DE69013216T2 - Herstellung von Stearidonsäure. - Google Patents
Herstellung von Stearidonsäure.Info
- Publication number
- DE69013216T2 DE69013216T2 DE69013216T DE69013216T DE69013216T2 DE 69013216 T2 DE69013216 T2 DE 69013216T2 DE 69013216 T DE69013216 T DE 69013216T DE 69013216 T DE69013216 T DE 69013216T DE 69013216 T2 DE69013216 T2 DE 69013216T2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- fatty acids
- stearidonic acid
- mixture
- column
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 title claims abstract description 30
- OPGOLNDOMSBSCW-CLNHMMGSSA-N Fursultiamine hydrochloride Chemical compound Cl.C1CCOC1CSSC(\CCO)=C(/C)N(C=O)CC1=CN=C(C)N=C1N OPGOLNDOMSBSCW-CLNHMMGSSA-N 0.000 title claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 239000000203 mixture Substances 0.000 claims abstract description 49
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 41
- 239000000194 fatty acid Substances 0.000 claims abstract description 41
- 229930195729 fatty acid Natural products 0.000 claims abstract description 41
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 40
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims abstract description 8
- 239000003480 eluent Substances 0.000 claims abstract description 6
- 208000001435 Thromboembolism Diseases 0.000 claims abstract description 5
- 238000004007 reversed phase HPLC Methods 0.000 claims abstract description 5
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 4
- 230000002526 effect on cardiovascular system Effects 0.000 claims abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 14
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 235000021323 fish oil Nutrition 0.000 claims description 6
- 235000019198 oils Nutrition 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- 230000005526 G1 to G0 transition Effects 0.000 claims description 3
- 235000001466 Ribes nigrum Nutrition 0.000 claims description 3
- 239000003463 adsorbent Substances 0.000 claims description 3
- 235000016954 Ribes hudsonianum Nutrition 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- 235000011483 Ribes Nutrition 0.000 claims 1
- 241000220483 Ribes Species 0.000 claims 1
- 240000001890 Ribes hudsonianum Species 0.000 claims 1
- 210000000614 rib Anatomy 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 abstract description 3
- 150000002632 lipids Chemical class 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 9
- 239000004202 carbamide Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 8
- 210000001772 blood platelet Anatomy 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000010473 blackcurrant seed oil Substances 0.000 description 6
- VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 description 6
- 235000020664 gamma-linolenic acid Nutrition 0.000 description 6
- 238000004220 aggregation Methods 0.000 description 5
- 230000002776 aggregation Effects 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 4
- 235000021342 arachidonic acid Nutrition 0.000 description 4
- 229940114079 arachidonic acid Drugs 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 4
- VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 description 4
- 229960002733 gamolenic acid Drugs 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 108090000190 Thrombin Proteins 0.000 description 3
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 150000003173 prostaglandin H2 derivatives Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229960004072 thrombin Drugs 0.000 description 3
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 102000008186 Collagen Human genes 0.000 description 2
- 108010035532 Collagen Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000007995 HEPES buffer Substances 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241001312569 Ribes nigrum Species 0.000 description 2
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 2
- 229940087168 alpha tocopherol Drugs 0.000 description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229920001436 collagen Polymers 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 2
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 235000020778 linoleic acid Nutrition 0.000 description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
