WO2020262381A1 - Gel soluble dans l'eau d'acide hyaluronique et procédé de production associé - Google Patents

Gel soluble dans l'eau d'acide hyaluronique et procédé de production associé Download PDF

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Publication number
WO2020262381A1
WO2020262381A1 PCT/JP2020/024608 JP2020024608W WO2020262381A1 WO 2020262381 A1 WO2020262381 A1 WO 2020262381A1 JP 2020024608 W JP2020024608 W JP 2020024608W WO 2020262381 A1 WO2020262381 A1 WO 2020262381A1
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Prior art keywords
hyaluronic acid
water
soluble
mass
gel
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PCT/JP2020/024608
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English (en)
Japanese (ja)
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邦夫 米戸
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株式会社リタファーマ
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Priority to JP2020539103A priority Critical patent/JP6836820B1/ja
Publication of WO2020262381A1 publication Critical patent/WO2020262381A1/fr

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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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • 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
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • 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
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
    • A61L15/28—Polysaccharides or their derivatives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
    • C08J3/075—Macromolecular gels
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00

Definitions

  • the present invention relates to a water-soluble hyaluronic acid gel and a method for producing the same.
  • Hyaluronic acid which has excellent biocompatibility and exhibits many effective effects including moisturizing effect, has been attracting attention in the fields of beauty, medical care, food, and the like.
  • Hyaluronic acid is a linear high molecular weight polysaccharide in which ⁇ -DN-acetylglucosamine and ⁇ -D-glucuronic acid are alternately bound, and is distributed in the connective tissue of mammals, as well as in chicken combs. It is known to be present in the capsule of streptococci.
  • Commercially available hyaluronic acid is generally prepared by isolation and extraction from chicken combs, umbilical cords, etc., and fermentation methods using microorganisms such as Streptococcus.
  • gel compositions containing polymer materials have been used in the fields of beauty, medical care, foods, and the like.
  • gel compositions used in the fields of beauty, medical care, foods, etc. are applied to the human body, and are therefore required to have excellent safety and biocompatibility. Therefore, it has been studied to use hyaluronic acid, which is a natural material and has excellent safety and biocompatibility, as the polymer material contained in such a gel composition.
  • Patent Document 1 in an acidic transparent gel-like food containing 0.005 to 0.5% hyaluronic acid and / or a salt thereof, the Brix of the product is 20 to 40, and the product is deacylated. Blend gellan gum, soluble calcium salt, and 6 to 30% starch syrup (solid content equivalent), and add 60 or more starch syrup (solid content equivalent) to 1 part of hyaluronic acid and / or its salt.
  • a characteristic acidic transparent gel-like food is disclosed.
  • the acidic transparent gel-like food of Patent Document 1 has a transparent feeling even after heating by using a deacylated gellan gum and a soluble calcium salt as a gelling agent in addition to hyaluronic acid and further adding xanthan gum and the like. It discloses a technique for maintaining gel-like physical properties.
  • Patent Document 1 in a water-soluble gel composition containing hyaluronic acid, conventionally used polyacrylic acid or a salt thereof, xanthan gum, glucomannan, guar gum, locust bean, agar, carrageenan, polyvinyl alcohol and the like have been used. Attempts have been made to develop a hyaluronic acid gel in which hyaluronic acid is used alone as a gel-forming component without using the existing gel-forming component.
  • Patent Document 2 contains hyaluronic acid, sugar (excluding liquid polyhydric alcohol which is a liquid at 25 ° C.), and water, and has a water content of more than 30% by mass, other than the hyaluronic acid.
  • a water-soluble hyaluronic acid gel is disclosed that does not substantially contain the gel-forming component of the above and has a pH in the range of 1.9 to 6.3 as measured by a predetermined method.
  • the water-soluble hyaluronic acid gel disclosed in Patent Document 2 has a gel form that is excellent in stability not only at room temperature but also at low temperature, and is used for cosmetics, medical device compositions, food compositions, and pharmaceuticals. It can be suitably used as a composition or the like.
  • the content of water contained in the hyaluronic acid aqueous solution is an amount at which the hyaluronic acid aqueous solution does not gel at about room temperature (25 ° C.), and when preparing a water-soluble hyaluronic acid gel, most of the water from the hyaluronic acid aqueous solution is used. A step of evaporating is required.
  • the main object of the present invention is to provide a water-soluble hyaluronic acid gel that can be produced with high productivity without the need to provide a step of evaporating a large amount of water from the hyaluronic acid aqueous solution in the production of the water-soluble hyaluronic acid gel. And. Furthermore, it is also an object of the present invention to provide a method for producing the water-soluble hyaluronic acid gel, cosmetics using the water-soluble hyaluronic acid gel, medical device compositions, food compositions, or pharmaceutical compositions. ..
  • the present inventor has made diligent studies to solve the above problems. As a result, it is a water-soluble hyaluronic acid gel containing hyaluronic acid, water-soluble dietary fiber, an acid different from the hyaluronic acid, and water, and as the water-soluble dietary fiber, glucose is a constituent sugar, 1-4 bonds and 1
  • a water-soluble hyaluronic acid gel by using a polysaccharide having a bond other than -6 bond and not having a cyclic structure, and further setting the contents of water and water-soluble dietary fiber within predetermined ranges, respectively. It has been found that a water-soluble hyaluronic acid gel that can be produced with high productivity can be obtained without the need to provide a step of evaporating a large amount of water from the hyaluronic acid aqueous solution.
  • the property of softening / liquefying by preparing an aqueous solution of the water-soluble hyaluronic acid gel while heating, and gelling when cooled, for example, of a water-soluble hyaluronic acid gel.
  • a uniform hyaluronic acid aqueous solution that is fluid in a heating environment can be prepared, and the aqueous solution can be filled in a container as it is, or spread on a film to form a uniform sheet.
  • the water-soluble hyaluronic acid gel Since the water-soluble hyaluronic acid gel has such properties, it can be produced with high productivity, and even if the water-soluble hyaluronic acid gel is placed in a high temperature environment in the distribution process and softened / liquefied, for example. Since it gels again at room temperature, it has excellent stability as a product.
  • the present invention is an invention completed by further studies based on these findings.
  • the water-soluble hyaluronic acid gel is 1 to 300 parts by mass with respect to 1 part by mass of the hyaluronic acid.
  • Item 2. The water-soluble hyaluronic acid gel according to Item 1, wherein the pH of the aqueous solution measured by the following measuring method is in the range of 1.9 to 6.3. (Method for measuring pH) Of the components contained in the water-soluble hyaluronic acid gel in an amount containing 1 g of hyaluronic acid, all ionic components except water were dissolved in water to prepare an aqueous solution so as to have 200 mL. The pH of the obtained aqueous solution is measured.
  • Item 3. Item 2.
  • Item 4. Item 1 to 3, wherein the total content of the hyaluronic acid, the water-soluble dietary fiber, an acid different from the hyaluronic acid, and the water is 30% by mass or more in 100% by mass of the water-soluble hyaluronic acid gel.
  • Item 6. Item 2. The water-soluble hyaluronic acid gel according to any one of Items 1 to 5, which is in the form of a sheet.
  • Item 7. Item 2. The water-soluble hyaluronic acid gel according to any one of Items 1 to 5, which is granular.
  • Item 11. A pharmaceutical composition using the water-soluble hyaluronic acid gel according to any one of Items 1 to 8.
  • Item 13. Item 2. The method for producing a water-soluble hyaluronic acid gel according to any one of Items 1 to 8, wherein the hyaluronic acid, 1 to 300 parts by mass of the water-soluble dietary fiber with respect to 1 part by mass of the hyaluronic acid, and the above.
  • a method for producing a water-soluble hyaluronic acid gel comprising the step 2 of cooling the hyaluronic acid aqueous solution to a temperature of less than 40 ° C.
  • Item 14 Item 3. The method for producing a water-soluble hyaluronic acid gel according to Item 13, wherein the reduction rate of water from the water-soluble hyaluronic acid aqueous solution between the steps 1 and 2 is 50% by mass or less.
  • the present invention in the production of a water-soluble hyaluronic acid gel, it is not necessary to provide a step of evaporating a large amount of water from the hyaluronic acid aqueous solution, and it is possible to provide a water-soluble hyaluronic acid gel that can be produced with high productivity. .. According to the present invention, it is possible to provide a method for producing the water-soluble hyaluronic acid gel, cosmetics using the water-soluble hyaluronic acid gel, a composition for medical devices, a food composition, or a pharmaceutical composition.
