US 2013 0071525A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2013/0071525 A1 Kanaya et al. (43) Pub. Date: Mar. 21, 2013

(54) COATING FAT COMPOSITION AND Publication Classification PARTICULATE COMPOSITION USING THE SAME (51) Int. Cl. A2.3L. I./00 (2006.01) (75) Inventors: Kento Kanaya, Takasago-shi (JP); Masayuki Abe, Takasago-shi (JP); Akio (52) U.S. Cl. Sakaki, Takasago-shi (JP); Masao Sato, CPC ...... A23L I/0029 (2013.01) Takasago-shi (JP) USPC ...... 426/99: 426/609: 426/601 (73) Assignee: KANEKA CORPORATION, Osaka-shi, Osaka (JP) (57) ABSTRACT (21) Appl. No.: 13/638,137 A particulate composition, wherein a hydrophilic Substance (22) PCT Fled: Mar. 29, 2011 is polydispersed in a matrix of a fat composition having a solid fat content at 25 C of 58% or more and a solid fat content (86) PCT NO.: at 37 C of 90% or less; and a coating fat composition con S371 (c)(1), taining 45% by weight or more of a triglyceride comprising at (2), (4) Date: Dec. 5, 2012 least both a saturated fatty acid having 6 to 12 carbon atoms and a Saturated fatty acid having 14 or more carbon atoms as (30) Foreign Application Priority Data constituent fatty acids, wherein the proportion of the satu Mar. 29, 2010 (JP) ...... 2010-075.256 rated fatty acid having 14 or more carbon atoms in the con Nov. 4, 2010 (JP) ...... 2010-247766 stituent fatty acids of the whole fat exceeds 50% by weight. Patent Application Publication Mar. 21, 2013 US 2013/0071525 A1

