to be measured Prepare several standard solutions (miltenol, myrtenal) of the substance to be measured at different concentrations using methanol. Inject 10 μL of these solutions into a liquid chromatograph-mass spectrometer. Measure the peak area or height of each component using a data processing device. Create calibration curves with weight on the x-axis and peak area or height on the y-axis. <Conditions for liquid chromatography> Column: ODS column Mobile phase A: Water containing 0.1% formic acid: Mobile phase B: Acetonitrile containing 0.1% formic acid Flow rate: 0.3mL / min Gradient conditions (mobile phase A / B): 50 / 50 (3 min) - (4 min) - 30:70 Column temperature: 40℃ <Mass spectrometer conditions> • Ionization method: Electrospray ionization (ESI) • Monitoring ions: Myrtenol (135.1>91.0 or 135.1> Miltenard (151.1 > 81.1 or 151.1 > 79.1)

[0040] In this specification, the content of capsaicinoids, gingerol, shogaol, or piperine can be measured by LC-MSMS (liquid chromatography-mass spectrometry). Detailed methods for measuring capsaicinoids, gingerol, shogaol, and piperine are described below.

[0041] • Capsaicinoid analysis (1)Analysis method Add 20 mL of ethanol to 2 g of the sample and heat extract at 75°C for 1 hour. This solution is filtered, injected into a liquid chromatograph, and measured. (2) Calibration curve creation for the substance to be measured Standard solutions of several substances to be measured at different concentrations are prepared using ethanol. These solutions are injected into a liquid chromatograph, and the peak area or height of each component is measured using a data processing device. Calibration curves are then created with weight on the x-axis and peak area or height on the y-axis. <Liquid Chromatography Conditions> Column: ODS column, inner diameter 4.6 mm, length 150 mm, particle size 5 μm Mobile phase: 1% aqueous acetic acid solution / acetonitrile (60:40, v / v) Column flow rate: 1.5 mL / min Detector: Fluorescence detector Ex 280nm Em 325nm Injection volume: 20μL

[0042] Gingerol / Shogaol Analysis (1)Analysis method An 80% methanol aqueous solution is added to the sample, and extraction is performed by ultrasonic irradiation. This solution is filtered, injected into a liquid chromatograph, and measured. (2) Calibration curve creation for the substance to be measured Prepare standard solutions of several substances to be measured at different concentrations using 80% methanol. Inject these solutions into a liquid chromatograph and measure the peak area or height of each component using a data processing device. Create calibration curves with weight on the x-axis and peak area or height on the y-axis. <Liquid Chromatography Conditions> Column: ODS column, inner diameter 4.6 mm, length 250 mm, particle size 5 μm Mobile phase: Water / acetonitrile 30:70(3min)-(10min)-10:90(5min) Column flow rate: 1.0 mL / min Detector: UV-Vis absorbance detector 280nm Injection volume: 10μL

[0043] Piperine analysis (1)Analysis method Ethanol is added to the sample, and extraction is performed by heating under reflux. This solution is filtered, injected into a liquid chromatograph, and measured. (2) Calibration curve creation for the substance to be measured Prepare standard solutions of several substances to be measured at different concentrations using an ethanol aqueous solution. Inject these solutions into a liquid chromatograph and measure the peak area or height of each component using a data processing device. Create calibration curves with weight on the x-axis and peak area or height on the y-axis. <Liquid Chromatography Conditions> Column: ODS column, inner diameter 4.6 mm, length 250 mm, particle size 5 μm Mobile phase: 1% acetic acid aqueous solution / acetonitrile = 50 / 50 Column flow rate: 1.0 mL / min Detector: UV-Vis absorbance detector 343nm Injection volume: 10μL

[0044] (Methods to increase spiciness) The present invention relates to a method for enhancing spiciness, which involves contacting a compound represented by formula (1) with three types of spices, etc. The compound represented by formula (1) may be in the form of a food ingredient containing the compound represented by formula (1), or it may be a formulation containing an isolated compound represented by formula (1). Alternatively, the compound represented by formula (1) may be mixed with other arbitrary ingredients before being contacted with the three types of spices, etc. The definitions and preferred ranges of various terms are as described above.