  • the water-soluble hyaluronic acid gel of the present invention is a water-soluble hyaluronic acid gel containing hyaluronic acid, water-soluble dietary fiber, an acid different from the hyaluronic acid, and water, and the water-soluble dietary fiber contains glucose as a constituent sugar. It is a polysaccharide having bonds other than 1-4 bonds and 1-6 bonds and not having a cyclic structure, and the content of water is 1 to 300 parts by mass with respect to 1 part by mass of the hyaluronic acid. The content of the water-soluble dietary fiber is 1 to 300 parts by mass with respect to 1 part by mass of the hyaluronic acid.
  • the water-soluble hyaluronic acid gel of the present invention has such a structure, it is not necessary to provide a step of evaporating a large amount of water from the hyaluronic acid aqueous solution in the production of the water-soluble hyaluronic acid gel, and the productivity is high.
  • a uniform hyaluronic acid aqueous solution that is fluid in a heating environment can be prepared, and the aqueous solution can be filled in a container as it is or spread on a film to form a uniform sheet. Moreover, it has the property of forming a water-soluble hyaluronic acid gel when cooled to about room temperature. Since the water-soluble hyaluronic acid gel of the present invention has such properties, it can be produced with high productivity, and for example, the water-soluble hyaluronic acid gel is softened / liquefied by being placed in a high temperature environment in the distribution process. However, since it gels again at room temperature, it has excellent stability as a product.
  • the water-soluble hyaluronic acid gel of the present invention the method for producing the water-soluble hyaluronic acid gel, cosmetics using the water-soluble hyaluronic acid gel, medical device compositions, food compositions, or pharmaceutical compositions (external use, Oral, etc.) will be described in detail.
  • the water-soluble hyaluronic acid gel of the present invention contains hyaluronic acid, water-soluble dietary fiber, an acid different from the hyaluronic acid, and water.
  • the water-soluble hyaluronic acid gel of the present invention contains, for example, hyaluronic acid, 1 to 300 parts by mass of water-soluble dietary fiber with respect to 1 part by mass of hyaluronic acid, an acid different from hyaluronic acid, and hyaluronic acid.
  • the heated hyaluronic acid aqueous solution can be suitably produced by the production method including the step 2, and it is not necessary to include a step of evaporating a large amount of water in the production method. That is, when the heated hyaluronic acid aqueous solution is cooled to about room temperature, the water-soluble hyaluronic acid gel of the present invention having substantially the same composition as the hyaluronic acid aqueous solution can be obtained.
  • the reduction rate of water from the water-soluble hyaluronic acid aqueous solution between steps 1 and 2 is 50% by mass or less (that is, the content of water contained in the hyaluronic acid aqueous solution is 100% by mass (reference)).
  • the content of water contained in the water-soluble hyaluronic acid gel can be 50% by mass or more).
  • hyaluronic acid is contained as a gel-forming component.
  • hyaluronic acid is substantially alone as a gel-forming component, and other gel-forming components are not substantially contained.
  • the water-soluble hyaluronic acid gel of the present invention may contain a small amount of other gel-forming components in addition to hyaluronic acid, as long as the effects of the present invention are not impaired.
  • gel-forming components are not particularly limited, but are, for example, polyacrylic acid or a salt thereof, xanthan gum, gellan gum, glucomannan, guar gum, locust bean gum, agar, gelatin, pectin, malariaenine, arabic rubber, carrageenan, agarose, etc.
  • Known gel-forming components such as alginic acid, propylene glycol alginate, sodium carboxymethyl cellulose, hydroxypropyl cellulose, polyvinyl alcohol, carboxyvinyl polymer, starch / acrylate graft copolymer, methyl vinyl ether / maleic anhydride copolymer and the like can be mentioned. ..
  • the content of the other gel-forming components is determined by the composition of the water-soluble hyaluronic acid gel of the present invention from the viewpoint of utilizing the characteristics of the water-soluble hyaluronic acid gel of the present invention.
  • the amount is preferably less than or equal to the amount at which gel is not formed.
  • the content of other gel-forming components varies depending on the type of other gel-forming components, but is 5% by mass or less, preferably 2.5% by mass or less, more preferably in the water-soluble hyaluronic acid gel of the present invention. Is 1% by mass or less, more preferably 0.5% by mass or less, and even more preferably 0.1% by mass or less.
  • the water-soluble hyaluronic acid gel of the present invention does not substantially contain at least one of the deacylated gellan gum and the soluble calcium salt disclosed in Patent Document 1.
  • the fact that the deacylated gellan gum is substantially not contained means, for example, that the content of the deacylated gellan gum is less than 0.05% by mass, more preferably 0.03% by mass or less, still more preferably 0.01% by mass or less.
  • the fact that the soluble calcium salt is substantially not contained means, for example, that the content of the soluble calcium salt is less than 0.01% by mass, more preferably 0.005% by mass or less, still more preferably 0.003% by mass or less.
  • the deacylated gellan gum is a deacylated form of a microbial polysaccharide produced by Sphingomonas elodea.
  • the soluble calcium salt is a calcium salt that functions as a gelling aid, for example, calcium lactate, calcium chloride, calcium acetate, calcium gluconate, calcium monophosphate, calcium fumarate, calcium malate, calcium succinate, etc.
  • a gelling aid for example, calcium lactate, calcium chloride, calcium acetate, calcium gluconate, calcium monophosphate, calcium fumarate, calcium malate, calcium succinate, etc.
  • calcium citrate for example, calcium citrate.
  • hyaluronic acid is used in the concept of including hyaluronic acid and a salt thereof. Therefore, in the present invention, “hyaluronic acid and / or a salt thereof” is simply referred to as “hyaluronic acid” unless otherwise specified as "a salt of hyaluronic acid”.
  • the salt of hyaluronic acid is not particularly limited, and examples thereof include sodium hyaluronate, potassium hyaluronate, magnesium hyaluronate, and calcium hyaluronate. In the present invention, one type of hyaluronic acid may be used alone, or two or more types may be used in combination.
  • the molecular weight of hyaluronic acid is not particularly limited as long as it can form a gel even when hyaluronic acid is used alone as a gel-forming component, but as described above, a water-soluble hyaluronic acid gel that can be produced with high productivity can be obtained. From the viewpoint of providing more preferably, it is preferably about 5.0 ⁇ 10 4 to 5.0 ⁇ 10 6 daltons, more preferably about 1.0 ⁇ 10 5 to 2.3 ⁇ 10 6 daltons, and even more preferably about 1.0 ⁇ 10 5 to 2.3 ⁇ 10 6 daltons. Examples thereof include 3.5 ⁇ 10 5 to 1.6 ⁇ 10 6 . As the hyaluronic acid, one having a single molecular weight may be used, or one having a plurality of types of molecular weights may be mixed and used.
  • the origin of hyaluronic acid is not particularly limited, and for example, those isolated and extracted from chicken combs, umbilical cords, etc., and those prepared by a fermentation method using microorganisms such as Streptococcus can be preferably used.
  • a commercially available product can be used as the hyaluronic acid. Since the water-soluble hyaluronic acid gel of the present invention does not need to be chemically modified as hyaluronic acid, it has excellent biocompatibility and can exhibit the characteristics of natural hyaluronic acid.
  • water-soluble hyaluronic acid gel of the present invention only hyaluronic acid that is not substantially chemically modified may be used as the hyaluronic acid.
  • the water-soluble hyaluronic acid gel of the present invention may further contain chemically modified hyaluronic acid as long as it does not inhibit the effect of the present invention.
  • chemically modified hyaluronic acid examples include hydroxypropyltrimonium hyaluronate, hydrolyzed alkyl hyaluronate (C12-13) glyceryl, propylene glycol hyaluronate, and acetylated sodium hyaluronate.
  • the chemically modified hyaluronic acid may be used alone or in combination of two or more.
  • the content of hyaluronic acid is not particularly limited as long as the gel can be formed, but as described above, the water-soluble hyaluronic acid gel that can be produced with high productivity is more preferable. From the viewpoint of providing the above, for example, about 0.2 to 50% by mass, preferably about 0.3 to 30% by mass, and more preferably about 0.4 to 10% by mass.
  • the content of hyaluronic acid in the water-soluble hyaluronic acid gel is less than 0.2% by mass, the gel may not be formed from the aqueous hyaluronic acid solution.
