DE334553C - Process for the preparation of coagulations of cholic acids - Google Patents

Process for the preparation of coagulations of cholic acids

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Publication number
DE334553C
DE334553C DE1916334553D DE334553DD DE334553C DE 334553 C DE334553 C DE 334553C DE 1916334553 D DE1916334553 D DE 1916334553D DE 334553D D DE334553D D DE 334553DD DE 334553 C DE334553 C DE 334553C
Authority
DE
Germany
Prior art keywords
preparation
coagulations
acid
cholic acids
cholic acid
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.)
Expired
Application number
DE1916334553D
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German (de)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Honeywell Riedel de Haen AG
Original Assignee
JD Riedel AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by JD Riedel AG filed Critical JD Riedel AG
Application granted granted Critical
Publication of DE334553C publication Critical patent/DE334553C/en
Expired legal-status Critical Current

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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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Description

Verfahren zur Darstellung von Abkömmlingen der Cholsäure. Es wurde gefunden, daß man aus den Estern der Cholsäure, insbesondere aus dem leicht herzustellenden Methylester durch Behandeln mit wasserentziehenden Mitteln, wie Kaliumbisultat, leicht Wasser abspalten kann. Die zunächst erhaltenen Ester la-,sen sich leicht verseifen und in die zugehörigen Säuren überführen. Diese haben im allgemeinen die Eigenschaften der Cholsäure, unterscheiden sich aber von ihr vorteilhaft durch Geschmacklosigkeit und stark lösende Wirkung ihrer wäßrigen Salzlösungen für viele unlösliche Substanzen.Process for the preparation of derivatives of cholic acid. It was found that you can use the esters of cholic acid, especially from the easy to prepare Methyl ester by treating with dehydrating agents such as potassium bisultate, can easily split off water. The esters initially obtained can easily be saponify and convert into the associated acids. These generally have the Properties of cholic acid, but differ from it advantageously in tastelessness and their aqueous salt solutions have a strong dissolving effect on many insoluble substances.

Beispiel. 5o g Cholsäuremethylester werden mit 75 9 kristallisierter Glykolsäure erhitzt, bis eine homogene Flüssigkeit entstanden ist. Darauf trägt man 5 g geschmolzenes und fein gepulvertes Kaliumbisulfat unter Umrühren ein und erhitzt rasch auf 130'. Nach kurzer Zeit tritt eine Entmischung der Reaktionsflüssigkeit ein, indem die entstehenden ' ungesättigten Ester sich abscheiden. Man läßt erkalten und behandelt zur Entfernung_ der Glykolsäure und des Kaliumbisulfats mit heißem Wasser. Der unlösliche Rückstand wird dann mit überschüssiger Natronlauge erhitzt, bis Lösung erfolgt ist, aus der nach dem Erkalten durch Ansäuern mit Salzsäure ein Gemisch ungesättigter Säuren ausgefällt wird. Diese werden abgesaugt und getrocknet.Example. 50 g of methyl cholic acid are heated with 75 g of crystallized glycolic acid until a homogeneous liquid has formed. Then add 5 g of melted and finely powdered potassium bisulfate with stirring and heat quickly to 130 °. After a short time separation of the reaction liquid occurs by the resultant 'unsaturated ester separate out. It is allowed to cool and treated with hot water to remove the glycolic acid and potassium bisulfate. The insoluble residue is then heated with excess sodium hydroxide solution until it has dissolved, from which, after cooling, a mixture of unsaturated acids is precipitated by acidification with hydrochloric acid. These are suctioned off and dried.

Zur Trennung löst man in der gleichen Menge j Eisessig unter Erhitzen auf und läßt über Nacht i stehen. Es kristallisiert die Eisessigverbindung der bisher nicht bekannten Apocholsäure in Gestalt gut ausgebildeter Nadeln aus, die nach vorhergehendem Sintern zwischen 150 und i.6o' schmelzen.To separate, dissolve the same amount of glacial acetic acid while heating up and let i stand overnight. It crystallizes the glacial acetic acid that has been used so far unknown apocholic acid in the form of well-developed needles, which according to the preceding Melt sintering between 150 and i.6o '.

Analyse der Eisessig-Verbindung: OJ420 9 gaben 0,3626 CO., und 0,1174 H.0. Gefunden: Berechnet auf C.,H3,0,+CH,COOH: C 69,64 Prozent, 69,--8 Prozent, H 9,0-5 - . 9,40 - . Die durch Abspaltung von Essigsäure daraus leicht erhältliche freie Apocholsäure ist nahezu geschmacklos. In Äther, Benzol, Petroläther ist sie schwer, leicht dagegen in Alkohol löslich.Analysis of the glacial acetic acid compound: OJ420 9 gave 0.3626 CO., And 0.1174 H.0. Found: Calculated C, H3,0, + CH, COOH: C 69.64 percent, 69 - 8 percent, 9.0 to 5 H -. 9.40 -. The free apocholic acid, which can easily be obtained from it by splitting off acetic acid, is almost tasteless. It is heavy in ether, benzene, and petroleum ether, but easily soluble in alcohol.

Aus der Eisessig-Mutterlauge lassen sich durch Ausfällen mit Wasser andere ungesättigte Gallensäuren gewinnen, die sich durch größere Löslichkeit in den meisten organischen Lösungsmitteln von der Apocholsäure unterscheiden.The glacial mother liquor can be precipitated with water win other unsaturated bile acids, which are more soluble in most organic solvents differ from apocholic acid.

Claims (1)

PATENT-A.xLSPRUCII-# Verfahren zur Darstellung von Abkömmlingen der Cholsäure, dadurch gekennzeichnet, daß man die Ester der Cholsäure in bekannter Weisel:mit wasserabspaltenden Mitteln behandelt, die entstandenen Produkte verseift und durch Ansäuern die entsprechenden Säuren abscheidet.PATENT-A.xLSPRUCII- # Method for the representation of descendants of the Cholic acid, characterized in that the esters of cholic acid are known in the art Weisel: treated with water-releasing agents, the resulting products saponified and the corresponding acids are separated by acidification.
DE1916334553D 1916-05-30 1916-05-30 Process for the preparation of coagulations of cholic acids Expired DE334553C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE334553T 1916-05-30

Publications (1)

Publication Number Publication Date
DE334553C true DE334553C (en) 1921-03-14

Family

ID=6217114

Family Applications (1)

Application Number Title Priority Date Filing Date
DE1916334553D Expired DE334553C (en) 1916-05-30 1916-05-30 Process for the preparation of coagulations of cholic acids

Country Status (1)

Country Link
DE (1) DE334553C (en)

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