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Α-Tocopherol

| NFPA-H = 1 | NFPA-F = 1 | NFPA-R = 0

α-Tocopherol (alpha-tocopherol) is a type of vitamin E. Its E number is "E307". Vitamin E exists in eight different forms, four tocopherols and four tocotrienols. All feature a chromane ring, with a hydroxyl group that can donate a hydrogen atom to reduce free radicals and a hydrophobic side chain, along with an aromatic ring is situated near the carbonyls in the fatty acyl chains of the phospholipid bilayer, allows for penetration into biological membranes. It is found most in the membrane's non-raft domains, associated with omega-3 and 6 fatty acids, to partially prevent oxidation. The most prevalent form, α-tocopherol, is involved in molecular, cellular, biochemical processes closely related to overall lipoprotein and lipid homeostasis. Compared to the others, α-tocopherol is preferentially absorbed and accumulated in humans.

Vitamin E is found in a variety of tissues, being lipid-soluble, and taken up by the body in a wide variety of ways. Ongoing research is believed to be "critical for manipulation of vitamin E homeostasis in a variety of oxidative stress-related disease conditions in humans." One of these disease conditions is the α-tocopherol role in the use by malaria parasites to protect themselves from the highly oxidative environment in erythrocytes. A second of these disease conditions is the α-tocopherol antioxidant properties' role cardiovascular heart disease. In preventing LDL (low-density lipoprotein) oxidation, it is able to decrease chances of atherosclerosis and arterial build-up.

Synthesis

To synthesize the ⍺-diastereomer selectively, tocol acetate is transformed to the naturally occurring, kinetically favored α-tocopherol after being catalyzed by the lipase enzyme. This reaction occurs under biological conditions, commonly in the digestive system.

Stereoisomers

α-Tocopherol has three stereocenters, so it is a chiral molecule. The eight stereoisomers of α-tocopherol differ in the configuration of these stereocenters. RRR-α-tocopherol is the natural one. The older name of RRR-α-tocopherol is d-α-tocopherol, but this d/l naming should no longer be used, because whether l-α-tocopherol should mean SSS enantiomer or the SRR diastereomer is not clear, from historical reasons. The SRR may be named 2-epi-α-tocopherol, the diastereomeric mixture of RRR-α-tocopherol and 2-epi-α-tocopherol may be called 2-ambo-α-tocopherol (formerly named dl-α-tocopherol). The mixture of all eight diastereomers is called all-rac-α-tocopherol. The α-Tocopherol is the most active diastereomer biologically, while being maintained at a high level in plasma and tissues of many different animal species.

One IU of tocopherol is defined as milligram of RRR-α-tocopherol (formerly named d-α-tocopherol). 1 IU is also defined as 0.9 mg of an equal mix of the eight stereoisomers, which is a racemic mixture, all-rac-α-tocopheryl acetate. This mix of stereoisomers is often called dl-α-tocopheryl acetate. Starting with May 2016, the IU unit is made obsolete, such that 1 mg of "Vitamin E" is 1 mg of d-alpha-tocopherol or 2 mg of dl-alpha-tocopherol.

  • Tocopherol
  • Tocotrienol --

References

References

  1. ''Merck Index'', 11th Edition, '''9931'''.
  2. (1 June 1986). "Vitamin E: application of the principles of physical organic chemistry to the exploration of its structure and function". Accounts of Chemical Research.
  3. (May 2010). "The location and behavior of α-tocopherol in membranes". Molecular Nutrition & Food Research.
  4. (2007). "Absorption, transport, and tissue delivery of vitamin E". Molecular Aspects of Medicine.
  5. (2019). "Probucol induces the generation of lipid peroxidation products in erythrocytes and plasma of male cynomolgus macaques". Journal of Clinical Biochemistry and Nutrition.
  6. (21 August 2005). "Vitamin e, Oxidative Stress, and Inflammation". Annual Review of Nutrition.
  7. (January 1993). "An enzyme-catalyzed synthesis of natural α-tocopherol". Tetrahedron: Asymmetry.
  8. (2007). "Alpha-tocopherol stereoisomers". Vitamins and Hormones.
  9. (July 1999). "Vitamin E: function and metabolism". FASEB Journal.
  10. [https://web.archive.org/web/20201122071533/https://www.qmul.ac.uk/sbcs/iupac/misc/toc.html IUPAC Nomenclature of Tocopherols and Related Compounds], from https://www.degruyter.com/document/doi/10.1351/pac198254081507/pdf
  11. (March 2006). "Bioavailability of α-tocopherol stereoisomers in rats depends on dietary doses of all-rac - or RRR-α-tocopheryl acetate". British Journal of Nutrition.
  12. (February 2008). "Composition of Foods Raw, Processed, Prepared USDA National Nutrient Database for Standard Reference, Release 20". [[USDA]].
  13. "Unit Conversions". [[National Institutes of Health]].
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