NO840361L - PROCEDURE FOR PHRAPHATION OF PHOSPHATIDES - Google Patents
PROCEDURE FOR PHRAPHATION OF PHOSPHATIDESInfo
- Publication number
- NO840361L NO840361L NO840361A NO840361A NO840361L NO 840361 L NO840361 L NO 840361L NO 840361 A NO840361 A NO 840361A NO 840361 A NO840361 A NO 840361A NO 840361 L NO840361 L NO 840361L
- Authority
- NO
- Norway
- Prior art keywords
- phosphatides
- polar
- stated
- resin
- fractions
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- 239000002798 polar solvent Substances 0.000 claims abstract description 13
- 150000002632 lipids Chemical class 0.000 claims abstract description 12
- 229920005989 resin Polymers 0.000 claims abstract description 8
- 239000011347 resin Substances 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000011574 phosphorus Substances 0.000 claims abstract description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 5
- 238000005194 fractionation Methods 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000003995 emulsifying agent Substances 0.000 claims description 6
- 235000019441 ethanol Nutrition 0.000 claims description 5
- 239000003921 oil Substances 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 239000003463 adsorbent Substances 0.000 claims description 3
- 230000001804 emulsifying effect Effects 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 238000010828 elution Methods 0.000 claims description 2
- 230000007928 solubilization Effects 0.000 claims 1
- 238000005063 solubilization Methods 0.000 claims 1
- 230000003381 solubilizing effect Effects 0.000 abstract description 2
- 239000000470 constituent Substances 0.000 abstract 1
- 229930186217 Glycolipid Natural products 0.000 description 7
- 229930182558 Sterol Natural products 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 150000003432 sterols Chemical class 0.000 description 6
- 235000003702 sterols Nutrition 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 4
- 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 description 4
- 238000000926 separation method Methods 0.000 description 4
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 3
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 102000002322 Egg Proteins Human genes 0.000 description 2
- 108010000912 Egg Proteins Proteins 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 235000013345 egg yolk Nutrition 0.000 description 2
- 210000002969 egg yolk Anatomy 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 1
- 244000258044 Solanum gilo Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000002196 fr. b Anatomy 0.000 description 1
- 210000003918 fraction a Anatomy 0.000 description 1
- 210000000540 fraction c Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 235000016236 parenteral nutrition Nutrition 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
- C07F9/103—Extraction or purification by physical or chemical treatment of natural phosphatides; Preparation of compositions containing phosphatides of unknown structure
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Food Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Medicines Containing Plant Substances (AREA)
- General Preparation And Processing Of Foods (AREA)
Abstract
Fremgangsmåte for fraksjonering av fosfatider, ved at man solubiliserer lipidfraksjoner ved hjelp av et ikke-polart eller lite polart løsningsmiddel, den derved oppnådde løs-ning bringes til å renne over en harpiks som foretrukket fikserer de fosforholdige derivater, de andre bestanddeler enn fosfatidene fjernes ved eluering ved hjelp av et ikke-polart eller lite polart løsningsmiddel og man eluerer fosfatidene med et polart lsningsmiddel eller en blanding av polare løsningsmidler.Process for the fractionation of phosphatides, by solubilizing lipid fractions with the aid of a non-polar or low-polar solvent, the solution thus obtained is run over a resin which preferably fixes the phosphorus-containing derivatives, the constituents other than the phosphatides being removed by eluting with a non-polar or slightly polar solvent and eluting the phosphatides with a polar solvent or a mixture of polar solvents.
Description
Foreliggende oppfinnelse vedrører en fremgangsmåte for fraksjonering av fosfatider, og det særegne ved fremgangsmåten i henhold til oppfinnelsen er at lipidfraksjonene solubiliseres ved hjelp av et ikke-polart eller lite polart løsningsmiddel, den derved oppnådde løsning bringes til å renne over en harpiks som foretrukket fikserer de fosforholdige derivater, man fjerner de andre bestanddeler enn fosfatidene ved eluering ved hjelp av et ikke-polart eller lite polart løsningsmiddel og man eluerer fosfatidene med et polart løsningsmiddel eller en blanding av polare løsningsmidler. The present invention relates to a method for the fractionation of phosphatides, and the distinctive feature of the method according to the invention is that the lipid fractions are solubilized with the aid of a non-polar or slightly polar solvent, the resulting solution is made to flow over a resin which preferably fixes the phosphorus-containing derivatives, the components other than the phosphatides are removed by elution using a non-polar or slightly polar solvent and the phosphatides are eluted with a polar solvent or a mixture of polar solvents.
