JP6073545B2 - Lignan-containing fine particles and composition - Google Patents

Description

The present invention relates to solid fine particles of a lignan compound having an average particle diameter of 20 to 1,000 nm as measured by a dynamic light scattering method, and a method for producing the same.
The present invention also relates to a composition containing the lignan fine particles and a method for producing the same.

The lignan compounds include sesamin, sesamolin, episesamin, sesaminol, sesamolinol, pinoresinol, symploxide aglycone, etc., but the main ones are sesamin (C ₂₀ H ₁₈ O ₆ , molecular weight 354, melting point 122.5-124 ° C. ), Sesamolin (C ₂₀ H ₁₈ O ₇ , molecular weight 370, melting point 93.8 ° C.). Various in vivo effects have been reported for lignan compounds. For example, sesamin is effective in alleviating alcoholism and withdrawal symptoms of alcohol and smoking (USP 4,427,694), and sesaminol and episesaminol are effective in the treatment and prevention of allergies such as bronchial asthma (special Kaihei 2-138120) has been reported. Furthermore, various uses have been developed for lignan compounds, and so far blood cholesterol lowering (patent 3001589), Δ5-desaturase inhibition (patent 3070611), liver function improvement (patent 3075358), Cholesterol lowering (patent 3075360), sickness prevention (patent 3124062), cholesterol and bile acid metabolism inhibition, cholesterol lowering (patent 3283274), carcinogenesis suppression (Japanese Patent Application No. 2-281939), breast cancer suppression (Japanese Patent Application No. Hei) No. 3-200277), lipid peroxide production suppression (Japanese Patent Application No. 3-212295), and active oxygen removal (Japanese Patent Application No. 5-14884) have been confirmed.

  However, sesamin, which is the main lignan compound, is only taken in a very small amount from a normal diet, and it is difficult to expect the above-mentioned effects. It is usually taken in tablets or capsules. To do.

  Therefore, beverages and various foods to which sesamin is added have been proposed as methods for efficiently ingesting sesamin. Addition of sesamin to foods and drinks taken on a daily basis is significant because it raises the expectation of improving its action and facilitates continuous intake of sesamin.

  However, since sesamin has very low solubility in water and fats and oils, its use in foods and drinks has been greatly restricted. For example, when sesamin is blended in a beverage, there is a problem that due to its poor solubility, precipitation occurs during storage, or an unpleasant flavor or texture is exhibited such as a rough feeling.

  Moreover, in many sesamin containing compositions, since sesamin was dissolved using fats and oils as a solvent, it was inevitable to take fats and oils simultaneously with sesamin. There is a report case that the sesamin content in sesame oil and fat is 0.36% (Non-patent Document 1), that is, ingesting sesamin with sesame oil and fat is also inevitable at the same time.

USP 4427694 JP-A-2-138120 Patent 3001589 Japanese Patent No. 3070611 Japanese Patent No. 3075358 Patent 3075360 Patent 3124062 Japanese Patent No. 3283274 Japanese Patent Application No.2-281839 Japanese Patent Application No. 3-200777 Japanese Patent Application No. 3-212295 Japanese Patent Application No.5-14884

Sesame Science and Functionality Mitsuo Namiki Edition

  The subject of this invention is providing the lignan compound containing composition which was excellent in dispersion stability, food texture, flavor, etc., when added to food-drinks.

The present invention provides the following inventions as means for solving the above problems.
(1) Solid fine particles of a lignan compound having an average particle size of 20 to 1,000 nm as measured by a dynamic light scattering method.
(2) A lignan compound, an emulsifier, and a continuous phase component in which the lignan compound is dispersed, and the lignan compound has an average particle size of 20 to 1,000 nm when measured by a dynamic light scattering method. A lignan compound-containing composition in the form of solid fine particles.
(3) The composition of (2) substantially free of fats and oils.
(4) Production of fine particles of (1) or a composition of (2) or (3), comprising a step of pulverizing a mixture containing a lignan compound, an emulsifier, and a liquid continuous phase component in which the lignan compound is dispersed. Method.
(5) The method according to (4), wherein the liquid continuous phase component is a mixture of a polyhydric alcohol and an aqueous solvent.

