WO2005035477A1 - キノン骨格を有する化合物の安定化方法及び安定化された組成物 - Google Patents
キノン骨格を有する化合物の安定化方法及び安定化された組成物 Download PDFInfo
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- WO2005035477A1 WO2005035477A1 PCT/JP2004/014824 JP2004014824W WO2005035477A1 WO 2005035477 A1 WO2005035477 A1 WO 2005035477A1 JP 2004014824 W JP2004014824 W JP 2004014824W WO 2005035477 A1 WO2005035477 A1 WO 2005035477A1
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- Prior art keywords
- compound
- antioxidant
- quinone skeleton
- oil
- coating medium
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
- C07C50/28—Quinones containing groups having oxygen atoms singly bound to carbon atoms with monocyclic quinoid structure
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
- A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
- A61K9/1623—Sugars or sugar alcohols, e.g. lactose; Derivatives thereof; Homeopathic globules
-
- 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
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
-
- 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
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1658—Proteins, e.g. albumin, gelatin
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5015—Organic compounds, e.g. fats, sugars
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5052—Proteins, e.g. albumin
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5052—Proteins, e.g. albumin
- A61K9/5057—Gelatin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
Definitions
- the present invention relates to a method for stabilizing a compound having a quinone skeleton and a stabilized composition.
- the present invention relates to a method for stabilizing a composition containing a compound having a quinone skeleton.
- Ubidecarenone is a compound that is useful as an excellent food, nutritious food, food for specified health use, nutritional supplement, nutritional supplement, animal drug, beverage, feed, cosmetic, pharmaceutical, therapeutic, prophylactic, etc.
- coenzyme Q ubiquinone
- ubiquinone a benzoquinone derivative widely distributed in the living world
- Coenzyme Q is an essential component widely distributed in living organisms from bacteria to mammals, and constitutes the mitochondrial electron transport system in cells in living organisms.
- Coenzyme Q is in mitochondria! It is known that, by repeating oxidation and reduction, it functions as a transfer component in the electron transfer system.
- the physiological effects of coenzyme Q include activation of energy production by mitochondrial activation, activation of cardiac function, stabilization of cell membranes, protection of cells by antioxidation, and the like.
- the main component is coenzyme Q, which has 10 isoprene units, and in vivo, usually about 40-90%
- coenzyme Q also called ubidecarenone
- ubidecarenone is used as a health food in Europe and the United States.
- vitamin Q is an ingredient that rejuvenates the body as a nutrient source that returns weakened cell activity to a healthy state.
- Vitamin K which is a general name of a derivative of 2-methyl-1,4 naphthoquinone having blood coagulation activity, is also known as an essential component in a living body.
- vitamin K1 phytoquinone
- vitamin K2 has 4 to 13 isoprene units at position 3.
- menaquinone-4 menatetrenone
- prothrombin which is a precursor of an enzyme (thrombin) that causes a blood coagulation reaction
- thrombin an enzyme that causes a blood coagulation reaction
- the antioxidant itself decomposes under the above-described conditions.
- dehydroascorbic acids generated by decomposition when vitamin Cs (ascorbic acids) are used and oxalic acid generated by further decomposition are different from ascorbic acids and are highly harmful.
- oxalic acid generated by further decomposition are different from ascorbic acids and are highly harmful.
- There are concerns about side effects such as (Non-Patent Document 1) and the like, which also causes problems in product quality.
- Non-patent Document 1 Nutriton Research, 13th volume, 667-676 pages, 1993
- the present invention provides a food containing a compound having a quinone skeleton, a nutritionally functional food, a food for specified health use, a nutritional supplement, a nutrient, an animal drug, a beverage, a feed, a cosmetic, a pharmaceutical, a therapeutic drug.
- Quinone skeleton capable of stably retaining a compound having a quinone skeleton even in a composition in which a compound having a quinone skeleton and an antioxidant coexist when preparing a drug or a prophylactic agent, or a material or composition thereof. It is an object of the present invention to provide a method for stabilizing a compound having the formula and a stabilized composition.
