1. AN ASSIGNMENT ON
Pharmaceutical importance of lipids
COURSE TITLE : ORGANIC PHARMACY II
COURSE CODE : PHR122
Submitted To: Submitted By:
SUBRATO KUMAR BARMAN Md. Faiazule Hoque Lamem
Lecturer ID No: 19200006
Department of Pharmacy Department of Pharmacy
Ranada Prasad Shaha University
DATE OF SUBMISSION: 15.04.2020
2. Contents Index
Assignment title : Pharmaceutical importance of lipids
Sl
No Topics
01 Abstract
02 Definition
03 Classification of Lipids
04 Simple Lipids
➢ Fats and oils
➢ Waxes
05 Compound Lipids
➢ Phospholipids
➢ Glycolipids
06 Derived Lipids
➢ Steroids
➢ Cholesterol
07 Properties of Lipids
08 Functions of Lipids
09 Fats and Oils
10 Physical properties of oils and fats
11 Chemistry of Oils and Fats
12 Chemical Properties of Fatsand Oils
13 Importance Of Fats and Oils
14 Phospholipids
15 Properties of Phospholipids
16 Importanceof Phospholipids
3. The word “lipid” comes from the Greek word lipos, meaning fat greasy to the
touch. Lipids are diverse group of organic compounds found in plants , animal and
micro-organisms. They comprise one of the three large classes of foods and, with
proteins and carbohydrates, are components of all living cells.
Lipids are a broad group of naturally occurring and molecules, soluble in non polar
solvent and insoluble in polar solvent. A clear advantage of the lipid is their
structure resembles to that of biological lipids which decreases the danger of acute
and chronic toxicity. Lipids used in pharmaceutical industries exhibit unique
physical and chemical properties. Their composition, crystalline structure, melting
properties and ability to associate with water and other non-lipid molecules are
especially important to their functional properties.
Lipids used in pharmaceutical industries exhibit unique physical and chemical
properties. Their composition, crystalline structure, melting properties and ability
to associate with water and other non-lipid molecules are especially important to
their functional properties.
Definition : Any of a class of organic compounds that are fatty acids or their
derivatives and are insoluble in water but soluble in organic solvents is called
Lipids. They include many natural oils, waxes, and steroids.
Classification of Lipids
4. There are several specific types of lipids important to live, including fatty acids,
triglycerides, glycerophospho lipids, sphingo lipids, and steroids. These are
broadly classified as simple lipids , complex lipids , derived lipids.
1. Simple Lipids
Simple lipids are esters of fatty acid linked with various alcohols.
➢ Fats and oils
These esters of fatty acid have glycerol, a trihydroxy alcohol. Fat is solid at room
temperature, while oil is in liquid form.
Triglycerides are abundant and constitute about 98 percent of all dietary lipids. The
rest consists of cholesterol, its esters and phospholipids. Unlike carbohydrates,
which can be stored only for a short time in the body, triglycerides are stored in the
body in large amounts as body fat, which can last for years.
An average man weighing about 70 kg, has at least 10 to 20 percent of his body
weight in lipid, most of which is triacylglycerol. This is found in adipose (fat)
tissue, as well as all other organs of the body. Body fat is a reservoir of chemical
energy.
➢ Waxes
Waxes are long-chain saturated and unsaturated fatty acid esters with
monohydroxy alcohols, which have high molecular weight.
Waxes are produced naturally by skin glands as a protection, to keep it lubricated,
pliable, and water-proof. Wax also covers hair, feathers, and wool.
2. Compound Lipids
These are another classifications of lipids. Heterolipids are fatty acid esters with
alcohol and additional groups.
➢ Phospholipids
Phospholipids contain fatty acids, glycerol, nitrogen bases, phosphoric acid, and
other substituents. They are most abundant in cell membranes and serve as
structural components. They are not stored in large quantities. As their name
5. implies, phospholipids contain phosphorus in the form of phosphoric acid groups.
Their molecular structure is polar, consisting of one hydrophilic head group and
two hydrophobic tails.
➢ Glycolipids
Glycolipids are fatty acids with carbohydrates and nitrogen but without phosphoric
acid. Glycolipids also include some compounds like sulfolipids, gangliosides, and
sulfatids which are structurally-related.
These cerebrosides are important constituents of the brain and other tissues. They
consist of at least one sugar unit, so they are also called glycosphingosides. They
are like phospholipids because they have a hydrophobic region, with a polar region
and two long hydrocarbon tails. Like phospholipids, glycolipids form lipid bilayers
that are self-sealing and form the structure of cellular membranes.
3. Derived Lipids
These substances are derived by hydrolysis from compound and simple lipids.
These fatty acids include alcohols, mono- and diglycerides, carotenoids, steroids,
and terpenes.
