Oil-based paste-like composition containing mustard seeds, method for producing same, and food containing same

The oil-based paste composition produced by crushing and heating mustard seeds in fat or oil effectively reduces pungency while maintaining the unique flavors of mustard seeds, suitable for use in food products.

WO2026028555A1PCT designated stage Publication Date: 2026-02-05HOUSE FOODS CORPORATION +1
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Patent Information

Application Number
PCT/JP2025/017581
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Priority Date
2024-07-30
Filing Date
2025-05-14
Publication Date
2026-02-05

AI Technical Summary

Technical Problem

Existing methods for producing mustard seed-based products struggle to balance the reduction of pungency while retaining the unique flavor characteristics of mustard seeds, such as sweetness, due to the volatility of pungent components like allyl isothiocyanate.

Method used

A method involving the production of an oil-based paste composition by crushing mustard seeds in a mixture with fat or oil, followed by heating and grinding to an average particle size of 300 μm or less, which reduces pungency and enhances desirable flavors like sweetness.

Benefits of technology

The resulting oil-based paste composition has reduced pungency and retains the characteristic flavors of mustard seeds, making it suitable for incorporation into various foods without affecting texture or appearance.

✦ Generated by Eureka AI based on patent content.

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Abstract

The purpose of the present invention is to provide a composition that has a favorable flavor that is unique to mustard seeds, such as sweetness, and that has suppressed pungency. Firstly, the present invention relates to a method for producing an oil-based paste-like composition containing pulverized mustard seeds, the method comprising a step of pulverizing the mustard seeds in a mixture of mustard seeds and an oil or fat. Secondly, the present invention relates to an oil-based paste-like composition containing pulverized mustard seeds in which the content of allyl isothiocyanate is significantly lower than that of untreated mustard seeds, and the content of one or more of 2-methyltetrahydrofuran-3-one, 2-furfurylthiol, α-angelica lactone, 2-methyltetrahydrothiophen-3-one, tetrahydrothiophen-3-one, β-angelica lactone, γ-crotonolactone, dimethyl sulfone, furfuryl methyl sulfide, 1-furfuryl pyrrole, and guaiacol is remarkably higher than that of untreated mustard seeds.
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Description

Oil-based paste composition containing mustard seeds, method for producing the same, and food containing the same

[0001] The present invention relates to an oil-based paste-like composition containing crushed mustard seeds, a method for producing the same, and a food product containing the same.

[0002] Mustard seeds are a spice with a distinctive, spicy flavor and are used as an ingredient in mustard and dressings.

[0003] Patent Document 1 describes a method for producing a seasoning using mustard seeds as a raw material, by extracting new umami components from the mustard seeds in a short time, stably and reliably, thereby significantly improving the overall flavor. Specifically, Patent Document 1 describes a method for producing a seasoning, which comprises crushing mustard seeds, treating the crushed mustard seeds to remove pungent components and / or glycosides of the pungent components, and then enzymatically treating the residue with a protease.

[0004] Patent Document 2 describes a physicochemical treatment of seeds (mustard seeds) such as mustard greens, with the aim of providing mustard seeds and mustard that can be eaten in large quantities while suppressing the development of pungency and bitterness. Patent Document 2 describes that the physical treatment involves soaking mustard seeds in a sufficient amount of salt water with a salt concentration of 15% or more at room temperature for 10 days or more.

[0005] Patent Document 3 describes a problem in that the pungency of mustard seeds is due to components such as allyl isothiocyanate, which are easily volatile and the unique flavor of mustard seeds is easily lost over time. Patent Document 3 then describes, as a means of solving this problem, a mustard seed-containing emulsified seasoning, which contains 5 to 50% by mass of whole mustard seeds and ground brown mustard seeds in a total content of 5 to 50% by mass, a ratio of the whole mustard seeds to the ground brown mustard seeds of 1:1 to 20, at least 65% by mass of the ground brown mustard seeds having a 32 Tyler mesh size, and contains 0.5% by mass or more of an edible oil. The mustard seed-containing emulsified seasoning described in Patent Document 3 is an aqueous composition in which the edible oil is dispersed as a dispersed phase.

[0006] JP 2005-176705 A JP 2018-57351 A JP 2019-10034 A Japanese Patent No. 7498381 A

[0007] Mustard seeds have a pungent taste but also have a uniquely pleasant flavor such as sweetness. There is a need for a technology that can reduce the pungency of mustard seeds while retaining the inherently pleasant flavor of mustard seeds.

[0008] Therefore, an object of the present invention is to provide a composition that has a pleasant flavor, such as the sweetness, that is characteristic of mustard seeds, and that has reduced pungency.

[0009] The present inventors have discovered that an oil-based paste composition containing crushed mustard seeds, produced by a method including a step of crushing mustard seeds in a mixture of mustard seeds and fat or oil, has a pleasant flavor, such as sweetness, that is characteristic of mustard seeds, and has a reduced pungency.

