NO319194B1 - Lipase-katalysert forestringsfremgangsmate av marine oljer - Google Patents
Lipase-katalysert forestringsfremgangsmate av marine oljer Download PDFInfo
- Publication number
- NO319194B1 NO319194B1 NO20025456A NO20025456A NO319194B1 NO 319194 B1 NO319194 B1 NO 319194B1 NO 20025456 A NO20025456 A NO 20025456A NO 20025456 A NO20025456 A NO 20025456A NO 319194 B1 NO319194 B1 NO 319194B1
- Authority
- NO
- Norway
- Prior art keywords
- dha
- lipase
- epa
- fatty acids
- free fatty
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 46
- 238000005886 esterification reaction Methods 0.000 title claims description 30
- 230000032050 esterification Effects 0.000 title claims description 21
- 239000003921 oil Substances 0.000 title description 37
- MBMBGCFOFBJSGT-KUBAVDMBSA-N docosahexaenoic acid Natural products 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 110
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 108
- 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 82
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 82
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 81
- 108090001060 Lipase Proteins 0.000 claims description 44
- 239000004367 Lipase Substances 0.000 claims description 44
- 102000004882 Lipase Human genes 0.000 claims description 44
- 235000019421 lipase Nutrition 0.000 claims description 44
- 235000019198 oils Nutrition 0.000 claims description 38
- 235000021588 free fatty acids Nutrition 0.000 claims description 35
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 31
- 229930195729 fatty acid Natural products 0.000 claims description 31
- 239000000194 fatty acid Substances 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 30
- 150000004665 fatty acids Chemical class 0.000 claims description 27
- 235000021323 fish oil Nutrition 0.000 claims description 27
- 238000000526 short-path distillation Methods 0.000 claims description 23
- 239000007858 starting material Substances 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000006136 alcoholysis reaction Methods 0.000 claims description 11
- 101001003495 Pseudomonas fluorescens Lipase Proteins 0.000 claims description 10
- 101001064559 Pseudomonas fluorescens Lipase Proteins 0.000 claims description 10
- -1 alkyl ester fatty acid Chemical class 0.000 claims description 10
- 125000005456 glyceride group Chemical group 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 125000005907 alkyl ester group Chemical group 0.000 claims description 7
- 150000003626 triacylglycerols Chemical class 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 101000968489 Rhizomucor miehei Lipase Proteins 0.000 claims description 4
- 241000223258 Thermomyces lanuginosus Species 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 229940090949 docosahexaenoic acid Drugs 0.000 claims description 2
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 2
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- 125000005233 alkylalcohol group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 49
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 27
- 238000011084 recovery Methods 0.000 description 27
- 125000004494 ethyl ester group Chemical group 0.000 description 25
- 238000010932 ethanolysis reaction Methods 0.000 description 22
- 239000012141 concentrate Substances 0.000 description 15
- 238000004821 distillation Methods 0.000 description 15
- 208000015707 frontal fibrosing alopecia Diseases 0.000 description 13