  • the content of hyaluronic acid in the water-soluble hyaluronic acid gel exceeds 50% by mass, the water-soluble hyaluronic acid gel becomes too hard, and the cosmetics, food compositions, pharmaceutical compositions, or medical device compositions described below are used. It may be difficult to use it as an object.
  • the water-soluble dietary fiber is a polysaccharide having glucose as a constituent sugar, having bonds other than 1-4 bonds and 1-6 bonds, and not having a cyclic structure. Therefore, for example, indigestible cyclodextrin having a cyclic structure is not included in the water-soluble dietary fiber.
  • the component that is not hydrolyzed by glucoamylase is preferably 30% by mass or more, more preferably 50% by mass or more, further preferably 70% by mass or more, still more preferably 80% by mass or more, and particularly preferably 90% by mass. % Or more.
  • the water-soluble dietary fiber include isomaltodextrin, indigestible dextrin, indigestible glucan, polydextrose and the like, and preferably isomaltodextrin and reduced indigestible dextrin, which are less colored by heating. , And reduced polydextrose and the like.
  • the component that is not hydrolyzed by glucoamylase is preferably 30% by mass or more, more preferably 50% by mass or more, still more preferably 70% by mass or more, still more preferably 80% by mass or more, particularly. It is preferably 90% by mass or more.
  • the water-soluble dietary fiber contained in the water-soluble hyaluronic acid gel of the present invention may be one kind or two or more kinds.
  • Isomaltodextrin is a highly branched multi-branched ⁇ -glucan composed only of ⁇ -linked glucose by allowing an enzyme to act on starch such as cornstarch, and is a water-soluble food that has been desalted and decolorized as necessary. A fiber that has indigestible characteristics. Examples of commercially available isomaltodextrin products include Fiberlixa (manufactured by Hayashibara Co., Ltd.) and the like.
  • Indigestible dextrin requires roasted dextrin obtained by acidifying (for example, adding hydrochloric acid) and / or heating starch derived from plants such as corn, wheat, rice, beans, potatoes, and tapioca.
  • a water-soluble dietary fiber that has been subjected to enzymatic treatment with ⁇ -amylase and / or glucoamylase, and then desalted and decolorized as necessary, and has indigestible characteristics.
  • the indigestible dextrin shall also include a reduced product of the indigestible dextrin produced by hydrogenation.
  • indigestible dextrin Commercially available products of indigestible dextrin include, for example, Fibersol 2 (manufactured by Matsutani Chemical Industry Co., Ltd.), Amirets C-70099M (manufactured by Oji Corn Starch Co., Ltd.), Nutriose (manufactured by Rocket Foil Co., Ltd.), Promiter 85 (Tate) & Made by Lyle), etc.
  • Fibersol 2 manufactured by Matsutani Chemical Industry Co., Ltd.
  • Amirets C-70099M manufactured by Oji Corn Starch Co., Ltd.
  • Nutriose manufactured by Rocket Foil Co., Ltd.
  • Promiter 85 Tate
  • & Made by Lyle etc.
  • a commercially available product of a reduced product of indigestible dextrin Reduced indigestible dextrin
  • Fiber Sol 2H manufactured by Matsutani Chemical Industry Co., Ltd.
  • the indigestible glucan is a water-soluble dietary fiber obtained by heat-polymerizing a starch decomposition product (preferably a starch decomposition product having a dextrose equivalent (DE) of 70 to 100), and is characterized by being indigestible. It means what you have. At this time, the raw material may contain monosaccharides other than glucose, oligosaccharides containing these monosaccharides, and the like.
  • the "indigestible glucan" may be the indigestible glucan itself, or may be an indigestible glucan enzyme-treated product obtained by treating the indigestible glucan with a glycolytic enzyme, and the indigestible glucan enzyme.
  • indigestible glucan fractionated product obtained by fractionating the treated product, or may be an indigestible glucan reduced product obtained by reducing the aldehyde group at the reducing end of the indigestible glucan to a hydroxyl group.
  • examples of commercially available products of indigestible glucan include Fit Fiber # 80 (manufactured by Nihon Shokuhin Kako Co., Ltd.).
  • Polydextrose is a highly branched and randomly bound water-soluble dietary fiber obtained by polymerizing D-glucose at a high temperature in the presence of sorbitol and an acid (for example, citric acid or phosphoric acid). Those with digestible characteristics. Polydextrose shall also include a reduced product of polydextrose. Examples of commercially available products of polydextrose include Starlight III (manufactured by Koyo Shokai Co., Ltd.), Lites (manufactured by Pfizer Inc.), Lites II (manufactured by Danisco), and the like. Examples of commercially available products of reduced polydextrose (reduced polydextrose) include Starlight Elite (manufactured by Koyo Shokai Co., Ltd.).
  • the content of the water-soluble dietary fiber is 1 to 300 parts by mass with respect to 1 part by mass of hyaluronic acid.
  • the content of the water-soluble dietary fiber is preferably 2 to 2 to 1 part by mass of hyaluronic acid.
  • the content of water-soluble dietary fiber in the water-soluble hyaluronic acid gel of the present invention can be expressed as "containing dietary fiber" as shown in "Cabinet Office Ordinance Food Labeling Standards". 3% by mass or more is preferable in 100% by mass of the hyaluronic acid gel, and since it is possible to express that "containing a high concentration of water-soluble dietary fiber", 6% by mass in 100% by mass of the water-soluble hyaluronic acid gel is possible. % Or more is more preferable.
  • the acid different from hyaluronic acid is not particularly limited as long as it is mixed with water and exhibits acidity, and either an inorganic acid or an organic acid can be used.
  • the inorganic acid include phosphoric acid, hydrochloric acid, sulfuric acid, nitric acid, perchloric acid, carbonic acid and the like, and preferably phosphoric acid, hydrochloric acid and sulfuric acid.
  • organic acids monocarboxylic acids such as formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, lipoic acid; dicarboxylic acids such as succinic acid, phthalic acid, fumaric acid, oxalic acid, malonic acid and glutaric acid.
  • monocarboxylic acids such as formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, lipoic acid
  • dicarboxylic acids such as succinic acid, phthalic acid, fumaric acid, oxalic acid, malonic acid and glutaric acid.
  • Acids such as glycolic acid, citric acid, lactic acid, pyruvate, malic acid, tartaric acid, adipic acid, salicylic acid; polyhydroxy acids such as glucono- ⁇ -lactone and lactopionic acid; acidic amino acids such as glutamate and aspartic acid Amino acid derivatives such as Narsgen (registered trademark, methyl carboxymethylphenylaminocarboxypropylphosphonate); Ascorbic acid such as ascorbic acid, ethyl ascorbate, ascorbic acid glucoside or derivatives thereof, preferably acetic acid, ascorbic acid, citrus Examples thereof include acids, glycolic acids, lactic acid, malic acid, tartaric acid, salicylic acid, ethyl ascorbate, ascorbic acid glucoside, glucono- ⁇ -lactone and lactopionic acid.
  • oxycarboxylic acids such as glycolic acid, citric acid, lactic acid, pyruvate, malic
  • examples of the acid for oral ingestion include citric acid, tartaric acid, ascorbic acid, ascorbic acid derivative, malic acid, fumaric acid, succinic acid, adipic acid, and lactic acid, which are also good acidulants.
  • One type of acid may be used alone, or two or more types may be used in combination.
  • the pH of the aqueous solution measured by the following measuring method is preferably in the range of 1.9 to 6.3, more preferably in the range of 2.0 to 5.2. , 2.0 to 4.6, more preferably.
  • the pH can be adjusted by blending an acid different from hyaluronic acid.
  • the pH of the aqueous solution prepared by the above-mentioned measuring method is measured.
  • the pH of the aqueous solution prepared by the above-mentioned measuring method is measured.
  • the water-soluble hyaluronic acid gel contains a large amount of nonionic water-soluble dietary fiber, sugar, etc., it becomes difficult to accurately measure the pH. Therefore, in the present invention, among the components to be blended in the water-soluble hyaluronic acid gel, only all the ionic components except water are dissolved in water, and the pH of the obtained aqueous solution is measured.
  • the water content is 1 to 300 parts by mass with respect to 1 part by mass of the hyaluronic acid.
  • the water content is preferably about 2 to 200 parts by mass with respect to 1 part by mass of hyaluronic acid. , More preferably about 5 to 200 parts by mass, still more preferably about 5 to 150 parts by mass, still more preferably about 8 to 150 parts by mass, still more preferably about 2 to 100 parts by mass, still more preferably about 3 to 100 parts by mass. Is about 5 to 100 parts by mass, more preferably about 8 to 100 parts by mass.
