JP6163687B2 - タンパク質マトリックス中にホップ酸塩を含む小ビーズ - Google Patents
タンパク質マトリックス中にホップ酸塩を含む小ビーズ Download PDFInfo
- Publication number
- JP6163687B2 JP6163687B2 JP2014552558A JP2014552558A JP6163687B2 JP 6163687 B2 JP6163687 B2 JP 6163687B2 JP 2014552558 A JP2014552558 A JP 2014552558A JP 2014552558 A JP2014552558 A JP 2014552558A JP 6163687 B2 JP6163687 B2 JP 6163687B2
- Authority
- JP
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- Prior art keywords
- small beads
- protein
- weight
- beadlets
- total weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 102000004169 proteins and genes Human genes 0.000 title claims description 54
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- 239000011324 bead Substances 0.000 title claims description 53
- 239000011159 matrix material Substances 0.000 title description 13
- 235000008694 Humulus lupulus Nutrition 0.000 title description 2
- 235000018102 proteins Nutrition 0.000 claims description 53
- 239000002253 acid Substances 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 25
- 239000000843 powder Substances 0.000 claims description 23
- 241001465754 Metazoa Species 0.000 claims description 9
- 229920002472 Starch Polymers 0.000 claims description 8
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- 239000008107 starch Substances 0.000 claims description 8
- 239000011248 coating agent Substances 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 6
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- 108010046377 Whey Proteins Proteins 0.000 claims description 5
- 102000007544 Whey Proteins Human genes 0.000 claims description 5
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- 229920000159 gelatin Polymers 0.000 claims description 4
- 239000008273 gelatin Substances 0.000 claims description 4
- 235000019322 gelatine Nutrition 0.000 claims description 4
- 235000011852 gelatine desserts Nutrition 0.000 claims description 4
- MJYQFWSXKFLTAY-OVEQLNGDSA-N (2r,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol;(2r,3r,4s,5s,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O.C1=C(O)C(OC)=CC(C[C@@H](CO)[C@H](CO)CC=2C=C(OC)C(O)=CC=2)=C1 MJYQFWSXKFLTAY-OVEQLNGDSA-N 0.000 claims description 3
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- 240000005979 Hordeum vulgare Species 0.000 claims description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 3
- 244000017020 Ipomoea batatas Species 0.000 claims description 3
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- 235000014647 Lens culinaris subsp culinaris Nutrition 0.000 claims description 3
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- 108010011756 Milk Proteins Proteins 0.000 claims description 2
- 240000000528 Ricinus communis Species 0.000 claims description 2
- 235000004443 Ricinus communis Nutrition 0.000 claims description 2
- 239000005018 casein Substances 0.000 claims description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 claims description 2
- 235000021240 caseins Nutrition 0.000 claims description 2
- 235000021239 milk protein Nutrition 0.000 claims description 2
- 150000004760 silicates Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 description 30
- 239000000203 mixture Substances 0.000 description 21
- 150000007513 acids Chemical class 0.000 description 18
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- 150000001875 compounds Chemical class 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 235000012054 meals Nutrition 0.000 description 5
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 5
- 239000000600 sorbitol Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- QRDZSRWEULKVNW-UHFFFAOYSA-N 6-hydroxy-2-oxo-1h-quinoline-4-carboxylic acid Chemical compound C1=C(O)C=C2C(C(=O)O)=CC(=O)NC2=C1 QRDZSRWEULKVNW-UHFFFAOYSA-N 0.000 description 4
- RWECBKPOUYVUPL-UHFFFAOYSA-N Prehumulone Chemical compound CC(C)CCC(=O)C1=C(O)C(O)(CC=C(C)C)C(=O)C(CC=C(C)C)C1=O RWECBKPOUYVUPL-UHFFFAOYSA-N 0.000 description 4
- 239000011247 coating layer Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
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- 239000008120 corn starch Substances 0.000 description 3
- 238000004945 emulsification Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- RGLRXNKKBLIBQS-XNHQSDQCSA-N leuprolide acetate Chemical compound CC(O)=O.CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 RGLRXNKKBLIBQS-XNHQSDQCSA-N 0.000 description 3
