Method and composition for masking vegetable protein odor

Abstract

To provide a vegetable protein composition improved in stuffy odor and powdery odor of vegetable protein caused by components other than n-hexanal, and to provide a method for producing the same, and further to provide a method for improving odor of plant proteins caused by components other than n-hexanal in a plant-derived protein composition.SOLUTION: By using alcohol and phenol compounds, it is possible to mask odor such as stuffy or powdery odor of vegetable proteins by 2-(2-ethoxyethoxy)-ethanol, a linear alkane having 14 to 20 carbon atoms, or 2-methylnaphthalene.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a method for masking the odor of vegetable proteins. [Background technology]

[0002] In recent years, as the demand for protein increases with the global population growth, there are concerns that the supply will be insufficient. For this reason, much research has been done with the aim of using protein materials derived from plants, microorganisms, insects, etc. as food. In particular, plant-derived proteins (vegetable proteins) are less expensive than animal-derived proteins, and are therefore attracting attention as a future source of protein and an alternative meat ingredient. However, soybeans and other plant proteins have a unique odor, and it is known that the odor described as grassy is particularly due to aldehyde compounds, particularly n-hexanal, which has created issues in using them as food.

[0003] For this reason, hexanal has been studied as a method for masking the characteristic odor derived from vegetable protein in food systems. For example, soy milk compositions containing fumaric acid (Patent Document 1) and soy milk containing methylpyrazine compounds (Patent Document 2) have been reported as soy milk with masked vegetable protein odor. In addition, a method of including benzothiazole in vegetable milk has been reported to mask the grassy odor that occurs during storage of vegetable milk such as soy milk (Patent Document 3).

[0004] However, vegetable protein odors include not only a grassy smell, but also a stuffy smell (stuffy smell) and a powdery smell, and there have been no reports on the components that contribute to the vegetable protein odor other than the grassy smell, and on methods for masking the vegetable protein odor caused by these components. Therefore, methods that focus on the grassy smell, i.e., aldehyde compounds such as n-hexanal, have not been able to provide a satisfactory masking effect, and there has been a demand for methods to identify the components of the vegetable protein odor other than the grassy smell derived from vegetable proteins and to further improve it. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Patent Publication No. 2021-019523 [Patent Document 2] JP 2017-169481 A [Patent Document 3] JP 2021-176284 A Summary of the Invention [Problem to be solved by the invention]

[0006] The present invention aims to provide a vegetable protein composition in which the stuffy odor or powdery odor of vegetable protein caused by components other than n-hexanal is improved, and a method for producing the same, and also to provide a method for improving the vegetable protein odor caused by components other than n-hexanal in a protein composition derived from a plant. [Means for solving the problem]

[0007] As a result of intensive research into solving the above problems, the inventors discovered that 2-(2-ethoxyethoxy)-ethanol, linear alkanes having 14 to 20 carbon atoms, or 2-methylnaphthalene contribute to odors such as the stuffy odor and powdery odor of vegetable proteins, and further discovered that the vegetable protein odor caused by these components can be masked by using alcohols and phenolic compounds, thereby completing the present invention.

[0008] That is, the present invention relates to the following first to eighth aspects. The first method is to mask the characteristic aroma of plant-derived proteins by masking the odor of one or more compounds that are involved in the characteristic aroma of plant proteins: 2-(2-ethoxyethoxy)-ethanol, linear alkanes with 14 to 20 carbon atoms, and 2-methylnaphthalene. The second method is a method for masking the characteristic odor of a plant-derived protein by adding a compound or composition capable of masking the odor of one or more compounds selected from the group consisting of 2-(2-ethoxyethoxy)-ethanol, linear alkanes having 14 to 20 carbon atoms, and 2-methylnaphthalene to the plant protein. Third, the method according to the second aspect, wherein the compound or composition is ethanol and a phenolic compound. Fourth, an odor masking composition containing one or more compounds selected from the group consisting of 2-(2-ethoxyethoxy)-ethanol, linear alkanes having 14 to 20 carbon atoms, and 2-methylnaphthalene. Fifth, the masking composition according to the fourth aspect contains ethanol and a phenolic compound as active ingredients. Sixth, a method for screening a masking composition is provided using as an index the masking of odor caused by one or more of the compounds 2-(2-ethoxyethoxy)-ethanol, linear alkanes having 14 to 20 carbon atoms, and 2-methylnaphthalene, which are involved in the characteristic odor of vegetable proteins. Seventh, a plant-derived protein-containing composition in which odor caused by one or more of the compounds 2-(2-ethoxyethoxy)-ethanol, linear alkanes having 14 to 20 carbon atoms, and 2-methylnaphthalene, which are involved in the characteristic odor of vegetable proteins, is masked. Eighth, there is provided a method for producing a plant-derived protein-containing composition, which includes a step of masking odor caused by one or more compounds, namely, 2-(2-ethoxyethoxy)-ethanol, a linear alkane having 14 to 20 carbon atoms, and 2-methylnaphthalene, which are involved in the characteristic odor of plant proteins. Effect of the Invention

