WO2006062238A1 - アミノ酸の微粉末及びその懸濁液 - Google Patents
アミノ酸の微粉末及びその懸濁液 Download PDFInfo
- Publication number
- WO2006062238A1 WO2006062238A1 PCT/JP2005/022905 JP2005022905W WO2006062238A1 WO 2006062238 A1 WO2006062238 A1 WO 2006062238A1 JP 2005022905 W JP2005022905 W JP 2005022905W WO 2006062238 A1 WO2006062238 A1 WO 2006062238A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- amino acid
- suspension
- fine powder
- soluble amino
- cystine
- Prior art date
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- 150000001413 amino acids Chemical class 0.000 title claims abstract description 68
- 239000000725 suspension Substances 0.000 title claims abstract description 61
- 239000000843 powder Substances 0.000 title claims abstract description 36
- 239000002245 particle Substances 0.000 claims abstract description 37
- 238000001238 wet grinding Methods 0.000 claims abstract description 6
- 235000001014 amino acid Nutrition 0.000 claims description 63
- 229960003067 cystine Drugs 0.000 claims description 33
- 239000002270 dispersing agent Substances 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 235000013361 beverage Nutrition 0.000 claims description 19
- 238000010298 pulverizing process Methods 0.000 claims description 16
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 15
- 235000010445 lecithin Nutrition 0.000 claims description 15
- 239000000787 lecithin Substances 0.000 claims description 15
- 229940067606 lecithin Drugs 0.000 claims description 15
- 235000013305 food Nutrition 0.000 claims description 12
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 10
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 10
- 235000003704 aspartic acid Nutrition 0.000 claims description 10
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 229920000609 methyl cellulose Polymers 0.000 claims description 10
- 239000001923 methylcellulose Substances 0.000 claims description 10
- 235000010981 methylcellulose Nutrition 0.000 claims description 10
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 8
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 6
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 6
- 235000013922 glutamic acid Nutrition 0.000 claims description 6
- 239000004220 glutamic acid Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 235000002374 tyrosine Nutrition 0.000 claims description 6
- 239000001814 pectin Substances 0.000 claims description 4
- 235000010987 pectin Nutrition 0.000 claims description 4
- 229920001277 pectin Polymers 0.000 claims description 4
- LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 claims 5
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 28
- 238000000227 grinding Methods 0.000 description 19
- 238000004062 sedimentation Methods 0.000 description 12
- 238000009826 distribution Methods 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- 239000003814 drug Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 5
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 5
- 230000036541 health Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 235000021056 liquid food Nutrition 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 235000016709 nutrition Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000011324 bead Substances 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000035764 nutrition Effects 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002250 progressing effect Effects 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- -1 methylcellulose Chemical class 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000010951 particle size reduction Methods 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000011496 sports drink Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
- A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/17—Amino acids, peptides or proteins
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- the present invention relates to a suspension in which hardly soluble amino acids such as cystine, aspartic acid, tyrosine, glutamic acid and tryptophan are uniformly and stably dispersed.
- Amino acid is an essential component for the growth of the human body and animals, and in recent years, in addition to its nutritional value, various values related to various health functionalities have been discovered. For this reason, products with amino acids added to foods, beverages or pharmaceuticals are expected.
- cystine has been found to be effective in preventing infection by ingesting more than a certain amount, and is expected for health foods and health drinks.
- a poorly soluble amino acid with low solubility in water, the required amount cannot be dissolved, especially when trying to add it to beverages, and a poorly soluble amino acid generally has a high specific gravity (for example, cystine) The true specific gravity is 1.6). It is difficult to disperse this uniformly and stably because of its high sedimentation. Therefore, even if enteral nutrients and infusion solutions containing poorly water-soluble amino acids have been present, none of them contained more than the solubility.
- the problem to be solved by the present invention is to provide a suspension in which a hardly soluble amino acid is uniformly and stably dispersed, and a fine powder suitable for preparing the suspension.
- the present inventors have intensively studied, and the average particle diameter is kept constant by wet grinding of poorly soluble amino acids such as crystalline or amorphous cystine, aspartic acid, tyrosine, glutamic acid, and tryptophan. The following fine powder was obtained, and when it was suspended, the sedimentation property was remarkably lowered, and it was found that a uniform and stable suspension state was achieved thereby completing the present invention. .