- the present invention provides a composition comprising a compound having a quinone skeleton and an antioxidant, wherein at least one of the compound having a quinone skeleton and the antioxidant is coated with a non-oil-soluble coating medium.
- Quinone wherein the quinone is present in an oily substance in a state where the compound has a quinone skeleton and at least one of an antioxidant and a water-insoluble coating medium. This is a method for stabilizing a compound having a skeleton.
- the present invention comprises a compound having a quinone skeleton and an antioxidant, and at least one of the compound having a quinone skeleton and the antioxidant is coated with a non-oil-soluble coating medium. Characterized in that it is made to coexist in an oily substance in a state, or is made to coexist in an aqueous substance in a state where at least one of a compound having a quinone skeleton and an antioxidant is coated with a water-insoluble coating medium. And a compound having a quinone skeleton.
- a composition comprising a compound having a quinone skeleton and an antioxidant is an oil-based composition in which at least one of the compound having a quinone skeleton and the antioxidant is coated with a non-oil-soluble coating medium. Coexist in a substance, or coexist in an aqueous substance with at least one of a compound having a quinone skeleton and an antioxidant coated with a water-insoluble coating medium.
- the compound having a quinone skeleton preferably both the compound having a quinone skeleton and the antioxidant, can be stably used. Can be held.
- At least one of a compound having a quinone skeleton and an antioxidant is coexisted in an oily substance in a state of being coated with a non-oil-soluble coating medium.
- composition of the present invention comprising a compound having a quinone skeleton and an antioxidant may be a combination of an antioxidant and a compound having a coated quinone skeleton, or a compound having a quinone skeleton. And a combination of a coated antioxidant. Needless to say, those coated with both a compound having a quinone skeleton and an antioxidant are preferred.
- both the compound having a quinone skeleton and the antioxidant are coated means that the compound having a quinone skeleton and the antioxidant are coated individually or together. Point. In particular, it is preferable that a compound having a quinone skeleton and an antioxidant are individually coated.
- the coating in the present invention means a compound having a quinone skeleton and crystals of Z or an antioxidant, and a part of the surface of Z or a melt (including an oily substance) is covered with a coating medium.
- a coating medium for the compound having a quinone skeleton or the antioxidant is coated, and in this case, it is preferably coated at least 50% of the surface area of the material to be coated, more preferably at least 60%. More preferably 70% or more is particularly preferred. 80% or more is particularly preferred. 90% or more is particularly preferred.
- both the compound having a quinone skeleton and the antioxidant are coated, it is preferably coated at least 50% of the total surface area of the compound having the quinone skeleton and the antioxidant, and preferably coated at least 60%. It is more preferable that the coating is 70% or more. Particularly preferable is that the coating is 80% or more. It is particularly preferable that the coating is 90% or more. Needless to say, a compound having a quinone skeleton and all of the surface area of Z or an antioxidant are coated, and the most preferable is.
- Examples of the compound having a quinone skeleton that can be used in the present invention include quinone skeletons such as benzoquinone, naphthoquinone, anthraquinone, and quinoline quinone used for foods and pharmaceuticals. Needless to say, any compound having o-quinone or p-quinone can be used. Preferred are ubiquinone, filoquinone, menaquinone, menadione, quinoline quinoline quinone, and more preferred are ubiquinone, filoquinone, menaquinone and the like, and particularly preferred are ubidecarenone, filoquinone and menatetrenone. Two or more of these compounds having a quinone skeleton can be used in combination.
- quinone skeletons such as benzoquinone, naphthoquinone, anthraquinone, and quinoline quinone used for foods and pharmaceuticals.
- the compound having a quinone skeleton used in the present invention can be obtained by a conventionally known method such as synthesis, fermentation, or extraction from a natural product, and is obtained by fermentation or extraction from a natural product. Things like,.
- the antioxidant is not particularly limited as long as it is acceptable for use in foods and pharmaceuticals.
- the coating medium used in the present invention is not particularly limited.
- the non-oil-soluble coating medium include gelatin, sugar, gum arabic, sugar esters of higher fatty acids, sugar esters of higher fatty acids, and tragacanth, which have high, medium or low gelling properties. , Pectin, pullulan, dried egg white, milk, shellac, curdlan, cellulose derivatives, casein, casein ligase, starch and the like.
