Edible vegetable oils and fats

VN10061875BActive Publication Date: 2026-09-25KUKI SANGYO CORP
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Patent Information

Application Number
VN1202307403
Authority / Receiving Office
VN · VN
Patent Type
Patents
Current Assignee / Owner
Priority Date
2021-04-26
Filing Date
2022-04-25
Publication Date
2026-09-25
Estimated Expiration
2042-04-25

AI Technical Summary

Technical Problem

Existing edible vegetable oils fail to enhance the aroma of sesame oil effectively, despite research on its components, leading to a demand for stronger sesame oil flavors.

Method used

Incorporating specific aroma components like 2-methylpyrazine, dimethylpyrazine, 2-furanmethanol, and furfural in predetermined ratios into edible vegetable oils to create a stronger sesame oil aroma, while maintaining the unique characteristics of sesame oil.

Benefits of technology

The enhanced aroma of sesame oil is achieved, making the edible vegetable oil more potent and reminiscent of sesame oil, suitable for various culinary uses and applications.

✦ Generated by Eureka AI based on patent content.

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Abstract

The invention relates to an edible vegetable oil and fat with an enhanced sesame oil flavor. This edible vegetable oil and fat has a sesame oil flavor and contains 2-methylpyrazine, dimethylpyrazine, 2-furanmethanol, furfural and pyrazine. The content of 2-methylpyrazine is 6 µg or greater in 100 mg of edible vegetable oil and fat and is greater than the content of dimethylpyrazine and the content of 2-furanmethanol. The ratio of the content of dimethylpyrazine to 2-methylpyrazine is between 0.40 and 0.90.
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Description

edible vegetable oil

[0001] The present invention relates to an edible vegetable oil having the aroma of sesame oil.

[0002] Sesame seeds contain dietary fiber, calcium, iron, zinc, and other components such as sesamin, making them highly nutritious and known for their excellent antioxidant and other functional properties. Sesame seeds are widely used for both home and commercial use in the form of sesame oil, roasted sesame seeds, ground sesame seeds, and sesame paste.

[0003] The fragrant aroma unique to sesame oil is expected to stimulate consumer appetite, and sesame oil is often used as a flavoring agent. Sesame oil is a type of edible oil with a unique aroma and flavor, and is used in a wide range of applications, including frying oil, stir-frying oil, and dressings. In recent years, various types of sesame oil have been sold due to the diversification of consumer preferences. In addition, many blended oils that blend sesame oil with rapeseed oil or soybean oil are also sold, and the market for edible vegetable oils with the aroma and flavor of sesame oil is expanding.

[0004] The aroma of sesame oil has been analyzed, and it is known that sesame oil contains a variety of aroma components (Non-Patent Document 1). In recent years, many studies have been conducted on seasonings containing sesame, and attempts have been made to maintain the aroma of sesame oil for a long period of time by blending specific flavorings (for example, Patent Document 1).

[0005] Japanese Patent Application Laid-Open No. 2008-154476

[0006] Journal of the Japan Oil Chemists' Society, Vol. 47, No. 3, 1998, pp. 257-261

[0007] In particular, edible vegetable oils with a strong sesame oil aroma are suitable for flavoring dishes, and demand for such oils has been increasing in recent years. Although research into the aroma of sesame oil has been conducted, there is still room for improvement in enhancing the aroma of sesame oil in edible vegetable oils.

[0008] The present invention has been made in view of the above background, and has as its object to provide an edible vegetable oil having an enhanced sesame oil aroma.

[0009] The edible vegetable oil of the present invention is an edible vegetable oil having a sesame oil aroma, and is characterized by containing 2-methylpyrazine, dimethylpyrazine, and 2-furanmethanol, wherein the content of 2-methylpyrazine is 6 μg or more per 100 mg of the edible vegetable oil and is greater than the respective contents of dimethylpyrazine and 2-furanmethanol.