- the present invention is as follows.
- FIG. 1 is a graph showing changes in the cystine particle size distribution with and without lecithin.
- FIG. 2 is a graph showing changes in the cystine particle size distribution of lecithin 10%.
- Fig. 3 is a graph showing the change (1) in the cystine particle size distribution of the methylcellulose 13% system.
- Figure 4 is a graph showing the change (2) in the cystine particle size distribution of methylcellulose 13%.
- Fig. 5 is a graph showing the change in the average cystine particle size with the flour treatment time.
- “sparingly soluble” means amino acids that are sparingly soluble in water, as well as organic solvents such as ethanol, and mixtures thereof. In the present invention, “sparingly soluble” means a solubility of about 1 g ZlO 0 00 g or less (20 ° C.).
- Examples of the “slightly soluble amino acid” in the present invention include cystine, aspartic acid, tyrosine, glutamic acid, tryptophan, etc., preferably cystine, aspartic acid, tyrosine, and particularly preferably cystine.
- the “suspension” refers to a suspension, preferably an aqueous suspension, in which a fine powder of the hardly soluble amino acid of the present invention is dispersed in water, a medium such as ethanol, or a mixture thereof.
- a preferred aqueous suspension in the present invention may contain salts, buffers, organic solvents, etc. in addition to water as a medium.
- the amino acid before pulverizing the hardly soluble amino acid may be crystalline or amorphous, but is preferably crystalline.
- the “average particle size” of fine powder means, for example, that when measured with a laser light forward scattering type particle size analyzer (for example, SK Microanalyzer PR07100 manufactured by Seishin Enterprise Co., Ltd.) 5 refers to a volume-based particle diameter d 5 0 is 0%.
- a laser light forward scattering type particle size analyzer for example, SK Microanalyzer PR07100 manufactured by Seishin Enterprise Co., Ltd.
- a poorly soluble amino acid such as cystine, aspartic acid, tyrosine, gnoretamic acid, tryptophan, etc. (average particle size of about 20 to 50 m as crystals of amino acid) uniformly and stably in a water medium.
- the present inventors first tried dry pulverization.
- the average particle size that can be obtained with dry-type powder mash is limited to about 5 to 10 / xm. With this size, poorly water-soluble amino acids are uniformly distributed in water. And it could not be stably dispersed. It is not preferable to grind more than this because the possibility that the amino acid is denatured due to heat generation increases.
- the present inventors found for the first time that a poorly soluble amino acid such as cystine can be obtained as a fine powder having an average particle size of about 0.1 to 5 ⁇ , It has been found that the fine powder is suitable for forming a stable suspension.
- the fine powder of the present invention is uniformly dispersed in water, a medium such as ethanol, or a mixture thereof to form a stable suspension.
- any wet pulverizer may be used.
- an apparatus for rotating a rotating cylinder or a disk in a cylindrical container preferably Continuous annular type bead mill that rotates a cylinder with protrusions (for example, Spike Mill (trade name), manufactured by Inoue Seisakusho Co., Ltd. (SHG-4 Bessel capacity 860 ml)).
- the powdering conditions are, for example, a flow rate of 20 Om l / min, an inner shaft rotation speed of 2,900 rpm, a bead filling rate of 50%, 9 circulation cycles, temperature: 27 ° C at the start of grinding, and an average of 38 ° C during powdering is there.
- the concentration of amino acid in the medium during wet milling is determined from the viewpoint of industrial efficiency of grinding and effectiveness during grinding, and varies depending on the desired grinding conditions and the type of amino acid to be ground. 0.1 to 30% by weight, preferably about 2 to 20% by weight. When the concentration is higher than this, the viscosity of the suspension increases, and when it is lower, the efficiency of the grinding decreases.
- the concentration of the amino acid in the medium is determined from the weight of the amino acid added to the solution, or from a solution sampled from a suspension and dissolved by an appropriate method such as addition of acid or alkali, and then a general analysis such as an amino acid analyzer. It can be determined by the method.
- the concentration of the hardly soluble amino acid in the suspension is, for example, 10 mg Z 100 g suspension to 30 g Zl 00 g suspension, preferably 10 mg / 100 g suspension.