[0045] (Method of producing food composition) The method for producing the first food composition of the present invention involves contacting a compound represented by formula (1) with three kinds of spices, etc. The compound represented by formula (1) may be in the form of a food ingredient containing the compound represented by formula (1), or it may be in the form of an isolated compound represented by formula (1). Alternatively, the compound represented by formula (1) may be mixed with any other ingredients before being contacted with the three kinds of spices, etc. The three kinds of spices, etc. may be prepared in-house or purchased from others. The definitions and preferred ranges of various terms are as described above. The method for producing the first food composition of the present invention may optionally include steps such as sterilization, homogenization, cooling, and packaging of a mixture of the compound represented by formula (1) and three types of spices, etc. The definitions and preferred ranges of various terms are as described above.

[0046] (Second food composition) The second food composition of the present invention contains a compound represented by formula (1), and capsaicinoids, gingerol, shogaol, or piperine (particularly capsaicinoids, gingerol, or shogaol) in an amount of 1 ppm to 10.0% by mass based on the total amount of the composition. The definitions and preferred ranges of various terms described above in the first food composition of the present invention can be applied to the second food composition of the present invention, but the second food composition of the present invention may or may not contain three spices, extracts of three spices, or foods containing these.

[0047] (Method for producing the second food composition) The method for producing the second food composition of the present invention involves contacting a compound represented by formula (1) with a capsaicinoid, gingerol, shogaol, or piperine (particularly a capsaicinoid, gingerol, or shogaol). Regarding the method for producing the second food composition of the present invention, the definitions and preferred ranges of various terms described above in the method for producing the first food composition of the present invention may be applied. However, the second food composition in the method for producing the second food composition of the present invention may be three spices, extracts of three spices, or a food containing these, or it may not be three spices, extracts of three spices, or a food containing these. The definitions and preferred ranges of various terms are as described above. [Examples]

[0048] The present invention will be specifically described below with reference to examples, but these examples are not intended to limit the scope of the invention. Unless otherwise specified, % refers to mass %. Myrtenol or myrtenal is isolated myrtenol or myrtenal purchased from Sigma Aldrich.

[0049] Example 1: Investigation of the effect of enhancing the spiciness of chili pepper extract. In this example, experiments were conducted using chili pepper extract and myrtenol. A commercially available chili pepper extract was used, diluted 50 times with water. The diluted chili pepper extract contained approximately 52 ppm of capsaicinoids on a total basis. Diluted chili pepper extract and myrtenol were mixed at various concentrations, and six trained panelists evaluated whether the spiciness of the diluted chili pepper extract with added myrtenol was enhanced compared to the diluted chili pepper extract without added myrtenol (control). The evaluation criteria were as follows: • N; No effect (same as or less spicy than the control), 0 points A; Weak effect (slightly spicier than the control), 1 point • AA; Effective (spicier than the control), 2 points • AAA; Highly effective (Spicier than the control), 3 points

[0050] The evaluation results from the six trained panelists are shown below. [Table 1] The left column shows the concentration of myrtenol based on the total volume of the diluted chili pepper extract. In all cases where the myrtenol concentration ranged from 0.1 to 100,000 ppb, the effect of adding myrtenol to enhance the spiciness of diluted chili pepper extract was confirmed. Furthermore, the spiciness-enhancing effect increased with increasing myrtenol concentration, and at concentrations of 100 ppb or higher, the spiciness of the diluted chili pepper extract was significantly enhanced compared to the control. Furthermore, the six panelists assessed that the spiciness of the capsaicinoids was enhanced in the diluted chili pepper extract. In addition, the six panelists assessed that the flavors other than spiciness in the diluted chili pepper extract were not affected by myrtenol. From the above, it was found that adding myrtenol to chili pepper extract enhances the spiciness of the chili pepper extract and / or capsaicinoids.