[0009] According to the present invention, a vegetable protein composition in which the vegetable protein odor derived from components other than n-hexanal is masked can be obtained by coexisting a predetermined amount of alcohol or phenolic compound with a vegetable protein raw material. The vegetable protein composition can be used as a protein source in general foods and supplements because the characteristic aroma of vegetable protein, which is expressed as stuffy odor or powdery odor, is masked. In addition, a method for screening vegetable protein odor masking compositions can be provided using as an index the odor caused by 2-(2-ethoxyethoxy)-ethanol, linear alkanes having 14 to 20 carbon atoms, or 2-methylnaphthalene, which are components that contribute to vegetable protein odor other than n-hexanal. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] The vegetable protein material in the present invention refers to a protein itself obtained from an edible plant and containing one or more of 2-(2-ethoxyethoxy)-ethanol, a linear alkane having 14 to 20 carbon atoms, and 2-methylnaphthalene, or a plant-derived protein that is subjected to a process such as extraction, defatting, acid treatment, alkali treatment, enzyme treatment, neutralization, heating, drying, powderization, and texturization to produce one or more of 2-(2-ethoxyethoxy)-ethanol, a linear alkane having 14 to 20 carbon atoms, and 2-methylnaphthalene.

[0011] The plant from which the plant protein material is derived is not limited as long as it is a plant that can generally be used for food, and examples thereof include beans, grains, and nuts. Examples of the beans include soybeans, adzuki beans, lentils, chickpeas, peas, broad beans, kidney beans, and mung beans. Examples of the grains include wheat, barley, oats, rice, corn, and buckwheat. Examples of nuts include almonds, cacao, cashew nuts, pistachios, and macadamia nuts. Among these plants, soybeans, peas, and wheat are preferred.

[0012] The characteristic aroma of vegetable protein in the present invention refers to an unpleasant odor that is said to be stuffy or powdery, and is caused by any one of 2-(2-ethoxyethoxy)-ethanol (CAS number: 111-90-0), linear alkanes having 14 to 20 carbon atoms, and 2-methylnaphthalene (CAS number: 91-57-6). Among the linear alkanes having 14 to 20 carbon atoms, tetradecane (CAS number: 629-59-4), heptadecane (CAS number: 629-78-7), and octadecane (CAS number: 593-45-3) particularly contribute to the vegetable protein odor.

[0013] In the present invention, masking of the vegetable protein odor can be achieved by making it difficult to sense the vegetable protein odor caused by any one or more of the compounds that cause the characteristic aroma of the vegetable protein.

[0014] The compound capable of suppressing the characteristic aroma of vegetable protein can be used as the vegetable protein odor masking composition of the present invention. For example, a composition containing ethanol can be mentioned, and the ethanol content in the composition is preferably 5 to 50% by weight, more preferably 8 to 30 parts by weight. The ethanol content can be quantified by a conventional method, and a commonly available measurement kit may be used.

[0015] Furthermore, the masking composition of the present invention preferably contains a phenolic compound having a phenolic skeleton in its structure. The phenolic compound may be a monomer or a polymer. Examples of the phenolic compound include ferulic acid, 4-vinylphenol, p-coumaric acid, 4-vinylguaiacol, eugenol, isoeugenol, vanillin, caffeic acid, chlorogenic acid, coniferyl alcohol, catechol, resorcinol, gallic acid, pyrogallol, and compounds obtained by oxidizing these compounds in the presence of oxygen, irradiating them with light, or treating them with an enzyme, and polyphenolic compounds. The composition of the present invention may contain one or more of the above phenolic compounds, or may be prepared by adding the above phenolic compounds in a desired amount. The amount of the phenolic compounds in the composition is preferably 200 to 8000 ppm (parts by weight), more preferably 300 to 6500 ppm (parts by weight). When the amount of the phenolic compounds in the composition is less than the desired amount, it may be prepared by adding a commonly available phenolic compound. The amount of the phenolic compounds in the composition can be quantified by the Folin-Denis method.

[0016] The composition obtained by the method in the upper row can be made to coexist with a vegetable protein material to mask the characteristic aroma of the vegetable protein material. The method of making the composition coexist can be appropriately set depending on the form of the vegetable protein material. For example, the composition of the present invention can be added as is or in a diluted form to a powdery, paste-like, granular or fibrous vegetable protein material to make the composition coexist with the vegetable protein material, thereby masking the vegetable protein odor. In addition, if the vegetable protein material is in a dry state and structured in a granular or fibrous form, the masking effect can be obtained by adding the composition to the water used for reconstitution with water.

[0017] Since 2-(2-ethoxyethoxy)-ethanol, linear alkanes with 14 to 20 carbon atoms, or 2-methylnaphthalene in vegetable proteins contribute to the unpleasant odors of vegetable proteins, such as stuffy or powdery odors, the masking effect of vegetable protein odors can be determined by evaluating the level of the unpleasant odors, such as stuffy or powdery odors, through sensory evaluation.

[0018] As long as the masking effect of the vegetable protein odor is observed, the amount of the composition of the present invention to be added is not particularly limited, but for example, 0.3 to 15 parts by weight, preferably 0.4 to 12 parts by weight, and more preferably 0.5 to 10 parts by weight of the composition of the present invention may be added per 100 parts by weight of the dry weight of the vegetable protein material. When a dried vegetable protein material is reconstituted with water, the masking effect can also be obtained by adding the composition of the present invention in the above-mentioned amount to the water used for reconstitution.

[0019] In addition, since 2-(2-ethoxyethoxy)-ethanol, linear alkanes having 14 to 20 carbon atoms, or 2-methylnaphthalene in vegetable proteins contribute to the characteristic aroma of vegetable proteins that is expressed as stuffy or powdery, it is possible to screen for compositions that suppress vegetable protein odors that are expressed as stuffy or powdery by evaluating the level of unpleasant odors that are said to be stuffy or powdery through sensory evaluation. For example, a test substance is added to a vegetable protein material in a group, and a test substance is not added in a group. After heating as necessary, the strength of the vegetable protein odor is evaluated through sensory evaluation, thereby screening for compounds or compositions that can mask the vegetable protein odor caused by one or more of 2-(2-ethoxyethoxy)-ethanol and linear alkanes having 14 to 20 carbon atoms. EXAMPLES

[0020] The present invention will be specifically described below using examples, but the present invention is not limited to these.

[0021] <Vegetable protein odor and its masking> As the alcohol-containing seasoning A, which is the masking composition of the present invention, "Albono PR Red" (11% alcohol, 5900 ppm phenolic compounds; Mitsubishi Corporation Life Sciences) was used. In addition, as the plant-derived protein material, commercially available granular dried soy protein was used. The masking effect was confirmed as follows. One part by weight of dried soy protein was immersed in 3 parts by weight of water containing 2.0% by weight of alcohol-containing seasoning A for 15 minutes to obtain a sample of Example 1. In addition, the same operation was performed as in Comparative Example 1, except that water to which ethanol was added was used to obtain the same final concentration (0.71% by weight) as the alcohol-containing seasoning A-added group, instead of the alcohol-containing seasoning A, to obtain the water to which the soy protein was returned. Next, each sample was placed in a vial with a lid, the lid was put on, and the sample was heated at 85°C for 15 minutes and then allowed to cool. Then, 20 μL of 1% cyclohexanol was added as an internal standard, and the gas in the headspace of each vial was subjected to micro solid-phase extraction using an SPME fiber (50 / 30 μm, DVB / CAR / PDMS) and analyzed by a gas chromatograph mass spectrometer (GC-MS). The GC-MS analysis conditions were as follows: A 7890A gas chromatograph and a 5975C EI Inert Plus Turbo Pump mass spectrometer (both manufactured by Agilent) were used. Inlet mode, temperature: splitless, 250℃ Separation column: DB-WAX column 122-7062 (0.25 mm x 60 m x 0.25 μm; Agilent Technologies) Carrier gas and flow rate: Helium, 1.8mL / min Ionization method: EI Detection: Scan Mode 2-(2-ethoxyethoxy)-ethanol (retention time: around 48.3 minutes) Octadecane (retention time: around 54.8 minutes) 2-Methylnaphthalene (retention time: around 56.9 minutes)

[0022] <Vegetable protein odor and masking results> The GC-MS analysis results are shown in Table 1. The analytical values ​​in the table are the peak area values ​​of each compound divided by the peak area value of the internal standard. As a result, it was revealed that the values ​​of 2-(2-ethoxyethoxy)-ethanol, octadecane, and 2-methylnaphthalene contained in the sample of Example 1 were all lower than those of the sample of Comparative Example 1. In addition, a sensory evaluation of the odor of each sample revealed that the vegetable protein odor was suppressed in the sample of Example 1, whereas an unpleasant stuffy odor like wet beans was felt in the sample of Comparative Example 1. From the above, the masking effect of the alcohol-containing seasoning A on 2-(2-ethoxyethoxy)-ethanol, octadecane, and 2-methylnaphthalene was confirmed.

[0023] [Table 1]

[0024] <Test 1 for adding substances that cause vegetable protein odor> We decided to add 2-(2-ethoxyethoxy)-ethanol, octadecane, and 2-methylnaphthalene, which are components contained in vegetable protein materials other than n-hexanal, to confirm whether the vegetable protein odor would be enhanced and whether the enhanced vegetable protein odor would be masked. In the test group using alcohol-containing seasoning A, a liquid was prepared by adding either 2-(2-ethoxyethoxy)-ethanol, octadecane, 2-methylnaphthalene or n-hexanal and alcohol-containing seasoning A to the water used to rehydrate commercially available granular dried soy protein, and 1 part by weight of soy protein was soaked in 3 parts by weight of each prepared liquid for 15 minutes to rehydrate the soy protein. The alcohol-containing seasoning A was added to a final concentration of 2% by weight, 2-(2-ethoxyethoxy)-ethanol to a final concentration of 0.0035% by weight, octadecane to a final concentration of 0.0071% by weight, 2-methylnaphthalene to a final concentration of 0.00070%, and n-hexanal to a final concentration of 0.0035% by weight. In addition, a similar procedure was carried out to obtain a comparative soy protein, except that water containing ethanol was added in place of the alcohol-containing seasoning A so that the final concentration of ethanol was the same. The rehydrated soy protein was placed in a container with a lid, covered, heated at 85°C for 15 minutes, then allowed to cool, and the smell of the vegetable protein was evaluated by sensory evaluation.

[0025] <Results of Test 1 on Addition of Substances Causing Vegetable Protein Odor> The results are shown in Table 2. In the test sections to which none of 2-(2-ethoxyethoxy)-ethanol, octadecane, 2-methylnaphthalene, and n-hexanal was added, it was shown that the vegetable protein odor was suppressed by adding the alcohol-containing seasoning A. Even in the 2-(2-ethoxyethoxy)-ethanol-added area, it was shown that the addition of alcohol-containing seasoning A weakened the vegetable protein odor overall, but in the area where alcohol-containing seasoning A was not added, the unpleasant stuffy odor (stuffy odor) was enhanced. Furthermore, in the area where octadecane was added, the presence of alcohol-containing seasoning A reduced the unpleasant heavy odor, resulting in a clean, less lingering odor, whereas in the area where alcohol-containing seasoning A was not added, the vegetable protein odor was increased. Furthermore, in the area where 2-methylnaphthalene was added, the stuffy smell (stuffy smell) was reduced in the presence of alcohol-containing seasoning A and the overall smell was also weakened, but in the area where alcohol-containing seasoning A was not added, there was a stuffy smell and a muffled smell, and the stuffy smell persisted. Finally, in the area where n-hexanal, known to have a vegetable protein odor, was added, the grass-like, green odor caused by hexanal was reduced in the area where alcohol-containing seasoning A was added, but the stuffy odor was felt to the same extent as in the test area without any added substance or alcohol-containing seasoning A. On the other hand, in the area where alcohol-containing seasoning A was not added, the vegetable protein odor felt at the beginning became stronger and the green odor was enhanced. Based on these results and the GC-MS results described above, it was believed that alcohol-containing seasoning A inhibits the migration of 2-(2-ethoxyethoxy)-ethanol, octadecane, and 2-methylnaphthalene to the gas phase, making the vegetable protein odor caused by 2-(2-ethoxyethoxy)-ethanol, octadecane, or 2-methylnaphthalene less noticeable when eaten, i.e., masking the vegetable protein odor.

