JP6777528B2 - Oil composition - Google Patents

Description

The present invention relates to an oil / fat composition rich in α-linolenic acid.
The present invention

In response to the growing health consciousness in recent years, many studies have been conducted on the function of fatty acids in fats and oils. For example, prevention of coronary artery disease, stroke, etc. by ω3 polyunsaturated fatty acids such as α-linolenic acid (C18: 3, ALA), eicosapentaenoic acid (C20: 5, EPA), docosahexaenoic acid (C22: 6, DHA) It has been reported to be effective. Since ω3 polyunsaturated fatty acids cannot be synthesized in vivo and deficiency causes dermatitis, etc., it is desirable to use fats and oils containing a large amount of them. In 2005, the Ministry of Health, Labor and Welfare announced that ω3 polyunsaturated fatty acids. A total intake target amount (adult) of 1 g / day is set.

On the other hand, it has been reported that fats and oils containing diacylglycerol in a high concentration have physiological effects such as suppressing the increase of blood triglyceride (neutral fat) after meals and having less accumulation in the body.
Therefore, so far, in order to effectively express the physiologically active functions of ω3 highly unsaturated fatty acids such as α-linolenic acid and diacylglycerol, diglyceride 40 to 99.7% by weight and the like are contained and diglyceride is formed. Proposed oil and fat compositions (Patent Document 1) and the like having an ω3 unsaturated acyl group content of 15 to 89.5% by weight and a monoene acyl group content of 10 to 84.5% by weight among the acyl groups. There is.

Japanese Unexamined Patent Publication No. 2001-40386

However, according to the research of the present inventor, diacylglycerol-containing fats and oils containing abundant α-linolenic acid in the constituent fatty acids may have a green odor. In particular, in fats and oils having a high diacylglycerol content, this tendency was remarkable.
Therefore, the present invention relates to providing a fat and oil containing a high amount of diacylglycerol, which has a low green odor and is rich in α-linolenic acid.

The inventor of the present invention has conducted diligent studies to solve the above problems, and found that if the fat and oil contains a Japanese pepper flavor or a sesame oil flavor, the green odor is improved. However, it was found that when trying to sufficiently reduce the green odor, a pungent scent and a burnt odor that are not suitable for cooking oil are felt. Therefore, the present inventor further investigated such a problem, and found that if the oil and fat contained a predetermined amount of a sunshaw flavor and a sesame oil flavor, the green odor was reduced, and the fragrance and charring were irritating. It has been found that such odors are also suppressed, and a fat and oil composition suitable as an edible oil can be obtained.

That is, the present invention describes the following components (A), (B) and (C):
(A) Fats and oils in which 15 to 60% by mass of the constituent fatty acids are α-linolenic acid,
(B) Japanese pepper flavor 0.05 to 0.3% by mass,
(C) Sesame oil flavor 0.5-5% by mass
To provide an oil / fat composition containing diacylglycerol in an amount of 70% by mass or more of the component (A) oil / fat.

According to the present invention, it is possible to provide an oil / fat composition having a high content of α-linolenic acid and diacylglycerol, which has an excellent physiological effect and a small green odor.

In the present invention, the substance (A) constituting the fat and oil includes not only diacylglycerol but also monoacylglycerol and triacylglycerol. In the present invention, the fat and oil (A) contains any one or more of monoacylglycerol, diacylglycerol and triacylglycerol. The type of fat and oil is not particularly limited, and any fat or oil that can be used as an edible fat or oil may be used.
From the viewpoint of usability, the content of the fat (A) in the fat composition is preferably 90% by mass (hereinafter, simply referred to as "%") or more, more preferably 94% or more, and further preferably 94.5. % Or more, preferably 99.45% or less, and more preferably 99% or less.

