JP2010532418A5 - - Google Patents
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- JP2010532418A5 JP2010532418A5 JP2010515186A JP2010515186A JP2010532418A5 JP 2010532418 A5 JP2010532418 A5 JP 2010532418A5 JP 2010515186 A JP2010515186 A JP 2010515186A JP 2010515186 A JP2010515186 A JP 2010515186A JP 2010532418 A5 JP2010532418 A5 JP 2010532418A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- ester
- polyunsaturated fatty
- fatty acid
- 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.)
- Pending
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- 239000000203 mixture Substances 0.000 claims description 86
- 238000000034 method Methods 0.000 claims description 84
- 150000002148 esters Chemical class 0.000 claims description 71
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims description 65
- 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 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- 125000004494 ethyl ester group Chemical group 0.000 claims description 22
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 20
- 229940090949 docosahexaenoic acid Drugs 0.000 claims description 19
- 235000021294 Docosapentaenoic acid Nutrition 0.000 claims description 17
- 244000005700 microbiome Species 0.000 claims description 15
- 150000003626 triacylglycerols Chemical class 0.000 claims description 15
- 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 claims description 12
- 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 12
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 12
- 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 11
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 11
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 11
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 11
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 9
- 229960004488 linolenic acid Drugs 0.000 claims description 9
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 206010012289 Dementia Diseases 0.000 claims description 6
- 235000021342 arachidonic acid Nutrition 0.000 claims description 6
- 229940114079 arachidonic acid Drugs 0.000 claims description 6
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 6
- 241000199914 Dinophyceae Species 0.000 claims description 5
- 238000004061 bleaching Methods 0.000 claims description 4
- 238000004332 deodorization Methods 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 238000007670 refining Methods 0.000 claims description 4
- 241000894006 Bacteria Species 0.000 claims description 3
- 241000195493 Cryptophyta Species 0.000 claims description 3
- 241000233866 Fungi Species 0.000 claims description 3
- 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 claims description 3
- 108010030975 Polyketide Synthases Proteins 0.000 claims description 3
- 150000004703 alkoxides Chemical class 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 235000020664 gamma-linolenic acid Nutrition 0.000 claims description 3
- 229960002733 gamolenic acid Drugs 0.000 claims description 3
- 238000012239 gene modification Methods 0.000 claims description 3
- 230000005017 genetic modification Effects 0.000 claims description 3
- 235000013617 genetically modified food Nutrition 0.000 claims description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical group [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 3
- JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 claims description 3
