CA2692355C - Production and purification of esters of polyunsaturated fatty acids - Google Patents
Production and purification of esters of polyunsaturated fatty acids Download PDFInfo
- Publication number
- CA2692355C CA2692355C CA2692355A CA2692355A CA2692355C CA 2692355 C CA2692355 C CA 2692355C CA 2692355 A CA2692355 A CA 2692355A CA 2692355 A CA2692355 A CA 2692355A CA 2692355 C CA2692355 C CA 2692355C
- Authority
- CA
- Canada
- Prior art keywords
- composition
- ester
- acid
- fatty acid
- polyunsaturated fatty
- 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.)
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- 235000020777 polyunsaturated fatty acids Nutrition 0.000 title claims abstract description 240
- 150000002148 esters Chemical class 0.000 title claims abstract description 209
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- 238000000746 purification Methods 0.000 title description 7
- 239000000203 mixture Substances 0.000 claims abstract description 328
- 238000000034 method Methods 0.000 claims abstract description 143
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 110
- 150000003626 triacylglycerols Chemical class 0.000 claims abstract description 81
- 150000004665 fatty acids Chemical group 0.000 claims abstract description 49
- 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 141
- 125000004494 ethyl ester group Chemical group 0.000 claims description 81
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 71
- 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 70
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 70
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- 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 19
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- SOQKXJABGLKWQX-UHFFFAOYSA-N octacosa-4,7,10,13,16,19,22,25-octaenoic acid Chemical compound CCC=CCC=CCC=CCC=CCC=CCC=CCC=CCC=CCCC(O)=O SOQKXJABGLKWQX-UHFFFAOYSA-N 0.000 claims description 12
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- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
- A21D2/14—Organic oxygen compounds
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/158—Fatty acids; Fats; Products containing oils or fats
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- 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
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/115—Fatty acids or derivatives thereof; Fats or oils
- A23L33/12—Fatty acids or derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- 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
- A61P3/06—Antihyperlipidemics
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
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- 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
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
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| US60/947,284 | 2007-06-29 | ||
| PCT/US2008/068613 WO2009006317A1 (en) | 2007-06-29 | 2008-06-27 | Production and purification of esters of polyunsaturated fatty acids |
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| MX (2) | MX2010000263A (OSRAM) |
| WO (1) | WO2009006317A1 (OSRAM) |
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| US7169946B1 (en) * | 2004-03-05 | 2007-01-30 | Twin Rivers Technologies, L.P. | Alternatives to distilled oleo chemicals in derivatives and production thereof |
| SG155189A1 (en) * | 2004-08-06 | 2009-09-30 | Transform Pharmaceuticals Inc | Novel fenofibrate formulations and related methods of treatment |
| US7666234B2 (en) * | 2004-10-20 | 2010-02-23 | Council Of Scientific And Industrial Research | Process for the preparation of fatty acid methyl ester from triglyceride oil by transesterification |
| DE102005003624A1 (de) * | 2005-01-26 | 2006-07-27 | Nutrinova Nutrition Specialties & Food Ingredients Gmbh | Herstellung und Anwendung eines antioxidativ wirksamen Extraktes aus Crypthecodinium sp. |
| US7700793B2 (en) * | 2005-06-09 | 2010-04-20 | Biosphere Environmental Energy Llc | Systems and methods for esterification and transesterification of fats and oils |
| CA2692355C (en) * | 2007-06-29 | 2018-09-11 | Martek Biosciences Corporation | Production and purification of esters of polyunsaturated fatty acids |
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2008
- 2008-06-27 CA CA2692355A patent/CA2692355C/en active Active
- 2008-06-27 JP JP2010515186A patent/JP2010532418A/ja active Pending
- 2008-06-27 US US12/163,555 patent/US20090023808A1/en not_active Abandoned
- 2008-06-27 MX MX2010000263A patent/MX2010000263A/es active IP Right Grant
- 2008-06-27 AU AU2008269989A patent/AU2008269989B2/en not_active Ceased
- 2008-06-27 WO PCT/US2008/068613 patent/WO2009006317A1/en not_active Ceased
- 2008-06-27 CN CN200880104965A patent/CN101796014A/zh active Pending
- 2008-06-27 MX MX2015006380A patent/MX374545B/es unknown
- 2008-06-27 EP EP08781103.0A patent/EP2173699A4/en not_active Ceased
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2009
- 2009-12-29 US US12/649,178 patent/US20110098356A1/en not_active Abandoned
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2014
- 2014-01-13 US US14/154,140 patent/US9796658B2/en not_active Expired - Fee Related
- 2014-05-27 AU AU2014202880A patent/AU2014202880B2/en not_active Ceased
Also Published As
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|---|---|
| CN101796014A (zh) | 2010-08-04 |
| AU2014202880B2 (en) | 2017-08-31 |
| EP2173699A1 (en) | 2010-04-14 |
| AU2008269989A1 (en) | 2009-01-08 |
| US20140128465A1 (en) | 2014-05-08 |
| JP2010532418A (ja) | 2010-10-07 |
| MX374545B (es) | 2025-03-06 |
| AU2014202880A1 (en) | 2014-06-19 |
| US20110098356A1 (en) | 2011-04-28 |
| AU2008269989B2 (en) | 2014-02-27 |
| WO2009006317A1 (en) | 2009-01-08 |
| MX2010000263A (es) | 2010-03-11 |
| CA2692355A1 (en) | 2009-01-08 |
| US9796658B2 (en) | 2017-10-24 |
| US20090023808A1 (en) | 2009-01-22 |
| EP2173699A4 (en) | 2014-04-16 |
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