- 238000000926 separation method Methods 0.000 description 13
- 108090000790 Enzymes Proteins 0.000 description 12
- 102000004190 Enzymes Human genes 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 10
- 239000003026 cod liver oil Substances 0.000 description 9
- 235000012716 cod liver oil Nutrition 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 241001454694 Clupeiformes Species 0.000 description 7
- 235000019513 anchovy Nutrition 0.000 description 7
- 241000251468 Actinopterygii Species 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 235000019688 fish Nutrition 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 241000252203 Clupea harengus Species 0.000 description 5
- 241001125048 Sardina Species 0.000 description 5
- 235000019514 herring Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 235000019512 sardine Nutrition 0.000 description 5
- 238000005809 transesterification reaction Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000589774 Pseudomonas sp. Species 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 3
- 238000012746 preparative thin layer chromatography Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 235000003441 saturated fatty acids Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000007039 two-step reaction Methods 0.000 description 3
- 240000007124 Brassica oleracea Species 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
- 101710180366 CDP-L-myo-inositol myo-inositolphosphotransferase Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 108010048733 Lipozyme Proteins 0.000 description 2
- 241001661345 Moesziomyces antarcticus Species 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 241000589516 Pseudomonas Species 0.000 description 2
- 241000235403 Rhizomucor miehei Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 108010084311 Novozyme 435 Proteins 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- JSQFXMIMWAKJQJ-UHFFFAOYSA-N [9-(2-carboxyphenyl)-6-(ethylamino)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(NCC)=CC=C2C=1C1=CC=CC=C1C(O)=O JSQFXMIMWAKJQJ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 238000007738 vacuum evaporation Methods 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
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
-
- 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
- C11B3/00—Refining fats or fatty oils
- C11B3/12—Refining fats or fatty oils by distillation
-
- 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
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
-
- 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
- C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
- C11C1/025—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by saponification and release of fatty acids
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO20025456A NO319194B1 (no) | 2002-11-14 | 2002-11-14 | Lipase-katalysert forestringsfremgangsmate av marine oljer |
| CA2506537A CA2506537C (en) | 2002-11-14 | 2003-10-31 | Lipase-catalysed esterification of marine oil |
| CNB2003801063262A CN100338010C (zh) | 2002-11-14 | 2003-10-31 | 脂酶－催化的海产品油的酯化 |
| AU2003283872A AU2003283872A1 (en) | 2002-11-14 | 2003-10-31 | Lipase-catalysed esterification of marine oil |
| ES03776079.0T ES2477584T3 (es) | 2002-11-14 | 2003-10-31 | Esterificación de aceite marino catalizada por lipasa |
| JP2004551300A JP2006506483A (ja) | 2002-11-14 | 2003-10-31 | リパーゼ触媒した海産油のエステル化 |
