JP2002512256A5 - - Google Patents
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- Publication number
- JP2002512256A5 JP2002512256A5 JP2000544746A JP2000544746A JP2002512256A5 JP 2002512256 A5 JP2002512256 A5 JP 2002512256A5 JP 2000544746 A JP2000544746 A JP 2000544746A JP 2000544746 A JP2000544746 A JP 2000544746A JP 2002512256 A5 JP2002512256 A5 JP 2002512256A5
- Authority
- JP
- Japan
- Prior art keywords
- concentrate
- ester
- xanthophyll
- trans
- xanthophyll ester
- 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.)
- Granted
Links
- 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 claims description 158
- 229960005375 lutein Drugs 0.000 claims description 145
- 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 claims description 144
- 235000008210 xanthophylls Nutrition 0.000 claims description 134
- 239000012141 concentrate Substances 0.000 claims description 125
- -1 xanthophyll ester Chemical class 0.000 claims description 120
- 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 claims description 87
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 44
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 39
- 239000002904 solvent Substances 0.000 claims description 37
- 241000196324 Embryophyta Species 0.000 claims description 33
- 241000736851 Tagetes Species 0.000 claims description 31
- 235000005881 Calendula officinalis Nutrition 0.000 claims description 30
- 239000000463 material Substances 0.000 claims description 29
- 241001573881 Corolla Species 0.000 claims description 25
- 239000000284 extract Substances 0.000 claims description 25
- 239000004215 Carbon black (E152) Substances 0.000 claims description 23
- 229930195733 hydrocarbon Natural products 0.000 claims description 23
- 150000002430 hydrocarbons Chemical class 0.000 claims description 23
- 238000002156 mixing Methods 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 20
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 claims description 18
- 235000016709 nutrition Nutrition 0.000 claims description 18
- 239000012535 impurity Substances 0.000 claims description 16
- 239000013589 supplement Substances 0.000 claims description 15
- 235000012680 lutein Nutrition 0.000 claims description 14
- 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 claims description 12
- 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 claims description 12
- 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 claims description 12
- 235000015872 dietary supplement Nutrition 0.000 claims description 12
- 239000001656 lutein Substances 0.000 claims description 12
- 239000000575 pesticide Substances 0.000 claims description 12
- 235000010930 zeaxanthin Nutrition 0.000 claims description 12
- 239000001775 zeaxanthin Substances 0.000 claims description 12
- 229940043269 zeaxanthin Drugs 0.000 claims description 12
- 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 claims description 11
- 238000001514 detection method Methods 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 6
- 230000035764 nutrition Effects 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 235000013399 edible fruits Nutrition 0.000 claims description 5
- 241001106041 Lycium Species 0.000 claims description 3
- 244000064622 Physalis edulis Species 0.000 claims description 3
- 239000000447 pesticide residue Substances 0.000 claims description 3
- 235000004213 low-fat Nutrition 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 238000010298 pulverizing process Methods 0.000 claims 1
- 150000003735 xanthophylls Chemical class 0.000 description 34
- 239000008601 oleoresin Substances 0.000 description 22
- 150000002148 esters Chemical class 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 17
- 238000000605 extraction Methods 0.000 description 13
- 150000002658 luteins Chemical class 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 238000002798 spectrophotometry method Methods 0.000 description 9
- 229940107604 lutein esters Drugs 0.000 description 8