- the water-insoluble coating medium include sugar esters of higher fatty acids, starch, shellac and the like.
- non-oil-soluble coating media described above, and particularly preferred are gelatin, sugar, gum arabic, pullulan, curdlan, cellulose derivatives and starch.
- the water-insoluble Z non-oil-soluble coating medium described in the present specification is usually about 50% by weight or less, preferably about 40% by weight, as a solubility in an aqueous substance Z oily substance described below at room temperature.
- the following refers to substances which are particularly preferably up to about 30% by weight, particularly preferably up to about 20% by weight, particularly preferably up to about 10% by weight.
- water-insoluble and oil-insoluble coating media such as sugar esters of higher fatty acids, starch and shellac, can also be used.
- examples of the sugar include glucose, fructose, ratatose, maltose, starch sugar, mannitol, sorbitol, galactose, sucrose, dextrin, maltodextrin and the like.
- glucose, sucrose, dextrin, and maltodextrin are used.
- starch examples include corn starch, potato starch, sweet potato starch, wheat starch and the like. Preferably, it is corn starch.
- cellulose derivative examples include methylcellulose, ethylcellulose, carboxymethyl senorellose, hydroxypropinoresenolellose, hydroxyethynolemethinoresenorelose, hydroxypropyl methylcellulose, and crystalline cellulose.
- it is methylcellulose.
- Examples of the higher fatty acid sugar ester include sucrose palmitate and the like.
- casein ligated product examples include sodium caseinate.
- polyvinyl alcohol polyvinylpyrrolidone, glycerin fatty acid ester
- Stem higher alcohol, hydrogenated oil, alginate, phospholipids such as lecithin, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polysorbate, a to emulsifier such as tocopheryl polyethylene glycol succinate, etc.
- phospholipids such as lecithin, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polysorbate, a to emulsifier such as tocopheryl polyethylene glycol succinate, etc.
- the ratio of the coating medium to the coated compound having a quinone skeleton and Z or the antioxidant is not particularly limited, but is usually about 0.1 lwZw% or more, preferably about lwZw% or more by weight. , More preferably about 5 wZw% or more, particularly preferably about 10 wZw% or more.
- the upper limit is usually about 90 wZw%, preferably about 80 wZw%, more preferably about 70 wZw%, particularly preferably about 60 wZw%, particularly preferably about 50 wZw%. Normally, it is preferable to set the most appropriate weight ratio in view of the cost and the like that can be suitably performed at about 0.1 to 90 wZw%.
- the compound or compound having a quinone skeleton and Z or an antioxidant may be added to the solution or suspension of the coating medium.
- the solution or suspension of the coating medium may be added to the solution or suspension of the compound having a quinone skeleton and Z or an antioxidant.
- a solution or suspension of the compound having a quinone skeleton and Z or an antioxidant may be mixed with the solution or suspension of the coating medium.
- antioxidants When two or more of the above-mentioned antioxidants are used in combination, they may be coated alone or as a mixture of two or more. When two or more compounds having a quinone skeleton described above are used in combination, they may be coated alone or as a mixture of two or more.
- the solvent for preparing the above solution or suspension varies depending on the solubility of the compound having a quinone skeleton to be coated and Z or the antioxidant, and cannot be uniformly defined.
- alcohols include ethanol, isopropanol, and the like.
- hydrocarbons include hexane, heptane, toluene and the like.
- esters include ethyl acetate, isopropyl acetate, ethyl ethyl formate and the like.
- the conditions such as temperature, stirring, mixing and the like when mixing the compound having a quinone skeleton and Z or the antioxidant with the above-mentioned coating medium are not particularly limited, but the mixture may be heated to obtain an appropriate dispersion. Alternatively, the stirring strength or the mixing strength may be increased.