[0010] In this specification, the content of each component refers to the content per 100 mg of edible vegetable oil. Furthermore, dimethylpyrazine is a concept that includes 2,5-dimethylpyrazine, 2,6-dimethylpyrazine, and 2,3-dimethylpyrazine, and the content of dimethylpyrazine refers to the total amount of these. It is relatively difficult to detect each of these components as separate peaks in HPLC, and in the present invention, the combined content of these components is defined. The edible vegetable oil of the present invention contains at least one of 2,5-dimethylpyrazine, 2,6-dimethylpyrazine, and 2,3-dimethylpyrazine.

[0011] The content ratio of the dimethylpyrazine to the 2-methylpyrazine is 0.40 to 0.90, and the mass ratio of the dimethylpyrazine to the 2-furanmethanol is 70:30 to 40:60.

[0012] The edible vegetable oil further contains furfural and pyrazine.

[0013] The ratio of the content of the furfural to the content of the 2-methylpyrazine is 0.20 or less.

[0014] The edible vegetable oil of the present invention has the aroma of sesame oil and contains 2-methylpyrazine, dimethylpyrazine, and 2-furanmethanol, with the 2-methylpyrazine content being 6 μg or more per 100 mg of the edible vegetable oil and being greater than the respective contents of dimethylpyrazine and 2-furanmethanol. As a result, the edible vegetable oil has a stronger aroma (stronger aroma potency) than commercially available sesame oil while maintaining the fragrant aroma characteristic of sesame oil.

[0015] The ratio of the content of dimethylpyrazine to 2-methylpyrazine is 0.40 to 0.90, and the mass ratio of dimethylpyrazine to 2-furanmethanol is 70:30 to 40:60, so that the aroma characteristic of sesame oil can be easily maintained.

[0016] The above-mentioned edible vegetable oil further contains a predetermined amount of furfural (having an almond-like aroma), so that the edible vegetable oil has a richer aroma more like sesame oil.

[0017] 1 is a graph showing the contents of aroma components in Examples 1 to 3 and Comparative Example 1. 2 is a graph showing the contents of aroma components in Reference Examples 1 to 5. 3 is a graph showing the content ratios of specific components in each test example. 4 is a graph showing the contents of aroma components in Examples 4 and 5.

[0018] The present inventors have conducted extensive research to obtain an edible vegetable oil with an enhanced sesame oil aroma, and have found that by incorporating a predetermined amount or more of 2-methylpyrazine, which has been known to be one of the aroma components of sesame oil, and also incorporating dimethylpyrazine and 2-furanmethanol in specific ratios into the edible vegetable oil, the aroma can be enhanced while maintaining the unique sesame oil aroma. The present invention is based on this finding.

[0019] The edible vegetable oil of the present invention is an edible vegetable oil having the aroma of sesame oil. In addition to sesame oil, this edible vegetable oil can also be soybean oil, rapeseed oil, rice bran oil, corn oil, palm oil, coconut oil, sunflower oil, olive oil, cottonseed oil, safflower oil, etc. Sesame oil is preferably used.

[0020] The edible vegetable oil of the present invention contains at least 2-methylpyrazine, dimethylpyrazine, and 2-furanmethanol as aroma components.

[0021] 2-Methylpyrazine is a compound with a nutty or cocoa-like aroma, and is a component produced by roasting coffee, cacao, and the like. The 2-methylpyrazine content in the edible vegetable oil of the present invention is 6 μg or more. As will be shown in the Examples below, the 2-methylpyrazine content in commercially available sesame oil is at most about 2 μg to 3 μg, and the edible vegetable oil of the present invention contains about twice as much 2-methylpyrazine as that amount.

[0022] The content of 2-methylpyrazine in edible vegetable oils and fats is preferably 10 μg or more, more preferably 20 μg or more. There are no particular limitations on the upper limit of the 2-methylpyrazine content, but it may be, for example, 100 μg or less, or 70 μg or less. The content of 2-methylpyrazine in edible vegetable oils and fats can be measured using high performance liquid chromatography (HPLC) by the method described in the Examples. The same applies to dimethylpyrazine, 2-furanmethanol, furfural, pyrazine, etc.

