Chemistry of biomolecules

Lecturer 7
1
 Fatty Acids
 Fatty acids are aliphatic mono-carboxylic acids
that are mostly obtained from the hydrolysis of
natural fats and oils.

 They have the general formula R-(CH2)n-COOH and

mostly have straight chain (a few exceptions have
branched and heterocyclic chains).

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 In this formula "n" is mostly an even number of
carbon atoms (2-34) with a few exceptions that have
an odd number or even zero in acetic acid and may
not contain a radical at all as is formic acid (HCOOH).
They may be hydroxylated in a few examples.

3
 Fats and oils

• Fats and oils are used in our diets to provide us with energy. They play an
important role in the transport of vitamins which are soluble in fats around
the human body.
• Many fats and oils are obtained from plant sources (sunflower oil, palm oil,
coconut oil) and animal sources (lard, cod liver oil)
• Fatty acids are long chain carboxylic acids ranging from C4 to C28.
• Common fatty acids including stearic acid and oleic acid have eighteen
carbon atoms in their chains.
• The acid molecules can either be saturated or unsaturated. The fats and oils
formed are also known as triglycerides.
4
 Oils and fats are important nutrients in a healthy diet. Structurally, they
are esters of glycerol with three fatty acids.
 As such, they are scientifically called triacylglycerols but are commonly
referred to in the food industry as triglycerides.

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Fats formation

6
 Q- Explain this statement :
Oils are liquids at room temperature, while fats are solid
at room temperature.

• Like other esters, fats and oils are formed by a reversible reaction.
• Oils (liquids at room temperature) contain more carbon to carbon double
bonds than fats (solid at room temperature).
• The lower melting point of oils is related to the higher degree of
unsaturation. The presence of carbon to carbon double bonds in the oil
molecules distorts the long fatty acid chains and the molecule’s shape. As a
result the molecules cannot pack closely together.

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 Fat molecules do not have the same degree of distortion and can pack
closely together. This increases their melting point.

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9
Fatty acids are classified according
to several bases as follows:
I. I. According to presence or absence
of double bonds they are classified
into:

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A. Saturated Fatty Acids:
 They contain no double bonds with 2-24 or more
carbons. They are solid at room temperature
except if they are short chained.
 They may be even or odd numbered.
 They have the following molecular formula:
CnH2n+1COOH.
Examples are:

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 Saturated fatty acids
MELTING
COMMON NAME FORMULA
POINT

ºC 45 lauric acid CH3(CH2)10CO2H

ºC 55 myristic acid CH3(CH2)12CO2H

ºC 63 palmitic acid CH3(CH2)14CO2H

ºC 69 stearic acid CH3(CH2)16CO2H

ºC 76 arachidic acid CH3(CH2)18CO2H

B. Unsaturated fatty acids:
 Presence of double bonds affects physical properties,
e.g., lower melting temperature; therefore, all
unsaturated fatty acids are liquids at room
temperature.
 They are further classified according to the number
of double bonds into:

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1. Monounsaturated fatty acids:
Palmitoleic acid.
 It is found in all fats, it is C16:1∆9, i.e., has 16
carbons and one double bond located at carbon
number 9 and involving carbon 10.

CH3 (C H 2 ) 5 CH CH (C H 2 ) 7 COOH

P alm ito leic acid

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Oleic acid.
 It is the most common fatty acid in natural fats. It is
C18:1∆9, i.e., has 18 carbons and one double bond located
at carbon number 9 and involving carbon 10.

CH3 (C H 2 ) 7 CH CH (C H 2 ) 7 COOH

O leic acid

COOH

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 Elaidic acid
 Elaidic acid is a 9-trans-form of oleic (9-trans-
Octadecenoic acid) and present in hydrogenated and
ruminant fats.

9-trans-Octadecenoic acid

16
Nervonic acid
 Nervonic acid is unsaturated lignoceric acid. It is
C24:115. It has 24 carbons and one double bond located
at carbon number 15 and involving carbon 16. It is found
in cerebrosides. 15-Tetracosenoic acid, (Z)-; cis-15-
tetracosenoic acid; nevonic acid; selacholeic acid. It is
rare in most lipid classes, found enriched in
sphingomyelin.