- Viscosity can be measured with, for example, a rotating disk type viscometer (DVM-B type (manufactured by Tokyo Keiki Co., Ltd.)), and can be measured for non-Yuton fluids by devising rotation conditions
- DVM-B type manufactured by Tokyo Keiki Co., Ltd.
- rotor B can be used (30 rpm, 50 seconds, 20 ° C.).
- amino acid crystals with an average particle size of usually 20-50 / zm can be made into fine powder with an average particle size of 0.1-5 ⁇ , preferably 0.1-3.5 ⁇ . it can. Unlike inorganic materials, it is soft and easily increases in viscosity. In the case of amino acid, which is an organic material, if it is finely ground, it becomes difficult to increase viscosity due to surface friction.
- the wet pulverization may be carried out only in the presence of a medium (preferably water), but preferably a dispersant is added.
- the dispersant may be added at the time of wet milling, but may not be added at the time of milling but may be added to the suspension after pulverization. If a dispersant is added at the time of powdering, the increase in viscosity at the time of wet pulverization is suppressed, so that finer powdering can be achieved, and the dispersion stability of the fine powder during storage is enhanced.
- Examples of the dispersant used in the present invention include lecithin, methylcellulose, and vectin, and preferably lecithin and methylcellulose.
- a “dispersant” is a suspension that has an affinity for a part of the surface of the substance in which the hydrophobic structure is suspended, and the hydrophilic structure is compatible with the solvent to be dispersed, for example, water. Improve the affinity between the turbid substance and the solvent, or the association between suspended substances A force that can improve the homogeneity and stability of the suspension by suppressing the water, for example, a bipolar substance such as lecithin, a water-soluble polysaccharide such as methylcellulose, and the like.
- the amount of dispersant added depends on the type, the nature of the solvent, and the purpose of the addition, but is generally about 0.2 to 20%, preferably 1 to 1, based on the substance to be suspended. Add about 0%. Depending on conditions, other addition amounts may be appropriate.
- Hard particles may coexist during wet pulverization. Hard particles have a higher hardness than the material to be powdered, or have a relatively high specific gravity, so that the material particles to be powdered can be given sufficient grinding energy.
- An example is zirconium.
- the particle size of the hard particles is, for example, 100 to 700 ⁇ m, and preferably 400 ⁇ m. The optimum amount to be added varies depending on the conditions of the hard particles and the object, but for example, it may be added about half of the capacity of the grinding container.
- the suspension after wet pulverization can be blended as it is or after appropriately diluting into beverages, other foods, or pharmaceuticals ⁇ .
- the finely powdered sparingly soluble amino acid of the present invention is obtained by removing the solvent from the suspension obtained by wet milling and drying.
- the drying method depends on the type of the suspension medium, but may be any method such as drying under reduced pressure, freeze drying, or natural drying by casting on a flat plate, but freeze drying is preferred.
- the fine powder of the present invention can be blended in beverages, other foods, pharmaceuticals and the like.
- various preparations can be prepared by ordinary preparation techniques such as granulation by adding granulation as appropriate, or encapsulating in capsules.
- the blending amount of the fine powder and / or suspension of the present invention into beverages, other foods, pharmaceuticals, etc. is set to an amount necessary and sufficient for each amino acid to exhibit its intended function.
- each amino acid is stably suspended in the form of fine particles, so that transparency and low viscosity can be maintained even at high concentrations. Is also preferable.
- the amino acid is in a fine particle state, and the intestinal absorbability can be stably and significantly improved in mammals including humans. It is possible to maintain the therapeutic effect effectively and stably, and it is useful for maintaining health or treating.
- the spike mill used in the examples is SHG-4 (crushed space volume 75 m 1, vessel capacity 8 60 m 1) manufactured by Inoue Mfg. Co., Ltd.
- the inner shaft speed was 2,900 rpm and the bead diameter was 400 / zm.
- the particle size distribution was measured using a laser light forward scattering type particle size analyzer (manufactured by Seishin Co., Ltd .: SK Micron Sizer PR07100). With regard to the dispersion stability of the suspension, the suspension and its 10-fold diluted solution were allowed to stand, and the state of amino acid sedimentation (sedimentation speed, sedimentation volume) was observed.
- FIG. 1 shows the case Do added lecithin, and particle size distribution in the case of lecithin was added 1 wt 0/0 for cystine (average particle diameter 2 5 ⁇ ⁇ ). The two are almost the same, and there is no change in the particle size just by adding the dispersant, so the cystine is not an agglomerate that is broken up by the dispersant. It has become clear that particle size reduction by pulverization is necessary.