  The lignan compound fine particles and the lignan compound-containing composition provided by the present invention can improve the texture such as dispersion stability and roughness in the added food and drink.

I. Material 1. Lignan compounds In the present invention, examples of the lignan compounds include sesamin, sesamorin, episesamin, sesaminol, episesaminol, sesamol and the like.

  The lignan compound used in the present invention is not limited at all by its form, production method and the like. For example, when sesamin is selected as the lignan compound, sesamin extracted from sesame oil by a known method (for example, a method described in JP-A-4-9331) (referred to as sesamin extract or concentrate) Can also be used.

2. Emulsifier The emulsifier used in the present invention is not particularly limited, and includes those used as pharmaceuticals or foods or used in the future.

  Here, HLB is a hydrophilic-hydrophobic balance that is usually used in the field of surfactants, and a commonly used calculation formula such as the Kawakami formula can be used. Kawakami's formula is shown below.

HLB = 7 + 11.7log (Mw / M0)
Here, Mw is the molecular weight of the hydrophilic group, and M0 is the molecular weight of the hydrophobic group.

  Moreover, you may use the numerical value of HLB described in the catalog etc. Further, as can be seen from the above formula, an emulsifier having an arbitrary HLB value can be obtained by utilizing the additivity of HLB.

  The emulsifier that can be used in the present invention is not particularly limited as long as it is an emulsifier that dissolves in an aqueous medium. For example, a nonionic surfactant having an HLB of 10 or more, preferably 12 or more, more preferably 14 to 16 is used. Is preferred. If the HLB is too low, the emulsifying power may be insufficient.

  The emulsifier that can be used in the present invention is not particularly limited, but a nonionic emulsifier is preferable. Examples of the nonionic emulsifier include glycerin fatty acid ester, organic acid monoglyceride, polyglycerin fatty acid ester, propylene glycol fatty acid ester, polyglycerin condensed ricinoleic acid ester, sorbitan fatty acid ester, sucrose fatty acid ester, and lecithin. More preferred are glycerin fatty acid esters, polyglycerin fatty acid esters, and sucrose fatty acid esters. The emulsifier is not necessarily highly purified by distillation or the like, and may be a reaction mixture.

  Examples of glycerin fatty acid esters used in the present invention include monooleic acid monoglyceride, monostearic acid monoglyceride, monopalmitic acid monoglyceride, monomyristic acid monoglyceride, monolauric acid monoglyceride, and the like. Of these, monooleic acid monoglyceride and monostearic acid monoglyceride are preferable. In the present invention, these polyglycerin fatty acid esters can be used alone or in combination. Examples of commercially available products include Exel T-95, Excel VS-95, Excel P-40S, Excel O-95R, Excel 200, Excel 122V, and Nikko Chemicals, manufactured by Kao Corporation. NIKKOL MGU, NIKKOL MGM, NIKKOL MGS-AV, NIKKOL MGS-AMV, NIKKOL MGS-ASEV, NIKKOL MGS-BV, NIKKOL MGS-BMV -DEXV, NIKKOL MGS-F20V, NIKKOL MGS-F40V, NIKKOL MGS-F50V, NIKKOL MGS-F50SEV, NIKKOL MGS-F75V, NIKKOL M GS-TGV, NIKKOL MGS-TGLV, NIKKOL MGS-150V, NIKKOL MGIS, NIKKOL MGO, NIKKOL MGOL-70, NIKKOL MGC, NIKKOL DGO-80, etc.