- the method of drying the mixture of the compound having a quinone skeleton and Z or the antioxidant and the above-mentioned coating medium is not particularly limited, but may be a spray dryer, a drum dryer, a freeze dryer, a fluid dryer, or a fluidized bed built-in type. Drying can be performed by a generally known method using a spray drier, a vacuum drier or the like. Generally, drying is performed under normal pressure or reduced pressure until the solvent content is about 15 wZw% or less, preferably about 10 wZw% or less, more preferably about 6 wZw% or less. Alternatively, drying using microwaves is also possible.
- the drying temperature is not particularly limited, and drying can be performed at room temperature or lower, but is usually about 30 ° C or higher, preferably about 40 ° C or higher. Needless to say, a method of drying at a high temperature of about 100 ° C. or higher for a short time is also preferably used.
- the thus obtained compound having a coated quinone skeleton and Z or an antioxidant can also separate large particles and fine particles if necessary before, after or during drying.
- a known method such as a method of passing through a sieve or classification using an air flow can be used. Needless to say, a separate crushing operation can be incorporated.
- the particle size range is not particularly limited, but is preferably about 10 ⁇ m-lmm.
- Granulation can be performed by a generally known method using a fluidized granulator or the like. Any of a method of granulation after drying, a method of drying after granulation, and a method of simultaneously performing drying and granulation may be used. Therefore, a method of spraying and adding the above-mentioned coating medium solution to a compound having a quinone skeleton and Z or an antioxidant, followed by drying and granulation can also be adopted. By drying and granulating in this manner, a part or all of the compound having a quinone skeleton and Z or the antioxidant can be coated.
- a composition containing a desired compound having a quinone skeleton and an antioxidant can be obtained.
- the compound having a quinone skeleton and z or the antioxidant used herein may be a combination of an antioxidant and a compound having a coated quinone skeleton, or a compound having a quinone skeleton and a coated antioxidant. A combination may be used. Needless to say, a compound coated with both a compound having a quinone skeleton and an antioxidant is also preferable. Preferably, it is coated with a compound having a quinone skeleton.
- the compound having a quinone skeleton coated with a non-oil-soluble coating medium and Z or an antioxidant are allowed to coexist in an oily substance.
- Z or an antioxidant coexists in the aqueous substance.
- An embodiment in which the compound having a coated quinone skeleton and Z or an antioxidant coexist in an oily substance or an aqueous substance is, for example, a compound having a quinone skeleton coated in an oily substance or an aqueous substance. And z or an antioxidant are added and mixed.
- the oily substance described in the present specification is a solvent that usually forms two layers with water, that is, a solvent that forms two layers with water when no substance having an emulsifying action such as a surfactant is present. If there is, there is no particular limitation.
- the aqueous substance include, for example, oils and fats, hexane, and ethyl acetate, which will be described later.
- the aqueous substance is not particularly limited as long as it is a solvent that forms one layer with water, and includes, for example, water and ethanol. Needless to say, the embodiment includes only water that can be used, and also includes the embodiment in which water is mixed with an organic solvent such as ethanol to form a single layer.
- the above-mentioned solvent used in the solution or suspension for preparing the coated compound having a quinone skeleton and Z or the antioxidant may also be used as an oily substance or an aqueous substance, depending on its properties. A little monster.
- the proportion of the compound having a quinone skeleton contained in the composition is determined by the amount of the compound having a quinone skeleton that is sufficient to provide the expected effect of the compound having the quinone skeleton. Since it depends on the type, it cannot be uniformly defined, but in the total composition, for example, about 0.01 wt% or more, preferably about 0.1 wt% or more, more preferably about lwt% or more, and particularly preferably about 5 wt% or more. Among them, preferably about 1 ( ⁇ % or more.
- the upper limit is usually about 99 wt%, preferably about 95 wt%, more preferably about 90 wt%, particularly preferably about 85 wt%, particularly preferably about 80 wt%, particularly preferably about 80 wt%. Is about 70 wt%.
- the ratio of the antioxidant to the compound having a quinone skeleton is not particularly limited as long as the antioxidant has the expected effects and effects.
- the weight ratio is usually about 0.01 wZw. % Or more, preferably about 0.1 lwZw% or more, more preferably about lwZw% or more, particularly preferably about 5 wZw% or more, especially about 10 wZw% or more.