- 238000011282 treatment Methods 0.000 claims description 3
- 241000199913 Crypthecodinium Species 0.000 claims description 2
- 239000006186 oral dosage form Substances 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- DVSZKTAMJJTWFG-SKCDLICFSA-N (2e,4e,6e,8e,10e,12e)-docosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C=C\C(O)=O DVSZKTAMJJTWFG-SKCDLICFSA-N 0.000 claims 1
- GZJLLYHBALOKEX-UHFFFAOYSA-N 6-Ketone, O18-Me-Ussuriedine Natural products CC=CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O GZJLLYHBALOKEX-UHFFFAOYSA-N 0.000 claims 1
- KAUVQQXNCKESLC-UHFFFAOYSA-N docosahexaenoic acid (DHA) Natural products COC(=O)C(C)NOCC1=CC=CC=C1 KAUVQQXNCKESLC-UHFFFAOYSA-N 0.000 claims 1
- 150000004665 fatty acids Chemical group 0.000 description 14
- SOQKXJABGLKWQX-UHFFFAOYSA-N octacosa-4,7,10,13,16,19,22,25-octaenoic acid Chemical compound CCC=CCC=CCC=CCC=CCC=CCC=CCC=CCC=CCCC(O)=O SOQKXJABGLKWQX-UHFFFAOYSA-N 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 150000004671 saturated fatty acids Chemical class 0.000 description 6
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 3
- MJYQFWSXKFLTAY-OVEQLNGDSA-N (2r,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol;(2r,3r,4s,5s,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O.C1=C(O)C(OC)=CC(C[C@@H](CO)[C@H](CO)CC=2C=C(OC)C(O)=CC=2)=C1 MJYQFWSXKFLTAY-OVEQLNGDSA-N 0.000 description 2
- 241001133760 Acoelorraphe Species 0.000 description 2
- 235000017060 Arachis glabrata Nutrition 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 description 2
- 235000018262 Arachis monticola Nutrition 0.000 description 2
- 240000004355 Borago officinalis Species 0.000 description 2
- 235000007689 Borago officinalis Nutrition 0.000 description 2
- 241000219198 Brassica Species 0.000 description 2
- 235000003351 Brassica cretica Nutrition 0.000 description 2
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 2
- 240000002791 Brassica napus Species 0.000 description 2
- 235000006008 Brassica napus var napus Nutrition 0.000 description 2
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 2
- 235000003343 Brassica rupestris Nutrition 0.000 description 2
- 244000188595 Brassica sinapistrum Species 0.000 description 2
- 244000020518 Carthamus tinctorius Species 0.000 description 2
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 2
- 244000045195 Cicer arietinum Species 0.000 description 2
- 235000010523 Cicer arietinum Nutrition 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 241000219146 Gossypium Species 0.000 description 2
- 244000020551 Helianthus annuus Species 0.000 description 2
- 235000003222 Helianthus annuus Nutrition 0.000 description 2
- 235000014647 Lens culinaris subsp culinaris Nutrition 0.000 description 2
- 244000043158 Lens esculenta Species 0.000 description 2
- 235000004431 Linum usitatissimum Nutrition 0.000 description 2
- 240000006240 Linum usitatissimum Species 0.000 description 2
- 241000235575 Mortierella Species 0.000 description 2
- 208000012902 Nervous system disease Diseases 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- 241000219925 Oenothera Species 0.000 description 2
- 235000004496 Oenothera biennis Nutrition 0.000 description 2
- 240000007817 Olea europaea Species 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 241000233671 Schizochytrium Species 0.000 description 2
- 244000042324 Trifolium repens Species 0.000 description 2
