CA1202809A - Preparation of finely divided pulverulent carotinoid and retinoid compositions - Google Patents
Preparation of finely divided pulverulent carotinoid and retinoid compositionsInfo
- Publication number
- CA1202809A CA1202809A CA000402846A CA402846A CA1202809A CA 1202809 A CA1202809 A CA 1202809A CA 000402846 A CA000402846 A CA 000402846A CA 402846 A CA402846 A CA 402846A CA 1202809 A CA1202809 A CA 1202809A
- Authority
- CA
- Canada
- Prior art keywords
- carotinoid
- retinoid
- water
- particle size
- solvent
- 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
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 25
- 150000004492 retinoid derivatives Chemical class 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims description 10
- 239000002904 solvent Substances 0.000 claims abstract description 44
- 238000000034 method Methods 0.000 claims abstract description 32
- 238000002156 mixing Methods 0.000 claims abstract description 31
- 239000000243 solution Substances 0.000 claims abstract description 31
- 239000002245 particle Substances 0.000 claims abstract description 23
- 239000006185 dispersion Substances 0.000 claims abstract description 20
- 239000000084 colloidal system Substances 0.000 claims abstract description 16
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- 239000000843 powder Substances 0.000 claims description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000009826 distribution Methods 0.000 claims description 8
- 239000003381 stabilizer Substances 0.000 claims description 7
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 239000004014 plasticizer Substances 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 3
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 claims description 2
- 208000036366 Sensation of pressure Diseases 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 35
- FDSDTBUPSURDBL-LOFNIBRQSA-N canthaxanthin Chemical compound CC=1C(=O)CCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C(=O)CCC1(C)C FDSDTBUPSURDBL-LOFNIBRQSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000725 suspension Substances 0.000 description 13
- 108010010803 Gelatin Proteins 0.000 description 12
- 239000008273 gelatin Substances 0.000 description 12
- 229940014259 gelatin Drugs 0.000 description 12
- 235000019322 gelatine Nutrition 0.000 description 12
- 235000011852 gelatine desserts Nutrition 0.000 description 12
- 229920000159 gelatin Polymers 0.000 description 11
- 238000001694 spray drying Methods 0.000 description 10
- 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 8
- 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 8
- 229960004592 isopropanol Drugs 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- OOUTWVMJGMVRQF-DOYZGLONSA-N Phoenicoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C(=O)C(O)CC1(C)C)C=CC=C(/C)C=CC2=C(C)C(=O)CCC2(C)C OOUTWVMJGMVRQF-DOYZGLONSA-N 0.000 description 7
- 235000012682 canthaxanthin Nutrition 0.000 description 7
- 239000001659 canthaxanthin Substances 0.000 description 7
- 229940008033 canthaxanthin Drugs 0.000 description 7
- 239000008121 dextrose Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000004375 Dextrin Substances 0.000 description 5
- 229920001353 Dextrin Polymers 0.000 description 5
- UPYKUZBSLRQECL-UKMVMLAPSA-N Lycopene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1C(=C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=C)CCCC2(C)C UPYKUZBSLRQECL-UKMVMLAPSA-N 0.000 description 5
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 5
- 235000019425 dextrin Nutrition 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- -1 invert sugar Chemical compound 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000004217 Citranaxanthin Substances 0.000 description 4
- SLQHGWZKKZPZEK-JKEZLOPUSA-N Citranaxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C(=O)C)C=CC=C(/C)C=CC1=C(C)CCCC1(C)C SLQHGWZKKZPZEK-JKEZLOPUSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 4
- 239000012736 aqueous medium Substances 0.000 description 4
- 235000010385 ascorbyl palmitate Nutrition 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 235000005473 carotenes Nutrition 0.000 description 4
- 150000001746 carotenes Chemical class 0.000 description 4
- 235000019247 citranaxanthin Nutrition 0.000 description 4
