DE913893C - Process for obtaining valuable steroids from tomato plants - Google Patents

Process for obtaining valuable steroids from tomato plants

Info

Publication number
DE913893C
DE913893C DEB17901A DEB0017901A DE913893C DE 913893 C DE913893 C DE 913893C DE B17901 A DEB17901 A DE B17901A DE B0017901 A DEB0017901 A DE B0017901A DE 913893 C DE913893 C DE 913893C
Authority
DE
Germany
Prior art keywords
tomato plants
obtaining valuable
parts
valuable steroids
steroids
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
DEB17901A
Other languages
German (de)
Inventor
Dr Richard Kuhn
Dr Irmentraut Loew
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to DEB17901A priority Critical patent/DE913893C/en
Application granted granted Critical
Publication of DE913893C publication Critical patent/DE913893C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

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

Description

Verfahren zur Gewinnung wertvoller Steroide aus Tomatenpflanzen Das Patent gii 26o betrifft ein Verfahren zur Gewinnung wertvoller Steroide aus Tomatenpflanzen durch Abtrennung des in diesen enthaltenen Tomatins und Überführung in ein Triacyltomatidin, insbesondere Triacetyltomatidin, bei dem das Triacyltomatidin einer oxydierenden Behandlung mit Kaliumpermanganat oder Wasserstoffperoxyd in Gegenwart stark wirkender Katalysatoren unterworfen wird.Method of Obtaining Valuable Steroids from Tomato Plants That Patent gii 26o relates to a process for obtaining valuable steroids from tomato plants by separating the tomatin contained in these and converting them into a triacyltomatidin, in particular triacetyltomatidin, in which the triacyltomatidin is an oxidizing Treatment with potassium permanganate or hydrogen peroxide in the presence of powerful substances Is subjected to catalysts.

Es wurde nun gefunden, daß man ebenfalls in einfacher Weise zu hochwertigen Produkten gelangt, wenn man ein aus dem Tomatin der Tomatenpflanzen erhältliches Diacyltomatidin, insbesondere das leicht zu gewinnende Diacetyltomatidin, einer oxydierenden Behandlung mit Chromsäure in Eisessig unterwirft. Die Oxydation erfolgt schon bei Zimmertemperatur. Auch die so erhältlichen Produkte sind in der Pharmazie und Kosmetik mit Vorteil verwendbar.It has now been found that high quality can also be obtained in a simple manner Products obtained when one obtainable from the tomatin of the tomato plants Diacyltomatidin, especially the easy to obtain diacetyltomatidin, one Subjected to oxidizing treatment with chromic acid in glacial acetic acid. The oxidation takes place even at room temperature. The products available in this way are also used in pharmacy and cosmetics can be used with advantage.

Beispiel Eine Lösung von i Gewichtsteil Diacetyltomatidin (Schmelzpunkt 186 bis Z87°) in 2o Volumteilen Eisessig und eine Lösung von o,2 Gewichtsteilen Chromtrioxyd in 2o Volumteilen Eisessig läßt man gleichzeitig innerhalb io bis 15 Minuten in 2o Volumteile Eisessig einfließen. Die Lösung färbt sich dabei schmutzigbraun. Nach i stündigem Stehen bei Zimmertemperatur wird sie in 5oo Volumteile Wasser gegossen und die grünliche, saure Lösung mehrmals ausgeäthert. Der Äther wird sodann mit etwa 4%iger Natronlauge säurefrei gewaschen, anschließend noch zweimal mit Wasser durchgeschüttelt und getrocknet. Nach dem Abdampfen des Äthers hinterbleiben o,92 Gewichtsteile eines zähen gelblichen Öles.Example A solution of 1 part by weight of diacetyltomatidine (melting point 186 to Z87 °) in 20 parts by volume of glacial acetic acid and a solution of 0.2 parts by weight Chromium trioxide in 20 parts by volume of glacial acetic acid is left simultaneously within 10 to 15 Pour glacial acetic acid into 2o parts by volume for minutes. The solution turns dirty brown. After standing for 1 hour at room temperature, it is poured into 500 parts by volume of water and etherified the greenish, acidic solution several times. The ether then becomes with about 4% Washed acid-free sodium hydroxide solution, then twice more shaken with water and dried. Remain after evaporation of the ether 92 parts by weight of a viscous yellowish oil.

Beim ChromatographierenaufAlz03 (Brockmann, mit Methanol inaktiviert) werden mit Zoo Volumteilen Benzol 0,33 Gewichtsteile eines kristallisierten Produktes erhalten, das vermutlich 3-Acetyl-tigogeninlacton ist. Nach dem Umkristallisieren aus Methanol oder dem Sublimieren bei 16o bis i7o° unter o,ooimm Druck zeigen die in Nadelform vorliegenden Kristalle den Schmelzpunkt 214 bis 2z5°. Die Ausbeute beträgt 42 °/o der Theorie. When chromatographing on Alz03 (Brockmann, inactivated with methanol), 0.33 parts by volume of benzene are obtained with zoo parts by volume of a crystallized product which is presumably 3-acetyl-tigogenin lactone. After recrystallization from methanol or sublimation at 160 ° to 170 ° under pressure, the needle-shaped crystals have a melting point of 214 to 25 °. The yield is 42% of theory.

Claims (1)

PATENTANSPRUCH: Weiterbildung des Verfahrens des Patents 9ii 26o zur Gewinnung wertvoller Steroide aus Tomatenpflanzen, dadurch gekennzeichnet, daß man ein aus dem Tomatin gewonnenes Diacyltomatidin, insbesondere Diacetyltomatidin, einer oxydierenden Behandlung mit Chromsäure in Eisessig unterwirft.PATENT CLAIM: Further development of the process of the patent 9ii 26o for Obtaining valuable steroids from tomato plants, characterized in that one a diacyltomatidine obtained from the tomatin, in particular diacetyltomatidine, subjected to an oxidizing treatment with chromic acid in glacial acetic acid.
DEB17901A 1951-11-29 1951-11-29 Process for obtaining valuable steroids from tomato plants Expired DE913893C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEB17901A DE913893C (en) 1951-11-29 1951-11-29 Process for obtaining valuable steroids from tomato plants

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB17901A DE913893C (en) 1951-11-29 1951-11-29 Process for obtaining valuable steroids from tomato plants

Publications (1)

Publication Number Publication Date
DE913893C true DE913893C (en) 1954-06-21

Family

ID=6959521

Family Applications (1)

Application Number Title Priority Date Filing Date
DEB17901A Expired DE913893C (en) 1951-11-29 1951-11-29 Process for obtaining valuable steroids from tomato plants

Country Status (1)

Country Link
DE (1) DE913893C (en)

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