DE1047597B - Process for the production of natural choline phosphoric acid diglyceride esters poor in colaminphosphoric acid diglyceride esters - Google Patents
Process for the production of natural choline phosphoric acid diglyceride esters poor in colaminphosphoric acid diglyceride estersInfo
- Publication number
- DE1047597B DE1047597B DEN13867A DEN0013867A DE1047597B DE 1047597 B DE1047597 B DE 1047597B DE N13867 A DEN13867 A DE N13867A DE N0013867 A DEN0013867 A DE N0013867A DE 1047597 B DE1047597 B DE 1047597B
- Authority
- DE
- Germany
- Prior art keywords
- acid diglyceride
- diglyceride esters
- phosphoric acid
- inert gas
- production
- 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
Links
- 150000002148 esters Chemical class 0.000 title claims description 21
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title claims description 18
- 229960001231 choline Drugs 0.000 title claims description 13
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 title claims description 13
- 229910000147 aluminium phosphate Inorganic materials 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- SUHOOTKUPISOBE-UHFFFAOYSA-N O-phosphoethanolamine Chemical compound NCCOP(O)(O)=O SUHOOTKUPISOBE-UHFFFAOYSA-N 0.000 title description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000011261 inert gas Substances 0.000 claims description 8
- 238000000605 extraction Methods 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 235000013311 vegetables Nutrition 0.000 claims description 7
- 235000010469 Glycine max Nutrition 0.000 claims description 6
- 244000068988 Glycine max Species 0.000 claims description 6
- 230000007717 exclusion Effects 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 230000001476 alcoholic effect Effects 0.000 claims description 5
- 239000011435 rock Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 235000004626 essential fatty acids Nutrition 0.000 description 8
- 239000000787 lecithin Substances 0.000 description 8
- 235000010445 lecithin Nutrition 0.000 description 8
- 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 description 7
- 229940067606 lecithin Drugs 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 208000019423 liver disease Diseases 0.000 description 3
- 150000003904 phospholipids Chemical class 0.000 description 3
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 229920002527 Glycogen Polymers 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 229940114079 arachidonic acid Drugs 0.000 description 2
- 235000021342 arachidonic acid Nutrition 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- -1 fatty acid ester Chemical class 0.000 description 2
- 229940096919 glycogen Drugs 0.000 description 2
- 235000020778 linoleic acid Nutrition 0.000 description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
- CFWRDBDJAOHXSH-SECBINFHSA-N 2-azaniumylethyl [(2r)-2,3-diacetyloxypropyl] phosphate Chemical compound CC(=O)OC[C@@H](OC(C)=O)COP(O)(=O)OCCN CFWRDBDJAOHXSH-SECBINFHSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 241000589614 Pseudomonas stutzeri Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 238000003811 acetone extraction Methods 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000013345 egg yolk Nutrition 0.000 description 1
- 210000002969 egg yolk Anatomy 0.000 description 1
- 230000003212 lipotrophic effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000002367 phosphate rock Substances 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000005672 tetraenes Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 238000010626 work up procedure Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/683—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols
- A61K31/685—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols one of the hydroxy compounds having nitrogen atoms, e.g. phosphatidylserine, lecithin
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Medicines Containing Plant Substances (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DEUTSCHESGERMAN