[0023] Dimethylpyrazine, another essential component of the edible vegetable oil of the present invention, has a nutty or cocoa-like aroma. 2-Furanmethanol (furfuryl alcohol) is a compound with a roasted aroma. The contents of these compounds are all lower than the content of 2-methylpyrazine. If the contents of these compounds are higher than the content of 2-methylpyrazine, the balance of the aroma components is disrupted, and the unique aroma of sesame oil is lost, as shown in the examples.

[0024] The ratio of the dimethylpyrazine content to the 2-methylpyrazine content in edible vegetable oils and fats (dimethylpyrazine content / 2-methylpyrazine content) is preferably 0.40 to 0.90, more preferably 0.40 to 0.80, and even more preferably 0.40 to 0.70. By adjusting the ratio within the above numerical range, a sesame oil-like aroma is achieved. A specific dimethylpyrazine content is, for example, 1.5 μg to 50 μg.

[0025] The ratio of the 2-furanmethanol content to the 2-methylpyrazine content in the edible vegetable oil (2-furanmethanol content / 2-methylpyrazine content) is preferably 0.30 to 0.90, more preferably 0.30 to 0.80. A specific 2-furanmethanol content is, for example, 2.0 μg to 50 μg.

[0026] The mass ratio of dimethylpyrazine to 2-furanmethanol is, for example, 70:30 to 40:60, and preferably 55:45 to 45:55. When both components are contained in equal amounts, the characteristic aroma of sesame oil is more easily exhibited.

[0027] The edible vegetable oil of the present invention preferably further contains furfural and pyrazine as aroma components. Furfural is a type of aromatic aldehyde and is a compound having an almond-like aroma. Pyrazine is a compound having a roasted aroma. The pyrazine content is, for example, 0.5 μg to 10 μg. The pyrazine content is preferably greater than the furfural content and less than the respective contents of dimethylpyrazine and 2-furanmethanol.

[0028] The ratio of the furfural content to the 2-methylpyrazine content in the edible vegetable oil (furfural content / 2-methylpyrazine content) is preferably 0.20 or less, more preferably 0.10 or less. A specific furfural content is, for example, 0.3 μg to 3 μg.

[0029] In addition to the aroma components described above, the edible vegetable oil of the present invention may contain aroma components contained in ordinary sesame oil. For example, trimethylpyrazine, 2-ethyl-5-methylpyrazine, 2-ethyl-6-methylpyrazine, 2-acetylpyrazine, pentanal, hexanal, heptanal, 2-pentylfuran, 2,4-dimethylthiazole, etc. Furthermore, the edible vegetable oil of the present invention may further contain other aroma components within a range that does not impair the effects of the present invention.

[0030] In the edible vegetable oil of the present invention, the method for adjusting the content of each component, such as the above-mentioned 2-methylpyrazine, is not particularly limited. For example, commercially available components may be used, or a flavoring containing each component may be used. In this case, the edible vegetable oil of the present invention can be obtained by adding a predetermined amount of each component to, for example, existing sesame oil.

[0031] Sesame oil is generally produced through roasting, pressing, and filtering processes. Sesame seeds used as raw materials include white sesame, black sesame, golden sesame, yellow sesame, and brown sesame, which are selected according to various criteria (size, weight, etc.).

[0032] Roasting the selected raw sesame seeds produces the fragrant aroma characteristic of sesame oil. The roasting machine and roasting method used in the roasting process are not particularly limited. For example, a continuous roaster or a batch roaster can be used as the roasting machine. Roasting can be performed using direct flame, hot air, far infrared rays, microwaves, or the like, and is carried out at a temperature of about 150°C to 250°C. The roasted sesame seeds are placed in a kettle and steamed in the kettle. The sesame seeds are then pressed in a press to extract the oil. The pressed oil is left to stand and then filtered to remove solids and sediments. The filtration process is usually carried out multiple times. Finally, sesame oil is obtained.

