DE2915614A1 - Removal of impurities from plant phosphatide(s) - by dissolving the crude lecithin in a non-polar solvent followed by column chromatography - Google Patents
Removal of impurities from plant phosphatide(s) - by dissolving the crude lecithin in a non-polar solvent followed by column chromatographyInfo
- Publication number
- DE2915614A1 DE2915614A1 DE19792915614 DE2915614A DE2915614A1 DE 2915614 A1 DE2915614 A1 DE 2915614A1 DE 19792915614 DE19792915614 DE 19792915614 DE 2915614 A DE2915614 A DE 2915614A DE 2915614 A1 DE2915614 A1 DE 2915614A1
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- phosphatide
- fractions
- starting material
- impurities
- pref
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- 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.)
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Links
- 239000000787 lecithin Substances 0.000 title claims abstract description 4
- 235000010445 lecithin Nutrition 0.000 title claims abstract description 4
- 238000004440 column chromatography Methods 0.000 title claims description 6
- 239000012454 non-polar solvent Substances 0.000 title claims description 4
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 title abstract description 3
- 229940067606 lecithin Drugs 0.000 title abstract description 3
- 239000012535 impurity Substances 0.000 title abstract 3
- 238000000034 method Methods 0.000 claims abstract description 21
- 239000000463 material Substances 0.000 claims abstract description 9
- 239000007858 starting material Substances 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 238000005194 fractionation Methods 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims description 9
- 239000011435 rock Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 235000013311 vegetables Nutrition 0.000 claims description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 2
- 239000008158 vegetable oil Substances 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 12
- 239000000741 silica gel Substances 0.000 abstract description 11
- 229910002027 silica gel Inorganic materials 0.000 abstract description 11
- 229930182558 Sterol Natural products 0.000 abstract description 8
- 235000003702 sterols Nutrition 0.000 abstract description 8
- 150000003432 sterols Chemical class 0.000 abstract description 7
- 102000004196 processed proteins & peptides Human genes 0.000 abstract description 6
- 108090000765 processed proteins & peptides Proteins 0.000 abstract description 6
- 150000001720 carbohydrates Chemical class 0.000 abstract description 5
- 235000014633 carbohydrates Nutrition 0.000 abstract description 5
- 235000021588 free fatty acids Nutrition 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract 1
- 239000010773 plant oil Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 239000003208 petroleum Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 150000003626 triacylglycerols Chemical class 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
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Chemical class 0.000 description 2
- 229930195729 fatty acid Chemical class 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 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 2
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 2
- 150000003905 phosphatidylinositols Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000001719 carbohydrate derivatives Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000469 ethanolic extract Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 125000001095 phosphatidyl group Chemical group 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- -1 sterol esters Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Steroid Compounds (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
Verfahren zur Gewinnung von reinen PhosphatidenProcess for the production of pure phosphatides
Das bei der Speiseölherstellung anfallende pflanzliche Rohlecithin enthält ebenso wie aus tierischem Gewebe gewonnes neben Phosphatidylcholin, Phosphatidyläthanolamin, Phosphatidylinosit und anderen phosphorhaltigen Glycerinester Begleitsubstanzen wie Peptide, Aminosäuren, Sterine, Sterinester, Mono-, und Di-und Triglyceride, freie Fettsäuren und Kohlenhydratderivate.The raw vegetable lecithin produced in the production of edible oil as well as obtained from animal tissue, contains phosphatidylcholine, phosphatidylethanolamine, Phosphatidylinositol and other phosphorus-containing glycerol esters accompanying substances such as peptides, amino acids, sterols, sterol esters, mono-, and di- and triglycerides, free fatty acids and carbohydrate derivatives.
Diese Begleitsubstanzen sind sowohl für pharmazeutische als auch lebensmittel technische Anwendungen unerwünscht bzw. schädlich.These accompanying substances are common to both pharmaceutical and food products technical applications undesirable or harmful.
