CA2216320C - Stable emulsions and dry powders of mixtures of fat-soluble vitamins, their preparation and use - Google Patents
Stable emulsions and dry powders of mixtures of fat-soluble vitamins, their preparation and use Download PDFInfo
- Publication number
- CA2216320C CA2216320C CA002216320A CA2216320A CA2216320C CA 2216320 C CA2216320 C CA 2216320C CA 002216320 A CA002216320 A CA 002216320A CA 2216320 A CA2216320 A CA 2216320A CA 2216320 C CA2216320 C CA 2216320C
- Authority
- CA
- Canada
- Prior art keywords
- vitamin
- stable
- mixture
- appropriate
- 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
- 229940088594 vitamin Drugs 0.000 title claims abstract description 107
- 229930003231 vitamin Natural products 0.000 title claims abstract description 107
- 235000013343 vitamin Nutrition 0.000 title claims abstract description 107
- 239000011782 vitamin Substances 0.000 title claims abstract description 107
- 239000000203 mixture Substances 0.000 title claims abstract description 85
- 239000000839 emulsion Substances 0.000 title claims abstract description 56
- 239000000843 powder Substances 0.000 title claims abstract description 51
- 238000002360 preparation method Methods 0.000 title abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 33
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 96
- 150000003722 vitamin derivatives Chemical class 0.000 claims description 83
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 claims description 68
- 235000019155 vitamin A Nutrition 0.000 claims description 64
- 239000011719 vitamin A Substances 0.000 claims description 64
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 claims description 57
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 claims description 57
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 57
- 229940045997 vitamin a Drugs 0.000 claims description 57
- 235000019166 vitamin D Nutrition 0.000 claims description 54
- 239000011710 vitamin D Substances 0.000 claims description 54
- 239000011709 vitamin E Substances 0.000 claims description 54
- 235000019165 vitamin E Nutrition 0.000 claims description 54
- 229930003316 Vitamin D Natural products 0.000 claims description 49
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 claims description 49
- 150000003710 vitamin D derivatives Chemical class 0.000 claims description 49
- 229940046008 vitamin d Drugs 0.000 claims description 49
- 229930003427 Vitamin E Natural products 0.000 claims description 48
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 48
- 229940046009 vitamin E Drugs 0.000 claims description 48
- 235000019168 vitamin K Nutrition 0.000 claims description 42
- 239000011712 vitamin K Substances 0.000 claims description 42
- 229930003448 Vitamin K Natural products 0.000 claims description 37
- 150000003721 vitamin K derivatives Chemical class 0.000 claims description 37
- 229940046010 vitamin k Drugs 0.000 claims description 37
- 239000000084 colloidal system Substances 0.000 claims description 32
- 230000001681 protective effect Effects 0.000 claims description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 230000001804 emulsifying effect Effects 0.000 claims description 25
- 239000011248 coating agent Substances 0.000 claims description 20
- 238000000576 coating method Methods 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 20
- 239000000654 additive Substances 0.000 claims description 18
- 235000000346 sugar Nutrition 0.000 claims description 17
- 238000001035 drying Methods 0.000 claims description 16
- 150000005846 sugar alcohols Chemical class 0.000 claims description 16
- 150000008163 sugars Chemical class 0.000 claims description 15
- 238000002156 mixing Methods 0.000 claims description 14
- 238000004945 emulsification Methods 0.000 claims description 10
- 229930006000 Sucrose Natural products 0.000 claims description 9
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000005720 sucrose Substances 0.000 claims description 9
- 244000215068 Acacia senegal Species 0.000 claims description 8
- 229920000084 Gum arabic Polymers 0.000 claims description 8
- 235000010489 acacia gum Nutrition 0.000 claims description 8
- 239000000205 acacia gum Substances 0.000 claims description 8
