Introduction to Organic

Chemistry
CHEM 108
Credit hrs.: (3+1)

King Saud University

College of Science, Chemistry Department

CHAPTER 9: 1
Lipids
o Lipids are biological molecules that are insoluble in water but
soluble in nonpolar solvents (nonpolar).
o The word lipid comes from the Greek lipos, which means “fat.”

o Lipids are the waxy, greasy, or oily compounds found in plants and
animals.
- wax coating that protects - used as energy - structural
plants storage components (cell
- insulation against membranes)
cold

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 Classification of Lipids
Lipids are divided into:
Saponifiable (Hydrolyzable) Nonsaponifiable
- They containlipids
esters, - (Nonhydrolyzable)
They do not contain ester lipids
- They can undergo groups,
saponification (hydrolysis - They cannot be saponified
under basic conditions) (cannot be cleaved into
smaller molecules by aqueous
hydrolysis)
Simple Complex
lipidstwo
contain lipids
contain more than two components
components (fatty acids, an alcohol, and other
(fatty acid and an components)
alcohol)

Triglycerides Waxes phosphoglyceri Sphingolipids. steroids prostaglandins

(Fats & oils) des 3
Fatty Acids

o Fatty acids are long-chain unbranched carbon attached to a

carboxyl group (-COOH).

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Fatty Acids
Characteristics of Fatty
Acids:
 They are usually have straight chains (no branches) that are about 10 to
20 carbon atoms in length.
 They usually have an even number of carbon atoms (counting the
carboxyl carbon).
 The carbon chains may be;
• saturated (all single bonds) or
• unsaturated (containing double bonds).
 i.e. Functional groups are only the carboxyl group and the double
bonds.
 The double bonds are usually in cis configurations:
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Fatty Acids
Saturated and Unsaturated
Fatty Acids fatty acids have no double bonds in their long
o Saturated
hydrocarbon chains.
Stearic acid: CH3(CH2)16COOH
Stearic Acid
(m.p. 71ºC)

They are solids at room temperature. Stearic acid is found in palm oil,
which is frequently used in
handmade soap.

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Fatty Acids
Saturated and Unsaturated
Fatty Acids
o Unsaturated fatty acids have 1 or more double bonds (generally
cis) in their long hydrocarbon chains. Oleic Acid
(m.p. 13ºC)
 Oleic acid (one double bond),
and
 Linoleic acid (two double
bonds)
 All have 18 carbons in the
o Oleic acid is derived mainly from “olive” oil. Linoleic Acid
(m.p. -5ºC)
chain, but their melting points
sesame oil, Sunflower, shea butter, coconut
are different
oil, ... etc.
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o Linoleic acid is found in soybean oil
Fatty Acids
Essential Fatty
Acids
o Most of the fatty acids we need can be synthesized in the body.
o Two fatty acids, linoleic acid and linolenic acid, both polyunsaturated fatty acids
with 18-carbon chains, cannot be synthesized in the body and must be obtained
from the diet.
o These are essential fatty acids.
o Both are found in plant and fish oils.
o In the body, they are used to produce hormone-like substances that regulate
blood pressure, blood clotting, blood lipid levels, the immune response, and
inflammatory reactions.

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Fatty Acids
Essential Fatty
oAcids
All fatty acids that bear the “omega” label are unsaturated,
containing one or more double bonds.
Omega-n acids n: the position of the first double bond

Linoleic acid is called an omega-6 acid, because of the position of the

first C=C in the nonpolar chain.

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Fatty Acids
Essential Fatty
Acids
Linolenic acid is called an omega-3 acid, because of the position of
the first C=C in the nonpolar chain.

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Fatty Acids
Some Important Fatty
Acids

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Triglycerid
es Simple lipids
o Animal fats and vegetable oils are esters composed of three molecules of a
fatty acid connected to a glycerol molecule, producing a structure called a
triglyceride or a triacylglycerol:

Esterification
O
O
CH2 OH HO C (CH2)14CH3
CH2 O C (CH2)14CH3
O O
CH OH HO C (CH2)14CH3 CH O C (CH2)14CH3 + 3H2O
O Acid

CH2 OH HO C (CH2)14CH3 O
CH2 O C (CH2)14CH3 12
Triglycerid
es Simple lipids
o Simple triacylglycerols have three identical fatty acid side chains.

o Mixed triacylglycerols have two or three different fatty acids.

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Fats &
oils Simple lipids
o The fatty acids in a triglyceride molecule are usually not all the
same;
o Natural triglycerides are often mixtures of different triglyceride
molecules.

