CH163890A - Process for the production of a long-life salt of Primula saponius. - Google Patents
Process for the production of a long-life salt of Primula saponius.Info
- Publication number
- CH163890A CH163890A CH163890DA CH163890A CH 163890 A CH163890 A CH 163890A CH 163890D A CH163890D A CH 163890DA CH 163890 A CH163890 A CH 163890A
- Authority
- CH
- Switzerland
- Prior art keywords
- primula
- salt
- saponin
- ammonia
- production
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 241000245063 Primula Species 0.000 title claims description 4
- 235000000497 Primula Nutrition 0.000 title claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 22
- DQUUSJCGJNQFPG-CBMAJASRSA-N Primulasaponin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@@H]2[C@H]([C@H](O[C@@H]3C([C@H]4[C@]([C@@H]5[C@@]([C@@]6(C[C@@H](O)[C@]78CO[C@]6([C@@H]7CC(C)(C)CC8)CC5)C)(C)CC4)(C)CC3)(C)C)O[C@@H]([C@H]2O)C(O)=O)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)O[C@H](CO)[C@H](O)[C@@H]1O DQUUSJCGJNQFPG-CBMAJASRSA-N 0.000 claims description 14
- DQUUSJCGJNQFPG-UHFFFAOYSA-N Primulasaponin Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(OC3C(C4C(C5C(C6(CC(O)C78COC6(C7CC(C)(C)CC8)CC5)C)(C)CC4)(C)CC3)(C)C)OC(C2O)C(O)=O)OC2C(C(O)C(O)C(CO)O2)O)OC(CO)C(O)C1O DQUUSJCGJNQFPG-UHFFFAOYSA-N 0.000 claims description 14
- 229910021529 ammonia Inorganic materials 0.000 claims description 10
- 150000003863 ammonium salts Chemical class 0.000 claims description 6
- 238000005187 foaming Methods 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000012675 alcoholic extract Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000000284 extract Substances 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 2
- 229940012189 methyl orange Drugs 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical class C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical class O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/256—Polyterpene radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Steroid Compounds (AREA)
Description
Verfahren zur Herstellung eines haltbaren Salzes des Primula-Saponins. Die Erfindung betrifft ein Verfahren zur Herstellung eines haltbaren Salzes des Pri- mula-Saponins, welches dadurch gekennzeich net ist, dass man Primula-Saponin mit Am moniak absättigt. Das so erhaltene Ammon- salz des Primula - Saponins schmilzt unter starkem Aufschäumen bei 212 und 213 0, ist leicht löslich in Wasser und gibt beim Kochen mit Alkalien Ammoniak ab.
1 gr des Salzes verbrauchen bei der Titration mit
EMI0001.0013
HCl bis zum Eintritt saurer Reaktion gegen Methyl- orange 8 cm3
EMI0001.0018
HCl. Das Salz enthält mit hin<B>18,6</B> mgr Ammoniak pro Gramm. Das Salz ist ein pharmazeutisch wertvolles Pro dukt.
Es kann auch als Ausgangsmaterial für die Herstellung wichtiger pharmazeutischer Verbindungen, beispielsweise zur Herstellung von Codeinsalz, Morphinsalz des Primula- Saponins, verwendet werden.
Zur Herstellung des Ammonsalzes des Primula - Saponins ist es nicht erforderlich, vom reinen Primula - Saponin selbst auszu- gehen. Man kann auch Extrakte, insbesondere alkoholische Extrakte, aus Primula - Drogen, die das Primula-Saponin enthalten, mit Am moniak absättigen. Auch dabei scheidet sich das Ammonsalz des Primula - Sapouins ab, das dureh Umkristallisieren gereinigt werden kann.
<I>Beispiele</I> 1. 10 kg Radix primulae werden mit 50 kg 96 0%igen Alkohol der Extraktion unter worfen und aus der erhaltenen alkoholischen Lösung wird der Alkohol soweit verdampft, bis der Rückstand ca. 18 kg wiegt. Alsdann wird derselbe, noch heiss, vorsichtig mit wäs serigem Ammoniak bis zur deutlich alka lischen Reaktion versetzt. Nach dem Erkal ten scheidet sich das Ammoniumsalz des Pri- mula-Saponins ab, das durch mehrfaches Um lösen aus verdünntem Alkohol unter Anwen dung von Kohle in rein weissem Zustand er halten wird.
Es schmilzt unter starkem Auf schäumen bei 212 - 213 0, ist leicht löslich in Wasser und gibt beim Kochen mit Alka- lien Ammoniak ab. 1 gr des Salzes verbraucht bis zum Eintritt saurer Reaktion gegen Methylorange 8 cmg
EMI0002.0003
HCl, enthält also 13,6 mgr Ammoniak.
2. 1 gr Primula-Saponin wird mit 5 cm' Alkohol und 3 gr etwa 20 o/oiger wässeriger Ammoniaklösung verrieben. Dabei scheidet sich das Ammonsalz des Primula - Saponins ab, das die gleichen Eigenschaften wie das Erzeugnis nach Beispiel 1 besitzt.
Process for the production of a long-life salt of Primula saponin. The invention relates to a method for producing a durable salt of primula saponin, which is characterized in that primula saponin is saturated with ammonia. The ammonium salt of Primula saponin thus obtained melts with strong foaming at 212 and 213 0, is easily soluble in water and releases ammonia when boiled with alkalis.
Use 1 gram of the salt when titrating with
EMI0001.0013
HCl until an acidic reaction occurs against methyl orange 8 cm3
EMI0001.0018
HCl. The salt contains <B> 18.6 </B> mgr ammonia per gram. The salt is a pharmaceutically valuable product.
It can also be used as starting material for the production of important pharmaceutical compounds, for example for the production of codeine salt, the morphine salt of Primula saponin.
In order to produce the ammonium salt of Primula saponin, it is not necessary to start from the pure Primula saponin itself. You can also saturate extracts, especially alcoholic extracts, from Primula drugs that contain the Primula saponin with ammonia. Here, too, the ammonium salt of Primula sapouin separates, which can be purified by recrystallization.
<I> Examples </I> 1. 10 kg of Radix primulae are subjected to extraction with 50 kg of 96 0% alcohol and the alcohol is evaporated from the alcoholic solution obtained until the residue weighs approx. 18 kg. Then it is carefully mixed with aqueous ammonia, while it is still hot, until the reaction is clearly alkaline. After cooling, the ammonium salt of the primula saponin is deposited, which is obtained in a pure white state by repeated dissolving from diluted alcohol using charcoal.
It melts with strong foaming at 212 - 213 0, is easily soluble in water and gives off ammonia when boiled with alkali. 1 gram of the salt consumed 8 cmg until an acidic reaction against methyl orange occurs
EMI0002.0003
HCl, so contains 13.6 mgr ammonia.
2. 1 gram of Primula saponin is triturated with 5 cm 'of alcohol and 3 grams of about 20% aqueous ammonia solution. The ammonium salt of Primula saponin, which has the same properties as the product according to Example 1, separates out.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH163890T | 1932-10-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH163890A true CH163890A (en) | 1933-09-15 |
Family
ID=4416933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH163890D CH163890A (en) | 1932-10-10 | 1932-10-10 | Process for the production of a long-life salt of Primula saponius. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH163890A (en) |
-
1932
- 1932-10-10 CH CH163890D patent/CH163890A/en unknown
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