L I P I D S

What is lipid?

any of a group of organic compounds
that are fatty acids or their derivatives
and are insoluble in water but soluble in
organic solvents. They include many
natural oils, waxes, and steroids.


fatty acids are classified as saturated
and unsaturated according to whether
they have carbon-carbon double bonds
or not.

Element bromine (Br2) is a substance
that eagerly attacks these double bonds.
The product of this reaction is a
brominated fatty acid.


OBJECTIVES

To be able to classify substances
which are insoluble in water in
any organic solvents.

To be able to determine the
degree of unsaturated of lipids.

To be able to determine the
cleansing power of soap and
detergents
Test for Solubility
Sample Solvent Used Result





Cottonseed Oil
Distilled water 3 secs, insoluble
Ethyl alcohol 2-3 secs, soluble
Ether 2-3 secs, soluble
Chloroform 2-3 secs, soluble
Benzene 2- 3 secs soluble
5 % hydrochloric acid 3 secs, insoluble
5 % sodium
hydroxide
3 secs, insoluble
Discussion
Lipids are soluble only in nonpolar
solvents because lipids, themselves,
are nonpolar. Water, 5 %
hydrochloric acid, 5 % sodium
hydroxide are polar; Ethyl alcohol
ether, chloroform, and benzene are
not.

Test for Unsaturation
Sample Solvent Used Reagent
Added
Result
Oleic Acid Distilled water Bromine in
CCl4
The color
orange fainted
after 8 drops
Palmitic Acid Ethyl alcohol Chloroform
Hanus Iodine
From color
light pink to
yellow (24:44
mins)
Oleic Acid Ether Chloroform
Hanus Iodine
Color light
pink to yellow
(28 mins)
Cottonseed Oil Chloroform Chloroform
Hanus Iodine
Light pink to
color yellow
Discussion


Test for unsaturation identifies the level
of saturation and the number of bonds a
lipid has. The more unsaturated, multi-
bond the lipid is, the more it absorbs
iodine. The less iodine it absorbs, it
considered to be saturated, single
bonded.
Acrolein Test
Sample Solvent Used Reagent
Added
Result
Glycerol Distilled water KHSO4 Odor is
pungent
Palmitic Acid Cottonseed oil KHSO4 Odor is
pungent
Discussion
The purpose of acrolein test is to find
out whether there is a presence of
glycerin or fats in a compound. The
way to perform this test is to heat a
sample with potassium bisulfate
(KHSO4) If acrolein is released, then
the test is positive
When a fat is heated strongly in the
presence of a dehydrating agent such
as KHSO4, the glycerol portion of the
molecule is dehydrated to form the
unsaturated aldehyde, acrolein
(CH2=CH-CHO), which causes a
pungent odor.
Test for Rancidity
Sample Reagent Added Result



Fresh coconut oil

Phenolphthalein Transparent color
and two layers
formed
Methyl Orange Color light orange
and formed two
layers


Rancid coconut oil

pH paper Did not change in
color
Phenolphthalein Brownish yellow
with two layers
Discussion
Rancidity is a term generally used to
denote unpleasant odors and flavors
in foods resulting from weakening in
the fat or oil portion of a food.

Saponification
Sample Reagent Added Result


Coconut Oil



10 % KOH

Bubble formation
and jelly-like
substance
Discussion
Saponification is a process by which
triglycerides are reacted with sodium or
KOH to produce glycerol and a fatty acid
salt that is called 'soap'. Lipids that
contain fatty acid ester linkages can
undergo hydrolysis. This reaction is
catalyzed by a strong acid or base.
Saponification is the alkaline hydrolysis
of the fatty acid esters.

A positive test is indicated by:

Properties of Soap Salting Out
Sample Reagent Added Result


Soap Solution



NaCl

Crystal formation
and white substance
was formed and it
has a coconut odor
Sample Reagent Added Result


Soap Solution



10 % HCl


A thicke white
precipate formed
Formation of Fatty Acids
Sample Reagent Added Result





Soap Solution










5 % CaCl2


A thick white
precipitate formed

5 % MgCl2

Slight clear white
color formed
Insoluble Soaps
Sample Reagent Added Result






Detergent










5 % CaCl2


It became cloudy

5 % MgCl2

It became cloudy
Discussion
Carboxylic acids and salts show signs of
unusual behavior in water due to the
presence of both hydrophilic (CO2) and
hydrophobic (alkyl) regions in the same
molecule. Such molecules are
termed amphiphilic (Gk. amphi = both)
or amphipathic. Fatty acids made up of ten
or more carbon atoms are nearly insoluble
in water, and because of their lower density,
float on the surface when mixed with water.
Sample Reagent Added Result


Cholesterol

CHCl2
Acetic
Anhydride
Conc. H2SO4

Orange color then
after 2 mins, color
changed to blue
Liebermann Burchard Test for Cholesterol
Discussion
This test is used for the detection
of cholesterol. The formation of a green
or green-blue colour after a few minutes
is positive. The colour is due to the
hydroxyl group (-OH) of cholesterol
reacting with the reagents and increasing
the conjugation of the un-saturation in
the adjacent fused ring.
Emulsifying Action of Lecithin
Sample Reagent Added Result

2 % Albumin
Cholesterol White color that is
slightly thick
Cholesterol Lecithin Yellowish white
color that is thick

2 % Albumin
Cholesterol White color that is
slightly thick
Cholesterol Lecithin Yellowish white
color that is thick
Discussion
Lecithin, a lipid material composed of
choline and inositol, is found in all
living cells as a major component of
cell membranes, which regulate the
nutrients entering and exiting the
cell.
Answers to Questions:
1. Why are fatty acids insoluble in water?

Because they are hydrophobic that is lack
of infinity of water, and fatty acids are
having a long hydrocarbons chain,
making it not insoluble in water.

The hydrocarbons chain can be also called
as tail which shows hydrophobic
properties due to the chain ( as the
number of hydrocarbons increases, its
solubility in water decreases. ) And water
is polar compound and hydrocarbons are
non-polar and as like dissolved like.
(there are some exceptions.) because,
fatty acids are soluble only in fats.

2. Explain why the cis-form is the
predominant configuration of unsaturated
fatty acids?

Trans forms are often more
thermodynamically stable (lower in
energy) than cis and might be expected to
predominate except that the two are not
formed in a random manner

Such compounds are usually formed in bio-
chemically important reactions involving
enzymes which often only produce one of
the possible isomers that could be
formed. If the cell has a use for the cis
isomer only then is likely that it will have
evolved enzymes that will produce the cis
form exclusively.

Because if the double bond is a cis bond the
carbon atoms are on the same side this
causes a spontaneous breaking in the
chain allowing different and more rigid
shapes to be formed.

A trans bond has a carbon atoms on
opposite sides leaving the structure
similar to the saturated form, trans fatty
acids are generally a product of
processing ( hydrogenation ) that no
usual found naturally making it difficult
to invent properly.
3. What type of rancidity occurs in vegetable
shortenings? How can it be prevented?

The type of rancidity that occurs in
vegetable shortenings is oxidative
rancidity.


4. Show the structure of the parent
compound of cholesterol.

Cholesterol is a parent compound of
practically every steroid in your body.
cholestrol is a steroid, which has 4 rings of
carbon, 3 6-carbon rings and a 5 carbon
ring, fused together, and on one end has a
8 carbon hydrocarbon, and an OH on the
other..
Structure of Cholesterol
5. Explain the cooperative effect of lecithin
and albumin.

Lecithin is an emulsifier consisting of a
variety of ingredients, the active
components being phospholipids - these
are long chain polar lipids.

The emulsifying properties of lecithin result
from this combination of a polar
(hydrophilic) group attached to a non-
polar (hydrophobic) lipid chain, and
means that they can help disperse an oil
phase into an aqueous solution or vice
versa, creating an emulsion (oil-in-water
or water-in-oil respectively).
These emulsions are not solutions, but
rather are very well dispersed micro-
droplets of the secondary phase, and this
explains why emulsions are opaque rather
than completely transparent, Albumins
are water-soluble proteins a - massive
polar molecules
Conclusion:
We therefore conlude that, Lipids are a family of
substances that are insoluble in water but
soluble in nonpolar solvents and solvents of low
polarity, such as diethyl ether. It functions as
Energy Storage; Membrane Components and
Messengers.

Classified into different groups: Complex lipids,
Fats, Steroids, Prostaglandins, Thromboxanes and
Lukotrienes.
http://www.australianolives.com.au/assets/fil
es/pdfs/Media/Health%20Effects%20of%20Ra
ncid%20Oils.pdf
http://chemistry.about.com/library/glossary/
bldef825.htm
http://www.harpercollege.edu/tm-
ps/chm/100/dgodambe/thedisk/food/sapon/sa
pon.htm