WO2011078367A1 - 乳化組成物 - Google Patents
乳化組成物 Download PDFInfo
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- WO2011078367A1 WO2011078367A1 PCT/JP2010/073456 JP2010073456W WO2011078367A1 WO 2011078367 A1 WO2011078367 A1 WO 2011078367A1 JP 2010073456 W JP2010073456 W JP 2010073456W WO 2011078367 A1 WO2011078367 A1 WO 2011078367A1
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/02—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by the production or working-up
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
Definitions
- the present invention relates to an emulsified composition suitable for adding an oil-soluble component such as a capsinoid compound to an aqueous phase system.
- capsaicinoid capsaicin, dihydrocapsicin
- Capsinoid compounds are very unstable because the ester bond existing between the vanillyl group and the fatty acid side chain is easily hydrolyzed. Therefore, in order to add to an aqueous food or drink such as a beverage, a technique of mixing or dispersing in the aqueous medium while maintaining stability is required. As such a technique, a technique of emulsifying capsinoid-containing oil with various emulsifiers has been reported (see Patent Document 2).
- a thickener is added to the oil phase containing the capsinoid compound to increase the viscosity of the oil in the oil phase, thereby improving the stability of the capsinoid compound in the emulsion composition.
- the technique of making it report has been reported (refer patent document 3).
- turbidity is also important.
- the turbidity of the emulsion composition is evaluated by the transmittance and average particle diameter of the emulsion composition. Generally, the smaller the average particle diameter of the emulsion composition, the lower the turbidity, and the average particle diameter is 100 nm or less. If there is, it tends to be a transparent emulsion composition.
- Patent Document 2 shows stability in the acidic region of the capsinoid-containing emulsion composition
- an aqueous beverage to which the emulsion composition is actually added is prepared, the emulsion composition is stored at room temperature. There is a problem that the capsinoid in it is gradually decomposed.
- the emulsion composition described in Patent Document 3 it is necessary to add a thickener to increase the viscosity of the oil phase. Furthermore, the emulsion composition prepared as described above has the storage stability of capsinoid, but its transparency has not been studied.
- an object of the present invention is to provide an emulsified composition that is excellent in storage stability of oil-soluble components that are unstable in an aqueous phase system, including capsinoids, and that is excellent in transparency when added to an aqueous phase system. It was.
- the present inventors have found that the stability of the oil-soluble component is increased when the fatty acid composition of the oil phase is set to a specific ratio.
- the quality such as transparency, emulsification stability, and storage stability of oil-soluble components such as capsinoids, caprylic acid, capric acid, lauric acid, and myristic acid are found in the fatty acid composition of fats and oils in the oil phase component. It has proved important to be present in a certain range of proportions.
- the present invention includes at least the following contents.
- an emulsion composition comprising (A) an oil phase component containing an oil-soluble component and fats and oils, (B) a polyglycerin fatty acid ester, and (C) an aqueous phase component
- the fatty acid composition of the fats and oils in the oil phase component of (A) is 20-97 capric acid, 28-6000 lauric acid, and 11-2100 myristic acid in a weight ratio to caprylic acid 100.
- Emulsified composition [2] The emulsion composition according to the above [1], which contains 1 to 2000 parts by weight of the oil phase component of (A) with respect to 100 parts by weight of the polyglycerin fatty acid ester of (B).
- the polyglycerol fatty acid ester of (B) is an ester of polyglycerol containing 30% by weight or more of polyglycerol having a polymerization degree of 10 or more and a fatty acid containing 90% by weight or more of myristic acid.
- the emulsion stability is high when stored for a long period of time, and when added to an aqueous phase, the transparency is high and the sensory is excellent, and the oil such as a capsinoid compound contained in the composition.
- An emulsified composition in which decomposition of the soluble component is suppressed can be provided.
- the emulsion composition according to the present invention is an emulsion composition containing (A) an oil phase component containing an oil-soluble component and fats and oils, (B) a polyglycerin fatty acid ester, and (C) an aqueous phase component.
- the fats and oils in the oil phase component of A) are characterized by having a specific range of fatty acid composition.
- the oil phase component (A) includes an oil-soluble component and fats and oils.
- an oil-soluble component useful for a living body, or an oil-soluble component useful when used for food or drink or cosmetics is preferably used.
- oil-soluble ingredients include oil-soluble drugs such as liver oil, vitamin A, vitamin A oil, vitamin D 3 , vitamin B 2 butyric acid ester, ascorbic acid fatty acid ester, natural vitamin E mixture, vitamin K and the like.
- Oil-soluble pigments such as paprika pigment, anato pigment, tomato pigment, marigold pigment, ⁇ -carotene, astaxanthin, canthaxanthin, lycopene, chlorophyll; and perfume such as orange oil, peppermint oil, spearmint oil, cinnamon oil; , Linalool, nerol, citronellol, geraniol, citral, l-menthol, eugenol, cinnamic aldehyde, anethole, perilaldehyde, vanillin, ⁇ -undecalactone, and other essential oils; coenzyme Q 10 , ⁇ -lipoic acid, ⁇ - Linolenic acid ⁇ -3 fatty acids such as eicosapentaenoic acid and docosahexaenoic acid, ⁇ -6 fatty acids such as linoleic acid and ⁇ -linolenic acid, and physiologically active ingredients such as plant sterols,
- An effective amount is included.
- hydrolysis, oxidative degradation, and other general preparations, and unstable components that easily react in products such as oil-soluble vitamins such as capsinoid compounds, vitamin A, ascorbic acid fatty acid esters, omega-3 fatty acids, etc.
- oil-soluble vitamins such as capsinoid compounds, vitamin A, ascorbic acid fatty acid esters, omega-3 fatty acids, etc.
- a capsinoid compound can be suitably used as the oil-soluble component.
- the capsinoid compound preferably refers to a fatty acid ester of vanillyl alcohol, and representative components thereof include capsiate, dihydrocapsiate, nordihydrocapsiate, which have been identified as components contained in red peppers, and Various fatty acid esters of various linear or branched chain fatty acids and vanillyl alcohol having the same fatty acid chain length as those of capsiates such as vanillyl decanoate, vanillyl nonanoate, vanillyl octanoate and nordihydrocapsiate. Including, but not limited to.