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  The source of nevonic acid is Liver oil of
spiny dogfish shark

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Vaccenic acid
 Vaccenic acid is present in all tissues.
 Present in virtually all lipid classes at a low
concentration.
 18:1n7 is present at about 25% of the concentration
of 18:1n9 in most phospholipids.
 A notable exception is the phospholipid cardiolipin,
which often contains as much 18:1n7 as 18:1n9.

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  Dietary source is butter fat and animal fat.

CH 3 (CH 2 ) 5 CH CH (CH 2 ) 9 CO O H

Vaccenic acid

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Chaulmoogric acid
 Chaulmoogric acid is heterocyclic C18:115. It is
present in chaulmoogra oil that was used previously
in treatment of leprosy ‫الجزام‬.

(CH2 )12 COOH

Chaulmoogric acid
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Polyunsaturated fatty acids

(Essential fatty acids)

They are essential fatty acids that cannot

be synthesized in the human body and
must be taken in adequate amounts in the
diet. They are required for normal growth
and metabolism. They are liquids at room
temperature.

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Deficiency:
 Their deficiency in the diet leads to nutrition
deficiency disease.
Its symptoms include: poor growth and health
with susceptibility to infections, dermatitis,
decreased capacity to reproduce, impaired
transport of lipids, fatty liver, and lowered
resistance to stress.
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 Importance:

A. They are useful in the treatment of atherosclerosis

‫ تصلب الشراين‬by help transporting blood cholesterol and
lowering it and transporting triglycerides.
B. The hormone-like eicosanoids are synthesized from
them.
C. They participate in structure of all cellular and
subcellular membranes and the transporting plasma
phospholipids.
D. They are essential for skin integrity ‫سالمة‬, normal
growth and reproduction.

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E. They have an important role in blood clotting
(intrinsic factor).
F. Important in preventing and treating fatty liver.
G. Important role in health of the retina ‫ الشبكية‬and
vision.
H. They can be oxidized for energy production.

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Source:
 The main source is vegetable oils such as corn oil,
linseed oil, peanut oil, olive oil, cottonseed oil,
soybean oil and many other plant oils, cod liver oil
and animal fats.

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 Examples: Q

Linoleic:
C18:29, 12. It is the most important since
other essential fatty acids can be
synthesized from it in the body.

CH3 (C H 2 ) 4 CH CH CH2 CH CH (C H 2 ) 7 COOH

L in o le ic ac id

COOH

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 -Linolenic acid:
 C18:39, 12, 15, in corn, linseed, peanut, olive,
cottonseed and soybean oils.

CH3 CH2 CH CH CH2 CH CH CH2 CH CH (C H 2 ) 7 COOH

 -L in o len ic ac id
COOH

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 Arachidonic acid:
 C20:45, 8, 11, 14. It is an important component of
phospholipids in animal and in peanut oil from
which prostaglandins are synthesized.

C H 3 (C H 2 ) 4 C H C H C H 2 C H C H C H 2 C H C H C H 2 C H C H (C H 2 ) 3 C O O H
A ra c h id o n ic a c id

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 Clupandonic acid:
 C22:57, 10, 13, 16, 19. It is present in fish oils and
brain phospholipids.

C H 3 C H 2 C H C H C H 2 C H C H C H 2 C H C H C H 2 C H C H C H 2 C H C H (C H 2 ) 5 C O O H
C lup and onic acid
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 Unsaturated fatty acids
MELTING COMMON
POINT NAME
FORMULA

palmitoleic
ºC 0
acid
CH3(CH2)5CH=CH(CH2)7CO2H

ºC 13 oleic acid CH3(CH2)7CH=CH(CH2)7CO2H

linoleic
ºC 5-
acid
CH3(CH2)4CH=CHCH2CH=CH(CH2)7CO2H
linolenic CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7CO2H
ºC 11-
acid
arachidonic
ºC 49- CH3(CH2)4(CH=CHCH2)4(CH2)2CO2H
acid
 Q- Explain this statement :
The melting point of unsaturated oil, affected by
the no of db.

 A second double bond lowers the melting point further

(linoleic acid, mp —5°C), and a third double bond lowers it
still further (linolenic acid. mp — 11°C).

 The trans double bonds in eleostearic acid (mp 49°C) have

a smaller effect on the melting point than the cis double
bonds of linolenic acid.
 The geometry of a trans double bond is similar to the zigzag
conformation of a saturated acid, and it does not kink the
chain as much as a cis double bond.

