CA2856715A1 - Compositions comprising 20-carbon fatty acids and methods of making and using same - Google Patents
Compositions comprising 20-carbon fatty acids and methods of making and using same Download PDFInfo
- Publication number
- CA2856715A1 CA2856715A1 CA2856715A CA2856715A CA2856715A1 CA 2856715 A1 CA2856715 A1 CA 2856715A1 CA 2856715 A CA2856715 A CA 2856715A CA 2856715 A CA2856715 A CA 2856715A CA 2856715 A1 CA2856715 A1 CA 2856715A1
- Authority
- CA
- Canada
- Prior art keywords
- fatty acids
- carbon
- seed oil
- carbon fatty
- eta
- 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.)
- Abandoned
Links
- 229910052799 carbon Inorganic materials 0.000 title claims abstract description 232
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 232
- 239000000194 fatty acid Substances 0.000 title claims abstract description 232
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 232
- 239000000203 mixture Substances 0.000 title claims abstract description 160
- 238000000034 method Methods 0.000 title claims abstract description 104
- 230000008569 process Effects 0.000 claims abstract description 74
- 235000015112 vegetable and seed oil Nutrition 0.000 claims abstract description 62
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 57
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 239000003921 oil Substances 0.000 claims description 95
- 235000019198 oils Nutrition 0.000 claims description 95
- 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 claims description 93
- HOBAELRKJCKHQD-UHFFFAOYSA-N (8Z,11Z,14Z)-8,11,14-eicosatrienoic acid Natural products CCCCCC=CCC=CCC=CCCCCCCC(O)=O HOBAELRKJCKHQD-UHFFFAOYSA-N 0.000 claims description 86
- AHANXAKGNAKFSK-PDBXOOCHSA-N all-cis-icosa-11,14,17-trienoic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCCCC(O)=O AHANXAKGNAKFSK-PDBXOOCHSA-N 0.000 claims description 63
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 51
- 241000196324 Embryophyta Species 0.000 claims description 48
- 239000002904 solvent Substances 0.000 claims description 44
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 41
- -1 carbon fatty acids Chemical class 0.000 claims description 29
- 235000021588 free fatty acids Nutrition 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 238000001816 cooling Methods 0.000 claims description 14
- 239000013078 crystal Substances 0.000 claims description 14
- 239000010473 blackcurrant seed oil Substances 0.000 claims description 13
- 150000004702 methyl esters Chemical class 0.000 claims description 13
- 235000020660 omega-3 fatty acid Nutrition 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 12
- 229940012843 omega-3 fatty acid Drugs 0.000 claims description 12
- 239000006014 omega-3 oil Substances 0.000 claims description 11
- 235000020665 omega-6 fatty acid Nutrition 0.000 claims description 11
- 229940033080 omega-6 fatty acid Drugs 0.000 claims description 11
- 125000004494 ethyl ester group Chemical group 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000005907 alkyl ester group Chemical group 0.000 claims description 9
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 239000003610 charcoal Substances 0.000 claims description 6
- 239000000377 silicon dioxide Substances 0.000 claims description 6
- 102000004190 Enzymes Human genes 0.000 claims description 5
- 108090000790 Enzymes Proteins 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 230000001877 deodorizing effect Effects 0.000 claims description 5
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 238000000194 supercritical-fluid extraction Methods 0.000 claims description 5
- 241001053394 Buglossoides Species 0.000 claims description 4
- 241001071905 Echium Species 0.000 claims description 4
- 241000295545 Hackelia Species 0.000 claims description 4
- 241000219925 Oenothera Species 0.000 claims description 4
- 235000004496 Oenothera biennis Nutrition 0.000 claims description 4
- 241001180933 Trichodesma <angiosperm> Species 0.000 claims description 4
- 238000013375 chromatographic separation Methods 0.000 claims description 4
- 150000005690 diesters Chemical class 0.000 claims description 4
- 241000024188 Andala Species 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 150000007860 aryl ester derivatives Chemical class 0.000 claims description 3
- 235000021324 borage oil Nutrition 0.000 claims description 3
- 239000010474 borage seed oil Substances 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 230000000911 decarboxylating effect Effects 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 208000020016 psychiatric disease Diseases 0.000 claims description 3
- 208000017520 skin disease Diseases 0.000 claims description 3
- 238000000638 solvent extraction Methods 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 239000004367 Lipase Substances 0.000 claims description 2
