Fatty Acids Prepared by Harsha Damale and Arya khadpe

1. Harsha Damale
MITU20BTFT0037
Arya Khadpe
MITU20BTFT0016

2. INTRODUCTION
• The acids which are combined with glycerol
in the naturally occurring fats are
called fatty acids.
• These acids contain even number of
carbon atoms linked together in long
chains which are in general un-branched.
• The chain contains from six to about twenty
carbon atoms in plant triglycerides and
the most frequent number being 16 or 18.
• The long chain molecule possesses the
carboxyl group at one end, while the
remainder part consists of carbon and hydrogen atoms only

4.  CLASSIFICATION OF FATTY ACID
SATURATED
FATTY ACID
UNSATURAT
ED FATTY
ACID
DEPENDING
ON CHAIN
LENGTH
ESSENTIAL
AND NON
ESSENTIAL
MONOSATURATE
D FATTY ACID
POLYSATURATE
D FATTY ACID
OMEGA
9
OMEGA
6
OMEGA
3
SHORT
CHAIN
MEDIUM
CHAIN
LONG CHAIN
VERY
LONG
CHAIN

5. Saturated Fatty Acid
• Saturated fatty acids have no double bonds in the chain or
contain single chain.
• Their general formula is CH, (CH, )n-COOH, where n
specifies the number of methylene groups between the
methyl and carboxyl carbons.
• They have higher melting points
• They are solid at room temperature.
• Examples- lauric, myristic, palmitic acid etc.

6. Unsaturated Fatty Acid
• These fatty acids contain one or more double bonds along the
length of the hydrocarbon chain.
• They are liquid at room temperature.
• Have low melting point.
• The commonly used system for designating the position of
double bond in unsaturated fatty acid is the delta (Δ)
numbering system.
• Example- linoleic acid, oleic acid, palmitoleic acid.
• In the naturally occurring unsaturated fatty acid the double
bond are in cis configuration and trans fatty acid are produced
by fermentation in the rumen of dairy animals and are obtained
from dairy products and meat.

7. Monounsaturated fatty acid:
• They contain only one double bond per fatty acid.
• The double bond is between C-9 and C-10(Δ⁹)
• Omega-9 fatty acids are a family of unsaturated fatty acids which have in commo
a final carbon–carbon double bond in the omega−9 position; that is, the ninth
bond from the methyl end of the fatty acid.
Omega 9
Omega-9 fatty acids are a family of unsaturated fatty acids which have in
common a final carbon–carbon double bond in the omega−9 position; that
is, the ninth bond from the methyl end of the fatty acid

8. Polyunsaturated fatty acid or PUFAS:
They contain two or more double bonds along the length of the
hydrocarbon chains.
PUFAs are also known as essential fatty acid.
Examples- linoleic and linolenic acid
Omega 6 fatty acid
Omega-6 fatty acids are a type of polyunsaturated fat found in vegetable
oils, nuts and seeds. When eaten in moderation and in place of the
saturated fats found in meats and dairy products, omega-6 fatty acids can
be good for your heart.
Omega 3 fatty acid
an unsaturated fatty acid of a kind occurring chiefly in fish oils, with double
bonds between the carbon atoms that are third and second from the end of
the hydrocarbon chain.

9. depending only on chain length they can be functionally divided into:
1. Short chain FA (SCFA): up to 6 carbon atoms;
2. Medium chain FA (MCFA): from 8 to 12 carbon atoms
3. Long chain FA (LCFA): from 14 to 18 carbon atoms;
4. Very long chain FA (VLCFA): from 20 carbon atoms onwards
On the basis of the ability or not to synthesize them from endogenous precursors by
animal
Non-Essential Fatty Acids
• Fatty acids which can be synthesized by the body.
• Fat that is not needed for vital functions is called non-essential fat.
• This extra or excess fat is used for storage for insulation and to protect vital
organs.
• Non-essential fats might be stored around organs (called visceral fat) or be might
be stored throughout the body underneath the skin (called subcutaneous fat).

10. Essential Fatty Acids
• The term essential fatty acids refer to fatty acids required for biological processes
but does not include the fats that only act as fuel.
• It should not be confused with essential oils which are essential in sense of being
a concentrated essence.
• Only two fatty acids are known to be essential for humans: alpha linolenic acid (an
omega 3 fatty acid) and gamma linolenic fatty acid (an omega 6 fatty acid).
• Some other fatty acids are classified as conditionally essential; they can become
essential under some development or disease condition example:
docosahexaenoic acid (an omega 3 fatty acids) ang gamma linolenic fatty acids
(an omega 6 fatty acids).
• When two EFAs were discovered in 1923, they were designated vitamin F but in
1929, research on rats showed that the two EFAs are better classified as fats
rather than vitamins.

11. acylglycerol
• an ester of glycerol and fatty acids that occurs naturally as fats and fatty
oils; "fresh fats contain glycerides of fatty acids and very little free acid
• glyceride
• animal oil - any oil obtained from animal substances
• fat - a soft greasy substance occurring in organic tissue and consisting of a
mixture of lipids (mostly triglycerides); "pizza has too much fat"
• triglyceride - glyceride occurring naturally in animal and vegetable tissues; it
consists of three individual fatty acids bound together in a single large
molecule; an important energy source forming much of the fat stored by the
body

12. Triacylglycerols
• Triacylglycerols (also called triglycerides) are tri-fatty acid esters of
glycerol
• Triacylglycerols are the major form of fatty acid storage in plants and
animals
• Triacylglycerols can be classified as fats or oils
• fats are solid at room temperature and most come from animals
• oils are usually liquid at room temperature and come from plants (palm
and coconut oils are solids at room temperature)

13. Cis and Trans Unsaturated Fatty Acids
Natural unsaturated fatty acids have cis double bonds
When unsaturated vegetable oils are hydrogenated to form more saturated oils
(as in margarine), some of the cis fatty acids are isomerized to trans fatty acids
Trans fatty acids are much more linear than cis fatty acids, so their melting
points are higher and studies have shown that trans fats may act similarly to
saturated fats and could contribute to heart disease and some cancers.

14. Functions of fatty acids
• They are the constituents of phospholipids and glycolipids (component of
biological membranes). Fatty acids are fuel molecules.
• They are stored as triacylglycerols, which are uncharged esters of glycerol.
They provide physical protection for the organ of the body.
• Fatty acid derivatives such as prostaglandins, leukotriene's
and thromboxane's serve as local hormones and
as a intracellular messenger in cell signaling
mechanism.

15. METABOLISM OF FATTY ACIDS
• Lyposisis carried out by lipase
• Once freed from glycerol, fatty acid can enter in cell & muscles by
diffusion
• Beta oxidation splits long carbon chains into acetyl CoA which
enter TCA cycle generates energy

16. PHYSICAL PROPERTIES
1. Fats and fatty acids are soluble in organic solvents, such as petroleum
ether, benzene and chloroform. They are insoluble in water.
2. Saturated fatty acids are solid at room temperature, while unsaturated
fatty acids are liquid.
3. Unsaturated fatty acids show cis-trans isomerism due to presence of
double bonds.
4. They are bad conductors of heat.
5. Saturated glycerides containing fats require high temperature for
melting, whereas unsaturated glycerides containing fats require
relatively lower temperature for its melting.

17. CHEMICAL PROPERTIES
1. Hydrolysis.
• Fats undergo hydrolysis when treated with mineral acids, the alkalis or fat
splitting enzyme lipase or hydrolases to yield glycerol and the constituent
fatty acids.
• Hydrolysis by alkalis, such as NaOH or KOH leads to the formation of sodium
or potassium salts of fatty acids. The salts are known as soaps and process of
its formation is saponification.

18. . 2.Hydrogenation:
• Oils containing unsaturated fatty acids can be hydrogenated in
presence of high temperature, pressure and finely divided nickel. By
this process the oils are converted into solid fats (glycerides of
saturated fatty acids). This reaction forms the basis of the industrial
production of hydrogenated oil (vegetable ghee).

19. 3. Hydrogenolysis:
• Oils and fats are converted into glycerol and a long chain aliphatic alcohol
when excess of hydrogen is passed through them under pressure and in
presence of copper-chromium catalyst. This splitting of fat by hydrogen is
called hydrogenolysis.
4. Halogenation:
• When unsaturated fatty acids are treated with halogens, such as iodine and
chlorine, they take up iodine or other halogens at their double bond site.
• This process of taking of iodine is called halogenation which is an indication of
unsaturation. Iodine number is the percentage of iodine absorbed by a fat.

20. 5. Rancidity:
• Oils and fats on long storage in contact with heat, light, air and moisture,
develop an unpleasant odor. Such oils and fats are known as rancid oils and
fats. The rancidity develops due to certain chemical changes taking place in
the fat.
• These changes include:
(i) Enzymatic hydrolysis,
(ii) Air oxidation of unsaturated fatty acids, and
(iii) β- oxidation of saturated fatty acids.
• In all above mentioned changes, hydrolysis of fats is caused by enzyme lipase
which is produced by microorganisms present in them. To check the rancidity,
it becomes essential to protect oils and fats from air, light and moisture during
storage.

21. 6. Emulsification:
• The process of breaking of large-sized fat molecules into smaller ones is
called emulsification. In animals, this process is brought about by bile juice
liberated from liver. Other emulsifying agents are water, soaps, proteins and
gums.

22. Availability
• Over half of the fatty acid residues of plant and animal lipids are
unsaturated and are often polyunsaturated.
• Bacterial fatty acid residues are rarely polyunsaturated but are
commonly branched, hydroxylated, or contain cyclopropane rings.
• Unusual fatty acids such as hydroxy fatty acids also occur as
components of the oils and waxes (esters of FAs and long chain
alcohols) produced by certain plants.
• There are more than 100 different FAs in nature and most FAs have an
even number of carbon atoms (mainly due to the mechanism of
biosynthesis-the concatenation of C2 units)
• Mainly present in the form of esters (not free)
• In higher plants and animals, the predominant FA residues are those of
the C16 and C18 species (palmitic, oleic, linoleic, and stearic acids).
• FAs with less than 14 and more than 20 carbon atoms are uncommon