M6-Properties of Lipids

L1 Lipids; L2 Physical & Chemical Properties

L3 Chemical Reactions
LIPIDS
 Are heterogeneous group of compounds (fats,
oils, steroids, waxes and related compounds),
that are related more by their physical than by
their chemical properties
 Common properties
(1)Relatively insoluble in water
(2) Soluble in nonpolar solvents
LIPIDS
 Major roles:
1. They serve as structural components of
biological membranes.
2. They provide energy reserves,
predominantly in the form of
triacylglycerols or triglycerides
3. Both lipids and lipid derivatives serve as
vitamins and hormones
LIPIDS
 Classification:
A. Based on ability to be saponified/hydrolyzed
1. Saponifiable lipids - can be hydrolysed by
base, ex. simple and complex lipids
2. Non-saponifiable lipids - not hydrolysed
by base, ex. derived lipids
B. Based on their structures:
1. Simple lipids ( also called neutral fats or
true fats, waxes)
LIPIDS
2. Compound or Complex lipids
( lipoproteins, glycolipids, phospholipids)
3. Derived or Miscellaneous lipids ( steroids,
hormones, fat-soluble vitamins )
FATTY ACIDS
 Building blocks of simple lipids and some
compound lipids
 are carboxylic acids (RCOOH) with
long C chains of 12-20 C atoms.
FATTY ACIDS
 Naturally occurring fatty acids have an even
number of C atoms.
 Saturated fatty acids have no double bonds
In their long hydrocarbon chains
 Unsaturated fatty acids have 1 or more double
bonds (generally cis) in their long hydrocarbon
chains.
 Essential fatty acids are fatty acids that cannot
FATTY ACIDS
be produced by the body and must be
consumed.
 Non-essential fatty acids are fatty acids that
can be produced by the body.
FATTY ACIDS
FATTY ACIDS
FATTY ACIDS
NEUTRAL FATS
 Fats may be considered to be triesters formed
from the glycerol and three molecules of fatty
acids.
 Most of the fatty acids in these esters have 14-
18 carbons.
 Because there are three ester groups per
glycerol, the molecules are called
triacylglycerols, or triglycerides.
NEUTRAL FATS
 The three R groups are usually different
WAXES
 Waxes are esters of high-molar-mass fatty
acids and high-molar-mass alcohols.
 The alcohol (ROH) contributes up to about 30
carbons, and the fatty acid (R’COOH) also
provides an equivalent number of carbons.
 Waxes are very large molecules with almost
no polar groups.
 Coating that prevents loss of water by leaves
of plants
WAXES
PHYSICAL PROPERTIES OF NEUTRAL FATS
1. Have characteristic greasy feel
2. Penetrate substance like paper producing
translucent spot
3. Pure neutral fats are odorless, tasteless and
colorless
4. Insoluble in ordinary solvents but readily
dissolves in chloroform, benzene, ether and
boiling alcohol
PHYSICAL PROPERTIES OF NEUTRAL FATS
5. Non-volatile
6. Neutral fats containing large amount of
unsaturated fatty acids are liquid at room
temperature.
7. Neutral fats containing large amount of
saturated fatty acids are solid at room
temperature.
8. Fats floats on water because it has lower
specific gravity (or density).
EXPERIMENTAL RESULTS
A.Solubility Test
 Fats/Oil Samples: butter, margarine, corn oil,
oleic acid, Cholesterol, coconut oil
 Observation:
a. insoluble in water, 5% HCl and ethyl alcohol,
b. Slightly soluble in 5% NaOH due to
saponification reaction
c. Soluble in ether and n-hexane
EXPERIMENTAL RESULTS
EXPERIMENTAL RESULTS
Other Properties
Lipid Samples:
a. Coconut oil – slightly viscous liquid
b. Oleic acid – pale yellow oily liquid with
lard-like odor
c. Butter – semi-solid
d. Margarine – semi-solid
e. Lanolin – greasy yellow semi-solid substance
f. Cholesterol – coarse white powder
EXPERIMENTAL RESULTS
 f. mustard seed oil
 g. olive oil
 h. sesame oil
 i. peanut oil
 J. lard
 K. tallow
EXPERIMENTAL RESULTS
 B. Acrolein Test

EXPERIMENTAL RESULTS
Reaction:

Acrolein or propenal has pungent odor

KHSO4 acts as dehydrating agent.
EXPERIMENTAL RESULTS
Test for Glycerol (Acrolein Test)
EXPERIMENTAL RESULTS
C. Reaction with Iodine

Hanus I2
EXPERIMENTAL RESULTS
EXPERIMENTAL RESULTS
EXPERIMENTAL RESULTS
 Iodine number is a measure of the degree of
unsaturation in fats and oils.
 It is expressed as the number of grams of
iodine that chemically reacts with 100 g of fat.
 The higher the iodine number, the more
unsaturated fatty acids are present in the
sample.
 Unsaturated fatty acids contain one or more
double bonds in their structure.
EXPERIMENTAL RESULTS
D. Reaction with Bromine
EXPERIMENTAL RESULTS
EXPERIMENTAL RESULTS
 E. Base Hydrolysis ( Soap Making)
EXPERIMENTAL RESULTS
 Saponification – process of making soap
EXPERIMENTAL RESULTS
F. Hydrolysis of fats by dilute acid

Upper layer: fatty acid layer

Lower layer: aqueous layer containing glycerol
EXPERIMENTAL RESULTS
Reaction:
EXPERIMENTAL RESULTS
 Triacylglycerols are hydrolyzed with water in
the presence of acid, base, or enzymes (in the
body).
 Hydrolysis is the breaking down of a complex
molecules by water in the presence of acid,
base or enzyme to form simpler substances.
EXPERIMENTAL RESULTS
G. Salkowski test for Cholesterol
Other reactions
 Rancidity – cause by hydrolysis and oxidation
of fats which leads to unpleasant odor and
taste when allowed to stand at room
temperature.
Hydrolysis:
Fats + H2O → fatty acids + glycerol
Oxidation:
Volatile fatty acids → short chain aldehydes
and ketones
M7