Die Erfindung betrifft ein Verfahren zur Gewinnung von colaminphosphorsäurediglyceridesterarmen natürlichen Cholinphosphorsäurediglyceridestern aus pflanzlichen Rohphosphatiden, insbesondere aus solchen, die aus Sojabohnen in bekannter Weise hergestellt werden. Die Cholin- und Colaminphosphorsäurediglyceridester sind bekanntlich Vertreter der im Tier- und Pflanzenreich außerordentlich weit verbreiteten Esterphosphatide (vergleiche z. B. Paul Karr er, Lehrbuch der organischen Chemie, 1950, S. 247). Diese Ester kommen immer, insbesondere in den Rohphosphatiden pflanzlic'her Herkunft, vergesellschaftet vor. Dieses Stoö'gemisch wird im Handel und in der Technik mit dem Namen Lecithin bezeichnet. Nach der chemischen Nomenklatur werden allerdings unter Lecithin bzw. Lecithinen nur die Vertreter aus der Körperklasse der Phosphatide verstanden, die als basische Gruppe Cholin führen; wenn Colamin den basischen Anteil darstellt, spricht der Chemiker von Kephalin (vgl. Karrer, a.a.O., S. 247). Diese Esterphosphatide weisen folgende Strukturformel auf:The invention relates to a process for the production of colaminophosphoric acid diglyceride ester poor natural choline phosphoric acid diglyceride esters from vegetable rock phosphatides, in particular from those that are made from soybeans in a known manner. The choline and colamine phosphoric acid diglyceride esters are known to be representatives of the extremely widespread in the animal and plant kingdom Ester phosphatides (compare e.g. Paul Karr er, Textbook of Organic Chemistry, 1950, P. 247). These esters always come together, especially in the rock phosphatides of vegetable origin before. This mixture of substances is referred to in trade and industry by the name of lecithin. According to the chemical nomenclature, however, lecithin or lecithins only represent the representatives the body class of phosphatides, which have choline as a basic group; when Colamin den represents a basic component, the chemist speaks of kephalin (cf. Karrer, op. cit., p. 247). These ester phosphatides have the following structural formula:
CH2O-COCnH2n + 1 CH 2 O-COC n H 2n + 1
CH0-C0CmH2m + 1 CH0-COC m H 2m + 1
CH2OP^-OCH2CH2N(CHa)3OH
XOHCH 2 OP ^ -OCH 2 CH 2 N (CHa) 3 OH
X OH
Lecithin
(Cholinphosphorsäurediglyceridester)Lecithin
(Choline phosphoric acid diglyceride ester)
CH2O · COCnHCH 2 O • COC n H
CHO-coc,»:CHO-coc, »:
CH2OP-1OCH2CH2NH2 CH 2 OP- 1 OCH 2 CH 2 NH 2
OHOH
Kephalin
(Colaminphosphorsäurediglyceridester)Cephalin
(Colaminphosphoric acid diglyceride ester)
Es wurde gefunden, daß sich aus Rohphosphatiden pflanzlicher Herkunft, insbesondere auch aus Sojabohnen-Ro'hphosphatid, colaminphosphorsäurediglyceridesterarme natürliche Cholinphosphorsäurediglyceridester mit einem hohen Gehalt an essentiellen Fettsäuren gewinnen lassen, die ihrerseits für die medizinisch-therapeutische Aktivität der biologisch wichtigen Cholinphosphorsäurediglyceridester zusätzlich von ausschlaggebender Bedeutung sind.It has been found that raw phosphatides of vegetable origin, especially soybean raw phosphatide, Low-colamine phosphoric acid diglyceride ester, natural choline phosphoric acid diglyceride ester with a high content of essential fatty acids, which in turn for the Additional medicinal and therapeutic activity of the biologically important choline phosphoric acid diglyceride ester are of vital importance.
Unter den essentiellen Fettsäuren werden nach medizinischem Sprachgebrauch ganz allgemein dieAccording to medical parlance, the essential fatty acids are generally referred to as
Verfahren zur GewinnungMethod of extraction
von colaminphosphorsäure-of colaminophosphoric acid
diglyceridesterarmen natürlichenLow diglyceride ester natural
CholinphosphorsäurediglyceridesternCholine phosphoric acid diglyceride esters
Anmelder:Applicant:
A. Nattermann & Cie.,
Köln-Braunsfeld, Eupener Str. 159A. Nattermann & Cie.,
Cologne-Braunsfeld, Eupener Str. 159
Dr. Hans Eikermann, Köln-Braunsfeld,
ist als Erfinder genannt wordenDr. Hans Eikermann, Cologne-Braunsfeld,
has been named as the inventor
lebensnotwendigen Fettsäuren verstanden, die der Körper sich nicht selbst aufbauen kann. Es handelt sich um mehrfach ungesättigte Fettsäuren ganz bestimmter Konfiguration, von welchen der Linolsäure für den menschlichen Organismus eine Schlüsselstellung zukommt, da im Körper aus ihr z. B. die sehr aktive essentielle Arachidonsäure, eine C20-Tetraen-Säure, aufgebaut wird. Die Bedeutung, die die essentiellen Fettsäuren für den menschlichen Organismus besitzen, ergibt sich unter anderem aus folgenden Veröffentlichungen :Understand the essential fatty acids that the body cannot produce by itself. These are polyunsaturated fatty acids of a very specific configuration, of which linoleic acid has a key position for the human organism, since it is made up of e.g. B. the very active essential arachidonic acid, a C 20 tetraene acid, is built up. The importance that essential fatty acids have for the human organism results from the following publications, among others:
Rieckehoff und Mitarbeiter (Arch. Biochem., 25, S. 1 bis 12, 1950) fanden in Tierversuchen, daß bei Fettmangeldiät schon eine kleine Menge von Linolsäure genügt, um die Arachidonsäure im Körper zu synthetisieren. Schulz (Medizin., 29/30. VII, S. 1007, 1954) stellt fest, daß bei akuten Leberparenchymkrankheiten durch Gaben von mehrfach ungesättigten Fettsäuren die Krankheitsdauer verkürzt wird. Auch bei chronischen Hepatopathien wird ein deutlicher Erfolg" verzeichnet. Allegri (Crch. Sc. med. Torino, 97, S. 6 1954) zeigte an Tierversuchen, daß im Vergleich mit Kontrolltieren teilhepatektomierte Ratten, die mit ungesättigten Fettsäuren gefüttert worden waren, eine schnellere Regeneration der übriggebliebenen Leber — gemessen an Gewicht und histologischem Bild — (starke karyokinetische Aktivität) und erhebliche Zunahme der Kerndurchmesser aufwiesen. Kn i ppi ng (Münch. med. Wschr., 97, 28, VII, S. 901, 1955) bewies, daß die mehrfach ungesättigten Fettsäuren die leichten und mittelschweren Hepatopathien und vor allem die so schwer zu beeinflussende Phase zwischen Hepatopathie und Wiederherstellung abzukürzen vermögen.Rieckehoff and co-workers (Arch. Biochem., 25, pp. 1 to 12, 1950) found in animal experiments that a small amount of Linoleic acid is enough to synthesize arachidonic acid in the body. Schulz (Medicine., 29/30. VII, S. 1007, 1954) states that in acute liver parenchymal diseases by giving polyunsaturated Fatty acids the disease duration is shortened. Even with chronic hepatopathies, a significant success "recorded. Allegri (Crch. Sc. med. Torino, 97, p. 6 1954) showed in animal experiments, that in comparison with control animals partially hepatectomized Rats fed unsaturated fatty acids regenerated faster of the remaining liver - measured by weight and histological picture - (strong karyokinetic Activity) and showed a significant increase in core diameter. Kn i ppi ng (Münch. Med. Wschr., 97, 28, VII, p. 901, 1955) proved that the polyunsaturated fatty acids the light and moderate hepatopathies and especially the difficult to influence phase between hepatopathy and abbreviate restoration.
809 700/348809 700/348
Im Tierversuch wird die Läppchenverfettung zurückgebildet, und die Glycogenspeicherung in der Leber iMtnnit zu. Ferner wird die Gallensekretion angeregt und der Brenztraubensäurespiegel gesenkt. Nach Schettler haben mehrfach ungesättigte essentielle Fettsäuren nicht nur eine lipotrope Wirkung, sondern auch einen begünstigenden Einfluß auf die Glycogensynthese. Im Hinblick auf die Bedeutung, die den cholinführenden Phospholipiden im allgemeinen und den essentiellen Fettsäuren insbesondere für die Heilkunde zukommt, haben sich die Erfinder die Aufgabe gestellt, die Aufarbeitung von pflanzlichen Phosphatides insbesondere von Sojabohnenrohphosphatiden, so durchzuführen, daß einerseits die im natürlichen Zustand in den Esterphosphatiden enthaltenen essentiellen Fettsäuren erhalten bleiben, d. h. auf einen erwünscht hohen Wert gebracht werden, und andererseits aber gleichzeitig möglichst viele Begleitstoffe, darunter auch alle Esterphosphatide, die als basische Komponente nicht Cholin aufweisen, weitgehend abgetrennt werden.In animal experiments, the lobular fatty tissue is reduced, and the glycogen storage in the liver iMtnnit too. It also stimulates the secretion of bile and lowered the pyruvic acid level. According to Schettler, polyunsaturated have essentials Fatty acids not only have a lipotropic effect, but also a beneficial influence on the Glycogen synthesis. With regard to the importance of the choline-carrying phospholipids in general and essential fatty acids in particular for medicine, the inventors have set the task of processing plant phosphatides, in particular raw soybean phosphatides, to be carried out in such a way that, on the one hand, those in the natural state in the ester phosphatides essential fatty acids contained are preserved, d. H. brought to a desired high value and on the other hand as many accompanying substances as possible, including all ester phosphatides, which do not have choline as a basic component, are largely separated off.
Es ist bekannt, lecithinhaltige Stoffe, wie Eidotter oder Gehirnsubstanz, in Kühlgefäßen unter Ausschluß von Licht und Luft mehrfach mit Aceton zu behandeln, und die zurückbleibende Masse unter vermindertem Druck bei 30° C in sauerstofffreier Atmosphäre, z. B. unter Stickstoff oder Kohlendioxyd, bei Ausschluß von Licht mit wasserfreiem Äthylalkohol zu extrahieren und darauf die alkoholische Lecithinlösung mit einer alkoholischen Lösung von Aluminiumoxydsol zu versetzen, wobei sich Lecithin in Form einer komplexen Verbindung als gallertige Masse ausscheidet, die erst auf Lecithin aufgearbeitet werden muß. Auf diese Weise lassen sich aus pflanzlichen Rohphosphat!'den keine colaminphosphorsäurediglyceridarme natürliche Cholinphosphorsäurediglyceridester gewinnen. Zwar wird der Colaminphosphorsäurediglyceridfettsäureester von Alkohol schwer aufgenommen, jedoch steigt die Löslichkeit dieses Esters in Gegenwart von Cholinphosphorsäurediglyceridfettsäureester. It is known to store lecithin-containing substances, such as egg yolks or brain matter, in cooling vessels to the exclusion from light and air to treat several times with acetone, and the remaining mass under reduced Pressure at 30 ° C in an oxygen-free atmosphere, e.g. B. under nitrogen or carbon dioxide Exclusion of light with anhydrous ethyl alcohol and then the alcoholic lecithin solution to put with an alcoholic solution of aluminum oxide sol, with lecithin in Form of a complex compound excretes as a gelatinous mass, which is only worked up on lecithin must become. In this way, vegetable rock phosphate cannot be converted into low levels of colaminophosphoric acid diglyceride Obtain natural choline phosphoric acid diglyceride esters. It is true that the colamine phosphoric acid diglyceride fatty acid ester Hardly absorbed by alcohol, but the solubility of this ester increases in the presence of choline phosphoric acid diglyceride fatty acid ester.
Um die der Erfindung zugrunde liegende Aufgabe zu lösen, wird der im Vakuum und in Gegenwart eines inerten Gases von Aceton befreite Extraktionsrückstand von pflanzlichen Rohphosphatiden, z. B. von pflanzlichem Sojabohnenrohphosphid, einer mehrmaligen Extraktion mit Alkohol unterworfen, und die alkoholischen Lösungen werden mehrere Tage stehengelassen, dann von den suspendierten bzw. kolloidal mitgelösten Stoffen befreit und schließlich im Vakuum bei gleichzeitigem Nachziehen eines inerten Gases ein~ geengt. Auf diese Weise werden in praktisch befriedigender Ausbeute Phospholipide erhalten, die als basische Komponente überwiegend Cholin enthalten und dazu in bezug auf die Gesamtfettsäuren 60% essentielle Fettsäuren aufweisen.In order to solve the problem on which the invention is based, the in a vacuum and in the presence an inert gas freed from acetone extraction residue of vegetable rock phosphatides, z. B. from raw vegetable soybean phosphide, subjected to repeated extraction with alcohol, and the alcoholic solutions are left to stand for several days, then from the suspended or colloidal released substances and finally in a vacuum with simultaneous drawing in of an inert gas ~ narrowed. In this way, phospholipids are obtained in a practically satisfactory yield, which as basic components contain predominantly choline and in relation to the total fatty acids 60% have essential fatty acids.
Vorteilhafterweise wird unter Ausschluß von Licht gearbeitet.It is advantageous to work with the exclusion of light.