[0010] [1] A method for producing an oil-based paste-like composition containing ground mustard seeds, comprising a step of grinding the mustard seeds in a mixture of mustard seeds and fats and oils. [2] The method according to [1], further comprising a step of heating the mustard seeds to obtain heat-treated mustard seeds, wherein the mixture is a mixture of the heat-treated mustard seeds and the fats and oils. [3] The method according to [2], wherein the step of obtaining heat-treated mustard seeds comprises heating the mustard seeds in an open system under conditions such that the heat number is 200 or higher. [4] The method according to any one of [1] to [3], wherein the step of grinding the mustard seeds comprises grinding the mustard seeds to an average particle size of 300 μm or less. [5] The method according to any one of [1] to [4], wherein the mixture comprises 50 to 200 parts by mass of the fats and oils per 100 parts by mass of the mustard seeds. [6] The method according to any one of [1] to [5], wherein the mixture has a moisture content of 5% by mass or less. [7] An oil-based paste-like composition containing crushed mustard seeds, wherein a sample is prepared by adding 4-methylthiazole to the oil-based paste-like composition in an amount equivalent to 1.0 μg / g of the mustard seed equivalent of the oil-based paste-like composition, and the volatile components are extracted from the sample by solid phase microextraction-gas chromatography-mass spectrometry (SPME-GC-MS) at an extraction temperature of 60°C for 10 minutes. In the chromatogram obtained, (1) the area ratio of the peak area derived from allyl isothiocyanate to the peak area derived from 4-methylthiazole is 10.0 or less, and (2) the area ratio of the peak area derived from 2-methyltetrahydrofuran-3-one to the peak area derived from 4-methylthiazole is 1.0 or more, and (3) the area ratio of the peak area derived from 2-furfurylthiol to the peak area derived from 4-methylthiazole is 0.010 or more. (4) the area ratio of the peak area derived from α-angelicalactone to the peak area derived from 4-methylthiazole is 0.020 or more;(5) the area ratio of the peak area derived from 2-methyltetrahydrothiophen-3-one to the peak area derived from 4-methylthiazole is 0.30 or more, (6) the area ratio of the peak area derived from tetrahydrothiophen-3-one to the peak area derived from 4-methylthiazole is 0.060 or more, (7) the area ratio of the peak area derived from β-angelicalactone to the peak area derived from 4-methylthiazole is 0.045 or more, (8) the area ratio of the peak area derived from γ-crotonolactone to the peak area derived from 4-methylthiazole is 0.40 or more, (9) the area ratio of the peak area derived from dimethyl sulfone to the peak area derived from 4-methylthiazole is 0.13 or more, (10) the area ratio of the peak area derived from furfuryl methyl sulfide to the peak area derived from 4-methylthiazole is 0.050 or more, (11) An oil-based paste-like composition that satisfies one or more of the following: (11) The area ratio of the peak area derived from 1-furfurylpyrrole to the peak area derived from 4-methylthiazole is 0.010 or more, and (12) The area ratio of the peak area derived from guaiacol to the peak area derived from 4-methylthiazole is 0.020 or more. [8] An oil-based paste-like composition produced by the method according to any one of [1] to [6], or a food product comprising the oil-based paste-like composition according to [7].

[0011] This specification includes the disclosure of Japanese Patent Application No. 2024-123506, from which the present application claims priority.

[0012] Furthermore, all publications, patents, and patent applications cited herein are hereby incorporated by reference in their entirety.

[0013] The method of the present invention makes it possible to produce an oil-based paste composition that has the pleasant flavor, such as sweetness, that is characteristic of mustard seeds, and that has reduced pungency.

[0014] The oil-based paste composition according to the present invention has a pleasant flavor, such as sweetness, that is characteristic of mustard seeds, and has a reduced pungency.

[0015] The oil-based paste-like composition produced by the production method of the present invention and foods containing the oil-based paste-like composition of the present invention have a pleasant flavor unique to mustard seeds.

[0016] 1 shows the peak area ratios of specific components in the oil-based paste composition prepared in Example 1(2) and raw unheated mustard seeds to the internal standard (1.0 μg / g of 4-methylthiazole based on the mustard seeds) in extracted ion chromatograms obtained by SPME-GC-MS. 1 shows the peak area ratios of specific components in the oil-based paste composition prepared in Example 1(2) and raw unheated mustard seeds to the internal standard (1.0 μg / g of 4-methylthiazole based on the mustard seeds) in extracted ion chromatograms obtained by SPME-GC-MS. 1 shows the peak area ratios of specific components in the oil-based paste composition prepared in Example 1(2) and raw unheated mustard seeds to the internal standard (1.0 μg / g of 4-methylthiazole based on the mustard seeds) in extracted ion chromatograms obtained by SPME-GC-MS. 1 shows the peak area ratios of specific components in the oil-based paste composition prepared in Example 1(2) and raw unheated mustard seeds to the internal standard (1.0 μg / g of 4-methylthiazole based on the mustard seeds) in extracted ion chromatograms obtained by SPME-GC-MS. FIG. 1 shows the peak area ratios of specific components in the oil-based paste composition prepared in Example 1(2) and raw uncooked mustard seeds to an internal standard (1.0 μg / g 4-methylthiazole in mustard seeds) in extracted ion chromatograms obtained by SPME-GC-MS.