- CST dihydrocapsiate
- DCT dihydrocapsiate
- NDCT nordihydrocapsiate
- Capsinoid compounds are mostly contained in plants belonging to the genus Capsicum (hereinafter referred to as “capsicum”), and therefore can be prepared by separating and purifying from capsicum plants and / or fruits.
- the capsicum used for purification is not particularly limited as long as it contains capsinoid, and it may be a capsicum-derived capsicum varieties typified by ⁇ Nikko '' and ⁇ Five colors '', but it is a spicy variety. Pepper is preferred. Among them, spicy varieties such as “CH-19 Ama”, “Manganji”, “Fushimi Amecho”, etc., as well as shishitou and bell pepper contain a lot of capsinoid compounds and can be used preferably.
- CH-19 sweet which is a spicy taste varieties is more preferable because the content of the component is high.
- CH-19 sweet means a group of varieties including “CH-19 sweet” varieties and progeny related varieties derived from “CH-19 sweet”. Separation and purification of capsinoid compounds can be carried out by solvent extraction well-known to those skilled in the art, various types of chromatography such as silica gel chromatography, and high-performance liquid chromatography for preparation alone or in combination. For example, the method described in Patent Document 1 described above can be used.
- said capsinoid compound can also be synthesize
- it can be synthesized by other reaction methods well known to those skilled in the art based on the structural formula.
- it can be easily prepared by a synthesis method using an enzyme. For example, according to the method described in JP-A No. 2000-31598 and Kobata et al. (Biosci. Biotechnol.
- a fatty acid ester corresponding to a desired compound and / or A desired capsinoid compound can be easily obtained by utilizing the reverse reaction of lipase using a fatty acid-containing compound such as triglyceride and vanillyl alcohol as a substrate.
- the capsinoid compound When used for preparing the emulsified composition of the present invention, the capsinoid compound may be any of the above-described extract or synthetic product, or may be a single capsinoid compound or a mixture of two or more. Also good. Furthermore, the capsinoid compound to be used may contain free fatty acids, vanillyl alcohol, and the like, which are decomposition products thereof.
- oils and fats used in the present invention include vegetable oils and fats such as soybean oil, coconut oil, rice oil, corn oil, palm oil, palm kernel oil, safflower oil, rapeseed oil and olive oil; saturated with 6 to 10 carbon atoms
- Medium chain saturated fatty acid triglycerides (hereinafter also referred to as “MCT”) composed of fatty acids (eg, capric acid, caprylic acid and the like) and glycerin as main constituents; beef tallow, pork tallow, chicken tallow, fish oil, etc.
- Animal oils and fats fatty acids such as lauric acid, myristic acid, palmitic acid and oleic acid, and mixtures thereof.
- fats and oils include, in addition to the oil-soluble components described above, antioxidants such as rosemary extract, butylhydroxyanisole (BHA), dibutylhydroxytoluene (BHT), t-butylhydroquinone (TBHQ), and propyl gallate.
- antioxidants such as rosemary extract, butylhydroxyanisole (BHA), dibutylhydroxytoluene (BHT), t-butylhydroquinone (TBHQ), and propyl gallate.
- Specific gravity adjusters and the like can also be contained in combination of one or more.
- the fatty acid composition of the fats and oils in the oil phase component is such that caprylic acid is 20 to 97, lauric acid is 28 to 6000, and myristic acid is 11 to 2100 by weight with respect to caprylic acid 100. It is important to select and use oils and fats. Within this range, the lower the ratio of capric acid, lauric acid, and myristic acid to caprylic acid, the higher the stability of oil-soluble components such as capsinoid compounds, which is preferable. However, if the ratio of capric acid, lauric acid, and myristic acid is reduced beyond this range, the emulsion stability of the emulsion composition is adversely affected, which is not preferable.
- caprylic acid 100 is preferably used in a range of capric acid 20 to 95, lauric acid 28 to 600, and myristic acid 11 to 1000 in terms of weight ratio. More preferably, it is used in the range of 31 to 95, lauric acid of 30 to 250, and myristic acid of 11 to 80.
- the fatty acid composition of fats and oils can be measured using a well-known method, for example, the method used normally, such as a gas chromatograph method, is used. The percentage of each peak area with respect to the total sum of chromatogram peaks obtained by this method is used as the fatty acid composition.
- the fatty acid composition is determined by the following equation. ⁇ Fatty acid composition of fat and oil A ⁇ mixing ratio of fat and oil A when the total amount is 1 (weight basis) ⁇ + ⁇ Fatty acid composition of fat and oil B ⁇ mixing ratio of fat and oil B when the total amount is 1 (weight basis) ⁇
- the emulsified composition of the present invention is not particularly limited except that the emulsifier containing the polyglycerin fatty acid ester (B) is used, and various emulsifiers conventionally used in foods and drinks. Can be used in combination with a polyglycerol fatty acid ester.
- emulsifiers examples include monoglycerin fatty acid ester, diglycerin fatty acid ester, triglycerin fatty acid ester, monoglycerin fatty acid ester derivative, monoethylene glycol fatty acid ester, diethylene glycol fatty acid ester, propylene glycol fatty acid ester, sorbitan fatty acid ester, poly Examples thereof include oxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, lecithin, and quilla extract.
- the polyglycerin fatty acid ester (B) used in the present invention is preferably a polyglycerin fatty acid ester having an average polymerization degree of 6 or more in consideration of the transparency of the resulting emulsion composition, and considering the taste and flavor, myristin. Acid esters are preferably used.
- quality of the final product containing the emulsified composition appearance, that is, transparency or turbidity is important, and in the case of foods and drinks, taste, flavor and smell are also important.
- aldehydes and ketones generated by hydrolysis of fatty acid esters used as emulsifiers in emulsion compositions and further reactions such as oxidation of fatty acids may cause different flavors and odors.
- myristic acid is a fatty acid having a relatively good functionality with little occurrence of the above-mentioned different flavor.
