AT142026B - Process for the preparation of hydrogenation products of the follicular hormone. - Google Patents
Process for the preparation of hydrogenation products of the follicular hormone.Info
- Publication number
- AT142026B AT142026B AT142026DA AT142026B AT 142026 B AT142026 B AT 142026B AT 142026D A AT142026D A AT 142026DA AT 142026 B AT142026 B AT 142026B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- hydrogenation products
- hormone
- follicular hormone
- follicular
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 title claims description 3
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 title description 2
- 229940088597 hormone Drugs 0.000 claims description 4
- 239000005556 hormone Substances 0.000 claims description 4
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- APLGXMKUJWCEBP-UHFFFAOYSA-N 1-butoxy-4-[(4-methylphenyl)methoxy]benzene Chemical compound C1=CC(OCCCC)=CC=C1OCC1=CC=C(C)C=C1 APLGXMKUJWCEBP-UHFFFAOYSA-N 0.000 description 1
- 229910003310 Ni-Al Inorganic materials 0.000 description 1
- 229910018054 Ni-Cu Inorganic materials 0.000 description 1
- 229910018481 Ni—Cu Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003325 follicular Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 125000003198 secondary alcohol group Chemical group 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
<Desc/Clms Page number 1>
EMI1.1
Das Follikelhonaon der Formel C18H22O2 lässt sieh durch gelinde Reduktionsmethoden unter Aufnahme von zwei Atomen Wasserstoff in ein Isomerengemiseh kristallisierter Reduktionsprodukte von der Formel CjsHOa überführen, welche durch Fiaktionieiungsverfahren voneinander getrennt werden können, z. B. in ein Kristallisat vom F. P. 168-170 und ein solches vom Schmelzpunkt 198-202 J.
Nach der von Butenandt, Zeitschrift für angewandte Chemie 1932 (Bericht iiber den Vortrag auf der Versammlung deutscher Natuiforscher und Ärzte in Wiesbaden 1932), als besonders wahischeinlich angegebenen Konstitution des Follikelhormons muss man annehmen, dass in den erhaltenen Reduktionsprodukten die Carbonylgruppe zur sekundären Alkoholgruppe reduziert ist, während der in dem Follikelhormon enthaltene Benzolkern erhalten geblieben ist.
Es wurde nun gefunden, dass man sowohl das Isomerengemisch der Formel C18H24O2 als solches, wie die daraus abgetrennten chemischen Individuen der gleichen Zusammensetzung durch katalytische Hydrierung unter Verwendung solcher Katalysatoren, welche den Benzolkern anzugreifen gestatten, wie z. B. Ni-Cu-Sulfat. Ni-AI-Oxyd, Platinoxyd, kolloidales Platin, Palladiumschwarz u. dgl. (s. z. B. Houben #Die Methoden der organischen Chemie". 3. Auf !., Bd. II, S. 326 ff., insbesondere die Hydrierungsmethode von Sabatier und Senderens auf S. 328 und die Platinmetallkatalyse auf S. 329), zu dem voll-
EMI1.2
von 160-170 behandelt. Nach vollendeter Reaktion wird durch versetzen mit Wasser die hydrierte Verbindung isoliert.
Durch Umkristallisieren aus Methanol lässt sich das Präparat in einen kristallisierten und einen öligen Anteil trennen, welche beide im Kapaunenkammtest wirksam sind.
EMI1.3
atmosphäre geschüttelt. Die vom Katalysator befreite Reaktionslösung wird im Vakuum zur Trockne gedampft, der Rückstand in Äther aufgenommen und die ätherische Lösung zur Entfernung von eventuell noch vorhandenen Spuren nicht hydrierter Substanz mit wässerigem Alkali durchgeschüttelt. Nach dem Verjagen des Äthers wird ein helles, sehr konsistentes Harz gewonnen, dessen CH-Bestimmung auf
EMI1.4
diesem Präparat lassen sich durch Umkristallisieren und anschliessende fraktionierte Destillation im Hochvakuum kristallisierte Fraktionen abtrennen,
die schon mit 0#5 mg im Kapaunenkammtest eine physiologische Wirkung zeigen.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
EMI1.1
The follicular honeycomb of the formula C18H22O2 can be converted into an isomer mixture of crystallized reduction products of the formula CjsHOa by mild reduction methods with the uptake of two atoms of hydrogen, which can be separated from one another by functionalization processes, e.g. B. in a crystallizate from F. P. 168-170 and such a melting point 198-202 J.
According to the constitution of the follicle hormone, which was stated to be particularly likely, in the reduction products obtained, the carbonyl group is reduced to the secondary alcohol group according to the constitution of the follicle hormone, which was given by Butenandt, Zeitschrift für angewandte Chemie 1932 (report on the lecture at the gathering of German natural researchers and doctors in Wiesbaden, 1932) , while the benzene nucleus contained in the follicular hormone is retained.
It has now been found that both the isomer mixture of the formula C18H24O2 as such, as well as the separated chemical individuals of the same composition by catalytic hydrogenation using catalysts which allow the benzene nucleus to be attacked, such as B. Ni-Cu sulfate. Ni-Al oxide, platinum oxide, colloidal platinum, palladium black, etc. The like (see, for example, Houben "The Methods of Organic Chemistry". 3. Auf!., Vol. II, p. 326 ff., in particular the hydrogenation method of Sabatier and Senderens on p. 328 and platinum metal catalysis on p. 329) to the full
EMI1.2
treated from 160-170. When the reaction is complete, the hydrogenated compound is isolated by adding water.
By recrystallizing from methanol, the preparation can be separated into a crystallized and an oily part, both of which are effective in the capon comb test.
EMI1.3
atmosphere shaken. The reaction solution freed from the catalyst is evaporated to dryness in vacuo, the residue is taken up in ether and the ethereal solution is shaken with aqueous alkali to remove any traces of non-hydrogenated substance that may still be present. After the ether has been chased away, a light-colored, very consistent resin is obtained whose CH determination is based on
EMI1.4
This preparation can be separated from crystallized fractions by recrystallization and subsequent fractional distillation in a high vacuum,
which already show a physiological effect with 0 # 5 mg in the capon comb test.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE142026X | 1932-10-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT142026B true AT142026B (en) | 1935-06-11 |
Family
ID=5668995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT142026D AT142026B (en) | 1932-10-27 | 1933-10-06 | Process for the preparation of hydrogenation products of the follicular hormone. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT142026B (en) |
-
1933
- 1933-10-06 AT AT142026D patent/AT142026B/en active
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