[0017] <Mustard Seeds> In the present disclosure, the mustard seeds used may be seeds of brown mustard (Brassica juncea), black mustard (Brassica nigra), or white mustard (Sinapis alba), and preferably brown mustard seeds are used. The mustard seeds used as a raw material in the method for producing an oil-based paste composition according to the present disclosure are preferably in the form of whole seeds.

[0018] <Oils and Fats> In the present disclosure, oils and fats that are acceptable for use as food can be used. Examples of oils and fats that are acceptable for use as food include oils and fats derived from plants, animals, microorganisms, etc., and may be a mixture of multiple oils and fats. The oils and fats may be liquid or solid at 20°C, but are preferably liquid at 20°C. Examples of oils and fats that are liquid at 20°C include rapeseed oil, high oleic rapeseed oil, soybean oil, high oleic soybean oil, corn oil, sesame oil, sesame salad oil, perilla oil, linseed oil, peanut oil, safflower oil, high oleic safflower oil, sunflower oil, high oleic sunflower oil, cottonseed oil, grapeseed oil, macadamia nut oil, hazelnut oil, perilla oil, olive oil, rice bran oil, and wheat germ oil. The melting point of the oils and fats may be adjusted by techniques such as fatty acid transesterification or hydrogenation.

[0019] <Method for producing an oil-based pasty composition containing crushed mustard seeds> The present disclosure first relates to a method for producing an oil-based pasty composition containing crushed mustard seeds, the method comprising a step of crushing the mustard seeds in a mixture of mustard seeds and oil (hereinafter referred to as the "crushing step").

[0020] The oil-based paste composition produced by the production method according to the present disclosure is a paste composition comprising a fat or oil and crushed mustard seeds dispersed in a continuous phase of the fat or oil. The oil-based paste composition has a mild pungency characteristic of mustard seeds and a pleasant flavor such as sweetness inherent to mustard seeds, and therefore can be incorporated into various foods to impart a pleasant flavor.

[0021] Allyl isothiocyanate, known as the component responsible for the pungent taste of mustard seeds, is usually produced by an enzymatic reaction that occurs during the grinding of mustard seeds. During the grinding process, when mustard seeds are ground in a mixture with oil, there is thought to be insufficient water, which acts as a solvent for the enzymatic reaction, making it difficult for allyl isothiocyanate to be produced.

[0022] On the other hand, components such as 2-methyltetrahydrofuran-3-one, 2-furfurylthiol, α-angelicalactone, 2-methyltetrahydrothiophen-3-one, tetrahydrothiophen-3-one, β-angelicalactone, γ-crotonolactone, dimethyl sulfone, furfuryl methyl sulfide, 1-furfurylpyrrole, and guaiacol, which are thought to give rise to the flavor unique to mustard seeds, have a high affinity for fats and oils and are therefore thought to be extracted from mustard seeds into fats and oils during the crushing process.

[0023] It is believed that these mechanisms are the reason why the oil-based paste composition produced by the production method according to the present disclosure, which includes the grinding step, contains fewer pungent components and retains the unique flavor inherent to mustard seeds. However, the scope of the present invention is not limited by the mechanisms described above.

[0024] In the grinding step, the mustard seeds in the mixture are preferably ground to an average particle size of 300 μm or less, more preferably 200 μm or less, and even more preferably 100 μm or less. Here, the average particle size refers to the average value of the particle size distribution (volume basis) obtained by measuring the particle size distribution (volume basis) of the particles in the ground mixture using a laser diffraction particle size analyzer (the value of 10 μ where μ is the average value of the particle size distribution (volume basis) on a common logarithmic scale). An oil-based paste-like composition containing mustard seeds finely ground to an average particle size within the above range has a smooth texture and does not affect the texture of foods. Furthermore, the appearance of the mustard seed particles is inconspicuous when visually inspected, making it suitable for incorporation into various foods. In particular, even when brown mustard, black mustard, or heat-treated mustard seeds, which tend to have a noticeable appearance, are used as mustard seeds, grinding them to an average particle size within the above range allows for an oil-based paste-like composition with an inconspicuous appearance to be obtained. The crushed mustard seed particles dispersed in the oil-based paste composition of the present disclosure are less likely to swell with water even after being incorporated into foods containing water, and the above-mentioned effects can be maintained.

[0025] When mustard seeds are ground without adding oil or fat, the oil exuded from the mustard seeds causes the ground seeds to bind together and not pass through a sieve, making it difficult to grind them to an average particle size of 300 μm or less. Even when mustard seeds are ground with the addition of a powder component such as dextrin that can absorb oil or fat, grinding the mustard seeds to an average particle size of 300 μm or less is difficult. On the other hand, it is possible to classify and recover mustard seeds with an average particle size of 300 μm or less by sieving, but the yield is low. Furthermore, when ground mustard seeds that are not dispersed in oil or fat and that have been classified by sieving are incorporated into foods, they tend to swell in the presence of water in the food, resulting in undesirable appearance and texture. The manufacturing method of the present disclosure is advantageous in that it easily produces an oil-based paste-like composition containing fine ground mustard seeds that has a smooth texture and an inconspicuous appearance when incorporated into foods.

