Pungency enhancer

Abstract

The problem to be solved by the present invention is to provide a novel hot taste enhancing method using an ingredient that is not known to have a hot taste enhancing effect until now. The present invention provides a hot taste enhancer for a product containing a hot taste ingredient, the hot taste enhancer comprising at least one component selected from the group consisting of citral and a citral analogue represented by general formula (1): H3C-C(CH3)=CH-CH2-CH2-C(CH3)=CH-R1-R2 [wherein R1 represents -CH(OH)-, -C(=O)- or -CH(OAc)-; Ac represents an acetyl group; and R2 represents an alkyl group having 1 to 4 carbon atoms].

Description

[Technical Field]

[0001] This application claims priority to Japanese Patent Application No. 2021-045405, filed on 19 March 2021 (the entire disclosure thereof is incorporated herein by reference). The present invention relates to a spiciness enhancer, a method for enhancing spiciness, a product containing a spiciness component, and a method for producing the same. [Background technology]

[0002] The spiciness imparted to food and beverages by chili peppers, wasabi, mustard, black pepper, Japanese pepper, ginger, etc., can enhance the flavor, add an accent to the taste, or be enjoyed for its spiciness itself, thus stimulating appetite. For this reason, spicy food and beverages are enjoyed in a wide variety of forms across different cultures.

[0003] Because spiciness is a flavor enjoyed by many, spices that produce spiciness have been sought after since ancient times. In recent years, there have also been attempts to enhance the spiciness of food ingredients, and there is a strong desire for the development of new ingredients that enhance the spiciness of food and beverages. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2020-195333 [Patent Document 2] Japanese Patent Publication No. 2020-196775 [Patent Document 3] Japanese Patent Publication No. 2011-019457 [Patent Document 4] Patent No. 4384246 [Patent Document 5] Patent No. 3115245 [Patent Document 6] Patent No. 3271824 [Patent Document 7] Special fair 05-082186 [Overview of the Initiative] [Problem to be Solved by the Invention]

[0005] An object of the present invention is to provide a novel pungency enhancing method using a component that has not been previously known to have a pungency enhancing effect. [Means for Solving the Problem]

[0006] Under such circumstances, as a result of intensive studies, the present inventors have found that such problem can be solved by using citral or a specific analog thereof. The present invention is based on such new finding. Accordingly, the present invention provides the following items:[ Item 1. A pungency enhancer for a pungent component-containing product, comprising at least one selected from the group consisting of citral and a citral analog represented by the following general formula (1): H3C-C(CH3)=CH-CH2-CH2-C(CH3)=CH-R 1 -R 2 (1) [In the formula, R 1 represents -CH(OH)-, -C(=O)- or -CH(OAc)-, Ac represents an acetyl group, and R 2 represents an alkyl group having 1 to 4 carbon atoms.] Item 2. The pungency enhancer for a pungent component-containing product according to Item 1, wherein when the pungency enhancer comprises a citral analog represented by general formula (1), R 2 represents an alkyl group having 1 carbon atom. Item 3. A method for enhancing pungency of a pungent component-containing product, comprising adding at least one selected from the group consisting of citral and a citral analog represented by the following general formula (1) to the pungent component-containing product: H3C-C(CH3)=CH-CH2-CH2-C(CH3)=CH-R 1 -R 2 (1) [In the formula, R 1 represents -CH(OH)-, -C(=O)- or -CH(OAc)-, Ac represents an acetyl group, and R 2 represents an alkyl group having 1 to 4 carbon atoms.] Item 4. The method described in Item 3, in which a citral analog represented by general formula (1) is added to the product containing the pungent component, R 2 A method for representing an alkyl group having 1 carbon atom. Item 5. A method for producing a spicy flavor product, comprising adding a spicy flavor enhancer described in Item 1 or 2 to the spicy flavor product. Item 6. A product containing a spicy ingredient, which contains the spicy flavor enhancer described in Item 1 or 2. [Effects of the Invention]

[0007] According to the present invention, it is possible to provide a novel method for enhancing spiciness using a component that was previously not known to have a spiciness-enhancing effect. [Modes for carrying out the invention]

