UA75650C2 - Process for the preparation of xanthophyll - Google Patents
Process for the preparation of xanthophyll Download PDFInfo
- Publication number
- UA75650C2 UA75650C2 UA20031110543A UA20031110543A UA75650C2 UA 75650 C2 UA75650 C2 UA 75650C2 UA 20031110543 A UA20031110543 A UA 20031110543A UA 20031110543 A UA20031110543 A UA 20031110543A UA 75650 C2 UA75650 C2 UA 75650C2
- Authority
- UA
- Ukraine
- Prior art keywords
- iodine
- xanthophyll
- carotenoid
- containing compound
- carotene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 42
- 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 title abstract description 35
- 229960005375 lutein Drugs 0.000 title abstract description 26
- 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 title abstract description 26
- 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 title abstract description 25
- 235000008210 xanthophylls Nutrition 0.000 title abstract description 22
- 238000002360 preparation method Methods 0.000 title abstract description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 22
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- 150000001747 carotenoids Chemical class 0.000 claims abstract description 20
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 20
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- -1 halogen derivative of iodine Chemical class 0.000 claims description 8
- 229910001511 metal iodide Inorganic materials 0.000 claims description 4
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- 229910001516 alkali metal iodide Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 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 abstract description 23
- 238000007254 oxidation reaction Methods 0.000 abstract description 20
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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 abstract description 11
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- 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 abstract description 11
- 229960002747 betacarotene Drugs 0.000 abstract description 11
- 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 abstract description 10
- 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 abstract description 9
- 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 abstract description 9
- 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 abstract description 9
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- 239000001168 astaxanthin Substances 0.000 abstract description 7
- 229940022405 astaxanthin Drugs 0.000 abstract description 7
- 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 abstract description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
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- 239000012071 phase Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 150000003735 xanthophylls Chemical class 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000001688 paprika extract Substances 0.000 description 4
- 235000012658 paprika extract Nutrition 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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- 238000006243 chemical reaction Methods 0.000 description 3
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- VYIRVAXUEZSDNC-TXDLOWMYSA-N (3R,3'S,5'R)-3,3'-dihydroxy-beta-kappa-caroten-6'-one 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=CC(=O)[C@]1(C)C[C@@H](O)CC1(C)C VYIRVAXUEZSDNC-TXDLOWMYSA-N 0.000 description 2
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- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000002635 lutein group Chemical group 0.000 description 1
- 235000012661 lycopene Nutrition 0.000 description 1
- 239000001751 lycopene Substances 0.000 description 1
- OAIJSZIZWZSQBC-GYZMGTAESA-N lycopene Chemical compound CC(C)=CCC\C(C)=C\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C=C(/C)CCC=C(C)C OAIJSZIZWZSQBC-GYZMGTAESA-N 0.000 description 1
- 229960004999 lycopene Drugs 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- NALMPLUMOWIVJC-UHFFFAOYSA-N n,n,4-trimethylbenzeneamine oxide Chemical compound CC1=CC=C([N+](C)(C)[O-])C=C1 NALMPLUMOWIVJC-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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 239000012285 osmium tetroxide Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 description 1
- 239000011697 sodium iodate Substances 0.000 description 1
- 235000015281 sodium iodate Nutrition 0.000 description 1
- 229940032753 sodium iodate Drugs 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 description 1
- 229910001488 sodium perchlorate Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- ZCIHMQAPACOQHT-ZGMPDRQDSA-N trans-isorenieratene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/c1c(C)ccc(C)c1C)C=CC=C(/C)C=Cc2c(C)ccc(C)c2C ZCIHMQAPACOQHT-ZGMPDRQDSA-N 0.000 description 1
- FXOJASSPEGUXFT-UHFFFAOYSA-N tribromo-$l^{3}-iodane Chemical compound BrI(Br)Br FXOJASSPEGUXFT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000005406 washing Methods 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyrane Compounds (AREA)
- Compounds Of Unknown Constitution (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01109976A EP1253131A1 (en) | 2001-04-24 | 2001-04-24 | Process for the preparation of an xanthophyll |
| PCT/EP2002/005455 WO2002085831A1 (en) | 2001-04-24 | 2002-04-18 | Process for the preparation of an xanthophyll |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA75650C2 true UA75650C2 (en) | 2006-05-15 |
Family
ID=8177224
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20031110543A UA75650C2 (en) | 2001-04-24 | 2002-04-18 | Process for the preparation of xanthophyll |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7041854B2 (ru) |
| EP (2) | EP1253131A1 (ru) |
| JP (1) | JP2004529151A (ru) |
| KR (1) | KR20040008161A (ru) |
| CN (1) | CN1246309C (ru) |
| AT (1) | ATE348802T1 (ru) |
| AU (1) | AU2002304635B2 (ru) |
| BR (1) | BR0209093A (ru) |
| CA (1) | CA2443945A1 (ru) |
| DE (1) | DE60216913D1 (ru) |
| HU (1) | HUP0402027A3 (ru) |
| MX (1) | MXPA03009685A (ru) |
| PL (1) | PL367703A1 (ru) |
| RU (1) | RU2284992C2 (ru) |
| UA (1) | UA75650C2 (ru) |
| WO (1) | WO2002085831A1 (ru) |
| ZA (1) | ZA200308182B (ru) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1371641A1 (en) * | 2002-06-10 | 2003-12-17 | Adisseo France S.A.S. | Process for the formation and isolation of carotenoid crystals |
| ES2223270B1 (es) * | 2003-04-10 | 2006-04-16 | Carotenoid Technologies, S.A. | Procedimiento para la sintesis de astaxantina. |
| BRPI0516202A (pt) | 2004-09-28 | 2008-08-26 | Chemaphor Inc | produto para alimentação de um animal, uso, kit e método de preparação deste produto |
| TWI385169B (zh) | 2005-10-31 | 2013-02-11 | Eisai R&D Man Co Ltd | 經雜環取代之吡啶衍生物及含有彼之抗真菌劑 |
| ES2311422B1 (es) * | 2007-07-28 | 2009-10-13 | Investigaciones Quimicas Y Farmaceuticas, S.A | Formulacion de carotenoides dispersables en agua. |
| JP2011500733A (ja) | 2007-10-26 | 2011-01-06 | ケマファー インコーポレーテッド | 免疫応答を増強するための組成物および方法 |
| MX2011005264A (es) * | 2008-11-19 | 2011-08-03 | Innova Andina S A | Metodo para la preparacion de oxicarotenoides. |
| EP2424512B1 (en) | 2009-04-30 | 2020-06-03 | Avivagen Inc. | Methods and compositions for improving the health of animals |
| TWI394610B (zh) * | 2010-09-09 | 2013-05-01 | Nat Univ Chung Hsing | Purification program of zeaxanthin in algae-flavored flavonoids with high recovery rate from renewable adsorbent |
| RU2553213C2 (ru) * | 2012-05-30 | 2015-06-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Российский химико-технологический университет им. Д.И. Менделеева" (РХТУ им. Д.И. Менделеева) | Способ получения биомассы каротинсинтезирующих микроорганизмов |
