Course Code: PHA 040 (Pharmacognosy and Plant Chemistry)

Student Activity Sheet

SAS #6

Name: ____________________________________________________________ Class number: _______

Section: ____________ Schedule: ____________________________________ Date: ______________

Lesson title: Lipids Materials:

1.Student Activity sheet
Lesson Objectives: 2. Pen
At the end of this module, you are expected to;
1. Identify the Pharmaceutical and pharmacological uses of lipid- References:
related Crude drugs -Shah, biren. (latest ed.). Textbook of
2. Identify the sources of the lipid-related crude drugs pharmacognosy and phytochemistry.
India : elsevier.
1. -Tyler, varro. Pharmacognosy, , phila. :
lea & febiger, latest ed.

Productivity Tip:
“We can achieve anything we desire if we give ourselves the time and the right resources to learn, but these are
worthless without focus and determination to be successful. “ – R. Peck

A. LESSON PREVIEW/REVIEW

Introduction (5 mins)

Lipids (fixed oils, fats, and waxes) are esters of long-chain fatty acids and alcohols, or of closely related
derivatives)The chief difference between these substances is the type of alcohol; in fixed oils and fats, glycerol
combines with the fatty acids; in waxes, the alcohol has a higher molecular weight, e.g., cetvl alcohol. Fats and
fixed oils are obtained from either plants (olive oil, peanut oil) or animals (lard). Their primary function is food
(energy) storage. The fixed oils and fats are important products used pharmaceutically, industrially, and
nutritionally. Waxes may also he of plant or animal origin. Many drugs contain fixed oils and fats as their principal
constituents; the fixed oils and fats are often separated from the crude vegetable drugs (by expression) or the
crude animal drugs (by rendering or extraction) and are employed as drugs in the refined state. Fixed oils and fats
differ only as to melting point; those that are liquid at normal temperatures are known as fatty or fixed oils,
whereas those that are semisolid or solid at ordinary temperatures are known as fats. Although most vegetable
oils are liquid at ordinary temperatures and most animal fats are solid, there are notable exceptions, such as
cocoa butter, which is a solid vegetable oil, and cod liver oil, which is a liquid animal fat.

Figure 1- Primary composition of a lipid (Glycerol and a Fatty Acid)

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 Course Code: PHA 040 (Pharmacognosy and Plant Chemistry)
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Activity 1: What I Know Chart, part 1 (5 mins)

What I Know Questions: What I Learned (Activity 4)

1. What is the difference between fats
and Fixed oils
2. What is a an example of a Solid
Fixed oil?
3. Is there a connection between
Lipids and Vitamins?

B.MAIN LESSON

Activity 2: Content Notes (90 mins)

The lipids are a large and diverse group of possible. Since the fatty acids in these triglycerides
naturally occurring organic compounds that are contain the maximum possible amount of
related by their solubility in nonpolar organic hydrogens, these would be called saturated fats.
solvents (e.g. ether, chloroform, acetone, and The hydrocarbon chains in these fatty acids are,
benzene) and are generally insoluble in water. There thus, fairly straight and can pack closely together,
is great structural variety among the lipids and making these fats solid at room temperature. Oils,
comprise of fixed oils, fats, and waxes. The lipids of mostly from plant sources, have some double bonds
physiological importance for humans have the between some of the carbons in the hydrocarbon
following major functions: tail, causing bends or ‘kinks’ in the shape of the
1. They serve as structural components of molecules. Because some of the carbons share
biological membranes. double bonds, they are not bonded to as many
2. They provide energy reserves, predominantly hydrogens as they could if they weren’t double
in the form of triacylglycerols. bonded to each other. Therefore these oils are
3. Both lipids and lipid derivatives serve as called unsaturated fats. Because of the kinks in the
vitamins and hormones. hydrocarbon tails, unsaturated fats can’t pack as
4. Lipophilic bile acids aid in lipid solubilization. closely together, making them liquid at room
Fixed oils and fats are obtained from plants or temperature.
animal. They are rich in calories and in plant source,
they are present mostly in the seeds, as reserve
substances and in animals they are present in
subcutaneous and retroperitoneal tissues. They
differ only according to their melting point and
chemically they belong to the same group. If a
substance is liquid at 15.5–16.5°C it is called fixed
oil and solid or semisolid at the above temperature,
it is called fat. They are made from two kinds of
molecules: glycerol (a type of alcohol with a hydroxyl
group on each of its three carbons) and three fatty
acids joined by dehydration synthesis. Since there
are three fatty acids attached, these are known as
triglycerides. These fatty acids may be saturated,
monounsaturated or polyunsaturated. The terms
saturated, mono-unsaturated, and poly-unsaturated
refer to the number of hydrogens attached to the
hydrocarbon tails of the fatty acids as compared to
the number of double bonds between carbon atoms
in the tail. Fats, which are mostly from animal
sources, have all single bonds between the carbons
in their fatty acid tails, thus all the carbons are also Example of saturated and unsaturated Fatty acid
bonded to the maximum number of hydrogens

