CA2718374C - Extraction and winterization of lipids from oilseed and microbial sources - Google Patents
Extraction and winterization of lipids from oilseed and microbial sources Download PDFInfo
- Publication number
- CA2718374C CA2718374C CA2718374A CA2718374A CA2718374C CA 2718374 C CA2718374 C CA 2718374C CA 2718374 A CA2718374 A CA 2718374A CA 2718374 A CA2718374 A CA 2718374A CA 2718374 C CA2718374 C CA 2718374C
- Authority
- CA
- Canada
- Prior art keywords
- lipid
- lipid composition
- polar solvent
- acetone
- dha
- 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
- 150000002632 lipids Chemical class 0.000 title claims abstract description 184
- 238000000605 extraction Methods 0.000 title claims description 30
- 230000000813 microbial effect Effects 0.000 title claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 193
- 238000000034 method Methods 0.000 claims abstract description 92
- 230000008569 process Effects 0.000 claims abstract description 77
- 239000000203 mixture Substances 0.000 claims abstract description 74
- 235000020978 long-chain polyunsaturated fatty acids Nutrition 0.000 claims abstract description 49
- 239000002798 polar solvent Substances 0.000 claims abstract description 38
- 239000002904 solvent Substances 0.000 claims abstract description 35
- 230000007935 neutral effect Effects 0.000 claims abstract description 16
- 239000000463 material Substances 0.000 claims abstract description 5
- 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 107
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 56
- 229940090949 docosahexaenoic acid Drugs 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 43
- 239000002028 Biomass Substances 0.000 claims description 29
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 28
- 239000000194 fatty acid Substances 0.000 claims description 28
- 229930195729 fatty acid Natural products 0.000 claims description 28
- 125000005456 glyceride group Chemical group 0.000 claims description 27
- 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 claims description 26
- 150000003626 triacylglycerols Chemical class 0.000 claims description 26
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 26
- 150000004665 fatty acids Chemical class 0.000 claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 241000233671 Schizochytrium Species 0.000 claims description 15
- 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 claims description 14
- 229930182558 Sterol Natural products 0.000 claims description 13
- 239000012454 non-polar solvent Substances 0.000 claims description 13
- 235000003702 sterols Nutrition 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims description 12
- -1 sterol esters Chemical class 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 claims description 9
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 9
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 9
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 9
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 9
- 150000003432 sterols Chemical class 0.000 claims description 9
- 108090000623 proteins and genes Proteins 0.000 claims description 8
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 8
- 235000021294 Docosapentaenoic acid Nutrition 0.000 claims description 7
- 235000021342 arachidonic acid Nutrition 0.000 claims description 7
- 229940114079 arachidonic acid Drugs 0.000 claims description 7
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 claims description 6
- 241000235575 Mortierella Species 0.000 claims description 6
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 claims description 6
- 239000004164 Wax ester Substances 0.000 claims description 6
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims description 6
- 229940031439 squalene Drugs 0.000 claims description 6
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 claims description 6
- 235000019386 wax ester Nutrition 0.000 claims description 6
- 241000199914 Dinophyceae Species 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
- 241001467333 Thraustochytriaceae Species 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 239000011574 phosphorus Substances 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 235000020660 omega-3 fatty acid Nutrition 0.000 claims description 4
- 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 claims description 3
- GZJLLYHBALOKEX-UHFFFAOYSA-N 6-Ketone, O18-Me-Ussuriedine Natural products CC=CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O GZJLLYHBALOKEX-UHFFFAOYSA-N 0.000 claims description 3
- 241000233675 Thraustochytrium Species 0.000 claims description 3
- KAUVQQXNCKESLC-UHFFFAOYSA-N docosahexaenoic acid (DHA) Natural products COC(=O)C(C)NOCC1=CC=CC=C1 KAUVQQXNCKESLC-UHFFFAOYSA-N 0.000 claims description 3