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 Stearic acid , mp70 oC oleic acid, mp 4o C

The cis double bond in oleic acid lowers the melting point by 66oC

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 Fats and oils also have melting points that
depend on the unsaturation (especially cis
double bonds) in their fatty acids.
 A triglyceride derived from saturated fatty
acids has a higher melting point because it
packs more easily into a solid lattice than a
triglyceride derived from kinked, unsaturated
fatty acids.

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 Figure 3 shows" typical conformations of triglycerides
containing saturated and unsaturated fatty acids.
 Tristearin (mp 72°C) is a saturated fat that packs
well in a solid lattice.
 Triolein (mp -4°C) has the same number of carbon
atoms as tristearin, but triolein has three cis double
bonds, whose kinked conformations prevent optimum
packing in the solid.

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Figure 3

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Figure 3:
Unsaturated triglycerides have lower melting
point because their unsaturated fatty acids do
not pack as well in a solid lattice.

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 Most saturated triglycerides are fats, because
they are solid at room temperature.
 Most triglycerides with several unsaturations
are oils.

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 Most naturally occurring fats and oils are mixtures of
triglycerides containing a variety of saturated and
unsaturated fatty acids. In general, oils from plants
and cold-blooded animals contain more unsaturations
than fats from warm-blooded animals.
 Table 2 gives the approximate composition of the
fatty acids obtained from hydrolysis of some common
fats and oils.

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 Table 2: Fatty Acid Composition of Some Fats
and Oils, ( % by weight).

Unsaturated Fatty Acids Saturated Fatty Acids

Stearic Lauric Source
Linolenic Linoleic Oleic Palmitic Myristic
0 2 49 14 27 6 0 Beef fat

0 10 47 9 24 1 0 Lard

0 10 48 8 27 3 1 Human fat

30a 0 0 3 14 5 0 Herring oil

0 34 50 3 10 1 0 Corn oil

0 5 84 2 7 0.1 0 Olive oil

7 51 29 2 10 0.1 0.2 Soybean oil

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 *Although vegetable oil could be produced cheaper and in
greater quantities, consumers were unwilling to use vegetable
oils because they were accustomed ‫ معتاد‬to using white, creamy
fat.
 *Then vegetable oils were treated with hydrogen gas and a
nickel catalyst, reducing some of the double bonds to give a
creamy, white vegetable shortening that resembles fat.

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II- According to the length of their
hydrocarbon chain they are
classified into:
[1] Short-chain fatty acids:
They have 1-10 carbons, and saturated or
unsaturated. They are soluble in water and
are present in milk in high amount and are
further classified into:

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Volatile short-chain fatty acids:
 They are liquid in nature and contain
1-6 carbon atoms, water-soluble and
volatile at room temperature, e.g.,
formic, acetic, propionic, butyric,
valeric and caproic acids. See the
following for examples of saturated
fatty acids,
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Volatile fatty acids
H COOH CH 3 COOH CH 3 CH 2 COOH CH 3 (CH 2 )2 COOH
Formic acid Acetic acid Propionc acid Butyric acid
CH 3 (CH 2) 3 COOH CH 3 (CH 2)4 COOH
Valeric acid Caproic acid

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Non-volatile short-chain fatty acids:
 They are solids (if saturated) or liquid
(if unsaturated) at room temperature
and contain 7-10 carbon atoms. They
are water-soluble and non-volatile at
room temperature. Examples of non-
volatile short-chain fatty acids include,
caprylic and capric acids, see the
above figure. 45
Short-chain non-volatile fatty acids
CH 3 (CH 2 ) 6 COOH CH 3 (CH 2 ) 8 COOH
Caprylic acid Capric acid

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[2] Long-chain fatty acids:
 They contain more than 10 carbon atoms.

They occur in hydrogenated oils, animal fats,

butter and coconut and palm oils and other
plant oils. They are non-volatile, water-
insoluble and solid (if saturated) or liquid (if
unsaturated) at room temperature.
Examples of saturated long-chain fatty acids
include, lauric, myristic, palmitic, stearic,
arachidic, behenic and lignoceric acids, see
the above figure. 47
Long-chain fatty acids
CH3 (CH2)10COOH CH3 (CH2)12COOH CH3 (CH2)14COOH
Lauric acid Myristic acid Palmitic acid
CH3 (CH2)16COOH CH3 (CH2)18COOH
Stearic acid Arachidic acid
CH3 (CH2)20COOH CH3 (CH2)22COOH
Behenic acid Lignoceric acid

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Hydroxy fatty acids:
 They contain one or more hydroxyl groups, e.g.,
ricinoleic (18:19, hydroxy at C12), oxynervonic
(24:115, hydroxy at C2), cerebronic (24: hydroxy
at C2), and dihydroxy-stearic acids (18: dihydroxy
at C9 and C10) found in castor oil and brain
glycolipids. They are toxic in their free form. This
is why castor oil ‫ زيت الخروع‬is non-edible.