  The polyglycerin fatty acid ester used in the present invention has an average degree of polymerization of 2 or more, preferably 6 to 15, more preferably 8 to 10 and fatty acid having 8 to 18 carbon atoms, such as caprylic acid and caprin. Esters with acids, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, and linoleic acid. Preferred examples of polyglycerol fatty acid esters include hexaglycerol monooleate, hexaglycerol monostearate, hexaglycerol monopalmitate, hexaglycerol monomyristate, hexaglycerol monolaurate, decaglycerol monooleate , Decaglycerin monostearic acid ester, decaglycerin monopalmitic acid ester, decaglycerin monomyristic acid ester, decaglycerin monolauric acid ester and the like. These polyglycerin fatty acid esters can be used alone or in combination. Commercially available products include, for example, Nikko Chemicals Co., Ltd., NIKKOL DGMS, NIKKOL DGMO-CV, NIKOL DGMO-90V, NIKKOL DGDO, NIKKOL DGMIS, NIKKOL DGTIS, NIKKOL DGTIS, NIKKOL DGTIS Tetraglyn 3-S, NIKKOL Tetraglyn 5-S, NIKKOL Tetraglyn 5-O, NIKKOL Hexaglyn 1-L, NIKKOL Hexaglyn 1-M, NIKKOL Hexaglyn 1-SV, NIKKOL Hexaglyn 1-O, NIKKOL Hexaglyn 3-S, NIKKOL Hexaglyn 4 -B, NIKKOL Hexaglyn 5-S, IKKOL Hexaglyn 5-O, NIKKOL Hexaglyn PR-15, NIKKOL Decaglyn 1-L, NIKKOL Decaglyn 1-M, NIKKOL Decaglyn 1-SV, NIKKOL Decaglyn 1-50SV, NIKKOL Decaglyn 1-ISV, NIKKOL Decaglyn 1-O, NIKKOL Decaglyn 1-OV, NIKKOL Decaglyn 1-LN, NIKKOL Decaglyn1-PVEX, NIKKOL Decaglyn 2-SV, NIKKOL Decaglyn 2-ISV, NIKKOL Decaglyn 3-SV, NIKKOL Decaglyn 3-OV, NIKKOL Decaglyn 5-SV, NIKKOL Decaglyn 5 HS, NIKKOL Decaglyn 5-IS, NIKKOL Decaglyn 5-OV, NIKKOL Decaglyn 5-O-R, NIKKOL Decaglyn 7-S, NIKKOL Decaglyn 7-O, NIKKOL Decaglyn 10-SV, NIKKOL Decaglyn 10-IS, NIKKOL Decaglyn 10- OV, NIKKOL Decaglyn 10-MAC, NIKKOL Decaglyn PR-20, Ryoto polyglycerate L-10D, L-7D, M-10D, M-7D, P-8D, S-28D, manufactured by Mitsubishi Chemical Foods Co., Ltd. S-24D, SWA-20D, SWA-15D, SWA-10D, O-50D, O-15D, B-100D, B-70D, ER-60D, Taiyo Kagaku Co., Ltd. Examples include Sunsoft Q-17UL, Sunsoft Q-18S, Sunsoft Q-14S, Sunsoft A-141C, Poem DO-100, Poem J-0021 manufactured by Riken Vitamin Co., Ltd., and the like.

  The sucrose fatty acid ester used in the present invention preferably has a fatty acid having 12 or more carbon atoms, more preferably 12-20. Preferred examples of sucrose fatty acid esters include sucrose dioleate, sucrose distearate, sucrose dipalmitate, sucrose dimyristic ester, sucrose dilaurate, sucrose monooleate, sucrose Examples thereof include sugar monostearate, sucrose monopalmitate, sucrose monomyristate, and sucrose monolaurate. In the present invention, these sucrose fatty acid esters can be used alone or in combination. Examples of commercially available products include Ryoto Sugar Esters S-070, S-170, S-270, S-370, S-370F, S-570, S-770, and S-970 manufactured by Mitsubishi Chemical Foods Corporation. , S-1170, S-1170F, S-1570, S-1670, P-070, P-170, P-1570, P-1670, M-1695, O-170, O-1570, OWA-1570, L -195, L-595, L-1695, LWA-1570, B-370, B-370F, ER-190, ER-290, POS-135, DK former FD manufactured by Daiichi Kogyo Seiyaku Co., Ltd., DK ester F10, F10P, F20, F20P, F20W, F50, F50P etc. are mentioned.