- an ester of a polyglycerol containing 30% by weight or more of a polyglycerol having a polymerization degree of 10 or more and a fatty acid containing 90% by weight or more of myristic acid is preferable to use a polyglycerin monomyristic acid ester as a main component.
- the polymerization degree distribution and fatty acid composition of polyglycerin constituting the polyglycerin fatty acid ester can be analyzed using high performance liquid chromatograph mass spectrometry (LC / MS).
- the aqueous phase component used in the emulsion composition of the present invention is for preparing an oil-in-water emulsion composition by emulsifying the oil phase.
- sugars such as sugar and chickenpox
- polyhydric alcohols such as glycerin, sorbitol, maltitol, erythritol, isomalt and propylene glycol
- lower alcohols such as ethanol
- metals such as sodium chloride, potassium chloride and calcium chloride Salts
- water-soluble vitamins such as vitamin B 1 , vitamin B 2 , vitamin B 6 and their salts
- the pH of the aqueous phase component is preferably adjusted to the pH in the acidic region, more preferably pH 2-6.
- the acidic substance used for pH adjustment is not particularly limited, and examples thereof include citric acid, adipic acid, succinic acid, tartaric acid, lactic acid, fumaric acid, DL-malic acid, benzoic acid, gluconic acid, and glucono delta lactone.
- the lower the content ratio of the oil phase component relative to the emulsifier the easier it is to obtain an emulsified composition with high transparency.
- the content of the oil phase component in the emulsion composition decreases, The content of the oil-soluble component having a function in the oil phase component is also reduced.
- the oil phase component is preferably contained in an amount of 1 to 2000 parts by weight per 100 parts by weight of the polyglycerol fatty acid ester.
- the content ratio of the oil phase component and the emulsifier is high, the emulsion composition becomes highly viscous and difficult to handle.
- the water phase component is preferably contained in an amount of 20% by weight or more, and more preferably 40% by weight or more. More preferably. Since emulsification becomes unstable when the content ratio of the oil phase component and the emulsifier is too low, it is preferable to contain the water phase component at 95% by weight or less.
- the content of the oil-soluble component with respect to the total amount of the emulsified composition is suitably 0.0001 wt% to 50 wt%. Within this range, the greater the content of the oil-soluble component, the more the amount of the oil-soluble component contained in the aqueous food or drink when the emulsion composition is added to the aqueous food or drink.
- the content of the oil-soluble component is small.
- the content of the oil-soluble component relative to the total amount of the emulsified composition is further preferably 0.01% by weight to 10% by weight, and more preferably 0.1% by weight to 2% by weight.
- oil-soluble components such as capsinoid compounds are preferably dissolved in fats and oils having the above fatty acid composition, and usually used for mechanical emulsification, phase inversion emulsification, liquid crystal emulsification, D phase emulsification and the like.
- the emulsified composition can be appropriately prepared by the emulsification method of the obtained fats and oils.
- an oil phase containing an oil-soluble component such as a capsinoid compound is first mixed with an aqueous phase in which the above emulsifier is heated and dissolved in water, and the pH of the emulsified composition is adjusted as necessary.
- an emulsion composition having excellent stability can be prepared.
- polyhydric alcohol is contained as an aqueous phase component
- an emulsifier is dissolved in the polyhydric alcohol to form phase D, and after the oil phase component is gradually added thereto and pre-emulsified,
- the D phase emulsification method of adding, mixing and emulsifying can also be used preferably.
- the average particle diameter is measured by a dynamic light scattering method.
- the emulsion composition of the present invention preferably exhibits transparency without turbidity when added to an aqueous phase system in consideration of application to foods and drinks such as aqueous beverages and liquid pharmaceuticals such as liquids.
- Turbidity can be evaluated by a commonly used method, for example, a method of measuring the transmittance of light having a wavelength of 600 nm. When the transmittance exceeds 90%, transparency is exhibited even when an aqueous product containing the emulsified composition is placed in a transparent container, which is also preferable in terms of functionality.
- the emulsified composition of the present invention when the composition is added and dispersed in water so as to contain 0.25% by weight of an oil phase containing an oil-soluble component, the light transmittance of the dispersion at a wavelength of 600 nm is obtained. It is preferably 90% or more.
- the emulsified composition of the present invention is an aqueous beverage; a dairy product such as yogurt; a frozen confectionery such as ice cream; a confectionery such as chocolate, candy or chewing gum; a bakery; a processed fishery food; a processed meat food; a retort food; By blending an appropriate amount of these foods and drinks, it can be provided as foods and drinks to which physiological actions of oil-soluble components such as capsinoid compounds are stably imparted for a long period of time. Especially, it is preferable to provide as an aqueous drink containing a capsinoid etc.
- the said food-drinks may be provided as health functional foods, such as food for specified health use, nutrition functional foods, and nutritional supplement foods.
- the blending amount of the emulsified composition of the present invention with respect to the food or drink varies depending on the purpose, type, form, etc. of the food or drink, but is generally blended in the range of 0.001 to 10% by weight. .
- the total oil phase component derived from the emulsified composition is preferably blended so as to be in the range of 0.00005 wt% to 5 wt% with respect to the food and drink. It is more preferable to blend so as to be in the range of wt%. If it is less than 0.00005% by weight, it may not be preferable in terms of stability of oil-soluble components such as capsinoids, and if it is 5% by weight or more, it may not be preferable in terms of transparency, taste, and flavor.
- an emulsified composition containing an oil-soluble drug in an oil phase can be dispersed in an aqueous carrier and provided as an aqueous drug.
- aqueous carrier water; lower alcohols such as ethanol; polyhydric alcohols such as propanediol, 1,3-butanediol, glycerin, sorbitol, and maltitol can be used.
- the aqueous drug according to the present invention can be provided as a liquid, elixir, emulsion, syrup, liniment, limonade, lotion, etc., and can be used for non-oral administration, injection, external use, transgastrointestinal administration, etc. Also suitable for oral administration.