[0033] The edible vegetable oil of the present invention can also be obtained by contacting aroma components generated during the above-mentioned sesame oil production process with a target oil (e.g., edible vegetable oil produced on a production line different from that of the sesame oil.) In this case, the edible vegetable oil to be contacted may be sesame oil, soybean oil, rapeseed oil, rice bran oil, corn oil, palm oil, coconut oil, sunflower oil, olive oil, cottonseed oil, safflower oil, or the like.

[0034] The edible vegetable oil of the present invention can be used not only as cooking oil or dressing in the home but also as an additive for various processed foods, such as cereals, powdered soups, breads, cakes, noodles, confectioneries, jellies, frozen foods, ice cream, dairy products, and beverages, by mixing or kneading it into these foods.

[0035] The edible vegetable oil of the present invention has an enhanced sesame oil aroma, so even a small amount can sufficiently impart the aroma of sesame oil. This allows for a reduction in the amount of edible vegetable oil itself, leading to lower calorie dishes and low-calorie products. Furthermore, dispersing the edible vegetable oil of the present invention in soups and other dishes is expected to increase the umami aftertaste and also impart richness. In particular, "reduced-salt products," which are expected to see market expansion, often feature products that enhance umami and richness in place of salt, and this edible vegetable oil can be applied to the reduced-salt market.

[0036] [Examples 1 to 3, Comparative Example 1] Sesame oil was produced as an example of an edible vegetable oil. The raw material sesame was roasted, pressed, and filtered. Specifically, the sesame was roasted at 150°C to 250°C for 5 to 15 minutes, pressed using a press, and then solid matter was filtered off using a filter press. Note that the oil was contacted with aroma components generated during the production process during the intermediate stage after pressing.

[0037] [Reference Examples 1 to 5] Four types of commercially available sesame oil of a strong flavor were used for comparison in Reference Examples 1 to 4. In Reference Example 5, a flavor used for imparting the aroma of sesame oil to seasonings and the like was used.

[0038] <Measurement of Aroma Components> The aroma components of Examples 1 to 3, Comparative Example 1, and Reference Examples 1 to 5 were extracted from each oil and fat according to the following method, and then measured by HPLC.

[0039] (1) Extraction of aroma components This was carried out according to the following procedure. 1. 3 ml of methanol was added to 3 g of oil. 2. Ultrasonic extraction was carried out for 10 minutes. 3. Centrifugation was carried out at 3,500 rpm for 10 minutes. 4. The supernatant was collected. 5. 3 ml of methanol was added to the residue. 6. Steps 2 to 5 above were repeated a total of three times. 7. The volume was increased to 10 ml with methanol. 8. The extract after filtration was used for the following measurements.

[0040] (2) Quantitative Analysis of Aroma Components 5 μl of the extract obtained in (1) above was injected into HPLC and quantitative analysis was carried out under the following conditions.

[0041] <HPLC conditions> Column: ODS, column length 150 mm x column inner diameter 3 mm, particle size 3 μm Oven: 35°C Detection wavelength: 215 nm, 270 nm Mobile phase A: 0.1% formic acid water Mobile phase B: acetonitrile Flow rate: 0.43 ml / min Delivery of each mobile phase: The mixing ratio of mobile phase A and mobile phase B was changed as shown in Table 1

[0042]

[0043] The aroma components were quantified by the standard addition method using the peak areas detected by HPLC. Measurements were performed under the above-mentioned HPLC conditions using a standard sample of each aroma component diluted with methanol as a quantitative marker. In this example, the dimethylpyrazine content was calculated as the total content of 2,5-dimethylpyrazine and 2,6-dimethylpyrazine.

[0044] A sensory evaluation was also conducted on the sesame oils of Examples 1 to 3 and Comparative Example 1. In the sensory evaluation, the aroma of the sesame oil of Reference Example 2 was used as the standard, and the sesame oils were evaluated based on two criteria: the intensity of the aroma and whether it sounded like sesame oil. The results are shown in Tables 2 and 3. FIG. 1 is a graph showing the contents of aroma components of Examples 1 to 3 and Comparative Example 1 in Table 2, and FIG. 2 is a graph showing the contents of aroma components of Reference Examples 1 to 5 in Table 3.

