Following administration of d-α-tocopherol-C14 to rats, a previously uncharacterized metabolite of the vitamin was isolated from the liver. This compound was shown by cochromatography and carrier crystallization to be identical to an oxidation product of α-tocopherol obtained by treatment with alkaline K3Fe(CN)6. Evidence is presented that the compound is a dimer of α-tocopherol.
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The synthesis of the compound was achieved by a slight modification of the procedure of Martius and Eilingsfeld (3). d+Tocopherol, 2.0 g., was dissolved in 100 ml. petroleum ether (30-60”) and combined with 40 ml. of 0.2 N NaOH containing 4.0 g. K3Fe(CN) 6. The mixture was shaken for 1 hr. in a water bath at 45°C. After removal of the organic phase, the aqueous phase was washed with two 100-ml. portions of petroleum ether, and the combined ether phases were backwashed five times with 100 ml. water. The petroleum ether was dried over anhydrous NatSOd, and the solvent was re- 1 This investigation was supported by grants from the National Science Foundation (G-21374) and the Muscular Dystrophy Associations of America, Inc.