Disse og andre trekk ved oppfinnelsen fremgår av patent-kravene. These and other features of the invention appear in the patent claims.
Emulgering av oljer anvendt i næringsmidler, innenfor dermatologien og kosmetologien anvender syntetiske eller naturlige emulgeringsmidler. Det synes som om bare naturlige emulgeringsmidler har en god biologisk tålbarhet ved humane anvendelsesområder. Disse emulgeringsmidler ekstraheres ved hjelp av klassiske metoder fra lipidholdige fraksjoner, enten vegetabilske (soyabønner, mais) eller animalske (f.eks. eggeplomme). Emulsification of oils used in foodstuffs, in dermatology and cosmetology uses synthetic or natural emulsifiers. It seems that only natural emulsifiers have a good biological tolerance in human areas of application. These emulsifiers are extracted using classic methods from lipid-containing fractions, either vegetable (soybeans, corn) or animal (e.g. egg yolk).
Ved hjelp av disse metoder ekstraheres de fosforholdige forbindelser: fosfatidene fosfatidylcholin (PC) og fos-fatidyletanolamin (PE) som er assosiert med glykolipidene, sterolene og de nøytrale lipider. Using these methods, the phosphorus-containing compounds are extracted: the phosphatides phosphatidylcholine (PC) and phosphatidylethanolamine (PE) which are associated with the glycolipids, sterols and the neutral lipids.
Formålet for den foreliggende oppfinnelse er å separere fosfatidene fra glykolipidene, sterolene og de nøytrale lipider, videre å fraksjonere disse fosfatider og even-tuelt rekombinere de oppnådde fraksjoner for å oppnå et emulgeringsmiddel alt etter den type emulsjon som ønskes. The purpose of the present invention is to separate the phosphatides from the glycolipids, sterols and neutral lipids, to further fractionate these phosphatides and possibly recombine the obtained fractions to obtain an emulsifier depending on the type of emulsion desired.
Separeringen av fosfatidene fra steroler, nøytrale lipider og glykolipider er i henhold til litteraturen gjen- According to the literature, the separation of the phosphatides from sterols, neutral lipids and glycolipids is
nomført ved hjelp av flere metoder.carried out using several methods.
1 - Separering ved hjelp av ekstrasjoner med aceton og etanol gir alltid blandinger av fosfatider og glykolipider (R. Ajena og medarbeidere, Fette - Seifen - Anstrichmittel Nr. 10, 643-651 (1971), videre W. Van Nieuwenhuyzen J. Amer. Oil Chemists' Soc. Vol. 53, 425-429 (1976)) . 2 - Separering ved hjelp av adsorpsjonsmidler som alumini-umoksyd og magnesiumoksyd fører til en systematisk anrikning av fosfatidylcholin (se fransk ansøkning 79 27081) . 3 - Metoden med separering ved hjelp av kiselsyre anvendt analytisk viser seg kostbar og lite anvendbar i indu-strien (G. Rouser og medarbeidere, J. Amer. Oil Chemists'Soc. Vol. 42, 215-227 (1965), videre Technigues of Lipidology Lab. Techn. Biochem. Mol. Biol. (1972) og J. Hirsch og medarbeidere, J. Biol. Chem. 233, nr. 2, 311-320 (1958) . 1 - Separation by means of extractions with acetone and ethanol always gives mixtures of phosphatides and glycolipids (R. Ajena et al., Fette - Seifen - Anstrichmittel Nr. 10, 643-651 (1971), further W. Van Nieuwenhuyzen J. Amer. Oil Chemists' Soc. Vol. 53, 425-429 (1976)). 2 - Separation using adsorbents such as aluminum oxide and magnesium oxide leads to a systematic enrichment of phosphatidylcholine (see French application 79 27081). 3 - The method of separation by means of silicic acid applied analytically proves to be expensive and of little use in industry (G. Rouser and co-workers, J. Amer. Oil Chemists'Soc. Vol. 42, 215-227 (1965), further Technigues of Lipidology Lab. Techn. Biochem. Mol. Biol. (1972) and J. Hirsch et al., J. Biol. Chem. 233, No. 2, 311-320 (1958).
