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LIPIDS

Chapter Outline
Introduction
Detailed study of;
Fixed Oils: Castor oil, Cotton seed oil, Olive oil, Peanut oil, Sun flower oil, Corn oil, Coconut
oil, Almond oil, Linseed oil, Mustard oil, Sesame oil, Soybean oil
Fats and Related Compounds: Theobroma oil, Lanolin
Waxes: Bees wax, Carnauba wax, Spermaceti, Jojoba oil

Introduction

Long chain fatty acids (Saturated)


Caproic acid C = 06 CH3 (CH2)4 COOH
Caproylic acid C = 08 CH3 (CH2)6 COOH
Capric acid C = 10 CH3 (CH2)8 COOH
Lauric acid C = 12 CH3 (CH2)10 COOH
Myristic acid C = 14 CH3 (CH2)12 COOH
Palmitic acid C = 16 CH3 (CH2)14 COOH
Stearic acid C = 18 CH3 (CH2)16 COOH
Arachidic acid C = 20 CH3 (CH2)18 COOH

Long chain fatty acids (Un-saturated) (C = 18)


Oleic acid CH3 (CH2)7 CH = 9CH (CH2)7 COOH
Linoleic acid CH3 (CH2)4 CH = 12CH CH2 CH = 9CH (CH2)7 COOH
Linolenic acid CH3 CH2 CH = 15CH CH2 CH = 12CH CH2 CH = 9CH (CH2)7 COOH
Ricinoleic acid CH3 (CH2)5 12CH CH2 CH = 9CH (CH2)7 COOH
OH

Lipids (fixed oils, fats and waxes) are esters of long chain fatty acids and alcohols, or of closely related
derivatives

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Fixed oils
These are the triglycerides of long chain unsaturated fatty acids
Examples: Peanut oil, Coconut oil, Castor oil etc.
CH2 OH
CH2 OH CH3 (CH2)7 CH = CH (CH2)7 COOH
+
CH2 OH Oleic acid (3 molecules)
Glycerol -3H2O

CH2 O CO (CH2)7 CH = CH (CH2)7 CH3


CH2 O CO (CH2)7 CH = CH (CH2)7 CH3
CH2 O CO (CH2)7 CH = CH (CH2)7 CH3
Triolein

Fats
These are the triglycerides of long chain saturated fatty acids
Examples: Lanolin, Cocao butter etc.

CH2 OH CH2 O CO (CH2)16 CH3


CH3 (CH2)16 COOH
CH2 OH CH2 O CO (CH2)16 CH3
+ Stearic acid -3H2O
CH2 OH CH2 O CO (CH2)16 CH3
(3 molecules)
Glycerol Tristearin

Waxes
These are the esters of long chain, higher molecular weight monohydric primary alcohol with long chain
fatty acid which can be saturated as well as unsaturated
Examples: Bees wax, Carnauba wax, Spermaceti etc.

C15H31 COOH C16H33 OH C15H31 CO O C16H33


+ -H2O
Palmitic acid Cetyl alcohol Cetyl palmitate

Acid value
It is the number of mg of KOH required to neutralize free fatty acids in 1 g of fixed oil
Every fixed oil has its own acid value
This test is used to determine that to which extent the hydrolysis has taken pace

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Saponification value
It is the number of mg of KOH required to neutralize free fatty acids and to hydrolyse the esters in 1 g of
fixed oil
Ester value
It is the number of mg of KOH required to hydrolyse the esters in 1 g of fixed oil
Ester value = Saponification value Acid value
Iodine value
It is the number of g of iodine absorbed by 100 g of fixed oil
This test is used to determine the unsaturation in fixed oils
Acetyl value
It is the number of mg of KOH required to neutralize acetic acid freed from 1 g of acetylated fixed oil
This test is used to determine the number of OH group in fixed oil

Fixed Oils: Castor Oil, Cotton Seed Oil, Olive Oil, Peanut Oil, Sun Flower Oil, Corn Oil, Coconut
Oil, Almond Oil, Linseed Oil, Mustard Oil, Sesame Oil, Soybean Oil
Castor oil (Castor )

