JP4268473B2 - Oil composition - Google Patents

Description

  The present invention has a specific glyceride composition and a fatty acid composition, has a good flavor, and has a remarkable gelation property and water uptake property, so that it has excellent processing characteristics and an excellent peroxisome proliferator-activated receptor (Peroxisome Proliferator Activated Receptor (hereinafter referred to as PPAR) The present invention relates to an oil-and-fat composition useful as a food, medicine, feed or the like having an activation action and β-oxidation activation action.

  In recent years, interest in maintenance and promotion of health and prevention / treatment of diseases has increased, and fish oil and its components, icosapentaenoic acid (C20: 5, hereinafter referred to as IPA) and docosahexaenoic acid (C22: 6, hereinafter referred to as DHA) are described. ) Many studies on health functions have been conducted. Specifically, an anti-arteriosclerosis action, a brain function improvement action, a visual function improvement action, an antitumor action, an anti-inflammatory action, etc. are known (Non-patent Document 1 etc.).

  However, these components have a severe deterioration odor during storage, and their practical use is extremely limited in terms of flavor. In addition, it has been pointed out that IPA has an effect of inhibiting platelet aggregation and extending the bleeding time (Non-patent Documents 2, 3 and the like).

  On the other hand, the present inventors have found that ω3 unsaturated monoglyceride and diglyceride containing IPA and DHA have a body fat burning action (Patent Document 1). Further, it has been found that monoglyceride, particularly IPA monoglyceride, has a high PPAR activation action (Patent Document 2). However, the PPAR activation action of DHA monoglyceride has not yet been clarified.

  Here, PPAR is a kind of nuclear receptor and is a receptor that is activated by a peroxisome proliferator (Peroxisome Proliferator Activated Receptor). Recent research has revealed that this PPAR is involved in a great number of physiological and pathological phenomena. That is, since it has been clarified that fibrates, which are drugs for treating hyperlipidemia, and thiazolidine derivatives, which are known as drugs for treating diabetes, are agonists of PPAR, hyperlipidemia and insulin resistance following these compounds. Attempts have been made to develop drugs for improving sex and diabetes (Non-Patent Documents 4 to 6).

  In addition, various techniques relating to monoglycerides have been disclosed. Patent documents 3-7 etc. are indicated as a manufacturing method of monoglyceride. Patent Document 8 discloses a highly unsaturated fatty acid-containing monoglyceride. However, all of these monoglycerides have a problem in flavor.

Furthermore, Patent Documents 9 and 10 disclose partial glycerides including monoglycerides. Since these techniques have diglyceride as a main component, they are more dispersible in water than triglyceride. However, there is a problem in terms of processing characteristics such that water cannot be taken in due to a small amount of monoglyceride.
As described above, various health functions have been elucidated in fats and oils containing IPA and DHA. However, there are problems in terms of processing characteristics, flavor, and the like, and the current situation is that sufficient technology has not been established.
Journal of the Japan Oil Chemists' Society, 48, 1017 (1999) Atherosclerosis, 50, 3-10 (1984) Lipids, 32, 1129-1136 (1997) Cell, 31 (6), 218-234 (1999) J. Lipid Res. 37, 907-925 (1996) Curr. Opin. Lipidol. 10, 151-159 (1999) JP 2001-64672 A JP 2001-354558 A Japanese Patent Laid-Open No. 3-103499 Japanese Patent Laid-Open No. 8-214892 Japanese Patent Laid-Open No. 10-57086 JP 2000-212588 A JP 2001-329291 A JP-A-7-39302 JP-A-8-60181 Japanese Patent Laid-Open No. 10-265795

  From this point of view, it is desired to develop an oil and fat composition having good processing characteristics and flavor as food and having excellent physiological action.

  The inventor has made various studies on the fatty acid composition of monoglyceride. As a result, the monoglyceride mixture containing specific amounts of IPA and DHA as constituent fatty acids has good flavor, and has outstanding gelling properties and water uptake properties, and thus has excellent processing characteristics, and has a PPAR activation effect, β The present inventors have found that the oxidative activation action is extremely strong and useful as a health-beneficial food, feed and medicine.

