LIPIDS
MC 2 - Biochemistry
Content
• General properties
• Biological role of lipids
• The Fatty acids
• Classification of Lipids
• Reactions of Lipids
• The Cell Membrane
General Properties
1. Organic compounds of biological origin.
2. Insoluble in water and alcohol.
3. Soluble in non-polar solvents such as ether, acetone, chloroform, and benzene.
4. Contain carbon, hydrogen, oxygen, and sometimes nitrogen and phosphorus.
5. In most cases, yield fatty acids on hydrolysis or combine with fatty acids to
form esters.
6. Take part in plant and animal metabolism.
The Biological Role of Lipids
• Source of energy
• Insulation
• Cell membrane
• Regulation
The Fatty Acids
Fatty acids
• straight chain organic acids
• building blocks of lipids
• usually found in fats and oils with C4-C26,
most common are C12 – C18;
• fatty acids found in natural fats usually contain
an even number of carbon atoms.
Fatty acids
• Saturated fatty acids
- contain only single bonds
• Unsaturated fatty acids
- contain double bonds
- have lower melting points
- the greater the degree of
unsaturation, the lower the
melting point
Table1. Some Naturally occurring Saturated Fatty Acids
Number Common Name Formula Occurence MP, 0C
of C
Atoms
4 butyric CH3(CH2)2COOH 4-5 % butter -7.9
6 caproic CH3(CH2)4COOH Goat’s milk -3.4
8 caprylic CH3(CH2)6COOH 16.3
10 capric CH3(CH2)8COOH 31.2
12 lauric CH3(CH2)10COOH Vegetable oils especially 43.9
coconut oil
14 myristic CH3(CH2)12COOH Animals, vegetables, 54.1
palm oil, milk, sperm
whale oil
Table1. Some Naturally occurring Saturated Fatty Acids
Number of Common Name Formula Occurence MP, 0C
C Atoms
16 palmitic CH3(CH2)14COOH Extensively found in many 62.7
fats and oils
18 stearic CH3(CH2)16COOH Extensively found in many 69.9
fats and oils
20 arachidic CH3(CH2)18COOH Peanut oil 75.4
22 behemic CH3(CH2)20COOH Minor constituents of most 79.9
seed oils, marine animal
fats
24 lignoceric CH3(CH2)22COOH Seed fat from an Indian 84.2
tree
26 cerotic CH3(CH2)24COOH Bees wax 87.7
Table 2. Some naturally occurring unsaturated fatty acids
*essential fatty acids
Number of Common Structure MP, 0C
C Atoms Name
16 Palmitoleic CH3(CH2)5CH=CH(CH2)7COOH 0.5
18 Oleic CH3(CH2)7CH=CH(CH2)7COOH 13.4
18* Linoleic CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH -5 to -5.27
18* Linolenic CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOH -10 to -11.3
20* Arachidonic CH3(CH2)4CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(CH2)6COO -49.0
H
Symbolic name: given as x:y Δ a,b,c
where x is the number of C’s in the
chain, y is the number of double
bonds, and a, b, and c are the
positions of the start of the double
bonds counting from C1 - the
carboxyl C.
Medical View of Fatty Acids
• Essential precursor fatty acids are
substrates for intracellular enzymes
• The need to lower the amount of
saturated fat in the diet has been well-
publicized and many individuals, as
well as commercial establishments, have
switched to vegetable oils for food
preparation. Saturated fats are found in
meat and dairy products and oils such as
palm oil. Dietary saturated fats increase
the blood levels of low-density
lipoproteins (LDL), which aid in the
deposition of cholesterol on artery walls.
Classification of
Lipids
(Based on composition)
• Simple Lipids
• Complex Lipids
• Derived Lipids
Simple Lipids
• esters of fatty acids
• also known as triacylglycerols, triacylglycerides, and neutral fats
• main storage form of fatty acids
1. Fats and oils - esters formed by the combination of a fatty
acid with one particular alcohol, glycerol
Physical properties
[Link] fats and oils are generally white or yellow solids and
liquids, respectively.
