CH177155A - Process for the preparation of a cholesterol ester. - Google Patents
Process for the preparation of a cholesterol ester.Info
- Publication number
- CH177155A CH177155A CH177155DA CH177155A CH 177155 A CH177155 A CH 177155A CH 177155D A CH177155D A CH 177155DA CH 177155 A CH177155 A CH 177155A
- Authority
- CH
- Switzerland
- Prior art keywords
- cholesterol
- preparation
- cholesterol ester
- heated
- process according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 150000001840 cholesterol esters Chemical class 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 16
- 235000012000 cholesterol Nutrition 0.000 claims description 8
- SRELFLQJDOTNLJ-UHFFFAOYSA-N Hydnocarpic acid Natural products OC(=O)CCCCCCCCCCC1CCC=C1 SRELFLQJDOTNLJ-UHFFFAOYSA-N 0.000 claims description 5
- SRELFLQJDOTNLJ-HNNXBMFYSA-N (R)-hydnocarpic acid Chemical compound OC(=O)CCCCCCCCCC[C@@H]1CCC=C1 SRELFLQJDOTNLJ-HNNXBMFYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 229940126601 medicinal product Drugs 0.000 claims description 2
- 101100495769 Caenorhabditis elegans che-1 gene Proteins 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- -1 hydnocarpic acid cholesteryl ester Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Description
Verfahren zur Darstellung eines Cholesterinesters. In dem Patent<B>170615</B> ist die Darstellung eines therapeutisch wertvollen Cholesterin- esters durch Veresterung von Chaulmoogra- säure mit Cholesterin beschrieben.
Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Darstellung eines Cholesterin- esters, das dadurch gekennzeichnet ist, dass man Cholesterin zur Umsetzung bringt mit einer Verbindung der Formel
EMI0001.0010
worin X einen bei der Umsetzung mit Chol esterin sich abspaltenden Rest bedeutet.
Das so erhaltene neue Produkt bildet weisse Blättchen vom Schmelzpunkt 63-65 C. Es soll als Arzneimittel Verwendung finden. <I>Beispiel:</I> 10 gr Cholesterin und 30 gr Hydnocarp- säure werden im Ölbad unter Durchleiten von Kohlensäure 5 Stunden auf 250-270 er hitzt. Nach teilweisem Erkalten wird in 250 cm3 abs. Alkohol gegossen, woraus nach einiger Zeit der Hydnocarpsäurecholesterylester in weissen Blättchen ausfällt.
Durch Umkristalli- sieren aus Alkohol-Essigester wird die neue Verbindung in Blättchen vom Schmelzpunkt 63-65 erhalten. Die Ausbeute beträgt 14 gr. An Stelle der Hy dnocarpsäure kann auch die entsprechende Menge Hydnocarpsäurechlorid zur Verwendung gelangen.
Process for the preparation of a cholesterol ester. The patent <B> 170615 </B> describes the preparation of a therapeutically valuable cholesterol ester by esterifying chaulmograic acid with cholesterol.
The present invention relates to a process for the preparation of a cholesterol ester, which is characterized in that cholesterol is reacted with a compound of the formula
EMI0001.0010
where X is a radical which is split off on reaction with cholesterol.
The new product obtained in this way forms white flakes with a melting point of 63-65 C. It is said to be used as a medicinal product. <I> Example: </I> 10 grams of cholesterol and 30 grams of hydnocarpic acid are heated to 250-270 for 5 hours in an oil bath while passing through carbonic acid. After partial cooling, abs. Poured alcohol, from which after a while the hydnocarpic acid cholesteryl ester precipitates in white flakes.
Recrystallization from alcohol / ethyl acetate gives the new compound in flakes with a melting point of 63-65. The yield is 14 g. Instead of hy dnocarpic acid, the corresponding amount of hydnocarpic acid chloride can also be used.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH170615T | 1933-06-29 | ||
| CH177155T | 1933-06-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH177155A true CH177155A (en) | 1935-05-15 |
Family
ID=25718943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH177155D CH177155A (en) | 1933-06-29 | 1933-06-29 | Process for the preparation of a cholesterol ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH177155A (en) |
-
1933
- 1933-06-29 CH CH177155D patent/CH177155A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH177155A (en) | Process for the preparation of a cholesterol ester. | |
| AT129782B (en) | Process for the preparation of 0,0-diacetyldiphenolisatin. | |
| DE764747C (en) | Process for the preparation of derivatives of androstediol-3, 17 and androstenediol-3, 17 | |
| AT159314B (en) | Process for the preparation of 17-oxy-3-oxo- or 3.17-dioxycyclopentanopolyhydrophenanthrenes or their esters. | |
| CH201506A (en) | Process for the preparation of a quaternary aminobenzylacylamine. | |
| DE699309C (en) | Process for the preparation of pregnenolones | |
| AT160488B (en) | Process for the preparation of compounds in the 3-position of the estradiol type. | |
| CH201505A (en) | Process for the preparation of a quaternary aminobenzylacylamine. | |
| CH175234A (en) | Process for the preparation of 4-amino-3-ethoxy-4'-methoxy-diphenylamine. | |
| CH190546A (en) | Process for the preparation of 5-benzoylamino-m-phenanthroline. | |
| CH201511A (en) | Process for the preparation of a quaternary aminobenzylacylamine. | |
| CH229775A (en) | Process for the production of testosterone cyclohexyl enol ether. | |
| CH180874A (en) | Process for the preparation of an acylated dihydrofollicle hormone. | |
| CH207493A (en) | Process for the preparation of a monoester of the androstane series. | |
| CH85310A (en) | Process for the preparation of allyl morphine. | |
| CH181176A (en) | Process for the preparation of a derivative of 5,5-phenylethylhydantoin. | |
| CH562214A5 (en) | N-substd ortho-anisamides prepn | |
| CH201508A (en) | Process for the preparation of a quaternary aminobenzylacylamine. | |
| CH365066A (en) | Process for the preparation of 16a-methyl-pregnan-3a-ol-11,20-dione-3-acetate | |
| CH201507A (en) | Process for the preparation of a quaternary aminobenzylacylamine. | |
| CH228146A (en) | Process for the preparation of 5-5-C-C- 1-Cycloheptenylethylbarbituric acid. | |
| CH143262A (en) | Process for the preparation of a compound with a hydrogenated ring system. | |
| CH151195A (en) | Process for the preparation of the α-bromoisocrotonic acid ester of 4-glycolylaminobenzene-1-arsic acid. | |
| CH180595A (en) | Process for the preparation of 2-butoxy-5-acetylaminopyridine. | |
| DE1122950B (en) | Process for the preparation of í¸-17ª ‡ -hydroxyprogesterone esters |