- 241000199912 Crypthecodinium cohnii Species 0.000 claims description 2
- 238000000926 separation method Methods 0.000 abstract description 4
- 239000000356 contaminant Substances 0.000 abstract 2
- 238000001556 precipitation Methods 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 84
- 239000007787 solid Substances 0.000 description 32
- 239000003921 oil Substances 0.000 description 28
- 235000019198 oils Nutrition 0.000 description 28
- 239000013049 sediment Substances 0.000 description 23
- 239000007788 liquid Substances 0.000 description 22
- 230000008018 melting Effects 0.000 description 19
- 238000002844 melting Methods 0.000 description 19
- 238000001914 filtration Methods 0.000 description 17
- 238000011084 recovery Methods 0.000 description 15
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 12
- 238000004809 thin layer chromatography Methods 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 11
- 238000005119 centrifugation Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 208000016444 Benign adult familial myoclonic epilepsy Diseases 0.000 description 9
- 238000004061 bleaching Methods 0.000 description 9
- 230000001413 cellular effect Effects 0.000 description 9
- 208000016427 familial adult myoclonic epilepsy Diseases 0.000 description 9
- ZGNITFSDLCMLGI-UHFFFAOYSA-N flubendiamide Chemical compound CC1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C1NC(=O)C1=CC=CC(I)=C1C(=O)NC(C)(C)CS(C)(=O)=O ZGNITFSDLCMLGI-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000010586 diagram Methods 0.000 description 8
- 238000007670 refining Methods 0.000 description 8
- 235000021588 free fatty acids Nutrition 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 230000001877 deodorizing effect Effects 0.000 description 6
- 239000003925 fat Substances 0.000 description 6
- 235000019197 fats Nutrition 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- UPYKUZBSLRQECL-UKMVMLAPSA-N Lycopene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1C(=C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=C)CCCC2(C)C UPYKUZBSLRQECL-UKMVMLAPSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000003365 glass fiber Substances 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- 150000003904 phospholipids Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 239000012620 biological material Substances 0.000 description 4
- 235000005473 carotenes Nutrition 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000001030 gas--liquid chromatography Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- ZAZKJZBWRNNLDS-UHFFFAOYSA-N methyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC ZAZKJZBWRNNLDS-UHFFFAOYSA-N 0.000 description 4
- 235000003441 saturated fatty acids Nutrition 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 229930003799 tocopherol Natural products 0.000 description 4
- 239000011732 tocopherol Substances 0.000 description 4
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 235000021314 Palmitic acid Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000021466 carotenoid Nutrition 0.000 description 3
- 150000001747 carotenoids Chemical class 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 3
- 150000002943 palmitic acids Chemical class 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 238000005498 polishing Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 125000002640 tocopherol group Chemical class 0.000 description 3
- 235000019149 tocopherols Nutrition 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000598397 Schizochytrium sp. Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 2
- OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 2
- 238000011021 bench scale process Methods 0.000 description 2
- 235000013734 beta-carotene Nutrition 0.000 description 2
- 239000011648 beta-carotene Substances 0.000 description 2
- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 description 2
- 229960002747 betacarotene Drugs 0.000 description 2
- FDSDTBUPSURDBL-LOFNIBRQSA-N canthaxanthin Chemical compound CC=1C(=O)CCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C(=O)CCC1(C)C FDSDTBUPSURDBL-LOFNIBRQSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000004332 deodorization Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000011344 liquid material Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229940105132 myristate Drugs 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229940068065 phytosterols Drugs 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 229930003802 tocotrienol Natural products 0.000 description 2
- 239000011731 tocotrienol Substances 0.000 description 2
- 229940068778 tocotrienols Drugs 0.000 description 2
- KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 description 2
- 238000012795 verification Methods 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 2
