Method for producing oil-and-fat composition, method for producing interesterified oil-and-fat composition, method for suppressing crystal precipitation of oil-and-fat composition, and method for suppressing crystal precipitation of interesterified oil-and-fat composition

Abstract

Provided is a method for producing an oil-and-fat composition (excluding oils and fats for hard butter and puff pastry margarine), the method for producing an oil-and-fat composition including a step for obtaining an interesterified oil-and-fat composition by interesterification of an oil-and-fat raw material that includes a triglyceride composed of a saturated fatty acid having 13-15 carbon atoms and a non-animal oil and fat other than the triglyceride, wherein 2-20 mass% of the saturated fatty acid having 13-15 carbon atoms is contained in the total fatty acids of the oil-and-fat composition.

Description

Method for producing an oil and fat composition, method for producing an ester-exchanged oil and fat composition, method for suppressing crystallization of an oil and fat composition, and method for suppressing crystallization of an ester-exchanged oil and fat composition

[0001] The present invention relates to a method for producing an oil and fat composition, a method for producing an ester-exchanged oil and fat composition, a method for suppressing crystallization of an oil and fat composition, and a method for suppressing crystallization of an ester-exchanged oil and fat composition.

[0002] As a technique for obtaining an oil and fat composition having desired properties, there are those described in Patent Documents 1 to 6. Patent Document 1 (Japanese Patent Application Laid-Open No. 55-61780) describes a method for producing a butter flavor having a good and strong butter flavor using inexpensive raw materials that are naturally abundant (left column, page 1), and after adding and decomposing a lipolytic enzyme to an oil and fat, further adding and decomposing a lipoxygenase. A method for producing a butter flavor is described (Claim 1). Further, it is described in the same document that beef tallow and a plurality of specific triglycerides were mixed and subjected to ester exchange (Example 2).

[0003] Patent Document 2 (Japanese Patent Application Laid-Open No. 2001-40386) describes an oil and fat composition containing specific amounts of triglyceride, diglyceride, monoglyceride and free fatty acid, and containing a specific amount of ω3 unsaturated acyl group and a specific amount of monoene acyl group in the acyl groups constituting the diglyceride (Claim 1). Such an oil and fat composition is said to be difficult to oxidize, have fluidity, be excellent in flavor, and be able to effectively exhibit the physiological activity of ω3 unsaturated fatty acids (paragraph 0045).

[0004] Patent Document 3 (Japanese Patent Application Laid-Open No. 6-7090) describes, as a material that can be a substitute for the paraffin component of a chewing gum base without adversely affecting the properties of the chewing gum base (paragraph 0003), a chewing gum base containing a conventional natural and / or synthetic elastic and / or resinous component and further containing a specific amount of a triglyceride composition having a specific saturated fatty acid content and a solid fat index (Claim 1).

[0005] Patent Document 4 (International Publication No. 2013 / 051388) describes a technique for providing an oil and fat composition for bakery foods that can suppress the whitening of the bakery food portion and blooming of the oily food portion that occur over time in a composite food combining bakery foods and oily foods (paragraph 0010), and describes an oil and fat composition in which the oil and fat satisfies specific conditions (claim 1).

[0006] Furthermore, Patent Document 5 (International Publication No. 2023 / 100847) describes an oil for a frozen mix containing a plurality of randomly transesterified oils having a specific composition (Claim 1), which is said to make it possible to obtain a frozen dessert that melts easily in the mouth, has a refreshing aftertaste, and is rich in flavor (Paragraph 0010).

[0007] Japanese Patent Publication No. 55-61780, Japanese Patent Publication No. 2001-40386, Japanese Patent Publication No. 6-7090, International Publication No. 2013 / 051388, International Publication No. 2023 / 100847

[0008] Through the inventors' research, it has become clear that saturated fatty acids having 13 to 15 carbon atoms are prone to crystallization when they are included in an oil and fat composition in the form of triglycerides composed of saturated fatty acids having 13 to 15 carbon atoms.

[0009] Therefore, the present invention provides a technique for suppressing the crystal precipitation of oil and fat compositions.

[0010] The present invention provides the following manufacturing methods and methods: [1] A method for producing an oil and fat composition (excluding hard butter and oil and fat for puff pastry margarine), comprising the step of transesterifying a raw oil and fat containing a triglyceride composed of saturated fatty acids having 13 to 15 carbon atoms and a non-animal oil and fat other than the triglyceride to obtain a transesterified oil and fat composition, wherein the total fatty acids of the oil and fat composition contain 2% to 20% by mass of saturated fatty acids having 13 to 15 carbon atoms. [2] The manufacturing method according to [1], further comprising the step of mixing the transesterified oil and fat composition with an edible oil and fat other than the transesterified oil and fat composition having a solid fat content of 5% or less at 20°C. [3] The manufacturing method according to [2], wherein the content of the transesterified oil and fat composition in the oil and fat composition is 10% to less than 100% by mass of the entire oil and fat composition. [4] The method for producing an edible oil other than the transesterified oil composition, wherein the solid fat content at 20°C is 5% or less, and the edible oil comprises one or more selected from the group consisting of rapeseed oil, olive oil, sesame oil, soybean oil, flaxseed oil, and medium-chain triglyceride. [5] The method for producing an edible oil composition according to [1], wherein the content of the transesterified oil composition in the oil composition is greater than 0% by mass and 100% by mass or less with respect to the entire oil composition. [6] The method for producing an edible oil composition according to any one of [1] to [5], wherein the content of saturated fatty acids having 13 to 15 carbon atoms in the total fatty acids of the transesterified oil composition is 2% by mass or more and 40% by mass or less. [7] A method for producing a transesterified fat composition (excluding fats for hard butter and puff pastry margarine), comprising the step of transesterifying a raw oil containing a triglyceride composed of saturated fatty acids having 13 to 15 carbon atoms and a non-animal fat other than the triglyceride to obtain a transesterified fat composition, wherein the total fatty acids of the transesterified fat composition contain 2% to 40% by mass of saturated fatty acids having 13 to 15 carbon atoms. [8] The method for producing a transesterified fat composition according to any one of [1] to [5] and [7], wherein the non-animal fat is rapeseed oil.[9] The manufacturing method according to any one of [1] to [5], wherein the content of fatty acids having 12 carbon atoms in the total fatty acids of the oil and fat composition is 15% by mass or less.