- the upper limit is about 100% or less, preferably about 500% or less, more preferably about 300% or less, and particularly preferably about 200% or less.
- the substance that can be contained in the composition of the present invention is not particularly limited.
- a compound having a quinone skeleton and an antioxidant for example, fats and oils, a surfactant, glycerin, polyethylene glycol, water , Ethanol and the like.
- the substance can be used as an oily substance or an aqueous substance depending on its properties.
- the fats and oils may be natural fats and oils from animals and plants, or synthetic fats or processed fats and oils. More preferably, it is acceptable for food or medicine.
- vegetable oils include, for example, coconut oil, palm oil, palm kernel oil, linseed oil, camellia oil, brown rice germ oil, rapeseed oil, rice oil, peanut oil, corn oil, wheat germ oil, soybean oil, perilla oil , Cottonseed oil, castor seed oil, kapok oil, evening primrose oil, shea butter, monkey fat, cocoa butter, sesame oil, safflower oil, olive oil, and the like.
- Animal oils and fats include, for example, pig fat, milk fat, Examples thereof include fish oil, beef tallow, and the like, and further include fats and oils (for example, hardened oils) obtained by fractionating, hydrogenating, transesterifying and the like. Needless to say, medium chain fatty acid triglycerides (MCT) can also be used. Moreover, you may use these
- medium-chain fatty acid triglyceride examples include, for example, triglycerides having 6 to 12, preferably 8 to 12, carbon atoms of fatty acids.
- fats and oils vegetable fats, synthetic fats and processed fats and oils are considered to be easy to handle and odor. preferable. These are preferably selected in consideration of the price of oils and fats, the stability and solubility of the compound having a quinone skeleton, and the like.
- coconut oil, palm oil, palm kernel oil, rapeseed oil, rice oil, soybean oil, cottonseed oil, safflower oil, olive oil, rice oil, soybean oil, rapeseed oil, safflower oil, MCT etc. are preferred. Particularly preferred.
- surfactant examples include partial glycerides of fatty acids, propylene glycol fatty acid esters, phospholipids, sucrose fatty acid esters, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, and the like.
- each of the fatty acids has 6 to 18 carbon atoms, preferably
- propylene glycol fatty acid ester for example, monoglyceride diglyceride having 6 to 18, preferably 6 to 12 carbon atoms of the fatty acid can be exemplified.
- Examples of the phospholipid include egg yolk lecithin, purified soy lecithin, phosphatidylcholine, phosphatidylethanolamine, phosphatidylserine, sphingomyelin, dicetyl phosphoric acid, stearylamine, phosphatidylglycerol, phosphatidic acid, and phosphatidyluinositolamine. , Cardiolipin, ceramide phosphorylethanolamine, ceramide phosphorylglycerol, and mixtures thereof.
- Such materials are not particularly limited, and include, for example, excipients, disintegrants, lubricants, binders, colorants, anti-agglomeration agents, absorption promoters, solubilizers, stabilizers, and the like. Can be. Needless to say, it does not prevent coexistence of a compound having a quinone skeleton and an active ingredient other than an antioxidant.
- the above additives may be coated individually or together with a compound having a quinone skeleton and Z or an antioxidant as necessary. Good.
- the above-mentioned excipient is not particularly limited, but examples thereof include sucrose, ratatose, and glucose. And starch, mannitol, crystalline cellulose, calcium phosphate, calcium sulfate, and the like described above.
- the disintegrant is not particularly restricted but includes, for example, starch, agar, calcium citrate, calcium carbonate, sodium hydrogencarbonate, dextrin, crystalline cellulose, carboxylmethylcellulose, tragacanth and the like.
- the lubricant is not particularly limited, but examples thereof include talc, magnesium stearate, and silica.
- the binder is not particularly restricted but includes, for example, ethyl cellulose, methylcellulose, hydroxypropylmethylcellulose, tragacanth, shellac, gelatin, gum arabic, polybutylpyrrolidone, polybutyl alcohol, polyacrylic acid, polymethacrylic acid, Sorbitol and the like can be mentioned.
- the colorant is not particularly limited, and examples thereof include those which are allowed to be added to pharmaceuticals and foods.
