DE2020407A1 - Technical process for the isolation of Silimarin - Google Patents
Technical process for the isolation of SilimarinInfo
- Publication number
- DE2020407A1 DE2020407A1 DE19702020407 DE2020407A DE2020407A1 DE 2020407 A1 DE2020407 A1 DE 2020407A1 DE 19702020407 DE19702020407 DE 19702020407 DE 2020407 A DE2020407 A DE 2020407A DE 2020407 A1 DE2020407 A1 DE 2020407A1
- Authority
- DE
- Germany
- Prior art keywords
- isolation
- silimarin
- extracted
- technical process
- solution
- 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
- 238000000034 method Methods 0.000 title claims description 8
- 238000002955 isolation Methods 0.000 title claims description 4
- SEBFKMXJBCUCAI-UHFFFAOYSA-N 3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one Chemical compound C1=C(O)C(OC)=CC(C2C(OC3=CC=C(C=C3O2)C2C(C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 SEBFKMXJBCUCAI-UHFFFAOYSA-N 0.000 title description 4
- 239000003925 fat Substances 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- -1 Fatty acid ester Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SEBFKMXJBCUCAI-HKTJVKLFSA-N silibinin Chemical compound C1=C(O)C(OC)=CC([C@@H]2[C@H](OC3=CC=C(C=C3O2)[C@@H]2[C@H](C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 SEBFKMXJBCUCAI-HKTJVKLFSA-N 0.000 description 3
- 229960004245 silymarin Drugs 0.000 description 3
- 235000017700 silymarin Nutrition 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 102100023708 Coiled-coil domain-containing protein 80 Human genes 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 101000978383 Homo sapiens Coiled-coil domain-containing protein 80 Proteins 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013861 fat-free Nutrition 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 231100000234 hepatic damage Toxicity 0.000 description 1
- 230000008818 liver damage Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
Landscapes
- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Microbiology (AREA)
- Animal Behavior & Ethology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Medicinal Chemistry (AREA)
- Alternative & Traditional Medicine (AREA)
- Mycology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
Description
Ir.B.Janiak
Kelkheim
Kapellenbergstr.6Ir.B.Janiak
Kelkheim
Kapellenbergstrasse 6
Technisches Verfahren zur Isolierung von SilymarinTechnical process for the isolation of silymarin
Beschreibungdescription
las Silymarin, ein Flavolignan^ 'wurde im Jahre 1959 von mir isoliert^ 'und hat sich heute als wirksame Substanz zur Heilung von Leberschäden erwiesen*·*^.las Silymarin, a Flavolignan ^ 'was made by me in 1959 isolated ^ 'and has now proven to be an effective substance for healing liver damage * · * ^.
In der Veröffentlichung^) wurden von mir zwei Isolationsverfahren angegeben, von denen das eine nach vollständiger Entfettung der Droge Fructus Cardui mariae mittels Petrolaether, amschließend edne Essigesterextraktion erforderte. Auch die von MADAUB angemeldeten ' Verfahren P 1767666.3 und P 1923082,1 beruhen auf dem von mir bereifcs I960 ^2) veröffentlichten Prinzip, wenn auch durch die aus der Gelherstellung bekannte Vorentfettung mittels Spindelpresse,eine Zeitverkürzung erzielt werden konnte. Bennoch iet auch bei diesem Verfahren für die anschließender Essigesterextraktion eine Zeit von -24- Stunden~~@rforderTich. Darüberhinaus stören die nicht vollständig entfernten Fette erheblich die Extraktdarstellung. Unter großem technischem Einsatz von Separatoren und Emulgatoren wird eine Ausbeute von 2,2% erzielt.In the publication ^) I used two isolation methods indicated, one of which after complete defatting of the drug Fructus Cardui mariae using petroleum ether, then edne Acetic ester extraction required. Also those registered by MADAUB ' Processes P 1767666.3 and P 1923082.1 are based on the principle published by me in 1960 ^ 2), albeit through the Pre-degreasing known from gel production using a screw press, a Time reduction could be achieved. Bennoch is also involved with this one Procedure for the subsequent ethyl acetate extraction a time of -24- hours ~~ @ rforderTich. In addition, they do not completely interfere removed fats significantly the extract presentation. With great technical use of separators and emulsifiers, a yield becomes of 2.2% achieved.
Das zweite von mir veröffentlichte Verfahren (2) ging von einer Auskochung der nicht entfetteten Droge mit Wasser aus und führte nach anschließender Essigesterexti'aktion des Wassers wesentlich rascher zum Ziel. Nachteilig war die geringe Ausbeute von 0,4-% und der hohe Stromverbrauch.The second method I published (2) was from one Decoction of the non-defatted drug with water and, after subsequent Essigesterexti'action of the water, resulted faster to the goal. The disadvantage was the low yield of 0.4% and the high power consumption.