- the viscosity increased with each treatment, but the average particle size d 5 . Can be evaluated as miniaturization is progressing. An average particle size d 50 of 3 zm was obtained after 9 treatments. The suspension after pulverization was stable for about one week and showed no sedimentation.
- a sample was prepared by adding 60,000 g of cystine and 60 g of lecithin (10% by weight with respect to cystine) to 5400 g of water, and this was processed with a spike mill in the same manner as in Example 2. .
- Figure 2 shows the changes in the particle size distribution when a dispersion experiment was conducted on this sample.
- Flat Hitoshitsubu ⁇ d 5. Can be evaluated as the miniaturization is progressing. The increase in viscosity is small even after repeated treatments, and it is thought that the addition of lecithin promoted grinding.
- Dispersion stability with a diluted solution adjusted to 1% concentration of the suspension is improved in terms of reduced sedimentation volume compared to when lecithin is not added. Although it was seen, it was found that the time required for sedimentation was short. This is probably because the increase in the viscosity of the dispersion was suppressed.
- Fig. 3 shows the change in particle size distribution by the number of treatments
- Fig. 4 shows the change in particle size distribution by treatment time
- Figure 5 shows the transition of the average particle size according to the processing time.
- a hardly soluble amino acid such as cystine, aspartic acid, tyrosine, glutamic acid, tryptophan, etc., which has been difficult to be conventionally mixed in a high concentration from the viewpoint of solubility or suspension.
- the suspension of the present invention can be used to produce beverages, liquid foods, pharmaceuticals, and the like that contain a sufficient amount of a poorly soluble amino acid necessary for expressing a nutrient-specific function in a high concentration and uniformly dispersed state.
- the slightly soluble amino acid fine powder or suspension of the present invention has excellent intestinal absorbability in mammals including humans, and can effectively express the desired nutrition and specific functions. It is extremely useful in the pharmaceutical field.
- amino acids excellent in nutrition and specific health functions can be used in beverages and foods, especially in low-viscosity and highly transparent beverages such as teas and sports drinks, or in jelly and
- This application is based on Japanese Patent Application No. 2004-354391 filed in ⁇ , the contents of which are incorporated in full herein.
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Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05816740A EP1839502A4 (en) | 2004-12-07 | 2005-12-07 | FINE AMINO ACID POWDER AND SUSPENSION THEREOF |
JP2006546790A JPWO2006062238A1 (ja) | 2004-12-07 | 2005-12-07 | アミノ酸の微粉末及びその懸濁液 |
US11/759,320 US20070286887A1 (en) | 2004-12-07 | 2007-06-07 | Fine powder of amino acid and suspension thereof |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004-354391 | 2004-12-07 | ||
JP2004354391 | 2004-12-07 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/759,320 Continuation US20070286887A1 (en) | 2004-12-07 | 2007-06-07 | Fine powder of amino acid and suspension thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006062238A1 true WO2006062238A1 (ja) | 2006-06-15 |
Family
ID=36578048
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2005/022905 WO2006062238A1 (ja) | 2004-12-07 | 2005-12-07 | アミノ酸の微粉末及びその懸濁液 |
Country Status (4)
Country | Link |
---|---|
US (1) | US20070286887A1 (ja) |
EP (1) | EP1839502A4 (ja) |
JP (1) | JPWO2006062238A1 (ja) |
WO (1) | WO2006062238A1 (ja) |
Cited By (5)
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---|---|---|---|---|