| DK13153895.1T DK2602308T3 (en) | 2002-11-14 | 2003-10-31 | Lipase-catalyzed esterification of oil extracted from fish or marine mammals |
| US10/534,708 US7491522B2 (en) | 2002-11-14 | 2003-10-31 | Lipase-catalysed esterification of marine oil |
| EP03776079.0A EP1560803B1 (en) | 2002-11-14 | 2003-10-31 | Lipase-catalysed esterification of marine oil |
| PCT/NO2003/000364 WO2004043894A1 (en) | 2002-11-14 | 2003-10-31 | Lipase-catalysed esterification of marine oil |
| DK03776079.0T DK1560803T3 (da) | 2002-11-14 | 2003-10-31 | Lipase-katalyseret esterificering af marineolie |
| EP13153895.1A EP2602308B1 (en) | 2002-11-14 | 2003-10-31 | Lipase-catalysed esterification of marine oil |
| ES13153895T ES2702273T3 (es) | 2002-11-14 | 2003-10-31 | Esterificación catalizada por lipasa de aceite marino |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO20025456A NO319194B1 (no) | 2002-11-14 | 2002-11-14 | Lipase-katalysert forestringsfremgangsmate av marine oljer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20025456D0 NO20025456D0 (no) | 2002-11-14 |
| NO319194B1 true NO319194B1 (no) | 2005-06-27 |
Family
ID=19914177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20025456A NO319194B1 (no) | 2002-11-14 | 2002-11-14 | Lipase-katalysert forestringsfremgangsmate av marine oljer |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7491522B2 (zh) |
| EP (2) | EP1560803B1 (zh) |
| JP (1) | JP2006506483A (zh) |
| CN (1) | CN100338010C (zh) |
| AU (1) | AU2003283872A1 (zh) |
| CA (1) | CA2506537C (zh) |
| DK (2) | DK1560803T3 (zh) |
| ES (2) | ES2477584T3 (zh) |
| NO (1) | NO319194B1 (zh) |
| WO (1) | WO2004043894A1 (zh) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| HRP20020885B1 (en) | 2002-11-11 | 2007-05-31 | GlaxoSmithKline istra�iva�ki centar Zagreb d.o.o. | SUBSTITUTED 9a-N-{N'-[4-(SULFONYL)PHENYLCARBAMOYL]}DERIVATIVES 9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERITHROMYCIN A AND 5-O-DESOZAMINYL-9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERITHRONOLIDE A |
| WO2006117668A1 (en) | 2005-05-04 | 2006-11-09 | Pronova Biopharma Norge As | Fatty acid analogues, i.e. dha derivatives for uses as a medicament |
| CA2609341C (en) * | 2005-05-23 | 2011-10-04 | Natural Asa | Concentration of fatty acid alkyl esters by enzymatic reactions with glycerol |
| ES2559959T3 (es) | 2005-06-16 | 2016-02-16 | Dsm Nutritional Products Ag | Enzimas inmovilizadas y métodos para usar las mismas |
| ES2292341B1 (es) * | 2006-03-13 | 2009-03-16 | Universidad De Almeria | "procedimiento para la purificacion de acido eicosapentaenoico (epa)". |
| DK2084175T3 (da) | 2006-10-10 | 2011-04-18 | Medivir Ab | HCV nucleosidinhibitor |
| KR101438177B1 (ko) | 2006-11-01 | 2014-09-05 | 프로노바 바이오파마 너지 에이에스 | 페록시솜 증식자-활성화 수용체의 활성자 또는 조절자인 알파-치환된 오메가-3 지질 |
| EP1978102B1 (de) | 2007-04-02 | 2010-07-07 | Cognis IP Management GmbH | Ein Gemisch enthaltend Fettsäureglyceride |
| EP1978101A1 (de) | 2007-04-02 | 2008-10-08 | Cognis IP Management GmbH | Verfahren zur Anreicherung mehrfach ungesättigter Fettsäuren |
| EP2147088A4 (en) * | 2007-04-26 | 2010-05-05 | Patrick Adlercreutz | FERTILIZED MILK OILS COMPRISING MULTIPLE-UNSATURATED FATTY ACIDS, COMPRISING EICOSAPENTAIC ACID (EPA) AND DOCOSAHEXAIC ACID (DHA), AND MANUFACTURING METHOD THEREFOR |