Es wird im nachfolgenden ein Verfahren beschrieben, das innerhalb von 3 stunden ausgehend von der nicht entfetteten Droge zu einem fettfreien, direkt zur Trockne einengbaren Wirkstoffextrakt führt. Die Ausbeute beträgt zwischen 2,5 und 4%.The following describes a process that takes 3 hours from the non-defatted drug to a fat-free active ingredient extract that can be constricted directly to dryness. The yield is between 2.5 and 4%.
Mittels einem mehrkomponentigen für Silymarin selektiv wirkenden Lösungsmittel, bestehend aus mit Wasser mischbaren Alkoholen, Wasserf und niederen Fettsäureestern oder niederen Kohlenwasserstoffen, auch Mischungen von letzteren, werden die Fette weitgehend; in der Droge belassen und die dennoch extrahierten Fettanteile lassen sich leicht dusch Stehenlassen der etwas eingeengten Lösung abtrennen.By means of a multicomponent Silymarin for selectively acting solvent consisting of water-miscible alcohols, water f and lower Fettsäureestern or lower hydrocarbons, and mixtures of the latter, the fats are largely; Left in the drug and the extracted fat parts can easily be separated from the somewhat concentrated solution.
109846/1913109846/1913
6253 Kelkheim
Kapellenbergstr,66253 Kelkheim, Germany
Kapellenbergstrasse, 6
ü&a Verhältnis der einseelaea K©ap©aeafcea ist variabel jedoch lassen sich gute ürgetaisse erzielen,, wenn der Alkohol den Hauptanteil stellt, zweckmäßig 40 - 60 % unä wenn der wässrige Anteil 20 - 40% und die niederen F©t-t@äiis?a@ste2» eflor Kohlenwasserstoffe 10 ««· 30% nicht überschreiten» ü & a ratio of the einseelaea K © ap © aeafcea is variable, however, good ürgetaisse can be achieved, if the alcohol makes up the main part, expediently 40 - 60% and if the aqueous part 20 - 40% and the lower F © tt @ äiis? a @ ste2 »eflor hydrocarbons 10« «· Do not exceed 30%»
Die gemahlene ©rage wird sw©eksaäSig la eise» Kessel in der Siedehitze mit des obea BBgs§©öQa<iaB Sosiäsagsmittel ©strahiert, ein gleichzeitiges Riihven hat sieö ale gitoffeig erwiesen«, Is kann unter Druck oder auch bei !©rmalärmck rsiürfeeis E'i-alifliaSkähier extrahiert werden» Falls auf besoaöers hohe Amsbe^tea ftöiet jg©l@gl? wird9 kann der ExferaktlonsvorgangThe ground © rage is sw © eksaäSig la eise »Kettle in the boiling heat with the obea BBgs§ © öQa <iaB Sosiäsagsmittel ©, a simultaneous riihven has shown all gitoffeig«, Is can be done under pressure or also with! 'i-alifliaSkähier are extracted »if on besoaöers high Amsbe ^ tea ftöiet jg © l @ gl? becomes 9 can the Exferaktlonsvorgang
Verfahrenprocedure
In eis®» 1000 1 K©ssg1 ai^ !uhrwerk usd Hiickflußkühler werden 250 kg gemahlene Frm@frais CaMuI nar-ia® nit @lm@y SSisehung von 250 1 Methanol 150 1 ftaaser BEdI 100 I Sc^igsaiarssstiiylester 1 όtunde gekocht« Anschließend wird mittels Prasse ©ä<s& Zaatrlfiige das Lösungsmittel entder fiüeksfeaisd eraeiit alt eiaer aeuen Mischung obiger Zu-"aBg 2 Sfeuagasi g©k@©h"öe Hach d©a erneuten Abpressen werden die Lösiai5g®i3i-fetei ver@iB.igt imä soweit eiageeagt» daß das Volumen um 10 bis 4-0% ueraiBdeiot wii'd# Saa laßt es 30 min stehen,bis der mitextrahiert® Fettaateil sieb auf der Lösung abgesetzt hat und leicht entferat; werdea kaaa» Iii© irerblaibeasi© -fettreie Lösung läßt sich direkt über- einsn geeigaetea Tr©ekaer6 ^©.rsisgsweise einem Sprühtrockner zur Trockne:- einengen® Maa erhälfe S -10% ©iaes 40% Siljsiarinextraktes. Aus die-sea kaae Mittels limki?3,stallisati©a aus 50fs Methanol wie bei(2) beschrielbeiii das reis® öilysarcis dargestellt werden«In Eis® »1000 1K © SSG1 ai ^! Clockwork usd Hiickflußkühler 250 kg of ground frm @ frais Camui nar-ia® nit @ lm @ y SSisehung 