NO319194B1 - Lipase-katalysert forestringsfremgangsmate av marine oljer - Google Patents

Lipase-katalysert forestringsfremgangsmate av marine oljer Download PDF

Info

Publication number: NO319194B1
Authority: NO; Norway
Prior art keywords: dha; lipase; epa; fatty acids; free fatty
Prior art date: 2002-11-14

Application number

NO20025456A

Other languages

English (en)

Norwegian (no)

Other versions

NO20025456D0 (no

Inventor

Gudmundur G Haraldsson

Olav Thorstad

Arnar Halldorsson

Original Assignee

Pronova Biocare As

Priority date (The priority date 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 date listed.)

2002-11-14

Filing date

2002-11-14

Publication date

2005-06-27

2002-11-14 Application filed by Pronova Biocare As filed Critical Pronova Biocare As

2002-11-14 Priority to NO20025456A priority Critical patent/NO319194B1/no

2002-11-14 Publication of NO20025456D0 publication Critical patent/NO20025456D0/no

2003-10-31 Priority to CA2506537A priority patent/CA2506537C/fr

2003-10-31 Priority to ES13153895T priority patent/ES2702273T3/es

2003-10-31 Priority to JP2004551300A priority patent/JP2006506483A/ja

2003-10-31 Priority to US10/534,708 priority patent/US7491522B2/en

2003-10-31 Priority to PCT/NO2003/000364 priority patent/WO2004043894A1/fr

2003-10-31 Priority to EP13153895.1A priority patent/EP2602308B1/fr

2003-10-31 Priority to CNB2003801063262A priority patent/CN100338010C/zh

2003-10-31 Priority to DK13153895.1T priority patent/DK2602308T3/en

2003-10-31 Priority to ES03776079.0T priority patent/ES2477584T3/es

2003-10-31 Priority to EP03776079.0A priority patent/EP1560803B1/fr

2003-10-31 Priority to DK03776079.0T priority patent/DK1560803T3/da

2003-10-31 Priority to AU2003283872A priority patent/AU2003283872A1/en

2005-06-27 Publication of NO319194B1 publication Critical patent/NO319194B1/no

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)

NO20025456A 2002-11-14 2002-11-14 Lipase-katalysert forestringsfremgangsmate av marine oljer NO319194B1 (no)

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
AU2003283872A AU2003283872A1 (en)	2002-11-14	2003-10-31	Lipase-catalysed esterification of marine oil
EP13153895.1A EP2602308B1 (fr)	2002-11-14	2003-10-31	Estérification catalysée par lipase d'huile marine
ES13153895T ES2702273T3 (es)	2002-11-14	2003-10-31	Esterificación catalizada por lipasa de aceite marino
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
US10/534,708 US7491522B2 (en)	2002-11-14	2003-10-31	Lipase-catalysed esterification of marine oil
PCT/NO2003/000364 WO2004043894A1 (fr)	2002-11-14	2003-10-31	Esterification de petrole marin catalysee par des lipases
CA2506537A CA2506537C (fr)	2002-11-14	2003-10-31	Esterification de petrole marin catalysee par des lipases
CNB2003801063262A CN100338010C (zh)	2002-11-14	2003-10-31	脂酶－催化的海产品油的酯化
DK13153895.1T DK2602308T3 (en)	2002-11-14	2003-10-31	Lipase-catalyzed esterification of oil extracted from fish or marine mammals
ES03776079.0T ES2477584T3 (es)	2002-11-14	2003-10-31	Esterificación de aceite marino catalizada por lipasa
EP03776079.0A EP1560803B1 (fr)	2002-11-14	2003-10-31	Esterification d'huile d'animaux marins catalysee par des lipases
DK03776079.0T DK1560803T3 (da)	2002-11-14	2003-10-31	Lipase-katalyseret esterificering af marineolie

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 (fr)
EP (2)	EP1560803B1 (fr)
JP (1)	JP2006506483A (fr)
CN (1)	CN100338010C (fr)
AU (1)	AU2003283872A1 (fr)
CA (1)	CA2506537C (fr)
DK (2)	DK1560803T3 (fr)
ES (2)	ES2702273T3 (fr)
NO (1)	NO319194B1 (fr)
WO (1)	WO2004043894A1 (fr)

Families Citing this family (54)

* Cited by examiner, † Cited by third party
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EP2295529B2 (fr)	2002-07-11	2022-05-18	Basf As	Procédé de diminution des polluants environnementaux dans une huile ou une graisse et produit d'alimentation pour poissons
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
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 (fr)	2005-05-04	2006-11-09	Pronova Biopharma Norge As	Analogues d'acides gras, autrement dit derives dha utilises comme medicament
EP1891189B1 (fr) *	2005-05-23	2020-09-23	Epax Norway AS	Concentration d'esters alkyliques d'acides gras produite par des reactions enzymatiques avec du glycerol
PL2439268T3 (pl)	2005-06-16	2016-06-30	Dsm Nutritional Products Ag	Immobilizowane enzymy i sposoby ich stosowania
ES2292341B1 (es) *	2006-03-13	2009-03-16	Universidad De Almeria	"procedimiento para la purificacion de acido eicosapentaenoico (epa)".
AP2009004812A0 (en)	2006-10-10	2009-04-30	Medivir Ab	HCV nucleoside inhibitor
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 (fr)	2007-04-02	2010-07-07	Cognis IP Management GmbH	Un mélange comprenant des glycérides d'acides gras
EP1978101A1 (fr)	2007-04-02	2008-10-08	Cognis IP Management GmbH	Procédé d'enrichissement en acides gras polyinsaturés
CA2685272A1 (fr) *	2007-04-26	2008-11-06	Patrick Adlercreutz	Huile marine enrichie en acide gras polyinsature (pufa), comprenant l'acide eicosapentaenoique (epa) et l'acide docosahexaenoique (dha) et son procede de fabrication
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
JP6113954B2 (ja) *	2008-10-31	2017-04-12	リピッドファーマシューティカルズイーエイチエフ．	医薬として使用するための脂肪酸
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.
PE20130491A1 (es)	2009-12-30	2013-05-02	Basf Pharma Callanish Ltd	Proceso simulado de separacion cromatografica de lecho movil para la purificacion de acidos grasos poliinsaturados
US9476008B2 (en)	2010-06-25	2016-10-25	Epax As	Process for separating polyunsaturated fatty acids from long chain unsaturated or less saturated fatty acids
US20120184760A1 (en) *	2011-01-14	2012-07-19	Pharma Marine As	Removal of monoglycerides from fatty acid concentrates
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2003
- 2003-10-31 EP EP03776079.0A patent/EP1560803B1/fr not_active Expired - Lifetime
- 2003-10-31 AU AU2003283872A patent/AU2003283872A1/en not_active Abandoned
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- 2003-10-31 WO PCT/NO2003/000364 patent/WO2004043894A1/fr not_active Ceased
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DK2602308T3 (en)	2019-01-14
JP2006506483A (ja)	2006-02-23
CN100338010C (zh)	2007-09-19
AU2003283872A1 (en)	2004-06-03
CN1726181A (zh)	2006-01-25
WO2004043894A8 (fr)	2004-08-26
EP2602308A2 (fr)	2013-06-12
EP2602308B1 (fr)	2018-10-03
ES2477584T3 (es)	2014-07-17
ES2702273T3 (es)	2019-02-28
NO20025456D0 (no)	2002-11-14
US20060148047A1 (en)	2006-07-06
WO2004043894A1 (fr)	2004-05-27
EP1560803B1 (fr)	2014-04-23
DK1560803T3 (da)	2014-06-23
EP2602308A3 (fr)	2014-04-02
EP1560803A1 (fr)	2005-08-10
CA2506537A1 (fr)	2004-05-27
CA2506537C (fr)	2011-02-22
US7491522B2 (en)	2009-02-17

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Publication	Publication Date	Title
NO319194B1 (no)	2005-06-27	Lipase-katalysert forestringsfremgangsmate av marine oljer
JP2006506483A5 (fr)	2009-12-17
KR101357298B1 (ko)	2014-01-28	오메가-3계 고도불포화 지방산의 고순도 정제방법
RU2480993C2 (ru)	2013-05-10	Эквиваленты какао-масла, полученные способом ферментативной внутримолекулярной переэтерификации, и способ их получения
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JP2025526387A (ja)	2025-08-13	植物性油のｓｏｓトリグリセリド含有量を増加させるための酵素的方法
PING	2002	AN ENZYMATIC TRANSESTERIFICATION OF REFINED, BLEACHED AND DEODORIZED PALM OIL DURING DRY-FRACTIONATION IN A PILOT-SCALE FRACTIONATION PLANT