[0026] The grinding step can be carried out using a grinding device capable of grinding (wet grinding) the mustard seeds in the mixture containing mustard seeds and fats and oils. As the grinding device, a grinding device that grinds the mustard seeds in the mixture by grinding force, such as a Comitrol (registered trademark), a colloid mill, a ball mill, or an attritor, is preferred.

[0027] The mixing ratio of mustard seeds and fats and oils in the mixture can be adjusted as appropriate, and the mixture preferably contains 20 to 500 parts by mass, more preferably 50 to 200 parts by mass, and even more preferably 80 to 120 parts by mass of fats and oils per 100 parts by mass of mustard seeds.

[0028] The mixture of mustard seeds and fats and oils to be subjected to the grinding step preferably has a water content of 5% by mass or less in the entire mixture. When a mixture with a water content of 5% by mass or less is subjected to the grinding step, the enzymatic reaction that produces allyl isothiocyanate is unlikely to occur, and an oily paste-like composition with reduced pungency is likely to be obtained.

[0029] The mixture of mustard seeds and fats and oils to be subjected to the grinding step may contain other ingredients in addition to the mustard seeds and fats and oils, but the total amount of mustard seeds and fats and oils is preferably 95% by mass or more, more preferably 98% by mass or more, and even more preferably 99% by mass or more of the total amount of the mixture. It is particularly preferred that the mixture consists of mustard seeds and fats and oils.

[0030] In the method for producing an oil-based paste composition according to the present disclosure, the mustard seeds ground together with the oil or fat may be either heat-treated or unheated, but heat-treated mustard seeds are preferred. The method for producing an oil-based paste composition according to the present disclosure preferably further includes a step of heating the mustard seeds to obtain heat-treated mustard seeds (hereinafter referred to as the "heating step") prior to the grinding step. The mixture of the heat-treated mustard seeds and the oil or fat can be subjected to the grinding step. As described in Patent Document 4, heat-treated mustard seeds have enhanced sweetness and savory flavor, and can be incorporated into foods to enhance their flavor. Furthermore, heat-treated mustard seeds have reduced enzymatic activity, making them less likely to produce allyl isothiocyanate during grinding in the grinding step. Therefore, the oil-based paste composition produced by the method according to the present disclosure, which includes the heating and grinding steps, is preferred because it further reduces the pungency characteristic of mustard seeds and further enhances their desirable flavors, such as sweetness and savory flavor. In addition, the oil-based paste composition produced by the method of the present disclosure, which includes a heating step and a grinding step, is also preferable in that it has the effect of enhancing the taste of food when added to food.

[0031] The mustard seeds to be subjected to the heating step are preferably in the form of whole seeds. The heating step is more preferably a dry heating step in which the mustard seeds are heated without being mixed with liquid ingredients such as oils, fats, water, etc., and even more preferably a step in which only the mustard seeds are heated.

[0032] A more preferred embodiment of the heating step includes heating the mustard seeds in an open system under conditions such that the heat value is at least 200. The heat-treated mustard seeds obtained by this embodiment have a particularly strong effect of enhancing desirable flavors such as sweetness and savory aromas, as well as taste.

[0033] In the heating step of this embodiment, the heating temperature and time are set so that the heating value is 200 or more, more preferably 600 or more, even more preferably 800 or more, and most preferably 950 or more. Furthermore, it is preferable to set the temperature and time so that the heating value is preferably 200 or more and 10,000 or less, more preferably 600 or more and 6,000 or less, even more preferably 800 or more and 6,000 or less, and most preferably 950 or more and 6,000 or less. Mustard seeds heat-treated in an open system under conditions that result in a heating value within the above range have significantly enhanced sweetness and savory flavor compared to mustard seeds heat-treated under conditions that result in a heating value of less than 200. Heating conditions that result in a heating value within the above range can preferably include heating at the temperature and time described below.

[0034] In the present disclosure, "heat value" refers to the value obtained by integrating the value expressed by the following formula (hereinafter referred to as "CV value") over the heating time (minutes). In the present disclosure, the "reference temperature" in the following formula is set to 110°C, and the "Z value" is set to 30 (°C). (Formula): CV value = 10 [(product temperature - reference temperature) / Z value]

[0035] In the heating step of this embodiment, the maximum temperature (product temperature) of the mustard seeds can be, for example, 130° C. or higher, preferably 140° C. or higher, and more preferably 160° C. or higher, and can be, for example, 130° C. or higher and 200° C. or lower, preferably 140° C. or higher and 200° C. or lower, and more preferably 160° C. or higher and 200° C. or lower. The heating time within the above temperature range can be appropriately adjusted so that the heating value falls within a predetermined range, and can be, for example, within a range of 3 minutes to 30 minutes.

