General lipids

1. Lipids

2. Lipids
• Group of naturally occurring,
non polar, water insoluble
and hydrophobic substances
found in cells
• These are extractible with
non polar organic solvents
• They have both commercial
as well as biological
importance

3. Biological Importance
• Lubricants in alimentary canal and other
sites of metabolism
• Primary transport system for non polar
compounds
• Important constituents of cell membrane
and cell organelles
• Good food due to high caloric value
• Important for the functioning of nervous
system
• Essential fatty acids in the diet
• Starting materials for other products
• Lipids like fat soluble vitamins and
hormones are important for normal
biological functions

4. Classification of lipids
• Simple lipids
– Fats, oils and waxes (esters of
alcohol and fatty acids)
• Compound lipids (additional
moiety other than alcohol and
acid)
– Phospholipids
– Glycolipids
– Lipoproteins
• Derived lipids (which qualify the
general criteria but cant be grouped in
above classes)
– Steroids and carotenoids

5. Classification of lipids

6. Lipids
• Lipids (fixed oils, fats, and waxes)
are esters of long-chain fatty acids
and alcohols, or of closely related
derivatives. The chief difference
between these substances is the
type of alcohol; in fixed oils and fats,
glycerol combines with the fatty
acids; in waxes, the alcohol has a
higher molecular weight, e.g., cetyl
alcohol[CH3(CH2)15OH].

7. • Fats and oils are made from two
kinds of molecules: glycerol (a
type of alcohol with a hydroxyl
group on each of its three
carbons) and three fatty acids
joined by dehydration synthesis.
Since there are three fatty acids
attached, these are known as
triglycerides

8. Triglyceride
H2C
HC
H2C
O
O
O
C
C
C
R
R'
R''
O
O
O
• where R, R', and R" are long alkyl
chains; the three fatty acids
RCOOH, R'COOH and R"COOH
can be all different, all the same,
or only two the same.

9. Structure of Fatty Acids
• The “tail” of a fatty acid is a long
hydrocarbon chain, making it
hydrophobic. The “head” of the
molecule is a carboxyl group which is
hydrophilic. Fatty acids are the main
component of soap, where their tails
are soluble in oily dirt and their
heads are soluble in water to
emulsify and wash away the oily
dirt. However, when the head end iswhen the head end is
attached to glycerol to form a fat, thatattached to glycerol to form a fat, that
whole molecule is hydrophobicwhole molecule is hydrophobic.
(CH2)6COOH
H3C
Linoleic acid

10. •The terms saturated, mono-
unsaturated, and poly-unsaturated
refer to the number of hydrogens
attached to the hydrocarbon tails
of the fatty acids as compared to
the number of double bonds
between carbon atoms in the tail.
• Cyclic acids
The only known cyclic acid is
chaulmoogric acid, which is 13
(cyclopentenyl)-tridecanoic acid

11. • Fats, which are mostly
from animal sources, have
all single bonds between the
carbons in their fatty acid
tails, thus all the carbons
are also bonded to the
maximum number of
hydrogens possible.

12. • Since the fatty acids in these
triglycerides contain the
maximum possible amount of
hydrogens, these would be
called saturated fats.
• The hydrocarbon chains in these
fatty acids are, thus, fairly
straight and can pack closely
together, making these fatsfats
solid at roomsolid at room
temperaturetemperature.

13. • Oils, mostly from plant
sources, have some double
bonds between some of the
carbons in the hydrocarbon tail,
causing bends or “kinks” in the
shape of the molecules.
• Because some of the carbons
share double bonds, they’re not
bonded to as many hydrogens as
they could if they weren’t double
bonded to each other. Therefore
these oils are called
unsaturated fats.

14. • Because of the kinks in the
hydrocarbon tails, unsaturated
fats (or oils) can’t pack as
closely together, making them
liquid at roomliquid at room
temperaturetemperature.

15. • In unsaturated fatty acids, there
are two ways the pieces of the
hydrocarbon tail can be arranged
around a C=C double bond (cis
and trans).
• In cis bonds, the two pieces of
the carbon chain on either side
of the double bond are either
both “up” or both “down,” such
that both are on the same side of
the molecule.
• In trans bonds, the two pieces of
the molecule are on opposite
sides of the double bond, that is,
one “up” and one “down” across
from each other.

16. • Naturally-occurring
unsaturated vegetable
oils have almost all cis
bonds, but using oil for
frying causes some of
the cis bonds to convert
to trans bonds.

17. • If oil is used only once like
when you fry an egg, only a
few of the bonds do this so
it’s not too bad. However, if
oil is constantly reused, like
in fast food French fry
machines, more and more of
the cis bonds are changed
to trans until significant
numbers of fatty acids with
trans bonds build up. The
reason for this concern, is
that fatty acids with trans
bonds are carcinogenic, or
cancer-causing.

18. • Although most vegetable oils are
liquid at ordinary temperatures
and most animal fats are solid,
there are notable exceptions,
such as cocoa butter, which is
a solid vegetable oil, and cod
liver oil, which is a liquid animal
fat.

19. Production of fixed oils and fats
• Fixed oils and fats of
vegetable origin are obtained
by:
1. Extraction by pressing
Fixed oils are obtained by pressing in
hydraulic presses. If the pressing is
carried out in the cold, the oil is known
as a "virgin oil" or a "cold-pressed
oil." In contrast, if the pressing is
carried out in heat, the oil is known as
a "hot-pressed oil."
2. Extraction by solvents
Sometimes organic solvents are used
for the extraction of oils.

20. • Animal fats are separated from
other tissues by steam, with or
without pressure. The heat melts
the fat, which rises to the top and
may be separated by
decantation.

21. Biosynthesis of lipids
• In plants, biosynthesis of
saturated and unsaturated
fatty acids is from
combinations of acetate
units (acetate pathway).

22. Applications of fixed oils and fats
1. Soap manufacture
2. Suppositories, tablet coating
3. Dietary supplements
4. Emulsifying agents
5. Manufacture of paints,
varnishes and lubricants
6. Therapeutic uses (castor oil).

23. Examples
• Castor oil
• Olive oil
• Peanut oil
• Soybean oil
• Sesame oil
• Almond oil
• Cottonseed oil
• Corn oil
• Sunflower oil
• Cocoa butter

24. Waxes
• Like fats, waxes are esters
of fatty acids. The alcohol,
however, is not glycerol but
usually a long-chain, high-
molecular weight alcohol.
• In plants, waxes are
generally found covering the
external parts, like the
epidermis of leaves and
fruits, where their main
function is to prevent the
loss of water.

25. • Wax is also produced by
insects, e.g. the
honeycombs of bees and
wasps.
USES OF WAX
1. Wax is used in pharmacy to
make soft ointments harder
and to prepare lip salves.
2. The technical uses of waxes
are substantial, e.g. in shoe
polishes and car waxes.

26. Waxes × fixed oils and fats
• Wax has a melting point
above approximately 45 °C
(113 °F) (which
differentiates waxes from
fats and oils).
• Fats and oils my be
saponified by means of
either aqueous or alcoholic
alkali but waxes are only
saponified by alcoholic
alkali. (this fact is used for the
detection of fats when added as
adulterants to waxes).

27. Examples
• Jojoba wax (Simmondsia
chinensis)
• Carnauba wax (Copernicia
cerifera)
• Beeswax (Apis mellifera)

28. Chemical properties of fatty acids
• Salt Formation
• Ester
formation
• Hydrogenation
• Halogenation

29. • Oxidation
– With alkaline KMnO4
(hydroxylation takes place)
– With KMnO4 at elevated
temperature (after
hydroxylation cleavage takes
place to produce lower fatty
acids)
– Ozonolysis (first O3 adds
forming ozonoid which
then produce mixture of
aldehydes)
– Autoxidation (epoxides, peroxides
which undergo reduction to form
alcohols-polymerization to form resins)