- 102000004882 Lipase Human genes 0.000 claims description 2
- 108090001060 Lipase Proteins 0.000 claims description 2
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 2
- 230000002757 inflammatory effect Effects 0.000 claims description 2
- 235000019421 lipase Nutrition 0.000 claims description 2
- 230000000926 neurological effect Effects 0.000 claims description 2
- 230000000241 respiratory effect Effects 0.000 claims description 2
- 235000020664 gamma-linolenic acid Nutrition 0.000 description 69
- 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 67
- HQPCSDADVLFHHO-LTKCOYKYSA-N all-cis-8,11,14,17-icosatetraenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/CCCCCCC(O)=O HQPCSDADVLFHHO-LTKCOYKYSA-N 0.000 description 66
- JIWBIWFOSCKQMA-LTKCOYKYSA-N all-cis-octadeca-6,9,12,15-tetraenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O JIWBIWFOSCKQMA-LTKCOYKYSA-N 0.000 description 65
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 35
- IUKXMNDGTWTNTP-OAHXIXLCSA-N 15(S)-HETrE Chemical compound CCCCC[C@H](O)\C=C\C=C/C\C=C/CCCCCCC(O)=O IUKXMNDGTWTNTP-OAHXIXLCSA-N 0.000 description 23
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 20
- 201000010099 disease Diseases 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 208000035475 disorder Diseases 0.000 description 16
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 14
- 238000004817 gas chromatography Methods 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 10
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 10
- 239000005642 Oleic acid Substances 0.000 description 10
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 10
- 235000021314 Palmitic acid Nutrition 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 10
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 10
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 9
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
- 235000021355 Stearic acid Nutrition 0.000 description 8
- 235000020778 linoleic acid Nutrition 0.000 description 8
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 8
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 8
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 8
- 150000003138 primary alcohols Chemical group 0.000 description 8
- 239000008117 stearic acid Substances 0.000 description 8
- 239000003880 polar aprotic solvent Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 208000024891 symptom Diseases 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000002632 lipids Chemical class 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 5
- BITHHVVYSMSWAG-KTKRTIGZSA-N (11Z)-icos-11-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCC(O)=O BITHHVVYSMSWAG-KTKRTIGZSA-N 0.000 description 4
- XSXIVVZCUAHUJO-AVQMFFATSA-N (11e,14e)-icosa-11,14-dienoic acid Chemical compound CCCCC\C=C\C\C=C\CCCCCCCCCC(O)=O XSXIVVZCUAHUJO-AVQMFFATSA-N 0.000 description 4
- 102000009515 Arachidonate 15-Lipoxygenase Human genes 0.000 description 4
- 108010048907 Arachidonate 15-lipoxygenase Proteins 0.000 description 4
- 235000021297 Eicosadienoic acid Nutrition 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- UWHZIFQPPBDJPM-FPLPWBNLSA-M Vaccenic acid Natural products CCCCCC\C=C/CCCCCCCCCC([O-])=O UWHZIFQPPBDJPM-FPLPWBNLSA-M 0.000 description 4
- 235000021322 Vaccenic acid Nutrition 0.000 description 4
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical class COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 4
- 229940108623 eicosenoic acid Drugs 0.000 description 4
- BITHHVVYSMSWAG-UHFFFAOYSA-N eicosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCC(O)=O BITHHVVYSMSWAG-UHFFFAOYSA-N 0.000 description 4
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
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- 239000003826 tablet Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- UWHZIFQPPBDJPM-BQYQJAHWSA-N trans-vaccenic acid Chemical compound CCCCCC\C=C\CCCCCCCCCC(O)=O UWHZIFQPPBDJPM-BQYQJAHWSA-N 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- 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 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 150000001649 bromium compounds Chemical class 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
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- 235000019387 fatty acid methyl ester Nutrition 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- JSFATNQSLKRBCI-UHFFFAOYSA-N 15-Hydroxyeicosatetraenoic acid Chemical compound CCCCCC(O)C=CC=CCC=CCC=CCCCC(O)=O JSFATNQSLKRBCI-UHFFFAOYSA-N 0.000 description 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 244000269722 Thea sinensis Species 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 2
- 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 2
- 230000003078 antioxidant effect Effects 0.000 description 2
