Tocopherols TCP) are a class of organic chemical compounds (more precisely, various methylated phenols), many of which have vitamin E activity. Because the vitamin activity was first identified in 1936 from a dietary fertility factor in rats, it was given the name "tocopherol" using the Greek words "τÏŒκος" [tókos, birth], and "φέρειν", [phérein, to bear or carry] meaning in sum "to carry a pregnancy," with the ending "-or" signifying its status as chemical alcohol.

α-Tocopherol is the main source found in supplements and in the European diet, where the main dietary sources are olive and sunflower oils, while γ-tocopherol is the most common form in the American diet due to a higher intake of soybean and corn oil.

Tocotrienols, which are related compounds, also have vitamin E activity. All of these various derivatives with vitamin activity may correctly be referred to as "vitamin E". Tocopherols and tocotrienols are fat-soluble antioxidants but also seem to have many other functions in the body.

The tocotrienols have the same methyl structure at the ring and the same Greek letter-methyl-notation but differ from the analogous tocopherols by the presence of three double bonds in the hydrophobic side chain. The unsaturation of the tails gives tocotrienols only a single stereoisomeric carbon (and thus two possible isomers per structural formula, one of which occurs naturally), whereas tocopherols have three centers (and eight possible stereoisomers per structural formula, again, only one of which occurs naturally).

Each form has a different biological activity. In general, the unnatural l-isomers of tocotrienols lack almost all vitamin activity, and half of the possible 8 isomers of the tocopherols (those with 2S chirality at the ring-tail junction) also lack vitamin activity. Of the stereoisomers that retain activity, increasing methylation, especially full methylation to the alpha-form, increases vitamin activity. In tocopherols, this is due to the preference of the tocopherol binding protein for the alpha-tocopherol form of the vitamin.

Alpha-tocopherol is the form of vitamin E that is preferentially absorbed and accumulated in humans.The measurement of "vitamin E" activity in international units (IU) was based on fertility enhancement by the prevention of miscarriages in pregnant rats relative to alpha-tocopherol.

Although the mono-methylated form ddd-gamma-tocopherol is the most prevalent form of vitamin E in oils, there is evidence that rats can methylate this form to the preferred alpha-tocopherol, since several generations of rats retained alpha-tocopherol tissue levels, even when those generations were fed only gamma-tocopherol through their lives.

Last Updated on: May 20, 2024