8 kg Sojabohnenrohphosphatid werden bei einer 35° C nicht übersteigenden Temperatur mit etwa 1501 Aceton in wiederholtem Aufarbeiten von den öligen Bestandteilen befreit. Das Ungelöste wird im Vakuum und in Gegenwart eines inerten Gases von Aceton befreit, worauf eine mehrmalige Extraktion des Rückstandes mit Äthanol erfolgt, und zwar wiederum bei einer maximalen Temperatur von 35° C und unter Ausschluß von Licht, Luft bzw. Sauerstoff, indem durch die Extraktionsanlage ein inertes Gas geleitet wird. Die alkoholischen Lösungen werden durch mehrtägiges Stehenlassen von den in ihnen suspendierten bzw. kolloidal mitgelösten Stoffen gereinigt. Durch Einengen der Lösungen im Vakuum bei gleichzeitigem Nachziehen eines inerten Gases, wie z. B. Stickstoff oder Kohlendioxyd, wird in etwa 25- bis 30%iger Ausbeute eine Phospholipidfraktion erhalten, die in bezug auf die Gesamtfettsäuren 60% essentielle Fettsäuren aufweist, was dem Anteil dieser wesentlichen Komponente im Gesamtmolekül zu etwa 45% entspricht.8 kg soybean crude phosphatide are at a temperature not exceeding 35 ° C with about 1501 acetone freed from the oily components in repeated work-up. The unsolved becomes in the Vacuum and freed from acetone in the presence of an inert gas, followed by multiple extraction the residue takes place with ethanol, again at a maximum temperature of 35 ° C and with the exclusion of light, air or oxygen by entering through the extraction system inert gas is passed. The alcoholic solutions are removed from the in them suspended or colloidally dissolved substances cleaned. By narrowing down the solutions in the Vacuum with simultaneous drawing in of an inert gas, such as. B. nitrogen or carbon dioxide a phospholipid fraction obtained in a yield of about 25 to 30% which, based on the total fatty acids 60% essential fatty acids, which is the proportion of this essential component in the overall molecule corresponds to about 45%.
Claims (2)
Deutsche Patentschrift Nr. 617 508.Considered publications:
German patent specification No. 617 508.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEN13867A DE1047597B (en) | 1957-07-09 | 1957-07-09 | Process for the production of natural choline phosphoric acid diglyceride esters poor in colaminphosphoric acid diglyceride esters |
| DEN13873A DE1053299B (en) | 1957-07-09 | 1957-07-10 | Process for the production of natural choline phosphoric acid diglyceride esters free of colaminphosphoric acid diglyceride esters |
| CH6103158A CH393057A (en) | 1957-07-09 | 1958-06-25 | Process for the production of natural phospholipids |
| NL229049A NL229049A (en) | 1957-07-09 | 1958-06-26 | |
| BE569235A BE569235A (en) | 1957-07-09 | 1958-07-08 | |
| GB21837/58A GB877031A (en) | 1957-07-09 | 1958-07-08 | A process for the production of natural phospholipids and related substances |
| US26954A US3031478A (en) | 1957-07-09 | 1960-05-05 | Process for the production of natural phospholipids and substances produced thereby |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEN13867A DE1047597B (en) | 1957-07-09 | 1957-07-09 | Process for the production of natural choline phosphoric acid diglyceride esters poor in colaminphosphoric acid diglyceride esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1047597B true DE1047597B (en) | 1958-12-24 |
Family
ID=7339787
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEN13867A Pending DE1047597B (en) | 1957-07-09 | 1957-07-09 | Process for the production of natural choline phosphoric acid diglyceride esters poor in colaminphosphoric acid diglyceride esters |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1047597B (en) |
| GB (1) | GB877031A (en) |
| NL (1) | NL229049A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5214171A (en) * | 1988-12-08 | 1993-05-25 | N.V. Vandemoortele International | Process for fractionating phosphatide mixtures |
| US7465717B2 (en) | 2004-09-27 | 2008-12-16 | Soymor | Process for releasing and extracting phosphatides from a phosphatide-containing matrix |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE617508C (en) * | 1932-06-22 | 1935-08-20 | I G Farbenindustrie Akt Ges | Process for the production of pure lecithin |
-
1957
- 1957-07-09 DE DEN13867A patent/DE1047597B/en active Pending
-
1958
- 1958-06-26 NL NL229049A patent/NL229049A/nl unknown
- 1958-07-08 GB GB21837/58A patent/GB877031A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE617508C (en) * | 1932-06-22 | 1935-08-20 | I G Farbenindustrie Akt Ges | Process for the production of pure lecithin |
Also Published As
| Publication number | Publication date |
|---|---|
| GB877031A (en) | 1961-09-13 |
| NL229049A (en) | 1963-07-15 |
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