LIPIDS

LIPIDS
▷ is an organic compound found in living
organisms formed mainly from alcohol
and fatty acids combined together by
ester

▷ They are hydrophobic, nonpolar

molelcules.
• They are soluble in nonpolar solvent.
• They are insoluble in polar solvents

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LIPIDS

▷ known as fat provide a or way of storing

chemical energy and carbon atoms in the
body
▷ Fats also surround and insulate vital
body organs, providing protection from
mechanical shock, and pr even t i n g
excessive loss of heat energy

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 Structure &
Classification

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Based on biochemical
structure:
1. Energy-storage
• triacylglycerols
2. Membrane lipids
• phospholipids, sphingoglycolipids, cholesterol
3. Emulsification lipids
• bile acids
4. Messenger lipids
• steroid hormones & eicosanoids
5. Protective -coating lipids
• biological wax
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Based upon whether or nor
saponification occurs, when lipid
is placed in basic aqueous:
1. Saponifiable lipids - are converted
into smaller molecules when
hydrolysis occurs

○ Triacylglycerides
○ Phospholipids
○ Spingoglycolipids
○ Biological waxes

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2. Nonsaponifiable lipids - cannot
be broken up into smaller units since
they do not react on water

○ Cholesterol
○ Steriod hormone, bile acids, and
eicosanoids

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Fatty Acids

▷ is a naturally occurring monocarboxylic

acid
▷ also contain long hydrocarbon chain

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Fatty Acids

Based on carbon chain length

▷ Long-chain - C12 to C26
▷ Medium-chain - C8 and C10
▷ Short-chain - C4 and C6

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Types of Fatty Acid

1. Saturated Fatty Acid

▷ is a fatty acid with a carbon chain in which
all carbon bonds are single bonds

IUPAC name: hexadecanoic acid

Common name: Palmitic acid

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2. Unsaturated Fatty Acids

a) Monounsaturated fatty acid

▷ is a fatty acid with a carbon chain in which
one carbon-carbon double bond is present

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b) Polysaturated Fatty Acids
▷ is a fatty acid with a carbon chain in which
two or more carbon- carbon double
bonds are present

Linoleic Acid

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 EXERCISE
1.

2.

18:1 Δ9

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Physical Properties of FA

1. Water solubillity
• solubility decreases as carbon chain
length increases
• ↑ carbon chain =↓ water solubility
2. Melting points
• strongly influenced by both carbon
chain length and degree of unsaturation
• ↑ carbon chain = ↑ MP
• ↑ double bonds = ↓ MP

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The cis double bonds produce kinks which
prevent from packing together.

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1. Energy-Storage
Lipids:
Triacyglycerols
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Triacylglycerol
▷ it functions within the body as energy-
storage material
▷ are concentrated primarily in special cells
(adipocytes)
▷ has three ester functional groups and a
glycerol

Glycerol

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Triacylglycerol
▷ defined as a lipid form formed by
esterification of three fatty acids to a
glycerol molecule
▷ simple or mixed

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Simple triacylglycerol
▷ is a triester formed from the esterification
of glycerol with three identical fatty acid
molecules
▷ rare

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Mixed triacylglycerol
▷ is a triester formed from the esterification
of glycerol with more than one kind of fatty
acid molecules
▷ most biochemically important
triacylglycerol

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Fats and Oils

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 Fats and Oils
▷ both are naturally occuring mixtures
of triacylglycerol which many
different triacylgycerol molecules
are present

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 Fat Oil
▷ solid or semi-solid ▷ liquid at room
at room temperature
temperature (25℃)
(25℃) ▷ generally, oils are
▷ generally, fats are obtained from
obtained from plant sources
animal sources ▷ contain large
▷ composed largely amount of mono
of triacyglycerol or poly
which saturated unsaturated fatty
FA predominate acids
and some
unsaturated FA
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▷ Pure fats and pure oils are
colorless, odorless and tasteless.

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Dietary
Considerations

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Bad fat vs Good fat

▷ saturated fat?
▷ monounsaturated fat?
▷ polyunsaturated fat?