Fremgangsmåten i henhold til oppfinnelsen går ut på å solubilisere de lipidholdige fraksjoner (animalsk eller vegetabilsk opprinnelse) oppnådd ved klassiske metoder ved hjelp av et ikke-polart eller lite polart løsningsmiddel (etylacetat, kloroform) for å la denne oppløsning renne over harpiks (kationiske svakt sure, anioniske svakt basiske, ikke-ioniske eller lite ioniske adsorpsjonsmidler) som foretrukket fikserer de fosforholdige derivater (fosfatider) og ikke de andre bestanddeler (glykolipider, steroler, nøytrale lipider). The method according to the invention consists in solubilizing the lipid-containing fractions (animal or vegetable origin) obtained by classical methods with the help of a non-polar or slightly polar solvent (ethyl acetate, chloroform) in order to allow this solution to flow over resin (cationic weakly acidic, anionic weakly basic, non-ionic or slightly ionic adsorbents) which preferentially fix the phosphorus-containing derivatives (phosphatides) and not the other components (glycolipids, sterols, neutral lipids).
Etter fiksering elueres fosfatidene med et løsningsmiddel eller en blanding av løsningsmidler, i begge tilfeller med polar karakter (alkohol). After fixation, the phosphatides are eluted with a solvent or a mixture of solvents, in both cases with a polar character (alcohol).
Fremgangsmåten i henhold til oppfinnelsen tillater således oppnåelse av fosfatider etter å ha separert glykolipidene, sterolene og de nøytrale lipider. The method according to the invention thus allows obtaining phosphatides after separating the glycolipids, sterols and neutral lipids.
Ved fremgangsmåten i henhold til oppfinnelsen oppnås fraksjoner av fosfatider hvori forholdet PE/PC varieres. With the method according to the invention, fractions of phosphatides are obtained in which the ratio PE/PC is varied.
Metoden er spesielt anvendbar for fraksjonering av fosfatider fra soya, mais, eggeplomme. The method is particularly applicable for the fractionation of phosphatides from soya, maize, egg yolk.
EKSEMPELEXAMPLE
Man anbringer 1 liter av en harpiks "Amberlite" IRC 50 i en glasskolonne og man vasker med vann og deretter med alkohol og endelig med 1 liter etylacetat. Man oppløser i 400 ml etylacetat 515 g av en alkoholoppløselig fraksjon av rått soyalecitin. 1 liter of a resin "Amberlite" IRC 50 is placed in a glass column and washed with water, then with alcohol and finally with 1 liter of ethyl acetate. 515 g of an alcohol-soluble fraction of crude soy lecithin are dissolved in 400 ml of ethyl acetate.
Den oppnådde oppløsning bringes til å renne gjennom kol-onnen etterfulgt av 150 ml etylacetat. The solution obtained is allowed to flow through the column followed by 150 ml of ethyl acetate.
Det oppnådde eluat inneholder glykolipidene, sterolene og de nøytrale lipider. The eluate obtained contains the glycolipids, sterols and neutral lipids.
Til slutt elueres med etylalkohol.Finally, elute with ethyl alcohol.
De oppnådde initiale fraksjoner tas bort og man tar vare på 7 fraksjoner: The obtained initial fractions are taken away and 7 fractions are kept:
1. Fraksjon A : 5.8 g1. Fraction A : 5.8 g
2. Fraksjon B : 6.6 g2. Fraction B : 6.6 g
3. Fraksjon C : 5.8 g3. Fraction C: 5.8 g
4. Fraksjon D : 5.6 g4. Fraction D : 5.6 g
5. Fraksjon E : 4.4 g5. Fraction E : 4.4 g
6. Fraksjon F : 3.0 g6. Fraction F : 3.0 g
7. Fraksjon G : 3.7 g7. Fraction G : 3.7 g
Den analyserte sammensetning av disse fraksjoner er følg-ende : The analyzed composition of these fractions is as follows:
De forskjellige fraksjoner av fosfatider oppnådd på denne måte kan anvendes alene eller rekombineres som emulgeringsmidler for emulgering av oljer. The different fractions of phosphatides obtained in this way can be used alone or recombined as emulsifiers for emulsifying oils.
De derved oppnådde emulsjoner kan anvendes for parenterale eller enterale næringsmidler, innenfor kosmetologien, dermatologien og for bearbeidelse av liposomer. The resulting emulsions can be used for parenteral or enteral foodstuffs, within cosmetology, dermatology and for the processing of liposomes.
To eksempler på anvendelse av fraksjoner av. fosfatider oppnådd ved fremgangsmåten i henhold til oppfinnelsen for emulgering av soyaolje er gitt i det følgende. Two examples of the application of fractions of. phosphatides obtained by the method according to the invention for emulsifying soybean oil are given below.
Soyaoljene emulgert på denne måte kan tjene til parenteral næringstilførsel. The soybean oils emulsified in this way can be used for parenteral nutrition.
