LIPIDS

LIPIDS
• Refers to a collection of organic
molecules of varying chemical
composition
• Are grouped together on the basis of
their solubility in nonpolar solvents
• 4 main groups
– Fatty Acids (Saturated and Unsaturated)
– Glycerides (Glycerol-containing Lipids)
– Nonglyceride Lipids (Sphingolipids,Steroids,Wax)
– Complex Lipids (Lipoproteins)
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 Saturated
Fatty
Acids
Unsaturated

Neutral
Glycerides
Glycerides
Phosphoglycerides
LIPIDS
Complex
Lipids Lipoproteins

Sphingomyelins
Sphingolipids
Glycolipids
Nonglycerides Lipids Steroids

Waxes

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 BIOLOGICAL FUNCTIONS
OF LIPIDS
• Energy Source
– When oxidized, each gram of fat releases 9 kcal of
energy, or more than twice the energy released by
oxidation of a gram of carbohydrate
• Energy Storage
– In the form of triglycerides (TAG) in adipocytes
• Cell Membrane Structural Components
– Phosphoglycerides, sphingolipids, and steroids
make up the basic structure of all cell membranes

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 BIOLOGICAL FUNCTIONS
OF LIPIDS
• Hormones
– Steroid Hormones
• Vitamins
– Lipid-soluble vitamins (A,D,E, and K)
• Vitamin Absorption
– Dietary fat serves as a carrier of the lipid-soluble
vitamins
• Protection – fats as shock absorber
• Insulation – subcutaneous fat
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 (1) FATTY ACIDS
• Are long-chain
O
monocarboxylic
acids R C OH
• Generally contain an
even number of #1 Carbon Acid Group
carbon atoms

O
R C OH Polar End - Hydrophilic End

Non-polar End - Hydrophobic End

(Fat-s oluble tail)
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 CLASSIFICATIONS OF
FATTY ACID

• Length of the Carbon Chain

– Long-chain, medium-chain, short-chain
• Degree of Unsaturation
– Saturated, Unsaturated (Mono, Poly)
• Location of Double Bonds
– Omega-3 Fatty Acid, Omega-6 Fatty Acid

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 (1) FATTY ACIDS
• Short-Chain Fatty Acids
– Less than 6 carbons

• Medium-Chain Fatty Acids

– 6-10 carbons

• Long-Chain Fatty Acids

– More than 12 carbons

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 (1) FATTY ACIDS
• Saturated Fatty Acids
– Each C being “saturated” with H
– General Formula: CH3(CH2)nCOOH

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LAURIC ACID

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 (1) FATTY ACIDS
• Unsaturated Fatty Acids
– Composed of at least one carbon-to-
carbon double bond
– Almost are in the cis configuration

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 (1) FATTY ACIDS
• Monounsaturated Fatty Acids (MUFA)
– Composed of one carbon-to-carbon
double bond

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 (1) FATTY ACIDS
• Polyunsaturated Fatty Acids (MUFA)
– Composed of more than one carbon-to-
carbon double bond

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 (1) FATTY ACIDS
• Polyunsaturated Fatty Acids (MUFA)
– are identified by position of the double
bond nearest the methyl end (CH3) of the
carbon chain; this is described as an
omega number;
– If PUFA has first double bond 3 carbons
away from the methyl end = omega 3 FA
– 6 carbons from methyl end = omega 6 FA

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 (1) FATTY ACIDS
• cis-Fatty Acid
– H’s on same side of the double bond; fold
into a U-like formation; naturally occurring

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 (1) FATTY ACIDS
• trans-Fatty Acid
– H’s on the opposite side of the double
bond; occur in partially hydrogenated food

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 PROPERTY SATURATED UNSATURATED
FATTY ACIDS FATTY ACID
C-C Bonds within Only C-C single At least one C-C
the hydrocarbon bonds double bond
chain
Hydrocarbon chains are Alkanes Alkenes
characteristic of what
group of hydrocarbon

“Shape” of Linear, Fully Bend in carbon

Hydrocarbon chain extended chain at site of C-C
double bond
Physical state at Solid Liquid
room temperature
Melting Point Higher Lower

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 BUT, ARE ALL TRANS-FAT
BAD?
• Omega-3:
– Eicosopentaenoic acid (EPA)
– Docosahexaenoic acid (DHA)
– Alpha-linolenic acid (ALA)
• flaxseed--most, canola (rapeseed), soybean,
walnut, wheat germ
• body can make some EPA and DHA from ALA
• Omega-6
– corn, safflower, cottonseed, sesame,
sunflower
– Linoleic acid
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 CHEMICAL REACTIONS
OF FATTY ACID
• Esterification
– Fatty acids react with alcohols to form
esters and water

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 CHEMICAL REACTIONS
OF FATTY ACID
• Acid Hydrolysis
– Producing fatty acids from esters
– Opposite of esterification
• Saponification
– Is the base-catalyzed hydrolysis of an
ester
– the product of this reaction, an ionized
salt, is a soap
• Have a long uncharged hydrocarbon tail and a
negatively charged terminus (the carboxylate
terminus 30
 CHEMICAL REACTIONS
OF FATTY ACID
• Saponification
– Is the base-catalyzed hydrolysis of an
ester

– the product of this reaction, an ionized

salt, is a soap
• Have a long uncharged hydrocarbon tail and a
negatively charged terminus (the carboxylate
terminus), they form micelles that dissolve oil
and dirt particles

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 CHEMICAL REACTIONS
OF FATTY ACID
• Reaction at the Double Bond
(Unsaturated Fatty Acids)
– Hydrogenation
• Used in the food industry to convert
polyunsaturated vegetable oils into saturated
solid fats
– Partial Hydrogenation
• Carried out to add hydrogen to some, but not
all, double bonds in polyunsaturated oils
• In this way liquid vegetable oils are converted
into solid form (Crisco and margarine)
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 (2) GLYCERIDES
• Are lipid esters that contain the
glycerol molecule and fatty acids
– 2 Classes
• Neutral Glycerides – nonionic and
nonpolar

• Phosphoglycerides – have polar region,

the phosphoryl group, in addition to the
nonpolar fatty acid tails

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 (2) GLYCERIDES
• Neutral Glycerides
– Produce after the esterification of glycerol
with a fatty acid
– Esterification may occur at one, two, or all
three positions, producing:
• Monoglycerides
• Diglycerides
• Triglycerides – most important and main
storage form of lipids in man (adipocytes)

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 FAT vs. OIL
• Fat
– A mixture of triglycerides containing high
proportion of long-chain, saturated fatty
acids
• Animals – generally solids
• Plants or Fish – usually liquids
• Oil
– Liquid fat
– Contain high proportion of unsaturated
fatty acids and saturated fatty acids
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 (2) GLYCERIDES
• Neutral Glycerides
– There are no charges (+ or -) on these
molecules
– These long molecules readily stack with
one another and constitute the majority of
the lipids stored in the body’s fat cells
– Primary function is to store energy
• More energy-rich nutrients are consumed than
are required for metabolic processes, much of
the excess is converted to neutral glycerides
and stored as TAG in fat cells
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 (2) GLYCERIDES
• Phosphoglycerides
– Phospholipids – are
group of lipids that are
phosphate esters
• The presence of the
phosphoryl group results
in a molecule with a polar
head (the phosphoryl
group) and a nonpolar tail
(the alkyl chain of the fatty
acid)

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 (2) GLYCERIDES
• Phosphoglycerides
– Most abundant membrane lipids and
derived from glycerol-3-phosphate
– Contain acyl groups derived from long
chain fatty acids at C-11 and C-2 of
glycerol-3-phosphate
– At C-3 the phosphoryl group is joined to
glycerol by a phosphoester bond
• Phosphatidate – simplest phosphoglyceride
contains a free phosphoryl group

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