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 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.

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