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Fixed oils and fats are insoluble in water and peroxide value to rancidity. High peroxide values are a
alcohol and are soluble in lipid solvents like light definite indication of rancid fat, but moderate values may
petroleum, ether, chloroform, and benzene. The only be the result of the depletion of peroxides after reaching
exception in this solubility is castor oil which is soluble in high concentrations.
alcohol because of its hydroxyl group of ricinoleic acid. Waxes are esters of long-chain fatty acids and
They float in water since their specific gravity is less than alcohols. The fatty acids are the same in wax and fats,
one. They produce a permanent translucent stain on the but the difference is saponification. Waxes are
paper and are called fixed oils. Fixed oils and fats cannot saponified only by alcoholic alkali but the fats may be
be distilled without their decomposition. Since the saponified either by alcoholic alkali or by aqueous alkali.
Physical characteristics of the lipids are almost similar to Along with fatty acids, it also contains monohydroxy
each other, thus they need to be assayed, and alcohols of high molecular weight especially cetyl
According to the United States Pharmacopeia, the alcohol, melissyl alcohol, and myricyl alcohol.
determination of. …. Sometimes cholesterol or phytosterols are also present.
1. Iodine value: The iodine value is the mass of As such they are not suitable as food because
iodine in grams that is consumed by 100 g of fats or oil. hydrolyzing enzymes of wax are not present in the
An iodine solution is violet in color and any chemical system. Waxes are widely distributed in nature. The
group in the substance that reacts with iodine will make leaves and fruits of many plants have waxy coatings,
the color disappear at a precise concentration. The which may protect them from dehydration and small
amount of iodine solution thus required to keep the predators. The feathers of birds and the fur of some
solution violet is a measure of the amount of iodine- animals have similar coatings which serve as water
sensitive reactive groups. It is a measure of the extent of repellent. Spermaceti, beeswax, carnuba wax, etc. are
unsaturation and the higher the iodine value, the more examples of waxes.
chance for rancidity.
2. Saponification value: The saponification + LIPIDS
value is the number of milligrams of potassium hydroxide Coconut oil (Coconut oil, coconut butter, copra
required to saponify 1 g of fat under the conditions oil) - Is the fixed oil obtained by expression or extraction
specified. It is a measure of the average molecular from the seed kernel of the coconut palm Cocos
weight of all the fatty acids present. nucifera. In temperate region below 23°C coconut oil is
3. Hydroxyl value: The hydroxyl value is the concrete oil. Coconut butter is a white or pearl white
number of mg of potassium hydroxide (KOH) required to unctuous mass, odourless or with peculiar coconut
neutralize acetic acid combined to hydroxyl groups, odour and bland taste. Its melting point is 23°C to 26°C.
when 1 g of a sample is acetylated. It is soluble in two volumes of alcohol at 60°C but highly
4. Ester value: The ester value is the number of soluble in chloroform, ether and carbon disulphide. The
mg of potassium hydroxide (KOH) required to saponify oil readily becomes rancid on exposure to air. The
the ester contained in 1 g of a sample. coconut oil has the highest saponification value, 250–
5. Unsaponifiable matter: The principle is the 264 and the lowest iodine value, 7–10 among the
saponification of the fat or oil by boiling under reflux with vegetable oils in common use. Coconut obtained from
an ethanolic potassium hydroxide solution. the hard, dried endocarp consists of a mixture of
Unsaponifiable matter is then extracted from the soap triglycerides of saturated fatty acids. The oil contains
solution by diethyl ether. The solvent is evaporated and about 95% of saturated fatty acids with 8 and 10 carbon
then the residue is dried and weighed. atoms. It shows the presence of caprylic acid, 2%; capric
6. Acid value: It is the amount of free acid acid, 50–80%; lauric acid, 3%; and myristic acid about
present in fat as measured by the milligrams of 1%.
potassium hydroxide needed to neutralize it. As the
glycerides in fat slowly-decompose the acid value
increases.
7. Peroxide value: One of the most widely used
tests for oxidative rancidity; peroxide value is a measure
of the concentration of peroxides and hydroperoxides
formed in the initial stages of lipid oxidation.
Milliequivalents of peroxide per kg of fat are measured
by titration with iodide ion. Peroxide values are not static
and care must be taken in handling and testing samples.
It is difficult to provide a specific guideline relating Figure 2 – Coconut Tree