[0036] In the heating step of this embodiment, the mustard seeds are heat-treated in an open system. Heat treatment in an open system refers to a heat treatment in an unsealed environment where volatile components, including moisture and aroma components, can volatilize into the surrounding atmosphere during heat treatment. Heating mustard seeds in oil (roasting in oil) does not qualify as an open-system heat treatment because the oil prevents the evaporation of moisture and volatile components from the mustard seeds. As described in Patent Document 4, mustard seeds heat-treated in an open system under conditions resulting in a heating value of 200 or higher have superior sweetness and savory flavor compared to mustard seeds heat-treated in a sealed container or mustard seeds roasted in oil, and when incorporated into foods, they have a particularly strong effect of enhancing flavors such as richness. Examples of heat treatment devices that can be used for open-system heat treatment include roasters equipped with open containers such as pans, rotary cylindrical kettles, and pots, as well as ovens and hot-air roasters with open chambers. Heat treatment in such an open system can be referred to as "roasting." The heat treatment in an open system can be carried out under non-pressurized conditions.

[0037] The mixture of mustard seeds and fats containing crushed mustard seeds obtained through the above-mentioned crushing step or the above-mentioned heating step and crushing step can be used as an oil-based paste composition. The produced oil-based paste composition can be incorporated into food products. Specific embodiments of the food products are described below.

[0038] <Oil-based paste-like composition containing crushed mustard seeds> The present disclosure secondly provides an oil-based paste-like composition containing crushed mustard seeds, wherein a sample is prepared by adding 4-methylthiazole to the oil-based paste-like composition in an amount that is 1.0 μg / g relative to the amount of mustard seeds in the oil-based paste-like composition, and the sample is analyzed by solid phase microextraction-gas chromatography-mass spectrometry (SPME-GC-MS), which involves extracting volatile components from the oil-based paste-like composition at an extraction temperature of 60°C for an extraction time of 10 minutes. In the resulting chromatogram, (1) the area ratio of the peak area derived from allyl isothiocyanate to the peak area derived from 4-methylthiazole is 10.0 or less, and preferably 0 or more and 2.0 or less, and (2) to (12) below: (2) the area ratio of the peak area derived from 2-methyltetrahydrofuran-3-one to the peak area derived from 4-methylthiazole is 1.0 or more, and preferably 1.4 or more and 7.4 or less, (3) the area ratio of the peak area derived from 2-furfurylthiol to the peak area derived from 4-methylthiazole is 0.010 or more, preferably 0.015 or more and 0.30 or less, (4) the area ratio of the peak area derived from α-angelicalactone to the peak area derived from 4-methylthiazole is 0.020 or more, preferably 0.030 or more and 0.430 or less, (5) the area ratio of the peak area derived from 2-methyltetrahydrothiophen-3-one to the peak area derived from 4-methylthiazole is 0.30 or more, preferably 0.45 or more and 2.75 or less, (6) the area ratio of the peak area derived from tetrahydrothiophen-3-one to the peak area derived from 4-methylthiazole is 0.060 or more, preferably 0.10 or more and 0.55 or less, (7) the area ratio of the peak area derived from β-angelicalactone to the peak area derived from 4-methylthiazole is 0.045 or more, preferably 0.08 or more and 0.36 or less, (8) the area ratio of the peak area derived from γ-crotonolactone to the peak area derived from 4-methylthiazole is 0.40 or more, preferably 0.65 or more and 3.25 or less,(9) the area ratio of the peak area derived from dimethyl sulfone to the peak area derived from 4-methylthiazole is 0.13 or more, preferably 0.20 or more and 1.09 or less; (10) the area ratio of the peak area derived from furfuryl methyl sulfide to the peak area derived from 4-methylthiazole is 0.050 or more, preferably 0.15 or more and 0.76 or less; (11) the area ratio of the peak area derived from 1-furfurylpyrrole to the peak area derived from 4-methylthiazole is 0.010 or more, preferably 0.025 or more and 0.14 or less; and (12) the area ratio of the peak area derived from guaiacol to the peak area derived from 4-methylthiazole is 0.020 or more, preferably 0.040 or more and 0.25 or less.

[0039] The oil-based paste composition according to the present disclosure has a low concentration of allyl isothiocyanate, which is responsible for the pungency unique to mustard seeds, resulting in a weak pungency, and a high concentration of one or more of 2-methyltetrahydrofuran-3-one, 2-furfurylthiol, α-angelicalactone, 2-methyltetrahydrothiophen-3-one, tetrahydrothiophen-3-one, β-angelicalactone, γ-crotonolactone, dimethyl sulfone, furfuryl methyl sulfide, 1-furfurylpyrrole, and guaiacol, which are responsible for the flavor, such as sweetness, unique to mustard seeds, resulting in a strong flavor unique to mustard seeds. The oil-based paste composition according to the present disclosure can be incorporated into various foods for the purpose of imparting a pleasant flavor unique to mustard.

[0040] Solid-phase microextraction-gas chromatography mass spectrometry is a method in which the volatile components of a measurement sample are adsorbed by solid-phase microextraction (SPME) (a static extraction method in which a fiber is exposed to the gas phase and the volatile components are collected on an adsorbent), and then the measurement is performed by gas chromatography mass spectrometry (GS-MS). Specifically, the oil-based paste composition of the present disclosure or a diluted product thereof is placed in a 20 mL GC vial so that the equivalent amount is approximately 80 mg to 120 mg (e.g., 100 mg) of mustard seed, and 4-methylthiazole is added in an amount that is 1.0 μg / g of the oil-based paste composition equivalent to mustard seed, after which the vial is sealed. The volatile components in the headspace within the vial are adsorbed onto an adsorption resin (SPMEarrow fiber) and extracted at an extraction temperature of 60°C for 10 minutes, and then processed using a thermal desorption system, after which the vial can be introduced into a gas chromatography mass spectrometer for analysis. Specific conditions for the solid-phase microextraction-gas chromatography mass spectrometry method include those described in the Examples.

