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Vitamin E

life science Maturity 5-7 Next article →

Vitamin E is a vital group of eight related compounds. These molecules are known as tocochromanols. This group includes four tocopherols and four tocotrienols. Scientists classify vitamin E as an essential nutrient for humans. This means the human body requires it to function properly. Most government organizations recommend that adults consume between 3 and 15 mg per day. A 2016 worldwide review found a median dietary intake of 6.2 mg per day.

Tocopherols
Tocopherols

These compounds function primarily as fat-soluble antioxidants. They work to protect cell membranes from reactive oxygen species. These species are often called free radicals.

TocophMech
TocophMech

The mechanism involves the vitamin donating a hydrogen atom to a radical. This process is possible because the O-H bond in tocopherols is relatively weak. At 323 kJ/mol, this bond is about 10% weaker than most other phenols. By donating the atom, the vitamin stops the radical from causing damage. The resulting tocopheroxyl radical is then recycled. Other antioxidants, such as vitamin C or retinol, help return it to its active form.

All eight vitamers share a specific molecular structure. They all feature a chromane double ring. They also possess a hydrophobic side chain. This side chain allows the molecule to penetrate into biological membranes. The eight forms are divided into two main groups. The first group consists of four tocopherols. The second group consists of four tocotrienols.

Alpha-Tocopherol Structural Formulae V.1
Alpha-Tocopherol Structural Formulae V.1

The main difference is in their side chains. Tocotrienols have unsaturated side chains with three carbon-carbon double bonds. In contrast, tocopherols have saturated side chains.

Each of the two groups contains four distinct types. These types are named alpha (α), beta (β), gamma (γ), and delta (δ). These names are determined by the number and position of methyl groups on the ring. For example, alpha-tocopherol has three methyl groups at specific sites. Delta-tocopherol has only one methyl group at a specific site.

Beta-tocopherol
Beta-tocopherol

The tocotrienols follow the same naming pattern. While tocopherols are essential nutrients, tocotrienols are not classified as such by government organizations. Some research suggests tocotrienols might help with inflammation or heart disease, but clinical outcomes are not yet certain.

History shows how our understanding of this nutrient has evolved. Vitamin E was first discovered in 1922. Scientists isolated the substance in 1935. By 1938, the first synthetic version was created. The name "tocopherol" comes from Greek words meaning "birth" and "to bear." This name was chosen because the vitamin was found to be essential for fertilized eggs in rats to result in live births.

In the United States, the use of vitamin E supplements has changed over time. Use of these supplements peaked around the year 2002. However, use declined by more than 50% by 2006. This decline was likely due to meta-analyses of scientific studies. These studies suggested that very high doses might offer no benefit or could even have negative consequences.

Codliveroilcapsules
Codliveroilcapsules

While population studies once linked vitamin E to lower rates of cancer or heart disease, placebo-controlled clinical trials using 2,000 mg of alpha-tocopherol did not always show the same results.

Plants synthesize these compounds in their plastids. They use the Shikimate pathway to create the chromanol ring. They use the MEP pathway to create the hydrophobic tail.

Synthesis Tocopheryl acetate
Synthesis Tocopheryl acetate

Plants use vitamin E for several important reasons. In leaves, alpha-tocopherol protects against damage from ultraviolet sunlight. In seeds, tocochromanols protect lipids from oxidizing and becoming rancid. This helps ensure the seed can successfully germinate. Environmental stress can even change how much vitamin E a plant makes. For instance, drought or heat can increase the levels of tocopherols in almonds and olives.

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🖼️ Images & Media (10)
File:Tocopherols.svg
Tocopherols.svg
File:Alpha-Tocopherol Structural Formulae V.1.svg
Alpha-Tocopherol Structural Formulae V.1.svg
File:Tocopherol, alpha-.svg
Tocopherol, alpha-.svg
File:Beta-tocopherol.png
Beta-tocopherol.png
File:Gamma-tocopherol.png
Gamma-tocopherol.png
File:Delta-tocopherol.png
Delta-tocopherol.png
File:Tocopheryl acetate.png
Tocopheryl acetate.png
File:TocophMech.svg
TocophMech.svg
File:Synthesis Tocopheryl acetate.svg
Synthesis Tocopheryl acetate.svg
File:Codliveroilcapsules.jpg
Codliveroilcapsules.jpg
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