3. Polyhydric alcohol Polyhydric alcohol can be suitably used as one of continuous phase components in which a lignan compound is dispersed in the present invention.

  In the present invention, the polyhydric alcohol is not particularly limited, and includes those used in pharmaceuticals, cosmetics, foods, or used in the future, such as glycerin, propylene glycol, butylene glycol, pentanediol, Examples include hexanediol and sugar alcohol (such as sorbitol). A particularly preferred polyhydric alcohol in the present invention is glycerin.

4). Aqueous solvent An aqueous solvent can be suitably used as one of the continuous phase components in which the lignan compound is dispersed in the present invention.

  In the present invention, the aqueous solvent is a general term for water and a water-soluble solvent, and specifically includes those composed only of water, those composed only of a water-soluble solvent, and those combined with water and a water-soluble solvent. Moreover, the water-soluble solvent may use 1 type, or may use 2 or more types together. The water-soluble solvent used is not particularly limited, and includes those used as pharmaceuticals or foods, or those used in the future. For example, methanol, ethanol, isopropanol and acetone, preferably ethanol.

II. Fine particles of the present invention The first embodiment of the present invention is solid fine particles containing a lignan compound. The fine particles have an average particle diameter measured by a dynamic light scattering method when the fine particles are dispersed in water at room temperature (25 ° C.) (according to the international standard ISO test method ISO 13321: 1996 (E) of the International Organization for Standardization). Are preferably 20 to 1000 nm, and more preferably 100 to 500 nm. When the average particle size of the fine particles of the present invention is 20 to 1000 nm, the lignan compound can be stably dispersed in the added food and drink, and the rough and granular feeling of the added food and drink is improved. Can do.

  The fine particles of the present invention are fine particles of a solid lignan compound. Solid fine particles can be produced by pulverizing a powder of a lignan compound by a method such as a wet pulverization method described later. The fine particles of the present invention may be fine particles in which a plurality of solid primary particles are aggregated, or may be fine particles composed of solid primary particles, as long as they have predetermined dimensions. It may be a mixture of The fine particles of the present invention are in the form of a solid, and thus emulsified fine particles comprising a liquid oil phase in an emulsified dispersion formed by emulsifying and dispersing a liquid oil phase in which a lignan compound is dissolved in an aqueous phase. It is clearly distinguished from (oil droplets).

  The fine particles of the present invention may be provided in any form, and the fine particles may be separated from each other, or may be in the form of a composition containing the fine particles and other components. The shape of the composition containing the fine particles of the present invention and other components may be any shape, and may be a liquid, solid or semi-solid shape.

III. Composition of the Present Invention A second embodiment of the present invention comprises a lignan compound, an emulsifier, and a continuous phase component in which the lignan compound is dispersed, and the lignan compound is measured by a dynamic light scattering method. The lignan compound-containing composition is in the form of solid fine particles having an average particle diameter of 20 to 1,000 nm. The definition of the average particle size of the lignan compound, the preferred range, and the effects produced thereby are as described above for the fine particles of the present invention.

  The composition of the present invention may be in any form, and may take a form corresponding to the form of the continuous phase component. The form of the continuous phase component can be liquid, solid, semi-solid, etc. at room temperature, and the composition of the present invention can be liquid, solid, semi-solid, etc. at room temperature. it can. The composition of the present invention is preferably a liquid composition in which solid fine particles of a lignan compound are dispersed by the action of an emulsifier in a liquid continuous phase component.