- 235000013540 Trifolium repens var repens Nutrition 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 238000004807 desolvation Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 235000004426 flaxseed Nutrition 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000010460 mustard Nutrition 0.000 description 2
- 235000020232 peanut Nutrition 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 241000256111 Aedes <genus> Species 0.000 description 1
- 241000238424 Crustacea Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241001467333 Thraustochytriaceae Species 0.000 description 1
- 241000233675 Thraustochytrium Species 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94728407P | 2007-06-29 | 2007-06-29 | |
| PCT/US2008/068613 WO2009006317A1 (en) | 2007-06-29 | 2008-06-27 | Production and purification of esters of polyunsaturated fatty acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010532418A JP2010532418A (ja) | 2010-10-07 |
| JP2010532418A5 true JP2010532418A5 (https=) | 2011-08-18 |
Family
ID=40226489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010515186A Pending JP2010532418A (ja) | 2007-06-29 | 2008-06-27 | 多価不飽和脂肪酸のエステルの製造方法および精製方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US20090023808A1 (https=) |
| EP (1) | EP2173699A4 (https=) |
| JP (1) | JP2010532418A (https=) |
| CN (1) | CN101796014A (https=) |
| AU (2) | AU2008269989B2 (https=) |
| CA (1) | CA2692355C (https=) |
| MX (2) | MX374545B (https=) |
| WO (1) | WO2009006317A1 (https=) |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0613358A8 (pt) * | 2005-07-08 | 2017-12-26 | Dsm Ip Assets Bv | ácidos de gordura poli - insaturada para o tratamento da demência e condições relacionadas à pré-demência |
| JP2010532418A (ja) * | 2007-06-29 | 2010-10-07 | マーテック バイオサイエンシーズ コーポレーション | 多価不飽和脂肪酸のエステルの製造方法および精製方法 |
| US20090071064A1 (en) * | 2007-07-27 | 2009-03-19 | Machacek Mark T | Continuous algal biodiesel production facility |
| CA2751275A1 (en) * | 2009-02-02 | 2010-08-05 | Martek Biosciences Corporation | Use of docosahexaenoic acid in treating mild cognitive impairment |
| US20110177061A1 (en) | 2009-07-10 | 2011-07-21 | Martek Biosciences Corporation | Methods of treating and preventing neurological disorders using docosahexaenoic acid |
| DE102009038354B4 (de) * | 2009-08-21 | 2018-09-20 | Auto-Kabel Management Gmbh | Batteriepolklemme |
| US20110082205A1 (en) * | 2009-10-01 | 2011-04-07 | Panker Cynthia A | Docosahexaenoic Acid Gel Caps |
| EP2488190B1 (en) * | 2009-10-13 | 2017-09-20 | DSM IP Assets B.V. | Reducing the risk of pathological effects of traumatic brain injury |
| US9247547B2 (en) * | 2009-10-15 | 2016-01-26 | Qualcomm Incorporated | Downlink and uplink resource element mapping for carrier extension |
| PE20130491A1 (es) | 2009-12-30 | 2013-05-02 | Basf Pharma Callanish Ltd | Proceso simulado de separacion cromatografica de lecho movil para la purificacion de acidos grasos poliinsaturados |
| WO2011097273A1 (en) * | 2010-02-02 | 2011-08-11 | Martek Biosciences Corporation | Methods and compositions for treating non-alcoholic fatty liver disease with docosahexaenoic acid and n-acetyl lcystenine |
| US8372465B2 (en) * | 2010-02-17 | 2013-02-12 | Bunge Oils, Inc. | Oil compositions of stearidonic acid |
| EP2555761B1 (en) | 2010-04-09 | 2023-11-15 | DSM IP Assets B.V. | Thermally stable oil-in-water emulsions containing an oil that contains polyunsaturated fatty acids |
