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STRUCTURE OF LIPID

Name/NPM: Afrah Alatas/1406641792


Group: 3

I.

ABSTRACT
Lipids are important constituent of the diet because they are a source of high energy value. Lipids
are also important because of the fat-soluble vitamins, and essential fatty acids found in the fat of
the natural food stuffs. Body fat serves as a very good source of energy, it is stored in adipose
tissues. They also act as insulating material in the subcutaneous tissues and are also seen around
certain organs. Lipids combined with proteins are important constituents of the cell membranes
and mitochondria of the cell. Lipids are not generally macromolecules.
Lipids are naturally occurring organic compounds, commonly known as oils and fats. Lipids occur
throughout the living world in microorganisms, higher plants and animals and also in all cell types.
Lipids contribute to cell structure, provide stored fuel and also take part in many biological
processes.

II.

GENERAL STRUCTURE OF LIPID


Lipid is not actually a polymer, since it has no repeating chains of molecules. Lipid is built-up with
fatty acid and glycerol, connected with ester bond.

Figure 1. Illustration of
structure

lipids

Fatty Acids: A fatty acid is a long hydrocarbon chain capped by a carboxyl group
(COOH). The COOH cap is what makes these molecules acids. Fatty acids are carboxylic
acids (or organic acid), often with a long aliphatic tails (long chains), either saturated or
unsaturated.1 When a fatty acid is saturated it is an indication that there are no carboncarbon double bonds and if the fatty acid is saturated it is an indication that it has at least
one carbon-carbon double bond. As the following data indicate, the saturated acids have
higher melting points than unsaturated acids of corresponding size. If a fatty acid has more
than one double bond, then this is an indication that it is a polyunsaturated fatty acid.

Figure 2. Some examples of fatty


acids, compared to acetic acids
structure. As we can see, the fatty
acids are like acetic acid, but they
have much longer carbon chains.

Glycerol: Glycerol (also called glycerine or glycerin) is a simple polyol (sugar alcohol)
compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic.
Glycerol has three hydroxyl groups that are responsible for its solubility in water and its
hygroscopic nature. According to its IUPAC name, it is known as propane-1,2,3-triol.

Figure 3. Structure of glycerol

Formation of fat:
No
.
1

Procedure
The glycerol and fatty acids are
oriented such that the hydroxyl
and acid groups are close to each
other.

Illustration

III.

In an enzyme-catalyzed reaction,
the hydroxyl oxygens of glycerol
form a bond to the carboxyl
carbons of the fatty acids,
releasing water in the process.

Ester bonds are left between


glycerol and the fatty acids.

SATURATED AND UNSATURATED FATTY ACIDS


Based on its chemical bond, fatty acids can be classified whether it is saturated or unsaturated.
Saturated fatty acid means that it has no double bonds, while the unsaturated one has at least one
double bond. The other differences can be seen from the table below:
Type of bonds
Recommended
consumption
Health Effects

Cholesterol

Commonly
found in

Shelf Life
Melting Point
Physical state at
room
temperature
Rancidity
Examples

Saturated Fatty Acids


Consist of single bond only
Not more than 10% of total
calories per day
Excessive consumption is not
good because of their association
with atherosclerosis and heart
diseases.
Saturated fats increase Low
Density Lipoproteins (LDL or bad
cholesterol) & Very Low Density
Lipoproteins (VLDL's) Sources of
bad cholesterol are foods rich in
trans fatty acids, refined
carbohydrates, such as white
sugar, and flour.
Butter, coconut oil, whole milk,
meat, peanut, butter, margarine,
cheese, vegetable oil, fried foods,
& frozen dinners
These are long lasting and do not
spoil quickly
High
Solid (Trans Fats & Saturated
Fats)
Low
Hydrogenated Oils, Butter,
Processed Meats