The content of each essential component in the composition of the present invention is not particularly limited.
The content of the lignan compound in the composition of the present invention is not particularly limited as long as the desired effect is exhibited, but it is 0.5 to 20% by weight with respect to the total weight of the composition. Preferably, it is 5 to 10% by weight. When the amount is 0.5% by weight or more, the amount of the composition added to the final product is reduced, and the product design value is improved. When the amount is 20% by weight or less, the composition is obtained using a wet pulverization method described later. This is because when the product is produced, the raw material mixture can be sufficiently pulverized. Since the composition of the present invention can contain a lignan compound at a high concentration, the amount of the lignan-containing composition to be ingested or used can be reduced.

  The content of the emulsifier is preferably 0.1 to 20% by weight and more preferably 1 to 10% by weight with respect to the total weight of the composition. When the amount is 0.1% by weight or more, it is easy to maintain a sufficiently finely pulverized state. When the amount is 20% by weight or less, the flavor is not adversely affected, and the ground product is not partially solubilized. This is because the grinding efficiency is improved.

  The content of the continuous phase component is not particularly limited as long as it can act as a medium for dispersing the lignan compound fine particles. When the continuous phase component is liquid, the content of the continuous phase component is preferably 80 to 99.4% by weight, and preferably 90 to 95% by weight, based on the total weight of the composition. More preferred. When the continuous phase component is solid, the content of the continuous phase component is preferably 10 to 99.4% by weight, and preferably 50 to 95% by weight, based on the total weight of the composition. Is more preferable. The continuous phase component may be composed of a single component or may be composed of two or more components. When the continuous phase component is composed of a plurality of components, the forms of the solid phase component such as “solid” and “liquid” refer to forms in which the plurality of components are combined in the composition. For example, when the continuous phase component comprises a solid first component and a liquid second component, when the composition is prepared by combining both, the solid first component becomes a liquid second component. When dissolved to become liquid, the continuous phase component is said to be liquid.

  The composition of the present invention is preferably substantially free of fats and oils. Specifically, the content of fats and oils in the composition of the present invention is preferably at most 5% by weight, more preferably at most 1% by weight, based on the total weight of the composition. More preferably it is not included. The oil and fat in the composition in the present invention is at most 5% by weight, so that the amount of oil and fat to be ingested can be reduced as compared with the conventional lignan compound-containing composition. Conventional lignan compound-containing compositions have the problem that the fat content is inevitably increased because the fat and oil in which the oil-soluble lignan compound is dissolved is emulsified and dispersed in the aqueous phase. According to the invention, since the lignan compound is finely divided and dispersed, it is possible to reduce the fat content.

  The composition of the present invention contains other components in appropriate amounts, for example, 0 to 20% by weight, preferably 0 to 10% by weight, based on the total weight of the composition (referring to the total weight of the solid content of the composition; the same applies hereinafter). More preferably 0 to 5% by weight, still more preferably 0 to 2% by weight, and most preferably no other components. Here, “including 0%” means not including. That is, “0 to XX wt%” of the other components means that the other components are not included or even if included, the maximum XX wt%. Other components are not particularly limited as long as they are acceptable components in final forms such as foods and drinks and pharmaceuticals.

  In particular, the composition of the present invention can contain sodium chloride, saccharides, pH adjusters, preservatives, antioxidants and the like as other components.

  The continuous phase component is not particularly limited as long as it is a component that does not substantially dissolve the lignan compound fine particles and can be dispersed as solid fine particles. In embodiments where the continuous phase component is liquid, preferably the component is a hydrophilic liquid component. As the liquid continuous phase component, a combination of an aqueous solvent and a polyhydric alcohol is preferable. Therefore, a preferred embodiment in which the continuous phase component is a liquid continuous phase component of an aqueous solvent and a polyhydric alcohol will be described in detail below.

  In the preferred embodiment, the content of the aqueous solvent is preferably 20 to 95% by weight and more preferably 50 to 95% by weight with respect to the total weight of the composition. When the amount is 20% by weight or more, the viscosity of the liquid composition is not significantly increased and can be easily pulverized. When the amount is 95% by weight or less, the amount of the active ingredient can be prevented from being reduced. This is because the value is not impaired. When the aqueous solvent is a mixture of water and a water-soluble solvent, the content of the water-soluble solvent is preferably 0.001 to 2 for the water-soluble solvent relative to water 1, and 0.01 to 0. .5 is more preferable.

