LIPIDS, FATS AND WAXES

Lipids are naturally occurring non-polar, water insoluble and hydrophobic

substances found in the cells. They are important constituents of cell
membrane and cell organelles. Fats and oils are made from are made from
two kinds of molecules, the glycerol (type of alcohol with hydroxyl group on
each of its three carbons) and three fatty acids joined by dehydration
synthesis. Like fats and waxes are esters of fatty acids. In plants, waxes are
generally found covering the external parts (epidermis of leaves and fruits),
where their main function is to prevent loss of water.

Why are lipids insoluble in water and hydrophobic substances? Write

your answer with presentation of Lipids structure in the space provided
below
 DISSECT

Lipids are a heterogeneous group of compounds related, either

actually or potentially, to the fatty acids. They are water insoluble organic
molecules that can be extracted from cells and tissues by non-polar solvents.
Lipids are derivatives of fatty acids, and their naturally existing compounds.
Biologically, lipids have a wide range of uses such as source of fuel,
protective coat and component of membranes of every living cell. Lipids are
classified as;

Simple lipids which are esters of fatty acids with various alcohol and
include:
1. Neutral fats – ester of fatty acids with glycerol
- liquid fats are known as oil
2. Waxes – ester of fatty acids with higher molecular weight non-hydric
alcohol

Complex lipids are esters of fatty acids containing other groups in

addition to an alcohol and a fatty acids such as:

1. phospholipids – containing a phosphoric acid residue and frequently have

nitrogen-containing bases and other compounds like:
a. Glycerophospholipid (alcohol is glycerol)
b. sphingophospholipid (alcohol is sphingisine)
2. Glycolipods (glycosphingolipids) – contains fatty acid, sphingosine, and
carbohydrates
3. Other complex lipids – includes sulfolipids and aminolipids

Precursor and Derived lipids:

- product of hydrolysis of simple and complex lipids but still exhibiting
the general physical characteristics of lipids
- these include fatty acids, glycerol, steroids, alcohols (in addition to
glycerol and sterols), fatty aldehydes and ketone bodies, hydrocarbons,
lipid-soluble vitamins, and hormones
- glycerides, cholesterol, and cholesterol esters are called neutral fats
because they are without charge.

Lipids can be found from the following sources:

 - True fats generally constitute the storage material for energy in both
plants and animals.
- fat depot of the animal body which is made up of excess fats derived
from ingested food.
- found in the subcutaneous and intra molecular connective tissues
(omentum) which serves as heat insulator and reserves supply for energy.
- compound lipids such as cerebrosides are constituents of highly
specialized brain and nervous tissues.
- phospholipids and sterols are intimately related with bile acids,
vitamin D and sex hormones.

The following are some common lipids:

Fatty acids
- Most abundant naturally occurring lipids.
- building blocks of several classes of lipids like the neutral fats,
phosphoglycerides, glycolipids, cholesterol esters, and waxes
- possessed long hydrocarbon chain and a terminal carboxyl group
- chain may be saturated (without double bonds) or unsaturated (with
1or more double bonds)
- with few exceptions, they have an even number of carbon atoms.

There are two types of fatty acids:

1. Saturated Fatty Acids:
-belong to the acetic series and have the general formula C nH2nO2.
- IUPAC name end in IC + acids.
-have only single bond only their structure.
-with low molecular weight.
-Liquid at ordinary temperature.
-With low melting point and are volatile. Their melting point increases with
increasing molecular weight.
-characteristic of animal fats.

* IUPAC = International Union of Pure and Applied Chemistry.

(the standard, universal system for nomenclature of organic
compounds).

The following are examples of saturated fatty acids.

Butyric Acid, Caproic Acid, Capric Acid, Lauric Acid, Palmitic Acid,
Stearic acid, Arachidic acid, Lignoceric acid

Each carbon in the chain has two hydrogen atoms attached to it. It is
"saturated" with hydrogen atoms.

2. Unsaturated fatty acids:

- unstable and reactive due to the presence of double bonds.
- IUPAC name ends in EIC + acid.
- reactivity increases with increasing double bonds.
- liquid at ordinary temperature and are non-volatile.
- the greater the degree of unsaturation, the lower are their melting.
- characteristic of vegetable fats.

The following are examples of unsaturated fatty acids:

- Myristoleic acid, Palmitoleic acid, Oleic acid, Linoleic acid ,

Linolenic acid
- plasmatic acid makes about 50% of total fatty acids in fats.

- Oleic acid is the most abundant fatty acid in nature forming about
50% of the total fatty acids in many fats and is found in all naturally existing
fats.
 With low Molecular Weight and with the occurrence of double bonds
Neutral fats

1. Triglycerides – ester of glycerol and fatty acid

- When R, R1 and R2 are the same, the compound is a simple
triglyceride.
- Natural fats possess mixed glycerides; thus if R is oleic acid, R1 is
stearic acid, and R2 is palmitic acid, the glyceride is called alphaoleyl, beta
stearyl, alpha’ – palmitin
- Glycerides of saturated fatty acids have higher melting points than
glycerides of unsaturated fatty acids, thus vegetable fats, olive oil,
castor sees oil contain more unsaturated fatty acids than animal fats such as
lard and tallow
- Ester groups are readily broken down by alkali through a process
called saponification, a commercial method for the production of
glycerol and soap.

2. Waxes
- neutral fats that are ester of fatty acids and high molecular weight
of alcohols, the most important of which is cholesterol.
- alcohols range in length from 14-34 carbon atoms
Example: sperm oil, bees wax, lanolin

Complex lipids

1. Phosphoglycerides
- sometimes called phospholipids
- esters formed by the union of different alcohols with phosphatidic
acid in which the alpha and beta positions are esterified with fatty
acids and the alpha position with phosphoric acid
- fatty acid in alpha’ position is usually a long chain saturated fatty
acid, such as palmitic or stearic; fatty acid in beta position usually
unsaturated such as oleic, linoleic, or arachidonic acid.
 - phospholipids of physiological importance are:

a. phosphatidyl cholines (lecithins)

- present in eggyolk, liver and nervous tissues.
- soluble in all fat solvents except acetone
- white, waxy substances that form emulsions
- soybeans lecithin used as emulsifying agent in food industry.
- Enzyme lecithinase found in cobra venom and poisonous
spiders hydrolysis lecithin producing lysolecithin which has
hemolyzing effect upon TBC thus poisonous effects of venom of cobra
and insects.

b. phosphatidyl ethanolamines and phosphatidyl serines

(collectively referred to as cephalins)
- Found in all tissues and cells but particularly abundant in brain
and other nerve tissues
- property very much similar to the lecithins.
- A thromboplastic substance which initiates blood clotting.

c. phosphatidyl inositols (lipositol)

- occur in all cells and tissues

3. Sphingolipids (glycolipids)
- formed by some fatty acids called ceramides and sphingosine
- generally structure of sphingolipids indicated below where
ceramides are in either linkage to different compounds
a. sphingomyelins – found in all tissues but very abundant in brain
and nervous tissues
b. cerebrosides – found in membranes of brain tissues, particularly in
the white tissue
c. gangliosides - usually found on the surface of cell
membranes, especially of nerve cells
3. Prostaglandins
- family of compounds comprising 14 fatty acids each containing 20
carbon atoms and having the same basic skeleton prostanoic acid
- involved in a number of biochemical interactions like regulation of
blood supply, development of inflammatory response, regulation of
ions influx across epithelial membrane, etc.

4. Steroids
- found in association with fats and separated from the fats after
saponification in the “unsaponifiable residue”
 - all possess similar cyclic nucleus resembling phenanthrene (rings A,
B, and C) to which a cyclopentane ring attached

a. cholesterol
- widely distributed in all cells particularly in the nervous tissue
- major component of the plasma membrane
- also found underneath the skin and serves as the precursor of
vitamin D synthesis.

c. coprosterol
- occurs in faces as a result of the reduction of the double bonds of
cholesterol by bacteria in the intestine
d. bite salts
- constituent of bile
- strong emulsifying agent that help disperse fatty materials
- stimulate intestinal motility

e. steroidal hormones
- sex hormones; testosterone, estrogen, progesterone
- ACTH

GENERAL PROPERTIES OF FATS

B. Physical properties:
1. Greasy.
2. Penetrate some materials like paper producing a translucent effect.
3. Neutral fats when pure are odorless, tasteless, and colorless.
4. Insoluble in ordinary in solvent but soluble in organic solvent.
5. Non – volatile.
6. Produce characteristic crystals with definite melting point.
7. maybe solid or liquid (oil) at ordinary temperature.
8. Floats on water because of its low specific gravity. When
shaken with water, fast break into fine particles forming a temporary
emulsion.

C. Chemical Properties:

1. Hydrolysis – readily broken down by acids, enzymes or stream

liberating fatty acids and alcohol.
2. Saponification – formation of metallic salt of fatty acid (soap) when
heated with alkali.
 3. Rancidity – become rancid or acidic when expose to air. This is due
to hydrolysis resulting in the liberation of volatile fatty acids, which are then
oxidized forming odoriferous volatile aldehydes and ketones.
4. Identification – by the use of certain chemical constants such as:
a. Iodine number – number of grams of iodine taken up
by 100 g. of fat. It is the measure of the degree of unsaturation
of a given fat/mole.
b. Saponification number – number of milligram of an alkali
required in neutralize the fatty acids contain in 1 gram of fats. It is the
measure of fatty acids in a given fats/mole.
c. Acetyl number – number of milligram of KOH necessary to
neutralize the acetic acid liberated from the hydrolysis of 1 g. of acetylated
fat. Measure the number of hydroxyl group present in a given fat/mole
d. Reichert-Meiss1 number – amount of 0.1 N of an alkali
required to neutralize the volatile fatty acids distilled from 5 g. of fat. Use in
the detection of butter substances.

FUNCTIONS

Lipids Functions are:

1. membrane structural components
2. intracellular storage debuts of metabolic fuels.
3. transport form of metabolic fuel
4. protective form of cell walls of many bacteria, of leaves of higher plants, of
the exoskeleton of insects, and the skin of vertebrates
5. regulatory substances
6. transport forms of some neurotransmitters
7. receptors in nerve ending membranes
8. determinants of immunological specificity
9. enzymes factors

DEEPEN

KEY POINTS

Lipids are non-polar substances wit key function as energy storage, signaling
and acting as structural components of cell membranes. Major types include
fats, and oils, waxes and phospholipids and steroids. Fats are stored form of
energy and are also known as triglycerides or triglycerols. Fats are made up
of fatty acids and either glycerol or sphingosine.

WORK ON THIS

Direction: Read and analyze the given questions before answering. Write
your answers in the space provided after each question.

1. Illustrate a graphic organizer showing the classification of lipids.

2. Explain what makes a fat saturated or unsaturated.

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3. Describe what is being formed with the combination of glycerol and fatty
acids by a dehydration reaction.

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