That is, the present invention includes the following components (A) and (B):
(A) 20 to 75% by weight of the constituent fatty acid is docosahexaenoic acid (DHA), 0.1 to 25% by weight is icosapentaenoic acid (IPA), and their weight ratio (DHA / IPA) is 2 or more. 80-99.9% by weight monoglyceride,
(B) Diglyceride 0.1-20% by weight
The oil-and-fat composition containing this is provided.
Moreover, this invention provides the foodstuffs, feed, and pharmaceutical which contain the said oil-fat composition.

  The oil and fat composition of the present invention has excellent processing characteristics, good flavor, excellent PPAR activation and β-oxidation activation, and is useful as a food and feed in addition to pharmaceutical use for diabetes, hyperlipidemia and obesity. is there.

  Of the fatty acids constituting the monoglyceride (component (A)) of the oil and fat composition of the present invention, the content of docosahexaenoic acid (DHA) is 20 to 75% by weight in terms of physiological effects, processing characteristics and flavor, and further 30 It is preferable to be -65% by weight, especially 35-55% by weight.

  Of the fatty acids constituting the monoglyceride (component (A)), the content of icosapentaenoic acid (IPA) is 0.1 to 25% by weight in terms of physiological effects, processing characteristics, and flavor, It is preferably 20% by weight, in particular 0.1 to 15% by weight.

  The weight ratio of DHA to IPA in monoglyceride (DHA / IPA) needs to be 2 or more from the viewpoint of flavor, processing characteristics, and physiological effects, preferably 2 to 20, more preferably 3 to 13, and further It is preferable that it is 4-11, especially 5-8.

  The remaining constituent fatty acids of monoglyceride (component (A)) include ω9 unsaturated fatty acids, ω6 unsaturated fatty acids, saturated fatty acids and the like. Here, the ω9 unsaturated fatty acid having 8 to 22 carbon atoms such as oleic acid is 0 to 50% by weight, more preferably 0.1 to 25% by weight, particularly 0% from the viewpoint of industrial productivity and fatty acid intake balance. It is preferable to contain 1 to 15% by weight.

Further, for example, ω6-unsaturated fatty acids having 8 to 22 carbon atoms such as linoleic acid and γ-linolenic acid are 0.1 to 25% by weight, more preferably 0.1 to 25% in terms of industrial productivity and fatty acid intake balance. It is preferable to contain 10% by weight, particularly 0.2 to 5% by weight.
Further, the saturated fatty acid is preferably contained in an amount of 0 to 30% by weight, more preferably 0.1 to 20% by weight, and particularly preferably 0.5 to 15% by weight from the viewpoint of industrial productivity and physiological effects.

  Such monoglyceride (component (A)) needs to be contained in the oil / fat composition of the present invention in an amount of 80 to 99.9% by weight, preferably 90 to 99% by weight, and further 92 in terms of physiological effects and processing characteristics. It is preferably contained in 9 to 97% by weight, particularly 93 to 97% by weight.

Diglyceride (component (B)) is required to be contained in the oil / fat composition of the present invention in an amount of 0.1 to 20% by weight, preferably 1 to 10% by weight in terms of processing characteristics, industrial productivity, and flavor. Further, it is preferable to contain 2.9 to 7% by weight, particularly 3 to 7% by weight.
The constituent fatty acid of diglyceride (component (B)) is preferably the same as monoglyceride from the viewpoint of industrial productivity.

In the oil and fat composition of the present invention, the triglyceride content is preferably 19.9% by weight or less, more preferably from 0 to 9% by weight, particularly preferably from the viewpoint of physiological effects, processing characteristics, and industrial productivity. It is preferably 01 to 4% by weight, more preferably 0.1 to 4% by weight.
The constituent fatty acid of triglyceride is preferably the same as that of monoglyceride from the viewpoint of industrial productivity.

In the oil and fat composition of the present invention, the content of free fatty acid or a salt thereof is preferably 5% by weight or less from the viewpoint of flavor, stability, and industrial productivity, and further 0 to 2.5% by weight, In particular, it is preferably 0.01 to 1% by weight, more preferably 0.1 to 0.5% by weight.
In terms of industrial productivity, the free fatty acid or salt thereof of the oil and fat composition of the present invention is preferably the same as the constituent fatty acid of monoglyceride.

