LIPIDS

(fats, fixed oil & wax)

By:
Dr Rasha Saad
Department of Pharmaceutical Chemistry at MSU
 Introduction
• Lipids are the substances of animal or plant
origin and comprise of fixed oils, fats and
waxes.
• The basic function of oils and fats is storage
of energy, apart of their several uses in
medicines and industries.
• They are obtained by expression or
extraction methods.
 Fats and oils

Naturally occurring

Animal fat Vegetable oil Marine oil

lard sunflower oil cod liver oil

suet coconut oil whale oil
 Properties
1. Fixed oils are thick, yellow colored liquids (In case
of fixed oil) & semi solid (in case of fats, viscous
with characteristic odour.
2. They are non-volatile and cannot be distilled.
3. They do have food value & they can be converted
into soap by heating with alkali (Saponification).
4. They turn rancid on storage due to free acidity.
5. Fixed oils and fats are insoluble in water and ethyl
alcohol, but soluble in organic solvents.
6. Fats and oils are esters of glycerol.
7. Fat: - “ Fats are solid or semisolid at 15.50 to
16.50 C while fixed oils are liquid at this temp.
 Lipids chemistry
• Fats and oils are esters of glycerol
H
(three carbon trihydric alcohol)
H C OH
• The fatty acids of natural fats
H C OH have 4 to 24 carbon atoms ( and in
any even number).
H C OH

H • These fatty acids may be

saturated, monounsaturated,
Glycerol
polyunsaturated.
 Fats and oils
Fats and oils are built from an alcohol with three -O-H groups.

glycerol

Systematic name is propane-1,2,3-triol

 Triglyceride
O
H2C O C R
O
HC O C R'
O
H2C O C R''

• where R, R', and R" are long alkyl chains; the three
fatty acids RCOOH, R'COOH and R"COOH can be all
different, all the same, or only two the same.
 Fats and oils
Fats and oils are ESTERS of
glycerol and
long chain carboxylic acids
 Classification of Fats & oils
Vegetable oils and fats

Fats Nondrying Semi-drying Drying

Oil oil oil
Nutmeg butter Arachis Oil Castor oil Linseed oil
Kokum butter Almond oil Mustard oil Poppy oil
Coconut oil Olive oil Cottonseed oil Hemp oil

Animal oils and fats

Marine animals Terrestrial animal

Fats Fats Oil

Oil
Cod liver oil Butter Suet Lard oil
Bone tallow
Shark liver oil
 Lipids extraction

• Extraction of fixed oils and

fats
1. Vegetable origin –
expression
a. cold expression – cold-
pressed oil or virgin oil
b. hot expression – hot
pressed oil
2. Animal origin – steam with
or without pressure
 Waxes
• Waxes are esters of fatty
acid along with high
molecular weight
monohydric alcohols such as
cetyl alcohol, cholesterol,
melissyl alcohol.
• They are insoluble in water.
They are soluble in organic
solvents, solids. They have
characteristic waxy luster
they milt on heating. They
are unctuous to touch.
 Waxes
e. g.
a) Animal wax Bees
wax, spermaceti.
b) Vegetable wax Japan
wax, carnauba waxes.
c) Mineral Hard
paraffin ceresin

The difference between fats & waxes is

that, waxes can be saponified only by
alcoholic solution of alkali while fixed
oil can be saponified by aqueous as well
as alcoholic solution of alkali.
 Analytical parameters for Oils
and Fats
• USP specifications to determine
identity, purity, quality of fixed
oils(chemical constituents) of fatty
acids
1. Acid value (acid number)
2. Saponification value
3. Iodine value
4. melting point
5. Specific gravity
6. Refractive index
 Arachis oil
• Synonyms: Peanut oil, Groundnut oil
• Peanut oil: is an organic material oil
derived from peanuts, noted to have the
aroma and taste of its parent legume
• cultivated in tropical Africa, India, Brazil,
southern USA and Australia
• Method of preparation: From seeds of
Arachis hypogaea (Leguminosae) -
groundnut
• world’s 4th largest source of a fixed oil
• seeds contain 40-50% oil
• fruits shelled by a machine
• kernels difficult to express; crushed and
‘cooked’ at low pressure
• Chemical contituents:
• oleic acid ~ 60%
• linoleic acid 24%
• palmitic acid 9%
• arachidonic acid

