LIPIDS

INTRODUCTION
 Lipids are the substance of animal and plant origin.
 Generally insoluble in water.
 Comprise of fixed oils, fats & waxes.
 Obtained by expression or extraction methods.
 Major functions:
o They serve as structural components of biological membrane
o Provide energy reserves in the form of triacylglycerols
o Hormone synthesis
o Bile acid synthesis
o Cell differentiation and growth
CLASSIFICATION
LIPIDS

SIMPLE LIPIDS
These are esters of fatty acids with various types of alcohols. Eg; fixed oil, fats and waxes
FIXED OIL & FATS
Differ only according to their melting point, chemically belongs to the same group.
Fixed oils: substances are found to be present in a liquid at room temperature.
Fats: these are found to be either in a solid/semi-solid state at this temperature.
Chemically they are mixtures of glycerides - esters of glycerol with fatty acids. Fixed oils and fats are
made from 2 kinds of molecules, glycerol & 3 fatty acids joined by dehydration synthesis. Since there are
3 fatty acids are attached, these are known as triglycerides.

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WAXES
 These are esters of fatty acid with high weight monohydric alcohol, such as cholesterol, cetyl
alcohol etc.
 Insoluble in water, but soluble in most organic solvents.
 Waxes are similar to fats but difficult to saponify. They are only saponified by alcoholic alkali
whereas fats are saponified by aqueous and alcoholic alkali.
 Widely distributed in nature.
 Examples:
 Animal : Beeswax, Wool fat
 Plant : Spermaceti wax, Sesame wax
 Mineral : Paraffin
 Waxes are also present in the outer cell wall of epidermal tissues in fruits and leaves.
 Used in the preparation of ointments, creams etc.
Unsuitable for internal consumption, since there is no enzyme in human body to hydrolyze them
internally.
COMPOUND LIPIDS
Compound lipids are esters of fatty acids with alcohol, but contain some other substances also.
1. Phospholipids: having a Nitrogen-containing base & a phosphate group in addition to fatty
acids & glycerol.
 Eg, lacithin, cephalin
2. Glycolipids : having fatty acids, an amino alcohol & a carbohydrates.
3. Lipoproteins : contains lipids (phospholipids) & proteins in the molecules.
DERIVED LIPIDS
Formed from the hydrolysis of simple & compound lipids. Eg; fatty acids, glycerol.
FATTY ACIDS
These are carboxylic acid with long hydrocarbon side chain.
Two types:
o Saturated fatty acids

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 o Unsaturated fatty acids
Saturated and unsaturated fatty acids
Saturated FA: contains C–C bonds
Unsaturated FA: contains one or more C=C bonds

Difference between Saturated and unsaturated fatty acids

Saturated Unsaturated
Contain only C–C bonds Contain one or more C=C bonds
Closely packed Nonlinear chains do not allow molecules to pack
closely
Strong attractions between chains Few interactions between chains

High melting points Low melting points

Solids at room temperature Liquids at room temperature

Examples of saturated & unsaturated fatty acids

Fatty acids Source
Saturated fatty acids
Butyric acid Butter fat
Lauric acid Coconut oil
Myristic acid Palm oil
Palmitic acid Arachis oil, sesame oil

Stearic acid Arachis oil

Arachidic acid Mustard oil
Unsaturated fatty acids
Linolenic acid Linseed oil
Linoleic acid Sesame oil, sunflower oil
Arachidonic acid Arachis oil
Oleic acid Sunflower oil, corn oil

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ANALYTICAL PARAMETERS OF FATS AND OILS
Physical constants
 Viscosity
 Specific gravity
 Refractive index
 Solidification pints etc
Chemical constants
 Iodine value
 Acid value
 Peroxide value
 Saponification value
 Unsaponifiable matter
 Gas chromatographic detection (Novel method)

1. Iodine value: is the mass of iodine in grams that is consumed by 100g of fats & oils. Higher the
iodine value more the chance of rancidity.
2. Saponification value: Number of mg of KOH required to neutralize the fatty acids resulting from
complete hydrolysis of 1g of the sample of oil or fat.
3. Hydroxyl value: Number of mg of KOH required to neutralize the acetic acids combined to
hydroxyl groups, when 1g of sample is acetylated.
4. Acetyl value: Number of mg of KOH required to neutralize the acetic acids obtained when 1g of
sample acetylated oil is saponified. Most oils & fats (3-15), castor oil (150).
5. Unsaponifiable matter: it is the matter present in fats and oils which after saponification by
caustic alkali and subsequent extraction with an organic solvent, remain non-volatile on drying at
80ºC. It includes sterols, oil soluble vitamins etc.
6. Acid value: Number of mg of KOH required to neutralize the free acids present in 1g sample of
fat or oil. Rancidity causes the free acid liberation. Hence acid value is used as an indication of
rancid state.
7. Peroxide value: measure of peroxides present in oil. Peroxide value is less than 10 mEq/kg in
fresh samples of oil. Due to temperature or storage, rancidity occurs causing increase in peroxide
values.
8. Kreis test (Rancidity index): Phloroglucinol produces red colour with oxidized fat.
9. Ester value: Number of mg of KOH required to saponify the ester contained in 1g of sample.
Difference between saponfication value and acid value is ester value.

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 10. Polesnki value: number of milliliters of N/10 potassium hydroxide solution required to neutralize
water-soluble, steam-distillable acids liberated by hydrolysis of 5g of fat.
CASTOR OIL
Biological source: it is the fixed oil obtained by cold expression of the seeds of Ricinus communis Linn,
Family: Euphorbiaceae.
GS: All tropical & subtropical countries. India is the second largest producer of castor seeds in the world.
Description
 Colour : Pale yellow or almost colourless liquid
 Odour : Slight and characteristic
 Taste : First it is bland but afterwards slightly acrid, and usually nauseating
 Others:
o Viscous and transparent liquid
o Soluble in alcohol, miscible in chloroform, solvent ether, glacial acetic acid and pet.
ether.
o Insoluble in mineral oil
Standards
Wt per ml - 0.945 to 0.965 at 25°C
Refractive index - 1.4758 to 1.4798 at 25°C
Acid value - NMT 2.0
Optical rotation - Between +3.5° and +6.0°
Iodine value - 82-90
Acetyl value - NLT 143
Saponification value - 177-185
Soldifyng point - -10° to -18°
Viscosity - 6-8 centipoises
Chemical constituents
Consists of Glycerides of-
 Ricinoleic acid (80%)
 Isoricinoleic acid
 Stearic acid
 Dihydroxy stearic acid
 Viscosity of castor oil is due to the Ricinoleic acid
CH3 (CH2)6 CHOH CH2 CH= CH (CH2)7 COOH
Ricinoleic acid

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Others:
 Heptaldehyde (heptanal)
 Undecenoic acid
 Sebacic acid
Chemical test
 Castor oil is mixes with half its volume of light Pet. Ether (40-60ºC), but insoluble in double the
volume of petroleum ether.
 Add to the oil an equal volume of ethanol; clear liquid is obtained. On cooling at 0ºC and on
storage for 3 hrs, the liquid remains clear (distinction from other fixed oils).
Uses
 Purgative
 Emollient
 Ointment base
 Ricinoleic acid is used in contraceptive creams and jellies.
 Ingredient in hair oil
 Cathartic property of castor oil is due to the irritant action of ricinoleic acid
 Used in the preparation of paints, varnishes, grease etc.
Commercial utility of castor oil
 In the food industry, food grade castor oil is used in food additives, flavorings, candy, chocolate,
as a mold inhibitor, and in packaging. Polyoxyethylated castor oil is widely used in the food
industry.
 The United States Food and Drug Administration has approved castor oil as a safe and effective
laxative and for over-the-counter use on skin disorders. It is an excipient or additive in many
modern drugs.
 Castor oil has numerous applications in transportation, cosmetics, pharmaceutical and
manufacturing industries. It is used in the manufacture of adhesives, brake fluids, caulks, dyes,
electrical liquid dielectrics, humectants, hydraulic fluids, inks, lacquers, leather treatments,
lubricating greases, machining oils, paints, pigments, polyurethane adhesives, refrigeration
lubricants, sealants, textiles, washing powders, and waxes.
 Castor oil, like currently less expensive vegetable oils, can be used as feedstock in the production
of biodiesel. The resulting fuel is superior for cold winters.
Modified forms of castor oil
 Dehydrated castor oil: The oil on heat treatment yield DCO by removing the hydroxyl group from
ricinoleic acid.

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  Turkey Red oil: Treatment of castor oil with H2SO4 under controlled conditions yield TRO.
 Hydrogenated castor oil: on controlled hydrogenation yield a tasteless hard brittle waxy material
with a characteristic fatty odour and a cream to milk colour.
Method of preparation
 Obtained from castor seeds
 Usually the oil obtained after removing the seed coat, but sometimes it is obtained from seeds as
such & it is of inferior quality.
 For removing the seed coat, seeds are placed in grooved rollers & crushed when testa becomes
loosened & is removed by blowing in air current.
 The kernels are placed in oil-expellers & expressed at room temp with 1-2 tons pressure per
square inch till about 30% oil is obtain. Oil is filtered, but it contains poisonous principle ricin
and enzyme lipase.
 To remove ricin, steam is passed into the oil at a temp between 80-100ºC when ricin is coagulated
& precipitated and lipase becomes inactive.
 Oil is filtered & is used for medicinal purpose.
 Oil cake contains ricin, lipase & about 20% oil. It is crushed & expressed at 40-80ºC with 3 tons
pressure per square inch. The oil is obtained is inferior & not used medicinally, but used in
industries. The acidity of oil is 5%.
 The residual cake still contains about 6-10% oil which can be extracted in Soxhlet with lipid
solvents. The oil is also used in industry.
 The residual cake, because of presence of ricin cannot be used as an animal food, but is used as
manures & for production of lipase which hydrolyses fats in glycerine & fatty acids.
 Dose: 4-16 ml as laxative and pharmaceutical aid
 Storage : Store in a well closd container in a cool place.
HYDNOCARPUS OIL
Sym: Chaulmoogra oil
Biological source: it is the fixed oil obtained by cold expression method from ripe seeds of the plant
 Taraktogenos kurzii
 Hydnocarpus anthelmintic
 Hydnocarpus heterophylla and other species of Hydnocarpus; Family: Flacourtriaceae.
GS: Native of Myanmar, Thailand & E.India. Also in Sri Lanka, Bangladesh.
Description
 Colour : yellow to brownish-yellow coloured liquid
 Odour : Characteristic

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  Taste : Acrid
 Solubility : Slightly soluble in alcohol, soluble in CHCl3, ether, benzene & carbon disulphide.
 Other : soft white solid below 25ºC.
Method of preparation:
 Seeds are cleaned, washed & dried.
 They are cracked to remove testa.
 The kernels are reduced to a paste & the oil is expressed, filtered & stored in air-tight
containers.
Chemical constituents
 Contains esters of unsaturated fatty acids like:
 Chaulmoogric acid (27%)
 Hydnocarpic acid (48%)
 Goric acid (15%)
 Oleic and palmitic acid
 Proteins (20%)
 Cyanophoric glycosides

Uses
 Useful in the treatment of TB, Leprosy, Psoriasis and Rheumatism.
 Unsaturated fatty acids possess strong bactericidal effect against Mycobacterium leprae & M.
tuberculosis.
 Intended only for external use, seeds contain cyanophoric glycosides, oil cake is not edible &
cannot be used as food for animals.
BEESWAX
Sym: White beeswax, yellow beeswax
Biological source: it is the purified wax obtained from the honey comb of the bees Apis mellifera and
other species of Apis, Family: Apidae.
GS: Jamaica, Egypt, Africa, India, france, Itali, California etc.
Method of preparation
 The comb and capping of honey comb are broken & boiled in soft water.
 These are enclosed in a porous bag weighed to keep under water.
 The boiling causes oozing of the wax, which get collected outside the bag & forms a cake after
cooling. The debris on outer surface is removed by scrapping.
 Beeswax is purified by heating in boiling water or dil. H2SO4 a & settling.

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  The process is repeated several times & finally wax is skimmed off.
 White beeswax is obtained from yellow beeswax by bleaching. Various methods are adopted to
bleach wax, such as treatment with hydrogen peroxide, chromic acid, charcoal, potassium
permanganate etc. natural bleaching is done by exposing the wax to the sunlight in thin layers is
also preferred.
Description
 Colour: yellow to yellowish brown
 Odour: agreeable & honey like
 Extra features: it is a non-crystalline solid. It is soft in touch and crumble under the pressure
of fingers to plastic mass. Under molten condition, it can be given any desired shape. It
breaks with granular fracture.
 Solubility: insoluble in water. Soluble in hot alcohol, ether, CHCl3, CCl4, fixed & volatile
oils.
Standards
 Melting point : 62-65°C
 Specific gravity : 0.958-0.967
 Acid value : 5-10
 Saponification value : 90-103
 Ester value : 80-95
Chemical constituents
 Consists of esters of straight chain monohydric alcohols with straight chain acids.
 The chief constituent is myricin ie; myricyl palmitate (80%)
 Others:
o Free cerotic acid (15%),
o Small quantities of melissic acid
o Aromatic substance, cerolin
Chemical test
Saponification claud test: Boil 0.5g of beeswax with 20 ml aqueous caustic soda solution for 10 min &
cool. No turbidity is produced.
Uses
 Used in the preparation of ointment, plasters and polishes.
 Manufacture of candles, moulds & in dental & electronic industries.
 Used in cosmetics for preparation of lipsticks & face cream.

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  Pharmaceutically used as an ingredient of paraffin ointment IP.
WOOL FAT (HYDROUS WOOL FAT)
Sym: Lanolin
Biological source: It is the purified fat like substance obtained from the wool of the sheep Ovis aries;
Family: Bovidae. It contains 25-30% of water. It is the secretion of sebaceous glands of sheep deposited
onto the wool fibres.
Method of preparation
 Raw wool contains about 31% wool fibres, wool sweat, 32% earthy matter & 25% wool grease or
crude lanolin.
 Crude lanolin is separated by washing with H2SO4 or suitable organic solvent or soap solution.
 It is further purified & bleached. The product is known as anhydrous lanolin or wool fat.
 Hydrous wool fat is produced by intimately mixing wool fat with 30% of water.
Chemical constituents:
 It is a complex mixture of esters & polyesters of 33 high molecular weight alcohols & 36 fatty
acids.
 Hydrous wool fat contains mainly esters of cholesterol & isocholesterol with carnaubic, oleic,
myristic, palmitic, lignoceric & lanopalmitic acids.
 Water (50%)
Chemical test: Dissolve 0.5 g hydrous wool fat in CHCl3 & to it add 1 ml of acetic anhydride & 2 drops
of H2SO4. A deep green colour is produced indicating the presence of cholesterol.
Uses
 It is mainly used as water absorbable ointment base.
 It is a common ingredient & base for several water soluble creams & cosmetic preparations.

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