Fig. 1

US 2013/007 1525 A1 Mar. 21, 2013

COATING FAT COMPOSITION AND Document 4), but there are problems, such as the deformation PARTICULATE COMPOSITION USING THE of a coating fat during storage and the Sticking of coating fats. SAME 0008 Moreover, as to enteric properties, a coating fat is required to have a characteristic that it does not disintegrate in TECHNICAL FIELD the stomach in oral ingestion, and it rapidly releases the enclosure on arrival at the intestines. However, it is hard to be 0001. The present invention relates to a particulate com said that a conventional coating fat sufficiently satisfies the position in which a hydrophilic Substance is polydispersed in above characteristic. a matrix of a fat composition, and to a coating fat composition 0009 Patent Document 1: JP-A-2003-252751 that is a Solid at room temperature. O010 Patent Document 2: JP 4038585 0011 Patent Document 3: JP-A-2004-143084 BACKGROUND ART 0012 Patent Document 4: JP-A-2003-61576 0002 An S/O type or W/O type microcapsule can be employed for various applications such as foods, functional DISCLOSURE OF THE INVENTION nutritive foods, specific health foods, medicines, cosmetics, feeds, and agrochemicals, by enclosing an useful component Problems to be Solved by the Invention (core Substance) in a predominately solid fat phase. For 0013 An object of the present invention is to provide a fine microcapsules to be used for Such applications, there are particulate composition which is a Solid at room temperature, demands not only for an increase in yield, a high content of a which has excellent oxidative stability, which encapsulates a core Substance, and a wide choice range of capsule particle large quantity of an enclosure such as a hydrophilic Sub diameter but also for control of a pattern of the release of a stance, which, when coating the enclosure, causes only mini core substance from the viewpoint of DDS. mal heat-induced damage to the enclosure, which has enteric 0003. On the other hand, examples of the S/O type micro properties to be capable of rapidly releasing the coated enclo capsules heretofore known include microcapsules produced Sure when the composition reaches the intestines, and which by the in-liquid drying process (Patent Document 1). Such can be employed for a wide variety of applications such as microcapsules are difficult to use for food applications foods and medicines; and a fat composition which can be used because organic solvents harmful to the human body, Such as in the particulate composition. halogenated hydrocarbons or ethers, are used in their produc tion. Moreover, the microcapsules produced by the in-liquid Means for Solving the Problems drying process can be used as controlled release microcap 0014. The present inventors have investigated earnestly in Sules, but they are problematic in that physical fine pores order to solve the aforementioned problems of the present appeareasily in a capsule casing, a core substance easily leaks invention and, as a result, they have found that a particulate out of the casing or the like. composition using a fat composition having a solid fat content 0004. There has been proposed an S/O type microcapsule within a specific range as a matrix can encapsulate a hydro produced by preparing a fine W/O/W emulsion by membrane philic Substance in a high content and also control the release emulsification using a solid fatas a shell material, followed by of an enclosed hydrophilic Substance in the intestinal tract, freeze-drying (Patent Document 2), but it is difficult to and therefore have completed a first invention. enclose a high content of a core Substance and there are 0015 That is, the first present invention relates to a par problems, such as pressure loss or clogging during membrane ticulate composition, wherein a hydrophilic Substance is emulsification and durability of membranes. polydispersed in a matrix of a fat composition having a solid 0005 Moreover, there are known a W/O type or S/O type fat content at 25 C of 58% or more and a solid fat content at 37 microcapsule in which a hydrophilic bioactive Substance has C of 90% or less. A preferred embodiment thereof relates to a been coated with tripalmitin and a method for its production particulate composition, wherein the fat composition is com by spray drying (Patent Document 3). In this document, the posed of 95 to 60% by weight of a high-melting-point fathigh release characteristic of an enclosed Substance has been melting-point fat and 5 to 40% by weight of a low-melting revealed by immersing the microcapsule in a simulated intes point oil. tinal fluid containing lipase. However, the microcapsule fails 0016. Moreover, the present inventors have investigated to exhibit a sufficient rate in releasing the enclosure in spite of earnestly in order to solve a problem of a second present the fact that it is a fine particle produced by spray-drying. invention and, as a result, they have found that a fat compo 0006 Moreover, since the melting point of the tripalmitin sition having a specific Saturated fatty acid composition as a to be used is high, this method requires an operation of bring constituent fatty acid can be processed at low temperatures ing the enclosure into contact with tripalmitin molten at a high because its melting point is not very high, but it can hold its temperature of 70 C or higher when dispersing the enclosure Solid state at room temperature and is excellent in oxidative in a fat. For this reason, in the event that a material having low stability and also it exhibits excellent enteric properties by heat resistance is used for the enclosure, there is a problem coating an enclosure with the fat composition, and therefore that the deterioration or damage of the enclosure is caused, so have completed the second invention. that expected bioactive effects fail to be demonstrated suffi 0017. That is, the second present invention relates to a ciently. coating fat composition containing 45% by weight or more of 0007 Incidentally, coating fats are used as base materials a triglyceridehaving at least both a saturated fatty acid having of microcapsules enclosing bioactive Substances as described 6 to 12 carbon atoms and a Saturated fatty acid having 14 or above and also are in use for coating of foods, and the like. On more carbon atoms as constituent fatty acids, wherein the the other hand, in conventional coating of foods, for example, proportion of the saturated fatty acid having 14 or more semi-solid fats have been used for coating Snack foods (Patent carbon atoms in the constituent fatty acids of the whole fat US 2013/007 1525 A1 Mar. 21, 2013 exceeds 50% by weight. The coating fat composition can be 0026. The fat composition to be used for the particulate used as the fat composition in the first present invention. composition of the present invention is not particularly restricted as far as its solid fat content at 25 C is 58% or more Effects of the Invention and its solid fat content at 37 C is 90% or less as described above. A fat composition having a solid fat content at 25 C of 0018. According to the present invention, there can be less than 58% cannot exhibit solidity at normal temperature provided a fine particulate composition which is a Solid at (usually 25C); even if such a fat composition is used, it is not room temperature, which has excellent oxidative stability, possible to produce a particulate composition or, even if it is which can include an enclosure such as a hydrophilic Sub possible, a resulting particulate composition will be particles stance at a high content, and further which, when coating the which are semi-solid and sticky at normal temperature and it enclosure, causes only minimal heat-induced damage to the will be very difficult to handle the particles due to the occur enclosure because the coating can be performed at an opera rence of sticking of the particles together or the like. From tion temperature of, for example, 60 C or lower, at which Such a viewpoint, the fat composition preferably has a solid coating using conventional coating fats is difficult to perform, fat content at 25 C of 60% or more. If the solid fat content at and which can release the enclosure in the intestines effi 37C exceeds 90%, the release rate of a hydrophilic substance ciently without decomposing the enclosure in the stomach. in the intestines is low and therefore sufficient enteric prop Moreover, the present invention can be developed into a wide erties cannot be achieved. From the ease of production, a fat variety of application fields, not only to the fields of medi composition having a solid fat content at 37C of 50% or more cines and agrochemicals but also to the field of foods. and 90% or less is preferred, and a fat composition having a 0019. Furthermore, a coating fat composition capable of solid fat content at 37 C of 60% or more and 80% or less is being used as a matrix base of the aforementioned particulate more preferred. From the viewpoint of enteric properties, a fat composition can also be provided. The coating fat composi composition having a solid fat content at 37C of 50% or more tion can be developed into a wide variety of application fields and 85% or less is preferred, a fat composition having a solid because it is of high safety, for example, it can be used as an fat content at 37 C of 50% or more and 75% or less is more edible fat, and it can be applied easily not only to medicines in preferred, and a fat composition having a solid fat content at view of DDS, but also to the field of foods and functional 37 Cof 50% or more and 70% or less is particularly preferred. foods. On the other hand, in view of ease of handling, a fat compo sition having a solid fat content at 37 C of 60% or more and BRIEF DESCRIPTION OF THE DRAWINGS 90% or less is preferred. The fat composition to be used for 0020 FIG. 1 is a SEM photograph of a particulate com the particulate composition of the present invention is a fat position produced in Example 1. composition that has the above-described solid fat content 0021 FIG. 2 is a SEM photograph of a particulate com and it is usually a fat composition that is a Solid or exhibits position after a disintegration test performed in Example 1. solidity at normal temperature as described above. 0027. The fat composition to be used for the particulate PREFERRED MODE FOR CARRYING OUT THE composition of the present invention is not particularly INVENTION restricted if it is one having the above-described solid fat content. For example, naturally occurring fats or industrially 0022. Embodiments of the present invention will be produced fats can be used as they are or ones obtained by described in detail below. separating and/or curing Such fats can be used. Moreover, a 0023 (First Present Invention) fat composition prepared by mixing two or more of the fats 0024. The particulate composition of the first present described above is also usable. Furthermore, a fat composi invention is a particulate composition, wherein a hydrophilic tion produced using a transesterification reaction can also be Substance is polydispersed in a matrix of a fat composition used. From the viewpoint of enteric properties, a fat compo having a solid fat content at 25 C of 58% or more and a solid sition produced using a transesterification reaction is pre fat content at 37 C of 90% or less. ferred. 0025. A solid fat content (solid fat index) is generally a 0028. As the fat composition having the above-described proportion accounted for by a fat component having been Solid fat content, the coating fat composition in the second crystallized and solidified at a specific temperature in a fat; present invention can be used, and the composition will be and in the present application, a fat composition having a described below. solid fat content at 25 C of 58% or more and a solid fat content 0029. The fat composition having the above-described at 37 C of 90% or less is used as a matrix of the particulate Solid fat content can be prepared by mixing a high-melting composition. In the present application, the solid fat contentis point fat having a melting point of 40 C or higher and a determined by heating a fat composition to be measured to or low-melting-point oil having a melting point of 35C or lower above its melting point to melt it completely, holding it at a in desired proportions. This is desirable in the application to prescribed temperature, that is, 25 C or 37 C, for one week, food because the solid fat content in the fat composition can and then performing measurement by a known method. The be freely controlled by simple procedures and it is possible to known method for measuring the solid fat content is not produce the fat composition of the present invention without particularly restricted, and any method may be used such as a using an organic solvent during its production. More prefer method in which a dilatometer is used and an NMR method, able from the viewpoint of enteric properties is a mixture of a which are disclosed in The JOCS Standard Methods for the fat having a melting point of 45 C or higher which is a solid, Analysis of Fats, Oils and Related Materials (edited by Japan disintegration-resistant, hard form at normal temperature as Oil Chemists’ Society) or the like; in Examples disclosed the high-melting-point fat and a liquid fat having a melting below, the NMR method is adopted by which measurement point of 25 C or less which is liquid at normal temperature as can be performed more easily. the low-melting-point oil. The terms “high-melting-point fat” US 2013/007 1525 A1 Mar. 21, 2013 and “low-melting-point oil as used herein each mean a prop oxidative stability, use of rapeseed oil, corn oil, coconut oil, a erty which is exhibited by a whole mixture where two or more low melting fraction of fish oil, medium chain fatty acid components are combined together as fats to be used. triglyceride, and on the like is preferred. 0030 The high-melting-point fat to be used for the present 0032. When the mixture of the high-melting-point fat and invention is not particularly restricted if it is a fat having a the low-melting-point oil is used as the fat composition to be melting point of 40 C or higher. Examples of such a fat used for the particulate composition of the present invention, include animal and vegetable fats, such as palm oil, shea their mixing ratio is not particularly restricted. However, a butter, sal butter, illipe butter, lard, and beef tallow; hydroge mixture of 95 to 60% by weight of the high-melting-point fat nated animal and vegetable oils, such as palm hardened oil, and 5 to 40% by weight of the low-melting-point oil is pre fully hardened palm oil, hardened rapeseed oil, fully hard ferred. If the content of the high-melting-point fat is 95% by ened rapeseed oil, hardened soybean oil, hardened lard oil, weight or more, resulting particles are hard and excellent in and hardened fish oil; fractionated oils obtained by fraction handleability, but release of a hydrophilic substance in the ally purifying high boiling fractions of animal and vegetable intestines tends to become slow. On the other hand, if the fats and their hydrogenated products, such as fractionated content of the high-melting-point fat is less than 60% by coconut oil, fractionated palm kernel oil, fractionated palm weight, since resulting particles will become soft, it may oil, fractionated cacao butter oil, fractionated shea butter oil, become difficult to handle the particles. In ease of production, fractionated lard oil, fractionated hardened soybean oil, and preferred is a mixture of 85 to 70% by weight of the high fractionated hardened fish oil; saturated fatty acid triglycer melting-point fat and 15 to 30% by weight of the low-melt ides, such as tristearin, tripalmitin, and trilaurin; their partial ing-point oil, and more preferred from the viewpoint of glycerides, such as monoglycerides, diglycerides, and fatty enteric properties is a mixture of 80 to 60% by weight of the acids; and edible waxes, such as cera flava, candelilla wax, high-melting-point fat and 20 to 40% by weight of the low and rice bran wax. As the high-melting-point fat in the present melting-point oil. In ease of handling, more preferred is a invention, these may be used alone or two or more of them mixture of 95 to 70% by weight of the high-melting-point fat may be used in combination. As such a high-melting-point and 5 to 30% by weight of the low-melting-point oil. More fat, use of hardened oils, such as fractionated palm oil, hard over, in ease of production, particularly preferred is a mixture ened palm oil, hardened rapeseed oil, tristearin, and tripalm of 80 to 70% by weight of the high-melting-point fat and 20 itin, and fractionated oils of high melting fractions is pre to 30% by weight of the low-melting-point oil, and particu ferred from the viewpoint of easy availability and ease for larly preferred from the viewpoint of enteric properties is a performing melting and solidification by cooling. Moreover, mixture of 70 to 60% by weight of the high-melting-point fat use of fully hardened palm oil, fully hardened rapeseed oil, and 30 to 40% by weight of the low-melting-point oil. In ease fractionated palm oil, tristearin, tripalmitin, and the like is of handling, particularly preferred is a mixture of 90 to 80% preferred from the viewpoint of containing no trans-fatty by weight of the high-melting-point fat and 10 to 20% by acid. Among the above-mentioned high-melting-point fats, at weight of the low-melting-point oil. least one member selected from the group consisting of frac 0033 Moreover, the particulate composition of the tionated palm oil, hardened palm oil, fully hardened palm oil, present invention may contain a hydrophobic component hardened rapeseed oil, fully hardened rapeseed oil, tristearin other than the above-mentioned fats together with the fat and tripalmitin is more preferred. composition to be used as a matrix. Use of bioactive Sub 0031. The low-melting-point oil to be used for the present stances or other useful components as Such a hydrophobic invention is not particularly restricted if it is a fat having a component is preferable because it can cause resulting par melting point of 35C or lower. Examples of such a fat include ticulate compositions to contain not only hydrophilic Sub animal and vegetable fats, such as rapeseed oil, rice oil, pea stances but also hydrophobic components. nut oil, olive oil, corn oil, soybean oil, perilla oil, cotton seed 0034. The hydrophobic substance to be used in this case oil, sunflower oil, Oenothera Biennis oil, sesame oil, saf may be selected according to an intended application as far as flower oil, coconut oil, cacao butter, palm kernel oil, and fish it is a Substance capable of being dispersed or dissolved in the oil; seaweed-derived fats, such as brown seaweed oil and sea fat composition to be used. Examples of the hydrophobic tangle oil; microalgae-derived fats, such as Spirulina Substance include carotenoids, such as -carotene, -carotene, extracted oil; microorganism fats, such as yeast extracted oil lycopene, lutein, astaxanthin, Zeaxanthin, and fucoxanthin; and Mortierella extracted oil; fractionated oils obtained by hydrophobic flavonoids, such as quercetin, catechin, cur fractionally purifying Such low melting fractions, such as a cumin, and coumarin; low water-soluble anthocyanins. Such low melting fraction of palm oil, a low melting fraction of fish as piperine, quercitrin, myricitrin, and maringin; alkaloids, oil, and a low melting fraction of shea butter, medium chain Such as capsaicin, capsiate, caffeine, berberine, and Vincris fatty acid triglycerides, such as tricaprylin and tricaprin; tine; hydrophobic vitamins, such as vitamin A, vitamin D, unsaturated fatty acid triglycerides, such as triolein and trili -tocopherol, -tocopherol, and vitamin K; hydrophobic lign nol; their partial glycerides, such as monoglycerides and dig ans, such as sesamin, Sesamolin, and sesaminol; hydrophobic lycerides; and fatty acids, such as oleic acid, linoleic oil, coenzymes, such as coenzyme Q10. These Substances may be linolenic acid, arachidonic acid, eicosapentaenoic acid, and used alone and two or more of them may be used in combi docosahexaenoic acid. As the low-melting-point oil in the nation. present invention, these may be used alone or two or more of 0035. The hydrophilic substance to be enclosed in the them may be used in combination. As such a low-melting particulate composition of the present invention may be point oil, use of rapeseed oil, rice oil, corn oil, soybean oil, selected according to an intended application as far as it is a olive oil, Sunflower oil, perilla oil, palm kernel oil, diglycer substance that is soluble in water. Examples of the hydro ide, oleic acid, coconut oil, a low melting fraction of fish oil, philic Substance include proteins, peptides, amino acids, anti medium chain fatty acid triglyceride, and the like is preferred biotics, nucleic acids, organic acids, water-soluble vitamins, from the viewpoint of easy availability. From the viewpoint of water-soluble polyphenols, water-soluble coenzymes, miner US 2013/007 1525 A1 Mar. 21, 2013 als, saccharides, terpene glycosides, and viable bacteria. The 0045 Examples of the minerals include calcium, magne above-mentioned substances may be used in the form of sium, iron, Zinc, potassium, Sodium, copper, Vanadium, man derivatives or salts as far as they are hydrophilic. These sub ganese, selenium, molybdenum, cobalt, and the like, as well stances may be used alone and two or more of them may be as compounds to which Such a mineral is bonded. used in combination. 0046 Examples of the saccharides include monosaccha 0036) Examples of the proteins include enzymes, antibod rides, disaccharides, oligosaccharides, Sugar alcohols, and ies, antigens, and hormones. Specific examples thereof other polysaccharides. Specific examples of the monosaccha include proteases, amylases, cellulases, kinases, glucanases, ride include arabinose, Xylose, ribose, glucose, fructose, pectinases, isomerases, lipases, pectinases, interferon, inter galactose, mannose, Sorbose, and rhamnose. Specific leukin, BMP, immunoglobulin, serum albumin, and milk pro examples of the disaccharide include maltose, cellobiose, tein-derived ingredients (e.g., lactoferrin, lactoglobulin, lac trehalose, lactose, and Sucrose. Specific examples of the oli toalbumin, and lactoperoxidase). gosaccharide include maltotriose, raffinose saccharide, and 0037 Examples of the peptides include luteinizing hor stachyose. Specific examples of the Sugar alcohol include mone releasing hormone (LH-RH), insulin, Somatostatin, arabitol, Xylitol, adonitol, mannitol, Sorbitol, and dulcitol. growth hormone, growth hormone releasing hormone (GH Examples of the other polysaccharides include chitin, chito RH), prolactin, erythropoietin, adrenocortical hormone, mel san, agarose, heparin, hyaluronic acid, Xyloglucan, starch, anocyte stimulating hormone, thyrotropin releasing hormone glycogen, pectin, chondroitin Sulfate, heparan Sulfate, and (TRH), thyroid stimulating hormone, luteinizing hormone, keratan Sulfate. follicle stimulating hormone, Vasopressin, oxytocin, calcito 0047. Examples of the terpene glycosides include stevio nin, gastrin, secretin, pancreozymin, cholecystokinin, angio side and glycyrrhizin. tensin, human placental lactogen, human chorionic gonadot 0048. The above-described viable bacteria are preferably ropin, enkephalin, endorphin, kyotorphin, tuftsin, ones Suitable for mammals to oral consume; and examples thymopoietin, thymosin, thymothymulin, thymic humoral thereof include lactobacillus, bifidobacteria, yeast, aspergil factors, blood thymic factors, tumor necrosis factors, colony lus, acetic acid bacteria, butyric acid bacteria, propionic acid inducing factors, motilin, dynorphin, bombesin, neurotensin, bacteria, and saccharification bacteria. cerulein, bradykinin, glutathione, imidazole dipeptides (e.g., 0049. Examples of the lactobacillus include Lactobacillus carnosine, anserine, homoanserine, balenine, and aspartame), acidophilus, Lactobacillus bulgaricus, Lactobacillus brevis, atrial natriuretic factors, nerve growth factors, cell growth Lactobacillus casei, Lactobacillus delbruekii, Lactobacillus factors, neurotrophic factors, peptides having endothelin fermrintii, Lactobacillus fermentum, Lactobacillus gasseri, antagonism, etc., and derivatives thereof, as well as fragments Lactobacillus lactis, Lactobacillus leichmanii, Lactobacillus thereof and derivatives of such fragments. helveticus, Lactobacillus plantarum, Lactobacillus rhamno 0038 Specific examples of the amino acids include gly sus, Lactobacillus salivarius, Lactobacillus thermophilus, cine, alanine, Valine, leucine, isoleucine, phenylalanine, Lactobacilluspentosus, Lactococcus lactis, Lactococcus cre tyrosine, tryptophan, serine, threonine, proline, hydroxypro moris, Pediococcus acidilacticii, Pediococcus cerevisiae, line, cysteine, methionine, aspartic acid, glutamic acid, Pediococcus pentosaceus, Leuconostoc mesenteroides, Leu lysine, arginine, and histidine. conostoc lactis, Streptococcus lactis, Streptococcus cre 0039 Examples of the antibiotics include -lactam type, moris, Streptococcus thermophilus, Streptococcus bulgari aminoglycoside type, tetracyclin type, chloramphenicol type, cus, Enterococcus faecalis, and Enterococcus faecium. macrollide type, ketolide type, polyene macrollide type, gly 0050 Examples of the bifidobacteria include Bifidobacte copeptide type, nucleic acid type, and pyridonecarboxylic rium adolescentis, Bifidobacterium angulatum, Bifidobacte acid type antibiotics. rium animalis, Bifidobacterium bifidum, Bifidobacterium 0040 Specific examples of the nucleic acids include breve, Bifidobacterium catenulatum, Bifidobacterium denti inosinic acid, guanylic acid, Xanthylic acid, ATP, GTP, DNA, colens, Bifidobacterium dentium, Bifidobacterium gallicum, and RNA. Bifidobacterium infantis, Bifidobacterium inopinatum, Bifi 0041) Specific examples of the organic acids include ace dobacterium longum, and Bifidobacterium pseudocatenula tic acid, butyric acid, propionic acid, citric acid, Succinic acid, tliin fumaric acid, lactic acid, gluconic acid, malic acid, tartaric 0051 Examples of the yeast include Saccharomyces bou acid, and pyruvic acid. lardi, Saccharomyces cerevisiae, and Saccharomyces sake. 0042 Specific examples of the water-soluble vitamins 0.052 Examples of the aspergillus include Aspergillus include vitamin B1, vitamin B2, vitamin B6, vitamin B12, Oryzae, Aspergillus niger, and Aspergillus soiae. ascorbic acid, niacin, pantothenic acid, folic acid, lipoic acid, 0053 Examples of the acetic acid bacteria include Aceto and biotin. bacter aceti, Acetobacter xylinum, and Acetobacter Orienta 0043 Specific examples of the water-soluble polyphenols lis. Examples of the butyric acid bacteria include Bacillus include tea flavonoids, such as epigallocatechin gallate, epi tovoi, Bacillus licheniformis, Clostridium butyricum, and catechin gallate, gallocatechin gallate, epigallocatechin, Clostridium acetobutyricum. Examples of the propionic acid theaflavin, and theaflavingallate; anthocyanins, such as nasu bacteria include Propionibacterium shermanii and Propioni nin, shisonin, and enin, flavonoids, such as maringin, hespe bacterium feudenreichii. Examples of the saccharification ridin, and rutin; water-soluble lignans, such as Sesaminol bacteria include Bacillus subtilis, Bacillus mesentericus, and glucosides and pyredinol glycosides; and chlorogenic acid. Bacillus polyfermenticus. 0044 Examples of the water-soluble coenzymes include 0054. In addition, examples of those suitable for mammals thiamine diphosphate, NADH, NAD, NADP, NADPH, FMN, to oral consume include Bacillus coagulans and Bacillus FAD, coenzyme A, pyridoxal phosphate, and tetrahydrofolic pumilus. These viable bacteria may be used alone and also as acid. a mixture of two or more of them. US 2013/007 1525 A1 Mar. 21, 2013

0055. In the particulate composition of the present inven than the melting point but is lower than the boiling point of the tion, the weight ratio of the hydrophilic substance to the fat fat composition, thereby forming an S/OSuspension, and then composition is preferably within the range of from 0.01/99.99 the S/O suspension is cooled to lower than the melting point to 70/30 and more preferably within the range of from 1790 to of the fat composition while holding the Suspension in a liquid 40/60. In the event that the weight ratio of the hydrophilic droplet dispersion state in a gas phase or an aqueous phase to Substance to the fat composition is low, since the content of solidify the fat composition, thereby forming an S/O type the hydrophilic Substances in a resulting particulate compo solid particle. Alternatively, it is permitted to form an S/O sition becomes low, it becomes necessary, for example, to type Solid particle by dispersing a hydrophilic Substance to be take a large amount of the particulate composition when a enclosed directly into a fat composition, which is a matrix prescribed amount of the hydrophilic substance is orally component, at a temperature equal to or higher than the melt administered. On the other hand, in the event that the weight ing point of the fat composition, thereby preparing an S/O ratio of the hydrophilic substance to the fat composition is Suspension, and then cooling the S/O Suspension to lower excessively high, it is undesirable because the encapsulation than the melting point of the fat composition while holding yield of the hydrophilic substance will decrease, for example, the Suspension in a liquid droplet dispersion state in a gas the hydrophilic Substance will leak to the outeracqueous phase phase oran aqueous phase to Solidify the fat composition; and in the production process. it is also permitted to form a W/O type solid particle by 0056. The particulate composition of the present invention emulsifying and dispersing a mixture of a fat composition, may further contain a surfactant, a thickener, a hydrophilic which is a matrix component, and a hydrophilic Substance to organic solvent, and the like. These may be ones used in the be enclosed or an aqueous Solution of the hydrophilic Sub production of the particulate composition. stance at a temperature equal to or higher than the melting 0057 The particulate composition of the present invention point of the fat composition, thereby preparing a W/O emul is a particulate composition in which the hydrophilic Sub Sion, and then cooling the emulsion to lower than the melting stance is polydispersed in the fat composition having the point of the fat composition without removing moisture while above-described specific solid fat content, and it is a so-called holding the emulsion in a liquid droplet dispersion state to S/O type or W/O type microcapsule. Solidify the fat composition. Examples of a method of cooling 0058. The dispersion diameter of the hydrophilic sub the S/O suspension or the W/O emulsion to lower than the stance in the particulate composition of the present invention melting point of the fat composition while holding it in a is not particularly restricted, but it is preferably within the liquid droplet dispersion state in a gas phase includes spray range of 0.01 to 50 m, more preferably within the range of cooling methods. Examples of a method of cooling the S/O 0.01 to m, and most preferably within the range of 0.01 to 10 suspension or the W/O emulsion to lower than the melting m. The particulate composition of the present invention point of the fat composition while holding it in a liquid droplet exhibits a particle-like shape at normal temperature and the dispersion state in an aqueous phase include methods in average particle diameter of the particles is preferably 1 to which the S/O suspension or the W/O emulsion is added to an 2000 m, more preferably within the range of 10 to 1000 m, aqueous phase prepared separately (preferably, an aqueous and even more preferably within the range of 100 to 500 m. phase containing a surfactant, a thickener, a hydrophilic 0059 A method of producing the particulate composition organic solvent, and the like), thereby preparing an S/O/W of the present invention is not particularly restricted and emulsion or a W/O/W emulsion, and then cooling the result methods of producing known S/O type microcapsules or W/O ing S/O/W emulsion or the W/O/W emulsion to lower than type microcapsules can be employed. For example, a Solid the melting point of the fat composition. particulate composition can be obtained by a method in which 0061 The present invention can provide a fine particulate a fat composition, which is a matrix component, is adjusted to composition which has a wide range of a particle diameter a temperature equal to or higher than its melting point, then a and in which a hydrophilic Substance is enclosed in a high hydrophilic Substance being in a solid or having been dis content. The particulate composition of the present invention Solved in water is mixed and dispersed in the fat composition, has enteric properties due to use of a fat component decom and then the resultant is Subjected to liquid droplet dispersion posable by lipase as a matrix of the particulate composition in a gas phase or in a liquid phase and cooled to lower than the and can be used as a formulation which allows a hydrophilic melting point of the fat composition. The S/O type microcap Substance easily decomposable by the stomach, such as a sule as used herein refers to a solid particle in which a hydro protein, a peptide, or an enzyme, to be absorbed efficiently by philic Solid Substance is polydispersed in a matrix base com the intestines without being decomposed in the stomach. posed of a fat composition, and it differs from an S/O Moreover, in the present invention, since the solubility or Suspension in which a solid Substance is dispersed in a liquid disintegrativity of a fat composition in the body, especially in oil phase and from an S/O/W emulsion in which the S/O the intestines, can be controlled through the adjustment of the Suspension is suspended in an aqueous phase. Solid fat content of the fat composition to be used as a matrix 0060. One preferred example of methods of making the component to a desired range, it is possible to freely control dispersion diameter of a hydrophilic substance to be dis the degree and timing of release of the enclosed hydrophilic persed in a microcapsule as Small as possible and making the Substance from the particulate composition. The disintegrat content of the hydrophilic Substance as high as possible is a ivity in the intestines of the particulate composition of the method in which a mixture of a fat composition, which is a present invention can be set according to an intended purpose; matrix component, and a hydrophilic Substance to be for example, as for the release rate of a hydrophilic substance enclosed oran aqueous solution of the hydrophilic Substance in an intestinal disintegration test described below, the release is emulsified and dispersed at a temperature equal to or higher rate of the hydrophilic substance to be exhibited after treat than the melting point of the fat composition, thereby prepar ment at 37 C for one hour is generally 20% or more, prefer ing a W/O emulsion, then the moisture contained in the W/O ably 40% or more, more preferably 50% or more, even more emulsion is removed at a temperature that is equal to or higher preferably 60% or more, and particularly preferably 70% or US 2013/007 1525 A1 Mar. 21, 2013

more. Although it is needless to say that the upper limit of the fatty acid having 8 to 12 carbon atoms and a saturated fatty release rate is 100%, a rate of about 95% is high enough for acid having 16 or 18 carbon atoms as constituent fatty acids. usual purposes. The content of the triglyceride including at least both a satu 0062 (Second Present Invention) rated fatty acid having 8 to 12 carbon atoms and a saturated 0063. The coating fat composition of the second present fatty acid having 16 or 18 carbon atoms in the coating fat invention contains, as a main component, a triglyceride composition of the present invention is preferably 50% by including at least both a saturated fatty acid having 6 to 12 weight or more, more preferably 60% by weight or more, and carbon atoms and a saturated fatty acid having 14 or more even more preferably 70% by weight or more. Although the carbon atoms as constituent fatty acids. Triglycerides have upper limit of the content of the triglyceride is not particularly three constituent fatty acids, and the triglyceride that is the restricted, it is preferably 90% by weight or less from the main component of the coating fat composition of the present viewpoint of enteric properties. invention has at least one Saturated fatty acid having 6 to 12 0066. The coating fat composition of the present invention carbonatoms and at least one saturated fatty acid having 14 or is not be particularly restricted if it is one having the afore more carbon atoms as constituent fatty acids. The remaining mentioned constituent fatty acid composition and can be one constituent fatty acid in the above-mentioned triglyceride obtained by fractionating and/or hardening naturally occur is not restricted; it may be either a saturated fatty acid or an ring fats or industrially produced fats or mixing such fats so unsaturated fatty acid, and the number of carbon atoms that the aforementioned constituent fatty acid composition thereof may be chosen within an arbitrary range. From the may be achieved, but preferably it is produced by using a viewpoint of controlling physical properties such as a melting transesterification reaction because a specific triglycerideas a point, preferred is one containing, as a main component, a main component can be obtained easily. The transesterifica triglyceride composed only of saturated fatty acid(s) having 6 tion reaction as used herein can be performed by using a fat, to 12 carbon atoms and Saturated fatty acid(s) having 14 or a fatty acid, a fatty acid ester, and the like as raw materials. more carbonatoms as constituent fatty acids (namely, a trig Specific examples thereof include transesterification between lyceride containing one Saturated fatty acid having 6 to 12 two or more types of fats, transesterification between one or carbonatoms and two saturated fatty acids having 14 or more more types of fats and one or more types of fatty acids, a carbon atoms as constituent fatty acids or a triglyceride con transesterification reaction between one or more types of fats taining two saturated fatty acids having 6 to 12 carbon atoms and one or more types of fatty acid esters, and a transesteri and one saturated fatty acid having 14 or more carbon atoms fication reaction between one or more types of fats, one or as constituent fatty acids). The term “main component as more types of fatty acids, and one or more types of fatty acid used herein means that the content thereof in the fat compo esters, but any one of them may be employable. The fat to be sition accounts for at least 45% by weight, preferably 50% by used as a raw material of the transesterification reaction is not weight or more, more preferably 60% by weight or more, and particularly restricted, and examples thereof include animal even more preferably 70% by weight or more. If the content and vegetable fats, such as coconut oil, palm oil, palm kernel of the aforementioned triglyceride in the coating fat compo oil, cacao butter, shea butter, sal butter, illipe butter, lard, beef sition of the present invention is less than 45% by weight, the tallow, rapeseed oil, rice oil, peanut oil, olive oil, corn oil, enclosure coated with the coating fat composition of the Soybean oil, perilla oil, cotton seed oil, Sunflower oil, present invention may be released at a low rate in the intes Oenothera Biennis oil, sesame oil, safflower oil, palm kernel tines, so that sufficient enteric properties may not beachieved. oil, and fish oil; hydrogenated animal and vegetable oils, such 0064. Furthermore, the coating fat composition of the as hardened palm oil, hardened rapeseed oil, hardened soy present invention is characterized in that as for the constituent bean oil, hardened lard, hardened fish oil, fully hardened palm fatty acid proportion in the whole fat contained in the com oil, and fully hardened rapeseed oil; fractionated oils obtained position, the proportion accounted for by the Saturated fatty by fractionating these, Such as fractionated coconut oil, frac acid having 14 or more carbonatoms exceeds 50% by weight. tionated palm kernel oil, fractionated palm oil, fractionated If that proportion is 50% by weight or less, there is a tendency cacao butter oil, fractionated sheabutter oil, fractionated lard that the coating fat composition becomes liquid or semi-solid oil, fractionated hardened soybean oil, and fractionated hard at room temperature, and therefore it is impossible to form a ened fish oil; Saturated fatty acid triglycerides, such as particulate composition or a resulting particulate composi tristearin, tripalmitin, and trilaurin; medium chain fatty acid tion is so soft that it is difficult to handle the composition or it triglycerides. Such as tricaprylin and tricaprin; and unsatur has poor flowability. ated fatty acid triglycerides, such as triolein and trilinol, and 0065. That is, the coating fat composition of the present their partial glycerides, such as monoglycerides and diglyc invention is a coating fat composition containing 45% by erides. Further, examples of the fatty acid or fatty acid ester to weight or more of a triglyceride including at least both a be used as a raw material of the transesterification reaction saturated fatty acid having 6 to 12 carbon atoms and a satu include, but are not limited to, fatty acids, such as caprylic rated fatty acid having 14 or more carbonatoms as constituent acid, capric acid, lauric acid, myristic acid, palmitic acid, fatty acids, wherein the proportion of the saturated fatty acid Stearic acid, oleic acid, linoleic oil, linolenic acid, arachidonic having 14 or more carbon atoms in the constituent fatty acids acid, eicosapentaenoic acid, and docosahexaenoic acid; and of the whole fat exceeds 50% by weight. From the viewpoint fatty acid esters, such as methyl esters or ethyl esters thereof. of easy availability of raw materials, the coating fat compo 0067. The transesterification that can be performed in the sition of the present invention is preferably one containing, as present invention may be either a chemical transesterification a main component, a triglyceride including at least both a reaction using an alkaline catalyst or the like or an enzymatic saturated fatty acid having 8 to 12 carbon atoms and a satu transesterification using an enzyme or a microorganism. rated fatty acid having 16 or more carbonatoms as constituent There may or may not be a difference in composition between fatty acids, and more preferably one containing, as a main the fatty acid of the 1- or 3-position and the fatty acid of the component, a triglyceride including at least both a saturated 2-position of the resulting transesterified fat. US 2013/007 1525 A1 Mar. 21, 2013