Die übliche Reinigung sieht eine Behandlung mit Aceton zur Abtrennung von Neutrallipiden vor. Dabei bleiben weiterhin die Sterinderivate sowie Kohlenhydrate und Peptide als unerwünschte Begleitsubstanzen mit den Phosphatiden vergesellschaftet.The usual cleaning involves treatment with acetone for separation of neutral lipids. The sterol derivatives and carbohydrates still remain and peptides associated with the phosphatides as undesirable accompanying substances.
Daran schliesst sich üblicherweise eine ein oder mehrmalige Extraktion mit niederen Alkoholen wie Methanol, Athanol, Propanol etc.This is usually followed by one or more extraction with lower alcohols such as methanol, ethanol, propanol etc.
an wie dies z.B. in den Patenten U.S. 1.955.514 und Ger. 261.212 beschrieben ist.as shown, for example, in U.S. patents. 1.955.514 and Ger. 261.212 is.
Hierbei lassen sich zwar Kohlenhydrate und Peptide abtrennen, aber nicht die Sterinderivate.Carbohydrates and peptides can be separated here, but not the sterol derivatives.
Zur Gewinnung von sterinfreien Phosphatiden, insbesondere Phosphatidylcholin, erfolgt die weitere Reinigung durch chromatographische Methoden mit Kieselgel, Aluminiumoxid, Florisil, lonenaustauscher oder andere Materialien (12.01.73 JA 006399 und U.S. 2.554.955) Dies kann sowohl säulenchromatographisch als auch durch Rühren rnit der Trennmaterial erFrlrjeti (DT - 61/6/9) Die am meisten benutzte Methode sieht eine säulenchromatograpische Reinigungmit Kiese gel als Trennmaterial vor. Das Verhältnis von Trennmaterial zu Rohprodukt liegt ülicherweise zwischen 100 : 1.For obtaining sterol-free phosphatides, especially phosphatidylcholine, further purification is carried out by chromatographic methods with silica gel, aluminum oxide, Florisil, ion exchange or other materials (1/12/73 JA 006399 and U.S. 2.554.955) This can be done both by column chromatography and by stirring with the Release material erFrlrjeti (DT - 61/6/9) The most widely used method sees one purification by column chromatography with silica gel as separating material. The relationship from separating material to raw product is usually between 100: 1.
und 10 : 1. Zur Elution benutzt man Lösungsmittelgradienten aus chlorierten Kohlenwasserstoffen, wie Methylenchlorid, Chloroform, DichToräthan etc. und niedere Alkohole, wie Methanol, Athanol usw. Es werden so in der Reihenfolge ihrer Polarität zuerst die Neutrallipide, die Sterinderivate und erst am Schluss die Phospholipide eluiert.and 10: 1. Chlorinated solvent gradients are used for elution Hydrocarbons such as methylene chloride, chloroform, dichloroethane, etc. and lower Alcohols such as methanol, ethanol etc. They are so in the order of their polarity first the neutral lipids, the sterol derivatives and only at the end the phospholipids eluted.
Das Verhältnis Ausgangsmaterial (g) zu Lösungsmittel (Vol.) beträgt 1 : 50 bis 1 : 200.The ratio of starting material (g) to solvent (by volume) is 1: 50 to 1: 200.
Man kann auf diese Art und Weise nur kleine Mengen Rohmaterial reinigen und benötigt zusätzlich grosse Mengen an verschiedenen Lösungsmittelgemischen.You can only clean small amounts of raw material in this way and also requires large amounts of different solvent mixtures.
Es wurde nun überraschenderweise gefunden, dass man die Phosphatide in einem Arbeitsschritt von sämtlichen Begleitstoffen wie Peptide, Kohlenhydrate, Mono-, Di- und Triglyceride, Fettsäuren sowie Sterinderivate durch ein säulenchromatographisches Verfahren befreien kann.It has now surprisingly been found that the phosphatides in one step of all accompanying substances such as peptides, carbohydrates, Mono-, di- and triglycerides, fatty acids and sterol derivatives by means of column chromatography Procedure can exempt.
Verfahrensgemäss wird dabei das Trennmaterial, z.B. Kieselgel, mit einem unpolaren Lösungsmittel wie Kohlenwasserstoff oder Kohlenwasserstoffgemischen in die Säule gefüllt.According to the method, the separating material, e.g. silica gel, is included a non-polar solvent such as hydrocarbon or hydrocarbon mixtures filled into the column.