- LSDULPZJLTZEFD-UHFFFAOYSA-N lupulone Chemical class CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O LSDULPZJLTZEFD-UHFFFAOYSA-N 0.000 description 3
- -1 sodium or potassium Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
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- 238000003860 storage Methods 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 150000005846 sugar alcohols Chemical class 0.000 description 3
- LDXMPKMQIKGJFN-OKKPIIHCSA-N (6r)-3,5,6-trihydroxy-2-(2-methylbutanoyl)-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one Chemical compound CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)[C@](O)(CC=C(C)C)C1=O LDXMPKMQIKGJFN-OKKPIIHCSA-N 0.000 description 2
- ICKPYUKAWSXKMY-UHFFFAOYSA-N 3,5,6-trihydroxy-4,6-bis(3-methylbut-2-enyl)-2-propanoylcyclohexa-2,4-dien-1-one Chemical compound CCC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(O)(CC=C(C)C)C1=O ICKPYUKAWSXKMY-UHFFFAOYSA-N 0.000 description 2
- LDXMPKMQIKGJFN-SPLOXXLWSA-N Adhumulone Natural products O=C([C@@H](CC)C)C=1C(=O)[C@@](O)(C/C=C(\C)/C)C(O)=C(C/C=C(\C)/C)C=1O LDXMPKMQIKGJFN-SPLOXXLWSA-N 0.000 description 2
- DRSITEVYZGOOQG-UHFFFAOYSA-N Cohumulone Chemical compound CC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C(O)(CC=C(C)C)C1=O DRSITEVYZGOOQG-UHFFFAOYSA-N 0.000 description 2
- DRSITEVYZGOOQG-HXUWFJFHSA-N Cohumulone Natural products CC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)[C@](O)(CC=C(C)C)C1=O DRSITEVYZGOOQG-HXUWFJFHSA-N 0.000 description 2
- RMFGNMMNUZWCRZ-UHFFFAOYSA-N Humulone Natural products CC(C)CC(=O)C1=C(O)C(O)(CC=C(C)C)C(O)=C(CC=C(C)C)C1=O RMFGNMMNUZWCRZ-UHFFFAOYSA-N 0.000 description 2
- 108010000817 Leuprolide Proteins 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- 108010009736 Protein Hydrolysates Proteins 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- VMSLCPKYRPDHLN-NRFANRHFSA-N humulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)[C@@](O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-NRFANRHFSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- 229940087857 lupron Drugs 0.000 description 2
- 244000144977 poultry Species 0.000 description 2
- 239000003531 protein hydrolysate Substances 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
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- 244000046052 Phaseolus vulgaris Species 0.000 description 1
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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- 241000282849 Ruminantia Species 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
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- 239000013543 active substance Substances 0.000 description 1
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- 125000000539 amino acid group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000019730 animal feed additive Nutrition 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 235000021120 animal protein Nutrition 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- IQDXNHZDRQHKEF-UHFFFAOYSA-N dialuminum;dicalcium;dioxido(oxo)silane Chemical compound [Al+3].[Al+3].[Ca+2].[Ca+2].[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O IQDXNHZDRQHKEF-UHFFFAOYSA-N 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001493 electron microscopy Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
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- 239000012530 fluid Substances 0.000 description 1
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- 238000010438 heat treatment Methods 0.000 description 1
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- 238000009776 industrial production Methods 0.000 description 1
- 239000002555 ionophore Substances 0.000 description 1
- 230000000236 ionophoric effect Effects 0.000 description 1
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- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000009304 pastoral farming Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 235000021118 plant-derived protein Nutrition 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 102000003601 transglutaminase Human genes 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 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
- A61K31/12—Ketones
- A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/105—Aliphatic or alicyclic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/142—Amino acids; Derivatives thereof
- A23K20/147—Polymeric derivatives, e.g. peptides or proteins