0068. The catalyst capable of being used in performing the may be enclosed directly or powders or tablets containing chemical transesterification reaction in the present invention bioactive substances or effective ingredients, or the like may is not particularly restricted as far as it is a catalyst generally be enclosed. Moreover, foods and food base materials may known as a transesterification catalyst. Specific examples also be coated. The bioactive substances or the other effective thereof include alkali metals, such as lithium, Sodium, and ingredients may be any of hydrophilic Substances and hydro potassium; alkaline earth metals, such as magnesium, cal phobic Substances, or may be both, and can be selected appro cium, and barium; metals such as Zinc, cadmium, titanium, priately according to an intended application. tin, antimony, lead, manganese, cobalt, and nickel; and 0072 Examples of the hydrophilic substances and the acetates, carbonates, borates, oxides, hydroxides, hydrides, hydrophobic Substances that can be coated with the coating oralcoholate. Such as methylate, thereof. In the present inven fat composition of the second present invention include the tion, the chemical transesterification reaction can be per hydrophilic substances and the hydrophobic substances that formed by, for example, fully drying raw materials such as a are mentioned above for the first present invention. fat, a fatty acid, and a fatty acid ester, adding the aforemen 0073. The above-mentioned hydrophobic substance can tioned catalyst to the raw materials in an amount of 0.1 to 1% be added either in a form in which it is enclosed as a mixture by mass, and then stirring under reduced pressure at 80 to 120 with other ingredients within a coating fat composition with C for 0.5 to 1 hour in accordance with a routine procedure. out being mixed completely with the coating fat composition After the completion of the transesterification reaction, the or in a form in which it exists together with a coating fat catalyst is washed away with water, and then decolorization composition while being completely or partially mixed there and deodorization treatments may be performed which are with. For example, there may be employed a form in which performed in common purification steps for edible oils. the surface of a particulate composition, tablet or the like 0069. Although the enzyme or microorganism usable in enclosing the hydrophobic substance is coated with the coat performing the enzymatic transesterification reaction in the ing fat composition of the present invention. Moreover, a present invention is not particularly restricted as far as it is an material prepared by dissolving the hydrophobic Substance in enzyme generally known to be usable for a transesterification the coating fat composition in advance also can be used as a reaction, lipase or a microorganism that produces lipase is base material for microcapsules or as a coating fat. usually used. As to lipase to be used, any of a lipase solution, 0074. In the present invention, the form of coating the a lipase powder, and immobilized lipase in which a lipase enclosure as described above with the coating fat composition powder is immobilized to a carrier Such as cerite or an ion of the present invention is not particularly restricted, and exchange resin may be used. Examples of the lipase usable for examples thereof include, in addition to a form of an S/O type the enzymatic transesterification reaction in the present microcapsule and a form of a W/O type microcapsule, forms invention include lipase derived from genus Alcaligenes (e.g., of coated particles and coated tablets. Among these, the coat lipase QLM and lipase PL produced by Meito Sangyo Co., ing fat composition of the present invention is very Suitable as Ltd., etc.), lipase derived from genus Candida (e.g., lipase OF the matrix base of an S/O type microcapsule as described produced by Meito Sangyo Co., Ltd., etc.), and immobilized above. lipase derived from Rhizomucor miehei (e.g., LipoZime 0075. In the present invention, a method of producing an TLIM and Lipozyme RMIM produced by Novozymes, etc.). S/O type microcapsule using the coating fat composition of Moreover, microorganisms which are sources of Such lipase the present invention is not particularly restricted; however, can be used as a catalyst for the enzymatic transesterification the above-described methods are preferred, and specific reaction directly in the form of dried fungus or an immobi examples thereof include production methods by a liquid lized fungus. In the present invention, the enzymatic transes phase process in which an S/O Suspension in which a hydro terification may be performed by, for example, adding an philic Substance is polydispersed in a coating fat composition enzyme such as the aforementioned lipase to the aforemen molten at equal to or higher than the melting point of the tioned raw materials in an amount of 0.02 to 10% by mass, coating fat composition is prepared in advance, then the Sus and preferably 0.04 to 5% by mass, while stirring the mixture pension is suspended in an aqueous phase to form liquid at 40 to 85C, and preferably 40 to 80C for 0.5 to 48 hours, and droplets, and cooling the droplets to lower than the melting preferably 0.5 to 24 hours. After the completion of the trans point of the coating fat composition, thereby obtaining Solid esterification reaction, the enzyme such as a lipase powder or particles, and by a gas phase process in which the S/O Sus immobilized lipase, or fungus is removed by filtration or the pension is directly sprayed and cooled to cool liquid droplets like, and fatty acids or fatty acid esters are removed if neces of the S/O suspension to lower than the melting point of the fat sary in the event that they are present after the reaction, and composition, thereby solidifying the fat composition. thereafter decolorization and deodorization treatments may 0076. In this case, a method of preparing the S/O suspen be performed which are performed in common purification sion is not particularly restricted as far as it is a method steps for edible oils. capable of dispersing the hydrophilic Substance uniformly in 0070 Moreover, in the present invention, in order to adjust a molten coating fat composition; and for example, an S/O constituent fatty acid composition or physical properties Such Suspension can be obtained by mixing an aqueous solution as melting point and solid fat content after the transesterifi containing a hydrophilic Substance dissolved therein and a cation reaction, it is possible to further fractionate or crystal Surfactant into a molten coating fat composition, followed by lize the resulting transesterified fat or mix the fat with other emulsification with a homogenizer or the like, thereby pre fats or edible waxes such as cera flava, candelilla wax, and paring a W/O emulsion, and then removing only moisture at rice bran wax. As the other fats to be mixed in this case, fats high temperature under reduced pressure. On the other hand, such as those described above can be used. as for materials low in heat resistance Such as those Suffer 0071. The enclosure that can be coated with the coating fat from deterioration, extinction, etc. at high temperature like composition of the present invention is not particularly proteins, peptides, and viable bacteria, an S/O Suspension can restricted; bioactive substances or other effective ingredients be obtained by directly adding a hydrophilic substance and a US 2013/007 1525 A1 Mar. 21, 2013

Surfactant that aids dispersion into a molten coating fat com I0084 (Intestinal Disintegration Test) position, and then fully dispersing them with a stirrer, a I0085. In a disintegration test of a particulate composition, homogenizer, or the like. evaluation was performed using a simulated intestinal fluid 0077. In the event that an S/O type microcapsule is pro containing bile and lipase. The simulated intestinal fluid was duced using the coating fat composition of the present inven prepared by dissolving a bile powder (produced by Wako tion, the weight ratio of a hydrophilic Substance as an enclo Pure Chemical Industries, Ltd.) and lipase derived from por Sure to the coating fat composition is preferably within the cine pancreas (produced by Sigma) in a Disintegration Test range of from 0.01/99.99 to 70/30, and more preferably Fluid 2 of pH 6.8 (produced by Kanto Chemical Co., Inc.) within the range of from 1/90 to 40/60. In the event that the with concentrations of 0.5% by weight, respectively. A par weight ratio of the hydrophilic Substance to the coating fat ticulate composition enclosing Food Red No. 102 (produced composition is low, since the content of the hydrophilic Sub by Wako Pure Chemical Industries, Ltd.) as a hydrophilic stance in a resulting S/O type microcapsule becomes low, it substance was added to the simulated intestinal fluid and becomes necessary, for example, to take a large amount of shaken at 37 C for one hour, and then a 50% trichloroacetic microcapsules when orally administering a prescribed acid (produced by Wako Pure Chemical Industries, Ltd.) amount of the hydrophilic substance. On the other hand, if the aqueous solution was added and then Subjected to centrifugal weight ratio of the hydrophilic Substance to the coating fat separation (MX-200, manufactured by Tomy Seiko Co. Ltd.) composition is excessively high, it is difficult to obtain par at 37 C, 12000 rpm for 5 minutes. By the measurement of ticles which are spherical and excellent in flowability and absorption at 510 nm of the supernatant solution after the because of insufficient coating of an enclosed Substance, most centrifugation by using a spectrophotometer (U-2000A Type, of the enclosed substance is released in the stomach before manufactured by Hitachi High-Technologies Corporation), microcapsules arrive at the intestines when orally taken, so the concentration of the hydrophilic substance in the super that an enteric effect will fail to be demonstrated sufficiently. natant solution was calculated. Assuming that the release rate For example, when proteins, viable bacteria, or the like with achieved at the complete release of the hydrophilic substance low resistance to stomach acid are used as the enclosed Sub contained in the particulate composition was considered to be stance, their deterioration or extinction is caused, so that an 100%, the release rate of the hydrophilic substance achieved expected bioactive effect may not be demonstrated. when treated at 37 C for one hour with the simulated intestinal fluid was calculated. 0078. On the other hand, in obtaining a coated particle or I0086 (Measurement of Average Particle Diameter of Par coated tablet in which the surface of aparticulate composition ticulate Composition) or tablet is coated with the coating fat composition of the I0087 Measurement was performed by using a particle present invention, a coating method is not particularly diameter measurement device (LA-950, manufactured by restricted and, for example, it can be produced by spraying a HORIBA, Ltd.). molten coating fat composition to the Surface of a particulate I0088 (Content of Hydrophilic Substance in Particulate composition or tablet by using a pan coating device, fluidized Composition) bed granulation, or a coating device, thereby forming a film I0089. The particulate composition obtained was liquefied layer. by being heated to temperature equal to or higher than the 007.9 The coating fat composition of the present invention melting point of the solid fat used, and then it was mixed with keeps a Solid at room temperature and exhibits excellent water, so that the hydrophilic Substance encapsulated in the intestinal disintegrativity even though it is easy to handle particulate composition was extracted into the aqueous phase. formulations or the like after coating therewith. For this rea The concentration of the hydrophilic substance extracted into son, S/O type microcapsules, coated particles and coated the aqueous phase was measured by HPLC and then the net tablets prepared using the coating fat composition of the content of the hydrophilic Substance in the particulate com present invention are excellent as enteric formulations which position was calculated. protect their enclosure from stomach acid in the stomach and (0090 (Encapsulation Yield of Hydrophilic Substance into release the enclosure rapidly after their arrival at the intes Particulate Composition) tines. 0091 An encapsulation yield was calculated from the weight of the hydrophilic Substance used during production EXAMPLES and the content of the hydrophilic substance in the particulate composition calculated by the above-described method. 0080. The present invention will be described more spe cifically below with reference to examples, but the invention Production Example 1 is not limited thereto. In the examples, “part(s) and “96” mean “part(s) by weight' and “% by weight,” respectively. Preparation of Fish Oil Low Melting Fraction 0092. One hundred parts of fish oil deacidfied and I0081 (First Present Invention) bleached by a routine procedure was melted at 40 C and then I0082 (Measurement of Solid Fat Content) cooled to 10 C undergentle agitation and further held at 10C 0083. A fat composition to be measured was heated to for 12 hours, so that crystals were precipitated. Subsequently, equal to or higher than its melting point, thereby being melted the resulting crystals were collected by suction filtration, completely. Then, it was held at prescribed temperature (25C whereby a fish oil low melting fraction that was liquid at 25C or 37 C) for one week, and thereafter a solid fat content at the was obtained. prescribed temperature was measured inaccordance with The Production Example 2 JOCS Standard Methods for the Analysis of Fats, Oils and Related Materials (edited by Japan Oil Chemists’ Society), Preparation of Fractionated Palm Oil 2.2.9-2003 by using a magnetic nuclear resonance instrument 0093. Two hundred parts of hexane was added to 100 parts MINISPEC mc20 (manufactured by Bruker Optics Inc). of hardened palm part, which was then dissolved completely US 2013/007 1525 A1 Mar. 21, 2013