[0041] The oil-based paste composition according to the present disclosure comprises a fat or oil and crushed mustard seeds dispersed in a continuous phase comprising the fat or oil. The mixing ratio of the mustard seeds and the fat or oil contained in the oil-based paste composition according to the present disclosure can be adjusted as appropriate. For example, the oil or oil is preferably contained in a ratio of 50 to 200 parts by mass, more preferably 80 to 120 parts by mass, per 100 parts by mass of mustard seeds.

[0042] The average particle size of the ground mustard seeds contained in the oil-based paste-like composition according to the present disclosure is preferably 300 μm or less, more preferably 200 μm or less, and even more preferably 100 μm or less. The definition of average particle size is as described above. The oil-based paste-like composition according to the present disclosure containing mustard seeds with an average particle size in this range has a smooth texture on the tongue and does not affect the texture of foods. Moreover, the appearance of the mustard seed particles is not noticeable when the food containing the oil-based paste-like composition is visually inspected, so that the oil-based paste-like composition can be incorporated into a variety of foods.

[0043] The oil-based paste composition according to the present disclosure preferably has a water content of 5% by mass or less in the entire composition, since an enzymatic reaction that produces allyl isothiocyanate is unlikely to occur in a composition with a water content of 5% by mass or less.

[0044] The oil-based paste-like composition according to the present disclosure may contain other ingredients in addition to the crushed mustard seeds and fats and oils, but the total amount of the crushed mustard seeds and fats and oils relative to the total amount of the composition is preferably 95% by mass or more, more preferably 98% by mass or more, and even more preferably 99% by mass or more. It is particularly preferred that the oil-based paste-like composition according to the present disclosure consists of crushed mustard seeds and fats and oils.

[0045] The oil-based paste-like composition according to the present disclosure can be produced by the above-described production method according to the present disclosure, which includes a grinding step of grinding mustard seeds in a mixture of mustard seeds and fat or oil. Preferred aspects of the production method are as described above.

[0046] <Food> Thirdly, the present disclosure relates to an oil-based paste-like composition produced by the production method according to the present disclosure, or a food containing the oil-based paste-like composition according to the present disclosure.

[0047] Examples of foods according to the present disclosure include an oil-based paste-like composition produced by the production method according to the present disclosure, or a food composition that can be used as a seasoning or the like, comprising an oil-based paste-like composition according to the present disclosure in combination with other food ingredients such as other fats and oils, excipients, aqueous seasonings, oil-based seasonings, spices, sugars, sweeteners, salt, minerals, antioxidants, etc. The food composition may be an oil-based paste-like composition itself, or an oil-based liquid composition. For example, the food composition may be an oil-based paste-like composition produced by the production method according to the present disclosure, or an oil-based paste-like or liquid composition comprising an oil-based paste-like composition according to the present disclosure and a liquid fat or oil that is liquid at 20°C. The oil-based paste-like or liquid composition may further comprise a polysaccharide such as dextrin. The food composition may be an oil-based paste-like composition produced by the production method of the present disclosure, an emulsion composition containing the oil-based paste-like composition of the present disclosure, or an oil-based diluent thereof as a dispersed phase, or an emulsion composition containing the oil-based paste-like composition of the present disclosure, or an oil-based diluent thereof as a continuous phase. The food composition is useful as a seasoning used to impart the pleasant flavor characteristic of mustard seeds to other foods.

[0048] Another example of a food product according to the present disclosure includes a food product formulated with an oil-based paste-like composition produced by the production method according to the present disclosure, or an oil-based paste-like composition according to the present disclosure, or a food composition containing one or more of these (e.g., the food composition described in the preceding paragraph). The food product has a pleasant flavor characteristic of mustard seeds. The type of food product is not particularly limited. Examples include foods based on rice, noodles, meat, etc.

[0049] Unless otherwise specified, the experiments described below were conducted in a room whose temperature was controlled to within a range of approximately 22°C to 25°C by air conditioning with a set temperature of 23°C, and therefore room temperature refers to a temperature between 22°C and 25°C, e.g., 23°C.

[0050] Example 1: Oil-based paste composition using roasted mustard seeds (1) Roasting of brown mustard seeds Whole seeds of brown mustard (Brassica juncea) (hereinafter referred to as "mustard seeds") were roasted in the following manner: (a) 100 kg of mustard seeds were placed in an electromagnetically heated open kettle (open system). (b) The kettle was rotated at 20 rpm and stirred while heating for 24 minutes until the product temperature reached 169°C. (c) Heating was stopped, and the product was cooled to 90°C while stirring in the same kettle.

[0051] The heating value in the heat treatment under the above conditions was 1001. The definition of the heating value is as described above.