- the blending amount of the emulsified composition in the aqueous carrier and the content of the oil-soluble component in the total amount of the aqueous pharmaceutical product are the same as in the case of the above food and drink. Further, additives that are usually used in aqueous pharmaceuticals such as stabilizers, preservatives, buffering agents, flavoring agents, flavoring agents, solubilizing agents, coloring agents, thickeners and the like are included within the range not impairing the characteristics of the present invention. be able to.
- an emulsified composition containing an oil-soluble emollient, a skin cell activating component and the like in an oil phase can be dispersed in an aqueous carrier and provided as a liquid cosmetic.
- aqueous carrier the same carrier as that described above can be used.
- Liquid cosmetics according to the present invention include skin cosmetics such as lotions, milky lotions, and cosmetics; makeup cosmetics such as liquid foundations, eyeliners, and mascaras; cosmetics for cleaning such as facial cleansers and cleansing agents, and body lotions. Etc. can be provided as body cosmetics.
- medium-chain fatty acid triglycerides MCT
- palm oil and coconut oil were used as fats and oils.
- Their fatty acid composition is shown in Table 1.
- Emulsified composition 20 parts by weight of an emulsifier mainly composed of decaglycerin monomyristic acid ester ("Sunsoft AB", manufactured by Taiyo Kagaku Co., Ltd.) was added to glycerin ("edible glycerin-S", JP 45 parts by weight (manufactured by Oil Co., Ltd.) and mixed at 70 ° C. to 80 ° C. and uniformly dissolved. To this, 0.075 parts by weight of dihydrocapsiate (“DCT”, manufactured by Ajinomoto Co., Inc.) was mixed in advance with 24.93 parts by weight of each fat and oil shown in Table 2 at 50 ° C. to 60 ° C.
- DCT dihydrocapsiate
- Examples 6 to 10 Aqueous beverage To the aqueous solution having the composition shown in Table 3, the emulsified composition of Examples 1 to 5 was added so as to have a content of 1%, and 40 mL was filled into a 100 mL glass bottle, did. The mixture was sterilized by heating at 80 ° C. for 20 minutes and then cooled to about room temperature with running water to obtain aqueous beverages of Examples 6 to 10.
- Table 4 shows the polymerization degree distribution of the constituent polyglycerin for the emulsifier (“Sunsoft AB”, manufactured by Taiyo Kagaku Co., Ltd.) mainly composed of decaglycerin monomyristic acid ester used in the preparation of the above Examples.
- the proportion of the polyglycerin having a polymerization degree of 10 or more in the constituent polyglycerin was 36.1%.
- the polymerization degree distribution of the constituent polyglycerol was determined by high performance liquid chromatography / mass spectrometry (LC / MS) under the following analysis conditions.
- Emulsified composition 20 parts by weight of the above-mentioned emulsifier (“Sunsoft AB”, manufactured by Taiyo Chemical Co., Ltd.) mainly composed of decaglycerin monomyristic acid ester was added to glycerin (“edible glycerin-S”, Each of the fats and oils shown in Table 5 is mixed with 55 parts by weight of NOF Co., Ltd. and 70 to 80 ° C. and dissolved uniformly, and then 0.045 parts by weight of dihydrocapsiate (“DCT”, manufactured by Ajinomoto Co., Inc.) in advance. 14. 96 parts by weight and an oil phase prepared by mixing and dissolving at 50 ° C. to 60 ° C.
- TK robotics manufactured by PRIMIX Corporation
- Table 5 shows the fatty acid composition of the used fats and oils.
- An aqueous phase component in which 0.05 part by weight of citric acid (“citric acid (crystal)”, manufactured by Mitsubishi Tanabe Pharma Co., Ltd.) was dissolved in 9.95 parts by weight of water was added, and an ultrahigh pressure homogenizer (“Micro Fluidizer”, (Mizho Kogyo Co., Ltd.) for one pass at a pressure of 100 MPa and homogenized to obtain emulsion compositions of Comparative Examples 1-9.
- Comparative Examples 10 to 18 Aqueous beverage To the aqueous solution having the composition shown in Table 3 above, the emulsified composition of Comparative Examples 1 to 9 was added to a content of 1%, and 40 mL was filled in a 100 mL glass bottle. Sealed. The mixture was sterilized by heating at 80 ° C. for 20 minutes, and then cooled to about room temperature with running water to obtain aqueous beverages of Comparative Examples 10 to 18.
- an emulsifier (Sunsoft AB", manufactured by Taiyo Kagaku Co., Ltd.) mainly composed of decaglycerin monomyristic acid ester was added to glycerin ("food additive glycerin-S", NOF Corporation) (Company) 45 parts by weight and mixed at 70 ° C. to 80 ° C.
- DCT dihydrocapsiate
- Table 6 The oil phase prepared by mixing and dissolving at 50 ° C to 60 ° C was added little by little, and pre-emulsified with TK Robotics (manufactured by PRIMIX Corporation) at 8,000 rpm and 60 ° C to 65 ° C for 3 minutes. .
- Table 6 also shows the fatty acid composition of the used fats and oils.
- aqueous phase component in which 0.05 part by weight of citric acid (“citric acid (crystal)”, manufactured by Mitsubishi Tanabe Pharma Co., Ltd.) was dissolved in 9.95 parts by weight of water was added, and an ultrahigh pressure homogenizer (“Micro Fluidizer”, The emulsion composition of Comparative Example 19 was obtained by homogenizing by one pass treatment at a pressure of 100 MPa by Mizuho Kogyo Co., Ltd.
- Comparative Example 20 Aqueous beverage To the aqueous solution having the composition shown in Table 3 above, the emulsified composition of Comparative Example 19 was added to a content of 1%, and 40 mL was filled in a 100 mL glass bottle and sealed. After sterilization by heating at 80 ° C. for 20 minutes, the mixture was cooled to about room temperature with running water to obtain an aqueous beverage of Comparative Example 20.
- the transmittance of light having a wavelength of 600 nm was measured for the emulsified compositions of the above Examples and Comparative Examples.
- the measurement method of the transmittance is as follows. Each of the emulsified compositions of Examples 1 to 5 and Comparative Examples 1 to 9 and 19 was diluted with ion-exchanged water to 1%, and a spectrophotometer (self-recording spectrophotometer; model U-3210, Hitachi, Ltd.) ) And the transmittance of light having a wavelength of 600 nm was measured using ion-exchanged water as a control.