Castor oil is a fixed oil obtained from the ripe seed of Ricinus communis (Fam. Euphorbiaceae)
Preparation of castor oil
Seeds are passed through a decorticator to remove the testa
Kernels are subjected to pressure
Oil obtained is steamed to destroy albumins
Filtered and bleached
Cold pressed oil (using hydraulic pressure): Yield is 60%. It is of light colored and good grade
Solvent extracted (remainder part of oil): Darker, low grade oil
Properties of castor oil
Pale yellowish or almost colorless, transparent, viscid liquid
Faint, mild odor
Bland, characteristic taste
Constituents of castor seeds
Fixed oil (45-55%)
Protein (20%) [globulin, albumin, nucleoalbumin, glycoprotein]
Ricin (a toxic substance)
Alkaloid (ricinine)
Lipases

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Composition of castor oil
Mixture of triglycerides;
85% of which is triricinolein
Remainder consist of diricinolein, with a third acyl group representing either oleic, linoleic, dihydroxy
stearic acid or a saturated fatty acid like palmitic acid
In duodenum, triricinolein is hydrolysed by lipase; ricin oleic acid is released
Ricin oleic acid exerts a cathartic effect

CH2 O CO (CH2)7 CH = CH CH2 CH (CH2)5 CH3


OH
CH2 O CO (CH2)7 CH = CH CH2 CH (CH2)5 CH3 Triricinolein
OH
CH2 O CO (CH2)7 CH = CH CH2 CH (CH2)5 CH3
OH
CH2 O CO (CH2)14 CH3

CH2 O CO (CH2)7 CH = CH CH2 CH (CH2)5 CH3 Palmito diricinolein


OH
CH2 O CO (CH2)7 CH = CH CH2 CH (CH2)5 CH3
OH
Pharmacology and biological activities
Castor oil is cathartic, act on small intestine, produces purgation after 2-8 hour of ingestion
Usual dose is 15 ml
Larger doses produce beside purgation, nausea, vomiting and colic
Has emollient properties on skin and is soothing to eyes
Facilitates the absorption of oil soluble anthelmintic and never be used with them
Castor seed is very toxic due to ricin. It is absent in castor oil
Its one seed can expire a child of 6-7 years
The allergen present in seed can cause serious symptoms i.e. skin rashes, asthma, hay fever in certain
individuals
Pharmaceutical and cosmetic uses
Used as cathartic in constipation, food poisoning, bowel evacuation before x-ray examination
Used as solvent or vehicle in some parenteral or ophthalmic preparations
As ingredient in ointment, cream, lotion, suppositories
Used as a component of protective coating in tablets

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In folk medicine it was used in constipation, abscesses, as oral contraceptive

Cotton seed oil (Cotton )

It is the refined fixed oil obtained from seeds of cultivated plants of various varieties of Gossypium
hirsutum or other species of Gossypium (Fam. Malvaceae)
Preparation
After ginning off the fibers, the cotton seeds are decorticated and cleaned of hulls
The kernels are steamed and pressed at about 1500 lb pressure to yield about 30% of oil
The oil thus obtained is turbid and reddish in color
It is refined b filtering, decolorizing and winter chilling, which removes the stearin
Properties
Pale yellow oily liquid
Almost odorless and has a bland taste
Composition
Consist of a mixture of triglycerides with component acids of the following approximate composition;
Linoleic acid (45%)
Oleic acid (30%)
Palmitic acid (20%) Structures (Page No. 1)
Myristic acid (3%)
Stearic acid and arachidic acid (1%)
Uses
Used as solvent in injections
In manufacture of soap

Olive oil / Sweet oil (Olive )

It is a fixed oil obtained by expression from ripe fruit of Olea europaea (Fam. Oleaceae)
Preparation of olive oil
Olives (olive fruit) are gathered from November to April
Handpicked olives are used
Oil is obtained promptly before decomposition produces fatty acids
Olive oil is offered in the market with several grades of purity
Virgin oil: Obtained by gently pressing the peeled pulp, free from endocarp
First and second grades of edible oil: Obtained from crushed pulp, the first grade with little pressure and
the second grade from the same pulp but with greater pressure
Technical oil: Obtained by treating the marc with hot water, and pressing again; or marc is treated with
carbon disulfide (as solvent) to get oil of inferior quality
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Tournant oil: Obtained from fallen, decomposed and refused olives. This oil contains large amounts of
free fatty acids
Properties of olive oil
Pale yellow or light greenish yellow oily liquid
Odor is slight but characteristic
Taste is bland to faintly acrid
Miscible with carbon disulfide, ether and chloroform
Slightly soluble in alcohol
Specific gravity is 0.912-0.915
Composition of olive oil
Olive oil from different sources differs somewhat in composition. It may be due to use of different varieties
of olives or due to climate differences
Turkish variety contains;
Oleic acid (75%)
Palmitic acid (10%) Structures (Page No. 1)
Linoleic acid (9%)
Stearic acid, myristic acid, hexadecenoic acid, arachidic acid (in lesser amount)
Italian variety contains;
Oleic acid (65%)
Palmitic acid (15%)
Linoleic acid (15%)
Stearic acid, myristic acid, hexadecenoic acid, arachidic acid (in lesser amount)
Uses
Used as a pharmaceutic aid
Setting retardant for dental cements
In the preparation of soaps, plasters and liniments
Demulcent
Emollient
Laxative
Nutrient
Widely used as salad oil

