JP5111363B2 - 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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- JP5111363B2 JP5111363B2 JP2008510998A JP2008510998A JP5111363B2 JP 5111363 B2 JP5111363 B2 JP 5111363B2 JP 2008510998 A JP2008510998 A JP 2008510998A JP 2008510998 A JP2008510998 A JP 2008510998A JP 5111363 B2 JP5111363 B2 JP 5111363B2
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- fatty acid
- oil
- unsaturated fatty
- highly unsaturated
- reaction
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- 235000021122 unsaturated fatty acids Nutrition 0.000 title claims description 23
- 150000004670 unsaturated fatty acids Chemical class 0.000 title claims description 23
- 238000004519 manufacturing process Methods 0.000 title claims description 16
- 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 98
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 80
- 235000019198 oils Nutrition 0.000 claims description 80
- 108090001060 Lipase Proteins 0.000 claims description 55
- 239000004367 Lipase Substances 0.000 claims description 55
- 102000004882 Lipase Human genes 0.000 claims description 55
- 235000019421 lipase Nutrition 0.000 claims description 55
- 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 54
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 54
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 54
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 51
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 51
- 229940090949 docosahexaenoic acid Drugs 0.000 claims description 50
- 239000000395 magnesium oxide Substances 0.000 claims description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 42
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 39
- 229930195729 fatty acid Natural products 0.000 claims description 39
- 239000000194 fatty acid Substances 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 37
- 150000004665 fatty acids Chemical class 0.000 claims description 37
- 125000005456 glyceride group Chemical group 0.000 claims description 34
- 235000019197 fats Nutrition 0.000 claims description 27
- 238000006136 alcoholysis reaction 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 10
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 6
- 239000000920 calcium hydroxide Substances 0.000 claims description 6
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 6
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000292 calcium oxide Substances 0.000 claims description 6
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 6
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 6
- 239000000347 magnesium hydroxide Substances 0.000 claims description 6
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 6
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 6
- 244000005700 microbiome Species 0.000 claims description 6
- 241000223258 Thermomyces lanuginosus Species 0.000 claims description 5
- 235000021323 fish oil Nutrition 0.000 claims description 4
- 241000589540 Pseudomonas fluorescens Species 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 241000588810 Alcaligenes sp. Species 0.000 claims description 2
- 241000589513 Burkholderia cepacia Species 0.000 claims description 2
- 241000223257 Thermomyces Species 0.000 claims description 2
- 241000588986 Alcaligenes Species 0.000 claims 1
- 239000003921 oil Substances 0.000 description 70
- 239000003925 fat Substances 0.000 description 24
- 238000011084 recovery Methods 0.000 description 19
- 238000000034 method Methods 0.000 description 15
- 102000004190 Enzymes Human genes 0.000 description 13
- 241001125048 Sardina Species 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 235000019512 sardine Nutrition 0.000 description 12
- 108010048733 Lipozyme Proteins 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 description 11
- 108090000790 Enzymes Proteins 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 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
- 230000032050 esterification Effects 0.000 description 6
- 238000005886 esterification reaction Methods 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
- 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 5
- 235000021294 Docosapentaenoic acid Nutrition 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 238000004458 analytical method Methods 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
- 238000004821 distillation Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 235000014593 oils and fats Nutrition 0.000 description 3
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 3
- 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
- 239000012159 carrier gas Substances 0.000 description 2
- 239000003153 chemical reaction reagent 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
- 239000012141 concentrate Substances 0.000 description 2
- 239000003814 drug 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
- 238000000199 molecular distillation Methods 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
- 239000000843 powder Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 108090000623 proteins and genes Proteins 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
- 239000000126 substance Substances 0.000 description 2
- 150000003626 triacylglycerols Chemical class 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
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 229920000064 Ethyl eicosapentaenoic acid Polymers 0.000 description 1
- 241000208818 Helianthus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 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
- 235000019486 Sunflower oil Nutrition 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
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000019961 diglycerides of fatty acid Nutrition 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
- 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
- 229940013317 fish oils Drugs 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
- 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
- 210000004185 liver Anatomy 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
- 230000000813 microbial effect Effects 0.000 description 1
- 235000019960 monoglycerides of fatty acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 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
- 238000000526 short-path distillation Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 230000014616 translation Effects 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Fats And Perfumes (AREA)
Description
キャピラリーカラム:DB-WAX(J&W Scientific)、Fused Silica Capillary Column、0.25mmI.D.×30m ,0.25μm film thickness
キャリヤーガス:ヘリウム
検出器:250℃,FID
注入口250℃,スプリット比=100:1
カラム温度.:180℃→3℃/min →230℃(15min)
装置:Hewlett Packard 6890
リパーゼPS(バーカホリデリア セパシア、天野エンザイム(株)製)3.3mg(100unit/g)についても同様の条件で反応させた。
精製イワシ油(EPA 28.2%, DHA 12.5%、日本水産(株)製)1kgにリパーゼQLM(アルカリゲネス エスピー、名糖産業(株)製)0.83g、水17g、MgO 2.5g、エタノールを173ml加え、40℃で16時間撹拌した。遠心分離後、固形分を除き、エタノールを留去し、1.06kg得た。希硫酸で洗浄後、湯洗浄し、薄膜蒸留装置により、エステル、脂肪酸を留去し、グリセリド画分としてのEPA濃縮油を583g得た。脂肪酸組成を測定したところ、EPA48.3%、DHA17.3%であった。
精製マグロ油(EPA 6.75%、DHA 24.3%)1kgにリポザイムTLIM(サーモマイセス、ノボザイム社製)1g、水 17g、MgO 5g、エタノール173mlを加え、40℃16時間撹拌した。固形分をろ過後、エタノールを留去し、1.07kgを得た。リン酸で洗浄後、湯洗浄し、分子蒸留装置により、エステル、脂肪酸を留去し、グリセリド画分としてのDHA濃縮油416gを得た。脂肪酸組成を測定したところ、EPA 9.4%、DHA 52.8%であった。
実施例1と同じ条件、すなわち、精製イワシ油(EPA 28.2%, DHA 12.5%、日本水産(株)製)1gにリパーゼQLMを1.65 mg(100 unit/g)、水を17μl、MgO(油に対し0〜10%w/w))、エタノールを170μl(脂肪酸に対し0.75当量)加え、40℃16時間撹拌という条件でアルコリシスを行った。
精製イワシ油(EPA 28.2%, DHA 12.5%、日本水産(株)製)1gにリパーゼQLMを0.83 mg(50 unit/g)、水をエタノール量に対して3.5〜20%(v/v)、MgO(油に対し0.25%w/w))、エタノールを170μl(脂肪酸に対し0.75当量)加え、40℃16時間撹拌するという条件でアルコリシスを行った。
精製イワシ油(EPA 28.2%, DHA 12.5%、日本水産(株)製)1gにリパーゼQLMを0.83 mg(50 unit/g)、水を17μl、MgO(油に対し0.25%w/w))、エタノールを脂肪酸に対し0.5〜1.5当量加え、40℃16時間撹拌するという条件でアルコリシスを行った。
精製イワシ油(EPA 28.2%、DHA12.5%、日本水産(株)製)1gにリパーゼQLMを10〜50 unit/g、水を17μl、MgO(油に対し0.25~1%w/w))、エタノールを脂肪酸に対し0.75当量加え、40℃で16時間撹拌するという条件でアルコリシスを行った。
精製イワシ油(EPA28.2%, DHA 12.5%、日本水産(株)製)1gにリパーゼQLMを1.65mg(100 unit/g)、水を17μl、MgO(油に対し0.25%w/w))、エタノールを脂肪酸に対し1当量加え、40℃で0〜24時間撹拌するという条件でアルコリシスを行った。
MgO、水を使用しない場合のリパーゼの反応
精製イワシ油(EPA 28.2%, DHA 12.5%、日本水産(株)製)1gにリパーゼQLMを100〜1000 unit/g)、エタノールを脂肪酸に対し1当量加え、40℃で16時間撹拌するという条件でアルコリシスを行った。
ギンザケ抽出油(EPA 9.8%, DHA 14.0%)1gにリポザイムTLIM(サーモマイセス ラヌギノサス、ノボザイム社製)を2mg(0.2%)、水を10μl、MgO(純正化学(株)特級試薬99%以上)(油に対し0.5%(w/w)または2.5%(w/w))、エタノールを170μl(脂肪酸に対し0.75当量)加え、40℃で16時間撹拌した。反応後、固形分をろ別し、分取TLCでグリセリド画分を分離し、メチルエステル化後、ガスクロマトグラフィ−にて脂肪酸組成の分析を行った。ガスクロマトグラフィの分析条件は以下に示す。
キャピラリーカラム:DB-WAX(J&W Scientific)、Fused Silica Capillary Column、0.25mmI.D.×30m ,0.25μm film thickness
キャリヤーガス:ヘリウム
検出器:250℃,FID
注入口250℃,スプリット比=100:1
カラム温度.:180℃→3℃/min →230℃(15min)
装置:Hewlett Packard 6890
また、比較例として、水及びMgO無添加以外は上記の条件でエタノリシス反応を行った。
スケトウダラ抽出油(EPA12.3%, DHA 7.9%)を原料として用い、油脂1gにリパーゼQLM 1.65mg(100 unit/g)、水17μl、MgO 2.5%(w/w)、およびエタノール170μlを加え、40℃で16時間エタノリシス反応を行った。またリポザイムTLIM 5mg(0.5%)についても同様に水、MgOを添加し、エタノリシス反応を行った。EPA、DHA面積%、回収率、グリセリド回収率の結果を表15に示す。リパーゼQLMではEPAが濃縮され、リポザイムTLIMではDHAが濃縮された。いずれもEPAとDHAを合わせた面積%は原料の倍以上に濃縮された。
マンボウ肝油(アラキドン酸(AA) 5.1%、EPA 4.2%, ドコサペンタエン酸(DPA)7.7%、DHA 10.5%)を原料として用い、油脂1gにリパーゼQLM 1.65mg(100 unit/g)、水17μl、MgO 2.5%(w/w)、およびエタノール170μlを加え、40℃で16時間エタノリシス反応を行った。またリポザイムTLIM 5mg(0.5%)についても同様に水、MgOを添加し、エタノリシス反応を行った。AA、EPA、DPA、DHA面積%、回収率、グリセリド回収率の結果を表17に示す。リパーゼQLMではAA、EPA、DPAおよびDHAが濃縮されたのに対し、リポザイムTLIMはDHAのみが濃縮された。
イワシ油(EPA 15.7%, DHA 9.0%、日本水産(株)製)を原料として用い、油脂1gにリパーゼQLM 1.65mg(100 unit/g)とリポザイムTLIM 5mg(0.5%)を組み合わせて、水10μl、MgO 2.5%または0.25% (w/w)、およびエタノール 170μlを加え、40℃で16時間エタノリシス反応を行った。EPA、DHA面積%、回収率、グリセリド回収率の結果を表19に示す。EPA濃縮効果のあるリパーゼQLMとDHA濃縮効果のあるリポザイムTLIMを組み合わせることで、EPA、DHAのいずれも濃縮することが可能であった。
Claims (7)
- 反応添加物として酸化マグネシウム、水酸化マグネシウム、酸化カルシウム、水酸化カルシウムの中から選ばれた少なくとも1種の化合物、及びアルコールに対して1〜30%(w/w)の添加量の水の存在下で、油脂を構成する脂肪酸として高度不飽和脂肪酸を含有する油脂をリパーゼによるアルコリシス反応に付す工程、および、高度不飽和脂肪酸が濃縮されたグリセリド画分を分離する工程、を含む高度不飽和脂肪酸濃縮油の製造方法。
- 反応添加物が酸化マグネシウムである、請求項1に記載の高度不飽和脂肪酸濃縮油の製造方法。
- アルコリシス反応がエタノリシスである、請求項1又は2に記載の高度不飽和脂肪酸濃縮油の製造方法。
- 高度不飽和脂肪酸がエイコサペンタエン酸及び/又はドコサヘキサエン酸である、請求項1〜3のいずれかに記載の高度不飽和脂肪酸濃縮油の製造方法。
- 高度不飽和脂肪酸含有油脂が魚油である、請求項1〜4のいずれかに記載の高度不飽和脂肪酸濃縮油の製造方法。
- 反応添加物の添加量が高度不飽和脂肪酸含有油に対して0.01〜30%(w/w)である、請求項1〜5のいずれかに記載の高度不飽和脂肪酸濃縮油の製造方法。
- リパーゼが、アルカリゲネス エスピー(Alcaligenes sp.)、サーモマイセス ラヌギノサス(Thermomyces lanuginosus)、バークホリデリア セパシア(Burkholderia cepacia)、シュードモナス フルオレッセンス(Pseudomonas fluorescens)のいずれかに属する微生物から得られるリパーゼから選択される、請求項1〜6のいずれかに記載の高度不飽和脂肪酸濃縮油の製造方法。
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