at 45 C and thereafter was held at 20 C for 20 hours, whereby heat-mixing 70 g of the fractionated palm oil prepared in a high melting fraction was precipitated. Subsequently, the Production Example 2, 20g of fully hardened rapeseed oil resulting high melting fraction was collected by Suction fil (produced by Yokozeki Oil & Fat Industries Co., Ltd., melting tration and hexane was evaporated with an evaporator, fol point 67 C), and 10g of medium chain fatty acid-containing lowed by steam distillation at 250 C, whereby fractionated triglyceride (product name Actor M1, produced by Riken palm oil (melting point 52C) was obtained. Vitamin Co., Ltd., melting point -6 C) was used as a fat composition. The Solid fat content of the fat composition used Example 1 and the results of the intestinal disintegration test of the par 0094 Ninety grams of fully hardened palm oil (product ticulate composition obtained were shown in Table 1. name “RHPL', produced by Taiyo Yushi Corporation, melt ing point 57 C) and 10g of medium chain fatty acid triglyc Example 3 eride (product name “Actor M2, produced by Riken Vitamin 0098. A particulate composition was obtained in the same Co., Ltd., melting point -12 C) were mixed under heating, manner as in Example 1 except that a material prepared by affording a fat composition. The solid fat content of the result heat-mixing 95 g of the fractionated palm oil prepared in ing fat composition was measured by the above-described Production Example 2 and 5 g of the fish oil low melting method. fraction prepared in Production Example 1 was used as a fat 0095 To an oily component composed of 20 g of a fat composition. The Solid fat content of the fat composition used composition having been melted by being heated to a tem and the results of the intestinal disintegration test of the par perature of 70 C in advance and 1.0 g of tetraglycerol con ticulate composition obtained were shown in Table 1. densed ricinoleate (product name “POEM PR-100', pro duced by Riken Vitamin Co., Ltd.), 10 mL of a 10% by weight Example 4 Food Red No. 102 aqueous solution was added, followed by performing emulsification and dispersion with a homog 0099. A particulate composition was obtained in the same enizer (T.K. Homomixer MARK II 20 type, manufactured by manner as in Example 1 except that a material prepared by PRIMIX Corporation), whereby a W/O emulsion was pre heat-mixing 80 g of fully hardened rapeseed oil (produced by pared. Subsequently, the W/O emulsion was subjected to Yokozeki Oil & Fat Industries Co., Ltd.) and 20 g of medium moisture removal while being stirred at a temperature of 70 C chain fatty acid triglyceride (product name “Actor M2, pro for 30 minutes under a reduced pressure condition of 13 kPa, duced by Riken Vitamin Co., Ltd.) was used as a fat compo whereby an S/O suspension was obtained. The S/O suspen sition. The solid fat content of the fat composition used and sion was added to 200 mL of an aqueous solution having been the results of the intestinal disintegration test of the particu heated to 70 C in advance and containing 0.5% by weight of late composition obtained were shown in Table 1. gum arabic (product name “Gum Arabic SD, produced by San-Ei Gen F.F.I., Inc.) and 0.03% by weight of decaglycerol Example 5 monooleate (product name “POEMJ-0381V, produced by Riken Vitamin Co., Ltd.) and the mixture was stirred with a 0100. A particulate composition was obtained in the same disk turbine blade, whereby an S/O/W emulsion was pre manner as in Example 1 except that a material prepared by pared. Thereafter, the S/O/W emulsion was added in one heat-mixing 60 g of fully hardened rapeseed oil (produced by portion to 400 mL of an aqueous solution having been cooled Yokozeki Oil & Fat Industries Co., Ltd.) and 40g of medium to 5 C in advance and containing 0.5% by weight of gum chain fatty acid triglyceride (product name “Actor M2, pro arabic and 0.03% by weight of decaglycerol monooleate to be duced by Riken Vitamin Co., Ltd.) was used as a fat compo cooled rapidly, followed by suction filtration and vacuum sition. The solid fat content of the fat composition used and drying, whereby a particulate composition was obtained. An the results of the intestinal disintegration test of the particu intestinal disintegration test of the resulting particulate com late composition obtained were shown in Table 1. position was performed by the above-mentioned method. The solid fat content of the fat composition used and the results of Example 6 the intestinal disintegration test of the particulate composi tion obtained were shown in Table 1. 0101 A particulate composition was obtained in the same 0096. The average particle diameter of the resulting par manner as in Example 1 except that a material prepared by ticulate composition was 351 m, and the encapsulation yield heat-mixing 85g of fully hardened rapeseed oil (produced by of Food Red No. 102 into the particulate composition in this Yokozeki Oil & Fat Industries Co., Ltd.) and 15g of olive oil example was 93.5%. Moreover, when the resulting particu (produced by The Nisshin OilliO Group, Ltd.) was used as a late composition was observed with a scanning electron fat composition. The solid fat content of the fat composition microscope (S-4800, manufactured by Hitachi, Ltd.; herein used and the results of the intestinal disintegration test of the after SEM), aparticle shapehaving a smooth surface structure particulate composition obtained were shown in Table 1. as shown in FIG. 1 was observed. Furthermore, when the surface structure after the disintegration test of the particulate Example 7 composition was observed by SEM, fine pores illustrated in 0102) A particulate composition was obtained in the same FIG. 2 were observed. It is conceivable that Food Red No. manner as in Example 1 except that a material prepared by 102, which is the enclosed substance, was released through heat-mixing 85g of fully hardened rapeseed oil (produced by the pores. Yokozeki Oil & Fat Industries Co., Ltd.) and 15 g of sun flower oil (produced by Showa Sangyo Co., Ltd.) was used as Example 2 a fat composition. The solid fat content of the fat composition 0097. A particulate composition was obtained in the same used and the results of the intestinal disintegration test of the manner as in Example 1 except that a material prepared by particulate composition obtained were shown in Table 1. US 2013/007 1525 A1 Mar. 21, 2013

Example 8 solution containing 30% by weight of anserine (produced by Yaizu Suisankagaku Industry Co., Ltd.) was added, followed 0103) A particulate composition was obtained in the same by performing emulsification and dispersion with a homog manner as in Example 1 except that a material prepared by enizer (T.K. Homomixer MARK II20, manufactured by PRI heat-mixing 85g of fully hardened rapeseed oil (produced by MIX Corporation), whereby a W/O emulsion was prepared. Yokozeki Oil & Fat Industries Co., Ltd.) and 15 g of perilla oil Subsequently, the W/O emulsion was subjected to moisture (produced by Ohta Oil Mill Co., Ltd.) was used as a fat removal while being stirred at a temperature of 70 C for 30 composition. The Solid fat content of the fat composition used minutes under a reduced pressure condition of 13 kPa, and the results of the intestinal disintegration test of the par whereby an S/O suspension was obtained. The S/O suspen ticulate composition obtained were shown in Table 1. sion was added to 200 mL of an aqueous solution having been Example 9 heated to 70 C in advance and containing 0.5% by weight of gum arabic (product name “Gum Arabic SD, produced by 0104. A particulate composition was obtained in the same San-Ei Gen F.F.I., Inc.) and 0.03% by weight of decaglycerol manner as in Example 1 except that a material prepared by monooleate (product name “POEMJ-0381V, produced by heat-mixing 85g of fully hardened rapeseed oil (produced by Riken Vitamin Co., Ltd.) and the mixture was stirred with a Yokozeki Oil & Fat Industries Co., Ltd.) and 15 g of diglyc disk turbine blade, whereby an S/O/W emulsion was pre eride (product name “Econa', produced by Kao Corporation) pared. Thereafter, the S/O/W emulsion was added in one was used as a fat composition. The solid fat content of the fat portion to 400 mL of an aqueous solution having been cooled composition used and the results of the intestinal disintegra to 5 C in advance and containing 0.5% by weight of gum tion test of the particulate composition obtained were shown arabic and 0.03% by weight of decaglycerol monooleate to be in Table 1. cooled rapidly, followed by suction filtration and vacuum drying, whereby a particulate composition was obtained. The Example 10 average particle diameter of the resulting particulate compo 0105. A particulate composition was obtained in the same sition was 285 m, and the encapsulation yield of anserine into manner as in Example 1 except that a material prepared by the particulate composition in this example was 89.0%. heat-mixing 85g of fully hardened rapeseed oil (produced by Yokozeki Oil & Fat Industries Co., Ltd.) and 15 gofoleic acid Example 14 (produced by Wako Pure Chemical Industries, Ltd.) was used 0109) A particulate composition was obtained in the same as a fat composition. The solid fat content of the fat compo manner as in Example 1 except that a material prepared by sition used and the results of the intestinal disintegration test heat-mixing 90 g of the fractionated palm oil prepared in of the particulate composition obtained were shown in Table Production Example 2 and medium chain fatty acid triglyc 1. eride was used as a fat composition. The Solid fat content of Example 11 the fat composition used and the results of the intestinal disintegration test of the particulate composition obtained 0106 A particulate composition was obtained in the same were shown in Table 1. manner as in Example 1 except that a material prepared by heat-mixing 85g of trilaurin (produced by Wako Pure Chemi Example 15 cal Industries, Ltd., melting point 45 C) and 15 g of palm kernel oil (produced by Kaneka Corporation, melting point 0110. A fat composition was obtained by heat-mixing 90 g 27 C) was used as a fat composition. The solid fat content of of the fractionated palm oil prepared in Production Example the fat composition used and the results of the intestinal 2 and 10g of medium chain fatty acid triglyceride (product disintegration test of the particulate composition obtained name Actor M2, produced by Riken Vitamin Co., Ltd.). were shown in Table 1. Then, 5g of lactoferrin (produced by Wako Pure Chemical Industries, Ltd.) and 1.5 g of Sucrose erucate (product name Example 12 “ER-290, produced by Mitsubishi-Kagaku Foods Corpora tion) were added to 200 mL of ethanol and dispersed with a 0107. A particulate composition was obtained in the same homogenizer while being heated to 40 C, whereby a mixed manner as in Example 1 except that a material prepared by liquid was prepared. Ethanol was removed by stirring the heat-mixing 85g of fully hardened rapeseed oil (produced by mixed liquid at 45 C for 30 minutes under a reduced pressure Yokozeki Oil & Fat Industries Co., Ltd.) and 15 g of rapeseed condition of 13 kPa, whereby a complex of lactoferrin and oil (produced by Kaneka Corporation) was used as a fat Sucrose erucate was obtained. To 18 g of a fat composition composition. The Solid fat content of the fat composition used having been melted by heating to a temperature of 55 C in and the results of the intestinal disintegration test of the par advance, the complex obtained above was added and then ticulate composition obtained were shown in Table 1. dispersed with a homogenizer, whereby an S/O Suspension Example 13 containing the lactoferrin complex dispersed therein was obtained. Subsequently, the S/O suspension was added to 300 0108. A fat composition was obtained by heat-mixing 85g mL of an aqueous solution having been heated to 55 C in of fully hardened rapeseed oil (produced by Yokozeki Oil & advance and containing 0.5% by weight of gum arabic (prod Fat Industries Co., Ltd.)and 15g of rapeseed oil (produced by uct name "Gum Arabic SD, produced by San-Ei Gen F.F.I., Kaneka Corporation). To an oily component composed of 20 Inc.) and 0.01% by weight of decaglycerol monolaurate g of a fat composition having been melted by being heated to (product name “ML-750', produced by Sakamoto Yakuhin a temperature of 70 C in advance and 1.0 g of tetraglycerol Kogyo Co., Ltd.) and stirred with a disk turbine blade for 10 condensed ricinoleate (product name “POEM PR-100', pro minutes, whereby an S/O/W emulsion was prepared. There duced by Riken Vitamin Co., Ltd.), 5 mL of an aqueous after, the S/O/W emulsion was added in one portion to 300 US 2013/007 1525 A1 Mar. 21, 2013