[0051] Example 2: Investigation of the effect of enhancing the spiciness of ginger. In this example, experiments were conducted using grated ginger juice and myrtenol. The grated ginger juice was prepared by grating commercially available ginger. Grated ginger juice and myrtenol were mixed at various concentrations, and six trained panelists evaluated whether the spiciness of the ginger juice with added myrtenol was enhanced compared to grated ginger juice without added myrtenol (control). The evaluation criteria were as follows: • N; No effect (same as or less spicy than the control), 0 points A; Weak effect (slightly spicier than the control), 1 point • AA; Effective (spicier than the control), 2 points • AAA; Highly effective (Spicier than the control), 3 points

[0052] The evaluation results from the six trained panelists are shown below. [Table 2] The left column shows the concentration of myrtenol based on the total amount of grated ginger juice. In all cases where the myrtenol concentration ranged from 0.1 to 100,000 ppb, the effect of adding myrtenol to enhance the spiciness of grated ginger juice was confirmed. Furthermore, the spiciness-enhancing effect increased with higher myrtenol concentrations, and at concentrations of 1 ppb or higher, the spiciness of grated ginger juice was significantly enhanced compared to the control. The six panelists assessed that the spiciness of gingerol and shogaol was enhanced in grated ginger juice. Specifically, the six panelists assessed that both the sharp spiciness of gingerol and the mild, lingering spiciness of shogaol were enhanced. Furthermore, the six panelists assessed that the flavors of the grated ginger juice, other than its spiciness, were not affected by myrtenol. From the above, it was found that adding myrtenol to grated ginger juice enhances the pungent taste of grated ginger juice, gingerol, and / or shogaol.

[0053] Example 3: Investigation of the effect of enhancing the spiciness of pepper. In this example, experiments were conducted using a hot water extract of pepper and myrtenol. The hot water extract of pepper was prepared by adding 50g of hot water to 10g of commercially available black pepper, letting it stand overnight, and then centrifuging to obtain only the supernatant. Hot water extracts of pepper and myrtenol were mixed at various concentrations, and five trained panelists examined whether the hot water extracts of pepper with added myrtenol were more pungent than the hot water extracts of pepper without added myrtenol (control). The evaluation criteria were as follows: • N; No effect (same as or less spicy than the control), 0 points A; Weak effect (slightly spicier than the control), 1 point • AA; Effective (spicier than the control), 2 points • AAA; Highly effective (Spicier than the control), 3 points

[0054] The evaluation results from the five trained panelists are shown below. [Table 3] The left column shows the concentration of myrtenol based on the total amount of hot water extract from pepper. In all cases where the myrtenol concentration ranged from 0.1 to 10,000 ppb, the effect of myrtenol addition on enhancing the spiciness of hot water extracts of pepper was confirmed. Furthermore, the spiciness-enhancing effect increased with increasing myrtenol concentration, and at concentrations of 1 ppb or higher, the spiciness of the hot water extracts of pepper was significantly enhanced compared to the control. The five panelists assessed that the spiciness of piperine was enhanced in the hot water extract of pepper. Furthermore, the five panelists assessed that the flavors of the hot water extract of pepper, other than its spiciness, were not affected by myrtenol. From the above, it was found that adding myrtenol to a hot water extract of pepper enhances the spiciness of the hot water extract of pepper and / or piperine.

[0055] Example 4: Investigation of the effect of enhancing the spiciness of curry powder. In this example, experiments were conducted using curry powder extract and myrtenol. The curry powder used was S&B Foods Co., Ltd.'s Red Can Curry Powder. The curry powder extract was prepared by adding 50g of hot water to 10g of pure curry powder, shaking, letting it stand for 10 minutes, filtering, and collecting the supernatant. Curry powder contains various spices in addition to pepper, chili peppers, and ginger. Curry powder extract and myrtenol were mixed to a myrtenol concentration of 10,000 ppb. Three trained panelists then evaluated whether the curry powder extract with added myrtenol had enhanced spiciness compared to the curry powder extract without added myrtenol (control). The evaluation criteria were as follows. In Example 4, all samples, from those with weak effects to those with strong effects, were rated as A. • N; No effect (same as or less spicy than the control) • A; Effective (spiciness is increased compared to the control)

[0056] The evaluation results from the three trained panelists are shown below. [Table 4] The left column shows the concentration of myrtenol based on the total amount of curry powder extract. At a myrtenol concentration of 10,000 ppb, the effect of adding myrtenol on enhancing the spiciness of curry powder extract was confirmed. Furthermore, the three panelists assessed that the flavors of the curry powder extract, other than its spiciness, were not affected by myrtenol. From the above, it was found that adding myrtenol to curry powder extract enhances the spiciness of the curry powder extract.

