Oil and fat composition

Abstract

To provide a high-diacylglycerol-content fat that contains α-linolenic acid in abundance and keeps a good flavor even after exposure.SOLUTION: A fat composition satisfies the following (A)-(E): (A) the content of diacylglycerol in the fat is 15 mass% or more; (B) the content of α-linolenic acid in the fatty acids constituting the fat is 20 mass% or more; (C) the content of a vitamin C fatty acid ester is 0.025-0.30 mass%; (D) the mass ratio [(DAG) / (VC)] of the content of the diacylglycerol in the fat to the content of the vitamin C fatty acid ester in the fat composition is 150 or more; and (E) the mass ratio [(ALA) / (VC)] of the content of the α-linolenic acid in the fatty acids constituting the fat to the content of the vitamin C fatty acid ester in the fat composition is 100-1,200.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to an oil and fat composition.

Background Art

[0002] α-Linolenic acid (C18:3, ALA) abundantly contained in flaxseed (linseed) etc. is known to be converted into highly physiologically active eicosapentaenoic acid (C20:5) and docosahexaenoic acid (C22:6) when it enters the body. In recent years, the use of oils and fats rich in this has been desired. On the other hand, it has been reported that oils and fats containing a high concentration of diacylglycerol have physiological effects such as suppressing an increase in postprandial blood triglycerides (neutral fat) and having little accumulation in the body. Therefore, heretofore, in order to effectively express the physiological activity functions of α-linolenic acid and diacylglycerol, 15 to 17% by weight of diglyceride in which less than 15% by weight of the constituent fatty acids are ω3 unsaturated fatty acids, and 30 to 85% by weight of triglyceride in which 15% by weight or more of the constituent fatty acids are ω3 unsaturated fatty acids (Patent Document 1), an oil and fat composition containing 5 to 59.9% by weight of diglyceride in which 15 to 90% by weight of the constituent fatty acids are ω3 unsaturated fatty acids having less than 20 carbon atoms, triglyceride and monoglyceride (Patent Document 2), etc. have been proposed.

[0003] However, oils and fats rich in α-linolenic acid have very low oxidation stability and easily generate an unpleasant odor. Therefore, usually, an antioxidant is contained in the oil and fat to prevent deterioration of the flavor of the oil and fat. As antioxidants for oils and fats, tocopherol, rosemary extract, ascorbic acid fatty acid ester, lecithin, etc. are used. For example, Patent Document 1 discloses mixing 0.025 parts of vitamin C palmitate with respect to 100 parts of a mixture containing diglyceride oil and flaxseed oil, and Patent Document 2 discloses mixing 0.02 parts of vitamin C palmitate with respect to 100 parts of diglyceride oil.

Prior Art Documents

Patent Documents

[0004] [Patent Document 1] Japanese Patent Publication No. 2003-160794 [Patent Document 2] Japanese Patent Publication No. 2002-138297 [Overview of the Initiative] [Problems that the invention aims to solve]

[0005] However, even with conventional methods, stability against light is particularly low, and flavor preservation is insufficient. Therefore, the present invention relates to providing a diacylglycerol-rich oil that is rich in alpha-linolenic acid and retains its flavor even after exposure. [Means for solving the problem]

[0006] In order to solve the above problems, the inventors focused on hexanal and propionic acid, which are odor components produced by the photo-oxidation of alpha-linolenic acid, and conducted diligent research. They found that by including vitamin C fatty acid esters in oils and fats within a specific range, hexanal is preferentially produced among the two odor components, the pungent odor and spoilage odor caused by propionic acid are suppressed, and a flavor suitable for edible oil is maintained. Furthermore, while vitamin C fatty acid esters have low solubility in oils and fats and tend to precipitate at low temperatures, we found that including diacylglycerol in oils and fats at a specific ratio or higher relative to vitamin C fatty acid esters suppresses the precipitation of vitamin C fatty acid esters at low temperatures.

[0007] In other words, the present invention relates to the following (A) to (E): (A) The diacylglycerol content in the oil is 15% by mass or more. (B) The alpha-linolenic acid content in the fatty acids constituting the oil is 20% by mass or more. (C) Vitamin C fatty acid ester content is 0.025-0.30% by mass. (D) The mass ratio of the content of diacylglycerol in the oil and fat composition to the content of vitamin C fatty acid ester in the oil and fat composition [(DAG) / (VC)] is 150 or more, (E) The mass ratio of the content of α-linolenic acid in the fatty acids constituting the oil and fat to the content of vitamin C fatty acid ester in the oil and fat composition [(ALA) / (VC)] is 100 to 1200. This invention provides an oil and fat composition that satisfies the following conditions. [Effects of the Invention]

[0008] According to the present invention, it is possible to provide a fat and oil composition that has a high content of α-linolenic acid and diacylglycerol, exhibits excellent physiological effects, and retains its flavor with little irritating or spoiled odor even after exposure. Moreover, the fat and oil composition of the present invention suppresses the precipitation of vitamin C fatty acid esters even at low temperatures. [Modes for carrying out the invention]

[0009] The oil and fat composition of the present invention satisfies the following (A) to (E). (A) The diacylglycerol content in the oil is 15% by mass or more. (B) The alpha-linolenic acid content in the fatty acids constituting the oil is 20% by mass or more. (C) Vitamin C fatty acid ester content is 0.025-0.30% by mass. (D) The mass ratio of the content of diacylglycerol in the oil and fat composition to the content of vitamin C fatty acid ester in the oil and fat composition [(DAG) / (VC)] is 150 or more, (E) The mass ratio of the content of α-linolenic acid in the fatty acids constituting the oil and fat to the content of vitamin C fatty acid ester in the oil and fat composition [(ALA) / (VC)] is 100 to 1200.

