WO2007119811A1 - 高度不飽和脂肪酸濃縮油の製造方法 - Google Patents
高度不飽和脂肪酸濃縮油の製造方法 Download PDFInfo
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- WO2007119811A1 WO2007119811A1 PCT/JP2007/058134 JP2007058134W WO2007119811A1 WO 2007119811 A1 WO2007119811 A1 WO 2007119811A1 JP 2007058134 W JP2007058134 W JP 2007058134W WO 2007119811 A1 WO2007119811 A1 WO 2007119811A1
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- WIPO (PCT)
- Prior art keywords
- fatty acid
- unsaturated fatty
- highly unsaturated
- lipase
- epa
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 title abstract description 30
- 108090001060 Lipase Proteins 0.000 claims abstract description 65
- 239000004367 Lipase Substances 0.000 claims abstract description 65
- 102000004882 Lipase Human genes 0.000 claims abstract description 65
- 235000019421 lipase Nutrition 0.000 claims abstract description 65
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 56
- 125000005456 glyceride group Chemical group 0.000 claims abstract description 38
- 238000006136 alcoholysis reaction Methods 0.000 claims abstract description 15
- 239000000292 calcium oxide Substances 0.000 claims abstract description 7
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims abstract description 7
- 239000000347 magnesium hydroxide Substances 0.000 claims abstract description 7
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims abstract description 7
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims abstract description 6
- 239000000920 calcium hydroxide Substances 0.000 claims abstract description 6
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims abstract description 6
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 4
- 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 135
- 239000003921 oil Substances 0.000 claims description 82
- 235000019198 oils Nutrition 0.000 claims description 82
- 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 74
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 74
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 74
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 74
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 69
- 229940090949 docosahexaenoic acid Drugs 0.000 claims description 68
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 55
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 40
- 229930195729 fatty acid Natural products 0.000 claims description 40
- 239000000194 fatty acid Substances 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 39
- 150000004665 fatty acids Chemical class 0.000 claims description 38
- 239000003925 fat Substances 0.000 claims description 27
- 235000019197 fats Nutrition 0.000 claims description 27
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 23
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 17
- 239000000654 additive Substances 0.000 claims description 13
- 238000010932 ethanolysis reaction Methods 0.000 claims description 12
- 230000000996 additive effect Effects 0.000 claims description 8
- 229940087373 calcium oxide Drugs 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 244000005700 microbiome Species 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 235000021323 fish oil Nutrition 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 241000589540 Pseudomonas fluorescens Species 0.000 claims description 3
- 241000223258 Thermomyces lanuginosus Species 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 241000589513 Burkholderia cepacia Species 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- 241000588810 Alcaligenes sp. Species 0.000 claims 1
- 235000012255 calcium oxide Nutrition 0.000 claims 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 abstract description 88
- 239000000395 magnesium oxide Substances 0.000 abstract description 46
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 abstract description 5
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 abstract description 4
- 238000011084 recovery Methods 0.000 description 44
- 108010048733 Lipozyme Proteins 0.000 description 16
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 241001125048 Sardina Species 0.000 description 14
- 235000019512 sardine Nutrition 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 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 12
- 235000021294 Docosapentaenoic acid Nutrition 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 102000004190 Enzymes Human genes 0.000 description 10
- 108090000790 Enzymes Proteins 0.000 description 10
- 239000002994 raw material Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 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 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 238000012746 preparative thin layer chromatography Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- -1 alcohol ester Chemical class 0.000 description 3
- 235000021342 arachidonic acid Nutrition 0.000 description 3
- 229940114079 arachidonic acid Drugs 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 235000014593 oils and fats Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 241000208818 Helianthus Species 0.000 description 2
- 235000003222 Helianthus annuus Nutrition 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
- 241001098054 Pollachius pollachius Species 0.000 description 2
- 241000785681 Sander vitreus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000223257 Thermomyces Species 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 235000012716 cod liver oil Nutrition 0.000 description 2
- 239000003026 cod liver oil Substances 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000005350 fused silica glass Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 235000013402 health food Nutrition 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 238000000199 molecular distillation Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000010422 painting Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- DVSZKTAMJJTWFG-SKCDLICFSA-N (2e,4e,6e,8e,10e,12e)-docosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C=C\C(O)=O DVSZKTAMJJTWFG-SKCDLICFSA-N 0.000 description 1
- GZJLLYHBALOKEX-UHFFFAOYSA-N 6-Ketone, O18-Me-Ussuriedine Natural products CC=CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O GZJLLYHBALOKEX-UHFFFAOYSA-N 0.000 description 1
- 241000588986 Alcaligenes Species 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 108090000994 Catalytic RNA Proteins 0.000 description 1
- 102000053642 Catalytic RNA Human genes 0.000 description 1
- 241000269817 Centrarchidae Species 0.000 description 1
- 101710093617 Dihydroxyacetone synthase Proteins 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
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 241001315609 Pittosporum crassifolium Species 0.000 description 1
- 101000968491 Pseudomonas sp. (strain 109) Triacylglycerol lipase Proteins 0.000 description 1
- PPWHTZKZQNXVAE-UHFFFAOYSA-N Tetracaine hydrochloride Chemical compound Cl.CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 PPWHTZKZQNXVAE-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 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
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- KAUVQQXNCKESLC-UHFFFAOYSA-N docosahexaenoic acid (DHA) Natural products COC(=O)C(C)NOCC1=CC=CC=C1 KAUVQQXNCKESLC-UHFFFAOYSA-N 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
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000002035 hexane extract Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 229960004232 linoleic acid Drugs 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- JBXYCUKPDAAYAS-UHFFFAOYSA-N methanol;trifluoroborane Chemical compound OC.FB(F)F JBXYCUKPDAAYAS-UHFFFAOYSA-N 0.000 description 1
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 108091092562 ribozyme Proteins 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- PVFDPMYXCZLHKY-MLLWLMKGSA-M sodium [(1R,2R,4aR,8aS)-2-hydroxy-5-[(2E)-2-[(4S)-4-hydroxy-2-oxooxolan-3-ylidene]ethyl]-1,4a,6-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl sulfate Chemical compound [Na+].C([C@@H]1[C@](C)(COS([O-])(=O)=O)[C@H](O)CC[C@]11C)CC(C)=C1C\C=C1/[C@H](O)COC1=O PVFDPMYXCZLHKY-MLLWLMKGSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 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
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/195—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from bacteria
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/195—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from bacteria
- C07K14/21—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from bacteria from Pseudomonadaceae (F)
-
- 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
-
- 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
-
- 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
- C12P7/6409—Fatty acids
- C12P7/6427—Polyunsaturated fatty acids [PUFA], i.e. having two or more double bonds in their backbone
- C12P7/6432—Eicosapentaenoic acids [EPA]
-
- 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
-
- 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
-
- 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
- C12P7/6454—Glycerides by esterification
Definitions
- the present invention relates to a process for producing fats and oils containing polyunsaturated fatty acid (hereinafter abbreviated as PUFA) at a high concentration by alcoholysis using lipase.
- PUFA polyunsaturated fatty acid
- Eicosapentaenoic acid hereinafter abbreviated as EPA
- docosahexaenoic acid which are n-3 PUFAs
- DHA has various physiological functions and is used as a medicine, health food, food material, and the like.
- EPA ethyl ester is used as a treatment for arteriosclerosis and hyperlipidemia, and beverages containing fish oil containing EPA and DHA are also approved as foods for specified health use.
- domestic and overseas demand for supplements is also very high.
- Non-patent Document 1 it is known that water plays an important role in the expression of enzyme activity both in the conventional force and in enzyme reactions in organic solvents. It has been reported that the addition of water promotes the lipase reaction when concentrating PUFA from cod liver oil using the alcoholysis reaction, which is a reaction that cleaves fatty acids from glycerides by the action of alcohol (Non-patent Document 2). ). On the other hand, it is also disclosed that similar alcoholysis proceeds under almost anhydrous conditions with a specific enzyme (Patent Document 2). Strength Productivity is very high with lipase usage of 10% of oil For above, it is necessary to fix the lipase.
- the component to be removed is a fatty acid lower alcohol ester, which can be easily removed by distillation or the like.
- Patent Document 1 JP-A-58-165796
- Patent Document 2 Japanese Patent Publication No. 9 510091
- Patent Document 1 J. S. Dordick, Enzymatic catalysis in monophasic organic solvents, Enzyme Microb. TechnoL, 1989, 11, April, 194-211
- Non-Patent Document 2 L. Zui and O. P. Ward, "Lipase- catalyzed alcoholysis to concentrate the n ⁇ 3 polyunsaturated fatty acid of cod liver oil", Enzyme Microb. TechnoL, 1993, 15, July, 601-606
- An object of the present invention is to provide a method for concentrating PUFA, particularly EPA, DHA and the like contained in a raw material oil.
- the present invention provides PUFA in the presence of at least one compound selected from the group consisting of magnesium oxide, magnesium hydroxide, calcium oxide, calcium hydroxide as a reaction additive, and a small amount of water.
- a compound selected from the group consisting of magnesium oxide, magnesium hydroxide, calcium oxide, calcium hydroxide as a reaction additive, and a small amount of water.
- At least one compound selected from the group consisting of acid magnesium, magnesium hydroxide, acid calcium, and calcium hydroxide as a reaction additive, and a small amount A step of subjecting a fat or oil containing a highly unsaturated fatty acid as a fatty acid constituting a fat to an alcoholysis reaction by lipase in the presence of water, and a step of separating a glyceride fraction as the fatty acid constituting the fat or oil.
- a process for producing a highly unsaturated fatty acid concentrated oil is provided.
- the present invention increases the reactivity of the enzyme by adding a small amount of an inexpensive additive and water, and also improves the selectivity that it is difficult to act on PUFA that is ester-bonded to glycerides. As a result, a concentrated oil containing a high amount of PUFA can be produced at a high yield and at a low cost.
- a polyunsaturated fatty acid means a fatty acid having 16 or more carbon atoms and 2 or more double bonds.
- Well known ones include eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), arachidonic acid, linolenic acid, linoleic acid and the like.
- the highly unsaturated fatty acid-containing fat of the present invention is not particularly limited as long as it contains the highly unsaturated fatty acid as a fatty acid constituting the fat, and includes marine oils such as fish oil, microbial oil, including PUFA, Examples include algal oil and vegetable oil.
- the method of the present invention is suitable for the concentration of fatty acids having 20 or more carbon atoms, 4 to 6 double bonds, particularly 20 to 22 carbon atoms, and 6 to 6 double bonds among polyunsaturated fatty acids. Yes.
- fatty acids suitable for the method of the present invention include EPA, DHA, arachidonic acid, and docosapentaenoic acid.
- Oils and fats usually mean triglycerides of fatty acids, but in the present invention, they mean glycerides including diglycerides and monodalides.
- the concentration of highly unsaturated fatty acids means that “the amount of highly unsaturated fatty acids Z total amount of fatty acids” after reaction is larger than “the amount of highly unsaturated fatty acids Z total amount of fatty acids” of the raw oil and fat. This means that fats and oils that have a greater “amount of highly unsaturated fatty acids Z total amount of fatty acids” compared to raw oils and fats are highly unsaturated fatty acid concentrates.
- glyceride is a general term for fatty acid triglycerides, diglycerides, and monodalides.
- the lipase used in the present invention is not particularly limited as long as it has a property that catalyzes the alcoholysis reaction and hardly acts on PUFA.
- lipases obtained from microorganisms belonging to Alcaligenes (lipase QLM, lipase QLC, lipase P, all manufactured by Meika Sangyo Co., Ltd.) and microorganisms belonging to Burkholderia cepacia.
- Lipase lipase PS, manufactured by Amano Enzym Co., Ltd.
- lipase obtained from microorganisms belonging to Pseudomonas fluorescens Lipase AK, manufactured by Amano Enzym Co., Ltd.
- Thermomyces lanuginosa Thermomvce s lanuginosa
- lipases obtained from microorganisms belonging to the group Lipozyme TLIM, manufactured by Novozym.
- the amount of lipase used is not particularly limited, but for powder lipase, it is preferable to use 10 units / g or more for fats and oils, and 30 units / g or more for practical use considering the reaction rate.
- the lipase content is preferably 0.01% (w / w) or more based on the fat and oil.
- reaction additive MgO, magnesium hydroxide, calcium oxide, calcium hydroxide can be used. MgO is particularly preferable because it can be used for food applications that are highly effective. Powders, fine granules, granules and the like can be handled or used immediately for industrial use.
