FATS AND OILS

NAEMAA MOHAMAD
Faculty of Applied Sciences
Universiti Teknologi MARA
 LESSON OUTCOMES
At the end of this chapter, students should be
able to:-

a) Differentiate the sources of fats and oils.

b) Classify between different groups of fats and oils.
c) Draw the basic structure of fats and oils.
d) Differentiate between physical and chemical
properties of fats and oils.
e) Explain rancidity in fats and oils..
Classification of lipids

Source

Structures of triglycerides (TG) and fatty

acids (FA)

Physical and chemical properties of oils

Rancidity
INTRODUCTION
 Lipids-Broad group of chemically diverse compounds that are
soluble in organic solvents such as chloroform and alcohol

 Food lipids: Generally referred to as fats (solid) and oils (liquid)

indicating their physical state at ambient temperatures.

 Also classified as nonpolar (eg: triacyglycerol and cholesterol) or

polar (eg: phospholipids) to indicate their differences in the
solubility and functional properties)
◦ Polar lipids contain hydrophilic head group that has high affinity for water,
attched to a lipophilic tail group that has high affinity for oil.

 Food lipids play an important role in food quality by contributing

to attributes such as texture, flavour, nutrition, and caloric density.

 General term used to describe a large group of naturally occuring

fat-like substances
PHOSPHOLIPIDS
◦ important compound concerned with the transport of lipids in
the blood stream
◦ Eg. Lecithin play a major part in the digestion of fats
◦ Similar to fats structure based on glycerol but instead of 3
hydroxy group being combined with fatty acid only two are
being combined, the third being combined with phosphate
linked to choline
STEROIDS
◦ Classified as lipids but not fatty acid derivatives and dissimilar in
structure (eg: cholesterol, hormones)
CHOLESTEROLS
◦ A white fat substances which present in body tissue and is found in
variety of animal foods notably brain, kidney, liver and egg yolk.
WAXES
◦ Made from fatty acid combined with any of alcohol except glycerol
 SOURCES

ANIMAL NATURALLY VEGETABLE

ORIGIN OCCURING
ORIGIN
1) Mammal 1)Seed oils
depot fat
(eg: soybean oil,
(eg.lard and canola oil)
tallow)
2) Fruit coat fats
2) Milk fat
(eg: palm and olive
3)Marine oils oils)
(eg. Code liver 3) Kernel oils
oil and whale
oil) (eg:Coconut oil
and palm kernel)
 BASIC CHEMICAL STRUCTURE OF FATS AND OILS

Triglyceride (TG) and Fatty acids(FA)

 Triglycerides: Esters of glycerol with 3 fatty acids

 Basically fats and oils may be consider as mixtures of
triglycerides (TG)
 Comprised solely of Carbon, Hydrogen and Oxygen.
 They make up 40% of the calories in the average diet.
 Diglyceride/ diacylglycerol= glycerol attached to 2 fatty
acids.
 Monoglyceride/ monoacylglycerol = glycerol attached to 1
fatty acid.
Fig: Triglyceride structure
 Glycerol or sometimes referred as glycerin is a simple organic
compound of 3-carbon molecule containing three alcohol groups.
 Fatty acid : organic molecule contains chain of carbon bound to
hydrogen, plus an acid group (COOH) at one end and a methyl
group (CH3) at the other.
 Ester bonds hold fatty acid to glycerol, joining OH groups of
glycerol to the COOH groups of FA, with the loss of water.
 Any fatty acid not linked to glycerol molecule in a fat or oil
is referred to as free fatty acid
 The major component of all fats and oils is made up of TG
which represent 95% of the weight of most food fats in the
form in which they are consumed.
Fatty acid (FA)
 Fatty acid : organic molecule contains chain of carbon bound to hydrogen, plus a
carboxylic acid group (COOH) at one end and a methyl group (CH3) at the other.

 Most natural fatty acids have even number of carbons in a straight chain because of the
biological process of fatty acid elongation where two carbons are added at a time.

 Majority range from 14 to 24 carbons in nature.

 Some fats contain FA with <14 carbons –significant levels of short chain FA mainly
found in tropical oil and dairy fats.
 Odd carbon number and branched chain of fatty acids can be found in microorganism
and dairy fats.

 FA generally classsified as either saturated or unsaturated (containing double bonds).

 Unsaturated FA can be either monounsaturated (1 double bond) or polyunsaturated ( 2
or more double bonds).

 FA can be described by systematic , common and abbreviated names.

 Sources of FA
1. Saturated FA;
 Primarily animal sources: meat, poultry, milk, butter cheese, egg yol
and lard
 Plant sources: chocolate, coconut, coconut oil, palm oil, vegetable
shortening.

2. Monounsaturated FA;
 Avocado, peanuts, peanut butter, olives/olive oil

3. Polyunsaturated FA (PUFA);
 Primarily plant sources: vegetable oils (corn, safflower, soybean,
canole, etc), margarine, certain nuts (almond, walnut, pecan)
 Animal sources: fish
Nomenclature of saturated fatty acid
 IUPAC system names the parent hydrocarbon (HC) of the FA on
the basis of the number of carbons (eg. Ten carbons would be
decane).

 Since FA contains carboxylic acid group, the terminal e in the HC is

replace by oic (eg. Decanoic).

 Normally start the numbering from the carboxyl end

 Many common names originate from the source that the FA was
commonly or traditionally isolated (eg. Palmitic acids and palm
oil).

 A numerical system use for abbreviated names. The first number

in the system designates the number of carbons in the FA, while
the second number designates the number of double bonds.
◦ Eg. Hexadecanoic=palmitic= 16:0
◦  second number will always be zero for the saturated fatty acids
Nomenclature of unsaturated fatty acid
 In IUPAC system, anoic designation is changed to enoic (for the
presence of double bond).

 On the basis of the number of double bonds, the terms di-, tri-,
terta- and so on are added.
 Common name exist except for the long chain polyunsaturated
fatty acids

 Numerical abbreviation is similar with the previous with the second

number indicating the number of double bonds (eg.
Octadecadieonic = 18:2).

 The position of double bonds in IUPAC system numbered by the

delta (Δ), indicating the position of double bond from the carboxylic
acid end of FA.
◦ Eg. Oleic acid (18 carbons and 1 double bond)= 9-octadecenoic acid = 18:1 Δ 9
Linoleoc acid (18 carbons and 2 double bonds) = 9,12-octadecenoic acid =
18 :2 Δ 9,12
 Cont.
 Alternative numbering system indicates position of
the double bond from methyl end of FA known as
the omega (ω) system.
 For omega-3 or omega- 6 FA, the numbering start
at methyl end.
 Useful as it can group FA on the basis of their
biological activity and biosynthetic origin.
 Eg. The ω-3 fatty acids able to decrease blood
triacylglycerol levels.
 The omega-3 and omega-6 are considered as
essential fatty acid (EFAs).
Essential fatty acid (EFAs)
 EFAs are essential to human health and cannot be made
by the body
 All EFAs are unsaturated and must be provided from food.
 Occur in fish oil and variety of seed oil.
 The two omega-3 essential FA are:
◦ Eicopentaenoic acid (EPA) and docosahexaenoic acid (DHA)
 Coldwater fish are the best sources of omega-3 EFAs.
 Plant sources contain precursor to EPA and DHA called
alpha-linoleic acid (ALA).
 ALA can be converted into EPA, and EPA into DHA.
 Several function of EFAs;
◦ Required as cell membrane components.
◦ Strengthen immune cells.
◦ Lubricate body joins
◦ Insulation of body again heat loss
◦ Prevention in skin drying
◦ Provide energy
The omega 6 essential FA include linoleic
acid (LA) and gamma-linoleic acid (GLA)
Found in seeds; evening primrose,
sunflower and black currant.
 Unsaturated FA comes in 2 configurations.
◦ Cis- and trans- configurations

 Natural configuration of double bonds in unsaturated FA

is the cis- configuration, the hydrogen atoms bonding
to the C=C located on the same side of the double
bond.

 Trans-configuration; the hydrogen atoms attached to

the carbon atoms of the double bond are opposite
each other (eg. in meat, poultry and processed diary
product)

 Thesestructural differences affect properties such as

melting point.
HOW?????
Cont
 Doublebond in cis- configuration will cause the FA in bent
configuration, thus are not linear making it difficult for
them to orient themselves in tight packing configurations.

 Relatively
weak van der Waals interactions between
unsaturated FA, their melting point is low.

 Therefore , exist mainly in liquid state.

 FAwith double bond in trans configuration are more

linear than unsaturated FA in the cis- configuration.

 Resultingtighter packing and high melting point.