[Link] fats and oils are also odorless and tasteless but became
rancid over a period of time and develop an unpleasant odor
and taste.
[Link] in water but are soluble in some organic liquids.
[Link] are lighter than water and have a greasy feeling.
Reactions of Fats and Oils
• Oxidation – leads to rancidity
Rancid is a term used to indicate that fat has spoiled. The fat
takes on an unpleasant flavor when exposed to air and heat.
• Hydrogenation - a process to add hydrogen atoms into double
bonds of unsaturated fatty acids
Reactions of Fats and Oils
• Hydrolysis
Hydrolysis in the presence of a base is known as
saponification reaction
The Soap Micelle
Simple Lipids
2. Waxes - compounds produced by the reaction of a fatty acid with a
high molecular mass monohydric alcohol.
- Primarily esters of long-chain fatty acids with an even
number of carbon atoms and long-chain alcohols, also with
an even number of carbon atoms.
- Insoluble in water, nonreactive and flexible.
- Protective coatings in feathers of birds, the fur of animals,
and leaves of plants to prevent excessive loss of water.
Complex Lipids
- yields one or more fatty acids, an alcohol and some other type of
compounds upon hydrolysis.
1. Phospholipids
- contain fatty acids, alcohol, a nitrogen compound, and
phosphoric acid.
- found in all tissues in the human body, particularly in the
brain liver, liver, spinal tissue, and cell membranes.
Complex Lipids
a. Phosphoglycerides - an amino alcohol attached is a glycerol.
Complex Lipids
b. Sphingophospholipids - contain the alcohol sphingosine
Complex Lipids
2. Glycolipids
- similar to sphingomyelins except
that they contain a carbohydrate,
often galactose, in place of
choline and phosphoric acid.
- also called cerebrosides because
they are found in large amounts of
the brain tissue
Derived Lipids
- formed by the metabolic transformation of fatty acids
- includes ketone bodies (muscles), steroids (energy giving molecules), fatty
aldehydes, prostaglandins (natural anesthesia), and lipid-soluble vitamins.
Types:
a. Eicosanoids – biologically active compounds derived from
arachidonic acids.
b. Steroids – high molecular mass, four-ring compounds; contains OH
groups are sterols.
c. Isoprenoids - lipids derived from isoprene molecules that have many
physiological roles and a variety of commercial applications
Derived Lipids
Eicosanoids
1. Prostaglandins
- Natural defense of the body against all
forms of change
2. Thromboxanes - substance produced by
platelets, lead to occlusion of blood vessels by
fueling blood clots inside the vascular system.
3. Leukotriene - Leukotrienes are
inflammatory chemicals the body releases
after coming in contact with an allergen or
allergy.
4. Lipoxin - are endogenous anti-inflammatory,
pro-resolving molecules that play a vital role
in reducing excessive tissue injury and chronic
inflammation
Derived Lipids
Steroids
1. Cholesterol - found in
animal fats; in all animal
tissues, particularly in
brain and nervous tissue,
in the blood stream and
as gallstones.
2. Sex hormones
3. Bile Salts
4. Adrenal cortex
Derived Lipids
Isoprenoids
• Terpenes
Classification of
Lipids
(According to reaction with NaOH)
• Saponifiable lipids – produce fatty acid(s) upon
treatment of NaOH
Ex. Fats, waxes, phospholipids, glycolipids
• Non-saponifiable lipids
Ex. Steroids and terpenes (found in plants)
References
• LEHNINGER, AL. Biochemistry (3rd ed). USA: Worth Publishers, Inc.
• ODIAN, G and I. BLEI. Schaum’s Outline Series: Theory and Problems in General, Organic and
Biological Chemistry. USA: McGraw-Hill, J914.
• SY, MC and AC WEI. (1995) Basic Biochemistry. USA: Merriam Webster.
• CAMPBELL, MK and FARELL, SO. (2012) Biochemistry (7th Ed). Belmont, CA: Cengage
Learning.
• BAILEY, R. (07 October, 2019) Cell Membrane Function and Structure. Retrieved from
[Link]
• (05 May, 2013) Lipids. Retrieved from
[Link]
