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Unit 5 Lipids
Unit 5 Lipids
2
Introduction
The types of lipids that we will look at include.
• Fatty Acids
• In the carboxylic acid family
• Waxes
• Fatty Acids + Alcohols
• Triglycerides
• 3 Fatty acids + glycerol
• Phospholipids and glycolipids
• 2 fatty acids + glycerol + phosphate + X
• Steroids
• Derivatives of cholesterol
• Eicosanoids
• Derivatives of the Fatty acid arachidonic acid
• Membranes
• Formed from phospholipids and glycolipids
3
Fatty Acids
Fatty acids contain a carboxylic acid group
• This should make them quite polar
However, they also contain a long hydrocarbon tail
• Which overall, makes them nonpolar.
nonpolar polar
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Fatty Acids
Fatty acids typically contain between 12 and 20 carbons
• The number is usually always even.
nonpolar polar
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Fatty Acids
Melting points for saturated fatty acids:
Melting Temperature {°C}
No. of Carbons
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Fatty Acids
Some fatty acids contain double bonds
• unsaturated
• monounsaturated
• polyunsaturated
• polyunsaturated
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Fatty Acids
The common fatty acids found in biological systems are
shown in Table 8.1 of Raymond.
Text
9
Fatty Acids
The cis double bonds produce kinks, which disrupt the
London forces by preventing the tails from packing close to
one another.
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Fatty Acids
As acids, the carboxylic acid group in fatty acids can react
with a base to produce a carboxylate ion
• By donating its proton (H+) to the base the fatty acid
becomes negatively charged.
• We will talk more about acids and bases in Unit 6
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1
Fatty Acids
The negative charge makes the polar head portion of the the
fatty acid even more more polar and hydrophilic.
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2
Fatty Acids
The salts of fatty acids are also called soaps, and are
considered amphipathic, meaning they have a part that is
very hydrophobic along with a part that is very hydrophilic.
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3
Biochemical Compounds &
Their Interactions with Water (Unit 3)
When placed in water,
amphipathic molecules,
form structures, such as
micelles, which attempt to
address the conflict.
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Fatty Acids
The salts of fatty acids are also called soaps, and are
considered amphipathic, meaning they have a part that is
very hydrophobic along with a part that is very hydrophilic.
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Waxes
Waxes are made by combining fatty acids with long chain
alcohols.
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Alcohols, Carboxylic Acids & Esters (Unit 2)
We look now at three families that are distinguished by a
functional group that contains the element oxygen.
Esters
• Chemically, esters can be synthesize by reacting a
carboxylic acid with and alcohol:
O
CH3 CH2 C O CH2 CH3
Carboxylic Alcohol
acid part part
Ethyl propanoate
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Waxes
Waxes are esters.
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Waxes
Waxes are very hydrophobic and are used by plants and
animals for protective, water-proof coatings
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0
Questions
Draw the skeletal structures for the products formed when
beeswax undergoes base-catalzyed hydrolysis
(saponification).
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1
Reactions Involving Water (Unit 4)
Hydrolysis
• Hydrolysis can also be catalyzed using a base (OH-):.
O O
H2O
CH3 CH2 CH2 C O CH2 CH3 CH3 CH2 CH2 C O + HO CH2 CH3
OH-
2
2
Triglycerides
Triglycerides are a storage form of fatty acids in mammals.
• Often when blood tests are done, they measure your
triglycyeride levels.
• High triglyceride levels in the blood are a risk indicator for
artherosclerosis.
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3
Triglycerides
Triglycerides are a combination of three 3 fatty acid
molecules with a glycerol molecule.
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4
Triglycerides
Glycerol, which is also called glycerin,
is an alcohol with three hydroxyl
groups.
HO CH2
• As with the waxes, the fatty acids
can react with the hydroxyl groups to
form esters. HO CH
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Triglycerides
For triglycerides, all three hydroxyls of the glycerol have a
fatty acid residue attached to it.
O
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2C O CH2
O
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2C O CH
O
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2C O CH2
fatty acid glycerol
residues residue
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Figure 8.6
from
Raymond
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Triglycerides
Just as with fatty acids, where the presence of cis double
bonds lower the melting points, triglycerides made from
unsaturated fatty acids have lower melting points than those
made from saturated fatty acids.
• Triglycerides from animals tend to have a higher proportion
of saturated fatty acids.
• Most are solids at room temperature and are called fats.
• Examples include: butter, lard and bacon grease
• Triglycerides from plants tend to have a higher proportion of
unsaturated fatty acids.
• Most are liquids at room temperature and are called oils.
• Examples include: corn oil, canola oil, peanut oil and olive oil.
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Triglycerides
Triglycerides as primarily used as a form of stored energy.
• This is why when you eat more than you need to meet your
energy requirements, the excess energy is stored in the
form of fat.
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Triglycerides
Reactions that involve triglycerides include:
• Hydrogenation
• Oxidation
• Base-catalyzed hydrolysis (saponification)
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Transport of fats:
VLDL moves triglycerides
from liver to tissues.
LDL transfers
cholesterol to HDL carries
tissues from liver. cholesterol from
tissues to liver.
live r
g a ll
b la d de r
O
O
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Fun Topic !: Fake Fats
Side effects?
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Oxidation and Reduction (Unit 4)
Hydrogenation
• Another type of oxidation/reduction reaction is the
hydrogenation reaction:
H H
H H
C C + H2 H C C H
platinum
H H catalyst
H H
unsaturated saturated
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5
Triglycerides
Hydrogenation of triglycerides
• This is the same reaction that we saw in Unit 4 with the
hydrogenation of alkenes.
• Unsaturated fats and oils contain alkenes and can be
hydrogenated to produce saturated fats.
• Commercially, vegetable oils are often hydrogenated to
produce a solid product that has better qualities for making
baked goods.
• Animal fats, such as butter and lard, which are naturally saturated,
can also be used in baking, but unlike the vegetable oils, they come
with cholesterol, which is undesirable for health reasons.
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Triglycerides
Hydrogenation of triglycerides
• Total hydrogenation
liquid solid
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Triglycerides
Hydrogenation of triglycerides
• Partial hydrogenation
liquid solid
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Triglycerides
Hydrogenation of
triglycerides
• Partial
hydrogenation
cab produce
trans fats.
• Trans fats have
been found to
lower your HDL
(“Good
cholesterol”)
levels.
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Triglycerides
Saturated vs Unsaturated Fats
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Triglycerides
Saturated vs Unsaturated Fats
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Triglycerides
Saturated vs Unsaturated Fats
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Triglycerides
Saturated vs Unsaturated Fats
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Triglycerides
Saturated vs Unsaturated Fats
saturated fat O
C
O CH2
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4
Triglycerides
Oxidation of triglycerides
• Unsaturated triglycerides can react with oxygen to produce
small change fatty acids another small molecules.
• These often do not smell very good
• This makes solid fats and oils more stable than liquid oils
and is why the solid fats are preferred for deep frying.
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Triglycerides
Oxidation of triglycerides
These stink !
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Triglycerides
Saponification of triglycerides
• Saponification is the base-catalyzed hydrolysis of the ester
bonds in a triglyceride.
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Reactions With Water (Unit 4)
Hydrolysis example:
• The base catalyzed hydrolysis of fats produces soap and
glycerol O
C
O CH2
H O
C 3 H2O
O CH
OH-
H
H O
H C
O CH2
Fat
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Reactions With Water (Unit 4)
Hydrolysis example:
• The base catalyzed hydrolysis of fats produces soap and
glycerol O
C
O HO CH2
H O
3 H2O C
O + HO CH
OH-
H
H O
H C
O HO CH2
Soap Glycerol
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Phospholipids and Glycolipids
Phospholipids and Glycolipids are the stuff that biological
membranes are made of.
• Like the soaps, these molecules are highly aphipathic, and
when mixed with water spontaneously form membranes
that are described as lipid bilayers.
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Phospholipids and Glycolipids
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Phospholipids and Glycolipids
Phospholipids and Glycolipids are the stuff that biological
membranes are made of.
• Like the soaps, these molecules are highly aphipathic, and
when mixed with water spontaneously form membranes
that are described as lipid bilayers.
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2
Phospholipids and Glycolipids
Phosphospholipids
• There a are two types of phospholipids
• Glycerophospholipids
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Phospholipids and Glycolipids
Phosphospholipids
• There a are two types of phospholipids
• Sphingolipids
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4
Phospholipids and Glycolipids
Phosphospholipids
• The Glycerophospholipids have a structure similar to
triglycerides, with one of the fatty acids replaced with a
phosphate.
There is usually
an additional
alcohol attached
to the other side
of the phosphate
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Phospholipids and Glycolipids
Phosphospholipids
• The Glycerophospholipids have a structure similar to
triglycerides, with one of the fatty acids replaced with a
phosphate.
phosphoester
bonds
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Phospholipids and Glycolipids
Phosphospholipids
• The Glycerophospholipids have a structure similar to
triglycerides, with one of the fatty acids replaced with a
phosphate.
“Phosphotidyl-”
refers to everything
but the X
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Phospholipids and Glycolipids
Phosphospholipids
• Phospholipids are used commercially as emulsifying
agents.
• An emulsifying agent stabilizes an emulsion.
• An emulsion is a colloidal suspension of one liquid in another.
‣ An example is mayonnaise, which is a colloidal suspension of oil and
water.
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Phospholipids and Glycolipids
Phosphospholipids
• The sphingolipids function similarly to the
glycerophospholipids, but structurally they are different.
• There is not glycerol core
• The glycerol and one of the fatty acids found in glycerophospholipids
is replaced with a molecule called sphingosine.
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Phospholipids and Glycolipids
Phosphospholipids
• The sphingolipids are found in the myelin membranes that
insulate the nerve cells.
• Some sphingolipids use sugars for the alcohol portion of
the molecule
• These are called glycolipids.
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Steroids
Steroids are a type of lipid that is not derived form a fatty
acid.
• They are based instead on a system of five cycloalkane
rings that are fused together.
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1
Steroids
Steroids are a type of lipid that is not derived form a fatty
acid.
• They are based instead on a system of five cycloalkane
rings that are fused together.
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2
Steroids
Cholesterol is the steroid that used as the starting point for
the synthesis of other steroids.
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3
Steroids
• Cholesterol is only found in animals
• Besides being used to synthesize the other steroids,
cholesterol is dissolved in membranes to keep them fluid.
• Plants use the alternative strategy of using polyunsaturated fatty
acids to make their phospholipids.
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4
Lipoproteins
Lipoproteins are used to transport the
water insoluble lipids such as
triglycerides, phospholipids and
cholesterol, in the blood.
• Lipoproteins contain lipids and
proteins.
• They include:
• Chylomicrons transport primarily
triglycerides from the digestive track.
• LDLs (low density lipoproteins) transport
cholesterol, triglycerides and phospholipids
from the liver to other tissues.
• HDLs (high density lipoproteins) transport
cholesterol and phospholipids back to the
liver.
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5
Lipoproteins
The HDL and LDL levels in the blood can be used to assess
ones risk for atherosclerosis.
• High levels of HDL is considered good
• This is why HDL is sometimes referred to as “good cholesterol”
• > 40 mg/dL is good.
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Eicosanoids
Eicosanoids are derived from arachidonic acid:
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Membranes
Fluid mosaic model
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Membranes
Transport across membranes
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The End