JPH064653B2 - ホスフアチジルコリンの単離方法 - Google Patents
ホスフアチジルコリンの単離方法Info
- Publication number
- JPH064653B2 JPH064653B2 JP60281251A JP28125185A JPH064653B2 JP H064653 B2 JPH064653 B2 JP H064653B2 JP 60281251 A JP60281251 A JP 60281251A JP 28125185 A JP28125185 A JP 28125185A JP H064653 B2 JPH064653 B2 JP H064653B2
- Authority
- JP
- Japan
- Prior art keywords
- phosphatidylcholine
- solvent mixture
- egg
- water
- egg powder
- 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 - Lifetime
Links
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 26
- 239000011877 solvent mixture Substances 0.000 claims abstract description 22
- 239000000843 powder Substances 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000000741 silica gel Substances 0.000 claims abstract description 14
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 14
- 239000003208 petroleum Substances 0.000 claims abstract description 8
- 238000010828 elution Methods 0.000 claims abstract description 4
- 238000009835 boiling Methods 0.000 claims abstract description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- 238000004440 column chromatography Methods 0.000 claims description 9
- 239000007858 starting material Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000007796 conventional method Methods 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 235000013601 eggs Nutrition 0.000 description 27
- RYCNUMLMNKHWPZ-SNVBAGLBSA-N 1-acetyl-sn-glycero-3-phosphocholine Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C RYCNUMLMNKHWPZ-SNVBAGLBSA-N 0.000 description 16
- 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 16
- 150000003904 phospholipids Chemical class 0.000 description 16
- 150000002632 lipids Chemical class 0.000 description 15
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 9
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 9
- HVYWMOMLDIMFJA-UHFFFAOYSA-N 3-cholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 HVYWMOMLDIMFJA-UHFFFAOYSA-N 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 102000002322 Egg Proteins Human genes 0.000 description 6
- 108010000912 Egg Proteins Proteins 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 235000013345 egg yolk Nutrition 0.000 description 6
- 210000002969 egg yolk Anatomy 0.000 description 6
- 239000008344 egg yolk phospholipid Substances 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 239000003480 eluent Substances 0.000 description 5
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- CWRILEGKIAOYKP-SSDOTTSWSA-M [(2r)-3-acetyloxy-2-hydroxypropyl] 2-aminoethyl phosphate Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCCN CWRILEGKIAOYKP-SSDOTTSWSA-M 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 150000003905 phosphatidylinositols Chemical class 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 235000019728 animal nutrition Nutrition 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- YHHSONZFOIEMCP-UHFFFAOYSA-O phosphocholine Chemical compound C[N+](C)(C)CCOP(O)(O)=O YHHSONZFOIEMCP-UHFFFAOYSA-O 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
- A23J7/00—Phosphatide compositions for foodstuffs, e.g. lecithin
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Insulating Materials (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Meat, Egg Or Seafood Products (AREA)
- Fodder In General (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843445950 DE3445950A1 (de) | 1984-12-17 | 1984-12-17 | Verfahren zur isolierung von lysophosphatidylcholin-freiem phosphatidylcholin aus ei-pulver |
| DE3445950.2 | 1984-12-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61145189A JPS61145189A (ja) | 1986-07-02 |
| JPH064653B2 true JPH064653B2 (ja) | 1994-01-19 |
Family
ID=6252976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60281251A Expired - Lifetime JPH064653B2 (ja) | 1984-12-17 | 1985-12-16 | ホスフアチジルコリンの単離方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4857236A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0185235B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPH064653B2 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE44150T1 (cg-RX-API-DMAC7.html) |
| DE (2) | DE3445950A1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK166363C (cg-RX-API-DMAC7.html) |
| ES (1) | ES8701769A1 (cg-RX-API-DMAC7.html) |
| GR (1) | GR853024B (cg-RX-API-DMAC7.html) |
| IE (1) | IE58399B1 (cg-RX-API-DMAC7.html) |
| PT (1) | PT81684B (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA859570B (cg-RX-API-DMAC7.html) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3445949A1 (de) * | 1984-12-17 | 1986-06-19 | A. Nattermann & Cie GmbH, 5000 Köln | Verfahren zur isolierung eines begleitphospholipid-freien phosphatidylcholins |
| WO1988003797A1 (en) * | 1986-11-28 | 1988-06-02 | The Liposome Company, Inc. | Phospholipid composition |
| FR2614621B1 (fr) * | 1987-04-29 | 1989-08-11 | Ire Celltarg Sa | Procede de purification des phosphatidylcholines et produits obtenus |
| IL84840A0 (en) * | 1987-12-16 | 1988-06-30 | Rapaport Erich | Dietary supplement |
| JP3025590B2 (ja) * | 1992-10-14 | 2000-03-27 | エーザイ株式会社 | 粗製物の精製法 |
| JP3100783B2 (ja) * | 1992-10-15 | 2000-10-23 | キユーピー株式会社 | ホスファチジルコリンおよびその製造方法 |
| CN1042134C (zh) * | 1994-11-25 | 1999-02-17 | 沈阳药科大学 | 亲油性表面活性剂蛋黄磷脂及其制备方法 |
| JP3267868B2 (ja) * | 1995-08-29 | 2002-03-25 | キユーピー株式会社 | 卵黄リン脂質組成物 |
| US5917068A (en) * | 1995-12-29 | 1999-06-29 | Eastman Chemical Company | Polyunsaturated fatty acid and fatty acid ester mixtures free of sterols and phosphorus compounds |
| US6063946A (en) * | 1996-01-26 | 2000-05-16 | Eastman Chemical Company | Process for the isolation of polyunsaturated fatty acids and esters thereof from complex mixtures which contain sterols and phosphorus compounds |
| US6200624B1 (en) | 1996-01-26 | 2001-03-13 | Abbott Laboratories | Enteral formula or nutritional supplement containing arachidonic and docosahexaenoic acids |
| US5883273A (en) * | 1996-01-26 | 1999-03-16 | Abbott Laboratories | Polyunsaturated fatty acids and fatty acid esters free of sterols and phosphorus compounds |
| DE19724604A1 (de) * | 1997-06-11 | 1998-12-17 | Sueddeutsche Kalkstickstoff | Verfahren zur Herstellung von ölfreiem Eilecithin mit einem reduzierten Cholesteringehalt |
| JP3589904B2 (ja) * | 1999-06-17 | 2004-11-17 | 花王株式会社 | 酸性水中油型乳化組成物 |
| US20040175776A1 (en) * | 2001-05-31 | 2004-09-09 | Yasushi Kanai | Assay method for platelet-activating factor |
| CN100500676C (zh) * | 2006-04-17 | 2009-06-17 | 江南大学 | 一种不含溶血磷脂的高纯大豆磷脂酰胆碱的制备方法 |
| CN104262387B (zh) * | 2014-09-19 | 2016-06-29 | 河南省农科院农副产品加工研究所 | 一种硅胶柱色谱分离纯化溶血磷脂酰乙醇胺的方法 |
| JP7357471B2 (ja) * | 2019-06-13 | 2023-10-06 | キユーピー株式会社 | リン脂質の精製方法 |
| CN111039976A (zh) * | 2019-12-26 | 2020-04-21 | 江苏汉斯通药业有限公司 | 梯度法纯化大豆磷脂酰胆碱的方法 |
| CN114644650B (zh) * | 2020-12-21 | 2025-01-07 | 广州白云山汉方现代药业有限公司 | 一种从蛋黄粉中提取高纯度鞘磷脂的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4221731A (en) * | 1978-04-19 | 1980-09-09 | A. E. Staley Manufacturing Company | Process for recovery of high-grade lecithin and solvents from ternary solvent system containing crude vegetable oil |
| DE2915614A1 (de) * | 1979-04-18 | 1980-10-30 | Guenter Dr Heidemann | Verfahren zur gewinnung von reinen phosphatiden |
| DE3047012A1 (de) * | 1980-12-13 | 1982-07-22 | A. Nattermann & Cie GmbH, 5000 Köln | Verfahren zur abtrennung von acylierten phospholipiden aus diese enthaltenden phosphatidylcholin-produkten |
| DE3047048A1 (de) * | 1980-12-13 | 1982-07-29 | A. Nattermann & Cie GmbH, 5000 Köln | Verfahren zur abtrennung von oel und/oder phosphatidylethanolamin aus diese enthaltenden alkoholloeslichen phosphatidylcholin-produkten |
| DE3047011A1 (de) * | 1980-12-13 | 1982-07-22 | A. Nattermann & Cie GmbH, 5000 Köln | Verfahren zur abtrennung von oel und/oder phosphatidylethanolamin aus diese enthaltenden alkoholloeslichen phosphatidylcholin-produkten |
-
1984
- 1984-12-17 DE DE19843445950 patent/DE3445950A1/de not_active Withdrawn
-
1985
- 1985-11-29 AT AT85115167T patent/ATE44150T1/de not_active IP Right Cessation
- 1985-11-29 DE DE8585115167T patent/DE3571134D1/de not_active Expired
- 1985-11-29 EP EP85115167A patent/EP0185235B1/de not_active Expired
- 1985-12-13 ZA ZA859570A patent/ZA859570B/xx unknown
- 1985-12-16 GR GR853024A patent/GR853024B/el unknown
- 1985-12-16 DK DK584285A patent/DK166363C/da not_active IP Right Cessation
- 1985-12-16 PT PT81684A patent/PT81684B/pt not_active IP Right Cessation
- 1985-12-16 ES ES549963A patent/ES8701769A1/es not_active Expired
- 1985-12-16 IE IE318385A patent/IE58399B1/en unknown
- 1985-12-16 JP JP60281251A patent/JPH064653B2/ja not_active Expired - Lifetime
-
1987
- 1987-05-26 US US07/057,695 patent/US4857236A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES549963A0 (es) | 1986-12-01 |
| US4857236A (en) | 1989-08-15 |
| ATE44150T1 (de) | 1989-07-15 |
| EP0185235A2 (de) | 1986-06-25 |
| DK584285A (da) | 1986-06-18 |
| ZA859570B (en) | 1986-08-27 |
| PT81684B (pt) | 1987-10-20 |
| IE853183L (en) | 1986-06-17 |
| EP0185235B1 (de) | 1989-06-21 |
| DE3445950A1 (de) | 1986-06-19 |
| EP0185235A3 (en) | 1987-05-27 |
| GR853024B (cg-RX-API-DMAC7.html) | 1986-04-08 |
| ES8701769A1 (es) | 1986-12-01 |
| IE58399B1 (en) | 1993-09-08 |
| PT81684A (en) | 1986-01-01 |
| JPS61145189A (ja) | 1986-07-02 |
| DK166363B (da) | 1993-04-13 |
| DE3571134D1 (en) | 1989-07-27 |
| DK166363C (da) | 1993-09-06 |
| DK584285D0 (da) | 1985-12-16 |
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