  The oil / fat composition of the present invention having such a specific glyceride composition and fatty acid composition is, for example, an esterification reaction between glycerin and a fatty acid using an enzyme such as lipase, or transesterification of glycerin and an oil / fat using an alkali catalyst or the like. It can be produced by reaction or the like. In addition, as shown in the production examples described later, after a protective group such as dioxolane is bonded to glycerin, a transesterification reaction is performed with oil and fat, and then the protective group is removed to produce a desired oil and fat composition.

  The oil and fat composition of the present invention is preferably used after purification such as degumming, deoxidation, washing with water, decolorization, deodorization, etc. in terms of flavor and stability, and in particular, the peroxide value (POV) is 20 or less, It is preferably 10 or less, more preferably 7 or less, still more preferably 5 or less, particularly preferably 3 or less, and most preferably 0.1 to 1. Furthermore, it is preferable that the color (10R + Y) by the Loby bond method (using a 5 1/4 inch glass cell) is 50 or less, preferably 40 or less, more preferably 30 or less, especially 5 to 25.

  It is preferable from the viewpoint of flavor and stability that an antioxidant (component (C)) is added to the oil and fat composition of the present invention. Antioxidants may be any as long as they are usually used in foods and pharmaceuticals, but catechins, tocopherols, vitamin C fatty acid esters, butylhydroxytoluene (BHT), butylhydroxyanisole (BHA), tertiary butylhydroquinone ( TBHQ), a phospholipid, and one or more combinations of natural antioxidant components are preferable, and tocopherol and catechin are particularly preferable. Examples of vitamin C fatty acid esters include palmitic acid esters and stearic acid esters, and examples of natural antioxidant components include herbs such as rosemary, extracts from peach leaves and roots, and the like. The antioxidant is preferably added to the oil and fat composition of the present invention in an amount of 0.01 to 5% by weight, particularly 0.05 to 1% by weight.

  The oil and fat composition of the present invention preferably contains a plant sterol (component (D)) in terms of cholesterol lowering effect. The plant sterol is preferably contained in the oil / fat composition of the present invention in an amount of 0.05 to 19.9% by weight, more preferably 0.3 to 4.7% by weight, particularly 1.2 to 4.7% by weight. Is preferred. Examples of plant sterols include free forms such as α-sitosterol, β-sitosterol, stigmasterol, campesterol, α-sitostanol, β-sitostanol, stigmasteranol, campestanol, and cycloartenol, and the like. And fatty acid esters, ferulic acid esters, cinnamic acid esters and the like.

  It is preferable in terms of appearance and workability to add a crystallization inhibitor to the oil and fat composition of the present invention. Examples of the crystallization inhibitor used in the present invention include polyglycerin condensed ricinoleic acid ester, polyglycerin fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, and polyol fatty acid ester of propylene glycol fatty acid ester. . The polyol fatty acid ester is preferably a polyglycerol fatty acid ester, a sucrose fatty acid ester, or a sorbitan fatty acid ester having an HLB (Griffin calculation formula) of 4 or less, particularly 3 or less. In the oil and fat composition of the present invention, the crystallization inhibitor is preferably contained in an amount of 0.02 to 5% by weight, particularly 0.05 to 2% by weight.

  The oil and fat composition thus obtained has an excellent PPAR activation action and β-oxidation activation action, and further has excellent gelling properties and water uptake properties, so that it has excellent processing characteristics and flavor. Since it has such excellent characteristics, the oil and fat composition of the present invention can be used for foods, feeds and pharmaceuticals.

  As food, it can be used for oil-containing foods and food additives containing the oil composition as a part of food. Examples of such fat-containing foods include health foods that exhibit specific functions to promote health. In addition, food additives include emulsification, demulsification, solubilization, dispersion, wetting, coating, foaming, defoaming, penetration, mold release, washing, antibacterial, quality improvement, etc. Can be used as supplementary foods.