- PRDJTOVRIHGKNU-ZWERVMMHSA-N citranaxanthin Chemical compound CC(=O)\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C PRDJTOVRIHGKNU-ZWERVMMHSA-N 0.000 description 4
- PRDJTOVRIHGKNU-UHFFFAOYSA-N citranaxanthine Natural products CC(=O)C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C PRDJTOVRIHGKNU-UHFFFAOYSA-N 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
- 229960001295 tocopherol Drugs 0.000 description 4
- 239000011732 tocopherol Substances 0.000 description 4
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229920000084 Gum arabic Polymers 0.000 description 3
- 241000978776 Senegalia senegal Species 0.000 description 3
- 235000010489 acacia gum Nutrition 0.000 description 3
- 239000000205 acacia gum Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000010525 oxidative degradation reaction Methods 0.000 description 2
- 239000001814 pectin Substances 0.000 description 2
- 235000010987 pectin Nutrition 0.000 description 2
- 229920001277 pectin Polymers 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 description 2
- DNISEZBAYYIQFB-PHDIDXHHSA-N (2r,3r)-2,3-diacetyloxybutanedioic acid Chemical compound CC(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(C)=O DNISEZBAYYIQFB-PHDIDXHHSA-N 0.000 description 1
- DMASLKHVQRHNES-UPOGUZCLSA-N (3R)-beta,beta-caroten-3-ol Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C DMASLKHVQRHNES-UPOGUZCLSA-N 0.000 description 1
- JKQXZKUSFCKOGQ-JLGXGRJMSA-N (3R,3'R)-beta,beta-carotene-3,3'-diol Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C[C@@H](O)CC1(C)C JKQXZKUSFCKOGQ-JLGXGRJMSA-N 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- 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
- 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 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
- 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 description 1
- JEBFVOLFMLUKLF-IFPLVEIFSA-N Astaxanthin Natural products CC(=C/C=C/C(=C/C=C/C1=C(C)C(=O)C(O)CC1(C)C)/C)C=CC=C(/C)C=CC=C(/C)C=CC2=C(C)C(=O)C(O)CC2(C)C JEBFVOLFMLUKLF-IFPLVEIFSA-N 0.000 description 1
- RAFGELQLHMBRHD-VFYVRILKSA-N Bixin Natural products COC(=O)C=CC(=C/C=C/C(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C(=O)O)/C)C RAFGELQLHMBRHD-VFYVRILKSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 239000004212 Cryptoxanthin Substances 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
- 206010013786 Dry skin Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 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 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 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 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 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 description 1
- JKQXZKUSFCKOGQ-LQFQNGICSA-N Z-zeaxanthin Natural products C([C@H](O)CC=1C)C(C)(C)C=1C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC1=C(C)C[C@@H](O)CC1(C)C JKQXZKUSFCKOGQ-LQFQNGICSA-N 0.000 description 1
- QOPRSMDTRDMBNK-RNUUUQFGSA-N Zeaxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCC(O)C1(C)C)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C QOPRSMDTRDMBNK-RNUUUQFGSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- JKQXZKUSFCKOGQ-LOFNIBRQSA-N all-trans-Zeaxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C JKQXZKUSFCKOGQ-LOFNIBRQSA-N 0.000 description 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
- 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 description 1
- RAFGELQLHMBRHD-UHFFFAOYSA-N alpha-Fuc-(1-2)-beta-Gal-(1-3)-(beta-GlcNAc-(1-6))-GalNAc-ol Natural products COC(=O)C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC(O)=O RAFGELQLHMBRHD-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000001670 anatto Substances 0.000 description 1
- 235000012665 annatto Nutrition 0.000 description 1
- 125000003289 ascorbyl group Chemical group [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 description 1
- 235000013793 astaxanthin Nutrition 0.000 description 1
- 239000001168 astaxanthin Substances 0.000 description 1
- MQZIGYBFDRPAKN-ZWAPEEGVSA-N astaxanthin Chemical compound C([C@H](O)C(=O)C=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C(=O)[C@@H](O)CC1(C)C MQZIGYBFDRPAKN-ZWAPEEGVSA-N 0.000 description 1