[0045]

[0046]

[0047] As shown in Table 2, the sesame oils of Examples 1 to 3 contained 6 μg or more of 2-methylpyrazine, and this content was higher than the respective contents of dimethylpyrazine and 2-furanmethanol. As a result, while maintaining the aroma of sesame oil, the sesame oil aroma was stronger than that of commercially available sesame oil. On the other hand, Comparative Example 1 had a very strong aroma, but the aroma was different from that of sesame oil. As can be seen from the graphs in Figure 1, the ratio of dimethylpyrazine to 2-methylpyrazine and the ratio of 2-furanmethanol to 2-methylpyrazine were higher in Comparative Example 1 than in Examples 1 to 3. Therefore, it is believed that the balance between the aroma components was disrupted, impairing the fragrant aroma unique to sesame oil.

[0048] Furthermore, as shown in Table 3 and Figure 2, the commercially available sesame oils (Reference Examples 1 to 4) had roughly similar component balances, although there were differences in the content of each component. On the other hand, as shown in Figure 3, the ratio of the furfural content to the 2-methylpyrazine content in the flavor samples was significantly different from that of the other test examples.

[0049] [Examples 4 and 5] Sesame oil of Example 4 was produced in the same manner as in Examples 1 to 3. In addition, soybean oil of Example 5 was produced by contacting commercially available soybean oil with aroma components generated during the sesame oil production process.

[0050] The results of the aroma analysis of the sesame oils and soybean oils of Examples 4 and 5 as described above are shown in Table 2 and Figure 4. As shown in Figures 4(a) and (b), all of the oils contained 10 μg or more of 2-methylpyrazine, and exhibited a similar component balance to Examples 1 to 3 in Figure 1. In fact, the oils of Examples 4 and 5 had a stronger aroma than commercially available sesame oil (Reference Example 2). It was found that even vegetable oils other than sesame oil can be imparted with the fragrant aroma unique to sesame oil by adding specific components.

[0051] The edible vegetable oil of the present invention has an enhanced sesame oil aroma, and can easily impart the fragrant aroma of sesame oil to dishes and the like, and can be widely used as a cooking oil, dressing, or added to processed foods.

Claims

1. An edible vegetable oil having the aroma of sesame oil, comprising 2-methylpyrazine, dimethylpyrazine, and 2-furanmethanol, wherein the content of the 2-methylpyrazine is 6 μg or more in 100 mg of the edible vegetable oil, and is more than the respective contents of the dimethylpyrazine and the 2-furanmethanol.

2. The edible vegetable oil according to claim 1, wherein the ratio of the content of the dimethylpyrazine to the content of the 2-methylpyrazine is 0.40 to 0.

90.

3. The edible vegetable oil according to claim 2, wherein the mass ratio of the dimethylpyrazine and the 2-furanmethanol is 70:30 to 40:

60.

4. The edible vegetable oil according to any one of claims 1 to 3, wherein the edible vegetable oil further contains furfural and pyrazine.

5. The edible vegetable oil according to claim 4, wherein the ratio of the content of the furfural to the content of the 2-methylpyrazine is 0.20 or less.

6. The content of the 2-methylpyrazine is 10 μg to 100 μg in 100 mg of the edible vegetable oil, the ratio of the content of the dimethylpyrazine to the content of the 2-methylpyrazine is 0.40 to 0.70, and the mass ratio of the dimethylpyrazine and the 2-furanmethanol is 55:45 to 45:

55. The edible vegetable oil according to claim 1, characterized in that.

7. The edible vegetable oil according to claim 6, further comprising furfural and pyrazine, the ratio of the content of the furfural to the content of the 2-methylpyrazine is 0.20 or less, the content of the pyrazine is more than the content of the furfural, and is less than the respective contents of the dimethylpyrazine and the 2-furanmethanol.