[10] The manufacturing method according to any one of [1] to [5], wherein the content of fatty acids having 12 carbon atoms in the total fatty acids of the oil and fat composition is 2.5 or less by mass relative to the content of fatty acids having 13 to 15 carbon atoms.

[11] The manufacturing method according to any one of [1] to [5] and [7], further comprising the step of reacting a saturated fatty acid having 13 to 15 carbon atoms with glycerin to obtain the triglyceride.

[12] The manufacturing method according to any one of [1] to [5] and [7], further comprising the step of adding an emulsifier after the step of obtaining the transesterified oil and fat composition.

[13] A method for suppressing crystal precipitation of an oil and fat composition (excluding hard butter and oil and fat for puff pastry margarine), comprising the step of transesterifying a raw oil and fat containing a triglyceride composed of saturated fatty acids having 13 to 15 carbon atoms and a non-animal oil other than the triglyceride to obtain a transesterified oil and fat composition, wherein the oil and fat composition contains 2% to 20% by mass of saturated fatty acids having 13 to 15 carbon atoms in the total fatty acids.

[14] The method according to

[13] , further comprising the step of mixing the transesterified oil and fat composition with an edible oil other than the transesterified oil and fat composition having a solid fat content of 5% or less at 20°C.

[15] A method for suppressing crystal precipitation of a transesterified fat composition (excluding hard butter and fats for puff pastry margarine), comprising the step of transesterifying a raw oil containing a triglyceride composed of saturated fatty acids having 13 to 15 carbon atoms and a non-animal fat other than the triglyceride to obtain a transesterified fat composition, wherein the transesterified fat composition contains 2% to 40% by mass of saturated fatty acids having 13 to 15 carbon atoms in its total fatty acid content.

[0011] Furthermore, according to the present invention, it is also possible to provide, for example, a transesterified fat composition and a fat composition obtained by the manufacturing method of the present invention for use in the manufacture of food products.

[0012] Furthermore, according to the present invention, it is also possible to provide a method for producing food, which includes the steps of obtaining a transesterified oil composition or an oil composition by the production method of the present invention, and the steps of obtaining food by blending the obtained transesterified oil composition or oil composition with other raw materials.

[0013] According to the present invention, the crystal precipitation of oil and fat compositions can be suppressed.

[0014] Embodiments of the present invention will be described below. In these embodiments, the composition may contain each component individually or in combination of two or more. In this specification, the "~" indicating a numerical range represents "greater than or equal to" and "less than or equal to," including both of the numerical values ​​at either end. Furthermore, when upper and lower limits of a numerical range are indicated, the upper and lower limits may be combined as appropriate, and the resulting numerical range is also disclosed.

[0015] (Method for producing the fat and oil composition) In this embodiment, the method for producing the fat and oil composition (excluding fats and oils for hard butter and puff pastry margarine) includes the following step 10. (Step 10) A step of transesterifying raw fats and oils containing triglycerides composed of saturated fatty acids having 13 to 15 carbon atoms and non-animal fats and oils other than triglycerides to obtain a transesterified fat and oil composition. The fat and oil composition obtained in this embodiment contains, specifically, 2% to 20% by mass of saturated fatty acids having 13 to 15 carbon atoms in the total fatty acids of the fat and oil composition.

[0016] In this embodiment, since the method for producing the oil and fat composition includes step 10, by adjusting the content of saturated fatty acids having 13 to 15 carbon atoms in the total fatty acids of the oil and fat composition to, for example, the range described above, an oil and fat composition in which crystallization is suppressed can be obtained. Here, in this embodiment, crystallization specifically refers to the formation of crystals to the extent that the oil and fat composition does not melt even after being stored at a low temperature of about 4°C or below and then stored at room temperature (for example, 20 to 25°C) for about 7 hours. Furthermore, according to this embodiment, it is also possible to obtain an oil and fat composition in which the crystals formed in the oil and fat composition have excellent meltability. Details of step 10 will be described later.

[0017] From the viewpoint of more stably suppressing the crystallization of the oil and fat composition, the content of saturated fatty acids having 13 to 15 carbon atoms in the total fatty acids of the oil and fat composition is, for example, 2% by mass or more, preferably 3% by mass or more, and more preferably 4% by mass or more. Similarly, from the viewpoint of more stably suppressing the crystallization of the oil and fat composition, the content of saturated fatty acids having 13 to 15 carbon atoms in the total fatty acids of the oil and fat composition is, for example, 20% by mass or less, preferably 18% by mass or less, more preferably 16% by mass or less, even more preferably 14% by mass or less, even more preferably 12% by mass or less, and even more preferably 10% by mass or less. Furthermore, from the viewpoint of more stably suppressing the crystallization of the oil and fat composition, the content of saturated fatty acids having 13 to 15 carbon atoms in the total fatty acids of the oil and fat composition is 2% by mass or more and 20% by mass or less, preferably 3% by mass or more and 18% by mass or less, more preferably 3% by mass or more and 16% by mass or less, even more preferably 3% by mass or more and 14% by mass or less, even more preferably 4% by mass or more and 12% by mass or less, and even more preferably 4% by mass or more and 10% by mass or less.

[0018] The content of saturated fatty acids having 13 to 15 carbon atoms in the total fatty acids of the oil and fat composition can be adjusted, for example, by at least one of the following: (i) adjusting the amount of transesterified oil and fat composition in the oil and fat composition, and (ii) adjusting the content of saturated fatty acids having 13 to 15 carbon atoms in the total fatty acids of the transesterified oil and fat composition in step 10.

[0019] With respect to (i) above, the content of the transesterified oil composition in the oil composition is, for example, more than 0% by mass and 100% by mass or less, preferably more than 0% by mass and less than 100% by mass, more preferably 5% by mass or more and less than 100% by mass, more preferably 10% by mass or more and less than 100% by mass, even more preferably 10% by mass or more and 99% by mass or less, even more preferably 15% by mass or more and 95% by mass or less, even more preferably 20% by mass or more and 90% by mass or less, even more preferably 25% by mass or more and 80% by mass or less, even more preferably 30% by mass or more and 70% by mass or less, even more preferably 35% by mass or more and 60% by mass or less, and even more preferably 45% by mass or more and 50% by mass or less.