- 238000004090 dissolution Methods 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 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 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 244000241872 Lycium chinense Species 0.000 description 5
- 235000015468 Lycium chinense Nutrition 0.000 description 5
- 235000021466 carotenoid Nutrition 0.000 description 5
- 150000001747 carotenoids Chemical class 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000003306 harvesting Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 235000005911 diet Nutrition 0.000 description 4
- 238000004710 electron pair approximation Methods 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 241000282412 Homo Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000000919 ceramic Substances 0.000 description 3
- 239000000576 food coloring agent Substances 0.000 description 3
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 2
- 244000144730 Amygdalus persica Species 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 2
- 235000004936 Bromus mango Nutrition 0.000 description 2
- 240000006432 Carica papaya Species 0.000 description 2
- 235000009467 Carica papaya Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 2
- 235000015459 Lycium barbarum Nutrition 0.000 description 2
- 240000007228 Mangifera indica Species 0.000 description 2
- 235000014826 Mangifera indica Nutrition 0.000 description 2
- 244000141353 Prunus domestica Species 0.000 description 2
- 235000006040 Prunus persica var persica Nutrition 0.000 description 2
- 235000009184 Spondias indica Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 230000000378 dietary effect Effects 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- RDYMFSUJUZBWLH-SVWSLYAFSA-N endosulfan Chemical compound C([C@@H]12)OS(=O)OC[C@@H]1[C@]1(Cl)C(Cl)=C(Cl)[C@@]2(Cl)C1(Cl)Cl RDYMFSUJUZBWLH-SVWSLYAFSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 201000005202 lung cancer Diseases 0.000 description 2
- 208000020816 lung neoplasm Diseases 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- KBPHJBAIARWVSC-DKLMTRRASA-N 4-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-2-en-1-ol Chemical compound CC=1CC(O)CC(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\C1C(C)=CC(O)CC1(C)C KBPHJBAIARWVSC-DKLMTRRASA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 206010025421 Macule Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 1
- 101100269495 Rattus norvegicus Ina gene Proteins 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- 235000012308 Tagetes Nutrition 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 206010064930 age-related macular degeneration Diseases 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000005907 cancer growth Effects 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000002864 food coloring agent Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002443 hepatoprotective effect Effects 0.000 description 1
- 238000012994 industrial processing Methods 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 208000002780 macular degeneration Diseases 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 150000003749 zeaxanthins Chemical class 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8229398P | 1998-04-20 | 1998-04-20 | |
| US60/082,293 | 1998-04-20 | ||
| US8580498P | 1998-05-18 | 1998-05-18 | |
| US60/085,804 | 1998-05-18 | ||
| US09/229,041 US6191293B1 (en) | 1998-04-20 | 1999-01-12 | Trans-xanthophyll ester concentrates of enhanced purity and methods of making same |
| US09/229,041 | 1999-01-12 | ||
| PCT/US1999/008142 WO1999054408A1 (en) | 1998-04-20 | 1999-04-14 | Trans-xanthophyll ester concentrates of enhanced purity and methods of making same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002512256A JP2002512256A (ja) | 2002-04-23 |
| JP2002512256A5 true JP2002512256A5 (enExample) | 2007-08-30 |
| JP4958335B2 JP4958335B2 (ja) | 2012-06-20 |
Family
