Oil and fat composition

Abstract

The present invention provides an oil or fat having a high content of diacylglycerol, which is rich in α-linolenic acid and still has a good flavor after being exposed to light. The oil or fat composition of the present invention satisfies the following (A) to (E): (A) the content of diacylglycerol in the oil or fat is 15% by mass or more; (B) the content of α-linolenic acid in the fatty acids constituting the oil or fat is 20% by mass or more; (C) the content of vitamin C fatty acid ester is 0.025 to 0.30% by mass; (D) the mass ratio [(DAG) / (VC)] of the content of diacylglycerol in the oil or fat to the content of vitamin C fatty acid ester in the oil or fat composition is 150 or more; and (E) the mass ratio [(ALA) / (VC)] of the content of α-linolenic acid in the fatty acids constituting the oil or fat to the content of vitamin C fatty acid ester in the oil or fat composition is 100 to 1200.

Description

Technical Field

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

[0002] Regarding α-linolenic acid (C18:3, ALA) rich in flaxseed (linseed), etc., it is known that when it enters the body, it is converted into eicosapentaenoic acid (C20:5) or docosahexaenoic acid (C22:6) with high physiological activity. In recent years, oils and fats containing a large amount of α-linolenic acid have been expected.

[0003] On the other hand, regarding oils and fats containing a high concentration of diacylglycerol, it has been reported that they have the following physiological effects, that is, they inhibit the increase in blood triglycerides (neutral fats) after eating and have a low accumulation in the body, etc.

[0004] Therefore, heretofore, in order to effectively exhibit the physiological activity functions of α-linolenic acid and diacylglycerol, an oil and fat composition containing 15 to 17% by weight of diglyceride and 30 to 85% by weight of triglyceride has been proposed, in which less than 15% by weight of the structural fatty acids of the diglyceride are ω3 series unsaturated fatty acids, and 15% by weight or more of the structural fatty acids of the triglyceride are ω3 series unsaturated fatty acids (Patent Document 1); and an oil and fat composition containing 5 to 59.9% by weight of diglyceride, triglyceride, and monoglyceride, in which 15 to 90% by weight of the structural fatty acids of the diglyceride are ω3 series unsaturated fatty acids having less than 20 carbon atoms (Patent Document 2), etc.

[0005] However, the oxidative stability of oils and fats rich in α-linolenic acid is very low, and it easily emits an unpleasant odor. Therefore, antioxidants are usually contained in the oils and fats to prevent the deterioration of the flavor of the oils and fats.

[0006] As antioxidants for oils and fats, tocopherol, rosemary extract, ascorbyl fatty acid ester, lecithin, etc. are used. For example, it is disclosed in Patent Document 1 above that 0.025 parts of vitamin C palmitate is mixed with respect to 100 parts of a mixture of diglyceride oil and linseed oil; and it is disclosed in Patent Document 2 that 0.02 parts of vitamin C palmitate is mixed with respect to 100 parts of diglyceride oil.

[0007] (Patent Document 1) Japanese Patent Laid-Open No. 2003-160794

[0008] (Patent Document 2) Japanese Patent Laid-Open No. 2002-138297 Summary of the Invention

[0009] The present invention provides an oil and fat composition, wherein,

[0010] the following (A) to (E) are satisfied:

[0011] (A) The content of diacylglycerol in the oil or fat is 15% by mass or more;

[0012] (B) The content of α-linolenic acid in the fatty acids constituting the oil or fat is 20% by mass or more;

[0013] (C) The content of vitamin C fatty acid ester is 0.025 to 0.30% by mass;

[0014] (D) The mass ratio [(DAG) / (VC)] of the content of diacylglycerol in the oil or fat to the content of vitamin C fatty acid ester in the oil or fat composition is 150 or more; and

[0015] (E) The mass ratio [(ALA) / (VC)] of the content of α-linolenic acid in the fatty acids constituting the oil or fat to the content of vitamin C fatty acid ester in the oil or fat composition is 100 to 1200. Detailed Description of the Invention

[0016] However, even existing methods have relatively low light stability and insufficient flavor retention.

[0017] Therefore, the present invention relates to providing an oil or fat with a high content of diacylglycerol, which is rich in α-linolenic acid and has a good flavor even after being exposed to light.

[0018] The present inventors focused on hexanal and propionic acid, which are odor components generated by the photooxidation of α-linolenic acid, and conducted intensive research. As a result, it was found that by containing vitamin C fatty acid ester in a specific range in the oil or fat, hexanal among the above two odor components is preferentially generated, thereby suppressing the pungent odor and putrid odor generated by propionic acid and maintaining a flavor suitable for edible oil.

[0019] Furthermore, it was found that vitamin C fatty acid ester has low solubility in the oil or fat and is likely to precipitate at low temperatures. At this time, if diacylglycerol is contained in the oil or fat at a specific mass ratio or more relative to vitamin C fatty acid ester, the precipitation of vitamin C fatty acid ester at low temperatures is suppressed.

[0020] According to the present invention, an oil or fat composition can be provided, which has a high content of α-linolenic acid and diacylglycerol, excellent physiological effects, and less pungent odor and putrid odor even after being exposed to light, and the flavor is maintained. Moreover, in the oil or fat composition of the present invention, the precipitation of vitamin C fatty acid ester is suppressed even at low temperatures.

[0021] The oil or fat composition of the present invention satisfies the following (A) to (E).

[0022] (A) The content of diacylglycerol in the oil or fat is 15% by mass or more;

[0023] (B) The content of α-linolenic acid in the fatty acids constituting the oil or fat is 20% by mass or more;

[0024] (C) The content of the vitamin C fatty acid ester is 0.025 to 0.30% by mass;

[0025] (D) The mass ratio [(DAG) / (VC)] of the content of diacylglycerol in the oil or fat to the content of the vitamin C fatty acid ester in the oil or fat composition is 150 or more; and

[0026] (E) The mass ratio [(ALA) / (VC)] of the content of α-linolenic acid in the fatty acids constituting the oil or fat to the content of the vitamin C fatty acid ester in the oil or fat composition is 100 to 1200.

