Vitamin E (Tocopherol)

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Vitamin E (Tocopherol) is a biomolecular substance mostly found in plants and animals. It is classified as a substance with many properties, such as serving as an antioxidant, strengthening the immunity and preventing various diseases, including blood pressure, kidney disease, cancer and vascular disease.

Vitamin E is an unsaturated alcohol that is a liquid (yellow oil) and is well soluble in fat. It is well resistant to heat and acids, but deteriorates easily when exposed to alkalis, sunlight and ultra-violet rays. In addition, there will be an oxidation when exposed to air, which can lead to rancidity. Alpha – tocopherol is the most important type because it is the most common type and can serve as a good antioxidant.

Physical and Chemical Properties
• Physical State : Liquid
• Chemical Formula : C31H52O3
• Molecular Weight : 472.73 g/mole
• Color : Slightly yellowish
• Odor : Characteristic, bland
• Boiling Point : 443°C (829.4 °F)
• Melting Point : -27.5°C (-17.5 °F)
• Specific Gravity : 0.9533
• Flash Point : 200 °F
• Auto-Ignition Temperature : 320 °C
• Solubility in Water : Insoluble
• CAS Number : 7695-91-2

History
Vitamin E was first discovered in 1992 by Evans and Bishop who found it by chance based on a doubt in experiments with female mice that there was a substance making these mice have a normal pregnancy while receiving this substance insufficiently caused a miscarriage. As a result, such substance was named as antisterrility vitamin.

Later in 1936, Evans and his colleagues could extract and separate such substance from the wheat germ oil successfully and named it as tocopherol (tocols means a child and phero means giving birth). (Wolf et al, 1998)(5)

vitamin E

Molecular structure
The molecular structure of vitamin E includes the polar part of chroman ring, which is the head acting as an antioxidant, and the tail of tocopherol that is a group replacing the sides by non-polar part from phytyl group while the tail of tocotrienol is polyisosophenoid group. This tail serves to embed and attach to the lipid in the cell membranes. Each kind of lipoprotein core varies in terms of their number and position of methyl group (-CH3) with chroman ring at carbon positions 5, 7 and 8.

Type of Vitamin E
• Tocopherol type
– Alpha-tocopherol
– Gamma-tocopherol
– Beta-tocopherol
– Delta-tocopherol

• Tocotrienol type
– Alpha-tocotrienol
– Gamma-tocotrienol
– Beta-tocotrienol
– Delta-tocotrienol

Chemical Formula of  Vitamin E at Each (Eitenmiller and Lander, 1999)(2)
1. α-T
– Molecular Weight : 430.71
– Chemical Formula : C29H50O2
– Wavelength absorption (nm) : 292
2. β-T
– Molecular Weight : 416.69
– Chemical Formula : C28H48O2
– Wavelength absorption (nm) : 296
3. γ-T
– Molecular Weight : 416.69
– Chemical Formula : C28H48O2
– Wavelength absorption (nm) : 298
4. δ-T
– Molecular Weight : 402.66
– Chemical Formula : C27H46O2
– Wavelength absorption (nm) : 298
5. α-T3
– Molecular Weight : 424.67
– Chemical Formula : C29H44O2
– Wavelength absorption (nm) : 292
6. β-T3
– Molecular Weight : 410.64
– Chemical Formula : C28H42O2
– Wavelength absorption (nm) : 296
7. γ-T3
– Molecular Weight : 410.64
– Chemical Formula : C28H42O2
– Wavelength absorption (nm) : 297
8. δ-T3
– Molecular Weight : 396.61
– Chemical Formula : C27H40O2
– Wavelength absorption (nm) : 297

Results of deficiency
Body’s lack of vitamin E will be assessed from the ratio of vitamin E in the plasma to the total amount of fat in plasma. If the value is less than 0.8 mg/g, it indicates that vitamin E is deficient. In general, when vitamin E is deficient, physical symptoms are different between animals and humans.
• Vitamin E deficiency in animals will result in lower fertility rates and muscle weakness.
• Vitamin E deficiency in humans will show neurological symptoms, including eye muscle weakness and lower shaking sensation. In addition, there are blood symptoms in newborns, including blood platelet cohesion and cancer.

Vitamin E deficiency is very rare in people, but it is more common in patients with fat malab sorption, such as patients with cirrhosis of cholestasis and cystic fibrosis for decades. In addition, there is a greater risk in newborns because these infants have the low ability to absorb fat.

Side effects of ingesting Vitamin E in high doses and for a long time have not been much investigated. There was a report on the use of less than 2000 units of vitamin E with no side effects. However, there are general symptoms due to high doses of Vitamin E as a side effect of vitamin E itself and of fat content, including nausea, vomiting, stomachache, abdominal distension, diarrhea, headache, amblyopia, fatigue, higher level of cholesterols and triglycerides, and even bleeding in the brain. In addition, it can stimulate existing symptoms in patients with bleeding disorders because vitamin E can decrease the absorption of vitamin K and increase the level of warfarin in the blood causing the decreased clumping of platelets.

Medicinal effects
• Vitamin E is an important antioxidant in the body.
• It strengthens the immune system and increases the number of white blood cells and antibodies.
• It maintains the normal balance of the functioning mechanism of hormones in the body.
• It can treat the anemiae specially in newborns with broken blood cells.
• It nourishes the body and treats the malnutrition disorder. If receiving vitamin E, fat will always be given as well because vitamin E is well soluble in fat.
• It is used as a component of cream cosmetics cream for reducing wrinkles and dark spots.
• It also serves as an antioxidant and helps eliminate dead cells and radicals around dark spots.It helps treat the leg muscle aches due to constricted blood vessels that cause a lack of oxygen to the muscles.

