CH215341A - Process for the preparation of Eriodictyol-Cellobiosid. - Google Patents

Process for the preparation of Eriodictyol-Cellobiosid.

Info

Publication number
CH215341A
CH215341A CH215341DA CH215341A CH 215341 A CH215341 A CH 215341A CH 215341D A CH215341D A CH 215341DA CH 215341 A CH215341 A CH 215341A
Authority
CH
Switzerland
Prior art keywords
eriodictyol
split
parts
cellobiosid
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie 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 Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH215341A publication Critical patent/CH215341A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/06—Benzopyran radicals
    • C07H17/065—Benzo[b]pyrans
    • C07H17/07—Benzo[b]pyran-4-ones

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  • 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)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Herstellung von     Eriodictyol-cellobiosid.       Das Hauptpatent     betrifft    ein Verfahren  zur     Herstellung    von     Eriodictyolglukosid,     welches dadurch gekennzeichnet ist, dass  man ein     Alkalisalz    des     Briodictyols    mit  einer     Acetohalogenglukose    zur Umsetzung       bringt        und        aus    dem so erhaltenen     Acetyl-          glukosid    mit Hilfe     eines    alkalisch reagieren  den Mittels die     Acetylgruppen    abspaltet.  



  Es wurde weiter     gefunden,    dass man in  analoger Weise     Eriodictyolcellobiosid    her  stellen kann, indem man ein     Alkalisalz    des       Eriodictyols        mit    einer     Heptaacetohalogen-          cellobiose    zur Umsetzung     bringt    und aus dem  so erhaltenen     Heptaacetylcellobiosid        mit     Hilfe eines alkalisch reagierenden     Mittels    die       Acetylgruppen    abspaltet.

   Als     Heptaaceto-          halogencellobiose        kommt    in erster Linie       Heptaacetobromcellobiose    in Betracht.  



  Die neue     Verbindung    entspricht der For  mel  
EMI0001.0032     
    Sie ist wegen ihrer     physiologischen    Wirk  samkeit von Interesse und soll für therapeu  tische Zwecke Verwendung finden. Sie bil  det ein in Wasser, Methylalkohol und     Äthyl-          alkohol    leicht, in Aceton schwerer, in Äther,  Chloroform und Benzol kaum lösliches gel  bes     Pulver.    Sie gibt die     Anthocyanidin-          reaktion    und wird durch Säuren gespalten.

    <I>Beispiel:</I>  23 Gewichtsteile     Eriodictyol    werden un  ter     Luftabschluss    in 300     Volumteilen    Aceton  und 160     Volumteilen        n-Natronlauge    gelöst.  Hierzu gibt man eine Lösung von 56 Ge-           wichtsteilen        Heptaacetobromcellobiose    in 800       Volumteilen    Aceton und lässt das Gemisch  über Nacht stehen. Alsdann säuert man mit  Essigsäure an und giesst in Essigester. Nach  dem Ausschütteln der     Essigesterlösung    mit  Wasser und     Bikarbonatlösung    wird sie mit  Natriumsulfat getrocknet und dann einge  dampft.

   Der     Eindampfrückstand    wird in  Chloroform gelöst und mit trockenem Äther  und     Gasolin    gefällt.  



  Dieses     Heptaacetylcellobiosid    bildet ein  gelbliches Pulver ohne scharfen Schmelz  punkt.  



  31 Gewichtsteile     Eriodictyol-heptaacetyl-          cellobiosid    werden in 60     Volumteilen    Me  thanol gelöst     und    mittels einer Lösung von  4     Gewichtsteilen    Natrium in 80     Volumteilen     Methanol in das     Natriumsalz    verwandelt, das       abgesaugt    und mittels Essigsäure zerlegt  wird. Man dampft ein, löst in Methanol und  fällt mit Äther. Das so     erhaltene        Cellobiosid     ist in Wasser sehr leicht löslich und hat  keinen     Schmelzpunkt,    sondern bläht sich  beim Erhitzen auf.



  Process for the preparation of Eriodictyol-Cellobiosid. The main patent relates to a process for the production of eriodictyol glucoside, which is characterized in that an alkali salt of briodictyol is reacted with an acetohalogenglucose and the acetyl groups are split off from the acetyl glucoside thus obtained with the aid of an alkaline agent.