- 235000013305 food Nutrition 0.000 claims description 8
- 108010010803 Gelatin Proteins 0.000 claims description 5
- 229920000159 gelatin Polymers 0.000 claims description 5
- 239000008273 gelatin Substances 0.000 claims description 5
- 235000019322 gelatine Nutrition 0.000 claims description 5
- 235000011852 gelatine desserts Nutrition 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 3
- 108010082495 Dietary Plant Proteins Proteins 0.000 claims description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 3
- 239000005913 Maltodextrin Substances 0.000 claims description 3
- 229920002774 Maltodextrin Polymers 0.000 claims description 3
- 229920000881 Modified starch Polymers 0.000 claims description 3
- 239000008101 lactose Substances 0.000 claims description 3
- 229940035034 maltodextrin Drugs 0.000 claims description 3
- 235000019426 modified starch Nutrition 0.000 claims description 3
- 239000004368 Modified starch Substances 0.000 claims description 2
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 claims description 2
- 229940100486 rice starch Drugs 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims 2
- 229920002261 Corn starch Polymers 0.000 claims 1
- 239000008120 corn starch Substances 0.000 claims 1
- VYGQUTWHTHXGQB-FFHKNEKCSA-N Retinol Palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C VYGQUTWHTHXGQB-FFHKNEKCSA-N 0.000 description 28
- 239000003921 oil Substances 0.000 description 27
- 235000019198 oils Nutrition 0.000 description 27
- 239000000243 solution Substances 0.000 description 21
- 235000005282 vitamin D3 Nutrition 0.000 description 19
- 239000011647 vitamin D3 Substances 0.000 description 19
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 19
- 229940021056 vitamin d3 Drugs 0.000 description 19
- VYGQUTWHTHXGQB-UHFFFAOYSA-N Retinol hexadecanoate Natural products CCCCCCCCCCCCCCCC(=O)OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C VYGQUTWHTHXGQB-UHFFFAOYSA-N 0.000 description 14
- 229940108325 retinyl palmitate Drugs 0.000 description 14
- 235000019172 retinyl palmitate Nutrition 0.000 description 14
- 239000011769 retinyl palmitate Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- ABSPRNADVQNDOU-UHFFFAOYSA-N Menaquinone 1 Natural products C1=CC=C2C(=O)C(CC=C(C)C)=C(C)C(=O)C2=C1 ABSPRNADVQNDOU-UHFFFAOYSA-N 0.000 description 12
- 229920002472 Starch Polymers 0.000 description 12
- 235000019175 phylloquinone Nutrition 0.000 description 12
- 239000011772 phylloquinone Substances 0.000 description 12
- MBWXNTAXLNYFJB-NKFFZRIASA-N phylloquinone Chemical compound C1=CC=C2C(=O)C(C/C=C(C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C)=C(C)C(=O)C2=C1 MBWXNTAXLNYFJB-NKFFZRIASA-N 0.000 description 12
- 229960001898 phytomenadione Drugs 0.000 description 12
- 239000008107 starch Substances 0.000 description 12
- 235000019698 starch Nutrition 0.000 description 12
- 239000007921 spray Substances 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- -1 invert sugar Chemical compound 0.000 description 4
- 235000016709 nutrition Nutrition 0.000 description 4
- 230000035764 nutrition Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000003240 coconut oil Substances 0.000 description 3
- 235000019864 coconut oil Nutrition 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 102000011632 Caseins Human genes 0.000 description 2
- 108010076119 Caseins Proteins 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 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 description 1
- BVCOHOSEBKQIQD-UHFFFAOYSA-N 2-tert-butyl-6-methoxyphenol Chemical compound COC1=CC=CC(C(C)(C)C)=C1O BVCOHOSEBKQIQD-UHFFFAOYSA-N 0.000 description 1
- BKZXZGWHTRCFPX-UHFFFAOYSA-N 2-tert-butyl-6-methylphenol Chemical compound CC1=CC=CC(C(C)(C)C)=C1O BKZXZGWHTRCFPX-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 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 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 239000004258 Ethoxyquin Substances 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 1
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000019728 animal nutrition Nutrition 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 235000010385 ascorbyl palmitate Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 229920001222 biopolymer Polymers 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- 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 description 1