- the above-mentioned aggregation preventing agent is not particularly restricted but includes, for example, stearic acid, talc, light anhydrous silicic acid, hydrated diacid and dicarboxylic acid.
- the absorption promoter is not particularly limited, and examples thereof include higher alcohols and higher fatty acids.
- the solubilizer is not particularly limited, and examples thereof include organic acids such as fumaric acid, succinic acid, and malic acid.
- the above-mentioned stabilizer is not particularly limited, and examples thereof include benzoic acid, sodium benzoate, ethyl ethyl paraoxybenzoate, and honey moth.
- Examples of the active ingredient other than the compound having a quinone skeleton and the antioxidant include amino acids, vitamins, minerals, polyphenols, organic acids, saccharides, peptides, proteins, and the like.
- the ratio of the fat or oil to the whole composition is not particularly limited, but is usually, for example, about 10 wt% or more, preferably from the viewpoint of the viscosity and fluidity of the composition. Is about 20 wt% or more, more preferably about 30 wt% or more, and the upper limit is usually about 99 wt%, preferably about 95 wt%, more preferably about 90 wt%, particularly preferably about 80 wt%. More preferably, it is about 70% by weight.
- the ratio of the surfactant, glycerin, and Z or polyethylene glycol to the total composition is usually about lwt%.
- the content is preferably at least about 3 wt%, more preferably at least about 5 wt%, particularly preferably at least about 10 wt%.
- the ratio of the water and Z or ethanol to the whole composition is usually about lwt% or more, preferably about 5wt% or more. It is preferably at least about 10% by weight, particularly preferably at least about 20% by weight, particularly preferably at least about 30% by weight, and the upper limit is usually about 99.9% by weight, preferably about 99% by weight, more preferably about 95% by weight, Particularly preferably, it is about 90 wt%, particularly preferably about 80 wt%.
- composition capable of stably retaining a compound having a quinone skeleton can be obtained even when a compound having a quinone skeleton and an antioxidant coexist.
- composition containing the compound having a quinone skeleton and the antioxidant obtained as described above is used as a food, a nutritionally functional food, a food for specified health use, a nutritional supplement, a nutritional supplement, an animal drug, a beverage, It is preferably used as feed, cosmetics, pharmaceuticals, therapeutics, prophylactics and the like.
- composition containing the compound having the quinone skeleton and the antioxidant can be used as it is, but in particular, food, nutritionally functional food, food for specified health use, nutritional supplement, nutrient, animal drug
- the above compositions are used as capsules (node capsules, soft capsules, microcapsules, etc.), tablets (including chewable tablets), syrups, beverages, etc.
- Particularly preferred are capsules, especially soft capsules.
- the capsule base material is not particularly limited, and other base materials (for example, carrageenan, which can be used as a food additive, including gelatin derived from bovine bone, cow skin, pig skin, fish skin, and the like). , Thickening stabilizers such as seaweed-derived products such as alginic acid, and plant seed-derived products such as locust bean gum and guar gum; production agents containing celluloses, etc.) may also be used.
- base materials for example, carrageenan, which can be used as a food additive, including gelatin derived from bovine bone, cow skin, pig skin, fish skin, and the like.
- Thickening stabilizers such as seaweed-derived products such as alginic acid, and plant seed-derived products such as locust bean gum and guar gum; production agents containing celluloses, etc.
- composition containing the compound having a quinone skeleton and the antioxidant of the present invention and the above-mentioned capsules are appropriately added and used when cooking bread, pasta, porridge, cooked rice, cake, confectionery and the like, for example. You can also. Needless to say, it does not prevent the use of other forms of food.
- the compound having a quinone skeleton is replaced with a compound having a quinone skeleton ( (The ratio of the weight of the compound after storage to the weight of the compound before storage for a predetermined period) of about 92% by weight or more, preferably about 95% by weight or more, more preferably about 97% by weight or more, and particularly preferably Is expected to be maintained at about 98% by weight or more, especially about 99% by weight or more.
- the storage period is, for example, one day or more, preferably one week or more, more preferably one month or more, particularly preferably six months or more, particularly preferably one year or more, and particularly preferably two years or more.