[0010] In the present invention, the oil content in the oil composition is preferably 90% by mass (hereinafter simply referred to as "%") or more, more preferably 95% or more, and also preferably 99.975% or less, and more preferably 99.950% or less, from the viewpoint of usability. The oil and fat content in the oil and fat composition is preferably 90 to 99.975%, and more preferably 95 to 99.950%. In the present invention, the oil or fat contains one or more of monoacylglycerols, diacylglycerols, and triacylglycerols. There are no particular restrictions on the type of oil or fat; any oil or fat that can be used as an edible oil or fat is acceptable.

[0011] In the present invention, the diacylglycerol content in the oil and fat is 15% or more. The diacylglycerol content in the oil and fat is 15% or more, preferably 20% or more, more preferably 25% or more, even more preferably 30% or more, even more preferably 50% or more, even more preferably 60% or more, even more preferably 70% or more, and even more preferably 80% or more, and from the viewpoint of industrial productivity, it is preferably 99.5% or less, more preferably 98% or less, even more preferably 95% or less, and even more preferably 90% or less. The diacylglycerol content in the oil is 15% or more, preferably 20-99.5%, more preferably 25-98%, even more preferably 30-95%, even more preferably 60-90%, even more preferably 70-90%, and even more preferably 80-90%.

[0012] The fatty acids constituting diacylglycerol are not particularly limited and may be either saturated or unsaturated fatty acids as described later. However, in the present invention, it is preferable that the α-linolenic acid content in the fatty acids constituting diacylglycerol is 20% or more, from the viewpoint of effectively exhibiting the effects and physiological effects. The α-linolenic acid content in the fatty acids constituting diacylglycerol is preferably 30% or more, more preferably 40% or more, and even more preferably 50% or more. Furthermore, from the viewpoint of oxidative stability, it is preferably 80% or less, more preferably 70% or less, and even more preferably 60% or less. Note that the amount of fatty acids in this specification is expressed on a free fatty acid basis.

[0013] The oil or fat of the present invention preferably contains triacylglycerol, and its content is preferably 1% or more, more preferably 2% or more, still more preferably 5% or more, still more preferably 10% or more from the viewpoint of the industrial productivity of the oil or fat. Also, it is preferably 85% or less, more preferably 80% or less, still more preferably 75% or less, still more preferably 50% or less, still more preferably 25% or less. The content of triacylglycerol in the oil or fat is preferably 1 to 85%, more preferably 2 to 80%, still more preferably 2 to 75%, still more preferably 5 to 50%, still more preferably 10 to 25%.

[0014] The content of monoacylglycerol in the oil or fat is preferably 5% or less, more preferably 3% or less, still more preferably 2% or less, still more preferably 1.5% or less, and also preferably more than 0% from the viewpoints of flavor, industrial productivity of the oil or fat, and oxidation stability. The content of monoacylglycerol in the oil or fat may be 0%. The content of free fatty acid or its salt in the oil or fat is preferably 3% or less, more preferably 2% or less, still more preferably 1% or less, and also preferably more than 0% from the viewpoints of flavor and oxidation stability. The content of free fatty acid or its salt in the oil or fat composition may be 0%. The fatty acid compositions of triacylglycerol, diacylglycerol and monoacylglycerol may be the same or different.

[0015] In the present invention, the content of α-linolenic acid in the fatty acids constituting the oil or fat is 20% or more. The content of α-linolenic acid in the fatty acids constituting the oil or fat is 20% or more from the viewpoint of physiological effects, more preferably 25% or more, still more preferably 30% or more, still more preferably 40% or more, still more preferably 45% or more, still more preferably 50% or more, still more preferably 52% or more. Also, from the viewpoint of oxidation stability, it is preferably 80% or less, more preferably 70% or less, still more preferably 65% or less, still more preferably 60% or less. The content of α-linolenic acid in the fatty acids constituting the oil or fat is 20% or more, preferably 20 - 80%, more preferably 25 - 70%, still more preferably 30 - 70%, still more preferably 40 - 70%, still more preferably 45 - 70%, still more preferably 50 - 65%, and still more preferably 52 - 60%.

[0016] In the present invention, the constituent fatty acids other than α-linolenic acid constituting the oil or fat are not particularly limited and may be either saturated fatty acids or unsaturated fatty acids. From the viewpoints of the flavor and industrial productivity of the oil or fat, the content of unsaturated fatty acids in the fatty acids constituting the oil or fat is preferably 60 - 100%, more preferably 70 - 100%, and still more preferably 80 - 99.5%. From the viewpoint of physiological effects, the number of carbon atoms of the unsaturated fatty acids is preferably 14 - 24, and more preferably 16 - 22.

[0017] Among them, from the viewpoint of industrial productivity, the content of linoleic acid (C18:2) in the fatty acids constituting the oil or fat is preferably 5% or more, more preferably 10% or more, and is preferably 40% or less, more preferably 30% or less, and still more preferably 20% or less. The content of linoleic acid in the fatty acids constituting the oil or fat is preferably 5 - 40%, more preferably 5 - 30%, and still more preferably 10 - 20%.

[0018] Also, from the viewpoint of industrial productivity, the content of oleic acid (C18:1) in the fatty acids constituting the oil or fat is preferably 10% or more, and is preferably 65% or less, more preferably 50% or less, and still more preferably 30% or less. The content of oleic acid in the fatty acids constituting the oil or fat is preferably 10 - 65%, more preferably 10 - 50%, and still more preferably 10 - 30%.

[0019] From the viewpoints of appearance, physiological effects, and industrial productivity of the oil or fat, the total content of saturated fatty acids in the fatty acids constituting the oil or fat is preferably 30% or less, more preferably 20% or less, still more preferably 10% or less, and still more preferably 7% or less, and is preferably 0.5% or more. The number of carbon atoms in saturated fatty acids is preferably 14 to 24, more preferably 16 to 22.

[0020] The oil and fat composition of the present invention contains a vitamin C fatty acid ester. The vitamin C fatty acid ester used in the present invention is an ester of L-ascorbic acid and a higher fatty acid, and commercially available products, preferably commercially available products for food and beverages, can be used. As the higher fatty acid, a linear saturated fatty acid having 12 to 22 carbon atoms is preferred. One or more types of vitamin C fatty acid esters may be used. Vitamin C fatty acid esters are preferably vitamin C palmitate, vitamin C stearate, or a combination thereof, and more preferably vitamin C palmitate, as they suppress pungent odors and spoilage odors even after exposure, thus improving the flavor.

[0021] In the present invention, the content of vitamin C fatty acid ester in the oil and fat composition is 0.025 to 0.30%. From the viewpoint of effectively exhibiting the effects, the content of vitamin C fatty acid ester in the oil and fat composition is 0.025% or more, preferably 0.027% or more, more preferably 0.030% or more, even more preferably 0.040% or more, and even more preferably 0.050% or more. Furthermore, from the viewpoint of effectively exhibiting the appearance, flavor, and effects, it is 0.30% or less, preferably 0.25% or less, more preferably 0.20% or less, even more preferably 0.15% or less, and even more preferably 0.10% or less. The content of vitamin C fatty acid ester in the oil composition is 0.025 to 0.30%, preferably 0.027 to 0.25%, more preferably 0.030 to 0.20%, even more preferably 0.040 to 0.15%, and even more preferably 0.050 to 0.10%.

[0022] In the present invention, the mass ratio of diacylglycerol content in the oil and fat composition to the vitamin C fatty acid ester content [(DAG) / (VC)] is 150 or more. Vitamin C fatty acid esters have low solubility in oils and fats and tend to precipitate at low temperatures. By including diacylglycerol in the oil and fat at a specific amount ratio or higher relative to the vitamin C fatty acid ester, the solubility of the vitamin C fatty acid ester in oils and fats can be increased, thereby suppressing precipitation at low temperatures. Therefore, in the present invention, the oil and fat composition can be made suitable for edible oils by maintaining its flavor and achieving low-temperature stability. The mass ratio of the diacylglycerol content in the oil and fat composition to the vitamin C fatty acid ester content [(DAG) / (VC)] is 150 or more, preferably 180 or more, more preferably 200 or more, and even more preferably 240 or more, from the viewpoint of appearance, solubility of vitamin C fatty acid ester, and effective expression of its effects. Furthermore, from the viewpoint of flavor, it is preferably 4000 or less, more preferably 3800 or less, even more preferably 3500 or less, even more preferably 3000 or less, and even more preferably 2000 or less. The mass ratio of the diacylglycerol content in the oil and fat composition to the vitamin C fatty acid ester content [(DAG) / (VC)] is 150 or more, preferably 150 to 4000, more preferably 150 to 3800, even more preferably 180 to 3500, even more preferably 200 to 3000, and even more preferably 240 to 2000.

[0023] Furthermore, in the present invention, the mass ratio [(ALA) / (VC)] of the content of α-linolenic acid in the fatty acids constituting the oil and fat to the content of vitamin C fatty acid ester in the oil and fat composition is 100 to 1200. The mass ratio [(ALA) / (VC)] of the content of α-linolenic acid in the fatty acids constituting the oil and fat to the content of vitamin C fatty acid ester in the oil and fat composition is 100 or more, preferably 120 or more, more preferably 150 or more, even more preferably 200 or more, even more preferably 300 or more, and even more preferably 500 or more, and also 1200 or less, preferably 1150 or less, more preferably 1100 or less, even more preferably 1000 or less, even more preferably 700 or less, and even more preferably 600 or less, from the viewpoint of effectively expressing flavor and effects. The mass ratio [(ALA) / (VC)] of the α-linolenic acid content in the fatty acids constituting the oil and fat to the vitamin C fatty acid ester content in the oil and fat composition is 100 to 1200, preferably 120 to 1150, more preferably 150 to 1100, even more preferably 200 to 1000, even more preferably 200 to 700, even more preferably 300 to 700, and even more preferably 300 to 600.

[0024] Alpha-linolenic acid undergoes photo-oxidation to produce hexanal and propionic acid, which are odor-causing compounds. Hexanal has a characteristic grassy smell. Propionic acid, on the other hand, is a component that causes the pungent and spoiled odor of oils and fats. In the oil and fat composition of the present invention, by satisfying (A) to (E) above, as shown in the examples below, hexanal is preferentially produced from propionic acid and hexanal produced by photo-oxidation of α-linolenic acid. Therefore, in the sensory evaluation of the oil and fat composition, even after exposure, the grassy smell of hexanal is strongly present, and the pungent odor and spoilage odor caused by propionic acid are less noticeable, thus maintaining a flavor suitable for edible oil. In the oil and fat composition after exposure storage evaluation as described in the examples below, the ratio of the peak area of ​​hexanal to the peak area of ​​propionic acid in the headspace solid-phase microextraction / gas chromatography-mass spectrometry (HS SPME / GC / MS) described in the examples is preferably 1.0 or higher, more preferably 1.5 or higher, even more preferably 1.6 or higher, and even more preferably 2.0 or higher, from the viewpoint of reducing the pungent odor and spoilage odor.

[0025] The oil and fat composition of the present invention can be prepared from a diacylglycerol-containing oil or fat that contains α-linolenic acid as one of its constituent fatty acids. For example, it can be obtained by adding a vitamin C fatty acid ester and, if necessary, other components to a diacylglycerol-containing oil or fat that contains α-linolenic acid as one of its constituent fatty acids, and then appropriately heating, stirring, etc. Ordinary edible oils and fats may also be added as needed.

[0026] Diacylglycerol-containing oils and fats that include alpha-linolenic acid among their constituent fatty acids can be obtained by esterification reactions between fatty acids derived from oils and fats and glycerol, or by transesterification reactions (glycerolysis) between oils and fats and glycerol. Esterification reactions and glycerol-lysis reactions are broadly classified into chemical methods using chemical catalysts such as alkali metals or their alloys, oxides or hydroxides of alkali metals or alkaline earth metals, and alkoxides of alkali metals or alkaline earth metals, and enzymatic methods using enzymes such as lipases. In particular, the esterification reaction between fractional fatty acids derived from oils and fats and glycerol, as described later, is preferred because it allows for control of the fatty acid composition.

[0027] In the present invention, the oils and fats (edible oils and fats) may be either vegetable oils or animal oils. For example, vegetable oils such as soybean oil, rapeseed oil, safflower oil, rice oil, corn oil, sunflower oil, cottonseed oil, olive oil, sesame oil, peanut oil, Job's tears oil, wheat germ oil, perilla oil, linseed oil, egoma oil, chia seed oil, sacha inchi 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, palm oil, palm olein, palm stearin, coconut oil, palm kernel oil, cocoa butter, sal fat, shea butter, and algae oil; animal oils such as fish oil, lard, beef tallow, and butter fat; or transesterified oils, hydrogenated oils, fractionated oils, etc. of these can be cited. In particular, from the standpoint of usability, it is preferable to use vegetable oils, and even more preferably to use liquid oils with excellent low-temperature tolerance, and even more preferably to use perilla oil, linseed oil, and erythritol, which are rich in alpha-linolenic acid. It is preferable to use at least one oil selected from sesame oil, chia seed oil, and sacha inchi oil. Liquid oil refers to oil that is liquid at 20°C when a cooling test is performed according to the standard oil analysis test method 2.3.8-27.

[0028] Fatty acids derived from oils and fats can be obtained by hydrolyzing them. Methods for hydrolyzing oils and fats include high-temperature, high-pressure hydrolysis and enzymatic hydrolysis. High-temperature, high-pressure hydrolysis is a method in which oils and fats are mixed with water and reacted under high temperature and high pressure conditions to obtain fatty acids and glycerol. Enzymatic hydrolysis is a method in which oils and fats are mixed with water and reacted under low temperature conditions using an oil hydrolase as a catalyst to obtain fatty acids and glycerol. The hydrolysis reaction can be carried out according to conventional methods.

[0029] After hydrolysis of oils and fats, it is preferable to separate the hydrolysis reaction products and remove the solids. Separation methods include solvent fractionation, natural fractionation (dry fractionation), and wetting agent fractionation. Methods for removing precipitated solids include static separation, filtration, centrifugation, and separation by mixing fatty acids with an aqueous solution of a wetting agent.

[0030] The esterification reaction between fatty acids derived from oils and fats and glycerol is preferable to be carried out under mild conditions using an enzymatic method, as this method offers superior flavor and other advantages. The amount of enzyme used can be determined appropriately considering the enzyme activity, but in order to improve the reaction rate, when immobilized enzymes are used, it is preferably 1 to 30%, more preferably 2 to 20%, of the total mass of the esterification reaction raw materials. The reaction temperature for the esterification reaction is preferably 0 to 100°C, more preferably 20 to 80°C, and even more preferably 30 to 60°C, from the standpoint of improving the reaction rate and suppressing enzyme deactivation. The reaction time is preferably within 15 hours, more preferably 1 to 12 hours, and even more preferably 2 to 10 hours, from the standpoint of industrial productivity. Methods for bringing fatty acids and glycerol into contact include immersion, stirring, and passing the solution through a column packed with immobilized lipase using a pump or the like.

[0031] Following the esterification reaction, refining processes commonly used for oils and fats may be carried out. Specifically, these may include distillation, acid treatment, washing, decolorization, and deodorization.