  In the preferred embodiment, the content of the polyhydric alcohol is preferably 1 to 50% by weight, more preferably 5 to 30% by weight, based on the total weight of the composition. When the polyhydric alcohol is 1% by weight or more, the occurrence of agglomeration after pulverization is suppressed and the solution is difficult to precipitate. When the polyhydric alcohol is 50% by weight or less, the viscosity does not increase. This is because the pulverization efficiency is prevented from being significantly reduced. The content of the polyhydric alcohol is preferably from 0.1 to 50, and more preferably from 0.5 to 10, based on the weight 1 of the water-soluble solvent.

IV. Method for Producing Fine Particles and Composition of the Present Invention The fine particles and composition of the present invention include a wet pulverization step of pulverizing a mixture containing a lignan compound, an emulsifier, and a liquid continuous phase component in which the lignan compound is dispersed. Can be manufactured. The liquid continuous phase component used in the mixture is preferably a hydrophilic liquid component that does not substantially dissolve the lignan compound. Solid fine particles of a lignan compound produced by wet pulverization are preferred because they do not feel rough when added to food and taken orally.

  A mixture containing a lignan compound, an emulsifier, and a liquid continuous phase component can be obtained by mixing these components, preferably in the proportions detailed in III above. Although the mixing order of each component is not particularly limited, in a preferred embodiment, the mixture can be obtained by dispersing a lignan compound in a medium in which an emulsifier and a liquid continuous phase component are mixed.

  In the fine particles of the present invention, the average particle diameter of the solid fine particles of the lignan compound measured by a dynamic light scattering method (25 ° C.) by wet pulverization is 20 to 1000 nm, more preferably 100 to 500 nm. It can prepare by grind | pulverizing until it becomes.

  The wet pulverization for refining the lignan compound in the present invention is not particularly limited as long as the average particle size of the solid fine particles of the lignan compound falls within the above-mentioned range. A grinder can be used. As a wet pulverizer, a bead type wet pulverizer (OB mill, ultra apex mill, etc.); a planetary ball mill; a roll mill; a medium stirring mill flow pipe mill (sand grinder); a stirring tank mill (attritor, etc.); Other examples include a colloid mill. You may combine these 1 type (s) or 2 or more types, or you may repeat a refinement | miniaturization process with the same apparatus.

  The mixture after wet pulverization can itself be used as the composition of the present invention described in detail in III above. From the mixture after wet pulverization, further to a dry product or concentrate obtained by removing all or part of volatile components such as an aqueous solvent in the mixture, or to the mixture or dry product or concentrate after wet pulverization. A composition in which other components such as a continuous phase component are further added can also be used as the composition of the present invention described in detail in III above. For example, in an embodiment in which the mixture after wet pulverization contains a water-based solvent and a polyhydric alcohol such as sugar alcohol as a liquid continuous phase component, the water-based solvent is dried by appropriate means such as drying from the mixture after wet pulverization. The composition obtained by removing can be used as the composition of the present invention containing a polyhydric alcohol as a continuous phase component.

  The lignan compound-containing solid fine particles of the present invention may be provided in the form of the above-mentioned various compositions, and from these compositions, suitable solid-liquid separation means such as centrifugation and filtration, drying, etc. It may be provided in the form of solid fine particles containing a lignan compound separated by using the volatile component removing means. Here, the “separated solid fine particles containing lignan compound” are not necessarily composed only of solid fine particles containing lignan compound, and emulsifiers contained in the mixture after wet pulverization It may further include at least a part of the continuous phase component.