- water-based drink or ion-exchange water which added a certain emulsion composition by a certain ratio is known, the transmittance
- the oil phase component content was 0.25% from the transmittance of the diluted solution (oil phase component content was 0.15%) with 1% ion exchange water.
- the transmittance of the diluted solution was calculated. The results are shown in Table 7.
- the emulsion composition is diluted to contain 0.25% as an oil phase component in an aqueous beverage or ion-exchanged water, either the measured value of transmittance or the calculated value by the above formula is 90% or more.
- the transparency when added to the aqueous phase system was judged to be suitable for the purpose of the present invention.
- Table 7 shows that the emulsion compositions of Examples 1 to 5 of the present invention each had a transmittance of 90% or more when diluted in ion-exchanged water so that the oil phase component content was 0.25%.
- the transparency when added to the aqueous phase system was suitable for the purpose of the present invention.
- the emulsified compositions of Comparative Examples 1 to 3 among the emulsified compositions of Comparative Examples where the fatty acid composition of the oil and fat constituting the oil phase is not within the range of the composition ratio in the present invention, the oil phase component content
- the transmittance of the 0.25% aqueous beverage was less than 90%, and the transparency was not suitable for the purpose of the present invention.
- each emulsified composition prepared in Examples and Comparative Examples was evaluated by the following method.
- the emulsified composition was mixed well and then dispensed in 2 g portions into a glass bottle, and the lid was tightly wrapped with parafilm and sealed to avoid moisture evaporation during storage. It was shielded from light and stored at 37 ° C. (acceleration condition), 5 ° C. (refrigeration condition), 24 ° C. (distribution condition) for 1 week, light transmittance (%) of wavelength 600 nm before and after storage and average particle diameter ( nm). The transmittance was measured or calculated in the same manner as described above, and the average particle size was measured by the method shown below.
- each emulsified composition was diluted with ion-exchanged water so as to be 1%, and the average particle size was measured using a particle size distribution meter (dynamic light scattering type particle size distribution measuring instrument “NICOMP380”; manufactured by Particle Sizing Systems). It was measured. Evaluation was made in the order of 1 to 10 points and 10 points in order from the state where the transmittance and average particle diameter during storage were small and stable emulsification was maintained. In addition, the reference
- the emulsion compositions of Examples 1 to 5 of the present invention showed almost no change in transmittance and particle diameter after storage at any temperature, and good emulsion stability was observed. It was. On the other hand, with respect to the emulsified compositions other than Comparative Examples 7 and 19, a decrease in transmittance or an increase in particle diameter was observed over time, and sufficient emulsification stability was not recognized.
- DCT dihydrocapsiate
- the present invention is excellent in emulsion stability when stored for a long period of time, can stably contain oil-soluble components having various physiological functions, and has good transparency when blended in an aqueous phase system.
- the present invention provides an emulsified composition suitable for use in foods and beverages such as aqueous beverages, pharmaceuticals such as internal liquids and liquids, cosmetics such as skin lotions, and cosmetics.
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Abstract
Description
[1](A)油溶性成分と油脂類を含有する油相成分、(B)ポリグリセリン脂肪酸エステル、及び(C)水相成分を含有する乳化組成物において、
(A)の油相成分中の油脂類の脂肪酸組成が、カプリル酸100に対し、重量比で、カプリン酸が20~97、ラウリン酸が28~6000、及びミリスチン酸が11~2100である、乳化組成物。
[2](B)のポリグリセリン脂肪酸エステル100重量部に対し、(A)の油相成分を1~2000重量部含有する、上記[1]に記載の乳化組成物。
[3](A)の油相成分を0.25重量%含むように水に分散した水分散液の波長600nmの光の透過率が90%以上である、上記[1]に記載の乳化組成物。
[4](B)のポリグリセリン脂肪酸エステルが、重合度10以上であるポリグリセリンを30重量%以上含むポリグリセリンと、ミリスチン酸を90重量%以上含有する脂肪酸とのエステルであるポリグリセリンモノミリスチン酸エステルを主成分とするものである、上記[1]に記載の乳化組成物。
[5](A)の油溶性成分が、カプシノイド化合物より選択される1種又は2種以上である、上記[1]~[4]のいずれかに記載の乳化組成物。
[6]カプシノイド化合物より選択される1種又は2種以上が、カプシエイト、ジヒドロカプシエイトおよびノルジヒドロカプシエイトよりなる群から選択される、上記[5]に記載の乳化組成物。
[7]上記[1]~[6]のいずれかに記載の乳化組成物を0.001重量%~10重量%含有する、飲食品。
本発明において、(A)の油相成分は、油溶性成分と油脂類を含むことを特徴とする。本発明で用いる油溶性成分としては、生体に有用な油溶性成分、又は飲食用もしくは化粧品用に利用する際に有用な油溶性成分が好ましく用いられる。かかる油溶性成分としては、油溶性薬剤の他、肝油、ビタミンA、ビタミンA油、ビタミンD3、ビタミンB2酪酸エステル、アスコルビン酸脂肪酸エステル、天然ビタミンE混合物、ビタミンK等の油溶性ビタミン類;パプリカ色素、アナトー色素、トマト色素、マリーゴールド色素、β-カロテン、アスタキサンチン、カンタキサンチン、リコピン、クロロフィル等の油溶性色素類;オレンジ油、ペパーミント油、スペアミント油、シンナモン油等の香料類;リモネン、リナロール、ネロール、シトロネロール、ゲラニオール、シトラール、l-メントール、オイゲノール、シンナミックアルデヒド、アネトール、ペリラアルデヒド、バニリン、γ-ウンデカラクトン等の植物精油類;コエンザイムQ10、α-リポ酸、α-リノレン酸、エイコサペンタエン酸、ドコサヘキサエン酸等のω-3系脂肪酸、リノール酸、γ-リノレン酸等のω-6系脂肪酸、植物ステロール等の生理活性成分などが挙げられ、医薬品や化粧料、飲食品用等として有効な量を含有させる。本発明では、加水分解や酸化分解など、一般の製剤、製品中で反応しやすく不安定な成分、たとえば、カプシノイド化合物、ビタミンA、アスコルビン酸脂肪酸エステルなどの油溶性ビタミン、ω-3系脂肪酸などでも用いることができるため好ましい。
{油脂Aの脂肪酸組成 × 総量を1とした場合の油脂Aの混合比率(重量基準)} +
{油脂Bの脂肪酸組成 × 総量を1とした場合の油脂Bの混合比率(重量基準)}
本発明の乳化組成物を調製するには、(B)のポリグリセリン脂肪酸エステルを含有する乳化剤を用いること以外は特に制限されるものではなく、従来から飲食品等に用いられている各種の乳化剤を、ポリグリセリン脂肪酸エステルと併用して使用することができる。併用し得る乳化剤としては、たとえば、モノグリセリン脂肪酸エステル、ジグリセリン脂肪酸エステル、トリグリセリン脂肪酸エステル、モノグリセリン脂肪酸エステル誘導体、モノエチレングリコール脂肪酸エステル、ジエチレングリコール脂肪酸エステル、プロピレングリコール脂肪酸エステル、ソルビタン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル、ショ糖脂肪酸エステル、レシチン、キラヤ抽出物等を挙げることができる。
本発明の乳化組成物に使用する水相成分は、上記油相を乳化して水中油型の乳化組成物を調製するためのものである。必要に応じて、砂糖、水飴等の糖類;グリセリン、ソルビトール、マルチトール、エリスリトール、イソマルト、プロピレングリコール等の多価アルコール類;エタノールなどの低級アルコール類;塩化ナトリウム、塩化カリウム、塩化カルシウム等の金属塩類;ビタミンB1、ビタミンB2、ビタミンB6等の水溶性ビタミン及びその塩類;アラビアガム、ガッティガム、トラガントガム、グアーガム、カラヤガム、キサンタンガム、ペクチン、アルギン酸及びその塩類、カラギーナン、ゼラチン、カゼイン、アクリル酸・メタクリル酸アルキル共重合体、ヒドロキシエチルセルロース、カルボキシメチルセルロース等のセルロース誘導体、化工でん粉、オクテニルコハク酸澱粉等の水溶性高分子化合物;カテキン、ビタミンC、亜硫酸水素ナトリウム、エリソルビン酸ナトリウム、茶抽出物等の酸化防止剤;クロシン(クチナシ色素)、アントシアニン、フィコシアニン等の水溶性色素類等を適宜配合することもできる。
本発明の乳化組成物の調製にあたっては、カプシノイド化合物等の油溶性成分を、好ましくは上記脂肪酸組成を有する油脂類に溶解し、機械乳化、転相乳化、液晶乳化、D相乳化等、通常用いられる油脂の乳化方法により、適宜乳化組成物を調製することができる。たとえば、好ましい1つの実施形態において、まずカプシノイド化合物等の油溶性成分を含有する油相と、水に上記乳化剤を加熱溶解させた水相とを混合し、必要に応じて乳化組成物のpHが2~6の範囲となるように上記酸性物質で調整し、ホモミキサー、コロイドミル、高圧ホモジナイザー、マイクロフルイダイザー等を用いて混合・均質化処理を行うことにより、カプシノイド化合物等の油溶性成分の安定性に優れた乳化組成物を調製することができる。また、水相成分として多価アルコールを含有させる場合には、乳化剤を多価アルコールに溶解してD相を生成し、これに油相成分を徐々に添加して予備乳化した後、水相成分を添加、混合して乳化するD相乳化法も好ましく用いることができる。透明な乳化組成物を得る目的においては、平均粒子径が100nm以下の微細な乳化粒子を調製する必要があるが、高剪断力を有する超高圧ホモジナイザー(マイクロフルイダイザー)、高圧ホモジナイザーなどを用いて乳化することが、短時間で微細な乳化組成物を得ることができ、好ましい。なお、本発明においては、前記平均粒子径は動的光散乱法により測定される。
本発明の乳化組成物は、水性飲料;ヨーグルトなどの乳製品;アイスクリームなどの冷菓;チョコレート、キャンディ、チューイングガムなどの菓子類;ベーカリー類;水産加工食品;畜肉加工食品;レトルト食品;冷凍食品等の飲食品類に適当量を配合することにより、カプシノイド化合物などの油溶性成分の生理作用が長期間安定に付与された飲食品類として提供することができる。中でも、カプシノイド等を含有する水性飲料として提供することが好ましい。水性飲料としては、必要に応じ、果汁、ビタミン類、アミノ酸類、香料、糖類、酸、塩基、塩類等を添加し、清涼飲料又は炭酸飲料として提供することができる。また本発明においては、前記飲食品は、特定保健用食品、栄養機能食品等の保健機能食品や、栄養補助食品として提供されるものであってもよい。前記の飲食品に対する本発明の乳化組成物の配合量は、飲食品の使用目的、種類、形態等によって異なるが、一般的には、0.001重量%~10重量%の範囲で配合される。さらに、乳化組成物に由来する全油相成分が、前記飲食品に対して0.00005重量%~5重量%の範囲となるように配合するのが好ましく、0.1重量%~0.3重量%の範囲となるように配合するのがより好ましい。0.00005重量%未満ではカプシノイド等油溶性成分の安定性の点で好ましくない場合があり、5重量%以上では透明性、味、風味の点で好ましくない場合がある。