• GU3, GSU2 like olive oil

• Chemical test: UV → blue fluorescence

• acid and saponification values similar
to olive oil
• Uses: intramuscular injection,
liniments, plasters, and soap
• if fatty acids are separated
(hydrolysis) the presence of
arachidonic acid gives a melting point
>710C
– used as a test for adulteration of olive oil
 Castor oil

Synonym: Tangan - tangan

Origin: fixed oil obtained from the ripe seed of Ricinus
communis (Euphorbiaceae)
Constituents:
contains 45 - 55% fixed oil(mixture of 85% triricinoleoyl
glycerol, diricinoleoylglycerol and acyl group: oleic, linoleic,
dihydroxystearic and saturated fatty acids (palmitic or stearic),
20% protein substances :globulin, albumin, nucleo -
albumin, glycoprotein;
- ricin - toxic lectin or hemagglutin
- alkaloid - ricinine
 Castor oil

Use:
stimulant cathartic
externally: emollient, plasticizer(flexible
collodion)
commercially: manufacture of soap
lubricant (internal combustion engines)
- hydrogenated castor oil - stiffening agent in
pharmaceutical preparations
 Castor oil
Allied drugs of castor oil
1. Croton oil – Croton tiglium (Euphorbiaceae)
- crotin; ingested violent cathartic
2. Physic nut/purging nut
- Jatropha curcas (Euphorbiaceae)
- curcin
- powerful purgative
3. Prayer beads – Abrus precatorius (Fabaceae)
- abrin, alkaloids (abrine, hyaphorine,
precatorine
- employed as contraceptive
 Castor oil
• Composition of seeds

• Preparation of medicinal castor oil

• Description

• Chemical constituents

• Identification

• uses
 Olive oil

Synonym: Sweet oil, salad oil

Origin: fixed oil obtained from the ripe fruit of Olea
europea (Oleaceae)
- oil is marketed in several grades
1. Virgin oil - obtained from gently pressing
peeled pulp free from endocarp
2. 1st grade - crushed pulp that is less pressed
3. 2nd grade - crushed pulp that is more pressed
4. Inferior grade - crushed pulp after the 2
grades extracted using water or CS2
(sulfur olive oil)
 Olive oil
5. Low grade tournant oil - refused decomposed
olives and allowed to ferment, contains
abundant fatty acids
Constituents: fatty acids:
palmitic, stearic, oleic, linoleic

Use: pharmaceutical aid

- setting retardant (dental cements)
- prep. Of soaps, plasters, liniment
- salad oil and cooking oil
 Coca butter
• Synonym:Theobroma oil; Caco butter.
• Bio source: roasted seeds of Theoproma
cacao L.

Cultivation of Cocoa:
 1000 m above see level
 Good quality soil
 Sufficient organic matter
 Its sun loving
 Cocoa plants survive for 60 to 70 years and
start bearing fruits after three years of
planting.
Preparation of Coca butter

• Cocoa seeds contain about 50% of

cocoa butter.
• The seeds are separated from the pods
→ ferment in tubes colour ( white to
brown) → roast the seeds in 100-
140⁰C (remove seed coat, looses of
water and acetic acid)→ cool
immediately → fed to nibbling machine
to remove the shells → winnowing →
kernels fed to hot rollers → pasty
mass → purification → cocoa butter
 Coca butter
• Description: Cocoa butter yellow- white
solid, pleasant chocolate odour and taste.
• Chemical constituents: glycerides of
stearic, palmitic, oleic acids and small
amounts of arachidic and linoleic acid.
Uses:
 Base for suppositories and ointments,
manufacture of creams and toilet soap
 Yellow bees wax
Synonym: yellow beeswax, Cera de Abejas, Pagket
(Tag)
Origin: purified wax from the honeycomb of the
bee, Apis mellifera (Apidae)
Constituents:
- wax consists of alkyl esters of fatty and wax
acids (myricyl palmitate, myricyl cerotate,
myricyl hypogaeate and ceryl 2 – hydroxy -
palmitate
- minor constituents:moisture, pollen,
propolis (bee glue)
 Yellow bees wax