  Specific foods include capsules, tablets, granules, powders, breads, cakes, cookies, pies, pizza crusts, bakery mixes and other bakery foods, soups, sauces, ice creams, coffees, etc. Oil-in-water emulsified food such as whitener, dressing, mayonnaise, whipped cream, water-in-oil emulsified food such as margarine, spread, butter cream, confectionery such as chocolate, candy, caramel, tablet, sausage, ham, hamburg In addition to processed meat foods, beverages, noodles, prepared dishes, frozen foods, retort foods and the like can be mentioned. Such foods can be produced by adding commonly used food materials in addition to the above-described oil / fat composition, depending on the type of the oil / fat-containing foods and food additives.

  The blending amount of the oil and fat composition of the present invention into the oil and fat-containing food varies depending on the type of food, but is generally 0.1 to 100% by weight, particularly 1 to 80% by weight. Moreover, although the compounding quantity to the food additive of the oil-fat composition of this invention changes with uses of a food additive, generally 1 to 100 weight%, especially 80 to 100 weight% is preferable. The blending amount of the food additive of the present invention in the food varies depending on the use of the food additive, but is generally 0.01 to 10% by weight, particularly preferably 0.1 to 5% by weight.

  Examples of the pharmaceutical include oral preparations such as solid preparations such as powders, granules, capsules, pills and tablets, liquids such as liquids, suspensions and emulsions. In addition to the oil and fat composition described above, this oral administration agent includes excipients, disintegrants, binders, lubricants, surfactants, alcohols, water, water-soluble high-concentration agents that are generally used depending on the form of the oral administration agent. Molecules, sweeteners, flavoring agents, acidulants and the like can be added for production. Examples of drugs for oral administration include diabetes preventive and therapeutic agents, obesity preventive and hyperlipidemia preventive and therapeutic agents based on PPAR activating action and β-oxidation activating action. The blending amount of the oil and fat composition of the present invention into a pharmaceutical product for oral administration varies depending on the use and form of the pharmaceutical product, but is generally 0.1 to 100% by weight, particularly preferably 1 to 80% by weight. Moreover, it is preferable to administer 0.1-50g per day as an oil-fat composition divided into 1 to several times.

  Examples of the feed include not only food for animals such as pigs, chickens, and fish, but also pet food for pets such as dogs and cats. The blending amount of the oil and fat composition of the present invention in the feed is preferably 1 to 40% by weight, more preferably 1 to 30% by weight, and particularly preferably 2 to 20% by weight. The oil and fat composition of the present invention can be used by replacing all or part of the oil and fat in the feed.

  In addition to the oil and fat composition, the feed is produced by mixing with commonly used feed materials such as meat, protein, grains, bran, potatoes, sugars, vegetables, vitamins and minerals. As meat, beef, pig, sheep (mutton or lamb), rabbit, kangaroo and other livestock meat, beef and its by-products, processed products; meat balls, meat bone meal, chicken meal and other raw materials rendered above; Examples include seafood such as bonito, horse mackerel, sardine, scallops, scallops, and fish meal (fishmeal). Examples of proteins include milk proteins such as casein and whey, plant proteins such as soybean protein, and examples of grains include wheat, barley, rye, milo, and corn. Examples of rice bran include rice bran and bran, and examples of rice bran include soybean meal. The total amount of meat, protein, grains, bran and potatoes in the feed is preferably 5 to 95% by weight. Examples of the saccharide include glucose, oligosaccharide, sugar, sugar beet, starch, liquid sugar and the like, and it is preferably contained in the feed in an amount of 5 to 80% by weight. Examples of vegetables include vegetable extracts and the like, and preferably 1 to 30% by weight in the feed. Examples of vitamins include A, B1, B2, D, E, niacin, pantothenic acid, carotene, and the like, and it is preferably contained in the feed in an amount of 0.05 to 10% by weight. Examples of minerals include calcium, phosphorus, sodium, potassium, iron, magnesium, zinc and the like, and it is preferably contained in the feed in an amount of 0.05 to 10% by weight. In addition, a gelling agent, a shape-retaining agent, a pH adjuster, a seasoning, an antiseptic, a nutrition reinforcing agent and the like that are generally used in feeds can also be contained.