- the addition amount of the reaction additive is not particularly limited, but is preferably 0.01% (w / w) to 30% (w / w), more preferably 0.05% (w / w) to 5% (based on the raw material fats and oils). Used in the range of w / w).
- the addition of a small amount of water is very effective, preferably lo / o ( v / v ) to 30 % ( v / v ) to the alcohol used, more preferably 5% (v / v) to 20 Add% (v / v).
- the alcohol used in the reaction is not particularly limited, but ethanol is one of the preferred alcohols.
- the amount of alcohol used is 0.2 to 5 equivalents, more preferably 0.2 to 1.5 equivalents, relative to the fatty acid.
- the reaction method is not particularly limited as long as a predetermined amount of raw oil and fat, water, reaction additive, and alcohol can be mixed, but at a reaction temperature at which the enzyme exhibits high activity (for example, 20 ° C to 60 ° C) for 1 hour. Or In general, the reaction time is about 24 hours and the mixture is stirred so that it is well mixed.
- An immobilized enzyme filled in a column or the like may be used for the reaction.
- PUFA concentrated oil can be obtained as a glyceride fraction by removing reaction additives, enzymes, etc. by filtration, washing with an aqueous solution, etc., and separating and purifying glycerides.
- the separation method of the glyceride fraction is not particularly limited, but for example, a distillation method such as molecular distillation or short-path distillation or a separation method using various chromatographies can be used.
- a distillation method such as molecular distillation or short-path distillation or a separation method using various chromatographies
- Examples of the purification method that can be used for the purification of oils and fats include various chromatography and steam distillation.
- the present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples.
- the PUFA content of the raw oil and glyceride fraction was determined by gas chromatography area ratio after methyl esterification.
- the methyl esteri koji performed before the gas chromatography measurement was conducted according to the standard oil test method defined by the Japan Oil Chemists' Society (Japan Oil Chemical Society established standard oil analysis method (1) 1996 version, 2.4 1 Fatty acid derivatization method, 2. 4. 1. 2- 1996 Methyl esterification method (boron trifluoride methanol method)).
- the glyceride fraction was separated by preparative TLC by the method described below (unless otherwise specified, subsequent preparative TLC was performed by the same method).
- 150 L of hexane extract was applied to a preparative TLC (silica gel 60F254 plate manufactured by Merck) and developed with hexane: jetyl ether: acetic acid (70: 30: 1, volume ratio). After the development, fractions other than ethyl ester were collected as glyceride fractions.
- the obtained glyceride fraction was methyl esterified and the fatty acid composition was analyzed by gas chromatography.
- the analysis conditions for gas chromatography are shown below.
- Capillary column DB-WAXO & W Scientific
- Fused Silica Capillary Column 0.25m ml.D.X 30m, 0.25 ⁇ m film thickness
- Carrier gas helium
- each lipase was subjected to an ethanolysis reaction under the above conditions except that water and MgO were not added, only water was added, and only MgO was added at 0.25% (w / w).
- the lipid composition of the glyceride fraction was TLC / FID (Iatroscan TH-10, manufactured by Mitsubishi Chemical Co., Ltd.), after spotting a 5 wt% hexane solution (1 ⁇ 1) on a silica gel rod, Analysis was performed with hexane: jetyl ether: acetic acid (90: 10: 1, volume ratio). As a result, the peak area ratio of glyceride and ester was obtained from the obtained chart, and based on this, the recovery rate of dalyceride was calculated.
- TLC / FID Iatroscan TH-10, manufactured by Mitsubishi Chemical Co., Ltd.
- the recovery rate of PUFA such as EPA and DHA is calculated by (PUFA ratio of glyceride after reaction (%) X glyceride content (%)) / (PUFA ratio before reaction (%))).
- Table 1 shows the results of EPA and DHA area%, EPA and DHA fatty acid recovery and glyceride recovery, and Table 2 shows the results of the comparative examples.
- Patent Document 2 Japanese Patent Publication No. 9-510091
- g 0.165% for lipase QLM and 0.33% for lipase PS
- the effect of adding water and MgO on the concentration of EPA, etc. is clear even if the amount of lipase is the same.
- EPA was concentrated as the amount of Mg 0 added increased.
- the fatty acid selectivity of the reaction which has a very high EPA recovery rate, is retained.
- sardine oil (EPA 15.7%, EPA, DHA content less than sardine oil used in Example 1)
- Table 3 shows the results of EPA, DHA 3 ⁇ 4%, recovery rate, and glyceride recovery rate.
- Table 4 shows the fatty acid recovery rate and glyceride recovery rate of EPA and DHA
- Table 5 shows the area%, fatty acid recovery rate, and glyceride recovery rate of EPA and DHA in the comparative example.
- DHA is very concentrated by adding water and MgO. As the amount of MgO added increased, the concentration of DHA concentration improved. In the comparative example, DHA was hardly concentrated even though the same amount of enzyme was used.
- reaction additives other than MgO 9 types of reaction additives were added to the feedstock oil at l% (w / w) under the same reaction conditions as in Example 1.
- refined sardine oil EPA 28.2%, DHA 12.5%, manufactured by Nihon Suisan Co., Ltd.
- 9 types of reaction additives shown in Table 6 On the other hand, l% (w / w) and 170 / zl of ethanol (0.75 equivalent with respect to the fatty acid) were added, and the mixture was stirred at 40 ° C. for 16 hours. After the reaction, the solid content was filtered off, and the glyceride fraction was separated by preparative TLC. After methyl esterification, the fatty acid composition was measured. Table 6 shows the EPA area% of the glyceride fraction. In addition to MgO, EPA concentration effects were observed in magnesium hydroxide, magnesium oxide, calcium oxide, and calcium hydroxide.
- Refined sardine oil (EPA 28.2%, DHA 12.5%, manufactured by Nippon Suisan Co., Ltd.) 1kg of lipase QLM (Alcarigenes SP, manufactured by Meito Sangyo Co., Ltd.) 0.83g, water 17g, MgO 2.5g, ethanol 173m 1
- the mixture was stirred at 40 ° C for 16 hours. After centrifugation, solids were removed and ethanol was distilled off to obtain 1.06 kg. After washing with dilute sulfuric acid, it was washed with hot water, and the ester and fatty acid were distilled off using a thin-film distillation apparatus to obtain 583 g of EPA concentrated oil as a glyceride fraction.
- the fatty acid composition was measured and found to be E PA 48.3% and DHA 17.3%.
- Example 2 Same conditions as in Example 1, namely refined sardine oil (EPA 28.2%, DHA 12.5%, manufactured by Nihon Suisan Co., Ltd.) lg with lipase QLM 1.65 mg (100 unit / g), water 17 ⁇ 1, MgO ( 0-10 for oil
- Refined sardine oil (EPA 28.2%, DHA 12.5%, manufactured by Nihon Suisan Co., Ltd.) lg with lipase QLM 0.83 mg (50 unit / g), water with ethanol amount 3.5 to 20% (v / v), Alcolysis was performed under the condition of adding MgO (0.25% w / w to oil) and ethanol / 170 / zl (0.75 equivalent to fatty acid) and stirring at 40 ° C for 16 hours.
- the alcoholysis was carried out under the condition that 0.5 to 1.5 equivalent amount was added and the mixture was stirred at 40 ° C for 16 hours.
- Table 9 shows the results.
- the amount of ethanol used was 0.5 to 1.5 equivalents to the amount of fatty acids.
- Refined sardine oil (EPA 28.2%, DHA 12.5%, manufactured by Nihon Suisan Co., Ltd.) 1.65 mg (100 unit / g) of lipase QLM, 17 ⁇ 1 of water, gO (0.25% w / w to oil) )), 1 equivalent of ethanol was added to the fatty acid and stirred at 40 ° C for 0-24 hours.
- the alcoholysis was performed under the condition that 1 equivalent amount of ethanol was added to the fatty acid and stirred at 40 ° C for 16 hours.
- Coho salmon extract EPA 9.8%, DHA 14.0%
- Lipozyme TLIM Thermomyces la Nuginosas, Novozym
- water 10 ⁇ 1 MgO (Pure Chemical Co., Ltd. (Above) (0.5% (w / w) or 2.5% (w / w) based on oil), 1701 ethanol (0.75 equivalent based on fatty acid) was added, and the mixture was stirred at 40 ° C for 16 hours.
- the solid content was filtered off, and the glyceride fraction was separated by preparative TLC. After methyl esterification, the fatty acid composition was analyzed by gas chromatography. The analysis conditions for gas chromatography are shown below.
- Capillary column DB-WAXO & W Scientific), Fused Silica Capillary Column, 0.25m ml.D.X 30m, 0.25 ⁇ m film thickness
- Carrier gas helium
- the ethanolysis reaction was performed under the above conditions except that water and MgO were not added.
- glyceride fraction EPA the area of DHA 0/0, EPA, the results of fatty acid recovery and glyceride recovery of DHA in Table 13, Table 14 shows the results of Comparative Examples.
- Table 16 shows the results of the ethanolysis reaction under the above conditions except that MgO and water were not added.
- Table 18 shows the results of ethanolysis reaction under the above conditions except that MgO and water were not added.
- sardine oil EPA 15.7%, DHA 9.0%, Nihon Suisan Co., Ltd.
- fat and oil lg combined with lipase QLM 1.65mg (100 unit / g) and lipozyme TLIM 5mg (0.5%) 10 ⁇ l, MgO 2.5% or 0.25% (w / w), and ethanol 170 ⁇ l were collected and subjected to ethanolysis reaction at 40 ° C for 16 hours.
- Table 19 shows the results of EPA, DHAffi3 ⁇ 4%, recovery rate, and glyceride recovery rate. It was possible to concentrate both EPA and DHA by combining lipase QLM with EPA concentration effect and Lipozyme TL IM with DHA concentration effect.
- Table 20 shows the results of ethanolysis reaction under the above conditions except that MgO and water were not added.
- fats and oils containing PUFA such as EPA and DHA in high concentration can be provided.
- PUFA such as EPA or DHA
- a certain amount of PUFA such as EPA or DHA is added to health foods, a smaller amount of oil or fat is added than before.
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Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
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EP07741570.1A EP2006389B1 (en) | 2006-04-13 | 2007-04-13 | Process for preparing concentrated polyunsaturated fatty acid oil |
CA2649337A CA2649337C (en) | 2006-04-13 | 2007-04-13 | Process for preparing concentrated polyunsaturated fatty acid oil |
JP2008510998A JP5111363B2 (ja) | 2006-04-13 | 2007-04-13 | 高度不飽和脂肪酸濃縮油の製造方法 |
US12/296,786 US9150817B2 (en) | 2006-04-13 | 2007-04-13 | Process for preparing concentrated polyunsaturated fatty acid oil |
DK07741570.1T DK2006389T3 (en) | 2006-04-13 | 2007-04-13 | Process for preparing concentrated polyunsaturated fatty acid oil |
NO20084220A NO20084220L (no) | 2006-04-13 | 2008-10-08 | Fremgangsmate for fremstilling av kondensert polyumettet fettsyreolje |
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JP2006-111039 | 2006-04-13 | ||
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US (1) | US9150817B2 (ja) |
EP (1) | EP2006389B1 (ja) |
JP (1) | JP5111363B2 (ja) |
CA (1) | CA2649337C (ja) |
DK (1) | DK2006389T3 (ja) |
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WO (1) | WO2007119811A1 (ja) |
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58165796A (ja) * | 1982-03-26 | 1983-09-30 | Asahi Denka Kogyo Kk | 長鎖高度不飽和脂肪酸グリセリドの濃縮法 |
JPS5914793A (ja) * | 1982-07-16 | 1984-01-25 | Nippon Oil & Fats Co Ltd | 高度不飽和脂肪酸低級アルコ−ルエステルの濃縮分離方法 |
JPS63287492A (ja) * | 1987-05-20 | 1988-11-24 | Kao Corp | 油脂類のエステル交換反応方法 |
WO1990013656A1 (en) * | 1989-05-01 | 1990-11-15 | Enzytech, Inc. | Enzymatic production of glycerides containing omega-3 fatty acids |
JPH03108489A (ja) * | 1989-09-22 | 1991-05-08 | Meito Sangyo Kk | 長鎖高度不飽和脂肪酸モノグリセリドの製造法 |
WO1995024459A1 (en) * | 1994-03-08 | 1995-09-14 | Norsk Hydro A.S | Refining oil compositions |
JP2004222595A (ja) * | 2003-01-23 | 2004-08-12 | Kao Corp | ジグリセリドの製造方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3274159A (en) * | 1963-01-07 | 1966-09-20 | Union Carbide Corp | Polyester imides of trimellitic anhydride |
US5968792A (en) * | 1996-12-19 | 1999-10-19 | Henkel Corporation | Calcium activation of lipase enzyme in process of pressure splitting glycerides |
DE102005002711A1 (de) | 2005-01-19 | 2006-07-27 | Cognis Deutschland Gmbh & Co. Kg | Herstellung und Verwendung von Monoglyceriden |
-
2007
- 2007-04-13 WO PCT/JP2007/058134 patent/WO2007119811A1/ja active Application Filing
- 2007-04-13 JP JP2008510998A patent/JP5111363B2/ja active Active
- 2007-04-13 DK DK07741570.1T patent/DK2006389T3/en active
- 2007-04-13 US US12/296,786 patent/US9150817B2/en not_active Expired - Fee Related
- 2007-04-13 EP EP07741570.1A patent/EP2006389B1/en not_active Not-in-force
- 2007-04-13 CA CA2649337A patent/CA2649337C/en not_active Expired - Fee Related
-
2008
- 2008-10-08 NO NO20084220A patent/NO20084220L/no not_active Application Discontinuation
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58165796A (ja) * | 1982-03-26 | 1983-09-30 | Asahi Denka Kogyo Kk | 長鎖高度不飽和脂肪酸グリセリドの濃縮法 |
JPS5914793A (ja) * | 1982-07-16 | 1984-01-25 | Nippon Oil & Fats Co Ltd | 高度不飽和脂肪酸低級アルコ−ルエステルの濃縮分離方法 |
JPS63287492A (ja) * | 1987-05-20 | 1988-11-24 | Kao Corp | 油脂類のエステル交換反応方法 |
WO1990013656A1 (en) * | 1989-05-01 | 1990-11-15 | Enzytech, Inc. | Enzymatic production of glycerides containing omega-3 fatty acids |
JPH03108489A (ja) * | 1989-09-22 | 1991-05-08 | Meito Sangyo Kk | 長鎖高度不飽和脂肪酸モノグリセリドの製造法 |
WO1995024459A1 (en) * | 1994-03-08 | 1995-09-14 | Norsk Hydro A.S | Refining oil compositions |
JPH09510091A (ja) | 1994-03-08 | 1997-10-14 | ノルスク・ヒドロ・アクシェセルスカープ | 精油組成物 |
JP2004222595A (ja) * | 2003-01-23 | 2004-08-12 | Kao Corp | ジグリセリドの製造方法 |
Non-Patent Citations (5)
Title |
---|
HATA K. ET AL.: "EPA, DHA no Bunri Gijutsu", BUNRI GIJUTSU, vol. 30, no. 6, 2000, pages 451 - 454, XP003018817 * |
J. S. DORDICK: "Enzymatic catalysis in monophasic organic solvents", ENZYME MICROB. TECHNOL., vol. 11, April 1989 (1989-04-01), pages 194 - 211 |
L. ZUI; O.P WARD: "Lipase-catalyzed alcoholysis to concentrate the n-3 polyunsaturated fatty acids of cod liver oil", ENZYME MICROB. TECHNOL., 15 July 1993 (1993-07-15), pages 601 - 606 |
See also references of EP2006389A4 |
ZUYI L. ET AL.: "Lipase-catalyzed alcoholysis to concentrate the n-3 polyunsaturated fatty acid of cod liver oil", ENZYME MICROB. TECHNOL., vol. 15, 1993, pages 601 - 606, XP003018816 * |
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Also Published As
Publication number | Publication date |
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US9150817B2 (en) | 2015-10-06 |
DK2006389T3 (en) | 2017-08-28 |
EP2006389A9 (en) | 2009-04-08 |
JP5111363B2 (ja) | 2013-01-09 |
NO20084220L (no) | 2009-01-13 |
EP2006389A2 (en) | 2008-12-24 |
CA2649337A1 (en) | 2007-10-25 |
EP2006389A4 (en) | 2013-01-09 |
EP2006389B1 (en) | 2017-05-31 |
JPWO2007119811A1 (ja) | 2009-08-27 |
US20090176284A1 (en) | 2009-07-09 |
CA2649337C (en) | 2014-11-18 |
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