JP2008069184A - Oil-and-fat composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an oil-and-fat composition having excellent antiobesity effect, anorexigenic effect and storage stability. <P>SOLUTION: The oil-and-fat composition contains (A) 100 pts.mass of an oil-and-fat containing ≥15 mass% diacylglycerol having an unsaturated fatty acid content of ≥80 mass%, a conjugated linoleic acid content of 2-85 mass% and an ω3 unsaturated fatty acid content of <15 mass% in the constitutent fatty acids and having a monoacylglycerol content of ≤5 mass% and a free fatty acid content of ≤5 mass% and (B) 0.001-2 pts.mass of tocopherol. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to an oil / fat composition having a high diacylglycerol content containing conjugated linoleic acid.

Various researches have been conducted on the physiological effects of fats and oils against the background of health orientation in the world. For example, conjugated linoleic acid has been found to have a therapeutic effect on diabetes and syndrome X in addition to anti-obesity and anti-tumor effects (see Patent Documents 1 to 5 and Non-Patent Document 1). Application of conjugated linoleic acid having such a function to foods has been reported (see Patent Document 6).
On the other hand, anti-obesity action and the like have also been found in diacylglycerol (see Patent Documents 7 and 8). Furthermore, fats and oils containing diacylglycerol having a high specific fatty acid content such as ω3 fatty acid and linoleic acid are known (see Patent Documents 9 to 11).
In addition, an oil composition that combines diacylglycerol and plant sterol has been found to have an effect of improving blood cholesterol level (see Patent Document 12).
Since conjugated linoleic acid is a free fatty acid, it is not suitable for ingestion or use in foods due to the unique taste of fatty acids. Then, the trial which extends an application range is made by making conjugated linoleic acid into an ester body (refer patent documents 13-18, nonpatent literature 2).

However, even if it is an ester form, the above compound is not satisfactory in terms of flavor and storage stability when the content of conjugated linoleic acid is increased.
International Publication No. 96/06605 Pamphlet WO 97/46230 pamphlet JP 2003-171272 A International Publication No. 02/009691 Pamphlet International Publication No. 02/009693 Pamphlet International Publication No. 00/21379 Pamphlet Japanese Unexamined Patent Publication No. 4-300826 Japanese Patent Laid-Open No. 10-176181 International Publication No. 01/109899 Pamphlet International Publication No. 02/11552 Pamphlet European Publication No. 0679712 WO99 / 48378 pamphlet International Publication No. 00/64854 Pamphlet International Publication No. 04/96748 Pamphlet JP 2003-113396 A US Pat. No. 6,432,453 US Pat. No. 6,608,222 European Publication No. 1097708 "Lipids", 1997, 32, p.853-858 "Biotechnology Letters", 1998, Volume 20, Issue 6, p.617-621

  An object of the present invention is to provide an oil and fat composition having a high diacylglycerol content, including conjugated linoleic acid, which has a remarkable anti-obesity effect and excellent stability.

  As a result of investigations by the present inventors, it has been found that the above problems can be solved by adjusting the diacylglycerol content, the conjugated linoleic acid content, the tocopherol content, etc. in the diacylglycerol to a specific range. Furthermore, it discovered that the obtained oil-fat composition had an eating suppression effect, and resulted in this invention.

That is, the present invention includes the following components (A) and (B):
(A) 15% by mass or more of diacylglycerol having an unsaturated fatty acid content in the constituent fatty acid of 80% by mass or more, a conjugated linoleic acid content of 2 to 85% by mass, and an ω3 unsaturated fatty acid content of less than 15% by mass An oil and fat composition containing 100 parts by mass of (B) tocopherol 0.001 to 2 parts by mass of an oil and fat containing a monoacylglycerol content of 5% by mass or less and a free fatty acid content of 5% by mass or less. .

  According to the present invention, a fat and oil composition containing a conjugated linoleic acid having a specific composition and a high diacylglycerol content and a tocopherol can be used to provide a remarkable anti-obesity effect and feeding suppression effect when ingested. Furthermore, the storage stability as an oil and fat composition can be remarkably improved.

  The oil and fat composition of the present invention contains the oil and fat of component (A) as an essential component. The fat or oil (A) contains 15% by mass (hereinafter simply referred to as%) or more of diacylglycerol (DAG), preferably 15 to 95%, more preferably 20 to 95%, and further 35 to 95. %, Particularly 60 to 90%, particularly 70 to 85%, is preferable in terms of physiological effects, industrial productivity of fats and oils, appearance, food application and the like.

  The diacylglycerol contained in the oil (A) used in the present invention comprises 80 to 100% of unsaturated fatty acids, preferably 85 to 100%, more preferably 90 to 98%, and particularly 93 to 98%. % Is preferable in terms of appearance, physiological effect, and industrial productivity of fats and oils. Here, it is preferable that carbon number of this unsaturated fatty acid is 14-24, and also 16-22.

  Of the fatty acids constituting the diacylglycerol contained in the fat (A), the content of conjugated linoleic acid (CLA) is 2 to 85%, preferably 5 to 80%, more preferably 15 to 75%, especially 35 to 70%. Particularly preferred is 40 to 55% in terms of reduction in body fat, suppression of feeding, storage stability, appearance, and intake balance of fatty acids.

