CA2621901C - Enzymatic oil interesterification - Google Patents
Enzymatic oil interesterification Download PDFInfo
- Publication number
- CA2621901C CA2621901C CA2621901A CA2621901A CA2621901C CA 2621901 C CA2621901 C CA 2621901C CA 2621901 A CA2621901 A CA 2621901A CA 2621901 A CA2621901 A CA 2621901A CA 2621901 C CA2621901 C CA 2621901C
- Authority
- CA
- Canada
- Prior art keywords
- oil
- lipase
- base
- enzyme
- composition
- Prior art date
- 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.)
- Expired - Fee Related
Links
- 238000009884 interesterification Methods 0.000 title claims abstract description 47
- 230000002255 enzymatic effect Effects 0.000 title abstract description 5
- 239000003921 oil Substances 0.000 claims abstract description 161
- 108090001060 Lipase Proteins 0.000 claims abstract description 93
- 102000004882 Lipase Human genes 0.000 claims abstract description 93
- 239000004367 Lipase Substances 0.000 claims abstract description 92
- 235000019421 lipase Nutrition 0.000 claims abstract description 92
- 238000000034 method Methods 0.000 claims abstract description 60
- 230000008569 process Effects 0.000 claims abstract description 45
- 239000002738 chelating agent Substances 0.000 claims abstract description 30
- 235000019198 oils Nutrition 0.000 claims description 160
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 93
- 239000000203 mixture Substances 0.000 claims description 67
- 108090000790 Enzymes Proteins 0.000 claims description 62
- 102000004190 Enzymes Human genes 0.000 claims description 62
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 48
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 44
- 235000017550 sodium carbonate Nutrition 0.000 claims description 44
- 229910052751 metal Inorganic materials 0.000 claims description 22
- 239000002184 metal Substances 0.000 claims description 22
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 16
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 16
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 12
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 12
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 12
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims description 9
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000003240 coconut oil Substances 0.000 claims description 8
- 235000019864 coconut oil Nutrition 0.000 claims description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 8
- 235000010288 sodium nitrite Nutrition 0.000 claims description 8
- 239000008158 vegetable oil Substances 0.000 claims description 8
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 claims description 7
- 241000223257 Thermomyces Species 0.000 claims description 7
- 230000002538 fungal effect Effects 0.000 claims description 7
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 claims description 7
- 101710098554 Lipase B Proteins 0.000 claims description 6
- 241000223258 Thermomyces lanuginosus Species 0.000 claims description 6
- 239000003549 soybean oil Substances 0.000 claims description 6
- 235000012424 soybean oil Nutrition 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 108010048733 Lipozyme Proteins 0.000 claims description 5
- 239000008157 edible vegetable oil Substances 0.000 claims description 5
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 claims description 5
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 5
- 239000004471 Glycine Substances 0.000 claims description 4
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 4
- 235000004279 alanine Nutrition 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 229910000069 nitrogen hydride Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 239000001632 sodium acetate Substances 0.000 claims description 4
- 235000017281 sodium acetate Nutrition 0.000 claims description 4
- 235000012343 cottonseed oil Nutrition 0.000 claims description 3
- 239000002385 cottonseed oil Substances 0.000 claims description 3
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims description 3
- 240000002791 Brassica napus Species 0.000 claims description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims description 2
- 235000019482 Palm oil Nutrition 0.000 claims description 2
- 235000019486 Sunflower oil Nutrition 0.000 claims description 2
- 239000000828 canola oil Substances 0.000 claims description 2
- 235000019519 canola oil Nutrition 0.000 claims description 2
- 235000005687 corn oil Nutrition 0.000 claims description 2
- 239000002285 corn oil Substances 0.000 claims description 2
- 239000003346 palm kernel oil Substances 0.000 claims description 2
- 235000019865 palm kernel oil Nutrition 0.000 claims description 2
- 239000002540 palm oil Substances 0.000 claims description 2
- 239000002600 sunflower oil Substances 0.000 claims description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 11
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000007787 solid Substances 0.000 description 20
- 235000010469 Glycine max Nutrition 0.000 description 15
- 101710098556 Lipase A Proteins 0.000 description 13
- 101710099648 Lysosomal acid lipase/cholesteryl ester hydrolase Proteins 0.000 description 13
- 102100026001 Lysosomal acid lipase/cholesteryl ester hydrolase Human genes 0.000 description 13
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 8
- 238000002203 pretreatment Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003925 fat Substances 0.000 description 6
- 235000019197 fats Nutrition 0.000 description 6
- 125000005456 glyceride group Chemical group 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000005313 fatty acid group Chemical group 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
- 238000004061 bleaching Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 4
- 108010093096 Immobilized Enzymes Proteins 0.000 description 3
- 239000010775 animal oil Substances 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000009886 enzymatic interesterification Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 235000014593 oils and fats Nutrition 0.000 description 3
- 230000036961 partial effect Effects 0.000 description 3
- 238000003259 recombinant expression Methods 0.000 description 3
- 241000228212 Aspergillus Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 240000008415 Lactuca sativa Species 0.000 description 2
- 108091028043 Nucleic acid sequence Proteins 0.000 description 2
- 241000612118 Samolus valerandi Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- -1 e.g. Substances 0.000 description 2
- 235000012041 food component Nutrition 0.000 description 2
- 239000005417 food ingredient Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000008173 hydrogenated soybean oil Substances 0.000 description 2
- 230000003100 immobilizing effect Effects 0.000 description 2
- 230000002779 inactivation Effects 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- CKQVRZJOMJRTOY-UHFFFAOYSA-N octadecanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCCCC(O)=O CKQVRZJOMJRTOY-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 235000012045 salad Nutrition 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 2
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- 208000020154 Acnes Diseases 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241000223194 Fusarium culmorum Species 0.000 description 1
- 241000146406 Fusarium heterosporum Species 0.000 description 1
- 241000223221 Fusarium oxysporum Species 0.000 description 1
- 241000159512 Geotrichum Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 241000223198 Humicola Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000235395 Mucor Species 0.000 description 1
- 241000498617 Mucor javanicus Species 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 241000235403 Rhizomucor miehei Species 0.000 description 1
- 241000235527 Rhizopus Species 0.000 description 1
- 241000303962 Rhizopus delemar Species 0.000 description 1
- 240000005384 Rhizopus oryzae Species 0.000 description 1
- 235000013752 Rhizopus oryzae Nutrition 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 238000010367 cloning Methods 0.000 description 1
- 150000001875 compounds Chemical group 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000005293 duran Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 235000019626 lipase activity Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000005373 porous glass Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- 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
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
- C12N11/02—Enzymes or microbial cells immobilised on or in an organic carrier
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
- C12N9/18—Carboxylic ester hydrolases (3.1.1)
- C12N9/20—Triglyceride splitting, e.g. by means of lipase
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Fats And Perfumes (AREA)
- Enzymes And Modification Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71623105P | 2005-09-12 | 2005-09-12 | |
| US60/716,231 | 2005-09-12 | ||
| PCT/US2006/035043 WO2007033013A2 (en) | 2005-09-12 | 2006-09-11 | Enzymatic oil interesterification |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2621901A1 CA2621901A1 (en) | 2007-03-22 |
| CA2621901C true CA2621901C (en) | 2016-07-26 |
Family
ID=37865460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2621901A Expired - Fee Related CA2621901C (en) | 2005-09-12 | 2006-09-11 | Enzymatic oil interesterification |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8349594B2 (https=) |
| EP (1) | EP1934362B1 (https=) |
| JP (2) | JP2009507497A (https=) |
| KR (1) | KR101294635B1 (https=) |
| BR (1) | BRPI0615897B1 (https=) |
| CA (1) | CA2621901C (https=) |
| MX (1) | MX2008003376A (https=) |
| MY (1) | MY148921A (https=) |
| RU (1) | RU2415178C2 (https=) |
| WO (1) | WO2007033013A2 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3760180B1 (en) | 2009-07-29 | 2024-10-30 | ICU Medical, Inc. | Fluid transfer devices |
| CN102666868A (zh) * | 2009-10-21 | 2012-09-12 | 诺维信公司 | 油处理方法 |
| KR20130004286A (ko) * | 2010-03-01 | 2013-01-09 | 트랜스 바이오디젤 엘티디. | 지방산 알킬 에스테르의 효소적 합성을 위한 방법 |
| EA021491B1 (ru) * | 2011-06-09 | 2015-06-30 | Товарищество С Ограниченной Ответственностью "Казахский Научно-Исследовательский Институт Переработки Сельскохозяйственной Продукции" | Способ получения комбинированного жира на основе козьего жира и сафлорового масла |
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| JPS6239684A (ja) | 1985-08-12 | 1987-02-20 | House Food Ind Co Ltd | 酸化防止用組成物 |
| DK122686D0 (da) | 1986-03-17 | 1986-03-17 | Novo Industri As | Fremstilling af proteiner |
| DE3854249T2 (de) * | 1987-08-28 | 1996-02-29 | Novonordisk As | Rekombinante Humicola-Lipase und Verfahren zur Herstellung von rekombinanten Humicola-Lipasen. |
| JP2570774B2 (ja) | 1987-11-02 | 1997-01-16 | 味の素株式会社 | 油脂の改質法 |
| EP0320132B1 (en) | 1987-12-09 | 1995-06-21 | Kao Corporation | Immobilized enzyme and esterification and interesterification therewith |
| JP2722600B2 (ja) | 1989-02-03 | 1998-03-04 | 味の素株式会社 | 油脂の改質方法 |
| JP2722599B2 (ja) * | 1989-02-03 | 1998-03-04 | 味の素株式会社 | 油脂の改質方法 |
| US6022577A (en) | 1990-12-07 | 2000-02-08 | Nabisco Technology Company | High stearic acid soybean oil blends |
| JP2678341B2 (ja) | 1993-09-27 | 1997-11-17 | 富士紡績株式会社 | 固定化リパーゼ |
| ATE247707T1 (de) | 1994-02-21 | 2003-09-15 | Novozymes As | Verfahren zur herstellung einer immobilisierten enzympräparation und ihre verwendung |
| PT893064E (pt) * | 1997-07-22 | 2003-04-30 | Nestle Sa | Composicao lipidica para formulacao infantil e processo de preparacao |
| US6297279B1 (en) * | 1997-07-22 | 2001-10-02 | Nestac S.A. | Lipid composition for infant formula and method of preparation |
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| DE102004015781A1 (de) | 2004-03-31 | 2005-10-20 | Cognis Ip Man Gmbh | Verfahren zur enzymatischen Synthese von Triglyceriden ungesättigter Fettsäuren |
| CA2587730A1 (en) | 2004-11-17 | 2006-05-26 | Natural Asa | Enzymatically synthesized marine phospholipids |
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| KR20080055799A (ko) | 2008-06-19 |
| WO2007033013A3 (en) | 2007-10-11 |
| BRPI0615897B1 (pt) | 2022-05-31 |
| RU2008114354A (ru) | 2009-10-20 |
| MY148921A (en) | 2013-06-14 |
| MX2008003376A (es) | 2008-03-27 |
| US20080241897A1 (en) | 2008-10-02 |
| JP2013051971A (ja) | 2013-03-21 |
| EP1934362A2 (en) | 2008-06-25 |
| US8349594B2 (en) | 2013-01-08 |
| EP1934362A4 (en) | 2011-12-28 |
| EP1934362B1 (en) | 2016-07-27 |
| BRPI0615897A2 (pt) | 2011-05-31 |
| KR101294635B1 (ko) | 2013-08-16 |
| CA2621901A1 (en) | 2007-03-22 |
| JP5727449B2 (ja) | 2015-06-03 |
| RU2415178C2 (ru) | 2011-03-27 |
| WO2007033013A2 (en) | 2007-03-22 |
| JP2009507497A (ja) | 2009-02-26 |
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