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Branched chain fatty acids:
 There are fatty acids with branched
chains such as phytanic acid that is a
by-product of chlorophyll catabolism in
human and animal that is present in
butter. If it is not oxidized in the body it
will be toxic.

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 Q

Isomerism in fatty acids:

 Geometrical (stereo-isomerism) isomerism exists
as cis-trans isomerism, e.g., oleic and its 9-trans-
isomer elaidic acid. Most natural unsaturated fatty
acids occur mainly in the cis form.
 Also there is structural positional isomerism due to
variation in position of double bonds, e.g., - and
-linolenic acids (see above).
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 Q
(CH2)7 COOH H (CH2)7 COOH H (CH2)7 COOH H (CH2)7 COOH
H

H3C (CH2)7 H H (CH2)7 CH3 H3C (CH2)7 H H (CH2)7 CH3

Elaidic acid Oleic acid Elaidic acid Oleic acid

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53
 Chemical Reactions of
Lipids
1. Hydrolysis:
 Fats and oils are hydrolyzed into their
constituents (fatty acids and glycerol) by the
action of super heated steam, acid, alkali or
enzyme (e.g., lipase of pancreas).
 During their enzymatic and acid hydrolysis
glycerol and free fatty acids are produced.

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 Alkaline hydrolysis produces glycerol and
salts of fatty acids (soaps).
 This is why alkaline hydrolysis of fats and oils
is called saponification.

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 The saponifiable fraction is that portion of total lipid
which after treatment with hot alkali becomes
soluble in water and insoluble in ether.
 The unsaponifiable fraction is that portion of lipid,
which cannot be saponified by alkali and insoluble in
water but soluble in ether.
 They include high molecular weight alcohols,
ketones, waxes, steroids and hydrocarbons.

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57
58
 Types of Soaps:
1. Ordinary or hard soap are made by saponification of neutral fats
by NaOH.
Separation of soap from saponification mixture may be done by
addition of NaCl, which renders soaps sparingly soluble.
2. Green soap (or soft soap) is potassium soap.
3. Calcium and magnesium soaps are useless insoluble soap.
4. Soaps with high molecular weight unsaturated fatty acids or with
sodium-ricinoleate are germicidal and detoxify diphtheria and
tetanus toxins.

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 The cleaning action of soaps is due to their ability to lower
surface tension and thus facilitate emulsification of oils and
grease ‫ شحم‬, which can be easily washed away by water.
 However, soaps have slight irritating alkaline reaction due to
reverse hydrolysis into free NaOH.
Irritation is preventable by adding excess of fatty acid or
sodium oleate (not easily hydrolyzed) to toilet soaps in
particular.

O O

R1 C O Na + HOH R1 C O H + NaOH
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 Cleaning action of soap
 The cleaning action of soap may be due to their
ability to lower surface tension and thus facilitate
emulsification of oils and grease, which can be easily
washed away by water.
 Oils and grease (hydrophobic) may also be
incorporated inside the micelles (hydrophobic side)
which can be easily go away by water

61
 The presence of a soap or a detergent in water
facilitates the wetting of all parts of the object to be
cleaned, and removes water-insoluble dirt by
incorporation in micelles.

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Dirties incorporated in micelles
.

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Soap and Detergents

64
 What is the iodine number of a lipid?

 The iodine number equals the number of mg of

iodine required to saturate the fatty acids present in
100 mg of the oil or fat.
 Oils rich in saturated fatty acids have low iodine
numbers, while oils rich in unsaturated fatty acids
have high iodine numbers.

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2. Addition reactions of fat and oils (due to
unsaturation):
Neutral fats containing unsaturated fatty acids
have the ability of adding halogens.
Examples; hydrogen or hydrogenation and
iodine or iodination at the double bonds.

