AU742247B2 - Trans-xanthophyll ester concentrates of enhanced purity and methods of making same - Google Patents
Trans-xanthophyll ester concentrates of enhanced purity and methods of making same Download PDFInfo
- Publication number
- AU742247B2 AU742247B2 AU35597/99A AU3559799A AU742247B2 AU 742247 B2 AU742247 B2 AU 742247B2 AU 35597/99 A AU35597/99 A AU 35597/99A AU 3559799 A AU3559799 A AU 3559799A AU 742247 B2 AU742247 B2 AU 742247B2
- Authority
- AU
- Australia
- Prior art keywords
- xanthophyll
- ester
- trans
- concentrate
- esters
- 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.)
- Ceased
Links
- 229960005375 lutein Drugs 0.000 title claims abstract description 97
- 239000012141 concentrate Substances 0.000 title claims abstract description 90
- 238000000034 method Methods 0.000 title claims abstract description 37
- 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 abstract description 71
- 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 abstract description 58
- 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 abstract description 56
- 235000008210 xanthophylls Nutrition 0.000 claims abstract description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 38
- -1 Xanthophyll ester Chemical class 0.000 claims abstract description 30
- 235000005881 Calendula officinalis Nutrition 0.000 claims abstract description 28
- 241000196324 Embryophyta Species 0.000 claims abstract description 28
- 239000002904 solvent Substances 0.000 claims abstract description 27
- 150000003735 xanthophylls Chemical class 0.000 claims abstract description 24
- 239000000284 extract Substances 0.000 claims abstract description 21
- 239000000463 material Substances 0.000 claims abstract description 20
- 241001573881 Corolla Species 0.000 claims abstract description 19
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 18
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 18
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 18
- 239000012535 impurity Substances 0.000 claims abstract description 14
- 239000000447 pesticide residue Substances 0.000 claims abstract description 9
- 238000001514 detection method Methods 0.000 claims abstract description 6
- 238000001704 evaporation Methods 0.000 claims abstract description 5
- 150000002148 esters Chemical class 0.000 claims description 33
- 241000736851 Tagetes Species 0.000 claims description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 24
- 239000007787 solid Substances 0.000 claims description 20
- 235000012680 lutein Nutrition 0.000 claims description 15
- 235000011468 Albizia julibrissin Nutrition 0.000 claims description 14
- 241001070944 Mimosa Species 0.000 claims description 14
- 235000015872 dietary supplement Nutrition 0.000 claims description 13
- 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 10
- 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 10
- 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 10
- 239000001656 lutein Substances 0.000 claims description 10
- 235000010930 zeaxanthin Nutrition 0.000 claims description 10
- 229940043269 zeaxanthin Drugs 0.000 claims description 10
- 239000001775 zeaxanthin Substances 0.000 claims description 10
- 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 9
- 239000000203 mixture Substances 0.000 claims description 8
- 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 claims description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- 235000021028 berry Nutrition 0.000 claims description 4
- 235000016709 nutrition Nutrition 0.000 claims description 4
- 230000035764 nutrition Effects 0.000 claims description 4
- 241001106041 Lycium Species 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 2
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 240000000785 Tagetes erecta Species 0.000 abstract 1
- 239000008601 oleoresin Substances 0.000 description 27
- 238000000605 extraction Methods 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- 238000000746 purification Methods 0.000 description 12
- 238000002156 mixing Methods 0.000 description 11
- 238000003306 harvesting Methods 0.000 description 7
- 229940107604 lutein esters Drugs 0.000 description 7
- 150000002658 luteins Chemical class 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000575 pesticide Substances 0.000 description 6
- 238000002798 spectrophotometry method Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 235000021466 carotenoid Nutrition 0.000 description 5
- 150000001747 carotenoids Chemical class 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 244000241872 Lycium chinense Species 0.000 description 4
- 235000015468 Lycium chinense Nutrition 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 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 3
- 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 class 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 3
- 241001465754 Metazoa Species 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000004710 electron pair approximation Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 235000002864 food coloring agent Nutrition 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 244000144730 Amygdalus persica Species 0.000 description 2
- 241000249058 Anthracothorax Species 0.000 description 2
- 235000004936 Bromus mango Nutrition 0.000 description 2
- 235000009467 Carica papaya Nutrition 0.000 description 2
- 241000219172 Caricaceae Species 0.000 description 2
- 241000282412 Homo 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
