CH208086A - Process for the preparation of dl-acetyl-a-tocopherol. - Google Patents

Process for the preparation of dl-acetyl-a-tocopherol.

Info

Publication number
CH208086A
CH208086A CH208086DA CH208086A CH 208086 A CH208086 A CH 208086A CH 208086D A CH208086D A CH 208086DA CH 208086 A CH208086 A CH 208086A
Authority
CH
Switzerland
Prior art keywords
tocopherol
acetyl
preparation
parts
acetate
Prior art date
Application number
Other languages
German (de)
Inventor
F Hoffmann- Aktiengesellschaft
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of CH208086A publication Critical patent/CH208086A/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • A61K31/355—Tocopherols, e.g. vitamin E
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
    • C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

       

  Verfahren zur Darstellung von     dl-Acetyl-a-tocopherol.       Die kürzlich aufgefundene Synthese des       Vitamin-E    führt zu     racemischen        Toco-          pherolen.    So erhält man zum Beispiel durch  Kondensation von     Trimethylhydrochinon    und       Phytol    das     dl-a-Tocopherol.    Dieses Produkt  ist gegenüber Oxydationsmitteln (z. B. Luft)  und Feuchtigkeit empfindlich.  



  Es     wurde    nun     gefunden,    dass das     dl-Ace-          tyl-a-tocopherol    stärker wirksam und auch  beständiger ist als das     unveresterte        Toco-          pherol.     



  Gegenstand vorliegenden Patentes     ist    ein  Verfahren zur Darstellung von     dl-Acetyl-a-          tocopherol,    welches dadurch     gekennzeichnet     ist, dass man auf     dl-a-Tocopherol        Acetylie-          rungsmittel    einwirken lässt.  



  Das durch     Einwirkung    von     Acetylie-          rungsmitteln    auf     dl-a-Tocopherol    hergestellte       dl-Acetyl-a-tocopherol    ist ein hellgelbes,  sehr     viscoses        Öl;    sein     Brechungsexponent          (ii2D)    beträgt 1,4965. Es siedet bei     einem     Druck von 0,3 mm bei 224'. In     methyl-          alkoholischer    Lösung reduziert es neutrales    Silbernitrat nicht und     Tollens    Reagens nur  allmählich.

   Es löst sich in 25 Teilen     Me-          thyl-    und in 5 Teilen Äthylalkohol. Spielend  löslich ist es in Benzol, Äther,     Petroläther,     Aceton, Essigester und Chloroform. Alko  holische Laugen verseifen das Acetat zu     dl-          a-Tocopherol.     



  Das dl -     Acetyl    - a -     tocopherol    soll. als       Arzneimittel    verwendet werden.    <I>Beispiel:</I>  10 Teile     dl-a-Tocopherol    werden     in    40  Teilen     Essigsäureanhydrid    gelöst.     Man    rührt  die     Mischung        kräftig,    leitet Wasserstoff ein  und fügt eine kleine Menge konzentrierter  Schwefelsäure zu. Die Lösung wird sofort  rot und erwärmt sich. Dann wird die Farbe  der Lösung bald graugrün.

   Man hält die       Temperatur    für 2 Stunden auf 40  , neutrali  siert darauf die Schwefelsäure durch Zu  fügen von wenig     Natriumacetat    und dampft  im Vakuum das     Essigsäureanhydrid    voll  ständig ab. Der Rückstand wird im Hoch-           vakuum    destilliert oder     in    einer     Molekular-          Destillationsapparatur    verdampft. Die Aus  beute ist beinahe quantitativ.



  Process for the preparation of dl-acetyl-a-tocopherol. The recently discovered synthesis of vitamin E leads to racemic tocopherols. For example, by condensing trimethylhydroquinone and phytol, dl-a-tocopherol is obtained. This product is sensitive to oxidizing agents (e.g. air) and moisture.



  It has now been found that the dl-acetyl-a-tocopherol is more effective and also more stable than the unesterified tocopherol.