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 It is a very important property to determine
the degree of unsaturation of the fat or oil
that determines its biological value (see
iodine value).
67
Hydrogenation or hardening of oils:

 It is a type of addition reactions accepting hydrogen at the

double bonds of unsaturated fatty acids.
 The hydrogenation is done under high pressure of
hydrogen and is catalyzed by finely divided nickel or
copper and heat.
 It is the base of hardening of oils (margarine
manufacturing), e.g., change of oleic acid (liquid) of fats into
stearic acid (solid).

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 It is advisable not to saturate all double bonds
in oils; otherwise margarine produced will be
very hard, of very low biological value and
difficult to digest.

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 3) Oxidation Reactions:
 Unsaturated fatty acids are also oxidizable at the
double bonds to give peroxide derivatives that
decompose into aldehydes, ketones, resins and
short chain fatty acids that form hard transparent
water-proofing film on spreading in thin layers.
 This is the base of the drying oils after exposure to
atmospheric oxygen.
 Example is linseed oil ‫زيت بذر الكتان‬, which is used in
paints and varnishes manufacturing.

70
 Rancidity
What is Rancidity?
 It is a physico-chemical change in the natural
properties of the fat and oils leading to the
development of unpleasant odor or taste or abnormal
color particularly on aging after exposure to
atmospheric oxygen, light, moisture, bacterial or fungal
contamination and/or heat.
 Saturated fats resist rancidity more than unsaturated
fats that have unsaturated double bonds.

71
 What is Rancidity?
 Rancidity refers to the oxidation of unsaturated fats or
oils in food that results in a bad smell and taste. When
oxygen molecules interact with food and oil, the normal
composition of the food is damaged which causes a
change in taste and smell, and thus the food is not
recommended to be consumed.

72
 Factors affecting Rancidity
 There are various factors that affect rancidity. Some of the
factors are discussed below:
 Oxygen: The primary cause of rancidity is exposure to
oxygen. Oxygen is more soluble in fats, which leads to
food damage and oxidation by releasing free radicals.

73
 Microorganisms: Many microorganisms release an
enzyme known as lipase which leads to the hydrolysis of
lipids. These microorganisms use their enzyme on food
materials and destroy their chemical composition.
 Physical factors: Physical factors like Heat, light, and
temperature plays an important role in rancidification. Heat
and light stimulate the process of oxidation and are the
main source for the production of free radicals. Light
promotes the decomposition of unsaturated fatty acids.
 Trace elements: The rate of rancidity can be increased by
trace elements like Fe and Zn. This is another important
factor that affects rancidity. 74
 Prevention of Rancidity

There are many possible ways to prevent Rancidity. Some of them

are:
 Antioxidants can be added to foods that contain oils and fats to
slow down oxidative deterioration.
 To slow down the process of rancidification, food can be stored
in airtight containers.
 Vacuum packing can be done to keep oxygen out.
 By adding inert gas such as nitrogen to the bag to replace
oxygen.
 Food items can be kept in the refrigerator. It will reduce the rate
of most reactions that take part in rancidity.
 By storing food in dark places.

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Types of Rancidity

Rancidity is divided into three types:

 Hydrolytic Rancidity

 Oxidative Rancidity

 Microbial Rancidity

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 1- Hydrolytic Rancidity
 Hydrolytic Rancidity refers to the smell or odour that occurs
when free fatty acids are released and triglycerides are
hydrolyzed.
 Triglyceride is a combination of three fatty acids present in
oily food.
 Hydrolytic Rancidity occurs more quickly in the presence of
enzymes like lipase and with moisture and heat.
 It results in the hydrolysis of the fats with the liberation of
either one or more volatile fatty acids.

77
78
 2- Oxidative Rancidity
 Oxidative Rancidity causes oxygen damage to a food substance. It
occurs with unsaturated fats.
 The natural oil structure is damaged and interrupted by oxygen
molecules in such a way that it changes its colour, taste, and smell.
 It leads to the formation of toxic compounds like peroxides that
damage Vitamins A and E in foods.
 In Oxidative Rancidity, unsaturated fatty acids of glycerides are
oxidized at their double bonds.
 Thus, this reaction causes the release of ketones, volatile aldehydes,
and acids.
 It can be prevented by an oxygen-free atmosphere, light-proof
packaging, and the addition of antioxidants.

79
80
3- Microbial Rancidity
 Microbial Rancidity occurs when microorganisms
such as moulds or bacteria use their enzymes like
lipases to break down chemical structures of fat in
oil-producing unwanted smell and taste.
 This process can be reduced by inhibiting
microorganisms or by destroying them.
 It can also be reduced by pasteurization and the
addition of antioxidant ingredients like vitamin E.

81
 Prevention of Rancidity

 There are many possible ways to prevent Rancidity. Some of them

are:
 Antioxidants can be added to foods that contain oils and fats to
slow down oxidative deterioration.
 To slow down the process of rancidification, food can be stored in
airtight containers.
 Vacuum packing can be done to keep oxygen out.
 By adding inert gas such as nitrogen to the bag to replace oxygen.
 Food items can be kept in the refrigerator. It will reduce the rate of
most reactions that take part in rancidity.
 By storing food in dark places.

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Hazards of Rancid Fats:
1. The products of rancidity are toxic, i.e., causes
food poisoning and cancer.
2. Rancidity destroys the fat-soluble vitamins
(vitamins A, D, K and E).
3. Rancidity destroys the polyunsaturated
essential fatty acids.
4. Rancidity causes economical loss because
rancid fat is inedible ‫غير صالح لألكل‬.
83
84
 Analysis and Identification of fats
and oils (Fat Constants)
Fat constants or numbers are tests
used for:
1. Checking the purity of fat for detection of
adulteration ‫الغش‬.
2. To quantitatively estimate certain properties of fat.
3. To identify the biological value and natural
characteristics of fat.
4. Detection of fat rancidity and presence of toxic
hydroxy fatty acids.
85
 Iodine number IN (or value):
 It is the number of grams of iodine absorbed
by 100 grams of fat or oil.
 It is a measure for the degree of unsaturation of
the fat, as a natural property for it.
 Unsaturated fatty acids absorb iodine at their
double bonds, therefore, as the degree of
unsaturation increases iodine number and hence
biological value of the fat increase.
86
 It is used for identification of the type of fat,
detection of adulteration ‫ فساد‬and determining the
biological value of fat.
 Saturated fatty acids have iodine number IN = 0,
oleic acid IN = 90, linoleic acid IN = 181. Iodine
number of olive oil is 79-88, cotton seed oil is
103-111, and linseed oil ‫ زيت بذر الكتان‬is 175-202.

87
Saponification number (or value):
 It is the number of milligrams of KOH required to
completely saponify one gram of fat.
 Since each carboxyl group of a fatty acid reacts with
one mole of KOH during saponification, therefore, the
amount of alkali needed to saponify certain weight of
fat depends upon the number of fatty acids present
per weight.

88
 Thus, fats containing short-chain acids will have more
carboxyl groups per gram than long chain fatty acids and
consume more alkali, i.e., will have higher saponification
number.
 Saponification number increases as the molecular weight
of fat or oil decrease.
 Saponification number of butter fat (rich in butyric and
caproic acids) is 220- 230 and oleomargarine is less than
195.
89
 Thus, it is used to study the natural characteristics
of fats (identification of fat), and detect fat
adulteration (‫اد‬PP‫ )فس‬and selection of more suitable
type of fat for soap manufacturing.
 Toilet soap is manufactured from fat with low
saponification number, whereas, cleansing soap
from fat with high saponification number.

90
 Solved Problem I
Draw the chemical structure of triolein
1) What is the type of this triglyceride?
2) Calculate the Iodine number for triolein
3) Calculate the Saponification value for triolein
[Mol.Wt of triolein = 885.43; A.Wt. of iodine =127; Mol.Wt. KOH =56]

Solution
O
CH 2 O C (CH 2) 7 CH=CH (CH2 )7 CH 3
O

- the chemical structure of triolein H C O C (CH2 )7 CH=CH (CH 2) 7 CH3

O
1- simple triglyceride CH 2 O C (CH 2) 7 CH=CH (CH2 )7 CH 3

2-since the molecule of triolein contains three doubles ; the

molecule absorbs 3 moles of iodine(6 iodine atoms), so you
can calculate the amount of iodine in grams absorbed by
100 grams of triolein to get the iodine number
91
 O O
CH 2 O C (CH 2) 7 CH=CH (CH2 )7 CH 3 CH 2 O C (CH2 )7 CHI-CHI (CH 2 )7 CH3
O O
H C O C (CH 2) 7 CH=CH (CH2 )7 CH3 + 3 I2 H C O C (CH2 )7 CHI-CHI (CH 2) 7 CH3
O O
CH 2 O C (CH 2) 7 CH=CH (CH2 )7 CH 3 CH 2 O C (CH2 )7 CHI-CHI (CH 2 )7 CH3

Molecular Weight: 885.43 3x2x127

100 grams ?
? = Iodine number = 100x(3x2x127) / 885.43= 86.06

3-since the molecule of triolein contains three ester groups ;

the molecule require 3 moles of potassium hydroxide, so
you can calculate the amount of KOH in milligrams required
to hydrolyze one gram of triolein to get the saponification
number
92
..

