VITAMIN E (MEDICINAL CHEMISTRY) BY P.RAVI SANKAR. [INTRODUCTION,STRUCTURES OF TOCOPHEROLS,CHEMISTRY OF VITAMIN E,RECOMMENDED DAILY INTAKE,DIETARY SOURCES ANS SUPPLEMENTS, PHYSIOLOGICAL ROLE RO IMPORTANCE,USES OF VITAMIN E, SIDE EFFECTS/ADVERSE EFFECTS, VITAMIN E PREPARATIONS

1. (tocopherols)
VITAMIN
Prof. Ravisankar
Vignan Pharmacy college
Valdlamudi
Guntur Dist.
Andhra Pradesh
India.
banuman35@gmail.com
00919059994000

2.  In the year 1922,Herbert M.Evans reported the existence of vitaminE.
Infact vitamin E is the antisterility factor which is necessary for
fertility of the male and the birth process of the female and
therefore it is also called tocopherols because the word ….
Tokos(Greek) means = for child birth
phero = to bear
ol = alcohol.
It is very essential for the birth process in female
and fertility in males and at the same time the compound reacts
like an alcohol.
. The vitamin E represents a group of eight compounds which are
collectively called tocopherols. Out of 8, α-tocopherol is most active.β andγ-
tocopherols possess half the activity of the α-isomer.
the tocopherols (4-forms and tocotrienols 4-forms
Both structures are similar except the tocotrienol structure has double bonds on
the isoprenoid units.
There are many derivatives of these structures due to the different substituents

3. TOCOPHEROL TOCOTRIENOL
Position of methyl
groups on aromatic ring
Tocopherol structure Tocotrienol structure
5,7,8 trimethyltocol) alpha-Tocopherol (α) alpha-Tocotrienol
5,8 diemthyltocol) beta-Tocopherol (β) beta-Tocotrienol
7,8 dimethyltocol) Gamma tocopherol
(γ)
Gamma-Tocotirenol
8 mono methyl tocol Delta-tocopherol (δ) Delta-tocotrienol
(occurs wheat germ oil)
(occurs wheat germ oil)
(cotton seed oil)
1 2
3
4
5
6
7
8
11
21
31
41
51
61
71
81
91
101
111
121
Tocopherols are 6-Hydroxy chroman
Isoprenoid side chain at C2
The difering factor between tocopherols is the substitutions
On c5,c7,and c8
(3 W)

4.  CHEMISTRY OF VITAMIN E (TOCOPHEROLS)
 Vitamin E refers to a family of eight molecules having a chromanol ring
(chroman ring with an alcoholic hydroxyl group) and a 12-carbon aliphatic
side chain containing two methyl groups in the middle and two more methyl
groups at the end.
 For the four tocopherols the side chain is saturated, whereas for the four
tocotrienols the side chain contains three double-bonds, all of which adjoin
a methyl group.
 The four tocopherols and the four tocotrienols have an alpha, beta, gamma and
delta form — named on the basis of the number and position of the methyl
groups on the chromanol ring.
 The alpha form has three methyl groups, the beta & gamma forms have two
methyl groups and the delta for has only one methyl group.
12
2 Middle methyl groups
2 methyl groups
At the end6
12
Carbon side chain

5.  Tocotrienols (found in high
concentrations in palm oil) are
many times more potent as
anti-oxidant than are tocopherols,
but they are poorly assimilated by
digestion, are poorly distributed to
tissues in blood and are rapidly
metabolized and eliminated from
the body.
 But tocotrienols are well-
absorbed by the skin and thus
are well suited for use as a
Vitamin E cream.

TOCOTRIENOLS

6.  Recommended daily intake
 The Food and Nutrition Board at the Institute of Medicine report
the following dietary reference intakes for vitamin E.
 Infants
 0 to 6 months: 4 mg/day
 7 to 12 months: 5 mg/day
 Children
 1 to 3 years: 6 mg/day
 4 to 8 years: 7 mg/day
 9 to 13 years: 11 mg/day
 14 years and adults: 15 mg/day

7.  Dietary sources and
supplements
 The following foods are rich in
vitamin E.
 fortified cereals
 seeds and seed oils, like sunflower
and safflower.
 nuts and nut oils, like almonds
 green leafy vegetables, like spinach,
turnip.
 tomato products
 pumpkin
 sweet potato
 blue crab
 rockfish
 mangoes
 asparagus
 broccoli
 papayas
The Avocado - Rich in Vitamin E
Hight amount found
In livers of hourse
And cattle.
Small amounts
Found in the muscles
Of heart,kidney,
Placenta,egg etc,.