mL of an aqueous Solution having been cooled to 15 C in encapsulation yield of lactoferrin into the particulate compo advance and containing 0.5% by weight of gum arabic and sition in this example was 94.8%. 0.01% by weight of decaglycerol monolaurate to be cooled rapidly, followed by Suction filtration and vacuum drying, Comparative Example 1 whereby a particulate composition was obtained. 0114. To an oily component composed of 20 g of tripalm 0111. The resulting particulate composition did not disin itin (produced by Wako Pure Chemical Industries, Ltd.) hav tegrate even though it was added to a simulated gastric liquid, ing been melted by being heated to a temperature of 80 C in and when the particulate composition was removed from the advance and 1.0 g of tetraglycerol condensed ricinoleate simulated gastric liquid 120 minutes after addition and then (product name “POEM PR-100', produced by Riken Vitamin the lactoferrin enclosed in the particulate composition was Co., Ltd.), 10 mL of an aqueous solution containing 10% by analyzed, it was confirmed that the lactoferrin in the particu weight of Food Red No. 102 was added, followed by perform late composition was present without being decomposed. ing emulsification and dispersion with a homogenizer, That is, it was demonstrated that the lactoferrin polydispersed whereby a W/O emulsion was prepared. Subsequently, the in the particulate composition of this example was provided W/O emulsion was subjected to moisture removal while with digestive enzyme resistance in the stomach. being stirred for 20 minutes at a temperature of 80 C under a reduced pressure condition of 13 kPa, whereby an S/O sus Example 16 pension was obtained. The S/O suspension was added to 300 mL of an aqueous solution having been heated to 70 C in 0112 A particulate composition was obtained in the same advance and containing 0.5% by weight of gum arabic (prod manner as in Example 1 except that a material prepared by uct name "Gum Arabic SD, produced by San-Ei Gen F.F.I., heat-mixing 18 g of the fractionated palm oil prepared in Inc.) and 0.05% by weight of decaglycerol monooleate and Production Example 2, 2 g of medium chain fatty acid trig stirred with a disk turbine blade, wherebyan S/O/W emulsion lyceride (product name “Actor M2, produced by Riken Vita was prepared. Thereafter, the S/O/W emulsion was added in min Co., Ltd.) and 10 g of Coenzyme Q10 (produced by one portion to 400 mL of an aqueous solution having been Kaneka Corporation) was used as a fat composition. The Solid cooled to 5 C in advance and containing 0.5% by weight of fat content of the fat composition used and the results of the gum arabic and 0.03% by weight of decaglycerol monooleate intestinal disintegration test of the particulate composition (product name “ML-750', produced by Sakamoto Yakuhin obtained were shown in Table 1. Kogyo Co., Ltd.) to be cooled rapidly, followed by suction filtration and vacuum drying, whereby a particulate compo Example 17 sition was obtained. The solid fat content of tripalmitin and the results of the intestinal disintegration test of the particu 0113. A fat composition was obtained by heat-mixing 18g late composition obtained were shown in Table 1. of the fractionated palm oil prepared in Production Example 2, 2 g of medium chain fatty acid triglyceride (product name Comparative Example 2 Actor M2, produced by Riken Vitamin Co., Ltd.) and 10 g of Coenzyme Q10 (produced by Kaneka Corporation). Then, 0115 The preparation of a particulate composition was 4.2 g of lactoferrin (produced by Wako Pure Chemical Indus attempted in the same manner as in Example 1 except that a tries, Ltd.) and 0.9 g of sucrose erucate (product name “ER material prepared by heat-mixing 50 g of fully hardened 290, produced by Mitsubishi-Kagaku Foods Corporation) rapeseed oil (produced by Yokozeki Oil & Fat Industries Co., were added to 200 mL of ethanol and dispersed with a homog Ltd.) and 50 g of medium chain fatty acid triglyceride (prod enizer while being heated to 40 C, whereby a mixed liquid uct name “Actor M2, produced by Riken Vitamin Co., Ltd.) was prepared. Ethanol was removed by stirring the mixed was used as a fat composition. However, even though the liquid at 45 C for 30 minutes under a reduced pressure con S/O/W emulsion was added to an aqueous solution of gum dition of 13 kPa, whereby a complex of lactoferrin and arabic and decaglycerol monooleate cooled to 5 C, the oil Sucrose erucate was obtained. To 15 g of a fat composition phase part did not solidify, so that any desired particulate having been melted by heating to a temperature of 58 C in composition could not be obtained. The solid fat content of advance, the complex was added and then dispersed with a the fat composition used was shown in Table 1. homogenizer, whereby an S/O Suspension containing the lactoferrin complex dispersed therein was obtained. Subse TABLE 1 quently, the S/O suspension was added to 300 mL of an Solid fat content at each Release rate of aqueous Solution having been heated to 55 C in advance and temperature offat hydrophilic Substance in containing 0.5% by weight of gum arabic (product name composition used (% intestinal disintegration “Gum Arabic SD, produced by San-Ei Gen F.F.I., Inc.) and 0.01% by weight of decaglycerol monolaurate (product name 25 C. 37 C. test (%) “ML-750, produced by Sakamoto Yakuhin Kogyo Co., Ltd.) Example 1 93.2 88.2 22.5 Example 2 67.9 67.9 56.9 and stirred with a disk turbine blade for 10 minutes, whereby Example 3 70.2 70.2 42.4 an S/O/W emulsion was prepared. Thereafter, the S/O/W Example 4 81.6 73.7 45.1 emulsion was added in one portion to 300 mL of an aqueous Example 5 60.2 53.1 80.2 Solution having been cooled to 15C in advance and contain Example 6 88.3 84.4 62.O ing 0.5% by weight of gum arabic and 0.01% by weight of Example 7 88.0 83.5 77.5 Example 8 87.6 83.2 52.8 decaglycerol monolaurate to be cooled rapidly, followed by Example 9 88.0 83.7 SO.O Suction filtration and vacuum drying, whereby a particulate Example 10 87.7 83.1 88.7 composition was obtained. The average particle diameter of Example 11 8O.S 71.7 94.2 the resulting particulate composition was 374 m, and the US 2013/007 1525 A1 Mar. 21, 2013 12

TABLE 1-continued whereby a transesterified fat was obtained. Nine hundred grams of n-hexane was added to 300 g of the resulting trans Solid fat content at each Release rate of temperature offat hydrophilic Substance in esterified fat and heated to 45 C, whereby the transesterified composition used (% intestinal disintegration fat was dissolved completely. Then, a solution of the transes terified fat in hexane was cooledata rate of 0.5 C/minute to 20 25 C. 37 C. test (%) C under stirring. After holding at 20 C for 40 minutes, it was Example 12 87.4 83.1 66.5 subjected to suction filtration and thereby a crystalline frac Example 14 66.4 66.4 52.4 tion was removed. The resulting filtrate fraction was heated to Example 16 87.8 87.8 40.6 35 C, held for 10 minutes, and cooled at a rate of 0.5 C/minute Comparative 99.6 99.3 14.5 to 0 C under stirring. After holding at 0C for 30 minutes, the Example 1 Comparative 45.5 38.8 crystalline fraction obtained was collected by suction filtra Example 2 tion and hexane was evaporated with an evaporator, followed by steam distillation at 210 C, whereby a medium melting fraction was obtained. The triglyceride composition of the 0116 Table 1 clearly shows that the particulate composi resulting medium melting fraction, the contents of the respec tions of the examples in which a fat composition having a tive components, and the proportion of Saturated fatty acids solid fat content of 50% or more and 90% or less was used as having 14 or more carbon atoms are shown in Table 2. a matrix were fine particulate compositions in which a hydro I0127. An S/O type microcapsule containing the medium philic Substance was encapsulated in a high content and were melting fraction of the transesterified fat as a matrix was particulate compositions exhibiting good enteric properties prepared as follows. To an oily component composed of 20 g indicated by a release rate of a hydrophilic Substance in a of a medium melting fraction having been melted by being simulated intestinal fluid of 20% or more. heated to a temperature of 35 C in advance and 1.0 g of 0117 (Second Present Invention) tetraglycerol condensed ricinoleate (product name “POEM 0118 PR-100', produced by Riken Vitamin Co., Ltd.), 10 mL of a 0119 Fifty milligrams of a fat to be analyzed was dis 10% by weight Food Red No. 102 aqueous solution was solved in 5 ml of isooctane, then 1 ml of a 0.2 mol/L sodium added, followed by performing emulsification and dispersion methylate/methanol Solution was added, and then a reaction with a homogenizer (T.K. Homomixer MARK II20, manu was performed at 70 C for 15 minutes, whereby constituent factured by PRIMIX Corporation), whereby a W/O emulsion fatty acids in the fat were methylesterificated. After the reac was prepared. Subsequently, the W/O emulsion was sub tion liquid was neutralized with acetic acid, an appropriate jected to moisture removal while being stirred at a tempera amount of water was added, and the fatty acid methyl esters in ture of 35C for 30 minutes under a reduced pressure condi the resulting organic phase were detected by gas chromato tion of 13 kPa, whereby an S/O suspension was obtained. The graph (model specification: 6890N. manufactured by Agi S/O suspension was added to 200 mL of an aqueous solution lent), whereby the constituent fatty acid composition in the having been heated to 70 C in advance and containing 0.5% analyzed fat was analyzed. by weight of gum arabic (product name "Gum Arabic SD', 0120 produced by San-Ei Gen F.F.I., Inc.) and 0.03% by weight of 0121 The composition of each of the triglycerides con decaglycerol monooleate (product name “POEM J-0381V. tained in the fat to be analyzed and its content were deter produced by Riken Vitamin Co., Ltd.) and stirred with a disk mined from retention times and peak area ratios of a chart turbine blade, whereby an S/O/W emulsion was prepared. produced by analysis with gas chromatograph equipped with Thereafter, the S/O/W emulsion was added in one portion to a flame ionization detector and fitted with a capillary column. 400 mL of an aqueous solution having been cooled to 5 C in The measurement conditions are as follows: advance and containing 0.5% by weight of gum arabic and 0122 Column: TAP-CB (manufactured by GL Sciences 0.03% by weight of decaglycerol monooleate to be cooled Inc.), 0.2 mm in inner diameter, 25 m in length rapidly, followed by Suction filtration and vacuum drying, 0123 Temperature conditions: onset temperature was 100 whereby an S/O type microcapsule was obtained. A disinte C; after temperature elevation up to 320 C at a rate of tem gration test was performed using the microcapsule. The perature elevation of 10 C/minute, the temperature was held results are shown in Table 3. at 320 C for 8 minutes. 0.124

added and dispersed with a homogenizer (T.K. Homomixer tion at 90 C and a degree of vacuum of 4.0 kPa for 20 minutes. MARK II20, manufactured by PRIMIX Corporation), After the reaction, the reaction was terminated by the addition whereby an S/O suspension was obtained. The S/O suspen of enough water and at the same time a soap content generated sion was fed to a double-fluid nozzle (hollow cone spray was removed. Then, heat-dehydration was performed at 90 C noZZle, manufactured by Ikeuchi Co., Ltd.) at a pressure of and a degree of vacuum of 4.0 kPa, 20g of white clay (pro 0.3 MPa with a pump and sprayed into a cooling field of 10C. duced by Mizusawa Industrial Chemicals, Ltd.) was added whereby an S/O type microcapsule enclosing lactoferrin was and held for 10 minutes, and then the white clay was removed obtained. by Suction filtration using filter paper (produced by Advantec Toyo Kaisha, Ltd.; No. 1), whereby a transesterified fat was Example 22 obtained. Nine hundred grams of n-hexane was added to 300 g of the resulting transesterified fat and heated to 45 C. 0134) To 900 g of tripalmitin, 400 g of capric acid (pro whereby the transesterified fat was dissolved completely. A duced by Wako Pure Chemical Industries, Ltd.) and 2400 g of solution of the transesterified fat in hexane was cooled at a hexane (produced by Wako Pure Chemical Industries, Ltd.) rate of 0.5 C/minute to 20 Cunder stirring. After holding at 20 were added and heated to 55 C. Thirteen grams offixed lipase C for 40 minutes, it was subjected to suction filtration and (product name “Lipozyme RMIM, produced by thereby a crystalline fraction was removed. The resulting Novozymes) was added thereto and a transesterification reac filtrate fraction was heated to 35 C, held for 10 minutes, and tion was performed for 8 hours under stirring at 55 C. After cooled at a rate of 0.5 C/minute to 0 C under stirring. After the completion of the reaction, the fixed lipase was removed holding at 0C for 30 minutes, the crystalline fraction obtained by suction filtration at 80 C using filter paper (produced by was collected by Suction filtration and hexane was evaporated Advantec Toyo Kaisha, Ltd.; No. 1). Thereafter, hexane and a with an evaporator, followed by steam distillation at 210 C, fatty acid were removed by using a thin film distillation whereby a medium melting fraction was obtained. The trig instrument (manufactured by Sibata Scientific Technology lyceride composition of the resulting medium melting frac Ltd.) at a flow rate of 100 mL/hour, a distillation temperature tion, the contents of the respective components, and the pro of 200 C, and a degree of vacuum of 6.7 Pa. Nine hundred portion of Saturated fatty acids having 14 or more carbon grams of n-hexane was added to 300 g of the resulting trans atoms are shown in Table 2. esterified fat and heated to 45 C, whereby the transesterified 0.137 An S/O type microcapsule containing the medium fat was dissolved completely. A solution of the transesterified melting fraction of the transesterified fat as a matrix was fat in hexane was cooled at a rate of 0.5 C/minute to 20 C prepared as follows. To an oily component composed of 20 g under stirring. After holding at 20 C for 40 minutes, it was of a fractionated fat having been melted by being heated to a subjected to suction filtration and thereby a crystalline frac temperature of 60 C in advance and 1.0 g of tetraglycerol tion was removed. The resulting filtrate fraction was heated to condensed ricinoleate (product name “POEM PR-100', pro 35 C, held for 10 minutes, and cooled at a rate of 0.5 C/minute duced by Riken Vitamin Co., Ltd.), 10 mL of a 30% glu to 0 C under stirring. After holding at 0C for 30 minutes, the tathione aqueous solution was added, followed by performing crystalline fraction obtained was collected by suction filtra emulsification and dispersion with a homogenizer (T.K. tion and hexane was evaporated with an evaporator, followed Homomixer MARK II20, manufactured by PRIMIX Corpo by steam distillation at 210 C, whereby a medium melting ration), whereby a W/O emulsion was prepared. Subse fraction was obtained. The triglyceride composition of the quently, the W/O emulsion was subjected to moisture resulting medium melting fraction, the contents of the respec removal while being stirred at a temperature of 35C for 30 tive components, and the proportion of Saturated fatty acids minutes under a reduced pressure condition of 13 kPa, having 14 or more carbon atoms are shown in Table 2. whereby an S/O suspension was obtained. The S/O suspen 0135 An S/O type microcapsule containing the medium sion was added to 200 mL of an aqueous solution having been melting fraction of the transesterified fat as a matrix was heated to 35 C in advance and containing 0.5% by weight of prepared as follows. To an oily component composed of 20 g gum arabic (product name “Gum Arabic SD, produced by of a fractionated fat having been melted by being heated to a San-Ei Gen F.F.I., Inc.) and 0.03% by weight of decaglycerol temperature of 40C in advance and 1.0 g of Sucrose erucate monooleate (product name “POEMJ-0381V, produced by (product name “ER-290, produced by Mitsubishi-Kagaku Riken Vitamin Co., Ltd.) and stirred with a disk turbine blade, Foods Corporation), 1 g of lactoferrin was added and dis whereby an S/O/W emulsion was prepared. Thereafter, the persed with a homogenizer (T.K. Homomixer MARK II20, S/O/W emulsion was added in one portion to 400 mL of an manufactured by PRIMIX Corporation), whereby an S/O aqueous solution having been cooled to 5 C in advance and Suspension was obtained. The S/O Suspension was fed to a containing 0.5% by weight of gum arabic and 0.03% by double-fluid nozzle (hollow cone spray nozzle, manufactured weight of decaglycerol monooleate to be cooled rapidly, fol by Ikeuchi Co., Ltd.) at a pressure of 0.3 MPa with a pump and lowed by Suction filtration and vacuum drying, whereby an sprayed into a cooling field of 10 C, whereby an S/O type S/O type microcapsule enclosing glutathione was obtained. microcapsule enclosing lactoferrin was obtained. Example 24 Example 23 0.138. To 900 g of fully hardened rapeseed oil (produced 0.136 Five hundred grams of medium chain fatty acid by Taiyo Yushi Corporation), 400 g of capric acid (produced triglyceride (product name Actor M2, produced by Riken by Wako Pure Chemical Industries, Ltd.) and 2400 g of hex Vitamin Co., Ltd.) and 500 g of fully hardened rapeseed oil ane (produced by Wako Pure Chemical Industries, Ltd.) were (produced by Taiyo Yushi Corporation) were mixed, and the added and heated to 55 C. Thirteen grams of fixed lipase mixture was subjected to heat-dehydration at 90 C and a (product name “Lipozyme RMIM, produced by degree of vacuum of 4.0 kPa, and then 1 g of sodium methy Novozymes) was added thereto and a transesterification reac late was added thereto, followed by a transesterification reac tion was performed for 8 hours under stirring at 55 C. After US 2013/007 1525 A1 Mar. 21, 2013

the completion of the reaction, the fixed lipase was removed duced by Advantec Toyo Kaisha, Ltd.; No. 1). Then, hexane by suction filtration at 80 C using filter paper (produced by and a fatty acid were removed by using a thin film distillation Advantec Toyo Kaisha, Ltd.; No. 1). Then, hexane and a fatty instrument (manufactured by Sibata Scientific Technology acid were removed by using a thin film distillation instrument Ltd.) at a flow rate of 100 mL/hour, a distillation temperature (manufactured by Sibata Scientific Technology Ltd.) at a flow of 200 C, and a degree of vacuum of 6.7 Pa, whereby a rate of 100 mL/hour, a distillation temperature of 200 C, and transesterified fat was obtained. To 20 g of the resulting a degree of vacuum of 6.7 Pa, whereby a transesterified fat transesterified fat was added 10g of medium chain fatty acid was obtained. Nine hundred grams of n-hexane was added to triglyceride (product name Actor M2, produced by Riken 300 g of the resulting transesterified fat and heated to 45 C. Vitamin Co., Ltd.) at 40 C, followed by mixing, whereby a whereby the transesterified fat was dissolved completely. mixed fat was prepared. The triglyceride composition of the Then, a solution of the transesterified fat in hexane was cooled resulting mixed fat, the contents of the respective compo at a rate of 0.5 C/minute to 20 C under stirring. After holding nents, and the proportion of saturated fatty acids having 14 or at 20 C for 40 minutes, it was subjected to suction filtration more carbon atoms are shown in Table 2. and thereby a crystalline fraction was removed. The resulting 0.141. An S/O type microcapsule containing the mixed fat filtrate fraction was heated to 35 C, held for 10 minutes, and composed of the transesterified fat and the medium chain cooled at a rate of 0.5 C/minute to 0 C under stirring. After fatty acid triglyceride as a matrix was prepared as follows. holding at 0C for 30 minutes, the crystalline fraction obtained 0142. To an oily component composed of the above-de was collected by Suction filtration and hexane was evaporated scribed mixed fat having been melted by being heated to a with an evaporator, followed by steam distillation at 210 C, temperature of 40C in advance and 1.0 g of tetraglycerol whereby a medium melting fraction was obtained. The trig condensed ricinoleate (product name “POEM PR-100', pro lyceride composition of the resulting medium melting frac duced by Riken Vitamin Co., Ltd.), 10 mL of an aqueous tion, the contents of the respective components, and the pro solution containing 10% by weight of Food Red No. 102 was portion of Saturated fatty acids having 14 or more carbon added, followed by performing emulsification and dispersion atoms are shown in Table 2. with a homogenizer (T.K. Homomixer MARK II20, manu 0.139. An S/O type microcapsule containing the medium factured by PRIMIX Corporation), whereby a W/O emulsion melting fraction of the transesterified fat as a matrix was was prepared. Subsequently, the W/O emulsion was sub prepared as follows. To an oily component composed of 20 g jected to moisture removal while being stirred at a tempera of a fractionated fat having been melted by being heated to a ture of 40C for 30 minutes under a reduced pressure condi temperature of 40C in advance and 1.0 g of tetraglycerol tion of 13 kPa, whereby an S/O suspension was obtained. The condensed ricinoleate (product name “POEM PR-100', pro S/O suspension was added to 200 mL of an aqueous solution duced by Riken Vitamin Co., Ltd.), 10 mL of a 30% glu having been heated to 40 C in advance and containing 0.5% tathione aqueous solution was added, followed by performing by weight of gum arabic (product name "Gum Arabic SD', emulsification and dispersion with a homogenizer (T.K. produced by San-Ei Gen F.F.I., Inc.) and 0.03% by weight of Homomixer MARK II20, manufactured by PRIMIX Corpo decaglycerol monooleate (product name “POEM J-0381V. ration), whereby a W/O emulsion was prepared. Subse produced by Riken Vitamin Co., Ltd.) and stirred with a disk quently, the W/O emulsion was subjected to moisture turbine blade, whereby an S/O/W emulsion was prepared. removal while being stirred at a temperature of 40C for 30 Thereafter, the S/O/W emulsion was added in one portion to minutes under a reduced pressure condition of 13 kPa, 400 mL of an aqueous solution having been cooled to 5 C in whereby an S/O suspension was obtained. The S/O suspen advance and containing 0.5% by weight of gum arabic and sion was added to 200 mL of an aqueous solution having been 0.03% by weight of decaglycerol monooleate to be cooled heated to 40 C in advance and containing 0.5% by weight of rapidly, followed by Suction filtration and vacuum drying, gum arabic (product name “Gum Arabic SD, produced by whereby an S/O type microcapsule was obtained. San-Ei Gen F.F.I., Inc.) and 0.03% by weight of decaglycerol monooleate (product name “POEMJ-0381V, produced by Example 26 Riken Vitamin Co., Ltd.) and stirred with a disk turbine blade, whereby an S/O/W emulsion was prepared. Thereafter, the 0.143 To 300 g of medium chain fatty acid triglyceride S/O/W emulsion was added in one portion to 400 mL of an (product name Actor M2, produced by Riken Vitamin Co., aqueous solution having been cooled to 5 C in advance and Ltd.), 700 g of stearic acid (produced by Wako Pure Chemical containing 0.5% by weight of gum arabic and 0.03% by Industries, Ltd.) and 2000 g of hexane (produced by Wako weight of decaglycerol monooleate to be cooled rapidly, fol Pure Chemical Industries, Ltd.) were added and heated to 55 lowed by Suction filtration and vacuum drying, whereby an C. Thirteen grams of fixed 1,3-position specific lipase (prod S/O type microcapsule enclosing glutathione was obtained. uct name “Lipozyme RMIM, produced by Novozymes) was added thereto and a transesterification reaction was per Example 25 formed for 8 hours under stirring at 55 C. After the comple tion of the reaction, the fixed lipase was removed by suction 0140. To 450 g of fully hardened rapeseed oil (produced filtration at 80 C using filter paper (produced by Advantec by Taiyo Yushi Corporation), 500 g of lauric acid (produced Toyo Kaisha, Ltd.; No. 1). Thereafter, hexane and a fatty acid by Wako Pure Chemical Industries, Ltd.) and 1900 g of hex were removed by using a thin film distillation instrument ane (produced by Wako Pure Chemical Industries, Ltd.) were (manufactured by Sibata Scientific Technology Ltd.) at a flow added and heated to 55 C. Fifteen grams of fixed 1,3-position rate of 100 mL/hour, a distillation temperature of 200 C, and specific lipase (product name “Lipozyme RMIM, produced a degree of vacuum of 6.7 Pa. Nine hundred grams of n-hex by Novozymes) was added thereto and a transesterification ane was added to 300 g of the resulting transesterified fat and reaction was performed for 8 hours under stirring at 55 C. heated to 45 C, whereby the transesterified fat was dissolved After the completion of the reaction, the fixed lipase was completely. Then, a solution of the transesterified fat in hex removed by suction filtration at 80 C using filter paper (pro ane was cooledata rate of 0.5 C/minute to 20 Cunder stirring. US 2013/007 1525 A1 Mar. 21, 2013

