CA2693070A1 - Procédé de fabrication d'une huile enrichie en epa et d'une huile enrichie en dha - Google Patents

Procédé de fabrication d'une huile enrichie en epa et d'une huile enrichie en dha Download PDF

Info

Publication number: CA2693070A1
Authority: CA; Canada
Prior art keywords: dha; epa; lipase; oil; reaction
Prior art date: 2007-07-30
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.): Abandoned

Application number

CA 2693070

Other languages

English (en)

Inventor

Kiyomi Furihata

Hiroyuki Kawahara

Hideaki Yamaguchi

Hideo Ikemoto

Nobushige Doisaki

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Nissui Corp

Original Assignee

Individual

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.)

2007-07-30

Filing date

2008-07-29

Publication date

2009-02-05

2008-07-29 Application filed by Individual filed Critical Individual

2009-02-05 Publication of CA2693070A1 publication Critical patent/CA2693070A1/fr

Status Abandoned legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 8
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims abstract description 124
239000003921 oil Substances 0.000 claims abstract description 97
108090001060 Lipase Proteins 0.000 claims abstract description 94
102000004882 Lipase Human genes 0.000 claims abstract description 94
239000004367 Lipase Substances 0.000 claims abstract description 93
235000019421 lipase Nutrition 0.000 claims abstract description 93
238000006243 chemical reaction Methods 0.000 claims abstract description 86
125000005456 glyceride group Chemical group 0.000 claims abstract description 77
239000000395 magnesium oxide Substances 0.000 claims abstract description 69
235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 65
229930195729 fatty acid Natural products 0.000 claims abstract description 65
239000000194 fatty acid Substances 0.000 claims abstract description 65
150000004665 fatty acids Chemical class 0.000 claims abstract description 60
235000014593 oils and fats Nutrition 0.000 claims abstract description 32
239000000654 additive Substances 0.000 claims abstract description 20
238000006136 alcoholysis reaction Methods 0.000 claims abstract description 20
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims abstract description 17
230000000996 additive effect Effects 0.000 claims abstract description 13
239000000758 substrate Substances 0.000 claims abstract description 12
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 134
235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 128
235000020669 docosahexaenoic acid Nutrition 0.000 claims description 127
235000019198 oils Nutrition 0.000 claims description 95
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 70
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 59
108010048733 Lipozyme Proteins 0.000 claims description 26
FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 claims description 26
238000000034 method Methods 0.000 claims description 25
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 10
239000000920 calcium hydroxide Substances 0.000 claims description 10
229910001861 calcium hydroxide Inorganic materials 0.000 claims description 10
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 10
239000000292 calcium oxide Substances 0.000 claims description 10
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 10
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 9
239000000347 magnesium hydroxide Substances 0.000 claims description 9
229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 9
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
229940090949 docosahexaenoic 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
229960005135 eicosapentaenoic acid Drugs 0.000 claims description 7
150000001875 compounds Chemical class 0.000 claims description 6
241000223258 Thermomyces lanuginosus Species 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
230000007062 hydrolysis Effects 0.000 claims description 5
238000006460 hydrolysis reaction Methods 0.000 claims description 5
244000005700 microbiome Species 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
241000588810 Alcaligenes sp. Species 0.000 claims description 4
239000000470 constituent Substances 0.000 claims description 4
235000021323 fish oil Nutrition 0.000 claims description 4
239000000203 mixture Substances 0.000 description 42
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
241001125048 Sardina Species 0.000 description 20
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 description 20
235000019512 sardine Nutrition 0.000 description 20
125000004494 ethyl ester group Chemical group 0.000 description 19
150000002632 lipids Chemical class 0.000 description 16
238000004821 distillation Methods 0.000 description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
238000012746 preparative thin layer chromatography Methods 0.000 description 12
238000010932 ethanolysis reaction Methods 0.000 description 11
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 description 10
235000021294 Docosapentaenoic acid Nutrition 0.000 description 10
235000021342 arachidonic acid Nutrition 0.000 description 10
229940114079 arachidonic acid Drugs 0.000 description 10
230000032050 esterification Effects 0.000 description 10
238000005886 esterification reaction Methods 0.000 description 10
235000020777 polyunsaturated fatty acids Nutrition 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
108090000790 Enzymes Proteins 0.000 description 9
102000004190 Enzymes Human genes 0.000 description 9
235000021588 free fatty acids Nutrition 0.000 description 9
238000004817 gas chromatography Methods 0.000 description 9
239000000047 product Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
238000004458 analytical method Methods 0.000 description 7
150000003626 triacylglycerols Chemical class 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
-1 alcohol ester Chemical class 0.000 description 6
OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 6
230000000052 comparative effect Effects 0.000 description 6
239000007858 starting material Substances 0.000 description 6
230000000694 effects Effects 0.000 description 5
239000000843 powder Substances 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
239000000243 solution Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
241000269817 Centrarchidae Species 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
235000013305 food Nutrition 0.000 description 3
210000004185 liver Anatomy 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
238000000199 molecular distillation Methods 0.000 description 3
238000000746 purification Methods 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
238000000526 short-path distillation Methods 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
241000013355 Mycteroperca interstitialis Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
241000277338 Oncorhynchus kisutch Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000012267 brine Substances 0.000 description 2
ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000006911 enzymatic reaction Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
235000020660 omega-3 fatty acid Nutrition 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
241000588986 Alcaligenes Species 0.000 description 1
206010003210 Arteriosclerosis Diseases 0.000 description 1
241000972773 Aulopiformes Species 0.000 description 1
241001474374 Blennius Species 0.000 description 1
241001453380 Burkholderia Species 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
241000222120 Candida <Saccharomycetales> Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
SBJKKFFYIZUCET-JLAZNSOCSA-N Dehydro-L-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(=O)C1=O SBJKKFFYIZUCET-JLAZNSOCSA-N 0.000 description 1
229920000064 Ethyl eicosapentaenoic acid Polymers 0.000 description 1
208000031226 Hyperlipidaemia Diseases 0.000 description 1
108010093096 Immobilized Enzymes Proteins 0.000 description 1
241001098054 Pollachius pollachius Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000269851 Sarda sarda Species 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000005456 alcohol based solvent Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
208000011775 arteriosclerosis disease Diseases 0.000 description 1
235000013361 beverage Nutrition 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
239000012159 carrier gas Substances 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003026 cod liver oil Substances 0.000 description 1
235000012716 cod liver oil Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000009795 derivation Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
235000019961 diglycerides of fatty acid Nutrition 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
SSQPWTVBQMWLSZ-AAQCHOMXSA-N ethyl (5Z,8Z,11Z,14Z,17Z)-icosapentaenoate Chemical compound CCOC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC SSQPWTVBQMWLSZ-AAQCHOMXSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
239000010408 film Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000005350 fused silica glass Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000005484 gravity Effects 0.000 description 1
235000013402 health food Nutrition 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
235000020978 long-chain polyunsaturated fatty acids Nutrition 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
235000014380 magnesium carbonate Nutrition 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229940127554 medical product Drugs 0.000 description 1
JBXYCUKPDAAYAS-UHFFFAOYSA-N methanol;trifluoroborane Chemical compound OC.FB(F)F JBXYCUKPDAAYAS-UHFFFAOYSA-N 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
235000019960 monoglycerides of fatty acid Nutrition 0.000 description 1
239000000346 nonvolatile oil Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
238000003822 preparative gas chromatography Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
235000019515 salmon Nutrition 0.000 description 1
229940119224 salmon oil Drugs 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
239000013589 supplement Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
239000010409 thin film Substances 0.000 description 1
238000007039 two-step reaction Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
- 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
- C11C1/04—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis
- C11C1/045—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis using enzymes or microorganisms, living or dead
- 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
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6458—Glycerides by transesterification, e.g. interesterification, ester interchange, alcoholysis or acidolysis
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6472—Glycerides containing polyunsaturated fatty acid [PUFA] residues, i.e. having two or more double bonds in their backbone

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Oil, Petroleum & Natural Gas (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Microbiology (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Biotechnology (AREA)
Health & Medical Sciences (AREA)
General Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Polymers & Plastics (AREA)
Food Science & Technology (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Fats And Perfumes (AREA)

CA 2693070 2007-07-30 2008-07-29 Procédé de fabrication d'une huile enrichie en epa et d'une huile enrichie en dha Abandoned CA2693070A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP2007-197253		2007-07-30
JP2007197253		2007-07-30
PCT/JP2008/063550 WO2009017102A1 (fr)	2007-07-30	2008-07-29	Procédé de fabrication d'une huile enrichie en epa et d'une huile enrichie en dha

Publications (1)

Publication Number	Publication Date
CA2693070A1 true CA2693070A1 (fr)	2009-02-05

Family

ID=40304332

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2693070 Abandoned CA2693070A1 (fr)	2007-07-30	2008-07-29	Procédé de fabrication d'une huile enrichie en epa et d'une huile enrichie en dha

Country Status (8)

Country	Link
US (1)	US9556401B2 (fr)
EP (1)	EP2172558B1 (fr)
JP (1)	JP5204776B2 (fr)
KR (1)	KR101502191B1 (fr)
CN (1)	CN101765662B (fr)
CA (1)	CA2693070A1 (fr)
DK (1)	DK2172558T3 (fr)
WO (1)	WO2009017102A1 (fr)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP5527983B2 (ja) *	2009-02-13	2014-06-25	花王株式会社	ドコサヘキサエン酸高含有油脂の製造方法
JP5405193B2 (ja) *	2009-05-15	2014-02-05	水澤化学工業株式会社	バイオ燃料の製造方法
RU2014146265A (ru)	2009-12-30	2015-07-10	Басф Фарма (Калланиш) Лимитед	Способ хроматографического разделения с псевдодвижущимся слоем
EP2578691A4 (fr) *	2010-05-28	2016-11-23	Nippon Suisan Kaisha Ltd	Procédé de production d'huile ou de graisse contenant un acide gras fortement insaturé au moyen d'une lipase
EP2401923B1 (fr) *	2010-06-30	2013-03-13	Loders Croklaan B.V.	Traitement d'huiles végétales
CA3026436A1 (fr) *	2011-02-11	2012-08-16	E. I. Du Pont De Nemours And Company	Procede d'obtention de composition contenant des lipides a partir de biomasse microbienne
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
GB201111589D0 (en)	2011-07-06	2011-08-24	Equateq Ltd	New modified process
GB201111595D0 (en)	2011-07-06	2011-08-24	Equateq Ltd	Improved process
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EP2172558A4 (fr)	2015-05-27
JPWO2009017102A1 (ja)	2010-10-21
JP5204776B2 (ja)	2013-06-05
US20100190220A1 (en)	2010-07-29
EP2172558B1 (fr)	2017-07-19
KR20100057015A (ko)	2010-05-28
CN101765662A (zh)	2010-06-30
DK2172558T3 (en)	2017-09-25
CN101765662B (zh)	2014-04-02
WO2009017102A1 (fr)	2009-02-05
US9556401B2 (en)	2017-01-31
EP2172558A1 (fr)	2010-04-07

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EP2585570B1 (fr)	2018-09-12	Procédé de séparation des acides gras polyinsaturés d'acides gras à chaîne longue insaturés ou moins saturés
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