8. Wheat germ oil. Sunflower seeds,
cooked spinach, almonds, safflower
oil,cottonseed oil,soybean.
and hazelnuts.
1 Tbsp. wheat germ oil = 20 mg
1/4 cup sunflower seeds = 12 mg
1 cup cooked spinach = 7 mg
1 ounce almonds (23 nuts) = 7 mg
1 Tbsp. safflower oil = 5 mg
1 ounce hazelnuts (21 nuts) = 4 mg
mustard greens, turnip greens, chard, sunflower seeds, almonds,,, parsley, kale,
papaya, olives, bell pepper, brussel sprouts, kiwifruit, tomato, blueberries, and
broccoli.
Vitamin E can be found in foods such as cooking oil, fish oil, multi-grain cereal,
apricots, pumpkins, mustard and poutry,olives.

9.  You can get vitamin E from 4
main groups:
 Vegetable oils. Corn, canola,
sunflower, sesame, cottonseed,
peanut, rice bran, and palm oils.
 Nuts - almonds, walnuts,
peanuts, pistachios and
hazelnuts.
 Oil seeds, legumes and grains.
Corn, lentils, wheat, rice,
northern beans,
chickpeas,Barley grass and
oats.
 Wheat germ oil Extracted from
the germ of wheat, Wheat germ
oil has been used since the '20s
as a vitamin E supplement. It
offers a good combination of
tocopherols plus tocotrienols.
. Wheat germ oil is great sources of natural vitamin E.

10.  Uses of vitamin E
 Vitamin E is also particularly vital in treating many skin problems and
diseases such as psoriasis.
 As for the treatment of scars, although many people have experienced and
claimed that vitamin E lotions help soften the appearance of acne and
surgical scars
 . They have nevertheless, help preventing skin damage and cancer due to
its sun protection quality and its powerful antioxidant properties.
 There was a 40% reduced risk of coronary artery disease for those who
took vitamin E supplements compared to those who did not.
 Many types of cancer are believed to result from oxidative damage to
DNA caused by free radicals. Antioxidants - such as vitamin E - help
protect against the damaging effects of free radicals, which may
contribute to the development of chronic diseases such as cancer.
Vitamin E also may block the formation of nitrosamines, which are
carcinogens formed in the stomach from nitrites consumed in the diet.
Vitamin E may also protect against the development of cancers by
enhancing immune function.

11.  Prostate cancer: some evidence associates higher intake of vitamin E with
a decreased incidence of prostate cancer.
 The study showed that pre-menopausal women with a family history of
breast cancer who consumed the highest quantity of vitamin E enjoyed a
43% reduction in breast cancer
 A potent antioxidant, Vitamin E is useful for a range of topical applications,
including treating burns,
 reducing wrinkles,
 healing irritations,
 and protecting against sun damage.
 Many physicians, surgeons, and wound technicians use and recommend
vitamin E to help reduce scarring from surgery or injury.
 Vitamin E is also a popular treatment for post-pregnancy stretch marks,
which is supported by a number of studies.
 The formation of amyloid plaques in the brain is one of the hallmarks of
Alzheimer's disease.

12. vitamin E can help prevent chronic age-related illnesses, including heart disease and Alzheimer’s.
 Vitamin E supports many of the body’s daily functions such as protecting
red blood cells and maintaining the immune system.
 It may also safeguard skin from harmful ultraviolet rays.
 Vitamin E, an antioxidant that protects the skin from free radicals. The top layer
(epidermis) protecting the skin from harsh weather and reducing the dryness that
causes ashy skin.
Vitamin E brings a lot of health benefits for the body and is particularly important
especially for our skins, hearts, muscles and red blood cells.
 In addition, Vitamin E also protects our cell membranes as well as keeping our
blood circulations and nerves healthy.
 In actual, one of the major benefits of Vitamin E is protecting Vitamin A from
the damage of free radicals which are substances that are known to damage
body cells and cause cancer.
 Vitamin E works to defends the body against tissue damage. As it also
protects the body’s red blood cells, it can ward of the possible
development of anemia.
 Other benefits of Vitamin E include helping to control blood pressure and
lowering blood sugar.

