Lipid Structure and

Function
 What are Lipids??
Lipids are a class of biological molecules insoluble in water and highly
soluble in organic solvents (e.g., ether, benzene, acetone, chloroform)

“lipid” is synonymous with “fat”, but also includes phospholipids, sterols,

etc.

Lipids are largely hydrocarbon in nature and represent highly reduced

forms of carbon and, upon oxidation in metabolism, yield large amounts
of energy. Lipids are thus the molecules of choice for metabolic energy
storage.
 Lipids or Glucose for Energy?
H2 H2 H2 H2 H2 H2 H2 H2
H3 C C C C C C C C C O
C C C C C C C C C
H2 H2 H2 H2 H2 H2 H2 H2 OH

More reduced state (more H bound to C)

HC O
 More potential for oxidation
HO CH
HC OH
HO CH
Less reduced state (more O bound to C)
HO CH  Less potential for oxidation
CH 2 OH

More highly reduced than CHO and give

off 2.25x more energy
 Structure of lipids
• Lipids are formed from carbon, hydrogen, and oxygen.
• They are formed from fatty acids, which are made of a methyl chain which
is connected to a carboxyl (the acid part).

• These fatty acids may be either saturated (with as many hydrogens bonded
to their carbon molecules as possible), or unsaturated (with double bonds).

• The main difference is that saturated fats are relatively straight and will
stick to each other, which may make them more solid like a fat.
Unsaturated fats are a little bent in their structure, which means they will
form a liquid, like an oil.

H2 H2 H2 H2 H2 H2 H2 H2
H3 C C C C C C C C C O
C C C C C C C C C
H2 H2 H2 H2 H2 H2 H2 H2 OH
Methyl chain Carbon groups Carboxyl group
Structure of lipids
Fat FAT OILS
Saturated fat
Oil Unsaturated fat
 Properties of Lipids
• Soluble in non-polar organic solvents
• Contain C, H, O
– Sometimes N & P
• Includes fats and oils – mostly triglycerides
– Fat: solid at room temperature
– Oil: liquid at room temperature
• More highly reduced than carbohydrates
– 2.25x more energy (9 kcal/gm)

Compared to carbohydrates, fatty acids contain more

hydrogen molecules per unit of carbon, thus, they are
in a more reduced form
 Functions of Lipids
• Lipoproteins/ phospholipids are constituents of cell
membrane.
A lipoprotein is a biochemical assembly that contains both
proteins and lipids, bound to the proteins, which allow fats to
move through the water inside and outside cells. The proteins
serve to emulsify the lipid molecules
 Functions of Lipids
• One more important function of dietary lipids is that
of supplying the so-called essential fatty acids which
are required in the body eg Linoleic acid and linolenic
acid

• Electrical insulation
– Protects nerves, help conduct electro-chemical
impulses (myelin sheath)
• Facilitate absorption of fat soluble vitamins i.e
A,D,E,K in the small intestines.
 Functions of Lipids
• Lipids are as а source of fuel when metabolized.
Thus fat is the most concentrated form in which
potential energy can be stored.
• Since fat is а bad conductor of heat, it provides
excellent insulation to maintain body temperature.
• Fat may also provide padding to protect the internal
organs( mechanical insulation)
• Some compounds derived from lipids are important
building blocks of biologically active materials eg
glycolipids
Glycolipids are lipids with a carbohydrate attached.
Their role is to provide energy and also serve as
markers for cellular recognition.
 Functions of Lipids
• Synthesis of prostaglandins from fatty acids
– Hormone-like compounds that modulates many body
processes
• Immune system, nervous systems, and GI secretions
• Regulatory functions: lower BP, blood clotting, uterine contractions
 Classification of Lipids
• There are two major types of lipids- simple
lipids and complex lipids. Simple lipids are
esters of fatty acids with various alcohols. For
eg., fats and waxes. On the contrary, complex
lipids are esters of fatty acids with groups
other than alcohol and fatty acids.
 Classification of Lipids
• Fatty Acids
• Triacylglycerides
• Phospholipids
• Prostaglandins
• Steroids: large molecular wt. alcohols found in nature and
combined w/FA’s (e.g., cholesterol)
• Fat soluble vitamins
• Waxes
• Terpenes
 Fatty acids
• Fatty acids are carboxylic acids with
unbranched carbon chain and even number of
carbon atoms.
Structure of fatty acid

=O
-H

-H
H - C - ( C )n - C - OH
-H

-H

Carboxyl
group
Methyl Carbon
group group(s)
 Characteristics of fatty acids
• They have an even number of carbon atoms
• They act as building blocks for more complex
lipids such as triglycerides, waxes etc
• They have low polarity which makes them
insoluble in polar solvents.
• Types of fatty acids
 Long-chain fatty acids (12 to 26 carbon atoms) are found in meats and
fish
 Medium-chain fatty acids (6 to 10 carbon atoms)
 Short-chain fatty acids (fewer than 6 carbon atoms)