- 229940022405 astaxanthin Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000002360 beta-cryptoxanthin Nutrition 0.000 description 1
- DMASLKHVQRHNES-ITUXNECMSA-N beta-cryptoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2=C(C)CCCC2(C)C DMASLKHVQRHNES-ITUXNECMSA-N 0.000 description 1
- RAFGELQLHMBRHD-SLEZCNMESA-N bixin Chemical compound COC(=O)\C=C\C(\C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C(O)=O RAFGELQLHMBRHD-SLEZCNMESA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 239000000969 carrier 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
- 238000013329 compounding Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000019244 cryptoxanthin Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000003311 flocculating effect Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 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
- 150000002500 ions Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000002356 laser light scattering Methods 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
- 239000007788 liquid Substances 0.000 description 1
- 235000012680 lutein Nutrition 0.000 description 1
- 239000001656 lutein Substances 0.000 description 1
- KBPHJBAIARWVSC-RGZFRNHPSA-N lutein Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C KBPHJBAIARWVSC-RGZFRNHPSA-N 0.000 description 1
- 229960005375 lutein Drugs 0.000 description 1
- ORAKUVXRZWMARG-WZLJTJAWSA-N lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C ORAKUVXRZWMARG-WZLJTJAWSA-N 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000003921 particle size analysis Methods 0.000 description 1
- 239000000049 pigment Substances 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
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000008476 powdered milk Nutrition 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229930002330 retinoic acid Natural products 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 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
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- FJHBOVDFOQMZRV-XQIHNALSSA-N xanthophyll Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C=C(C)C(O)CC2(C)C FJHBOVDFOQMZRV-XQIHNALSSA-N 0.000 description 1
- 235000010930 zeaxanthin Nutrition 0.000 description 1
- 239000001775 zeaxanthin Substances 0.000 description 1
- 229940043269 zeaxanthin Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
-
- 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
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/40—Colouring or decolouring of foods
- A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
- A23L5/43—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives
- A23L5/44—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives using carotenoids or xanthophylls
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fodder In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813119383 DE3119383A1 (de) | 1981-05-15 | 1981-05-15 | Verfahren zur herstellung von feinverteilten, pulverfoermigen carotinodpraeparaten |
| DEP3119383.8 | 1981-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1202809A true CA1202809A (en) | 1986-04-08 |
Family
ID=6132411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000402846A Expired CA1202809A (en) | 1981-05-15 | 1982-05-12 | Preparation of finely divided pulverulent carotinoid and retinoid compositions |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4522743A (enExample) |
| EP (1) | EP0065193B1 (enExample) |
| JP (1) | JPS57195161A (enExample) |
| AT (1) | ATE16814T1 (enExample) |
| AU (1) | AU553623B2 (enExample) |
| CA (1) | CA1202809A (enExample) |
| DE (2) | DE3119383A1 (enExample) |
| DK (2) | DK154395C (enExample) |
| IL (1) | IL65707A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0986963B1 (de) | 1998-09-14 | 2016-12-07 | Basf Se | Stabile, pulverförmige Lycopin-Formulierungen, enthaltend Lycopin mit einem Kristallinitätsgrad von grösser 20% |
Families Citing this family (122)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6272635A (ja) * | 1985-09-27 | 1987-04-03 | Toyo Soda Mfg Co Ltd | 臭素化アセナフチレン縮合体を製造する方法 |
| DE3610191A1 (de) * | 1986-03-26 | 1987-10-01 | Basf Ag | Verfahren zur herstellung von feinteiligen, wasserdispergierbaren carotinoid-praeparationen |
| DE3611229A1 (de) * | 1986-04-04 | 1987-10-08 | Basf Ag | Verfahren zur herstellung von feinverteilten, pulverfoermigen carotinoidpraeparaten |