ID=27374251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000544746A Expired - Lifetime JP4958335B2 (ja) | 1998-04-20 | 1999-04-14 | 高純度のトランス形キサントフィルエステル濃縮物及びその製造方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6191293B1 (enExample) |
| EP (1) | EP1073694B1 (enExample) |
| JP (1) | JP4958335B2 (enExample) |
| AT (1) | ATE244280T1 (enExample) |
| AU (1) | AU742247B2 (enExample) |
| CA (1) | CA2340429C (enExample) |
| DE (1) | DE69909279T2 (enExample) |
| DK (1) | DK1073694T3 (enExample) |
| ES (1) | ES2203118T3 (enExample) |
| PT (1) | PT1073694E (enExample) |
| WO (1) | WO1999054408A1 (enExample) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6169217B1 (en) * | 1999-10-20 | 2001-01-02 | Board Of Trustees Of The University Of Illinois | Method for extracting xanthophylls from corn |
| US6329557B1 (en) * | 2000-06-09 | 2001-12-11 | Prodemex, S.A. De C.V. | Purification of xanthophylls from marigold extracts that contain high levels of chlorophylls |
| EP1377547B1 (en) | 2001-02-23 | 2008-01-16 | Luis W. Levy | Novel carotenoid esters |
| WO2002094772A1 (en) * | 2001-05-18 | 2002-11-28 | Aventis Animal Nutrition S.A. | Process for the extraction of esters of xanthophyll and of carotenoids |
| US6784351B2 (en) * | 2001-06-29 | 2004-08-31 | Ball Horticultural Company | Targetes erecta marigolds with altered carotenoid compositions and ratios |
| US7575766B2 (en) * | 2001-06-29 | 2009-08-18 | Ball Horticultural Company | Tagetes erecta with altered carotenoid compositions and ratios |
| US7081478B2 (en) * | 2001-06-29 | 2006-07-25 | Chrysantis, Inc. | Mixed zeaxanthin ester concentrate and uses thereof |
| US6797303B2 (en) * | 2001-09-04 | 2004-09-28 | Lycored Natural Products Industries Ltd. | Carotenoid extraction process |
| US20040267033A1 (en) * | 2001-11-02 | 2004-12-30 | Rao Jonnalagadda Raghunath | Extraction of lutein from marigold meal |
| AU2002234248A1 (en) * | 2001-11-29 | 2003-06-17 | University Of Maryland | Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants |
| US6811801B2 (en) | 2001-12-12 | 2004-11-02 | Abbott Laboratories | Methods and compositions for brightening the color of thermally processed nutritionals |
| JP2003201497A (ja) * | 2002-01-08 | 2003-07-18 | Riken Vitamin Co Ltd | ルテイン脂肪酸エステル濃縮物の製造方法 |
| US7223909B2 (en) * | 2002-03-21 | 2007-05-29 | Ball Horticultural | 4-ketocarotenoids in flower petals |
| US6737535B2 (en) * | 2002-06-05 | 2004-05-18 | Kancor Flavours And Extracts Limited | Trans-lutein enriched xanthophyll ester concentrate and a process for its preparation |
| EP1371641A1 (en) * | 2002-06-10 | 2003-12-17 | Adisseo France S.A.S. | Process for the formation and isolation of carotenoid crystals |
| US6743953B2 (en) | 2002-08-26 | 2004-06-01 | Kancor Flavours & Extracts Ltd. | Process for the preparation of xanthophyll crystals |
| EP1400509B1 (en) | 2002-09-20 | 2007-04-11 | Riken Vitamin Co., Ltd. | A method for the purification of marigold oleoresin |
| EP1433387A1 (en) * | 2002-12-26 | 2004-06-30 | Adisseo France S.A.S. | Solid granules containing carotenoids |
| US7189218B2 (en) * | 2003-08-07 | 2007-03-13 | Edward Lichtenberg | Needle apparatus with quick/safe release mechanism |
| US7541166B2 (en) * | 2003-09-19 | 2009-06-02 | Microfluidic Systems, Inc. | Sonication to selectively lyse different cell types |
| PE20050398A1 (es) * | 2003-09-22 | 2005-06-03 | Rosales Jose Antonio Socla | Proceso y purificacion de las xantofilas de marigold |
| DE20319249U1 (de) * | 2003-12-10 | 2004-12-30 | Aquanova German Solubilisate Technologies (Agt) Gmbh | Lutein-Konzentrat |
| US7351424B2 (en) * | 2004-07-22 | 2008-04-01 | Bio Lut S.A. De C.V. | Enhanced purity trans-lutein-ester compositions and methods of making same |
| CA2597402A1 (en) * | 2005-02-11 | 2006-08-17 | Kalamazoo Holdings, Inc. | A capsicum variety exhibiting a hyper-accumulation of zeaxanthin and products derived therefrom |
| US8592662B2 (en) | 2005-02-11 | 2013-11-26 | Kalamazoo Holdings, Inc. | Capsicum variety exhibiting a hyper-accumulation of zeaxanthin and products derived therefrom |
