 Lipids:

Lipids are heterogenous organic compounds which are

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Tishk International University
Faculty of Dentistry
Department of Basic Science

Biochemistry and Oral Biochemistry

Lipid

3rd lecture
2nd grade

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 Types of lipids:
Within the lipid family, there are specific structures that distinguish
the different types of lipids.
Lipids such as waxes, fats, oils, and glycerophospholipids are esters
that can be hydrolyzed to give fatty acids along with other products,
including an alcohol.
Triacylglycerols and glycerophospholipids contain the alcohol
glycerol, whereas sphingolipids contain an alcohol called
sphingosine.
Steroids, which have a completely different structure, do not contain
fatty acids and cannot be hydrolyzed. Steroids are characterized by the
steroid nucleus of four fused carbon rings. 3
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 Fatty acids:
The fatty acids are the simplest type of lipids and are found
as components in more complex lipids. Fatty acids are
aliphatic carboxylic acid.
A fatty acid contains a long, unbranched carbon chain
attached to a carboxylic acid group at one end (R-COOH).
Although the carboxylic acid part is hydrophilic, the long
hydrophobic carbon chain makes long-chain fatty acids
insoluble in water.

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 Naturally occurring fatty acids have an even number of carbon
atoms, usually between 10 and 20 carbon atoms. The most prevalent
fatty acids in plants and animals are palmitic (C16), oleic (C18), linoleic
(C18), and stearic (C18) acids. An example of a fatty acid is lauric acid, a
12-carbon acid found in coconut oil. A variety of condensed structural
formulas, as well as the skeletal formula, can be drawn for as follows:
 In a saturated fatty acid, the long carbon chain is like an
alkane
because there are only single carbon–carbon bonds.
 Their molecular formula is [Cn H2n+1 COOH].
 In a monounsaturated fatty acid, the long carbon chain has one
double bond, which makes its properties similar to those of an
alkene.
 Their molecular formula is [CnH2n-1COOH].
 In a polyunsaturated fatty acid, there are at least two carbon–carbon
double bonds.

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 Cis and Trans isomers of unsaturated fatty Acids
Unsaturated fatty acids can be drawn as -cis and -trans
isomers in the same way as the -cis and -trans alkene
structures. For example, oleic acid, a monounsaturated fatty
acid, has one double bond at carbon 9. We can draw its cis and
trans structures using its skeletal formula. However, the cis
structure is found in almost all naturally occurring unsaturated
fatty acids. In the -cis isomer, the carbon chain has a “kink” at
the double bond site.

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 As we will see, the -cis bond has a major impact on the properties of
unsaturated fatty acids. The human body is capable of synthesizing most
fatty acids from carbohydrates or other fatty acids. However, humans
do not synthesize sufficient amounts of polyunsaturated fatty acids, such
as linoleic acid and arachidonic acid. Because these fatty acids must be
obtained from the diet, they are known as essential fatty acids.

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 Properties of fatty acids
Saturated fatty acids fit closely together in a regular pattern, which
allows many dispersion forces between the carbon chains. These
normally weak intermolecular forces of attraction can be significant
when molecules are close together. As a result, a significant amount of
energy and high temperatures are required to separate the fatty acids and
melt the fat. As the length of the carbon chain increases, more dispersion
forces occur between the carbon chains, which results in higher melting
points.

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 Saturated fatty acids are usually solids at room temperature. In
unsaturated fatty acids, the -cis double bonds cause the carbon chain to
bend or “kink,” which gives the molecules an irregular shape. As a result,
-cis fatty acids cannot stack as closely as saturated fatty acids, and
thus
have fewer dispersion forces between their carbon chains. We might
think of saturated fatty acids as potato chips with regular shapes that
stack closely together in a container. Similarly, irregularly shaped chips
would be like unsaturated fatty acids that do not pack closely together.
Thus, less energy is required to separate the fatty acid molecules, which
makes the melting points of unsaturated fats lower than those of
saturated fats. Most unsaturated fats are oils at room temperature.
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 Omega-6 and Omega-3 in fatty acids:
Both fish and vegetable oils have high levels of unsaturated
fats.
The fatty acids in vegetable oils are omega-6 acids, in
which the first double bond occurs at carbon 6 counting from
the methyl end of the carbon chain.
However, the fatty acids in fish oils are mostly the omega-3
type, in which the first double bond occurs at the third carbon
counting from the methyl group.