Im Gegensatz zu allen bisher üblichen Säulenchromatographiemethoden ist verfahrensgemäss das Trennmaterial - Rohprodukt Verhältnis zwischen 1,5 : 1 und 3 : 1.In contrast to all previously common column chromatography methods According to the process, the separation material - raw product ratio is between 1.5: 1 and 3: 1.
Zu erwarten war unter diesen Bedingungen, dass keinerlei Trennungseigenschaften mehr vorhanden waren und das ölhaltige Rohprodukt unverändert von der Säule heruntergewaschen würde.Under these conditions it was to be expected that no separation properties whatsoever were more present and the oily crude product was washed down unchanged from the column would.
Verfährt man erfindungsgemäss jedoch so, dass man mit einem einzigen unpolaren Lösungsmittel, wie Kohlenwasserstoffen, deren Gemische, Ather etc. eluiert, so erhält man eine saubere Trennung in der Form, dass im Gegensatz zu den bisher bekannten Verfahren ausschliesslich die Phosphatide wie Phosphatidyicholin, Phosphatidyläthanolamin, Phosphatidylinosit sowie sonstige Phosphatidylderivate eluiert werden und alle anderen Begleitstoffe wie Mono-, Di- und Triglyceride, Fettsäuren, Kohlenhydrate, Peptide sowie insbesondere Sterinderivate auf der Säule verbleiben.If one proceeds according to the invention, however, that one with a single non-polar solvents, such as hydrocarbons, their mixtures, ethers etc. elute, so you get a clean separation in the form that in contrast to the previous one known processes exclusively the phosphatides such as phosphatidyicholine, phosphatidylethanolamine, Phosphatidylinositol and other phosphatidyl derivatives are eluted and all others Accompanying substances such as mono-, di- and Triglycerides, fatty acids, carbohydrates, Peptides and especially sterol derivatives remain on the column.
tm Gegensatz zu den bisher bekannten Verfahren braucht man für ein Teil(g) Rohprodukt nur 5 - 8 Teile (Vol.) Elutionsmittel.In contrast to the previously known method, one needs for a Part (g) of crude product only 5 - 8 parts (vol.) Of eluent.
Man erhält also in einem, statt bisher mehreren Verfahrensschritten bei sehr viel geringerem Verbrauch eines einzigen Lösungsmittels ein reineres Produkt.So you get in one, instead of previously several process steps a purer product with a much lower consumption of a single solvent.
Weiterhin ist es verfahrensgemäss möglich, bifreie Phosphatidgemische von ihren Begleitstoffen zu trennen, indem man ihnen zwischen 20 % und 40 % an pflanzlichem 01 zusetzt und dann wie beschrIeben verfährt.Furthermore, according to the method, it is possible to use bi-free phosphatide mixtures to separate them from their accompanying substances by adding between 20% and 40% vegetable 01 is added and then proceed as described.
Weiterhin ist es verfahrensgemäss auch möglich, zuerst die Säule durch Zugabe von 20 - 40 % an pflanzlichem Öl so zu präparieren, dass bei einer anschliessenden Chromatographie eines ölfreien Phosphatidgemisches wiederum nur die Phosphatide und nicht die Begleitstoffe eluiert werden. Die Phosphatidausbeuten erreichen bei dem hier vorliegenden Verfahren bis zu 95 %.Furthermore, according to the method, it is also possible to first go through the column Add 20 - 40% of vegetable oil to prepare so that a subsequent Chromatography of an oil-free phosphatide mixture, in turn, only contains the phosphatides and the accompanying substances are not eluted. The phosphatide yields reach at the present process up to 95%.
Beispiele: Beispiel 1 100 g Kieselgel werden in 300 ml Petroläther aufgeschlämmt und in eine Chromatographiesäule (Durchmesser 4 cm) gefüllt. Man löst 50 g Rohphosphatid in 150 ml Petroläther und gibt die Lösung auf die vorbereitete Säule. Eluiert wird mit Petroläther,die einzelnen Fraktionen ä 50 ml werden über DC geprüft.Examples: Example 1 100 g of silica gel are dissolved in 300 ml of petroleum ether slurried and filled into a chromatography column (diameter 4 cm). One solves 50 g of rock phosphatide in 150 ml of petroleum ether and add the solution to the prepared Pillar. It is eluted with petroleum ether, the individual 50 ml fractions are over DC checked.