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 150000002009 diols Chemical group 0.000 description 2
- 235000013399 edible fruits Nutrition 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
- 238000002955 isolation Methods 0.000 description 2
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- 230000002265 prevention Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- VXRDAMSNTXUHFX-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;n,n-dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1.N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 VXRDAMSNTXUHFX-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 238000011725 BALB/c mouse Methods 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 241001164374 Calyx Species 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 235000015459 Lycium barbarum Nutrition 0.000 description 1
- 206010025421 Macule Diseases 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- 244000064622 Physalis edulis Species 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
- 239000002253 acid Substances 0.000 description 1
- 206010064930 age-related macular degeneration Diseases 0.000 description 1
- 229940094070 ambien Drugs 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
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- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
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- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000576 food coloring agent Substances 0.000 description 1
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- 230000002443 hepatoprotective effect Effects 0.000 description 1
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- 239000004615 ingredient Substances 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 229940105132 myristate Drugs 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000000485 pigmenting effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical class CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 229940035289 tobi Drugs 0.000 description 1
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- 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)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Obesity (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Hematology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Medicines Containing Plant Substances (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8229398P | 1998-04-20 | 1998-04-20 | |
| US60/082293 | 1998-04-20 | ||
| US8580498P | 1998-05-18 | 1998-05-18 | |
| US60/085804 | 1998-05-18 | ||
| US09/229041 | 1999-01-12 | ||
| US09/229,041 US6191293B1 (en) | 1998-04-20 | 1999-01-12 | Trans-xanthophyll ester concentrates of enhanced purity and methods of making same |
| PCT/US1999/008142 WO1999054408A1 (en) | 1998-04-20 | 1999-04-14 | Trans-xanthophyll ester concentrates of enhanced purity and methods of making same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU3559799A AU3559799A (en) | 1999-11-08 |
| AU742247B2 true AU742247B2 (en) | 2001-12-20 |
Family
ID=27374251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU35597/99A Ceased AU742247B2 (en) | 1998-04-20 | 1999-04-14 | Trans-xanthophyll ester concentrates of enhanced purity and methods of making same |
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 |
| BR0207405B1 (pt) | 2001-02-23 | 2012-09-18 | novos ésteres carotenóides. | |
| 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 |
| US7081478B2 (en) * | 2001-06-29 | 2006-07-25 | Chrysantis, Inc. | Mixed zeaxanthin ester concentrate and uses thereof |
| US7575766B2 (en) * | 2001-06-29 | 2009-08-18 | Ball Horticultural Company | Tagetes erecta with altered carotenoid compositions and ratios |
| US6797303B2 (en) * | 2001-09-04 | 2004-09-28 | Lycored Natural Products Industries Ltd. | Carotenoid extraction process |
| WO2003037833A1 (en) * | 2001-11-02 | 2003-05-08 | Sobhanadri, Jonnalagadda | Extraction of lutein from marigold meal |
| WO2003048284A1 (en) * | 2001-11-29 | 2003-06-12 | 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 |
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-
1999
- 1999-01-12 US US09/229,041 patent/US6191293B1/en not_active Expired - Lifetime
- 1999-04-14 DK DK99917487T patent/DK1073694T3/da active
- 1999-04-14 AT AT99917487T patent/ATE244280T1/de active
- 1999-04-14 EP EP99917487A patent/EP1073694B1/en not_active Expired - Lifetime
- 1999-04-14 PT PT99917487T patent/PT1073694E/pt unknown
- 1999-04-14 CA CA002340429A patent/CA2340429C/en not_active Expired - Fee Related
- 1999-04-14 JP JP2000544746A patent/JP4958335B2/ja not_active Expired - Lifetime
- 1999-04-14 AU AU35597/99A patent/AU742247B2/en not_active Ceased
- 1999-04-14 ES ES99917487T patent/ES2203118T3/es not_active Expired - Lifetime
- 1999-04-14 WO PCT/US1999/008142 patent/WO1999054408A1/en not_active Ceased
- 1999-04-14 DE DE69909279T patent/DE69909279T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US6191293B1 (en) | 2001-02-20 |
| CA2340429C (en) | 2006-08-01 |
| DE69909279T2 (de) | 2004-04-22 |
| CA2340429A1 (en) | 1999-10-28 |
| JP4958335B2 (ja) | 2012-06-20 |
| EP1073694B1 (en) | 2003-07-02 |
| DK1073694T3 (da) | 2003-10-20 |
| PT1073694E (pt) | 2003-11-28 |
| WO1999054408A1 (en) | 1999-10-28 |
| DE69909279D1 (de) | 2003-08-07 |
| JP2002512256A (ja) | 2002-04-23 |
| EP1073694A1 (en) | 2001-02-07 |
| ES2203118T3 (es) | 2004-04-01 |
| AU3559799A (en) | 1999-11-08 |
| ATE244280T1 (de) | 2003-07-15 |
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