[0020] In terms of more stably suppressing crystal precipitation in the oil and fat composition, the content of the transesterified oil and fat composition in the oil and fat composition is preferably 10% by mass or more, more preferably 15% by mass or more, even more preferably 25% by mass or more, even more preferably 35% by mass or more, and even more preferably 45% by mass or more, relative to the entire oil and fat composition. Similarly, the content of the transesterified oil and fat composition in the oil and fat composition is preferably 100% by mass or less, more preferably less than 100% by mass, even more preferably 99% by mass or less, even more preferably 95% by mass or less, and even more preferably 90% by mass or less, relative to the entire oil and fat composition.

[0021] On the other hand, in terms of suppressing crystal precipitation while using other oils and fats that are more readily available, the content of the transesterified oil and fat composition in the oil and fat composition is preferably more than 0% by mass relative to the total oil and fat composition, more preferably 5% by mass or more, even more preferably 10% by mass or more, even more preferably 15% by mass or more, even more preferably 20% by mass or more, even more preferably 25% by mass or more, and even more preferably 30% by mass or more. Similarly, the content of the transesterified oil and fat composition in the oil and fat composition is preferably 80% by mass or less relative to the total oil and fat composition, more preferably 70% by mass or less, even more preferably 60% by mass or less, and even more preferably 50% by mass or less.

[0022] In relation to the above-mentioned use of other oils and fats that are more readily available, the method for producing the oil and fat composition preferably further includes the following step 20: (Step 20) A step of mixing the transesterified oil and fat composition obtained in step 10 with an edible oil or fat other than the transesterified oil and fat composition that has a solid fat content of 5% or less at 20°C (hereinafter also referred to as "other edible oils and fats"). By further including step 20 in the method for producing the oil and fat composition, it is possible to select an edible oil or fat that is more readily available and use it in combination with the transesterified oil and fat composition, thereby making it easier to suppress crystal precipitation in the oil and fat composition.

[0023] In step 20, the other edible oil is any edible oil with a solid fat content of 5% or less at 20°C, other than the above-mentioned transesterified oil composition. The solid fat content (SFC) at 20°C is specifically measured according to Method I described in AOCS Official Method Cd16-93. The solid fat content of the other edible oil at 20°C is preferably 4% or less, more preferably 3% or less, even more preferably 2% or less, even more preferably 1% or less, and even more preferably 0%. Furthermore, the above solid fat content may specifically be 0% or more or greater than 0%.

[0024] Other edible oils and fats include, for example, rapeseed oil, olive oil, sesame oil, soybean oil, flaxseed oil, corn oil, sunflower oil, safflower oil, cottonseed oil, rice oil, peanut oil, perilla oil, palm oil, medium-chain triglycerides (MCTs), algal oils, and processed oils and fats obtained by fractionation, hydrogenation, transesterification, etc. The other edible oils and fats preferably include one or more selected from the group consisting of rapeseed oil, olive oil, sesame oil, soybean oil, flaxseed oil, and medium-chain triglycerides, and more preferably include one or more selected from the group consisting of rapeseed oil, olive oil, and sesame oil. This allows for more stable suppression of crystal precipitation while imparting a good flavor. Here, MCT is a medium-chain fatty acid, specifically a triglyceride composed of saturated fatty acids having 8 to 10 carbon atoms. Furthermore, in terms of more stably suppressing crystal precipitation, the other edible oils and fats are preferably vegetable oils and fats in which the content of fatty acids with 16 carbon atoms in the total fatty acids is 20% by mass or less, more preferably 18% by mass or less, and even more preferably 15% by mass or less.

[0025] The content of other edible oils in the oil composition can specifically be the remainder after subtracting the total content of components other than other edible oils in the oil composition. Furthermore, the content of other edible oils in the oil composition may be, for example, more than 0% by mass and less than 100% by mass, 1% by mass to 90% by mass, 2% by mass to 85% by mass, 5% by mass to 80% by mass, 10% by mass to 75% by mass, or 20% by mass to 70% by mass.

[0026] The content of fatty acids with 12 carbon atoms in the total fatty acids of the oil and fat composition is preferably 15% by mass or less, more preferably 10% by mass or less, even more preferably 5% by mass or less, even more preferably 1% by mass or less, and even more preferably 0% by mass. This allows for more stable suppression of crystal precipitation. Alternatively, the content of fatty acids with 12 carbon atoms in the total fatty acids of the oil and fat composition may be, for example, 0% by mass or more, or 0.1% by mass or more.

[0027] In the total fatty acids of the oil composition, the content of fatty acids having 12 carbon atoms is preferably 2.5 or less by mass ratio to the content of fatty acids having 13 to 15 carbon atoms, more preferably 2.0 or less, even more preferably 1.5 or less, even more preferably 1.0 or less, even more preferably 0.5 or less, and even more preferably 0. This allows for more stable suppression of crystal precipitation. Furthermore, the above mass ratio ((fatty acids with 12 carbon atoms) / (fatty acids with 13 to 15 carbon atoms)) may be, for example, 0 or more or 0.1 or more.

[0028] In the total fatty acids of the oil and fat composition, the content of fatty acids having 16 carbon atoms is preferably 2% by mass or more, more preferably 2.5% by mass or more, even more preferably 3% by mass or more, and even more preferably 3.5% by mass or more. This allows for more stable suppression of crystal precipitation. Similarly, in the total fatty acids of the oil and fat composition, the content of fatty acids having 16 carbon atoms is preferably 20% by mass or less, more preferably 10% by mass or less, and even more preferably 8% by mass or less.

[0029] The content of unsaturated fatty acids with 18 carbon atoms in the total fatty acids of the oil and fat composition is preferably 20% by mass or more, more preferably 30% by mass or more, even more preferably 40% by mass or more, even more preferably 50% by mass or more, and even more preferably 60% by mass or more. This allows for more stable suppression of crystal precipitation. Alternatively, the content of unsaturated fatty acids with 18 carbon atoms in the total fatty acids of the oil and fat composition may be, for example, 95% by mass or less, 90% by mass or less, or 88% by mass or less.

