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US 20100184864A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2010/0184864 A1 Hamajima et al. (43) Pub. Date: Jul. 22, 2010

(54) COMPOSITE MATERIAL AND METHOD FOR Publication Classification PRODUCTION THEREOF (51) Int. Cl. A6II 3/16 (2006.01) (75) Inventors: Tadashi Hamajima, A6IR 8/42 (2006.01) Higashi-Osaka-shi (JP); Tomomi A6IPI/00 (2006.01) Yanagibayashi, Higashi-Osaka-shi A6IP3/00 (2006.01) (JP); Ryuji Arakawa, A6IP 9/00 (2006.01) Higashi-Osaka-shi (JP); Morihiro A23D 9/007 (2006.01) Aoyagi, Higashi-Osaka-shi (JP); (52) U.S. Cl...... 514/627; 426/611 Masayoshi Kushi, Higashi-Osaka-shi (JP) (57) ABSTRACT Disclosed are: a material which contains a lipophilic compo Correspondence Address: nent having a pungent taste or flavor Such as a spicy compo MARSHALL, GERSTEIN & BORUN LLP nent (e.g., a ) and a bitter component (e.g., a tur 233 SOUTH WACKER DRIVE, 6300 WILLIS meric extract), in which the pungent taste and/or flavor of the TOWER lipophilic component can be reduced effectively, and in CHICAGO, IL 60606–6357 (US) which the separation among components contained therein is not caused; a method for producing the material; a composi (73) Assignee: HOUSE FOODS tion Such as a food, a beverage, a cosmetic and a medicine, CORPORATION, which contains the material; and a liquid composition having Higashi-Osaka-shi, Osaka (JP) such a form that the material is dispersed in water. Specifi cally disclosed are: a composite material comprising a lipo (21) Appl. No.: 12/665,021 philic component having a pungent taste and/or flavor, a -derived ester and a cyclodextrin; a compo (22) PCT Filed: Jun. 27, 2008 sition comprising the composite material; a liquid composi tion which comprises the composite material, water and a (86). PCT No.: PCT/UP2008/O61744 thickening agent and has such a form that the composite material is dispersed in water; and a method for producing a S371 (c)(1), composite material comprising a lipophilic component hav (2), (4) Date: Dec. 16, 2009 ing a pungent taste and/or flavor, a plant-derived cholesterol ester and a cyclodextrin, which comprises mixing the lipo (30) Foreign Application Priority Data philic component, the plant-derived cholesterol ester and the cyclodextrin in the presence of water to form the composite Jun. 29, 2007 (JP) ...... 2007-172987 material. US 2010/01 84864 A1 Jul. 22, 2010