[0027] In the present invention, from the viewpoint of usability, the content of the oil or fat in the oil or fat composition is preferably 90% by mass (hereinafter simply referred to as “%”) or more, more preferably 95% or more; and preferably 99.975% or less, more preferably 99.950% or less.

[0028] The content of the oil or fat in the oil or fat composition is preferably 90 to 99.975%, more preferably 95 to 99.950%.

[0029] In the present invention, the oil or fat contains any one or more of monoacylglycerol, diacylglycerol, and triacylglycerol. The type of the oil or fat is not particularly limited, and any type can be used as long as it can be used as an edible oil or fat.

[0030] In the present invention, the content of diacylglycerol in the oil or fat is 15% or more. Regarding the content of diacylglycerol in the oil or fat, from the viewpoints of effectively exhibiting the effects, physiological effects, and solubility of the vitamin C fatty acid ester, it is 15% or more, preferably 20% or more, more preferably 25% or more, further preferably 30% or more, further preferably 50% or more, further preferably 60% or more, further preferably 70% or more, further preferably 80% or more; and from the viewpoint of industrial productivity, it is preferably 99.5% or less, more preferably 98% or less, further preferably 95% or less, further preferably 90% or less.

[0031] The content of diacylglycerol in the oil or fat is 15% or more, preferably 20 to 99.5%, more preferably 25 to 98%, further preferably 30 to 95%, further preferably 60 to 90%, further preferably 70 to 90%, further preferably 80 to 90%.

[0032] The fatty acids constituting the diacylglycerol are not particularly limited and can be any of the saturated fatty acids or unsaturated fatty acids described below. In the present invention, in terms of effectively expressing the effects and physiological effects, the content of α-linolenic acid in the fatty acids constituting the diacylglycerol is preferably 20% or more.

[0033] The content of α-linolenic acid in the fatty acids constituting the diacylglycerol is preferably 30% or more, more preferably 40% or more, still more preferably 50% or more. Also, in terms of oxidation stability, it is preferably 80% or less, more preferably 70% or less, still more preferably 60% or less.

[0034] Furthermore, the amount of fatty acids in this specification is the amount in terms of free fatty acids.

[0035] The oil or fat of the present invention preferably contains triacylglycerol. Regarding the content of triacylglycerol, in terms of the industrial productivity of the oil or fat, it is preferably 1% or more, more preferably 2% or more, still more preferably 5% or more, and still more preferably 10% or more; also, it is preferably 85% or less, more preferably 80% or less, still more preferably 75% or less, still more preferably 50% or less, and still more preferably 25% or less.

[0036] 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%, and still more preferably 10 to 25%.

[0037] Regarding the content of monoacylglycerol in the oil or fat, in terms of flavor, the industrial productivity of the oil or fat, and oxidation stability, it is preferably 5% or less, more preferably 3% or less, still more preferably 2% or less, and still more preferably 1.5% or less; also, it is preferably more than 0%. The content of monoacylglycerol in the oil or fat can also be 0%.

[0038] Regarding the content of free fatty acids or their salts in the oil or fat, in terms of flavor and oxidation stability, it is preferably 3% or less, more preferably 2% or less, still more preferably 1% or less; also, it is preferably more than 0%. The content of free fatty acids or their salts in the oil or fat can also be 0%.

[0039] The fatty acid compositions of triacylglycerol, diacylglycerol, and monoacylglycerol can be the same or different.

[0040] In the present invention, the content of α-linolenic acid in the fatty acids constituting the oil or fat is 20% or more. Regarding the content of α-linolenic acid in the fatty acids constituting the oil or fat, from the aspect of physiological effects, it is 20% or more, more preferably 25% or more, further preferably 30% or more, further preferably 40% or more, further preferably 45% or more, further preferably 50% or more, further preferably 52% or more; also, from the aspect of oxidation stability, it is preferably 80% or less, more preferably 70% or less, further preferably 65% or less, further preferably 60% or less.

[0041] 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%, further preferably 30 - 70%, further preferably 40 - 70%, further preferably 45 - 70%, further preferably 50 - 65%, further preferably 52 - 60%.

[0042] In the present invention, the structural fatty acids other than α-linolenic acid constituting the oil or fat are not particularly limited and can be either saturated fatty acids or unsaturated fatty acids.

[0043] From the aspects of the flavor of the oil or fat and industrial productivity, the content of unsaturated fatty acids in the fatty acids constituting the oil or fat is preferably 60 - 100%, further preferably 70 - 100%, further preferably 80 - 99.5%. From the aspect of physiological effects, the number of carbon atoms of the unsaturated fatty acids is preferably 14 - 24, more preferably 16 - 22.

[0044] Among them, from the aspect 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; also, it is preferably 40% or less, more preferably 30% or less, further preferably 20% or less.

[0045] The content of linoleic acid in the fatty acids constituting the oil or fat is preferably 5 - 40%, more preferably 5 - 30%, further preferably 10 - 20%.

[0046] Also, from the aspect of industrial productivity, the content of oleic acid (C18:1) in the fatty acids constituting the oil or fat is preferably 10% or more; also, it is preferably 65% or less, more preferably 50% or less, further preferably 30% or less.

[0047] The content of oleic acid in the fatty acids constituting the oil or fat is preferably 10 - 65%, more preferably 10 - 50%, further preferably 10 - 30%.

[0048] In terms of industrial productivity aspects based on appearance, physiological effects, and oils and fats, the total content of saturated fatty acids in the fatty acids constituting the oils and fats is preferably 30% or less, more preferably 20% or less, still more preferably 10% or less, and still more preferably 7% or less; also, it is preferably 0.5% or more.

