3-hydroxybutyric acid-containing oil and fat composition

Abstract

This 3-hydroxybutyric-acid-containing oil and fat composition contains 3-hydroxybutyric acid and / or a salt thereof, an edible oil and fat, and a protein, and has improved dispersibility in water.

Description

[Technical Field]

[0001] The present invention relates to a 3-hydroxybutyric acid-containing oil or fat composition. [Background technology]

[0002] 3-hydroxybutyric acid (hereinafter simply referred to as "3HB") is a substance that is naturally present in the human body and is attracting attention as a revolutionary energy source that can replace carbohydrates.

[0003] 3HB is produced by ingesting medium-chain fatty acids (MCTs), such as those found in coconut oil, and is then metabolized in the body, enters the bloodstream, and is converted into energy. This process allows 3HB to be converted into energy more quickly than carbohydrates via the glycolysis pathway. In other words, ingesting 3HB from an external source allows it to be converted into energy more quickly than carbohydrates via the glycolysis pathway.

[0004] Furthermore, 3HB has the effect of suppressing the absorption of fat and sugar by cells. In other words, taking 3HB externally has the effect of suppressing sugar absorption and promoting fat burning, which is a dietary effect.

[0005] In addition to its role as a simple energy source, 3HB is also believed to improve cognitive function and long-term memory function, as well as prevent Alzheimer's disease.

[0006] In light of these functions of 3HB, its use as an energy substance for athletes or as a diet and health food is being considered.

[0007] On the other hand, 3HB and its salts (particularly the potassium salt) are highly water-soluble and deliquescent, making them extremely difficult to handle in a solid state such as a powder.

[0008] In addition, 3HB has a strong sour taste, which can be unpleasant when taken orally. While neutralizing 3HB to reduce this sour taste can be considered, this approach results in excessive salt content and is undesirable. Adding silicon dioxide, calcium silicate, or dextrin as an anti-caking agent is also an option, but these have upper intake limits and contain carbohydrates, making them undesirable in combination with 3HB. Summary of the Invention [Problem to be solved by the invention]

[0009] Under the circumstances described above, the present inventors have discovered that both the deliquescence and sourness of 3HB can be suppressed by preparing a composition containing 3HB and a specific oil (particularly, oil particles containing an oil component that is preferably a β-type oil containing XXX-type triglycerides).

[0010] To enhance the effects of 3HB by external administration, good dispersibility in water is required for oral ingestion. However, as described above, when a composition containing 3HB and a specific oil or fat (especially oil or fat particles containing an oil or fat component that is preferably a β-type oil or fat containing XXX-type triglycerides) is prepared, even if both the deliquescence and sourness of 3HB can be suppressed, the composition has poor dispersibility in water, resulting in separation of the 3HB and / or water from the oil or fat. For this reason, in its current state, it is difficult to apply the composition to oral ingestion applications such as dietary supplements.

[0011] The present invention is intended to solve the above-mentioned problems, and has an object to provide a composition containing 3HB and an oil or fat, which has improved dispersibility in water. [Means for solving the problem]

[0012] As a result of extensive research to achieve the above object, the present inventors have discovered that the inclusion of 3-hydroxybutyric acid and / or a salt thereof, edible oils and fats, and protein can improve the dispersibility in water of a composition containing 3HB and oils and fats. Based on this finding, the present inventors have conducted further research and completed the present invention. Specifically, the present invention encompasses the following features.

[0013] Item 1. A 3-hydroxybutyric acid-containing fat or oil composition containing 3-hydroxybutyric acid and / or a salt thereof, an edible fat or oil, and a protein.

[0014] Item 2. The 3-hydroxybutyric acid-containing fat and oil composition according to Item 1, wherein the edible fat and oil is a fat and oil particle containing a fat and oil component including one or more XXX-type triglycerides having a fatty acid residue X at positions 1 to 3 of glycerin.

[0015] Item 3. The 3-hydroxybutyric acid-containing oil composition according to Item 2, wherein the oil component contains a β-type oil.

[0016] Item 4. The 3-hydroxybutyric acid-containing oil or fat composition according to Item 2 or 3, wherein the number of carbon atoms in the fatty acid residue is an integer of 10 to 22.

[0017] Item 5. The 3-hydroxybutyric acid-containing oil or fat composition according to any one of Items 2 to 4, wherein the oil or fat particles have a plate-like shape.

[0018] Item 6. The 3-hydroxybutyric acid-containing fat and oil composition according to any one of Items 1 to 5, wherein the edible fat and oil content is 0.5 to 200 parts by mass per 100 parts by mass of the 3-hydroxybutyric acid and / or a salt thereof.

[0019] Item 7. The 3-hydroxybutyric acid-containing fat and oil composition according to any one of Items 1 to 6, wherein the protein is at least one selected from the group consisting of whey protein, casein protein, soy protein, pea protein, wheat protein, egg protein, and rice protein.

[0020] Item 8. The 3-hydroxybutyric acid-containing oil and fat composition according to any one of Items 1 to 7, wherein the content of the protein is 30 to 2000 parts by mass per 100 parts by mass of the 3-hydroxybutyric acid and / or a salt thereof.

[0021] Item 9. The 3-hydroxybutyric acid-containing oil or fat composition according to any one of Items 1 to 8, wherein the salt of 3-hydroxybutyric acid is at least one selected from the group consisting of alkali metal salts, alkaline earth metal salts, and ammonium salts of 3-hydroxybutyric acid.

[0022] Item 10. The 3-hydroxybutyric acid-containing oil or fat composition according to any one of Items 1 to 9, wherein the 3-hydroxybutyric acid and / or a salt thereof has an R configuration.

[0023] Item 11. The 3-hydroxybutyric acid-containing oil and fat composition according to any one of Items 1 to 10, which is an orally ingested 3-hydroxybutyric acid-containing oil and fat composition.

[0024] Item 12. The 3-hydroxybutyric acid-containing oil or fat composition according to any one of Items 1 to 11, which is an aqueous dispersion.

[0025] Item 13. The 3-hydroxybutyric acid-containing oil or fat composition according to any one of Items 1 to 11, which is solid.

[0026] Item 14. A method for producing the 3-hydroxybutyric acid-containing oil or fat composition according to any one of items 1 to 13, (1) mixing the 3-hydroxybutyric acid and / or a salt thereof, the edible oil and fat, and the protein; A manufacturing method comprising:

[0027] Item 15. The step (1) is carried out in water, and further (2) A step of removing water from the 3-hydroxybutyric acid-containing oil and fat composition in the form of an aqueous dispersion obtained in the step (1) and isolating the solid 3-hydroxybutyric acid-containing oil and fat composition. Item 15. The manufacturing method according to Item 14, comprising:

[0028] Item 16. The method according to Item 15, wherein the water is removed by freeze-drying.

[0029] Item 17. A nutritional supplement comprising the 3-hydroxybutyric acid-containing oil or fat composition according to any one of items 1 to 13.

[0030] Item 18. A method for improving the water dispersibility of a 3-hydroxybutyric acid-containing oil or fat composition containing 3-hydroxybutyric acid and / or a salt thereof by mixing 3-hydroxybutyric acid and / or a salt thereof, edible oil or fat, and protein. [Effects of the Invention]

[0031] According to the present invention, by adding a protein to a composition containing 3HB and an oil or fat, it is possible to provide a composition with improved dispersibility in water.

[0032] In particular, unlike emulsifiers, there is no upper limit to the amount of protein that can be orally ingested, and large amounts can be incorporated, making it easy to improve dispersibility in water. Furthermore, when a large amount of protein is incorporated, it is possible to simultaneously ingest energy from 3HB and protein from the protein.

[0033] Furthermore, when a specific oil or fat (particularly, oil or fat particles containing an oil or fat component that is preferably a β-type oil or fat containing XXX-type triglycerides) is used as the edible oil or fat, the deliquescence and sourness of 3HB are particularly easily suppressed. [Brief explanation of the drawings]

[0034] [Figure 1] 1 is a photograph showing the water dispersibility of Examples 1 to 5 and Comparative Example 1. [Figure 2] 1 is a photograph showing the water dispersibility of Examples 6 to 8. [Figure 3] 1 is a photograph showing the water dispersibility of Examples 9 to 12. [Figure 4] 1 is a photograph showing the water dispersibility of Examples 13 to 16. [Figure 5] 1 is a photograph showing the water dispersibility of Examples 17 to 20. [Figure 6] 1 is a photograph showing the water dispersibility of Examples 21 and 22. [Figure 7] 1 is a photograph showing the water dispersibility of Comparative Examples 2 to 10. [Figure 8] 1 is a photograph showing the appearance of the 3-hydroxybutyric acid-containing fat and oil compositions obtained in Examples 23 to 25 one week after preparation. DETAILED DESCRIPTION OF THE INVENTION

[0035] In this specification, the term "containing" is a concept that encompasses all of "comprise," "consist essentially of," and "consist only of."

[0036] In addition, in this specification, when a numerical range is expressed as "A to B," it means A or more and B or less.

[0037] Although the embodiments of the present invention will be described below, various modifications of the form and details are possible without departing from the spirit and scope of the claims.

[0038] 1,3-hydroxybutyric acid-containing oil and fat composition The 3-hydroxybutyric acid-containing fat and oil composition of the present invention contains 3-hydroxybutyric acid and / or a salt thereof, an edible fat and oil, and a protein.

[0039] (1-1) 3-Hydroxybutyric acid and / or its salts 3-Hydroxybutyric acid (3HB) is a compound represented by the following formula:

[0040] [ka]

[0041] 3HB may be in the form of a salt. The salt form of 3HB is not particularly limited, and examples include alkali metal salts (sodium salt, potassium salt, lithium salt, etc.), alkaline earth metal salts (magnesium salt, calcium salt, etc.), and ammonium salt.

[0042] 3HB and its salts can be used alone or in combination of two or more. Among these, potassium salt, which has a high upper limit for salt intake, is preferred to avoid excessive salt intake. When potassium salt of 3HB is included as 3-hydroxybutyric acid and / or its salt, the total amount of 3-hydroxybutyric acid and / or its salt is taken as 100% by mass, and the potassium salt content can be, for example, 20-100% by mass, 40-100% by mass, 60-100% by mass, or 80-100% by mass.

[0043] The three-dimensional structure of 3HB and / or its salts may be either the R configuration (R isomer) or the S configuration (S isomer). From the viewpoints of energy delivery to the body, water dispersibility, suppression of deliquescence, suppression of sourness, etc., the R configuration (R isomer) is preferred.

[0044] 3HB and / or a salt thereof may be in the form of either a liquid (e.g., an aqueous solution or an ethanol solution) or a solid, but a solid form is particularly preferred. Having such a form helps to suppress the deliquescence of the resulting composition. Furthermore, when preparing from a liquid, the 3HB content in the composition can be increased by removing the water or solvent remaining in the composition after or during mixing using an evaporator or freeze-drying, or by adding seed crystals to promote crystallization.

[0045] There are no particular limitations on the size of 3HB and / or its salt, and it can be set appropriately depending on the type of salt in the 3HB salt.

[0046] The method for producing 3HB used in the present invention is not particularly limited, and it can be produced by a conventionally known method. For example, the same applies to salts of 3-hydroxybutyric acid, which can be produced by conventionally used salt formation processes, desalting processes, salt exchange processes, etc.

[0047] In the 3-hydroxybutyric acid-containing oil and fat composition of the present invention, the content of 3HB and / or a salt thereof is not particularly limited. For example, when the 3-hydroxybutyric acid-containing oil and fat composition of the present invention is solid, the content of 3HB and / or a salt thereof is preferably 5 to 70% by mass, more preferably 10 to 40% by mass, based on 100% by mass of the total amount of the 3-hydroxybutyric acid-containing oil and fat composition of the present invention, from the viewpoints of energy provided to the body, water dispersibility, deliquescence suppression, sourness suppression, etc. When the 3-hydroxybutyric acid-containing oil and fat composition of the present invention is liquid (aqueous dispersion), the content of 3HB and / or a salt thereof is preferably 1 to 70% by mass, more preferably 2 to 40% by mass, based on 100% by mass of the total amount of the 3-hydroxybutyric acid-containing oil and fat composition of the present invention, from the viewpoints of energy provided to the body, water dispersibility, deliquescence suppression, sourness suppression, etc.

[0048] (1-2) Edible fats and oils There are no particular limitations on the edible oils and fats, and a wide variety of oils and fats can be used.

[0049] Examples of edible fats and oils include vegetable fats and oils such as milk fat, shea butter, olive oil, soybean oil, safflower oil, corn oil, sunflower oil, rapeseed oil, coconut oil, palm oil, palm kernel oil, and fractionated palm oil; and animal fats and oils such as lard and fish oil.

[0050] These edible oils and fats also include oils and fats synthesized from glycerin and fatty acids, fractionated oils thereof, interesterified oils, hydrogenated oils, and the like.

[0051] Examples of fats and oils synthesized from glycerin and fatty acids include medium-chain triglyceride (MCT) fats and oils.

[0052] Examples of fractionated oils include palm oil fractionated oils such as palm olein, palm superolein, palm stearin, and palm midfraction.

[0053] As interesterified oils, for example, interesterified oils of the above-mentioned oils and fats or fractionated oils thereof with other liquid oils and fats, or interesterified oils of medium-chain fatty acid triglyceride (MCT) oils and vegetable oils, etc. can be used.

[0054] Examples of the hydrogenated oil include hydrogenated oils of the above-mentioned fats and oils and fractionated oils thereof, as well as hydrogenated oils of interesterified oils.

[0055] These edible oils and fats also include refined oils and fats, and the refining method for the refined oils and fats when using refined oils and fats is not particularly limited, but examples include chemical refining, physical refining, etc. Chemical refining is a method of refining crude oil that has been pressed and extracted from a raw material by subjecting it to degumming, deacidification, bleaching, dewaxing, deodorization, etc. Physical refining is a method of refining crude oil that has been pressed from a raw material by subjecting it to degumming, bleaching, deacidification, deodorization, etc.

[0056] These edible oils and fats can be used alone or in combination of two or more.

[0057] The form of these edible oils and fats is not particularly limited, and they may be solid or liquid.

[0058] Among these, from the viewpoint of suppressing deliquescence, suppressing sourness, etc., fat particles containing a fat component containing one or more types of XXX-type triglycerides having a fatty acid residue X at positions 1 to 3 of glycerin are preferred.

[0059] oil particles The oil particles are particularly effective in suppressing the deliquescence and sourness of 3HB, but their water dispersibility tends to deteriorate. In the present invention, even in such cases, the water dispersibility can be improved by including a protein described below.

[0060] The fat or oil particles are solid in shape, but are preferably powdery solid at room temperature (20° C.) from the viewpoints of water dispersibility, suppression of deliquescence, suppression of sourness, and the like.

[0061] The loose bulk density of the fat or oil particles is 0.05 to 0.6 g / cm from the viewpoints of water dispersibility, suppression of deliquescence, suppression of sourness, etc. 3 is preferred, and 0.1 to 0.4 g / cm 3 More preferably, 0.1 to 0.3 g / cm 3 is more preferable.

[0062] Here, "loose bulk density" refers to the packing density of powder when allowed to fall naturally. Loose bulk density (g / cm 3 ) is measured by dropping an appropriate amount of oil particles into a measuring cylinder with an inner diameter of 15 mm and a volume of 25 mL from about 2 cm above the top opening of the measuring cylinder, and measuring the mass (g) of the particles and the volume (cm 3 ) and 1cm 3 The mass (g) of the oil particles per unit area is calculated and the average value of three measurements is taken.

[0063] The fat or oil particles are not particularly limited, but from the viewpoints of water dispersibility, suppression of deliquescence, suppression of sourness, etc., it is preferable that the particles have a plate-like shape.

[0064] Furthermore, although the fat and oil particles are not particularly limited, from the viewpoints of water dispersibility, suppression of deliquescence, suppression of sourness, etc., the average particle size (effective diameter) of the particles is, for example, preferably 0.5 to 200 μm, more preferably 1 to 100 μm, even more preferably 1 to 60 μm, and particularly preferably 1 to 30 μm.

[0065] Here, the average particle size (effective diameter) in the present invention is a value (d50: measured value of particle size at 50% of the cumulative value in the particle size distribution) measured by wet measurement based on a laser diffraction scattering method (ISO133201 and ISO9276-1) using a particle size distribution analyzer (manufactured by Nikkiso Co., Ltd., device name: Microtrac MT3300ExII).

[0066] The effective diameter means the particle size of a sphere when the measured diffraction pattern of the crystal to be measured matches the theoretical diffraction pattern obtained assuming the crystal is spherical.

[0067] In this way, in the case of the laser diffraction scattering method, the effective diameter is calculated by fitting the theoretical diffraction pattern obtained assuming a spherical shape to the actually measured diffraction pattern, so measurement can be performed on the same principle whether the object to be measured has a plate-like shape or a spherical shape. Here, the plate-like shape is not particularly limited, but from the viewpoints of water dispersibility, suppression of deliquescence, suppression of sourness, etc., the aspect ratio is preferably 1.1 or more, more preferably 1.2 to 3.0, even more preferably 1.3 to 2.5, and particularly preferably 1.4 to 2.0.

[0068] The aspect ratio here is defined as the ratio of the long side length to the short side length of a circumscribing rectangle that circumscribes the particle shape to minimize its area. Furthermore, when the particles are spherical, the aspect ratio is less than 1.1. In the conventional method of dissolving and directly spraying oils and fats with a high solid fat content at room temperature, such as extremely hardened oils, the oil and fat particles assume a spherical shape due to surface tension, resulting in an aspect ratio of less than 1.1. The aspect ratio is determined by directly observing arbitrarily selected particles with a scanning electron microscope, measuring their major and minor axis lengths, and averaging the measured number of particles.

[0069] Oil and fat components From the viewpoints of water dispersibility, suppression of deliquescence, suppression of sourness, etc., the fat and oil particles preferably contain a fat and oil component containing one or more XXX-type triglycerides having a fatty acid residue X at positions 1 to 3 of glycerin. The fat and oil component preferably contains at least one XXX-type triglyceride, but may contain other triglycerides.

[0070] The above-mentioned fat and oil component preferably contains β-type fats and oils from the viewpoints of water dispersibility, suppression of deliquescence, suppression of sourness, etc. Here, β-type fats and oils are fats and oils consisting only of β-type crystals, which is one of the crystalline polymorphs of fats and oils. Other crystalline polymorphs include β'-type fats and α-type fats, and β'-type fats and oils are fats and oils consisting only of β'-type crystals, which is one of the crystalline polymorphs of fats and oils. α-type fats and oils are fats and oils consisting only of α-type crystals, which is one of the crystalline polymorphs of fats and oils. Some fat and oil crystals have the same composition but different sublattice structures (crystal structures), and these are called crystalline polymorphs. Representative types include hexagonal, orthorhombic perpendicular, and triclinic parallel, which are called α-type, β'-type, and β-type, respectively.

[0071] The melting points of the polymorphs increase in the order of α-form, β'-form, and β-form, and the melting points of the polymorphs vary depending on the type of fatty acid residue X. Therefore, Table 1 below shows the melting points (°C) of the polymorphs for tricaprin, trilaurin, trimyristin, tripalmitin, tristearin, triarachydin, and tribehenin, respectively. Table 1 was prepared based on Nissim Garti et al., "Crystallization and Polymorphism of Fats and Fatty Acids," Marcel Dekker Inc., 1988, pp. 32-33. In preparing Table 1, the melting points (°C) were rounded to one decimal place. Furthermore, if the composition of a fat or oil and the melting points of each of its polymorphs are known, it is possible to detect at least whether or not a β-form fat or oil is present in the fat or oil.

[0072] [Table 1]

[0073] These polymorphs are identified by X-ray diffraction, and the diffraction conditions are as follows: 2dsinθ=nλ(n=1,2,3) is given by

[0074] Diffraction peaks appear at positions satisfying the above equation. Here, d is the lattice constant, θ is the diffraction (incidence) angle, λ is the wavelength of the X-ray, and n is a natural number. The diffraction peaks corresponding to the short spacing, 2θ = 16 to 27°, provide information about the lateral packing (sublattice) within the crystal, allowing for the identification of polymorphs. In particular, for triacylglycerols, characteristic peaks of β-type appear around 2θ = 19°, 23°, and 24° (around 4.6 Å, 3.9 Å, and 3.8 Å), while a characteristic peak of α-type fats and oils appears around 21° (4.2 Å). Note that each peak may have an error of ±0.5°. X-ray diffraction measurements are performed using an X-ray diffractometer (Rigaku Corporation, horizontal sample X-ray diffractometer UItima IV) maintained at 20°C. CuKα radiation (1.54 Å) is the most commonly used X-ray source.

[0075] Here, from the viewpoints of water dispersibility, suppression of deliquescence, suppression of sourness, etc., the oil and fat component preferably contains β-type oil or fats as the main component (50% by mass or more). In a preferred embodiment, the oil and fat component is essentially composed of β-type oil and fat, in a more preferred embodiment, the oil and fat component is composed of β-type oil and fat, and in a particularly preferred embodiment, the oil and fat component is composed solely of β-type oil and fat.

[0076] The case where the oil / fat component is composed only of β-type oils / fat means that α-type oils / fat and / or β'-type oils / fat are not detected by differential scanning calorimetry. Another preferred embodiment is when the oil / fat component (or oil / fat particles containing the oil / fat component) has a diffraction peak at around 4.5 to 4.7 Å, preferably around 4.6 Å, in X-ray diffraction measurement, and does not have an X-ray diffraction peak at the short spacing of α-type oils / fat and / or β'-type oils in Table 1, particularly does not have a diffraction peak at around 4.2 Å. In such a case, it can be determined that all of the oil / fat component is β-type oils / fat.

[0077] In a further aspect of the present invention, it is preferable that all of the above-mentioned fat and oil components are β-type fats, but this does not exclude the inclusion of other α-type fats or β'-type fats. Here, an indicator of the fat and oil component "containing β-type fats" in the present invention and the relative amount of β-type fats to the total amount of α-type fats and β-type fats can be estimated from the intensity ratio of the characteristic peak of β-type fats to the characteristic peak of α-type fats among X-ray diffraction peaks: [intensity of the characteristic peak of β-type fats / (intensity of the characteristic peak of α-type fats+intensity of the characteristic peak of β-type fats)] (hereinafter also referred to as peak intensity ratio).

[0078] Specifically, based on the findings of the above-mentioned X-ray diffraction measurement, the ratio of the peak intensity at 2θ=19° (4.6 Å), which is a characteristic peak of β-type fats, to the peak intensity at 2θ=21° (4.2 Å), which is a characteristic peak of α-type fats, is calculated as 19° / (19°+21°)[4.6 Å / (4.6 Å+4.2 Å)], which is an index representing the amount of β-type fats present in the above-mentioned fat and oil component, and it can be understood that "β-type fats are contained." In the present invention, from the viewpoints of water dispersibility, suppression of deliquescence, suppression of sourness, etc., it is most preferable that all of the above-mentioned fat and oil components are β-type fats (i.e., peak intensity ratio = 1). However, for example, the lower limit of the peak intensity ratio is preferably 0.4 or more, more preferably 0.5 or more, even more preferably 0.6 or more, particularly preferably 0.7 or more, especially preferably 0.75 or more, and especially especially preferably 0.8 or more. If the peak intensity is 0.4 or more, it can be considered that β-type fats and oils are contained as the main component (50% by mass or more). The upper limit of the peak intensity ratio is preferably 1, but may be 0.99 or less, 0.98 or less, 0.95 or less, 0.93 or less, 0.90 or less, 0.85 or less, 0.80 or less, etc. The peak intensity ratio may be any one of the above lower limit and upper limit values, or any combination thereof.

[0079] XXX triglycerides From the viewpoints of water dispersibility, suppression of deliquescence, suppression of sourness, etc., the above-mentioned oil and fat component preferably contains one or more XXX type triglycerides having a fatty acid residue X with a carbon number of x at positions 1 to 3 of glycerin. The XXX type triglycerides are triglycerides having a fatty acid residue X with a carbon number of x at positions 1 to 3 of glycerin, and each fatty acid residue X is the same as each other.

[0080] Here, the carbon number x is preferably an integer of 10 to 22, more preferably an integer of 12 to 22, still more preferably an integer of 14 to 20, and particularly preferably an integer of 16 to 18, from the viewpoints of water dispersibility, suppression of deliquescence, suppression of sourness, etc.

[0081] The fatty acid residue X may be a saturated or unsaturated fatty acid residue. Specific examples of the fatty acid residue X include, but are not limited to, residues of capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, etc. From the viewpoints of water dispersibility, suppression of deliquescence, suppression of sourness, etc., preferred fatty acids include lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, etc., more preferred are myristic acid, palmitic acid, stearic acid, arachidic acid, etc., and even more preferred are palmitic acid, stearic acid, etc.

[0082] The XXX triglycerides may be used alone or in combination of two or more kinds. From the viewpoints of water dispersibility, suppression of deliquescence, suppression of sourness, etc., one or two kinds are preferred, and one kind is more preferred.

[0083] The content of the XXX triglyceride is preferably 50 to 100% by mass, more preferably 60 to 99% by mass, even more preferably 70 to 97% by mass, and particularly preferably 80 to 95% by mass, based on the total amount of the fat and oil components contained in the fat and oil particles as 100% by mass, from the viewpoints of water dispersibility, suppression of deliquescence, suppression of sourness, etc. When a plurality of XXX triglycerides are contained in the fat and oil component, it is preferable to adjust the total amount thereof to be within the above range.

[0084] Other triglycerides The above-mentioned oil particles may contain, as an oil component, triglycerides other than the above-mentioned XXX triglycerides. The other triglycerides may be a plurality of types of triglycerides, and may be synthetic oils or natural oils.

[0085] Examples of synthetic oils include glyceryl tricaprylate and glyceryl tricaprate.

[0086] Examples of natural fats and oils include cocoa butter, sunflower oil, rapeseed oil, soybean oil, cottonseed oil, and the like.

[0087] The content of other triglycerides may be 1% by mass or more, for example, about 5 to 50% by mass, based on 100% by mass of the total amount of all triglycerides in the fat or oil particles. The content of other triglycerides is, for example, preferably 0 to 30% by mass, more preferably 0 to 18% by mass, even more preferably 0 to 15% by mass, and particularly preferably 0 to 8% by mass.

[0088] Other components contained in oil particles The fat particles may contain, in addition to the fat components such as the triglycerides, other components (additives) such as emulsifiers, flavorings, skim milk powder, whole milk powder, cocoa powder, sugar, dextrin, sweeteners, coloring agents, etc. These optional components can be added externally to the fat particles, but by including them in the fat particles in advance, these optional components can be reliably and easily adhered to the food base material.

[0089] The amount of these other ingredients can be any amount as long as it does not impair the effects of the present invention, but it is preferable that the amount is not too large, taking into account the use in oral ingestion.

[0090] The content of these other components is, for example, preferably 0.001 to 70% by mass, more preferably 0.01 to 65% by mass, and even more preferably 0.1 to 30% by mass, with the total amount of the fat or oil particles being 100% by mass.

[0091] However, taking into consideration water dispersibility, suppression of deliquescence, suppression of sourness, etc., as well as oral ingestion applications, it is preferable that the oil particles contained in the 3-hydroxybutyric acid-containing oil composition of the present invention consist essentially of the above-mentioned oil and fat components, and it is also preferable that the oil and fat components consist essentially of triglycerides.

[0092] Here, "consisting essentially of only the above-mentioned oil and fat components" means that the content of the oil and fat components contained in the oil and fat particles is, for example, 85 to 100% by mass, preferably 90 to 100% by mass, and more preferably 95 to 100% by mass, with the total amount of the oil and fat particles being 100% by mass.

[0093] When the 3-hydroxybutyric acid-containing oil and fat composition of the present invention is solid, the content of the edible oil and fat is preferably 1 to 50 mass% and more preferably 2 to 40 mass% relative to 100 mass% of the total amount of the 3-hydroxybutyric acid-containing oil and fat composition of the present invention, from the viewpoints of water dispersibility, suppression of deliquescence, suppression of sourness, etc. When the 3-hydroxybutyric acid-containing oil and fat composition of the present invention is liquid (aqueous dispersion), the content of the edible oil and fat is preferably 0.1 to 40 mass% and more preferably 0.5 to 10 mass% relative to 100 mass% of the total amount of the 3-hydroxybutyric acid-containing oil and fat composition of the present invention, from the viewpoints of water dispersibility, suppression of deliquescence, suppression of sourness, etc.

[0094] The 3-hydroxybutyric acid-containing oil and fat composition of the present invention contains 3HB and / or a salt thereof, the above-mentioned edible oil and fat, and a protein. From the viewpoints of water dispersibility, suppression of deliquescence, suppression of sourness, etc., the content of the edible oil and fat is preferably 0.5 to 200 parts by mass, more preferably 1 to 100 parts by mass, even more preferably 3 to 90 parts by mass, and particularly preferably 5 to 50 parts by mass, per 100 parts by mass of 3HB and / or a salt thereof. When the content of the edible oil and fat is not too low, deliquescence is easily suppressed, and when the content of the edible oil and fat is not too high, sourness is easily suppressed.

[0095] By blending 3HB and / or its salt, edible oil and fat, and protein in the above-mentioned blending ratio, the surface of the 3HB and / or its salt is coated with the edible oil and fat, making it easier to achieve the effects of suppressing deliquescence and sourness.

[0096] (1-3) Protein The protein is not particularly limited, and whey protein, casein protein, soy protein (soybean protein), pea protein, wheat protein, egg protein, rice protein, etc. can all be used. In the present invention, not only water-soluble whey proteins such as whey protein, but also water-insoluble proteins can improve the water dispersibility of 3HB while suppressing deliquescence and sourness. Among these, whey protein, casein protein, soy protein (soybean protein), etc. are preferred, and whey protein is more preferred, from the viewpoints of water dispersibility, suppression of deliquescence, suppression of sourness, etc.

[0097] These proteins may be partially hydrolyzed to facilitate improvement of water dispersibility and absorbability, and specific examples of such partially hydrolyzed proteins include water-soluble protein hydrolyzates obtained by partially hydrolyzing proteins contained in a protein raw material using a protease, acid, or the like.

[0098] The protein is preferably in powder form when used. Examples of the form of the protein include pulverized, powdered, powdered, flakes, granules, and the like, and the individual forms are not strictly limited.

[0099] The above proteins are not particularly limited, and known or commercially available products can be used.

[0100] When the 3-hydroxybutyric acid-containing oil and fat composition of the present invention is solid, the protein content is preferably 20 to 90% by mass, and more preferably 30 to 80% by mass, of the total amount of the 3-hydroxybutyric acid-containing oil and fat composition of the present invention, taken as 100% by mass, from the viewpoints of water dispersibility, deliquescence suppression, sourness suppression, etc. When the 3-hydroxybutyric acid-containing oil and fat composition of the present invention is liquid (aqueous dispersion), the protein content is preferably 1 to 90% by mass, and more preferably 2 to 90% by mass, of the total amount of the 3-hydroxybutyric acid-containing oil and fat composition of the present invention, taken as 100% by mass, from the viewpoints of water dispersibility, deliquescence suppression, sourness suppression, etc.

[0101] The 3-hydroxybutyric acid-containing fat and oil composition of the present invention contains 3HB and / or a salt thereof, the above-mentioned edible fat and oil, and a protein. From the viewpoints of water dispersibility, suppression of deliquescence, suppression of sourness, etc., the protein content is preferably 30 to 2,000 parts by mass, more preferably 40 to 1,000 parts by mass, and even more preferably 60 to 800 parts by mass, per 100 parts by mass of 3HB and / or a salt thereof. Note that, since protein can be ingested, an excess of protein can be contained as long as it improves water dispersibility. When water-soluble whey protein is used, an excess of protein can be contained in particular.

[0102] (1-4) Other ingredients The 3-hydroxybutyric acid-containing oil and fat composition of the present invention preferably contains other ingredients as appropriate within the scope of not impairing the objects and effects of the present invention. Such other ingredients are not particularly limited as long as they are edible, and examples thereof include powdered carbohydrates and dietary fiber.

[0103] Carbohydrates usually refer to carbohydrates other than dietary fiber. Examples of carbohydrates include edible sugars such as monosaccharides, disaccharides, oligosaccharides, sugar alcohols, isomerized sugar, and starch hydrolysates. More specifically, examples include glucose (monosaccharide), table sugar, maltose, lactose, trehalose (all disaccharides), maltitol, palatinit (all sugar alcohols), glucose-fructose corn syrup, fructose-glucose corn syrup (all isomerized sugar), starch syrup (a mixture of glucose, maltose, and dextrin), and dextrin (a starch hydrolysate).

[0104] Examples of dietary fiber include wheat bran, corn bran, oat bran, cellulose-based fibers extracted from plants (e.g., corn fiber, soybean dietary fiber, beet fiber, etc.), cellulose, crystalline cellulose, agar, chitosan, chitin, hemicellulose, lignin, glucan, etc.

[0105] When these other components are contained, the content thereof is preferably within a range that does not impair the objects and effects of the present invention. For example, when the 3-hydroxybutyric acid-containing oil-and-fat composition of the present invention is solid, the content of the other components is preferably 0 to 10% by mass, more preferably 0.01 to 5% by mass, based on 100% by mass of the total amount of the 3-hydroxybutyric acid-containing oil-and-fat composition of the present invention, from the viewpoints of water dispersibility, deliquescence suppression, sourness suppression, etc. When the 3-hydroxybutyric acid-containing oil-and-fat composition of the present invention is liquid (aqueous dispersion), the content of the other components is preferably 0 to 5% by mass, more preferably 0.01 to 3% by mass, based on 100% by mass of the total amount of the 3-hydroxybutyric acid-containing oil-and-fat composition of the present invention, from the viewpoints of water dispersibility, deliquescence suppression, sourness suppression, etc.

[0106] (1-5) 3-Hydroxybutyric Acid-Containing Oil and Fat Composition The 3-hydroxybutyric acid-containing oil or fat composition of the present invention can be in the form of a solid or a liquid (aqueous dispersion). That is, it can be stored as a solid such as a powder and orally ingested as is or in combination with water, or it can be dispersed in water to form an aqueous dispersion and orally ingested.

[0107] In any case, by mixing 3-hydroxybutyric acid and / or its salt with edible oils and fats and proteins, the water dispersibility of 3-hydroxybutyric acid and / or its salt can be improved and deliquescence and sourness can be suppressed, making it suitable for oral intake and allowing for the convenient intake of 3HB, an energy source, making it useful as a nutritional supplement, etc.

[0108] Method for producing 2,3-hydroxybutyric acid-containing oil and fat composition The method for producing the 3-hydroxybutyric acid-containing oil and fat composition of the present invention is not particularly limited, but may be, for example, (1) Adding 3HB and / or a salt thereof, edible oil and fat, and protein When the 3-hydroxybutyric acid-containing oil or fat composition of the present invention contains the other components described above, it is preferable to add the other components when carrying out step (1).

[0109] For example, when the 3-hydroxybutyric acid-containing oil and fat composition of the present invention is obtained as a liquid (aqueous dispersion), step (1) may be carried out, for example, as follows: (1A) A step of dispersing 3HB and / or a salt thereof, edible oil and fat, and protein in water. In this process, excellent water dispersibility can also be obtained by directly dispersing 3HB and / or a salt thereof, edible oil or fat, and protein in water without dry mixing.

[0110] When the 3-hydroxybutyric acid-containing oil and fat composition of the present invention is obtained as a solid, 3HB and / or a salt thereof, edible oil and fat, and protein can be dry mixed and pulverized, which also improves the water dispersibility of the resulting 3-hydroxybutyric acid-containing oil and fat composition of the present invention to a certain extent.

[0111] The mixing method is not particularly limited, and any known method can be used, such as mechanical mixing using a mixer or mill.

[0112] However, from the viewpoint of easily suppressing aggregation of the solid 3-hydroxybutyric acid-containing oil and fat composition and easily further improving the water dispersibility of the solid 3-hydroxybutyric acid-containing oil and fat composition, after the above step (1A), (2) A step of removing water from the 3-hydroxybutyric acid-containing oil and fat composition in the form of an aqueous dispersion obtained in the step (1A) and isolating the solid 3-hydroxybutyric acid-containing oil and fat composition. It is preferable to have:

[0113] In step (2), the method for removing water from the 3-hydroxybutyric acid-containing oil and fat composition in the form of an aqueous dispersion and isolating the solid 3-hydroxybutyric acid-containing oil and fat composition is not particularly limited, and examples thereof include methods for isolating water from the 3-hydroxybutyric acid-containing oil and fat composition in the form of an aqueous dispersion by concentration using an evaporator or the like, freeze-drying, etc. Among these, from the viewpoints of particularly easily suppressing aggregation and further improving water dispersibility, it is preferable to isolate water by freeze-drying.

[0114] When freeze-drying is employed in step (2), the freeze-drying method is not particularly limited. For example, the 3-hydroxybutyric acid-containing oil and fat composition as an aqueous dispersion can be frozen by leaving it to stand at −80 to −20° C., preferably −50 to −30° C., for 8 to 48 hours, preferably 12 to 24 hours, and then dried using a freeze dryer or the like for 12 to 72 hours, preferably 24 to 48 hours.

[0115] In step (1), the order of mixing the components is not particularly limited, and the components may be mixed simultaneously or sequentially. However, when dry mixing is used for oil particles containing an oil component containing one or more XXX-type triglycerides having a fatty acid residue X at positions 1 to 3 of glycerin, it is preferable to first mix 3-hydroxybutyric acid and / or a salt thereof with the edible oil and fat, and then mix with the protein. When 3HB and / or a salt thereof, edible oil and fat, and protein are dispersed in water as in step (1A) above, they can also be added simultaneously without dry mixing.

[0116] When the edible fat or oil is a fat or oil particle containing a fat or oil component containing one or more XXX-type triglycerides having a fatty acid residue X at positions 1 to 3 of glycerin, the method for producing the fat or oil particle is not particularly limited.

[0117] Specifically, the fat particles can be obtained by the following production method: A fat particle raw material containing one or more XXX-type triglycerides having a fatty acid residue X at positions 1 to 3 of glycerin is melted, and the melt is maintained at a specific cooling temperature to solidify the material, thereby obtaining powdery fat particles without employing special processing means such as spraying or mechanical pulverization using a pulverizer such as a mill.

[0118] More specifically, an example of a method includes (a) preparing a fat particle raw material containing the above-mentioned XXX triglycerides, optionally heating the fat particle raw material obtained in step (a) as step (b) to dissolve the triglycerides contained in the fat particle raw material to obtain the molten fat particle raw material, and (d) cooling and solidifying the fat particle raw material to obtain fat particles containing β-fat and having a plate-like particle shape. Note that the fat particles can also be produced by applying known pulverization means such as a hammer mill or a cutter mill to the solid obtained after cooling.

[0119] The cooling in the step (d) may be carried out, for example, by cooling the molten oil / fat particle raw material at a temperature lower than the melting point of the β-type oil / fat of the oil / fat component contained in the oil / fat particle raw material and satisfying the following formula: Cooling temperature (℃) = carbon number x x 6.6 - 68 It is preferable that the cooling temperature is equal to or higher than the cooling temperature determined by the following formula:

[0120] Cooling within this temperature range allows efficient production of β-type fats and oils, resulting in fine crystals, making it easy to obtain fat particles. The term "fine" as used herein refers to a case in which the primary particles (the smallest crystals) are, for example, 20 μm or less, preferably 15 μm or less, and more preferably 10 μm. Furthermore, cooling within this temperature range facilitates production of β-type fats and oils in a static state, and facilitates the formation of plate-like fat particles. The average particle size of the fat particles contained in the 3-hydroxybutyric acid-containing fat composition of the present invention is the same as described above.

[0121] For this purpose, the fat particles can be produced, for example, by the following steps: (a) preparing a raw material for fat or oil particles containing XXX triglycerides; (b) an optional step of optionally heating the fat or oil particle raw material obtained in step (a) to dissolve triglycerides contained in the fat or oil particle raw material to obtain the fat or oil particle raw material in a molten state; (d) cooling and solidifying the fat particle raw material to obtain fat particles containing β-type fats and oils and having a plate-like particle shape; It can be produced by a method comprising:

[0122] In addition, an optional step (c) for promoting particle generation, such as (c1) a seeding step, (c2) a tempering step, or (c3) a pre-cooling step, may be included between the above steps (b) and (d). Furthermore, in the above step (d), fat particles can also be obtained by applying impact (such as crushing, loosening, vibrating, or sieving) to the solid material having voids obtained after cooling.

[0123] The above steps (a) to (d) will be explained below.

[0124] (a) Raw material preparation process The fat particle raw material containing XXX triglycerides prepared in step (a) may be produced based on a method for producing fats and oils such as ordinary XXX triglycerides containing one or more XXX triglycerides having a fatty acid residue X with a carbon number of x at positions 1 to 3 of glycerin, or may be readily available on the market.

[0125] Here, the XXX triglyceride specified by the number of carbon atoms x and the fatty acid residue X is the same as that of the target fat and oil component to be finally obtained except for the crystal polymorphism. The raw material may also contain β-type fats and oils.

[0126] For example, the raw material may contain 0 to 0.1% by mass, 0.0001 to 0.05% by mass, or 0.0002 to 0.01% by mass of β-type fats. However, since β-type fats disappear when the raw material is heated or otherwise melted, the raw material may be in a molten state. When the raw material is in a molten state, for example, being substantially free of β-type fats does not necessarily mean that XXX triglycerides are present, but also means that substantially all of the fat and oil components are not β-type fats. The presence of β-type fats can be confirmed by the diffraction peaks attributable to β-type fats in the above-mentioned X-ray diffraction measurement, or by confirming β-type fats by differential scanning calorimetry. The amount of β-type fats present in a material that is "substantially free of β-type fats" can be estimated from the intensity ratio of the characteristic peak of β-type fats to the characteristic peak of α-type fats among the X-ray diffraction peaks [intensity of the characteristic peak of β-type fats / (intensity of the characteristic peak of α-type fats + intensity of the characteristic peak of β-type fats)] (peak intensity ratio). The peak intensity ratio of the fat or oil particle raw material is, for example, preferably 0 to 0.2, more preferably 0.0001 to 0.15, and even more preferably 0.0002 to 0.10. The fat or oil particle raw material may contain one or more of the above-mentioned XXX type triglycerides.

[0127] Specifically, the XXX triglyceride can be produced by direct synthesis using a fatty acid or a fatty acid derivative and glycerin. The direct synthesis method for the XXX triglyceride is as follows: (i) A method of directly esterifying a fatty acid having a carbon number X with glycerin (direct ester synthesis), (ii) A method of reacting a fatty acid alkyl (e.g., fatty acid methyl, fatty acid ethyl, etc.) in which the carboxyl group of a fatty acid X having a carbon number x is bonded to an alkoxyl group with glycerin under basic or acidic catalytic conditions (transesterification synthesis using a fatty acid alkyl); (iii) A method (acid halide synthesis) in which a fatty acid halide (e.g., fatty acid chloride, fatty acid bromide, etc.) in which the hydroxyl group of the carboxyl group of fatty acid X having carbon number x is substituted with a halogen atom is reacted with glycerin in the presence of a basic catalyst.

[0128] The XXX triglyceride can be produced by any of the above-mentioned methods (i) to (iii). From the viewpoint of ease of production, however, it is preferable to produce it by (i) direct ester synthesis or (ii) transesterification synthesis using a fatty acid alkyl, and it is more preferable to produce it by (i) direct ester synthesis.

[0129] To produce XXX triglycerides by (i) direct ester synthesis, it is preferable to use 3 to 5 moles, and more preferably 3 to 4 moles, of fatty acid X or fatty acid Y per mole of glycerin from the viewpoint of production efficiency.

[0130] The reaction temperature in (i) direct ester synthesis of XXX triglycerides may be any temperature at which the water produced by the esterification reaction can be removed from the system, and is, for example, preferably 120° C. to 300° C., more preferably 150° C. to 270° C., and even more preferably 180° C. to 250° C. By carrying out the reaction at 180 to 250° C., XXX triglycerides can be produced particularly efficiently.

[0131] In the (i) direct ester synthesis of XXX triglycerides, a catalyst that promotes the esterification reaction may be used. Examples of the catalyst include acid catalysts and alkaline earth metal alkoxides. The amount of the catalyst used is preferably about 0.001 to 1% by mass based on the total mass of the reaction raw materials.

[0132] In the (i) direct ester synthesis of XXX triglycerides, after the reaction, the catalyst and unreacted raw materials can be removed by carrying out known purification treatments such as washing with water, alkaline deoxidation and / or deoxidation under reduced pressure, and adsorption treatment. Furthermore, the obtained reaction product can be further purified by carrying out decolorization and deodorization treatment.

[0133] The amount of XXX triglycerides contained in the above-mentioned oil particle raw material is preferably 50 to 100% by mass, more preferably 55 to 95% by mass, even more preferably 60 to 90% by mass, and particularly preferably 65 to 85% by mass, when the total mass of all triglycerides contained in the raw material is 100% by mass.

[0134] Furthermore, commercially available triglyceride compositions or synthetic oils and fats can be used as raw materials for the oil and fat components contained in the oil and fat particles containing XXX triglycerides. Examples of triglyceride compositions include hard palm stearin (manufactured by Nisshin Oillio Group, Inc.), extremely hydrogenated rapeseed oil (manufactured by Yokoseki Oil & Fat Industries Co., Ltd.), and extremely hydrogenated soybean oil (manufactured by Yokoseki Oil & Fat Industries Co., Ltd.). Examples of synthetic oils and fats include tripalmitin (manufactured by Tokyo Chemical Industry Co., Ltd.), tristearin (manufactured by Sigma-Aldrich), tristearin (manufactured by Tokyo Chemical Industry Co., Ltd.), triarachidin (manufactured by Tokyo Chemical Industry Co., Ltd.), and tribehenin (manufactured by Tokyo Chemical Industry Co., Ltd.). Since extremely hydrogenated palm oil has a low content of XXX triglycerides, it can be used as a diluting component for triglycerides.

[0135] As described above, the fat and oil particles containing the XXX triglyceride may optionally contain other components such as partial glycerides, fatty acids, antioxidants, emulsifiers, and solvents such as water.

[0136] When the fat or oil particle raw material containing the XXX triglyceride contains a plurality of components, they may be mixed arbitrarily. Any known mixing method may be used for the mixing operation as long as a homogeneous reaction substrate can be obtained. For example, the mixing can be performed using a paddle mixer, an azihommixer, a disper mixer, or the like.

[0137] The mixing operation may be carried out under heating as necessary. The heating temperature is preferably about the same as that in step (b) described below. For example, the temperature is preferably 50 to 120°C, more preferably 60 to 100°C, even more preferably 70 to 90°C, and particularly preferably 78 to 82°C.

[0138] (b) A step of obtaining the molten oil / fat particle raw material Before the step (d), if the fat or oil particle raw material containing XXX triglycerides prepared in the step (a) is in a molten state when prepared, it is preferably cooled as is without heating. On the other hand, if it is not in a molten state when prepared, it is preferably optionally heated to melt the triglycerides contained in the fat or oil particle raw material to obtain a molten fat or oil particle raw material.

[0139] Here, the fat or oil particle raw material is preferably heated to a temperature equal to or higher than the melting point of the triglyceride contained in the fat or oil particle raw material, and more preferably to a temperature at which the XXX triglyceride can be melted. The heating temperature is preferably 70 to 200° C., more preferably 75 to 150° C., and even more preferably 80 to 100° C. Furthermore, heating can be continued for, for example, 0.1 to 3 hours, preferably 0.3 to 2 hours, and more preferably 0.5 to 1 hour.

[0140] (d) A step of cooling the molten oil particle raw material to obtain oil particles. It is preferable to further cool and solidify the molten fat particle raw material containing XXX triglycerides prepared in the above step (a) or (b) to incorporate β-type fats and oils into fat particles having a plate-like particle shape.

[0141] Here, in order to "cool and solidify the molten fat particle raw material," it is preferable to maintain the molten fat particle raw material at a temperature lower than the melting point of the β-type fat of the fat component contained in the fat particle raw material as the upper limit of the cooling temperature. For example, in the case of XXX triglyceride having three stearic acid residues with 18 carbon atoms, the melting point of the β-type fat is 74°C (Table 1), so the "temperature lower than the melting point" is preferably a temperature 1 to 30°C lower than the melting point (i.e., 44 to 73°C), more preferably a temperature 1 to 20°C lower than the melting point (i.e., 54 to 73°C), even more preferably a temperature 1 to 15°C lower than the melting point (i.e., 59 to 73°C), and particularly preferably a temperature 1 to 10°C lower than the melting point (i.e., 64 to 73°C).

[0142] In order to obtain β-type fats and oils, it is preferable to maintain the lower limit of the cooling temperature at a temperature equal to or higher than the cooling temperature calculated by the following formula. Cooling temperature (℃) = number of carbon x × 6.6 - 68 In the formula, the carbon number x represents the carbon number x of the XXX type triglyceride contained in the fat or oil particle raw material.

[0143] By setting the cooling temperature at or above this level, when the fat or oil is crystallized to obtain a beta fat or oil containing XXX triglycerides, the α fat or β' fat other than the beta fat or oil tends to be less likely to crystallize. Since the cooling temperature mainly depends on the molecular size of the XXX triglyceride, it can be understood that there is a certain correlation between the carbon number x and the lower limit of the optimal cooling temperature.

[0144] For example, when the XXX triglyceride contained in the fat or oil particle raw material is a XXX triglyceride having three stearic acid residues each having a carbon number of 18, the lower limit of the cooling temperature is preferably 50.8°C or higher. Therefore, in the case of a XXX triglyceride having three stearic acid residues each having a carbon number of 18, the temperature at which the molten fat or oil particle raw material is "cooled and solidified" is more preferably 50.8°C or higher and 72°C or lower.

[0145] Furthermore, when the XXX triglyceride is a mixture of two or more types, it is preferable to determine the lower limit of the cooling temperature according to the type having the smaller carbon number x. For example, when the XXX triglyceride contained in the oil / fat particle raw material is a mixture of an XXX triglyceride having three palmitic acid residues with a carbon number of 16 and an XXX triglyceride having three stearic acid residues with a carbon number of 18, it is preferable to set the lower limit of the cooling temperature to 37.6°C or higher according to the type having the smaller carbon number of 16.

[0146] In another embodiment, the lower limit of the cooling temperature is suitably a temperature equal to or higher than the melting point of the α-type oil or fat corresponding to the β-type oil or fat in the oil or fat particle raw material containing XXX-type triglyceride. For example, when the XXX-type triglyceride contained in the oil or fat particle raw material is an XXX-type triglyceride having three stearic acid residues with a carbon number of 18, the melting point of the α-type oil or fat in the XXX-type triglyceride having three stearic acid residues is 55°C (Table 1), and therefore, in such a case, the temperature for "cooling and solidifying the molten oil or fat particle raw material" is preferably 55°C or higher and 72°C or lower.

[0147] In yet another embodiment, the cooling of the molten oil / fat raw material containing XXX triglycerides is preferably carried out by cooling so that the final temperature is preferably -2 to 46°C, more preferably 12 to 44°C, and even more preferably 14 to 42°C, for example, when x is 10 to 12. The final temperature in cooling can be, for example, when x is 13 or 14, preferably 24 to 56°C, more preferably 32 to 54°C, and even more preferably 40 to 52°C; when x is 15 or 16, preferably 36 to 66°C, more preferably 44 to 64°C, and even more preferably 52 to 62°C; when x is 17 or 18, preferably 50 to 72°C, more preferably 54 to 70°C, and even more preferably 58 to 68°C; when x is 19 or 20, preferably 62 to 80°C, more preferably 66 to 78°C, and even more preferably 70 to 77°C; and when x is 21 or 22, preferably 66 to 84°C, more preferably 70 to 82°C, and even more preferably 74 to 80°C. At the above final temperature, the mixture can be allowed to stand for preferably 2 hours or more, more preferably 4 hours or more, and even more preferably 6 hours or more, and preferably for 2 days or less, more preferably 24 hours or less, and even more preferably 12 hours or less.

[0148] (c) Particle generation promotion step Furthermore, it is also preferable to provide a particle generation promoting step (c) before step (d) or between step (a) or (b) and step (d). In step (c), the molten oil / fat particle raw material used in step (d) may be treated by a seeding method, a tempering method, a pre-cooling method, or the like. That is, it is also preferable to configure step (c) as a seeding step (c1), a tempering step (c2), or a pre-cooling step (c3). These steps (c1) to (c3) may be performed alone or in combination. Here, "between step (a) or (b) and step (d)" means during step (a) or (b), after step (a) or (b) and before step (d), and during step (d).

[0149] The seeding method and tempering method are particle production promotion methods in which, in the production of the oil particles contained in the 3-hydroxybutyric acid-containing oil composition of the present invention, the molten oil particle raw material is treated before being cooled to the final temperature in order to make it easier to turn the molten oil particle raw material into a powder.

[0150] The seeding method is a method of promoting particle formation by adding a small amount of a particle core (seed) component to a molten fat particle raw material during cooling. Specifically, for example, a fat powder containing preferably 80% by mass or more, more preferably 90% by mass or more, of XXX triglycerides having the same carbon number as the XXX triglycerides in the molten fat particle raw material obtained in step (b) can be prepared as the core (seed) component. When the temperature of the molten fat particle raw material reaches, for example, a temperature of ±0 to +10°C of the final cooling temperature, preferably +5 to +10°C, during cooling, 0.1 to 1 part by mass, preferably 0.2 to 0.8 parts by mass of this core fat powder is added per 100 parts by mass of the molten fat particle raw material, thereby promoting particle formation of the fat particle raw material.

[0151] The tempering method is a method for cooling a molten fat particle raw material, in which the raw material is cooled once to a temperature lower than the cooling temperature in step (d), for example, 5 to 20°C lower, preferably 7 to 15°C lower, and more preferably about 10°C lower, for preferably 10 to 120 minutes, more preferably about 30 to 90 minutes, before allowing the raw material to stand at the final cooling temperature, thereby promoting granulation of the fat particle raw material.

[0152] Furthermore, the pre-cooling method is a method of temporarily cooling the molten fat particle raw material obtained in step (a) or (b) at a temperature between the temperature at which the fat particle raw material containing XXX triglycerides was prepared and the cooling temperature at which the fat particle raw material was cooled before being cooled in step (d). In other words, a method of temporarily pre-cooling at a temperature lower than the temperature at which the fat particle raw material was prepared in step (a) or (b) and higher than the cooling temperature in step (d). (c3) Following the pre-cooling step, it is preferable to cool the fat particle raw material at the cooling temperature at which the fat particle raw material was cooled in step (d). The temperature higher than the cooling temperature in step (d) may be, for example, a temperature 2 to 40°C higher, preferably 3 to 30°C higher, more preferably 4 to 30°C higher, and even more preferably about 5 to 10°C higher than the cooling temperature in step (d). The lower the pre-cooling temperature, the shorter the main cooling time at the cooling temperature in step (d).

[0153] In other words, unlike the seeding method and tempering method, the pre-cooling method is a method that can promote granulation of the fat particle raw material simply by gradually lowering the cooling temperature, and is therefore very advantageous when produced industrially.

[0154] The solid material having voids obtained after cooling in step (d) is preferably a solid material having voids whose volume is increased compared to the molten oil / fat particle raw material, and since the solid material having voids easily disintegrates into a powdery substance, the voids can be disintegrated into a powdery substance during the filling process of filling into a container or the transporting process, without the need for a special powdering process.

[0155] In more detail, it is preferable to first melt the fat particle raw material containing the XXX triglyceride to obtain a molten fat particle raw material, and then cool it to form a solid having voids whose volume is larger than that of the molten fat particle raw material. The solid fat particle raw material having voids can be crushed by applying a light impact, and the solid easily collapses into particles.

[0156] Here, the method of applying the impact is not particularly limited, but examples include a method of crushing the porous solid material using a normal crusher (hammer mill, cutter mill, etc.), a method of loosening the porous solid material with a spatula, rubber spatula, shovel, etc., a method of vibrating the porous solid material placed in a container, and a method of sieving the porous solid material and applying an impact.

[0157] Although the embodiments of the present invention have been described above, the present invention is not limited to these examples, and it goes without saying that the present invention can be embodied in various forms without departing from the spirit of the present invention. [Example]

[0158] Hereinafter, the embodiments of the present invention will be described in more detail based on examples, but the present invention is not limited to these examples.

[0159] In the following examples, (R)-3-hydroxybutyric acid crystals were obtained by concentrating an aqueous solution of R-3-hydroxybutyric acid produced according to the method described in Example 1 of JP 2019-176839 A in an evaporator set at 70 ° C. until no water was released, adding 30% by mass of ethyl acetate and seed crystals of R-3-hydroxybutyric acid relative to the weight of the concentrated solution, and leaving it overnight at 4 ° C. The crystals were filtered and dried and used in the following examples.

[0160] As the edible fat and oil, fat particles were produced according to the following Production Example 1. Furthermore, Coconard RK manufactured by Kao Corporation was used as the medium-chain fatty acid (MCT) oil, and BOSCO extra virgin olive oil manufactured by Nisshin Oillio Group, Ltd. was used as the olive oil.

[0161] The whey protein used was Isopro manufactured by BULKSPORTS (Body Plus International Co., Ltd.), the casein protein used was BigCasein manufactured by BULKSPORTS (Body Plus International Co., Ltd.), and the soy protein used was SoyPro manufactured by BULKSPORTS (Body Plus International Co., Ltd.).

[0162] <Analysis method> Triglyceride composition Gas chromatography analysis conditions DB1-ht (0.32mm x 0.1μm x 5m) Agilent Technologies (123-1131) Injection volume: 1.0μL Inlet: 370℃ Detector: 370℃ Split ratio: 50 / 1 35.1kPa constant pressure Column CT: 200℃ (0 min hold) ~ (15℃ / min) ~ 370℃ (4 min hold).

[0163] X-ray diffraction measurement Measurements were performed using an X-ray diffractometer, Ultima IV (Rigaku Corporation), with CuKα (λ=1.542 Å) as the radiation source, a Cu filter, an output of 1.6 kW, an operating angle of 0.96 to 30.0°, and a measurement speed of 2° / min. If the measurement showed only a peak near 4.6 Å and no peak near 4.1 to 4.2 Å, it was determined that all of the fat and oil components were beta-type fats and oils.

[0164] From the results of the X-ray diffraction measurements, the peak intensity ratio = [intensity of the characteristic peak of β type (2θ = 19° (4.6 Å)) / (intensity of the characteristic peak of α type (2θ = 21° (4.2 Å)) + intensity of the characteristic peak of β type (2θ = 19° (4.6 Å)))] was measured as an index representing the amount of β type fats and oils present.

[0165] Loose bulk density Loose bulk density of fat particles (g / cm 3) is measured by dropping oil particles into a measuring cylinder with an inner diameter of 15 mm and a volume of 25 mL from about 2 cm above the top opening of the measuring cylinder, and measuring the mass (g) of the oil particles and the volume (cm 3 ) and 1cm 3 The mass (g) of the fat particles per unit area was calculated.

[0166] Aspect Ratio The particles were directly observed using a scanning electron microscope S-3400N (manufactured by Hitachi High-Technologies Corporation), and the lengths of the major and minor axes of arbitrarily selected particles were measured using image analysis particle size distribution measurement software (Mac-View, manufactured by Mountec Co., Ltd.), and the average values ​​of the measured numbers were calculated.

[0167] ·Average particle size The average particle size of the obtained fat and oil particles was measured by wet measurement using a particle size distribution measuring device (manufactured by Nikkiso Co., Ltd., device name: Microtrac MT3300ExII) based on the laser diffraction scattering method (ISO133201 and ISO9276-1).

[0168] Specifically, a very small-volume circulator (Nikkiso Co., Ltd., device name: USVR) was attached to the particle size distribution analyzer, and water was circulated as the dispersion solvent. Also, 0.06 g of sample and 0.6 g of neutral detergent were placed in a 100 ml beaker and mixed with a spatula. After mixing, 30 ml of water was added, and the mixture was subjected to an ultrasonic cleaner (Aiwa Medical Industry Co., Ltd., device name: AU-16C) for 1 minute. The mixture was then dropped and circulated for measurement. The measured particle size (d50) at 50% of the cumulative value in the obtained particle size distribution was taken as the average particle size.

[0169] (Production Example 1: Preparation of oil particles) One kilogram of triglyceride (XXX type: 79.1% by mass, heavily hydrogenated rapeseed oil, manufactured by Yokoseki Oil & Fat Industries Co., Ltd.) having stearic acid residues (18 carbon atoms) at positions 1 to 3 was maintained at 80°C for 10 hours to completely melt, and then cooled in a 60°C thermostatic bath for 15 hours to form a solid with increased volume and voids. After crystallization was completed, the solid was cooled to room temperature (25°C). The resulting solid was pulverized in a hammer mill to produce a powdered oil (melting point: 67.4°C, loose bulk density: 0.2 g / cm). 3 The obtained particles had an aspect ratio of 1.6, an average particle size of 14.4 μm, an X-ray diffraction peak of 4.6 Å, and a peak intensity ratio of 0.89. These were used as fat particles.

[0170] (Examples 1 to 22 and Comparative Example 1) 35 g of distilled water and the amount of protein (whey protein, casein protein, or soy protein) shown in Tables 2 to 7 were added to a mill mixer (Iris Ohyama Co., Ltd., IJM-M800-W) and gently stirred. Then, the amounts of (R)-3-hydroxybutyric acid crystals shown in Tables 2 to 7 and the amounts of edible fats and oils shown in Tables 2 to 7 were added, and pulverization was performed four times for 5 seconds. However, for Examples 1 to 12 and 21 to 22 and Comparative Example 1 in Tables 2 to 4 and 7, which used the fat and oil particles of Production Example 1, the (R)-3-hydroxybutyric acid crystals and the fat and oil particles of Production Example 1 were first mixed by pulverization five times for 3 seconds using a mill mixer (Iris Ohyama Co., Ltd., IJM-M800-W), and the resulting mixture was added to water containing protein (whey protein, casein protein, or soy protein), and pulverization was performed in the same manner. The obtained 3-hydroxybutyric acid-containing oil and fat compositions of each Example and Comparative Example were transferred to a container and allowed to stand, and photographed and evaluated for appearance after 1 hour and 1 day. The evaluation criteria are as follows. The results are shown in Tables 2 to 7 and Figures 1 to 6. In Tables 2 to 7, the water dispersibility indicates the water dispersibility after 1 day.

[0171] S: Almost completely dispersed A: About half of it dispersed, but the rest settled. B: Almost no dispersion

[0172] [Table 2]

[0173] [Table 3]

[0174] [Table 4]

[0175] [Table 5]

[0176] [Table 6]

[0177] [Table 7]

[0178] (Comparative Examples 2 to 10) 0.8 g of (R)-3-hydroxybutyric acid crystals and 0.2 g of the fat and oil particles of Production Example 1 were mixed in advance using a mill mixer (Iris Ohyama Co., Ltd., IJM-M800-W).

[0179] Add 20g (20ml) of distilled water and 1g of the resulting mixture to a bottle, then 8 and 9 The emulsifiers shown in 8 and 9 In Comparative Example 2, no emulsifier was added.

[0180] The resulting mixture was then stirred with a stirrer for 30 minutes, and the appearance was evaluated immediately after stirring. The evaluation criteria were as follows. The results are shown in Tables 8 and 9 and FIG. 7.

[0181] S: Almost completely dispersed A: About half of it dispersed, but the rest settled. B: Almost no dispersion

[0182] [Table 8]

[0183] [Table 9]

[0184] From the above results, it can be seen that Examples 1 to 22 contain 3-hydroxybutyric acid and / or a salt thereof, edible oils and fats, and protein, and therefore have excellent water dispersibility, even compared to Comparative Example 1, which does not contain protein.

[0185] On the other hand, when various emulsifiers, including those contained in proteins such as Lesion P, are used as in Comparative Examples 3 to 10, even if the emulsifier is added up to the maximum amount that can be contained for oral ingestion, water dispersibility cannot be improved, and it can be seen that there is not much difference from Comparative Example 2, which does not contain an emulsifier. In other words, it can be seen that emulsifiers are inappropriate as water dispersants for compositions containing 3HB and edible oils and fats (particularly compositions for oral ingestion).

[0186] Examples 23 to 25 (R)-3-hydroxybutyric acid crystals, edible fats and oils, and protein were weighed out in the proportions shown in Table 10 below, and dry-pulverized five times for 3 seconds using a mill mixer (Iris Ohyama Co., Ltd., IJM-M800-W). 1 g of the resulting 3-hydroxybutyric acid-containing fat and oil composition (solid) from each Example was weighed into a petri dish and left uncovered in a room adjusted to 25°C for one week, after which the appearance was evaluated. The evaluation criteria were as follows. The results are shown in Table 10 and FIG. 8.

[0187] S: Highly fluid and smooth state A: Slightly moist, but in a fluid powder state B: A state in which aggregation or deliquescence occurs

[0188] [Table 10]

[0189] From the above results, it can be seen that the deliquescence of 3HB can be suppressed by containing 3-hydroxybutyric acid and / or its salt, edible oil and fat, and protein in Examples 23 to 25. Furthermore, when the sourness of Examples 23 to 25 was evaluated by three experienced panelists, all three panelists evaluated that the sourness of all Examples was suppressed.

[0190] Example 26 1.4 g of (R)-3-hydroxybutyric acid crystals, 0.6 g of the oil particles of Production Example 1 (Production Example 1), and 2.0 g of whey protein were added to 20 mL of distilled water, and the mixture was stirred five times for 3 seconds using a mill mixer (Iris Ohyama Co., Ltd., IJM-M800-W).

[0191] The resulting 3-hydroxybutyric acid-containing oil and fat composition was transferred to a container and allowed to stand. After one hour and one day, the composition was photographed and its appearance was evaluated. In both cases, the composition was found to be almost completely dispersed.

[0192] The obtained 3-hydroxybutyric acid-containing oil and fat composition was frozen overnight in a freezer at −30° C. and then treated with a freeze dryer (EYELA FREEZEDRYER FD-1) for 24 hours.

[0193] The solid obtained by freeze-drying was pulverized in the above-mentioned mill mixer, and then 1 g of the resulting powder was taken out and dispersed in 20 mL of water. It was almost completely dispersed, and even after one day it was still almost completely dispersed, with no precipitate observed.

[0194] Example 27 1.4 g of (R)-3-hydroxybutyric acid crystals, 0.6 g of the oil particles of Production Example 1 (Production Example 1), and 4.0 g of whey protein were added to 20 mL of distilled water, and the mixture was stirred five times for 3 seconds using a mill mixer (Iris Ohyama Co., Ltd., IJM-M800-W).

[0195] The resulting 3-hydroxybutyric acid-containing oil and fat composition was transferred to a container and allowed to stand. After one hour and one day, the composition was photographed and its appearance was evaluated. In both cases, the composition was found to be almost completely dispersed.

[0196] The obtained 3-hydroxybutyric acid-containing oil and fat composition was frozen overnight in a freezer at −30° C. and then treated with a freeze dryer (EYELA FREEZEDRYER FD-1) for 24 hours.

[0197] The solid obtained by freeze-drying was pulverized in the above-mentioned mill mixer, and then 1 g of the resulting powder was taken out and dispersed in 20 mL of water. It was almost completely dispersed, and even after one day it was still almost completely dispersed, with no precipitate observed.

[0198] Furthermore, the following are production examples of fat particles other than the fat particles of Production Example 1. The powdery fat particles obtained by these production examples can also be used in the same manner as the above examples, and exhibit the effects of the present invention.

[0199] (Manufacturing example 2):x=16 25 g of triglyceride (XXX type: 89.7% by mass, tripalmitin, manufactured by Tokyo Chemical Industry Co., Ltd.) having palmitic acid residues (16 carbon atoms) at positions 1 to 3 was maintained at 80°C for 0.5 hours to completely melt, and then cooled in a 50°C thermostatic bath for 12 hours to form a solid with increased volume and voids. After completing crystallization, the solid was cooled to room temperature (25°C). The resulting solid was loosened to obtain a powdery crystalline composition (loose bulk density: 0.2 g / cm). 3 The obtained powder had an aspect ratio of 2.0, an average particle size of 119 μm, an X-ray diffraction peak of 4.6 Å, and a peak intensity ratio of 0.90.

[0200] (Manufacturing example 3):x=16 25 g of triglyceride (XXX type: 69.9% by mass, hard palm stearin, manufactured by Nisshin Oillio Group Co., Ltd.) having palmitic acid residues (16 carbon atoms) at positions 1 to 3 was maintained at 80°C for 0.5 hours to completely melt, and then cooled in a 50°C thermostatic bath for 12 hours to form a solid with increased volume and voids. After completing crystallization, the solid was cooled to room temperature (25°C). The resulting solid was loosened to obtain a powdery crystalline composition (loose bulk density: 0.3 g / cm). 3 The obtained X-ray diffraction peak was 4.6 Å, the aspect ratio was 1.4, the average particle size was 99 μm, and the peak intensity ratio was 0.88.

[0201] (Production Example 4): x = 16, (c2) Tempering method 15 g of triglyceride (XXX type: 89.7% by mass, tripalmitin, manufactured by Tokyo Chemical Industry Co., Ltd.) having palmitic acid residues (16 carbon atoms) at positions 1 to 3 was maintained at 80°C for 0.5 hours to completely melt, cooled in a 30°C thermostatic bath for 0.01 hours, and then left to stand in a 60°C thermostatic bath for 2 hours to form a solid with increased volume and voids. After completing crystallization, the solid was cooled to room temperature (25°C). The resulting solid was loosened to obtain a powdery crystalline composition (loose bulk density: 0.2 g / cm). 3 The obtained powder had an aspect ratio of 2.0, an average particle size of 87 μm, an X-ray diffraction peak of 4.6 Å, and a peak intensity ratio of 0.89.

[0202] (Production Example 5): x = 16, (c1) Seeding method 15 g of triglyceride (XXX type: 89.7% by mass, tripalmitin, manufactured by Tokyo Chemical Industry Co., Ltd.) having palmitic acid residues (16 carbon atoms) at positions 1 to 3 was maintained at 80°C for 0.5 hours to completely melt, and then cooled in a 60°C thermostatic bath until the product temperature reached 60°C. Then, tripalmitin oil powder was added in an amount of 0.1% by mass relative to the raw oil and fat, and the mixture was allowed to stand in the 60°C thermostatic bath for 2 hours to form a solid with increased volume and voids. After completing crystallization, the mixture was cooled to room temperature (25°C). The resulting solid was loosened to obtain a powdered crystalline composition (loose bulk density: 0.2 g / cm). 3The obtained powder had an aspect ratio of 2.0, an average particle size of 92 μm, an X-ray diffraction peak of 4.6 Å, and a peak intensity ratio of 0.89.

[0203] (Manufacturing example 6):x=18 3 g of triglyceride (XXX type: 99.6% by mass, tristearin, manufactured by Sigma-Aldrich) having stearic acid residues (carbon number 18) at positions 1 to 3 was maintained at 80°C for 0.5 hours to completely melt, and then cooled in a 60°C thermostatic bath for 12 hours to form a solid with increased volume and voids. After completing crystallization, the solid was cooled to room temperature (25°C). The resulting solid was loosened to obtain a powdery crystalline composition (loose bulk density: 0.2 g / cm). 3 The obtained X-ray diffraction peak was 4.6 Å, the aspect ratio was 2.0, the average particle size was 30 μm, and the peak intensity ratio was 0.93.

[0204] (Manufacturing example 7):x=18 25 g of triglyceride (XXX type: 96.0% by mass, tristearin, manufactured by Tokyo Chemical Industry Co., Ltd.) having stearic acid residues (carbon number 18) at positions 1 to 3 was maintained at 80°C for 0.5 hours to completely melt, and then cooled in a 55°C thermostatic bath for 12 hours to form a solid with increased volume and voids. After completing crystallization, the solid was cooled to room temperature (25°C). The resulting solid was loosened to obtain a powdery crystalline composition (loose bulk density: 0.2 g / cm). 3 The obtained X-ray diffraction peak was 4.6 Å, the aspect ratio was 2.0, the average particle size was 31 μm, and the peak intensity ratio was 0.88.

[0205] (Production example 8):x=18 25 g of triglyceride (XXX type: 79.1% by mass, heavily hydrogenated rapeseed oil, manufactured by Yokoseki Oil & Fat Industries Co., Ltd.) having stearic acid residues (18 carbon atoms) at positions 1 to 3 was maintained at 80°C for 0.5 hours to completely melt, and then cooled in a 55°C thermostatic bath for 12 hours to form a solid with increased volume and voids. After completing crystallization, the solid was cooled to room temperature (25°C). The resulting solid was loosened to obtain a powdery crystalline composition (loose bulk density: 0.2 g / cm). 3The obtained powder had an aspect ratio of 1.6, an average particle size of 54 μm, an X-ray diffraction peak of 4.6 Å, and a peak intensity ratio of 0.89.

[0206] (Production example 9):x=18 25 g of triglyceride (XXX type: 66.7% by mass, extremely hardened soybean oil, manufactured by Yokozeki Oil & Fat Industries Co., Ltd.) having stearic acid residues (18 carbon atoms) at positions 1 to 3 was maintained at 80°C for 0.5 hours to completely melt, and then cooled in a 55°C thermostatic bath for 12 hours to form a solid with increased volume and voids, completing crystallization, and then cooled to room temperature (25°C). The resulting solid was loosened to obtain a powdery crystalline composition (loose bulk density: 0.3 g / cm). 3 The results were: aspect ratio: 1.4, average particle size: 60 μm, X-ray diffraction peak: 4.6 Å, peak intensity ratio: 0.91.

[0207] (Production example 10):x=18 A triglyceride (XXX type: 84.1% by mass, Nisshin Sunflower Oil (S) (high oleic sunflower oil), manufactured by Nisshin Oillio Group Co., Ltd.) having stearic acid residues (18 carbon atoms) at positions 1 to 3 was completely hydrogenated by a standard method to obtain a hydrogenated product (XXX type: 83.9% by mass). 25 g of the obtained high oleic sunflower oil was maintained at 80°C for 0.5 hours to completely melt it, and then cooled in a 55°C thermostatic bath for 12 hours to form a solid with increased volume and voids, completing crystallization, and then cooled to room temperature (25°C). The obtained solid was loosened to obtain a powdery crystalline composition (loose bulk density: 0.2 g / cm). 3 The obtained powder had an aspect ratio of 1.6, an average particle size of 48 μm, an X-ray diffraction peak of 4.6 Å, and a peak intensity ratio of 0.89.

[0208] (Production example 11):x=18 18.75 g of a triglyceride (XXX type: 66.7% by mass, extremely hydrogenated soybean oil, manufactured by Yokoseki Yushi Kogyo Co., Ltd.) having stearic acid residues (18 carbon atoms) at positions 1 to 3 and 6.25 g of another triglyceride (XXX type: 11.1% by mass, extremely hydrogenated palm oil, manufactured by Yokoseki Yushi Kogyo Co., Ltd.) having stearic acid residues (18 carbon atoms) at positions 1 to 3 were mixed to prepare a raw material oil (XXX type: 53.6% by mass). The raw material oil was maintained at 80°C for 0.5 hours to completely melt, and then cooled in a 55°C thermostatic bath for 12 hours to form a solid with increased volume and voids. After completing crystallization, the solid was cooled to room temperature (25°C). The resulting solid was loosened to obtain a powdery crystalline composition (loose bulk density: 0.3 g / cm). 3 The results were: aspect ratio: 1.4, average particle size: 63 μm, X-ray diffraction peak: 4.6 Å, peak intensity ratio: 0.78. Since the content of XXX-type triglycerides in the extremely hardened palm oil is extremely low, it was used as a diluent (hereinafter the same).