 Eg. Melting point of;
◦ stearic acid (octadecanoic) is 70°C
◦ Oleic acid (cis-9-octadecanoic ) is 5°C
◦ Elaidic acid (trans-9-octadecanoic) is 44°C
Table: Structure and melting point of some common fatty
acids
Chemical reaction of lipids

Hydrogenation
Hydrolysis
Interesterification (IE)
Fractionation
Polymerization
Oxidation

Deep fat frying

Hydrogenation
Cont’

Used in food industry to harden liquid oils into

semisolid fats.
This process raise the melting point of a fats.
Have tendency to change the percentage of cis-
unsaturated FA to trans-unsaturated FA.
Product produced from hydrogenation such as
margarines, shortenings, and partially
hydrogenated oils that improved oxidative stability.
Interesterification
 Removal of FAs from glycerol and their subsequent
arrangements, which differ from the original fat
molecule.

 Commercially important to produce monoglyceride

and diglyceride from TG that function as
emulsifying agent especially in food industry.

 Emulsifier
tend to hold fat and water together. Eg.
In mixing of cake batter.

 Could improve melting point, plastic range, crystal

structure and flavour stability but does not change
the degree of unsaturation.
Fractionation
 The process to splits an oil into its higher melting point
components (eg. Stearic acid) and lower melting point
component (eg. Oleic acid).

 Crystallization is accomplished, so the crystal portion (more

saturated or long chain) can be separated from the liquid
portion (more unsaturated and short chain).

 Commonly done to vegetable oil in a process called

winterization.
◦ The oil is simply cooled to about chilled temperature and
the crystallized material removed by filtration
◦ Useful in preparation of salad dressings
◦ Oil in salad dressing will not crystallize and disrupt the
emulsion when stored at a refrigerator temperature
Hydrolysis
 The reaction requiring heat plus the addition of
water molecules to separate the FA from the
glycerol portion of a lipid molecule.
 Glycerol can further changed to acrolein, which
produces irritating and odorous fumes in the
smoke of an overheated fats.
heat heat
TG + 3H2O 3 FA+ glycerol 3 FA + acrolein +
2H2O
Polymerization
Reactionof fat itself, whereby a relatively small molecules of fat or oil
combine to form much longer molecules.

Occur either at the point of unsaturation or at the juncture of the FA

and the glycerol molecule.

May 100 or 1000 times the molecular weight of the original molecules.

Can occur in deep frying of food (temp; 325-375F).

Reaction accelerated by frying at a high temperature (350F),presence

of O2, usage of poor quality fat and poor frying practice by heating for
long periods of time.

Cause physical changes

◦Gumlike material around the sides of the frying utensils
◦Increase viscosity of the frying oil
◦Foaming
◦Darker colour of frying oil
Fig: Summary of chemical reaction in
deep fat frying
CHEMICAL PROPERTIES OF
FATS AND OILS
• useful indicator of fat form;
> high IV fats are liquid, low IV fats are solid
RANCIDITY IN FATS AND OILS
 OXIDATIVE REACTION
 Like hydrogenation, the reactions also occur at the point of
unsaturation.
 
R – CH = CH – CH3 + O2 R – COH –
COH- CH3

 Oxidation changes in a three stages series of reaction;

1. Initiation
2. Propagation/ elongation
3. Termination
1) Initiation
 The hydrogen is abstracted from the fat/oil to
yield a free radical in the presence of the
initiators such as UV light, heat and heavy metal
such as copper.

Initiators
RH R• + H
Unsaturated fat free radical
2) Propagation

 Once the free radical formed, it will combine with

oxygen to form a peroxy free radical, which in
turn abstract hydrogen from another unsaturated
molecule to yield a peroxide and a new radical.
 The propagation reaction has started.

R• + O2 ROO• (peroxy free

radical)

ROO• + R H R O O H + R•
hydroperoxide

* The hydroperoxide formed in the propagation part of the

reactions are the primarily oxidation products.
3) Termination of the oxidation
 Ifthe free radicals react with themselves to yield
non- active products
ROO•+ R• ROOR
R• + R• R- R
R O O • + R O O• ROOR + O2

 Fat and oil antioxidant such as tocopherol, BHA,

BHT, gallic acid can react with initiating and
propagating radicals to produce harmless
products.
◦ Antioxidants are substances that can delay, or slow the
rate of oxidation.