DE438328C - Process for the production of a lecithin derivative - Google Patents
Process for the production of a lecithin derivativeInfo
- Publication number
- DE438328C DE438328C DEB118203D DEB0118203D DE438328C DE 438328 C DE438328 C DE 438328C DE B118203 D DEB118203 D DE B118203D DE B0118203 D DEB0118203 D DE B0118203D DE 438328 C DE438328 C DE 438328C
- Authority
- DE
- Germany
- Prior art keywords
- lecithin
- glycerin
- production
- glycerine
- enters
- 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
Links
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical class 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 claims description 26
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 42
- 239000000787 lecithin Substances 0.000 claims description 26
- 235000010445 lecithin Nutrition 0.000 claims description 25
- 229940067606 lecithin Drugs 0.000 claims description 25
- 235000011187 glycerol Nutrition 0.000 claims description 20
- 230000008961 swelling Effects 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000001661 cadmium Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- XYZZKVRWGOWVGO-UHFFFAOYSA-N Glycerol-phosphate Chemical compound OP(O)(O)=O.OCC(O)CO XYZZKVRWGOWVGO-UHFFFAOYSA-N 0.000 description 1
- -1 Lecithin cadmium salt Chemical class 0.000 description 1
- 102000006386 Myelin Proteins Human genes 0.000 description 1
- 108010083674 Myelin Proteins Proteins 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000008344 egg yolk phospholipid Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 210000005012 myelin Anatomy 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000019605 sweet taste sensations Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- General Preparation And Processing Of Foods (AREA)
Description
Verfahren zur Herstellung eines Lecithinderivates. Es ist aus der Patentliteratur (Patent'schrift 231z33, K1.3oh) bekannt, daß sich Lecithin in Glvcerin löst. So lassen sich klare, leicht bewegliche Lösungen herstellen, indem man Lecithin in der zehnfachen Menge Glycerin in der Kälte oder unter gelinder Erwärmung löst. Mischt man auf mechanischem Wege Glycerin und Lecithin innig, so kann man, selbst im Verhältnis von Z : z, homogene dicke, zähe Massen darstellen, die als- starre oder kolloidale Lösungen erscheinen und sich, ebenso wie die Lösungen von Lecithin in viel Glycerin, emulgieren lassen.Process for the production of a lecithin derivative. It's from the Patent literature (Patent'schrift 231z33, K1.3oh) known that lecithin is in Glvcerin solves. Clear, easily agile solutions can be made by adding lecithin dissolves ten times the amount of glycerine in the cold or under mild warming. If you mix glycerine and lecithin intimately by mechanical means, you can do it yourself in the ratio of Z: z, represent homogeneous thick, tough masses that are as- rigid or colloidal solutions appear and become, just like the solutions of lecithin in a lot of glycerine, let emulsify.
Es wurde nun gefunden, daß bei höherer Temperatur noch eine besondere Reaktion zwischen Lecithin und Glycerin vor sich geht, die nicht einen einfachen Lösungsvorgang darstellt.It has now been found that at a higher temperature there is still a special one Reaction between lecithin and glycerin is going on which isn't an easy one Represents solution process.
Läßt man Glycerin und Lecithin bei höherer Temperatur, z. B. zwischen go und zzo °, aufeinander einwirken, so tritt eine glasige Quellung auf, die die Eigenschaften des Lecithins beeinflußt. Wird das Lecithin in das heiße, wasserfreie Glycerin in dünnen, flachen Scheiben unter Rühren eingetragen, so verschwindet es schnell, und nach genügender Anreicherung der Flüssigkeit mit Lecithin verändert sie sich zu einer hellen, gequollenen, weicheren, völlig homogenen, leicht knetbaren, noch fließenden, aber zähen Masse. Die Färbung wird hierbei heller. Auf diese Weise wird bis zur gleichen Gewichtsmenge Lecithin vom Glycerin aufgenommen.Leaving glycerin and lecithin at a higher temperature, e.g. B. between go and zzo °, act on one another, a glassy swelling occurs, which the Properties of the lecithin influenced. Will the lecithin in the hot, anhydrous Glycerine added in thin, flat slices while stirring, so it disappears changed quickly and after the liquid has been sufficiently enriched with lecithin they turn into a light, swollen, softer, completely homogeneous, easily kneadable, still flowing but viscous mass. The color becomes lighter. In this way lecithin is absorbed by the glycerin up to the same weight.
Das neue Produkt ist sichtlich haltbarer und weniger der teilweisen Verseifung ausgesetzt als einfache Lösungen von Lecithin in Glycerin. Es läßt sich ebenso wie diese mit wasserhaltigen Stoffen vermischen, es bleibt aber in dieser Bindung besser gegen Verseifung geschützt, wie bereits am Geschmack leicht festzustellen ist. Es sei dahingestellt, ob diese Wirkung auf chemischem oder physikalischemWege zustande kommt, doch ist die Abdeckung von aktiven Gruppen in Lecithin, die Selbstzersetzung bedingen, durch Glycerin möglich. Einmal kann das letzte saure Hydroxyl der Glycerinphosphorsäure durch Veresterung, anderseits das basische Cholinhydro-xyl durch eine Art Alkoholatbindung unschädlich gemacht sein.The new product is visually more durable and less of partial Saponification exposed as simple solutions of lecithin in glycerin. It can be just like mixing them with water-containing substances, but it remains in this Binding better protected against saponification, as can be easily seen from the taste is. It remains to be seen whether this effect is chemical or physical comes about, but is the coverage of active groups in lecithin, the self-decomposition conditional, possible through glycerine. One can be the last acidic hydroxyl of glycerol phosphoric acid by esterification, on the other hand the basic choline hydroxyl by a kind of alcoholate bond be rendered harmless.