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Coconut oil is used as a dietary product in many Olive oil (Salad oil; sweet oil; oleum olival.) Olive
areas of the world. In European pharmacopeia, oil is a fixed oil obtained by expression of the ripe fruits
fractionated coconut oil is known as ‘Thin vegetable oil’. of Olea europoea Linn. or Indian olive (O. ferruginea),
It is useful as a nonaqueous medium for the oral belonging to family Oleaceae.Aka: Sweet oil/oil of
administration of some medicaments. Fractionated Europe. Olive oil is a pale yellow or light greenish-yellow
coconut oil is used as a basis for the preparation of an due to presence of chlorophyll or carotenes, nondrying
oral suspension of drugs unstable in aqueous media. oily liquid with a pleasanting delicate flavour. Taste is
Diets based on medium-chain triglycerides including bland becoming cloudy and at 0°C it usually forms a
preparations made from coconut oil are used in whitish granular mass. It becomes faintly acrid. It is
conditions associated with malabsorption of fat such as miscible with ether, chloroform, and carbon disulphide
cystic fibrosis, enteritis, and steatorrhea. Abdominal pain and is slightly soluble in alcohol. Upon cooling at +5 to
and diarrhea have been reported in patients taking a diet 10°, it becomes cloudy and at 0°C usually forms a
based on medium-chain triglycerides. whitish granular mass. It becomes rancid on exposure to
air. It has specific gravity of 0.914–0.919, acid value 0.2–
Palm oil – an oil from Elaeis guineensis 2.8, saponification value 187–196, and iodine value 79–
90. Olive oil contains mixed glycerides of oleic acid (56–
Castor oil/castor oil seed/ castor bean 85%), palmitic (7–20%), linoleic (3–20%), stearic (1–
(Castor bean oil, castor oil seed, oleum ricini, ricinus oil, 5%), arachidic (0.9%), palmitoleic (3%), linolenic,
oil of palma christi, cold-drawn castor oil.). Castor oil is eicosenoic, gadoleic, and lignoceric acids. The minor
the fixed oil obtained by cold expression of the seeds of constituents are squalene up to 0.7%, phytosterol and
Ricinus communis Linn., belonging to family tocopherols about 0.2%. Italy-Spain type olive oil is
Euphorbiaceae.Ricinus is latin and means a tick or bug, higher in oleic acid and Greece-Tunisia type oil has
reffering to the seed’s resemblance to some bugs in higher levels of linoleic acid. Olive oil is used in the
shape and markings. Medicinal or the first grade or Pale manufacture of pharmaceutical preparations, soaps,
pressed castor oil is colourless or slightly yellow textile lubricants, sulphonated oils, liniments, cosmetics,
coloured. It is a viscid liquid which has slight odour with plasters; as food in salads, and for cooking and baking.
slightly acrid taste. Castor oil is soluble in absolute It has demulcent, emollient, choleretic or cholagogue,
alcohol in all proportions; Specific gravity is 0.958 to and laxative properties. It is a good solvent for parenteral
0.969, refractive index at 40°C is 1.4695 to 1.4730, acid preparations.
value not more than 2, saponification value 177 to 187,
and acetyl value is about 150. Castor oil consists of
glyceride of ricinoleic acid, isoricinoleic, stearic, and
dihydroxy stearic acids. Ricinoleic acid is responsible for
laxative property. Castor oil also contains vitamin F. 90%
of the fatty acid content is ricinoleic acid. The ricinoleic
acid is an 18-carbon acid having a double bond in the 9–
10 position and a hydroxyl group on the 12th carbon.
This combination of hydroxyl group and unsaturation
occurs only in castor oil.. Castor oil is mild purgative,
fungistatic, used as an ointment base, as a plasticizer,
wetting agent, and as a lubricating agent. Ricinoleic acid
is used in contraceptive creams and jellies; it is also
used as an emollient in the preparation of lipsticks, in
tooth formulation, and as an ingredient in hair oil. The
dehydrated oil is used in the manufacture of linoleum Figure 3 – Image of Olive
and alkyl resin. The main use of castor oil is the Forms
industrial production of coatings, also employed to make
pharmaceuticals and cosmetics in the textile and leather Virgin olive oil
industries and for manufacturing plastics and fibers. Obtained by gentle pressure in the absence of
USE and DOSE: Cathartic (stimulant type) 15- heat
60ml. Found in flexible collodion. Cold press Tournant- fallen or decomposed
Ricin- toxic principle olives are allowed to ferment
Azelaic acid- anti acne Technical- “hot press” mixed with hot water
Tricinolein > ricinoleic acid Extra virgin olive oil- the most expensive
Irritant compound causing peristalsis Tea tree oil/camelia oil- adulterant for olive oil

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Corn oil (Corn oil, maize oil.) - Corn oil is a fixed oil pentosans, resins, wax, proteoses, peptones,
obtained by expression of the embryos of Zea mays L., phospholipids, inosite phosphates, phytosteroline,
belonging to family Graminae.Refined oil is obtained xanthophyll, chlorophyll, and mucilage substances.
from the plant embryo.Corn oil is a clear, light yellow, Cottonseed cake contains about 0.6% of a toxic
oily liquid that as a faint characteristic odor and taste. principle, gossypol, which occurs in secretory cavities in
Dried corn embryo yields around 20% of fixed oil. The all parts of the plant. It is present in cold-pressed oil and
fatty acid composition of the corn oil indicates the can be removed by treatment with alkalies. Cottonseed
presence of palmitic, 8–13%; stearic, 1–4.5%; oleic, 24– oil is used as a solvent for injections and for edible
33%; linoleic 55–62%; linolenic 0.5–1.5% about 0.5% of purposes. The oil possesses emollient properties and is
arachidic, gadoleic, and behenic acids. It shows the used in liniments, in several pharmaceutical
presence of about 0.8–2% of unsapoifiable matter preparations, as a substitute of olive oil and in large
containing major proportion of β-sitosterol and doses as lubricant cathartic. Low-grade oil is used in the
compesterol.. Maize oil shows the properties similar to manufacture of soaps, lubricants, sulphonated oils, and
those of olive oil. As the oil consists of higher contents of protective coatings.
unsaturated acids, it is regarded as of value in diets
designed to limit blood cholesterol level in patients with
hypercholesterolemia, particularly following cardiac
infarction. The oil has also indicated good results in the
patients with coronary heart disease and diabetes. It is
used in place of other vegetable oils, in pharmaceuticals
and cosmetic preparations. Corn oil is used as a solvent
for injections; it is also a solvent for irradiated ergosterol.
An emulsion containing 67% of corn oil is used as a high
calorie dietary supplement (Lipomul Oral ®)

Figure 5 – Structure of Gossypol

Figure 4 – Image of a corn plant

Cottonseed oil - Cottonseed oil is a refined fixed
oil obtained by expression of seeds of Gossypium
harbaceum Linn, belonging to family Malvaceae, in
hydraulic or other presses. Cottonseed oil is a pale
yellow, oily liquid. It is odorless and has a bland taste.
The important constituents of the glycerides of
cottonseed oil are linoleic (45–50%), oleic (23–29%),
palmitic (20–33%), myristic (1.5–3.5%), stearic (1.1–
2.7%), and arachidic acids (1.0%). The glycerides
present are palmitooleolinoleins (35–40%),
palmitodioleins (20%), and trioleoor lineo-disaturated
(12–13%). The unsaponifiable fraction contains β-
sitosterol, ergosterol, vitamin E, and tocopherols. The
phosphatides present are lecithin (29%) and cephalins
(71%). The minor constituents present in the oil are free Figure 6- Image of Cotton plant
fatty acids (0.3–5.6%), gossypol (0.05%), raffinose,

