NO328928B1 - Astaksantinestere - Google Patents
Astaksantinestere Download PDFInfo
- Publication number
- NO328928B1 NO328928B1 NO20043728A NO20043728A NO328928B1 NO 328928 B1 NO328928 B1 NO 328928B1 NO 20043728 A NO20043728 A NO 20043728A NO 20043728 A NO20043728 A NO 20043728A NO 328928 B1 NO328928 B1 NO 328928B1
- Authority
- NO
- Norway
- Prior art keywords
- astaxanthin
- denotes
- group
- derivative
- alkyl
- Prior art date
Links
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 150
- 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 claims description 103
- 239000001168 astaxanthin Substances 0.000 claims description 103
- 235000013793 astaxanthin Nutrition 0.000 claims description 103
- 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 claims description 103
- 229940022405 astaxanthin Drugs 0.000 claims description 103
- 150000001514 astaxanthins Chemical class 0.000 claims description 43
- -1 halogen ion Chemical class 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 25
- 239000000243 solution Substances 0.000 claims description 24
- 241001465754 Metazoa Species 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- 238000009472 formulation Methods 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 235000021466 carotenoid Nutrition 0.000 claims description 10
- 150000001747 carotenoids Chemical class 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 9
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000001413 amino acids Chemical class 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 235000013305 food Nutrition 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 150000008065 acid anhydrides Chemical class 0.000 claims description 5
- FFYPMLJYZAEMQB-UHFFFAOYSA-N diethyl pyrocarbonate Chemical compound CCOC(=O)OC(=O)OCC FFYPMLJYZAEMQB-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- SMNDYUVBFMFKNZ-UHFFFAOYSA-M 2-furoate Chemical compound [O-]C(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-M 0.000 claims description 4
- NQTOFVGQJZECML-UHFFFAOYSA-N CCOC(C(O)=O)=O.CCOC(C(O)=O)=O Chemical compound CCOC(C(O)=O)=O.CCOC(C(O)=O)=O NQTOFVGQJZECML-UHFFFAOYSA-N 0.000 claims description 4
- OKJIRPAQVSHGFK-UHFFFAOYSA-M N-acetylglycinate Chemical compound CC(=O)NCC([O-])=O OKJIRPAQVSHGFK-UHFFFAOYSA-M 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 239000000084 colloidal system Substances 0.000 claims description 4
- 239000000839 emulsion Substances 0.000 claims description 4
- 239000003925 fat Substances 0.000 claims description 4
- 238000001027 hydrothermal synthesis Methods 0.000 claims description 4
- 238000010348 incorporation Methods 0.000 claims description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
- 239000010773 plant oil Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 230000001681 protective effect Effects 0.000 claims description 4
- 238000001694 spray drying Methods 0.000 claims description 4
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 4
- 235000019871 vegetable fat Nutrition 0.000 claims description 4
- 239000008158 vegetable oil Substances 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- CAOMCZAIALVUPA-UHFFFAOYSA-N 3-(methylthio)propionic acid Chemical compound CSCCC(O)=O CAOMCZAIALVUPA-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 claims description 3
- 230000019612 pigmentation Effects 0.000 claims description 3
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
- PHELOKYCCWVWFE-UHFFFAOYSA-N 2,2-dimethoxyacetic acid Chemical compound COC(OC)C(O)=O PHELOKYCCWVWFE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- DQVWXLRNCXQVKH-UHFFFAOYSA-N acetyl 2-hydroxy-2-phenylacetate Chemical compound CC(=O)OC(=O)C(O)C1=CC=CC=C1 DQVWXLRNCXQVKH-UHFFFAOYSA-N 0.000 claims description 2
- 235000013795 astaxanthin dimethyldisuccinate Nutrition 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims 1
- 102000004169 proteins and genes Human genes 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 30
- 239000013078 crystal Substances 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000003756 stirring Methods 0.000 description 17
- 238000004128 high performance liquid chromatography Methods 0.000 description 16
- 238000001035 drying Methods 0.000 description 15
- 238000001914 filtration Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- 238000005406 washing Methods 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 241000251468 Actinopterygii Species 0.000 description 9
- 241000277331 Salmonidae Species 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000032050 esterification Effects 0.000 description 9
- 238000005886 esterification reaction Methods 0.000 description 9
- 235000013372 meat Nutrition 0.000 description 9
- 235000019688 fish Nutrition 0.000 description 8
- 239000002002 slurry Substances 0.000 description 8
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 230000015556 catabolic process Effects 0.000 description 7
- 238000006731 degradation reaction Methods 0.000 description 7
- 238000001125 extrusion Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000004040 coloring Methods 0.000 description 6
- 235000019621 digestibility Nutrition 0.000 description 6
- 235000015170 shellfish Nutrition 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 150000007517 lewis acids Chemical class 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- SCCCIUGOOQLDGW-UHFFFAOYSA-N 1,1-dicyclohexylurea Chemical compound C1CCCCC1N(C(=O)N)C1CCCCC1 SCCCIUGOOQLDGW-UHFFFAOYSA-N 0.000 description 3
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 3
- KXVSPEKPHLCWFE-UHFFFAOYSA-N 4-ethoxy-4-oxobutanoic acid Chemical compound CCOC(=O)CCC(O)=O.CCOC(=O)CCC(O)=O KXVSPEKPHLCWFE-UHFFFAOYSA-N 0.000 description 3
- 241000972773 Aulopiformes Species 0.000 description 3
- 241000238557 Decapoda Species 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 125000004450 alkenylene group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 238000009360 aquaculture Methods 0.000 description 3
- 244000144974 aquaculture Species 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 235000019515 salmon Nutrition 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- 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 description 2
- XIPKYVDPRSVTSK-UHFFFAOYSA-N 2-hydroxy-2-(oxan-2-yl)propanoic acid Chemical compound OC(=O)C(O)(C)C1CCCCO1 XIPKYVDPRSVTSK-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 2
- OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 2
- 241000277263 Salmo Species 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000378 calcium silicate Substances 0.000 description 2
- 229910052918 calcium silicate Inorganic materials 0.000 description 2
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical group C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 239000002612 dispersion medium Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000013505 freshwater Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229910052757 nitrogen Chemical group 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CSSBGISTZHPJPH-UHFFFAOYSA-N 2-(chloromethyl)-8-phenylmethoxyimidazo[1,2-a]pyridine Chemical compound C12=NC(CCl)=CN2C=CC=C1OCC1=CC=CC=C1 CSSBGISTZHPJPH-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- UYCUMNRCCJNSBR-UHFFFAOYSA-N 2-ethoxy-2-oxoacetic acid;hydrochloride Chemical compound Cl.CCOC(=O)C(O)=O UYCUMNRCCJNSBR-UHFFFAOYSA-N 0.000 description 1
- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 1
- KWFCSMSCNOVLBA-UHFFFAOYSA-N 2-hydroxy-3-oxobutanoic acid Chemical compound CC(=O)C(O)C(O)=O KWFCSMSCNOVLBA-UHFFFAOYSA-N 0.000 description 1
- XWGXLRRTBBCVMC-UHFFFAOYSA-N 2-methylbutanedioyl dichloride Chemical compound ClC(=O)C(C)CC(Cl)=O XWGXLRRTBBCVMC-UHFFFAOYSA-N 0.000 description 1
- SMJRBWINMFUUDS-UHFFFAOYSA-N 2-thienylacetic acid Chemical compound OC(=O)CC1=CC=CS1 SMJRBWINMFUUDS-UHFFFAOYSA-N 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 241000238017 Astacoidea Species 0.000 description 1
- 241000252229 Carassius auratus Species 0.000 description 1
- 241001609213 Carassius carassius Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000019733 Fish meal Nutrition 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- SGXDXUYKISDCAZ-UHFFFAOYSA-N N,N-diethylglycine Chemical compound CCN(CC)CC(O)=O SGXDXUYKISDCAZ-UHFFFAOYSA-N 0.000 description 1
- 241000277334 Oncorhynchus Species 0.000 description 1
- 241001327682 Oncorhynchus mykiss irideus Species 0.000 description 1
- 241001282110 Pagrus major Species 0.000 description 1
- 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 1
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- 241000316146 Salmo trutta trutta Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(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 OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 235000021120 animal protein Nutrition 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 235000013734 beta-carotene Nutrition 0.000 description 1
- 239000011648 beta-carotene Substances 0.000 description 1
- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene 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=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 description 1
- 229960002747 betacarotene Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 235000012682 canthaxanthin Nutrition 0.000 description 1
- 239000001659 canthaxanthin Substances 0.000 description 1
- 229940008033 canthaxanthin Drugs 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 235000018823 dietary intake Nutrition 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- FPULFENIJDPZBX-UHFFFAOYSA-N ethyl 2-isocyanoacetate Chemical compound CCOC(=O)C[N+]#[C-] FPULFENIJDPZBX-UHFFFAOYSA-N 0.000 description 1
- IXZFDJXHLQQSGQ-UHFFFAOYSA-N ethyl 4-chloro-4-oxobutanoate Chemical compound CCOC(=O)CCC(Cl)=O IXZFDJXHLQQSGQ-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 235000013332 fish product Nutrition 0.000 description 1
- 239000004467 fishmeal Substances 0.000 description 1
- 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 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
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- 238000009309 intensive farming Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229940006461 iodide ion Drugs 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229940116871 l-lactate Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 210000001087 myotubule Anatomy 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- JEDHEXUPBRMUMB-UHFFFAOYSA-N n,n-dimethylpyridin-3-amine Chemical compound CN(C)C1=CC=CN=C1 JEDHEXUPBRMUMB-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- RVEBJDGWKWKYBH-UHFFFAOYSA-N o-methyl propanethioate Chemical compound CCC(=S)OC RVEBJDGWKWKYBH-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
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- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
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- 239000005017 polysaccharide Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
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- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
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- 239000003381 stabilizer Substances 0.000 description 1
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- 125000003107 substituted aryl group Chemical group 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- AIILTVHCLAEMDA-UHFFFAOYSA-N thiopropionic acid S-methyl ester Natural products CCC(=O)SC AIILTVHCLAEMDA-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
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- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(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\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 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