- JKQXZKUSFCKOGQ-JLGXGRJMSA-N (3R,3'R)-beta,beta-carotene-3,3'-diol Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C[C@@H](O)CC1(C)C JKQXZKUSFCKOGQ-JLGXGRJMSA-N 0.000 description 1
- HOBAELRKJCKHQD-UHFFFAOYSA-N (8Z,11Z,14Z)-8,11,14-eicosatrienoic acid Natural products CCCCCC=CCC=CCC=CCCCCCCC(O)=O HOBAELRKJCKHQD-UHFFFAOYSA-N 0.000 description 1
- GJJVAFUKOBZPCB-ZGRPYONQSA-N (r)-3,4-dihydro-2-methyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2h-1-benzopyran-6-ol Chemical class OC1=CC=C2OC(CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-ZGRPYONQSA-N 0.000 description 1
- JEBFVOLFMLUKLF-IFPLVEIFSA-N Astaxanthin Natural products CC(=C/C=C/C(=C/C=C/C1=C(C)C(=O)C(O)CC1(C)C)/C)C=CC=C(/C)C=CC=C(/C)C=CC2=C(C)C(=O)C(O)CC2(C)C JEBFVOLFMLUKLF-IFPLVEIFSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000199913 Crypthecodinium Species 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- BDCFUHIWJODVNG-UHFFFAOYSA-N Desmosterol Natural products C1C=C2CC(O)C=CC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 BDCFUHIWJODVNG-UHFFFAOYSA-N 0.000 description 1
- 235000021298 Dihomo-γ-linolenic acid Nutrition 0.000 description 1
- 101100061188 Drosophila melanogaster dila gene Proteins 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- OPGOLNDOMSBSCW-CLNHMMGSSA-N Fursultiamine hydrochloride Chemical compound Cl.C1CCOC1CSSC(\CCO)=C(/C)N(C=O)CC1=CN=C(C)N=C1N OPGOLNDOMSBSCW-CLNHMMGSSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 1
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 1
- SSISHJJTAXXQAX-ZETCQYMHSA-N L-ergothioneine Chemical compound C[N+](C)(C)[C@H](C([O-])=O)CC1=CNC(=S)N1 SSISHJJTAXXQAX-ZETCQYMHSA-N 0.000 description 1
- JEVVKJMRZMXFBT-XWDZUXABSA-N Lycophyll Natural products OC/C(=C/CC/C(=C\C=C\C(=C/C=C/C(=C\C=C\C=C(/C=C/C=C(\C=C\C=C(/CC/C=C(/CO)\C)\C)/C)\C)/C)\C)/C)/C JEVVKJMRZMXFBT-XWDZUXABSA-N 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- OOUTWVMJGMVRQF-DOYZGLONSA-N Phoenicoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C(=O)C(O)CC1(C)C)C=CC=C(/C)C=CC2=C(C)C(=O)CCC2(C)C OOUTWVMJGMVRQF-DOYZGLONSA-N 0.000 description 1
- JKQXZKUSFCKOGQ-LQFQNGICSA-N Z-zeaxanthin Natural products C([C@H](O)CC=1C)C(C)(C)C=1C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC1=C(C)C[C@@H](O)CC1(C)C JKQXZKUSFCKOGQ-LQFQNGICSA-N 0.000 description 1
- QOPRSMDTRDMBNK-RNUUUQFGSA-N Zeaxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCC(O)C1(C)C)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C QOPRSMDTRDMBNK-RNUUUQFGSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- JKQXZKUSFCKOGQ-LOFNIBRQSA-N all-trans-Zeaxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C JKQXZKUSFCKOGQ-LOFNIBRQSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003289 ascorbyl group Chemical group [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 description 1
- 235000010385 ascorbyl palmitate Nutrition 0.000 description 1
- 235000013793 astaxanthin Nutrition 0.000 description 1
- 239000001168 astaxanthin Substances 0.000 description 1
- MQZIGYBFDRPAKN-ZWAPEEGVSA-N astaxanthin Chemical compound C([C@H](O)C(=O)C=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C(=O)[C@@H](O)CC1(C)C MQZIGYBFDRPAKN-ZWAPEEGVSA-N 0.000 description 1
- 229940022405 astaxanthin Drugs 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 235000012682 canthaxanthin Nutrition 0.000 description 1
- 239000001659 canthaxanthin Substances 0.000 description 1
- 229940008033 canthaxanthin Drugs 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001746 carotenes Chemical class 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 235000017471 coenzyme Q10 Nutrition 0.000 description 1
- 229940108924 conjugated linoleic acid Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- AVSXSVCZWQODGV-DPAQBDIFSA-N desmosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCC=C(C)C)C)[C@@]1(C)CC2 AVSXSVCZWQODGV-DPAQBDIFSA-N 0.000 description 1
- 238000009882 destearinating Methods 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- HOBAELRKJCKHQD-QNEBEIHSSA-N dihomo-γ-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O HOBAELRKJCKHQD-QNEBEIHSSA-N 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 238000007922 dissolution test Methods 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 description 1
- VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 description 1
- 235000020664 gamma-linolenic acid Nutrition 0.000 description 1
- 229960002733 gamolenic acid Drugs 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- AGBQKNBQESQNJD-UHFFFAOYSA-M lipoate Chemical compound [O-]C(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-M 0.000 description 1
- 235000019136 lipoic acid Nutrition 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 235000012680 lutein Nutrition 0.000 description 1
- 239000001656 lutein Substances 0.000 description 1
- 229960005375 lutein Drugs 0.000 description 1
- KBPHJBAIARWVSC-RGZFRNHPSA-N lutein Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C KBPHJBAIARWVSC-RGZFRNHPSA-N 0.000 description 1
- ORAKUVXRZWMARG-WZLJTJAWSA-N lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C ORAKUVXRZWMARG-WZLJTJAWSA-N 0.000 description 1
- 235000012661 lycopene Nutrition 0.000 description 1
- 239000001751 lycopene Substances 0.000 description 1
- OAIJSZIZWZSQBC-GYZMGTAESA-N lycopene Chemical compound CC(C)=CCC\C(C)=C\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C=C(/C)CCC=C(C)C OAIJSZIZWZSQBC-GYZMGTAESA-N 0.000 description 1
- 229960004999 lycopene Drugs 0.000 description 1
- 230000002934 lysing effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- CKQVRZJOMJRTOY-UHFFFAOYSA-N octadecanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCCCC(O)=O CKQVRZJOMJRTOY-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 229940092258 rosemary extract Drugs 0.000 description 1
- 235000020748 rosemary extract Nutrition 0.000 description 1
- 239000001233 rosmarinus officinalis l. extract Substances 0.000 description 1
- 235000021003 saturated fats Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229960002663 thioctic acid Drugs 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 235000019148 tocotrienols Nutrition 0.000 description 1
- ZCIHMQAPACOQHT-ZGMPDRQDSA-N trans-isorenieratene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/c1c(C)ccc(C)c1C)C=CC=C(/C)C=Cc2c(C)ccc(C)c2C ZCIHMQAPACOQHT-ZGMPDRQDSA-N 0.000 description 1
- 235000010692 trans-unsaturated fatty acids Nutrition 0.000 description 1
- 150000003669 ubiquinones Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- FJHBOVDFOQMZRV-XQIHNALSSA-N xanthophyll Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C=C(C)C(O)CC2(C)C FJHBOVDFOQMZRV-XQIHNALSSA-N 0.000 description 1
- 235000008210 xanthophylls Nutrition 0.000 description 1
- 150000003735 xanthophylls Chemical class 0.000 description 1
- 235000010930 zeaxanthin Nutrition 0.000 description 1
- 239000001775 zeaxanthin Substances 0.000 description 1
- 229940043269 zeaxanthin Drugs 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 235000019151 β-tocotrienol Nutrition 0.000 description 1
- 150000003782 β-tocotrienols Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/10—Production of fats or fatty oils from raw materials by extracting
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/006—Refining fats or fatty oils by extraction
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
- C11B7/0008—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents
- C11B7/0025—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents in solvents containing oxygen in their molecule
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Microbiology (AREA)
- Fats And Perfumes (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Extraction Or Liquid Replacement (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Edible Oils And Fats (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34118001P | 2001-12-12 | 2001-12-12 | |
| US60/341,180 | 2001-12-12 | ||
| CA2469647A CA2469647C (en) | 2001-12-12 | 2002-12-12 | Extraction and winterization of lipids from oilseed and microbial sources |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2469647A Division CA2469647C (en) | 2001-12-12 | 2002-12-12 | Extraction and winterization of lipids from oilseed and microbial sources |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2718374A1 CA2718374A1 (en) | 2003-06-19 |
| CA2718374C true CA2718374C (en) | 2013-05-07 |
Family
ID=23336542
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2718374A Expired - Fee Related CA2718374C (en) | 2001-12-12 | 2002-12-12 | Extraction and winterization of lipids from oilseed and microbial sources |
| CA2469647A Expired - Fee Related CA2469647C (en) | 2001-12-12 | 2002-12-12 | Extraction and winterization of lipids from oilseed and microbial sources |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2469647A Expired - Fee Related CA2469647C (en) | 2001-12-12 | 2002-12-12 | Extraction and winterization of lipids from oilseed and microbial sources |
Country Status (9)
| Country | Link |
|---|---|
| US (4) | US7419596B2 (enExample) |
| EP (3) | EP1453583B1 (enExample) |
| JP (3) | JP4647212B2 (enExample) |
| CN (1) | CN1267174C (enExample) |
| AT (1) | ATE522264T1 (enExample) |
| AU (3) | AU2002366642B2 (enExample) |
| CA (2) | CA2718374C (enExample) |
| NO (1) | NO20042929L (enExample) |
| WO (1) | WO2003049832A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11872201B2 (en) | 2018-06-21 | 2024-01-16 | Nuseed Nutritional Us Inc. | DHA enriched polyunsaturated fatty acid compositions |
| US12137701B2 (en) | 2018-06-21 | 2024-11-12 | Nuseed Nutritional Us Inc. | ALA enriched polyunsaturated fatty acid compositions |
Families Citing this family (83)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE485385T1 (de) | 2000-01-19 | 2010-11-15 | Martek Biosciences Corp | Lösungsmittelfreies extraktionsverfahren |
| JP4647212B2 (ja) | 2001-12-12 | 2011-03-09 | マーテック バイオサイエンシーズ コーポレーション | 脂肪種子および微生物供給源からの脂質の抽出および脱ろう |
| US7122216B2 (en) * | 2003-06-16 | 2006-10-17 | I.P. Holdings, L.L.C. | Vegetable oil extraction methods |
| DK1656449T3 (da) | 2003-08-21 | 2009-06-02 | Monsanto Technology Llc | Fedtsyredesaturaser fra primula |
| US20050215640A1 (en) | 2004-03-26 | 2005-09-29 | Baxter Jeffrey H | HMB compositions and uses thereof |
| ES2541537T3 (es) | 2004-04-16 | 2015-07-21 | Monsanto Technology, Llc | Expresión de desaturasas de ácido graso en maíz |
| EP1827123B1 (en) | 2004-11-04 | 2015-07-22 | Monsanto Technology, LLC | High pufa oil compositions |
| CN101098629B (zh) * | 2004-11-04 | 2010-10-13 | 孟山都技术公司 | 高pufa油组合物 |
| EP3238543B1 (en) | 2005-06-07 | 2019-03-20 | DSM Nutritional Products AG | Eukaryotic microorganisms for producing lipids and antioxidants |
| EP1903883A4 (en) * | 2005-07-01 | 2010-06-23 | Martek Biosciences Corp | OIL PRODUCT CONTAINING MULTIPLE UNSATURATED FATTY ACIDS AND ITS USES AND MANUFACTURING |
| EP1968564B1 (en) | 2005-12-19 | 2015-09-16 | Abbott Laboratories | Use of beta-hydroxy-beta-methylbutyrate to modulate the imbalance in type 1 and type 2 cytokine production |
| CA2988226C (en) | 2006-03-10 | 2022-04-26 | Monsanto Technology Llc | Soybean seed and oil compositions and methods of making same |
| US8318453B2 (en) | 2006-07-21 | 2012-11-27 | Xyleco, Inc. | Conversion systems for biomass |
| CA2659603C (en) | 2006-08-01 | 2017-03-07 | Ocean Nutrition Canada Limited | Oil producing microbes and methods of modification thereof |
| DE102007037783A1 (de) * | 2007-08-10 | 2009-02-19 | Cognis Ip Management Gmbh | Lipophile Zubereitungen |
| EP2262376B1 (en) * | 2008-03-17 | 2017-08-09 | Stepan Specialty Products, LLC | Process for refining a triglyceride oil |
| US8043496B1 (en) | 2008-03-18 | 2011-10-25 | Peter Allen Schuh | System for extracting oil from algae |
| US9896642B2 (en) | 2008-10-14 | 2018-02-20 | Corbion Biotech, Inc. | Methods of microbial oil extraction and separation |
| CN106367198A (zh) * | 2009-04-14 | 2017-02-01 | 泰拉瑞亚控股公司 | 微生物油提取和分离方法 |
| US9480271B2 (en) | 2009-09-15 | 2016-11-01 | Monsanto Technology Llc | Soybean seed and oil compositions and methods of making same |
| US8552098B2 (en) * | 2009-09-30 | 2013-10-08 | Dow Global Technologies Llc | Purified acetylated derivatives of castor oil and compositions including same |
| US20130101723A1 (en) * | 2009-11-03 | 2013-04-25 | Daniel Verkoeijen | Vegetable oil comprising a polyunsaturated fatty acid having at least 20 carbon atoms |
| CN102884201B (zh) | 2010-01-19 | 2016-04-13 | 帝斯曼知识产权资产管理有限公司 | 生产二十碳五烯酸的微生物、脂肪酸组成物及其制作方法与用途 |
| US8187861B1 (en) | 2010-01-26 | 2012-05-29 | Allen John Schuh | Phosphate removal-recovery and biofuel feedstock system |
| SG182808A1 (en) | 2010-01-29 | 2012-09-27 | Abbott Lab | Aseptically packaged nutritional liquids comprising hmb |
| WO2011094557A1 (en) | 2010-01-29 | 2011-08-04 | Abbott Laboratories | Nutritional emulsions comprising calcium hmb |
| US9693577B2 (en) | 2010-01-29 | 2017-07-04 | Abbott Laboratories | Method of preparing a nutritional powder comprising spray dried HMB |
| US8202425B2 (en) | 2010-04-06 | 2012-06-19 | Heliae Development, Llc | Extraction of neutral lipids by a two solvent method |
| US8313648B2 (en) | 2010-04-06 | 2012-11-20 | Heliae Development, Llc | Methods of and systems for producing biofuels from algal oil |
| WO2011127127A2 (en) | 2010-04-06 | 2011-10-13 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Extraction with fractionation of oil and co-products from oleaginous material |
| US8211308B2 (en) | 2010-04-06 | 2012-07-03 | Heliae Development, Llc | Extraction of polar lipids by a two solvent method |
| US20140005422A1 (en) * | 2010-04-06 | 2014-01-02 | Heliae Development, Llc | Method of extracting neutral lipids with two solvents |
| US8475660B2 (en) | 2010-04-06 | 2013-07-02 | Heliae Development, Llc | Extraction of polar lipids by a two solvent method |
| US8273248B1 (en) | 2010-04-06 | 2012-09-25 | Heliae Development, Llc | Extraction of neutral lipids by a two solvent method |
| US20130217904A1 (en) * | 2010-04-06 | 2013-08-22 | Heliae Development, Llc | Method of extracting polar lipids and neutral lipids with two solvents |
| US8211309B2 (en) | 2010-04-06 | 2012-07-03 | Heliae Development, Llc | Extraction of proteins by a two solvent method |
| US8308951B1 (en) | 2010-04-06 | 2012-11-13 | Heliae Development, Llc | Extraction of proteins by a two solvent method |