  The subject of the present patent is a process for the preparation of dl-acetyl-a-tocopherol, which is characterized in that dl-a-tocopherol acetylating agent is allowed to act.



  The dl-acetyl-a-tocopherol produced by the action of acetylating agents on dl-a-tocopherol is a light yellow, very viscous oil; its refraction exponent (ii2D) is 1.4965. It boils at a pressure of 0.3mm at 224 '. In methyl alcoholic solution it does not reduce neutral silver nitrate and Tollen's reagent only gradually.

   It dissolves in 25 parts of methyl and 5 parts of ethyl alcohol. It is easily soluble in benzene, ether, petroleum ether, acetone, ethyl acetate and chloroform. Alcoholic alkalis saponify the acetate to dl-a-tocopherol.



  The dl-acetyl-a-tocopherol is said to. be used as medicines. <I> Example: </I> 10 parts of dl-a-tocopherol are dissolved in 40 parts of acetic anhydride. The mixture is stirred vigorously, hydrogen is passed in and a small amount of concentrated sulfuric acid is added. The solution immediately turns red and warms up. Then the color of the solution will soon turn gray-green.

   The temperature is kept at 40 for 2 hours, the sulfuric acid is then neutralized by adding a little sodium acetate and the acetic anhydride is completely evaporated in vacuo. The residue is distilled in a high vacuum or evaporated in a molecular distillation apparatus. The yield is almost quantitative.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von dl-Acetyl- a-tocopherol, dadurch gekennzeichnet, daB auf dl-a-Tocopherol Acetylierungsmittel ein wirken gelassen werden. dl-Acetyl-a-tocopherol ist ein hellgelbes, sehr viskoses <B>01;</B> sein Brechungsexponent (0 n$D ) beträgt 1,4965. Es siedet bei einem Druck von 0,3 mm bei 224 . In methylalko- holischer Lösung reduziert es neutrales Sil bernitrat nicht und Tollens Reagens nur all mählich. PATENT CLAIM: Process for the preparation of dl-acetyl-a-tocopherol, characterized in that acetylating agents are allowed to act on dl-a-tocopherol. dl-Acetyl-a-tocopherol is a light yellow, very viscous <B> 01; </B> its refraction exponent (0 n $ D) is 1.4965. It boils at a pressure of 0.3mm at 224. In a methyl alcoholic solution it does not reduce neutral silver nitrate and Tollen's reagent only gradually. Es löst sich in 25 Teilen Methyl- und in 5 Teilen Äthylalkohol. Spielend lös lich ist es in Benzol, Äther, Petroläther, Ace ton, Essigester und Chloroform. Alkoholische Laugen verseifen das Acetat zu dl-a-Toco- pherol. Das dl - Acetyl - a - tocopherol soll als Arzneimittel verwendet werden. It dissolves in 25 parts of methyl alcohol and 5 parts of ethyl alcohol. It is easily soluble in benzene, ether, petroleum ether, acetone, ethyl acetate and chloroform. Alcoholic bases saponify the acetate to dl-a-tocopherol. The dl - acetyl - a - tocopherol should be used as a medicine.
CH208086D 1938-09-29 1938-09-29 Process for the preparation of dl-acetyl-a-tocopherol. CH208086A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH208086T 1938-09-29

Publications (1)

Publication Number Publication Date
CH208086A true CH208086A (en) 1939-12-31

Family

ID=4445888

Family Applications (1)

Application Number Title Priority Date Filing Date
CH208086D CH208086A (en) 1938-09-29 1938-09-29 Process for the preparation of dl-acetyl-a-tocopherol.

Country Status (6)

Country Link
CH (1) CH208086A (en)
DE (1) DE712744C (en)
DK (1) DK59294C (en)
FR (1) FR859834A (en)
GB (1) GB532364A (en)
SE (1) SE99384C1 (en)

Also Published As

Publication number Publication date
SE99384C1 (en) 1940-07-16
FR859834A (en) 1940-12-30
DE712744C (en) 1941-10-24
GB532364A (en) 1941-01-22
DK59294C (en) 1941-12-15

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