デカグリセリンモノミリスチン酸エステルを主成分とする乳化剤(「サンソフトAB」、太陽化学株式会社製)20重量部をグリセリン(「食添グリセリン-S」、日油株式会社製)45重量部と70℃~80℃で混合し、均一に溶解した。これに、あらかじめジヒドロカプシエイト(「DCT」、味の素株式会社製)0.075重量部を表2に示す各油脂24.93重量部と50℃~60℃で混合し、溶解して調製した油相を少しずつ添加し、TKロボミクス(PRIMIX株式会社製)で8,000rpm、60℃~65℃にて、3分間予備乳化した。用いた油脂の脂肪酸組成を表2に併せて示す。そこにクエン酸(「クエン酸(結晶)」、田辺三菱製薬株式会社製)0.05重量部を水9.95重量部に溶解した水相成分を加え、超高圧ホモジナイザー(「Micro Fluidizer」、みづほ工業株式会社製)により圧力100MPaで1パス処理して均質化し、実施例1~5の乳化組成物を得た。
表3に示す組成の水溶液に、実施例1~5の乳化組成物を1%の含有量となるように添加し、100mLのガラスビンに40mL充填して、密栓した。80℃で20分間加熱殺菌した後、流水で室温程度まで冷却し、実施例6~10の水性飲料を得た。
イオン化モード:APCI、negative
測定範囲:90-2000
カラム:TSKgel α-2500(7.8×300mm)
温度:40℃
溶離液:水/アセトニトリル 7/3
流量:0.8mL、100ppm
分析時間:20分
デカグリセリンモノミリスチン酸エステルを主成分とする上記乳化剤(「サンソフトAB」、太陽化学株式会社製)20重量部をグリセリン(「食添グリセリン-S」、日油株式会社製)55重量部と70℃~80℃で混合し、均一に溶解した後、あらかじめジヒドロカプシエイト(「DCT」、味の素株式会社製)0.045重量部を表5に示す各油脂14.96重量部と50℃~60℃で混合し、溶解して調製した油相を少しずつ添加し、TKロボミクス(PRIMIX株式会社製)で8,000rpm、60℃~65℃にて、3分間予備乳化した。用いた油脂の脂肪酸組成を表5に併せて示す。そこにクエン酸(「クエン酸(結晶)」、田辺三菱製薬株式会社製)0.05重量部を水9.95重量部に溶解した水相成分を加え、超高圧ホモジナイザー(「Micro Fluidizer」、みづほ工業株式会社製)により圧力100MPaで1パス処理して均質化し、比較例1~9の乳化組成物とした。
上記表3に示す組成の水溶液に、比較例1~9の乳化組成物を1%の含有量となるように添加し、100mLのガラスビンに40mL充填して、密栓した。80℃で20分間加熱殺菌した後、流水で室温程度まで冷却し、比較例10~18の水性飲料とした。
デカグリセリンモノミリスチン酸エステルを主成分とする乳化剤(「サンソフトAB」、太陽化学株式会社製)20重量部をグリセリン(「食添グリセリン-S」、日油株式会社製)45重量部と70℃~80℃で混合し、均一に溶解した後、あらかじめジヒドロカプシエイト(「DCT」、味の素株式会社製)0.075重量部を表6に示す油脂24.93重量部と50℃~60℃で混合し、溶解して調製した油相を少しずつ添加し、TKロボミクス(PRIMIX株式会社製)で8,000rpm、60℃~65℃にて、3分間予備乳化した。用いた油脂の脂肪酸組成を表6に併せて示す。そこにクエン酸(「クエン酸(結晶)」、田辺三菱製薬株式会社製)0.05重量部を水9.95重量部に溶解した水相成分を加え、超高圧ホモジナイザー(「Micro Fluidizer」、みづほ工業株式会社製)により圧力100MPaで1パス処理して均質化し、比較例19の乳化組成物とした。
上記表3に示す組成の水溶液に、比較例19の乳化組成物を1%の含有量となるように添加し、100mLのガラスビンに40mL充填して、密栓した。80℃で20分間加熱殺菌した後、流水で室温程度まで冷却し、比較例20の水性飲料とした。
y2=(y1/100)(x2/x1) ×100
で表される。油相成分含有量は、当該乳化組成物中の油相成分含有量に、乳化組成物の水性飲料もしくはイオン交換水への添加濃度を乗じた値である。ゆえに、ある乳化組成物をある比率で添加した水性飲料もしくはイオン交換水の透過率が分かれば、別の比率で添加した場合の透過率も計算できる。比較例1~9の乳化組成物については、それぞれ1%のイオン交換水による希釈液(油相成分含有量が0.15%)の透過率から、油相成分含有量が0.25%の希釈液の透過率を算出した。結果を表7に示す。なお、乳化組成物を水性飲料もしくはイオン交換水に油相成分として0.25%含有するように希釈したときの透過率の実測値、又は上記式による計算値のいずれかが90%以上であれば、水相系に添加したときの透明性において、本発明の目的に適すると判断した。
1点;平均粒子径及び透過率の変化がほとんどなく、安定な乳化が維持される
2点;平均粒子径又は透過率にわずかに変化が見られる
7点;24℃で1週間保存した後、目視で濁りが確認できる
10点;乳化組成物を調製した直後から分離、油浮き、強い濁りが確認される
残存率(%)=保存後のDCT含有量/保存前のDCT含有量×100
<安定性基準>
・乳化組成物由来の油相成分を水性飲料中に0.15%含有する場合:DCT残存率が82.0%以上
・乳化組成物由来の油相成分を水性飲料中に0.25%含有する場合:DCT残存率が85.0%以上
結果を表9に示す。
Claims (9)
- (A)油溶性成分と油脂類を含有する油相成分、(B)ポリグリセリン脂肪酸エステル、及び(C)水相成分を含有する乳化組成物において、
(A)の油相成分中の油脂類の脂肪酸組成が、カプリル酸100に対し、重量比で、カプリン酸が20~97、ラウリン酸が28~6000、及びミリスチン酸が11~2100である、乳化組成物。 - (B)のポリグリセリン脂肪酸エステル100重量部に対し、(A)の油相成分を1~2000重量部含有する、請求項1に記載の乳化組成物。
- (A)の油相成分を0.25重量%含むように水に分散した水分散液の波長600nmの光の透過率が90%以上である、請求項1に記載の乳化組成物。
- (B)のポリグリセリン脂肪酸エステルが、重合度10以上であるポリグリセリンを30重量%以上含むポリグリセリンと、ミリスチン酸を90重量%以上含有する脂肪酸とのエステルであるポリグリセリンモノミリスチン酸エステルを主成分とするものである、請求項1に記載の乳化組成物。
- (A)の油溶性成分が、カプシノイド化合物より選択される1種又は2種以上である、請求項1~4のいずれか1項に記載の乳化組成物。
- カプシノイド化合物より選択される1種又は2種以上が、カプシエイト、ジヒドロカプシエイトおよびノルジヒドロカプシエイトよりなる群から選択される、請求項5に記載の乳化組成物。
- 請求項1~4のいずれか1項に記載の乳化組成物を0.001重量%~10重量%含有する、飲食品。
- (A)の油溶性成分が、カプシノイド化合物より選択される1種又は2種以上である、請求項7に記載の飲食品。
- カプシノイド化合物より選択される1種又は2種以上が、カプシエイト、ジヒドロカプシエイトおよびノルジヒドロカプシエイトよりなる群から選択される、請求項8に記載の飲食品。
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA2784179A CA2784179A1 (en) | 2009-12-24 | 2010-12-24 | Emulsion composition |
MX2012007246A MX2012007246A (es) | 2009-12-24 | 2010-12-24 | Composicion de emulsion. |
US13/530,345 US20120328760A1 (en) | 2009-12-24 | 2012-06-22 | Emulsion composition |
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JP2009-293395 | 2009-12-24 | ||
