CH189980A - Process for the preparation of androstandion- (3,17). - Google Patents
Process for the preparation of androstandion- (3,17).Info
- Publication number
- CH189980A CH189980A CH189980DA CH189980A CH 189980 A CH189980 A CH 189980A CH 189980D A CH189980D A CH 189980DA CH 189980 A CH189980 A CH 189980A
- Authority
- CH
- Switzerland
- Prior art keywords
- trans
- oxidizing agent
- androstanol
- androstandion
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 2
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 241000219832 Onobrychis viciifolia Species 0.000 claims description 2
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical compound [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims 1
- 239000007858 starting material Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 125000005594 diketone group Chemical group 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- -1 chromium acid anhydride Chemical class 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Androstandion-(3,17). Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung von Andro- standion-(3,17), dadurch gekennzeichnet, dass man trans-Androstanol-(3)-on-(17) mit einem Oxydationsmittel behandelt, das die Hydr- oxylgruppe in eine Ketogruppe überführt.
Es ist dabei gleichgültig, aus welchen Ausgangsmaterialien das trans-Androstanol- (3)-on-(17) gewonnen wurde, ob aus tieri schen, pflanzlichen oder andern Produkten oder auf synthetischem Wege. Auch die Rohextrakte von Produkten, welche dasselbe enthalten, wie sie aus Harn, Körperflüssig- keiten, Organen und dergleichen gewonnen werden, lassen sich für das Verfahren als Ausgangsstoffe verwenden.
Die Oxydation kann in üblicher Weise durchgeführt werden, z. B. mit Verbindun gen des sechswertigen Chroms wie Chrom säureanhydrid bei gewöhnlicher Temperatur, jedoch kann man auch andere Oxydations mittel, wie Kupferoxyd und ähnliche Sub stanzen verwenden.
Der Reaktionsverlauf sei durch die fol genden Formelbilder veranschaulicht:
EMI0001.0013
Beispiel: 2,41 g trans-Androstanol-(3)-on-(17) wer den in 450 cm' Eisessig gelöst, mit der 1,5 Atomen Sauerstoff entsprechenden Menge Chromsäure versetzt und einen Tag bei Zim mertemperatur aufbewahrt. Das Lösungsmit- tel wird abgedunstet und aus der bis zur beginnenden Kristallisation konzentrierten Lösung das Diketon durch Zusatz von Was ser kristallin gefällt.
Durch Umlösen aus ver dünntem Alkohol erhält man ein Diketon der Formel C1@H2,02 in langen Nadeln vom Smp. 1.29 C. Die Ausbeute beträgt zirka 2 g, entsprechend 80 bis 85% der Theorie. Optische Drehung a=0,76 , (a) D 0 - l04,8 .
Das gemäss dem vorliegenden Verfahren erhältliche Androstandion-(3, 17) von der Zu sammensetzung C"H2,02 und vom Schmelz punkt 129 ist ein neues Produkt, es weist im Hahnenkammtest eine etwa fünffach stär kere Wirkung auf als das als Ausgangsmate rial dienende trans-Androstanol-(3)-on-(17).
Process for the preparation of androstandion- (3,17). The subject matter of the present patent is a process for the production of androstanol- (3, 17), characterized in that trans-androstanol- (3) -one- (17) is treated with an oxidizing agent which converts the hydroxyl group into a Keto group transferred.
It does not matter from which starting materials the trans-androstanol- (3) -one- (17) was obtained, whether from animal, vegetable or other products or by synthetic means. The crude extracts of products that contain the same as those obtained from urine, body fluids, organs and the like can also be used as starting materials for the process.
The oxidation can be carried out in a conventional manner, e.g. B. with compounds of hexavalent chromium such as chromium acid anhydride at ordinary temperature, but you can also use other oxidizing agents such as copper oxide and similar substances.
The course of the reaction is illustrated by the following equations:
EMI0001.0013
Example: 2.41 g of trans-androstanol- (3) -one- (17) who dissolved in 450 cm 'of glacial acetic acid, treated with the amount of chromic acid corresponding to 1.5 atoms of oxygen and stored at room temperature for one day. The solvent is evaporated and the diketone is precipitated in crystalline form from the solution, which has been concentrated until crystallization begins, by adding water.
Redissolving from diluted alcohol gives a diketone of the formula C1 @ H2.02 in long needles with a melting point of 1.29 C. The yield is about 2 g, corresponding to 80 to 85% of theory. Optical rotation a = 0.76, (a) D 0 - l04.8.
The androstandion- (3, 17) obtainable according to the present method with the composition C "H2.02 and melting point 129 is a new product, it has an effect about five times stronger in the Hahnenkamm test than the trans serving as the starting material -Androstanol- (3) -one- (17).
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE189980X | 1934-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH189980A true CH189980A (en) | 1937-03-31 |
Family
ID=5721592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH189980D CH189980A (en) | 1934-10-31 | 1935-02-21 | Process for the preparation of androstandion- (3,17). |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH189980A (en) |
-
1935
- 1935-02-21 CH CH189980D patent/CH189980A/en unknown
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