Peanut oil (Peanut )

It is a refined fixed oil obtained from seed kernels of one or more cultivated varieties of Arachis hypogaea
(Fam. Leguminosae)

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Properties of peanut oil
Colorless or a yellowish liquid
Slightly nutlike odor
Bland taste
Composition of peanut oil
Consist of a mixture of triglycerides with component acids of the following approximate composition;
Oleic acid (50-65%)
Linoleic acid (18-30%) Structures (Page No. 1)
Palmitic acid (10%)
Myristic acid, behenic acid, lignoceric acid (10-12% collectively)
Uses
As a pharmaceutic aid
Used in food items
As lubricant
Used to make soaps
As vehicle in IM injections

Sunflower oil (Sunflower )

It is the fixed oil obtained from the seeds of cultivated varieties of Helianthus annus (Fam.
Asteraceae/Compositae)
Composition of sunflower oil
The oil consists of mixture of glycosides that are rich in unsaturated acids
It contains;
Linoleic acid (66%)
Linolenic acid (44-75%) Structures (Page No. 1)
Oleic acid (23%)
Uses
Used as alternative to corn oil and safflower oil for cooking purpose
As an ingredient in a number of specialty dietary supplements

Corn oil (Corn )

It is the refined oil obtained from the embryo of Zea mays (Fam. Gramineae)
Preparation
The oil rich embryos (germs) are separated by a flotation process during the preparation of corn starch
Embryos are washed, are free of starch and gluten, and are subjected to pressure and heat to express the
oil
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The germ oil cake that remains is ground and sold as cattle feed
The crude oil is clarified by filtering and setting, refined by removing the fatty acids, refrigerating, filtering
and sterilizing
Properties
Clear light yellow oily liquid
Has a faint characteristic odor and taste
Constituents
Consist of a mixture of triglycerides with component acids of the following approximate composition;
Linoleic acid (50%)
Oleic acid (37%)
Palmitic acid (10%) Structures (Page No. 1)
Stearic acid (3%)
Uses
Solvent for injections
Solvent for irradiated ergosterol
An edible oil, used in food
An emulsion containing 67% of corn oil is used as high caloric dietary supplement
Used as an ingredient in a number of commination products for oral administration
When hydrogenated, oil becomes semisolid and used as margarine
Coconut oil
It is a fixed oil obtained by expression or extraction from seed kernels of Cocos nucifera (Fam. Palmae)
Constituents
It consists of a mixture of glycerides in which 80-85% of acids are saturated
Contains lauric acid (50%), myristic acid (20%)
Also contains glycerides of caproylic acid and capric acid
Uses
It yields high quality soaps and shampoos
Used as an ingredient in a number of commination products for oral administration

Almond oil (Almond )

It is a fixed oil obtained by expression from the seed kernels of different varieties of Prunus amygdalus
(Fam. Rosaceae)
Sweet almond: From Prunus amygdalus var. dulcis
Bitter almond: From Prunus amygdalus var. amara
Constituents of almond
Both varieties of almonds contain;
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Fixed oil (40-55%)
Proteins (21%)
Mucilage
Emulsin
Amygdalin (cyanophore glycoside) [Present only in bitter almond]
Preparation of almond oil and bitter almond oil
Seeds (bitter and sweet almonds) are grinded Expressed in canvass bags between slightly heated iron
plates Oil is clarified by filtration (it is a fixed oil, called almond oil)
Cake of bitter almonds (left after expressing) Macerated with water for some hours
Hydrolysis of amygdalin occurs Benzaldehyde and HCN are formed (It is a volatile oil, called bitter
almond oil)
Bitter almond oil contains benzaldehyde and HCN
Purified bitter almond oil consists mainly of benzaldehyde (HCN removed)
Uses
Emollient
Ingredient in cosmetics