  • the water content of the water-soluble hyaluronic acid gel of the present invention is preferably 15 to 90% by mass, more preferably 15 to 70% by mass, and further preferably 15 to 60% by mass in 100% by mass of the water-soluble hyaluronic acid gel. Mass% is mentioned.
  • the blending ratio of the water-soluble dietary fiber and water is preferably about 1: 0.2 to 15 on a mass basis. It is preferably about 1: 0.3 to 10, more preferably about 1: 0.4 to 5, and more preferably about 1: 0.5 to 2.
  • the total content of hyaluronic acid, water-soluble dietary fiber, an acid different from hyaluronic acid, and water is 30% by mass or more in 100% by mass of the water-soluble hyaluronic acid gel. It is preferably 40% by mass or more, more preferably 50% by mass or more, and further preferably 60% by mass or more.
  • the total content may be 70% by mass or more, 75% by mass or more, 85% by mass or more, or 90% by mass or more. However, it may be 95% by mass or more, or 100% by mass.
  • the other components include sugars (however, liquid liquid at 25 ° C.). (Excluding polyhydronic alcohol) is preferably contained.
  • the content of the other component is, for example, about 5 to 70% by mass, about 5 to 60% by mass, about 5 to 50% by mass, about 5 to 40% by mass, about 5 to 30% by mass, and 5 to 20% by mass. %, 5 to 10% by mass, and the like.
  • the sugar (excluding the liquid polyhydric alcohol that is liquid at 25 ° C.) is not particularly limited, and monosaccharides and sugars ranging from disaccharide to ten sugar can be used.
  • specific examples of sugars include glucose, fructose, xylitol, sorbitol, martitol, erythritol, lactitol, mannitol, trehalose, lactose, maltose, sucrose, raffinose, reduced isomaltose, oligosaccharides (fructo-oligosaccharides, galactooligosaccharides, mannan oligosaccharides) Sugar, lactose-fructose oligosaccharide, isomaltooligosaccharide, lactose oligosaccharide, maltooligosaccharide, soybean oligosaccharide, xylooligosaccharide, etc.), ⁇
  • the water-soluble hyaluronic acid of the present invention can be expected to have a synergistic effect with the water-soluble dietary fiber that regulates the intestinal environment by blending oligosaccharides that serve as nutrients for good bacteria such as bifidobacteria and lactic acid bacteria in the intestine. It is preferable to add oligosaccharide to the gel.
  • One type of sugar may be used alone, or two or more types may be used in combination.
  • the content of the sugar contained in the water-soluble hyaluronic acid gel is not particularly limited, but as described as the content of the other components, for example, about 5 to 70% by mass and 5 to 60% by mass. %, 5 to 50% by mass, 5 to 40% by mass, 5 to 30% by mass, 5 to 20% by mass, 5 to 10% by mass, and the like.
  • the sugar content means the total amount of all the sugars.
  • the water-soluble hyaluronic acid gel of the present invention may further contain a liquid polyhydric alcohol that is liquid at 25 ° C. under 1 atm.
  • the liquid polyhydric alcohol is not particularly limited, but is preferably glycerin such as glycerin and diglycerin; propylene glycol such as propylene glycol and dipropylene glycol; 1,3-propanediol and butanediol (1).
  • ethylene such as ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, etc.
  • examples thereof include glycols, and more preferably glycerin, diglycerin, propylene glycol, 1,3-butanediol, polyethylene glycol 200, polyethylene glycol 400, polyethylene glycol 600, 1,3-propanediol, and 1,2-pentanediol. , 1,2-Hexanediol and the like.
  • glycerin, diglycerin, butanediol and the like are particularly preferable.
  • One type of polyhydric alcohol may be used alone, or two or more types may be used in combination.
  • the content of the liquid polyhydric alcohol in the water-soluble hyaluronic acid gel of the present invention is not particularly limited, but as described as the content of the other components, for example, about 5 to 50% by mass, 5 to 40. About mass%, about 5 to 30% by mass, about 5 to 20% by mass, about 5 to 10% by mass, and the like.
  • the content of the liquid polyhydric alcohols means the total amount of all the liquid polyhydric alcohols.
  • the water-soluble hyaluronic acid gel of the present invention is suitably gelled even if it does not contain a liquid polyhydric alcohol. That is, the water-soluble hyaluronic acid gel of the present invention does not have to contain substantially a liquid polyhydric alcohol.
  • the content of the liquid polyhydric alcohol in the water-soluble hyaluronic acid gel of the present invention may be 1% by mass or less, further 0.1% by mass or less, or 0% by mass.
  • the water-soluble hyaluronic acid gel of the present invention may contain a water-soluble organic solvent (excluding the above-mentioned liquid polyhydric alcohol).
  • a water-soluble organic solvent excluding the above-mentioned liquid polyhydric alcohol.
  • the content thereof is 10% by mass or less, preferably 5% by mass or less, more preferably 2% by mass or less, 1% by mass or less, and 0% by mass. %.
  • the water-soluble organic solvent is not particularly limited, and examples thereof include ethanol, methanol, isopropanol, and acetone.
  • the water-soluble organic solvent may be used alone or in combination of two or more.
  • the water-soluble hyaluronic acid gel of the present invention is suitably used in the fields of beauty, medicine, and food as described later. From this point of view, it is preferable that the water-soluble hyaluronic acid gel of the present invention contains substantially no water-soluble organic solvent. Further, when a water-soluble organic solvent is used, the viscosity of the hyaluronic acid aqueous solution tends to increase, so that it may be difficult to spread the hyaluronic acid aqueous solution thinly on a substrate or the like. Therefore, when a water-soluble organic solvent is used, it may be difficult to form the water-soluble hyaluronic acid gel in the form of a sheet by a simple method such as a casting method. From this point of view, it is preferable that the water-soluble hyaluronic acid gel of the present invention substantially does not contain a water-soluble organic solvent.
  • the elasticity, mechanical strength, shape retention, etc. of the water-soluble hyaluronic acid gel of the present invention are determined by the content of each component in the water-soluble hyaluronic acid gel, the molecular weight of hyaluronic acid, or the pH of the aqueous solution in the above-mentioned pH measuring method. It can be adjusted by setting the range of. For example, when the content of hyaluronic acid in the water-soluble hyaluronic acid gel is increased (the ratio is increased), the water-soluble hyaluronic acid gel becomes hard, and the elasticity, mechanical strength, and shape retention of the water-soluble hyaluronic acid gel are improved. It tends to be higher.
  • the water-soluble hyaluronic acid gel tends to become hard, and the elasticity, mechanical strength, and shape retention of the water-soluble hyaluronic acid gel tend to increase.
  • the water-soluble hyaluronic acid gel of the present invention is water-soluble.
  • the water solubility of the water-soluble hyaluronic acid gel of the present invention means that a sheet-shaped water-soluble hyaluronic acid gel having a thickness of 100 ⁇ m, a length of 4 cm, and a width of 4 cm is placed in 100 mL of a phosphate buffer solution having a pH of 7.4 at 37 ° C. When agitated at 120 rpm using a stirrer, it means that it completely dissolves within 4 hours.
  • the shape of the water-soluble hyaluronic acid gel of the present invention is not particularly limited and can be appropriately set according to the intended use.
  • Examples of the shape of the water-soluble hyaluronic acid gel of the present invention include a sheet shape, a granular shape, and a lump shape.
  • the water-soluble hyaluronic acid gel when the water-soluble hyaluronic acid gel is in the form of a sheet (water-soluble hyaluronic acid gel sheet), as described later, for example, the water-soluble hyaluronic acid gel of the present invention may be attached to the skin, oral cavity, etc. It can be suitably used as a composition, a composition for medical devices, and the like. Further, the sheet-shaped water-soluble hyaluronic acid gel may be used as a food composition such as an oral hygiene improving film or an oral pharmaceutical composition such as an oral sustained release film.
  • the thickness of the water-soluble hyaluronic acid gel sheet is not particularly limited, and examples thereof include about 0.01 to 10 mm, preferably about 0.05 to 5 mm.
  • the water-soluble hyaluronic acid gel when it is in the form of a lump, it can be suitably used as a food composition such as a dietary supplement in a stick shape or a cup container, or as a cosmetic for massaging the face or body. it can. It can also be suitably used as a food composition such as a jelly beverage or an oral pharmaceutical composition such as a swallowing aid beverage.
  • a food composition such as a jelly beverage or an oral pharmaceutical composition such as a swallowing aid beverage.