Example 1 Production of Oil and Fat Composition The following oil and fat composition was produced. Table 1 shows the composition of the obtained oil and fat composition. The glyceride composition was measured by HPLC (column: “TSKgel G2500H” manufactured by Tosoh Corporation, elution solvent: THF, solvent flow rate: 0.4 mL / min, detector: RI). The fatty acid composition was measured by the GLC method after methyl esterification (Japan Oil Chemistry Association "standard oil analysis test method" 2.4.1.2-1996, 2.4.2.2-1996).

Oil composition 1 (product of the present invention)
In a four-necked flask, 422.9 g of 2,2-dimethyl-1,3-dioxolane-4-methanol and 0.64 g of sodium hydroxide were placed, dehydrated at 80 ° C. and alcoholated, and then 50 ° C. Cooled to. To this was added 355.3 g of DHA-rich oil “DHA-22” (manufactured by Maruha Co., Ltd.), reacted for 1.5 hours, and then neutralized with 50% sulfuric acid. Next, vacuum distillation was performed at 1.33 kPa and 80 to 100 ° C. to distill off water and 2,2-dimethyl-1,3-dioxolane-4-methanol. This was washed with water to obtain 451.4 g of monoglyceride acetal.
To 220 g of the obtained monoglyceride acetal, 13.2 g of acid clay (Galeon Earth NV, manufactured by Mizusawa Chemical Co., Ltd.) was added. Into the reaction system, 10% of water vapor was introduced per hour with respect to the monoglyceride acetal, and the deacetalization reaction was carried out for 6 hours while removing acetone generated during the reaction and excess water vapor from the system (70). ° C, 13.3 kPa). Next, after adding 6.6 g of an acid adsorbent (KW600S, manufactured by Kyowa Chemical Co., Ltd.), dehydration was performed for 0.5 hours (6.65 kPa, 70 ° C.). This was filtered to obtain 170.7 g of monoglyceride. Tocopherol “Emix D” (manufactured by Eisai Co., Ltd.) was added to this in an amount of 200 ppm to produce an oil and fat composition 1.

Oil composition 2 (product of the present invention)
The oil and fat composition 2 was produced in the same manner as the oil and fat composition 1, using “DHA-45” (manufactured by Maruha Co., Ltd.) as the DHA-rich oil.

Oil composition 3 (product of the present invention)
In a four-necked flask, 1000 g of DHA-rich oil “DHA-70G” (manufactured by Nippon Chemical Feed Co., Ltd.), 280 g of glycerin and 1 g of sodium hydroxide were placed, and the reaction was performed at 170 ° C. for 2 hours under a nitrogen stream. It was. After completion of the reaction, 0.88 g of phosphoric acid was added for neutralization. Subsequently, deglycerin was performed for 10 minutes (180 ° C., 0.667 kPa), and then thin film distillation was performed (185 ° C., 0.004 kPa). A fraction obtained by thin film distillation was collected, and 200 ppm of tocopherol “Emix D” (manufactured by Eisai Co., Ltd.) was added to obtain an oil and fat composition 3.

Oil composition 4 (comparative product)
As the oil and fat composition 4, DHA high content oil “DHA-22” (manufactured by Maruha Corporation) was used.

Oil composition 5 (comparative product)
The residue of the thin film distillation produced | generated at the time of manufacture of the fat composition 3 was extract | collected. This was subjected to silica gel column chromatography (“Wakogel C-200” (manufactured by Wako Pure Chemical Industries, Ltd.)), and hexane and ethyl acetate (first 100: 0, then 95: 5, then 90:10, then 80: 20 and finally 70:30, v / v). Subsequently, the solvent was distilled off with an evaporator. After mixing the obtained fractions, 200 ppm of tocopherol “Emix D” (manufactured by Eisai Co., Ltd.) was added to produce an oil and fat composition 5.
Oil composition 6 (comparative product)

  As the oil and fat composition 6, high purity monoglyceride “Excel O-95R” (manufactured by Kao Corporation) was used.

Oil composition 7 (comparative product)
“Eicosapentaenoic acid” (manufactured by Sigma) was used.

Oil composition 8 (comparative product)
“Docosahexaenoic acid” (manufactured by Sigma) was used.