➢ Steroids
The steroids are biological compounds that are some of the most studied types of
fat. They contain no fatty acids and unlike fats, are nonsaponifiable (cannot be
hydrolyzed to yield soap).
➢ Cholesterol
Cholesterol is a well-studied lipid, because of its strong correlation with the
incidence cardiovascular disease. It is an important component of cell membranes
and plasma lipoproteins, and is an important precursor of many biologically
important substances like bile acids and steroid hormones. It is abundant in nerve
tissues and is associated with gallstones.
Dietary cholesterol is found in saturated fats of animals (as butter and lard), but
vegetable oils do not contain cholesterol. Only a small portion of your body
cholesterol comes from the diet. Most of it is produced in the body. Eating
unsaturated fatty acids from vegetable oil helps lower blood cholesterol levels by
reducing cholesterol synthesis in the body. However, eating saturated fats from
6. animal fat elevates blood cholesterol and triglycerides and reduce the ratio of your
good to bad cholesterol.
Properties of Lipids
Lipids are a family of organic compounds, composed of fats and oils. These
molecules yield high energy and are responsible for different functions within the
human body. Listed below are some important characteristics of Lipids.
• Lipids are oily or greasy nonpolar molecules, stored in the adipose tissue of the
body.
• Lipids are a heterogeneous group of compounds, mainly composed of
hydrocarbon chains.
• Lipids are energy-rich organic molecules, which provide energy for different
life processes.
• Lipids are a class of compounds distinguished by their insolubility in water and
solubility in nonpolar solvents.
• Lipids are important in biological systems because they form the cell
membrane, a mechanical barrier that divides a cell from the external
environment.
• Solid triglycerols (Fats) have high proportions ofsaturated fatty acids.
• Liquid triglycerols (Oils) have high proportions ofunsaturated acids.
• Insoluble in water
• No ionic charges
• Soluble in organic solvents like alcohol, chloroform, acetone, benzene, etc
• Pure fats and oils are colorless, odorless, and tasteless.
7. Functions of Lipids
Lipids can serve a diverse range of functions within a cell, including:
• Storage of energy for long-term use (e.g. triglycerides)
• Hormonal roles (e.g. steroids such as oestrogen and testosterone)
• Insulation – both thermal (triglycerides) and electrical (sphingolipids)
• Protection of internal organs (e.g. triglycerides and waxes)
• Structural components of cells (e.g. phospholipids and cholesterol)
• Protection –e.g. protecting plant leaves from drying up
• Making Biological Membranes.
Fats and Oils :-
Fats and oils are the primary energy storage forms of animals and are also known
as triacylglycerols and triglycerides, since they consist of a glycerol molecule
linked via ester bonds to three fatty acids. Fats and oils have the same basic
structure. We give the name fat to those compounds that are solid at room
temperature and the name oil to those that are liquid at room temperature.
Physical properties of oils and fats :-
The analysis of the physical properties of oils and fats allows us to understand the
behavior and characteristics of these elements, as well as their differences. For this,
the crystallization, the melting point, the viscosity, the refractive index, the density,
the solubility, the plasticity and the emulsifying capacity will be analyzed.
Here we provide more detail on each of these.
➢ Crystallization
Fats differ from oils in their degree of solidification at room temperature, since in
these conditions the oils are in a liquid state (not crystallized) while the fats are in
the solid (crystallized) state.
8. The proportion of crystals in fats have great importance in determining the
physical properties of a product. Fats are considered solid when they have at least
10% of their crystallized components.
➢ Melting point
The melting point of a fat corresponds to the melting point of the β form which is
the most stable polymorphic form and is the temperature at which all the solids
melt.When short chain or unsaturated acids are present, the melting point is
reduced.
The melting point is of great importance in the processing of animal fats.
The melting points of pure fats are very precise, but since fats or oils are made up
of a mixture of lipids with different melting points we have to refer to the melting
zone which is defined as the melting point of the fat component. the fat that melts
at a higher temperature.
➢ Viscosity
The viscosity of a fat is due to the internal friction between the lipids that
constitute it. It is generally high due to the high number of molecules that make up
a fat.
By increasing the degree of unsaturation the viscosity decreases and when the
length of the chain increases the fatty acids components also increases the
viscosity.
➢ Refractive index
The refractive index of a substance is defined as the ratio between the speed of
light in air and in matter (oil or fat) that is analyzed.
Increasing the degree of unsaturation increases the refractive index and when the
length of the chain increases, the refractive index also increases and that is why it
is used to control the hydrogenation process.
As the temperature increases, the refractive index decreases.
The refractive index is characteristic of each oil and fat, which helps us to perform
a quality control on them.
9. ➢ Density
This physical property is of great importance when it comes to designing
equipment to process grease.
Density decreases when fats dilate when going from solid to liquid
When the fats melt, their volume increases and therefore the density decreases.
For the control of percentages of solid and liquid in commercial fat, dilatometric
curves are used.
➢ Solubility
Solubility has great relevance in the processing of fats.Fats are fully soluble apolar
solvents (benzene, hexan).Except for phospholipids, they are completely insoluble
in polar solvents (water, acetonitrile). They are partially soluble in solvents of
intermediate polarity (alcohol, acetone)
The solubility of fats in organic solvents decreases with increasing chain length
and degree of saturation.
Phospholipids can interact with water because the phosphoric acid and the alcohols
that compose them have hydrophilic groups.
Generally the surface tension increases with the length of the chain and decreases
with temperature. Surface tension and interfacial tension decrease with ease with
the use of surfactant agents such as monoglycerides and phospholipids.
➢ Plasticity
It is the property that has a body to preserve its shape by resisting a certain
pressure.The plasticity of a fat is caused by the presence of a three-dimensional
network of crystals inside which liquid fat is immobilized.
The plastic fats act as a solid until the deforming forces that are applied break the
crystal lattice and the grease passes to behave like a viscous liquid and therefore
can be smeared.
10. ➢ Emulsifying capacity
The emulsifying capacity is the capacity in the water / oil interface allowing the
formation of emulsion.
Chemistry of Oils and Fats
The carbon atom is the basic element in food chemistry, induding oils and fats.
Carbon atoms, with a valence of 4, may bond together with other carbon atoms to
form molecules with long chains. Fur-thermore, carbon's ability to form bonds or
react with other ele-ments such as hydrogen, oxygen, iodine, nitrogen, and
phosphorus is fundamental to understanding the chemistry of oils and fats.
Basically, oils and fats are mixtures of triglycerides. This is the manner in which
they are composed naturally.
H
H-C-OH
H-C-OH
H-C-OH
H
Glycerol
The glycerol molecule has three carbon atoms, together with five hydrogen
atoms and three OH or hydroxyl groups. It should be noted that there are
four bonds or linkages to each of the three car- bon atoms. When three fatty
acids are combined with one glycerol molecule, we have a triglyceride.
H
Triglyceride
H — C — Fatty acid
H — C — Fatty acid
H — C — Fatty acid
H
11. A triglyceride is called a fat if it is a solid at 25°C; it is called an oil if it is a liquid
at that temperature. These differences in melting points reflect differences in the
degree of unsaturation and number of carbon atoms in the constituent fatty acids.
Triglycerides obtained from animal sources are usually solids, while those of plant
origin are generally oils. Therefore, we commonly speak of animal fats and
vegetable oils. No single formula can be written to represent the naturally
occurring fats and oils because they are highly complex mixtures of triglycerides in
which many different fatty acids are represented.
Fats and oils can participate in a variety of chemical reactions for example,
because triglycerides are esters, they can be hydrolyzed in the presence of an acid,
a base, or specific enzymes known as lipases. The hydrolysis of fats and oils in the
presence of a base is used to make soap and is called saponification. Today most
soaps are prepared through the hydrolysis of triglycerides (often from tallow,
coconut oil, or both) using water under high pressure and temperature. Sodium
carbonate or sodium hydroxide is then used to convert the fatty acids to their
sodium salts (soap molecules):
Rancidity is a major concern of the food industry, which is why food chemists are
always seeking new and better antioxidants, substances added in very small
amounts (0.001%–0.01%) to prevent oxidation and thus suppress rancidity.
Antioxidants are compounds whose affinity for oxygen is greater than that of the
lipids in the food; thus they function by preferentially depleting the supply of
oxygen absorbed into the product. Because vitamin E has antioxidant properties, it
helps reduce damage to lipids in the body, particularly to unsaturated fatty acids
found in cell membrane lipids.
Fats and oils that are in contact with moist air at room temperature eventually
undergo oxidation and hydrolysis reactions that cause them to turn rancid,
12. acquiring a characteristic disagreeable odor. One cause of the odor is the release of
volatile fatty acids by hydrolysis of the ester bonds. Butter, for example, releases
foul-smelling butyric, caprylic, and capric acids. Microorganisms present in the air
furnish lipases that catalyze this process. Hydrolytic rancidity can easily be
prevented by covering the fat or oil and keeping it in a refrigerator.
Chemical Properties of Fats and Oils :-
➢ Hydrolysis: Fats are hydrolyzed by the enzyme lipase to fatty acids & glycerol.
• Reaction carried out at alkaline pH 7.5-8.5.
• The fats first splits to produce diglycerides, then monoglycerides & finally
to fatty acid & glycerol.
➢ Saponification: Hydrolysis offats by alkali is called Saponification.
• Soaps are of2 types:-hard soaps & soft soaps.
• Products ofsaponification are glycerol & salts offatty acids called soaps.
• Fatty acid salts ofcalcium, zinc, magnesium & lead are insoluble in water
Key Takeaways
• Fats and oils are composed of molecules known as triglycerides, which are
esters composed of three fatty acid units linked to glycerol.
• An increase in the percentage of shorter-chain fatty acids and/or unsaturated
fatty acids lowers the melting point of a fat or oil.
• The hydrolysis of fats and oils in the presence of a base makes soap and is
known as saponification.
• Double bonds present in unsaturated triglycerides can be hydrogenated to
convert oils (liquid) into margarine (solid).
• The oxidation of fatty acids can form compounds with disagreeable odors.
This oxidation can be minimized by the addition of antioxidants.
13. Importance Of Fats and Oils :-
Fixed oils and fats are important products used pharmaceutically, industrially and nutritionally.
INDUSTRIALLY: -
Manufacturing of detergents, soaps, paints, and varnishes and as lubricant.
PHARMACEUTICALLY : -
➢ As stimulant, cathartic, purgative e.g. castor oil.
➢ As emollient for ointments, liniment creams and other preparations e.g. almond
oil, coconut oil.
➢ As vehicle = peanut oil, seasam oil is used as solvent in the preparation of
certain I/ M injection.
NUTRITIONALLY:-
Others like corn oil with its high contents of unsaturated fatty acids is suggested in
diet instead of fixed oil or fats having high saturated fatty acids to reduce high
blood cholesterol level.
OCCURRENCE:-
Vegetable oil and fats may occur in various parts of the plant but a general rule,
seeds contain larger quantities of fats and oils than do other plant parts. Seeds are
the usual source of fixed oils. Few examples are cottonseed oil, linseed oil, sesame
oil, hemp seed oil, coconut oil castor beans, almond etc.
Other plants parts also yield considerable amounts of fixed oil e.g. pericarp of the
olive, in certain fungi e.g. ergot.
Fat is a characteristic food material from animal e.g. lard.
FATS VS FIXED OILS :-
Fats Fixed Oils
Solid at room temperature Liquid at room temperature
Contain saturated glycerides
e.g. glyceryl stearate
Contain unsaturated glycerides
e.g. glyceryl oleate
14. Phospholipids :-
Phospholipids are a class of lipids that are a major component of all cell
membranes. They can form lipid bilayers because of their amphiphilic
characteristic. The structure of the phospholipid molecule generally consists of two
hydrophobic fatty acid "tails" and a hydrophilic "head" consisting of a phosphate
group. The two components are usually joined together by a glycerol molecule.
The phosphate groups can be modified with simple organic molecules such as
choline, ethanolamine or serine.
Phospholipids are fat derivatives in which one fatty acid has been replaced by a
phosphate group and one ofseveral nitrogen-containing molecules.
Phospholipids are used in pharmaceutical technology as wetting agents,
emulsifiers, and builder or components of mesophases like liposomes, micelles,
mixed micelles, cubosomes, etc. These functional properties are used in many
formulation types, like suspensions, various types of emulsions, mixed micelles,
solid dispersions, drug–phospholipid complexes, etc.. Due to their physiological
role, phospholipids possess a very low toxicity profile and can be used for any
route of administration.
Properties of Phospholipids
➢ Phospholipids are the major component of all cell membranes.
➢ Phospholipids are structurally similar to fats.
➢ Fats contain three fatty acids attached to glycerol.
➢ Phospholipids contain two fatty acids attached to glycerol.
➢ The phosphate group is the negatively-charged polar head, which is
hydrophilic.
➢ If phospholipids are placed in water, they form into micelles, which are lipid
molecules that arrange themselves in a spherical form in aqueous solutions.
Importance of Phospholipids
• The biocompatibility of phospholipids makes them ideal candidates for drug
delivery systems.
• Phospholipids often form liposomes that can carry drug.
15. • Phospholipids also serve as good emulsifiers.
• Pharmaceutical companies can choose phospholipids from eggs, soybeans or
artificially constructed phospholipids to aid in drug delivery.
• Phospholipids can make liposomes, special vesicles that can better match cell
membrane structure.
• The emulsifying properties ofphospholipids make them ideal for intravenous
injection emulsions.
• If drugs have poor bioavailability, sometimes natural flavonoids can be used to
form complexes with phospholipids, aiding drug absorption. These complexes
tend to yield stable drugs with longer action.
• As continued research yields more information about the increasingly useful
phospholipids, science will benefit from the knowledge to better understand
cellular processes and to make more highly targeted medicines.
Conclusion
Lipids are essential for all life on Earth. They play many important roles in
maintaining the health of an organism. Arguably the most important function lipids
perform is as the building blocks of cellular membranes. Other functions include
energy storage, insulation, cellular communication and protection.