- 229940071162 caseinate Drugs 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 1
- 235000019285 ethoxyquin Nutrition 0.000 description 1
- 229940093500 ethoxyquin Drugs 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 229960004903 invert sugar Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229940080237 sodium caseinate Drugs 0.000 description 1
- XDLYMKFUPYZCMA-UHFFFAOYSA-M sodium;4-oct-1-enoxy-4-oxobutanoate Chemical group [Na+].CCCCCCC=COC(=O)CCC([O-])=O XDLYMKFUPYZCMA-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- 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
- A23K20/174—Vitamins
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- 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
- A23L33/15—Vitamins
-
- 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
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
-
- 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Nutrition Science (AREA)
- Dispersion Chemistry (AREA)
- Animal Husbandry (AREA)
- Epidemiology (AREA)
- Mycology (AREA)
- Zoology (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Colloid Chemistry (AREA)
- Fodder In General (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19642359.7 | 1996-10-14 | ||
| DE19642359A DE19642359A1 (de) | 1996-10-14 | 1996-10-14 | Stabile Emulsionen und Trockenpulver von Mischungen fettlöslicher Vitamine, deren Herstellung und Verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2216320A1 CA2216320A1 (en) | 1998-04-14 |
| CA2216320C true CA2216320C (en) | 2006-11-28 |
Family
ID=7808722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002216320A Expired - Fee Related CA2216320C (en) | 1996-10-14 | 1997-10-10 | Stable emulsions and dry powders of mixtures of fat-soluble vitamins, their preparation and use |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US6264986B1 (enExample) |
| EP (1) | EP0835613B1 (enExample) |
| JP (1) | JP3914619B2 (enExample) |
| AT (1) | ATE231347T1 (enExample) |
| AU (1) | AU4099197A (enExample) |
| CA (1) | CA2216320C (enExample) |
| DE (2) | DE19642359A1 (enExample) |
| DK (1) | DK0835613T3 (enExample) |
| ES (1) | ES2192243T3 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003518509A (ja) * | 1999-12-23 | 2003-06-10 | アベンティス・アニマル・ニユートリシヨン・エス・エー | 粒状ビタミン組成物 |
| AU2002240141A1 (en) * | 2001-01-26 | 2002-08-06 | Steven Baranowitz | Systemic formulations containing beta-carotene and derivatives thereof |
| US7595378B2 (en) | 2001-06-13 | 2009-09-29 | Genmab A/S | Human monoclonal antibodies to epidermal growth factor receptor (EGFR) |
| US20030228395A1 (en) * | 2002-01-31 | 2003-12-11 | Archer-Daniels Midland Company | Isotropic transparent structured fluids |
| US7501138B2 (en) * | 2002-04-11 | 2009-03-10 | Kyowa Hakko Food Specialities Co., Ltd. | Liquid food/drink containing fat-soluble vitamin and method of stabilizing fat-soluble vitamin |
| CN100502673C (zh) * | 2003-07-15 | 2009-06-24 | 帝斯曼知识产权资产管理有限公司 | 脂溶性活性成分的粉末状制剂 |
| US20050142263A1 (en) * | 2003-12-30 | 2005-06-30 | Lauren Keilbach | Fish food flakes |
| US9247765B2 (en) * | 2004-01-14 | 2016-02-02 | Omniactive Health Technologies Limited | Stable beadlets of lipophilic nutrients |
| US20050244568A1 (en) * | 2004-03-04 | 2005-11-03 | Sorsus Gmbh | Artificial fruit |
| DE102004030072A1 (de) * | 2004-06-23 | 2006-01-19 | Basf Ag | Wässrige Dispersionen schwer wasserlöslicher oder wasserunlöslicher Wirkstoffe und daraus hergestellte Trockenpulver |
| ATE492275T1 (de) * | 2005-04-15 | 2011-01-15 | Einstein Coll Med | Vitamin k zur vorbeugung und behandlung von hautausschlag infolge einer anti-egfr-therapie |
| US9428582B2 (en) * | 2006-07-03 | 2016-08-30 | Genmab A/S | Method of treating rash in patients undergoing anti-EGFR therapy |
| EP2124586A1 (en) * | 2007-01-31 | 2009-12-02 | DSM IP Assets B.V. | Premix emulsion |
| EP1955597A1 (en) * | 2007-01-31 | 2008-08-13 | DSMIP Assets B.V. | Premix emulsion |
| EP2011835A1 (en) | 2007-07-06 | 2009-01-07 | Chr. Hansen A/S | A colouring composition comprising starch derivatives as a hydrocolloid |
| EP2164975B1 (de) | 2007-07-06 | 2012-02-01 | Basf Se | Verfahren zur Herstellung einer konzentrierten wässrigen Glukoselösung aus Mais |