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- 235000017471 coenzyme Q10 Nutrition 0.000 description 2
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- IQLUYYHUNSSHIY-HZUMYPAESA-N eicosatetraenoic acid Chemical compound CCCCCCCCCCC\C=C\C=C\C=C\C=C\C(O)=O IQLUYYHUNSSHIY-HZUMYPAESA-N 0.000 description 2
- PRHHYVQTPBEDFE-UHFFFAOYSA-N eicosatrienoic acid Natural products CCCCCC=CCC=CCCCCC=CCCCC(O)=O PRHHYVQTPBEDFE-UHFFFAOYSA-N 0.000 description 2
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
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- 239000012038 nucleophile Substances 0.000 description 2
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- 230000020477 pH reduction Effects 0.000 description 2
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- 231100000402 unacceptable toxicity Toxicity 0.000 description 2
- DTOSIQBPPRVQHS-UHFFFAOYSA-N α-Linolenic acid Chemical compound CCC=CCC=CCC=CCCCCCCCC(O)=O DTOSIQBPPRVQHS-UHFFFAOYSA-N 0.000 description 2
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- 241001072256 Boraginaceae Species 0.000 description 1
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/005—Splitting up mixtures of fatty acids into their constituents
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/007—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids using organic solvents
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
- C11C1/025—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by saponification and release of fatty acids
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
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- 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
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- 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
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- 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
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- C12P7/6409—Fatty acids
- C12P7/6427—Polyunsaturated fatty acids [PUFA], i.e. having two or more double bonds in their backbone
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- 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
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- C12P7/6431—Linoleic acids [18:2[n-6]]
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- 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
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Landscapes
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- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Dermatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Fats And Perfumes (AREA)
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| US201161564652P | 2011-11-29 | 2011-11-29 | |
| US61/564,652 | 2011-11-29 | ||
| US201261711585P | 2012-10-09 | 2012-10-09 | |
| US61/711,585 | 2012-10-09 | ||
| PCT/US2012/067030 WO2013082265A1 (en) | 2011-11-29 | 2012-11-29 | Compositions comprising 20-carbon fatty acids and methods of making and using same |
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| CA2856715A1 true CA2856715A1 (en) | 2013-06-06 |
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| CA2856715A Abandoned CA2856715A1 (en) | 2011-11-29 | 2012-11-29 | Compositions comprising 20-carbon fatty acids and methods of making and using same |
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| EP (1) | EP2785852A4 (enExample) |
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| BR (1) | BR112014013098A2 (enExample) |
| CA (1) | CA2856715A1 (enExample) |
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| WO (1) | WO2013082265A1 (enExample) |
| ZA (1) | ZA201403784B (enExample) |
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| GB0907413D0 (en) | 2009-04-29 | 2009-06-10 | Equateq Ltd | Novel methods |
| US8293790B2 (en) | 2011-10-19 | 2012-10-23 | Dignity Sciences Limited | Pharmaceutical compositions comprising DGLA and benzoyl peroxide and methods of use thereof |
| CA2856715A1 (en) | 2011-11-29 | 2013-06-06 | Dignity Sciences Limited | Compositions comprising 20-carbon fatty acids and methods of making and using same |
| GB201301626D0 (en) | 2013-01-30 | 2013-03-13 | Dignity Sciences Ltd | Composition comprising 15-OHEPA and methods of using the same |
| JP2016538288A (ja) | 2013-11-15 | 2016-12-08 | ディグニティ サイエンシス リミテッド | 多価不飽和ヒドロキシ脂肪酸の薬学的に許容される塩 |
| US9820484B2 (en) | 2013-12-04 | 2017-11-21 | Nippon Suisan Kaisha, Ltd. | Dihomo-γ-linolenic acid-containing microbial oil and dihomo-γ-linolenic acid-containing microbial biomass |
| EP3151825B1 (en) | 2014-06-04 | 2020-03-25 | DS Biopharma Limited | Pharmaceutical compositions comprising dgla and use of same |
| MA41120A (fr) | 2014-12-02 | 2017-10-10 | Afimmune Ltd | Compositions comprenant le 15-hepe et méthodes de traitement ou de prévention de la fibrose à l'aide de celles-ci |
| EP3861995A1 (en) | 2015-07-21 | 2021-08-11 | Affimune Limited | Compositions comprising 15-hepe for use in treating or preventing neurologic disease |
| HK1252244A1 (en) * | 2015-08-31 | 2019-05-24 | Nissui Corporation | Free polyunsaturated fatty acid-containing composition and manufacturing method therefor |
| BR122023026625A2 (pt) | 2015-12-18 | 2024-01-16 | Afimmune Limited | Uso do ácido 15-hidroxieicosapentaenoico ou derivados farmaceuticamente aceitáveis do mesmo |
| CN105535064A (zh) * | 2016-01-19 | 2016-05-04 | 佛山科学技术学院 | 一种琉璃苣深加工方法及其深加工产物 |
| CN109796328B (zh) * | 2019-03-14 | 2022-03-25 | 浙江工业大学 | 一种高纯度香榧籽油金松酸的分离方法 |
| US20210315851A1 (en) | 2020-04-03 | 2021-10-14 | Afimmune Limited | Compositions comprising 15-hepe and methods of treating or preventing hematologic disorders, and/or related diseases |
| CN113004977A (zh) * | 2021-02-25 | 2021-06-22 | 华侨大学 | 高纯度多不饱和鱼油的制备方法以及鱿鱼油加工方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH663951A5 (fr) * | 1984-10-10 | 1988-01-29 | Nestle Sa | Procede d'enrichissement selectif en acides gras polyinsatures d'un melange contenant des acides gras fractions enrichies obtenues et compositions les contenant. |
| CH669208A5 (fr) * | 1986-12-17 | 1989-02-28 | Nestle Sa | Procede de fractionnement en continu d'un melange d'acides gras. |
| US5968809A (en) * | 1997-04-11 | 1999-10-19 | Abbot Laboratories | Methods and compositions for synthesis of long chain poly-unsaturated fatty acids |
| PL336077A1 (en) * | 1997-04-11 | 2000-06-05 | Calgene Llc | Methods of and compositions for synthesising long-chain polyunsaturated fatty acids in plants |
| 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 |
| AU2004290051A1 (en) * | 2003-11-12 | 2005-05-26 | E.I. Dupont De Nemours And Company | Delta-15 desaturases suitable for altering levels of polyunsaturated fatty acids in oilseed plants and oleaginous yeast |
| US7807849B2 (en) * | 2004-04-22 | 2010-10-05 | Commonwealth Scientific And Industrial Research Organisation | Synthesis of long-chain polyunsaturated fatty acids by recombinant cells |
| CA2649337C (en) * | 2006-04-13 | 2014-11-18 | Nippon Suisan Kaisha, Ltd. | Process for preparing concentrated polyunsaturated fatty acid oil |
| US20080125487A1 (en) | 2006-11-17 | 2008-05-29 | Tapas Das | Elongase gene and uses thereof |
| US20080213357A1 (en) * | 2007-02-12 | 2008-09-04 | Andrew Bruce Hebard | Plant Derived Lipid Useful for Nutraceutical and Cosemeceutical Applications |
| US8455035B2 (en) * | 2008-04-25 | 2013-06-04 | Basf Plant Science Gmbh | Plant seed oil |
| US8188335B2 (en) * | 2009-07-17 | 2012-05-29 | Abbott Laboratories | Δ9-elongase for production of polyunsaturated fatty acid-enriched oils |
| CA2856715A1 (en) | 2011-11-29 | 2013-06-06 | Dignity Sciences Limited | Compositions comprising 20-carbon fatty acids and methods of making and using same |
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2012
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- 2012-11-29 MX MX2014006478A patent/MX2014006478A/es unknown
- 2012-11-29 AU AU2012345942A patent/AU2012345942A1/en not_active Abandoned
- 2012-11-29 US US13/688,998 patent/US9096815B2/en not_active Expired - Fee Related
- 2012-11-29 WO PCT/US2012/067030 patent/WO2013082265A1/en not_active Ceased
- 2012-11-29 SG SG11201402653QA patent/SG11201402653QA/en unknown
- 2012-11-29 JP JP2014544878A patent/JP2015500639A/ja active Pending
- 2012-11-29 RU RU2014126356A patent/RU2014126356A/ru not_active Application Discontinuation
- 2012-11-29 EP EP12854347.7A patent/EP2785852A4/en not_active Withdrawn
- 2012-11-29 BR BR112014013098A patent/BR112014013098A2/pt not_active IP Right Cessation
- 2012-11-29 KR KR1020147017339A patent/KR20140113921A/ko not_active Withdrawn
- 2012-11-29 CN CN201280066370.4A patent/CN104114709A/zh active Pending
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2014
- 2014-05-22 IL IL232748A patent/IL232748A0/en unknown
- 2014-05-23 ZA ZA2014/03784A patent/ZA201403784B/en unknown
- 2014-05-29 PH PH12014501212A patent/PH12014501212A1/en unknown
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|---|---|
| CN104114709A (zh) | 2014-10-22 |
| KR20140113921A (ko) | 2014-09-25 |
| SG11201402653QA (en) | 2014-06-27 |
| JP2015500639A (ja) | 2015-01-08 |
| AU2012345942A1 (en) | 2014-06-12 |
| WO2013082265A1 (en) | 2013-06-06 |
| EP2785852A1 (en) | 2014-10-08 |
| PH12014501212A1 (en) | 2014-09-08 |
| US20130331448A1 (en) | 2013-12-12 |
| RU2014126356A (ru) | 2016-01-27 |
| BR112014013098A2 (pt) | 2017-06-13 |
| ZA201403784B (en) | 2015-09-30 |
| MX2014006478A (es) | 2015-02-12 |
| US9096815B2 (en) | 2015-08-04 |
| IL232748A0 (en) | 2014-07-31 |
| EP2785852A4 (en) | 2015-11-04 |
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