[0049] The number of carbon atoms of the saturated fatty acids is preferably 14 - 24, more preferably 16 - 22.

[0050] The oil and fat composition of the present invention contains 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 can be used, preferably commercially available products for food and drink. As the higher fatty acid, a straight - chain saturated fatty acid having 12 - 22 carbon atoms is preferred. The vitamin C fatty acid ester can be used singly or in combination of two or more.

[0051] In terms of suppressing pungent odors and putrid odors and improving the flavor even after exposure to light, the vitamin C fatty acid ester is preferably vitamin C palmitate, vitamin C stearate or a combination thereof, more preferably vitamin C palmitate.

[0052] In the present invention, the content of vitamin C fatty acid ester in the oil and fat composition is 0.025 - 0.30%. Regarding the content of vitamin C fatty acid ester in the oil and fat composition, in terms of effectively demonstrating the effect, it is 0.025% or more, preferably 0.027% or more, more preferably 0.030% or more, still more preferably 0.040% or more, and still more preferably 0.050% or more; also, in terms of appearance, flavor, and effectively demonstrating the effect, it is 0.30% or less, preferably 0.25% or less, more preferably 0.20% or less, still more preferably 0.15% or less, and still more preferably 0.10% or less.

[0053] The content of vitamin C fatty acid ester in the oil and fat composition is 0.025 - 0.30%, preferably 0.027 - 0.25%, more preferably 0.030 - 0.20%, still more preferably 0.040 - 0.15%, and still more preferably 0.050 - 0.10%.

[0054] In the present invention, the mass ratio [(DAG) / (VC)] of the content of diacylglycerol in the oil and fat to the content of vitamin C fatty acid ester in the oil and fat composition is 150 or more. The solubility of vitamin C fatty acid ester in the oil and fat is low, and it is likely to precipitate at low temperatures. At this time, by containing diacylglycerol in the oil and fat at a specific mass ratio or more relative to vitamin C fatty acid ester, the solubility of vitamin C fatty acid ester in the oil and fat can be increased, and precipitation at low temperatures can be inhibited. Thus, the present invention can achieve a flavor suitable for edible oil and low - temperature stability of the oil and fat composition.

[0055] Regarding the mass ratio [(DAG) / (VC)] of the content of diacylglycerol in the oil and fat to the content of vitamin C fatty acid ester in the oil and fat composition, in terms of appearance, solubility of vitamin C fatty acid ester, and effective manifestation of effects, it is 150 or more, preferably 180 or more, more preferably 200 or more, and further preferably 240 or more; also, in terms of flavor, it is preferably 4000 or less, more preferably 3800 or less, further preferably 3500 or less, further preferably 3000 or less, further preferably 2000 or less.

[0056] The mass ratio [(DAG) / (VC)] of the content of diacylglycerol in the oil and fat to the content of vitamin C fatty acid ester in the oil and fat composition is 150 or more, preferably 150 to 4000, more preferably 150 to 3800, further preferably 180 to 3500, further preferably 200 to 3000, further preferably 240 to 2000.

[0057] Also, 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. Regarding 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, in terms of flavor and effective manifestation of effects, it is 100 or more, preferably 120 or more, more preferably 150 or more, further preferably 200 or more, further preferably 300 or more, further preferably 500 or more; also, in terms of flavor and effective manifestation of effects, it is 1200 or less, preferably 1150 or less, more preferably 1100 or less, further preferably 1000 or less, further preferably 700 or less, further preferably 600 or less.

[0058] 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, preferably 120 to 1150, more preferably 150 to 1100, further preferably 200 to 1000, further preferably 200 to 700, further preferably 300 to 700, further preferably 300 to 600.

[0059] When α-linolenic acid is photo-oxidized, hexanal and propionic acid, which are odor components, are produced. Hexanal is characterized by having an odor like that of grass. Also, propionic acid is a component that causes the oil and fat to produce an irritating odor and a putrid odor.

[0060] By making the oil and fat composition of the present invention satisfy the above (A) to (E), as shown in the following examples, hexanal among hexanal and propionic acid generated by photooxidation of α-linolenic acid is preferentially generated. Therefore, in the sensory evaluation of the oil and fat composition, even after exposure to light, a grassy odor of hexanal is strongly emitted, making the irritating odor and putrid odor generated by propionic acid less perceptible, and maintaining a flavor suitable for edible oil. Regarding the oil and fat composition after the evaluation of storage under light described in the following examples, in consideration of reducing the irritating odor and putrid odor, the ratio of the peak area of hexanal to the peak area of propionic acid in headspace solid-phase microextraction / gas chromatography-mass spectrometry (HS SPME / GC / MS) described in the examples is preferably 1.0 or more, more preferably 1.5 or more, further preferably 1.6 or more, and further preferably 2.0 or more.

[0061] The oil and fat composition of the present invention can be prepared from an oil and fat containing diacylglycerol in which the constituent fatty acid contains α-linolenic acid. For example, by adding a vitamin C fatty acid ester to an oil and fat containing diacylglycerol in which the constituent fatty acid contains α-linolenic acid and further adding other components as needed, and appropriately heating, stirring, etc., the oil and fat composition of the present invention can be obtained. Conventional edible oils and fats can also be blended as needed.

[0062] An oil and fat containing diacylglycerol in which the constituent fatty acid contains α-linolenic acid can be obtained by an esterification reaction of a fatty acid from an oil and fat with glycerol, a transesterification reaction (glycerolysis) of an oil and fat with glycerol, etc.

[0063] The esterification reaction and glycerolysis reaction are roughly divided into a chemical method using a chemical catalyst such as an alkali metal or its alloy, an oxide or hydroxide of an alkali metal or alkaline earth metal, an alkoxide of an alkali metal or alkaline earth metal; and an enzymatic method using an enzyme such as lipase.