| US20070065487A1 (en) * | 2005-09-21 | 2007-03-22 | Bio Lut S.A. De C.V. | Trans-lutein xantophyll ester of high purity and high bioavailability in micellar solution and a process for the preparation thereof |
| US7297803B2 (en) * | 2006-02-06 | 2007-11-20 | Bioactives, Llc | Process for the preparation of lutein ester concentrate |
| CA2651583C (en) * | 2006-05-08 | 2013-07-02 | The Board Of Trustees Of The University Of Illinois | Method and system for production of zein and/or xanthophylls using chromatography |
| US20090118228A1 (en) * | 2007-11-07 | 2009-05-07 | Bristol-Myers Squibb Company | Carotenoid-containing compositions and methods |
| JP2009201503A (ja) | 2008-01-31 | 2009-09-10 | Yamaha Motor Co Ltd | アスタキサンチン含有抽出物の香味改善方法 |
| US8716533B2 (en) | 2009-05-29 | 2014-05-06 | Kalamazoo Holdings, Inc. | Methods of saponifying xanthophyll esters and isolating xanthophylls |
| US8247615B2 (en) | 2010-05-14 | 2012-08-21 | Kalamazoo Holdings, Inc. | Process of converting esterified xanthophylls from Capsicum to non-esterified xanthophylls in high yields and purities |
| JP5733696B2 (ja) * | 2010-08-16 | 2015-06-10 | 二村 芳弘 | 脂肪分解作用を呈するカロチノイド誘導体の製造方法 |
| CN103080238B (zh) * | 2010-08-25 | 2016-01-20 | 帝斯曼知识产权资产管理有限公司 | 用于制造含玉米黄质和/或其酯的高富集萃取物的方法 |
| ES2583004T3 (es) | 2010-10-13 | 2016-09-16 | Vigenent Inc. | Olleya marilimosa y su uso en un método para la preparación de una composición que contiene zeaxantina |
| EP2665805B1 (en) * | 2011-01-17 | 2019-11-13 | India Glycols Limited | Single stage lutein ester extraction from tagetes species-marigold flower meal |
| WO2013123618A1 (en) * | 2012-02-22 | 2013-08-29 | Dsm Ip Assets B.V. | Process for manufacture of extract containing zeaxanthin and/or its esters |
| WO2013127255A1 (en) * | 2012-02-27 | 2013-09-06 | Dsm Ip Assets B.V. | Process for manufacture of highly enriched extract containing zeaxanthin and/or its esters |
| CN104125987B (zh) * | 2012-02-27 | 2016-11-23 | 帝斯曼知识产权资产管理有限公司 | 制造高度富含玉米黄质和/或其酯的萃取物的方法 |
| US9580371B2 (en) | 2013-05-16 | 2017-02-28 | University Of Maryland, College Park | Process for simultaneous extraction and separation of esterified and unesterified monohydroxycarotenoids |
| CN104059007A (zh) * | 2014-04-30 | 2014-09-24 | 西安岳达植物科技有限公司 | 一种从万寿菊花朵中提取叶黄素酯的方法 |
| CN104387307B (zh) * | 2014-11-18 | 2016-02-03 | 晨光生物科技集团股份有限公司 | 一种叶黄素浸膏中乙氧基喹啉的去除方法 |
| CN105418472B (zh) * | 2015-11-21 | 2017-05-10 | 中国海洋大学 | 一种利用溶剂分级结晶分离虾青素单双酯的方法 |
| WO2022155338A1 (en) | 2021-01-14 | 2022-07-21 | Kemin Industries, Inc. | Process for crystallization of high purity lutein esters from marigold extracts |
| WO2022071914A2 (en) * | 2021-12-28 | 2022-04-07 | Sadirlar Alliance Tekstil A.Ş. | Yellow-colored vegetable textile dye composition and related dyeing method |
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| US3333962A (en) | 1963-12-02 | 1967-08-01 | Hoffman Taff Inc | Treatment of pyrethrum plant waste materials and utilization in feed |
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| US4048203A (en) * | 1976-12-06 | 1977-09-13 | Thomas Philip | Purification of lutein-fatty acid esters from plant materials |
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-
1999
- 1999-01-12 US US09/229,041 patent/US6191293B1/en not_active Expired - Lifetime
- 1999-04-14 JP JP2000544746A patent/JP4958335B2/ja not_active Expired - Lifetime
- 1999-04-14 DK DK99917487T patent/DK1073694T3/da active
- 1999-04-14 WO PCT/US1999/008142 patent/WO1999054408A1/en not_active Ceased
- 1999-04-14 PT PT99917487T patent/PT1073694E/pt unknown
- 1999-04-14 EP EP99917487A patent/EP1073694B1/en not_active Expired - Lifetime
- 1999-04-14 AT AT99917487T patent/ATE244280T1/de active
- 1999-04-14 CA CA002340429A patent/CA2340429C/en not_active Expired - Fee Related
- 1999-04-14 ES ES99917487T patent/ES2203118T3/es not_active Expired - Lifetime
- 1999-04-14 DE DE69909279T patent/DE69909279T2/de not_active Expired - Lifetime
- 1999-04-14 AU AU35597/99A patent/AU742247B2/en not_active Ceased
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