| US9023625B2 (en) | 2010-06-14 | 2015-05-05 | Io-Mega Holding Corporation | Methods for production of algae derived oils |
| SG187935A1 (en) * | 2010-09-03 | 2013-03-28 | Stepan Co | Elimination of organohalo and oxirane species in carboxylic acid ester streams |
| GB201111589D0 (en) | 2011-07-06 | 2011-08-24 | Equateq Ltd | New modified process |
| GB201111594D0 (en) | 2011-07-06 | 2011-08-24 | Equateq Ltd | New improved process |
| GB201111601D0 (en) | 2011-07-06 | 2011-08-24 | Equateq Ltd | New process |
| GB201111591D0 (en) | 2011-07-06 | 2011-08-24 | Equateq Ltd | Further new process |
| GB201111595D0 (en) | 2011-07-06 | 2011-08-24 | Equateq Ltd | Improved process |
| US20140323569A1 (en) * | 2011-07-21 | 2014-10-30 | Krishna Raman | Microbial oils enriched in polyunsaturated fatty acids |
| WO2013024174A1 (en) | 2011-08-18 | 2013-02-21 | Dsm Ip Assets B.V. | Dha triglyceride, dha free fatty acid, and dha ethyl ester emulsions, and methods of treating spinal cord injury |
| KR20140088599A (ko) | 2011-11-01 | 2014-07-10 | 디에스엠 아이피 어셋츠 비.브이. | 산화적으로 안정한 다중불포화된 지방산 함유 오일 |
| DK2858496T3 (da) | 2012-05-10 | 2023-07-24 | Solutex Na Llc | Olier med anti-inflammatorisk aktivitet, som indeholder naturlige specialiserede pro-afhjælpningsmediatorer og deres forløbere |
| FR2991337B1 (fr) * | 2012-05-29 | 2016-09-02 | Roquette Freres | Procede continu d'enrichissement en esters ethyliques de dha d'une huile produite par des microalgues |
| GB201300354D0 (en) | 2013-01-09 | 2013-02-20 | Basf Pharma Callanish Ltd | Multi-step separation process |
| HK1220479A1 (zh) * | 2013-03-13 | 2017-05-05 | Dsm Nutritional Products Ag | 从尿素/油复合物回收尿素和油 |
| WO2014152283A1 (en) | 2013-03-15 | 2014-09-25 | Heliae Development, Llc | Direct transesterification of algal biomass for synthesis of fatty acid ethyl esters (faee) |
| US9428711B2 (en) | 2013-05-07 | 2016-08-30 | Groupe Novasep | Chromatographic process for the production of highly purified polyunsaturated fatty acids |
| US8802880B1 (en) | 2013-05-07 | 2014-08-12 | Group Novasep | Chromatographic process for the production of highly purified polyunsaturated fatty acids |
| JP6302310B2 (ja) * | 2013-08-30 | 2018-03-28 | 備前化成株式会社 | 高純度オメガ３系脂肪酸エチルエステルの生産方法 |
| EP3733857A3 (en) * | 2013-12-04 | 2020-12-09 | Nippon Suisan Kaisha, Ltd. | Dihomo-gamma-linolenic acid-containing microbial oil and dihomo-gamma-linolenic acid-containing microbial biomass |
| FR3014436B1 (fr) * | 2013-12-11 | 2016-10-21 | Novasep Process | Procede de purification chromatographique d'un acide gras |
| EP2883860B1 (fr) | 2013-12-11 | 2016-08-24 | Novasep Process | Procédé chromatographique de production d'acides gras polyinsaturés |
| JP6303017B2 (ja) | 2014-01-07 | 2018-03-28 | ノヴァセプ プロセスＮｏｖａｓｅｐ Ｐｒｏｃｅｓｓ | 芳香族アミノ酸を精製する方法 |
| CN105779123B (zh) * | 2014-08-06 | 2020-03-10 | 石家庄搏澳增塑材料科技有限公司 | 氯化胆碱法解包尿素-饱和脂肪酸甲酯包合物的清洁工艺 |
| CN105566103B (zh) | 2014-10-13 | 2019-02-19 | 浙江医药股份有限公司新昌制药厂 | 一种甘油酯型多不饱和脂肪酸的制备方法 |
| WO2016182452A1 (en) * | 2015-05-13 | 2016-11-17 | Epax Norway As | Very long chain polyunsaturated fatty acids from natural oils |
| SG10202001800WA (en) | 2015-08-25 | 2020-04-29 | Dsm Ip Assets Bv | Refined oil compositions and methods for making |
| US10653703B2 (en) | 2015-09-03 | 2020-05-19 | Solutex Na Llc | Compositions comprising omega-3 fatty acids, 17-HDHA and 18-HEPE and methods of using same |
| SG10202003063WA (en) * | 2015-10-05 | 2020-05-28 | Dsm Ip Assets Bv | Oil compositions and methods of making |
| KR101815110B1 (ko) | 2015-10-16 | 2018-01-10 | 에이케이 앤 엠엔 바이오팜 주식회사 | 오메가-7계 불포화 지방산의 정제공정 |
| KR102405390B1 (ko) | 2016-07-13 | 2022-06-03 | 에보닉 오퍼레이션스 게엠베하 | 용해된 지질을 함유하는 바이오매스로부터 지질을 분리하는 방법 |
| CN110462014A (zh) | 2016-12-27 | 2019-11-15 | 赢创德固赛有限公司 | 从含有脂质的生物质中分离脂质的方法 |
| KR20200039704A (ko) | 2017-08-07 | 2020-04-16 | 디에스엠 아이피 어셋츠 비.브이. | 농축된 다중-불포화 지방산의 제조 방법 |
| 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 |
| WO2019219396A1 (en) | 2018-05-15 | 2019-11-21 | Evonik Operations Gmbh | Method of isolating lipids from a lysed lipids containing biomass by emulsion inversion |
| DK3794097T3 (da) | 2018-05-15 | 2024-12-16 | Evonik Operations Gmbh | Fremgangsmåde til isolering af lipider fra en lipid-indeholdende biomasse ved hjælp af hydrofob silica |
| EP3586643A1 (en) | 2018-06-21 | 2020-01-01 | Nuseed Pty Ltd | Dha enriched polyunsaturated fatty acid compositions |
| EP3586641A1 (en) * | 2018-06-21 | 2020-01-01 | Nuseed Pty Ltd | Dha enriched polyunsaturated fatty acid compositions |
| EP3586642A1 (en) * | 2018-06-21 | 2020-01-01 | Nuseed Pty Ltd | Ala enriched polyunsaturated fatty acid compositions |
| EP3586640A1 (en) * | 2018-06-21 | 2020-01-01 | Nuseed Pty Ltd | Dha enriched polyunsaturated fatty acid compositions |
| CN109061000A (zh) * | 2018-09-13 | 2018-12-21 | 中国科学院海洋研究所 | 一种衍生化处理植物油脂的混合液及其衍生化方法和应用 |
| CN109337939B (zh) * | 2018-09-30 | 2021-07-27 | 河北康睿达脂质有限公司 | 一种多不饱和脂肪酸结构脂质的制备方法 |
| NO20181574A1 (en) * | 2018-12-06 | 2020-06-08 | Epax Norway As | Very long chain fatty acids |
| EP3666082B1 (en) * | 2018-12-12 | 2022-05-04 | Nippon Suisan Kaisha, Ltd. | A composition containing highly unsaturated fatty acid or alkyl ester thereof and a method for producing the same |
| RU2709620C1 (ru) * | 2019-07-01 | 2019-12-19 | Федеральное государственное автономное образовательное учреждение высшего образования "Новосибирский национальный исследовательский государственный университет" (Новосибирский государственный университет, НГУ) | Водная эмульсия на основе диметоксинитробензиловых эфиров арахидоновой кислоты |
| FR3108622B1 (fr) | 2020-03-27 | 2024-08-23 | Polaris | Procédé de fractionnement d’acides gras à deux carbones de différence par distillation moléculaire |
| LU102019B1 (de) | 2020-08-26 | 2022-02-28 | K D Pharma Bexbach Gmbh | Verfahren zur Herstellung von Öl aus einem Mikroalgenerzeugnis |
| WO2025114579A2 (en) | 2023-12-01 | 2025-06-05 | Tate & Lyle Solutions Usa Llc | Methods of processing an oil composition |
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-
2008
- 2008-06-27 JP JP2010515186A patent/JP2010532418A/ja active Pending
- 2008-06-27 EP EP08781103.0A patent/EP2173699A4/en not_active Ceased
- 2008-06-27 CA CA2692355A patent/CA2692355C/en active Active
- 2008-06-27 CN CN200880104965A patent/CN101796014A/zh active Pending
- 2008-06-27 US US12/163,555 patent/US20090023808A1/en not_active Abandoned
- 2008-06-27 WO PCT/US2008/068613 patent/WO2009006317A1/en not_active Ceased
- 2008-06-27 MX MX2015006380A patent/MX374545B/es unknown
- 2008-06-27 AU AU2008269989A patent/AU2008269989B2/en not_active Ceased
- 2008-06-27 MX MX2010000263A patent/MX2010000263A/es active IP Right Grant
-
2009
- 2009-12-29 US US12/649,178 patent/US20110098356A1/en not_active Abandoned
-
2014
- 2014-01-13 US US14/154,140 patent/US9796658B2/en not_active Expired - Fee Related
- 2014-05-27 AU AU2014202880A patent/AU2014202880B2/en not_active Ceased
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