[0064] Among them, in consideration of controlling the fatty acid composition, the esterification reaction of the fractionated fatty acid from an oil and fat with glycerol described below is preferred.

[0065] In the present invention, the oil and fat (edible oil and fat) can be either vegetable oil or animal oil. For example, it can be exemplified: soybean oil, rapeseed oil, safflower oil, rice bran oil, corn oil, sunflower oil, cottonseed oil, olive oil, sesame oil, peanut oil, coix seed oil, wheat germ oil, perilla oil, linseed oil, perilla flaxseed oil, chia seed oil, Sacha Inchi Oil, walnut oil, kiwifruit seed oil, sage seed oil, grape seed oil, macadamia oil, hazelnut oil, pumpkin seed oil, camellia oil, tea seed oil, borage seed oil, palm oil, palm olein, palm stearin, coconut oil, palm kernel oil, cocoa butter, shorea robusta fat, shea butter, algal oil and other vegetable oils; fish oil, lard, beef tallow, milk fat and other animal oils; or their interesterified oils, hydrogenated oils, fractionated oils and other oil and fat types.

[0066] Among them, from the aspect of usability consideration, it is preferably to use vegetable oil, and further preferably to use a liquid oil with excellent low-temperature resistance, and further preferably to use at least one oil selected from perilla oil, linseed oil, perilla flaxseed oil, chia seed oil and Sacha Inchi Oil rich in α-linolenic acid. Furthermore, the liquid oil refers to the oil that is in a liquid state at 20°C when the cooling test is carried out according to the reference oil analysis test method 2.3.8-27.

[0067] The fatty acid from the oil and fat can be obtained by hydrolyzing the oil and fat. As the method for hydrolyzing the oil and fat, it can be exemplified: high-temperature and high-pressure decomposition method, and enzymatic decomposition method. The high-temperature and high-pressure decomposition method refers to adding water to the oil and fat and reacting under high-temperature and high-pressure conditions to obtain fatty acid and glycerol. Also, the enzymatic decomposition method refers to adding water to the oil and fat, using an oil and fat hydrolase as a catalyst and reacting under low-temperature conditions to obtain fatty acid and glycerol.

[0068] The hydrolysis reaction can be carried out according to a conventional method.

[0069] After hydrolyzing the oil and fat, it is preferably to fractionate the hydrolysis reactant to remove solids. As the fractionation method, it can be exemplified: solvent fractionation method, natural fractionation method (dry fractionation method), wetting agent fractionation method.

[0070] As the method for removing the precipitated solids, it can be exemplified: static separation, filtration, centrifugal separation, the method of separating by mixing an aqueous solution of a wetting agent in the fatty acid, etc.

[0071] From the viewpoint of being excellent in aspects such as flavor, the esterification reaction of the fatty acid and glycerol from the oil and fat is preferably carried out by an enzymatic method under mild conditions.

[0072] The amount of the enzyme used can be appropriately determined in consideration of the enzyme activity. From the aspect of increasing the reaction rate, when using an immobilized enzyme, the amount of the enzyme used is preferably 1 to 30%, more preferably 2 to 20% based on the total mass of the raw materials for the esterification reaction.

[0073] From the aspects of increasing the reaction rate and inhibiting enzyme inactivation, the reaction temperature of the esterification reaction is preferably 0 to 100°C, more preferably 20 to 80°C, and still more preferably 30 to 60°C. Also, from the aspect of industrial productivity, the reaction time is preferably within 15 hours, more preferably 1 to 12 hours, and still more preferably 2 to 10 hours.

[0074] Examples of the method for contacting the fatty acid and glycerol include: impregnation, stirring, a method of passing a liquid through a column filled with an immobilized lipase using a pump, etc.

[0075] After the esterification reaction, a refining process usually used for oils and fats can also be carried out. Specifically, examples include: distillation treatment, acid treatment, water washing, decolorization, deodorization, etc.

[0076] The oil and fat composition of the present invention can be used in the same manner as general edible oils and fats, and can be applied to various food and beverage products or feeds using oils and fats. As food and beverage products, in addition to ordinary food and beverage products, examples also include: specific health foods that claim the physiological effects of α-linolenic acid or diacylglycerol, functional labeled foods, etc.

[0077] As the form of food and beverage products, it can be solid, semi-solid, or liquid. For example, examples include beverages, foods containing water-in-oil emulsified oils, foods containing oil-in-water emulsified oils, baked foods, confectioneries, frozen foods, steamed foods, and further examples include nutritional supplement compositions such as tablets, capsules, and lozenges.

[0078] As feeds, examples include: livestock feeds for cattle, pigs, etc.; small animal feeds for rabbits, mice, etc.; fish and shellfish feeds for eels, shrimps, etc.; pet foods for dogs, cats, etc.

[0079] From the aspects of making the flavor good by suppressing pungent odors and putrid odors even after exposure to light and physiological effects, the oil and fat composition of the present invention preferably satisfies the following (A) to (E):

[0080] (A) The content of diacylglycerol in the oil and fat is 20% by mass or more;

[0081] (B) The content of α-linolenic acid in the fatty acids constituting the oil and fat is 20 to 80% by mass;

[0082] (C) The content of vitamin C fatty acid ester is 0.027 to 0.30% by mass;

[0083] (D) The mass ratio [(DAG) / (VC)] of the content of diacylglycerol in the oil to the content of vitamin C fatty acid ester in the oil composition is 200 or more; and

[0084] (E) The mass ratio [(ALA) / (VC)] of the content of α-linolenic acid in the fatty acids constituting the oil to the content of vitamin C fatty acid ester in the oil composition is 200 to 1100.

[0085] In terms of suppressing pungent odors and putrid odors even after exposure to light and thus improving the flavor, and in terms of physiological effects, the oil composition of the present invention preferably satisfies the following (A) to (E):

[0086] (A) The content of diacylglycerol in the oil is 20 to 98% by mass;

[0087] (B) The content of α-linolenic acid in the fatty acids constituting the oil is 20 to 70% by mass;

[0088] (C) The content of vitamin C fatty acid ester is 0.027 to 0.25% by mass;

[0089] (D) The mass ratio [(DAG) / (VC)] of the content of diacylglycerol in the oil to the content of vitamin C fatty acid ester in the oil composition is 200 or more; and

[0090] (E) The mass ratio [(ALA) / (VC)] of the content of α-linolenic acid in the fatty acids constituting the oil to the content of vitamin C fatty acid ester in the oil composition is 200 to 1100.

[0091] In terms of suppressing pungent odors and putrid odors even after exposure to light and thus improving the flavor, and in terms of physiological effects, the oil composition of the present invention preferably satisfies the following (A) to (E):

[0092] (A) The content of diacylglycerol in the oil is 20 to 95% by mass;

[0093] (B) The content of α-linolenic acid in the fatty acids constituting the oil is 25 to 70% by mass;

[0094] (C) The content of vitamin C fatty acid ester is 0.040 to 0.15% by mass;

[0095] (D) The mass ratio [(DAG) / (VC)] of the content of diacylglycerol in the oil to the content of vitamin C fatty acid ester in the oil composition is 200 or more; and

[0096] (E) 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 the vitamin C fatty acid ester in the oil and fat composition is 200 to 1100.

[0097] In view of suppressing pungent odors and putrid odors even after exposure to light and thus improving the flavor, and in view of physiological effects, the oil and fat composition of the present invention preferably satisfies the following (A) to (E):

[0098] (A) The content of diacylglycerol in the oil and fat is 20 to 95% by mass;

[0099] (B) The content of α-linolenic acid in the fatty acids constituting the oil and fat is 25 to 70% by mass;

[0100] (C) The content of the vitamin C fatty acid ester is 0.050 to 0.10% by mass;

[0101] (D) The mass ratio [(DAG) / (VC)] of the content of diacylglycerol in the oil and fat to the content of the vitamin C fatty acid ester in the oil and fat composition is 240 or more; and

[0102] (E) 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 the vitamin C fatty acid ester in the oil and fat composition is 300 to 600.

[0103] In view of suppressing pungent odors and putrid odors even after exposure to light and thus improving the flavor, and in view of physiological effects, the oil and fat composition of the present invention preferably satisfies the following (A) to (E):

[0104] (A) The content of diacylglycerol in the oil and fat is 30 to 90% by mass;

[0105] (B) The content of α-linolenic acid in the fatty acids constituting the oil and fat is 30 to 70% by mass;

[0106] (C) The content of the vitamin C fatty acid ester is 0.050 to 0.10% by mass;

[0107] (D) The mass ratio [(DAG) / (VC)] of the content of diacylglycerol in the oil and fat to the content of the vitamin C fatty acid ester in the oil and fat composition is 240 or more; and

[0108] (E) 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 the vitamin C fatty acid ester in the oil and fat composition is 300 to 600.

[0109] Regarding the above embodiments, the present invention further discloses the following oil and fat compositions.

[0110] <1> An oil and fat composition, wherein,

[0111] the following (A) to (E) are satisfied:

[0112] (A) The content of diacylglycerol in the oil and fat is 15% by mass or more;

[0113] (B) The content of α-linolenic acid in the fatty acids constituting the oil and fat is 20% by mass or more;

[0114] (C) The content of vitamin C fatty acid ester is 0.025 to 0.30% by mass;

[0115] (D) The mass ratio [(DAG) / (VC)] of the content of diacylglycerol in the oil and fat to the content of vitamin C fatty acid ester in the oil and fat composition is 150 or more; and

[0116] (E) 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.

[0117] <2> The oil and fat composition according to <1>, wherein the content of the oil and fat in the oil and fat composition is preferably 90% by mass or more, more preferably 95% by mass or more; further preferably 99.975% by mass or less, more preferably 99.950% by mass or less; further preferably 90 to 99.975% by mass, more preferably 95 to 99.950% by mass.

[0118] <3> The oil and fat composition according to <1> or <2>, wherein the content of diacylglycerol in the oil and fat is 15% by mass or more, preferably 20% by mass or more, more preferably 25% by mass or more, still more preferably 30% by mass or more, still more preferably 50% by mass or more, still more preferably 60% by mass or more, still more preferably 70% by mass or more, still more preferably 80% by mass or more; further preferably 99.5% by mass or less, more preferably 98% by mass or less, still more preferably 95% by mass or less, still more preferably 90% by mass or less; further preferably 20 to 99.5% by mass, more preferably 25 to 98% by mass, still more preferably 30 to 95% by mass, still more preferably 60 to 90% by mass, still more preferably 70 to 90% by mass, still more preferably 80 to 90% by mass.

[0119] <4> The oil and fat composition according to any one of <1> to <3>, wherein the content of α-linolenic acid in the fatty acids constituting the diacylglycerol is preferably 20% by mass or more, more preferably 25% by mass or more, still more preferably 30% by mass or more, still more preferably 40% by mass or more, still more preferably 50% by mass or more; further, it is preferably 80% by mass or less, more preferably 70% by mass or less, still more preferably 60% by mass or less; further, it is preferably 20 to 80% by mass, more preferably 25 to 70% by mass, still more preferably 30 to 70% by mass, still more preferably 40 to 60% by mass, still more preferably 50 to 60% by mass.

[0120] <5> The oil and fat composition according to any one of <1> to <4>, wherein the content of triacylglycerol in the oil and fat is preferably 1% by mass or more, more preferably 2% by mass or more, still more preferably 5% by mass or more, still more preferably 10% by mass or more; further, it is preferably 85% by mass or less, more preferably 80% by mass or less, still more preferably 75% by mass or less, still more preferably 50% by mass or less, still more preferably 25% by mass or less; further, it is preferably 1 to 85% by mass, more preferably 2 to 80% by mass, still more preferably 2 to 75% by mass, still more preferably 5 to 50% by mass, still more preferably 10 to 25% by mass.

[0121] <6> The oil and fat composition according to any one of <1> to <5>, wherein the content of monoacylglycerol in the oil and fat is preferably 5% by mass or less, more preferably 3% by mass or less, still more preferably 2% by mass or less, still more preferably 1.5% by mass or less; further, it is preferably more than 0% by mass.

[0122] <7> The oil and fat composition according to any one of <1> to <6>, wherein the content of free fatty acid or its salt in the oil and fat is preferably 3% by mass or less, more preferably 2% by mass or less, still more preferably 1% by mass or less; further, it is preferably more than 0% by mass.

[0123] <8> The oil and fat composition according to any one of <1> to <7>, wherein the content of α-linolenic acid 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, further preferably 40% by mass or more, further preferably 45% by mass or more, further preferably 50% by mass or more, further preferably 52% by mass or more; also, it is preferably 80% by mass or less, more preferably 70% by mass or less, further preferably 65% by mass or less, further preferably 60% by mass or less; also, it is preferably 20 to 80% by mass, more preferably 25 to 70% by mass, further preferably 30 to 70% by mass, further preferably 40 to 70% by mass, further preferably 45 to 70% by mass, further preferably 50 to 65% by mass, further preferably 52 to 60% by mass.

[0124] <9> The oil and fat composition according to any one of <1> to <8>, wherein the content of linoleic acid in the fatty acids constituting the oil and fat is preferably 5% by mass or more, more preferably 10% by mass or more; also, it is preferably 40% by mass or less, more preferably 30% by mass or less, further preferably 20% by mass or less; also, it is preferably 5 to 40% by mass, more preferably 5 to 30% by mass, further preferably 10 to 20% by mass.

[0125] <10> The oil and fat composition according to any one of <1> to <9>, wherein the content of oleic acid in the fatty acids constituting the oil and fat is preferably 10% by mass or more; also, it is preferably 65% by mass or less, more preferably 50% by mass or less, further preferably 30% by mass or less; also, it is preferably 10 to 65% by mass, more preferably 10 to 50% by mass, further preferably 10 to 30% by mass.

[0126] <11> The oil and fat composition according to any one of <1> to <10>, wherein the vitamin C fatty acid ester is preferably vitamin C palmitate, vitamin C stearate or a combination thereof, more preferably vitamin C palmitate.

[0127] <12>The oil and fat composition according to any one of <1> to <11>, wherein the content of the vitamin C fatty acid ester in the oil and fat composition is 0.025% by mass or more, preferably 0.027% by mass or more, more preferably 0.030% by mass or more, still more preferably 0.040% by mass or more, and still more preferably 0.050% by mass or more; further, it is 0.30% by mass or less, preferably 0.25% by mass or less, more preferably 0.20% by mass or less, still more preferably 0.15% by mass or less, and still more preferably 0.10% by mass or less; further, it is preferably 0.027 to 0.25% by mass, more preferably 0.030 to 0.20% by mass, still more preferably 0.040 to 0.15% by mass, and still more preferably 0.050 to 0.10% by mass.

[0128] <13>The oil and fat composition according to any one of <1> to <12>, wherein the mass ratio [(DAG) / (VC)] of the content of diacylglycerol in the oil and fat to the content of the vitamin C fatty acid ester in the oil and fat composition is 150 or more, preferably 180 or more, more preferably 200 or more, still more preferably 240 or more; further, it is 4000 or less, preferably 3800 or less, more preferably 3500 or less, still more preferably 3000 or less, and still more preferably 2000 or less; further, it is preferably 150 to 4000, more preferably 150 to 3800, still more preferably 180 to 3500, still more preferably 200 to 3000, and still more preferably 240 to 2000.

[0129] <14>The oil and fat composition according to any one of <1> to <13>, wherein the mass ratio [(ALA) / (VC)] of the content of α-linolenic acid in the fatty acid constituting the oil and fat to the content of the vitamin C fatty acid ester in the oil and fat composition is 100 or more, preferably 120 or more, more preferably 150 or more, still more preferably 200 or more, still more preferably 300 or more, and still more preferably 500 or more; further, it is 1200 or less, preferably 1150 or less, more preferably 1100 or less, still more preferably 1000 or less, still more preferably 700 or less, and still more preferably 600 or less; further, it is preferably 120 to 1150, more preferably 150 to 1100, still more preferably 200 to 1000, still more preferably 200 to 700, still more preferably 300 to 700, and still more preferably 300 to 600.

[0130] <15> The oil and fat composition according to any one of <1> to <14>, wherein, after the oil and fat composition is exposed to light with an illuminance of about 2000 lx for 7 days, the ratio of the peak area of hexanal to the peak area of propionic acid obtained by analysis using headspace solid-phase microextraction / gas chromatography-mass spectrometry is preferably 1.0 or more, more preferably 1.5 or more, still more preferably 1.6 or more, and still more preferably 2.0 or more.

[0131] <16> The oil and fat composition according to any one of <1> to <15>, which preferably contains an esterification reaction oil of fractionated fatty acids derived from oil and fat and glycerol.

[0132] <17> The oil and fat composition according to <16>, wherein the fractionated fatty acids are preferably derived from at least one oil and fat selected from perilla oil, linseed oil, sesame oil, chia seed oil, and sacha inchi oil.

[0133] <18> A food or drink containing the oil and fat composition according to any one of <1> to <17>.

[0134] <19> A feed containing the oil and fat composition according to any one of <1> to <17>.