[0057] Example 5: Examination of the spiciness-enhancing effect of myrthenal. In this example, experiments were conducted using diluted chili pepper extract or grated ginger juice with myrthenal. The diluted chili pepper extract and grated ginger juice were the same as those prepared in Examples 1 and 2. Diluted chili pepper extract or grated ginger juice was mixed with myrthenal to a concentration of 10,000 ppb. Four trained panelists then evaluated whether the spiciness of the diluted chili pepper extract or grated ginger juice with added myrthenal was enhanced compared to the diluted chili pepper extract or grated ginger juice without added myrthenal (control). The evaluation criteria were as follows. In Example 5, all results, from weak to strong effects, were rated as A. • N; No effect (same as or less spicy than the control) • A; Effective (spiciness is increased compared to the control)

[0058] The evaluation results from four trained panelists are shown in Tables 5 and 6 below. Table 5 shows the results for diluted chili extract, and Table 6 shows the results for grated ginger juice. [Table 5] [Table 6]

[0059] The left column shows the concentration of myrthenal based on the total volume of diluted chili pepper extract or grated ginger juice. At a myrthenal concentration of 10,000 ppb, the effect of adding myrthenal to diluted chili pepper extract or grated ginger juice in enhancing its spiciness was confirmed. The four panelists assessed that the spiciness of capsaicinoids, or gingerol and shogaol, was enhanced in the diluted chili extract or grated ginger juice, respectively. Furthermore, the four panelists assessed that the flavors of the diluted chili extract or grated ginger juice, other than the spiciness, were not affected by myrthenal. From the above, it was revealed that adding myrthenal to diluted chili pepper extract or grated ginger juice enhances the spiciness of the diluted chili pepper extract and / or capsaicinoids, or the spiciness of grated ginger juice, gingerol, and / or shogaol, respectively.

[0060] Example 6: Investigation of the effect of enhancing the spiciness of dried ginger. In this example, experiments were conducted using dried ginger and myrtenol. Fresh ginger contains more gingerol than shogaol, while dried ginger contains more shogaol than shogaol. Ginger tea was prepared by adding 100 times the amount of hot water (20 mL) to 0.2 g of dried ginger. Myrtenol was mixed into this ginger tea to a concentration of 4000 ppb, and four trained panelists examined whether the spiciness of the ginger tea with myrtenol was enhanced compared to ginger tea without myrtenol (control). The evaluation criteria were as follows: • N; No effect (same as or less spicy than the control), 0 points A; Weak effect (slightly spicier than the control), 1 point • AA; Effective (spicier than the control), 2 points • AAA; Highly effective (Spicier than the control), 3 points

[0061] The evaluation results from the four trained panelists are shown below. [Table 7] The left column shows the concentration of myrtenol based on the total volume of ginger tea. At a myrtenol concentration of 4,000 ppb, the effect of adding myrtenol on enhancing the spiciness of ginger tea was confirmed. The four panelists assessed that the spiciness of gingerol and shogaol was enhanced in ginger tea. Specifically, they assessed that both the sharp spiciness of gingerol and the mild, lingering spiciness of shogaol were enhanced. Furthermore, the four panelists assessed that the flavors of the ginger tea, other than its spiciness, were not affected by myrtenol. From the above, it was found that adding myrtenol to ginger tea prepared using dried ginger enhances the pungent taste of ginger tea, gingerol, and / or shogaol. [Industrial applicability]

[0062] According to the present invention, novel spiciness enhancers for chili peppers, ginger, or black pepper can be provided. Furthermore, according to the present invention, novel spiciness enhancers such as capsaicinoids, gingerol, shogaol, or piperine can be provided.

Claims

1. Compound represented by the following formula (1): 【Chemistry 1】 (In the formula, R is selected from a hydroxymethyl group (-CH₂OH), a formyl group (-CHO), a formyloxymethyl group (-CH₂OC(O)H), and an acetyloxymethyl group (-CH₂OC(O)CH₃)) A spice, a spice extract, or a spiciness enhancer in a food containing these, The aforementioned spice is a spice enhancer, which is chili pepper, ginger, or black pepper.

2. The spiciness enhancer according to claim 1, wherein the compound represented by formula (1) is administered in such a manner that it is present in a spice, spice extract, or food standard containing these ingredients at a concentration of 0.001 ppb to 1.0% by mass after addition.

3. Compound represented by the following formula (1): 【Chemistry 1】 (wherein R is selected from a hydroxymethyl group (-CH2OH), a formyl group (-CHO), a formyloxymethyl group (-CH2OC(O)H), and an acetyloxymethyl group (-CH2OC(O)CH3)), and Spices or spice extracts A food composition containing, A food composition in which the spice is chili pepper, ginger, or black pepper.

4. The compound represented by formula (1) is present in an amount of 0.001 ppb to 1.0% by mass, based on the total amount of the composition. The food composition according to claim 3, including the food composition according to claim 3.

5. The food composition according to claim 3 or 4, comprising 0.1 to 99% by mass of the spice or spice extract based on the total amount of the composition.

6. Compound represented by the following formula (1): 【Chemistry 1】 (wherein R is selected from a hydroxymethyl group (-CH2OH), a formyl group (-CHO), a formyloxymethyl group (-CH2OC(O)H), and an acetyloxymethyl group (-CH2OC(O)CH3)) Contact with spices, spice extracts, or foods containing them. A method for enhancing the spiciness of spices, spice extracts, or foods containing the same, A method for enhancing spiciness, wherein the spice is chili pepper, ginger, or black pepper.

7. The method according to claim 6, wherein the compound represented by formula (1) is brought into contact with the spice, spice extract, or food standard containing these in an amount of 0.001 ppb to 1.0% by mass after addition.

8. Compound represented by the following formula (1): 【Chemistry 1】 (In the formula, R is selected from a hydroxymethyl group (-CH₂OH), a formyl group (-CHO), a formyloxymethyl group (-CH₂OC(O)H), and an acetyloxymethyl group (-CH₂OC(O)CH₃)) and contact with spices, spice extracts, or foods containing them. A method for producing a food composition, including, A method for producing a food composition, wherein the spice is chili pepper, ginger, or black pepper.

9. The method according to claim 8, wherein the compound represented by formula (1) is brought into contact with the composition in an amount of 0.001 ppb to 1.0% by mass, based on the total amount of the composition.

10. Compound represented by the following formula (1): 【Chemistry 1】 (wherein R is selected from a hydroxymethyl group (-CH2OH), a formyl group (-CHO), a formyloxymethyl group (-CH2OC(O)H), and an acetyloxymethyl group (-CH2OC(O)CH3)), and A food composition containing 0.5 ppm to 10.0% by mass of capsaicinoids, gingerol, shogaol, or piperine based on the total amount of the composition.

11. The compound represented by formula (1) is present in an amount of 0.001 ppb to 1.0% by mass, based on the total amount of the composition. A food composition according to claim 10, including the food composition according to claim 10.

12. The compound represented by formula (1) is used in an amount of 0.01 ppb to 0.1% by mass based on the total amount of the composition, and Capsaicinoids, gingerol, shogaol, or piperine, at a concentration of 0.5 ppm to 1.0% by mass based on the total amount of the composition. A food composition according to claim 10 or 11, including the food composition according to claim 10 or 11.

13. The food composition according to claim 10 or 11, wherein the content of the compound represented by formula (1) on a total basis of the composition is 0.000001 to 10 by mass ratio to the content of capsaicinoid, gingerol, shogaol, or piperine on a total basis of the composition (content of the compound represented by formula (1) on a total basis of the composition / content of capsaicinoid, gingerol, shogaol, or piperine on a total basis of the composition).

14. Compound represented by the following formula (1): 【Chemistry 1】 (In the formula, R is selected from a hydroxymethyl group (-CH₂OH), a formyl group (-CHO), a formyloxymethyl group (-CH₂OC(O)H), and an acetyloxymethyl group (-CH₂OC(O)CH₃)) And, bring into contact with capsaicinoids, gingerol, shogaol, or piperine. A method for producing a food composition containing capsaicinoids, gingerol, shogaol, or piperine.

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