Linseed oil / Flax seed oil (Linseed )

It is the fixed oil obtained from dried ripe seeds of Linum usitatissimum (Fam. Linaceae)
Properties
Yellow liquid having a distinct odor and a disagreeable taste
When exposed to air, it gradually thickens and darkens in color
Composition
Consist of a mixture of triglycerides with component acids of the following approximate composition;
Linolenic acid (52%)
Oleic acid (19%)
Linoleic acid (19%) Structures (Page No. 1)
Stearic acid (7%)
Palmitic acid (6%)
Uses
Not suitable for edible purposes (due to high content of linolenic acid)
It is an important drying oil in paint and varnish industry

Mustard oil / Rapeseed oil (Mustard )

It is the fixed oil obtained from the seeds of Brassica compestris, B. juncea, B. napus (Fam. Brassicaceae)
Before 1970, commercial rapeseed oil contained upto 50% erucic acid, which has anti-nutritional property
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But now such verities have been developed which contain 0.2-2% erucic acid, and called as canola oil
Properties of canola oil
Has bland taste
Resists clouding at refrigeration temperature
Composition
Consist of a mixture of triglycerides with component acids of the following approximate composition;
Oleic acid (55-63%)
Linoleic acid (20-31%)
Palmitic acid (4-5%) Structures (Page No. 1)
Stearic acid (1-2%)
Uses
Used as salad oil
As frying oil
As margarine
Has specific industrial use

Sesame oil (Sesame )

It is the refined fixed oil obtained from the seeds of one or more cultivated varieties of Sesamum indicum
(Fam. Pedaliaceae)
Properties of oil
Pale yellow oily liquid
Almost odorless and has bland taste
Composition of seed
Fixed oil (45-55%)
Protein (22%)
Mucilage (4%)
Composition of oil
Consist of a mixture of triglycerides with component acids of the following approximate composition;
Oleic acid (43%)
Linoleic acid (43%)
Palmitic acid (9%) Structures (Page No. 1)
Stearic acid (4%)
The stability of oil is due to phenolic constituent sesamol, which is the hydrolytic product of a lignin
sesamolin
Uses
Pharmaceutic aid
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Solvent in IM injections
Nutritive
Laxative
Demulcent
Emollient
Sesamolin is an effective synergism for pyrethrum insecticides

Soybean oil (Soybean )

It is the refined fixed oil obtained from the ripe seeds of Glycine soja (Fam. Leguminosae)
The oil is obtained by expression and the yield seldom exceeds 10%
Composition of seeds
Protein (50%)
Carbohydrate (35%)
Fixed oil (20%)
Enzyme (urease)
Composition of oil
Consist of a mixture of triglycerides with component acids of the following approximate composition;
Linoleic acid (50%)
Oleic acid (30%) Structures (Page No. 1)
Linolenic acid (7%)
Palmitic acid and stearic acid (14%)
Uses
As in ingredient in parenteral nutrient
As a source of lecithin
Lecithin is an ingredient in a number of proprietary products which are used to control deranged lipid and
cholesterol metabolism
As a source of stigmasterol
Stigmasterol is obtained from lipid fraction of soybean. It is used for precursor for synthesis of steroidal
hormones
Oil is extensively is used in the manufacture of varnish and insulators
Soybean cake is used as food for livestock. It contains protein, oil, K and S
It can also be used for detection of urea nitrogen in drug serum by enzymatic action of urease

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Fats and Related Compounds: Theobroma Oil and Lanolin

Theobroma oil / Cacao butter


It is liquid physically, so called as oil
Chemically it is fat, because it contains high amount of saturated fatty acids
Saturated fatty acids: Present on 1,3 position of glycerol
Un-saturated fatty acids: Present on 2 position of glycerol
Theobroma oil
It is the fat obtained from roasted seeds of Theobroma cacao (Fam. Sterculiaceae)
Properties of oil
Yellowish white solid
Has a faint agreeable odor
Bland chocolate like taste
Melts between 30-35 C
Composition of seeds
Fixed oil (30-35%)
Starch (15%)
Protein (15%)
Theobromine (1-4%)
Caffeine (0.07-0.36%)
Composition of oil
Consist of a mixture of triglycerides with component acids of the following approximate composition;
Oleic acid (37%)
Stearic acid (34%)
Palmitic acid (26%) Structures (Page No. 1)
Linoleic acid (2%)
Oleopalmitostearin
Oleodipalmitin