V. Use Form / Use of Fine Particles or Composition of the Present Invention The fine particles or composition of the present invention includes a food / beverage product composition or a pharmaceutical composition, particularly a food / beverage product or a pharmaceutical product (including those classified as quasi drugs. The same applies hereinafter. Etc.) can be used by adding to the composition for oral intake. The fine particles or composition of the present invention is particularly useful as a raw material in the production of food and drink. Specific examples of the food / beverage composition or pharmaceutical composition containing the fine particles or composition of the present invention include blood cholesterol lowering, liver function improvement, food / beverage prevention for sickness use, pharmaceuticals, and the like.

  The aspect of the said food / beverage products is not limited, It can be aspects, such as a health food, a dietary supplement, a nutritional functional food, a food for specified health. The food and drink can be, for example, beverages, confectionery, seasonings, soups, processed foods, dairy products, noodles, bread and cooked rice. Examples of beverages include soy milk, milk, and lactic acid bacteria beverages.

  The embodiment of the pharmaceutical is not particularly limited, and examples thereof include liquids, capsules, tablets, granules, injections, suppositories, patches, ointments, fine granules, caplets, powders, troches and the like, especially for oral administration. Examples include pharmaceutical forms. For pharmaceuticals, the microparticles of the present invention can be used for other pharmaceutically acceptable formulation materials such as excipients, disintegrants, lubricants, binders, antioxidants, coloring agents, anti-aggregation agents, and absorption enhancers. It can be produced by formulating it in appropriate combination with an agent, a solubilizing agent, a stabilizer and the like.

  EXAMPLES Hereinafter, although an Example and a comparative example demonstrate this invention further in detail, this invention is not limited to the following Example.

[Example 1]
Decaglycerin monostearate ester (trade name: Sunsoft Q-18S, Taiyo Kagaku Co., Ltd.) 8 g was added to ion exchange water 140 g, heated to 80 ° C. and confirmed to be dissolved, and then allowed to cool to room temperature. . To this solution, 10 g of 99.5% fermented ethanol (manufactured by Nippon Alcohol Sangyo Co., Ltd.) and 30 g of glycerin (manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.) were added and mixed uniformly to make a dispersion solvent. After adding 500 g of 0.3 mm zirconia beads to a 500 mL zirconia vessel and filling the above dispersion solvent, 12 g of sesamin (manufactured by Orcas) was added, and then installed on a planetary ball mill P-6 (manufactured by Fritsch Japan). Then, after grinding for 60 minutes at a revolution of 200 rpm, the beads were filtered with a sieve to obtain the product 1 of the present invention which was a cloudy liquid composition. The average particle diameter of the lignan compound-containing fine particles measured by the dynamic light scattering method using ELS-Z (manufactured by Otsuka Electronics Co., Ltd.) was about 300 nm. .

[Example 2]
40 g of decaglycerin monopalmitate (trade name: Decaglyn1-PVEX, manufactured by Nikko Chemicals) and 40 g of decaglycerin monostearate (trade name: Ryoto Sugar Ester S-10D, manufactured by Mitsubishi Chemical Foods) 1 320 g, and after heating to 80 ° C. and confirming dissolution, the mixture was allowed to cool to room temperature. To this solution, 99.5% fermented ethanol (200 g) and glycerin (200 g) were added and mixed uniformly to obtain a dispersion solvent. Next, 0.3 mm zirconia beads were sealed in an OB mill (Freund Turbo) to give a vessel filling rate of 80%, and 200 g of sesamin was added while circulating the dispersion solvent with a pump. The product of the present invention 2 which is a liquid composition was obtained by setting the vessel rotation speed to 2000 rpm, collecting the solution in another container, and performing the process of recirculation three times. The average particle size of the lignan compound-containing fine particles of the product 2 of the present invention measured by the dynamic light scattering method in the same manner as in Example 1 was about 500 nm.