  Conjugated linoleic acid includes 9,11-octadecadienoic acid, 10,12-octadecadienoic acid, their position and geometric isomers, and mixtures thereof. Specific examples include cis-9, trans-11-octadecadienoic acid, trans-9, cis-11-octadecadienoic acid, trans-10, cis-12-octadecadienoic acid, and the like. Conjugated linoleic acid can be made from linoleic acid or oils with high linoleic acid content, biochemical conjugation using ruminant or microbial enzymes, and chemical conjugation by heating under alkaline conditions. Etc.

  Among the fatty acids that make up diacylglycerol, the content of oleic acid is 1 to 65%, preferably 2 to 50%, especially 3 to 30%, especially 4 to 15%. Desirable in terms of balance. Further, from the viewpoint of appearance and physiological effect, the content of dioleylglycerol in diacylglycerol is preferably less than 45%, particularly preferably 0 to 40%.

  Of the fatty acids constituting diacylglycerol, the content of ω3-unsaturated fatty acids is less than 15%, preferably 0 to 10% in view of stability, appearance, and fatty acid intake balance. Examples of the ω3 unsaturated fatty acid include α-linolenic acid, icosapentaenoic acid, docosahexaenoic acid, and the like.

  Of the fatty acids constituting diacylglycerol, the content of saturated fatty acids is less than 20%, but it is 0-10%, more preferably 0-7%, especially 2-7%, especially 2-6%. In terms of physiological effects and industrial productivity of fats and oils. As the saturated fatty acid, those having 14 to 24 carbon atoms, particularly 16 to 22 carbon atoms are preferable, and palmitic acid and stearic acid are most preferable.

  Among the fatty acids constituting diacylglycerol, the content of trans-unsaturated fatty acids other than conjugated linoleic acid is 0 to 3.5%, particularly 0.1 to 3%. Flavor, physiological effect, appearance, storage stability From the viewpoint of industrial productivity of fats and oils.

  In the fatty acid constituting diacylglycerol, the content of fatty acid having 12 or less carbon atoms is preferably 5% or less from the viewpoint of flavor, and further 0 to 2%, particularly 0 to 1%, substantially not contained. Is most preferred. The remaining constituent fatty acids preferably have 14 to 24 carbon atoms, particularly 16 to 22 carbon atoms.

  Further, from the viewpoint of physiological effect, storage stability, industrial productivity of fats and oils, and flavor, the ratio of 1,3-diacylglycerol in diacylglycerol is 50% or more, further 52 to 100%, further 54 to 90%, particularly It is preferred to use diacylglycerol which is 56-80%.

  The fats and oils (A) used in the fat and oil composition of the present invention are triacylglycerol (TAG) 4.9 to 84.9%, further 4.9 to 64.9%, and further 6.9 to 39.9. %, Especially 6.9 to 29.9%, especially 9.8 to 19.8%, is desirable in terms of physiological effects, industrial productivity of fats and oils, and appearance.

In the constituent fatty acid of triacylglycerol contained in the fat (A) used in the present invention, the content of conjugated linoleic acid is preferably 50% or less, more preferably 1 to 35%, particularly 2 to 20%, It is particularly preferably 5 to 15% from the viewpoint of storage stability, physiological effect, and industrial productivity of fats and oils.
The mass ratio (formula (1)) between the content of conjugated linoleic acid in the fatty acid constituting the diacylglycerol contained in the fat (A) and the content of conjugated linoleic acid in the fatty acid constituting the triacylglycerol is 1 Is preferably from 2 to 9, more preferably from 3 to 8, and particularly preferably from 4 to 7, from the viewpoints of storage stability and physiological effects.
CLA content in DG / CLA content in TG (1)

  The content of oleic acid in the constituent fatty acid of triacylglycerol contained in the fat (A) is preferably 15 to 70%, more preferably 20 to 65%, particularly 30 to 60%, and particularly 45 to 55%. It is preferable in terms of storage stability, physiological effect, and industrial productivity of fats and oils.

  The fatty acid (A) is composed of 70 to 100%, more preferably 80 to 100%, more preferably 90 to 100%, particularly 93 to 98%, especially 94 to 98% of unsaturated fatty acids. Is preferable in terms of physiological effects and industrial productivity of fats and oils. The number of carbon atoms of the unsaturated fatty acid is preferably 10 to 24, and more preferably 16 to 22 in view of physiological effects and industrial productivity of fats and oils.

  The fat and oil (A) used in the fat and oil composition of the present invention contains 0.1 to 5% monoacylglycerol (MAG), further 0.1 to 2%, more preferably 0.1 to 1.5%, especially 0. The content of 0.1 to 1.3%, particularly 0.2 to 1% is preferable in terms of flavor, appearance, fuming, industrial productivity of fats and oils, and food applications.

  The constituent fatty acid of monoacylglycerol contained in the fat (A) used in the present invention is preferably the same constituent fatty acid as diacylglycerol in view of physiological effects and industrial productivity of fats and oils.

  Moreover, it is preferable that the free fatty acid / salt (FFA) content contained in the fats and oils (A) used in the fat and oil composition of the present invention is reduced to 5% or less, further 0 to 3.5%, and further 0. From 2 to 2%, particularly from 0.01 to 1%, and more preferably from 0.05 to 0.5%, are preferred from the viewpoint of flavor, smoke generation, work comfort during cooking, and industrial productivity of fats and oils.