Example 2 PPARγ Activation Test The small intestine epithelial cell line IEC-6 was plated on a 12-well plate and cultured in DMEM (5% FCS) for 1 day. Here, a plasmid (pGAL4-PPARγ-LBD) expressing a chimeric molecule of GAL4-DNA binding domain (DBD) and PPARγ ligand binding domain (LBD), and a reporter plasmid (pREP) containing a GAL4 binding sequence upstream of the firefly luciferase gene Transfection reagent (Superfect transfectio) at 0.5 μg / well at the same time
n reagent; QIAGEN). In order to monitor the transfection efficiency, the Renilla luciferase gene was simultaneously incorporated into pGAL4-PPARγ-LBD. Thereafter, the culture solution was mixed with DMEM (+250 μM) containing the test substance (500 μM).
The medium was changed to BSA) and further cultured for 24 hours. After washing with PBS, cells were lysed using a dual luciferase assay system (Promega). Next, a substrate solution containing luciferin was added to the lysate, and firefly and Renilla luciferase activities were measured with a luminometer. Thus, the PPARγ activation ability was evaluated by measuring the transcriptional activity (luciferase activity) of the PPARγ-dependent gene. The PPARγ-dependent transcription activity (luciferase activity) was defined as follows.

  PPARγ-dependent gene transcription activity (luciferase activity) = (firefly luciferase activity by pREP) / (renilla luciferase activity by pGAL4-PPARγ-LBD).

  The PPARγ-dependent transcription activity in the control was defined as 100, and the relative value is shown in Table 1.

Example 3 Evaluation of Gelation Property In each oil / fat: water = 70: 30 (weight / weight), the gelation property was visually observed and evaluated according to the following evaluation criteria. The results are shown in Table 1.
A: There is no fluidity and it has gelled.
B: There is not so much fluidity and it has gelled a little.
C: It has fluidity and is partly gelled.
D: It has fluidity and is not gelled at all.

Example 4 Evaluation of Deteriorated Odor The sample (each oil: water = 70: 30) prepared in Example 3 was allowed to stand at room temperature for 1 week. This smell was sniffed, and sensory evaluation of the deteriorated odor was performed according to the following evaluation criteria. The results are shown in Table 1.
A: There is almost no deterioration odor and it is not unpleasant.
B: Although there is a slight deterioration odor, it is not unpleasant.
C: There is a deterioration odor and it is uncomfortable.
D: There is a strong deterioration odor and it is very uncomfortable.

Example 5 Evaluation of water uptake It was investigated every 5% by weight how much water can be taken into each sample heated to 50 ° C. with respect to the whole system. The value just before the point at which water separated was taken as the value of water uptake. The results are shown in Table 1.

Table 1 shows that the product of the present invention has a high gelling property and an excellent water uptake property, so that it is easy to form a gel containing a large amount of water, and the deterioration odor is small. Therefore, the oil and fat composition of the present invention is excellent in processing characteristics to various foods and has a good flavor. Since it has such characteristics, there are merits such as, for example, drip during freezing and thawing is reduced, water activity (Aw) is reduced, and storage stability is improved. On the other hand, Comparative products 4 and 5 having a low monoglyceride content have poor gelling properties and cannot take in water.
Moreover, it was shown that the oil-fat composition of the present invention has a very strong PPARγ activation action as compared with the comparative product 6 (monoglyceride content is high but the fatty acid composition is different).

Example 6 Animal experiment (β oxidation activation test)
C57BL / 6 mice (n = 6) were ingested for 10 days with 10 parts by weight of fat composition 2 (present product) or fat composition 6 (comparative product) added to the basic diet shown in Table 2 I let you. Dissected on the last day, the small intestine was collected and mRNA was isolated. Subsequently, the expression level of ACO (Acyl-CoA Oxidase) mRNA was measured by Real time RT-PCR. The results are shown in Table 3 as relative amounts with the amount of mRNA expressed by ingesting the fat composition 6 as 1.00.

  By ingesting the fat and oil composition 2 of the present invention, the mRNA expression level of ACO, which is a β-oxidation-related enzyme, markedly increased in the small intestine, indicating activation of β-oxidation.