In the present invention, the content of α-linolenic acid in the fatty acids constituting (A) fats and oils is 15 to 60%. The content of α-linolenic acid in the fatty acids constituting the fats and oils is preferably 17% or more, more preferably 20% or more, further preferably 30% or more, and oxidative stability, from the viewpoint of physiological effects. From the point of view, it is preferably 57% or less, more preferably 55% or less, still more preferably 53% or less. The amount of fatty acid in the present specification is a free fatty acid conversion amount.

In the present invention, the constituent fatty acids other than α-linolenic acid constituting (A) fats and oils are not particularly limited, and may be either saturated fatty acids or unsaturated fatty acids.
From the viewpoint of flavor and industrial productivity of fats and oils, the content of unsaturated fatty acids in the fatty acids constituting the fats and oils is preferably 60% or more and 100% or less, more preferably 70% or more and 100% or less, still more preferably. It is 80% or more and 100% or less. The number of carbon atoms of the unsaturated fatty acid is preferably 14 to 24, more preferably 16 to 22, from the viewpoint of physiological effects.

The content of linoleic acid (C18: 2) in the fatty acids constituting (A) fats and oils is preferably 5% or more, more preferably 10% or more, and preferably 40, from the viewpoint of industrial productivity. % Or less, more preferably 30% or less, still more preferably 20% or less.

Further, the content of oleic acid (C18: 1) in the fatty acid constituting (A) fat and oil is preferably 10% or more, and more preferably 50% or less, more preferably, from the viewpoint of industrial productivity. Is 40% or less, more preferably 30% or less.

(A) The total content of saturated fatty acids in the fatty acids constituting the fats and oils is preferably 40% or less, more preferably 30% or less, still more preferably 20 from the viewpoint of appearance, physiological effect, and industrial productivity of fats and oils. % Or less, and preferably 0.5% or more.
The number of carbon atoms of the saturated fatty acid is preferably 14 to 24, more preferably 16 to 22.

In the present invention, the content of diacylglycerol in (A) fats and oils is 70% or more. The content of diacylglycerol in fats and oils is preferably 75% or more, more preferably 78% or more, further preferably 80% or more, still more preferably 83% or more, still more preferably 85% or more, from the viewpoint of physiological effects. Also, from the viewpoint of industrial productivity, it is preferably 96% or less, more preferably 95% or less, still more preferably 94% or less.

(A) The content of triacylglycerol in the fat and oil is preferably 1% or more, more preferably 2% or more, still more preferably 3% or more, and preferably 3% or more, from the viewpoint of industrial productivity of the fat and oil. It is 30% or less, more preferably 20% or less, still more preferably 15% or less.
The content of monoacylglycerol in (A) fats and oils is preferably 3% or less, more preferably 0 to 2%, still more preferably 0 to 1% from the viewpoint of flavor and industrial productivity of fats and oils. is there.
(A) The content of free fatty acid or salt thereof contained in fats and oils is preferably 0 to 5%, more preferably 0 to 2%, still more preferably 0 to 1 from the viewpoint of flavor and industrial productivity of fats and oils. %.
It is preferable that the fatty acid compositions of triacylglycerol, diacylglucerol and monoacylglycerol are the same in terms of industrial productivity of fats and oils.

(A) There are no particular restrictions on the edible oils and fats that can be used as the origin of the oils and fats. Wheat germ oil, perilla oil, flaxseed oil, egoma oil, sacha inch oil, walnut oil, kiwi seed oil, salvia seed oil, grape seed oil, macadamia nut oil, hazelnut oil, pumpkin seed oil, camellia oil, tea seed oil, borage oil, Vegetable fats and oils such as palm oil, palm olein, palm stea, palm oil, palm kernel oil, cacao butter, monkey fat, shea butter and algae oil; animal fats and oils such as fish oil, lard, beef fat and butter fat; or them. Examples of oils and fats such as ester exchange oil, hydrogenated oil, and fractionated oil. Each of these oils may be used alone, or may be appropriately mixed and used. Among them, from the viewpoint of usability, it is preferable to use vegetable oils and fats, and it is preferable to use liquid oils and fats having excellent low temperature resistance, and one kind selected from the group consisting of perilla oil, linseed oil and perilla oil. It is preferable to use two or more kinds of fats and oils because they are rich in α-linolenic acid. The liquid fat and oil means a fat and oil that is liquid at 20 ° C. when a cooling test is carried out according to the standard fat and oil analysis test method 2.3.8-27. Further, the edible fat and oil is preferably a refined fat and oil that has undergone a refining step.