Mischungen und Emulsionen des neuen Produktes mit konzentrierten wässerigen Lösungen, z. B. zuckerhaltigen Lösungen, bleiben haltbar und wohlschmeckend und lassen sich durch Hitze sterilisieren. Das Verfahren läßt sich sowohl auf Lecithine animalischer Herkunft, z. B. Eierlecithin und Organlecithin, wie auf Pflanzenlecithin anwenden als auch auf Mischungen von diesen Stoffen.Mixtures and emulsions of the new product with concentrated aqueous Solutions, e.g. B. sugary solutions, remain long-lasting and tasty and can be sterilized by heat. The process can be applied to both lecithins animal origin, e.g. B. Egg lecithin and organ lecithin, such as on plant lecithin apply as well as on mixtures of these substances.
Das neue Produkt unterscheidet sich ferner von einer auf kaltem Wege hergestellten, 5oprozentigen, Lecithin enthaltenden Glycerinlösung dadurch, daß der süße Geschmack verändert ist. Es löst sich spielend leicht klar in der mehrfachen Menge Chloroform, während das kalt gelöste hierbei eine Trübung gibt. Es ist aus Chloroform weniger vollständig durch Aceton fällbar und ist auch in warmem Aceton löslich. Äther löst es völlig klar. Die Löslichkeitsverhältnisse des Glycerins werden also bei diesem Produkt nachweislich verändert gegenüber der einfachen Glycerin-Lecithin-Lösung.The new product is also different from one on the cold path prepared, 5%, lecithin-containing glycerol solution in that the sweet taste is changed. It is easily resolved in the multiple Amount of chloroform, while the cold solution gives a turbidity. It's over Chloroform is less completely precipitable by acetone and is also in warm acetone soluble. Aether resolves it completely clearly. The solubility ratios of the glycerol will be So this product has been demonstrably changed compared to the simple glycerin-lecithin solution.
Der Vorgang ist wahrscheinlich so zu erklären, daß eine Veresterung und Racemisierung durch Glycerin stattfindet und das so veränderte Lecithin mit dem nicht molekular gebundenen Glycerin eine starre Lösung oder Additionsbindung bildet, die die neuen physikalischen Eigenschaften zeigt.The process can probably be explained as that an esterification and racemization by glycerine takes place and that changed Lecithin with the non-molecularly bound glycerin is a rigid solution or addition bond which shows the new physical properties.
Das Cadmiumsalz ist körnig, zeigt eine sichtliche Hemmung der Myelinreaktion und enthält Glycerin gebunden. Lecithincadmiumsalz ist auch in einer Mischung von 2,13 Alkohol und 1/3 Glycerin in der Wärme völlig löslich.The cadmium salt is granular, shows a visible inhibition of the myelin reaction and contains glycerine bound. Lecithin cadmium salt is also available in a mixture of 2.13 alcohol and 1/3 glycerine completely soluble in the heat.
Das Lecithin wird durch das Erhitzen mit Glycerin vollständig und schnell racemisiert, wie dies für langes Erhitzen alkoholischer Lösungen bekannt ist. Die Lösungen des neuen Produktes sind optisch inaktiv. Im übrigen zeigen die Cadmiumsalze und Platindoppelsalze keine Abweichungen.The lecithin is completely and by heating with glycerin racemized quickly, as is known for prolonged heating of alcoholic solutions is. The solutions of the new product are optically inactive. Incidentally, they show Cadmium salts and platinum double salts no deviations.
Beispiel. 5 kg Glycerin vom spezifischen Gewicht 1,a6 werden auf go ° C erhitzt und unter stetem Rühren Lecithin in flachen ausgewalzten Scheiben eingetragen. Es tritt langsam Lösung ein. Wenn etwa 212 kg Lecithin eingetragen sind, beginnt die glasige Quellung. In. ungefähr zwei bis drei Stunden gelingt es bei starkem Rühren und Kneten, 5 kg Lecithin einzutragen. Zweckmäßig ist es, frisches, nicht verharztes Lecithin zu benutzen. Nach 24stündigem Stehen wird die Masse nochmals eine Stunde bei 7o bis go ° (Temperatur der Duellmasse an verschiedenen Stellen bestimmt) mechanisch durchgearbeitet, nachdem sie zuvor durch die Salbenmühle fein verteilt war. Ist die Masse noch nicht völlig homogen, wird die Behandlung in der Salbenmühle und nachfolgendes Erhitzen und Durchrühren nochmals wiederholt.Example. 5 kg of glycerine with a specific gravity of 1, a6 are on go ° C and added lecithin to flat rolled discs with constant stirring. Solution occurs slowly. When about 212 kg of lecithin have been entered, begins the glassy swelling. In. it takes about two to three hours with strong Stir and knead to add 5 kg of lecithin. It is not practical if it is fresh to use resinified lecithin. After standing for 24 hours, the mass becomes again one hour at 7o to go ° (temperature of the duel mass in different places determined) mechanically worked through, after having previously been finely processed by the ointment mill was distributed. If the mass is not yet completely homogeneous, the treatment in the Ointment mill and subsequent heating and stirring repeated again.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB118203D DE438328C (en) | 1925-02-17 | 1925-02-17 | Process for the production of a lecithin derivative |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB118203D DE438328C (en) | 1925-02-17 | 1925-02-17 | Process for the production of a lecithin derivative |
Publications (1)
Publication Number | Publication Date |
---|---|
DE438328C true DE438328C (en) | 1926-12-16 |
Family
ID=6994744
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEB118203D Expired DE438328C (en) | 1925-02-17 | 1925-02-17 | Process for the production of a lecithin derivative |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE438328C (en) |
-
1925
- 1925-02-17 DE DEB118203D patent/DE438328C/en not_active Expired
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