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Cottonseed cake – contains about 0.6% of gossypol

Gossypol
Male contraceptive
Removed with alkali treatment

Peanut oil (Groundnut oil; monkeynut oil; peanut

oil; katchung oil; earth-nut oil. Arachis oil)- Arachis oil is
obtained by the expression of shelled and skinned seeds
of Arachia hypogaea Linn., belonging to the family
Papilionaceae. The fruit is not a true nut because the
immature pod penetrates the soil and ripens
underground. It is a colorless or yellowish liquid with a
slightly nut-like odor and bland taste.
The important constituents of the glycerides of
groundnut oil are the fatty acids palmitic (8.3%), stearic
(3.1%), oleic (56%), linoleic (26%), arachidic (24%),
eicosenoic, behenic (3.1%), and lignoceric (1.1%) acids. Figure 7 – Peanut Plant
Myristic, hexacosanoic, erucic, caprylic, lauric, and trace
Sesame oil (Benne oil; teel oil; gingelli oil;
amounts of odd carbon fatty acids are also present. The sesamum seed oil.) - Sesame oil is obtained by refining
principal glycerides of the oil are triolein (11%), the expressed or extracted oil from the seeds of
dioleolinolein (21%), saturated oleolinoleins (22%), cultivated varieties of Sesamum indicum Linn., belonging
dilinoleoolein (12%), saturated diolein (15%), and to family Pedaliaceae.The seed are small, flattened, oval
saturated dilinoleoolein (6%). The yellow colour of the oil or ovate, smooth and shiny, and whitish, yellow, or
is due to the presence of carotenoid pigments, chiefly β- reddish brown. Their taste is sweet and oily. The oil is
expressed by hydraulic or low and mediumpowered
carotene and lutein. The unsaponifiable matter consists
screw presses. A good yield of the oil is obtained by
of sterols, (campesterol, stigmasterol, β-sitosterol and three successive expression. Prior to processing in the
cholesterol), sterol glycosides β-sitosterol-Dglycoside screw press, the seed is subjected to a cooking process.
and others), and triterpenoid alcohols (β-amyrin, If live steam is used for cooking, the cuticles separate
cycloartenol and 24-methylene cycloartenol). partly from the kernels and the mixture of kernels,
Tocopherols occur free in groundnut oil. Squalene, an cuticles, and seed slips in the cage and lumpy material is
unsaturated hydrocarbon, occurs in extremely small obtained instead of a firm cake. If the seed is heated in
cooker without the addition of steam or water, and water
amounts in the unsaponifiable fraction. Two other
is added at the point of entry of dried seed into the screw
unsaturated hydrocarbons, hypogene, and arachidene, press cage, the efficiency of oil extraction is greatly
have also been reported. The kernels contain fixed oil enhanced. Alkali refining, bleaching, hydrogenation, and
(40–50%), proteins (26.2%), water (1.8%), decolourization of sesame oil can be affected with very
carbohydrates (20.6%), ash, and high concentration of little loss. The sesame oil (40–50%) is pale yellow liquid,
thiamine. The chief proteins are arachin and conarchin, almost odourless, bland taste, saponification number
188–193, iodine number 103–122, soluble in chloroform,
both are globulins of different solubility. The vitamin
solvent, and petroleum ethers, carbon disulphide; slightly
content of groundnut is moderate, the largest being in soluble in alcohol and insoluble in water. Sesame oil
the episperm. Groundnut oil is used as an edible oil, in consists of a mixture of glycerides of oleic (43%), linoleic
control of pasture bloat, as a substitute for Olive oil, as a (43%), palmitic (9%), stearic (4%), arachidic,
solvent in pharmaceutical aid, in hydrogenated state as hexadecenoic, lignoceric, and myristic acids. It also
shortening, in mayonnaise, in confections; for the contains the lignan sesamin (1%), the related sesamolin
manufacture of margarine, soap, points, liniments, and vitamins A and E. During industrial refining,
sesemolin is readily converted into antioxidant phenols
plasters, and ointments, as vehicle for intramuscular
sesamol and sesamolinol. The seeds also contain a
medication and in the laboratory as heat transfer lignan sesamolinol, γ-tocopherol, sesaminol, pinoresmol,
medium in melting point apparatus. its glycosides, sesaminol glucosides VI, VII, and VIII,
Rich in thiamine

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triglucoside KP3, carbohydrates (20%), proteins (20– belonging to the family Compositae. It is a clear, faint
25%), sterols (campesterol, stigmasterol, β-sitosterol, yellowish liquid with a characteristic odor and taste. The
and ∆5 -avenasterol), γ- and δ-tocopherols. Sesame oil oil thickens and becomes rancid on exposure to air.
is used as demulcent, in dysentery and urinary Safflower oil is slightly soluble in alcohol and freely
complaints, as a solvent for injection of steroids, soluble in ether, chloroform, benzene, and petroleum
antibiotics, and hormones, as mild laxative, nutritive, ether. Specific gravity 0.9211 to 0.9215, acid value 01–9,
emollient, in manufacture of oleomargarine, cosmetics, refractive index 1.472 to 1.475, and saponification value
iodized oil, antiacids, and ointment. It is injectable as a 188–194. Safflower oil contains glycerides of palmitic
vehicle for fat soluble substances. The oil is also used in (6.5%), stearic (3.0%), arachidic (0.296%), oleic (13%),
insecticidal sprays. Sesamolin, present in the linoleic (76–79%), and linolenic acids (90.15%). The
unsaponifiable fraction of the oil, is an effective synergist polyunsaturated fatty acid content of the oil is the highest
for pyrethrum insecticides. An extract enriched in lignans (75%) and is said to be responsible to control cholesterol
as an antioxidant and radical scavenger is used in level in the blood, thereby, reducing the incidence of
cosmetic industry. heart attacks. The edible oil is used in the manufacture
of oleomargarine, as a dietary supplement in
hypercholesteremia and also in treatment of
atherosclerosis. Due to its high linoleic acid content, it is
consumed for preparation of vegetable ghee.
Industrially, it is used for preparation of soft-soap
varnishes, linoleum and water-proofing material.