CH2 O CO (CH2)14 CH3


CH2 O CO (CH2)7 CH = CH (CH2)7 CH3 Oleopalmitostearin
CH2 O CO (CH2)16 CH3

CH2 O CO (CH2)14 CH3


CH2 O CO (CH2)7 CH = CH (CH2)7 CH3 Oleodipalmitin
CH2 O CO (CH2)14 CH3
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Uses
Used as suppository base because it melts between 30-35 C
Lanolin / Wool fat
It is the purified fat like substance obtained from wool of sheep Ovis aries (Fam. Bovidae)
It contains 25-30% water, so commonly known as hydrous wool fat
Properties
Yellowish white ointment like mass
Has slight characteristic odor
Composition
Cholesterol and isocholesterol (chief constituents)
Other constituents: Esters of lanopalmitic acid, lanoceric acid, carnaubic acid, oleic acid, myristic acid and
other fatty acids
Uses
Used as water absorbable base of ointment
Used in many skin creams and cosmetics
Used for external preparations
Anhydrous wool fat (containing less than 0.25% water) has emollient properties

Waxes: Bees Wax, Carnauba Wax, Spermaceti, Jojoba Oil

Bees wax
Yellow wax or beeswax is the purified wax obtained from the honey comb of the bee Apis mellifera (Fam.
Apidae)
White wax is the bleached and purified wax obtained from the honey comb of the bee Apis mellifera (Fam.
Apidae)
Preparation
The honey comb is melted in water, cooled, re-melted, finally strained and allowed to harden in molds
Bleaching is done to prepare white wax
Properties
Yellow to greyish brown solid
Has an agreeable honey like odor
Faint characteristic taste
When cold, beeswax is somewhat brittle and exhibits a dull, granular, non-crystalline fracture
Composition
It consist principally of alkyl esters of fatty and wax acid (about 72%), chiefly myricyl palmitate
Free wax acids (about 14%), especially cerotic acid and its homologs
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Hydrocarbons (12%)
Moisture, pollen. propolis (minor constituents)
Uses
Stiffening agent
Ingredient in yellow ointment
Base for cerates and plasters
Commercially, it is contained in a number of polishes
White was: Used in ointments and in cold creams
Carnauba wax
It is obtained from the leaves of Copernicia prunifera (Fam. Palmae)
Composition
It consist principally of alkyl esters of wax acid (about 80%), chiefly myricyl cerotate
Free monohydric alcohols (10%)
A lactone
Resin
Uses
In the manufacture of;
Candles
Wax varnishes
Leather and furniture polishes
In place of beeswax
Spermaceti
It is a waxy substance obtained from the head of the sperm whale Physeter macrocephalus (Fam.
Physeteridae)
The sperm whale is an endangered species and spermaceti is no longer available
Efforts to find a substitute for spermaceti has led to the use of a synthetic spermaceti
Composition
Consist of a mixture of hexadecyl esters of fatty acids;
Hexadecyl dodecanoate (Cetyl laurate)
Hexadecyl tetradecanoate (Cetyl myristate)
Hexadecyl hexadecanoate (Cetyl palmitate)
Hexadecyl octadecanoate (Cetyl stearate)
Comprised at least 85% of total esters
C11H23 CO O C16H33 (Cetyl laurate) C15H31 CO O C16H33 (Cetyl palmitate)

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Uses
Emollient
In cold creams
In cosmetics
Jojoba oil
It is a liquid wax expressed from seeds of Simmondsia chinensis (Fam. Buxaceae)
Composition
Jojoba seeds contain 45-55% of an ester mixture (not triglycerides) that is liquid at ambient temperature
Major components identified upon hydrolysis of the mixture are;
Eicosenoic acid (35%) [a C20 unsaturated acid]
Eicosenol (22%) [a C20 unsaturated alcohol]
Docosenol (21%) [a C22 unsaturated alcohol]
Hydrogenation of oil yields a crystalline wax having the appearance and properties of spermaceti
CH3 (CH2)7 CH = 11CH (CH2)9 COOH 11-Eicosenoic acid
Uses
Emollient
Agents of pharmaceutic necessity
Reed Book (not notes) if you want to be a Good Professional

Hafiz Abdul Khaliq hakhaliq@yahoo.com pharmacist.hak@gmail.com

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