Unsaturated Fatty Acids


Consist of at least 1 double bond
Not more than 30% of total calories
per day
Unsaturated fats are considered good
to eat if you are watching your
cholesterol. Also high in antioxidants.
Unsaturated fats increase HighDensity Lipoprotein (HDL or good
cholesterol) and decrease Low Density
Lipoproteins (LDL or bad cholesterol).
Sources of HDL include onions and
Omega-3 fatty acids like flax oil, fish,
foods rich in fiber like grains.
Avocado, soybean oil, canola oil and
olive oil, sunflower oil, fish oils walnuts,
flax, & red meats
These spoil quickly
Low
Liquid (Monounsaturated &
Polyunsaturated Fats- Omega 3's &
9's)
High
Olive Oil, linoleic acid, alpha-linolenic
acid

Classification of saturated and unsaturated fatty acids:

Structure examples of saturated fatty acids:


1. Lauric acid (dodecanoic acid): CH3(CH2)10COOH

2. Myristic acid (tetradecanoic acid): CH3(CH2)12COOH

3. Palmitic acid (hexadecanoic acid): CH3(CH2)14COOH

4. Stearic acid (octadecanoic acid): CH3(CH2)16COOH

5. Arachidic acid (eicosanoic acid): CH3(CH2)18COOH

Structure examples of unsaturated fatty acids:


1. Palmitoleic acid: CH3(CH2)5CH=CH(CH2)7COOH

2. Oleic acid: CH3(CH2)7CH=CH(CH2)7COOH

3. Linoleic acid: CH3(CH2)4(CH=CHCH2)2(CH2)6COOH

4. Arachidonic acid

IV.

CIS AND TRANS STRUCTURE


Unsaturated fats can be either cis fats or trans fats. While cis fats are beneficial and can promote
good cholesterol, trans fats are considered harmful to cardiovascular health, especially those trans
fats which come from unnatural sources (e.g., hydrogenated oils in processed foods).
Natural unsaturated fatty acids are in configuration that is called cis, but partial hydrogenation can
flip the chemical bonds into a different configuration that is called trans. The difference between cis
and trans is that the two H atoms are on the same side of the double bond (cis), compared to
being on opposite sides (trans). This may not seem like much of a difference, but it affects the
shapes of the molecules. In a cis configuration, the double bond creates a kink in the fatty acid. In
the trans configuration, there is no kink. Therefore, a trans-fatty acid is structurally similar to a

saturated fatty acid (which has no kinks, either). The kinks in the molecules determine whether the
material is solid or liquid at room temperature.
The table below shows the comparison between cis and trans structure of fatty acid:
Health Effect

Occurs
naturally

Yes

Arrangement
of atoms

The chains of carbon atoms


are on the same side of the
double bond, resulting in a
kink.
Usually low. Some cis fats are
liquid at room temperature.

Melting Point

V.

Cis Structure
Generally good for health
unless
consumed
in
unreasonably high quantities.

Trans Structure
Detrimental lowers good cholesterol and
increases the level of bad cholesterol in the
body. Harmful to heart health could cause
cardiac death.
While some natural trans fats occur in meat
and dairy products, the majority of trans fats
come
from
processed
foods
(i.e.,
hydrogenated oils).
Hydrogen atoms are on the opposite side of
the double bonds of the carbon chain,
making the fat molecule straight.
Usually high. Trans fats, like saturated fats,
are solid at room temperature.

LIPID CLASSIFICATION
A. Waxes
Waxes are carboxylic acid esters, with long, straight hydrocarbon chains in both R groups;
they are secreted by sebaceous glands in the skin of animals and perform mostly external
protective functions. Waxes are derived from fatty acid and a long chain alcohol. Because
of their long, nonpolar carbon chains, waxes are extremely hydrophobic (meaning they lack
an affinity for water). Both plants and animals use this waterproofing characteristic as part
of their composition. Plants most noticeably use waxes for a thin protective covering of
stems and leaves to prevent water loss. Similarly, animals employ waxes for protective
purposes; for instance, earwax in humans prevents foreign material from entering and
possibly injuring the ear canal area. Waxes are found in nature as coatings on leaves and
stems. The wax prevents the plant from losing excessive amounts of water.

Figure 4. Main structure of wax

The waxes with their component alcohols and fatty acids are listed below:

Wax
Carnuba
Beeswax
Spermacetic

Alcohol
CH3(CH2)28CH2-OH
CH3(CH2)28CH2-OH
CH3(CH2)14CH2-OH

Fatty Acid
CH3(CH2)24COOH
CH3(CH2)14COOH
CH3(CH2)14COOH

Ester synthesis to produce wax:


Simple esters are made from an organic acid and an alcohol. The ester functional
group is of primary importance in the biochemical group of compounds called
waxes, triglycerides, and phospholipids. The simplified reaction reveals the process
of breaking some bonds and forming the ester and the by product, water. Refer to
the graphic on the left for the synthesis of carnuba wax.

Figure 5.
formation

Esterification

reaction

in

wax

B. Triacylglycerides
Triacylglycerides (or known as triacylglycerol) are the products of a reaction in which three
OH groups of glycerol are esterified with fatty acids. A simple triacylglycerol is a
triacylglycerol with three of the same fatty acid components. A mixed triacylglycerol is a
triacylglycerol that contains two or three different fatty acid components and are more
common than simple triacylglycerol.
Fat is the name given to a class of triglycerides that appear as solid or semisolid at room
temperature, fats are mainly present in animals. Oil is the name given to class triglycerides
that appear as a liquid at room temperature, oils are mainly present in plants and
sometimes in fish.
The fact that saturated fatty acid tails can bunch up closely together, its allows the
triacylglycerols relatively high melting points, which in turn allows them to appear as
solids at room temperature.
The opposite goes for unsaturated fatty acids; their tails cannot pack as closely
together so in turn they have relatively low melting points which causes them to
appear as liquids at room temperature.
Fats usually consist of saturated fatty acids while oils usually consist of unsaturated
fatty acids.
There is an easy way to remember the formation of triaclyglycerides, as in following:

Remove the alcohols from the glycerol


Remove the hydrogen (of the carboxylic acid) from each fatty acid
Bond the oxygen with now three lone pairs on it to one of the three outside carbons.
Now you have a triaclyglyceride.

Figure 6.
C. Phospholipids formation

Reaction

illustration

in

triaclyglyceride

Phospholipids are similar to fats except they have two fatty acid chains bonded to a glycerol
plus they contain the element phosphorus. Phospholipids are unique because they have a
hydrophobic and a hydrophilic (water-soluble) end. Phospholipids are biologically important

because they are the main structural components of cell membranes. The cell membrane is
called a phospholipid bilayer because it consists of two phospholipid layers oriented so that
the hydrophilic head of both molecules face the exterior and the hydrophobic tails of both
molecules create the interior of the membrane. Therefore, water and other cellular fluids are
contained. The hydrophobic ends for both molecules face each other on the inside and
allow for passage of acceptable, and some objectionable, materials through the cell
membrane.

Figure
7.
Components
supporting in a
single
phospholipid.

The hydrocarbon chains are hydrophobic (as in all fats). However, the charges on the
phosphate and amino groups (in red) make that portion of the molecule hydrophilic. The
result is an amphiphilic molecule.
Figure 8. Illustration of
phospholipid, in a single
structure (left) and in a
bilayer
arrangement
(right).

To imagine more clearly about the structure of phospholipid, we can follow these steps
below:
Take the structure of a triacylglyceride
Remove one fatty acid
Replace it with a phosphate
Now you have a phospholipid

Figure 9. Main structure of


phospholipid

D. Prostaglandins
Prostaglandin is any member of a group of lipid compounds that are derived enzymatically
from fatty acids and have important functions in the animal body. Every prostaglandin
contains 20 carbon atoms, including a 5-carbon ring.5 Prostaglandins are responsible for
an array of physiological effects, such as inflammation, blood pressure (PGE2, see below

for structure), blood clotting (PGI2, see below for structure), fever, pain, the induction of
labor (PGF2alpha, see below for structure), and sleep-wake cycle.

Figure 10. Structure of


prostaglandin

E. Steroids
Steroids are a type of hormone which are usually recognized by their tetracyclic skeleton,
consisting of three fused six-membered and one five-membered ring. The main feature of
steroids is the ring system of three cyclohexanes and one cyclopentane in a fused ring
system as shown below. There are a variety of functional groups that may be attached. The
main feature, as in all lipids, is the large number of carbon-hydrogens which make steroids
non-polar.

Figure 11. Structure of


steroid

Steroid biosynthesis: All steroids are products from the acetyl CoA biosynthetic
pathway which yields cholesterol. 7 Cholesterol is the most common steroid
encountered by animals.

Some important steroids:

F. Lipophilic Vitamins
Vitamin: An organic compound, other than fat, protein or carbohydrates, required for the
normal growth maintenance of animals. Vitamins A, D, E, and K are in the lipid family.
Vitamin A: Vitamin A, which is also known as retinol, serves its main purpose in
contributing to vision. It works together with the light-harvesting portion of rhodopsin
(vision protein). Beta-Carotene is sliced to create two molecules of vitamin A.

Vitamin K: Vitamin K plays a key role in allowing blood to clot properly. The letter K
is derived from koagulation, which is German for clotting.

Vitamin E: Vitamin E is a water-soluble compound that holds radicals in nonpolar


membranes. Some of these are which we encounter everyday in our daily food
consumption are known as preservatives or antioxidants. They are used to preserve
food by preventing unwanted radical reactions. It also prevents oxidative cellular
damage from radicals.

Vitamin D: Vitamin D is a hormone foundation such that its main purpose is to help
maintain normal levels of calcium and phosphorus in the blood. Vitamin D also
contributes in keeping a strong and sturdy skeleton

VI.

SUMMARY
Lipid is one of the most important molecule in organism, that is formed by fatty acid
and glycerol.
A fatty acid is a long hydrocarbon chain capped by a carboxyl group, while glycerol
is a sugar alcohol compound.
Based on the number of double bond, fatty acid can be classified into saturated
(with no double bond) and unsaturated (with at least 1 double bond).
The unsaturated fatty acid can also be divided into cis structure and trans structure.
These structure will give different effect. Such as, cis fats will beneficial while trans
fats are considered to be harmful.
There are 6 classification or modification of lipids: waxes, triacylglyceride,
phpspholipids, prostaglandins, steroids and lipophilic vitamins. Each modification
has different structure and function
There are 4 vitamins which are considered as the lipophilic: vitamin A, K, D, and E.

VII.

REFERENCES
1. Nelson, David L, Nelson, David L, Lehninger, Albert L and Cox, Michael M, 2008, Lehninger
principles of biochemistry. New York : W.H. Freeman.
2. http://science.howstuffworks.com/innovation/edible-innovations/fat1.htm
3. https://www.chem.wisc.edu/deptfiles/genchem/netorial/modules/biomolecules/modules/lipids/lipid3.
htm
4. http://www.diffen.com/difference/Cis_Fat_vs_Trans_Fat
5. http://www.foothill.edu/attach/1578/Mossman30Achpt_24p1.pdf
6. http://www.chem.ucla.edu/~harding/notes/notes_14C_lipids.pdf
7. http://www.chem.ucla.edu/~harding/ec_tutorials/tutorial91.pdf
8. http://www.infoplease.com/cig/biology/lipids.html
9. http://chemwiki.ucdavis.edu/Core/Biological_Chemistry/Lipids/Non-glyceride_Lipids/Wax
10. http://users.rcn.com/jkimball.ma.ultranet/BiologyPages/P/Phospholipids.html
11. http://hyperphysics.phy-astr.gsu.edu/hbase/organic/phoslip.html
12. http://chemwiki.ucdavis.edu/Core/Biological_Chemistry/Lipids/Steroids

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