Es werden 5 Fraktionen eingedampft, die 01- und Sterin-frei sind: Man erhält 30 g Phosphatid.5 fractions are evaporated, which are 01- and sterol-free: 30 g of phosphatide are obtained.
Dies entspricht einer Ausbeute von 92,3 /00, bezogen auf die Phosphatide im Rohphosphatid t65 % Phosphatide, 35 % Dialysierba res3.This corresponds to a yield of 92.3 / 00, based on the phosphatides in the rock phosphatide t65% phosphatide, 35% dialysable res3.
Beispiel 2 Wie unter Beispiel 1 nimmt man 100 g Kieselgel, füllt eine Säule und gibt dann 50 g eines ölhaltigen Rohphosphatidextraktionsrückstandes, die in 100 ml Petroläther gelöst sind, auf die Säule.Example 2 As in Example 1, 100 g of silica gel are taken and one is filled Column and then gives 50 g of an oil-containing raw phosphatide extraction residue that are dissolved in 100 ml of petroleum ether on the column.
Man erhält 30 g sauberes Produkt aus 5 Fraktionen. Dies entspricht einer Ausbeute von 92,3 %.30 g of clean product are obtained from 5 fractions. This matches with a yield of 92.3%.
Beispiel 3 450 g eines ölhaltigen Rohphosphatidextraktionsrückstandes werden in 1350 ml Petroläther (Kp.: 40 - 600C) gelöst und mit Hilfe von Celite Perlite J 100 filtriert. Das Filtrat wird auf eine vorbereitete 900 g-Kieselgelsäule gegeben. Eluiert wird mit Petroläther.Example 3 450 g of an oil-containing rock phosphatide extraction residue are dissolved in 1350 ml of petroleum ether (boiling point: 40-600C) and perlite with the help of Celite J 100 filtered. The filtrate is placed on a prepared 900 g silica gel column. It is eluted with petroleum ether.
Nach 5 Fraktionen ã 500 ml ist im Eluat kein Phosphatid mehr auf der DC-Platte zu sehen.After 5 fractions of 500 ml each, there is no longer any phosphatide in the eluate TLC plate to see.
Nach Eindampfen der Lösungen erhält man 275,48 g Produkt, dies enspricht 94,58 t der Theorie.After evaporation of the solutions, 275.48 g of product are obtained, this corresponds 94.58 t of theory.
Beispiel 4 100 g Kieselgel werden in 300 ml Petroläther (Hexan) rein (Kp.: 40 - 600C) aufgeschlämmt und in eine Chromatographtesäule von einem Durchmesser von 4 cm gefüllt.Example 4 100 g of silica gel are pure in 300 ml of petroleum ether (hexane) (Bp .: 40-600C) slurried and placed in a chromatograph column of a diameter of 4 cm filled.
16 g Soja-U1 roh werden in 20 ml Hexan gelöst und auf die vorbereitete Säule gegeben. Man lässteseinsickern und wäscht mit 50 ml Hexan nach. Dann gibt man 30 g entöltes Rohphosphatid, die in 50 ml Hexan gelöst sind, auf die Säule und eluiert mit Hexan.16 g of raw soy U1 are dissolved in 20 ml of hexane and added to the prepared Given column. It is allowed to seep in and washed with 50 ml of hexane. Then there one 30 g of deoiled rock phosphatide, which are dissolved in 50 ml of hexane, on the column and eluted with hexane.
Man fängt Fraktionen von 50 ml auf und prüft diese über Dünnschichtchromatographie. Ab der 5. Fraktion wird kein Phosphatid mehr eluiert, die Fraktionen 1 - 4 sind Cl- und Sterin-frei.Fractions of 50 ml are collected and checked by thin layer chromatography. From the 5th fraction onwards, no more phosphatide is eluted, fractions 1 - 4 are Cl- and sterol-free.
