•Fats- a mixture of triglycerides

containing a high proportion of long

chain saturated fatty acid

•Oils- a mixture of triglycerides

containing a high proportion of long
chain unsaturated fatty acid or short-
chain saturated fatty acid.

1
Types of Lipids
• Simple lipids
Fats and oils (trigycerides)
waxes
Compound lipids
Phospholipids (lecithin, cephaline)
glycolipids
lipoprotein
Derived lipids
fatty acids of various series
sterols (cholesterol, ergosterol)
2
Substances associated with lipids

•Carotenoids
•Tocopherols
•Vitamin k
•steroids

3
Fatty Acids

•Long-chain carboxylic acids

•Insoluble in water
•Typically 12-18 carbon atoms (even number)
•Some contain double bonds

corn oil contains 86%

unsaturated fatty acids and
14% saturated fatty acids

7
Saturated and Unsaturated Fatty Acids

Saturated = C–C bonds

Unsaturated = one or more C=C bonds

COOH
palmitic acid, a saturated acid
COOH

palmitoleic acid, an unsaturated fatty acid

8
Structures
Saturated fatty acids
• Fit closely in regular pattern
COOH
COOH
COOH

Unsaturated fatty acids

• Cis double bonds H H
C C

cis double bond COOH

9
Properties of Saturated
Fatty Acids
•Contain only single C–C bonds
•Closely packed
•Strong attractions between chains
•High melting points
•Solids at room temperature

10
Properties of Unsaturated
Fatty Acids
•Contain one or more double C=C
bonds
•Nonlinear chains do not allow
molecules to pack closely
•Few interactions between chains
•Low melting points
•Liquids at room temperature
11
Fats and Oils
Formed from glycerol and fatty acids

O
CH2 OH HO C (CH2)14CH3
O
CH OH + HO C (CH2)14CH3
O
CH2 OH HO C (CH2)14CH3
glycerol palmitic acid (a fatty acid)
12
Triglycerides (triacylglcerols)
Esters of glycerol and fatty acids

ester bonds
O
CH2 O C (CH2)14CH3 + H2O
O
CH O C (CH2)14CH3 + H 2O
O
CH2 O C (CH2)14CH3 + H 2O

13
Learning Check L2
What are the fatty acids in the following
triglyceride?

O
CH2 O C (CH2)16CH3
O
CH O C (CH2)7CH CH(CH2)7CH3
O
CH2 O C (CH2)12CH3
14
Solutions L2
What are the fatty acids in the following
triglyceride?

O Stearic acid
CH2 O C (CH2)16CH3
O Oleic acid
CH O C (CH2)7CH CH(CH2)7CH3
O
Myristic acid
CH2 O C (CH2)12CH3
15
Physical properties of fats and oils
•Odorless, colorless when pure
•Greasy feeling, produce translucent
grease spot
•Insoluble in water, soluble in organic
solvents
•Lighter than water
•Can be emulsified

16
 Chemical Properties of fats
Hydrogenation
•Unsaturated compounds react with H2
•Ni or Pt catalyst
•C=C bonds C–C bonds
Hydrolysis
•Split by water and acid or enzyme catalyst
•Produce glycerol and 3 fatty acids

17
 Hydrogenation

O
CH2 O C (CH2)5CH CH(CH2)7CH3
O
Ni
CH O C (CH2)5CH CH(CH2)7CH3 + 3 H2
O
CH2 O C (CH2)5CH CH(CH2)7CH3

18
 Product of Hydrogenation
O
CH2 O C (CH2)14CH3
O
CH O C (CH2)14CH3
O
CH2 O C (CH2)14CH3

Hydrogenation converts double bonds in oils to single

bonds. The solid products are used to make margarine
and other hydrogenated items.
19
 Hydrolysis
Triglycerides split into glycerol and three fatty
acids (H+ or enzyme catalyst)
O
CH2 O C (CH2)14CH3
O
H+
CH O C (CH2)14CH3 +3 H2O
O
CH2 O C (CH2)14CH3
CH2 OH O
CH OH + 3 HO C (CH2)14CH3

CH2 OH
20
Saponification and Soap

• Hydrolysis with a strong base

• Triglycerides split into glycerol and the salts of
fatty acids
• The salts of fatty acids are “soaps”
• KOH gives softer soaps

21
 Saponification

O
CH2 O C (CH2)16CH3
O
CH O C (CH2)16CH3 + 3 NaOH
O
CH2 O C (CH2)16CH3
CH2 OH O
+-
CH OH + 3 Na O C (CH2)14CH3
salts of fatty acids (soaps)
CH2 OH

22
 LIPIDS…Some interesting info

There are many different types of steroids.

They are all lipids. Their functions vary.
Some common steroids are:
SEX STEROIDS ANABOLIC STERIODS
CHOLESTEROL
They increase muscle
Like testosterone and estrogen
 Illegal Steroid Use in Women
Some additional effects…
Breasts will decrease in size, the opposite of what happens to
men.
The woman will start to grow facial hair, how quickly
depends on her genetic makeup. If she discontinues
use, the facial hair will still continue to grow.
If she is genetically predisposed to balding,
she will start to lose her hair, just as if she
was genetically male.
Her voice will start to deepen,how quickly
depends on her genetics. If she discontinues
use, her voice will remain deep.
Very Common Effects of Illegal Steroids
If used when the person is still growing, they will be shorter
as an adult, anabolic steroids will decrease bone growth.
Males will experience shrinking of the testicles, and with prolonged
use, the steroid will be turned into estrogen in the male body and it
will start to lay fatty tissue on the chest, otherwise known as breasts.
If genetically predisposed to becoming
bald, balding will happen more quickly.
If clean needles are not readily
available, there is a significantly higher
risk of getting AIDS.
Future risks of liver cancer & disease.
Enlarged heart (one pro athlete’s heart grew
to the size of a basketball…obviously he’s
dead)
29
 WAXES
• simple esters of fatty acids (usually saturated with long
chain monohydric alcohols)

H3C (CH2)14 C O CH2 (CH2)28 -CH3

fatty acid
long chain alcohol
Common waxes in nature

•Spermaceti wax
•From sperm whale, used in making
cosmetics and pharmaceuticals
products
•lubricants

31
Carnauba wax

•Polishes for automobiles, floors

and furnitures
•Shoe creams
•Carbon paper

32
Bees wax

•Used in raising melting point of

ointments and other cosmetics
•“cerumen”- protect against infection
by capturing airborne particles

33
lanolin

•Used as basis for many

ointments and creams,

•Used in lotion

34
lecithin

•Greek word “lekythos” meaning egg

yolk
•Composition of lipids
•Glycerol
•Fatty acids
•Phosphoric acid
•Quaternary base
•chloine
35
Properties of lecithin
• Physical
• Waxy, white, soluble in fat solvents
• Mix with water to form cloudy and colloidal
solutions
• Chemical
• when shaken with sulfuric acid the choline is
split off leaving phosphoric acid
• Readily hydrolyzed by boiling with bases and
mineral acids.
• Readily decompose into fatty acids, choline
glycerol and phosphoric acid

36
 Sphingomyelin (a ceramide)

HO R
O

NH R' usually palmitic acid

O-
O O
P N(CH3)+

O
phosphatidyl choline (also can be ethanolamine)

It is a phospholipid characterized by being white crystalline substance.

Sources are in the brain, nerve , in various organs and in blood
•Composition
•Fatty acids
•Phosphoric acid
•Choline
•sphingosine
•Properties
•White crystalline substance, stable in air,
insoluble in ether, upon hydrolysis it yeild
f,a, c, shingosine

38
glycolipids

•Glycolipids-
contains sugar
•Galactolipids-
galactose
•Cerebrosides
•Present in brain

39
sterol

•High molecular
weigh, solid
alcohols of a
cyclic structure
•Derivatives of
steroid

40
Functions of cholesterol

•It plays a role in the transportation

of fat
to the tissues and in the metabolism
of fats
Aids in the synthesis of bile salts
Substance of the sex and adrenal
cortical hormones
42
Test for cholesterol
•Salkowski’s Test- A solution of cholesterol in
chloroform with concentrated sulfuric acid
will give
•cherry red color.
•Liebermann-Burchard Test- the sterol is
treated with chloroform, acetic anhydrides
and conc, sulfuric acid. An
•emerald green color will be produced.
•Acrolein Test- test for glycerol

43
ergosterol

•Widely
distributed in
both plants
and animal
cells

44