  • the water-soluble hyaluronic acid gel when it is granular, it can be suitably used as a food composition such as a gummy-type dietary supplement or an oral pharmaceutical composition.
  • the water-soluble hyaluronic acid gel of the present invention contains hyaluronic acid having a moisturizing effect and the like, it can be applied to the skin and the like in the beauty field, the medical field and the like. Further, since it can be composed only of ingredients that can be used for food or medicine such as hyaluronic acid and sugar, it can be suitably applied to the oral cavity and the like. That is, the water-soluble hyaluronic acid gel of the present invention can be suitably used as a cosmetic, a food composition, a pharmaceutical composition, a composition for a medical device, or the like.
  • the water-soluble hyaluronic acid gel of the present invention is used as a cosmetic, pharmaceutical composition, or medical device composition
  • known components additives to be blended in cosmetics, quasi-drugs, pharmaceuticals, and medical devices.
  • Such components include whitening components, anti-aging components, oil components, various vitamins and their derivatives, various animal and plant extracts, anti-inflammatory agents, antioxidants, pigments, fragrances (aroma components), preservatives and the like. Be done.
  • a fat-soluble component additive
  • the fat-soluble component can be added in the state of liposome, emulsion, nanoemulsion or the like. These components may be used alone or in combination of two or more.
  • whitening ingredients include vitamin C or its derivatives, astaxanthin, and the like.
  • Specific examples of the anti-aging component include Narsgen (registered trademark, methyl carboxymethylphenylaminocarboxypropylphosphonate), pyrroloquinoline quinone, LR2412 (registered trademark, sodium tetrahydrojasmonate), and green peel (registered trademark, vegetable essential oil). ) And so on.
  • Specific examples of the oil component include squalane, jojoba oil, olive oil and the like.
  • the water-soluble hyaluronic acid gel of the present invention includes collagen, polyphyllin, proteoglycan, acetylglucosamine, hydroxypropyl cellulose, polyvinylpyrrolidone, polyvinyl alcohol, Lipidure (registered trademark, homopolymer or copolymer of 2-methacryloyloxyethyl phosphorylcholine).
  • a water-soluble polymer (additive) such as hyaluronic acid having a molecular weight of 10,000 or less or a salt thereof may be blended.
  • One type of water-soluble polymer may be used alone, or two or more types may be used in combination.
  • the water-soluble hyaluronic acid gel of the present invention can be used as it is as a packing agent for cosmetics. Can also be used as.
  • the water-soluble hyaluronic acid gel of the present invention is preferably in the form of a sheet.
  • the water-soluble hyaluronic acid gel sheet of the present invention is directly attached to the skin and held for a certain period of time to impart a moisturizing effect of hyaluronic acid to the skin.
  • the water-soluble hyaluronic acid gel of the present invention contains a known component (additive) to be blended in cosmetics, quasi-drugs, pharmaceuticals, and medical devices as described above, the water-soluble hyaluronic acid gel sheet of the present invention These components can be absorbed transdermally by directly attaching the substance to the skin.
  • the water-soluble hyaluronic acid gel of the present invention has water solubility, hyaluronic acid easily dissolves in water. Therefore, the water-soluble hyaluronic acid gel of the present invention has a high effect of moisturizing and firming the skin by hyaluronic acid when applied to the skin and the like, and is suitable for use in the beauty field and the like.
  • the moisturizing effect of the hyaluronic acid dissolved in water is further enhanced by massaging the skin while sprinkling water on the sheet and gradually dissolving the sheet. be able to.
  • the water-soluble hyaluronic acid gel of the present invention is excellent in safety and biocompatibility, and has high water absorption / water retention, so that it is suitable for use in medical devices that protect wound sites and pressure ulcer sites.
  • the water-soluble hyaluronic acid gel of the present invention is excellent in safety and biocompatibility, and has high water absorption / water retention. Therefore, it can be suitably used as a pad for an emergency adhesive plaster or a covering protective material for a pressure ulcer site. it can.
  • a healing promoting component such as epidermal growth factor or an antibacterial component (additive) can be blended in the water-soluble hyaluronic acid gel.
  • the water-soluble hyaluronic acid gel of the present invention may be used by being placed on a support.
  • a water-soluble hyaluronic acid gel sheet can be preferably obtained.
  • the support is not particularly limited, and examples thereof include non-woven fabric, woven fabric, woven fabric, paper, polymer film (polyethylene terephthalate, polyolefin such as polyethylene, vinyl chloride, film such as polyurethane), and more preferably.
  • a laminated film made of a non-woven fabric / polymer film, a non-woven fabric, and the like can be mentioned.
  • the water-soluble hyaluronic acid gel on the support may be fixed with an adhesive tape, a hydrogel tape, a supporter, a bandage, a mask, an eye mask or the like for the purpose of holding the water-soluble hyaluronic acid gel on the skin.
  • the water-soluble hyaluronic acid gel of the present invention can be used alone as a product as it is.
  • a product in which the gel is integrated with an adhesive tape or a support can be used as a product, or a water-soluble hyaluronic acid gel is used as a product, and an adhesive tape, hydrogel tape, supporter, bandage, mask, eye mask, etc.
  • the gel may be fixed and used.
  • the water-soluble hyaluronic acid gel of the present invention can be composed only of ingredients that can be used for food or medicine such as hyaluronic acid and sugar, a food composition containing the water-soluble hyaluronic acid gel, It can also be suitably used as an oral pharmaceutical composition or the like.
  • water-soluble hyaluronic acid gel of the present invention When used as a food composition, known components (additives) to be blended in the food composition can be further blended.
  • Such ingredients include, for example, sweeteners, high-sugar sweeteners (aspartame, sucralose, glycyrrhizin, saccharin, stevia, dulcin, trichlorosucrose, thaumatin, acesulfame potassium, etc.), fragrances, coloring agents, acidulants, etc. , Antioxidants, emulsifiers, preservatives, stabilizers and the like.
  • a known active ingredient (additive) to be blended in the dietary supplement composition can be further blended.
  • active ingredients include vitamins, minerals, amino acids, peptides, proteins, glucosamine, chondroitin, collagen, methylsulfonylmethane, carnitine, curcumin, ⁇ -lipoic acid, astaxanthin, lutein, docosahexaenoic acid, and eicosapentaenoic acid.
  • active ingredients include vitamins, minerals, amino acids, peptides, proteins, glucosamine, chondroitin, collagen, methylsulfonylmethane, carnitine, curcumin, ⁇ -lipoic acid, astaxanthin, lutein, docosahexaenoic acid, and eicosapentaenoic acid.
  • examples thereof include acid, coenzyme Q10, soybean isoflavone, animal and plant extracts, lactoferrin, bifidus
  • water-soluble hyaluronic acid gel of the present invention when used as an oral pharmaceutical composition, known components (additives) to be blended in the oral pharmaceutical composition can be further blended.
  • additives include medicinal ingredients, fragrances, colorants, acidulants, antioxidants, emulsifiers, preservatives, stabilizers and the like.
  • these components may be used alone or in combination of two or more.
  • the dietary supplement composition or oral pharmaceutical composition using the water-soluble hyaluronic acid gel of the present invention contains hyaluronic acid, by ingesting the dietary supplement composition or oral pharmaceutical composition orally, For example, it can be expected to have an effect of increasing the water content of the skin and enhancing the moisturizing effect of the skin. Furthermore, since the nutritional supplement composition and the oral pharmaceutical composition contain water-soluble dietary fiber, the effect of delaying the absorption speed of sugar (the effect of suppressing the increase in postprandial blood glucose), the intestinal regulation effect, and the absorption speed of fat It can be expected to have effects such as delaying action (suppressing the rise of triglyceride after meals), reducing visceral fat, and promoting absorption of minerals. Further, when the above-mentioned known components (additives) are contained, the effects of these components can also be exhibited.
  • the shapes thereof are not particularly limited, but for example, a sheet such as an oral hygiene improving film, a granule such as a gummy type, or a stick. It can be in the form of a dietary supplement composition in a cup container or in the form of a lump such as a swallowing supplement / jelly drink.
  • gummy candies have been attracting attention as a dosage form that allows delicious and easy ingestion of health foods and dietary supplements, and gummy-type granules have a suitable shape. That is, the water-soluble hyaluronic acid gel of the present invention is preferably a granular gummy composition.
  • the water-soluble hyaluronic acid gel of the present invention can also be suitably used as a hydrogel for crystallizing a protein used for X-ray crystallography in a solid phase.