The oil and fat composition of the present invention contains (B) Japanese pepper flavor and (C) sesame oil flavor.
As shown in Examples described later, the sansho flavor or sesame oil flavor improves the green odor of the oil and fat containing a high amount of diacylglycerol rich in α-linolenic acid, but the amount of the sansho flavor is to sufficiently reduce the green odor. If you increase the amount, a pungent scent that is not suitable for cooking oil will come out strongly. Sesame oil fragrance does not have a sufficient effect of reducing the green odor, and if the amount is further increased, a burnt odor will appear. On the other hand, if two kinds of fragrances, Japanese pepper fragrance and sesame oil fragrance, are contained in combination in predetermined amounts, the pungent fragrance and the burnt odor can be suppressed, and the odor is sufficient for green odor. Demonstrates a significant reduction effect.

The (B) Japanese pepper fragrance used in the present invention contains the aroma component of Japanese pepper (Zanthoxylum piperitum). As the aroma component, terpene hydrocarbons, terpene aldehydes, alcohols and the like are known.
There are no particular restrictions on the variety of Japanese pepper. Examples of the site where Japanese pepper is used include flowers, buds, leaves, branches, bark, roots, fruits, pericarp, and seeds. It is preferably a fruit.
As the Japanese pepper flavor, any of naturally derived, synthetic, or a mixture thereof can be used. A natural fragrance is preferable. Examples of the method for producing the Japanese pepper flavor include a cold pressing method by a pressing method, a steam distillation method, an extraction method and the like, and a steam distillation method is preferable. Examples of the form of Japanese pepper flavor include oil-soluble, emulsion, and powder. As the Japanese pepper flavor, one kind or two or more kinds may be used.
As the sunshaw fragrance, a commercially available product, preferably a commercially available product for food and drink can be used.

In the present invention, the content of the Japanese pepper flavor (B) in the fat and oil composition is 0.05 to 0.3%. The content of the Japanese pepper flavor is preferably 0.1% or more from the viewpoint of reducing the green odor of the oil and fat containing a large amount of diacylglycerol containing abundant α-linolenic acid. On the other hand, from the viewpoint of suppressing a pungent scent, it is preferably 0.25% or less, more preferably 0.2% or less.
Gas chromatography can be used to quantify the fragrance. For example, it can be analyzed by headspace gas chromatography.

The (C) sesame oil flavor used in the present invention contains the aroma component of sesame oil extracted from the seeds of sesame (Sesame indicum L.). Aldehydes, pyrazines and the like are known as the aroma components. The type of sesame is not particularly limited, and examples thereof include white sesame, gold sesame, black sesame, and brown sesame. The sesame seeds may be roasted roasted sesame seeds.
The sesame oil flavor can be of natural origin, synthetic, or a mixture thereof. It is preferably a natural fragrance, and sesame oil may be used as the sesame oil fragrance. Examples of the method for producing sesame oil include a pressing method and an extraction method. As the sesame oil flavor, one kind or two or more kinds may be used.
As the sesame oil flavor, a commercially available product, preferably a commercially available product for food and drink can be used.

In the present invention, the content of the (C) sesame oil flavor in the fat and oil composition is 0.5 to 5%. The content of the sesame oil flavor is preferably 1.0% or more, more preferably 2 from the viewpoint of reducing the green odor of the oil and fat containing a large amount of α-linolenic acid and suppressing the pungent scent. It is 0.0% or more. On the other hand, it is preferably 4% or less, more preferably 3% or less, from the viewpoint of suppressing a burnt odor.