- 229960004488 linolenic acid Drugs 0.000 description 2
- 238000000199 molecular distillation Methods 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003180 prostaglandins Chemical class 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229960000984 tocofersolan Drugs 0.000 description 2
- 229930003799 tocopherol Natural products 0.000 description 2
- 239000011732 tocopherol Substances 0.000 description 2
- 235000004835 α-tocopherol Nutrition 0.000 description 2
- 239000002076 α-tocopherol Substances 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 102100034544 Acyl-CoA 6-desaturase Human genes 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 102000008100 Human Serum Albumin Human genes 0.000 description 1
- 108091006905 Human Serum Albumin Proteins 0.000 description 1
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 1
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 1
- 108010037138 Linoleoyl-CoA Desaturase Proteins 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- PZZYQPZGQPZBDN-UHFFFAOYSA-N aluminium silicate Chemical class O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010385 ascorbyl palmitate Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940094199 black currant oil Drugs 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004332 deodorization Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940090949 docosahexaenoic acid Drugs 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000004626 essential fatty acids Nutrition 0.000 description 1
- -1 fatty acid salts Chemical class 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000004810 partition chromatography Methods 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/007—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids using organic solvents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Microbiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Fats And Perfumes (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1919/89A CH678181A5 (enExample) | 1989-05-22 | 1989-05-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69013216D1 DE69013216D1 (de) | 1994-11-17 |
| DE69013216T2 true DE69013216T2 (de) | 1995-03-02 |
Family
ID=4221649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69013216T Expired - Fee Related DE69013216T2 (de) | 1989-05-22 | 1990-05-19 | Herstellung von Stearidonsäure. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5130449A (enExample) |
| EP (1) | EP0399417B1 (enExample) |
| AT (1) | ATE112760T1 (enExample) |
| AU (1) | AU626082B2 (enExample) |
| CH (1) | CH678181A5 (enExample) |
| DE (1) | DE69013216T2 (enExample) |
| DK (1) | DK0399417T3 (enExample) |
| ES (1) | ES2063858T3 (enExample) |
| ZA (1) | ZA903455B (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5234952A (en) * | 1988-12-23 | 1993-08-10 | Nestec S.A. | Reduction of thrombogenicity with lipids of blackcurrant seed |
| FR2679109B1 (fr) * | 1991-07-18 | 1994-03-11 | Institut Recherche Biologique Sa | Nouveaux complements nutritionnels ou dietetiques anti-vieillissement a base d'acide gras poly-insature. |
| AU676910B2 (en) * | 1993-04-29 | 1997-03-27 | Norsk Hydro A.S | Processes for chromatographic fractionation of fatty acids and their derivatives |
| DE69417726T2 (de) * | 1994-05-09 | 1999-08-19 | Societe Des Produits Nestle S.A. | Verfahren zur Herstellung eines Konzentrates von Estern von mehrfach ungesättigten Fettsäuren |
| US6340485B1 (en) | 1996-06-03 | 2002-01-22 | Croda International Plc | Compositions and uses thereof |
| DE69720737T3 (de) * | 1996-06-03 | 2007-06-14 | Croda International Plc, Goole | Pflanzliche ölzusammensetzungen |
| DK0956013T3 (da) * | 1996-10-11 | 2003-08-04 | Scarista Ltd | Farmaceutisk præparat indeholdende eicosapentaensyre og/eller stearidonsyre |
| US7141266B2 (en) * | 1998-05-21 | 2006-11-28 | Beech-Nut Nutrition Corporation | Baby-food compositions enhancing visual acuity and methods therefor |
| US7413759B2 (en) * | 1998-05-21 | 2008-08-19 | Beech-Nut Nutrition Corporation | Method of enhancing cognitive ability in infant fed DHA containing baby-food compositions |
| US6149964A (en) * | 1998-05-21 | 2000-11-21 | Beech-Nut Nutrition Corporation | Egg yolk-containing baby food compositions and methods therefor |