JP2009286755A (ja) * | 2008-05-30 | 2009-12-10 | Nippon Rikagaku Yakuhin Kk | 難溶性アミノ酸類微細粒子、難溶性アミノ酸類含有混合組成物及びこれらの製造方法並びに皮膚外用剤及び食品添加物 |
JP2014196275A (ja) * | 2013-03-29 | 2014-10-16 | 富士フイルム株式会社 | 組成物及び化粧料 |
JP2015535423A (ja) * | 2012-11-14 | 2015-12-14 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | 細胞培養培地 |
US11298332B2 (en) | 2018-06-20 | 2022-04-12 | Axcella Health Inc. | Compositions for therapy and health containing amino acids with bitter taste |
US11679089B2 (en) | 2018-06-20 | 2023-06-20 | Axcella Health Inc. | Methods of manufacturing amino acid compositions |
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US20240138449A1 (en) * | 2021-11-04 | 2024-05-02 | Nanjing Nutrabuilding Bio-Tech Co., Ltd. | Method for Preparing Moisture-Proof Amino Acid Materials |
WO2023077710A1 (en) * | 2021-11-04 | 2023-05-11 | Nanjing Nutrabuilding Bio-Tech Co., Ltd. | Method for preparingmoisture‐proof amino acid materials |
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JPS63112519A (ja) * | 1986-10-28 | 1988-05-17 | Shin Etsu Chem Co Ltd | ニフエジピン製剤の製造方法 |
JPS642554A (en) * | 1987-06-23 | 1989-01-06 | Nippon Oil & Fats Co Ltd | Production of coated amino acids |
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JP2003121885A (ja) * | 2001-10-12 | 2003-04-23 | Fujitsu Ltd | 2色ボールの製造方法及び表示装置の製造方法 |
WO2004058216A2 (en) * | 2002-12-17 | 2004-07-15 | Elan Pharma International Ltd. | Milling microgram quantities of nanoparticulate candidate compounds |
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2005
- 2005-12-07 EP EP05816740A patent/EP1839502A4/en not_active Withdrawn
- 2005-12-07 JP JP2006546790A patent/JPWO2006062238A1/ja not_active Abandoned
- 2005-12-07 WO PCT/JP2005/022905 patent/WO2006062238A1/ja active Application Filing
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2007
- 2007-06-07 US US11/759,320 patent/US20070286887A1/en not_active Abandoned
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JPS63112519A (ja) * | 1986-10-28 | 1988-05-17 | Shin Etsu Chem Co Ltd | ニフエジピン製剤の製造方法 |
JPS642554A (en) * | 1987-06-23 | 1989-01-06 | Nippon Oil & Fats Co Ltd | Production of coated amino acids |
JPH09235238A (ja) * | 1995-12-25 | 1997-09-09 | Otsuka Pharmaceut Co Ltd | 乾燥組成物 |
JPH101616A (ja) * | 1996-03-11 | 1998-01-06 | Basf Ag | 微分散したカロチノイド又はレチノイド懸濁液の製法、カロチノイド又はレチノイド懸濁液及び食料品及び飼料の着色法 |
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WO2003070023A1 (fr) * | 2002-02-22 | 2003-08-28 | Ajinomoto Co., Inc. | Poudre d'acides amines et procede de production de cette poudre |
Cited By (9)
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JP2009286755A (ja) * | 2008-05-30 | 2009-12-10 | Nippon Rikagaku Yakuhin Kk | 難溶性アミノ酸類微細粒子、難溶性アミノ酸類含有混合組成物及びこれらの製造方法並びに皮膚外用剤及び食品添加物 |
JP2015535423A (ja) * | 2012-11-14 | 2015-12-14 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | 細胞培養培地 |
US10030225B2 (en) | 2012-11-14 | 2018-07-24 | Merck Patent Gmbh | Cell culture media |
JP2019030334A (ja) * | 2012-11-14 | 2019-02-28 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | 細胞培養培地 |
US10619131B2 (en) | 2012-11-14 | 2020-04-14 | Merck Patent Gmbh | Cell culture media |
JP2014196275A (ja) * | 2013-03-29 | 2014-10-16 | 富士フイルム株式会社 | 組成物及び化粧料 |
US11298332B2 (en) | 2018-06-20 | 2022-04-12 | Axcella Health Inc. | Compositions for therapy and health containing amino acids with bitter taste |
US11679089B2 (en) | 2018-06-20 | 2023-06-20 | Axcella Health Inc. | Methods of manufacturing amino acid compositions |
US11896570B2 (en) | 2018-06-20 | 2024-02-13 | Axcella (Assignment For The Benefit Of Creditors), Llc | Compositions for therapy and health containing amino acids with bitter taste |
Also Published As
Publication number | Publication date |
---|---|
EP1839502A4 (en) | 2010-03-24 |
JPWO2006062238A1 (ja) | 2008-06-12 |
EP1839502A1 (en) | 2007-10-03 |
US20070286887A1 (en) | 2007-12-13 |
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