  It has also been found that eriodictyolcellobioside can be prepared in an analogous manner by reacting an alkali salt of eriodictyol with a heptaacetohalogencellobiose and splitting off the acetyl groups from the heptaacetylcellobioside thus obtained with the aid of an alkaline agent.

   Heptaacetobromcellobiose comes primarily into consideration as heptaacetohalcellobiose.



  The new connection corresponds to the formula
EMI0001.0032
    It is of interest because of its physiological efficacy and should be used for therapeutic purposes. It forms a yellow powder that is easily soluble in water, methyl alcohol and ethyl alcohol, more difficult in acetone, and hardly soluble in ether, chloroform and benzene. It gives the anthocyanidin reaction and is split by acids.

    <I> Example: </I> 23 parts by weight of Eriodictyol are dissolved in 300 parts by volume of acetone and 160 parts by volume of n-sodium hydroxide solution in the absence of air. A solution of 56 parts by weight of heptaacetobromcellobiose in 800 parts by volume of acetone is added and the mixture is left to stand overnight. It is then acidified with acetic acid and poured into ethyl acetate. After shaking out the ethyl acetate solution with water and bicarbonate solution, it is dried with sodium sulfate and then evaporated.

   The evaporation residue is dissolved in chloroform and precipitated with dry ether and gasoline.



  This heptaacetyl cellobioside forms a yellowish powder with no sharp melting point.



  31 parts by weight of eriodictyol heptaacetyl cellobioside are dissolved in 60 parts by volume of methanol and converted into the sodium salt using a solution of 4 parts by weight of sodium in 80 parts by volume of methanol, which is filtered off with suction and broken down using acetic acid. It is evaporated, dissolved in methanol and precipitated with ether. The cellobioside obtained in this way is very easily soluble in water and has no melting point, but instead puffs up when heated.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Eriodic- tyolcellobiosid, dadurch gekennzeichnet, dass man ein Alkalisalz des Eriodictyols mit einer Heptaacetohalogencellobiose zur Um setzung bringt und aus dem so erhaltenen Acetylcellobiosid mit Hilfe eines alkalisch reagierenden Mittels die Acetylgruppen ab spaltet. Das Cellobiosid ist ein in Wasser, Me thylalkohol und Äthylalkohol leicht, in Ace ton schwerer, in Äther, Chloroform und Ben zol kaum lösliches gelbes Pulver. Es hat kei nen scharfen Schmelzpunkt, sondern bläht sich beim Erhitzen auf. PATENT CLAIM: A process for the production of eriodictyolcellobioside, characterized in that an alkali salt of eriodictyol is reacted with a heptaacetohalogencellobiose and the acetyl groups are split off from the acetylcellobioside thus obtained with the aid of an alkaline agent. Cellobioside is a yellow powder that is lightly soluble in water, methyl alcohol and ethyl alcohol, heavier in acetone, and hardly soluble in ether, chloroform and benzene. It doesn't have a sharp melting point, but rather puffs up when heated. Es gibt die Antho- cyanidinreaktion und wird durch Säuren ge spalten. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als Heptaaceto- halogencellobiose Heptaacetobromeellobiose verwendet. There is the anthocyanidin reaction and it is split by acids. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that heptaacetobromeellobiose is used as heptaacetohalcellobiose.
CH215341D 1936-12-24 1937-12-20 Process for the preparation of Eriodictyol-Cellobiosid. CH215341A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE215341X 1936-12-24

Publications (1)

Publication Number Publication Date
CH215341A true CH215341A (en) 1941-06-15

Family

ID=96230377

Family Applications (2)

Application Number Title Priority Date Filing Date
CH210424D CH210424A (en) 1936-12-24 1937-12-20 Process for the production of eriodictyol glucoside.
CH215341D CH215341A (en) 1936-12-24 1937-12-20 Process for the preparation of Eriodictyol-Cellobiosid.

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CH210424D CH210424A (en) 1936-12-24 1937-12-20 Process for the production of eriodictyol glucoside.

Country Status (1)

Country Link
CH (2) CH210424A (en)

Also Published As

Publication number Publication date
CH210424A (en) 1940-07-15

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