  • the method for producing the water-soluble hyaluronic acid gel of the present invention is not particularly limited, but for example, hyaluronic acid, 1 to 300 parts by mass of water-soluble dietary fiber with respect to 1 part by mass of hyaluronic acid, and an acid different from hyaluronic acid.
  • the heating temperature in step 1 is preferably 50 ° C. or higher, more preferably 60 ° C. or higher, still more preferably 70 ° C. or higher, as an upper limit, from the viewpoint of uniformly dissolving and dispersing each component contained in the hyaluronic acid aqueous solution. Is 100 ° C. or lower.
  • the cooling temperature in step 2 is not particularly limited as long as it is a temperature at which the hyaluronic acid aqueous solution gels to form a water-soluble hyaluronic acid gel, and is less than 40 ° C., 35 ° C. or lower, 30 ° C. or lower, 25 ° C. The following can be mentioned, and the lower limit is, for example, 0 ° C.
  • the water-soluble hyaluronic acid gel of the present invention In the method for producing a water-soluble hyaluronic acid gel of the present invention, it is not necessary to carry out a step of evaporating a large amount of water. That is, when the heated hyaluronic acid aqueous solution is cooled to a gelling temperature, the water-soluble hyaluronic acid gel of the present invention having substantially the same composition as the hyaluronic acid aqueous solution can be obtained.
  • the reduction rate of water from the water-soluble hyaluronic acid aqueous solution between steps 1 and 2 is preferably 50% by mass or less, more preferably 30% by mass or less, still more preferably 20% by mass or less, and particularly preferably 10% by mass.
  • the content of water contained in the water-soluble hyaluronic acid gel is preferably 50% by mass or more. It is more preferably 70% by mass or more, further preferably 80% by mass or more, and particularly preferably 90% by mass or more).
  • the mixing order of each component is not particularly limited, but a solution containing hyaluronic acid, water-soluble dietary fiber, and water is heated to obtain an acid different from hyaluronic acid. By adding, a homogeneous gel is easily formed from the hyaluronic acid aqueous solution.
  • the mixing method of each component is not particularly limited, and for example, stirring may be performed using a stirrer or the like.
  • the water-soluble dietary fiber or sugar in order to make the concentration of water-soluble dietary fiber or sugar equal to or higher than the saturated solubility, the water-soluble dietary fiber or sugar is dissolved in water so as to have a saturated solubility while heating. After that, a step of heating and concentrating this aqueous solution may be provided.
  • a water-soluble hyaluronic acid gel sheet can be easily produced by putting an aqueous hyaluronic acid solution in a container such as a tray or a bat so that the gel has a predetermined thickness and gelling the gel. it can. That is, by putting a heated hyaluronic acid aqueous solution in a container and cooling it, for example, the water-soluble hyaluronic acid gel sheet formed in the container can be used as a final product as it is, and the water-soluble hyaluronic acid gel sheet can be obtained. Processing steps such as cutting can be omitted.
  • a heated hyaluronic acid aqueous solution is placed in a container and cooled, so that, for example, the water-soluble hyaluronic acid gel formed in the container is put into a stick-shaped or cup container.
  • It can be used as a final product as it is as a food such as a nutritional supplement, a jelly drink, or a medicine such as a swallowing supplement.
  • a heated hyaluronic acid aqueous solution is filled in a mold formed on a starch or a mold such as silicone.
  • a granular water-soluble hyaluronic acid gel can be obtained.
  • a more elastic water-soluble hyaluronic acid gel having a gummy texture can be obtained.
  • a brightener, a mold release agent, or the like may be attached to the surface of Gumi.
  • a method for producing a granular hyaluronic acid gel such as a gummy type (that is, a method for producing a granular gummy composition)
  • an aqueous hyaluronic acid solution that can be kneaded while being heat-concentrated is prepared in the same manner as a general gummy production method. Then, by filling the hyaluronic acid aqueous solution into a mold formed in starch or a mold such as silicone, a granular water-soluble hyaluronic acid gel can be obtained.
  • a water-soluble hyaluronic acid gel (gummy composition) having a more elastic gummy texture can be obtained.
  • a brightener, a mold release agent, or the like may be attached to the surface of Gumi.
  • the above-mentioned various components to be blended in cosmetics, foods, quasi-drugs, pharmaceuticals, medical devices, etc.
  • the agent may be further provided.
  • the above-mentioned various components additives
  • the present invention will be described in detail below with reference to Examples and Comparative Examples. However, the present invention is not limited to the examples.
  • the reagents used in the following examples and comparative examples are as follows.
  • the unit of composition in each table is parts by mass.
  • Hyaluronic acid (2.3 million): Sodium hyaluronate, trade name "HYALURONSANHA-LQSH” manufactured by Kewpie Corp. (Product label: molecular weight 1.6 million to 2.9 million, average molecular weight 2.3 million) Hyaluronic acid (1.6 million): Sodium hyaluronate, trade name "HYALURONSANHA-LQH” manufactured by Kewpie Corp. (Product label: molecular weight 1.2 million to 2.2 million, average molecular weight 1.6 million) Hyaluronic acid (800,000): Sodium hyaluronate, trade name "Hiabest (J)” manufactured by Kewpie Corp.
  • Hyaluronic acid (350,000): Hyaluronic acid, trade name "Hyaluronic acid HA-LF-P" manufactured by Kewpie Corp.
  • Hyaluronic acid (100,000): Sodium hyaluronate, product name "Hyaluronic acid FCH-SU” manufactured by Kikkoman Biochemifa Co., Ltd.
  • Isomaltodextrin Product name manufactured by Hayashihara Co., Ltd.
  • Solid content approx. 75% by mass Fructooligosaccharide Product name "Meioligo P (powder)” manufactured by Meiji Food Material Co., Ltd. Lactose-fructose oligosaccharide; brand name "milk-fructose oligo 700" manufactured by Hayashibara Co., Ltd. Solid content approx. 75% by mass Dextrin: Product name "Paindex # 2" manufactured by Matsutani Chemical Industry Co., Ltd.
  • Xylitol Xylitol (special grade) manufactured by Wako Pure Chemical Industries, Ltd. Sorbitol; Sorbitol (special grade) manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.
  • Honey Approximately 80% by mass of refined honey solids manufactured by Api Co., Ltd.
  • Glucose D (+)-glucose (special grade) manufactured by Wako Pure Chemical Industries, Ltd.
  • Maltose D (+)-maltose monohydrate (special grade) manufactured by Wako Pure Chemical Industries, Ltd.
  • Sucrose Sucrose (special grade) manufactured by Wako Pure Chemical Industries, Ltd.
  • Fructose D (-)-fructose (special grade) manufactured by Wako Pure Chemical Industries, Ltd. Reduced Isomalz North; Brand name "Palatinit” manufactured by Mitsui Sugar Co., Ltd.
  • Glycerin Glycerin manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.
  • Citric acid Citric acid (special grade) manufactured by Wako Pure Chemical Industries, Ltd.
  • Acetic acid Acetic acid manufactured by Wako Pure Chemical Industries, Ltd.
  • Lactic acid DL-lactic acid (special grade) manufactured by Wako Pure Chemical Industries, Ltd.
  • Tartaric acid D (-)-tartaric acid (first grade) manufactured by Wako Pure Chemical Industries, Ltd.
  • Ascorbic acid (vitamin C) L (+)-ascorbic acid (special grade) manufactured by Wako Pure Chemical Industries, Ltd. Ascorbic acid glucoside; trade name "Asco Fresh” manufactured by Hayashibara Co., Ltd.
  • Aspartic acid DL-aspartic acid (special grade) manufactured by Wako Pure Chemical Industries, Ltd.
  • Phosphoric acid Phosphoric acid (special grade) manufactured by Wako Pure Chemical Industries, Ltd.
  • Sulfuric acid Sulfuric acid manufactured by Wako Pure Chemical Industries, Ltd. (special grade)
  • Examples 1 to 4 and Comparative Examples 1 to 9 In a room temperature environment (25 ° C.), hyaluronic acid (sodium hyaluronate) is uniformly dissolved in distilled water so as to have the compounding ratio (parts by mass) shown in Table 1, and then components other than citric acid (water-soluble) are further dissolved. (Distilled fiber or sugar) was added and heated at 50 ° C. for 24 hours to prepare an aqueous hyaluronic acid solution.
  • heterogeneous gel means a gel in which a hard part and a soft part are mixed.