[0008] (I) Pungency enhancer In a first embodiment, the present invention provides a spiciness enhancer for pungent flavoring products, comprising citral and at least one selected from the group consisting of citral analogs represented by the following general formula (1): H3C-C(CH3)=CH-CH2-CH2-C(CH3)=CH-R 1 -R 2 (1) [In the formula, R 1 R represents -CH(OH)-, -C(=O)-, or -CH(OAc)-, where Ac represents an acetyl group. 2 This represents an alkyl group with 1 to 4 carbon atoms. In the present invention, citral refers to a mixture of neral and geranial. Further, in the present specification, the citral analog represented by general formula (1) may be simply referred to as citral analog (1). In the present invention, in the above general formula (1), Ac represents an acetyl group. In addition, an alkyl group refers to a linear or branched saturated hydrocarbon group. In the present invention, the number of carbon atoms in the alkyl group is 1 to 4, preferably 1 to 3, more preferably 1 to 2, and still more preferably 1. More specifically, examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, and a tert-butyl group. Further, when citral analog (1) has isomers such as geometric isomers, stereoisomers, and optical isomers, these isomers are included in citral analog (1) unless otherwise specified. For example, general formula (1) can include each cis isomer, trans isomer, and mixtures thereof. More specifically, for example, when R 1 is -CH(OH)- (alcohol form), general formula (1) includes

[0009]

Chemical Formula

[0010] all of which may be included. Similarly, when R 1 is -C(=O)- (ketone form), general formula (1) includes

[0011]

Chemical Formula

[0012] all of which may be included. Further, when R 1 is -CH(OAc)- (ester form), general formula (1) includes

[0013]

Chemical Formula

[0014] All of these may be included.

[0015] In the present invention, "at least one selected from the group consisting of citral and citral analogs (1)" may be simply referred to as a citral compound.

[0016] Citral analogs (1) can be synthesized according to known or publicly known methods. Commercially available citral or citral analogs include, for example, citral F (manufactured by Shandong NHU Pharmaceutical Co., Ltd.) which is sold under trade names. In the present invention, these citral and citral analogs (1) may be used individually or in combination of multiple types.

[0017] In the spiciness enhancer of the present invention, citral or citral analog (1) may be used in a purified state, but is not limited thereto. Natural materials containing citral or citral analog (1) can be used as the spiciness enhancer of the present invention, as long as they do not impair the effects of the present invention. Such natural materials are not limited to these, but examples include lemons, citrus fruits, and the like as natural materials containing citral.

[0018] The spiciness enhancer of the present invention is used, for example, to enhance the spiciness of a product containing the target spicy component described later. Its form is not limited, but it can be in solid form such as powder, granules, tablets, or capsules, as well as in semi-solid or liquid form such as syrup, emulsion, liquid, or gel.

[0019] The spiciness enhancer of the present invention may consist solely of citral or a citral analog (1), or, in addition to citral or a citral analog (1), a pharmaceutically acceptable carrier or a carrier that can be incorporated into food and beverages may be appropriately added depending on its form. Examples of such carriers include oligosaccharides such as isomaltoligosaccharides, galactooligosaccharides, and fructooligosaccharides; polysaccharides such as dextrin, cellulose, gum arabic, and starch (corn starch, etc.); and solvents such as water and ethanol, provided that they do not affect the effects of the spiciness enhancer of the present invention. Furthermore, flavorings, colorings, acidulants, or shelf-life enhancers commonly used in food and beverages, pharmaceuticals, etc. may also be added, provided that they do not affect the effects of the spiciness enhancer of the present invention. In this embodiment, the total amount of citral or citral analog (1) in the pungent flavor enhancer of the present invention can be appropriately set from the range of 0.00000001 to 99% by mass (0.0001 to 990000 ppm) depending on the manner in which the pungent flavor enhancer of the present invention is used and the presence or absence of other components.

[0020] (II) Products containing spicy ingredients The present invention provides a product containing a pungent component, which includes the pungent component enhancer of the present invention. As described above, the pungent component enhancer of the present invention contains citral or a citral analog (1). Accordingly, the present invention provides a product containing a pungent component, which includes citral or a citral analog (1). The product containing the pungent component of the present invention can be easily prepared by adding the pungent component enhancer of the present invention, as described above, to a target product containing a pungent component, which will be described later.

[0021] The products containing pungent components that are the subject of this invention are products that contain pungent components, and are typically edible products that contain pungent components. Examples of target products include food and beverages; oral pharmaceuticals; oral pharmaceuticals; and oral care products such as toothpaste and mouthwash (including pharmaceuticals or quasi-drugs), and are preferably food and beverages.

[0022] Examples of pungent ingredients targeted by the present invention include capsaicin, allyl isothiocyanate, piperine, sanshool, diallyl disulfide, and gingerol. These may be used individually or in any combination of two or more. The pungent ingredients may also be used in the form of a food material or processed product containing one or more of the pungent ingredients. In such embodiments, for example, the food material may include chili peppers, wasabi, horseradish, Japanese mustard, pepper, sansho pepper, garlic, and ginger, and the processed products may include chili paste, yuzu pepper, tom yum paste, doubanjiang, spicy cod roe, powdered wasabi, paste wasabi, pickled wasabi, powdered mustard, paste mustard, powdered pepper, salt and pepper, powdered sansho pepper, garlic powder, grated garlic, and grated ginger. The form of these pungent ingredients is not particularly limited. For example, the product may be in powder, semi-solid, or liquid form. The proportion of the pungent component contained in the pungent component-containing product of the present invention can be appropriately set according to the purpose and / or type of the pungent component-containing product of the present invention. Although not limited, for example, the proportion of the pungent component contained in the pungent component-containing product of the present invention can be 0.000001 to 20% by mass. Furthermore, when capsaicin, materials containing capsaicin, processed products, etc. are used as the pungent component, the proportion of capsaicin contained in the pungent component-containing product of the present invention can be exemplified as 0.00001 to 10% by mass. When allyl isothiocyanate, materials containing allyl isothiocyanate, processed products, etc. are used as the pungent component, the proportion of allyl isothiocyanate contained in the pungent component-containing product of the present invention can be exemplified as 0.000001 to 10% by mass. When piperine, materials containing piperine, processed products, etc. are used as the pungent component, the proportion of piperine contained in the pungent component-containing product of the present invention can be exemplified as 0.001 to 20% by mass. When using gingerol, a material containing gingerol, or a processed product as a pungent component, the proportion of gingerol contained in the pungent component-containing product of the present invention can be exemplified as 0.001 to 10% by mass.Furthermore, in a preferred embodiment of the present invention, the spiciness-enhancing effect makes it possible to reduce the amount of spiciness components (compounds such as capsaicin, allyl isothiocyanate, and piperine) in products containing spiciness components, making it useful. The present invention is extremely useful because it can enhance not only any one of the following types of spiciness: capsaicin contained in chili peppers, allyl isothiocyanate contained in Japanese mustard, wasabi, horseradish, etc.; piperine contained in black pepper, etc.; sanshool contained in Japanese pepper, etc.; diallyl disulfide contained in garlic, etc.; gingerol contained in ginger, etc., but all of these different types of spiciness. Moreover, since citral and citral analogues (1) are not compounds that exhibit spiciness themselves, the effect of the present invention, which is that spiciness can be enhanced by adding them to products containing spiciness components, is something that could not be predicted from the prior art.