In the present invention, the mass ratio [(B) / (C)] of the component (B) to the component (C) contained in the oil / fat composition is preferably 0.02 or more from the viewpoint of suppressing the green odor. Further, from the viewpoint of suppressing a pungent scent, it is preferably 0.6 or less, more preferably 0.2 or less.

The oil and fat composition of the present invention preferably further contains an antioxidant from the viewpoint of oxidative stability.
The content of the antioxidant in the oil / fat composition is preferably 0.005% or more and 0.5% or less, more preferably 0.04% or more and 0.25, from the viewpoints of flavor, oxidative stability, color suppression and the like. % Or less, more preferably 0.08% or more and 0.2% or less.
The antioxidant is not particularly limited as long as it is used for food, but it is a natural antioxidant, lecithin, tocopherol, ascorbyl palmitate, ascorbyl stearate, dibutylhydroxytoluene (BHT) and butylhydroxyanisole (BHA). At least one selected from the above is preferable.

In the fat and oil composition of the present invention, for example, 15 to 60% of the constituent fatty acids of the component (A) are α-linolenic acid, and the fat and oil containing 70% or more of diacylglycerol, the component (B) Japanese pepper flavor, and the component ( C) It can be obtained by adding a sesame oil flavor and, if necessary, other components, and appropriately heating and stirring. Ordinary edible oils and fats may be blended if necessary.
The fat and oil component (A) can be obtained by an esterification reaction between a fatty acid derived from the fat and oil and glycerin, a transesterification reaction between the fat and oil and glycerin (glycerolisis), and the like according to a conventional method.
The fat and oil composition of the present invention can be used in the same manner as general edible fats and oils, and can be applied to various foods and drinks using fats and oils. Examples of foods and drinks include foods for specified health use and foods with functional claims, which advocate the physiological effects of α-linolenic acid and diacylglycerol, in addition to ordinary foods and drinks.

[Analysis method]
(I) Glycemic composition of fats and oils About 10 mg of fats and oils samples and 0.5 mL of a trimethylsilylating agent (“silylating agent TH”, manufactured by Kanto Chemical Co., Inc.) were added to a glass sample bottle, sealed, and heated at 70 ° C. for 15 minutes. To this, 1.0 mL of water and 1.5 mL of hexane were added and shaken. After standing, the upper layer was subjected to gas chromatography (GLC) for analysis.
<GLC analysis conditions>
(conditions)
Equipment: Agilent 6890 Series (manufactured by Agilent Technologies)
Integrator: ChemiStation B 02.01 SR2 (manufactured by Agilent Technologies)
Column: DB-1ht (manufactured by Agent J & W)
Carrier gas: 1.0 mL He / min
Injector: Split (1:50), T = 340 ° C
Detector: FID, T = 350 ° C
Oven temperature: Raise from 80 ° C to 340 ° C at 10 ° C / min and hold for 15 minutes

(Ii) Composition of fatty acids Fatty acid composition Fatty acid methyl esters are prepared and obtained according to "Preparation method of fatty acid methyl ester (2.4.1.-1996)" in "Standard Fatty Acid Analysis Test Method" edited by Japan Oil Chemists' Society. Fatty acid samples were prepared from American Oil Chemists. Measurements were made according to the Society Official Method Ce 1f-96 (GLC method).
<GLC analysis conditions>
Column: CP-SIL88 50m x 0.25mm x 0.2μm (VARIAN)
Carrier gas: 1.0 mL He / min
Injector: Split (1:50), T = 300 ° C.
Detector: FID, T = 300 ° C
Oven temperature: 150 ° C. 5 min holding → 1 ° C / min temperature rise → 160 ° C 5 min holding → 2 ° C / min temperature rise → 200 ° C 10 min holding → 10 ° C / min temperature rise → 220 ° C 5 min holding