COMPOSITE MATERIAL AND METHOD FOR icins and bitter components such as a turmeric extract, the PRODUCTION THEREOF material being capable of effectively inhibiting the irritating taste and/or odor of the lipophilic components and of avoid TECHNICAL FIELD ing the separation of the components; and a production method thereof. 0001. The present invention relates to: a composite mate 0010. Another object of the present invention is to provide rial containing a lipophilic component having an irritating a composition, such as foods, beverages, cosmetics and phar taste or odor typified by pungent components such as capsa maceutical drugs, including the above-described material icins and bitter components such as a turmeric extract; and a blended therein. production method thereof. 0011 Moreover, still another object of the present inven tion is to provide a liquid composition in which the above BACKGROUND ART described material is in a water dispersed form. 0002 , which are pungent components of cap (0012. The present invention provides a composite material sicum pepper, for example, and one of the lipophilic compo comprising: a lipophilic component having an irritating taste nents having an irritating taste or odor, are known to have and/or odor; a phytosterol ester, and a cyclodextrin. various effects useful for organisms, such as an effect of 0013. In addition, the present invention provides a com appetite stimulation, an effect of vasodilation and vasocon position comprising the composite material blended therein. striction, an effect of increasing salivation, an effect of 0014 Further, the present invention provides a liquid com increasing gastric acid secretion, an effect of increasing peri position comprising the composite material, water and a staltic movement of the intestinal tract, an effect of decreasing thickener, wherein the composite material is in a water dis the cholesterol level in the circulatory system, an effect of persed form. increasing energy metabolism, and an effect of increasing the 0015. Furthermore, the present invention provides a release of bioactive peptides. However, capsaicins have a method for producing a composite material comprising: a strong pungency, and hence the application range thereof to lipophilic component having an irritating taste and/or odor; a foods and beverages has been limited. phytosterol ester; and a cyclodextrin, the method comprising 0003) To inhibit the pungency of capsaicins, novel glyco the step of mixing the lipophilic component, the phytosterol side capsaicinoids have been proposed which are obtained by ester and the cyclodextrin with each other in the presence of modifying the molecular structure of capsaicinoids to elimi water, to thereby form the composite material. nate their strong pungency (Patent Document 1). However, 10016. The present invention makes it possible to provide: the glycoside capsaicinoids are novel chemically synthesized a material including lipophilic components having an irritat compounds, and hence are not approved for use in foods or ing taste or odor typified by pungent components such as beverages. capsaicins and bitter components such as a turmeric extract, 0004 Moreover, a masking agent which is characterized the material being capable of effectively inhibiting the irritat by including a polyglycerin condensed ricinoleate and a food ing taste and/or odor of the lipophilic components and of including the masking agent have been proposed (Patent avoiding the separation of the components; and a production Document 2). Specifically, a masking agent-containing chili method thereof. oil has been disclosed which is obtained by adding 0.1% of a (0.017. The present invention also makes it possible to pro capsicum pepper extract oil and 0.5% of hexaglycerin con vide a composition, such as foods, beverages, cosmetics and densed ricinoleate to sesame oil. However, the application pharmaceutical drugs, including the above-described mate range of this masking agent is limited to foods and beverages rial blended therein. containing a large oil component, and in addition, this mask 0018 Moreover, the present invention makes it possible to ing agent is likely to affect the flavor of foods and beverages provide a liquid composition in which the above-described because of a waxy odor thereof. material is in a water dispersed form. 0005. Furthermore, an edible microcapsule has been pro posed which is characterized in that an edible fat and oil BEST MODES FOR CARRYING OUT THE containing capsaicin is used as a core material, a wall mem INVENTION brane is formed of protein and a coacervate agent, and a trans 0019. A composite material of the present invention by glutaminase is used as an agent for curing and crosslinking which an irritating taste and/or odor from a lipophilic com the wall membrane (Patent Document 3). However, the ponent having the irritating taste and/or odor is inhibited present inventors have actually prepared this edible micro includes: the lipophilic component having the irritating taste capsule and stirred this edible microcapsule with hot water (at and/or odor; a phytosterol ester, and a cyclodextrin. 97°C.) in a beaker, and as a result, the core material leaked (0020 Typical examples of the lipophilic component hav and floating oil was observed. Therefore, the edible micro ing an irritating taste and/or odor and used in the present capsule was found not to be suitable for beverages. invention include capsaicins, which are one of the lipophilic 0006 Patent Document 1: Japanese Patent No. 31.56240 pungent components. The capsaicins include capsaicin, dihy 0007 Patent Document 2: Japanese Patent Application drocapsaicin, nordihydrocapsaicin, homocapsaicin, Vanillyl Publication No. 2002-65177 nonanamide, and vanillyl butyl ether. Since they contain a 0008 Patent Document 3: Japanese Patent Application large amount of capsaicins, capsicum pepper extracts such as Publication No. 2003-47.432 capsicum oleoresins are suitably used as a raw material con taining capsaicins. DISCLOSURE OF THE INVENTION 0021. Meanwhile, examples of the lipophilic component 0009. An object of the present invention is to provide: a other than the capsaicins include: (6)-, (6)-shogaol. material including lipophilic components having an irritating Zingerone, and (8),(10)-shogaol, which are pungent compo taste or odor typified by pungent components such as capsa nents of ginger; and piperanine, which are pungent US 2010/01 84864 A1 Jul. 22, 2010 components of pepper, Sanshool, which is a pungent compo 0028. The composite material of the present invention can nent Japanese pepper, and allyl , which is a be obtained by mixing the lipophilic component, the phy pungent component of Japanese horseradish, Western horse tosterol ester, and the cyclodextrin in the presence of water. radish, mustard and the like. A pepper extract, a ginger The amount of the phytosterol ester which is present in pro extract, and a Japanese pepper extract can be Suitably used as ducing the composite material of the present invention varies a raw material containing pungent components of pepper, depending on the target lipophilic component; when the lipo ginger, and Japanese pepper, respectively. philic component is, for example, capsaicins, the amount of 0022 Besides the pungent components, the present inven the phytosterol ester is preferably 30 to 30000 parts by tion can be applied to lipophilic bitter components such as a weight, relative to 1 part by weight of capsaicins. Meanwhile, turmeric extract containing a lipophilic component with a the amount of the cyclodextrin is, for example, preferably bitter taste. It was found that the present invention reduces not 0.01 to 1000 parts by weight, and more preferably 0.1 to 100 only irritating tastes, but also irritating odors of the above parts by weight, relative to 1 part by weight of the phytosterol mentioned Japanese pepper extract, allyl mustard oil, and the ester. The amount of water which is present in producing the like. composite material is, for example, preferably 0.01 to 100 0023 The phytosterol ester used in the present invention is parts by weight, and more preferably 0.1 to 10 parts by a Substance obtained by ester-bonding a fatty acid to a weight, relative to 1 part by weight of the cyclodextrin. Mean hydroxyl group in the skeleton of a plant sterol. while, in producing the composite material of the present Examples of a production method of the phytosterol ester invention, the mixing is performed with warming to prefer include: an enzymatic method utilizing an ; and the ably 40 to 90° C., and more preferably 50 to 85°C. like. Examples of the enzymatic method include: a method of 0029 More specifically, the composite material of the obtaining the phytosterol ester by mixing the phytosterol and present invention can be produced by any one of the following the fatty acid and by causing reaction therebetween (at 30 to methods (1) to (3); however, in order to more effectively 50° C. for approximately 48 hours), with a lipase or the like inhibit the taste or odor of the lipophilic component, the used as a catalyst; and the like. Other synthesis methods method (1) is particularly preferable. include: a method of obtaining the phytosterol ester by esteri (1) dissolving the lipophilic component in the phytosterol fication which involves dehydration of a plant sterol produced ester, preparing a mixture containing the cyclodextrin and from or the like with a fatty acid obtained from water; and mixing the phytosterolester in which the lipophilic oil, , or the like, in the presence of a catalyst; component is dissolved with the mixture. and the like. (2) preparing a mixture containing the cyclodextrin, water 0024 Examples of the plant sterol include con and the phytosterol ester; and mixing the lipophilic compo tained in vegetable fats and oils, and the like. For example, the nent and water with the mixture. plant Sterol may be one extracted and purified from a Veg (3) preparing a mixture containing the lipophilic component etable fat or oil of soybean, rapeseed, , or the and the cyclodextrin; and mixing water and the phytosterol like. The plant sterol may be a mixture containing B-sito ester with the mixture. sterol, , , , fucosterol, 0030. Of these methods, the method (1) will be more spe dimethylsterol, and the like. For example, a soybean sterol cifically described below. When the lipophilic component is, contains 53 to 56% of sitosterol. 