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/195—Antibiotics
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K40/00—Shaping or working-up of animal feeding-stuffs
- A23K40/10—Shaping or working-up of animal feeding-stuffs by agglomeration; by granulation, e.g. making powders
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K40/00—Shaping or working-up of animal feeding-stuffs
- A23K40/30—Shaping or working-up of animal feeding-stuffs by encapsulating; by coating
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Animal Husbandry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Fodder In General (AREA)
- Feed For Specific Animals (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12151681 | 2012-01-19 | ||
| EP12151681.9 | 2012-01-19 | ||
| PCT/EP2012/077023 WO2013107607A1 (en) | 2012-01-19 | 2012-12-28 | Beadlets comprising hop acid salts in a protein matrix |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015504682A JP2015504682A (ja) | 2015-02-16 |
| JP6163687B2 true JP6163687B2 (ja) | 2017-07-19 |
Family
ID=47471847
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014552558A Expired - Fee Related JP6163687B2 (ja) | 2012-01-19 | 2012-12-28 | タンパク質マトリックス中にホップ酸塩を含む小ビーズ |
Country Status (8)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017014620A1 (es) * | 2015-07-23 | 2017-01-26 | Laboratorios Minkab, S.A. De C.V. | Suplemento alimenticio a base de ferulato de etilo |
| CN111184074A (zh) * | 2018-11-14 | 2020-05-22 | 中国农业大学 | 乳清蛋白凝胶球在低脂干酪中的应用 |
| CA3140773C (en) * | 2019-05-23 | 2023-09-26 | Wisorig Technologies Pte. Limited | Feed composition comprising hexahydro-.beta.-acid component compounds and application thereof |
Family Cites Families (11)
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|---|---|---|---|---|
| JPS51121536A (en) * | 1975-04-16 | 1976-10-23 | Setsu Hiraiwa | Method of producing granulated powder of saccharine material |
| US4670247A (en) | 1983-07-05 | 1987-06-02 | Hoffman-Laroche Inc. | Process for preparing fat-soluble vitamin active beadlets |
| JPH09220460A (ja) * | 1995-12-14 | 1997-08-26 | Takeda Chem Ind Ltd | 冷却造粒方法およびその装置 |
| US6444227B1 (en) | 1999-08-05 | 2002-09-03 | Roche Vitamins Inc. | Process for preparing fat soluble beadlets |
| US20060013870A1 (en) * | 2002-05-06 | 2006-01-19 | Kuhrts Eric H | Pharmaceutical compositions of hops resins |
| EP1581065B1 (en) | 2003-01-10 | 2007-07-11 | DSM IP Assets B.V. | Process for the manufacture of powderous preparations of fat-soluble substances |
| US20070280982A1 (en) * | 2006-03-29 | 2007-12-06 | Mitsunori Ono | Antimicrobial compositions comprising hop acid alkali salts and uses thereof |
| AU2007238985B2 (en) * | 2006-04-07 | 2012-09-20 | Dsm Nutritional Products Ag | Emulsions and microcapsules with substances having low interfacial tension, methods of making and using thereof |
| US20090092735A1 (en) * | 2007-10-05 | 2009-04-09 | Betal, Llc | Method for preparing stable hop powder |
| AU2008340061B2 (en) * | 2007-12-21 | 2011-07-14 | Basf Se | Microcapsules comprising a fat -soluble active substance |
| AU2010239691B2 (en) * | 2009-04-21 | 2015-09-03 | Haas, John I. | Animal feed compositions and feeding methods |
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- 2012-12-28 US US14/372,302 patent/US9248106B2/en active Active
- 2012-12-28 JP JP2014552558A patent/JP6163687B2/ja not_active Expired - Fee Related
- 2012-12-28 WO PCT/EP2012/077023 patent/WO2013107607A1/en active Application Filing
- 2012-12-28 BR BR112014017889-5A patent/BR112014017889B1/pt not_active IP Right Cessation
- 2012-12-28 EP EP12809287.1A patent/EP2804489A1/en not_active Withdrawn
- 2012-12-28 IN IN5672DEN2014 patent/IN2014DN05672A/en unknown
- 2012-12-28 CN CN201280067665.3A patent/CN104066340A/zh active Pending
- 2012-12-28 KR KR1020147022975A patent/KR20140116938A/ko not_active Ceased
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|---|---|
| EP2804489A1 (en) | 2014-11-26 |
| US9248106B2 (en) | 2016-02-02 |
| WO2013107607A1 (en) | 2013-07-25 |
| BR112014017889B1 (pt) | 2019-11-05 |
| US20140370106A1 (en) | 2014-12-18 |
| BR112014017889A2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2017-06-20 |
| KR20140116938A (ko) | 2014-10-06 |
| CN104066340A (zh) | 2014-09-24 |
| BR112014017889A8 (pt) | 2017-07-11 |
| JP2015504682A (ja) | 2015-02-16 |
| IN2014DN05672A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2015-04-03 |
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