〔material〕
As the component (A) fat and oil, the following refined fat and oil a was used.
300 parts by mass of fatty acid obtained by hydrolyzing flaxseed oil with an enzyme and 47 parts by mass of glycerin are mixed, and an esterification reaction is carried out using a 1,3-position selective lipase (manufactured by Novozyme) immobilized on an ion exchange resin as a catalyst. went. After the immobilized enzyme was filtered off, the reaction-finished product was subjected to molecular distillation, acid treatment and washing with water (distilled water 3 times) to obtain a treated oil. The treated oil was deodorized to obtain refined oil a.
The glyceride composition of the refined fat a was 14.1% triacylglycerol, 85.2% diacylglycerol, 0.6% monoacylglycerol, and 0.1% free fatty acid. The fatty acid composition was C18: 1 23.2%, C18: 2 16.6%, C18: 3 51.7%, total saturated fatty acid 5.5%, and others 3%.

(B) As a Japanese pepper fragrance, a Japanese pepper oil flavor (manufactured by Ogawa fragrance) was used.
(C) Gold seal sesame oil (manufactured by Kadoya) was used as the sesame oil fragrance.

Examples 1-7 and Comparative Examples 1-11
[Preparation of oil and fat composition]
Refined fats and oils a, Japanese pepper flavor and sesame oil flavoring were mixed in the proportions shown in Table 1 to prepare fat and oil compositions.

〔Evaluation test〕
The test product obtained above was subjected to sensory evaluation. Specifically, the green odor, pungent scent, and burnt odor of the fat and oil composition were evaluated on a 7-point scale according to the following criteria, and the scores were decided through discussions with three expert panels. The results are shown in Table 1.
0: Not felt 1: Slightly felt 2: Slightly felt 3: Feeled 4: Slightly strong 5: Strongly felt 6: Very strong

As is clear from the results shown in Table 1, Comparative Example 1 having a high content of α-linolenic acid and diacylglycerol had a very strong green odor.
On the other hand, the oil and fat composition of the example in which a predetermined amount of Japanese pepper flavor and sesame oil flavor was blended had less green odor. It was also confirmed that the pungent scent and the burnt odor were suppressed.
On the other hand, in Comparative Examples 2 to 5 in which the Japanese pepper flavor was blended, the green odor decreased as the blending amount increased, but a pungent scent was felt, which was not preferable as an edible oil. Further, Comparative Examples 6 to 9 in which the sesame oil flavor was added were not preferable as edible oils because the effect of reducing the green odor was not sufficient and a burnt odor was felt as the amount of the sesame oil was increased. Further, Comparative Example 10 in which the amount of the Japanese pepper flavor and the sesame oil flavor is small does not have a sufficient effect of reducing the green odor, and Comparative Example 11 in which the amount of the Japanese pepper oil and the sesame oil flavor is large is stimulating and burnt. The smell was very strong.

Claims (4)

The following components (A), (B) and (C):
(A) 90 to 99.45% by mass of fats and oils in which 15 to 60% by mass of the constituent fatty acids are α-linolenic acid,
(B) Japanese pepper flavor 0.05 to 0.3% by mass,
(C) Sesame oil flavor 0.5-5% by mass
A fat and oil composition containing 70% by mass or more of the component (A) fat and oil, which is diacylglycerol. Component (A) fat and oil composition according to claim 1, wherein the content of linoleic acid in the fatty acids constituting the fat or oil is from 5 to 40 wt%. The oil / fat composition according to claim 1 or 2, wherein the content of oleic acid in the fatty acid constituting the component (A) oil / fat is 10 to 50% by mass. The fat or oil according to any one of claims 1 to 3 , wherein the content mass ratio [(B) / (C)] of the component (B) Japanese pepper flavor and the component (C) sesame oil flavor is 0.02 to 0.6. Composition.