20 to 23% of campesterol for example, capsaicins, 1 part by weight of capsaicins is and 17 to 21% of stigmasterol. As the plant sterol, one which dissolved in 30 to 30000 parts by weight of the phytosterol is commercially-available as “phytosterol F.' (produced by ester, in the step of dissolving the lipophilic component in the TAMA BIOCHEMICAL CO.,LTD.) can also be used. phytosterol ester, although this varies depending on the target 0025. The fatty acid may be plant-derived, for example, lipophilic component. For dissolving the lipophilic compo derived from rapeseed oil or , or animal-derived. nent in the phytosterol ester, the lipophilic component is Examples of the fatty acid include myristic acid, Stearic acid, preferably dissolved in a way that the lipophilic component is palmitic acid, arachidonic acid, oleic acid, linoleic acid, C.-li added to the phytosterol ester, and the resultant is warmed to nolenic acid, Y-linolenic acid, eicosapentaenoic acid, docosa 40 to 80° C., preferably to 50 to 70° C. Alternatively, the hexaenoic acid, palmitoleic acid, lauric acid, and the like. lipophilic component may be dissolved in a way that the 0026. Preferable examples of the phytosterol ester phytosterol ester is warmed to 40 to 80°C., preferably 50 to include: phytosterol esters each obtained from a phytosterol 70° C., in advance, and the lipophilic component is added derived from soybean and a fatty acid derived from rapeseed thereto. oil; phytosterol esters each obtained from a phytosterol 0031. In the step of preparing the mixture containing the derived from soybean or rapeseed and a fatty acid derived cyclodextrin and water, the amounts of the cyclodextrin and from palm oil; and the like. The former includes “San Sterol water are not particularly limited, as long as the composite NO. 3’ of San-Ei Gen F. F.I., Inc., and the latter includes material can be formed later with these amounts. For “phytosterol fatty acid ester of TAMA BIOCHEMICAL example, the amount of the cyclodextrin is, for example, 0.01 CO.,LTD. to 1000 parts by weight and preferably 0.1 to 100 parts by 0027. The cyclodextrinused in the present invention refers weight relative to 1 part by weight of the phytosterol ester. to a cyclic non-reducing maltooligosaccharide, whose con The amount of water is, for example, 0.01 to 100 parts by stitutional unit is glucose. Even though any one of C-cyclo weight, and preferably 0.1 to 10 parts by weight, relative to 1 dextrin with six glucose units, B-cyclodextrin with seven part by weight of the cyclodextrin. glucose units, and Y-cyclodextrin with eight glucose units 0032. In the step of mixing the phytosterol ester in which may be used, Y-cyclodextrin is preferable since Y-cyclodextrin the lipophilic component is dissolved with the above-de is decomposed by human digestive and since Y-cy scribed mixture, the mixing is continued until the composite clodextrin is easy to use for foods and beverages, particularly material of the present invention is formed. The thus formed for beverages because of its high solubility in water. composite material is deposited in the form of grains in the US 2010/01 84864 A1 Jul. 22, 2010 lowerpart of water after the mixing is stopped and the mixture provided as a liquid composition in which the composite is allowed to stand for a while. Note that the mixing here is material is in a water dispersed form. Specifically, although performed preferably by using a mixing apparatus with high the composite material tends to be deposited in water, the shearing force. Such as a kneader, for forming the composite inclusion of the thickener makes it possible to provide a liquid material by thoroughly kneading these components. composition in which the composite material is dispersedly 0033. The obtained composite material can be in any form. held in water. This liquid composition can also be provided as For example, by using a vehicle or the like, the composite a liquid composition in a container, Such as a beverage in a material may be formed into a powder form or a granular container. In this case, there are advantages in that the oil form. The composite material may be in a liquid form or paste components do not separate in the container and hence the oil form where the composite material is dispersed or emulsified components do not attach onto the inner Surface of the con in a solvent such as water. tainer. 0034. The thus obtained composite material of the present 0040. Here, examples of the thickener include gellangum, invention is advantageous in that the irritating taste and/or fermentation-derived cellulose, Xanthan gum, gum arabic, odor of the lipophilic component is effectively inhibited. The tamarindgum, guar gum, locust bean gum, karayagum, tara inhibition of the irritating taste and/or odor in the composite gum, agar, gelatin, , soybean , CMC material of the present invention has a mechanism different (carboxymethylcellulose), carrageenan, microcrystalline cel form that of what is called masking involving addition of a lulose, propylene glycol alginate, and the like. Of these, fer Sweet component, or the like. It is uncertain what structure the mentation-derived cellulose is preferably used, from the composite material of the present invention has; however, it is viewpoint that the composite material is dispersed uniformly conceivable that at least the lipophilic component contained in water and the composite material has a favorable texture in the composite material of the present invention is in Such a when ingested orally. state that the lipophilic component cannot bind to the receptor 0041. The amount of the thickener is not particularly lim of the taste. ited, as long as the composite material can be dispersed in 0035. In addition, the composite material of the present water with the amount. For example, it is preferable that 0.01 invention is advantageous in that the oil components do not to 1.0% by weight of the thickener be contained in the liquid separate. Incidentally, when a composite material is produced composition. by using a different oil instead of the phytosterol ester, a homogeneous composite material cannot be obtained and the INDUSTRIAL APPLICABILITY oil component separates. Hence, when blended into a bever age or the like, the composite material has a problem that the 0042. The composite material of the present invention oil components float and attaches to the inner Surface of a including the lipophilic component having an irritating taste container. In contrast, the composite material of the present and/or odor; the phytosterol ester; and the cyclodextrin is a invention is advantageous in that a homogeneous composite composite material where the irritating taste and/or odor of material can be obtained, and that the oil components do not the lipophilic component is inhibited. Hence, the composite separate, and hence the oil components do not attach onto the material of the present invention can be applied to foods, inner Surface of a container, when blended into a beverage or beverages, cosmetics, pharmaceutical drugs, and the like, to the like, with the use of the phytosterol ester. which a lipophilic component having an irritating taste and/or 0036 Moreover, the composite material of the present odor has not been applicable so far. Therefore this makes it invention is also thermally stable. For example, even when the possible to provide foods, beverages, cosmetics, pharmaceu composite material is blended into a food or beverage, and tical drugs, and the like, having various effects useful for heated to 65 to 100° C., the irritating taste and/or odor of the organisms such as an effect of appetite stimulation, an effect lipophilic component can be inhibited, and no oil components of vasodilation vasoconstriction, an effect of increasing sali separate. Vation, an effect of increasing gastric acid secretion, an effect 0037. The composite material of the present invention is of increasing peristaltic movement of the intestinal tract, an easily dispersed in water. Hence, the composite material can effect of decreasing the cholesterol level in the circulatory be blended into foods or beverages, pharmaceutical drugs, system, an effect of increasing energy metabolism, and an cosmetics and the like, and provided as various compositions. effect of increasing the release of bioactive peptides. 0038 More specifically, examples of the food or beverage into which the composite material of the present invention is EXAMPLES blended include beverages, jellies, tablets, and the like. Here, a case where the composite material of the present invention Example 1 is blended into a beverage is taken as an example. A heat sterilized beverage in a container can be produced, for (1) Production of Composite Material example, as follows. The composite material of the present invention is added to water. An acidulant is added thereto to 0043. To 0.303 parts by weight of a phytosterol ester, adjust the pH to 4.0 or less, preferably 2.5 to 3.5. Raw mate 0.024 parts by weight of a capsicum oleoresin were added. rials such as a Sweetener, a fruit juice, a flavor, a coloring With stirring, the mixture was warmed to 60° C., and the agent, and vitamin C are added and mixed thereto. This mix capsicum oleoresin was dissolved. Thus a phytosterolester in ture is heated to 65 to 100° C. for sterilization treatment. Then which capsaicins were dissolved was prepared. this mixture is filled into a container, and sealed. Moreover, a 0044 Separately, 8.15 parts by weight of Y-cyclodextrin jelly in a container can be produced by adding a gelatinizing and 4.075 parts by weight of water (at 60° C.) were mixed agent to the above-mentioned raw materials. with each other, to thereby prepare a mixture (a paste). 0039. The composition of the present invention compris 0045. To the mixed paste, the phytosterol ester in which ing the composite material, water and a thickener can be the capsaicins were dissolved was added. The mixture was US 2010/01 84864 A1 Jul. 22, 2010

kneaded for 10 minutes by using a mortar, while being 0049. To the mixed paste, the phytosterol ester in which warmed at 60°C. Thus, a composite material was produced. the capsaicins were dissolved was added. The mixture was kneaded for 10 minutes by using a mortar, while being (2) Production of Beverage warmed to 60°C. Thus a composite material was produced. 0046. To the composite material, 87.338 parts by weight of water was added to be mixed therewith. Subsequently, 0.1 (2) Production of Beverage parts by weight of citric acid and 0.01 parts by weight of trisodium citrate were added to be mixed therewith. Next, this 0050. To the composite material, 92.19 parts by weight of mixture was warmed to 93°C. with stirring, and this tempera water were added to be mixed therewith. Subsequently, 0.1 ture was kept for 3 minutes to perform heat sterilization. parts by weight of citric acid and 0.01 parts by weight of Thereafter, this mixture was filled into a container, and trisodium citrate was added to be mixed therewith. Next, this cooled. Thus, a beverage in the container was produced. Note mixture was warmed to 93°C. with stirring, and this tempera that the beverage had a pH of 3.1. The thus obtained beverage ture was kept for 3 minutes to perform heat sterilization. had almost no perceptible pungency. Note that the following Thereafter, the mixture was filled into a container, and cooled. Thus, a beverage in the container was produced. Note that this table 1 shows the composition of the beverage. beverage had a pH of 3.1. 0051. The thus obtained beverage had almost no percep TABLE 1. tible pungency. Note that the following Table 2 shows the Composition of Beverage Parts by weight composition of the beverage. Capsicum oleoresin (content of capsaicins: 4.25% by O.O24 weight) Comparative Example 1 phytosterol ester O.303 (San-Ei Gen F.F.I., Inc., “San Sterol NO. 3) Y-cyclodextrin 8.15 0052. In accordance with the description in Patent Docu (Cyclochem Co., Ltd., “CAVAMAXW8 Food') ment 3, an edible microcapsule including, as the core mate Water 91.413 rial, fat and fatty oil containing approximately 0.15% by Citric acid (San-Ei Gen F.F.I., Inc.) O.1 weight of a capsicum pepper extract was prepared. Into a Trisodium citrate (San-Ei Gen F.F.I., Inc.) O.O1 beaker with a capacity of 200 ml, 5 parts by weight of this edible microcapsule and 95 parts by weight of hot water (water temperature: 97°C.) were added, and stirred manually Example 2 with a spatula. As a result, oil floated on the water Surface, and also a viscous Substance was deposited, thereby giving a (1) Production of Composite Material whitish liquid. Thus, said liquid was unstable for use. 0047. To 0.185 parts by weight of a phytosterol ester (San El Gen F. F.I., Inc. “San Sterol NO. 3'), 0.015 parts by weight Comparative Examples 2 to 5 of a capsicum oleoresin were added. With stirring, the mix ture was warmed to 60° C., and the capsicum oleoresin was 0053. Each composite material and each beverage were dissolved. Thus, a phytosterol ester in which capsaicins were produced in the same manner as in Example 2, except that the dissolved was prepared. phytosterol ester was replaced with a corresponding one of 0048 Separately, 5.00 parts by weight of Y-cyclodextrin materials described in the following Table 2. The fol and 2.5 parts by weight of water (at 60°C.) were mixed with lowing Table 2 shows the compositions of the beverages and each other, to thereby prepare a mixture (a paste). sensory evaluation results thereof.

TABLE 2 Example Example Comparative Comparative Comparative Comparative 1 Example 2 Example 3 Example 4 Example 5

Compo- Capsicum oleoresin O.O24 Parts OO15 Parts O.O15Parts OO15 Parts OO15 Parts OO15 Parts sition Raw Phytosterol ester O3O3 Parts O.185 Parts material Palm oil O.185 Parts lipid Diglyceride O.185 Parts (“Kenko Econa manufactured by Kao Corporation) Soybean phospholipid O.185 Parts (“Lecithin manufactured by J OIL MILLS, Inc.) Medium-chain fatty O.185 Parts acid triglyceride (“COCONARD RK manufactured by Kao Corporation) Y-cyclodextrin 8.15 Parts 5.00 Parts S.OOParts 5.00 Parts S.OOParts S.OO Parts Water 91.413 Parts 94.69 Parts 94.69 Parts 94.69 Parts 94.69 Parts 94.69 Parts US 2010/01 84864 A1 Jul. 22, 2010

TABLE 2-continued Example Example Comparative Comparative Comparative Comparative 1 2 Example 2 Example 3 Example 4 Example 5 Citric acid O.1 Parts O.1 Parts O.1 Parts O.1 Parts O.1 Parts O.1 Parts Trisodium citrate O.O1 Parts O.O1 Parts O.O1 Parts O.O1 Parts O.O1 Parts O.O1 Parts

Total 1OOOOParts 1OOOO Parts 1OOOO Parts 1OOOO Parts 1OOOOParts 1OOOO Parts Amount of capsaicins contained O.001 Parts O.006 Parts O.OO6 Parts O.006 Parts O.006 Parts O.OO6 Parts Sensory evaluation Almost no Almost no Pungency Pungency Pungency Pungency pungency pungency perceived perceived perceived perceived perceived perceived

Example 3 0059 Separately, 8.2 parts by weight of Y-cyclodextrin and 4 parts by weight of water (at 75° C.) were mixed with (1) Production of Composite Material each other, to thereby prepare a mixture (a paste). 0054 150 parts by weight of a phytosterol ester (San-Ei 0060. To the mixed paste, the phytosterol ester in which Gen F.F.I., Inc. “San Sterol No. 3), and 1.42 parts by weight the pungent component or the bitter component was dis of a capsicum oleoresin (content of capsaicins: 35.21% by solved was added. The mixture was kneaded for 10 minutes weight) were weighted into a beaker. The mixture was by using a mortar, while being warmed at 75° C. Thus each warmed in hot water until the temperature thereofreached 60° composite material was produced. C., and the capsicum oleoresin was dissolved. Thus a phy tosterol ester in which the capsaicins were dissolved was prepared. (2) Production of Beverages 0055 Next, into a measurement kneader (jacket water 0061. To each of the composite materials, 87 parts by temperature: 30° C.) of a kneader (manufactured by Bra bender, DO-CORDER, DO330 model), 300 parts by weight weight of water were added to be mixed therewith. Subse of Y-cyclodextrin were added. With stirring at 66 rpm, 150 quently, 0.1 parts by weight of citric acid and 0.01 parts by parts by weight of water (at 30°C.) were added thereto. After weight of trisodium citrate were added to be mixed therewith. 5 minutes of stirring, 29 parts by weight of the above-de Next, this mixture was warmed to 93° C. with stirring, and scribed phytosterol ester containing the capsaicins were this temperature was kept for 3 minutes to perform heat sterilization. Thereafter, this mixture was filled into a con added thereto, and the mixture was stirred for 30 minutes. tainer, and cooled. Thus, each beverage in the container was Thus, a composite material was produced. produced. (2) Production of Beverage (3) Evaluation of Beverage 0056 To 28.82 parts by weight of the composite material, 770.3 parts by weight of water were added to be mixed 0062. As shown in evaluation results in Table 3, the thus thereto. Subsequently, 0.8 parts by weight of citric acid and produced beverages were Superior to those in Comparative 0.08 parts by weight of trisodium citrate were added to be Examples shown below interms of reduction in taste and odor mixed thereto. This mixture was heated to 93° C. with stir and appearance (floating oil, attachment onto the inner Sur ring, and this temperature was kept for 3 minutes to perform face of the container). heat sterilization. Thereafter, this mixture was filled into a 0063) Next, Comparative Examples 6 to 11 shown below container and cooled. Thus, a beverage in the container was correspond to Examples 4 to 10, except that a palm oil was produced. Note that this beverage had a pH of 2.9. The thus used in place of the phytosterol ester. obtained beverage had almost no perceptible pungency. 0057 Next, the following Examples 4 to 10 are examples in which a capsicum pepper extract, capsaicin, a ginger Comparative Examples 6 to 11 extract, a pepper extract, a Japanese pepper extract, an allyl mustard oil or a turmeric extract were used respectively, as the (1) Production of Composite Materials lipophilic component, as shown in Table 3. 0064. The corresponding one of the lipophilic compo nents described in Table 3 was added to 0.3 parts by weight of Examples 4 to 10 a palm oil (FUJI OIL CO.,LTD. “PALMACE 10'), which was used in place of the phytosterol ester. With stirring, this (1) Production of Composite Materials mixture was warmed to 60°C., and the lipophilic component 0058. The corresponding one of the lipophilic compo was dissolved. Thus a palm oil in which a pungent component nents described in Table 3 was added to 0.3 parts by weight of or a bitter component was dissolved was prepared. a phytosterol ester (San-Ei Gen F.F.I., Inc. “San 0065 Separately, 8.2 parts by weight of Y-cyclodextrin NO. 3’). With stirring, the mixture was warmed to 60° C. and and 4 parts by weight of water (at 75° C.) were mixed with the lipophilic component was dissolved. Thus a phytosterol each other, to thereby prepare a mixture (a paste). ester in which a pungent component or a bitter component 0066. To the mixed paste, the palm oil in which the pun was dissolved was prepared. gent component or the bitter component was dissolved was US 2010/01 84864 A1 Jul. 22, 2010

added. The mixture was kneaded for 10 minutes by using a lipophilic component was dissolved. Thus, a phytosterolester mortar, while being warmed at 75°C. Thus, each composite in which a pungent component or a bitter component was material was prepared. dissolved was prepared. 0071 Separately, 0.5 parts by weight of an emulsifier (2) Production of Beverages (Mitsubishi-Kagaku Foods Corporation, “RYOTO SWA 0067. To the composite material, 87 parts by weight of 1OD) were dissolved in 12 parts by weight of water (at 75° water were added to be mixed therewith. Subsequently, 0.1 C.). parts by weight of citric acid and 0.01 parts by weight of 0072 To the solution, the phytosterol ester in which the trisodium citrate were added to be mixed therewith. Next, this pungent component or the bitter component was dissolved mixture was warmed to 93°C. with stirring, and this tempera was added. The mixture was stirred (at 5000 rpm, for 10 ture was kept for 3 minutes to thereby perform heat steriliza minutes) by using a homogenizer. Thus, each emulsion was tion. Thereafter, this mixture was filled into a container and produced. cooled. Thus, each beverage in a container was produced. (2) Production of Beverages (3) Evaluation of Beverages 0073. To the emulsion, 87 parts by weight of water were 0068 Table 3 shows evaluation results of the beverages added to be mixed therewith. Subsequently, 0.1 parts by thus produced in Comparative Examples 6 to 11. Compara weight of citric acid and 0.01 parts by weight of trisodium tive Examples 6 to 11 were obviously inferior to Examples 4 citrate were added to be mixed therewith. Next, this mixture to 10 in terms of appearance (floating oil, deposition onto the was warmed to 93°C. with stirring, and this temperature was inner Surface of the container). kept for 3 minutes to perform heat sterilization. Thereafter, 0069. Next, the following Comparative Examples 12 to 17 this mixture was filled into a container, and cooled. Thus, correspond to Examples 4 to 10, except that in stead of y-cy each beverage in the container was produced. clodextrin, an emulsifier was used. (3) Evaluation of Beverages Comparative Examples 12 to 17 0074 Table 3 shows the evaluation results of the beverages (1) Production of Emulsions thus produced in Comparative Examples 12 to 17. Compara 0070 The corresponding one of the lipophilic compo tive Examples 12 to 17 were obviously inferior to Examples nents described in Table 3 was added to 0.3 parts by weight of 4 to 10, interms of reduction intaste and odor, and appearance a phytosterol ester (San-Ei Gen F. F.I., Inc. “San Sterol NO. (floating oil, attachment onto the inner Surface of the con 3’). With stirring, the mixture was warmed to 60°C., and the tainer).

TABLE 3

Amount of Evaluation results component Floating oil added (parts Attachment Overall Lipophilic component by weight) Oil YCD Taste Odor onto container evaluation Examp e 4 Pungent Capsicum OOOO284 PSE yCD Almost no — Not C3 component pepper extract Parts pungency observed (including perceived Comparative capsaicins) Palm YCD Pungency — Observed X Examp oil perceived O SOile degree Comparative PSE None Apparent — Observed X Example 12 (emulsifier) pungency eceWe Examp e5 Capsaicin OOOOO947 PSE yCD Almost no — Not C3 (purified product Parts pungency observed (reagent)) eceWe Examp Ginger extract PSE yCD Almost no — Not C3 (containing Parts pungency observed gingerol and eceWe Comparative shogaol) Palm YCD Almost no — Observed X Examp oil pungency eceWe Comparative PSE None Apparent — Observed X Example 13 (emulsifier) pungency eceWe Examp Paper extract PSE yCD Almost no — Not C3 (containing Parts pungency observed piperine) eceWe Comparative Palm YCD Almost no — Observed X Examp oil pungency eceWe US 2010/01 84864 A1 Jul. 22, 2010

TABLE 3-continued

Amount of Evaluation results component Floating oil added (parts Attachment Overall Lipophilic component by weight) Oil YCD Taste Odor onto container evaluation Comparative PSE. None Pungency — Observed X Example 14 (emulsifier) perceive O SOile degree Example 8 Japanese O.05 Parts PSE yCD Almost no No Not C3 pepper extract astringent unpleasant observed (containing aste odor Sanshool) perceived perceived Comparative Palm YCD Astringent No Observed X Example 9 oil aste unpleasant perceived odor O SOile perceived degree Comparative PSE. None Strong Unpleasant Observed X Example 15 (emulsifier) astringent Sweat-like aste OCO W8S perceived strong Example 9 Allyl mustard oil 0.01 Parts PSE yCD Almost no Almost no Not C3 (containing allyl pungency irritating observed isothiocyanate) perceived odor perceive Comparative Palm YCD Almost no Almost no Observed X Example 10 oil pungency irritating perceived odor perceive Comparative PSE. None Pungency Strong Observed X Example 16 (emulsifier) perceived irritating OCO perceive Example 10 Bitter Turmeric extract 0.06 Parts PSE yCD Almost no Almost no Not C3 component (containing bitter taste earthy odor observed essential oil perceive perceive Comparative component with Palm YCD Almost no Almost no Observed X Example 11 bitter taste) oil bitter taste earthy odor perceive perceive Comparative PSE. None Strong Strong Observed X Example 17 (emulsifier) bitter taste earthy odor perceive perceive

* PSE: Phytosterol ester, CD: Y-cyclodextrin

0075) Next, in the following Examples 11 to 13 composite parts by weight of citric acid and 0.01 parts by weight of materials were produced by respective methods different trisodium citrate were added to be mixed therewith. Next, this from one another. mixture was warmed to 93°C. with stirring, and this tempera Example 11 ture was kept for 3 minutes to perform heat sterilization. Thereafter, this mixture was filled into a container, and (1) Production of Composite Material cooled. Thus, a beverage in the container was produced. 0076 0.003 parts by weight of a capsicum oleoresin (con tent of capsaicins: 35.2%), which is a pungent component, Example 12 were added to 0.3 parts by weight of a phytosterol ester (San-Ei Gen F. F.I., Inc., “San Sterol NO. 3’). With stirring, (1) Production of Composite Material the mixture was warmed to 60° C., and the capsicum oleo 0080 0.3 parts by weight of a phytosterol ester (San-Ei resin was dissolved. Thus a phytosterol ester in which the Gen F. F.I., Inc., “San Sterol NO. 3') were warmed to 60° C. pungent component was dissolved was prepared. and dissolved with stirring. 0077 Separately, 8.2 parts by weight of Y-cyclodextrin I0081 Separately, 8.2 parts by weight of Y-cyclodextrin and 6 parts by weight of water (at 75° C.) were mixed with and each other, to thereby prepare a mixture (a paste). I0082 6 parts by weight of water (at 75° C.) were mixed 0078. To the mixed paste, the phytosterol ester in which with each other, to thereby prepare a mixture (a paste). the pungent component was dissolved was added. The mix I0083) To the mixed paste, the phytosterol ester was added, ture was subjected to a homogenizing treatment (at 5000 rpm and the mixture was Subjected to a homogenizing treatment for 10 minutes). Thus, a composite material was obtained. (at 5000 rpm for 10 minutes). (2) Production of Beverage I0084. To the homogenized product, 0.003 parts by weight 0079. To the composite material, 85 parts by weight of of a capsicum oleoresin (content of capsaicins: 35.2%), and 2 water were added to be mixed therewith. Subsequently, 0.1 parts by weight of water (at 75° C.) were added and the US 2010/01 84864 A1 Jul. 22, 2010 mixture was subjected to a homogenizing treatment (at 5000 0093. To the mixed paste, the phytosterol ester in which rpm for 1 minute). Thus, a composite material was obtained. the pungent component was dissolved was added. The mix ture was kneaded for 10 minutes by using a mortar, while (2) Production of Beverage being warmed at 75° C. Thus, each composite material was produced. 0085. To the composite material, 85 parts by weight of water were added to be mixed therewith, and 0.1 parts by (2) Production of Beverages weight of citric acid and 0.01 parts by weight of trisodium citrate were added to be mixed therewith. Subsequently, this 0094. To the composite material, 87 parts by weight of mixture was warmed to 93°C. with stirring, and this tempera water were added to be mixed therewith. Subsequently, 0.1 ture was kept for 3 minutes to perform heat sterilization. parts by weight of citric acid and 0.01 parts by weight of Thereafter, the mixture was filled into a container, and cooled. trisodium citrate were added to be mixed therewith. Next, this Thus a beverage in the container was produced. mixture was warmed to 93°C. with stirring, and this tempera ture was kept for 3 minutes to perform heat sterilization. Example 13 Thereafter, this mixture was filled into a container, and cooled. Thus, each beverage in the container was produced. (1) Production of Composite Material I0086 0.3 parts by weight of a phytosterol ester (San-Ei (Evaluation of Beverages) Gen F. F.I., Inc., “San Sterol NO. 3') were warmed to 60° C. 0.095 The beverages of Examples 14 and 15 had equally and dissolved with stirring. good pungency reduction effects, and appearances (no float 0087. A homogenizing treatment (at 5000 rpm for 10 min ing oil, and no attachment onto the inner Surface of the con utes) was performed on 8.2 parts by weight of Y-cyclodextrin, tainer). 0.003 parts by weight of a capsicum oleoresin (content of 0096. Next, the following Example 16 is a liquid compo capsaicins: 35.2%), the above-described phytosterol ester, sition (a beverage) in a container. This liquid composition and 6 parts by weight of water (at 75°C.), to thereby obtain a includes a composite material, water and a thickener, and the composite material. composite material is in a water dispersed form. (2) Production of Beverage Example 16 I0088. To the composite material, 85 parts by weight of (1) Production of Composite Material water were added to be mixed therewith, and 0.1 parts by 0097 0.003 parts by weight of a capsicum oleoresin (con weight of citric acid and 0.01 parts by weight of trisodium tent of capsaicins: 35.2%) were added to 0.3 parts by weight citrate were added to be mixed therewith. Subsequently, this of a phytosterol ester (San-Ei Gen F. F.I., Inc., “San Sterol mixture was warmed to 93°C. with stirring, and this tempera NO. 3). With stirring, this mixture was warmed to 60° C. ture was kept for 3 minutes to perform heat sterilization. and the capsicum oleoresin was dissolved. Thus, a phy Thereafter, this mixture was filled into a container, and tosterol ester in which the pungent component was dissolved cooled. Thus, a beverage in the container was produced. was prepared. 0.098 Separately, 8.2 parts by weight of Y-cyclodextrin (Evaluation of Beverages) and 4 parts by weight of water (at 75° C.) were mixed with 0089. In all of Examples 11 to 13, a pungency reduction each other to prepare a mixture (a paste). effect was observed. The magnitude of the pungency reduc 0099] To the mixed paste, the phytosterol ester in which tion effect was greatest in Example 11, second greatest in the pungent component was dissolved was added. The mix Example 12, and third greatest in Example 13. ture was kneaded for 10 minutes by using a mortar, while 0090 Next, in the following Examples 14 and 15 compos being warmed at 75° C. Thus, a composite material was ite materials were produced by using different phytosterol produced. esters. Specifically, in Example 14, “San Sterol NO. 3 of San-Ei Gen F. F.I., Inc. was used, whereas, in Example 15, (2) Production of Beverage “phytosterol fatty acid ester of TAMA BIOCHEMICAL 0100. To the composite material, citric acid, trisodium CO.,LTD. was used. citrate, a fermentation-derived cellulose preparation (San-Ei Gen F.F.I., Inc., “SAN ARTIST PX'), granulated sugar, and Examples 14 and 15 water were added at a proportion shown in Table 4, and mixed with stirring. Subsequently, this mixture was warmed to 93 (1) Production of Composite Materials C. with stirring, and this temperature was kept for 3 minutes 0091 0.003 parts by weight of a capsicum oleoresin (con to perform heat sterilization. Thereafter, this mixture was tent of capsaicins: 35.2%) were added to 0.3 parts by weight filled into a container, and cooled. Thus, a beverage in the of a phytosterolester (“San Sterol NO. 3 of San-Ei Gen F. F. container was produced. I., Inc. (Example 14) or “phytosterol fatty acid ester of TAMA BIOCHEMICAL CO., LTD. (Example 15)). With (3) Evaluation of Beverage stirring, the mixture was warmed to 60° C. and the capsicum 0101 The beverage in the container caused almost no oleoresin was dissolved. Thus, a phytosterol ester in which pungency to be perceived, and caused no floating oil and no the pungent component was dissolved was prepared. attachment onto the inner surface of the container. Moreover, 0092 Separately, 8.2 parts by weight of Y-cyclodextrin in this beverage, the composite material was not deposited, and 4 parts by weight of water (at 75° C.) were mixed with but instead was dispersed uniformly. Note that this beverage each other, to thereby prepare a mixture (a paste). had a pH of 3.5. US 2010/01 84864 A1 Jul. 22, 2010

4. A composition comprising the composite material TABLE 4 according to claim 1 blended therein. 5. A liquid composition comprising: Mixing proportion the composite material according to claim 1: Components (% by weight) water, and The above-described composite material 12.SO3 a thickener, Citric acid O.SO wherein the composite material is in a water dispersed Trisodium citrate O.25 Fermentation-derived cellulose preparation O.60 form. (San-Ei Gen F.F.I., Inc., “SAN ARTIST PX) 6. A method for producing a composite material compris Granulated Sugar 1O.O ing: a lipophilic component having an irritating taste and/or Water 76.147 odor; a phytosterol ester, and a cyclodextrin, the method comprising the step of mixing the lipophilic Total 100 component, the phytosterol ester and the cyclodextrin with each other in the presence of water, to thereby form 1. A composite material comprising: the composite material. a lipophilic component having an irritating taste and/or 7. The method for producing composite material according odor; to claim 6, comprising the steps of: a phytosterol ester, and dissolving the lipophilic component in the phytosterol a cyclodextrin. ester, 2. The composite material according to claim 1, preparing a mixture containing the cyclodextrin and water; obtained by mixing the lipophilic component, the phy and tosterol ester and the cyclodextrin with each other in the mixing the phytosterol ester which dissolves the lipophilic presence of water. component with the mixture, to thereby form the com 3. The composite material according to claim 1, posite material. wherein the lipophilic component is a pungent component or a bitter component.