- the compound having a quinone skeleton can be stably retained and easily produced.
- the method is widely applicable, such as being suitable for use as a composition for edible use or as an oral administration form, and therefore has a great advantage.
- the compound having a quinone skeleton can be stably retained.
- the present invention will be described in more detail with reference to Examples, but the present invention is not limited to only these Examples.
- the content of ubidecarenone and menatetrenone in the examples was determined by the following HPLC analysis. The obtained content of ubidecarenone does not define the limit value of purity in the present invention.
- ubidecarenone crystals 40 g were placed in an air-flow fluidized-granulation apparatus, and solutions of various coating media shown in Table 1 were sprayed to coat and granulate. Furthermore, drying under vacuum yielded coated ubidecarenone crystals. Particle size was 50 ⁇ m-600 ⁇ m. After that, with the help of a jewel, particles with a particle size of 255 ⁇ m-500 m were obtained. The content of the solvent contained in the granulated product was about 6-8%.
- Air inlet temperature 90 ° C
- Air outlet temperature Nariyuki (about 40-50 ° C)
- Airflow control dial 60-80
- Spray speed when spray is ON Approximately lmLZmin.
- menatetrenone crystals 40 g were placed in an air-flow granulator, and solutions of various coating media shown in Table 2 were sprayed to perform coating and granulation. Further drying under vacuum gave coated menatetrenone crystals. Particle size was 50 ⁇ m-600 ⁇ m. Note that the content of the solvent contained in the granulated product was about 6 to 8%.
- Air inlet temperature 90 ° C
- Air outlet temperature Nariyuki (about 40-50 ° C)
- Airflow control dial 60-80
- Spray speed when spray is ON Approximately lmLZmin.
- Air inlet temperature 90 ° C
- Air outlet temperature Nariyuki (about 40-50 ° C)
- Airflow control dial 60-80
- Spray speed when spray is ON Approximately lmLZmin.
- Example 29 Example 3
- Example 30 Example 1 9
- Example 31 Example 1 Uncoated Heart Tocopherol 1000.0
- Example 32 Uncoated Example 1 3
- rapeseed oil 10 g of hardened oil, 5 g of lecithin, and 5 g of nectar were mixed at 70 ° C.
- 25 g of glucose-coated ubidecarenone obtained in Example 1 (22.7 g of ubidecarenone)
- 25 g of glucose-coated L-ascorbic acid obtained in Example 11 (22.7 g of L-ascorbic acid) were obtained.
- the resulting mixture was mixed with ubidecarenone and L-ascorbic acid to obtain a composition.
- This composition was used as a soft capsule preparation of gelatin so as to give 310 mg per capsule (equivalent to 30 mg of ubidecarenone).
- rapeseed oil 20 g of tetraglycerin monooleate, 10 g of ginseng oil, 5 g of lecithin, and 5 g of honey tasting were mixed at 70 ° C.
- 25 g of ubidecarenone coated with glucose obtained in Example 1 (22.7 g as ubidecarenone) and 25 g of ⁇ -tocopherol coated with glucose obtained in Example 13 (22.7 g as a-tocopherol) were added.
- a composition containing ubidecarenone and ⁇ -tocopherol was obtained.
- This composition was used as a soft capsule preparation of gelatin so as to give 310 mg per capsule (equivalent to 30 mg of ubidecarenone).
- rapeseed oil 20 g of tetraglycerin monooleate, 10 g of ginseng oil, 5 g of lecithin, and 5 g of honey tasting were mixed at 70 ° C.
- This composition was used as a gelatin soft capsule formulation so as to give 305 mg (equivalent to 30 ⁇ g menatetrenone) per capsule.
- the compound having a quinone skeleton can be stably retained.
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WO2009048120A1 (ja) * | 2007-10-11 | 2009-04-16 | Nisshin Pharma Inc. | アスタキサンチン含有水溶性組成物 |
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JP2009539951A (ja) * | 2006-06-12 | 2009-11-19 | エルブイエムエイチ レシェルシェ | フリーラジカル捕捉化粧品組成物 |
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