Figure 8- Structures of the constituents of Sesame

Soybean oil - This is the refined, fixed oil

obtained from the seeds of the soya plant Glycine soja.
It is a Drying oil with an IV of 120-141 and is not useful
as a cooking oil. It is an ingredient in parenteral
nutrients. An abundant source of stigmasterol. Good
source of lecithin
Lecithin- an ingredient that is useful in controlling
deranged lipid and cholesterol metabolism.
Products
Partially hydrogenated soybean oil- an
ingredient in products which is used as to balance
dietary supplements
Soybean cake- the residue after pressing the Figure 9 – Image of Safflower plant
seed, has a high value as a livestock food.
Soybean meal- used for the detection of urea Almond oil/ Sweet almond oil/ bitter almond oil -
nitrogen in blood serum by enzymatic action of the Almond oil is a fixed oil obtained by expression from the
urease in soybean meal. seeds of Prunus amygdalus (Rosaceae) var. dulcis
(sweet almonds) or P. amygdalus var. amara (bitter
Persic oil (Apricot kernel oil/ Peach kernel oil)- almonds). Expressed almond oil is an emollient and an
From the varieties of Prunus persica/ Prunus armeniaca. ingredient in cosmetics. Almond oil is used as a laxative,
Used as a vehicle and pharmaceutic necessity emollient, in the preparation of toilet articles and as a
vehicle for oily injections. The volatile almond oils are
Sunflower oil - Is the fixed oil from the seeds of used as flavouring agents. Both varieties of almond
Helianthus annuus. The oil consists of a mixture of contain 40–55% of fixed oil, about 20% of proteins,
glycerides that are rich in unsaturated acids. Alternative mucilage and emulsin. The bitter almonds contain in
to corn oil and safflower oil for culinary purposes. addition 2.5–4.0% of the colourless, crystalline,
cyanogenelic glycoside amygdalin. Almond oil is
Safflower oil - It is a fixed oil obtained from the obtained by grinding the seeds and expressing, them in
ripe and dry seeds of Carthamus tinctorius Linn., canvas bags between slightly heated iron plates. The oil

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is clarified by subsidence and filtration. It is a pale yellow becoming dark brown in color. It is a radiopaque and
liquid with a slight odor and bland nutty taste. It contains used as a diagnostic aid in hysterosalpingography and
olein, with smaller quantities of the glycosides of linoleic lymphography.
and other acids. Bitter almonds, after maceration on
hydrolysis of amygdalin yield a volatile oil that is used as Linseed/Flaxseed oil (Flax seed) - Linseed is
a flavoring agent. Sweet almonds are extensively used the dried, ripe seed of Linum usitatissimum Linn.
as a food, but bitter almonds are not suitable for this Linseed oil is obtained by expression of linseeds,
purpose. The essential or volatile oil of almonds is belonging to family Linaceae. The dried seeds are
obtained from the cake left after expressing bitter crushed in rollers, moistened and heated to 80–90°C in
almonds. This is macerated with water for some hours to steam to soften the seed tissues. They are then pressed
allow hydrolysis of the amygdalin to take place. The through hot hydraulic press at a high pressure. The oil
benzaldehyde and hydrocyanic acid are then separated so obtained is treated with alkali to separate free fatty
by steam distillation. Almond oil consists of a mixture of acids and bleached with fuller’s earth or charcoal. On
glycerides of oleic (62–86%), linoleic (17%), palmitic cooling the oil waxy substances are removed. Linseed
(5%), myristic (1%), palmitoleic, margaric, stearic, oil is a yellowish liquid, with a peculiar odour and bland
linolenic, arachidic, gadoleic, behenic, and erucic acid. taste. On exposure to air it gradually thickens, becomes
Bitter almond oil contains benzaldehyde and 2–4% of darker and acquires a more pronounced odour and
hydrocyanic acid. The purified volatile oil of bitter taste. On drying it forms a hard varnish. It has a high
almonds has all its hydrocyanic acid removed and, iodine value (~170) which indicates the presence of
therefore, consists mainly of benzaldehyde. The excess amount of glycerides of unsaturated fatty acids.
unsaponifiable matter contains β-sitosterol, ∆5 - The oil is slightly soluble in alcohol, miscible with
avenasterol, cholesterol, brassicasterol, and chloroform, ether, petroleum ether, carbon disulphide,
tocopherols. Expressed almond oil is an emollient and and terpentine oil. It has density 0.925–0.935, viscosity
an ingredient in cosmetics. Almond oil is used as a 1.47, congealing point ~20°C, saponification number
laxative, and emollient, in the preparation of toilet articles 187–195, refractive index 1.47–1.48, and unsaponifiable
and as a vehicle for oily injections. The volatile almond matters not over 1.5%. A water-soluble resinous matter
oils are used as flavoring agents. with antioxidant properties has been isolated from the
oil. Linseed contains fixed oil (30–40%), mucilage (6–
10%), protein (25%) (linin and colinin), small amount of
enzyme lipase, and linamarin which is a cyanogenetic
glycoside. The carbohydrates present are sucrose,
raffinose, cellulose, and mucilage. Linamarin is a
glucose either of acetone cyanohydrin and is identical to
phaseolunatin. Unripe seeds contain starch which is
converted to mucilage on ripening the seeds. The
mucilage can be fractionated into a neutral fraction a
remified, arabinoxylan composed of D-xylose, L-
arabinose, D-glucose and D-galactose; and an acidic
fraction mainly com posed of L-rhamnose and D-
galactose. Mucilage swells with water and forms red
colour with ruthenium red. Linamarin on hydrolysis yields
acetone, hydrocyanic acid, and glucose. The other
constituents are phytin, lecithin, wax, resin, pigments,
malic acid, cyanogenic glycosides linustatin
neolinustatin, and secoisolariciresinol and
phenylpropanoid glucoside linusitamarin. On hydrolysis
Linseed oil produces unsaturated acids like linolenic acid
Figure 10 – Image of Almond tree and Seed (30–50%), linoleic acid (23–24%), oleic acid (10–18%)
together with saturated acids-myristic, stearic, and
Ethiodized oil injection - is an iodine addition palmitic (5–11%). Linseed is used as demulcent and in
product of ethyl ester of the fatty acids of poppy seed oil. form of poultices for gouty and rheumatic swellings.
It contains not less than 35.2% - 38.9% of organically Internally it is used for gonorrhoea and irritation of the
combined iodine. genito-urinary system. Linseed oil has emollient,
It decomposes when exposed to air and sunlight, expectorant, diuretic, demulcent, and laxative properties

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 Course Code: PHA 040 (Pharmacognosy and Plant Chemistry)
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and is utilized externally in lotions and liniments. cavities made in the earth for three to six days, and
Nonstaining iodine ointment soap, linoleum, greases, during fermentation, the colour of the seeds changes
polishes, polymers, varnishes, paints, putty, oil cloths, from white to dark reddish brown due to enzymatic
printing inks, artificial rubber, tracing cloth, tanning and reaction. If the seeds are not subjected to the process of
enameling leather, etc. are also prepared from Linseed fermentation and dried in sun, then they are more
oil. The mucilaginous infusion is used internally as a astringent, bitter-tasting, and of less value. After
demulcent in colds, coughs, bronchial affections, fermentation, the seeds are roasted at 100–140°C to
inflammation of the urinary tract, gonorrhea, and remove the acetic acid and water present in the seeds
diarrhea. and facilitate removal of the seed coat also. The seeds
are cooled immediately and are fed into a nibbling
machine to remove the shells followed by winnowing.
The kernels are then fed into hot rollers which yield a
pasty mass containing cocoa butter. The pasty mass is
further purified to give cocoa butter. Cocoa butter is a
yellowish-white solid and brittle below 25°C. It has a
pleasant chocolate odor and taste. It is insoluble in water
but soluble in chloroform, petroleum ether, ether and
benzene. The specific gravity ranges from 0.858 to
0.864, the melting point is between 30°C and 35°C, the
refractive index varies from 1.4637 to 1.4578, the
saponification value is 188–195, and the iodine value
35–40. It consists of glycerides of stearic (34%), palmitic
(25%), oleic (37%) acids, and a small amount of linoleic
acids and arachidic acid. The glyceride structure is
responsible for the nongreasiness of the product. It is
used as an emollient, as a base for suppositories and
ointments, manufacture of creams, and toilet soaps. It
reduces the formation of stretch marks during pregnancy
by keeping the skin supple. It is used as an ingredient in
lotion bars, lip balms, body butter, soaps, and belly
balms for expectant mothers.

Figure 11 - Image of Flax

Rapeseed oil - Is a Crude drug from Brassica

campestris. Prior to 1970, commercial rapeseed oil
contained up to 50% erucic acid- causes myocardial
lipidosis (fatty degeneration of the heart) and damages
the heart muscle in animals. Contains Canola oil Figure 12 – Image of Theobroma plant
Products
Theobroma Oil (Theobroma oil, cacao butter,
cocao beans, semina theobromatis.) - Are the roasted Sweet chocolate- bitter chocolate to which sugar
seeds of Theobroma cacao. Cocoa seeds contain and vanilla or other flavoring substance have been
nearly 50% of cocoa butter. The seeds are separated added.
from pods and are allowed to ferment. Fermentation Cocoa- is a powder prepared from roasted, cured
process takes place at 30–40°C in tubes, boxes or in kernels of the seed.