  • citric acid was rapidly gelled by adding citric acid to a water-soluble hyaluronic acid aqueous solution at room temperature, so that citric acid was present in the properties before heating (25 ° C.). It was not uniformly dispersed and such an inhomogeneous gel was formed.
  • the “homogeneous gel” means a gel in which the hardness of the entire gel is homogeneous.
  • the water-soluble hyaluronic acid gels of Examples 1 to 4 are water-soluble hyaluronic acid gels containing hyaluronic acid, water-soluble dietary fiber, an acid different from hyaluronic acid, and water, and are water-soluble.
  • Dietary fiber is a polysaccharide having glucose as a constituent sugar, having bonds other than 1-4 bonds and 1-6 bonds, and not having a cyclic structure, and has a water content of 1 to 1 to 1 parts by mass of hyaluronic acid. It is 300 parts by mass, and the content of water-soluble dietary fiber is 1 to 300 parts by mass with respect to 1 part by mass of hyaluronic acid.
  • the water-soluble hyaluronic acid gels of Examples 1 to 4 can be produced with high productivity without the need to provide a step of evaporating a large amount of water from the hyaluronic acid aqueous solution in the production of the water-soluble hyaluronic acid gel. Further, the water-soluble hyaluronic acid gels of Examples 1 to 4 have a property of liquefying when heated and gelling when cooled, and the composition of the water-soluble hyaluronic acid gel is fluid in a heating environment.
  • a uniform hyaluronic acid aqueous solution can be prepared, the aqueous solution can be filled in a container as it is, and it has a property of forming a water-soluble hyaluronic acid gel when cooled to about room temperature. Since the water-soluble hyaluronic acid gel has such properties, it can be produced with high productivity, and even if the water-soluble hyaluronic acid gel is placed in a high temperature environment in the distribution process and liquefied, it is at room temperature. Because it gels again in, it has excellent stability as a product.
  • the water-soluble hyaluronic acid gels of Comparative Examples 1 to 9 do not contain the predetermined amount of the predetermined water-soluble dietary fiber.
  • the water-soluble hyaluronic acid gels of Comparative Examples 1 to 9 can prepare an aqueous hyaluronic acid solution in a heating environment in the composition of the water-soluble hyaluronic acid gel, but do not have the property of gelling even when cooled. It was not manufactured with high productivity.
  • Hyaluronic acid sodium hyaluronate
  • distilled water distilled water in a sealable glass bottle so that the composition of the water-soluble hyaluronic acid gel has the compounding ratio (parts by mass) shown in Table 2, and then isomaltodextrin is added. It was added and heated at 50 ° C. for 24 hours to prepare an aqueous hyaluronic acid solution.
  • This aqueous hyaluronic acid solution is heated to 80 ° C., citric acid is added and dissolved while stirring using a propeller-type rotary stirrer, and then the hyaluronic acid aqueous solution is heated at 80 ° C.
  • Hyaluronic acid sodium hyaluronate
  • distilled water distilled water in a sealable glass bottle so that the composition of the water-soluble hyaluronic acid gel has the compounding ratio (parts by mass) shown in Table 3, and then isomaltodextrin is added. It was added and heated at 50 ° C. for 24 hours to prepare an aqueous hyaluronic acid solution.
  • This aqueous hyaluronic acid solution is heated to 80 ° C., citric acid is added and dissolved while stirring using a propeller-type rotary stirrer, and then the hyaluronic acid aqueous solution is heated at 80 ° C.
  • Hyaluronic acid sodium hyaluronate
  • distilled water distilled water in a sealable glass bottle so that the composition of the water-soluble hyaluronic acid gel has the compounding ratio (parts by mass) shown in Table 4, and then sugar (isomalto) is used.
  • Dextrin was added and heated at 50 ° C. for 24 hours to prepare an aqueous hyaluronic acid solution.
  • This aqueous hyaluronic acid solution is heated to 80 ° C.
  • citric acid is added and dissolved while stirring using a propeller-type rotary stirrer, and then the hyaluronic acid aqueous solution is heated at 80 ° C.
  • Hyaluronic acid sodium hyaluronate
  • distilled water distilled water in a sealable glass bottle so that the composition of the water-soluble hyaluronic acid gel has the compounding ratio (parts by mass) shown in Table 5, and then sugar (isomalto).
  • Dextrin sugar was added and heated at 50 ° C. for 24 hours to prepare an aqueous hyaluronic acid solution.
  • This hyaluronic acid aqueous solution is heated to 80 ° C., and acid is added and dissolved while stirring using a propeller type rotary stirrer, and then the hyaluronic acid aqueous solution is heated at 80 ° C.
  • Hyaluronic acid sodium hyaluronate
  • distilled water distilled water
  • a sealable glass bottle so that the composition of the water-soluble hyaluronic acid gel had the compounding ratio (parts by mass) shown in Table 6, and then isomaltodextrin
  • An aqueous hyaluronic acid solution was prepared by adding honey, xylitol, or isomalto-oligosaccharide and heating at 50 ° C. for 24 hours.
  • This aqueous hyaluronic acid solution is heated to 80 ° C., citric acid is added and dissolved while stirring using a propeller-type rotary stirrer, and then the hyaluronic acid aqueous solution is heated at 80 ° C. for 12 hours in a sealed state to make it uniform. A liquid material was obtained. Gels having the properties (25 ° C.) after cooling shown in Table 6 (that is, homogeneous gels) were obtained.
  • Example 59 to 62 Approximately 5 g of the gel-like products obtained in Examples 53, 54, 57, and 58 were placed in a petri dish, air-dried at room temperature, and adjusted to have the water content shown in Table 7. I got something.
  • Example 53 corresponds to Example 59
  • Example 54 corresponds to Example 60
  • Example 57 corresponds to Example 61
  • Example 58 corresponds to Example 62. All of these gel-like substances showed high elasticity, and the texture was equivalent to that of hard gummies.
  • Hyaluronic acid sodium hyaluronate
  • distilled water distilled water
  • a sealable glass bottle so that the composition of the water-soluble hyaluronic acid gel has the blending ratio (parts by mass) shown in Table 8, and then shown in Table 8.
  • Various sugars isomaltodextrin, etc. were added and heated at 90 ° C. for 2 hours to prepare an aqueous hyaluronic acid solution.
  • Example 67 to 70 Approximately 5 g of the gel-like products obtained in Examples 63, 64, 65, and 66 were placed in a petri dish, air-dried at room temperature, and adjusted to have the water content shown in Table 9. I got something.
  • Example 63 corresponds to Example 67
  • Example 64 corresponds to Example 68
  • Example 65 corresponds to Example 69
  • Example 66 corresponds to Example 70. All of these gel-like substances showed high elasticity, and the texture was equivalent to that of hard gummies.
  • Hyaluronic acid sodium hyaluronate
  • distilled water distilled water
  • a sealable glass bottle so that the composition of the water-soluble hyaluronic acid gel has the blending ratio (parts by mass) shown in Table 10, and then shown in Table 10.
  • Various sugars are added and heated at 90 ° C. for 2 hours to prepare an aqueous hyaluronic acid solution.
  • Example 78 to 84 Approximately 5 g of the gel-like products obtained in Examples 71, 72, 73, 74, 75, 76, and 77 are placed in a petri dish and air-dried at room temperature to obtain the water content shown in Table 11. A gel-like product prepared as described above was obtained.
  • Example 71 corresponds to Example 78
  • Example 72 corresponds to Example 79
  • Example 73 corresponds to Example 80
  • Example 74 corresponds to Example 81
  • Example 75 corresponds to Example 75.
  • Example 76 corresponds to Example 83
  • Example 77 corresponds to Example 84. All of these gel-like substances showed high elasticity, and the texture was equivalent to that of hard gummies.
  • Hyaluronic acid sodium hyaluronate
  • distilled water distilled water
  • a sealable glass bottle so that the composition of the water-soluble hyaluronic acid gel has the blending ratio (parts by mass) shown in Table 12, and then shown in Table 12.
  • Various sugars such as reducing indigestible dextrin
  • Example 88 to 90 About 5 g of the gel-like products obtained in Examples 85, 86, and 87 were placed in a petri dish and air-dried at room temperature to prepare a gel-like product adjusted to have the water content shown in Table 13. Obtained.
  • Example 85 corresponds to Example 88
  • Example 86 corresponds to Example 89
  • Example 87 corresponds to Example 90. All of these gel-like substances showed high elasticity, and the texture was equivalent to that of hard gummies.