[0023] Food and beverages specifically include the following: Confectionery containing the aforementioned spicy components, such as rice crackers, biscuits, pretzels, cakes, chocolates, gum, candy, gummies, and tablets; snack foods such as potato chips; soups such as instant soup and instant miso soup; frozen cooked foods such as frozen hamburgers and frozen takoyaki; chilled cooked foods such as chilled meatballs and chilled gyoza; other cooked foods such as omelets and corn dogs; alcoholic beverages such as chuhai and non-alcoholic chuhai; chilled desserts such as chilled pudding and fruit sauce; ice cream; frozen desserts such as soft serve mix and frozen desserts; dry desserts such as dried jelly and dessert bases; frozen rice products; rice products such as risotto; noodles such as cup noodles, instant noodles, chilled ramen, and frozen pasta; other staples such as prepared bread and okonomiyaki mix; chili paste, yuzu pepper, and tom yum. Condiments such as paste, wasabi powder, wasabi paste, mustard powder, mustard paste, mustard, pepper powder, salt and pepper, sansho pepper powder, garlic powder, grated garlic, grated ginger, dressings, yakiniku sauce, pickling mix, chili oil, doubanjiang, mayonnaise, etc.; seasoned foods such as retort curry, pasta sauce, fried rice mix, etc.; processed agricultural products such as pickles, pickled wasabi, seasoned bamboo shoots, etc.; ham products; processed livestock products such as salad chicken, etc.; processed seafood products; kelp tsukudani, spicy mentaiko Examples of products include processed marine products such as children's products; dairy products such as margarine and cheese; fruit beverages such as fruit juices and vegetable juices; carbonated beverages such as cola and ginger ale; dairy beverages such as lactic acid bacteria beverages and drinkable yogurt; beverages such as coffee, tea, and jelly drinks; health beverages such as drinks, functional soft drinks, and sports drinks; other beverages such as soft drinks and flavored water; and luxury items such as portioned coffee and premixed beverages.

[0024] Oral pharmaceuticals include lozenges, drinks, granules, powders, tablets, capsules, etc., containing the aforementioned pungent ingredients; oral pharmaceuticals include sprays, ointments, pastes, etc., containing the aforementioned pungent ingredients; and oral care products include liquid toothpaste, toothpaste, mouthwash, breath fresheners, etc., containing the aforementioned pungent ingredients.

[0025] In a preferred embodiment of the present invention, citral or citral analog (1) is blended into a pungent component-containing product such that the final concentration in the pungent component-containing product of the present invention is, for example, 0.005 to 200 ppm, more preferably 0.02 to 50 ppm, and even more preferably 0.1 to 10 ppm. In such an embodiment, if two or more types of citral or citral analog (1) are blended, it is preferable that each of them falls within the above concentration range. The final concentration of citral or citral analog (1) in such a pungent component-containing product can be appropriately set depending on the type of pungent component-containing product to be targeted, etc. For example, as a lower limit, as mentioned above, 0.005 ppm or more can be given, but preferably 0.02 ppm or more, and more preferably 0.1 ppm or more. As a higher limit for the final concentration of citral or citral analog (1) in the pungent component-containing product, as mentioned above, 200 ppm or less can be given, but preferably 50 ppm or less, and more preferably 10 ppm or less. Furthermore, when two or more types of citral or citral analogs (1) are blended, the total amount of citral or citral analogs (1) relative to the product containing the pungent component is preferably in the concentration range of 0.005 to 200 ppm, more preferably 0.02 to 50 ppm, and even more preferably 0.1 to 10 ppm.

[0026] Furthermore, if the pungent component-containing product of the present invention contains capsaicin, the blending ratio (mass ratio) of the citral compound to capsaicin is preferably 0.00000001 to 1, more preferably 0.000001 to 0.5, and even more preferably 0.0001 to 0.2. If the pungent component-containing product of the present invention contains allyl isothiocyanate, the blending ratio (mass ratio) of the citral compound to allyl isothiocyanate is preferably 0.0000001 to 1000, more preferably 0.00001 to 10, and even more preferably 0.001 to 0.1. If the pungent component-containing product of the present invention contains piperine, the blending ratio (mass ratio) of the citral compound to piperine is preferably 0.00000002 to 1, more preferably 0.000005 to 0.5, and even more preferably 0.001 to 0.2.

[0027] In the present invention, "spiciness" refers to the stimulating taste (or irritation, pain sensation) possessed by the aforementioned spicy component. Spiciness can be broadly divided into two categories: those derived from non-volatile components, such as chili peppers, black pepper, Japanese pepper, and ginger, which cause a burning sensation in the mouth; and those derived from volatile components, such as wasabi, mustard, and garlic, which cause irritation of the nasal mucosa. The present invention can enhance both of these categories of spiciness. Therefore, in the present invention, "spiciness" encompasses both of these categories. In a typical embodiment of the present invention, examples of spiciness include spiciness provided by at least one selected from the group consisting of capsaicin, allyl isothiocyanate, piperine, sanshool, diallyl disulfide, and gingerol, with capsaicin, allyl isothiocyanate, and piperine being preferred.

[0028] The spicy component-containing product of the present invention can be manufactured by adding the spicy flavor enhancer of the present invention to the spicy component-containing product. Accordingly, in one embodiment, the present invention provides a method for manufacturing a spicy component-containing product, which includes adding the spicy flavor enhancer of the present invention to the spicy component-containing product. As mentioned above, the spicy flavor enhancer of the present invention contains citral or a citral analog (1). Accordingly, in one embodiment, the present invention provides a method for manufacturing a spicy component-containing product, which includes adding at least one selected from the group consisting of citral and citral analog (1) to the spicy component-containing product. The meaning of each term in such manufacturing method, the mixing ratio of each component, etc., are the same as described above. Citral or a citral analog (1) can be added at any stage in the manufacturing process of the spicy component-containing product of the present invention.

[0029] By using the present invention, the spiciness of a product containing spicy components can be enhanced without increasing the amount and / or improving the quality of the spicy components. In other words, the manufacturing method of the present invention allows for the simple and inexpensive production of a spicy component-containing product with enhanced spiciness. Furthermore, by using the present invention, it is expected that the spiciness will be enhanced, the taste will be improved, and palatability will be enhanced. Conversely, according to the present invention, the amount of spicy components used can be reduced without significantly reducing or compromising the spiciness.

[0030] Whether or not the spiciness of the pungent component-containing product of the present invention is enhanced can be evaluated by comparing the spiciness of the pungent component-containing product of the present invention, which contains citral or a citral analog (1), with the spiciness of a composition (comparative composition) that has the same composition as the pungent component-containing product of the present invention except that it does not contain citral or a citral analog (1). If the spiciness of the pungent component-containing product of the present invention is higher than that of the comparative composition, it can be determined that the spiciness of the pungent component-containing product of the present invention is enhanced. Although not limited, the evaluation can be specifically performed according to the description of the examples described later. By enhancing the spiciness of the pungent component-containing product of the present invention through the inclusion of citral or a citral analog (1), it is possible to prepare a pungent component-containing product of the present invention that has a spiciness similar to that of a composition containing more pungent components than actually present.

[0031] (III) Methods for enhancing the spiciness of products containing spicy ingredients The present invention provides a method for enhancing the spiciness of a product containing a spicy component, comprising adding the spiciness enhancer of the present invention to the product. As described above, the spiciness enhancer of the present invention contains citral or a citral analog (1). Accordingly, in one embodiment, the present invention provides a method for enhancing the spiciness of a product containing a spicy component, comprising adding at least one selected from the group consisting of citral and a citral analog (1) to the product. The meaning of each term and the mixing ratio of each component in this method of enhancing spiciness are the same as described above. Citral or a citral analog (1) can be added at any stage in the manufacturing process of the pungent component-containing product of the present invention.

[0032] In this specification, the terms "contains" and "include" encompass the meanings of "substantially consist of" and "consist of."

[0033] The contents of the present invention will be specifically explained using the following experimental examples and embodiments. However, the present invention is not limited in any way to these. Unless otherwise specified below, the experiments were conducted under atmospheric pressure and room temperature conditions. Unless otherwise specified, "%" means "mass%" and "parts" means "parts by mass". [Examples]

[0034] In the following experimental examples, citral F (manufactured by Shandong NHU Pharmaceutical Co., Ltd.) was used as the citral. In addition, 4,8-dimethyl-3,7-nonadien-2-ol, 4,8-dimethyl-3,7-nonadien-2-yl acetate, and 4,8-dimethyl-3,7-nonadien-2-one were used as citral analogs.

[0035] Experimental Example 1: Evaluation of the spiciness-enhancing effect of spiciness enhancers. (1) Evaluation method Each pungent component listed in Table 1 was added to water at the concentrations indicated in the table, and each sample was added at the concentrations indicated in Table 1 to prepare the samples. As a control, samples were also prepared in which only each pungent component was added to water at the concentrations indicated in the table, without adding any of the samples. The spiciness of each sample was evaluated by a panel of eight individuals (the same as in the following experimental examples) who were trained in sensory evaluation of the taste quality of food and beverages and had passed in-house tests. 1 point: I didn't feel any spiciness enhancement effect at all (spiciness level was the same as the control version). 2 points: Slightly enhances the spiciness (spiciness level between 1 and 3 points) 3 points: Has a spiciness-enhancing effect (1.5 times spicier than the control version) 4 points: Strong spiciness enhancement effect (spiciness level between 3 and 5 points) 5 points: The spiciness enhancement effect is quite strong (more than twice as spicy as the control version). (2) Evaluation results The results are shown in Table 1.

[0036] [Table 1]

[0037] The results above show that both citral and citral analogs enhanced the spiciness of allyl isothiocyanate, piperine, and capsaicin. Furthermore, 4,8-dimethyl-3,7-nonadien-2-ol and 4,8-dimethyl-3,7-nonadien-2-yl acetate enhanced the spiciness of allyl isothiocyanate more strongly, 4,8-dimethyl-3,7-nonadien-2-yl acetate and 4,8-dimethyl-3,7-nonadien-2-one enhanced the spiciness of piperine more strongly, and 4,8-dimethyl-3,7-nonadien-2-one enhanced the spiciness of capsaicin more strongly.

[0038] Experimental Example 2: Evaluation of the spiciness-enhancing effect of spiciness enhancers. (1) Evaluation method Prepared the target foods listed in Table 2 by adding each sample at the type and concentration specified in the table. A control sample of the target food without any of the samples was also prepared. A panel of 10 members evaluated the spiciness of each sample. 1 point: I didn't feel any spiciness enhancement effect at all (spiciness level was the same as the control version). 2 points: Slightly enhances the spiciness (spiciness level between 1 and 3 points) 3 points: Has a spiciness-enhancing effect (1.5 times spicier than the control version) 4 points: Strong spiciness enhancement effect (spiciness level between 3 and 5 points) 5 points: The spiciness enhancement effect is quite strong (more than twice as spicy as the control version). The food products used in this test are as follows: Horseradish: Grated horseradish (S&B Horseradish, manufactured by S&B Spice Industry Co., Ltd.) Japanese mustard: Prepared mustard (House Foods Corporation's "Nerikarashi") Yuzu Kosho: A mixture of ground green chili peppers and yuzu peel (Fundokin Soy Sauce Co., Ltd.'s "Seven Premium Yuzu Kosho") Wasabi: Freshly grated real wasabi (S&B Foods Co., Ltd.'s "Hon Nama Hon Wasabi") (2) Evaluation results The results are shown in Table 2.

[0039] [Table 2]

[0040] The results above show that citral and citral analogs enhanced the spiciness of horseradish, Japanese mustard, yuzu pepper, and wasabi.

Claims

1. A pungent flavor enhancer for products containing pungent components, comprising at least one selected from the group consisting of citral and citral analogs represented by the following general formula (1): H 3 C-C(CH 3 )=CH-CH 2 -CH 2 -C(CH 3 )=CH-R 1 -R 2 (1) [In the formula, R 1 represents -CH(OH)-, -C(=O)- or -CH(OAc)-, and Ac represents an acetyl group. R 2 represents an alkyl group having 1 carbon atom.]]

2. A method for enhancing the spiciness of a product containing a pungent component, comprising adding at least one substance selected from the group consisting of citral and citral analogs represented by the following general formula (1) to the product containing the pungent component: H 3 C-C(CH 3 )=CH-CH 2 -CH 2 -C(CH 3 )=CH-R 1 -R 2 (1) [In the formula, R 1 R represents -CH(OH)-, -C(=O)-, or -CH(OAc)-, where Ac represents an acetyl group. 2 This represents an alkyl group with one carbon atom.

3. A method for producing a spicy component-containing product, comprising adding the spicy flavor enhancer described in claim 1 to the spicy component-containing product, A method for producing the pungent component, characterized in that at least one selected from the group consisting of citral and citral analogs represented by the general formula (1) is added to the pungent component-containing product such that the final concentration is 0.001 to 50 ppm.

4. A spicy component-containing product comprising the spicy flavor enhancer described in claim 1, A product containing a pungent component, characterized in that at least one selected from the group consisting of citral and citral analogs represented by the general formula (1) is added to the pungent component-containing product such that the final concentration is 0.001 to 50 ppm.

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