After holding at 20 C for 40 minutes, it was subjected to After holding at 20 C for 40 minutes, it was subjected to suction filtration and thereby a crystalline fraction was suction filtration and thereby a crystalline fraction was removed. The resulting filtrate fraction was heated to 35 C. removed. The resulting filtrate fraction was heated to 35 C. held for 10 minutes, and cooled at a rate of 0.5 C/minute to 0 held for 10 minutes, and cooled at a rate of 0.5 C/minute to 0 C under stirring. After holding at 0C for 30 minutes, the C under stirring. After holding at 0C for 30 minutes, the crystalline fraction obtained was collected by suction filtra crystalline fraction obtained was collected by suction filtra tion and hexane was evaporated with an evaporator, followed tion and hexane was evaporated with an evaporator, followed by steam distillation at 210 C, whereby a medium melting by steam distillation at 210 C, whereby a medium melting fraction was obtained. The triglyceride composition of the fraction was obtained. To 20g of the medium melting fraction resulting medium melting fraction, the contents of the respec was added 2.0 g of medium chain fatty acid triglyceride tive components, and the proportion of Saturated fatty acids (product name Actor M2, produced by Riken Vitamin Co., having 14 or more carbonatoms are shown in Table 2. An S/O Ltd.) at 45 C as liquid oil, followed by mixing, whereby a type microcapsule containing the medium melting fraction of mixed fat was prepared. The triglyceride composition of the the transesterified fat as a matrix was prepared as follows. To resulting mixed fat, the contents of the respective compo an oily component composed of 20 g of a medium melting nents, and the proportion of saturated fatty acids having 14 or fraction having been melted by being heated to a temperature more carbon atoms are shown in Table 2. of 50 C in advance and 1.0 g of tetraglycerol condensed 0145 An S/O type microcapsule containing the mixed fat ricinoleate (product name “POEM PR-100', produced by composed of the medium melting fraction of the transesteri Riken Vitamin Co., Ltd.), 10 mL of an aqueous solution fied fat and the liquid oil as a matrix was prepared as follows. containing 10% by weight of Food Red No. 102 was added, To an oily component composed of the above-described followed by performing emulsification and dispersion with a mixed fat having been melted by being heated to a tempera homogenizer (T.K. Homomixer MARK II20, manufactured ture of 45 C in advance and 1.0 g of tetraglycerol condensed by PRIMIX Corporation), whereby a W/O emulsion was ricinoleate (product name “POEM PR-100', produced by prepared. Subsequently, the W/O emulsion was subjected to Riken Vitamin Co., Ltd.), 10 mL of an aqueous solution moisture removal while being stirred at a temperature of 50C containing 10% by weight of Food Red No. 102 was added, for 30 minutes under a reduced pressure condition of 13 kPa, followed by performing emulsification and dispersion with a whereby an S/O suspension was obtained. The S/O suspen homogenizer (T.K. Homomixer MARK II20, manufactured sion was added to 200 mL of an aqueous solution having been by PRIMIX Corporation), whereby a W/O emulsion was heated to 50 C in advance and containing 0.5% by weight of prepared. Subsequently, the W/O emulsion was subjected to gum arabic (product name “Gum Arabic SD, produced by moisture removal while being stirred at a temperature of 45C San-Ei Gen F.F.I., Inc.) and 0.03% by weight of decaglycerol for 30 minutes under a reduced pressure condition of 13 kPa, monooleate (product name “POEMJ-0381V, produced by whereby an S/O suspension was obtained. The S/O suspen Riken Vitamin Co., Ltd.) and stirred with a disk turbine blade, sion was added to 200 mL of an aqueous solution having been whereby an S/O/W emulsion was prepared. Thereafter, the heated to 45 C in advance and containing 0.5% by weight of S/O/W emulsion was added in one portion to 400 mL of an gum arabic (product name “Gum Arabic SD, produced by aqueous solution having been cooled to 5 C in advance and San-Ei Gen F.F.I., Inc.) and 0.03% by weight of decaglycerol containing 0.5% by weight of gum arabic and 0.03% by monooleate (product name “POEMJ-0381V, produced by weight of decaglycerol monooleate to be cooled rapidly, fol Riken Vitamin Co., Ltd.) and stirred with a disk turbine blade, lowed by Suction filtration and vacuum drying, whereby an whereby an S/O/W emulsion was prepared. Thereafter, the S/O type microcapsule was obtained. A disintegration test S/O/W emulsion was added in one portion to 400 mL of an was performed using the microcapsule. The results are shown aqueous solution having been cooled to 5 C in advance and in Table 3. containing 0.5% by weight of gum arabic and 0.03% by weight of decaglycerol monooleate to be cooled rapidly, fol Example 27 lowed by Suction filtration and vacuum drying, whereby an 0144. To 300 g of medium chain fatty acid triglyceride S/O type microcapsule was obtained. A disintegration test (product name Actor M2, produced by Riken Vitamin Co., was performed using the microcapsule. The results are shown Ltd.), 700 g of stearic acid (produced by Wako Pure Chemical in Table 3. Industries, Ltd.) and 2000 g of hexane (produced by Wako Pure Chemical Industries, Ltd.) were added and heated to 55 Example 28 C. Thirteen grams of fixed 1,3-position specific lipase (prod uct name “Lipozyme RMIM, produced by Novozymes) was 0146 Fifty grams of crystalline cellulose for tablet coat added thereto and a transesterification reaction was per ing, 0.5g of magnesium Stearate, and 50g of lactoferrin were formed for 8 hours under stirring at 55 C. After the comple mixed and then pressed into a tablet with a tablet presser tion of the reaction, the fixed lipase was removed by suction (WPM-5, manufactured by Okada Seiko Co., Ltd.), using a filtration at 80 C using filter paper (produced by Advantec pounder with a diameter of 12.0mmata tabletting pressure of Toyo Kaisha, Ltd.; No. 1). Thereafter, hexane and a fatty acid 0.5 ton/cm, whereby a tablet was obtained. Then, the were removed by using a thin film distillation instrument medium melting fraction of the transesterified fat produced in (manufactured by Sibata Scientific Technology Ltd.) at a flow Example 26 was heated to 55C to be melted, thereby forming rate of 100 mL/hour, a distillation temperature of 200 C, and a coating fat. While the prepared tablet was rotated, the coat a degree of vacuum of 6.7 Pa. Nine hundred grams of n-hex ing fat was sprayed through a single-fluid nozzle (hollow ane was added to 300 g of the resulting transesterified fat and cone spray nozzle, manufactured by Ikeuchi Co., Ltd.) to heated to 45 C, whereby the transesterified fat was dissolved apply a coating treatment to the Surface of the tablet, whereby completely. Then, a solution of the transesterified fat in hex a coated tablet having a coating fat layer with a thickness of ane was cooledata rate of 0.5 C/minute to 20 C under stirring. about 0.5 mm on the tablet surface was obtained. US 2013/007 1525 A1 Mar. 21, 2013

Comparative Example 3 been adjusted to 45 C was mixed, whereby an oily component was prepared. The triglyceride composition of the resulting 0147 To an oily component composed of 20 g of tripalm oily component, the contents of the respective components, itin (produced by Wako Pure Chemical Industries, Ltd., tri and the proportion of Saturated fatty acids having 14 or more palmitin acid content 98.2% by weight) having been melted carbon atoms are shown in Table 2. by being heated to a temperature of 80 C in advance and 1.0 0149. To the above-mentioned oily component, 10 mL of g of tetraglycerol condensed ricinoleate (product name a 10% by weight Food Red No. 102 aqueous solution was “POEM PR-100', produced by Riken Vitamin Co., Ltd.), 10 added, the temperature thereof was adjusted to 35C, followed mL of an aqueous solution containing 10% by weight of Food by performing emulsification and dispersion with a homog Red No. 102 was added, followed by performing emulsifica enizer (T.K. Homomixer MARK II20, manufactured by PRI tion and dispersion with a homogenizer, whereby a W/O MIX Corporation), whereby a W/O emulsion was prepared. emulsion was prepared. Subsequently, the W/O emulsion was Subsequently, the W/O emulsion was subjected to moisture subjected to moisture removal while being stirred at a tem removal while being stirred at a temperature of 70 C for 30 perature of 80 C for 20 minutes under a reduced pressure minutes under a reduced pressure condition of 13 kPa, condition of 13 kPa, whereby an S/O suspension was whereby an S/O suspension was obtained. The S/O suspen obtained. An S/O type microcapsule was obtained in the same sion was added to 200 mL of an aqueous solution having been manner as in Example 18 except that the S/O suspension was heated to 45 C in advance and containing 0.5% by weight of added to 300 mL of an aqueous solution having been heated gum arabic (product name “Gum Arabic SD, produced by to 70 C in advance and containing 0.5% by weight of gum San-Ei Gen F.F.I., Inc.) and 0.03% by weight of decaglycerol arabic and 0.05% by weight of decaglycerol monooleate and monooleate (product name “POEMJ-0381V, produced by stirred with a disk turbine blade, whereby an S/O/W emulsion Riken Vitamin Co., Ltd.) and stirred with a disk turbine blade, was prepared. A disintegration test was performed using the whereby an S/O/W emulsion was prepared. Thereafter, the microcapsule. The results are shown in Table 3. S/O/W emulsion was added in one portion to 400 mL of an aqueous solution having been cooled to 5 C in advance and Comparative Example 4 containing 0.5% by weight of gum arabic and 0.03% by 0148. To 20 g of medium chain fatty acid triglyceride weight of decaglycerol monooleate to be cooled rapidly, fol (product name Actor M2, produced by Riken Vitamin Co., lowed by Suction filtration and vacuum drying, whereby an Ltd.) and 1.0 g of tetraglycerol condensed ricinoleate (prod S/O type microcapsule was obtained. The resulting microcap uct name “POEM PR-100', produced by Riken Vitamin Co., Sule was not capable of being handled because it was very soft Ltd.), 30 g of the fat of Example 20 whose temperature had and Sticky and particles thereof stuck together. TABLE 2 Solid fat content at Triglyceride compositions of fat compositions of respective examples and comparative each temperature of example, and their contents (% by weight) fat composition used Triglyceride (A) containing Saturated fatty acid having 6 to 12 carbon atoms (%) and Saturated fatty acid having 14 or more carbon atoms

25 C. 37 C. C8:C8:C18 C8:C18:C18 C10:C10:C16 C10:C10:C18 C10:C16:C16 C10:C18:C18

Example 18 87.8 25 7.5 72.2 Example 19 96.4 76.8 Example 20 95.2 74.8 Example 21 97.6 89.9 Example 22 96.9 88.1 8.2 4S.O Example 23 86.5 55.8 6.2 69.3 Example 24 89 65.2 7.2 68.2 Example 25 62.2 61.1 Example 26 94 88.3 7.2 85.2 Example 27 84 78.3 6.3 74.O Example 28 94 88.3 7.2 85.2 Comparative 57.1 44.9 Example 4 Triglyceride compositions* offat compositions of respective examples and Proportion of comparative example, and their contents (% by weight) Saturated fatty acid Triglyceride (A) containing Saturated fatty acid having 6 to 12 having 14 or more carbon atoms and Saturated fatty acid having 14 or more carbon atoms Other than carbon atoms C12:C12:C16 C12:C16:C16 C12:C12:C18 C12:C18:C18 Total (A) (% by weight)

Example 18 79.7 20.3 66 Example 19 19.6 43.4 63 37.0 61 Example 20 34.O 38.9 72.9 27.1 76 Example 21 21.3 53.5 74.8 25.2 60 Example 22 53.2 46.8 79 Example 23 75.5 24.5 67 Example 24 75.4 24.6 67 Example 25 22.8 26.1 48.9 51.1 51 US 2013/007 1525 A1 Mar. 21, 2013 18

TABLE 2-continued Example 26 92.4 7.6 65 Example 27 80.3 19.7 56 Example 28 92.4 7.6 65 Comparative 23.5 43.5 56.5 46 Example 4

TABLE 3 5. The particulate composition according to claim 1, wherein the fat composition is a mixture of 95 to 60% by Release rate of enclosed substance (% weight of a high-melting-point fat and 5 to 40% by weight of Time Example Example Example Comparative a low-melting-point oil. (min) 18 26 27 Example 3 6. The particulate composition according to claim 5. wherein the high-melting-point fat is at least one member O O O O O 2O 26.2 7.6 21.5 3.3 selected from the group consisting of fractionated palm oil, 40 53.2 16.2 SO.9 7.2 hardened palm oil, fully hardened palm oil, hardened rape 60 72.3 26.9 67.8 14.5 seed oil, fully hardened rapeseed oil, tristearin, and tripalm 360 100 96.4 100 1OO itin. 7. The particulate composition according to claim 5. 0150. The above-mentioned results show that good enteric wherein the low-melting-point oil is at least one member properties are exhibited by S/O type microcapsule formula selected from the group consisting of palm kernel oil, coconut tions using, as matrix components, fat compositions contain oil, medium chain fatty acid triglyceride, soybean oil, rice oil, ing 45% by weight or more of a triglyceride including at least corn oil, olive oil, rapeseed oil, sunflower oil, perilla oil, both a saturated fatty acid having 6 to 12 carbon atoms and a low-melting fractions of fish oil, diglyceride, and oleic acid. saturated fatty acid having 14 or more carbon atoms as con 8. The particulate composition according to claim 1, stituent fatty acids, wherein the proportion of the saturated wherein the fat composition is obtained by a transesterifica fatty acid having 14 or more carbon atoms in the constituent tion reaction. fatty acids of the whole fat exceeds 50% by weight. 9. The particulate composition according to claim 8. wherein an enzyme or a microorganism is used in the trans 1. A particulate composition, wherein a hydrophilic Sub esterification reaction. stance is polydispersed in a matrix of a fat composition hav 10. The particulate composition according to claim 1, ing a solid fat content at 25 C of 58% or more and a solid fat wherein the weight ratio of the hydrophilic substance to the content at 37 C of 90% or less. fat composition is within the range of from 0.01/99.99 to 2. The particulate composition according to claim 1, 70/30. wherein the solid fat content at 37 C of the fat composition is 11. The particulate composition according to claim 1, fur 50% or more. ther comprising a hydrophobic component. 3. The particulate composition according to claim 1, 12. The particulate composition according to claim 1, wherein the fat composition is a coating fat composition wherein the release rate of the hydrophilic substance in an containing 45% by weight or more of a triglyceride compris intestinal disintegration test is 40% or more. ing at least both a saturated fatty acid having 6 to 12 carbon 13. A coating fat composition containing 45% by weight or atoms and a saturated fatty acid having 14 or more carbon more of a triglyceride comprising at least both a saturated atoms as constituent fatty acids and the proportion of the fatty acid having 6 to 12 carbon atoms and a saturated fatty saturated fatty acid having 14 or more carbon atoms in the acid having 14 or more carbon atoms as constituent fatty constituent fatty acids of the whole fat composition exceeds acids, wherein the proportion of the saturated fatty acid hav 50% by weight. ing 14 or more carbon atoms in the constituent fatty acids of 4. The particulate composition according to claim 3, the whole fat composition exceeds 50% by weight. wherein in the coating fat composition, the content of a trig 14. The coating fat composition according to claim 13, lyceride comprising at least both a saturated fatty acid having wherein the fat composition is obtained by a transesterifica 8 to 12 carbonatoms and a saturated fatty acid having 16 or 18 tion reaction. carbon atoms as constituent fatty acids is 50 to 90% by weight.