250 1 150 1 methanol ftaaser Bedi 100 I Sc ^ igsaiarssstiiylester 1 ό tunde cooked "Subsequently, by means of Prasse © ä <s & Zaatrlfiige the solvent entder fiüeksfeaisd eraeiit old eiaer aeuen above mixture inlet" ABG 2 Sfeuagasi g © k @ © h "ö e Hach d © a re-pressing, the Lösiai5g®i3i-fetei ver @ iB.igt imä so far igeteagt »that the volume by 10 to 4-0% ueraiBdei o t wii'd # Saa let it stand for 30 min until the co-extracted® fat part sieve has settled on the solution and is easily removed; werdea kaaa »III © irerblaibeasi © -fat-free solution can be poured directly over a suitable Tr © ekaer 6 ^ ©, or a spray dryer to dryness: - concentrate® Maa get S -10% © iaes 40% Siljsiarin extract. From die-sea kaae by means of limki? 3, stallisati © a from 50fs methanol as described in (2) the reis® öilysarcis can be represented «
1» Hansel4 Siaipler DtscheApotfeefesr-stg 108,1985 (1%8) 2. JaaiakpHässel Planta EieÄisa S971 (l%0) 3· HahB,LehmaBn9Kurtes»,!l'slu£-l1iVögel,Arsaoiüslttelf. 18e698(1968)1 »Hansel 4 Siaipler DtscheApotfeefesr-stg 108.1985 (1% 8) 2. JaaiakpHässel Planta EieÄisa S 9 71 (l% 0) 3 · HahB, LehmaBn 9 Kurtes»,! L'slu £ -l 1i birds, Arsaoiüslttelf. 18 e 698 (1968)
109846/1913109846/1913
BAD ORIGINALBATH ORIGINAL
Claims (1)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702020407 DE2020407A1 (en) | 1970-04-27 | 1970-04-27 | Technical process for the isolation of Silimarin |
| FR7114669A FR2092095A1 (en) | 1970-04-27 | 1971-04-23 | Silymarin isolation |
| BE766228A BE766228A (en) | 1970-04-27 | 1971-04-23 | INDUSTRIAL PROCESS FOR ISOLATING SILYMARIN |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702020407 DE2020407A1 (en) | 1970-04-27 | 1970-04-27 | Technical process for the isolation of Silimarin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2020407A1 true DE2020407A1 (en) | 1971-11-11 |
Family
ID=5769446
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702020407 Pending DE2020407A1 (en) | 1970-04-27 | 1970-04-27 | Technical process for the isolation of Silimarin |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE766228A (en) |
| DE (1) | DE2020407A1 (en) |
| FR (1) | FR2092095A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008039271A1 (en) | 2007-12-23 | 2009-06-25 | Euromed Sa | New milk thistle extract, method of preparation and use |
| EP2959910A1 (en) | 2014-06-26 | 2015-12-30 | Bionorica Se | Milk thistle extract of fruit shells of Silybum marianum, process of manufacture and use |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3773932A (en) * | 1968-06-01 | 1973-11-20 | Madaus & Co Dr | Method for recovering silymarin comprising polyhydroxyphenyl chromanones |
-
1970
- 1970-04-27 DE DE19702020407 patent/DE2020407A1/en active Pending
-
1971
- 1971-04-23 FR FR7114669A patent/FR2092095A1/en active Granted
- 1971-04-23 BE BE766228A patent/BE766228A/en unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008039271A1 (en) | 2007-12-23 | 2009-06-25 | Euromed Sa | New milk thistle extract, method of preparation and use |
| EP2567703A2 (en) | 2007-12-23 | 2013-03-13 | Euromed SA | Novel Silybum marianum extract, method of manufacture and use |
| EP2959910A1 (en) | 2014-06-26 | 2015-12-30 | Bionorica Se | Milk thistle extract of fruit shells of Silybum marianum, process of manufacture and use |
| WO2015197854A1 (en) | 2014-06-26 | 2015-12-30 | Bionorica Se | Milk thistle extract from the fruit peels of milk thistle, method for production and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| BE766228A (en) | 1971-10-25 |
| FR2092095A1 (en) | 1972-01-21 |
| FR2092095B1 (en) | 1974-09-27 |
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