CA2779552C - Vegetable oil comprising a polyunsaturated fatty acid having at least 20 carbon atoms - Google Patents
Vegetable oil comprising a polyunsaturated fatty acid having at least 20 carbon atoms Download PDFInfo
- Publication number
- CA2779552C CA2779552C CA2779552A CA2779552A CA2779552C CA 2779552 C CA2779552 C CA 2779552C CA 2779552 A CA2779552 A CA 2779552A CA 2779552 A CA2779552 A CA 2779552A CA 2779552 C CA2779552 C CA 2779552C
- Authority
- CA
- Canada
- Prior art keywords
- oil
- seeds
- pufa
- less
- instance
- 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.)
- Active
Links
- 235000015112 vegetable and seed oil Nutrition 0.000 title claims abstract description 26
- 239000008158 vegetable oil Substances 0.000 title claims abstract description 26
- 125000004432 carbon atom Chemical group C* 0.000 title claims abstract description 16
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 title claims description 23
- 239000003921 oil Substances 0.000 claims abstract description 150
- 235000019198 oils Nutrition 0.000 claims abstract description 150
- 235000020978 long-chain polyunsaturated fatty acids Nutrition 0.000 claims abstract description 90
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 23
- 229930195729 fatty acid Natural products 0.000 claims abstract description 23
- 239000000194 fatty acid Substances 0.000 claims abstract description 23
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 23
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims abstract description 15
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000002978 peroxides Chemical class 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 72
- 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 claims description 38
- 238000001035 drying Methods 0.000 claims description 25
- 238000010438 heat treatment Methods 0.000 claims description 20
- 235000021342 arachidonic acid Nutrition 0.000 claims description 19
- 229940114079 arachidonic acid Drugs 0.000 claims description 19
- 241000196324 Embryophyta Species 0.000 claims description 16
- YUFFSWGQGVEMMI-JLNKQSITSA-N (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O YUFFSWGQGVEMMI-JLNKQSITSA-N 0.000 claims description 12
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 10
- 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 claims description 9
- 238000003825 pressing Methods 0.000 claims description 9
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 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 claims description 7
- HOBAELRKJCKHQD-QNEBEIHSSA-N dihomo-γ-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O HOBAELRKJCKHQD-QNEBEIHSSA-N 0.000 claims description 7
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 7
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 7
- -1 20:3 .omega.-6) Chemical compound 0.000 claims description 6
- 239000012530 fluid Substances 0.000 claims description 6
- 230000009261 transgenic effect Effects 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 5
- HOBAELRKJCKHQD-UHFFFAOYSA-N (8Z,11Z,14Z)-8,11,14-eicosatrienoic acid Natural products CCCCCC=CCC=CCC=CCCCCCCC(O)=O HOBAELRKJCKHQD-UHFFFAOYSA-N 0.000 claims description 4
- 241000219198 Brassica Species 0.000 claims description 4
- 235000021294 Docosapentaenoic acid Nutrition 0.000 claims description 4
- 230000001877 deodorizing effect Effects 0.000 claims description 4
- 229940090949 docosahexaenoic acid Drugs 0.000 claims description 4
- 235000011331 Brassica Nutrition 0.000 claims description 3
- 230000001143 conditioned effect Effects 0.000 claims description 3
- 238000000227 grinding Methods 0.000 claims description 3
- 241000219193 Brassicaceae Species 0.000 claims description 2
- 238000000638 solvent extraction Methods 0.000 claims description 2
- 235000013305 food Nutrition 0.000 claims 6
- 239000000839 emulsion Substances 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 235000013350 formula milk Nutrition 0.000 claims 4
- 238000002156 mixing Methods 0.000 claims 3
- 241001465754 Metazoa Species 0.000 claims 2
- 239000008346 aqueous phase Substances 0.000 claims 2
- 239000002537 cosmetic Substances 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 229960004488 linolenic acid Drugs 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 229930182558 Sterol Natural products 0.000 description 10
- 235000003702 sterols Nutrition 0.000 description 10
- 150000003432 sterols Chemical class 0.000 description 9
- 239000010779 crude oil Substances 0.000 description 8
- 235000021588 free fatty acids Nutrition 0.000 description 6
- DVSZKTAMJJTWFG-SKCDLICFSA-N (2e,4e,6e,8e,10e,12e)-docosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C=C\C(O)=O DVSZKTAMJJTWFG-SKCDLICFSA-N 0.000 description 5
- GZJLLYHBALOKEX-UHFFFAOYSA-N 6-Ketone, O18-Me-Ussuriedine Natural products CC=CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O GZJLLYHBALOKEX-UHFFFAOYSA-N 0.000 description 5
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 5
- 238000004061 bleaching Methods 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- KAUVQQXNCKESLC-UHFFFAOYSA-N docosahexaenoic acid (DHA) Natural products COC(=O)C(C)NOCC1=CC=CC=C1 KAUVQQXNCKESLC-UHFFFAOYSA-N 0.000 description 5
- 239000002028 Biomass Substances 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 108700019146 Transgenes Proteins 0.000 description 4
- 244000178993 Brassica juncea Species 0.000 description 3
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 3
- 235000006008 Brassica napus var napus Nutrition 0.000 description 3
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 3
- 244000188595 Brassica sinapistrum Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 235000011332 Brassica juncea Nutrition 0.000 description 2
- 235000014700 Brassica juncea var napiformis Nutrition 0.000 description 2
- 240000002791 Brassica napus Species 0.000 description 2
- 244000197813 Camelina sativa Species 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 1
- 241000219194 Arabidopsis Species 0.000 description 1
- 241000219195 Arabidopsis thaliana Species 0.000 description 1
- 244000031988 Brassica alba Species 0.000 description 1
- 235000006463 Brassica alba Nutrition 0.000 description 1
- 235000011303 Brassica alboglabra Nutrition 0.000 description 1
- 235000008427 Brassica arvensis Nutrition 0.000 description 1
- 235000005156 Brassica carinata Nutrition 0.000 description 1
- 244000257790 Brassica carinata Species 0.000 description 1
- 244000140786 Brassica hirta Species 0.000 description 1
- 235000011371 Brassica hirta Nutrition 0.000 description 1
- 235000017328 Brassica juncea var foliosa Nutrition 0.000 description 1
- 235000007539 Brassica juncea var juncea Nutrition 0.000 description 1
- 235000005855 Brassica juncea var. subintegrifolia Nutrition 0.000 description 1
- 244000024671 Brassica kaber Species 0.000 description 1
- 235000011293 Brassica napus Nutrition 0.000 description 1
- 235000011291 Brassica nigra Nutrition 0.000 description 1
- 244000180419 Brassica nigra Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000011302 Brassica oleracea Nutrition 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 235000016401 Camelina Nutrition 0.000 description 1
- 235000014595 Camelina sativa Nutrition 0.000 description 1
- 101800004637 Communis Proteins 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- GFRROZIJVHUSKZ-FXGMSQOLSA-N OS I Natural products C[C@@H]1O[C@@H](O[C@H]2[C@@H](O)[C@@H](CO)O[C@@H](OC[C@@H](O)[C@@H](O)[C@@H](O)CO)[C@@H]2NC(=O)C)[C@H](O)[C@H](O)[C@H]1O GFRROZIJVHUSKZ-FXGMSQOLSA-N 0.000 description 1
- 241001506137 Rapa Species 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004332 deodorization Methods 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 description 1
- 235000020664 gamma-linolenic acid Nutrition 0.000 description 1
- 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 1
- 229960002733 gamolenic acid Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 244000142032 leaf mustard Species 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940075999 phytosterol ester Drugs 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/10—Production of fats or fatty oils from raw materials by extracting
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings or cooking oils characterised by the production or working-up
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01C—PLANTING; SOWING; FERTILISING
- A01C1/00—Apparatus, or methods of use thereof, for testing or treating seed, roots, or the like, prior to sowing or planting
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/003—Compositions other than spreads
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
-
- 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
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/40—Complete food formulations for specific consumer groups or specific purposes, e.g. infant formula
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pediatric Medicine (AREA)
- Mycology (AREA)
- Nutrition Science (AREA)
- Environmental Sciences (AREA)
- Soil Sciences (AREA)
- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
- Lubricants (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25777209P | 2009-11-03 | 2009-11-03 | |
| US61/257,772 | 2009-11-03 | ||
| EP2009065593 | 2009-11-22 | ||
| EPPCT/EP2009/065593 | 2009-11-22 | ||
| PCT/EP2010/066599 WO2011054801A1 (en) | 2009-11-03 | 2010-11-02 | Vegatable oil comprising a polyunsaturaded fatty acid having at least 20 carbon atoms |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2779552A1 CA2779552A1 (en) | 2011-05-12 |
| CA2779552C true CA2779552C (en) | 2019-04-09 |
Family
ID=43969588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2779552A Active CA2779552C (en) | 2009-11-03 | 2010-11-02 | Vegetable oil comprising a polyunsaturated fatty acid having at least 20 carbon atoms |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US20130101723A1 (enExample) |
| CN (2) | CN107258936A (enExample) |
| AU (1) | AU2010317140B2 (enExample) |
| CA (1) | CA2779552C (enExample) |
| DK (1) | DK2496091T3 (enExample) |
| ES (1) | ES2750241T3 (enExample) |
| IN (1) | IN2012DN03815A (enExample) |
| WO (1) | WO2011054801A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013101559A1 (en) * | 2011-12-30 | 2013-07-04 | Dow Agrosciences Llc | Dha retention during canola processing |
| KR102716618B1 (ko) * | 2015-08-25 | 2024-10-14 | 디에스엠 아이피 어셋츠 비.브이. | 정제된 오일 조성물 및 제조 방법 |
| PT3253227T (pt) * | 2015-12-02 | 2020-10-19 | Nuseed Global Innovation Ltd | Método para remoção de glicosinolatos de farinhas de sementes oleaginosas |
| US11096403B1 (en) * | 2017-03-21 | 2021-08-24 | Covercress Inc. | Low glucosinolate pennycress meal and methods of making |
| US10610280B1 (en) | 2019-02-02 | 2020-04-07 | Ayad K. M. Agha | Surgical method and apparatus for destruction and removal of intraperitoneal, visceral, and subcutaneous fat |
| WO2025238190A1 (en) | 2024-05-15 | 2025-11-20 | Dsm Ip Assets B.V. | Spray-dried powders having high pufa content |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4063018A (en) | 1975-04-07 | 1977-12-13 | Daicel Ltd. | Process for preparing alkali metal salt of carboxymethyl cellulose ether |
| ATE110224T1 (de) * | 1987-12-31 | 1994-09-15 | Pioneer Hi Bred Int | Produktion von raps mit erhöhtem ölsäuregehalt. |
| US4948811A (en) | 1988-01-26 | 1990-08-14 | The Procter & Gamble Company | Salad/cooking oil balanced for health benefits |
| EP0928556A3 (en) * | 1993-04-27 | 1999-09-15 | Cargill, Incorporated | Non-hydrogenated canola oil for food applications |
| GB9321479D0 (en) | 1993-10-18 | 1993-12-08 | Scotia Holdings Plc | Stabilisation of polyunsaturates |
| US5625130A (en) * | 1995-03-07 | 1997-04-29 | Pioneer Hi-Bred International, Inc. | Oilseed Brassica bearing an endogenous oil wherein the levels of oleic, alpha-linolenic, and saturated fatty acids are simultaneously provided in an atypical highly beneficial distribution via genetic control |
| HUP9600336A3 (en) | 1996-02-15 | 1998-11-30 | Pozsgai Imre | Process for producing of plant fatoil mixture with multiple partial valence, essential fatty acid |
| US6964786B1 (en) * | 1999-07-15 | 2005-11-15 | Pushpa Khanna | Oil from Momordica charantia L., its method of preparation and uses |
| SE523094C2 (sv) | 2001-01-11 | 2004-03-30 | Karlshamns Ab | Förfarande för framställning av en fettkomposition som innehåller sterolestrar, fria steroler och glycerider, fettkomposition framställd genom förfarandet samt fettkompositionens användning |
| WO2003049832A1 (en) * | 2001-12-12 | 2003-06-19 | Martek Biosciences Boulder Corp. | Extraction and winterization of lipids from oilseed and microbial sources |
| US20040172682A1 (en) | 2003-02-12 | 2004-09-02 | Kinney Anthony J. | Production of very long chain polyunsaturated fatty acids in oilseed plants |
| US8084074B2 (en) * | 2003-02-12 | 2011-12-27 | E. I. Du Pont De Nemours And Company | Production of very long chain polyunsaturated fatty acids in oil seed plants |
| EP1710306B1 (en) | 2003-12-17 | 2011-06-01 | Suntory Holdings Limited | Arachidonic acid-containing plant and utilization of the same |
| EP4219670A3 (de) | 2004-02-27 | 2023-08-09 | BASF Plant Science GmbH | Verfahren zur herstellung mehrfach ungesättigter fettsäuren in transgenen pflanzen |
| JP4567047B2 (ja) * | 2004-02-27 | 2010-10-20 | ビーエーエスエフ プラント サイエンス ゲーエムベーハー | トランスジェニック植物における多価不飽和脂肪酸の製造方法 |
| WO2005083053A2 (de) * | 2004-02-27 | 2005-09-09 | Basf Plant Science Gmbh | Verfahren zur herstellung von ungesättigten omega-3-fettsäuren in transgenen organismen |
| CN101098629B (zh) * | 2004-11-04 | 2010-10-13 | 孟山都技术公司 | 高pufa油组合物 |
| JP5941606B2 (ja) * | 2004-11-04 | 2016-06-29 | モンサント テクノロジー エルエルシー | 高ｐｕｆａ油組成物 |
| WO2007021899A1 (en) * | 2005-08-10 | 2007-02-22 | Bunge Oils, Inc. | Edible oils and methods of making edible oils |
| US7867538B2 (en) * | 2005-12-20 | 2011-01-11 | Archer Daniels Midland Company | Processes of improving the quality of oil and products produced therefrom |
| AR059376A1 (es) * | 2006-02-21 | 2008-03-26 | Basf Plant Science Gmbh | Procedimiento para la produccion de acidos grasos poliinsaturados |
| NZ547429A (en) * | 2006-05-24 | 2009-09-25 | Ind Res Ltd | Extraction of highly unsaturated lipids with liquid dimethyl ether |
| DE102006034313A1 (de) * | 2006-07-21 | 2008-01-24 | Basf Plant Science Gmbh | Verfahren zur Herstellung von Arachidonsäure und/oder Eicosapentaensäure |
| BRPI0806354A2 (pt) | 2007-02-12 | 2011-09-06 | Du Pont | plantas oleaginosas transgências, sementes, óleos, produtos alimentìcios ou análogos a alimento, produtos alimentìcios medicinais ou análogos alimentìcios medicinais, produtos farmacêuticos, bebidas fórmulas para bebês, suplementos nutricionais, rações para animais domésticos, alimentos para aquacultura, rações animais, produtos de sementes inteiras, produtos de óleos misturados, produtos, subprodutos e subprodutos parcialmente processados |
| MX2009010574A (es) | 2007-04-03 | 2009-10-22 | Du Pont | Multienzimas y su uso en la fabricacion de acidos grasos poliinsaturados. |
| US8188338B2 (en) | 2007-04-10 | 2012-05-29 | E. I. Du Pont De Nemours And Company | Delta-8 desaturases and their use in making polyunsaturated fatty acids |
| US8119860B2 (en) | 2007-04-16 | 2012-02-21 | E. I. Du Pont De Nemours And Company | Delta-9 elongases and their use in making polyunsaturated fatty acids |
| US20090169650A1 (en) * | 2008-01-02 | 2009-07-02 | Wilkes Richard S | Food compositions incorporating stearidonic acid |
| CA2721879A1 (en) | 2008-04-25 | 2009-10-29 | Basf Plant Science Gmbh | Plant seed oil |
-
2010
- 2010-11-02 WO PCT/EP2010/066599 patent/WO2011054801A1/en not_active Ceased
- 2010-11-02 ES ES10773309T patent/ES2750241T3/es active Active
- 2010-11-02 AU AU2010317140A patent/AU2010317140B2/en active Active
- 2010-11-02 IN IN3815DEN2012 patent/IN2012DN03815A/en unknown
- 2010-11-02 US US13/504,148 patent/US20130101723A1/en not_active Abandoned
- 2010-11-02 DK DK10773309T patent/DK2496091T3/da active
- 2010-11-02 CA CA2779552A patent/CA2779552C/en active Active
- 2010-11-02 CN CN201710575286.XA patent/CN107258936A/zh active Pending
- 2010-11-02 CN CN2010800499768A patent/CN102595918A/zh active Pending
-
2014
- 2014-12-01 US US14/557,303 patent/US20150089692A1/en not_active Abandoned
-
2021
- 2021-02-09 US US17/171,748 patent/US12203048B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20130101723A1 (en) | 2013-04-25 |
| US20150089692A1 (en) | 2015-03-26 |
| AU2010317140B2 (en) | 2016-04-21 |
| ES2750241T3 (es) | 2020-03-25 |
| AU2010317140A1 (en) | 2012-05-24 |
| US20210163843A1 (en) | 2021-06-03 |
| CN102595918A (zh) | 2012-07-18 |
| CA2779552A1 (en) | 2011-05-12 |
| WO2011054801A1 (en) | 2011-05-12 |
| IN2012DN03815A (enExample) | 2015-08-28 |
| CN107258936A (zh) | 2017-10-20 |
| DK2496091T3 (da) | 2019-11-04 |
| US12203048B2 (en) | 2025-01-21 |
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