| CL2008002020A1 (es) | 2007-07-12 | 2008-11-14 | Ocean Nutrition Canada Ltd | Metodo de modificacion de un aceite, que comprende hidrolizar gliceridos con una solucion de lipasa thermomyces lanuginosus, separar la fraccion de acido graso saturado de la fraccion de glicerido hidrolizado y esterificar los gliceridos hidrolizados en la presencia de candida antarctica lipasa b; y composicion de aceite. |
| US9556401B2 (en) * | 2007-07-30 | 2017-01-31 | Nippon Suisan Kaisha, Ltd. | Method for producing EPA-enriched oil and DHA-enriched oil |
| KR101034458B1 (ko) * | 2008-03-03 | 2011-05-17 | 고려대학교 산학협력단 | 피놀레닌산 고함유 δ5-지방산의 제조방법 |
| KR101357298B1 (ko) * | 2008-06-20 | 2014-01-28 | 에이케이 앤 엠엔 바이오팜 주식회사 | 오메가-3계 고도불포화 지방산의 고순도 정제방법 |
| CN102245176B (zh) | 2008-10-31 | 2015-05-27 | 脂质医药有限公司 | 用作药物的脂肪酸 |
| CL2009001343A1 (es) * | 2009-06-02 | 2009-07-10 | Golden Omega S A | Proceso de obtencion concentrado de esteres de epa y dha a partir de aceite marino, que comprende agregar al aceite alcali y agua a menos de 100 grados celsius, agregar solvente, separar fase de refinado, agregar acido, separar la fase no acuosa y agregar alcohol y un catalizador a menos de 150 grados celsius, desolventilizar y destilar. |
| RU2014146265A (ru) | 2009-12-30 | 2015-07-10 | Басф Фарма (Калланиш) Лимитед | Способ хроматографического разделения с псевдодвижущимся слоем |
| EP2585570B1 (en) | 2010-06-25 | 2018-09-12 | Epax Norway AS | Process for separating polyunsaturated fatty acids from long chain unsaturated or less saturated fatty acids |
| WO2012095749A1 (en) * | 2011-01-14 | 2012-07-19 | Pharma Marine As | Removal of monoglycerides from fatty acid concentrates |
| JP5416861B2 (ja) * | 2011-03-03 | 2014-02-12 | 日本水産株式会社 | リパーゼによる高度不飽和脂肪酸含有油脂の製造方法 |
| KR101605595B1 (ko) | 2011-03-08 | 2016-03-22 | 코그니스 아이피 매니지먼트 게엠베하 | 지방산 에스테르의 증류 방법 |
| GB201107039D0 (en) * | 2011-04-26 | 2011-06-08 | Syngenta Ltd | Formulation component |
| GB201111595D0 (en) | 2011-07-06 | 2011-08-24 | Equateq Ltd | Improved process |
| GB201111591D0 (en) | 2011-07-06 | 2011-08-24 | Equateq Ltd | Further new process |
| GB201111589D0 (en) | 2011-07-06 | 2011-08-24 | Equateq Ltd | New modified process |
| GB201111601D0 (en) | 2011-07-06 | 2011-08-24 | Equateq Ltd | New process |
| GB201111594D0 (en) | 2011-07-06 | 2011-08-24 | Equateq Ltd | New improved process |
| EP2753305A1 (en) | 2011-09-06 | 2014-07-16 | Lipid Pharmaceuticals Ehf. | Coated suppositories |
| US8258330B1 (en) | 2012-01-04 | 2012-09-04 | Naturalis, S.A. | Carrier fluid composition comprising fatty acids ethyl esters and process for reducing the concentration of persistent organic pollutants in fish oil |
| WO2013103902A1 (en) | 2012-01-06 | 2013-07-11 | Omthera Pharmaceuticals, Inc. | Dpa-enriched compositions of omega-3 polyunsaturated fatty acids in free acid form |
| EP2846779A4 (en) | 2012-05-07 | 2015-12-16 | Omthera Pharmaceuticals Inc | STATIN AND OMEGA-3 FATTY ACID COMPOSITIONS |
| GB201300354D0 (en) | 2013-01-09 | 2013-02-20 | Basf Pharma Callanish Ltd | Multi-step separation process |
| CN104130860B (zh) * | 2013-05-03 | 2020-03-31 | 丰益(上海)生物技术研发中心有限公司 | 利用固定化疏棉状嗜热丝孢菌脂肪酶富集长链多不饱和脂肪酸的方法 |
| US9428711B2 (en) | 2013-05-07 | 2016-08-30 | Groupe Novasep | Chromatographic process for the production of highly purified polyunsaturated fatty acids |
| US8802880B1 (en) | 2013-05-07 | 2014-08-12 | Group Novasep | Chromatographic process for the production of highly purified polyunsaturated fatty acids |
| JP6302310B2 (ja) * | 2013-08-30 | 2018-03-28 | 備前化成株式会社 | 高純度オメガ３系脂肪酸エチルエステルの生産方法 |