[0030] The total content of EPA (eicosapentaenoic acid) and DHA (docosahexaenoic acid) in the total fatty acids of the oil and fat composition is preferably 20% by mass or less, more preferably 10% by mass or less, even more preferably 5% by mass or less, even more preferably 1% by mass or less, and even more preferably 0% by mass. This allows for more stable suppression of crystal precipitation. Alternatively, the total content of EPA and DHA in the total fatty acids of the oil and fat composition may be, for example, 0% by mass or more, or 0.1% by mass or more.

[0031] The content of polyunsaturated fatty acids in the total fatty acids of the oil and fat composition is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, and even more preferably 17% by mass or more. This allows for more stable suppression of crystal precipitation. Similarly, the content of polyunsaturated fatty acids in the total fatty acids of the oil and fat composition is preferably 50% by mass or less, more preferably 40% by mass or less, even more preferably 35% by mass or less, and even more preferably 32% by mass or less.

[0032] Next, step 10 will be described. (Step 10, Method for Producing Ester Oil Composition) As described above, step 10 is a step of obtaining a transesterified oil composition by transesterifying a raw oil containing triglycerides composed of saturated fatty acids having 13 to 15 carbon atoms and non-animal oils other than triglycerides. Step 10 is also a method for producing a transesterified oil composition (excluding oils for hard butter and puff pastry margarine). That is, in this embodiment, the method for producing a transesterified oil composition (excluding oils for hard butter and puff pastry margarine) includes step 10. The transesterified oil composition obtained in step 10 contains, specifically, 2% to 40% by mass of saturated fatty acids having 13 to 15 carbon atoms in the total fatty acids of the transesterified oil composition.

[0033] In this embodiment, since the method for producing the transesterified oil composition includes step 10, the content of saturated fatty acids having 13 to 15 carbon atoms in the total fatty acids of the transesterified oil composition can be adjusted to, for example, the range described above, that is, by (ii) above, an oil composition in which crystallization is suppressed can be obtained.

[0034] In the transesterified fat composition, the content of saturated fatty acids having 13 to 15 carbon atoms in the total fatty acids is, for example, 2% by mass or more, preferably 3% by mass or more, and more preferably 4% by mass or more. This allows for more stable suppression of crystal precipitation. Similarly, in the transesterified fat composition, the content of saturated fatty acids having 13 to 15 carbon atoms in the total fatty acids is preferably 20% by mass or less, more preferably 18% by mass or less, even more preferably 16% by mass or less, and even more preferably 14% by mass or less. In this case, the content of the transesterified fat composition in the fat composition is preferably high, for example 80% by mass or more, preferably 90% by mass or more, more preferably 95% by mass or more, and even more preferably 100% by mass.

[0035] On the other hand, in terms of suppressing crystal precipitation while using other oils and fats that are more readily available, the content of saturated fatty acids having 13 to 15 carbon atoms in the total fatty acids of the transesterified oil and fat composition is preferably 3% by mass or more, more preferably 5% by mass or more, even more preferably 6% by mass or more, and even more preferably 8% by mass or more. Similarly, the content of saturated fatty acids having 13 to 15 carbon atoms in the total fatty acids of the transesterified oil and fat composition is, for example, 40% by mass or less, preferably 35% by mass or less, more preferably 30% by mass or less, and even more preferably 25% by mass or less. In this case, the content of the transesterified oil and fat composition in the oil and fat composition is, for example, 2% by mass or more, preferably 5% by mass or more, and also, for example, 80% by mass or less, preferably 70% by mass or less, more preferably 60% by mass or less, even more preferably 50% by mass or less, even more preferably 40% by mass or less, and even more preferably 35% by mass or less.

[0036] In the total fatty acids of the transesterified oil composition, the content of fatty acids having 12 carbon atoms is preferably 15% by mass or less, more preferably 10% by mass or less, even more preferably 5% by mass or less, even more preferably 1% by mass or less, and even more preferably 0% by mass. This allows for more stable suppression of crystal precipitation. Alternatively, the content of fatty acids having 12 carbon atoms in the total fatty acids of the transesterified oil composition may be, for example, 0% by mass or more, or 0.1% by mass or more.

[0037] In the total fatty acids of the transesterified oil composition, the content of fatty acids having 12 carbon atoms is preferably 2.5 or less by mass ratio to the content of fatty acids having 13 to 15 carbon atoms, more preferably 2.0 or less, even more preferably 1.5 or less, even more preferably 1.0 or less, even more preferably 0.5 or less, and even more preferably 0. This allows for more stable suppression of crystal precipitation. Furthermore, the above mass ratio ((fatty acids with 12 carbon atoms) / (fatty acids with 13 to 15 carbon atoms)) may be, for example, 0 or more or 0.1 or more.

[0038] In the transesterified oil composition, the content of fatty acids having 16 carbon atoms in the total fatty acids is preferably 2% by mass or more, more preferably 2.5% by mass or more, and even more preferably 3% by mass or more. This allows for more stable suppression of crystal precipitation. Similarly, in the transesterified oil composition, the content of fatty acids having 16 carbon atoms in the total fatty acids is preferably 20% by mass or less, more preferably 10% by mass or less, even more preferably 8% by mass or less, and even more preferably 6% by mass or less.

[0039] In the transesterified oil composition, the content of unsaturated fatty acids having 18 carbon atoms in the total fatty acids is preferably 20% by mass or more, more preferably 30% by mass or more, even more preferably 40% by mass or more, even more preferably 50% by mass or more, and even more preferably 60% by mass or more. This allows for more stable suppression of crystal precipitation. Alternatively, the content of unsaturated fatty acids having 18 carbon atoms in the total fatty acids of the transesterified oil composition may be, for example, 95% by mass or less, 90% by mass or less, or 88% by mass or less.

[0040] The total content of EPA (eicosapentaenoic acid) and DHA (docosahexaenoic acid) in the total fatty acids of the transesterified oil composition is preferably 20% by mass or less, more preferably 10% by mass or less, even more preferably 5% by mass or less, even more preferably 1% by mass or less, and even more preferably 0% by mass. This allows for more stable suppression of crystal precipitation. Alternatively, the total content of EPA and DHA in the total fatty acids of the transesterified oil composition may be, for example, 0% by mass or more, or 0.1% by mass or more.