[0135] [Examples]

[0136] [Analysis method]

[0137] (i) Glyceride composition of oil and fat

[0138] Add about 10 mg of the oil and fat sample and 0.5 mL of a trimethylsilylating agent ("Silylating agent TH", manufactured by Kanto Chemical) to a glass sample bottle. After tightening the sample bottle, heat it at 70 °C for 15 minutes. Add 1.0 mL of water and 1.5 mL of hexane thereto, and shake. After standing, subject the upper layer to gas chromatography (GLC) for analysis.

[0139] <GLC analysis conditions>

[0140] (Conditions)

[0141] Apparatus: Agilent 7890B (manufactured by Agilent Technologies)

[0142] Column: DB-1ht 10 m × 0.25 mm × 0.2 μm (manufactured by Agilent J&W)

[0143] Carrier gas: 1.0 mL of helium / min

[0144] Syringe: Split (1:50), T = 340 °C

[0145] Detector: FID, T = 350 °C

[0146] Column oven temperature: Starting from 80 °C, heating at 10 °C / min to 340 °C and holding for 15 minutes

[0147] (ii) Structural fatty acid composition of fats and oils

[0148] Fatty acid methyl esters are prepared according to the "Method for the Preparation of Fatty Acid Methyl Esters (2.4.1.-1996)" in the "Standard Analytical Test Methods for Oils and Fats" compiled by the Japanese Oil Chemists' Society, and the obtained fat and oil samples are determined according to American Oil Chemists. Society Official Method Ce 1f-96 (GLC method).

[0149] <GLC analysis conditions>

[0150] Apparatus: Agilent 7890B (manufactured by Agilent Technologies)

[0151] Column: CP-SIL88 50m × 0.25mm × 0.2μm (manufactured by Agilent J&W)

[0152] Carrier gas: 1.0 mL helium / min

[0153] Syringe: Split (1:50), T = 300 °C

[0154] Detector: FID, T = 300 °C

[0155] Column oven temperature: Holding at 150 °C for 5 min → heating at 1 °C / min → holding at 160 °C for 5 min → heating at 2 °C / min → holding at 200 °C for 10 min → heating at 10 °C / min → holding at 220 °C for 5 min

[0156] (iii) Analysis of hexanal and propionic acid

[0157] The analysis of hexanal and propionic acid is carried out by headspace solid-phase microextraction / gas chromatography-mass spectrometry (HS SPME / GC / MS) method. The SPME fiber used is 50 / 30μm DVB / CAR / PDMS fiber (manufactured by SUPELCO), and the autosampler used is MPS-2 (manufactured by Gerstel).

[0158] Collect 1 g of fat and oil sample into a headspace vial (10 mL capacity, manufactured by GL Sciences), heat at 40 °C for 20 minutes, and then perform headspace sampling for 30 minutes through the SPME fiber. The determination is carried out by GC / MS.

[0159] <GC / MS Analysis Conditions>

[0160] Apparatus: Agilent 7890A / 5975 (manufactured by Agilent Technologies)

[0161] Column: VF-WAX 60m × 0.25mm × 1.0μm (manufactured by Agilent J&W)

[0162] Carrier gas: 1.0 mL helium / min

[0163] Syringe: Splitless, T = 240 °C

[0164] Oven temperature: Hold at 35 °C for 4 min → Heat at 3 °C / min → 185 °C → Heat at 10 °C / min → Hold at 240 °C for 10 min

[0165] Ionization method: EI (70 eV)

[0166] Ion source temperature: 230 °C

[0167] Measurement mode: Total ion scan range: m / z 30 - 500

[0168] Examples 1 - 8 and Comparative Examples 1 - 7

[0169] (1) Preparation of Oils and Fats a - d

[0170] Prepare oils and fats a - d shown in Table 1.

[0171] [Table 1]

[0172]

[0173] MAG: Monoacylglycerol

[0174] DAG: Diacylglycerol

[0175] TAG: Triacylglycerol

[0176] Oil and fat a: Mix soybean oil and rapeseed oil, hydrolyze to obtain fatty acids by enzyme, then cool step by step, and fractionate the precipitated fatty acids by centrifugation. Next, use immobilized 1,3 - specific lipase as a catalyst and carry out an esterification reaction between the fractionated fatty acids and glycerol under reduced pressure. After filtering and separating the immobilized enzyme, subject the reacted product to molecular distillation, wash with water, deodorize, and add 0.2 mass% tocopherol preparation (manufactured by Riken Vitamin Co., Ltd.) to obtain oil and fat a.

[0177] 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.

[0178] Oil c: Linseed oil (Nisshin Linseed Oil, manufactured by Nisshin OilliO Co., Ltd.) was used.

[0179] Oil d: Rapeseed oil (SEVEN PREMIUM Refreshing Taste Rapeseed Oil, manufactured by J-Oil Mills Inc.) was used.

[0180] (2) Preparation of Oils A to K

[0181] Oils A to K were prepared by mixing oils a to d at the ratios shown in Table 2. The mixing ratios, glyceride compositions, and fatty acid compositions of oils A to K are shown in Table 2.

[0182] [Table 2]

[0183]

[0184] MAG: Monoacylglycerol

[0185] DAG: Diacylglycerol

[0186] TAG: Triacylglycerol

[0187] (3) Preparation of Oil Compositions

[0188] In oils A to K, 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.) was mixed at the ratios shown in Table 3 to obtain oil compositions. Furthermore, in Table 3, the content of diacylglycerol is the content in the oil, the content of α-linolenic acid is the content in the fatty acids constituting the oil, and the content of vitamin C fatty acid ester is the content in the oil composition.

[0189] (4) Evaluation of Precipitation of Vitamin C Fatty Acid Ester at Low Temperature

[0190] The oil compositions of the examples and comparative examples were stored at 5°C for 3 days, and the precipitation of vitamin C fatty acid ester was observed. The oil compositions in which vitamin C fatty acid ester was precipitated were evaluated as "yes", and the oil compositions in which vitamin C fatty acid ester was not precipitated were evaluated as "no".