Example 7 Tablet 100 parts by weight of oil and fat composition 2, 0.02 part by weight of “Mixed vitamin E MDE-6000” (manufactured by Yatsushiro Co., Ltd.), catechin “Sankar No. 1” (manufactured by Taiyo Chemical Co., Ltd.) 0 .1 part by weight, 0.02 part by weight of “Vitamin C Palmitate” (Roche) and 2.0 part by weight of plant sterol “CANOLA STERYLESTERS” (manufactured by ADM) are mixed to obtain an oil and fat composition 7. It was. A mixture of 10 parts by weight of the oil composition, 44 parts by weight of corn starch, 40 parts by weight of crystalline cellulose, 5 parts by weight of carboxymethylcellulose calcium, 0.5 parts by weight of anhydrous silicic acid and 0.5 parts by weight of magnesium stearate was tableted. To produce tablets (200 mg / piece).

Example 8 Soft capsule 100 parts by weight of oil and fat composition 3, "mixed vitamin E MDE-6000" (manufactured by Yatsushiro Co., Ltd.) 0.02 parts by weight, catechin "Sankar No. 1" (manufactured by Taiyo Kagaku Co., Ltd.) 0 .5 parts by weight, 0.1 part by weight of rosemary extract “Herbarox type HT-O” (manufactured by Calsec) and 0.2 part by weight of polyglycerol fatty acid ester “THL-3” (manufactured by Sakamoto Pharmaceutical Co., Ltd.) The oil and fat composition 8 was obtained by mixing the parts. 300 mg of the oil / fat composition was enclosed in an oval soft capsule to prepare a soft capsule.

Example 9 Deep-fried Satsuma Oil composition 1 part by weight, 600 parts by weight of ground soup (surimi), 30 parts by weight of sugar, 30 parts by weight of soy sauce, 5 parts by weight of miso, 5 parts by weight of potato starch, 100 parts by weight of whole egg Stir and mix well. This was shaped into a small size of 50 g, and then fried for 4 minutes with 180 ° C. salad oil (manufactured by Nissin Oil Co., Ltd.) to make a sweet potato.

Example 10 Spread Oil phase: 0.5 parts by weight of fat composition 2, 68.8 parts by weight of partially cured soybean oil, 0.1 parts by weight of lecithin, 0.5 parts by weight of condensed ricinoleic acid ester, 0.1 parts by weight Part Aqueous phase: 28.4 parts by weight, skim milk powder 0.3 parts by weight, sodium chloride 1.3 parts by weight The above oil phase and aqueous phase were prepared, and then mixed for 10 minutes with a homomixer (special Kokuka Kogyo Co., Ltd.). Emulsification was performed. The obtained emulsion was quenched and plasticized by a conventional method to obtain a spread.

Example 11 Pet food 2 parts by weight of oil and fat composition 7, 15 parts by weight of corn flour, 8 parts by weight of meat meal, 26 parts by weight of wheat flour, 20 parts by weight of defatted soybean, 16 parts by weight of fish meal, 4 parts by weight of beet pulp, 2 bone meals Part by weight, 4 parts by weight of a vitamin / mineral mixture, and 3 parts by weight of lard were mixed to prepare a pet food for dogs.

Claims (6)

The following components (A) and (B):
(A) 20 to 65 % by weight of the constituent fatty acid is docosahexaenoic acid (DHA), 0.1 to 25% by weight is icosapentaenoic acid (IPA), and their weight ratio (DHA / IPA) is 2 or more. monoglyceride 80 to 99% by weight,
(B) Diglyceride 0.1-20% by weight
And a fat or oil composition containing 0.1 to 5% by weight of a free fatty acid or a salt thereof.   The oil or fat composition according to claim 1, further comprising (C) an antioxidant of 0.01 to 5% by weight.   The oil composition according to claim 1 or 2, further comprising (D) 0.05 to 19.9% by weight of plant sterol.   The foodstuff containing the oil-fat composition of any one of Claims 1-3.   The feed containing the oil-fat composition of any one of Claims 1-3.   The pharmaceutical containing the oil-fat composition of any one of Claims 1-3.