O O
CH 2 O C (CH 2) 7 CH=CH (CH2 )7 CH 3 CH 2 O C (CH2 )7 CHI-CHI (CH 2 )7 CH3
O O
H C O C (CH 2) 7 CH=CH (CH2 )7 CH3 + 3 I2 H C O C (CH2 )7 CHI-CHI (CH 2) 7 CH3
O O
CH 2 O C (CH 2) 7 CH=CH (CH2 )7 CH 3 CH 2 O C (CH2 )7 CHI-CHI (CH 2 )7 CH3

Molecular Weight: 885.43 3x2x127

100 grams ?
? = Iodine number = 100x(3x2x127) / 885.43= 86.06

93
..

O
CH 2 O C (CH 2) 7 CH=CH (CH2 )7 CH 3 CH 2 OH
O O

H C O C (CH 2) 7 CH=CH (CH2 )7 CH3 + 3 KOH H C OH + 3 KO C (CH 2 )7 CH=CH (CH 2)7 CH 3

O
CH 2 O C (CH 2) 7 CH=CH (CH2 )7 CH 3 CH 2 OH

Molecular Weight: 885.43 3x56

1 gram ?

? = Saponification number = 1x(3x56) / 885.43 x 1000 = 189.74

94
 O
CH 2 O C (CH 2) 7 CH=CH CH 2 CH=CH(CH2 )4 CH 3
O
H C O C (CH 2) 7 CH=CH CH 2CH=CH(CH 2 )4 CH3 + 6 I2
O
CH 2 O C (CH 2) 7 CH=CH CH 2 CH=CH(CH2 )4 CH 3
Chemical Formula: C57H98O6
Molecular Weight: 879.38
879.38 3x2x127
100 grams ?
? = Iodine number = 100x(6x2x127) / 879.38=173.30392
95
 Acid Number (or value):
 It is the number of milligrams of KOH required to
neutralize the free fatty acids present in one gram
of fat.
 It is used for detection of hydrolytic rancidity
because it measures the amount of free fatty acids
present.

96
 Reichert- Meissl Number (or value):
 It is the number of milliliters of 0.1 N KOH required to
neutralize the water-soluble fatty acids distilled from 5
grams of fat.
 The Reichert-Meissel number measures the quantity of short
chain fatty acids in the fat molecule. Short-chain fatty acid
(less than 10 carbons) is distillated by steam.

97
98
 Q

 This studies the natural composition of the

fat and is used for detection of fat
adulteration.
 Butter that has high percentage of short-
chain fatty acids has highest Reichert-Meissl
number compared to margarine.

99
 Acetyl Number (or value):

 It is number of milligrams of KOH needed to

neutralize the acetic acid liberated from
hydrolysis of 1 gram of acetylated fat
(hydroxy fat reacted with acetic anhydride).

100
 The natural or rancid fat that contains
fatty acids with free hydroxyl groups
are converted into acetylated fat by
reaction with acetic anhydride.
 Thus, acetyl number is a measure of number
of hydroxyl groups present. It is used for
studying the natural properties of the fat and
to detect adulteration and rancidity.
101
 Acetyl number for cod liver is 1.1, for olive oil is
10.5, for cottonseed oil is 21-25, whereas the toxic
castor oil ‫زيت الخروع‬is 146-150 due to its high
content of the hydroxy fatty acid ricinoleic acid.
 This is why castor oil is inedible ‫غير صالح لالكل‬.

102
103
 Acid value

 The acid value is defined as the number of

milligrams of Potassium hydroxide required to
neutralize the free fatty acids present in one
gram of fat.
 It is a relative measure of rancidity as free
fatty acids are normally formed during
decomposition of triglycerides.

104
Chemistry of biomolecules

Lecturer 8
105