[0191] (5) Evaluation of Storage under Light Exposure

[0192] For the oil and fat composition in which precipitation of vitamin C fatty acid ester was not observed at low temperature in the above (4), using an incubator with illumination (FLI-2010A manufactured by Tokyo Rika Kikai Co., Ltd.), after exposing it to light with an illuminance of about 2000 lx at 25°C for 7 days, component analysis and sensory evaluation of the odor were carried out. The sensory evaluation was carried out by 3 professional panelists according to the evaluation criteria shown below. Scoring was based on the agreement of the 3 professional panelists.

[0193] (Evaluation criteria)

[0194] 4: Strongly feel pungent odor and putrid odor

[0195] 3: Feel pungent odor and putrid odor, there is a problem

[0196] 2: Slightly feel pungent odor and putrid odor, but there is no problem

[0197] 1: Hardly feel pungent odor and putrid odor

[0198] (6) Results

[0199] The results are shown in Table 3.

[0200]

[0201] As shown in Table 3, in the oil and fat compositions of Examples 1 to 8 and Comparative Examples 1 to 3, precipitation of vitamin C fatty acid ester was not observed at a low temperature of 5°C. However, in the oil and fat compositions of Examples 1 to 8 and Comparative Examples 1 to 3, the amounts of hexanal and propionic acid generated after exposure to light were different. It was confirmed that in the oil and fat compositions of Examples 1 to 8, hexanal among hexanal and propionic acid was preferentially produced, and although an odor like that of grass was felt in the sensory evaluation, the pungent odor and putrid odor were suppressed. In contrast, in the oil and fat compositions of Comparative Examples 1 to 3, more propionic acid among hexanal and propionic acid was produced, and pungent odor and putrid odor generated by propionic acid were also felt in the sensory evaluation.

[0202] In the oil and fat compositions of Comparative Examples 4 to 7, vitamin C fatty acid ester precipitated at a low temperature of 5°C.

Claims

1. An oil and fat composition, wherein, Satisfy the following (A) to (E): (A) The content of diacylglycerol in the oil and fat is 15% by mass or more; (B) The content of α-linolenic acid in the fatty acids constituting the oil and fat is 20% by mass or more; (C) The content of vitamin C fatty acid ester is 0.025 to 0.30% by mass; (D) The mass ratio (DAG) / (VC) of the content of diacylglycerol in the oil and fat to the content of vitamin C fatty acid ester in the oil and fat composition is 150 or more; and (E) 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.

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

3. The oil and fat composition according to claim 1, wherein, (C) The content of α-linolenic acid in the fatty acids constituting the diacylglycerol is 20% by mass or more.

4. The oil and fat composition according to claim 1, wherein, (C) The content of α-linolenic acid in the fatty acids constituting the diacylglycerol is 25% by mass or more and 70% by mass or less.

5. The oil and fat composition according to claim 1, wherein, (C) The content of α-linolenic acid in the fatty acids constituting the diacylglycerol is 30% by mass or more and 70% by mass or less.

6. The oil and fat composition according to any one of claims 1 to 5, wherein, (A) The content of diacylglycerol in the oil and fat is 20% by mass or more and 99.5% by mass or less.

7. The oil and fat composition according to any one of claims 1 to 5, wherein, (B) The content of α-linolenic acid in the fatty acids constituting the oil and fat is 20% by mass or more and 70% by mass or less.

8. The oil and fat composition according to any one of claims 1 to 5, wherein, (B) The content of α-linolenic acid in the fatty acids constituting the oil and fat is 30% by mass or more and 70% by mass or less.

9. The oil and fat composition according to any one of claims 1 to 5, wherein, (C) The vitamin C fatty acid ester is vitamin C palmitate, vitamin C stearate or a combination thereof.

10. The oil and fat composition according to any one of claims 1 to 5, wherein, (C) The content of vitamin C fatty acid ester is 0.027% by mass or more and 0.25% by mass or less.

11. The oil and fat composition according to any one of claims 1 to 5, wherein, (C) The content of vitamin C fatty acid ester is 0.027% by mass or more and 0.15% by mass or less.

12. The oil and fat composition according to any one of claims 1 to 5, wherein, (D) The mass ratio (DAG) / (VC) of the content of diacylglycerol in the oil and fat to the content of vitamin C fatty acid ester in the oil and fat composition is 200 or more and 2000 or less.

13. The oil and fat composition according to any one of claims 1 to 5, wherein, (D) The mass ratio (DAG) / (VC) of the content of diacylglycerol in the oil and fat to the content of vitamin C fatty acid ester in the oil and fat composition is 240 or more and 2000 or less.

14. The oil and fat composition according to any one of claims 1 to 5, wherein, (E) 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 200 or more and 1100 or less.

15. The fat and oil composition according to any one of claims 1 to 5, wherein, (E) 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 500 or more and 600 or less.

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

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

18. The fat and oil composition according to any one of claims 1 to 5, wherein, (D) After the oil and fat composition is exposed to light with an illuminance of about 2000 lx for 7 days, the ratio of the peak area of hexanal to the peak area of propionic acid obtained by headspace solid-phase microextraction / gas chromatography-mass spectrometry analysis is 1.0 or more.

19. The fat and oil composition according to any one of claims 1 to 5, wherein, After the oil and fat composition is exposed to light with an illuminance of about 2000 lx for 7 days, the ratio of the peak area of hexanal to the peak area of propionic acid obtained by headspace solid-phase microextraction / gas chromatography-mass spectrometry analysis is 1.5 or more.

20. The fat and oil composition according to any one of claims 1 to 5, wherein, After the oil and fat composition is exposed to light with an illuminance of about 2000 lx for 7 days, the ratio of the peak area of hexanal to the peak area of propionic acid obtained by headspace solid-phase microextraction / gas chromatography-mass spectrometry analysis is 2.0 or more.

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