[0052] (2) Preparation of an Oil-Based Paste Composition Using a grinder (Comitroll, manufactured by Urschel Japan, micro cutter blade clearance 0.528 mm), 1000 g of roasted mustard seeds and 1000 g of rapeseed oil were added little by little at a mass ratio of 1:1 while being ground using a grinder with a stirring blade cutter blade rotating at a high speed of 3600 rpm. In this grinding process, the roasted mustard seeds were ground in the rapeseed oil to a particle size small enough to pass through the cutter blade clearance of 0.528 mm or smaller. This grinding process produced an oil-based paste composition of mustard seeds.

[0053] Sensory Test 1: Addition of the Oil-Based Paste Composition of Example 1 to Foods The oil-based paste composition of Example 1 prepared in Example 1(2) was added to commercially available processed foods, and the taste was evaluated. In all processed foods, the crushed mustard seeds in the added oil-based paste composition were barely discernible by visual inspection.

[0054] Commercially available frozen chicken rice was heated according to the product instructions. 0.17 g of the oil-based paste composition was added to 180 g of the heated chicken rice, and the resulting mixture was eaten. The deliciousness of fried ketchup was detected.

[0055] Fried rice commercially available as a frozen food was heated according to the product instructions. 0.19 g of the oil-based paste composition was added to 200 g of the heated fried rice, and the resulting mixture was eaten. A slightly browned, fragrant flavor was detected.

[0056] Another type of fried rice available commercially as a frozen food was heated according to the product instructions. 0.21 g of the oil-based paste composition was added to 230 g of the heated fried rice, and the resulting mixture was eaten. A slightly browned fragrant flavor was observed, and the umami flavor was enhanced.

[0057] Neapolitan spaghetti commercially available as a frozen food was heated according to the product instructions. 0.2 g of the oil-based paste composition was added to 360 g of heated spaghetti, and the resulting mixture was eaten. A slightly browned aroma was detected, and the umami flavor was enhanced.

[0058] Example 2: Oil-based paste composition using unroasted mustard seeds. The unroasted mustard seeds used as the raw material in Example 1 (1) were ground together with rapeseed oil by the following procedure. Specifically, a grinder (Comitroll, manufactured by Urschel Japan, microcutter blade clearance 0.528 mm) was used, rotating the stirring blade cutter blade at a high speed of 3600 rpm. 1000 g of unroasted mustard seeds and 1000 g of rapeseed oil were gradually added to the grinder at a mass ratio of 1:1. During this grinding process, the unroasted mustard seeds were ground in the rapeseed oil to a particle size small enough to pass through the cutter blade clearance of 0.528 mm or less. This grinding process resulted in the preparation of the unroasted mustard seed oil-based paste composition of Example 2.

[0059] Comparative Example 1: Unroasted mustard seed powder The unroasted mustard seeds used as the raw material in Example 1 (1) were ground into powder using a mill. The particle size of the resulting powder was 460 μm.

[0060] Comparative Example 2: Mixture of unroasted mustard seed powder and oil The unroasted mustard seed powder prepared in Comparative Example 1 was mixed with rapeseed oil in a mass ratio of 1:1 to prepare the mixture of Comparative Example 2.

[0061] Sensory Test 2: Addition of the Oil-Based Paste Composition of Example 2 to Food Neapolitan spaghetti, available commercially as a frozen food, was heated according to the product instructions. To 120 g of the heated spaghetti, 0.08 g of the unroasted mustard seed powder of Comparative Example 1, 0.16 g of the mixture of Comparative Example 2, or 0.16 g of the oil-based paste composition of Example 2 was added, and each sample was tasted and evaluated by three panelists.

[0062] As a control sample, 120 g of the above-mentioned heated spaghetti without any additives was prepared and eaten.

[0063] The taste of spaghetti samples to which the unroasted mustard seed powder of Comparative Example 1, the mixture of Comparative Example 2, and the oil-based paste composition of Example 2 were added was evaluated relative to the control sample, and the results are shown in the table below.

[0064]

[0065] Flavor Component Analysis (1) SPME-GC-MS Sample Preparation 100 mg of the ground mustard seeds used as the raw material in Example 1(1) or 100 mg of the oil-based paste composition prepared in Example 1(2) equivalent to the mustard seed mass was placed in a 20 mL GC vial. 4-Methylthiazole (Tokyo Chemical Industry Co., Ltd.) was added as an internal standard to a concentration of 1.0 μg / g relative to the mustard seed mass, and the vial was then sealed to prepare a solid-phase microextraction (SPME)-GC-MS sample (n=3).

[0066] (2) SPME-GC-MS Analysis Conditions The conditions for solid-phase microextraction are shown below.

[0067] SPME arrow fiber: Divinylbenzene / Carbon Wide Range / Polydimethylsiloxane (Restek) Volatile component extraction device: TRIPLUS RSH (Thermo Fisher Scientific) Preheating: 60°C, 5 minutes Volatile component extraction: 60°C, 10 minutes Desorption time: 240°C, 3 minutes The analytical conditions for GC-orbitrap-MS are shown below. Analytical equipment: GC: TRACE1310 (Thermo Fisher Scientific) MS: QExactiveGC (Thermo Fisher Scientific) Analytical column: TG-WAXMS [length] 60 m [inner diameter] 0.25 mm [film thickness] 0.25 μm (Thermo Fisher Scientific) Autosampler: TRIPLUS RSH (Thermo Fisher Scientific) GC conditions: Injection method: SPME arrow Gas: Helium, 120 kPa (pressure) Injection port temperature: 240°C Oven temperature: 40°C (hold for 1 minute) - 10°C / min - 110°C - 2°C / min - 180°C - 3°C / min - 240°C - 10°C / min - 250°C (hold for 6 minutes), total 70 minutes MS conditions: Transfer temperature: 240°C Ion source temperature: 230°C Ionization method: EI positive MS scan: m / z 30-250 Monitoring ions: shown in the table below.