| EP2883860B1 (fr) | 2013-12-11 | 2016-08-24 | Novasep Process | Procédé chromatographique de production d'acides gras polyinsaturés |
| EP3092218B1 (fr) | 2014-01-07 | 2022-03-09 | Novasep Process Solutions | Procédé de purification d'acides aminés aromatiques |
| US9163198B2 (en) | 2014-01-17 | 2015-10-20 | Orochem Technologies, Inc. | Process for purification of EPA (eicosapentanoic acid) ethyl ester from fish oil |
| CN104031950B (zh) * | 2014-05-07 | 2017-06-16 | 威海博宇食品有限公司 | 一种制备富含n‑3多不饱和脂肪酸磷脂的方法 |
| CN105779140A (zh) * | 2014-12-23 | 2016-07-20 | 浙江医药股份有限公司新昌制药厂 | 一种高含量epa乙酯型鱼油的制备方法 |
| US9546125B2 (en) | 2015-02-11 | 2017-01-17 | Orochem Technologies, Inc. | Continuous process for extraction of unsaturated triglycerides from fish oil |
| JP2018085931A (ja) * | 2015-04-01 | 2018-06-07 | キユーピー株式会社 | 低級アルコール脂肪酸エステル化物含有組成物の製造方法および低級アルコール脂肪酸エステル化物含有組成物 |
| JP6947370B2 (ja) * | 2015-10-05 | 2021-10-13 | ディーエスエム アイピー アセッツ ビー．ブイ．Ｄｓｍ Ｉｐ Ａｓｓｅｔｓ Ｂ．Ｖ． | 油組成物および製造方法 |
| CN105349587B (zh) * | 2015-11-10 | 2019-05-31 | 浙江工业大学 | 一种提高甘油酯型鱼油中epa和dha含量的方法 |
| EP3555283A4 (en) | 2016-12-19 | 2020-09-09 | Trans Bio-Diesel Ltd. | ENZYMATIC ENRICHMENT OF N-3 FATTY ACIDS IN THE FORM OF GLYCERIDES |
| CN108265090B (zh) * | 2016-12-30 | 2021-06-15 | 中粮集团有限公司 | 南极磷虾油替代物的制备方法 |
| ES2915598T3 (es) | 2018-12-12 | 2022-06-23 | Nippon Suisan Kaisha Ltd | Una composición que contiene un ácido graso altamente insaturado o un éster alquílico del mismo y un método para producirla |
| CN110029133B (zh) * | 2019-03-12 | 2021-03-19 | 自然资源部第三海洋研究所 | 一种分离dha藻油中饱和脂肪酸和不饱和脂肪酸的方法 |
| CN110438171A (zh) * | 2019-07-18 | 2019-11-12 | 武汉大学深圳研究院 | 一种磷脂型dha的酶法制备方法 |
| CN114057574A (zh) * | 2021-12-03 | 2022-02-18 | 浙江工商大学 | 一种制备高纯度epa乙酯的方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6291188A (ja) | 1985-10-17 | 1987-04-25 | Nisshin Oil Mills Ltd:The | 高度不飽和脂肪酸グリセリドの製造法 |
| JPH0225447A (ja) * | 1988-07-13 | 1990-01-26 | Nippon Oil & Fats Co Ltd | 高度不飽和脂肪酸類の製造方法 |
| DK95490D0 (da) | 1990-04-18 | 1990-04-18 | Novo Nordisk As | Fremgangsmaade til fremstilling af triglycerid og triglyceridsammensaetning |
| JP2715633B2 (ja) * | 1990-07-17 | 1998-02-18 | 鐘淵化学工業株式会社 | ファットブルーム耐性向上剤、及びこれを含有してなるハードバター、並びにそれらを用いたチョコレート類． |
| JPH06192683A (ja) * | 1992-12-24 | 1994-07-12 | Shokuhin Sangyo High Separeeshiyon Syst Gijutsu Kenkyu Kumiai | 遊離脂肪酸の分離方法 |
| GB9404483D0 (en) * | 1994-03-08 | 1994-04-20 | Norsk Hydro As | Refining marine oil compositions |
| DE4425987A1 (de) | 1994-07-22 | 1996-01-25 | Bosch Gmbh Robert | Verfahren und Vorrichtung zur Ansteuerung eines elektromagnetischen Verbrauchers |
| AU6610996A (en) | 1995-05-24 | 1996-12-11 | Loders Croklaan B.V. | Production of materials high in long chain polyunsaturated f atty acids |
| JP3785467B2 (ja) * | 1996-07-10 | 2006-06-14 | 旭電化工業株式会社 | 油脂組成物の製造方法 |
| JP3773315B2 (ja) * | 1996-11-22 | 2006-05-10 | 大阪市 | ω−３系高度不飽和脂肪酸エステルの精製方法 |
| JP3734905B2 (ja) * | 1996-12-18 | 2006-01-11 | 大阪市 | ω−３系高度不飽和脂肪酸の精製方法 |
| NO312973B1 (no) | 1999-02-17 | 2002-07-22 | Norsk Hydro As | Lipase-katalysert forestring av marine oljer |
| CA2273570A1 (en) * | 1999-05-31 | 2000-11-30 | Jfs Envirohealth Ltd. | Concentration and purification of polyunsaturated fatty acid esters by distillation-enzymatic transesterification coupling |
| GB2350610A (en) * | 1999-06-01 | 2000-12-06 | Jfs Envirohealth Ltd | Preparation of pure unsaturated fatty acids |
| JP4210437B2 (ja) * | 2000-09-27 | 2009-01-21 | 池田食研株式会社 | 食品用ステロール脂肪酸エステルの製造方法 |
-
2002
- 2002-11-14 NO NO20025456A patent/NO319194B1/no not_active IP Right Cessation
-
2003
- 2003-10-31 WO PCT/NO2003/000364 patent/WO2004043894A1/en active Application Filing
- 2003-10-31 US US10/534,708 patent/US7491522B2/en not_active Expired - Lifetime
- 2003-10-31 DK DK03776079.0T patent/DK1560803T3/da active
- 2003-10-31 EP EP03776079.0A patent/EP1560803B1/en not_active Expired - Lifetime
- 2003-10-31 DK DK13153895.1T patent/DK2602308T3/en active
- 2003-10-31 CN CNB2003801063262A patent/CN100338010C/zh not_active Expired - Fee Related
- 2003-10-31 CA CA2506537A patent/CA2506537C/en not_active Expired - Lifetime
- 2003-10-31 ES ES03776079.0T patent/ES2477584T3/es not_active Expired - Lifetime
- 2003-10-31 EP EP13153895.1A patent/EP2602308B1/en not_active Expired - Lifetime
- 2003-10-31 JP JP2004551300A patent/JP2006506483A/ja active Pending
- 2003-10-31 AU AU2003283872A patent/AU2003283872A1/en not_active Abandoned
- 2003-10-31 ES ES13153895T patent/ES2702273T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DK2602308T3 (en) | 2019-01-14 |
| EP2602308A3 (en) | 2014-04-02 |
| CA2506537A1 (en) | 2004-05-27 |
| CN100338010C (zh) | 2007-09-19 |
| CN1726181A (zh) | 2006-01-25 |
| ES2702273T3 (es) | 2019-02-28 |
| AU2003283872A1 (en) | 2004-06-03 |
| JP2006506483A (ja) | 2006-02-23 |
| ES2477584T3 (es) | 2014-07-17 |
| EP1560803A1 (en) | 2005-08-10 |
| NO20025456D0 (no) | 2002-11-14 |
| CA2506537C (en) | 2011-02-22 |
| US20060148047A1 (en) | 2006-07-06 |
| DK1560803T3 (da) | 2014-06-23 |
| EP2602308B1 (en) | 2018-10-03 |
| WO2004043894A1 (en) | 2004-05-27 |
| EP2602308A2 (en) | 2013-06-12 |
| US7491522B2 (en) | 2009-02-17 |
| WO2004043894A8 (en) | 2004-08-26 |
| EP1560803B1 (en) | 2014-04-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7491522B2 (en) | Lipase-catalysed esterification of marine oil | |
| JP2006506483A5 (zh) | ||
| Solaesa et al. | Production and concentration of monoacylglycerols rich in omega-3 polyunsaturated fatty acids by enzymatic glycerolysis and molecular distillation | |
| KR101357298B1 (ko) | 오메가-3계 고도불포화 지방산의 고순도 정제방법 | |
| RU2422498C2 (ru) | Способ получения диолеоил пальмитоил глицерида | |
| RU2480993C2 (ru) | Эквиваленты какао-масла, полученные способом ферментативной внутримолекулярной переэтерификации, и способ их получения | |
| Watanabe et al. | Diacylglycerol production in a packed bed bioreactor | |
| CA2362212C (en) | Lipase-catalysed esterification of marine oil | |
| CA2803477C (en) | Process for separating polyunsaturated fatty acids from long chain unsaturated or less saturated fatty acids | |
| EP2147088A1 (en) | A polyunsaturated fatty acid (pufa) enriched marine oil comprising eicosapentaenoic acid (epa) and docosahexaenoic acid (dha), and a process of production thereof | |
| DK3139770T3 (en) | FATTY ACID COMPOSITION, PROCEDURE FOR THE PREPARATION AND APPLICATION OF THEREOF | |
| WO2007029020A1 (en) | Triglyceride process | |
| JP2011225778A (ja) | 固体脂の製造法 | |
| US20160361285A1 (en) | Method for purifying stearidonic acid | |
| De | Comparison of bio-and autocatalytic esterification of oils using mono-and diglycerides | |
| Omega | Structured triacylglycerols comprising omega-3 polyunsaturated fatty acids | |
| WO2024030062A1 (en) | Enzymatic process for increasing the sos triglyceride content of a vegetable oil |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |