LIPIDS
Understand the biological importance,
functions and clinical significance of the lipids
Characterize lipids through its chemical
structures and name some of the common fatty
acids
Differentiate the saturated from unsaturated
fatty acids and cite some examples of their
food sources and naturally occurring fatty
acids
Lipid:An organic compound
found in living organisms that is
insoluble (or only sparingly
soluble) in water but soluble in
non-polar organic solvents.
Amphipathic, having non-polar
(hydrophobic) and a polar end
“Lipid” is synonymous with “fat”
Unlike other biomolecules, lipids do
not have a common structural
features that serves as the basis for
defining such compounds.
Storage form of energy
Important dietary components because
of their high energy value and also
because of fat-soluble vitamins and the
essential fatty acids contained in the fat
of natural foods
Structural components of biological
membranes
Serve as thermal insulators in the
subcutaneous tissues and around certain
organs
Provide shape and contour to the
body
Act as metabolic regulator
Serve as the means of transporting
lipids in the blood.
The following are
associated with
abnormal chemistry or
metabolism of lipids:
Obesity
Atherosclerosis
Diabetes Mellitus
Fatty liver
Lipid storage diseases
Classification: Based on two
methods
Biochemical function
Saponification (hydrolysis under
basic conditions)
• Energy-storage lipids - triacylglycerols
• Membrane lipids - phospholipids,
sphingoglycolipids, and cholesterol
• Emulsification lipids - bile acids
• Chemical messenger lipids - steroid
hormones and eicosanoids)
• Protective-coating lipids - biological waxes
Saponification reaction: Hydrolysis
reaction that occurs in a basic solution.
Based on saponification reactions lipids
are divided into two categories :
• Saponifiable lipids – triacylglycerols
phospholipids, sphingoglycolipids,
cholesterol and biological waxes
• Nonsaponifiable lipids - bile acids, steroid
hormones and eicosanoids)
Lipids exhibit
structural
diversity
Some are esters,
some are amides,
and some are
alcohols (acyclic
and cyclic) and
some are
polycyclic.
Carboxylicacids with linear (unbranched)
carbon chain - Fatty acids are naturally
occurring monocarboxylic acids
Even # of Carbon atoms:
Long chain fatty acids: C12 - C26
Medium chain fatty acids: C6 - C11
Short-chain fatty acids: C4 - C5
TwoTypes:
• Saturated - all C-C bonds are single bonds
• Unsaturated
Monounsaturated: one C=C bond
Polyunsaturated: 2 or more C=C bonds
present - up to six double bonds are
present in fatty acids
Some fatty acids and their common
names:
12:0 Lauric acid (n-Dodecanoic acid)
14:0 Myristic acid; (n-Tetradecanoic acid)
16:0 Palmitic acid; 16:1 cisD9 Palmitoleic acid
18:0 Stearic acid; 18:1 cisD9 Oleic acid
18:2 cisD9,12 Linoleic acid
18:3 cisD9,12,15 a-Linonenic acid
20:4 cisD5,8,11,14 Arachidonic acid
20:5 cisD5,8,11,14,17 Eicosapentaenoic acid (an
omega-3) (EPA)
22:6 cisD4,7,10,13,16,19 Docosahexaenoic acid
(DHA)
O
a C
4
3 1 O
2
9
fatty acid with a cis-D
double bond
Organicacid
(chain of
carbons with
hydrogens
attached) that
has an acid
group at one
end & a methyl
group at the
other end
glycerol + 3 fatty acids triglyceride + H2O
Fatty Acids – carbon
chains, vary in:
1. Length – affects
absorption
2. Saturation –chemical
structure; affects
cooking & storage
properties and health
Water solubility: Short chain
fatty acids have some
solubility whereas long
chain fatty acids are
insoluble
• Short chain fatty acids are
sparingly soluble because of
carboxylic acid polar group
Melting Point Depends
Upon:
• Length of carbon chain
• Degree of unsaturation (number
of double bonds in a molecule)
Space-Filling Molecules
The number of bends in a fatty acid chain
increase as the number of double bonds
increase
• Less packing occurs
• Melting point is lower
• Tend to be liquids at room temperature
Saturated Fatty Acids
Fatty acid with a carbon chain in which all C-C
bonds are single bonds
Numbering starts from the end of -COOH
group
Structural notation: it indicates number of C
atoms
Example - Lauric acid has 12 C atoms and no
double bonds so it is (12:0)
O
H 3C (CH) 10 C OH
O
or
C
11 9 7 5 3 1 OH
12 10 8 6 4 2
Unsaturated Fatty
Acids
Unsaturated fatty acid – carbon chains lack
some hydrogens (>1 C=C double bond)
1. Monounsaturated fat – triglyceride
containing fatty acids with 1 double
bond; i.e. canola & olive oil
2. Polyunsaturated fat- triglycerides
containing a high % of fatty acids with
>2 double bonds; i.e. corn, safflower,
soybean, sunflower oils and fish;
3. Appear liquid at room temperature
Unsaturated Fatty
Acids
A monounsaturated
fatty acid is a fatty
acid with a carbon
chain in which one
carbon–carbon
double bond is
present.
Different ways of
depicting the
structure
Unsaturated Fatty
Acids
Polyunsaturated Fatty Acids (PUFAs)
A polyunsaturated fatty acid is a fatty acid
with a carbon chain in which two or more
carbon–carbon double bonds are present.
Up to six double bonds are found in
biochemically important PUFAs.
Two types of unsaturated fatty acids.
• Omega (ω)-3 fatty acids - An unsaturated fatty acid with its
endmost double bond three carbon atoms away from its methyl
end.
• Omega (ω)-6 fatty acid is an unsaturated fatty acid with its
endmost double bond six carbon atoms away from its methyl end.
Unsaturated Fatty
Acids
Omega Acids
Essential Fatty Acids: Must be part of diet
Nutritionally important Omega-3 and Omega-6
fatty acids
• Linolenic acid – Omega-3
• Linoleic acid – Omega-6
Linoleic Acid Deficiency:
• Skin redness - becomes irritated
• Infections and dehydration
• Liver abnormalities
• Children need it the most
• Human milk has more than cow’s milk
Unsaturated Fatty
Acids
American Diet
Sufficient in omega 6 fatty acids
Deficient in omega 3 fatty acids
• Fish - good source for omega 3 fatty
acids
High rate of heart disease may be due
to imbalance in omega 3 and 6 fatty
acids
• Ideal ratio: Omega 6 : Omega 3 (4 - 10
g: 1g)
Studies indicate that type of dietary fat and
amount of dietary fat are important for a
balanced diet:
• Current recommended amounts are: total
fat intake in calories:
15% - Monounsaturated fat
10% - Polyunsaturated
<10% - Saturated fats
Studies also indicate that:
• Saturated fats are considered “bad fats”
• Monounsaturated fats are considered “good fats”
• Trans-monounsaturated fats are considered “bad fats”
• Polyunsaturated fats can be both “good fats” and “bad fats”
Omega 3 and 6 are important “good fats”
SATURATED UNSATURATED
o
Sat. Fatty Acids Formula Melting Point ( C)
Butyric C4H8O2 Liquid
Palmitic C16H22O2 63
Stearic C18H36O2 70
o
Unsat. Fatty Acids Formula Melting Point ( C)
Oleic C18H34O2 Liquid
Linoleic C18H32O2 Liquid
Linolenic C18H30O2 Liquid
1. Read further on the classifications of
lipids according to its biochemical function
and saponification.
2. Bring fresh coconut oil (gata) for our
experiment on Friday.
3. Create a food diary starting tomorrow on
what you are eating (include vitamins). We
will evaluate these foods we are eating
whether we are following the food pyramid
that is recommended.