[0041] The content of polyunsaturated fatty acids in the total fatty acids of the transesterified oil composition is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, and even more preferably 17% by mass or more. This allows for more stable suppression of crystal precipitation. Similarly, the content of polyunsaturated fatty acids in the total fatty acids of the transesterified oil composition is preferably 50% by mass or less, more preferably 40% by mass or less, even more preferably 35% by mass or less, even more preferably 30% by mass or less, and even more preferably 25% by mass or less.

[0042] In step 10, the triglyceride among the raw oils and fats may be composed of saturated fatty acids having 13 to 15 carbon atoms, and may be a triglyceride composed of a single fatty acid such as tritridecanoate glyceryl, tritetradecanoate glyceryl, or tripentadecanoate glyceryl, or a triglyceride composed of a mixed fatty acid having 13 to 15 carbon atoms. From the viewpoint of availability, the triglyceride is preferably at least one triglyceride selected from the group consisting of tritridecanoate glyceryl, tritetradecanoate glyceryl, and tripentadecanoate glyceryl, and more preferably tritetradecanoate glyceryl.

[0043] In addition, non-animal fats and oils specifically refer to fats and oils other than the following animal fats and oils. Animal fats and oils specifically include natural animal fats and oils (such as beef tallow, lard, fish oil, etc.); and synthetic fats and oils derived from animals (such as EPA triglyceride, etc.). Examples of non-animal fats and oils include vegetable fats and oils and algal oils. Specific examples of vegetable fats and oils include natural vegetable fats and oils such as rapeseed oil, soybean oil, corn oil, sesame oil, palm oil, palm kernel oil, rice bran oil, cottonseed oil, safflower oil, sunflower oil, olive oil, linseed oil, perilla oil, peanut oil, sal fat, cocoa butter, shea butter, etc.; and synthetic fats and oils derived from plants such as MCT, etc. Examples of algal oils include Euglena oil, etc. Further, the non-animal fats and oils may be processed fats and oils such as transesterified oils, fractionated oils, hydrogenated oils, etc. of vegetable fats and oils and algal oils.

[0044] In terms of obtaining a more stable crystal precipitation inhibiting effect, the non-animal fats and oils are preferably one or more selected from the group consisting of vegetable fats and oils and their processed fats and oils, more preferably one or more selected from the group consisting of rapeseed oil, soybean oil and corn oil, and even more preferably rapeseed oil. Also, in terms of more stably suppressing crystal precipitation, the non-animal fats and oils are preferably vegetable fats and oils in which the content of fatty acids having 16 carbon atoms in the total fatty acids is preferably 10% by mass or less, and the above content is more preferably 9% by mass or less, and even more preferably 7% by mass or less.

[0045] In step 10, transesterification can be carried out by known methods. The transesterification method may be random transesterification or specific transesterification of fatty acids bonded to the 1st and 3rd positions of glycerol, but random transesterification is preferred. Examples of catalysts used for transesterification include chemical catalysts such as sodium methoxide and enzyme catalysts such as lipase. The transesterified oil composition can be produced, for example, by the following method. That is, 0.3 parts by mass of sodium methoxide is added as a catalyst to 100 parts by mass of raw oil, which is a mixture of triglycerides composed of saturated fatty acids having 13 to 15 carbon atoms and non-animal oils other than triglycerides, and a random transesterification reaction is carried out with stirring for 60 minutes under conditions of 80°C and a vacuum of 2.0 kPa. After the random transesterification reaction, the catalyst is removed by washing with water. After washing with water, decolorization treatment is performed using activated clay, and then deodorization treatment is performed to obtain the transesterified oil composition.

[0046] The method for producing the oil and fat composition may further include at least one of the following steps 30 and 40: (Step 30) A step of reacting a saturated fatty acid having 13 to 15 carbon atoms with glycerin to obtain the above triglyceride. (Step 40) A step of adding an emulsifier after step 10.

[0047] (Step 30) Step 30 is specifically performed before step 10. In step 30, commercially available saturated fatty acids and glycerol having 13 to 15 carbon atoms can be used. Specifically, the saturated fatty acids having 13 to 15 carbon atoms are one or more fatty acids selected from the group consisting of tridecanoic acid, tetradecanoic acid (myristic acid), and pentadecanoic acid, and tetradecanoic acid is preferred.

[0048] Step 30 can be carried out by a conventional method. The triglyceride obtained in Step 30 may be a triglyceride composed of a single fatty acid such as glyceryl tritridecanoate, glyceryl tritetradecanoate, glyceryl tripentadecanoate, etc., or a triglyceride composed of a mixed fatty acid having 13 to 15 carbon atoms. The triglyceride obtained in Step 30 is preferably at least one triglyceride selected from the group consisting of glyceryl tritridecanoate, glyceryl tritetradecanoate, and glyceryl tripentadecanoate from the viewpoint of excellent production stability, and more preferably glyceryl tritetradecanoate.

[0049] (Step 40) Step 40 may be carried out after Step 10. The order of Step 40 and Step 20 may be either way, or they may be simultaneous. By providing Step 40, crystal precipitation can be more stably suppressed.

[0050] Examples of the emulsifier include nonionic surfactants. More specifically, one or more selected from the group consisting of polyglycerol fatty acid esters, polyglycerol condensed ricinoleic acid esters, monoglycerol fatty acid esters, organic acid monoglycerides, sorbitan fatty acid esters, propylene glycol fatty acid esters, sucrose fatty acid esters, and lecithin are included, and polyglycerol fatty acid esters are preferred.

[0051] The carbon number of the fatty acid constituting the polyglycerol fatty acid ester may be, for example, 8 to 22. Examples of the fatty acid constituting the polyglycerol fatty acid ester include caprylic acid, capric acid, lauric acid, myristic acid (tetradecanoic acid), palmitic acid, stearic acid, oleic acid, behenic acid, erucic acid, etc. These may be composed of a single fatty acid or a plurality of mixed fatty acids. Also, the average degree of polymerization of polyglycerol in the polyglycerol fatty acid ester is not limited and is, for example, 2 or more and 30 or less.

[0052] Examples of commercially available polyglycerin fatty acid esters include Sunsoft QMP-7, Sunsoft QMP-1, and Sunsoft QMP-5 (all manufactured by Taiyo Kagaku Co., Ltd.); and SY Glister THL-15, SY Glister THL-17, and SY Glister THL-44 (all manufactured by Sakamoto Pharmaceutical Co., Ltd.).

[0053] The amount of emulsifier in the oil and fat composition is preferably 0.01% by mass or more, more preferably 0.05% by mass or more, and even more preferably 0.08% by mass or more, relative to the entire oil and fat composition, in order to more stably suppress crystal precipitation. Similarly, the amount of emulsifier in the oil and fat composition is preferably 2% by mass or less, more preferably 1% by mass or less, even more preferably 0.5% by mass or less, and even more preferably 0.2% by mass or less, relative to the entire oil and fat composition.

[0054] The fat and oil composition and transesterified fat and oil composition obtained in this embodiment may be used as is or as a raw material for manufacturing, and can be suitably used, for example, in the manufacture of food. Specifically, it may be used as a fat and oil when cooking food, or as a raw material for manufacturing food products such as seasonings (dressings, mayonnaise, etc.), confectionery, bread, noodles, rice, processed foods (dressed dishes, fried foods, stir-fries, grilled foods, boiled foods, etc.), and beverages. Furthermore, the fat and oil composition and transesterified fat and oil composition obtained in this embodiment can be widely used for cooking, and are suitable for heating and cooking, such as stir-frying oil and frying oil, for example. Herein, when the fat and oil composition or transesterified fat and oil composition is used as is, these are not specifically hard butter (fat and oil for chocolate). Furthermore, when the fat and oil composition or transesterified fat and oil composition is used as a raw material for manufacturing food products, these are not specifically fat and oil for puff pastry or margarine.

[0055] (Method for suppressing crystal precipitation) In this embodiment, the method for suppressing crystal precipitation of an oil and fat composition (excluding hard butter and oil and fat for puff pastry margarine) (hereinafter also referred to as the "crystal precipitation suppression method") includes the above-described step 10, and specifically contains 2% by mass or more and 20% by mass or less of saturated fatty acids having 13 to 15 carbon atoms in the total fatty acids of the oil and fat composition. By including the above step 10, the content of saturated fatty acids having 13 to 15 carbon atoms in the total fatty acids of the oil and fat composition can be adjusted to, for example, the above range, thereby suitably suppressing crystallization of the oil and fat composition.

[0056] Furthermore, in this embodiment, the method for suppressing crystal precipitation of the transesterified fat composition (excluding fats for hard butter and puff pastry margarine) includes the above-described step 10, and specifically contains 2% to 40% by mass of saturated fatty acids having 13 to 15 carbon atoms in the total fatty acids of the transesterified fat composition. By including the above step 10, the content of saturated fatty acids having 13 to 15 carbon atoms in the total fatty acids of the transesterified fat composition can be adjusted to, for example, the above-described range, thereby suitably suppressing crystallization of the fat composition.

[0057] In this embodiment, the methods for suppressing crystal precipitation of the transesterified oil composition and the methods for suppressing crystal precipitation of the oil composition can be appropriately adapted to the manufacturing methods described above. For example, the method for suppressing crystal precipitation of the oil composition may further include a step of mixing the transesterified oil composition with an edible oil other than the transesterified oil composition that has a solid fat content of 5% or less at 20°C. This makes it easier to suppress crystal precipitation of the oil composition.

[0058] Furthermore, according to this embodiment, it is possible to improve the storage stability of the oil and fat composition at temperatures below 25°C, preferably below 4°C. In addition, according to this embodiment, it is possible to improve the disappearance of crystals that form when the oil and fat composition is stored at low temperatures (e.g., below 4°C) at room temperature (e.g., 20-25°C).

[0059] The embodiments of the present invention have been described above, but these are illustrative examples of the present invention, and various other configurations can be adopted. Examples of reference embodiments are listed below. 1. A method for producing an oil and fat composition (excluding hard butter and oil and fat for puff pastry margarine), comprising the step of transesterifying a raw oil and fat containing triglycerides composed of saturated fatty acids having 13 to 15 carbon atoms and non-animal oils other than the triglycerides to obtain a transesterified oil and fat composition, wherein the total fatty acids of the oil and fat composition contain 2% to 20% by mass of saturated fatty acids having 13 to 15 carbon atoms. 2. The method according to 1, further comprising the step of mixing the transesterified oil and fat composition with edible oils other than the transesterified oil and fat composition having a solid fat content of 5% or less at 20°C. 3. The method according to 2, wherein the content of the transesterified oil and fat composition in the oil and fat composition is 10% to less than 100% by mass of the entire oil and fat composition. 4. 2. A method for producing a transesterified fat composition, wherein the edible fat other than the transesterified fat composition, having a solid fat content of 5% or less at 20°C, comprises one or more selected from the group consisting of rapeseed oil, olive oil, sesame oil, soybean oil, flaxseed oil, and medium-chain triglycerides. 5. A method for producing a transesterified fat composition, wherein the content of saturated fatty acids having 13 to 15 carbon atoms in the total fatty acids of the transesterified fat composition is 2% by mass or more and 40% by mass or less. 6. A method for producing a transesterified fat composition (excluding fats for hard butter and puff pastry margarine), comprising the step of transesterifying a raw oil containing triglycerides composed of saturated fatty acids having 13 to 15 carbon atoms and non-animal fats other than the triglycerides to obtain a transesterified fat composition, wherein the transesterified fat composition contains 2% by mass or more and 40% by mass or less saturated fatty acids having 13 to 15 carbon atoms in the total fatty acids of the transesterified fat composition. 7. A method for producing an oil or fat according to any one of 1 to 4 and 6, wherein the non-animal oil or fat includes rapeseed oil. 8. A method for producing an oil or fat according to any one of 1 to 4, wherein the content of fatty acids having 12 carbon atoms in the total fatty acids of the oil or fat composition is 15% by mass or less.9. The manufacturing method according to any one of 1 to 4, wherein the content of fatty acids having 12 carbon atoms in the total fatty acids of the oil composition is 2.5 or less by mass ratio to the content of fatty acids having 13 to 15 carbon atoms. 10. The manufacturing method according to any one of 1 to 4 and 6, further comprising the step of reacting saturated fatty acids having 13 to 15 carbon atoms with glycerin to obtain the triglyceride. 11. The manufacturing method according to any one of 1 to 4 and 6, further comprising the step of adding an emulsifier after the step of obtaining the transesterified oil composition. 12. A method for suppressing crystal precipitation of an oil and fat composition (excluding hard butter and oils and fats for puff pastry margarine), comprising the step of transesterifying a raw oil and fat containing triglycerides composed of saturated fatty acids having 13 to 15 carbon atoms and non-animal oils and fats other than the triglycerides to obtain a transesterified oil and fat composition, wherein the oil and fat composition contains 2% to 20% by mass of saturated fatty acids having 13 to 15 carbon atoms in its total fatty acid content. 13. The method according to 12, further comprising the step of mixing the transesterified oil and fat composition with edible oils and fats other than the transesterified oil and fat composition having a solid fat content of 5% or less at 20°C. 14. A method for suppressing crystal precipitation of a transesterified fat composition (excluding fats for hard butter and puff pastry margarine), comprising the step of transesterifying a raw material fat containing a triglyceride composed of saturated fatty acids having 13 to 15 carbon atoms and a non-animal fat other than the triglyceride to obtain a transesterified fat composition, wherein the transesterified fat composition contains 2% to 40% by mass of saturated fatty acids having 13 to 15 carbon atoms in its total fatty acid content.