| WO2015009174A1 (es) * | 2013-07-17 | 2015-01-22 | Quimtia S.A. | Oxidación de meso-zeaxantina |
| US10017466B2 (en) | 2014-10-02 | 2018-07-10 | Basf Se | Process for purifying astaxanthin and canthaxanthin |
| CN106831520B (zh) * | 2017-04-13 | 2018-06-22 | 山东天音生物科技有限公司 | 一种由玉米黄质制备虾青素的方法 |
| CN108101817B (zh) * | 2017-12-23 | 2020-06-05 | 厦门金达威维生素有限公司 | β-胡萝卜素氧化制备斑蝥黄的方法 |
| CN108912028A (zh) * | 2018-07-31 | 2018-11-30 | 万华化学集团股份有限公司 | 一种氧化β-胡萝卜素制备角黄素的方法 |
| CN109369486B (zh) * | 2018-12-18 | 2020-06-23 | 厦门金达威维生素有限公司 | 一种斑蝥黄的制备方法 |
| CN109369487B (zh) * | 2018-12-24 | 2020-09-15 | 安徽工大化工科技有限公司 | 一种高纯度斑蝥黄制备方法 |
| CN109678770B (zh) * | 2018-12-24 | 2020-09-15 | 安徽工大化工科技有限公司 | 一种β-胡萝卜素氧化制备斑蝥黄的方法 |
| CN111825588B (zh) * | 2020-07-13 | 2022-07-12 | 万华化学集团股份有限公司 | 一种β-胡萝卜素氧化制备角黄素的方法 |
| CN112359045A (zh) * | 2020-11-18 | 2021-02-12 | 合肥工业大学 | 一种类胡萝卜素代谢途径相关基因及应用 |
| CN112552221B (zh) * | 2020-12-23 | 2022-08-16 | 厦门金达威维生素有限公司 | 一种斑蝥黄的制备方法 |
| CN112979521A (zh) * | 2021-03-10 | 2021-06-18 | 内蒙古民族大学 | 一种以玉米黄质合成虾青素的简便方法 |
| CN113416968B (zh) * | 2021-06-08 | 2022-11-08 | 万华化学集团股份有限公司 | 一种无氧化剂电化学催化制备角黄素的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2505869C3 (de) * | 1975-02-12 | 1978-05-18 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von symmetrischen Carotinoiden |
| CA1058626A (en) * | 1975-08-05 | 1979-07-17 | Joachim Paust | Manufacture of canthaxanthin |
| DE3377127D1 (en) * | 1982-08-20 | 1988-07-28 | Hoffmann La Roche | Process for the preparation of astaxanthine and intermediates in the astaxanthine synthesis |
-
2001
- 2001-04-24 EP EP01109976A patent/EP1253131A1/en not_active Withdrawn
-
2002
- 2002-04-18 PL PL02367703A patent/PL367703A1/xx unknown
- 2002-04-18 DE DE60216913T patent/DE60216913D1/de not_active Expired - Lifetime
- 2002-04-18 HU HU0402027A patent/HUP0402027A3/hu unknown
- 2002-04-18 CN CNB028088417A patent/CN1246309C/zh not_active Expired - Fee Related
- 2002-04-18 AU AU2002304635A patent/AU2002304635B2/en not_active Ceased
- 2002-04-18 RU RU2003133993/04A patent/RU2284992C2/ru not_active IP Right Cessation
- 2002-04-18 MX MXPA03009685A patent/MXPA03009685A/es active IP Right Grant
- 2002-04-18 AT AT02732721T patent/ATE348802T1/de not_active IP Right Cessation
- 2002-04-18 US US10/474,899 patent/US7041854B2/en not_active Expired - Fee Related
- 2002-04-18 WO PCT/EP2002/005455 patent/WO2002085831A1/en active IP Right Grant
- 2002-04-18 KR KR10-2003-7013906A patent/KR20040008161A/ko not_active Application Discontinuation
- 2002-04-18 BR BR0209093-7A patent/BR0209093A/pt not_active IP Right Cessation
- 2002-04-18 JP JP2002583362A patent/JP2004529151A/ja not_active Withdrawn
- 2002-04-18 EP EP02732721A patent/EP1392632B1/en not_active Expired - Lifetime
- 2002-04-18 UA UA20031110543A patent/UA75650C2/uk unknown
- 2002-04-18 CA CA002443945A patent/CA2443945A1/en not_active Abandoned
-
2003
- 2003-10-21 ZA ZA200308182A patent/ZA200308182B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0402027A2 (hu) | 2005-01-28 |
| DE60216913D1 (de) | 2007-02-01 |
| BR0209093A (pt) | 2006-02-07 |
| US20040074843A1 (en) | 2004-04-22 |
| MXPA03009685A (es) | 2004-12-06 |
| EP1392632B1 (en) | 2006-12-20 |
| EP1253131A1 (en) | 2002-10-30 |
| JP2004529151A (ja) | 2004-09-24 |
| ATE348802T1 (de) | 2007-01-15 |
| CN1505602A (zh) | 2004-06-16 |
| EP1392632A1 (en) | 2004-03-03 |
| AU2002304635B2 (en) | 2006-09-28 |
| PL367703A1 (en) | 2005-03-07 |
| KR20040008161A (ko) | 2004-01-28 |
| HUP0402027A3 (en) | 2005-10-28 |
| US7041854B2 (en) | 2006-05-09 |
| RU2003133993A (ru) | 2005-05-10 |
| ZA200308182B (en) | 2004-07-05 |
| WO2002085831A1 (en) | 2002-10-31 |
| CA2443945A1 (en) | 2002-10-31 |
| RU2284992C2 (ru) | 2006-10-10 |
| CN1246309C (zh) | 2006-03-22 |
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