JP2009293395A JP5581689B2 (ja) | 2009-12-24 | 2009-12-24 | 乳化組成物 |
Related Child Applications (1)
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US13/530,345 Continuation US20120328760A1 (en) | 2009-12-24 | 2012-06-22 | Emulsion composition |
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WO2011078367A1 true WO2011078367A1 (ja) | 2011-06-30 |
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PCT/JP2010/073456 WO2011078367A1 (ja) | 2009-12-24 | 2010-12-24 | 乳化組成物 |
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US (1) | US20120328760A1 (ja) |
JP (1) | JP5581689B2 (ja) |
CA (1) | CA2784179A1 (ja) |
MX (1) | MX2012007246A (ja) |
WO (1) | WO2011078367A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2018207921A1 (ja) * | 2017-05-12 | 2018-11-15 | 日清オイリオグループ株式会社 | 総ケトン体濃度上昇剤、油脂組成物、医薬組成物、食品組成物 |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102008041918A1 (de) * | 2008-09-09 | 2010-03-11 | Evonik Degussa Gmbh | Silanolkondensationskatalysatoren zur Vernetzung von gefüllten und ungefüllten Polymer-Compounds |
JP2010280628A (ja) | 2009-06-05 | 2010-12-16 | Ajinomoto Co Inc | 乳化製剤 |
WO2013146387A1 (ja) | 2012-03-28 | 2013-10-03 | 味の素株式会社 | 乳化分散剤及び乳化組成物 |
JP6012327B2 (ja) * | 2012-07-30 | 2016-10-25 | 日油株式会社 | 乳化状栄養組成物 |
JP6300780B2 (ja) * | 2015-12-24 | 2018-03-28 | 高砂香料工業株式会社 | アルコール飲料用乳化香料組成物 |
US11039623B2 (en) * | 2016-08-04 | 2021-06-22 | Tyratech, Inc. | Arthropod control formulations and methods |
EP3692803A1 (en) * | 2019-01-18 | 2020-08-12 | GNT Group B.V. | A composition comprising spirulina-extract |
CN111317142A (zh) * | 2020-02-27 | 2020-06-23 | 广东科贸职业学院 | 一种稳定的功能性藻蓝蛋白多重乳液及其制备方法与应用 |
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JPH08120187A (ja) * | 1994-10-26 | 1996-05-14 | Lion Corp | カロチノイド含有水性組成物及びカロチノイド含有飲料 |
JP2009072163A (ja) * | 2007-09-25 | 2009-04-09 | Riken Vitamin Co Ltd | 香味油組成物 |
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JP2007131619A (ja) * | 2005-10-14 | 2007-05-31 | Nisshin Pharma Inc | コエンザイムq10含有活性組成物 |
JP2007269714A (ja) * | 2006-03-31 | 2007-10-18 | Ajinomoto Co Inc | カプシノイド含有乳化組成物の製造方法 |
WO2007114128A1 (ja) * | 2006-03-31 | 2007-10-11 | Ajinomoto Co., Inc. | カプシノイド含有飲食品の製造方法 |
JP5196760B2 (ja) * | 2006-10-27 | 2013-05-15 | 一般財団法人 九州医療資源財団 | W/o/w型エマルジョン組成物 |
US20080131515A1 (en) * | 2006-12-01 | 2008-06-05 | Fujifilm Corporation | Emulsion composition, and foods and cosmetics containing the emulsion composition |
JP4302159B2 (ja) * | 2006-12-01 | 2009-07-22 | 富士フイルム株式会社 | エマルション組成物、該エマルション組成物を含む食品及び化粧品 |
JP4869266B2 (ja) * | 2008-03-03 | 2012-02-08 | 長谷川香料株式会社 | コエンザイムq10を含有する飲料用乳化組成物およびその製造方法 |
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2009
- 2009-12-24 JP JP2009293395A patent/JP5581689B2/ja not_active Expired - Fee Related
-
2010
- 2010-12-24 CA CA2784179A patent/CA2784179A1/en not_active Abandoned
- 2010-12-24 WO PCT/JP2010/073456 patent/WO2011078367A1/ja active Application Filing
- 2010-12-24 MX MX2012007246A patent/MX2012007246A/es not_active Application Discontinuation
-
2012
- 2012-06-22 US US13/530,345 patent/US20120328760A1/en not_active Abandoned
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WO2018207921A1 (ja) * | 2017-05-12 | 2018-11-15 | 日清オイリオグループ株式会社 | 総ケトン体濃度上昇剤、油脂組成物、医薬組成物、食品組成物 |
Also Published As
Publication number | Publication date |
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MX2012007246A (es) | 2012-07-30 |
US20120328760A1 (en) | 2012-12-27 |
CA2784179A1 (en) | 2011-06-30 |
JP2011132176A (ja) | 2011-07-07 |
JP5581689B2 (ja) | 2014-09-03 |
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