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 Course Code: PHA 040 (Pharmacognosy and Plant Chemistry)
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+ FAT
Lanolin / Hydrous wool fat (Wool fat; Oesipos;
Agnin; Alapurin; Anhydrous lanolin; Adeps lanae; Laniol)
Lanolin is the fat-like purified secretion of the sebaceous
glands which is deposited into the wool fibers of sheep,
Ovis aries Linn., belonging to family Bovidae. Lanolin is
a yellowish-white, ointment-like mass that has a slight
characteristic odor. Wool is cut and washed with soap or
alkali. An emulsion of wool fat, called wool grease, takes
place in water. Raw lanolin is separated by cracking the
emulsion with sulphuric acid. Wool grease floats on the
upper layer and fatty acids are dissolved in the lower
layer. Lanolin is purified by treating it with sodium
peroxide and bleaching it with reagents. Lanolin is a
complex mixture of esters and polyesters of 33 high
molecular weight alcohols and 36 fatty acids. The
alcohols are of three types; aliphatic alcohols, steroid
alcohols, and triterpenoid alcohols. The acids are also of
three types: saturated nonhydroxylated acids,
unsaturated nonhydroxylated acids, and hydroxylated Figure 13 – Image of Cod fish and Constituent found
acids. Liquid lanolin is rich in low molecular weight, in it.
branched aliphatic acids, and alcohols, whereas waxy
lanolin is rich in high molecular weight, straight-chain +WAXES
acids, and alcohols. The chief constituents of lanolin are Plant waxes
cholesterol, isocholesterol, unsaturated monohydric Carnauba wax (Brazil wax.) - It is an exudates
alcohols of the formula C27H45OH, both free and from pores of the leaves of the Brazilian wax-palm tree
combined with lanoceric (C30H60O4 ), lanopalmitic Copernicia prunifera and C. cerifera, belonging to family
(C16H22O3 ), carnaubic, and other fatty acids. Lanolin Palmae. The leaves of Brazilian wax-palm are collected,
also contains esters of oleic and myristic acids, aliphatic dried, and then spread on cloth. By brushing and
alcohols, such as cetyl, ceryl and carnaubyl alcohols, beating, the wax is separated. It is then melted,
lanosterol, and agnosterol. Lanolin is used as an processed further to purify, and poured into the moulds.
emollient, as water absorbable ointment base in many It contains esters of hydroxylated fatty acids, that is,
skin creams and cosmetic and for hoof dressing. Wool carnaubic and cerotic acid and melissyl cerotate.
fat is readily absorbed through skin and helps in Carnauba wax is used for preparation of cosmetic
increasing the absorption of active ingredients products, depilatories, and deodorant sticks. It is also
incorporated in the ointment. However, it may act as an used for tablet coating. High-quality shoe polishes and
allergenic contactant in hypersensitive persons. automobile waxes are other products made from
Cod Liver oil - It is processed from fresh liver of carnauba wax.
cod fish, Gadus morrhua and other species of Gadus,
belonging to family Gadidae. The oil is pale yellow in
colour; it has fishy odour and taste. Cod liver oil is
slightly soluble in alcohol and fully soluble in chloroform,
ether, carbon disulphide and petroleum ether. Specific
gravity: 0.922–0.929, Refractive index: 1.475–1.4745,
Acid value is less than 2, Iodine value 155–173. The oil
should be stored in well-filled airtight containers,
protected from light, and kept in a cool place. The cod
liver oil contains glycerides esters of saturated acids of
linoleic, oleic, myristic, gadoleic, palmitic, and other
acids. The oil has vitamin A and vitamin D. Cod liver oil
also contains about 1% unsaponifiable matter; like
cholesterol, fatty alcohol, squalene, α-glyceryl esters,
etc. Oil is used as a source of vitamins, in the treatment
of rickets, tuberculosis, and also as a nutritive. Figure 14- Image of Carnuba tree

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The wax consists of alkyl esters of wax acids (80%). permanganate, chromic acid or chlorine or charcoal.
Consituent: Myricyl cerotate Beeswax contains myricin, which is melissyl palmitate;
melting point 64°C, free cerotic acid (C26H52O2 ),
Jojoba oil - Is a liquid wax expressed from the myricyl alcohol (C30H61OH) is liberated when myricyl
seeds of Simmondsia chinensis Hydrogenation of the oil palmitate is saponified. Melissic acid, some unsaturated
yields a crystalline wax that has the appearance and acids of the oleic series, ceryl alcohol, and 12 to 13%
properties of spermaceti. higher hydrocarbons are present. Beeswax is used in
the preparation of ointments, plaster, and polishes.
Animal wax Beeswax is adulterated by solid paraffin, ceresin,
Spermaceti wax – is a wax from sperm whale- carnauba wax, or other fats and waxes of animal or
Physeter macrosephalus. It was formerly recognized as mineral origin. Spermaceti and lard render wax softer
a quality emollient and a desirable ingredient in cold and less cohesive, of a smoother and less granular
creams and other cosmetics. Cetyl ester wax (synthetic fracture and different odour when heated. The melting
spermaceti) point and specific gravity are lowered by tallow, suet,
Cetyl alcohol- is a mixture of solid alcohol consisting of lard, and especially by paraffin. Ceresin, a principle
chiefly of cetyl alcohol or 1-hexadecanol. It is used as an obtained from ozokerite is also employed as an
emulsifying aid and as a stiffening agent in adulterant. In yellow wax the iodine value is also of use
pharmaceutic preparation. as a test for detection of adulterants but in white wax the
Stearyl alcohol- a mixture of solid alcohols consisting bleaching process has altered the bodies which absorb
chiefly of stearyl alcohol or 1-octadecanol. the iodine.

Bees wax(White beeswax, yellow beeswax,

cera alba, and cera flava.) - Is Beeswax is the purified
wax obtained from honeycomb of hive bee, Apis
mellifera Linn and other species of Apis, belonging to
family Apidae. Wax is secreted in cells on the ventral
surface of the last 4 segments of the abdomen of worker
bees. Yellow beeswax – purified only; used as a
stiffening agent. White beeswax – purified and bleached;
employed pharmaceutically in ointments and in cold
creams. The worker bee secretes the wax due to the Figure 15- Bee
ability of maintaining a high temperature and the wax is
secreted in the last four segments of abdomen on the Prostaglandins -C20 lipid metabolites derived from
ventral surface. Just below the sterna it has a smooth essential, unsaturated fatty acid (arachidonic acid).
layer of cells form the chitinous area that secretes the Mediators of platelet aggregation, pain and inflammation
wax. The chitinous area has small pores through, which Dominant in seminal fluid. Activation of inflammatory
the wax exudes out. The wax is passed to the front leg response, production of pain and fever. Certain
and later to the mouth; in the mouth it gets mixed with prostaglandins are involved with the induction of labor
the saliva, which is then built on the comb. This wax and other reproductive processes A type of
forms a capping on the honey cells. Wax forms about prostaglandin called Thromboxane, stimulates
1/8th part of the honeycomb. After removal of honey, bronchoconstriction and platelet aggregation
honeycomb or the capping is melted in boiling water. On Prostaglandins are involved in several other organ such
cooling the melted wax gets solidified and floats on the as:
surface of water while the impurities settle below and + GI- inhibit acid synthesis and increase secretion of
honey leftovers get dissolved in water. The pure wax is protective mucus
then poured into earthen vessels wiped with damp cloth + Increase blood flow in kidneys
and the wax so obtained is yellow beeswax. White
beeswax is obtained from yellow beeswax. The yellow Prostaglandin classification
beeswax is runned on a thin stream of spinning wet Classes: based on the functional group around the
drum, from which long ribbon like strips are scrapped off. cyclopentane ring
The ribbon strips are placed on cloth in thin layers,  A- has an α,β-unsaturated keto groups
rotated from time to time and bleached in sunlight till the
outer layer becomes white. White beeswax is obtained
 E- has β-hydroxyketone
by treating yellow beeswax chemically with potassium  F- 1,3 diols

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 Course Code: PHA 040 (Pharmacognosy and Plant Chemistry)
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Prostaglandin analogs - Pyrexia

- Diarrhea
Carboprost /dinoprost - 15- Methyl prostaglandin F2α - Nausea
Stimulates contraction of gravid uterus like the - Headache and chills
contractions of the full term at labor
Used in terminating second trimester pregnancy Alprostadil (Prostaglandin E1)- Produces vasodilation,
administration.: slow injection through the amniotic sac. inhibits platelet aggregation, and stimulates intestinal
40mg dose. and uterine smooth muscle
Side effect: Use:
- Vomiting Palliative therapy to maintain temporarily neonates
- Diarrhea with patent ductus arteriosus and congenital heart
- Elevation of BP defects that restrict the pulmonary or systemic blood flow

Dinoprostone (Prostaglandin E2) - Another uterine Misoprostol (Methyl-1, 6-hydroxyprostaglandin E1

stimulant approved for termination of second-trimester methyl ester) - Inhibits gastric secretion, also produces
pregnancy uterine contractions that may endanger pregnancy by
Advantage: lack of vasoconstriction that results to causing abortion
hypertension Uses:
Administration: inserted in the vagina: 20mg suppository. Used orally in patients that are at high risk for
Side effects: developing ulcers during NSAID therapy
- Vomiting

Activity 3: Skill-building Activities (30 Mins)

Go to the nearest Pharmacy or supermarket, and look for a Lipid derivative product. Get a picture of the product ,
the Constituent found in the product (It should be an Active Ingredient), and Classify the Constituent found in the product
as to the class of the Lipid (Fixed oil, Fats or Wax)

LIPID DERIVATIVE CRUDE DRUGS

Classification (Fixed oil,
Image of the Product Constituent
Fats, or Wax)

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Activity 4: What I Know Chart, part 2 (5 mins)

Instruction: Please go back to the What I Know table which is placed in Activity 1. Please do read again the
question and answer the question allotted for activity 4 “What I learned”

Activity 5: Check for Understanding (30 mins)

Answer the following Questions. This questions are from the Module that you have just finished.

1. Are solid Long chain fatty acids combined with an alcohol.

a. lipids c. Fats
b. Waxes d. Fixed oils
2. The following are saturated fatty acids except:
a. Oleic acid c. Palmitic acid
b. Lauric acid d. butyric acid
3. The Number of milligrams of KOH required to neutralize the free acids and saponify esters present in 1g of the
substance.
a. Acid Value c. Iodine Value
b. Ester Value d. Saponification value
4. Solid fixed oil
a. Lanolin c. Cocoa oil
b. Linseed oil d. cod Liver oil
5. Liquid fat
a. spermaceti c. Codliver
b. beeswax d. Lanolin
6. The toxic component of Castor
a. Azelaic acid c. Tricinolein
b. Ricin d. Rcinoleic acid
7. Standard iodine value of drying oils.
a. <100 b. 100-120 c. >120

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 Course Code: PHA 040 (Pharmacognosy and Plant Chemistry)
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8. good fatty acid

a. Saturated fatty acid b. Unsaturated fatty acid

9. Palmitic acid is a fatty acid that contains how many carbon atoms
a. 10 c. 18 e. 14
b. 16 d. 20
10. Arachidic acid
a. Saturated fatty acid b. Unsaturated fatty acid

B. LESSON WRAP-UP

Activity 6: Thinking about Learning (5 mins)

A. Work Tracker
You are done with this session! Let’s track your progress. Shade the session number you just completed.
PHARMACOGNOSY AND PLANT CHEMISTRY
P1 P2 P3
1 2 3 4 5 6 7 8 9 10

B. Think about your Learning. Today was a good start, it was quite hard but the important thing is that you
learned new things. Please do tell me what is the highlight of the session for you and what are the things you
encountered in this session that inspired you to become The Best Pharmacist.

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FAQs

1. What are the salient points in identifying whether the crude drug is a Fixed oil, Fat, or wax?

The main points in classifying the crude drug as a Fixed oil, Fat, or wax, will be first its source, Note that all fixed oils are
isolated or collected from plants, while the Fat is isolated from the Animal, while for the wax, we can isolate them from
both Animal and plant Source. Next will be the melting point or form. Fats are solid at room temperature, except for Cod
oil, and Fixed oils are Liquid at room temperature Except for Theobroma oil. Lastly, the point for consideration for
classifying these, is the chemical composition, both fixed oil and fat are made up of Glycerol and simple fatty acids, while
waxes are made up of complicated Alcohol.

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