Claims (6)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8301519A FR2540119B1 (en) | 1983-02-01 | 1983-02-01 | PHOSPHATIDE FRACTIONATION PROCESS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO840361L true NO840361L (en) | 1984-08-02 |
Family
ID=9285481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO840361A NO840361L (en) | 1983-02-01 | 1984-01-31 | PROCEDURE FOR PHRAPHATION OF PHOSPHATIDES |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0115981A1 (en) |
| JP (1) | JPS59152392A (en) |
| AU (1) | AU2391684A (en) |
| DK (1) | DK42284A (en) |
| ES (1) | ES8500282A1 (en) |
| FI (1) | FI840394A (en) |
| FR (1) | FR2540119B1 (en) |
| GR (1) | GR79755B (en) |
| IE (1) | IE840234L (en) |
| IL (1) | IL70838A0 (en) |
| NO (1) | NO840361L (en) |
| PT (1) | PT78040B (en) |
| ZA (1) | ZA84730B (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6256497A (en) * | 1985-09-05 | 1987-03-12 | Nisshin Oil Mills Ltd:The | Production of phospholipid composition containing eicosapentaenoic acid |
| EP0259495B1 (en) * | 1986-02-10 | 1991-04-17 | Q.P. Corporation | Process for producing egg yolk lecithin containing a reduced amount of pe and/or containing substantially no impurities |
| JPS62281884A (en) * | 1986-02-10 | 1987-12-07 | Q P Corp | Production of egg yolk lecithin having reduced pe content and/or substantially containing no impurity |
| JPH0657715B2 (en) * | 1987-04-09 | 1994-08-03 | キユーピー株式会社 | Method for producing lysophospholipid containing almost no lysophospholipid other than LPC |
| EP0598989A1 (en) * | 1992-09-01 | 1994-06-01 | Societe Des Produits Nestle S.A. | Nutritional composition and process for its preparation |
| JPH0681142U (en) * | 1993-04-21 | 1994-11-15 | 日本コロムビア株式会社 | RDS receiver |
| FR2710523B1 (en) * | 1993-09-28 | 1996-01-12 | Ard | Wheat lipid extract and its manufacturing process. |
| AUPQ083599A0 (en) * | 1999-06-08 | 1999-07-01 | Technological Resources Pty Limited | Direct smelting vessel |
| US10392410B2 (en) * | 2014-12-05 | 2019-08-27 | Archer Daniels Midland Company | Processes for fractionating phospholipids |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1617680C3 (en) * | 1967-08-21 | 1974-01-31 | A. Nattermann & Cie Gmbh, 5000 Koeln | Process for the production of highly purified phosphatidylcholine |
| US3798246A (en) * | 1972-03-10 | 1974-03-19 | Ajinomoto Kk | Process for preparing soybean phosphatides |
-
1983
- 1983-02-01 FR FR8301519A patent/FR2540119B1/en not_active Expired
-
1984
- 1984-01-17 EP EP84400087A patent/EP0115981A1/en not_active Withdrawn
- 1984-01-31 ES ES529300A patent/ES8500282A1/en not_active Expired
- 1984-01-31 DK DK42284A patent/DK42284A/en not_active Application Discontinuation
- 1984-01-31 GR GR73664A patent/GR79755B/el unknown
- 1984-01-31 FI FI840394A patent/FI840394A/en not_active Application Discontinuation
- 1984-01-31 IL IL70838A patent/IL70838A0/en unknown
- 1984-01-31 IE IE840234A patent/IE840234L/en unknown
- 1984-01-31 NO NO840361A patent/NO840361L/en unknown
- 1984-01-31 AU AU23916/84A patent/AU2391684A/en not_active Abandoned
- 1984-01-31 PT PT78040A patent/PT78040B/en unknown
- 1984-01-31 JP JP59016919A patent/JPS59152392A/en active Pending
- 1984-01-31 ZA ZA84730A patent/ZA84730B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2391684A (en) | 1984-08-02 |
| GR79755B (en) | 1984-10-31 |
| DK42284A (en) | 1984-08-02 |
| EP0115981A1 (en) | 1984-08-15 |
| ES529300A0 (en) | 1984-10-01 |
| ES8500282A1 (en) | 1984-10-01 |
| JPS59152392A (en) | 1984-08-31 |
| FR2540119A1 (en) | 1984-08-03 |
| IL70838A0 (en) | 1984-04-30 |
| DK42284D0 (en) | 1984-01-31 |
| ZA84730B (en) | 1984-09-26 |
| IE840234L (en) | 1984-08-01 |
| FI840394A0 (en) | 1984-01-31 |
| FI840394A (en) | 1984-08-02 |
| FR2540119B1 (en) | 1986-10-17 |
| PT78040A (en) | 1984-02-01 |
| PT78040B (en) | 1986-06-02 |
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