[0026] [Table 2]

[0027] <Test 2 for the addition of substances that cause vegetable protein odor> As the masking composition of the present invention, alcohol-containing seasoning A was used, and as brewed seasoning B, "Nishikimi Junmai" (alcohol 14.5%, phenolic compounds 725 ppm; Mitsubishi Corporation Life Sciences) was used. One part by weight of dried soy protein was immersed for 15 minutes in 3 parts by weight of water containing 2% by weight of alcohol-containing seasoning A, 0.0035% by weight of 2-(2-ethoxyethoxy)-ethanol, 0.0071% by weight of octadecane, 0.00070% by weight of 2-methylnaphthalene, and 0.0035% by weight of n-hexanal, to obtain a sample of Example 2. The same procedure was carried out except that brewed seasoning B was added to the sample at 3% by weight instead of alcohol-containing seasoning A, to obtain a sample of Example 3. The same procedure was carried out except that alcohol-containing seasoning A was not included, to obtain a sample of Comparative Example 2. Each sample was placed in a vial, heated to 85°C for 15 minutes with the lid open, and then cooled. 20 μL of 1% cyclohexanol was added as an internal standard and the sample was subjected to GC-MS analysis. The retention time of n-hexanal is around 16.1 minutes.

[0028] <Results of Test 2 on Addition of Substances Causing Vegetable Protein Odor> The results are shown in Table 3. Compared to Comparative Example 2, Examples 2 and 3 showed lower values ​​for all items, indicating that the vegetable protein odor can be suppressed. The test results also showed that alcohol-containing seasoning A was highly effective in suppressing the odors of 2-(2-ethoxyethoxy)-ethanol and 2-methylnaphthalene. Furthermore, it was shown that brewed seasoning B was excellent in suppressing the vegetable protein odor caused by octadecane.

[0029] [Table 3]

[0030] <Addition test to foods containing vegetable protein> To confirm the effect on foods and beverages containing vegetable protein, 15.35 g of soy protein was soaked and rehydrated in a solution of 37.28 g of water and 1.07 g of brewed seasoning B. The ingredients were then mixed according to the recipe in Table 4, molded into 25 g portions, and baked at 180°C for 8 minutes to obtain the hamburger steak of Example 4. Moreover, the same procedure was carried out by adding an equal amount of water instead of the brewed seasoning B, to obtain a hamburger steak of Comparative Example 3.

[0031] [Table 4]

[0032] <Results of tests on foods containing vegetable protein> A sensory evaluation was carried out on each of the prepared hamburgers, and the stuffy odor and powdery unpleasant odor were evaluated. As a result, in Example 4, in which brewed seasoning B was added, the stuffy odor and powdery odor derived from the vegetable protein were suppressed, and the taste of the ingredients could be felt. On the other hand, in Comparative Example 3, the stuffy odor and powdery unpleasant odor derived from the vegetable protein odor were significantly felt.

[0033] These results indicate that 2-(2-ethoxyethoxy)-ethanol, octadecane, and 2-methylnaphthalene contribute to the vegetable protein odor, and that the vegetable protein odor can be suppressed by masking any of the odors.

Claims

1. A method for masking the characteristic odor of vegetable protein by masking the odor of one or more compounds involved in the characteristic odor of vegetable protein, namely, 2-(2-ethoxyethoxy)-ethanol, a straight-chain alkane having 14 to 20 carbon atoms, and 2-methylnaphthalene.

2. The method for masking the characteristic odor of a vegetable protein comprises adding to the vegetable protein a compound or composition capable of masking odors caused by one or more of the following compounds: 2-(2-ethoxyethoxy)-ethanol, a linear alkane having 14 to 20 carbon atoms, and 2-methylnaphthalene.

3. The method of claim 2 , wherein the compound or composition is ethanol and a phenolic compound.

4. An odor masking composition comprising one or more compounds selected from the group consisting of 2-(2-ethoxyethoxy)-ethanol, a linear alkane having 14 to 20 carbon atoms, and 2-methylnaphthalene.

5. The masking composition according to claim 4, comprising ethanol and a phenolic compound as active ingredients.

6. A method for screening masking compositions using as an indicator the masking of odor by one or more compounds involved in the characteristic odor of vegetable protein: 2-(2-ethoxyethoxy)-ethanol, a linear alkane having 14 to 20 carbon atoms, and 2-methylnaphthalene.

7. A plant-derived protein-containing composition in which the odor caused by one or more compounds involved in the characteristic odor of plant protein, namely 2-(2-ethoxyethoxy)-ethanol, a straight-chain alkane having 14 to 20 carbon atoms, and 2-methylnaphthalene, is masked.

8. A method for producing a plant-derived protein-containing composition, comprising a step of masking odors caused by one or more compounds involved in the characteristic odor of plant proteins: 2-(2-ethoxyethoxy)-ethanol, a linear alkane having 14 to 20 carbon atoms, and 2-methylnaphthalene.

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