[0068] (3) Data Analysis The exact mass of each component was extracted from the GC-MS chromatogram (the mass-to-charge ratio (m / z) of the base peak (high intensity peak in the mass spectrum) of each component shown in the table below is referred to as the "exact mass" of each component), and the peak area was obtained. The components in each sample were compared by calculating the peak area ratio (= peak area of ​​each component / peak area of ​​the internal standard).

[0069]

[0070] The peak area ratios of each component detected in the SPME-GC-MS specimens prepared from each sample relative to the internal standard are shown in Figures 1 to 4. The bars in the figures represent the standard deviation.

[0071] It was confirmed that allyl isothiocyanate, which is known as the component responsible for the pungent taste unique to mustard seeds, was hardly contained in the oil-based paste composition of Example 1(2).On the other hand, it was confirmed that the contents of 2-methyltetrahydrofuran-3-one, 2-furfurylthiol, α-angelicalactone, 2-methyltetrahydrothiophen-3-one, tetrahydrothiophen-3-one, β-angelicalactone, γ-crotonolactone, dimethyl sulfone, furfuryl methyl sulfide, 1-furfurylpyrrole, and guaiacol, which are thought to be involved in the aroma and taste unique to mustard seeds, were significantly higher in the oil-based paste composition of Example 1(2) than in the ground mustard seeds.

Claims

1. A method for producing an oil-based pasty composition containing ground mustard seeds, comprising the step of grinding the mustard seeds in a mixture of mustard seeds and oil.

2. The method of claim 1, further comprising the step of heating mustard seeds to obtain heat-treated mustard seeds, wherein the mixture is a mixture of the heat-treated mustard seeds and the oil.

3. The method of claim 2, wherein the step of obtaining heat-treated mustard seeds comprises heating the mustard seeds in an open system under conditions such that the heat number is 200 or higher.

4. The method according to any one of claims 1 to 3, wherein the step of grinding the mustard seeds comprises grinding the mustard seeds to an average particle size of 300 μm or less.

5. The method according to any one of claims 1 to 4, wherein the mixture contains 50 to 200 parts by weight of the oil per 100 parts by weight of the mustard seeds.

6. The method according to any one of claims 1 to 5, wherein the water content of the mixture is 5% by weight or less.

7. An oil-based paste-like composition containing crushed mustard seeds, wherein a sample is prepared by adding 4-methylthiazole to the oil-based paste-like composition in an amount equivalent to 1.0 μg / g of the mustard seed equivalent of the oil-based paste-like composition, and the volatile components are extracted from the sample by solid phase microextraction-gas chromatography-mass spectrometry (SPME-GC-MS) at an extraction temperature of 60°C for 10 minutes. In the resulting chromatogram, (1) the area ratio of the peak area derived from allyl isothiocyanate to the peak area derived from 4-methylthiazole is 10.0 or less, and (2) the area ratio of the peak area derived from 2-methyltetrahydrofuran-3-one to the peak area derived from 4-methylthiazole is 1.0 or more, and (3) the area ratio of the peak area derived from 2-furfurylthiol to the peak area derived from 4-methylthiazole is 0.010 or more. (4) the area ratio of the peak area derived from α-angelicalactone to the peak area derived from 4-methylthiazole is 0.020 or more, (5) the area ratio of the peak area derived from 2-methyltetrahydrothiophen-3-one to the peak area derived from 4-methylthiazole is 0.30 or more, (6) the area ratio of the peak area derived from tetrahydrothiophen-3-one to the peak area derived from 4-methylthiazole is 0.060 or more, (7) the area ratio of the peak area derived from β-angelicalactone to the peak area derived from 4-methylthiazole is 0.045 or more, (8) the area ratio of the peak area derived from γ-crotonolactone to the peak area derived from 4-methylthiazole is 0.40 or more, (9) the area ratio of the peak area derived from dimethyl sulfone to the peak area derived from 4-methylthiazole is 0.13 or more, (10) the area ratio of the peak area derived from furfuryl methyl sulfide to the peak area derived from 4-methylthiazole is 0.050 or more, (11) The area ratio of the peak area derived from 1-furfurylpyrrole to the peak area derived from 4-methylthiazole is 0.010 or more;(12) An oil-based paste composition that satisfies one or more of the above criteria: the area ratio of the peak area derived from guaiacol to the peak area derived from 4-methylthiazole is 0.020 or more.

8. A food product comprising an oil-based paste-like composition produced by the method according to any one of claims 1 to 6, or the oil-based paste-like composition according to claim 7.

Citation Information

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