| US8815953B2 (en) * | 2008-03-13 | 2014-08-26 | Spectrum Pharmaceuticals, Inc. | Formulations of vitamin K analogs for topical use |
| CA2759246C (en) * | 2008-04-23 | 2014-03-25 | The Penn State Research Foundation | Methods and compositions for improving the nutritional content of mushrooms and fungi |
| WO2010040683A1 (de) | 2008-10-07 | 2010-04-15 | Basf Se | Gebrauchfertige, stabile emulsion |
| CN108993329A (zh) * | 2012-10-19 | 2018-12-14 | 默克专利股份有限公司 | 微球 |
| IN2014CH01872A (enExample) | 2014-04-09 | 2015-05-08 | Nanoceutica Lab Pvt Ltd | |
| JP6811614B2 (ja) | 2014-05-05 | 2021-01-13 | ビーエイエスエフ・ソシエタス・エウロパエアＢａｓｆ Ｓｅ | 脂溶性ビタミン製剤 |
| US11638439B2 (en) * | 2018-05-21 | 2023-05-02 | Agthia | Vitamin D-fortified water and method of manufacturing thereof |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2756117A (en) * | 1952-03-13 | 1956-07-24 | Louis M Cotchett | Bolsters for spinning frames |
| US2756177A (en) | 1953-03-09 | 1956-07-24 | Hoffmann La Roche | Process for making fat-soluble vitamin active powder |
| US2897119A (en) | 1957-11-12 | 1959-07-28 | Camp Sea Food Company Inc Van | Stable powdered oil soluble vitamins and method of preparing stable powdered oil soluble vitamins |
| FI53651C (fi) | 1976-06-24 | 1979-05-15 | Farmos Oy | Fodervitaminloesning eller -emulsion |
| JPS58162517A (ja) * | 1982-03-19 | 1983-09-27 | Green Cross Corp:The | 脂溶性ビタミン含有脂肪乳剤 |
| US4486435A (en) * | 1983-05-16 | 1984-12-04 | Basf Wyandotte Corporation | Spray-dried vitamin powders using hydrophobic silica |
| US4670247A (en) | 1983-07-05 | 1987-06-02 | Hoffman-Laroche Inc. | Process for preparing fat-soluble vitamin active beadlets |
| DE3770940D1 (de) | 1987-04-06 | 1991-07-25 | Hoffmann La Roche | Verfahren zur herstellung von vitaminpraeparaten. |
| US4966779A (en) | 1989-12-21 | 1990-10-30 | Basf Corporation | Stable, water miscible emulsion comprising a fat-soluble vitamin |
| DE4141351A1 (de) * | 1991-12-14 | 1993-06-17 | Basf Ag | Stabile pulverfoermige vitamin- und/oder carotinoid-praeparate und verfahren zu deren herstellung |
| DE4200728A1 (de) * | 1992-01-14 | 1993-07-15 | Basf Ag | Stabile, fluessige praeparate fettloeslicher substanzen |
| EP0565989B1 (de) | 1992-04-14 | 1997-06-25 | F. Hoffmann-La Roche Ag | Präparate von fettlöslichen Substanzen |
| FR2703263B1 (fr) * | 1993-03-31 | 1995-05-19 | Rhone Poulenc Nutrition Animal | Procédé de préparation de sphérules de principes actifs. |
| DE4424085A1 (de) | 1994-07-11 | 1996-01-18 | Basf Ag | Kaltwasserdispergierbare Zubereitungen fettlöslicher Wirkstoffe |
| CN1048868C (zh) * | 1994-11-30 | 2000-02-02 | 王万梅 | 鱼肝油乳及其制备方法 |
-
1996
- 1996-10-14 DE DE19642359A patent/DE19642359A1/de not_active Withdrawn
-
1997
- 1997-10-09 US US08/948,061 patent/US6264986B1/en not_active Expired - Fee Related
- 1997-10-10 CA CA002216320A patent/CA2216320C/en not_active Expired - Fee Related
- 1997-10-14 AT AT97117759T patent/ATE231347T1/de not_active IP Right Cessation
- 1997-10-14 JP JP28014897A patent/JP3914619B2/ja not_active Expired - Fee Related
- 1997-10-14 DK DK97117759T patent/DK0835613T3/da active
- 1997-10-14 ES ES97117759T patent/ES2192243T3/es not_active Expired - Lifetime
- 1997-10-14 EP EP97117759A patent/EP0835613B1/de not_active Expired - Lifetime
- 1997-10-14 AU AU40991/97A patent/AU4099197A/en not_active Abandoned
- 1997-10-14 DE DE59709183T patent/DE59709183D1/de not_active Expired - Fee Related
-
2000
- 2000-03-21 US US09/531,816 patent/US6531157B1/en not_active Expired - Fee Related
-
2002
- 2002-11-18 US US10/298,114 patent/US7279180B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0835613B1 (de) | 2003-01-22 |
| US20030125310A1 (en) | 2003-07-03 |
| DE19642359A1 (de) | 1998-04-16 |
| US6264986B1 (en) | 2001-07-24 |
| AU4099197A (en) | 1998-04-23 |
| ES2192243T3 (es) | 2003-10-01 |
| JP3914619B2 (ja) | 2007-05-16 |
| US6531157B1 (en) | 2003-03-11 |
| ATE231347T1 (de) | 2003-02-15 |
| DE59709183D1 (de) | 2003-02-27 |
| DK0835613T3 (da) | 2003-02-24 |
| EP0835613A2 (de) | 1998-04-15 |
| EP0835613A3 (de) | 1998-04-22 |
| CA2216320A1 (en) | 1998-04-14 |
| JPH10127258A (ja) | 1998-05-19 |
| US7279180B2 (en) | 2007-10-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |