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:
They serve as structural components of biological membrane
Provide energy reserves in the form of triacylglycerols
Hormone synthesis
Bile acid synthesis
Cell differentiation and growth
LIPIDS
COMPOUND DERIVED
SIMPLE
1. Phospholipids
1. Fats and oils 1. Fatty acids
2. Glycolipids
2. Waxes 2. Alcohol
3. Lipoproteins (glycerol, sterol)
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.
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.
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.
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:
Saturated fatty acids
Unsaturated fatty acids
Saturated FA: contains C–C bonds
Unsaturated FA: contains one or more C=C
bonds
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
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
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.
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.
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.
Colour : Pale yellow or almost colourless liquid
Odour : Slight and characteristic
Taste : First it is bland but afterwards slightly acrid, and
usually nauseating
Others:
Viscous and transparent liquid
Soluble in alcohol, miscible in chloroform, solvent
ether, glacial acetic acid and pet. ether.
Insoluble in mineral oil
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
Others:
Heptaldehyde (heptanal)
Undecenoic acid
Sebacic acid
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).
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.
Dehydrated castor oil: The oil on heat treatment yield
DCO by removing the hydroxyl group from ricinoleic
acid.
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.
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.
Biological source: it is the fixed oil obtained by expression
from the seeds of Sesamum indicum, Family: Pedaliaceae.
GS: India, China, Japan, Africa, US
Description:
Colour: Pale yellowish liquid
Odour: Slight, characteristic
Taste: Bland
Solubility: slightly soluble in alcohol, miscible with CHCl3,
solvent ether, light petroleum and carbon disulphide.
Other: it does not solidify at 0ºC.
Consists of a mixture of glycerides of:
Oleic acid (43%)
Linoleic acid (43%)
Palmitic acid (9%)
Stearic acid (4%)
Arachidic acid
Lignan derivatives
Sesamin
Sesamolin
Phenol – Sesamol, responsible for the stability of oil
Carbohydrates and proteins
Vitamin A & E
Sterols
Badouin’s test:
Shake 2ml Sesame oil with 1ml of 1% solution of sucrose in
HCl, a pink/red colour is produced due to sesamol.
Uses:
Laxative
Nutritive
Demulscent
Emollient
Vehicle for intramuscular oily injections
Oil is used in insecticidal sprays
Used in the preparation of liniments, plasters, ointment &
soaps
Sym: Chaulmoogra oil
BS: 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.
Colour : yellow to brownish-yellow coloured liquid
Odour : Characteristic
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.
Contains esters of unsaturated fatty acids like:
Chaulmoogric acid (27%)
Hydnocarpic acid (48%)
Goric acid (15%)
Oleic and palmitic acid
Proteins (20%)
Cyanophoric glycosides
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.
Sym: Flax seed
BS: consists of fixed oil obtained from dried fully
ripe seeds of Linum usitatissimum Linn, Family :
Linaceae.
GS: Russia, Canada, USA, Argentina, Italy, India
etc.
Commercially linseed oil is produced by use of expellers.
Before the seeds are subjected to the expellers, they are
rolled into meal, then moistened and heated by means of
steam jacketed troughs to soften the seed tissue, filled over
the expellers.
The average yield of oil is 30-35%.
The expressed oil is tanked for a long period to settle the
colouring matter and mucilage.
The oil is then treated with alkali immediately after
filtration. Alkali treatment help to remove free fatty acids.
Bleaching of the oil is done by using either charcoal at
elevated temperature.
The refined oil is again chilled to separate wax.
Description
Colour : pale yellow coloured clear liquid
Odour : characteristic
Taste : pleasant
Slightly soluble in alcohol, insoluble in water and miscible
with ether, pet ether & CHCl3.
Standards
Sp. Gravity : 0.927-0.931
Refractive index : 1.4786-1.4815
Saponification value : 188-195
Iodine value : 160-200
Acid value : NMT 4
Unsaponofiable matter : NMT 1.5
Contains glycerides of
Palmitic acid
Stearic acid
Oleic acid
Linoleic acid
Linolenic acid
Unsaponifiable matter contains
Linamarin
Sterol
Tocopherol
Squalene
Cyanogenetic glycosides- Linamarin
Mucilage (5%)
Fixed oil (20-40%)
3-omega fatty acids
Demulcent and laxative properties
Emollient in lotions and liniments.
Used to prepare non-staining iodine ointments
Used in polishes, paints, varnishes, greases, polymers
etc.
Makes the fabric and paper water proof.
Linseed oil is adulterated with the following:
Boiled linseed oil
Cotton seed oil
Sun flower oil
Mineral oil
Rosin
Fish oils
Mustard oil
BS: fixed oil obtained by expression/extraction from the
seed kernels of the Coconut palm, Cocos nucifera,
family: Palmae.
Description:
Odourless and bland taste
melting point- 23-26ºC
Soluble in 2 volume of alcohol at 60ºC, highly soluble in
Chloroform, ether & carbon disulphide.
Readily become rancid on exposure to air.
Highest saponification value, lowest iodine value
Mainly contains mixture of glycerides in which 80-85% of
saturated acids.
Saturated fatty acids
Lauric acid (50%)
Myristic acid (20%)
Also contain glycerides of
Caprylic acid
Capric acid
Oleic acid
Palmitic acid
Stearic acid
Low iodine value and high saponification value.
Dietary supplement
Used in soap and shampoos
Ingredient in a number of combination products for
oral administration.
Oil is easily absorbed from GIT, which makes it of
value to patient patients with fat absorption problem.
Fractionated and purified oil of Cocos nucifera
Triglycerides containing only the short & medium
chain fatty acids (octanoic & decanoic acids)
Maintain low viscosity until solidification point (0ºC)
BS: is the fixed oil obtained from the rice bran (cuticle existing
between the rice and husk of paddy) of the seeds of Oryza
sativa Linn, family: Graminae. Contains about 15% fixed oil &
is obtained by solvent extraction methods.
Description
Golden yellow oil, difficult to bleach
Odour: Pleasant
Taste : Acrid
Not affected by temporary heating to 160ºC.
Insoluble in water, soluble in common fat solvents.
Saturated fatty acids (20-25%)
Unsaturated fatty acids as glycerides (80-85%)
Fatty acids are:
Oleic acid (40-45%)
Linoleic acid (30-40%)
Palmitic acid (12-18%)
Squalene
Antioxidant - Tocopherol
Gamma-oryzanol – protect & replenish skin
Emollient in the preparation of cosmetics.
Employed as preservative due to the presence of
antioxidants.
It is an edible oil & used in the preparation of
vegetable ghee.
Used in cosmetic baby formulations, hair & skin
products.
Sym: Theobroma oil, Cacao butter
BS: It is obtained from the roasted seeds (kernels) of
Theobroma cacao by expression; Family: Sterculiaceae.
GS: India, Central America, Brazil, Sri Lanka, West
Africa.
Cultivation: Refer Kokate
Cocoa seeds contains about 50% of cocoa butter.
Seeds are separated from the pods and are allowed to ferment wherein
the seeds change their colour from white to dark reddish brown due to
enzymatic reaction.
The fermentation process takes place at 30-40°C.
The process of fermentation carried out in tubes, boxes or in the
cavities made in the earth for 3-6 days.
After fermentation, the seeds are roasted at 100-140°C, which looses
water and acetic acid from the seeds and facilitates removal of seed
coat.
The seeds are then cooled immediately and are fed to nibbling machine
to remove the shells followed by winnowing.
The kernels are then fed to hot rollers which yield a pasty mass
containing cocoa butter. This is further purified to yield cocoa butter.
The cocoa shells are processed further to yield an alkaloid.
Appearance : Occurs as solid, brittle below 25°C.
Colour : Yellowish white
Odour : Faint, agreeable
Taste: Bland, Chocolate like
Density : 0.85-0.86
Melting point : Melts at body temperature (30-35°C)
Solubility: insoluble in water, slightly soluble in
alcohol, but soluble in ether, chloroform and benzene.
Cocoa butter consists of glycerides of
Stearic acid (34%)
Palmitic acid (25%)
Oleic acid (37%)
Small amount of arachidic & linoleic acid
The glycerides are present in the form of simple and mixed
glycerides.
Seed contains
Alkaloid – theobromin and caffeine
Fixed oil
Starch
Proteins
It is used as a base in ointment and suppositories
It is emollient for skin hence externally applied to
fissures of lips, hands and chapped skin.
Substitute
Mango kernel oil: solid fat at room temperature and
has a melting point of 35°C.