Use: stiffening agent

- ingredient in yellow ointment
- base for cerates and plasters
- commercial: manufacture of candles and
cosmetics, ingredient of some polishes
Note:
wax is prepared after removal of honey by
melting the comb under water (honey dissolves in
water and solid impurities sink) strained and the
wax is allowed to solidify in moulds
 Grape Seed Oil
• Grape Seed (Vitis Vinifera), also known as Red Wine
Extract, is an important source of one of nature’s
most potent antioxidants – Proanthocyanidins (also
called OPCs for Oligomeric Procyanidins, or PCOs for
Procyanidolic Oligomers).
• These nutritionally valuable substances have been
utilized to treat deteriorating diseases and
conditions with great success.
• Grape Seed helps vitamin C enter the body’s cells,
thus strengthening the cell membranes, and
protecting the cells from oxidative damage.
Research has shown that Proanthocyanidins (which
are bioflavonoids) are anti-inflammatory,
antihistamine, and antiallergenic, and are major
free radical scavengers.
 Grape Seed Oil
Chemistry
95% Proanthocyanidins – phenolic compounds in the form of polymers or
oligomers, built of flavan-3-ol units, such as catechin, epicatechin,
gallocatechin, epigallocatechin, afzelechin and epiafzelechin.

Botanical Description
Grown in warm, temperate regions of the world. It produces clusters of pale
green flowers. The fruit has green, yellow or reddish-purple skins and two to
four seeds inside the pulpy flesh.
Indicated for
Ageing, allergies, arm and leg numbness or tingling, arteriosclerosis, arthritis,
allergies, blood vessel damage, cataracts, cancer prevention, diabetes, eczema,
endemtriosis, eye-strain, fibromyalgia, gum disease, haemorrhoids, hair
problems, hardening of arteries, hayfever, heart disease prevention, high blood
pressure, high cholesterol, HIV, hives, impotence, improving circulation, leg
cramps,
Marine Oil
 Krill oil
• Krill oil is made from a species of krill
[Euphausia superba]. Two of the most
important nutrients in krill oil are:
(1) omega-3 fatty acids similar to those of
fish oil and
(2) Phospholipid-derived fatty acids (PLFA),
mainly phosphatidylcholine (alternatively
referred to as marine lecithin).
• Also, antioxidant experimental egg
products with krill oil likely contained
astaxanthin, a natural antioxidant.
• The fatty acid composition in the
phospholipids in krill oil has been
described in two papers.
• Several studies have shown toxic residues
in Antarctic krill and fish
Extraction of Krill oil
 Shark liver oil

• Synonym: oleum Selachoids

• Origin: fresh and carefully preserved livers
of various specious of the shark,
• Methods of preparation: The livers are
cleaned and minced mass is taken to boiling
point, then treat it with dehydrating agent to
remove traces of water. Centrifuge are used
to separate suspended materials in oil.
 Shark liver oil
Description:
Colour – Pale yellow to brown
Odour - Fishy but not rancid
Taste - Bland or fishy
Solubility: insoluble in water, soluble in ether,
chloroform.

Chemical constituents:
Vit A. + omega – 3- fatty acid + sequalene.
 Cod liver oil
Origin: partially destearinated
fixed oil obtained from the
fresh livers of Gadus morrhua /
G. callarias (Gadidae)
Constituents:
fixed oil contains glyceryl esters
of unsaturated and saturated
fatty acids
Use:
- sterile solution of sodium morrhuate injection -
sclerosing agent
- dietary supplement
- formulating oleovitamin A and D products
 Cod liver oil
Uses:
- topical emollient
- prevent and cure rickets
(undeveloped condition)
- Relief rheumatic pains, joints and
muscle stiffness
- reduce blood cholesterol
 Cod liver oil exteaction
(Dry Rendering)
 The dry rendering process, which is commonly used to
prepare animal proteins and fats, is not normally used in
the manufacture of fishmeal and oil.
 However the process is used with catfish by-products.
In this process the raw material is "cooked" to remove
the water (essentially the drying process in the fishmeal
wet rendering process.
 The resultant dry cake is then pressed to remove any
oil. Because the water has been removed, the lipid
fraction can contain high levels of phospholipids.
 The phospholipids normally hydrate in the wet rendering
process and are recovered with the water fraction.
 Cod liver oil exteaction
(Dry Rendering)
• In the dry rendering process, they
are not hydrated and therefore
remain dissolved in the lipid or oil
fraction.
• Since there is interest in the fish
phospholipids, it is possible to
produce a PL fraction by hydrating
the oil (also called degumming).
• The dry rendering process is shown
in Figure 5. Further embodiments of
this process, which is used in the
processing of animal protein by-
products have been reviewed by
Bimbo