Vitamin E in the cells will provide the electrons to free radicals creased by processes in the cells. Therefore, it can reduce the toxicity of these free radicals that can damage cells in the body and deform free radicals allowing the body to better eliminate free radicals in different systems.

Prevention of various diseases (Narasinga Rao, 2001)(4)
Vitamin E helps prevent various diseases, including thrombosis, vascular disease, atherosclerosis, swelling and blocked veins, kidney disease, cancer, hypertension, rheumatoid arthritis, heart disease, sterility in men, irregular menstrual cycle in women, and earlier aging.

Applications
• It is used as a source of vitamin E supplements in the form of vitamin E extracts, such as capsules and oral tablets.
• It is used as an ingredient in foods or drinks to supplement vitamin E or to maintain food quality.
• It is used as a component of cosmetics, such as creams for reducing wrinkles and scars.

Sources
Vitamin E is mostly found in green vegetables, meat, milk, eggs, whole grains and all kinds of vegetable oils. (Chow, 1985)(1), (Palm Oil Research Institute of Malaysia, 1987)(3)
• Soybean
– Total Vitamin E : 56-160 mg/100 g
Tocopherol (%)
– Alpha-α : 4-18
– Beta-β : Not detectable
– Gamma-γ : 58-69
– Delta-δ : 26
Tocotrienol (%)
– Alpha-α : Not detectable
– Beta-β : Not detectable
– Gamma-γ : Not detectable
– Delta-δ : Not detectable

• Corn
– Total Vitamin E : 53-162 mg/100 g
Tocopherol (%)
– Alpha-α : 11-24
– Beta-β : 5
– Gamma-γ : 76-89
– Delta-δ : Not detectable
Tocotrienol (%)
– Alpha-α : Not detectable
– Beta-β : Not detectable
– Gamma-γ : Not detectable
– Delta-δ : Not detectable

• Coconut
– Total Vitamin E : 1-4 mg/100 g
Tocopherol (%)
– Alpha-α : 14-67
– Beta-β : Not detectable
– Gamma-γ : Not detectable
– Delta-δ : < 17
Tocotrienol (%)
– Alpha-α : < 14
– Beta-β : < 3
– Gamma-γ : < 53
– Delta-δ : < 17

• Palm
– Total Vitamin E : 33-73 mg/100 g
Tocopherol (%)
– Alpha-α : 28-50
– Beta-β : Not detectable
– Gamma-γ : Not detectable
– Delta-δ : < 9
Tocotrienol (%)
– Alpha-α : 16-19
– Beta-β : 4
– Gamma-γ : 34-39
– Delta-δ : < 9

• Palm kernel
– Total Vitamin E : 3.4 mg/100 g
Tocopherol (%)
– Alpha-α : 1.3
– Beta-β :  Not detectable
– Gamma-γ : Not detectable
– Delta-δ : Not detectable
Tocotrienol (%)
– Alpha-α : 2.1
– Beta-β : Not detectable
– Gamma-γ : Not detectable
– Delta-δ : Not detectable

• Sunflower
– Total Vitamin E : 25-49 mg/100 g
Tocopherol (%)
– Alpha-α : 80-94
– Beta-β : Not detectable
– Gamma-γ : 39-52
– Delta-δ : 0.8
Tocotrienol (%)
– Alpha-α : Not detectable
– Beta-β : Not detectable
– Gamma-γ : Not detectable
– Delta-δ : Not detectable

• Bean
– Total Vitamin E : 20-32 mg/100 g
Tocopherol (%)
– Alpha-α : 48-61
– Beta-β : Not detectable
– Gamma-γ : 39-52
– Delta-δ : Not detectable
Tocotrienol (%)
– Alpha-α : Not detectable
– Beta-β : Not detectable
– Gamma-γ : Not detectable
– Delta-δ : Not detectable

vitamin-E

Picture from : www.medimoon.com

Demand
• Infants and children need about 30 IU of vitamin E per day.
• Teens need about 30-50 IU of vitamin E per day.
• People of working age and pregnant women need about 50-100 IU vitamin E per day.

Vitamin E supplements and recommendations
• Vitamin E supplements are typically produced in the form of extracted oil in capsules made from animal and vegetable oils, such as coconut oil and cod liver oil.
• Vitamin E for cosmetic products is often used to remove wrinkles and dark spots and most of the creams are for external skins.
• Vitamin E supplements can be eaten at any time, but they should be taken with foods or after meals to absorb it with foods at the same time.
• Taking cholestyramine oristat during getting vitamin E should be avoided because such drug can inhibit the absorption of vitamin E at the intestines.

Storage
• Vitamin E products should be stored in a tightly closed container, away from heat sources and sunshine, and in a well-ventilated and cold area with temperature of no more than 23 °C (73.4 °F).
• They should be kept away from oxidizing agents, acids and alkalis.
• Containers used for storage should be opaque and fire and heat resistant with a tight cover.

References
1. Chow, C.K., 1985. Vitamin E and Blood. World review of nutrition and dietetics.
2. Eitenmiller, R.R. and W.O. Lander, Jr., 1999. Vitamin Analysis for the Health and Food Science.
3. Palm Oil Research Institute of Malaysia, 1987. Fact about Palm Oil.
4. Narasinga Rao, B.S., 2001. Nonglyceride components of edible oil and fats1. Chemical and distribution.
5. Wolf R, Wolf D, Rvocco V., 1998. Vitamin E : the redical protector.