Fats are Oils are

 triglycerides that are solids at room  triglycerides that are liquids at room
temp. temp.
 usually derived from animals  usually derived from plants or fish
 mostly saturated fatty acids  mostly unsaturated fatty acids 14
Fats &
oils Simple lipids

A comparison of saturated and unsaturated fatty acids in

some foods.

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 Fats & oils Simple lipids
Chemical Properties of Fats and Oils
Hydrolysis of Triglycerides
Triglycerides can be broken apart with water and an acid catalyst
(hydrolysis), or by digestive enzymes called lipases:

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 Fats &
oils Simple lipids
Chemical Properties of Fats and Oils
Saponification of Triglycerides (Basic Hydrolysis)
Triglycerides react with strong bases (NaOH or KOH) to form the
carboxylate salts of the fatty acids, called soaps:

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 Fats & oils Simple lipids
Chemical Properties of Fats and Oils
Soaps
o NaOH produces a “hard” soap, commonly found in bar soaps;
o KOH produces a “soft” soap, such as those in shaving creams and
liquid soaps.
o These salts combine two solubility characteristics:
 a long, nonpolar, water-insoluble (hydrophobic) hydrocarbon
“tail.”
 a charged, water-soluble (hydrophilic) “head.”
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 Fats & oils Simple lipids
Chemical Properties of Fats and Oils
Soaps
In water, the “tails” become tangled, leaving the charged heads
sticking out into the solution, forming a structure called a micelle.

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 Fats & oils Simple lipids
Chemical Properties of Fats and Oils
Hydrogenation
o Alkenes are converted into alkanes with hydrogen gas (H2) and a
catalyst (Pt, Ni, or some other metal).
o This process is used to convert unsaturated vegetable oils, which
are liquids at room temp., to saturated fats, which are solids at
room temp.

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Waxes Simple lipids
Waxes are simple lipids contain a fatty acid joined to a long-chain (12-
32 carbons) alcohol:

Because of their long nonpolar C chains, waxes are very hydrophobic.

O
Beeswax CH3(CH2)14 C O(CH2)29CH3
(myricyl palmitate)
hydrophobic hydrophobic
region region
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Waxes Simple lipids
 Waxes are insoluble in water, and not as easily hydrolyzed as fats
and oils.
 Waxes often occur in nature as protective coatings on feathers, fur,
skin, leaves, and fruits.
 Waxes are used commercially to make cosmetics, candles,
ointments, and protective polishes.
Beeswax

Lanolin from wool

lotions

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 Phospholipid
s Complex lipids
o Phospholipids are lipids that contain a P
atom.
o There are two common types:
Phosphoglycerol Sphingolipids
Sphingolipids are complex lipids
that contain sphingosine instead of
glycerol.

sphingolip
ds

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 Phospholipid
s Complex lipids
Phosphoglycerols
o Phosphoglycerols are complex lipids that are major components of
cell membranes.
o Structurally, they resemble a triacylglycerol, except the third fatty
acid has been replaced with a phosphodiester bonded to an
alcohol.

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 Phospholipid
s Complex lipids
Phosphoglycerols
o There are two types of phosphoglycerols;

Choline
Ethanolamine

- Cephalins are found in most cell Lecithin can act as an emulsifying agent:
membranes, - important structural component of cell
- They are particularly abundant in brain membranes.
- play a role in the transport of lipids in the blood
tissue.
stream.
- They are also found in blood platelets, - Commercially, lecithin extracted from soybeans
and play a role in blood clotting. 25
is used as an emulsifying agent in margarine
and candies to provide a smooth texture.
Phospholipid
s Complex lipids
Sphingomyelins
They do not contain a glycerol backbone, they have a sphingosine backbone instead.

They do not contain an ester; their single fatty acid is bonded to the backbone by an
amide bond.

Sphingomyelins are found brain and nerve tissue, and in the myelin sheath that
26
protects nerves.
Phospholipid
s Complex lipids
Glycolipids
o Glycolipids are sphingolipids that contain carbohydrates (usually
monosaccharides).
o They are also referred to as cerebrosides because of their
abundance in brain tissue.

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 Cell
Membrane
Fluid mosaic model
Carbohydrate

Phospholipid
bilayer

Nonpolar
Hydrophobic

Polar
Hydrophilic

The cell membrane as being composed of a lipid bilayer, in which the nonpolar tails of
lipids point towards the “interior” of the bilayer, leaving the polar, hydrophilic portions
pointing outwards.
Semipermeable: selected nutrients can enter and waste products can leave. 28
 Nonsaponifiable
Steroids (Nonhydrolyzable)
lipids
o Steroids are classified as lipids because they are soluble in nonpolar
solvents.
o They are nonsaponifiable because the components are not held
together by ester linkages.
o The basic steroid structure contains four fused rings:

o Steroids have

nucleus which is 4 carbon rings.

attached groups that make the different types of
compounds.
no fatty acids. 29
 Nonsaponifiable
Steroids (Nonhydrolyzable)
lipids
Cholesterol
o Cholesterol is the most abundant steroid in
the body.
o It is an essential component of cell
membranes, and is a precursor for other
steroids, such as the bile salts, sex hormones,
vitamin D, and the adrenocorticoid hormones.
o There is apparently a correlation between high
levels of cholesterol in the blood and
Cholesterol is obtained from meats, milk, and eggs.
atherosclerosis.
Cholesterol is synthesized in the liver from fats, carbohydrates
and proteins.
No cholesterol in vegetable and plants. 30
 Nonsaponifiable
Steroids (Nonhydrolyzable)
lipids
Bile Salts
o Bile is a yellowish brown or green fluid produced in the liver and
stored in the gall bladder.
o Bile salts act like soaps and other emulsifiers: they contain both
polar and nonpolar regions, helping to break fats in foods into
smaller pieces, allowing them to be hydrolyzed more easily.

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 Nonsaponifiable
Steroids (Nonhydrolyzable)
lipids
Steroid Hormones
o A hormone is a molecule that is synthesized in one part of an
organism, which then elicits a response at a different site.
o Two types of steroids hormones:
1. Sex hormones
Estrogens & progestins in females
Androgens in males

2. Adrenal Cortical Steroids

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 Nonsaponifiable
Steroids (Nonhydrolyzable)
lipids
Steroid Hormones
Female Sex
Hormones
Estrogens Progestins
The estrogens estradiol and estrone control The progestin progesterone is called the
development of secondary sex characteristics, “pregnancy hormone”; it is responsible for
regulate the menstrual cycle, and are made in the preparation of the uterus for implantation
the ovaries. of a fertilized egg.

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 Nonsaponifiable
Steroids (Nonhydrolyzable)
lipids
Steroid Hormones
Male Sex
Hormones
Androgens
Testosterone and Androsterone are androgens made in the testes.
They control the development of secondary sex characteristics in
males.

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 Nonsaponifiable
Steroids (Nonhydrolyzable)
lipids
Steroid Hormones
Adrenocorticoid Hormones
o The adrenocorticoid hormones are produced in the adrenal
glands (located on the top of the kidney).
o Glucocorticoids such as cortisol affect the metabolism of
carbohydrates.
o Cortisol and its derivatives, cortisone and prednisolone
(synthetic) are powerful anti-inflammatory drugs used to treat
arthritis and asthma.

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 Nonsaponifiable
Steroids (Nonhydrolyzable)
lipids
Steroid Hormones
Adrenocorticoid Hormones
Mineralocorticoids regulate ion concentration (mainly Na+).
Aldosterone influences the absorption of Na+ and Cl- in kidney
tubules, thus regulating the retention of water in the body.

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 Prostaglandi Nonsaponifiable
ns (Nonhydrolyzable)
lipids
Prostaglandins are carboxylic acids that contain a five-membered
ring and have a wide range of biological activities.

Prostaglandins are responsible for inflammation.

o Prostaglandins also decrease gastric secretions, inhibit blood
platelet aggregation, stimulate uterine contractions, and relax
o smooth muscles.
Aspirin and ibuprofen relieve pain and inflammation by blocking the
synthesis of these molecules. 37
Vitamins
o They are organic compounds required in small quantities for normal
metabolism.
o They must be obtained from the diet (our cells cannot synthesize
them).
o Vitamins are either water soluble or fat soluble.

o The four fat-soluble vitamins (A, D, E, and K) are lipids and

nonpolar.
o They are found in fruits, vegetables, fish, liver, and dairy products.

o Excess vitamins are stored in adipose cells to be used when

needed.
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 Vitami
Vitamin A
ns

o It is found in liver, fish, and dairy products, and is made from β-

carotene (the orange pigment in carrots).

o It is needed for vision and for healthy mucous membranes.

o Vitamin A deficiency causes night blindness and dry eyes and skin.

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 Vitami
Vitamin D
ns
o Vitamin D can be synthesized from cholesterol.

o It can be obtained in the diet from many foods, especially milk, and
helps regulate Ca and P metabolism.
o A deficiency of vitamin D causes rickets (bone malformation).

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 Vitami
Vitamin E
ns
o Vitamin E is an antioxidant, protecting unsaturated side chains in
fatty acids from unwanted oxidation.
o Deficiency of vitamin E causes numerous neurological problems,
although it is rare.

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 Vitami
Vitamin K
ns

o Vitamin K regulates the synthesis of clotting proteins (prothrombin),

and deficiency of this leads to excessive or fatal bleeding.

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