[0060] The embodiment will be described in detail below with reference to examples, but this embodiment is not limited to these examples.

[0061] (Ingredients) The main ingredients (oils and fats, emulsifiers) used in the following examples are listed below. Rapeseed oil: AJINOMOTO Smooth Canola Oil, manufactured by J-Oil Mills (0% solid fat content at 20°C, 4.1% by mass of fatty acids with 16 carbon atoms in total fatty acids) Sesame oil: AJINOMOTO Pure Sesame Oil for Sesame Oil Lovers, manufactured by J-Oil Mills (0% solid fat content at 20°C, 9.0% by mass of fatty acids with 16 carbon atoms in total fatty acids) Extra virgin olive oil: AJINOMOTO Extra Virgin Olive Oil, manufactured by J-Oil Mills (0% solid fat content at 20°C, 12.0% by mass of fatty acids with 16 carbon atoms in total fatty acids) Glyceryl tritetradecanoate: Produced in Manufacturing Example 1 described below. Transesterified oils 1-14: Produced in Manufacturing Example 2 described below. Emulsifier 1: Sunsoft QMP-7, polyglycerin fatty acid ester, manufactured by Taiyo Kagaku Co., Ltd. Emulsifier 2: Sunsoft QMP-1, polyglycerin fatty acid ester, manufactured by Taiyo Kagaku Co., Ltd. Emulsifier 3: Sunsoft QMP-5, polyglycerin fatty acid ester, manufactured by Taiyo Kagaku Co., Ltd. Emulsifier 4: SY Glister THL-15, polyglycerin fatty acid ester, manufactured by Sakamoto Pharmaceutical Co., Ltd. Emulsifier 5: SY Glister THL-17, polyglycerin fatty acid ester, manufactured by Sakamoto Pharmaceutical Co., Ltd. Emulsifier 6: SY Glister THL-44, polyglycerin fatty acid ester, manufactured by Sakamoto Pharmaceutical Co., Ltd.

[0062] (Manufacturing Example 1) In this example, glyceryl tritetradecanoate was obtained by the following procedure. 89.7 parts by mass of myristic acid (tetradecanoic acid) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and 10.3 parts by mass of glycerin (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were mixed, and 0.1 parts by mass of sodium hydroxide was added as a catalyst. The mixture was stirred at 220°C and atmospheric pressure for 240 minutes while blowing in nitrogen to carry out the ester synthesis reaction. After the ester synthesis reaction, deoxidation was carried out by adding an aqueous sodium hydroxide solution to remove unreacted tetradecanoic acid. After deoxidation, decolorization treatment was performed using activated clay, and then deodorization treatment was performed to obtain glyceryl tritetradecanoate.

[0063] (Production Example 2) In this example, transesterified oils 1 to 14 were obtained by the following procedure. To 100 parts by mass of oil and fat obtained by mixing glyceryl tritetradecanoate (trimyristicin) obtained in Production Example 1 with rapeseed oil in the ratio shown in Table 1, 0.3 parts by mass of sodium methoxide was added as a catalyst, and a random transesterification reaction was carried out at 80°C and a vacuum of 2.0 kPa for 60 minutes while stirring. After the random transesterification reaction, the catalyst was removed by washing with water. After washing with water, decolorization treatment was performed using activated clay, and then deodorization treatment was performed to obtain each transesterified oil. The fatty acid composition of the obtained transesterified oils was analyzed by the following method. The results are shown in Table 1.

[0064] (Analysis Method for Fatty Acid Composition) After converting the fatty acids of each example into methyl esters using the boron trifluoride methanol method, the fatty acid composition was analyzed by gas chromatography (GC) under the following conditions, and the content (mass %) of each fatty acid in the total fatty acid composition was calculated. In the table, for example, "C14:0" represents a fatty acid with 14 carbon atoms and 0 unsaturated bonds, and "C18:1" represents a fatty acid with 18 carbon atoms and 1 unsaturated bond. From the obtained results, the amounts of unsaturated fatty acids with 18 carbon atoms, polyunsaturated fatty acids (PUFAs), and fatty acids with 16 carbon atoms were calculated. • GC instrument: Product name GC2010 (manufactured by Shimadzu Corporation) • Column: DB-23 (30m x 0.25mm x 0.25μm) (manufactured by Agilent Technologies) • Inlet temperature: 230℃ • Carrier gas: Helium (45.4 mL / min) • Split ratio: 50:1 • Column temperature: 80℃ 2 min → (35℃ / min) → 160℃ → (2℃ / min) → 230℃ 8 min • Detector: Flame ion detector (240℃)

[0065]

[0066] (Examples 1-47, Control Examples 1-4, Comparative Examples 1-4) In these examples, oil and fat compositions were prepared by blending each component according to the formulations shown in Tables 2-6, and the presence or absence of crystal precipitation was evaluated. The fatty acid composition of each oil and fat composition was also calculated using the method described above. The evaluation results and fatty acid compositions are shown in each table. Extra virgin olive oil was used as a control in the evaluation. Extra virgin olive oil is known to crystallize at low temperatures, such as in winter, and it is considered acceptable if the crystals disappear at room temperature or in a water bath. Therefore, the evaluation criteria were set on the premise that even if crystals form during home use or distribution, it is acceptable if the properties are equivalent to this.

[0067] (Method for preparing oil and fat compositions and method for crystal precipitation testing) 1. After heating the oil and fat as necessary to melt the crystals, the oil and fat and emulsifier were mixed in the specified proportions to prepare the oil and fat compositions for each example. In the example where an emulsifier was added, the mixture was stirred at 60°C for 5 minutes after mixing to completely dissolve the emulsifier. 2. 40 g of the oil and fat composition was weighed into a 50 mL vial (Laboran screw-cap vial 50 mL, manufactured by AS ONE Corporation). 3. To completely melt the crystals, the mixture was left to stand at 80°C for 1 hour. 4. The mixture was left to stand in a constant temperature bath set to 4°C. 5. After 24 hours, the presence or absence of crystals was visually observed and evaluated according to the following criteria A to C. A: No crystals B: Slight crystals (surface, bottom, etc.) or slight turbidity C: Clearly visible crystals

[0068] (Method of Crystallization Melting Test) For some examples, the crystallization melting test was performed using the following procedure: 1. The oil composition for each example was stored at 4°C for 14 to 30 days, and then stored at 20°C to 24°C. 2. After storage for the time indicated in each table (5 to 7 hours), the presence or absence of crystallization was observed visually and evaluated according to the above criteria A to C.

[0069] (Overall Evaluation) Based on the results of the crystal precipitation test and crystal melting test, the storage stability was evaluated according to the following criteria, and a score of 2 or higher was considered a pass. 4: Crystal precipitation test result is A 3: Crystal precipitation test result is B or C, but the crystal melting test result is A 2: Crystal precipitation test result is B or C, and the crystal melting test result is B 1: Crystal precipitation test result is B or C, and the crystal melting test result is C

[0070]

[0071]

[0072]

[0073]

[0074]

[0075] Tables 2 to 6 show that in each example, crystal precipitation of the oil composition was suitably suppressed, and even when crystals did form, they exhibited excellent meltability.

[0076] This application claims priority based on Japanese Patent Application No. 2024-173835, filed on 2 October 2024, and incorporates all of its disclosures herein.

Claims

1. A method for producing an oil and fat composition (excluding hard butter and oil and fat for puff pastry margarine), comprising the step of transesterifying a raw oil and fat containing triglycerides composed of saturated fatty acids having 13 to 15 carbon atoms and non-animal oils other than the triglycerides to obtain a transesterified oil and fat composition, wherein the oil and fat composition contains 2% to 20% by mass of saturated fatty acids having 13 to 15 carbon atoms in its total fatty acid content.

2. The manufacturing method according to claim 1, further comprising the step of mixing the transesterified fat composition with an edible fat other than the transesterified fat composition having a solid fat content of 5% or less at 20°C.

3. The manufacturing method according to claim 2, wherein the content of the transesterified oil composition in the oil composition is 10% by mass or more and less than 100% by mass of the entire oil composition.

4. The manufacturing method according to claim 2, wherein the edible oils and fats other than the transesterified oil composition, having a solid fat content of 5% or less at 20°C, comprises one or more selected from the group consisting of rapeseed oil, olive oil, sesame oil, soybean oil, flaxseed oil, and medium-chain triglyceride.

5. The manufacturing method according to claim 1, wherein the content of the transesterified oil composition in the oil composition is more than 0% by mass and 100% by mass or less with respect to the entire oil composition.

6. The manufacturing method according to any one of claims 1 to 5, wherein the content of saturated fatty acids having 13 to 15 carbon atoms in the total fatty acids of the transesterified oil composition is 2% by mass or more and 40% by mass or less.

7. A method for producing a transesterified fat composition (excluding fats for hard butter and puff pastry margarine), comprising the step of transesterifying a raw material fat containing a triglyceride composed of saturated fatty acids having 13 to 15 carbon atoms and a non-animal fat other than the triglyceride to obtain a transesterified fat composition, wherein the transesterified fat composition contains 2% to 40% by mass of saturated fatty acids having 13 to 15 carbon atoms in its total fatty acid content.

8. The manufacturing method according to any one of claims 1 to 5 and 7, wherein the non-animal fat includes rapeseed oil.

9. The manufacturing method according to any one of claims 1 to 5, wherein the content of fatty acids having 12 carbon atoms in the total fatty acids of the oil composition is 15% by mass or less.

10. The manufacturing method according to any one of claims 1 to 5, wherein the content of fatty acids having 12 carbon atoms in the total fatty acids of the oil composition is 2.5 or less by mass ratio to the content of fatty acids having 13 or more carbon atoms and 15 or less.

11. The manufacturing method according to any one of claims 1 to 5 and 7, further comprising the step of reacting a saturated fatty acid having 13 or more carbon atoms and glycerin to obtain the triglyceride.

12. The manufacturing method according to any one of claims 1 to 5 and 7, further comprising the step of adding an emulsifier after the step of obtaining the transesterified oil composition.

13. A method for suppressing crystal precipitation of an oil and fat composition (excluding hard butter and oil and fat for puff pastry margarine), comprising the step of transesterifying a raw oil and fat containing a triglyceride composed of saturated fatty acids having 13 to 15 carbon atoms and a non-animal oil other than the triglyceride to obtain a transesterified oil and fat composition, wherein the oil and fat composition contains 2% to 20% by mass of saturated fatty acids having 13 to 15 carbon atoms in its total fatty acid content.

14. The method according to claim 13, further comprising the step of mixing the transesterified fat composition with an edible fat other than the transesterified fat composition having a solid fat content of 5% or less at 20°C.

15. A method for suppressing crystal precipitation of a transesterified fat composition (excluding fats for hard butter and puff pastry margarine), comprising the step of transesterifying a raw fat containing a triglyceride composed of saturated fatty acids having 13 to 15 carbon atoms and a non-animal fat other than the triglyceride to obtain a transesterified fat composition, wherein the transesterified fat composition contains 2% to 40% by mass of saturated fatty acids having 13 to 15 carbon atoms in its total fatty acid content.

Images