13. Physiological role/importance of vitamin E
 Vitamin E plays an important role as an
antioxident and protect the body cells
from the damage caused by free
radicals.These free radicals are highly
reactive and distructive compounds
formed as a result of oxidative
deterioration(metabolism) of
polyunsaturated fats.
 Factors contributing for free radical
genaration in the body include smoking
and exposure to Uv- radiations.
 Tocopherols (Vitamin E) are equipped to
perform a unique function. They can
interrupt free radical chain reactions by
capturing the free radical; this imparts to
them their antioxidant properties. The
free hydroxyl group on the aromatic
ring is responsible for the
antioxidant properties. The hydrogen
from this group is donated to the
free radical, resulting in a relatively
stable free radical form of the
vitamin.

14.  Genarally the free radicals attack the cell membrane, proteins, and DNA
causing severe health problums such as cancer and cardivascular
diseases.
Vitamin E readily reacts with these free radicals and transforms them
into less reactive and non harmful forms.
Vitamin E providers the stability and intergrity of cellular membranes
and imparts protection from various pulmonary diseases,
cardiovascular diseases,neuronal diseases,dermal diseases and
other chronic diseases.
vitamin E aids in proper blood clotting and skeletal and cardiac
muscles.
It also useful in ----
Regulating cellular metabolism in the body including protein synthesis
muscles.
Provides vitamin C form oxidation.
production of red blood cells.
Stabilization of fats and amino acids.
Metabolism of nucleic aids and steroids.

15.  The Importance Of Vitamin E
 Vitamin E is also important to the health of our skins and nails.
 . When Vitamin E is added to skin lotions, it carries the effect of anti-
aging to the skin. It can reduce the appearance of lines and wrinkles
thereby making the skin looks younger.
 Vitamin E is also particularly vital in treating many skin problems and
diseases such as psoriasis.
 As for the treatment of scars, although many people have experienced
and claimed that vitamin E lotions help soften the appearance of acne
and surgical scars, recent research studies have shown otherwise.
 In fact, They have nevertheless, help preventing skin damage and
cancer due to its sun protection quality and its powerful antioxidant
properties.
 vitamin E supports a healthy circulatory and cardiovascular system,
aids in proper blood clotting, improves wound healing, is necessary
for tissue repair, promotes healthy hair and skin and can in effect slow
the aging process.
 As the "master antioxidant," vitamin E fights the harmful free radicals
which increase the risk of chronic disease and accelerate aging. It is
an essential component of every wellness and anti-aging program

16.  Rich in vitamin E, can help the protect your brain from Alzheimer’s, according
to a new study.
 a role in immune function
 DNA repair,
 the formation of red blood cells
 and vitamin K absorption.
 Getting rid of black heads.
 Getting rid of acne.
 Getting Rid of Dandruff.
 Getting rid of stretch marks.
 Vitamin E keeps your skin smooth.
 Vitamin E is used as a component of multivitamin preparation.
 Vitamin E helpful in the prevention of caronary heart disease by limiting the
oxidation of LDL cholesterol (bad cholesterol)
 Development of age related muscular degenaration (AMD)
 Vitamin E is helpful in protecting the retina from glaucomatous damage.
 Vitmin E +Vitamin C = is used as a prophylactic in Alzeimer’s disease.
 Genarally tocopherols are widely used in cosmetic and food industry as an
inexpensive preservative.

17.  Vitamin E is a powerful anti-aging agent because it could reverse age-
related declines in immune function.
Here is the list of conditions and diseases that Vitamin E can help in: Heart
disease, angina, cancer, multiple sclerosis, diabetes, Alzheimer’s
disease, cataracts, emphysema, high cholesterol, fibrocystic breast
condition intermittent claudication, infertility, impotence, genital
herpes, bedsores, leg cramps, muscle soreness, phlebitis, menopausal
discomforts, HIV, osteoarthritis, and chronic inflammatory diseases
such as lupus and rheumatoid arthritis.
 Regarding sex, Vitamin E plays an important role in the production of sex
hormones. It protects them from oxidation and degradation. Low vitamin E
levels can cause a decline in the formation of key sex hormones and enzymes
responsible for sperm production and ovarian health.
 Vitamin E also shows a protective effect on sperm cell membranes.
Supplementation with Vitamin E can also aid in improving sperm motility.

18.  The decline in sexual libido for women can sometimes be attributed to
the drop in levels of the sex hormones estrogen and progesterone.
Several studies have shown that Vitamin E possesses estrogenic,
androgenic and progesterone-like properties which can help in
combating this hormonal change. Thus, this vitamin can assist in
easing hormonal imbalances, hot flashes, low libido and even
combating vaginal changes.
Regarding sex, Vitamin E plays an important role in the production of sex hormones.
It protects them from oxidation and degradation .
 Vitamin E, long thought of as the “sex vitamin,” is also an antioxidant. When
erect, the penis is engorged with blood that carries vital oxygen. Vitamin E protects
this oxygen-rich blood from becoming filled with free radicals, in addition to helping
the heart during sex. Since it is almost impossible to get enough vitamin E from food,
Gittleman advises supplementing at least 400 IU each day, as well as eating such
foods as wheat germ, nuts, seeds and flaxseed oil.
 . These free-radical fighters, (antioxidants) which include vitamins A, C and E, help
protect and promote your sexual organs by reversing a low sex drive.

19.  What is the difference between natural vitaminE and synthetic vitamin E?
 Regarding the right form of Vitamin E to take, researchers said that Natural Vitamin E
(d-alpha tocopherol) is better than the synthetic ones (dl-alpha tocopherol) because
they are known to be retained in our body two times better than the latter
 In one word, the difference is: availability. Natural vitamin E has roughly twice the
availability of synthetic vitamin E.
 Here is the difference: The d-alpha-tocopherol in our food, the natural form, is a
single entity, in other words all the molecules are identical. By contrast, the synthetic
dl-alpha-tocopherol is a mixture of 8 different molecular entities, known in the
chemical jargon as "stereoisomers". Of these 8, only 1 is identical to the natural form.
The other 7 do not exist in nature.
 Synthetic dl-alpha-tocopherol is not harmful. But its value to your body is only 1/2 of
the natural.
 Read the label - it's the only way to tell if you
are getting natural or synthetic. Natural will say
"d-alpha-tocopherol", synthetic will say "dl-
alpha-tocopherol.

20.  Researchers are fairly certain that
oxidative modification of LDL-
cholesterol ("bad" cholesterol)
promotes blockages in coronary
arteries which may lead to
atherosclerosis and heart attacks.
 Vitamin E may help prevent
or delay coronary heart
disease by limiting the
oxidation of LDL-cholesterol

21. Side effects/adverse effects.
 Taking vitamin E supplements for up to 4 months at doses of 530 mg or 800 IU
(35 times the current RDA) had no negative side-effect on general health,
 body weight,
 levels of body proteins,
 lipid levels,
 liver or kidney function
 thyroid hormones
 amount or kinds of blood cells
 and bleeding time over doses may cause Nausea,vomitng,diarrhoea.
 vitamin E products in excess of 1200 IU daily may interfere with absorption and metabolism of
vitamins A and K. But one can get benefits with much lower levels of vitamin.
 individuals who are vitamin K(people who are on blood thinners) deficient should not take
alpha-tocopherol supplements without close medical supervision because of the increased risk
of hemorrhage.

22. Physico-chemical properties of vitamin E
 Colour : pale yellow
 State: oil
 Solubility: soluble in fats and organic
solvents.
hence it is stored in the adipose tissue of
the body.
stability : It is thermostable and
chemostable compound.
Hence acids and basis by the process of
hydrogenation or high temparature up to
1800
C.
Long exposure to UV- Radiation and
oxidising agents can distroy vitamin E.

23. Vitamin E preparations Vitamin E preparations are are available in single form(alpha
tocopherol) or with one or more other additivies.
 Commercially available vitamin E preparations(vitamin E range of
95% to 100% of the labelled amount.
 Evion(merck) ------ 200mg,400mg,600mg soft gelatin capsules.
 E-cap ------- 200mg,400mg capsules.
 Edge --------400 IU of gelatin capsules.
 Tocofer----- 200mg,400mg capsules.
 Monovitin--- 100 IU,200 IU,400 IU capsules.