[0209] (Production Example 12): x = 18, (c1) Seeding method 25 g of triglyceride (XXX type: 96.0% by mass, Tristearin, manufactured by Tokyo Chemical Industry Co., Ltd.) having stearic acid residues (18 carbon atoms) at positions 1 to 3 was maintained at 80°C for 0.5 hours to completely melt, and then cooled in a 70°C thermostatic bath until the product temperature reached 70°C. Tristearin oil powder was then added in an amount of 0.1% by mass relative to the raw oil and fat, and the mixture was allowed to stand in the 70°C thermostatic bath for 12 hours to form a solid with increased volume and voids. After completing crystallization, the mixture was cooled to room temperature (25°C). The resulting solid was loosened to obtain a powdered crystalline composition (loose bulk density: 0.2 g / cm). 3 The obtained X-ray diffraction peak was 4.6 Å, the aspect ratio was 2.0, the average particle size was 36 μm, and the peak intensity ratio was 0.88.

[0210] (Production Example 13): x = 18, (c2) Tempering method 15 g of triglyceride (XXX type: 79.1% by mass, extremely hardened rapeseed oil, manufactured by Yokoseki Oil & Fat Industries Co., Ltd.) having stearic acid residues (18 carbon atoms) at positions 1 to 3 was maintained at 80°C for 0.5 hours to completely melt, cooled in a 50°C thermostatic bath for 0.1 hours, and then left to stand in a 65°C thermostatic bath for 6 hours to form a solid with increased volume and voids. After completing crystallization, the solid was cooled to room temperature (25°C). The resulting solid was loosened to obtain a powdery crystalline composition (loose bulk density: 0.2 g / cm). 3 The obtained X-ray diffraction peak was 4.6 Å, the aspect ratio was 1.6, the average particle size was 50 μm, and the peak intensity ratio was 0.90.

[0211] (Production Example 14): x = 18, (c2) Tempering method 15 g of triglyceride (XXX type: 79.1% by mass, highly hydrogenated rapeseed oil, manufactured by Yokoseki Oil & Fat Industries Co., Ltd.) having stearic acid residues (18 carbon atoms) at positions 1 to 3 was maintained at 80°C for 0.5 hours to completely melt, cooled in a 40°C thermostatic bath for 0.01 hours, and then left to stand in a 65°C thermostatic bath for 2 hours to form a solid with increased volume and voids. After completing crystallization, the solid was cooled to room temperature (25°C). The resulting solid was loosened to obtain a powdery crystalline composition (loose bulk density: 0.2 g / cm). 3 The obtained powder had an aspect ratio of 1.6, an average particle size of 52 μm, an X-ray diffraction peak of 4.6 Å, and a peak intensity ratio of 0.89.

[0212] (Production Example 15): x = 18, (c3) Pre-cooling method 25 g of triglyceride (XXX type: 79.1% by mass, rapeseed hardened oil, manufactured by Yokoseki Oil & Fat Industries Co., Ltd.) having stearic acid residues (18 carbon atoms) at positions 1 to 3 was maintained at 80°C for 0.5 hours to completely melt, and the raw oil was kept in a 70°C thermostatic bath until it reached 70°C, and then cooled in a 65°C thermostatic bath for 8 hours to form a solid with increased volume and voids. After completing crystallization, the solid was cooled to room temperature (25°C). The obtained solid was loosened to obtain a powdery crystalline composition (loose bulk density: 0.2 g / cm). 3 The obtained powder had an aspect ratio of 1.6, an average particle size of 60 μm, an X-ray diffraction peak of 4.6 Å, and a peak intensity ratio of 0.89.

[0213] (Manufacturing example 16):x=20 10 g of triglyceride (XXX type: 99.5% by mass, Triarachidin, manufactured by Tokyo Chemical Industry Co., Ltd.) having arachidic acid residues (20 carbon atoms) at positions 1 to 3 was maintained at 90°C for 0.5 hours to completely melt, and then cooled in a 72°C thermostatic bath for 12 hours to form a solid with increased volume and voids. After completing crystallization, the solid was cooled to room temperature (25°C). The resulting solid was loosened to obtain a powdery crystalline composition (loose bulk density: 0.2 g / cm). 3 The obtained powder had an aspect ratio of 2.0, an average particle size of 42 μm, an X-ray diffraction peak of 4.6 Å, and a peak intensity ratio of 0.92.

[0214] (Manufacturing example 17):x=22 10 g of a triglyceride (XXX type: 97.4% by mass, tribehenin, manufactured by Tokyo Chemical Industry Co., Ltd.) having behenic acid residues (22 carbon atoms) at positions 1 to 3 was maintained at 90°C for 0.5 hours to completely melt, and then cooled in a 79°C thermostatic bath for 12 hours to form a solid with increased volume and voids. After completing crystallization, the solid was cooled to room temperature (25°C). The resulting solid was loosened to obtain a powdery crystalline composition (loose bulk density: 0.2 g / cm). 3 The obtained results were: aspect ratio: 2.0, average particle size: 52 μm, X-ray diffraction peak: 4.6 Å, peak intensity ratio: 0.93.

[0215] (Production example 18): x=16, 18 12.5 g of a triglyceride (XXX type: 89.7% by mass, tripalmitin, manufactured by Tokyo Chemical Industry Co., Ltd.) having palmitic acid residues (16 carbon atoms) at the 1st to 3rd positions and 12.5 g of a triglyceride (XXX type: 96.0% by mass, tristearin, manufactured by Tokyo Chemical Industry Co., Ltd.) having stearic acid residues (18 carbon atoms) at the 1st to 3rd positions were mixed to prepare a raw material fat (XXX type: 93.8%). The raw material fat was maintained at 80°C for 0.5 hours to completely melt, cooled in a 55°C thermostatic bath for 16 hours to form a solid with increased volume and voids, and then loosened to obtain a powdery crystalline composition (loose bulk density: 0.2 g / cm). 3The obtained X-ray diffraction peak was 4.6 Å, the aspect ratio was 1.6, the average particle size was 74 μm, and the peak intensity ratio was 0.90.

[0216] (Production example 19): x=16, 18 12.5 g of a triglyceride having palmitic acid residues (carbon number 16) at positions 1 to 3 (XXX type: 69.9% by mass, hard palm stearin, manufactured by Nisshin Oillio Group, Inc.) and 12.5 g of a triglyceride having stearic acid residues (carbon number 18) at positions 1 to 3 (XXX type: 79.1% by mass, hardened rapeseed oil, manufactured by Yokozeki Oil & Fat Industries Co., Ltd.) were mixed to prepare a raw material fat (XXX type: 75.3%). The raw material fat was maintained at 80°C for 0.5 hours to completely melt, cooled in a 55°C thermostatic bath for 16 hours to form a solid with increased volume and voids, and then loosened to obtain a powdery crystalline composition (loose bulk density: 0.3 g / cm). 3 The obtained powder had an aspect ratio of 1.4, an average particle size of 77 μm, an X-ray diffraction peak of 4.6 Å, and a peak intensity ratio of 0.88.

Claims

1. A 3-hydroxybutyric acid-containing fat and oil composition comprising 3-hydroxybutyric acid and / or a salt thereof, edible fat and oil, and protein, wherein the fat and oil component contains β-type fat and oil.

2. The 3-hydroxybutyric acid-containing fat and oil composition according to claim 1, wherein the edible fat and oil is a fat and oil particle containing a fat and oil component including one or more XXX triglycerides having a fatty acid residue X at positions 1 to 3 of glycerin.

3. 3. The 3-hydroxybutyric acid-containing oil or fat composition according to claim 2, wherein the number of carbon atoms in the fatty acid residue is an integer of 10 to 22.

4. The 3-hydroxybutyric acid-containing fat or oil composition according to claim 2 or 3, wherein the fat or oil particles have a plate-like shape.

5. 5. The 3-hydroxybutyric acid-containing fat and oil composition according to claim 1, wherein the content of the edible fat and oil is 0.5 to 200 parts by mass per 100 parts by mass of the 3-hydroxybutyric acid and / or a salt thereof.

6. The 3-hydroxybutyric acid-containing fat or oil composition according to any one of claims 1 to 5, wherein the protein is at least one selected from the group consisting of whey protein, casein protein, soy protein, pea protein, wheat protein, egg protein, and rice protein.

7. 7. The 3-hydroxybutyric acid-containing oil and fat composition according to claim 1, wherein the content of the protein is 30 to 2000 parts by mass per 100 parts by mass of the 3-hydroxybutyric acid and / or a salt thereof.

8. The 3-hydroxybutyric acid-containing oil or fat composition according to any one of claims 1 to 7, wherein the salt of 3-hydroxybutyric acid is at least one selected from the group consisting of alkali metal salts, alkaline earth metal salts, and ammonium salts of 3-hydroxybutyric acid.

9. 9. The 3-hydroxybutyric acid-containing oil or fat composition according to claim 1, wherein the 3-hydroxybutyric acid and / or salt thereof has an R configuration.

10. The 3-hydroxybutyric acid-containing oil or fat composition according to any one of claims 1 to 9, which is an orally ingested 3-hydroxybutyric acid-containing oil or fat composition.

11. The 3-hydroxybutyric acid-containing oil or fat composition according to any one of claims 1 to 10, which is an aqueous dispersion.

12. The 3-hydroxybutyric acid-containing oil or fat composition according to any one of claims 1 to 10, which is solid.

13. A method for producing the 3-hydroxybutyric acid-containing oil or fat composition according to any one of claims 1 to 12, (1) Adding the 3-hydroxybutyric acid and / or a salt thereof, the edible oil and fat, and the protein A manufacturing method comprising:

14. The step (1) is carried out in water, and further (2) A step of removing water from the 3-hydroxybutyric acid-containing oil and fat composition in the form of an aqueous dispersion obtained in the step (1) and isolating the solid 3-hydroxybutyric acid-containing oil and fat composition. The method of claim 13 , comprising:

15. The method of claim 14, wherein the method for removing water is freeze-drying.

16. A nutritional supplement comprising the 3-hydroxybutyric acid-containing oil or fat composition according to any one of claims 1 to 12.

17. A method for improving the water dispersibility of a 3-hydroxybutyric acid-containing oil and fat composition containing 3-hydroxybutyric acid and / or a salt thereof, by mixing 3-hydroxybutyric acid and / or a salt thereof, edible oil and fat, and protein, and causing the oil and fat component to contain β-type oil and fat.

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