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Natural Vitamin E < Home


Chemical Name and Class
d-alpha-tocopherol acetate; Vitamins

Common Names
Natural Vitamin E; d-alpha-tocopherol acetate, d-alpha-tocopheryl acetate, tocopheryl acetate

General Description
Vitamin E is found naturally derived from vegetable oils, primarily soybean, corn, canola, and sunflower oils. Vitamin E found in nature is commonly referred to as d-alpha-tocopherol or RRR-alpha-tocopherol, but other natural forms exist. Esters of natural-source alpha-tocopherol, such as acetate, succinate and etc, are also available. However, only the alpha isomer is currently recognized as measurable for nutritional supplementation. "Vitamin E" is the collective name for a group of fat-soluble compounds with distinctive antioxidant activities.

Naturally occurring vitamin E exists in eight chemical forms (alpha-, beta-, gamma-, and delta-tocopherol and alpha-, beta-, gamma-, and delta-tocotrienol) that have varying levels of biological activity. Alpha- (or α-) tocopherol is presently the only form that is recognized to meet human requirements.

Synthetic Vitamin E, which is commonly referred to as dl-alpha-tocopherol or all-rac-alpha-tocopherol, is a mixture of eight alpha-tocopherol stereoisomers, one isomer is the natural form of d-alpha-tocopherol and the remaining seven stereoisomers have different molecular configurations due to the manufacturing process.

Variations in molecular structures of the natural (d-alpha tocopherol) versus synthetic (dl-alpha tocopherol) forms impact the vitamin’s absorption in the body and thus, in turn its biological availability.

Natural Vitamin E maintains numerous biological advantages when compared to synthetic Vitamin E, for instance:

  • Vitamin E from natural sources (d-alpha tocopherol) is not exactly reproduced by synthetic (dl-alpha tocopherol) manufacturing methods. The resulted effect is that the synthetic form of Vitamin E is not absorbed as completely as its naturally derived counterpart.
  • Natural form d-alpha tocopherol is also retained longer and has greater absorption by the body in comparison to the synthetic dl-alpha tocopherol form. The bioavailability of natural source Vitamin E is twice that of synthetic.
  • A study published in the American Journal of Clinical Nutrition, March 1998, reported that the absorption of Vitamin E through the placenta is 3.5 times higher with the d-alpha tocopherol form versus the dl-alpha tocopherol form.
  • Synthetic Vitamin E is only produced as alpha tocopherol. However, natural Vitamin E is available as alpha tocopherol or a mixture of all four isomers (alpha, beta, gamma, and delta). Studies indicate that the beta, gamma and delta tocopherols could provide benefits previously unrecognized.

Forms of Vitamin E
The names of all types of vitamin E begin with either “d” or “dl,” which refer to differences in chemical structure. The “d” form is natural (also known as RRR-alpha tocopherol) and “dl” is synthetic (more correctly known as all-rac-alpha tocopherol). The natural form is more active and better absorbed. Little is known about how the “unnatural” “l” portion of the synthetic “dl” form affects the body, though no clear toxicity has been discovered.

In theory, when a vitamin E supplement is labeled “400 IU” it should have the same level of activity regardless of its source. This is purportedly achieved by using more synthetic vitamin E to reach the same potency as a lesser amount of natural vitamin E. For example, 100 IU of vitamin E requires about 67 mg of the natural form but closer to 100 mg of the synthetic. However, a recent review of the scientific evidence suggests that natural vitamin E probably has greater activity in the body than indicated on the label.1 Natural vitamin E may be as much as twice as bioavailable as synthetic vitamin E, not 1.36 times as is generally accepted.2 Many doctors advise people to use only the natural, the “d” form, of vitamin E.

After the “d” or “dl” designation, often the Greek letter “alpha” appears which also describes the structure. Synthetic “dl” vitamin E is found only in the alpha form—as in “dl-alpha tocopherol.” Natural vitamin E may be found either as alpha—as in “d-alpha tocopherol”—or in combination with beta, gamma, and delta, labeled “mixed”—as in mixed natural tocopherols.
Little is known about the importance of the beta and delta forms of vitamin E, but a debate has arisen concerning gamma tocopherol. In a test tube study, gamma tocopherol was found to be more effective than alpha tocopherol in protecting against certain specific types of oxidative damage.3 In addition, some research has shown that supplementation with large amounts of alpha tocopherol (such as 1,200 IU per day) increases the breakdown, and decreases blood levels, of gamma tocopherol.4

Human trials with vitamin E have almost always been done with the alpha (not gamma) form. Historically the synthetic “dl” form was used in most trials, but some trials are now using the natural form. The issue of alpha vs. gamma form requires more research before it can be fully understood.
Almost all vitamin E research shows that, when positive results are obtained, hundreds of units per day are required—an amount easily obtained with supplements but impossible with food. Therefore, switching to food sources, as suggested by some researchers, is impractical. On the other hand, the vitamin E occurring naturally in food contains gamma tocopherol and other tocopherols. Thus, it possibly may turn out to be more effective than the vitamin E taken in supplement form. Additional research is needed in this area.

Vitamin E forms are listed as either plain “tocopherol” or tocopheryl followed by the name of what is attached to it, as in “tocopheryl acetate.” The two forms are not greatly different. However, plain tocopherol may be absorbed a little better, while tocopheryl attached forms have a slightly better shelf life. Both forms are active when taken by mouth. However, the skin utilizes the tocopheryl forms very slowly,5 6 so those planning to apply vitamin E to the skin should buy plain tocopherol. The most common forms of vitamin E are d-alpha tocopherol and d-alpha tocopheryl acetate or succinate. Both of these d (natural) alpha forms are frequently recommended by doctors. Although the succinate form is slightly weaker than the acetate form, more milligrams of the succinate form are added to supplements to compensate for this small difference in potency. Therefore, 400 IU of either form should have equivalent potency.

1. VERIS Research Information Service. Summary finds superiority of natural vitamin E supplements over synthetic forms. Townsend Letter for Doctors & Patients 1999;July:100–5 [review].

2. Acuff RV, Thedford SS, Hidiroglou NN, et al. Relative bioavailability of RRR- and all-rac-alpha-tocopheryl acetate in humans: studies using deuterated compounds. Am J Clin Nutr 1994;60:397–402.

3. Christen S, Woodall AA, Shigenaga MK, et al. Gamma-tocopherol traps mutagenic electrophiles such as NO+ and complements alpha-tocopherol: physiological implications. Proc Natl Acad Sci 1997;94:3217–22.

4. Morinobu T, Yoshikawa S, Hamamura K, Tamai H. Measurement of vitamin E metabolites by high-performance liquid chromatography during high-dose administration of alpha-tocopherol. Eur J Clin Nutr 2003;57:410–4.

5. Beijersbergen van Henegouwen GM, Junginger HE, de Vries H. Hydrolysis of RRR-alpha-tocopheryl acetate (vitamin E acetate) in the skin and its UV protecting activity (an in vivo study with the rat). J Photochem Photobiol B 1995;29:45–51.

6. Norkus EP, Bryce GF, Bhagavan HN. Uptake and bioconversion of alpha-tocopheryl acetate to alpha-tocopherol in skin of hairless mice. Photochem Photobiol 1993;57:613–5.

Biochemical Functions
Serum concentrations of vitamin E (alpha-tocopherol) depend on the liver, which takes up the nutrient after the various forms are absorbed from the small intestine. The liver preferentially resecretes only alpha-tocopherol via the hepatic alpha-tocopherol transfer protein; the liver metabolizes and excretes the other vitamin E forms. As a result, blood and cellular concentrations of other forms of vitamin E are lower than those of alpha-tocopherol and have been the subjects of less research.

Vitamin E is a fat-soluble antioxidant that stops the production of reactive oxygen species (ROS) formed when fat undergoes oxidation. Scientists are investigating whether, by limiting free-radical production and possibly through other mechanisms, vitamin E might help chronic diseases associated with free radicals.

In addition to its activities as an antioxidant, vitamin E is involved in immune function and, as shown primarily by in vitro studies of cells, cell signaling, regulation of gene expression, and other metabolic processes. Alpha-tocopherol inhibits the activity of protein kinase C, an enzyme involved in cell proliferation and differentiation in smooth muscle cells, platelets, and monocytes. Vitamin-E–replete endothelial cells lining the interior surface of blood vessels are better able to resist blood-cell components adhering to this surface. Vitamin E also increases the expression of two enzymes that suppress arachidonic acid metabolism, thereby increasing the release of prostacyclin from the endothelium, which, in turn, dilates blood vessels and inhibits platelet aggregation.


  • Antioxidant (shield cells from damaging free radicals)
  • Inhibits coagulation (blood clotting)
  • Strengthens capillary walls
  • Stabilizes cell membranes
  • Guard against oxidation of proteins, lipids, hormones, and other substances
  • Skin conditions
  • Menopause
  • Restless legs syndrome
  • Heart disease


Research has not found any adverse effects from consuming vitamin E in food. However, high doses of alpha-tocopherol supplements can cause hemorrhage and interrupt blood coagulation in animals, and in vitro data suggest that high doses inhibit platelet aggregation.

Tolerable Upper Intake Levels (ULs) for Vitamin E**

Age Male Female Pregnancy Lactation
1-3 years 200 mg
(300 IU)
200 mg
(300 IU)
4-8 years 300 mg
(450 IU)
300 mg
(450 IU)
9-13 years 600 mg
(900 IU)
600 mg
(900 IU)
14-18 years
800 mg
(1,200 IU)

800 mg
(1,200 IU)
800 mg
(1,200 IU)
800 mg
(1,200 IU)
19+ years 1,000 mg
(1,500 IU)
1,000 mg
(1,500 IU)
1,000 mg
(1,500 IU)

1,000 mg
(1,500 IU)



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