Die Fraktionen werden eingedampft. Man erhält 24,69 g Phosphatid. Dies entspricht einer Ausbeute von 28,3 t bezogen auf das eingesetzt ERP.The fractions are evaporated. 24.69 g of phosphatide are obtained. This corresponds to a yield of 28.3 t in relation to the ERP used.
Beispiel 5 1500 g Kieselgel werden in 5000 ml Petroläther aufgeschlämmt und in eine Säule gefüllt. 240 g Soja-Ol werden anschliessend in 300 ml Petroläther gelöst und diese Lösung lässt man dann einsickern und wäscht mit 750 ml Petroläther nach.Example 5 1500 g of silica gel are suspended in 5000 ml of petroleum ether and filled into a column. 240 g of soy oil are then poured into 300 ml of petroleum ether dissolved and this solution is then allowed to seep in and washed with 750 ml of petroleum ether after.
Dann gibt man 450 g entöltes Rohphosphatid gelöst in 750 ml Petroläther auf die Säule und eluiert mit Petroläther.Then 450 g of deoiled rock phosphatide dissolved in 750 ml of petroleum ether are added onto the column and elute with petroleum ether.
6 Fraktionen 500 ml ergeben 300 g Phosphatid, dies entspricht einer Ausbeute von 67 t.6 fractions of 500 ml result in 300 g of phosphatide, this corresponds to one Yield of 67 t.
Beispiel 6 50 g eines Gemisches an entöltem Rohphosphatid und Soja-Ol im Verhältnis 65 : 35 werden in 150 ml n-Hexan gelöst und auf eine Säule gegeben, die zuvor mit 100 g Kieselgel, aufgeschlämmt in n-Hexan, gefüllt wird. Dann eluiert man mit n-Hexan.Example 6 50 g of a mixture of deoiled rock phosphatide and soy oil in a ratio of 65:35 are dissolved in 150 ml of n-hexane and placed on a column, which is previously filled with 100 g of silica gel suspended in n-hexane. Then eluted one with n-hexane.
4 Fraktionen à 60 ml werden eingedampft und man erhält 30 g sauberes Produkt, was einer Ausbeute von 92 t entspricht.4 fractions of 60 ml each are evaporated and 30 g of clean material are obtained Product, which corresponds to a yield of 92 t.
Beispiel 7 100 g Kieselgel werden mit 300 ml Petroläther (Kp.: 40 - 600C) aufgeschlämmt und in eine Chromatographie-Säule (Durchmesser 4 cm) gefällt.Example 7 100 g of silica gel are mixed with 300 ml of petroleum ether (boiling point 40 - 600C) slurried and precipitated in a chromatography column (diameter 4 cm).
30 g eines Athanolauszugs aus entöltem Rohphosphatid werden zusammen mit 20 g Soja-Ol in 100 ml Petroläther gelöst und auf die vorbereitete Säule gegeben. Man eluiert mit Petroläther.30 g of an ethanol extract from deoiled rock phosphatide are combined with 20 g of soy oil dissolved in 100 ml of petroleum ether and added to the prepared column. Elute with petroleum ether.
Die Fraktionen werden über DC geprüft. Die ersten 4 Fraktionen von 50 ml sind O1- und Sterin-frei. Sieergebeneine Ausbeute von 25,79 9, das sind ca. 86 % bezogen auf das eingesetzte Produkt.The fractions are checked via DC. The first 4 fractions of 50 ml are O1- and sterol-free. They give a yield of 25.79 9, that is approx. 86% based on the product used.