| DE3702030A1 (de) * | 1987-01-24 | 1988-08-04 | Basf Ag | Pulverfoermige, wasserdispergierbare carotinoid-zubereitungen und verfahren zu ihrer herstellung |
| DE3702029A1 (de) * | 1987-01-24 | 1988-08-04 | Basf Ag | Waessriges oder pulverfoermiges, wasserdispergierbares praeparat eines in wasser schwerloeslichen pharmazeutischen wirkstoffs und verfahren zu seiner herstellung |
| US4871551A (en) * | 1988-02-08 | 1989-10-03 | Microbio Resources, Inc. | Pigmentation supplements for animal feed compositions |
| DE59003205D1 (de) * | 1989-07-25 | 1993-12-02 | Hoffmann La Roche | Verfahren zur Herstellung von Carotinoidpräparaten. |
| DK546289D0 (da) * | 1989-11-02 | 1989-11-02 | Danochemo As | Carotenoidpulvere |
| US4966779A (en) * | 1989-12-21 | 1990-10-30 | Basf Corporation | Stable, water miscible emulsion comprising a fat-soluble vitamin |
| US5079016A (en) * | 1990-05-16 | 1992-01-07 | Kalamazoo Holdings, Inc. | Color-stabilized carotenoid pigment compositions and foods colored therewith having increased resistance to oxidative color fading |
| AU670777B2 (en) * | 1992-04-16 | 1996-08-01 | Ortho Pharmaceutical Corporation | Aqueous gel vehicles for retinoids |
| US20070117862A1 (en) * | 1993-02-22 | 2007-05-24 | Desai Neil P | Novel formulations of pharmacological agents, methods for the preparation thereof and methods for the use thereof |
| DE19609538A1 (de) * | 1996-03-11 | 1997-09-18 | Basf Ag | Feinverteilte Carotinoid- und Retinoidsuspensionen und Verfahren zu ihrer Herstellung |
| DE4329446A1 (de) * | 1993-09-01 | 1995-03-02 | Basf Ag | Verfahren zur Herstellung von feinteiligen Farb- oder Wirkstoffzubereitungen |
| ATE183500T1 (de) * | 1994-12-21 | 1999-09-15 | Hoffmann La Roche | Carotenoide ketone und ester |
| DE19603402A1 (de) * | 1995-02-24 | 1996-08-29 | Basf Ag | Weichgelatinekapseln |
| US5747544A (en) * | 1995-10-31 | 1998-05-05 | Applied Food Biotechnology, Inc. | Method of using pure 3R-3'R stereoisomer of zeaxanthin to treat or prevent retinal degeneration in humans |
| CA2188983C (en) | 1995-10-31 | 2001-02-27 | Kevin M. Garnett | Pure 3r-3'r stereoisomer of zeaxanthin for treating macular degeneration in humans |
| US5827652A (en) | 1995-10-31 | 1998-10-27 | Applied Food Biotechnology, Inc. | Zeaxanthin formulations for human ingestion |
| US5854015A (en) * | 1995-10-31 | 1998-12-29 | Applied Food Biotechnology, Inc. | Method of making pure 3R-3'R stereoisomer of zeaxanthin for human ingestion |
| JP3555640B2 (ja) * | 1996-05-10 | 2004-08-18 | ライオン株式会社 | 天然カロチノイドを包含した多芯型構造のマイクロカプセル並びに錠剤、食品用及び医薬品用配合剤 |
| ES2216079T3 (es) * | 1996-05-14 | 2004-10-16 | Dsm Ip Assets B.V. | Procedimiento para la elaboracion de composiciones de carotenoides. |
| DE19637517A1 (de) * | 1996-09-13 | 1998-03-19 | Basf Ag | Herstellung von pulverförmigen, kaltwasserdispergierbaren Carotinoid-Zubereitungen und die Verwendung der neuen Carotinoid-Zubereitungen |
| UA52701C2 (uk) | 1996-10-11 | 2003-01-15 | Басф Акцієнгезельшафт | Твердий засіб захисту рослин та спосіб його одержання, спосіб боротьби з небажаним ростом рослин, спосіб боротьби з шкідливими грибами і тваринами-шкідниками та спосіб регулювання росту рослин |
| DE19649062A1 (de) * | 1996-11-27 | 1998-05-28 | Basf Ag | Flüssige, mit Öl mischbare Carotinoid-Zubereitungen |
| DE19651681A1 (de) * | 1996-12-12 | 1998-06-18 | Basf Ag | Stabile, wäßrige Dispersionen und stabile, wasserdispergierbare Trockenpulver von Xanthopyllen, deren Herstellung und Verwendung |
| DE19653410A1 (de) | 1996-12-20 | 1998-06-25 | Basf Ag | Verwendung von Carotinoid-Solubilisaten zum Färben von Lebensmitteln und pharmazeutischen Zubereitungen |
| US6221417B1 (en) | 1997-05-14 | 2001-04-24 | Kemin Industries, Inc. | Conversion of xanthophylls in plant material for use as a food colorant |
| US5876782A (en) * | 1997-05-14 | 1999-03-02 | Kemin Industries, Inc. | Method for the conversion of xanthophylls in plant material |
| NZ502500A (en) * | 1997-06-27 | 2002-03-28 | Vivorx Pharmaceuticals Inc | Novel formulations of pharmacological agents, methods for the preparation thereof and methods for the use thereof |
| US6007856A (en) * | 1997-08-08 | 1999-12-28 | The Procter & Gamble Company | Oil-in-water dispersions of β-carotene and other carotenoids stable against oxidation prepared from water-dispersible beadlets having high concentrations of carotenoid |