[0032] The oil and fat composition of the present invention can be used in the same way as general edible oils and fats and can be applied to various foods, beverages, and animal feeds that use oils and fats. Examples of foods and beverages include not only ordinary foods and beverages, but also, for example, foods for specified health uses and foods with functional claims that claim the physiological effects of alpha-linolenic acid and diacylglycerol. Food and beverages can take the form of solid, semi-solid, or liquid, and examples include beverages, water-in-oil type oil-containing foods, oil-in-water type oil-containing foods, bakery foods, confectionery, frozen foods, retort foods, and nutritional supplement compositions such as tablets, capsules, and lozenges. Examples of animal feed include livestock feed for cattle and pigs, small animal feed for rabbits and mice, fish and shellfish feed for eels and shrimp, and pet food for dogs and cats.

[0033] The oil and fat composition of the present invention suppresses pungent odors and spoilage odors even after exposure, resulting in good flavor, and also has physiological effects as follows (A) to (E): (A) The diacylglycerol content in the oil is 20% by mass or more. (B) The alpha-linolenic acid content in the fatty acids that make up the oil is 20-80% by mass. (C) Vitamin C fatty acid ester content is 0.027-0.30% by mass. (D) The mass ratio of the content of diacylglycerol in the oil and fat composition to the content of vitamin C fatty acid ester in the oil and fat composition [(DAG) / (VC)] is 200 or more, (E) The mass ratio of the content of α-linolenic acid in the fatty acids constituting the oil and fat to the content of vitamin C fatty acid ester in the oil and fat composition [(ALA) / (VC)] is 200 to 1100. It is preferable that the oil composition satisfies the following conditions.

[0034] The oil and fat composition of the present invention suppresses pungent odors and spoilage odors even after exposure, resulting in good flavor, and also has physiological effects as follows (A) to (E): (A) The diacylglycerol content in the oil is 20-98% by mass. (B) The alpha-linolenic acid content in the fatty acids that make up the oil is 20-70% by mass. (C) Vitamin C fatty acid ester content is 0.027-0.25% by mass. (D) The mass ratio of the content of diacylglycerol in the oil and fat composition to the content of vitamin C fatty acid ester in the oil and fat composition [(DAG) / (VC)] is 200 or more, (E) The mass ratio of the content of α-linolenic acid in the fatty acids constituting the oil and fat to the content of vitamin C fatty acid ester in the oil and fat composition [(ALA) / (VC)] is 200 to 1100. It is preferable that the oil composition satisfies the following conditions.

[0035] The oil and fat composition of the present invention suppresses pungent odors and spoilage odors even after exposure, resulting in good flavor, and also has physiological effects as follows (A) to (E): (A) The diacylglycerol content in the oil is 20-95% by mass. (B) The alpha-linolenic acid content in the fatty acids constituting the oil is 25-70% by mass. (C) Vitamin C fatty acid ester content is 0.040-0.15% by mass. (D) The mass ratio of the content of diacylglycerol in the oil and fat composition to the content of vitamin C fatty acid ester in the oil and fat composition [(DAG) / (VC)] is 200 or more, (E) The mass ratio of the content of α-linolenic acid in the fatty acids constituting the oil and fat to the content of vitamin C fatty acid ester in the oil and fat composition [(ALA) / (VC)] is 200 to 1100. It is preferable that the oil composition satisfies the following conditions.

[0036] The oil and fat composition of the present invention suppresses pungent odors and spoilage odors even after exposure, resulting in good flavor, and also has physiological effects as follows (A) to (E): (A) The diacylglycerol content in the oil is 20-95% by mass. (B) The alpha-linolenic acid content in the fatty acids constituting the oil is 25-70% by mass. (C) Vitamin C fatty acid ester content is 0.050-0.10% by mass. (D) The mass ratio of the diacylglycerol content in the oil and fat composition to the vitamin C fatty acid ester content in the oil and fat composition [(DAG) / (VC)] is 240 or more, (E) The mass ratio of the content of α-linolenic acid in the fatty acids constituting the oil and fat to the content of vitamin C fatty acid ester in the oil and fat composition [(ALA) / (VC)] is 300 to 600. It is preferable that the oil composition satisfies the following conditions.

[0037] The oil and fat composition of the present invention suppresses pungent odors and spoilage odors even after exposure, resulting in good flavor, and also has physiological effects as follows (A) to (E): (A) The diacylglycerol content in the oil is 30-90% by mass, (B) The alpha-linolenic acid content in the fatty acids constituting the oil is 30-70% by mass. (C) Vitamin C fatty acid ester content is 0.050-0.10% by mass. (D) The mass ratio of the diacylglycerol content in the oil and fat composition to the vitamin C fatty acid ester content in the oil and fat composition [(DAG) / (VC)] is 240 or more, (E) The mass ratio of the content of α-linolenic acid in the fatty acids constituting the oil and fat to the content of vitamin C fatty acid ester in the oil and fat composition [(ALA) / (VC)] is 300 to 600. It is preferable that the oil composition satisfies the following conditions.

[0038] With regard to the embodiments described above, the present invention further discloses the following oil and fat compositions.

[0039] <1> The following (A) to (E): (A) The diacylglycerol content in the oil is 15% by mass or more. (B) The alpha-linolenic acid content in the fatty acids constituting the oil is 20% by mass or more. (C) Vitamin C fatty acid ester content is 0.025-0.30% by mass. (D) The mass ratio of the content of diacylglycerol in the oil and fat composition to the content of vitamin C fatty acid ester in the oil and fat composition [(DAG) / (VC)] is 150 or more, (E) The mass ratio of the content of α-linolenic acid in the fatty acids constituting the oil and fat to the content of vitamin C fatty acid ester in the oil and fat composition [(ALA) / (VC)] is 100 to 1200. A fat and oil composition that satisfies the requirements.

[0040] <2> The oil and fat content in the oil and fat composition is preferably 90% by mass or more, more preferably 95% by mass or more, and also preferably 99.975% by mass or less, more preferably 99.950% by mass or less, and also preferably 90 to 99.975% by mass, and more preferably 95 to 99.950% by mass. <1> The oil and fat composition described above. <3> The diacylglycerol content in the oil and fat is 15% by mass or more, preferably 20% by mass or more, more preferably 25% by mass or more, even more preferably 30% by mass or more, even more preferably 50% by mass or more, even more preferably 60% by mass or more, even more preferably 70% by mass or more, even more preferably 80% by mass or more, and also preferably 99.5% by mass or less, more preferably 98% by mass or less, even more preferably 95% by mass or less, even more preferably 90% by mass or less, and also preferably 20-99.5% by mass, more preferably 25-98% by mass, even more preferably 30-95% by mass, even more preferably 60-90% by mass, even more preferably 70-90% by mass, and even more preferably 80-90% by mass. <1> or <2> The oil and fat composition described above. <4> The α-linolenic acid content in the fatty acids constituting diacylglycerol is preferably 20% by mass or more, more preferably 25% by mass or more, even more preferably 30% by mass or more, even more preferably 40% by mass or more, even more preferably 50% by mass or more, and also preferably 80% by mass or less, more preferably 70% by mass or less, even more preferably 60% by mass or less, and also preferably 20-80% by mass, more preferably 25-70% by mass, even more preferably 30-70% by mass, even more preferably 40-60% by mass, and even more preferably 50-60% by mass. <1> ~ <3> The oil and fat composition according to any one of the following. <5> The triacylglycerol content in the oil is preferably 1% by mass or more, more preferably 2% by mass or more, even more preferably 5% by mass or more, even more preferably 10% by mass or more, and also preferably 85% by mass or less, more preferably 80% by mass or less, even more preferably 75% by mass or less, even more preferably 50% by mass or less, even more preferably 25% by mass or less, and also preferably 1 to 85% by mass, more preferably 2 to 80% by mass, even more preferably 2 to 75% by mass, even more preferably 5 to 50% by mass, and even more preferably 10 to 25% by mass. <1> ~ <4> The oil and fat composition according to any one of the following. <6> The monoacylglycerol content in the oil is preferably 5% by mass or less, more preferably 3% by mass or less, even more preferably 2% by mass or less, even more preferably 1.5% by mass or less, and also preferably more than 0% by mass. <1> ~ <5> The oil and fat composition according to any one of the following. <7> The content of free fatty acids or their salts in the oil is preferably 3% by mass or less, more preferably 2% by mass or less, even more preferably 1% by mass or less, and preferably more than 0% by mass. <1> ~ <6> The oil and fat composition according to any one of the following. <8> The α-linolenic acid content in the fatty acids constituting the oil and fat is 20% by mass or more, preferably 25% by mass or more, more preferably 30% by mass or more, even more preferably 40% by mass or more, even more preferably 45% by mass or more, even more preferably 50% by mass or more, even more preferably 52% by mass or more, and also preferably 80% by mass or less, more preferably 70% by mass or less, even more preferably 65% ​​by mass or less, even more preferably 60% by mass or less, and also preferably 20-80% by mass, more preferably 25-70% by mass, even more preferably 30-70% by mass, even more preferably 40-70% by mass, even more preferably 45-70% by mass, even more preferably 50-65% by mass, and even more preferably 52-60% by mass. <1> ~ <7> The oil and fat composition according to any one of the following. <9> The linoleic acid content in the fatty acids constituting the oil is preferably 5% by mass or more, more preferably 10% by mass or more, and also preferably 40% by mass or less, more preferably 30% by mass or less, even more preferably 20% by mass or less, and also preferably 5 to 40% by mass, more preferably 5 to 30% by mass, and even more preferably 10 to 20% by mass. <1> ~ <8> The oil and fat composition according to any one of the following. <10> The oleic acid content in the fatty acids constituting the oil is preferably 10% by mass or more, more preferably 65% ​​by mass or less, more preferably 50% by mass or less, even more preferably 30% by mass or less, and also preferably 10 to 65% by mass, more preferably 10 to 50% by mass, and even more preferably 10 to 30% by mass. <1> ~ <9> The oil and fat composition according to any one of the following. <11> The vitamin C fatty acid ester is preferably vitamin C palmitate, vitamin C stearate, or a combination thereof, and more preferably vitamin C palmitate. <1> ~ <10> The oil and fat composition according to any one of the following. <12> The content of vitamin C fatty acid ester in the oil composition is 0.025% by mass or more, preferably 0.027% by mass or more, more preferably 0.030% by mass or more, even more preferably 0.040% by mass or more, even more preferably 0.050% by mass or more, and also 0.30% by mass or less, preferably 0.25% by mass or less, more preferably 0.20% by mass or less, even more preferably 0.15% by mass or less, even more preferably 0.10% by mass or less, and also preferably 0.027 to 0.25% by mass, more preferably 0.030 to 0.20% by mass, even more preferably 0.040 to 0.15% by mass, and even more preferably 0.050 to 0.10% by mass. <1> ~ <11> The oil and fat composition according to any one of the following. <13> The mass ratio of the content of diacylglycerol in the oil and fat composition to the content of vitamin C fatty acid ester [(DAG) / (VC)] is 150 or more, preferably 180 or more, more preferably 200 or more, even more preferably 240 or more, also preferably 4000 or less, more preferably 3800 or less, even more preferably 3500 or less, even more preferably 3000 or less, even more preferably 2000 or less, also preferably 150 to 4000, more preferably 150 to 3800, even more preferably 180 to 3500, even more preferably 200 to 3000, and even more preferably 240 to 2000. <1> ~ <12> The oil and fat composition according to any one of the following. <14> The mass ratio of the α-linolenic acid content in the fatty acids constituting the oil to the vitamin C fatty acid ester content in the oil composition [(ALA) / (VC)] is 100 or more. Preferably, it is 120 or more, more preferably 150 or more, even more preferably 200 or more, even more preferably 300 or more, even more preferably 500 or more, and also 1200 or less, preferably 1150 or less, more preferably 1100 or less, even more preferably 1000 or less, even more preferably 700 or less, even more preferably 600 or less, and also preferably 120 to 1150, more preferably 150 to 1100, even more preferably 200 to 1000, even more preferably 200 to 700, even more preferably 300 to 700, and even more preferably 300 to 600. <1> ~ <13> The oil and fat composition according to any one of the following. <15> The ratio of the peak area of ​​hexanal to the peak area of ​​propionic acid, as analyzed by headspace solid-phase microextraction / gas chromatography-mass spectrometry of the oil composition after exposure to light at an illuminance of approximately 2000 lx for 7 days, is preferably 1.0 or higher, more preferably 1.5 or higher, even more preferably 1.6 or higher, and still more preferably 2.0 or higher. <1> ~ <14> The oil and fat composition according to any one of the following. <16> Preferably contains an esterification reaction oil of fractional fatty acids derived from oils and fats and glycerol. <1> ~ <15> The oil and fat composition according to any one of the following. <17> The fractional fatty acids are preferably derived from at least one oil selected from perilla oil, linseed oil, egoma oil, chia seed oil, and sacha inchi oil. <16> The oil and fat composition described above. <18> <1> ~ <17> Food and beverages containing the oil and fat composition described in any one of the following. <19> <1> ~ <17> A feed containing the oil and fat composition described in any one of the following. [Examples]

[0041] [Analysis method] (i) Glyceride composition of fats and oils Approximately 10 mg of oil sample and 0.5 mL of trimethylsilylation agent ("Silylation Agent TH," manufactured by Kanto Chemical Co., Ltd.) were added to a glass sample bottle, sealed tightly, and heated at 70°C for 15 minutes. 1.0 mL of water and 1.5 mL of hexane were added, and the mixture was shaken. After standing, the upper layer was analyzed by gas chromatography (GLC). <GLC Analysis Conditions> (Conditions) Equipment: Agilent 7890B (manufactured by Agilent Technologies) Column: DB-1ht 10m × 0.25mm × 0.2μm (manufactured by Agilent J&W) Carrier gas: 1.0 mL He / min Injector: Split (1:50), T = 340 °C Detector: FID, T = 350 °C Oven temperature: Heat from 80 °C to 340 °C at 10 °C / min and hold for 15 minutes

[0042] (ii) Constituent Fatty Acid Composition of Oils and Fats Fatty acid methyl esters were prepared according to the "Method for Preparation of Fatty Acid Methyl Esters (2.4.1.-1996)" in "Standard Oil Analysis Test Methods" edited by the Japanese Oil Chemists' Society, and the obtained oil and fat samples were measured in accordance with American Oil Chemists. Society Official Method Ce 1f-96 (GLC method). <GLC Analysis Conditions> Equipment: Agilent 7890B (manufactured by Agilent Technologies) Column: CP-SIL88 50m × 0.25mm × 0.2μm (manufactured by Agilent J&W) Carrier gas: 1.0 mL He / min Injector: Split (1:50), T = 300 °C Detector: FID, T = 300 °C Oven temperature: Hold at 150 °C for 5 min → Heat at 1 °C / min → Hold at 160 °C for 5 min → Heat at 2 °C / min → Hold at 200 °C for 10 min → Heat at 10 °C / min → Hold at 220 °C for 5 min

[0043] (iii) Analysis of Hexanal and Propionic Acid The analysis of hexanal and propionic acid was performed by headspace solid-phase microextraction / gas chromatography-mass spectrometry (HS SPME / GC / MS). A 50 / 30μm, DVB / CAR / PDMS fiber (manufactured by SUPELCO) was used as the SPME fiber, and an MPS-2 (manufactured by Gerstel) was used as the autosampler. 1 g of an oil sample was collected in a headspace vial (10 mL capacity; manufactured by GL Sciences), heated at 40°C for 20 minutes, and then the headspace phase was sampled for 30 minutes using an SPME fiber. The measurement was performed by GC / MS. <GC / MS analysis conditions> Equipment: Agilent 7890A / 5975 (manufactured by Agilent Technologies) Column: VF-WAX 60 m × 0.25 mm × 1.0 μm (manufactured by Agilent J&W) Carrier gas: 1.0 mL He / min Injector: Splitless, T = 240°C Oven temperature: Hold at 35°C for 4 min → Increase temperature at 3°C / min → 185°C → Increase temperature at 10°C / min → Hold at 240°C for 10 min Ionization method: EI (70 eV) Ion source temperature: 230°C Measurement mode: Pre-ion scan range: m / z 30 - 500

[0044] Examples 1 - 8 and Comparative Examples 1 - 7 (1) Preparation of oils a - d Oils a - d shown in Table 1 were prepared.

[0045]

Table 1

[0046] Oil and fat a: Soybean oil and rapeseed oil were mixed and hydrolyzed with an enzyme to obtain fatty acids. The mixture was then cooled in stages, and the precipitated fatty acids were separated by centrifugation. Next, the separated fatty acids and glycerol were esterified under reduced pressure using an immobilized 1,3-position selective lipase as a catalyst. After filtering off the immobilized enzyme, the reaction product was subjected to molecular distillation, washed with water, deodorized, and 0.2% by mass of a tocopherol preparation (manufactured by Riken Vitamin Co., Ltd.) was added to obtain oil and fat a. Oil b: Oil b was obtained in the same manner as oil a, except that linseed oil was used instead of soybean oil and rapeseed oil. Oil c: Linseed oil (Nisshin Linseed Oil; manufactured by Nisshin Oillio Co., Ltd.) was used. Oil / Fat d: Rapeseed oil (Seven Premium Lightly Finishing Canola Oil; manufactured by J-Oil Mills) was used.

[0047] (2) Preparation of fats A to K Oils a to d were mixed in the proportions shown in Table 2 to prepare oils A to K. The mixing ratios, glyceride composition, and fatty acid composition of oils A to K are shown in Table 2.

[0048] [Table 2]

[0049] (3) Preparation of oil and fat composition A to K of oils were mixed with vitamin C palmitate (L-ascorbic acid palmitate, manufactured by DSM) or vitamin C stearate (VCS): 6-O-Stearoyl-L-ascorbic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) in the proportions shown in Table 3 to obtain an oil composition. In Table 3, the diacylglycerol content is the content in the oil, the α-linolenic acid content is the content in the fatty acids constituting the oil, and the vitamin C fatty acid ester content is the content in the oil composition.

[0050] (4) Evaluation of vitamin C fatty acid ester precipitation at low temperatures The oil and fat compositions of the examples and comparative examples were stored at 5°C for 3 days, and the precipitation of vitamin C fatty acid esters was observed. Precipitation was indicated as "present," and non-precipitation was indicated as "absent."

[0051] (5) Exposure storage evaluation For the oil and fat compositions in which no precipitation of vitamin C fatty acid esters was observed at low temperatures as described in (4) above, the compositions were exposed to light at 25°C and an illuminance of approximately 2000 lx for 7 days using an illuminated incubator (FLI-2010A, manufactured by Tokyo Rikakikai Co., Ltd.), and then the odor was evaluated by component analysis and sensory perception. Sensory evaluation was conducted by a panel of three experts according to the evaluation criteria shown below. The scores were determined by the deliberation of the three expert panel members. (Evaluation Criteria) 4: A strong pungent or spoiled odor is detected. 3: A strong, unpleasant odor is detected; there is a problem. 2: There is a slight pungent odor and a smell of spoilage, but it is not a problem. 1: There is almost no pungent or spoiled smell.

[0052] (6) Results The results are shown in Table 3.

[0053] [Table 3]

[0054] As shown in Table 3, no precipitation of vitamin C fatty acid esters was observed in the oil compositions of Examples 1-8 and Comparative Examples 1-3 at a low temperature of 5°C. However, the amount of hexanal and propionic acid produced after exposure differed between the oil compositions of Examples 1-8 and Comparative Examples 1-3. In the oil compositions of Examples 1-8, hexanal was preferentially produced, and sensory evaluation confirmed that while a grassy odor was perceived, pungent odors and spoilage odors were suppressed. In contrast, in the oil compositions of Comparative Examples 1-3, propionic acid was produced in larger quantities than hexanal, and sensory evaluation revealed pungent odors and spoilage odors resulting from this. In the oil and fat compositions of Comparative Examples 4 to 7, vitamin C fatty acid esters precipitated at a low temperature of 5°C.

Claims

1. The following (A) to (E): (A) The diacylglycerol content in the oil is 30% by mass or more. (B) The α-linolenic acid content in the fatty acids constituting the oil is 20% by mass or more, and the α-linolenic acid content in the fatty acids constituting the diacylglycerol is 20% by mass or more, (C) Vitamin C fatty acid ester content is 0.025 to 0.30% by mass. (D) The mass ratio of the content of diacylglycerol in the oil and fat composition to the content of vitamin C fatty acid ester in the oil and fat composition [(DAG) / (VC)] is 150 or more, (E) The mass ratio of the content of α-linolenic acid in the fatty acids constituting the oil and fat to the content of vitamin C fatty acid ester in the oil and fat composition [(ALA) / (VC)] is 200 to 1000. A fat and oil composition that satisfies the requirements.

2. The oil and fat composition according to claim 1, comprising 90 to 99.975% by mass of oil and fat.

3. The oil and fat composition according to claim 1 or 2, wherein the content of α-linolenic acid in the fatty acids constituting diacylglycerol is 25% by mass or more.

4. The oil and fat composition according to any one of claims 1 to 3, wherein the linoleic acid content in the fatty acids constituting the oil and fat is 5 to 40% by mass.

5. The oil and fat composition according to any one of claims 1 to 4, wherein the oleic acid content in the fatty acids constituting the oil and fat is 10 to 65% by mass.

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