- 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
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/179—Colouring agents, e.g. pigmenting or dyeing agents
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/80—Feeding-stuffs specially adapted for particular animals for aquatic animals, e.g. fish, crustaceans or molluscs
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
- Y02A40/80—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in fisheries management
- Y02A40/81—Aquaculture, e.g. of fish
- Y02A40/818—Alternative feeds for fish, e.g. in aquacultures
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Insects & Arthropods (AREA)
- Nutrition Science (AREA)
- Marine Sciences & Fisheries (AREA)
- Birds (AREA)
- Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fodder In General (AREA)
- Feed For Specific Animals (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02002728 | 2002-02-06 | ||
| PCT/EP2003/000873 WO2003066583A1 (en) | 2002-02-06 | 2003-01-29 | Astaxanthin esters |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20043728D0 NO20043728D0 (no) | 2004-09-06 |
| NO20043728L NO20043728L (no) | 2004-09-06 |
| NO328928B1 true NO328928B1 (no) | 2010-06-21 |
Family
ID=27675607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20043728A NO328928B1 (no) | 2002-02-06 | 2004-09-06 | Astaksantinestere |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US7253297B2 (enExample) |
| EP (1) | EP1474388B2 (enExample) |
| JP (1) | JP4420675B2 (enExample) |
| KR (1) | KR100958483B1 (enExample) |
| CN (1) | CN100375740C (enExample) |
| AU (1) | AU2003205699B8 (enExample) |
| CA (1) | CA2474208C (enExample) |
| DE (1) | DE60317770T3 (enExample) |
| ES (1) | ES2297125T5 (enExample) |
| IN (1) | IN2004CH01714A (enExample) |
| MX (1) | MX247604B (enExample) |
| NO (1) | NO328928B1 (enExample) |
| WO (1) | WO2003066583A1 (enExample) |
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| US20080008798A1 (en) * | 2002-02-06 | 2008-01-10 | Arnold Gloor | Salts of astaxathin esters |
| EP2392562B1 (en) * | 2002-07-29 | 2018-03-07 | Cardax Pharma, Inc. | Structural carotenoid analogs for the inhibition and amelioration of disease |
| US7521584B2 (en) | 2002-07-29 | 2009-04-21 | Cardax Pharmaceuticals, Inc. | Carotenoid analogs or derivatives for the inhibition and amelioration of disease |
| US7345091B2 (en) | 2002-07-29 | 2008-03-18 | Cardax Pharmaceuticals, Inc. | Carotenoid ether analogs or derivatives for the inhibition and amelioration of disease |
| US7375133B2 (en) | 2002-07-29 | 2008-05-20 | Cardax Pharmaceuticals, Inc. | Pharmaceutical compositions including carotenoid ether analogs or derivatives for the inhibition and amelioration of disease |
| US7320997B2 (en) | 2002-07-29 | 2008-01-22 | Cardax Pharmaceuticals, Inc. | Pharmaceutical compositions including carotenoid ester analogs or derivatives for the inhibition and amelioration of disease |
| EP1563081A4 (en) * | 2002-10-25 | 2005-10-26 | PROCESS FOR PRODUCING ESTERIFIED ASTAXANTHIN FROM ESTERIFIED ZEAXANTHINE | |
| EP1750723A1 (en) * | 2004-04-14 | 2007-02-14 | Hawaii Biotech, Inc. | Carotenoid analogs or derivatives for the inhibition and amelioration of inflammation |
| AU2005289313B2 (en) | 2004-09-28 | 2012-02-09 | Avivagen Inc. | Compositions and methods for promoting weight gain and feed conversion |
| US20060178538A1 (en) | 2004-10-01 | 2006-08-10 | Lockwood Samuel F | Methods for the synthesis of chiral dihydroxy intermediates useful for the chiral synthesis of carotenoids |
| EP1797169A4 (en) | 2004-10-08 | 2008-11-19 | Coho Hydroclean Sa | PROCESS FOR THE CULTIVATION OF ANIMALS WITH THE DESIRED COLOR AND INCREASED GROWTH RATE |
| BRPI0609040B1 (pt) | 2005-03-18 | 2018-07-31 | Microbia, Inc. | Fungo recombinante do gênero yarrowia, método de produção de um carotenóide e método de preparo de um aditivo alimentício ou ração contendo um carotenóide |
| US20060270590A1 (en) | 2005-03-29 | 2006-11-30 | Lockwood Samuel F | Reduction in complement activation and inflammation during tissue injury by carotenoids, carotenoid analogs, or derivatives thereof |
| JP2009532041A (ja) * | 2006-04-05 | 2009-09-10 | ケマファー インコーポレーテッド | 食品栄養補助剤及びその使用 |
| US20070293568A1 (en) | 2006-06-16 | 2007-12-20 | Yamaha Hatsudoki Kabushiki Kaisha | Neurocyte Protective Agent |
| EP2078092A2 (en) | 2006-09-28 | 2009-07-15 | Microbia, Inc. | Production of carotenoids in oleaginous yeast and fungi |
| US8809398B2 (en) | 2007-01-16 | 2014-08-19 | Basf Se | Liquid formulations containing a carotinoid |
| EP1952845A1 (en) | 2007-01-26 | 2008-08-06 | DSMIP Assets B.V. | Use of an astaxathin derivative for cosmetic purposes |
| WO2009027499A2 (de) * | 2007-08-31 | 2009-03-05 | Basf Se | Verfahren zur herstellung von öligen lösungen von astaxanthin-derivaten |
| DK2214656T3 (en) | 2007-10-26 | 2019-03-25 | Avivagen Inc | COMPOSITIONS AND PROCEDURES TO ENHANCE IMMUNE RESPONSE |
| US11185093B2 (en) | 2007-11-29 | 2021-11-30 | Christian Köpsel | Pulverulent carotenoid preparation for colouring drinks |
| WO2009112506A1 (en) * | 2008-03-11 | 2009-09-17 | Dsm Ip Assets B.V. | Novel use of carotenoid (ester)s |
| US9375387B2 (en) | 2008-10-07 | 2016-06-28 | Basf Se | Ready-to-use, stable emulsion |
| EP2358217A4 (en) * | 2008-11-28 | 2014-04-30 | Pronova Biopharma Norge As | COMPOSITION WITH / WITHOUT AT LEAST ONE EASILY OXIDIZABLE COMPONENT WITH A PROCESSED EDIBLE OIL OR FAT MIXTURE FOR GROWTH PROMOTION IN ONE ANIMAL, OXIDATIVE STRESS INHIBITION, PREVENTION OF LIVER ENLARGEMENT IN FISHING AND FEED COMPOSITION |
| WO2010100232A2 (de) * | 2009-03-05 | 2010-09-10 | Basf Se | Formulierung von astaxanthin-derivaten und deren verwendung iii |
| CN102341004B (zh) * | 2009-03-05 | 2014-04-16 | 巴斯夫欧洲公司 | 虾青素衍生物的粉状组合物i |
| CN102341003A (zh) * | 2009-03-05 | 2012-02-01 | 巴斯夫欧洲公司 | 虾青素衍生物的配制剂及其应用ii |
| CN102340998B (zh) * | 2009-03-05 | 2014-03-26 | 巴斯夫欧洲公司 | 虾青素衍生物的配制剂及其应用i |
| ES2399986T3 (es) * | 2009-03-05 | 2013-04-04 | Basf Se | Procedimiento para la obtención de disoluciones de derivados de astaxantina |
| ES2400351T3 (es) * | 2009-03-05 | 2013-04-09 | Basf Se | Composiciones pulverulentas de derivados de astaxantina ll |
| AU2010242502B2 (en) | 2009-04-30 | 2016-11-10 | Avivagen Inc. | Methods and compositions for improving the health of animals |
| TWI501946B (zh) | 2010-02-08 | 2015-10-01 | Basf Se | 蝦紅素二琥珀酸二甲酯之製造方法 |
| US8492579B2 (en) | 2010-02-08 | 2013-07-23 | Basf Se | Method for producing astaxanthin dimethyldisuccinate |
| GB201009271D0 (en) | 2010-06-02 | 2010-07-21 | Promar As | Compositions |
| WO2015021352A2 (en) | 2013-08-08 | 2015-02-12 | Knipbio | Methylotrophs for aquaculture and animal feed |
| WO2015178404A1 (ja) | 2014-05-20 | 2015-11-26 | 富士化学工業株式会社 | カロテノイド誘導体、その薬学上許容される塩又はその薬学上許容されるエステル類若しくはアミド類 |
| CA2958386A1 (en) * | 2014-09-11 | 2016-03-17 | Basf Se | Method for preparing astaxanthin esters |
| EP3207028B1 (en) * | 2014-10-19 | 2020-05-27 | Shenkar College of Engineering and Design | Astaxanthin based polymer and uses thereof |
| CN106543323B (zh) * | 2015-09-23 | 2018-10-16 | 合肥炜烨光学科技有限公司 | 一种聚类胡萝卜素丙烯酸酯蓝光吸收剂及其制备方法 |
| CN105504865A (zh) * | 2015-12-15 | 2016-04-20 | 重庆大学 | 一种酯化修饰萝卜红色素的制备及纯化方法 |
| CN105646869B (zh) * | 2016-01-04 | 2018-01-16 | 中国海洋大学 | 一种水溶性虾青素衍生物及其制备方法 |
| CN109689610A (zh) * | 2016-09-16 | 2019-04-26 | 巴斯夫欧洲公司 | 制备作为类胡萝卜素的结构单元的12’-阿朴胡萝卜素醛酯的方法 |
| CN106748946A (zh) * | 2017-02-14 | 2017-05-31 | 烟台固特丽生物科技股份有限公司 | 一种含水溶性虾青素作物营养液的制备方法 |
| CN114761380A (zh) * | 2019-09-27 | 2022-07-15 | 科达士公司 | 虾青素酯及其使用方法 |
| WO2022140580A1 (en) | 2020-12-24 | 2022-06-30 | Orn Almarsson | Xanthophyll derivatives |
| EP4267118A4 (en) * | 2020-12-24 | 2025-01-22 | Axelyf ehf. | XANTHOPHYLL DERIVATIVES |
| EP4067342B1 (en) | 2021-04-02 | 2023-12-27 | Kemijski Institut / National Institute of Chemistry | Sustainable preparation of xanthophyll esters |
| CN118108646B (zh) * | 2024-04-22 | 2024-08-02 | 潍坊富邦药业有限公司 | 一种水溶性虾青素衍生物及其制备方法 |
| CN118063368B (zh) * | 2024-04-22 | 2024-08-02 | 潍坊富邦药业有限公司 | 一种水溶性虾青素衍生物及其合成方法 |
| CN118084755B (zh) * | 2024-04-22 | 2024-08-02 | 潍坊富邦药业有限公司 | 一种高水溶性虾青素衍生物及制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4871551A (en) | 1988-02-08 | 1989-10-03 | Microbio Resources, Inc. | Pigmentation supplements for animal feed compositions |
| JPH01202261A (ja) | 1988-02-09 | 1989-08-15 | Kyowa Hakko Kogyo Co Ltd | 赤色魚用餌料と赤色魚の養殖方法 |
| DE4322277A1 (de) * | 1993-07-05 | 1995-01-12 | Basf Ag | Verbessertes Verfahren zur Herstellung von Astaxanthin, neue Zwischenprodukte hierfür sowie ein Verfahren zu deren Herstellung |
| DE4430289A1 (de) * | 1993-09-04 | 1995-03-09 | Basf Ag | Verbessertes Verfahren zur Herstellung von Astaxanthin |
| JPH07300421A (ja) † | 1994-04-28 | 1995-11-14 | Itano Reitou Kk | 抗炎症剤 |
| DE19649062A1 (de) | 1996-11-27 | 1998-05-28 | Basf Ag | Flüssige, mit Öl mischbare Carotinoid-Zubereitungen |
| US5959138A (en) † | 1997-11-25 | 1999-09-28 | Industrial Organica S.A. De C.V. | Short chain diesters and process for making the same |
| CA2261456A1 (en) † | 1998-02-23 | 1999-08-23 | F. Hoffmann-La Roche Ag | Preparation of a finely divided pulverous carotenoid preparation |
| NL1010351C2 (nl) † | 1998-10-19 | 2001-01-08 | Werklust & Beheer B V | Esters van caroteno´den voor gebruik in de preventie en behandeling van oogaandoeningen. |
| NO309386B1 (no) * | 1999-04-19 | 2001-01-22 | Norsk Hydro As | Pigment |
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2003
- 2003-01-29 MX MXPA04007557 patent/MX247604B/es active IP Right Grant
- 2003-01-29 AU AU2003205699A patent/AU2003205699B8/en not_active Ceased
- 2003-01-29 CA CA2474208A patent/CA2474208C/en not_active Expired - Lifetime
- 2003-01-29 JP JP2003565958A patent/JP4420675B2/ja not_active Expired - Fee Related
- 2003-01-29 ES ES03702554T patent/ES2297125T5/es not_active Expired - Lifetime
- 2003-01-29 CN CNB038034018A patent/CN100375740C/zh not_active Expired - Fee Related
- 2003-01-29 DE DE60317770T patent/DE60317770T3/de not_active Expired - Lifetime
- 2003-01-29 US US10/503,696 patent/US7253297B2/en not_active Expired - Lifetime
- 2003-01-29 EP EP03702554A patent/EP1474388B2/en not_active Expired - Lifetime
- 2003-01-29 WO PCT/EP2003/000873 patent/WO2003066583A1/en not_active Ceased
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2004
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- 2004-08-05 KR KR20047012137A patent/KR100958483B1/ko not_active Expired - Fee Related
- 2004-09-06 NO NO20043728A patent/NO328928B1/no not_active IP Right Cessation
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2007
- 2007-01-10 US US11/652,263 patent/US20070110881A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CA2474208C (en) | 2011-03-29 |
| KR20040083437A (ko) | 2004-10-01 |
| MX247604B (es) | 2007-07-30 |
| CN100375740C (zh) | 2008-03-19 |
| CA2474208A1 (en) | 2003-08-14 |
| EP1474388B2 (en) | 2013-03-06 |
| DE60317770T2 (de) | 2008-10-30 |
| DE60317770D1 (en) | 2008-01-10 |
| NO20043728D0 (no) | 2004-09-06 |
| ES2297125T3 (es) | 2008-05-01 |
| ES2297125T5 (es) | 2013-07-03 |
| KR100958483B1 (ko) | 2010-05-17 |
| US20070110881A1 (en) | 2007-05-17 |
| US7253297B2 (en) | 2007-08-07 |
| AU2003205699B2 (en) | 2008-05-08 |
| WO2003066583A1 (en) | 2003-08-14 |
| JP4420675B2 (ja) | 2010-02-24 |
| MXPA04007557A (es) | 2004-11-10 |
| NO20043728L (no) | 2004-09-06 |
| CN1628097A (zh) | 2005-06-15 |
| DE60317770T3 (de) | 2013-07-25 |
| AU2003205699B8 (en) | 2008-06-05 |
| US20050096477A1 (en) | 2005-05-05 |
| JP2005517010A (ja) | 2005-06-09 |
| EP1474388B1 (en) | 2007-11-28 |
| IN2004CH01714A (enExample) | 2006-02-24 |
| EP1474388A1 (en) | 2004-11-10 |
| AU2003205699A1 (en) | 2003-09-02 |
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