Claims (7)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792915614 DE2915614A1 (en) | 1979-04-18 | 1979-04-18 | Removal of impurities from plant phosphatide(s) - by dissolving the crude lecithin in a non-polar solvent followed by column chromatography |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792915614 DE2915614A1 (en) | 1979-04-18 | 1979-04-18 | Removal of impurities from plant phosphatide(s) - by dissolving the crude lecithin in a non-polar solvent followed by column chromatography |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2915614A1 true DE2915614A1 (en) | 1980-10-30 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792915614 Withdrawn DE2915614A1 (en) | 1979-04-18 | 1979-04-18 | Removal of impurities from plant phosphatide(s) - by dissolving the crude lecithin in a non-polar solvent followed by column chromatography |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2915614A1 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0054768A2 (en) * | 1980-12-13 | 1982-06-30 | A. Nattermann & Cie. GmbH | A process for the separation of acylated phospholipids from phosphatidylcholin products containing them |
| EP0054770A2 (en) * | 1980-12-13 | 1982-06-30 | A. Nattermann & Cie. GmbH | A process for the separation of oil and/or phosphatidylethanolamine from alcohol soluble phosphatidylcholin products containing them |
| EP0054769A2 (en) * | 1980-12-13 | 1982-06-30 | A. Nattermann & Cie. GmbH | A process for the separation of oil and/or phosphatidylethanolamine from alcoholic phosphatidylcholin products containing them |
| US4857236A (en) * | 1984-12-17 | 1989-08-15 | A. Nattermann & Cie Gmbh | Process for isolating phosphatidylcholine free of lysophosphatidylcholine from egg powder |
| EP0365868A2 (en) * | 1988-10-28 | 1990-05-02 | Societe Des Produits Nestle S.A. | Process to separate glycolipides from a mixture of lipids, and use of the fractions obtained |
| US4983327A (en) * | 1984-12-17 | 1991-01-08 | A. Nattermann & Cie Gmbh | Process for isolating a phosphatidylcholine free of other phospholipids in the starting material |
| EP0592962A1 (en) * | 1992-10-14 | 1994-04-20 | Eisai Chemical Co., Ltd. | Purification method of crude product |
-
1979
- 1979-04-18 DE DE19792915614 patent/DE2915614A1/en not_active Withdrawn
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0054768A2 (en) * | 1980-12-13 | 1982-06-30 | A. Nattermann & Cie. GmbH | A process for the separation of acylated phospholipids from phosphatidylcholin products containing them |
| EP0054770A2 (en) * | 1980-12-13 | 1982-06-30 | A. Nattermann & Cie. GmbH | A process for the separation of oil and/or phosphatidylethanolamine from alcohol soluble phosphatidylcholin products containing them |
| EP0054769A2 (en) * | 1980-12-13 | 1982-06-30 | A. Nattermann & Cie. GmbH | A process for the separation of oil and/or phosphatidylethanolamine from alcoholic phosphatidylcholin products containing them |
| EP0054768A3 (en) * | 1980-12-13 | 1982-08-04 | A. Nattermann & Cie. Gmbh | A process for the separation of acylated phospholipids from phosphatidylcholin products containing them |
| EP0054770A3 (en) * | 1980-12-13 | 1982-08-04 | A. Nattermann & Cie. Gmbh | A process for the separation of oil and/or phosphatidylethanolamine from alcoholic phosphatidylcholin products containing them |
| EP0054769A3 (en) * | 1980-12-13 | 1982-08-04 | A. Nattermann & Cie. Gmbh | A process for the separation of oil and/or phosphatidylethanolamine from alcoholic phosphatidylcholin products containing them |
| US4857236A (en) * | 1984-12-17 | 1989-08-15 | A. Nattermann & Cie Gmbh | Process for isolating phosphatidylcholine free of lysophosphatidylcholine from egg powder |
| US4983327A (en) * | 1984-12-17 | 1991-01-08 | A. Nattermann & Cie Gmbh | Process for isolating a phosphatidylcholine free of other phospholipids in the starting material |
| EP0365868A2 (en) * | 1988-10-28 | 1990-05-02 | Societe Des Produits Nestle S.A. | Process to separate glycolipides from a mixture of lipids, and use of the fractions obtained |
| EP0365868A3 (en) * | 1988-10-28 | 1990-06-27 | Societe Des Produits Nestle S.A. | Process to separate glycolipides from a mixture of lipids, and use of the fractions obtained |
| US5284941A (en) * | 1988-10-28 | 1994-02-08 | Nestec S.A. | Process for obtaining glycolipids and phospholipids |
| EP0592962A1 (en) * | 1992-10-14 | 1994-04-20 | Eisai Chemical Co., Ltd. | Purification method of crude product |
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