| JPH1160980A (ja) * | 1997-08-13 | 1999-03-05 | Kagome Co Ltd | 水分散性カロテノイド色素製剤 |
| CA2261456A1 (en) * | 1998-02-23 | 1999-08-23 | F. Hoffmann-La Roche Ag | Preparation of a finely divided pulverous carotenoid preparation |
| JP2002503707A (ja) * | 1998-02-23 | 2002-02-05 | ビー・エイ・エス・エフ、コーポレーション | 非加水分解ゼラチンを基とする高い食用油含量を有する噴霧乾燥粉末およびかかる噴霧乾燥して錠剤製造可能な粉末の製造方法 |
| DE19831865A1 (de) | 1998-07-16 | 2000-01-20 | Basf Ag | Verwendung von Schwefel-organischen Verbindungen als Mittel zur bathochromen Verschiebung der UV/Vis-Absorptionsbande von Carotinoiden |
| PE20001227A1 (es) * | 1998-10-30 | 2000-11-06 | Hoffmann La Roche | Procesos para producir una composicion de isotretinoina |
| DE19919751A1 (de) * | 1999-04-29 | 2000-11-09 | Basf Ag | Stabile, wäßrige Dispersionen und stabile, wasserdispergierbare Trockenpulver von Xanthophyllen, deren Herstellung und Verwendung |
| US6582721B1 (en) | 1999-09-17 | 2003-06-24 | Alcon, Inc. | Stable carotene-xanthophyll beadlet compositions and methods of use |
| DE19956848A1 (de) * | 1999-11-26 | 2001-05-31 | Basf Ag | Curcumin-Formulierungen |
| US20050106219A1 (en) * | 2000-05-30 | 2005-05-19 | Karlheinz Bortlik | Primary composition comprising a lipophilic bioactive compound |
| DE60119315T2 (de) * | 2000-05-30 | 2006-08-31 | Société des Produits Nestlé S.A. | Primärzusammensetzung enthaltend einen lipophilen, bioaktiven stoff |
| DE10042833A1 (de) * | 2000-08-30 | 2002-03-14 | Basf Ag | Feste Zubereitungen mit einer Multi-Kern Struktur |
| CA2420597C (en) | 2000-08-31 | 2011-05-17 | Rtp Pharma Inc. | Milled particles |
| US7691406B2 (en) * | 2000-10-27 | 2010-04-06 | ZeaVision LLC. | Zeaxanthin formulations for human ingestion |
| US7105176B2 (en) | 2000-11-29 | 2006-09-12 | Basf Aktiengesellschaft | Production of solid preparations of water-soluble, sparingly water-soluble or water-insoluble active compounds |
| ES2282181T3 (es) * | 2000-11-29 | 2007-10-16 | Basf Aktiengesellschaft | Procedimiento para la obtemncion de preparaciones solidas de productos activos solubles en agua, dificilmente solubles en agua o insolubles en agua. |
| DE10064387A1 (de) * | 2000-12-21 | 2002-06-27 | Basf Ag | Verfahren zur Herstellung von Trockenpulvern eines oder mehrerer Sauerstoff-haltiger Carotinoide |
| EP1227082B1 (en) * | 2001-01-24 | 2004-06-16 | Kuraray Co., Ltd. | Process for producing carotenoid emulsion |
| DE10104494A1 (de) * | 2001-01-31 | 2002-08-01 | Basf Ag | Verfahren zur Herstellung von Trockenpulvern eines oder mehrerer Carotinoide |
| DE20109224U1 (de) * | 2001-06-01 | 2002-10-17 | Dr. Marcus GmbH & Co. KG, 21502 Geesthacht | Farbstoff-Gemisch für Lebensmittel, Pharmazeutika und Kosmetika |
| ES2238588T3 (es) | 2001-06-19 | 2005-09-01 | Dsm Ip Assets B.V. | Procedimiento para la preparacion de dispersiones. |
| IL146737A (en) | 2001-11-26 | 2010-02-17 | Lycored Natural Prod Ind Ltd | Method for protecting lycopene dispersed in tomato fibers |
| US6869501B2 (en) * | 2001-12-20 | 2005-03-22 | 3M Innovative Properties Company | Continuous process for controlled concentration of colloidal solutions |
| US6663900B2 (en) * | 2002-02-01 | 2003-12-16 | Kemin Foods, Lc | Microcapsules having high carotenoid content |
| DE10205362A1 (de) * | 2002-02-08 | 2003-08-21 | Abbott Gmbh & Co Kg | Verfahren zur Herstellung wasserdispergierbarer Trockenpulver von in Wasser schwer löslichen Verbindungen |
| US6936279B2 (en) * | 2002-06-18 | 2005-08-30 | Zeavision Llc | Microcrystalline zeaxanthin with high bioavailability in oily carrier formulations |
| GB0216700D0 (en) * | 2002-07-18 | 2002-08-28 | Astrazeneca Ab | Process |
| DE10246357A1 (de) * | 2002-10-04 | 2004-04-15 | Merck Patent Gmbh | Verwendung von 5-HT2Rezeptorantagonisten |
| EP1405572A1 (en) * | 2002-10-04 | 2004-04-07 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Modified lupin proteins for the preparation of water dispersible product forms of fat soluble compounds |
| US8088363B2 (en) | 2002-10-28 | 2012-01-03 | Zeavision Llc | Protection against sunburn and skin problems with orally-ingested high-dosage zeaxanthin |
| DE10253111A1 (de) * | 2002-11-13 | 2004-05-27 | Basf Ag | Pulverförmige Phytosterol-Formulierungen |
| US9192586B2 (en) | 2003-03-10 | 2015-11-24 | Zeavision Llc | Zeaxanthin formulations with additional ocular-active nutrients, for protecting eye health and treating eye disorders |
| US7785621B2 (en) * | 2003-01-31 | 2010-08-31 | Childrens Hospital Los Angeles | Oral compositions of fenretinide having increased bioavailability and methods of using the same |
| JP2004267041A (ja) * | 2003-03-06 | 2004-09-30 | Sanei Gen Ffi Inc | 微細化固形物分散製剤およびその製造方法 |
| US20070082066A1 (en) * | 2003-05-07 | 2007-04-12 | Gierhart Dennis L | Use of zeaxanthin to reduce light hyper-sensitivity, photophobia, and medical conditions relating to light hyper-sensitivity |
| JP4891773B2 (ja) * | 2003-05-22 | 2012-03-07 | アプライド ナノシステムズ ベー．フェー． | 微小粒子の生成 |
| DE602004022046D1 (de) * | 2003-05-22 | 2009-08-27 | Applied Nanosystems Bv | Herstellung von kleinen teilchen |
| CN1833052B (zh) * | 2003-08-08 | 2010-10-20 | 昭和电工株式会社 | 带有黑膜的基质的生产方法和带有黑膜的基质 |
| DE10342861A1 (de) * | 2003-09-15 | 2005-04-21 | Basf Ag | Pulverförmiger Zubereitungen, enthaltend eine Mischung von 2,4,6-Trianilino-p-(carbo-2'-ethylhexyl-1'-oxi)-1,3,5-triazin und Diethylamino-hydroxybenzoyl-hexyl-benzoat |
| DE10342860A1 (de) * | 2003-09-15 | 2005-04-21 | Basf Ag | Pulverförmiger Zubereitungen, enthaltend Diethylaminohydroxybenzoyl-hexyl-benzoat |
| US7541166B2 (en) * | 2003-09-19 | 2009-06-02 | Microfluidic Systems, Inc. | Sonication to selectively lyse different cell types |
| DE10351087A1 (de) * | 2003-10-31 | 2005-05-25 | Bayer Technology Services Gmbh | Feste Wirkstoff-Formulierung |
| US7941211B2 (en) * | 2003-11-17 | 2011-05-10 | Zeavision, Llc. | Preloading with macular pigment to improve photodynamic treatment of retinal vascular disorders |
| DE102004030072A1 (de) * | 2004-06-23 | 2006-01-19 | Basf Ag | Wässrige Dispersionen schwer wasserlöslicher oder wasserunlöslicher Wirkstoffe und daraus hergestellte Trockenpulver |
| US20070248683A1 (en) * | 2004-08-19 | 2007-10-25 | Elger Funda | Novel Compositions of Fat-Soluble Substances |
| DE102004046026A1 (de) * | 2004-09-21 | 2006-03-23 | Basf Ag | Verfahren zur Herstellung von Trockenpulvern eines oder mehrerer Carotinoide |
| US10463061B2 (en) | 2004-11-19 | 2019-11-05 | Dsm Ip Assets B.V. | Modified plant gums for preparations of active ingredients |
| DE102004057587A1 (de) * | 2004-11-29 | 2006-06-08 | Basf Ag | Wässrige Dispersionen eines Gemisches schwer wasserlöslicher oder wasserunlöslicher Wirkstoffe und eines Einzellerproteinmaterials und daraus hergestellte Trockenpulver |
| US20060182826A1 (en) * | 2005-02-11 | 2006-08-17 | Kalamazoo Holdings, Inc. | Extracts of Asteraceae containing reduced levels of phototoxic thiophene derivatives and methods for preparing same |
| US8592662B2 (en) | 2005-02-11 | 2013-11-26 | Kalamazoo Holdings, Inc. | Capsicum variety exhibiting a hyper-accumulation of zeaxanthin and products derived therefrom |
| EP1880007A2 (en) | 2005-05-05 | 2008-01-23 | Genencor International, Inc. | Personal care compositions and methods for their use |
| DE102005026755A1 (de) * | 2005-06-09 | 2006-12-14 | Basf Ag | Herstellung von festen Lösungen schwerlöslicher Wirkstoffe durch Kurzzeitüberhitzung und schnelle Trocknung |
| DE102005030952A1 (de) | 2005-06-30 | 2007-01-18 | Basf Ag | Verfahren zur Herstellung einer wässrigen Suspension und einer pulverförmigen Zubereitung eines oder mehrerer Carotinoide |
| DE102005031468A1 (de) * | 2005-07-04 | 2007-01-18 | Basf Ag | Wässrige Suspensionen schwer wasserlöslicher oder wasserunlöslicher Wirkstoffe und daraus hergestellte Trockenpulver |
| JP5275561B2 (ja) * | 2006-10-30 | 2013-08-28 | 富士フイルム株式会社 | 水分散可能なナノ粒子 |
| US20100041607A1 (en) * | 2007-01-16 | 2010-02-18 | Basf Se | Unctuous compositions |
| CN101583286B (zh) | 2007-01-16 | 2013-08-21 | 巴斯夫欧洲公司 | 含有类胡萝卜素的液体配制剂 |
| JP2010518829A (ja) * | 2007-02-23 | 2010-06-03 | ビーエーエスエフ ソシエタス・ヨーロピア | 味覚変容物質としての水分散性カロテノイドナノ粒子の使用、水分散性カロテノイドナノ粒子を含む味覚変容物質、および味覚変容方法 |
| DK2142011T3 (da) * | 2007-02-23 | 2011-04-18 | Brain Biotechnology Res & Information Network Ag | Fremgangsmåde til smagsmodulering af stofsammensætninger, der indeholder mindst ét højintensitetssødemiddel (HIS) |
| TW200918096A (en) * | 2007-06-22 | 2009-05-01 | Kaneka Corp | Composition comprising bioactive substance |
| TW200916090A (en) * | 2007-06-22 | 2009-04-16 | Kaneka Corp | Composition comprising coenzyme Q10 |
| ES2311422B1 (es) | 2007-07-28 | 2009-10-13 | Investigaciones Quimicas Y Farmaceuticas, S.A | Formulacion de carotenoides dispersables en agua. |
| US20110123505A1 (en) * | 2007-08-22 | 2011-05-26 | Kaneka Corporation | Method of producing reduced coenzyme q10 and method of stabilizing the same |
| 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 |
| DE102007048705A1 (de) | 2007-10-11 | 2009-04-16 | Bayer Healthcare Ag | Amorphe Formulierung |
| US11185093B2 (en) | 2007-11-29 | 2021-11-30 | Christian Köpsel | Pulverulent carotenoid preparation for colouring drinks |
| DK2343986T4 (da) | 2008-10-07 | 2021-07-26 | Basf Se | Brugsklar, stabil emulsion |
| US7803902B2 (en) | 2008-10-15 | 2010-09-28 | Danisco Us Inc. | Modified variant bowman birk protease inhibitors |
| US7772181B2 (en) | 2008-10-15 | 2010-08-10 | Danisco Us Inc. | Personal care compositions comprising modified variant Bowman Birk Protease Inhibitors |
| CN102245635B (zh) | 2008-10-15 | 2016-08-31 | 丹尼斯科美国公司 | 修饰的变体bowman birk蛋白酶抑制剂 |
| EP2210593A3 (en) | 2009-01-21 | 2011-05-18 | DSM IP Assets B.V. | Tablettable formulations of vitamin A and derivatives thereof |
| JP5149837B2 (ja) * | 2009-02-27 | 2013-02-20 | Ｊｘ日鉱日石エネルギー株式会社 | カロテノイドの製造方法 |
| DK2403360T3 (en) | 2009-03-05 | 2016-12-05 | Basf Se | Formulation of astaxanthin DERIVATIVES AND USE THEREOF III |
| CN102341006A (zh) | 2009-03-05 | 2012-02-01 | 巴斯夫欧洲公司 | 虾青素衍生物的粉状组合物ii |
| ES2400146T3 (es) | 2009-03-05 | 2013-04-05 | Basf Se | Composición pulverulenta de derivados de astaxantina l |
| CN101549273B (zh) | 2009-03-30 | 2011-06-15 | 浙江新和成股份有限公司 | 纳米分散的高全反式类胡萝卜素微胶囊的制备方法 |
| ES2621184T3 (es) | 2009-03-30 | 2017-07-03 | Basf Se | Suspensión estable, lista para su uso, de partículas de beta-caroteno parcialmente amorfas |
| WO2012017012A1 (de) | 2010-08-05 | 2012-02-09 | Basf Se | Stabilisator |
| DK2687103T4 (da) * | 2012-07-20 | 2024-10-14 | Basf Se | Fremgangsmåde til fremstilling af en vandig transparent olie-i-vand-emulsion, der omfatter et carotenoid, og en fremstillet emulsion |
| CN105188408B (zh) | 2012-12-19 | 2019-03-01 | 诺华丝国际股份有限公司 | 叶黄素类组合物和使用方法 |
| CN104274428B (zh) * | 2013-07-09 | 2016-04-13 | 浙江新维普添加剂有限公司 | 油分散性类胡萝卜素制剂的制备方法 |
| MX380860B (es) * | 2014-08-01 | 2025-03-12 | Firmenich & Cie | Dispersion solida de compuestos con sabor de amida. |
| BR112017022430A2 (pt) | 2015-04-22 | 2018-07-10 | Basf Se | ?dispersões, processos para preparar dispersões e partículas sólidas das dispersões, uso das dispersões, preparações, e, partículas sólidas? |
| JP2019516345A (ja) | 2016-03-02 | 2019-06-20 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 振動液滴形成 |
| CN108777981A (zh) * | 2016-03-24 | 2018-11-09 | 巴斯夫欧洲公司 | 多相活性物质制剂 |
| WO2018015346A1 (de) * | 2016-07-19 | 2018-01-25 | Basf Se | Propylgallathaltige vitaminzubereitungen |
| US20220298069A1 (en) | 2019-06-14 | 2022-09-22 | Basf Se | Stabilized gypsum particles |
| CN111903846B (zh) | 2020-07-31 | 2023-10-31 | 浙江新和成股份有限公司 | 一种稳定、高生物利用度的类胡萝卜素微胶囊及其制备方法 |
| EP4186370B1 (en) | 2021-11-26 | 2023-11-01 | Oterra A/S | Carotenoid coloring composition for cheese products |
| CN114276285B (zh) * | 2021-12-28 | 2024-06-04 | 大连医诺生物股份有限公司 | 一种类胡萝卜素制剂、其制备方法及应用 |
| WO2025008385A1 (en) | 2023-07-03 | 2025-01-09 | Basf Se | Solid preparations of beta-carotene |
| WO2025206390A1 (ja) * | 2024-03-29 | 2025-10-02 | 三栄源エフ・エフ・アイ株式会社 | カロテン含有組成物、及びその製造方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3125451A (en) * | 1964-03-17 | S-carotene | ||
| DE642307C (de) | 1929-12-08 | 1937-03-01 | I G Farbenindustrie Akt Ges | Verfahren zur gleichmaessigen Verteilung der fettloeslichen Vitamine in waessrigen Fluessigkeiten |
| US2650895A (en) | 1947-02-24 | 1953-09-01 | Mead Johnson & Co | Spray dried vitamin a and d emulsion |
| FR1056114A (fr) | 1950-12-06 | 1954-02-24 | Philips Nv | Produit vitaminé sec se prêtant au saupoudrage, obtenu par un séchage par pulvérisation, et son procédé de préparation |
| CH304023A (de) | 1951-01-15 | 1954-12-31 | Hoffmann La Roche | Verfahren zur Färbung von zur Herstellung von Nahrungsmitteln bestimmten Mitteln. |
| DE861637C (de) | 1951-01-16 | 1953-01-05 | Hoffmann La Roche Ag Deutsche | Verfahren zur Faerbung von Nahrungsmitteln |
| FR1219213A (fr) * | 1956-12-13 | 1960-05-16 | Hoffmann La Roche | Procédé pour la préparation de compositions de caroténoïdes dispersibles dans l'eau |
| DE1211911B (de) * | 1959-09-08 | 1966-03-03 | Hoffmann La Roche | Verfahren zur Herstellung eines insbesondere zum Faerben von Lebens- und Futtermitteln geeigneten Carotinoidpraeparates |
| US3110598A (en) * | 1959-09-08 | 1963-11-12 | Hoffmann La Roche | Process of making a carotenoid preparation |
| CH522717A (de) * | 1969-02-07 | 1972-06-30 | Hoffmann La Roche | Färbepräparat |
| US3734745A (en) * | 1970-11-23 | 1973-05-22 | Gen Foods Corp | Multi-layered, multi-colored desserts |
| JPS5124932Y2 (enExample) * | 1971-06-12 | 1976-06-25 | ||
| US3790688A (en) * | 1972-03-15 | 1974-02-05 | Us Agriculture | Water dispersible beta-carotene |
| IL44352A (en) * | 1973-03-16 | 1977-07-31 | Ciba Geigy Ag | Preparation of non-dusty easily wetted and readily soluble granulates |
| US3998753A (en) | 1974-08-13 | 1976-12-21 | Hoffmann-La Roche Inc. | Water dispersible carotenoid preparations and processes thereof |
| JPS5284232A (en) * | 1976-01-01 | 1977-07-13 | Hoffmann La Roche | Powder compositions containing waterrdispersible carotenoid |
| US4316917A (en) * | 1980-04-21 | 1982-02-23 | Hoffman-La Roche Inc. | Stable carotenoid solutions |
-
1981
- 1981-05-15 DE DE19813119383 patent/DE3119383A1/de not_active Withdrawn
-
1982
- 1982-05-05 EP EP82103838A patent/EP0065193B1/de not_active Expired
- 1982-05-05 AT AT82103838T patent/ATE16814T1/de not_active IP Right Cessation
- 1982-05-05 DE DE8282103838T patent/DE3267761D1/de not_active Expired
- 1982-05-07 IL IL65707A patent/IL65707A/xx not_active IP Right Cessation
- 1982-05-10 US US06/376,585 patent/US4522743A/en not_active Expired - Lifetime
- 1982-05-12 CA CA000402846A patent/CA1202809A/en not_active Expired
- 1982-05-13 DK DK216082A patent/DK154395C/da not_active IP Right Cessation
- 1982-05-14 JP JP57080314A patent/JPS57195161A/ja active Granted
- 1982-05-14 AU AU83725/82A patent/AU553623B2/en not_active Expired
-
1988
- 1988-06-17 DK DK334188A patent/DK157311C/da not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0986963B1 (de) | 1998-09-14 | 2016-12-07 | Basf Se | Stabile, pulverförmige Lycopin-Formulierungen, enthaltend Lycopin mit einem Kristallinitätsgrad von grösser 20% |
Also Published As
| Publication number | Publication date |
|---|---|
| AU553623B2 (en) | 1986-07-24 |
| JPS57195161A (en) | 1982-11-30 |
| DK334188A (da) | 1988-06-17 |
| IL65707A (en) | 1985-03-31 |
| EP0065193B1 (de) | 1985-12-04 |
| EP0065193A3 (en) | 1983-07-06 |
| JPH0335347B2 (enExample) | 1991-05-27 |
| DK154395C (da) | 1989-04-10 |
| IL65707A0 (en) | 1982-08-31 |
| EP0065193A2 (de) | 1982-11-24 |
| DK154395B (da) | 1988-11-14 |
| DK216082A (da) | 1982-11-16 |
| AU8372582A (en) | 1982-11-18 |
| DE3267761D1 (en) | 1986-01-16 |
| DK157311C (da) | 1990-05-07 |
| US4522743A (en) | 1985-06-11 |
| DK157311B (da) | 1989-12-11 |
| DE3119383A1 (de) | 1982-12-02 |
| DK334188D0 (da) | 1988-06-17 |
| ATE16814T1 (de) | 1985-12-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1202809A (en) | Preparation of finely divided pulverulent carotinoid and retinoid compositions | |
| US4726955A (en) | Preparation of finely divided, pulverulent carotenoid preparations | |
| CA2214480C (en) | The production of carotenoid preparations in the form of coldwater-dispersible powders, and the use of the novel carotenoid preparations | |
| CA1330270C (en) | Pulverulent, water-dispersable carotenoid formulations and their preparation | |
| JP4124821B2 (ja) | キサントフィル類の安定な水性分散液および安定な水−分散性乾燥粉末、それらの製造および使用 | |
| JP3884817B2 (ja) | 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 | |
| DK0986963T3 (en) | Stable, powdery lycopene formulations containing lycopene with a crystallinity degree greater than 20% | |
| EP0937412B1 (en) | Preparation of a finely divided pulverous carotenoid preparation | |
| US4844934A (en) | Preparation of finely divided, water-dispersable carotenoid formulations | |
| EP1794238A2 (de) | Verfahren zur herstellung von trockenpulvern eines oder mehrerer carotinoide | |
| JP2002327133A (ja) | １種以上のカロテノイドを含む乾燥粉末の製造方法 | |
| JP2007521812A (ja) | １種又は数種のカロチノイドの乾燥粉末の製造方法 | |
| EP0628258A1 (en) | Granular colorant and formula feed containing the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |