WO2003064576A2 - High linolenic acid flax - Google Patents
High linolenic acid flax Download PDFInfo
- Publication number
- WO2003064576A2 WO2003064576A2 PCT/CA2003/000116 CA0300116W WO03064576A2 WO 2003064576 A2 WO2003064576 A2 WO 2003064576A2 CA 0300116 W CA0300116 W CA 0300116W WO 03064576 A2 WO03064576 A2 WO 03064576A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- flax
- acid content
- seed
- linolenic acid
- linolenic
- 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
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01H—NEW PLANTS OR NON-TRANSGENIC PROCESSES FOR OBTAINING THEM; PLANT REPRODUCTION BY TISSUE CULTURE TECHNIQUES
- A01H5/00—Angiosperms, i.e. flowering plants, characterised by their plant parts; Angiosperms characterised otherwise than by their botanic taxonomy
- A01H5/10—Seeds
Definitions
- the present invention relates generally to the field of agriculture. More specifically, the present invention relates to flax seeds, plants and oils having altered fatty acid profiles.
- Unsaturated fatty acids consist of monosaturates and polyunsaturates (PuFA).
- PuFA's There are two classes of PuFA's, omega-3 and omega-6 which are considered as essential fatty acids (EFA) because humans, like all mammals, cannot synthesize them and most obtain them in their diet.
- Omega-3 is represented by alpha-linolenic acid (LNA) and linseed flax has the highest linolenic content of major seed oils.
- LNA is metabolized to eicosapentaenoic acid (EPA) and docosahexanoic acid (DHA), increasing the chain length and degree of unsaturation by adding double bonds to the carboxyl group. Humans and animals can convert LNA to EPA and DHA.
- Essential fatty acids have several vital functions: they increase metabolic rate, improve metabolism, increase oxygen uptake and increase energy production.
- EPA and their derivatives are components of membranes surrounding cells; they are required for the transport and metabolism of cholesterol and triglycerides; they are required for normal development of the brain and for brain function in adults; and from EPA's the body makes hormone-like substances called prostaglandins which have important regulating functions in the body, i.e. they regulate arterial muscle tone, sodium excretion through the kidneys, platelet
- omega-3 fatty acids may play an important role in the prevention and treatment of coronary artery disease, hypertension, diabetes, arthritis, and other inflammatory
- Linseed flax is grown primarily for its oil which has many industrial
- Linseed oil is also used as an anti-spalling and curing agent for concrete surfaces including highways and bridges.
- Linseed oil is used as an industrial oil because of its drying property, i.e. ability to dry rapidly to form a durable film upon exposure to air.
- the drying property of linseed oil is due to the high content of unsaturated fatty acids, particularly linolenic acid.
- the linolenic content of Canadian flax cultivars varies from 49-62% depending on cultivar and growing conditions. Temperature during seed formation and photoperiod influences the degree of unsaturation of the fatty acid in linseed oil. Cool temperatures and longer photoperiod increases linolenic content. Other factors which may affect the variability of linolenic content are soil moisture, soil fertility and presence of disease.
- High linolenic flax oil provides a valuable improved source of omega- 3 fatty acid for human nutrition, animal feed and pet foods.
- a flax seed having a linolenic acid content of greater than 65% of the total fatty acid content of said seed.
- a flax seed that is the product of a plant line designated M5791.
- a flax plant which produces seeds having a linolenic acid content of greater than 65% of the total fatty acid content of said seed.
- a flax plant designated M5791 According to a fourth aspect of the invention, there is provided a flax plant designated M5791.
- progeny of a flax plant designated M5791 wherein said progeny produce seeds having a linolenic acid content of greater than 65% of the total fatty acid content of said seed.
- a method of producing a flax plant line comprising the steps of:
- TABLE 1 shows the fatty acid composition of major seed oils.
- TABLE 2 shows fatty acid composition and iodine value of linseed flax and high linolenic flax (M 5791 ).
- TABLE 5 shows the analysis of linolenic acid content of M5791.
- FIGURE 1 shows the structural formula for fatty acids.
- the first number (before the colon) gives the number of carbon atoms in the molecule and the second gives the number of double bonds.
- ⁇ 3, ⁇ 6, and ⁇ 9 indicate the position of the first double bond in a given fatty acid molecule.
- FIGURE 2 shows the elongation and desaturation of n-6 and n-3 polyunsaturated fatty acids.
- FIGURE 3 shows the pedigree of high linolenic flax M 5791. DESCRIPTION OF THE PREFERRED EMBODIMENTS
- high linolenic flax refers to flax seeds or plants wherein the percentage of total fatty acid content that is linolenic acid is greater than 65%.
- inflammatory disease refers to diseases that are associated with an inappropriate or over-activation of the inflammation cascade.
- autoimmune disorder refers to diseases characterized by destruction of host tissue by the host immune system.
- the invention relates to flax seeds, plants or products made therefrom wherein linolenic acid is greater than 65% of the total fatty acid content.
- the linolenic acid content may be greater than 70% of the total fatty acid content. In yet other embodiments, the linolenic acid content may be 70-80% or 70-75% of the total fatty acid content.
- M5791 As discussed herein, the crossing of flax lines has produced a high linolenic flax line, designated M5791. As shown in Tables 4 and 5, M5791 shows much higher linolenic acid content relative to other flax lines. As will be appreciated by one knowledgeable in the art, and as discussed herein, growth conditions can affect linolenic acid content. However, flax line M5791 can be grown and processed using means known in the art for growing and processing flax.
- the linolenic content of M 5791 oil is not altered by any methods of extraction of oil from seed, i.e. solvent, cold press, or distillation.
- flax and/or linseed oil have are present in a number of industrial, nutritional and medicinal products.
- linseed oil is used as an industrial oil because of its drying properties, which are in turn directly proportional to the linolenic acid content.
- Industrial uses of this oil include but are by no means limited to the manufacture of brake linings, adhesives, manufacture of hardboard and fibreboard, protective coatings, paints, house paint primers, varnishes, lacquers, stains, alkyd resins, enamels, epoxidized oils, floor coverings, linoleum, oilcloth, tarpaulin and other coated fabrics, patent leather, industrial chemical, fatty acids, soap, glycerin, printing inks, grinding oils, newsprint, core oils, caulking compounds, waterproofing compounds, mastic cements, foundry binders, brake lining, hardboard, shoe polish, herbicide, pesticide carrier, antispalling and curing treatments for concrete, tempering oil, bonding oil, and highly conjugated oils for hardboards and the like.
- linseed oil from high linolenic acid flax will result in, for examples, faster drying paints, coatings, inks and the like.
- industrial uses of linseed oil include but are by no means limited to US Patents 5,965,633, 5,693,715, 5,653,789, 3,488,202 and 4,002,585.
- the meal remaining from the flax seed oil extraction includes but are by no means limited to US Patents 5,965,633, 5,693,715, 5,653,789, 3,488,202 and 4,002,585.
- meal from the high linolenic acid flax seeds may be used in any application known in the art for using meal from flax seeds, wherein the meal has the added benefit of having a
- the above-described flax seed may be used, for example, to
- the seed, oil, or meal may be used in feed for dairy and beef cattle, swine and/or poultry to increase levels of linolenic acid in the resulting food products, for example, eggs, meat and milk.
- the seed and meal may also be used in pet foods.
- the seed and oil may also be used as a source of linolenic acid for growing fish.
- polyunsatu rated fats for example, linolenic acid are essential fatty acids and are required for increased metabolism, oxygen uptake, and energy production.
- nutritional supplements or food products containing material produced or processed from the high linolenic acid flax line would be higher in polyunsatu rated fats and therefore of greater benefit.
- the high linolenic flax line, seeds or products derived therefrom can be used in, for
- linolenic acid also plays a role in the prevention and/or treatment of a number of diseases, including , for example, coronary artery disease, hypertension, diabetes, arthritis and other inflammatory or autoimmune disorders.
- supplements or pharmaceutical compositions including material derived from the high linolenic acid flax are prepared and used to treat and/or prevent the above-referenced diseases or disorders.
- Examples of medicinal uses for flax and/or linseed oil include but are by no means limited to US Patents 5,859,055, 4,415,554, 5,468,776 and 4,058,594.
- the high linolenic linseed oil or high linolenic flax may be included in a tablet, capsule, tincture, salve, paste, cream or the like.
- the high linolenic acid flax or linseed oil therefrom at therapeutically effective concentrations or dosages may be combined with a pharmaceutically or pharmacologically acceptable carrier, excipient or diluent, either biodegradable or non-biodegradable.
- Exemplary examples of earners include, but are by no means limited to, for example, poly(ethylene-vinyl acetate), copolymers of lactic acid and glycolic acid, poly(lactic acid), gelatin, collagen matrices, polysaccharides, poly(D,L lactide), poly(malic acid), poly(caprolactone), celluloses, albumin, starch, casein, dextran, polyesters, ethanol, mathacrylate, polyurethane, polyethylene, vinyl polymers, glycols, mixtures thereof and the like.
- Standard excipients include gelatin, casein, lecithin, gum acacia, cholesterol, tragacanth, stearic acid, benzalkonium chloride, calcium stearate, glyceryl monostearate, cetostearyl alcohol, cetomacrogol emulsifying wax, sorbitan esters, polyoxyethylene alkyl ethers, polyoxyethylene castor oil derivatives, polyoxyethylene sorbitan fatty acid esters, polyethylene glycols, polyoxyethylene stearates, colloidol silicon dioxide, phosphates, sodium dodecylsulfate, carboxymethylcellulose calcium, carboxymethylcellulose sodium, methylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethycellulose phthalate, noncrystalline cellulose, magnesium aluminum silicate, triethanolamine, polyvinyl alcohol, polyvinylpyrrolidone, sugars and starches. See, for example, Remington: The Science and Practice of
- oil from the seeds of the high linolenic acid is obtained from the seeds of the high linolenic acid
- flax plants are used as carriers or diluents for other pharmaceutical or medicinal compounds.
- the high linolenic acid flax line, seeds therefrom or products derived therefrom can be used in the production of any flax-containing products known in the art. As will be appreciated by one knowledgeable in the art, these products will have the added benefit of having a higher linolenic acid content.
- the flax plant designated M5791 can be used to perform genetic crosses with other flax lines using means known in the art.
- High Linolenic flax was developed by conventional plant breeding, ie. hybridization using cultivars, breeding lines and accessions, and selections for high linolenic acid content in segregating populations from crosses, at the AAFC Morden Research Centre, Morden, MB. The development of High Linolenic flax
- F6 lines were selected for high linolenic content at Morden and seed harvested in bulk. Seed of F7 lines was increased in a winter nursery. High linolenic flax was evaluated in replicated trials conducted in 1998, 1999 and 2000, and in field trials conducted in 1998 and 1999 (Table 5).
- Linolenic acid content determined by gas-liquid chromatography of the fatty acid esters using the method described by Daun et al., J. Amer. Oil Chemists' Society, 60, 1983. Table 6. Linolenic Acid Content of High Linolenic Flax (M 5791) in Field Trials, 1998 & 1999
- Linseed Oil Adhesives i.e. manufacture of hardboard and fibreboard
- Raw & Refined Floor Covering linoleum Boiled & Blown Oilcloth, tarpaulin and other coated fabrics Grinding Oils Patent leather Heat Boiled Industrial Chemicals: fatty acids, soap, glycerin
- Seed, oil, meal Dairy and beef cattle, swine and poultry feed and also to increase levels of linolenic acid in food products, i.e. eggs, meat and milk
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Physiology (AREA)
- Botany (AREA)
- Developmental Biology & Embryology (AREA)
- Environmental Sciences (AREA)
- Fats And Perfumes (AREA)
- Breeding Of Plants And Reproduction By Means Of Culturing (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Bakery Products And Manufacturing Methods Therefor (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2003203073A AU2003203073B2 (en) | 2002-01-30 | 2003-01-30 | High linolenic acid flax |
| EP03701378A EP1471784A2 (en) | 2002-01-30 | 2003-01-30 | High linolenic acid flax |
| JP2003564173A JP2005515774A (ja) | 2002-01-30 | 2003-01-30 | 高リノレン酸亜麻 |
| NZ534822A NZ534822A (en) | 2002-01-30 | 2004-08-19 | Flax seed used to produce oil comprising a specified linolenic acid content |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/059,080 | 2002-01-30 | ||
| US10/059,080 US6870077B2 (en) | 2002-01-30 | 2002-01-30 | High linolenic acid flax |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2003064576A2 true WO2003064576A2 (en) | 2003-08-07 |
| WO2003064576A8 WO2003064576A8 (en) | 2004-03-18 |
Family
ID=27658245
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/CA2003/000116 Ceased WO2003064576A2 (en) | 2002-01-30 | 2003-01-30 | High linolenic acid flax |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US6870077B2 (enExample) |
| EP (1) | EP1471784A2 (enExample) |
| JP (1) | JP2005515774A (enExample) |
| CN (1) | CN1642410A (enExample) |
| AU (1) | AU2003203073B2 (enExample) |
| NZ (1) | NZ534822A (enExample) |
| WO (1) | WO2003064576A2 (enExample) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7922811B2 (en) | 2005-06-02 | 2011-04-12 | W. R. Grace & Co.-Conn. | Biomass-derived grinding aids |
| EP2701698A4 (en) * | 2011-04-26 | 2014-10-15 | Retrotope Inc | DISEASES WITH PUFA OXIDATION |
| WO2018104596A1 (fr) * | 2016-12-09 | 2018-06-14 | Etablissements Andre Laboulet | Plantes de lin a haute teneur en omega-3 |
| US10052299B2 (en) | 2009-10-30 | 2018-08-21 | Retrotope, Inc. | Alleviating oxidative stress disorders with PUFA derivatives |
| US10058612B2 (en) | 2011-04-26 | 2018-08-28 | Retrotope, Inc. | Impaired energy processing disorders and mitochondrial deficiency |
| US10058522B2 (en) | 2011-04-26 | 2018-08-28 | Retrotope, Inc. | Oxidative retinal diseases |
| US10154983B2 (en) | 2011-04-26 | 2018-12-18 | Retrotope, Inc. | Neurodegenerative disorders and muscle diseases implicating PUFAs |
| US11447441B2 (en) | 2015-11-23 | 2022-09-20 | Retrotope, Inc. | Site-specific isotopic labeling of 1,4-diene systems |
| US11779910B2 (en) | 2020-02-21 | 2023-10-10 | Biojiva Llc | Processes for isotopic modification of polyunsaturated fatty acids and derivatives thereof |
| US12109194B2 (en) | 2021-02-05 | 2024-10-08 | Biojiva Llc | Synergistic combination therapy for treating ALS |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10151155A1 (de) * | 2001-10-19 | 2003-05-08 | Nutrinova Gmbh | Native PUFA-Triglyceridmischungen mit einem hohen Gehalt an mehrfach ungesättigten Fettsäuren sowie Verfahren zu deren Herstellung und deren Verwendung |
| US6870077B2 (en) * | 2002-01-30 | 2005-03-22 | Edward O. Kenaschuk | High linolenic acid flax |
| US20050132441A1 (en) | 2003-11-12 | 2005-06-16 | Damude Howard G. | Delta15 desaturases suitable for altering levels of polyunsaturated fatty acids in oilseed plants and oleaginous yeast |
| RU2008122057A (ru) * | 2005-11-03 | 2009-12-10 | Лиллиан ПИТЕРСОН (CA) | Высоколиноленовые композиции льняного масла |
| US20080069942A1 (en) * | 2006-09-15 | 2008-03-20 | Glenn Roy Pizzey | Flax-stabilized fatty acid compositions and methods |
| JP2010524493A (ja) * | 2007-04-29 | 2010-07-22 | シェメン インダストリーズ リミテッド | 乳児および幼児のための栄養供給用油組成物 |
| AU2009226019C1 (en) | 2008-03-20 | 2014-02-20 | Virun, Inc. | Emulsions including a PEG-derivative of tocopherol |
| CN103190631B (zh) | 2008-03-20 | 2016-01-20 | 维尔恩公司 | 非水性预乳液组合物及制备包含植物甾醇的饮料的方法 |
| US8337931B2 (en) * | 2008-06-23 | 2012-12-25 | Virun, Inc. | Compositions containing non-polar compounds |
| US20120237658A1 (en) * | 2009-09-10 | 2012-09-20 | Cargil, Incorporated | Oxidatively stable fats with elevated alpha-linolenic acid content |
| CN103037708B (zh) * | 2010-03-23 | 2015-05-20 | 维尔恩公司 | 含有蔗糖脂肪酸酯的纳米乳液 |
| WO2011162802A1 (en) | 2010-06-21 | 2011-12-29 | Virun, Inc. | Compositions containing non-polar compounds |
| US8877259B2 (en) | 2012-02-09 | 2014-11-04 | Mary Kay Inc. | Cosmetic formulation |
| WO2013120025A1 (en) | 2012-02-10 | 2013-08-15 | Virun, Inc. | Beverage compositions containing non-polar compounds |
| AU2014235283B2 (en) | 2013-03-15 | 2017-06-01 | Virun, Inc. | Formulations of water-soluble derivatives of vitamin E and compositions containing same |
| US9351517B2 (en) | 2013-03-15 | 2016-05-31 | Virun, Inc. | Formulations of water-soluble derivatives of vitamin E and compositions containing same |
| US9693574B2 (en) | 2013-08-08 | 2017-07-04 | Virun, Inc. | Compositions containing water-soluble derivatives of vitamin E mixtures and modified food starch |
| WO2016044805A1 (en) | 2014-09-18 | 2016-03-24 | Virun, Inc. | Soft gel compositions and pre-gel concentrates |
| US10016363B2 (en) | 2014-09-18 | 2018-07-10 | Virun, Inc. | Pre-spray emulsions and powders containing non-polar compounds |
| US9861611B2 (en) | 2014-09-18 | 2018-01-09 | Virun, Inc. | Formulations of water-soluble derivatives of vitamin E and soft gel compositions, concentrates and powders containing same |
| CA3054548A1 (en) * | 2016-02-26 | 2017-08-31 | Nathan Golas | High alpha linolenic acid flax |
| FR3073711B1 (fr) * | 2017-11-21 | 2021-03-12 | Valorex Sa | Procede de traitement de graines de lin en vue d'ameliorer leur valorisation a titre d'aliments |
| EP3693180B1 (en) | 2019-02-05 | 2023-09-13 | Flooring Industries Limited, SARL | Method for manufacturing a decorative foil and a panel comprising such foil |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5069903A (en) * | 1987-12-16 | 1991-12-03 | Stitt Paul A | Therapeutic and nutritive flax seed composition and methods employing the same |
| DE4042354A1 (de) * | 1990-09-21 | 1992-03-26 | Allkraft Futtermittel Gmbh | Futtermittel aus leinsamen |
| CA2124673C (en) | 1991-12-04 | 2008-08-05 | John Browse | Fatty acid desaturase genes from plants |
| US5288805A (en) * | 1992-08-14 | 1994-02-22 | Cargill, Incorporated | Linseed oil based polymeric vehicle |
| US5653789A (en) * | 1994-05-23 | 1997-08-05 | Permagrain Products, Inc. | Water base conditioner for acrylic wood flooring |
| US6060101A (en) * | 1994-09-02 | 2000-05-09 | Designing Health, Inc. | Dietary food supplement |
| DE19941609A1 (de) | 1999-09-01 | 2001-03-08 | Inst Pflanzenbiochemie Ipb | Fettsäure-Desaturase-Gen aus Pflanzen |
| US20030131737A1 (en) * | 2001-12-13 | 2003-07-17 | Wuwei Cui | Process and apparatus for flaxseed component separation |
| US6870077B2 (en) * | 2002-01-30 | 2005-03-22 | Edward O. Kenaschuk | High linolenic acid flax |
-
2002
- 2002-01-30 US US10/059,080 patent/US6870077B2/en not_active Expired - Lifetime
-
2003
- 2003-01-30 WO PCT/CA2003/000116 patent/WO2003064576A2/en not_active Ceased
- 2003-01-30 EP EP03701378A patent/EP1471784A2/en not_active Ceased
- 2003-01-30 AU AU2003203073A patent/AU2003203073B2/en not_active Expired
- 2003-01-30 JP JP2003564173A patent/JP2005515774A/ja active Pending
- 2003-01-30 CN CNA038060833A patent/CN1642410A/zh active Pending
-
2004
- 2004-08-19 NZ NZ534822A patent/NZ534822A/en not_active IP Right Cessation
- 2004-10-25 US US10/971,154 patent/US7763303B2/en not_active Expired - Lifetime
Non-Patent Citations (2)
| Title |
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| No Search * |
| See also references of EP1471784A2 * |
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9328021B2 (en) | 2005-06-02 | 2016-05-03 | Gcp Applied Technologies Inc. | Biomass derived grinding aids |
| US7922811B2 (en) | 2005-06-02 | 2011-04-12 | W. R. Grace & Co.-Conn. | Biomass-derived grinding aids |
| US10052299B2 (en) | 2009-10-30 | 2018-08-21 | Retrotope, Inc. | Alleviating oxidative stress disorders with PUFA derivatives |
| US11510888B2 (en) | 2009-10-30 | 2022-11-29 | Retrotope, Inc. | Alleviating oxidative stress disorders with PUFA derivatives |
| USRE49238E1 (en) | 2009-10-30 | 2022-10-11 | Retrotope, Inc. | Alleviating oxidative stress disorders with PUFA derivatives |
| US10154983B2 (en) | 2011-04-26 | 2018-12-18 | Retrotope, Inc. | Neurodegenerative disorders and muscle diseases implicating PUFAs |
| US11285125B2 (en) | 2011-04-26 | 2022-03-29 | Retrotope, Inc. | Oxidative retinal diseases |
| US10058612B2 (en) | 2011-04-26 | 2018-08-28 | Retrotope, Inc. | Impaired energy processing disorders and mitochondrial deficiency |
| US10058522B2 (en) | 2011-04-26 | 2018-08-28 | Retrotope, Inc. | Oxidative retinal diseases |
| US10154978B2 (en) | 2011-04-26 | 2018-12-18 | Retrotope, Inc. | Disorders implicating PUFA oxidation |
| US12156860B2 (en) | 2011-04-26 | 2024-12-03 | Biojiva Llc | Disorders implicating PUFA oxidation |
| US11241409B2 (en) | 2011-04-26 | 2022-02-08 | Retrotope, Inc. | Neurodegenerative disorders and muscle diseases implicating PUFAs |
| EP2701698A4 (en) * | 2011-04-26 | 2014-10-15 | Retrotope Inc | DISEASES WITH PUFA OXIDATION |
| AU2012249920B2 (en) * | 2011-04-26 | 2017-06-15 | Biojiva Llc | Disorders implicating PUFA oxidation |
| US11453637B2 (en) | 2015-11-23 | 2022-09-27 | Retrotope, Inc. | Site-specific isotopic labeling of 1,4-diene systems |
| US11447441B2 (en) | 2015-11-23 | 2022-09-20 | Retrotope, Inc. | Site-specific isotopic labeling of 1,4-diene systems |
| US12060324B2 (en) | 2015-11-23 | 2024-08-13 | Biojiva Llc | Site-specific isotopic labeling of 1,4-diene systems |
| FR3059870A1 (fr) * | 2016-12-09 | 2018-06-15 | Etablissements Andre Laboulet | Plantes de lin a haute teneur en omega-3 |
| WO2018104596A1 (fr) * | 2016-12-09 | 2018-06-14 | Etablissements Andre Laboulet | Plantes de lin a haute teneur en omega-3 |
| US11779910B2 (en) | 2020-02-21 | 2023-10-10 | Biojiva Llc | Processes for isotopic modification of polyunsaturated fatty acids and derivatives thereof |
| US12109194B2 (en) | 2021-02-05 | 2024-10-08 | Biojiva Llc | Synergistic combination therapy for treating ALS |
Also Published As
| Publication number | Publication date |
|---|---|
| US6870077B2 (en) | 2005-03-22 |
| AU2003203073A2 (en) | 2003-09-02 |
| JP2005515774A (ja) | 2005-06-02 |
| AU2003203073B2 (en) | 2008-05-15 |
| NZ534822A (en) | 2008-06-30 |
| US20030159172A1 (en) | 2003-08-21 |
| CN1642410A (zh) | 2005-07-20 |
| US20050198709A1 (en) | 2005-09-08 |
| EP1471784A2 (en) | 2004-11-03 |
| WO2003064576A8 (en) | 2004-03-18 |
| US7763303B2 (en) | 2010-07-27 |
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