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 Simple lipids:
1. Waxes:
Waxes are found in many plants and animals. Natural waxes are
found on the surface of fruits, on the leaves and stems of plants where
they help prevent loss of water and damage from pests. Waxes on the
skin, fur, and feathers of animals and birds provide a waterproof coating.
A wax is an ester of a saturated fatty acid and a long-chain alcohol, each
containing from 14 to 30 carbon atoms.

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 The formulas of some common waxes are given in table. Beeswax
obtained from honeycombs and carnauba wax from palm trees are used
to give a protective coating to furniture, cars, and floors. Jojoba wax is
used in making candles and cosmetics such as lipstick. Lanolin, a
mixture of waxes obtained from wool, is used in hand and facial lotions
to aid retention of water, which softens the skin.

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2. Fats & Oils (Triacylglycerol):
In the body, fatty acids are stored as fats and oils known as
triacylglycerols. These substances, also called triglycerides, are triesters
of glycerol (a trihydroxy alcohol) and fatty acids. The general formula of
a Triacylglycerols follows:
 We saw that esters are produced from the esterification reaction
between a carboxylic acid and an alcohol. In a triacylglycerol, three
hydroxyl groups on glycerol form ester bonds with the carboxyl groups
of three fatty acids. For example, glycerol and three molecules of stearic
acid form a triacylglycerol. For example, stearic acid is named as
stearate, which gives the name glyceryl tristearate. The common name of
this compound is tristearin.

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 Most fats and oils are mixed triacylglycerols that contain two or
three different fatty acids. For example, a mixed triacylglycerols might
be made from lauric acid, myristic acid, and palmitic acid. One possible
structure for the mixed triacylglycerols follows:

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 Melting points of fats and oils:
A fat is a triacylglycerol that is solid at room temperature and usually
comes from animal sources such as meat, whole milk, butter, and
cheese.
An oil is a triacylglycerol that is usually a liquid at room
temperature
and is obtained from a plant source.
Saturated fatty acids have higher melting points than
unsaturated
fatty acids because they pack together more tightly. Animal fats
usually contain more saturated fatty acids than do vegetable oils.
Therefore, the melting points of animal fats are higher than those of
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 Compound lipids:
1. Phospholipids:
The phospholipidsare a family of lipids similar in structure
to triacylglycerols; they include glycerophospholipids and
sphingomyelin. In a glycerophospholipid, two fatty acids form ester
bonds with the first and second hydroxyl group of glycerol. The third
hydroxyl group forms an ester with phosphoric acid, which forms
another phospho-ester
bond with an amino alcohol.
In a sphingomyelin, sphingosine replaces glycerol.

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 Amino Alcohols:

Three amino alcohols found in glycerophospholipids are choline,

amino alcohols are ionized.

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 Lecithins and cephalins are two types of glycerophospholipids that
are particularly abundant in brain and nerve tissues as well as in egg
yolks, wheat germ, and yeast.
 Steroids (Cholesterol):
Attaching other atoms and groups of atoms to the steroid
structure forms a wide variety of steroid compounds.
Cholesterol, which is one of the most important and abundant
steroids in the body, is a sterol because it contains an oxygen
atom as a hydroxyl group (OH) on carbon 3. Like many
steroids, cholesterol has methyl groups at carbons 10 and 13, a
carbon chain at carbon 17, and a double bond between
carbons 5 and 6.

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 HomeWorks:
1. Is glycerophospholipid soluble in non-polar solvents?
2. What are kinds of fatty acids according to the
nature of hydrocarbon chain?
3. Compare between triacylglycerol and
sphingomyelin according to their solubility in polar
solvent?

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References:
1. Lehinger principles of biochemistry, 5th edition.
2. W.H. Freeman and company illustrated
harpers
biochemistry,28th edition.
3. An introduction to general, organic and biological chemistry
by Timberlake, 11th edition.

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