[Comparative Example 1]
Decaglycerin monostearate (trade name: Sunsoft Q-18S, Taiyo Kagaku Co., Ltd.) 8 g was added to 170 g of ion-exchanged water, heated to 80 ° C. and dissolved, and allowed to cool to room temperature. A dispersion solvent was used. After adding 500 g of 0.3 mm zirconia beads to a 500 mL zirconia vessel and filling the above dispersion solvent, 12 g of sesamin (manufactured by Orcas Co.) was added, and then installed in a planetary ball mill P-6, at a revolution of 200 rpm. After pulverizing for 60 minutes, the mixture was filtered through a sieve to obtain Comparative Product 1 which was a cloudy liquid composition. The average particle size of the lignan compound-containing fine particles of Comparative Product 1 measured by the dynamic light scattering method in the same manner as in Example 1 was about 2,000 nm.

[Comparative Example 2]
Decaglycerin monostearate (trade name: Sunsoft Q-18S, Taiyo Kagaku Co., Ltd.) 8 g was added to 70 g of ion exchange water, heated to 80 ° C. and confirmed to be dissolved, and then allowed to cool to room temperature. . To this solution, 10 g of 99.5% fermented ethanol (manufactured by Nippon Alcohol Sangyo Co., Ltd.) and 100 g of glycerin (manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.) were added and mixed uniformly to make a dispersion solvent. After adding 500 g of 0.3 mm zirconia beads to a 500 mL zirconia vessel and filling the above dispersion solvent, 12 g of sesamin (manufactured by Orcas Co.) was added, and then installed in a planetary ball mill P-6, at a revolution of 200 rpm. The comparative product 2 which is a cloudy liquid composition was obtained by grinding for 60 minutes. Comparative product 2 was pasty and it was difficult to separate the beads and the solution. Moreover, the average particle diameter of the lignan compound-containing fine particles in the dispersion liquid diluted 100 times with ion-exchanged water and filtered was about 3,000 nm.

[Comparative Example 3]
40 g of decaglycerin monopalmitate (trade name: Decaglyn1-PVEX, manufactured by Nikko Chemicals) and 40 g of decaglycerin monostearate (trade name: Ryoto Sugar Ester S-10D, manufactured by Mitsubishi Chemical Foods) In addition to 1,520 g, after confirming that it was dissolved by heating to 80 ° C., the mixture was allowed to cool to room temperature, and then 200 g of 99.5% fermented ethanol was added as a dispersion solvent. Next, 0.3 mm zirconia beads were sealed in an OB mill (Freund Turbo) to give a vessel filling rate of 80%, and 200 g of sesamin was added while circulating the dispersion solvent with a pump. The vessel rotation speed was set to 2000 rpm, the solution was collected in a separate container and circulated again three times to obtain a comparative product 3 as a liquid composition. In Comparative Example 3, the average particle size of the lignan compound-containing fine particles measured by the dynamic light scattering method in the same manner as in Example 1 was about 2,000 nm, and a large amount of precipitate was confirmed in the pipe. It was suggested that the solid content of the liquid was lowered.

Claims (3)

A lignan compound-containing composition comprising a lignan compound, an emulsifier (except for citric acid monoglyceride and succinic acid monoglyceride) , and a liquid continuous phase component in which the lignan compound is dispersed, wherein the lignan compound is Solid microparticles that are at least one selected from sesamin, sesamolin, episesamin, sesaminol, episesaminol, and sesamol, and have an average particle size of 20 to 1,000 nm when measured by a dynamic light scattering method And the continuous phase component is a mixture of a polyhydric alcohol and an aqueous solvent containing water and a water-soluble solvent (excluding the polyhydric alcohol), and the content of the polyhydric alcohol is 1 by weight of the water-soluble solvent. The said lignan compound containing composition which is 0.5-10 with respect to. The content of fat is 5 wt% at most relative to the total weight of the composition of claim 1. A lignan compound, an emulsifier (excluding citric acid monoglyceride and succinic acid monoglyceride) , and a liquid continuous phase component in which the lignan compound is dispersed, comprising a polyhydric alcohol, water and a water-soluble solvent (polyhydric alcohol) And a step of pulverizing the mixture containing the continuous phase component having a polyhydric alcohol content of 0.5 to 10 with respect to the weight 1 of the water-soluble solvent. No method of 請 Motomeko 1 or 2 of the composition.