  Of the total fatty acids constituting the oil (A) used in the present invention, the content of unsaturated fatty acids is preferably 80 to 100%, more preferably 85 to 100%, particularly 90 to 100%, and particularly 93 to 93%. 98% is preferable in terms of physiological effects and industrial productivity of fats and oils.

  Among the total fatty acids constituting the oil (A) used in the present invention, the content of fatty acids having 4 or more carbon-carbon double bonds is oxidative stability, work comfort during cooking, physiological effects, and coloring. From the standpoint of flavor and the like, 0 to 40%, further 0 to 20%, further 0 to 10%, particularly preferably 0 to 1% are preferable, and it is most preferable that they are not substantially contained.

Of the total fatty acids constituting the fats and oils (A), the content of trans-unsaturated fatty acids is 0 to 4%, and more preferably 0.1 to 3.5% of flavor, physiological effect, appearance, fats and oils. It is preferable in terms of industrial productivity.
In the present invention, the content of trans-unsaturated fatty acid is a value measured by the AOCS method (American Oil Chem. Soc. Official Method: Ce1f-96, 2002).

  The content of conjugated linoleic acid in the total fatty acid constituting the fat (A) is preferably 2 to 85%, more preferably 5 to 75%, particularly 15 to 50%, and particularly 20 to 30% by mass. Is preferable in view of physiological effects, storage stability, application to foods, etc., and industrial productivity of fats and oils.

  Of the total fatty acids constituting the fat (A), the content of oleic acid is preferably 20 to 65%, more preferably 25 to 60%, particularly 30 to 55%, especially 35 to 50% by mass. Are preferable in terms of storage stability, application to foods and the like, and industrial productivity of fats and oils.

  Of the total fatty acids constituting the fat (A), the content of linolenic acid is preferably 15% or less, more preferably 0.1 to 12%, particularly 1 to 10%, particularly 3 to 8% by mass. Are preferable in terms of storage stability, application to foods and the like, industrial productivity of fats and oils, and physiological effects.

The origin of the fat (A) used in the fat composition of the present invention may be either vegetable or animal fat. Specific examples of the raw material include rapeseed oil, sunflower oil, corn oil, soybean oil, rice oil, safflower oil, cottonseed oil, and beef tallow. In addition, those obtained by separating and mixing these oils and fats, those prepared by adjusting the fatty acid composition by hydrogenation or transesterification, etc. can be used as raw materials, but those not hydrogenated constitute the oil and fat composition. It is preferable from the viewpoint of reducing the trans acid content in the total fatty acids.
Furthermore, as raw material fats and oils, deodorized oils and non-deodorized fats and oils that have not been deodorized in advance can be used. In the present invention, undeodorized fats and oils are used for some or all of the raw materials to reduce trans-unsaturated fatty acids other than conjugated linoleic acid and leave plant sterols, plant sterol fatty acid esters, and tocopherols derived from raw oils This is preferable.

  The fat (A) can be obtained by the above-described conjugated linoleic acid, esterification reaction of fatty acid derived from fat and glycerin, transesterification of fat and oil containing conjugated linoleic acid and glycerin, and the like. Excess monoacylglycerol produced by the reaction can be removed by molecular distillation or chromatography. These reactions can also be carried out by chemical reactions using an alkali catalyst or the like, but it is excellent in terms of flavor and the like to carry out the reaction under mild conditions enzymatically using a 1,3-position selective lipase or the like. It is preferable. In particular, diluting conjugated linoleic acid-rich diacylglycerols with vegetable oils or fats or transesterification of conjugated linoleic acid-rich diacylglycerols with vegetable oils is preferred in terms of flavor and storage stability.

  The oil and fat composition of the present invention must contain the component (B) tocopherol. (B) The content of tocopherol is 0.001 to 2 parts by mass with respect to 100 parts by mass of the fat (A) in terms of flavor, oxidation stability, coloring, etc., but 0.005 to 1.5 parts by mass. Part, preferably 0.01 to 1 part by weight, particularly 0.01 to 0.5 part by weight, especially 0.02 to 0.2 part by weight.

  (B) As tocopherol, α, β, γ, δ-tocopherol or a mixture thereof can be used. In particular, from the viewpoint of oxidation stability, δ-tocopherol is preferable. In addition, when the oil and fat composition of the present invention is mixed with water or used in foods containing water, and when stored for a long period of time or stored in a bright place, particularly using δ-tocopherol, This is preferable from the viewpoint of preventing flavor deterioration and off-flavor generation.

  Examples of commercially available tocopherols include Emix D, Emix 80 (manufactured by Eisai Co., Ltd.), MDE-6000 (manufactured by Yatsushiro Co., Ltd.), E oil-400 (manufactured by Riken Vitamin Co., Ltd.), and the like.

  In addition to (B) tocopherol, an antioxidant may be added to the oil and fat composition of the present invention. Any antioxidant can be used as long as it is usually used in foods. For example, butylhydroxytoluene (BHT), butylhydroxyanisole (BHA), tertiary butylhydroquinone (TBHQ), catechin, vitamin C or a derivative thereof, phospholipid, rosemary extract, etc., among these, vitamin C Alternatively, it is preferable to use a derivative thereof, catechin, or rosemary extract, and it is particularly preferable to use a mixture of one or more of these.