| JP2013526851A (ja) | 2010-04-06 | 2013-06-27 | ヘリアエ デベロップメント、 エルエルシー | カロテノイドおよびω−３が豊富な油を藻類から単離するための方法およびシステム |
| US8115022B2 (en) | 2010-04-06 | 2012-02-14 | Heliae Development, Llc | Methods of producing biofuels, chlorophylls and carotenoids |
| US10125331B2 (en) * | 2010-04-29 | 2018-11-13 | Advanced Energy Development | Renewable oil refining processes |
| EP2576801B1 (en) * | 2010-06-01 | 2019-10-02 | DSM IP Assets B.V. | Extraction of lipid from cells and products therefrom |
| TWI526161B (zh) | 2010-06-10 | 2016-03-21 | 亞培公司 | 包含鈣ｈｍｂ及可溶性蛋白質之實質上透明營養液 |
| WO2011159682A1 (en) | 2010-06-14 | 2011-12-22 | Raveendran Pottathil | Methods for the production of algae derived oils |
| ES2490619T3 (es) * | 2010-11-08 | 2014-09-04 | Neste Oil Oyj | Método de extracción de lípidos a partir de biomasa |
| US8999663B2 (en) | 2011-02-11 | 2015-04-07 | E L Du Pont De Nemours And Company | Method for obtaining a lipid-containing composition from microbial biomass |
| AU2012214285A1 (en) | 2011-02-11 | 2013-07-18 | E. I. Du Pont De Nemours And Company | Purification of triglyceride oil from microbial sources using short path distillation |
| US8365462B2 (en) | 2011-05-31 | 2013-02-05 | Heliae Development, Llc | V-Trough photobioreactor systems |
| USD661164S1 (en) | 2011-06-10 | 2012-06-05 | Heliae Development, Llc | Aquaculture vessel |
| USD679965S1 (en) | 2011-06-10 | 2013-04-16 | Heliae Development, Llc | Aquaculture vessel |
| USD682637S1 (en) | 2011-06-10 | 2013-05-21 | Heliae Development, Llc | Aquaculture vessel |
| US10383839B2 (en) * | 2011-06-30 | 2019-08-20 | Johnson & Johnson Vision Care, Inc. | Esters for treatment of ocular inflammatory conditions |
| CN103930104A (zh) | 2011-07-21 | 2014-07-16 | 帝斯曼知识产权资产管理有限公司 | 脂肪酸组合物 |
| KR20200003227A (ko) | 2011-11-01 | 2020-01-08 | 디에스엠 아이피 어셋츠 비.브이. | 산화적으로 안정한 다중불포화된 지방산 함유 오일 |
| US9200236B2 (en) | 2011-11-17 | 2015-12-01 | Heliae Development, Llc | Omega 7 rich compositions and methods of isolating omega 7 fatty acids |
| CN103156003B (zh) * | 2011-12-16 | 2015-04-29 | 丰益(上海)生物技术研发中心有限公司 | 一种调和油及其制备方法 |
| JPWO2013172087A1 (ja) * | 2012-05-17 | 2016-01-12 | 有限会社スキンマイケア | 一酸化窒素産生阻害活性を備える組成物 |
| US9632797B2 (en) | 2013-01-31 | 2017-04-25 | Hewlett Packard Enterprise Development Lp | Updating a commit list to indicate data to be written to a firmware interface variable repository |
| WO2014141098A1 (en) | 2013-03-13 | 2014-09-18 | Dsm Nutritional Products Ag | Engineering microorganisms |
| WO2015095690A2 (en) | 2013-12-20 | 2015-06-25 | Dsm Ip Assets B.V. | Processes for obtaining microbial oil from microbial cells |
| ES2909791T3 (es) | 2013-12-20 | 2022-05-10 | Dsm Ip Assets Bv | Procesos para obtener aceite microbiano a partir de células microbianas |
| EP3083545B1 (en) | 2013-12-20 | 2023-08-02 | DSM IP Assets B.V. | Processes for obtaining microbial oil from microbial cells |
| TWI698520B (zh) | 2013-12-20 | 2020-07-11 | 荷蘭商Ｄｓｍ智慧財產有限公司 | 用於從微生物細胞獲得微生物油之方法（三） |
| MX383112B (es) | 2013-12-20 | 2025-03-13 | Dsm Ip Assets Bv | Procedimientos para obtener aceite microbiano a partir de células microbianas. |
| PL3149133T3 (pl) | 2014-05-30 | 2019-08-30 | Drei Lilien Pvg GmbH&Co. KG | Sposób oczyszczania rafinowanych faz lipidowych |
| US11260095B2 (en) * | 2014-11-14 | 2022-03-01 | Basf Plant Science Company Gmbh | Modification of plant lipids containing PUFAs |
| AR104042A1 (es) | 2015-03-26 | 2017-06-21 | Mara Renewables Corp | Producción de alta densidad de biomasa y aceite utilizando glicerol en bruto |
| US9951326B2 (en) | 2015-07-13 | 2018-04-24 | MARA Renewables Corporation | Enhancing microbial metabolism of C5 organic carbon |
| US10851395B2 (en) | 2016-06-10 | 2020-12-01 | MARA Renewables Corporation | Method of making lipids with improved cold flow properties |
| KR102405390B1 (ko) | 2016-07-13 | 2022-06-03 | 에보닉 오퍼레이션스 게엠베하 | 용해된 지질을 함유하는 바이오매스로부터 지질을 분리하는 방법 |
| CN106343045A (zh) * | 2016-08-11 | 2017-01-25 | 青岛俏宝食品有限公司 | 一种富含长碳链多不饱和脂肪酸类脂质的营养强化型功能低温食用调和油脂 |
| ES2872009T3 (es) | 2016-12-27 | 2021-11-02 | Evonik Degussa Gmbh | Método de aislamiento de lípidos a partir de una biomasa que contiene lípidos |
| CN110267654A (zh) * | 2017-02-22 | 2019-09-20 | 嘉吉公司 | 含dha的油的纯化 |
| WO2019048327A1 (en) * | 2017-09-05 | 2019-03-14 | Evonik Degussa Gmbh | METHOD FOR SEPARATING LIPIDS IN A BIOMASS CONTAINING LYDE LIPIDS |
| EP3470502A1 (en) * | 2017-10-13 | 2019-04-17 | Evonik Degussa GmbH | Method of separating lipids from a lysed lipids containing biomass |
| EP3527664A1 (en) | 2018-02-15 | 2019-08-21 | Evonik Degussa GmbH | Method of isolating lipids from a lipids containing biomass |
| JP2021521882A (ja) * | 2018-04-20 | 2021-08-30 | ナノ アルジー ソリューションズ アーゲー | エイコサペンタエン酸オイル組成物を提供するための新規なプロセス |
| US11414621B2 (en) | 2018-05-15 | 2022-08-16 | Evonik Operations Gmbh | Method of isolating lipids from a lipids containing biomass with aid of hydrophobic silica |
| BR112020023222A2 (pt) | 2018-05-15 | 2021-03-23 | Evonik Operations Gmbh | método de isolamento de lipídios a partir de uma biomassa contendo lipídios lisados por inversão por emulsão |
| FR3085825B1 (fr) | 2018-09-14 | 2021-07-16 | Fermentalg | Huile de microorganismes riche en acide docosahexaenoique |
| FR3085962B1 (fr) | 2018-09-14 | 2021-06-18 | Fermentalg | Procede d'extracton d'une huile riche en pufa |
| CN109731102B (zh) * | 2019-01-31 | 2022-05-17 | 广州白云山汉方现代药业有限公司 | 一种降低橄榄油甲氧基苯胺值的方法 |
| KR102673054B1 (ko) * | 2023-05-31 | 2024-06-07 | 종근당건강 주식회사 | 산패 억제 및 산화 안정성이 우수한 유지조성물 및 이를 포함하는 연질캡슐 |
| CN117844647B (zh) * | 2023-12-15 | 2025-12-09 | 嘉必优生物技术（武汉）股份有限公司 | 一种产高含量、高澄清度油脂的裂殖壶菌及其应用 |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3541123A (en) * | 1968-10-21 | 1970-11-17 | Kao Corp | Process for the fractionation of oils and fats |
| US3944585A (en) * | 1973-03-05 | 1976-03-16 | The United States Of America As Represented By The Secretary Of Agriculture | Multi-step crystallization and blending process for making physiochemically designed fat compositions from tallow |
| US4205006A (en) * | 1973-03-05 | 1980-05-27 | The United States Of America As Represented By The Secretary Of Agriculture | Physiochemically designed fat compositions from tallow and process for making |
| JPS5959644A (ja) * | 1982-09-29 | 1984-04-05 | Kureha Chem Ind Co Ltd | 魚油中のエイコサペンタエン酸を濃縮する方法 |
| JPS5967241A (ja) | 1982-10-08 | 1984-04-16 | Kureha Chem Ind Co Ltd | 魚油中のエイコサペンタエン酸の濃縮方法 |
| JPS60133094A (ja) * | 1983-12-21 | 1985-07-16 | 日清製油株式会社 | 高純度エイコサペンタエン酸の製造法 |
| JPS61192292A (ja) * | 1985-02-21 | 1986-08-26 | Agency Of Ind Science & Technol | γ−リノレン酸含有グリセリドの濃縮方法 |
| WO1986004354A1 (en) | 1985-01-22 | 1986-07-31 | Japan As Represented By Director General Of Agency | Method for obtaining lipids from fungus bodies |
| US4792418A (en) * | 1985-08-14 | 1988-12-20 | Century Laboratories, Inc. | Method of extraction and purification of polyunsaturated fatty acids from natural sources |
| CA2077914C (en) * | 1990-03-12 | 2000-05-30 | Einar Sola | Process for enrichment of fat with regard to polyunsaturated fatty acids and phospholipids, and application of such enriched fat |
| US5658767A (en) | 1991-01-24 | 1997-08-19 | Martek Corporation | Arachidonic acid and methods for the production and use thereof |
| JP3354582B2 (ja) * | 1991-09-30 | 2002-12-09 | サントリー株式会社 | オメガ９系高度不飽和脂肪酸およびこれを含有する脂質の製造方法 |
| DE4219360C2 (de) * | 1992-06-12 | 1994-07-28 | Milupa Ag | Verfahren zur Gewinnung von Lipiden mit einem hohen Anteil von langkettig-hochungesättigten Fettsäuren |
| AU729424B2 (en) * | 1995-11-24 | 2001-02-01 | Unilever Plc | Composition based on fish oil |
| US6255505B1 (en) * | 1996-03-28 | 2001-07-03 | Gist-Brocades, B.V. | Microbial polyunsaturated fatty acid containing oil from pasteurised biomass |
| ES2205202T5 (es) * | 1996-03-28 | 2015-11-26 | Dsm Ip Assets B.V. | Procedimiento para la preparación de una biomasa microbiana granular y aislamiento de compuestos valiosos contenidos en ella |
| JP2000510513A (ja) * | 1996-05-15 | 2000-08-15 | ヒスト―ブロカデス・ベスローテン・フェンノートシャップ | 低ステロール且つ高トリグリセライドの微生物性油を得るための極性溶媒によるステロール抽出 |
| ES2362476T3 (es) | 1996-07-23 | 2011-07-06 | Nagase Chemtex Corporation | Proceso para preparar ácido docosahexanoico y ácido docosapentanoico. |
| IN1998CH01219A (en) * | 1997-06-04 | 2005-03-04 | Calgene Llc | Production of polyunsaturated fatty acid by expression of polyketide-like synthesis genes in plants |
| ATE485385T1 (de) * | 2000-01-19 | 2010-11-15 | Martek Biosciences Corp | Lösungsmittelfreies extraktionsverfahren |
| JP3425622B2 (ja) * | 2000-03-30 | 2003-07-14 | 独立行政法人産業技術総合研究所 | ラビリンチュラ属菌を用いた高度不飽和脂肪酸含有培養物および高度不飽和脂肪酸含有油脂の製造方法 |
| US6344574B1 (en) * | 2000-07-20 | 2002-02-05 | The United States Of America As Represented By The Secretary Of Agriculture | Solvent fractionation of chicken fat for making lipid compositions enriched in unsaturated fatty acid-containing triacylglycerols |
| EP1178103A1 (en) * | 2000-08-02 | 2002-02-06 | Dsm N.V. | Purifying crude pufa oils |
| CN1109093C (zh) * | 2000-09-28 | 2003-05-21 | 中国科学院武汉病毒研究所 | 一种微生物油脂的制备方法 |
| CN100567483C (zh) * | 2000-09-28 | 2009-12-09 | 生物源食物及科学公司 | 脂肪酸去饱和酶家族成员fad4、fad5、fad5-2和fad6及它们的应用 |
| EP1215274A1 (en) * | 2000-12-15 | 2002-06-19 | Dsm N.V. | Enrichment of microbial oils |
| US6492537B2 (en) * | 2001-02-20 | 2002-12-10 | The United States Of America As Represented By The Secretary Of Agriculture | Solvent fractionation of menhaden oil and partially hydrogenated menhaden oil for making lipid compositions enriched in unsaturated fatty acid-containing triacylglycerols |
| DE10151155A1 (de) * | 2001-10-19 | 2003-05-08 | Nutrinova Gmbh | Native PUFA-Triglyceridmischungen mit einem hohen Gehalt an mehrfach ungesättigten Fettsäuren sowie Verfahren zu deren Herstellung und deren Verwendung |
| JP4647212B2 (ja) * | 2001-12-12 | 2011-03-09 | マーテック バイオサイエンシーズ コーポレーション | 脂肪種子および微生物供給源からの脂質の抽出および脱ろう |
| US20040209953A1 (en) * | 2002-12-06 | 2004-10-21 | Wai Lee Theresa Siu-Ling | Glyceride compositions and methods of making and using same |
| US7528612B2 (en) * | 2006-09-29 | 2009-05-05 | Rockwell Automation Technologies, Inc. | System and method for monitoring a motor control center |
| US7561412B2 (en) * | 2006-09-29 | 2009-07-14 | Rockwell Automation Technologies, Inc. | System and method for automatically securing a motor control center |
| US8228067B2 (en) * | 2006-11-02 | 2012-07-24 | Production Resource Group, Llc | Load bank |
-
2002
- 2002-12-12 JP JP2003550880A patent/JP4647212B2/ja not_active Expired - Fee Related
- 2002-12-12 AT AT02791414T patent/ATE522264T1/de not_active IP Right Cessation
- 2002-12-12 CA CA2718374A patent/CA2718374C/en not_active Expired - Fee Related
- 2002-12-12 EP EP02791414A patent/EP1453583B1/en not_active Revoked
- 2002-12-12 CN CNB028280431A patent/CN1267174C/zh not_active Expired - Fee Related
- 2002-12-12 AU AU2002366642A patent/AU2002366642B2/en not_active Ceased
- 2002-12-12 EP EP10166318A patent/EP2239028A1/en not_active Withdrawn
- 2002-12-12 WO PCT/US2002/039930 patent/WO2003049832A1/en not_active Ceased
- 2002-12-12 CA CA2469647A patent/CA2469647C/en not_active Expired - Fee Related
- 2002-12-12 EP EP10176356A patent/EP2261312A1/en not_active Withdrawn
- 2002-12-12 US US10/498,598 patent/US7419596B2/en not_active Expired - Lifetime
-
2004
- 2004-07-08 NO NO20042929A patent/NO20042929L/no unknown
-
2008
- 2008-08-01 US US12/184,974 patent/US7695626B2/en not_active Expired - Lifetime
-
2009
- 2009-02-24 AU AU2009200718A patent/AU2009200718B2/en not_active Expired - Fee Related
-
2010
- 2010-03-16 JP JP2010058682A patent/JP2010196060A/ja active Pending
- 2010-04-09 US US12/757,383 patent/US8012354B2/en not_active Expired - Fee Related
-
2011
- 2011-09-06 US US13/226,324 patent/US8480904B2/en not_active Expired - Fee Related
- 2011-11-10 AU AU2011250697A patent/AU2011250697A1/en not_active Abandoned
-
2013
- 2013-01-18 JP JP2013007324A patent/JP2013100530A/ja not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11872201B2 (en) | 2018-06-21 | 2024-01-16 | Nuseed Nutritional Us Inc. | DHA enriched polyunsaturated fatty acid compositions |
| US12137701B2 (en) | 2018-06-21 | 2024-11-12 | Nuseed Nutritional Us Inc. | ALA enriched polyunsaturated fatty acid compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010196060A (ja) | 2010-09-09 |
| CA2469647C (en) | 2011-02-15 |
| US20050115897A1 (en) | 2005-06-02 |
| EP2239028A1 (en) | 2010-10-13 |
| JP4647212B2 (ja) | 2011-03-09 |
| US20120059180A1 (en) | 2012-03-08 |
| CA2718374A1 (en) | 2003-06-19 |
| AU2002366642B2 (en) | 2008-12-11 |
| US7695626B2 (en) | 2010-04-13 |
| CN1267174C (zh) | 2006-08-02 |
| US8480904B2 (en) | 2013-07-09 |
| CA2469647A1 (en) | 2003-06-19 |
| AU2011250697A1 (en) | 2011-12-01 |
| JP2013100530A (ja) | 2013-05-23 |
| NO20042929L (no) | 2004-07-08 |
| ATE522264T1 (de) | 2011-09-15 |
| EP1453583A2 (en) | 2004-09-08 |
| JP2005513051A (ja) | 2005-05-12 |
| AU2009200718A1 (en) | 2009-03-19 |
| EP1453583B1 (en) | 2011-08-31 |
| AU2009200718B2 (en) | 2011-08-11 |
| EP1453583A4 (en) | 2005-08-17 |
| EP2261312A1 (en) | 2010-12-15 |
| CN1620330A (zh) | 2005-05-25 |
| AU2002366642A1 (en) | 2003-06-23 |
| US20090099379A1 (en) | 2009-04-16 |
| US7419596B2 (en) | 2008-09-02 |
| US8012354B2 (en) | 2011-09-06 |
| WO2003049832A8 (en) | 2003-10-23 |
| WO2003049832A1 (en) | 2003-06-19 |
| US20100261919A1 (en) | 2010-10-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2718374C (en) | Extraction and winterization of lipids from oilseed and microbial sources | |
| Chew et al. | Refining of edible oils | |
| Čmolík et al. | Physical refining of edible oils | |
| JP4537887B2 (ja) | 無溶媒抽出プロセス | |
| CN103635564B (zh) | 一种分离磷脂的方法 | |
| Peña et al. | Extraction of free fatty acids from wet Nannochloropsis gaditana biomass for biodiesel production | |
| Narayan et al. | Extraction and purification of oryzanol from rice bran oil and rice bran oil soapstock | |
| CN102143690A (zh) | 来自生物质的含有一种或多种长链多不饱和脂肪酸磷脂的油 | |
| WO2010010364A2 (en) | Process for the purification of oils | |
| AU2006260947B2 (en) | Process for obtaining lipid from cells | |
| HK1149228A (en) | Extraction and winterization of lipids from microbial sources | |
| HK1152070A (en) | Extraction and winterization of lipids from oilseed and microbial sources | |
| EP1215274A1 (en) | Enrichment of microbial oils | |
| HK1252707B (en) | Winterization of fish oil | |
| HK1123066A (en) | Process for obtaining lipid from cells |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20141212 |