| US6579551B1 (en) | 1998-05-21 | 2003-06-17 | Beech-Nut Nutrition Corporation | Baby-food compositions containing egg yolk and methods therefor |
| EP1196518B1 (en) | 1999-02-26 | 2004-08-11 | Martek Biosciences Corporation | Process for separating a triglyceride comprising a docosahexaenoic acid residue from a mixture of triglycerides |
| AU2001232786A1 (en) | 2000-01-11 | 2001-07-24 | Monsanto Company | Process for making an enriched mixture of polyunsaturated fatty acid esters |
| FR2804023B1 (fr) * | 2000-01-26 | 2002-09-20 | Johnson & Johnson Consumer Fr | Complement nutritionnel a base d'huile de pepins de cassis |
| KR20010008387A (ko) * | 2000-11-30 | 2001-02-05 | 이성권 | 결정화방법을 이용한 고순도 불포화지방산의 분리 정제 방법 |
| JP2005519939A (ja) * | 2002-03-08 | 2005-07-07 | モンサント テクノロジー エルエルシー | 炎症性疾患の治療および予防 |
| SE0202188D0 (sv) * | 2002-07-11 | 2002-07-11 | Pronova Biocare As | A process for decreasing environmental pollutants in an oil or a fat, a volatile fat or oil environmental pollutants decreasing working fluid, a health supplement, and an animal feed product |
| EP2295529B2 (en) | 2002-07-11 | 2022-05-18 | Basf As | Use of a volatile environmental pollutants-decreasing working fluid for decreasing the amount of pollutants in a fat for alimentary or cosmetic use |
| AU2004268196B2 (en) * | 2003-08-21 | 2010-03-04 | Monsanto Technology Llc | Fatty acid desaturases from primula |
| JP2007533310A (ja) * | 2004-04-16 | 2007-11-22 | モンサント テクノロジー エルエルシー | トウモロコシにおける脂肪酸デサチュラーゼの発現 |
| US20050266051A1 (en) * | 2004-05-27 | 2005-12-01 | The Procter & Gamble Company | Pet food compositions and methods |
| EP2218334B1 (en) | 2004-11-04 | 2016-09-28 | Monsanto Technology LLC | Processes for preparation of oil compositions |
| BRPI0708535A2 (pt) * | 2006-03-03 | 2011-05-31 | Monsanto Technology Llc | meios para melhora da saúde cardiovascular |
| BR122018075948B1 (pt) | 2006-03-10 | 2023-05-16 | Monsanto Technology Llc | Métodos de produzir uma planta de soja com teor de ácidos graxos de semente alterados |
| US8060617B2 (en) * | 2008-12-19 | 2011-11-15 | Cisco Technology, Inc. | Reserving network resources during scheduling of meeting event |
| US9480271B2 (en) | 2009-09-15 | 2016-11-01 | Monsanto Technology Llc | Soybean seed and oil compositions and methods of making same |
| US8372465B2 (en) * | 2010-02-17 | 2013-02-12 | Bunge Oils, Inc. | Oil compositions of stearidonic acid |
| WO2024262581A1 (ja) * | 2023-06-22 | 2024-12-26 | 株式会社ニッスイ | 高度不飽和脂肪酸エステル組成物の製造方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4701468A (en) * | 1983-04-15 | 1987-10-20 | Roussel-Uclaf | Oxidized triglycerides having therapeutic utility |
| CH663951A5 (fr) * | 1984-10-10 | 1988-01-29 | Nestle Sa | Procede d'enrichissement selectif en acides gras polyinsatures d'un melange contenant des acides gras fractions enrichies obtenues et compositions les contenant. |
| CH669208A5 (fr) * | 1986-12-17 | 1989-02-28 | Nestle Sa | Procede de fractionnement en continu d'un melange d'acides gras. |
-
1989
- 1989-05-22 CH CH1919/89A patent/CH678181A5/fr not_active IP Right Cessation
-
1990
- 1990-05-03 AU AU54748/90A patent/AU626082B2/en not_active Ceased
- 1990-05-07 ZA ZA903455A patent/ZA903455B/xx unknown
- 1990-05-09 US US07/521,311 patent/US5130449A/en not_active Expired - Fee Related
- 1990-05-19 DE DE69013216T patent/DE69013216T2/de not_active Expired - Fee Related
- 1990-05-19 EP EP90109553A patent/EP0399417B1/fr not_active Expired - Lifetime
- 1990-05-19 DK DK90109553.9T patent/DK0399417T3/da not_active Application Discontinuation
- 1990-05-19 ES ES90109553T patent/ES2063858T3/es not_active Expired - Lifetime
- 1990-05-19 AT AT90109553T patent/ATE112760T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU5474890A (en) | 1990-11-22 |
| AU626082B2 (en) | 1992-07-23 |
| EP0399417A2 (fr) | 1990-11-28 |
| ZA903455B (en) | 1991-02-27 |
| EP0399417A3 (fr) | 1992-01-22 |
| ES2063858T3 (es) | 1995-01-16 |
| ATE112760T1 (de) | 1994-10-15 |
| DK0399417T3 (da) | 1995-02-06 |
| CH678181A5 (enExample) | 1991-08-15 |
| DE69013216D1 (de) | 1994-11-17 |
| EP0399417B1 (fr) | 1994-10-12 |
| US5130449A (en) | 1992-07-14 |
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| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |