Bean odor masking agent

Abstract

To provide a novel bean odor masking agent, a food composition containing the same, and a method for producing the same. [Solution] A bean odor masking agent comprising one or more compounds selected from the group consisting of lauric acid, α-terpinene, butyric acid, nerolidol, 2-pentanone, and sabinene hydrate.

Description

Technical Field

[0001] The present invention relates to a bean odor masking agent, a food composition, and a method for producing the same.

Background Art

[0002] Proteins derived from beans such as soybeans have attracted attention with the improvement of health consciousness as vegetable proteins excellent in digestibility and absorbability. For example, soy-derived protein has also been reported to have nutritional physiological effects such as a lipid metabolism promoting effect and a muscle fatigue recovery effect. However, when applying proteins derived from beans to foods, "bean odor" (also referred to as off-flavor) becomes a problem. When bean odor is perceived in foods, the consumer's palatability decreases.

[0003] Patent Document 1 discloses a masking agent containing ethanolamine as an active ingredient, which can mask off-flavors and flavors that are too strong as flavors of food and beverages with a very small amount of addition without changing the texture and basic flavor balance of the food and beverage.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0005] In Patent Document 1, ethanolamine is proposed as a masking agent, and specifically, its effect as a masking agent for hamburg, cream cheese sauce, soy milk, consommé onion soup, etc. has been evaluated. However, the technique described in Patent Document 1 has a problem that, for example, it cannot obtain a sufficient masking effect with respect to the bean odor that comes out during chewing. The present invention relates to a novel bean odor masking agent, as well as a food composition containing the same and a method for producing the same. [Means for solving the problem]

[0006] As a result of diligent research, the inventors have discovered that a specific compound can be used as a bean odor masking agent. The present invention encompasses the following embodiments [1] to [6]. [1] A bean odor masking agent comprising one or more compounds selected from the group consisting of lauric acid, α-terpinene, butyric acid, nerolidol, 2-pentanone, and sabinene hydrate. [2] (I) Lauric acid, and, (II) The bean odor masking agent according to [1], comprising one or more compounds selected from the group consisting of α-terpinene, butyric acid, nerolidol, 2-pentanone, and sabinene hydrate. [3] A bean odor masking agent according to [1] or [2], comprising lauric acid, α-terpinene, butyric acid, nerolidol, 2-pentanone, and sabinene hydrate. [4] A bean odor masking agent described in any one of [1] to [3], wherein the bean odor is a soy off-flavor. [5] A food composition comprising a bean-derived ingredient and one or more compounds selected from the group consisting of lauric acid, α-terpinene, butyric acid, nerolidol, 2-pentanone, and sabinene hydrate. [6] A method for producing a food composition in which the bean odor is masked, comprising the step of mixing a bean-derived ingredient with one or more compounds selected from the group consisting of lauric acid, α-terpinene, butyric acid, nerolidol, 2-pentanone, and sabinene hydrate. [Effects of the Invention]

[0007] The present invention provides a novel bean odor masking agent, a food composition containing the same, and a method for producing the same. [Brief explanation of the drawing]

[0008] [Figure 1]Figure 1 shows the results of the evaluation of the responsiveness of olfactory receptors OR4E2 and OR5P3 to n-hexanal. (n=3, mean ± standard deviation) [Figure 2] Figure 2 shows the results of the evaluation of the responsiveness of the olfactory receptor OR5K1 to 2-acetyl-2-thiazoline. [Modes for carrying out the invention]

[0009] [Bean odor masking agent] The bean odor inhibitor of the present invention comprises one or more compounds selected from the group consisting of lauric acid, α-terpinene, butyric acid, nerolidol, 2-pentanone, and sabinene hydrate. <Bean odor masking agent> The bean odor masking agent of the present invention masks the bean odor caused by bean-derived food ingredients, suppressing it to the point where it becomes partially or completely undetectable. In the present invention, the beans from which the bean odor originates are not particularly limited, but are preferably soybeans, broad beans, mung beans, etc. More preferably, the bean odor is a soybean odor originating from soybeans. A bean odor masking agent can be included in products such as foods, beverages, and supplements containing bean-derived ingredients, resulting in products with masked bean odors. The product may be in solid, gel, or liquid form.

[0010] The bean-like odor can be rephrased as an off-flavor. An "off-flavor" refers to an unusual flavor that is not inherently present in a product or sample. For example, it is defined in JIS Z8144:2004. In a preferred embodiment of the present invention, soy off-flavor refers to an odor that originates from soybeans and is also described as a "beany smell." In the present invention, the substances that cause soy off-flavor are preferably n-hexanal, 2-acetyl-2-thiazoline, and the like. Soybeans are the seeds of the legume plant Glycine max.

[0011] <Compound> The active ingredient of the soybean odor inhibitor of the present invention is one or more compounds selected from the group consisting of lauric acid, α - terpinene, butyric acid, nerolidol, 2 - pentanone and sabinene hydrate. Sabinene hydrate may be either the cis - form or the trans - form, or a mixture thereof. The above - mentioned compounds can be used alone or in combination of two or more.

[0012] In a preferred embodiment of the present invention, the soybean odor masking agent (I) lauric acid, and (II) one or more compounds selected from the group consisting of α - terpinene, butyric acid, nerolidol, 2 - pentanone and sabinene hydrate. In this embodiment, the soybean odor masking agent essentially contains lauric acid of group (I) and further contains one or more compounds selected from the five compounds of group (II). More preferably, it contains six compounds: lauric acid, α - terpinene, butyric acid, nerolidol, 2 - pentanone and sabinene hydrate.

[0013] The usage amount of each compound constituting the soybean odor inhibitor can be appropriately set by those skilled in the art. The "usage amount" is the final concentration at the time of eating. The content of lauric acid is preferably 0.1 ppm to 100 ppm, more preferably 1 ppm to 50 ppm. The content of α - terpinene is preferably 0.001 ppm to 10 ppm, more preferably 0.1 ppm to 2 ppm. The content of butyric acid is preferably 0.1 ppm to 10 ppm, more preferably 1 ppm to 5 ppm. The content of nerolidol is preferably 0.01 ppm to 10 ppm, more preferably 0.1 ppm to 1 ppm. The content of 2 - pentanone is preferably 0.1 ppm to 1000 ppm, more preferably 1 ppm to 100 ppm. The sabinene hydrate content is preferably 0.01 ppm to 100 ppm, more preferably 0.1 ppm to 10 ppm.

[0014] [Food composition] The food composition of the present invention comprises a bean-derived ingredient and one or more compounds selected from the group consisting of lauric acid, α-terpinene, butyric acid, nerolidol, 2-pentanone, and sabinene hydrate.

[0015] Food compositions are products such as food, beverages, and supplements. Food compositions may be solid, gel-like, or liquid.

[0016] The bean-derived ingredients are not particularly limited as long as they are derived from legumes such as soybeans, broad beans, and mung beans. The bean-derived ingredients are preferably soybean-derived ingredients. Examples of bean-derived ingredients include whole beans, processed beans, and extracted bean protein.

[0017] The following details examples of soy-derived food ingredients. Processing methods for soybeans include heat treatment, steaming, drying, and fermentation. Soy milk, which is the supernatant obtained by grinding soybeans after adding water, and okara, which is the residue; soybean oil, which is obtained by pressing soybeans, and soybean meal, which is the residue, are all included in soybean processed products. Specific examples of processed soy products include tofu, miso, soy sauce, yuba (tofu skin), kinako (roasted soybean flour), natto (fermented soybeans), and soy milk.

[0018] Soy protein can be extracted, for example, from soybean or soybean plants by known extraction and / or separation methods. Soy protein can be obtained in either a dry or wet form. Dry soy protein can be used, for example, by mixing it with water to form a paste.

[0019] Specific examples of food compositions include substitute foods that utilize soy protein. More specifically, these include imitation meats in which animal protein is replaced with soy protein; and products in which grain ingredients such as wheat and rice are replaced with soy protein. Processed products such as tofu bars and protein bars are also examples. Products that substitute soy protein for grain ingredients such as wheat and rice include dried ingredients for instant noodles (instant cup noodles) and instant cup rice. The food composition of the present invention contains one or more compounds selected from the group consisting of lauric acid, α-terpinene, butyric acid, nerolidol, 2-pentanone, and sabinene hydrate. The preferred combinations and amounts of the above compounds are as described in the "Soybean Odor Masking Agents" section above.

[0020] In the food composition of the present invention, preferably, the above compound is an ingredient added to a bean-derived food ingredient. That is, preferably, the above compound is an ingredient that does not originate from bean-derived food ingredients or other food ingredients. Accordingly, the food composition of the present invention can be obtained by a manufacturing method that includes the step of mixing a bean-derived ingredient with one or more compounds selected from the group consisting of lauric acid, α-terpinene, butyric acid, nerolidol, 2-pentanone, and sabinene hydrate.

[0021] The food composition of the present invention is a food composition in which the beany odor originating from bean-derived ingredients is masked. [Examples]

[0022] The present invention will be described in detail below with reference to examples, but the present invention is not limited in any way to these examples.

[0023] [Method for evaluating odor response using olfactory receptor response as an indicator] Odor responses were evaluated using olfactory receptor responses as indicators, according to the methods described in Japanese Patent Application No. 2024-049441 (filing date: March 26, 2024) and Japanese Patent Application No. 2024-049442 (filing date: March 26, 2024). The specific methods are as follows:

[0024] (1) Generation of HEK293T cells expressing olfactory receptors A reaction solution with the composition shown in Table 1 below was prepared and added to the wells of a 96-well plate. After standing in a clean bench for 20 minutes, HEK293T cells (1.4 × 10⁶) were administered. 5 Cells (100 μL / ml) were seeded into each well and cultured for 24 hours in an incubator at 37°C and 5% CO2.

[0025] [Table 1]

[0026] The pME18S-RTP1S vector encodes the chaperone protein RTP1S (Receptor Transporting Protein 1S) on the eukaryotic cell expression vector pME18S. The pME18S-Rho OR4E2 vector, pME18S-Rho OR5P3 vector, and pME18S-Rho OR5K1 vector encode the olfactory receptor OR4E2, olfactory receptor OR5P3, and olfactory receptor OR5K1, respectively, which have an N-terminal Rho tag.

[0027] Olfactory receptors OR4E2, OR5P3, and OR5K1 are human (Homo sapiens) olfactory receptors. As shown in Reference Example 1 below, olfactory receptors OR4E2 and OR5P3 respond specifically to n-hexanal, the causative component of soy off-flavor. As shown in Reference Example 2 below, olfactory receptor OR5K1 responds specifically to 2-acetyl-2-thiazoline, the causative component of soy off-flavor. Hereinafter, n-hexanal and 2-acetyl-2-thiazoline will be collectively referred to as "odor substances." The amino acid sequences of olfactory receptors OR4E2, OR5P3, and OR5K1 are registered in GenBank, provided by the National Center for Biotechnology Information (NCBI), under the following accession numbers (if multiple revisions are registered, the latest revision is assumed to be the one being referred to): Human olfactory receptor OR4E2: NP_001001912 Human olfactory receptor OR5P3: NP_703146 Human olfactory receptor OR5K1: NP_001004736

[0028] The resulting HEK293T cells express olfactory receptors OR4E2, OR5P3, or OR5K1 on their cell membrane through the function of the chaperone protein RTP1S. Furthermore, the olfactory receptor bound to the ligand odor substance is G, which is endogenously expressed by HEK293T cells. αs By activating adenylyl cyclase in conjunction with pGL4.29, the intracellular cAMP level is increased. Cells express firefly luciferase (luc2P) under the control of the cAMP response element CRE via the pGL4.29 vector, and thus express firefly luciferase in accordance with the intracellular cAMP level. In addition, cells express sea urchin luciferase (hRluc) under the control of the HSV-TK promoter via the pGL4.74 vector and use it as an internal standard.

[0029] (2) Luciferase assay The culture medium was removed from each well containing HEK293T cells expressing the olfactory receptor obtained in (1) above, and 60 μL of the test solution was added to the well. The cells were cultured for 3 hours in an incubator at 37°C and 5% CO2 to allow sufficient expression of firefly luciferase and sea urchin luciferase within the cells.

[0030] Luciferase activity was measured using the Dual-Glo Luciferase Assay System (Promega) according to the manufacturer's instructions. The relative activity of firefly luciferase when an odorant was added was divided by the relative activity of firefly luciferase when no odorant was added. This value was calculated as the fold increase at the given concentration and used as an indicator of the cell's response intensity to the odorant. The relative activity value of firefly luciferase is the value obtained by standardizing the measured activity value (luminescence) of firefly luciferase by the activity value (luminescence) of hRluc.

[0031] Reference example 1 In accordance with the "Evaluation Method Using Olfactory Receptor Response as an Indicator" described above, HEK293T cells expressing olfactory receptor OR4E2 and HEK293T cells expressing olfactory receptor OR5P3 were generated, and a luciferase assay was performed using 60 μL of n-hexanal solution with the composition shown in Table 2 below as the test solution.

[0032] [Table 2]

[0033] The Response (%) was calculated for each concentration of n-hexanal according to the following formula. Figure 1 shows a semi-logarithmic graph with the logarithmic value (log) of the n-hexanal concentration on the X axis and the Response (%) on the Y axis.

[0034] Response(%) = (XY) × 100 / (ZY) X: Fold increase at the n-hexanal concentration in question Fold increase without the addition of Y:n-hexanal Maximum Fold increase when Z:n-hexanal is added.

[0035] Furthermore, the hexanal concentration corresponding to half of the maximum response value is measured in EC. 50 This was requested.50 This is shown below. Olfactory receptor OR4E2: 36.4 μM Olfactory receptor OR5P3: 103.5 μM

[0036] Olfactory receptors OR4E2 and OR5P3 respond to n-hexanal in a concentration-dependent manner. In particular, olfactory receptor OR4E2 responds more strongly to n-hexanal than olfactory receptor OR5P3. 50 The small value suggested a response to n-hexanal at lower concentrations.

[0037] Example 1: Selection of an inhibitor of n-hexanal In accordance with the "Evaluation Method Using Olfactory Receptor Response as an Indicator" described above, HEK293T cells expressing the olfactory receptor OR4E2 were generated, and a luciferase assay was performed using 60 μL of the screening solution (1) with the composition shown in Table 3 below as the test solution. The concentration of each test substance was selected to avoid affecting HEK293T cells.

[0038] [Table 3]

[0039] The fold increase was calculated for each test substance. Then, the inhibition rate (%) was calculated according to the following formula. Candidate substances for the next sensory evaluation were selected based on whether the inhibition rate (%) was 30% or higher.

[0040] Suppression rate (%)=(1-B / A)×100 A: Fold increase when n-hexanal alone is added. B: Fold increase when n-hexanal and the test substance combination is added.

[0041] The results are shown in Table 4. Lauric acid and α-terpinene were selected as candidate substances for inhibiting n-hexanal.

[0042] [Table 4]

[0043] Reference example 2 In accordance with the "Evaluation Method Using Olfactory Receptor Response as an Indicator" described above, HEK293T cells expressing the olfactory receptor OR5K1 were generated, and a luciferase assay was performed using 60 μL of 2-acetyl-2-thiazoline solution with the composition shown in Table 5 below as the test solution.

[0044] [Table 5]

[0045] As a control, cells transfected with a pME18S-Rho vector that does not encode olfactory receptors (ORs) instead of the pME18S-Rho OR5K1 vector were similarly tested (mock). The results are shown in Figure 2.

[0046] The olfactory receptor OR5K1 responds to 2-acetyl-2-thiazoline in a concentration-dependent manner.

[0047] Example 2: Selection of inhibitors for 2-acetyl-2-thiazoline In accordance with the "Evaluation Method Using Olfactory Receptor Response as an Indicator" described above, HEK293T cells expressing the olfactory receptor OR5K1 were prepared, and a screening solution (2) with the composition shown in Table 6 below was prepared. A luciferase assay was performed using 60 μL of the test solution. The concentration of each test substance was selected to avoid affecting HEK293T cells.

[0048] [Table 6]

[0049] The fold increase was calculated for each test substance. Then, the inhibition rate (%) was calculated according to the following formula. Candidate substances for the next sensory evaluation were selected based on whether the inhibition rate (%) was 30% or higher.

[0050] Suppression rate (%)=(1-B / A)×100 A: Fold increase when 2-acetyl-2-thiazoline alone is added. B: Fold increase when 2-acetyl-2-thiazoline and the test substance are added.

[0051] The results are shown in Table 7. Butyric acid, nerolidol, 2-pentanone, and sabinene hydrate were selected as candidate substances for inhibiting 2-acetyl-2-thiazoline.

[0052] [Table 7]

[0053] Example 3 Sensory evaluation (1) (1) Soybean sample As the soybean sample, we used "Veggie Plus 2900" (product name, manufactured by Fuji Oil Co., Ltd.), a soybean protein material. After rehydrating Veggie Plus 2900 in 20 times its volume of hot water for 5 minutes, it was chopped using a food processor.

[0054] (2) Sensory evaluation The soybean samples obtained above were given candidate odor inhibitors diluted with ethanol at various concentrations, and sensory evaluations were conducted. The candidate inhibitors were adjusted so that their concentrations were achieved when 1% by mass of ethanol containing the candidate substance was added to the soybean samples. For the sensory evaluation, two trained panelists proficient in odor evaluation assessed the effect of suppressing the soybean odor perceived upon consumption, according to the following criteria. • Evaluation criteria 0: The soy odor is not suppressed at all, meaning it is the same as a sample to which no inhibitor compound has been added. 1: Minimum effect on suppressing soybean odor ~ 10: Maximum effect on suppressing soybean odor

[0055] The results are shown in Table 8.

[0056] [Table 8]

[0057] Next, we evaluated the effect of combining inhibitory compounds on suppressing soybean odor. Table 9 shows the evaluation results of the inhibitory effects when lauric acid, which showed the highest inhibitory effect in the above tests, was combined with other compounds.

[0058] [Table 9]

[0059] Furthermore, soy odor inhibitors were prepared by mixing six compounds in the compositions shown in Table 10, and their effect in suppressing soy odor when added to soybean samples was evaluated. The soy odor inhibitors were prepared using ethanol as a solvent. The evaluation results are shown in Table 11.

[0060] [Table 10]

[0061] [Table 11]

[0062] Example 4 Sensory evaluation (2) (1) Bean sample As bean samples, we used "Orprotein FP-AC" (product name, manufactured by Organo Food Tech Co., Ltd.), a broad bean protein material, and "Orprotein MP-AC" (product name, manufactured by Organo Food Tech Co., Ltd.), a mung bean protein material. Each powdered material was dispersed in nine times its volume of water. (2) Sensory evaluation A mixture of inhibitors with the composition shown in Table 10 above was added to each bean sample, and a sensory evaluation was conducted. In the sensory evaluation, two trained panelists proficient in aroma evaluation assessed the effect of suppressing off-flavors perceived during consumption according to the following criteria. • Evaluation criteria 0: Off-flavors are not suppressed at all, i.e., the same as a sample without any suppressing compound added. 1: Minimum off-flavor suppression effect ~ 10: Maximum off-flavor suppression effect

[0063] The results are shown in Table 12.

[0064] [Table 12]

Claims

1. A bean odor masking agent comprising one or more compounds selected from the group consisting of lauric acid, α-terpinene, butyric acid, nerolidol, 2-pentanone, and sabinene hydrate.

2. (I) Lauric acid, and, (II) The bean odor masking agent according to claim 1, comprising one or more compounds selected from the group consisting of α-terpinene, butyric acid, nerolidol, 2-pentanone, and sabinene hydrate.

3. A bean odor masking agent according to claim 1, comprising lauric acid, α-terpinene, butyric acid, nerolidol, 2-pentanone, and sabinene hydrate.

4. The bean odor masking agent according to claim 1, wherein the bean odor is a soy off-flavor.

5. A food composition comprising a bean-derived ingredient and one or more compounds selected from the group consisting of lauric acid, α-terpinene, butyric acid, nerolidol, 2-pentanone, and sabinene hydrate.

6. A method for producing a food composition in which the bean odor is masked, comprising the step of mixing a bean-derived ingredient with one or more compounds selected from the group consisting of lauric acid, α-terpinene, butyric acid, nerolidol, 2-pentanone, and sabinene hydrate.

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