Vitamin C or a derivative thereof is preferably one that dissolves in fats and oils (A), more preferably a higher fatty acid ester of vitamin C, such as a fatty acid ester having an acyl group having 12 to 22 carbon atoms, L-ascorbyl palmitate, L -Ascorbic acid stearate is particularly preferred, L-ascorbic acid palmitate is most preferred.
In this invention, it is preferable that content of vitamin C or its derivative (s) is 0.004-0.1 mass part as ascorbic acid with respect to 100 mass parts of fats and oils (A), and also 0.006-0. It is preferably 08 parts by mass, particularly 0.008 to 0.06 parts by mass.

  In addition, when the oil and fat composition of the present invention is mixed with water or used in foods containing water and is stored for a long time or in a light place, L-ascorbic acid fatty acid ester as an antioxidant Is preferable from the viewpoint of preventing flavor deterioration and occurrence of off-flavors.

The oil and fat composition of the present invention preferably contains plant sterols as component (C). In the present invention, plant sterols include not only those in which the hydroxyl group is in an ester bond with a fatty acid but in a free state (free form), and derivatives thereof such as ester forms.
In the oil and fat composition of the present invention, the content of the component (C) is preferably 0.05 to 30 parts by mass, more preferably 0.1 to 15 parts by mass with respect to 100 parts by mass of the oil and fat (A). In particular, 0.3 to 8 parts by mass, particularly 0.5 to 4.7 parts by mass is preferable from the viewpoint of cholesterol lowering effect, flavor, appearance, and industrial productivity of fats and oils.

  In the present invention, (C) plant sterols include plant stanols. As plant sterols, for example, brassicasterol, isofucosterol, stigmasterol, 7-stigmasterenol, α-sitosterol, β-sitosterol, campesterol, brassicastanol, isofucostanol, stigmasteranol, 7-sutanol Examples include free forms such as tigmasteranol, α-sitostanol, β-sitostanol, campestanol, cycloartenol, cholesterol, and avenasterol, and ester forms thereof such as fatty acid esters, ferulic acid esters, and cinnamic acid esters. Among these plant sterols, brassicasterol, campesterol, stigmasterol, and β-sitosterol are preferable in terms of industrial productivity and flavor of fats and oils.

  (C) In plant sterols, the total content of brassicasterol, campesterol, stigmasterol and β-sitosterol is preferably 90% or more, more preferably 92 to 100%, particularly 94 to 99%. , Flavor, appearance, industrial productivity of fats and oils, crystal precipitation, storage at low temperature, and physiological effects are preferable.

(C) The content of brush casterol in plant sterols is preferably 0.5 to 8%, more preferably 1 to 7.5%, particularly 3 to 7%, flavor, appearance, fats and oils. In terms of industrial productivity, crystal precipitation, storage at low temperature, and physiological effects.
The content of campesterol in the plant sterols is preferably 10 to 40%, more preferably 15 to 35%, particularly 22 to 30%, which is flavor, appearance, industrial productivity of fats and oils, crystals It is preferable in terms of precipitation, storage stability at low temperatures, and physiological effects.
(C) The content of stigmasterol in the plant sterols is preferably 3 to 30%, more preferably 5 to 25%, particularly 7 to 15%, which is an industrial flavor, appearance, and oil and fat. It is preferable in terms of productivity, crystal precipitation, storage at low temperature, and physiological effects.
(C) The content of β-sitosterol in the plant sterols is preferably 30 to 60%, more preferably 35 to 58%, particularly 40 to 56%, which is an industrial flavor, appearance, and oil and fat. It is preferable in terms of productivity, crystal precipitation, storage at low temperature, and physiological effects.

  (C) The content of cholesterol in the plant sterols is preferably 1% or less, more preferably 0.01 to 0.8%, particularly 0.1 to 0.7%, and particularly 0.2 to 0. 6% is preferable in terms of lowering blood cholesterol and industrial productivity of fats and oils.

  When the plant sterol fatty acid ester is contained in the component (C), the content of unsaturated fatty acid among the constituent fatty acids is preferably 80% or more, more preferably 85 to 100%, particularly 86 to 98%, Particularly preferred is 88 to 93% in view of flavor, appearance, storage stability at low temperature, crystal precipitation, industrial productivity of fats and oils, oxidation stability, and physiological effects.

  In the oil and fat composition of the present invention, it is preferable to further add a crystallization inhibitor (D). 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 propylene glycol fatty acid ester. Polyglycerin fatty acid ester, sucrose fatty acid ester, and sorbitan fatty acid ester are preferable, and polyglycerol fatty acid ester is particularly preferable. The polyol fatty acid ester has an HLB value (Griffin's calculation formula, J. Soc. Cosmet. Chem., 1, 311 (1949)) of 4 or less, particularly preferably 0.1 to 3.5.

  In the present invention, among the fatty acids constituting the polyglycerol fatty acid ester, the content of unsaturated fatty acids is preferably 50 to 95%, more preferably 51 to 80%, and particularly 52 to 60%. From the viewpoint of solubility in fats and oils and oxidation stability. In order to easily dissolve the polyglycerin fatty acid ester in the oil and fat, the content of the unsaturated fatty acid needs to be 50% or more. Moreover, in order to suppress crystallization of fats and oils, it is necessary to make content of unsaturated fatty acid 95% or less. The unsaturated fatty acid preferably has 10 to 24 carbon atoms, more preferably 16 to 22 carbon atoms. Specific examples include palmitoleic acid, oleic acid, petrothelic acid, elaidic acid, linoleic acid, linolenic acid, gatrenic acid, erucic acid, and the like, with oleic acid, linoleic acid, and gatrenic acid being preferred. In the unsaturated fatty acid constituting the polyglycerin fatty acid ester, the content of oleic acid is preferably 80% or more, and particularly 90 to 99.8% is crystal suppression, solubility in fats and oils, cost, oxidation It is preferable in terms of stability and flavor. The content of linoleic acid is preferably 10% or less in the constituent unsaturated fatty acid of polyglycerin fatty acid ester, and particularly 0.1 to 5% is crystal suppression, solubility in fats and oils, cost, oxidation stability It is preferable in terms of properties and flavor. In the unsaturated fatty acid of polyglycerin fatty acid ester, the content of gatrenic acid is preferably 10% or less, and particularly 0.1 to 5% is crystal suppression, solubility in fats and oils, cost, oxidation stability It is preferable in terms of properties and flavor.

  In the present invention, among the fatty acids constituting the polyglycerol fatty acid ester, the content of saturated fatty acid is preferably 5 to 50%, more preferably 20 to 49%, and particularly preferably 40 to 48%, crystal suppression, It is preferable in terms of solubility in fats and oils and oxidation stability. The saturated fatty acid preferably has 10 to 24 carbon atoms, more preferably 12 to 22 carbon atoms. Specific examples include lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid and the like, and myristic acid, palmitic acid, and stearic acid are preferable. In the saturated fatty acid constituting the polyglycerin fatty acid ester, the content of palmitic acid is preferably 80% or more, and particularly 90 to 99.8% is crystal suppression, solubility in fats and oils, cost, oxidation stability It is preferable in terms of properties and flavor. The content of myristic acid in the constituent saturated fatty acid of the polyglycerin fatty acid ester is preferably 10% or less, particularly 0.1 to 5% is crystal suppression, solubility in fats and oils, cost, oxidation stability. It is preferable in terms of flavor. The content of stearic acid in the saturated fatty acid of the polyglycerol fatty acid ester is preferably 10% or less, and particularly 0.1 to 5% is crystal suppression, solubility in fats and oils, cost, oxidation stability. It is preferable in terms of flavor.

  In this invention, content of a crystal | crystallization inhibitor (D) is 0.01-2 mass parts with respect to 100 mass parts of fats and oils (A), Furthermore, 0.02-0.5 mass part, Especially 0.05-0. .2 parts by mass is preferable from the viewpoints of solubility in fats and oils, cost, flavor, and crystal suppression.

  In the oil and fat composition of the present invention, it is preferable to further add an organic carboxylic acid / salt having 2 to 8 carbon atoms. It is preferable that content of C2-C8 organic carboxylic acid is 0.001-0.01 mass part with respect to 100 mass parts of fats and oils (A), Furthermore, 0.0012-0.007 mass part In particular, 0.0015 to 0.0045 parts by mass, particularly 0.0025 to 0.0034 parts by mass is preferable in terms of flavor, appearance, and oxidation stability. As the organic carboxylic acid, citric acid is preferable.

  In the oil and fat composition of the present invention, the raw material fat and oil and the production method are selected so that the component (A) of the composition has a predetermined ratio, and the component (B) is added thereto, and further, the component (C) and It can be obtained by adding component (D), antioxidant, organic carboxylic acid / salt, etc., and appropriately heating and stirring.

The oil and fat composition thus obtained is excellent in terms of storage stability, flavor, texture, appearance, work comfort during cooking, physiological effects, and the like, and can be applied to various foods.
As food, it can be used for processed oils and fats containing the oil and fat composition as part of the food. Examples of such processed oils and fats include health foods, functional foods, foods for specified health use, and the like that exhibit specific functions to promote health. Specific products include bakery foods such as bread, cakes, biscuits, pies, pizza crusts, bakery mixes, oil-in-water emulsions such as soups, sauces, dressings, mayonnaise, coffee whiteners, ice creams, whipped creams, Water-in-oil emulsion such as margarine, spread, butter cream, snack confectionery such as potato chips, confectionery such as chocolate, caramel, candy, dessert, meat processed food such as ham, sausage, hamburger, milk, cheese, yogurt, etc. Examples include dairy products, dough, enrober oils and fats, filling oils and fats, noodles, frozen foods, retort foods, beverages and roux. In addition to the oil and fat composition described above, food raw materials generally used can be added depending on the type of processed oil and fat food. The amount of the oil / fat composition of the present invention to be added to food varies depending on the type of food, but is generally 0.1 to 100%, particularly preferably 1 to 80%.

  Moreover, it can be used as a food material such as cooking oil used for fried food or fried food. Especially, croquettes, tempura, tonkatsu, fried fish, fried fish, spring rolls, etc. Suitable for cooking.

  In addition, from the relation of formulation preparation, when fats and oils derived from food raw materials are included, the mass ratio of the fats and oils derived from food raw materials and the oil and fat composition of the present invention is preferably 95: 5 to 1:99, 95 : 5 to 5:95 is more preferable, 85:15 to 5:95 is more preferable, and 40:60 to 5:95 is particularly preferable.

  The oil and fat composition of the present invention can be used for an oil-in-water emulsion. The mass ratio of the oil phase to the water phase is oil phase / water phase = 1/99 to 90/10, preferably 10/90 to 80/20, and particularly preferably 30/70 to 75/25. It is preferable to contain an emulsifier in an amount of 0.01 to 5%, particularly 0.05 to 3%. Examples of emulsifiers include egg protein, soybean protein, milk protein, proteins separated from these proteins, various proteins such as (partial) degradation products of these proteins, sucrose fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester Glycerin fatty acid monoester, polyglycerin fatty acid ester, polyglycerin condensed ricinoleic acid ester, glycerin organic acid fatty acid ester, propylene glycol fatty acid ester, lecithin or enzymatic degradation product thereof. The stabilizer is preferably contained in an amount of 0 to 5%, particularly 0.01 to 2%. Examples of the stabilizer include thickening polysaccharides such as xanthan gum, gellan gum, guar gum, carrageenan, pectin, tragacanth gum, and konjac mannan, starch, and the like. In addition, salt, sugar, vinegar, fruit juice, seasonings such as seasonings, flavors such as spices and flavors, colorants, preservatives, antioxidants, and the like can be used. Using these raw materials, oil-in-water type oil-and-fat-containing foods such as mayonnaise, dressing, coffee whitener, ice cream, whipped cream and beverages can be prepared by conventional methods.

  The oil and fat composition of the present invention can be used for a water-in-oil emulsion. The mass ratio of the water phase to the oil phase is water phase / oil phase = 85/15 to 1/99, preferably 80/20 to 10/90, and particularly preferably 70/30 to 35/65. It is preferable to contain an emulsifier in an amount of 0.01 to 5%, particularly 0.05 to 3%. Examples of emulsifiers include egg protein, soybean protein, milk protein, proteins separated from these proteins, various proteins such as (partial) degradation products of these proteins, sucrose fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester Glycerin fatty acid monoester, polyglycerin fatty acid ester, polyglycerin condensed ricinoleic acid ester, glycerin organic acid fatty acid ester, propylene glycol fatty acid ester, lecithin or enzymatic degradation product thereof. Also, salt, sugar, vinegar, fruit juice, seasonings such as seasonings, flavors such as spices and flavors, stabilizers such as thickening polysaccharides and starches, colorants, preservatives, antioxidants, etc. are used. be able to. Using these raw materials, a water-in-oil type oil-containing food such as margarine, spread, butter cream and the like can be prepared by a conventional method.

  The oil and fat composition of the present invention has a body fat accumulation inhibitory action, a visceral fat accumulation inhibitory action, a body weight gain inhibitory action, a serum triglyceride increase inhibitory action, an insulin resistance improving action, a blood sugar level rise inhibiting action, a HOMA index improving action, a feeding Excellent physiological activity such as inhibitory action. Because of having such excellent properties, the oil and fat composition of the present invention can be used for pharmaceuticals in the form of capsules, tablets, granules, powders, liquids, gels and the like. As pharmaceuticals, in addition to the oil and fat composition described above, excipients, disintegrants, binders, lubricants, surfactants, alcohols, water, water-soluble polymers, sweeteners, and flavoring agents that are generally used depending on the form. In addition, it can be produced by adding a sour agent or the like. The amount of the oil / fat composition of the present invention to be added to a pharmaceutical varies depending on the use and form of the pharmaceutical, but is generally 0.1 to 80%, more preferably 0.2 to 50%, particularly 0.5 to 30%. Is preferred. Moreover, it is preferable to administer 0.2-50g per day as an oil-fat composition divided into 1 to several times. The administration period is preferably 1 month or more, 2 months or more, and 3 to 12 months.

  The oil and fat composition of the present invention can be used for feed. As feed, for example, livestock feed used for cattle, pigs, chickens, sheep, horses, goats, etc., feed for small animals used for rabbits, rats, mice, etc. Examples include pet food used for dogs, cats, small birds, squirrels, and the like. The blending amount of the oil and fat composition of the present invention in the feed varies depending on the use of the feed and the like, but is generally 1 to 30%, particularly preferably 1 to 20%. 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 described above, the feed is produced by mixing with commonly used feed ingredients such as meat, protein, grains, bran, potatoes, sugars, vegetables, vitamins, and minerals.
Meats include cattle, pigs, sheep (mutton or lamb), rabbits, kangaroos and other meats, animal meat and by-products, processed products (rendered products of meatballs, meatbone meal, chicken meal, etc.), tuna And seafood such as bonito, horse mackerel, sardines, scallops, scallops, and fish meal (fish meal). Examples of the protein include milk proteins such as casein and whey, animal proteins such as egg protein, and plant proteins such as soybean protein. Examples of cereals include wheat, barley, rye, milo, and corn. Rice bran includes rice bran and bran. Examples of potatoes include soybean meal. The total amount of meat, protein, grains, bran and potatoes in the feed is preferably 5 to 93.9%.

  Examples of the saccharide include glucose, oligosaccharide, sugar, molasses, starch, liquid sugar and the like, and preferably 5 to 80% in the feed. As vegetables, vegetable extracts etc. are illustrated and it is preferable to contain 1-30% in feed. Examples of vitamins include A, B1, B2, D, E, niacin, pantothenic acid, carotene, and the like, and 0.05 to 10% in feed is preferable. Examples of minerals include calcium, phosphorus, sodium, potassium, iron, magnesium, zinc and the like, and it is preferable to contain 0.05 to 10% in the feed. In addition, a gelling agent, a shape-retaining agent, a pH adjuster, a seasoning, a preservative, a nutritional reinforcing agent and the like that are generally used in feed can be contained as necessary.

Example 1 Preparation of Oil and Fat (1) Preparation of Conjugated Linoleic Acid (CLA) After mixing 1050 g of propylene glycol and 350 g of potassium hydroxide, the temperature was raised to 60 ° C. with stirring to completely dissolve potassium hydroxide. Thereafter, nitrogen bubbling was performed at 60 ° C. for 30 minutes to remove dissolved oxygen. Subsequently, this was heated up to 130 degreeC and 700 g of linoleic acid (made by Tokyo Chemical Industry) was added little by little. Under a nitrogen atmosphere, the temperature was raised to 157 ° C. and stirred for 4 hours to carry out a conjugation reaction. After cooling to room temperature, 1 L of 5N hydrochloric acid was added to adjust the pH to 3. Hexane was added to the reaction product to perform solvent extraction, and the solvent was distilled off with an evaporator to obtain 700 g of CLA.

(2) Production of fat / oil A 1100 parts by mass of CLA prepared in (1) and 110 parts by mass of immobilized lipase were mixed and heated to 40 ° C. in a nitrogen atmosphere. Next, 180.5 parts by mass of glycerin was added, and an esterification reaction was performed at 40 ° C. for 7 hours under reduced pressure (2 to 5 torr). After removing the immobilized enzyme by filtration, the reaction product (TG5.7%, DG73.2%, MG12.8%, FA8.3%) was subjected to silica gel column chromatography (Wako C-200, Wako Pure Chemical Industries). The product was purified by elution with an organic solvent. That is, hexane, hexane-ethyl acetate (97: 3, V / V), hexane-ethyl acetate (9: 1, V / V), hexane-ethyl acetate (4: 1, V / V), Elution with hexane-ethyl acetate (3: 1, V / V) and hexane-ethyl acetate (2.5: 1, V / V) in this order gave a DG fraction. Oils and fats A were obtained by adding 0.02 parts by mass of tocopherol (mixed tocopherol MDE-6000, manufactured by Yatsushiro) to 100 parts by mass of the oils and fats obtained by distilling off the solvent with an evaporator. The glyceride composition and fatty acid composition are shown in Table 1.

(3) Manufacture of fats and oils B CLA520 mass part prepared by (1) and 52 mass parts of fixed lipase were mixed, and it heated at 40 degreeC by nitrogen atmosphere. Subsequently, 56.9 parts by mass of glycerin was added, and an esterification reaction was performed at 50 ° C. for 20 hours under reduced pressure (2 to 5 torr). After removing the immobilized enzyme by filtration, the reaction product (TG 41.8%, DG 36.8%, MG 1.2%, FA 20.2%) was subjected to silica gel column chromatography (Wako C-200, Wako Pure Chemical Industries). And eluted with an organic solvent (hexane-ethyl acetate (97: 3, V / V)) to remove the DG and MG fractions. This was further subjected to Florisil column chromatography for purification. That is, the TG fraction was eluted with hexane and hexane-ethyl acetate (30: 1, V / V), and then the solvent was distilled off with an evaporator. Oil and fat B was obtained by adding 0.02 part by mass of tocopherol (mixed tocopherol MDE-6000, manufactured by Yatsushiro) to 100 parts by mass of the obtained oil and fat. The glyceride composition and fatty acid composition are shown in Table 1.

(4) Preparation of fat / oil C 400 parts by weight of fish oil (manufactured by Kao) and 16 parts by weight of glycerin are mixed, and in the presence of 1.2 parts by weight of sodium methylate under reduced pressure (0.133 kPa) at 100 ° C. for 4 hours. An exchange reaction was performed. The obtained reaction product was purified by silica gel chromatography in the same manner as in (2), and the solvent was distilled off with an evaporator. Next, 0.02 parts by mass of tocopherol (mixed tocopherol MDE-6000, manufactured by Yatsushiro) was added to 100 parts by mass of the obtained fats and oils to obtain fats and oils C. The glyceride composition and fatty acid composition are shown in Table 1.

(5) Preparation of Oil D: 400 parts by mass of medium chain fatty acid triglyceride (Coconard MT, manufactured by Kao) and 16 parts by mass of glycerin were mixed, and 1.2 parts by mass of sodium methylate was present under reduced pressure (0.133 kPa ) Transesterification was performed at 100 ° C for 4 hours. The obtained reaction product was purified by silica gel chromatography in the same manner as in (2), and the solvent was distilled off with an evaporator. Next, 0.02 parts by mass of tocopherol (mixed tocopherol MDE-6000, manufactured by Yatsushiro) was added to 100 parts by mass of the obtained fats and oils to obtain fats and oils D. The glyceride composition and fatty acid composition are shown in Table 1.

(6) Preparation of fat and oil E 75 parts by mass of potassium hydroxide was completely dissolved in 225 parts by mass of propylene glycol, and after nitrogen bubbling for 20 minutes, the temperature was raised to 120 ° C. in a nitrogen atmosphere. Next, 180 parts by mass of safflower oil was added dropwise, and the reaction was performed at 170 ° C. for 2.5 hours. 300 parts by mass of the obtained reaction product and 12 parts by mass of glycerin were subjected to a transesterification reaction in the presence of 0.8 parts by mass of sodium methylate under reduced pressure (0.133 kPa) at 100 ° C. for 4 hours. This was fractionated by silica gel chromatography in the same manner as (2), and the solvent was distilled off by an evaporator. Subsequently, fat E was obtained by adding 0.02 part by mass of tocopherol (mixed tocopherol MDE-6000, manufactured by Yatsushiro) to 100 parts by mass of the fat obtained by mixing each fraction. The glyceride composition and fatty acid composition are shown in Table 1.

(7) Preparation of fat and oil F Tocopherol (mixed tocopherol MDE-6000, manufactured by Yatsushiro) is 0.02 parts by weight, plant sterol fatty acid ester, based on 100 parts by weight of fat and oil mixed with fat E and rapeseed oil in a mass ratio of 1: 2. 4 parts by mass of (CardioAid-S, manufactured by ADM) was added to obtain oil and fat F. Table 1 shows the glyceride composition and fatty acid composition of the fat F.

[Analysis method]
(I) Glyceride distribution 10 mg of a sample and 0.5 mL of a trimethylsilylating agent (“silylating agent TH”, manufactured by Kanto Chemical) were added to a glass sample bottle, sealed, and then heated at 70 ° C. for 15 minutes. After 1 mL of water was added, 2 mL of hexane was added and shaken well. After standing, the hexane phase was extracted and subjected to analysis by gas chromatography (GLC).
GLC condition: Hewlett Packard 6890 type column; DB-1HT (J & W Scientific) 7m
Column temperature; initial = 80 ° C, final = 340 ° C
Temperature increase rate = 10 ° C / min, hold for 20 minutes at 340 ° C Detector; FID, temperature = 350 ° C
Injection part; split ratio = 50: 1, temperature = 320 ° C.
Sample injection volume: 1 μL
Carrier gas; helium, flow rate = 1.0 mL / min

(Ii) Constituent fatty acid composition 0.6 mL of a 1 / 2N sodium hydroxide / methanol solution was added to about 12 mg of a sample. Subsequently, after adding 0.6 mL of boron trifluoride methanol complex methanol solution (made by Wako Pure Chemical Industries), it heated at 70 degreeC for 30 minute (s). After adding 1 mL of saturated saline, 1 mL of hexane was added and shaken well. The hexane phase was extracted, and anhydrous sodium sulfate was added to prepare a fatty acid methyl ester.
The methyl esterified fatty acid was subjected to analysis by GLC.
GLC conditions Equipment: Hewlett Packard 6890 type column; CP-Sil88 for Fame (manufactured by GL Sciences)
0.25mm × 50m
Column temperature; initial = 150 ° C, final = 225 ° C
Hold at 150 ° C for 5 minutes, then heat up at 2 ° C / minute and hold at 225 ° C for 15 minutes Detector; FID, temperature = 250 ° C
Injection part; split ratio = 40: 1, temperature = 250 ° C.
Sample injection volume: 1 μL
Carrier gas; helium, flow rate = 1.0 mL / min

Example 2 Storage Test A storage test was performed using the fats and oils A and B by the following method. A glass sample bottle (50 mL) was charged with 20 g of oil and fat, sealed with nitrogen, and sealed. This was stored in a -20 ° C freezer. Five years later, the mixture was allowed to stand at room temperature, thawed and opened, and the odor and appearance were subjected to sensory evaluation based on the following criteria. The results are shown in Table 2.

Odor a: Deterioration odor and chemical odor are hardly felt and good.
b: Deteriorated odor is somewhat felt, but there is no chemical odor and is somewhat good.
c: There is a deterioration odor and a chemical odor, and it is somewhat poor.
d: Deterioration odor and chemical odor are strong and poor.

Appearance a: Same liquid as normal oil (salad oil) and good.
b: Slightly higher in viscosity than normal oil and slightly better.
c: There is a gel-like part, which is somewhat poor.
d: The gel-like part occupies most and is bad.

  The product of the present invention was shown to have better odor and appearance and better storage than the comparative product.

Example 3 Animal Experiment With the composition shown in Table 3, a feed was produced according to a conventional method. 6-7 week old Zucker rats were divided into 4 groups of 6 rats per group. First, the feed 1 was preliminarily raised for 4 days (constant food intake). Subsequently, each feed was bred for 9 days. The amount of food intake at this time was measured every day. On the last day of the administration of the feed, dissection was performed, and the liver, perirenal adipose tissue, and adipose testis adipose tissue were removed and their weights were measured. In addition, the amount of triglyceride in the liver was measured. The results are shown in Table 4.

  When a feed containing the product of the present invention (Feed 2) is administered, the amount of triglycerides in the liver, the amount of fatty tissue around the kidney, and the amount of fatty tissue around the epididymis may be lower than those of the comparative products (Feed 1, 3, 4). It became clear. In addition, the total amount of food intake was significantly reduced, indicating that it has an antifeedant effect.

Claims (5)

The following components (A) and (B):
(A) Containing 15 mass% or more of diacylglycerol having an unsaturated fatty acid content of 80 mass% or more, a conjugated linoleic acid content of 2 to 85 mass%, and an ω3 unsaturated fatty acid content of less than 15 mass% An oil composition containing 100 parts by mass of (B) tocopherol 0.001 to 2 parts by mass of a fat and oil having a monoacylglycerol content of 5% by mass or less and a free fatty acid content of 5% by mass or less.   Furthermore, the fats and oils composition of Claim 1 which contains 0.05-30 mass parts of (C) plant sterols.   The foodstuff containing the oil-fat composition of Claim 1 or 2.   A feed containing the oil or fat composition according to claim 1.   A pharmaceutical comprising the oil or fat composition according to claim 1 or 2.