As chain length increases, melting point increases

• Fatty Acid Saturation
Saturated - no double bonds
Unsaturated – contain double bonds
Monounsaturated – one double bond
Polyunsaturated - >1 double bond
The double bond is a point of unsaturation
As number of double bonds increases, melting point decreases
 Saturated Fatty Acids
• All the chemical bonds between the carbon are
single bondsC-C-C-
• No double bonds
• No space for more H atoms; fully “saturated”
• Solid at room temperature
– Butter, coconut oil, palm oil, and fully hydrogenated
vegetable oils
– Poultry skin, whole milk
 Unsaturated fatty acids
Mono unsaturated fatty acids
 These have only one double bond
 Liquid at room temperature
Olive oil, canola oil, peanut oil
Other sources: avocado, almonds, cashews, pecans and sesame seeds
Poly unsaturated fatty acids
 These have two or more double bonds
Include omega-3 and omega-6 fatty acids (essential fatty acids)
Linolenic acid: omega 3 fatty acid
Linoleic acid: omega 6 fatty acid
Richest sources of poly-unsaturated fatty acids include:
Vegetable oils
Corn, sunflower, cotton seed oils
 Chain Length
• The chain length of the majority of fatty acids will
determine the “hardness” of the fat
– <10 carbons = liquid
– Between 10 and 20 carbons = ???
– >20 carbons = solid

Acetic Acid (2 C) Vinegar Liquid

Stearic Acid (18 C) Beef Tallow Solid

Arachidic Acid (20 C) Butter Solid

Derivatives of polyunsaturated fatty acids
Structure of fatty acids
Isomers (most common in unsaturated FA)
• Geometrical isomers due to • Chain branching
double bond
– Cis – Straight
• occurs naturally • Synthesized by
• bend in acyl chain mammals and plants
– Trans – Branched
• Not as common • Synthesized by
• Found in hydrogenated bacteria
oils
• Results from bacterial
synthesis
– In fats in
ruminants!!
• Straight acyl chains
 Cis Fatty Acids

Bending is due to steric hindrance

between the hydrogen ions
 Cis or Trans fatty-acids

• Named according to location of H’s

– Cis or trans fatty acids

Cis-9-octadecenoic acid Trans-9-octadecenoic acid

(Oleic acid) (Elaidic acid)
 Melting Points

• Affected by chain length

– Longer chain = higher melting temp

Fatty acid: C12:0 C14:0 C16:0 C18:0 C20:0

Melting point: 44°C 58°C 63°C 72°C 77°C

Which fatty acids are liquid at room temperature?

Which fatty acids are solid at room temperature?
 Melting Points

• Affected by number of double bonds

– More saturated = higher melting temp
– Unsaturated = low melting temp

Fatty acid: C18:0 C18:1 C18:2 C18:3

Melting point: 72°C 16°C –5°C –11°C

Which fatty acid is liquid at room temperature?

Which fatty acids are solid at room temperature?
 Examples of fatty acids
Acids Carbons Double bonds Abbreviation Source
Acetic 2 0 2:0 bacterial metabolism
Propionic 3 0 3:0 bacterial metabolism
Butyric 4 0 4:0 butterfat
Caproic 6 0 6:0 butterfat
Caprylic 8 0 8:0 coconut oil
Capric 10 0 10:0 coconut oil
Lauric 12 0 12:0 coconut oil
Myristic 14 0 14:0 palm kernel oil
Palmitic 16 0 16:0 palm oil
Palmitoleic 16 1 16:1 animal fats
Stearic 18 0 18:0 animal fats
Oleic 18 1 18:1 olive oil
Linoleic 18 2 18:2 grape seed oil
Linolenic 18 3 18:3 flaxseed (linseed) oil
Arachidonic 20 4 20:4 peanut oil, fish oil
 Triacylglycerides
• Triacyl glycerols (triglycerides)
– Lipid storage form
• Where in the body? Adipocytes!! (fat cells)
– Most lipids consumed are triglycerides
 Triglycerides
Structure of Triglycerides
• Composed of one glycerol molecule and three fatty acids
connected by an ester bond (bond between an alcohol
and organic acid)
– Fatty acids may be same or mixed
– Lipid storage form
• Where in the body? Adipocytes!! (fat cells)

Fatty Acid

Fatty Acid
Glycerol

Fatty Acid
Reaction leading to the formation of
triacylglycerol
 Triglyceride Structure

• Fatty acid composition of triglyceride varies

according to function
– Membrane lipids must be fluid at all temperatures
• Contain more unsaturated fatty acids
– Lipids in tissues subjected to cooling
(e.g., hibernators or tissues in extremities)
• Contain more unsaturated FAs
 Most Common Fatty Acids in Di- and
Triglycerides
Fatty acid Carbon:Double bonds Double bonds
Myristic 14:0
Palmitic 16:0
Palmitoleic 16:1 Cis-9
Stearic 18:0
Oleic 18:1 Cis-9
Linoleic 18:2 Cis-9,12
Linolenic 18:3 Cis-9,12,15
Arachidonic 20:4 Cis-5,8,11,14
Eicosapentaenoic 20:5 Cis-5,8,11,14,17
Docosahexaenoic 22:6 Cis-4,7,10,13,16,19
 Group assignment
• Write short notes on the following classes of
lipids
1) Phospholipids
2) Prostaglandins
3) Steroids ie Cholesterol, Bile and ergosterol.
4) Terpenes (plant lipids)
5) Wax
Complex Lipids - Phospholipids

• Two primary types:

– Glycerophosphatides
• Core structure is glycerol
• Part of cell membranes, chylomicrons, lipoproteins
– Sphingophosphatides
• Core structure is sphingosine
• Part of sphingomyelin
 Lipidbilayer
Lipid bilayerof
of plasma
plasma membrane
membrane
 Phospholipids
• Significant use in feed industry as emulsifiers
– Lipids form emulsion in water
• Phospholipid sources:
– Liver, egg yolk,
– Soybeans, wheat germ
– Peanuts