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DL-α-Tocopherol

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DL-α-Tocopherol Basic information
DL-α-Tocopherol Chemical Properties
Safety Information
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DL-α-Tocopherol Usage And Synthesis
  • Chemical Properties1mg = 1.1 IU
  • Chemical PropertiesAlpha tocopherol is a natural product. The PhEur 6.0 describes alpha-tocopherol as a clear, colorless or yellowish-brown, viscous, oily liquid.
  • UsesAn antioxidant that protects cell membrane lipids from oxidative damage
  • Production MethodsNaturally occurring tocopherols are obtained by the extraction or molecular distillation of steam distillates of vegetable oils; for example, alpha tocopherol occurs in concentrations of 0.1–0.3% in corn, rapeseed, soybean, sunflower, and wheat germ oils.Beta and gamma tocopherol are usually found in natural sources along with alpha tocopherol. Racemic synthetic tocopherols may be prepared by the condensation of the appropriate methylated hydroquinone with racemic isophytol.
  • Pharmaceutical ApplicationsAlpha tocopherol is primarily recognized as a source of vitamin E, and the commercially available materials and specifications reflect this purpose. While alpha tocopherol also exhibits antioxidant properties, the beta, delta, and gamma tocopherols are considered to be more effective as antioxidants.
    Alpha-tocopherol is a highly lipophilic compound, and is an excellent solvent for many poorly soluble drugs.Of widespread regulatory acceptability, tocopherols are of value in oil- or fat-based pharmaceutical products and are normally used in the concentration range 0.001–0.05% v/v. There is frequently an optimum concentration; thus the autoxidation of linoleic acid and methyl linolenate is reduced at low concentrations of alpha tocopherol, and is accelerated by higher concentrations. Antioxidant effectiveness can be increased by the addition of oil-soluble synergists such as lecithin and ascorbyl palmitate.
    Alpha tocopherol may be used as an efficient plasticizer. It has been used in the development of deformable liposomes as topical formulations.
    d-Alpha-tocopherol has also been used as a non-ionic surfactant in oral and injectable formulations.
  • SafetyTocopherols (vitamin E) occur in many food substances that are consumed as part of the normal diet. The daily nutritional requirement has not been clearly defined but is estimated to be 3.0–20.0 mg. Absorption from the gastrointestinal tract is dependent upon normal pancreatic function and the presence of bile. Tocopherols are widely distributed throughout the body, with some ingested tocopherol metabolized in the liver; excretion of metabolites is via the urine or bile. Individuals with vitamin E deficiency are usually treated by oral administration of tocopherols, although intramuscular and intravenous administration may sometimes be used.
    Tocopherols are well tolerated, although excessive oral intake may cause headache, fatigue, weakness, digestive disturbance, and nausea. Prolonged and intensive skin contact may lead to erythema and contact dermatitis.
    The use of tocopherols as antioxidants in pharmaceuticals and food products is unlikely to pose any hazard to human health since the daily intake from such uses is small compared with the intake of naturally occurring tocopherols in the diet.
    The WHO has set an acceptable daily intake of tocopherol used as an antioxidant at 0.15–2.0 mg/kg body-weight.
  • storageTocopherols are oxidized slowly by atmospheric oxygen and rapidly by ferric and silver salts. Oxidation products include tocopheroxide, tocopherylquinone, and tocopherylhydroquinone, as well as dimers and trimers. Tocopherol esters are more stable to oxidation than the free tocopherols but are in consequence less effective antioxidants.
    Tocopherols should be stored under an inert gas, in an airtight container in a cool, dry place and protected from light.
  • Purification MethodsDissolve dl--tocopherol in anhydrous MeOH (15mL/g) cool to -6o for 1hour, then chill in a Dry-ice/acetone bath; crystallisation is induced by scratching with a glass rod. The dl--acetate [52225-20-4] (see DL-vitamin E actetate below) is a viscous yellow liquid with m -7o, b 184o/0.01mm, 224o/0.3mm, d 4 20 0.953, n D 20 1.496. It is used as a standard for Vitamin E activity where the unit of activity is attained with 1mg of pure dl--acetate. [Friedrich “Vitamins” Water de Guyter Publ, Berlin 1988, Beilstein 17/4 V 168.]
  • IncompatibilitiesTocopherols are incompatible with peroxides and metal ions, especially iron, copper, and silver. Tocopherols may be absorbed into plastic.
  • Regulatory StatusGRAS listed. Accepted in Europe as a food additive. Included in the FDA Inactive Ingredients Database (IV injections, powder, lyophilized powder for liposomal suspension; oral capsules, tablets, and topical preparations). Included in the Canadian List of Acceptable Non-medicinal Ingredients. Included in nonparenteral medicines licensed in the UK.
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