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Essential Fatty Acids

▷ fatty acid needed in the human

body that must be obtained from
dietary sources because it cannot
be synthesized within the body

▷ Linoleic Acid
▷ Linolenic Acid

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What will hapen if these
acids are missing in the diet?

▷ red and irritated skin

▷ infection
▷ dehydration
▷ liver abnormalities

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Purpose

▷ for proper membrane structure

▷ serve as a starting material for
production of several nutritionally
important longer chain omega-6
and omega-3 acids

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 Linoleic Acid (18:2)
▷ Starting material for biosynthesis of
arachidonic acid (20:4)

▷ Arachidonic acid is a major starting

material for eicosanoids substances that
help regulate blood pressure, clotting, and
several other important body function.

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Linolenic Acid (18:3)

▷ Starting material for biosynthesis of two

additional omega-3 FA
▷ EPA (20:5)
▷ DHA (22:6)
○ Important constituents of the communication
membranes of the brain and are necessary for
normal brain development
○ Active in the retina of the eye

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Chemical Reactions of
Triacylglycerol

▷ Hydrolysis
▷ Saponification
▷ Hydrogenation
▷ Oxidation

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Hydrolysis
▷ reverse of the esterification
reaction by which it was formed
▷ requires the presence of acid and
base

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Complete hydrolysis -all three fatty
acids are removed

Partial hydrolysis - one or more fatty

acid residues remain attached to the
glycerol

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Saponification

▷ reaction carried out in an alkaline

solution
▷ Fat and oil products are glycerol
and fatty acid salts

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 Hydrogenation

▷ involves hydrogen addition across carbon-carbon

multiple bonds, which increases the degree of
saturation as some double bonds are converted to
single bonds
▷ ↑MP

-CH2-CH2 CH=CH-CH2-CH2 → -CH2-CH2-CH2-CH2-CH2-CH2

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 Steps

1. Fats or oils + 3H2O → 3 fatty acids + Glycerol

▷ Hydrolysis of the ester linkages to produce glycerol and
3 fatty acids

2. 3 fatty acids + 3NaOH → 3 fatty acids salts+ 3H2O

▷ Acid-base reaction that produces water plus salts

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 Oxidation

▷ the C-C double bonds present in fatty acid

residues are subject to oxidation with
molecular oxygen as the oxidizing agent
* Short-chain *Short-chain
O O
Unsaturated FA → Aldehydes → Carboxylic acid

*produce objectionable odor

= rancid
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2. Membrane
Lipids:
Phospholipids
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Phospholipids
▷ most abundant type of membrane lipid
▷ lipid that contains one or more fatty acids
and phosphate group
▷ a platform molecule to which the FA and a
phosphate group are attached, and an
alcohol that is attached to phosphate group
▷ There are two types of phospholipids:
○ Glycero-
○ Sphingo-

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Glycerophospholipid
• contains 2 fatty acids and a phoshate group esterified
to a glycerol molecule and an alcohol esterified to
phosphate group

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Phosphotidylcholine
▷ also known as lecithin
▷ waxy solids that form colloidal suspension
in water
▷ good dietary source: egg yolks, soy beans
▷ use as emulsifiers, to promote mixing of
immiscible materials

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Phosphatidylethanolamine

▷ also known as cephalin

▷ found in heart and liver tissues &
high conc. in brain
▷ important in blood clotting

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▷ Sphingophospholipid
• structure based on the 18 carbon
monosaturated aminodialcohol sphingosine
• contains one fatty acid and one phophate
group attached to a sphingosine and alcohol
attached to phosphate group

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Sphingomyelin

▷ found in all cell membranes

▷ important in structural component
of myelin sheath

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Membrane Lipids:
Sphingoglycolipids

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Sphingoglycolipids

▷ contains both fatty acid and carbohydrate

components attached to a sphingosine.

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Cerebrosides
▷ simplest sphingoglycolipid,
contain a single monosaccharide
unit - either glucose or galactose
• Also present in myelin sheath of nerves

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Ganglioside

▷ more complex, branched chain up to

seven monosaccharide residues
▷ occurs in the gray matter of the brain as
well as in myelin sheath

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