  • Hyaluronic acid sodium hyaluronate
  • distilled water distilled water
  • a sealable glass bottle so that the composition of the water-soluble hyaluronic acid gel has the blending ratio (parts by mass) shown in Table 14, and then shown in Table 14.
  • Various sugars are added and heated at 90 ° C. for 2 hours to prepare an aqueous hyaluronic acid solution.
  • Example 94 to 96 Approximately 5 g of the gel-like products obtained in Examples 91, 92, and 93 were placed in a petri dish and air-dried at room temperature to prepare a gel-like product adjusted to have the water content shown in Table 15. Obtained.
  • Example 91 corresponds to Example 94
  • Example 92 corresponds to Example 95
  • Example 93 corresponds to Example 96. All of these gel-like substances showed high elasticity, and the texture was equivalent to that of hard gummies.
  • Hyaluronic acid sodium hyaluronate
  • distilled water distilled water
  • a sealable glass bottle so that the composition of the water-soluble hyaluronic acid gel has the blending ratio (parts by mass) shown in Table 16, and then shown in Table 16.
  • Various sugars are added and heated at 90 ° C. for 2 hours to prepare an aqueous hyaluronic acid solution.
  • Example 100 to 102 Approximately 5 g of the gel-like products obtained in Examples 97, 98, and 99 were placed in a petri dish and air-dried at room temperature to prepare a gel-like product adjusted to have the water content shown in Table 17. Obtained.
  • Example 97 corresponds to Example 100
  • Example 98 corresponds to Example 101
  • Example 99 corresponds to Example 102. All of these gel-like substances showed high elasticity, and the texture was equivalent to that of hard gummies.
  • Hyaluronic acid sodium hyaluronate
  • distilled water distilled water
  • a sealable glass bottle so that the composition of the water-soluble hyaluronic acid gel has the blending ratio (parts by mass) shown in Table 18, and then shown in Table 18.
  • Various sugars are added and heated at 90 ° C. for 2 hours to prepare an aqueous hyaluronic acid solution.
  • Example 110 to 116 About 5 g of the gel-like products obtained in Examples 103, 104, 105, 106, 107, 108, and 109 are placed in a petri dish and air-dried at room temperature to obtain the water content shown in Table 19. A gel-like product prepared as described above was obtained.
  • Example 103 corresponds to Example 110
  • Example 104 corresponds to Example 111
  • Example 105 corresponds to Example 112
  • Example 106 corresponds to Example 113
  • Example 107 corresponds to Example.
  • Example 109 corresponds to Example 116. All of these gel-like substances showed high elasticity, and the texture was equivalent to that of hard gummies.
  • Hyaluronic acid sodium hyaluronate
  • a wide-mouthed bottle in twice the mass of distilled water having the compounding ratio (parts by mass) shown in Table 20, and then propeller-type rotation while heating at 90 ° C.
  • various sugars isomaltodextrin, etc.
  • citric acid is further added to uniformly dissolve the sugar, and then the water is evaporated.
  • a uniform high-viscosity gummy composition having a composition of the water-soluble hyaluronic acid gel having the compounding ratio (part by mass) shown in Table 20 was obtained.
  • Example 120 to 122 About 5 g of the gel-like product contained in the petri dish obtained in Examples 117, 118, and 119 was naturally dried at room temperature to obtain a gel-like product adjusted to have the water content shown in Table 21. ..
  • Example 117 corresponds to Example 120
  • Example 118 corresponds to Example 121
  • Example 119 corresponds to Example 122. All of these gel-like substances showed high elasticity, and the texture was equivalent to that of hard gummies.
  • Hyaluronic acid sodium hyaluronate
  • distilled water distilled water
  • a sealable glass bottle so that the composition of the water-soluble hyaluronic acid gel has the blending ratio (parts by mass) shown in Table 22, and then shown in Table 22.
  • Various sugars are added and heated at 90 ° C. for 2 hours to prepare an aqueous hyaluronic acid solution.
  • hyaluronic acid and acid are added to 200 mL of distilled water using a propeller formula so that the blending ratio (parts by mass) shown in Tables 1 to 22 is obtained with respect to 1 g of hyaluronic acid (sodium hyaluronate) and 1 g of acid.
  • the mixture was uniformly mixed using a rotary stirrer to obtain an aqueous hyaluronic acid solution for pH measurement.
  • the pH of the obtained aqueous hyaluronic acid solution was measured using a FiveEasy (registered trademark) pH meter manufactured by METTLER TOLEDO.

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Abstract

L'invention concerne un procédé de production de gel soluble dans l'eau d'acide hyaluronique qui peut être produit à une productivité élevée et sans avoir besoin d'une étape d'évaporation d'une grande quantité d'eau à partir d'une solution d'acide hyaluronique.　Ce gel soluble dans l'eau d'acide hyaluronique contient de l'acide hyaluronique, des fibres alimentaires solubles dans l'eau, un acide autre que l'acide hyaluronique et de l'eau : les fibres alimentaires solubles dans l'eau étant des polysaccharides qui présentent du glucose en tant que sucre constitutif, qui contiennent des liaisons autres que des liaisons 1-4 et des liaisons 1-6 et qui ne présentent pas de structure cyclique ; la teneur en eau étant de 1 à 300 parties en masse pour 1 partie en masse de l'acide hyaluronique ; et la teneur en fibres alimentaires solubles dans l'eau étant de 1 à 300 parties en masse pour 1 partie en masse de l'acide hyaluronique.
PCT/JP2020/024608 2019-06-26 2020-06-23 Gel soluble dans l'eau d'acide hyaluronique et procédé de production associé WO2020262381A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114644719A (zh) * 2022-03-24 2022-06-21 珠海中科先进技术研究院有限公司 一种海茸多糖提取液及其制备方法与应用
CN114796012A (zh) * 2022-04-08 2022-07-29 华熙生物科技股份有限公司 一种透明质酸皮脂膜组合物及其制备方法

Citations (7)

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Publication number Priority date Publication date Assignee Title
JPH10150934A (ja) * 1996-11-20 1998-06-09 Matsutani Chem Ind Ltd 還元難消化性水飴およびこれを用いた食品
JP2000060487A (ja) * 1998-08-27 2000-02-29 Kao Corp 便秘改善剤
JP2010088339A (ja) * 2008-10-08 2010-04-22 Q P Corp 酸性透明ゲル状食品
JP2011136218A (ja) * 2011-04-11 2011-07-14 Denki Kagaku Kogyo Kk ヒアルロン酸ゲルの製造方法及びそれを含有する医用材料
WO2016121245A1 (fr) * 2015-01-29 2016-08-04 株式会社リタファーマ Gel d'acide hyaluronique hydrosoluble et procédé de production associé
WO2016121611A1 (fr) * 2015-01-29 2016-08-04 株式会社リタファーマ Gel d'acide hyaluronique hydrosoluble et son procédé de production
WO2017085964A1 (fr) * 2015-11-17 2017-05-26 株式会社リタファーマ Gel d'acide hyaluronique hydrosoluble et son procédé de production

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10150934A (ja) * 1996-11-20 1998-06-09 Matsutani Chem Ind Ltd 還元難消化性水飴およびこれを用いた食品
JP2000060487A (ja) * 1998-08-27 2000-02-29 Kao Corp 便秘改善剤
JP2010088339A (ja) * 2008-10-08 2010-04-22 Q P Corp 酸性透明ゲル状食品
JP2011136218A (ja) * 2011-04-11 2011-07-14 Denki Kagaku Kogyo Kk ヒアルロン酸ゲルの製造方法及びそれを含有する医用材料
WO2016121245A1 (fr) * 2015-01-29 2016-08-04 株式会社リタファーマ Gel d'acide hyaluronique hydrosoluble et procédé de production associé
WO2016121611A1 (fr) * 2015-01-29 2016-08-04 株式会社リタファーマ Gel d'acide hyaluronique hydrosoluble et son procédé de production
WO2017085964A1 (fr) * 2015-11-17 2017-05-26 株式会社リタファーマ Gel d'acide hyaluronique hydrosoluble et son procédé de production

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114644719A (zh) * 2022-03-24 2022-06-21 珠海中科先进技术研究院有限公司 一种海茸多糖提取液及其制备方法与应用
CN114796012A (zh) * 2022-04-08 2022-07-29 华熙生物科技股份有限公司 一种透明质酸皮脂膜组合物及其制备方法
CN114796012B (zh) * 2022-04-08 2024-03-29 华熙生物科技股份有限公司 一种透明质酸皮脂膜组合物及其制备方法

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