DE358873C - Process for the preparation of verbenaline - Google Patents

Process for the preparation of verbenaline

Info

Publication number
DE358873C
DE358873C DER49785D DER0049785D DE358873C DE 358873 C DE358873 C DE 358873C DE R49785 D DER49785 D DE R49785D DE R0049785 D DER0049785 D DE R0049785D DE 358873 C DE358873 C DE 358873C
Authority
DE
Germany
Prior art keywords
verbenaline
preparation
lead
vinegar
glycoside
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
DER49785D
Other languages
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
Priority to DER49785D priority Critical patent/DE358873C/en
Application granted granted Critical
Publication of DE358873C publication Critical patent/DE358873C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification
    • C07H1/08—Separation; Purification from natural products

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)
  • Compounds Of Unknown Constitution (AREA)
  • Saccharide Compounds (AREA)

Description

Verfahren zur Darstellung von Verbenalin. Die Darstellung des in Verbena officinalis vorkommenden Glykosids Verbenalin hat B o iu r d i e r (Arch. d. Ph. -246, -27.2) beschrieben. Die Darstellung nach diesem Verfahren ist sehr umständlich und geschieht unter ausschließlicher Verwendung größerer Mengen teurer organischer Lösungsmittel, weshalb sie für den Großbetrieb ungeeignet ist.Process for the preparation of verbenaline. The representation of the glycoside verbenalin occurring in Verbena officinalis has been described by B o iu r d ier (Arch. D. Ph. -246, -27.2) . The representation according to this method is very cumbersome and is done with the exclusive use of larger amounts of expensive organic solvents, which is why it is unsuitable for large-scale operations.

Es wurde nun gefunden, daß man (die mit Wasser oder Alkohol erhaltenen Auszügedes Pflanzenmaterials idurch. Zusatz von Erdalka11- oder Schwermetallsalzen, insbesondere Bleiessig, von der Hauptmenge der Ballaststoffe befreien kann, während das Verbenalin restlos in Lösung bleibt. Die Abscheidung des GIvkosids beruht auf der -bisher nicht bekannten Eigenschaft desselben, durch Ammoniak und Bleiessig vollständig fällbar zu sein. Der Bleiniederschlag wird in bekannter Weise durch Schwefelwasserstoff zerlegt, die wäßrige Lösung zweckmäßig im Vakuum konzentriert und das Verbenalin durch Behandeln mit geeigneten organischen Lösungsmitteln, wie Es,sigäther, abgeschieden.It has now been found that (those obtained with water or alcohol Extracts of the plant material by. Addition of alkaline earth or heavy metal salts, In particular, lead vinegar can get rid of the bulk of fiber while the verbenaline remains completely in solution. The deposition of the GIvkosids is based on the previously unknown property of ammonia and lead acetic acid to be fully precipitable. The lead precipitation is carried out in a known manner Disassembled hydrogen sulfide, the aqueous solution conveniently concentrated in vacuo and the verbenaline by treatment with suitable organic solvents such as It, sigether, separated.

B e i s p i e 1 : Der wäßrige Auszug von i kg käuflicher Droge von Verbena officinalis wird so lange mit Bleiessig versetzt, als noch ein Niederschlag entsteht. Darauf filtriert man ab, wäscht den Filterrückstand erschöpfend mit Wasser aus und fällt aus dem vereinigten Filtrat das Verbenalin mit Amnioniak und Bileiessig. Der Niederschlag wir-d abfiltriert, ausgewaschen, in Wasser suspendiert und mit Schwefelwasserstoff zerlegt. Die vom Bleisulfid abfiltrierte Glykosid-lösung wird im Vakuum eingeengt und der syr-upöse Rückstand wiederholt mit heißem EssigÜther extrahiert. Nach dem Erkalten des nötigenfalls eingedampften Essigätherauszuges kristallisieren 7 g Verbenalin aus. Durch Umkristallisieren aus Alkohol erhält man 6 g reines Produkt in farblosen Prismen vom SmP 179 bis i8o' (unkorr.).B ice p e 1: The aqueous extract of i kg commercially available drug of Verbena officinalis is so long treated with lead acetate as a precipitate is formed. It is then filtered off, the filter residue is washed exhaustively with water and verbenaline is precipitated from the combined filtrate with amnionia and bilious acetic acid. The precipitate is filtered off, washed out, suspended in water and decomposed with hydrogen sulfide. The glycoside solution filtered off from the lead sulfide is concentrated in vacuo and the syrupy residue is extracted repeatedly with hot vinegar-ether. After the vinegar extract, which may have been evaporated, has cooled down, 7 g of verbenaline crystallize out. Recrystallization from alcohol gives 6 g of pure product in colorless prisms from SmP 179 to 18o '(uncorr.).

Claims (1)

PATENT-ANspRucii: Verfahren zur Darstellung von Verbenalin, dadurch gekennzeichnet, daß man Auszüge des Pflanzenmaterials durch Fällen mit Erdalkali- oder Schwermetallsalzen von der Hauptmenge der Ballaststoffe befreit, aus dem Filtrat das Glykosid mit Ainmoniak und Bleiessig fällt, den erhaltenen Niederschlag entbleit, die das Glykos-i#d enthaltene wäßrige Lösung zweckmäßig unter Zuhilfenahme des Vakuums einengt und ausdern Rückstand das G#ykosid mit einem organischen Lösungsmittel, wie Essigäther, abscheidet.PATENT-ANspRucii: Process for the preparation of verbenaline, thereby characterized in that extracts of the plant material by precipitating with alkaline earth or heavy metal salts freed from the bulk of the dietary fiber from the filtrate the glycoside falls with ammonia and lead acetic acid, the precipitate obtained is discharged, the aqueous solution containing the Glykos-i # d expediently with the aid of the vacuum concentrates and ausdern residue the G # ykosid with an organic solvent, like vinegar.
DER49785D 1920-03-09 1920-03-09 Process for the preparation of verbenaline Expired DE358873C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DER49785D DE358873C (en) 1920-03-09 1920-03-09 Process for the preparation of verbenaline

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DER49785D DE358873C (en) 1920-03-09 1920-03-09 Process for the preparation of verbenaline

Publications (1)

Publication Number Publication Date
DE358873C true DE358873C (en) 1922-09-14

Family

ID=7408830

Family Applications (1)

Application Number Title Priority Date Filing Date
DER49785D Expired DE358873C (en) 1920-03-09 1920-03-09 Process for the preparation of verbenaline

Country Status (1)

Country Link
DE (1) DE358873C (en)

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