Pharmacognosy (Lipids and derivatives)
The extra two lectures (record 25)
Done by: Aseel Al.Qabbani.
In the last lecture we were talking about lipids, and we started
talking about fatty acids, we could distinguish two types of fatty
acids which are: saturated and unsaturated fatty acids.
Regarding the unsaturated which are the most important, we talked
about the essential fatty acids which are essential and important
for human nutrition.
Also we talked about fatty acids with 18,20 and 22 carbon
skeletons.
**Examples on 18 carbons unsaturated fatty acids:1) Oleic acid: It is not an essential fatty acid, but it is a
monounsaturatedoctadecenoic acid. It is available in many fixed oils
(olive oil, peanut oil). It has a nutritional value but it is not essential.
2) Linoleic acid: Essential fatty acids start with this one. It is an 18
carbons fatty acid with 2 unsaturations (double bonds)
diunsaturated. Its systematic chemical name is: 9,12octadecadienoic acid.
3) α and γ-Linolenic acids: These are other essential fatty acids
with 18 carbon skeletons and they are α and γ isomers of each
other. These two are very important with high nutritional & dietary
values. Since they have dietary values, they are added to dietary
supplements.
**Note that not all fatty acids are added to dietary supplements, if
you remember we talked about omega 3 and omega 6 fatty acids
that are generally added to dietary supplements as essential
nutritional components, principally such as: α, γ-Linolenic acids, in
addition to 2 fatty acids with 20 and 22 carbon chains which are
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EPA (eicosapentaenoic acid, 20 carbons with 5 double bonds) and
DHA (docosahexaenoic acid, also another essential fatty acid). Both
EPA and DHA are available in the Cod liver oil.
So, essential fatty acids are: α, γ-Linolenic acids, DHA and EPA and
these are the most important ones. Also, linoleic acid and
arachidonic acid can be considered as essential fatty acids but
these are less important. Arachidonic acid is one of the main
components of the phospholipids and thus it is very necessary for
good integrity and strength of our cells and cell membranes, and
this component is obtained by diet so it is essential. (Either it is
obtained from diet as such or it is biosynthesized in our body but
from biosynthetic precursors that are obtained from external
sources, and in both cases the compound is considered as essential).
**Note:We should focus on the structures of the compounds that are
mentioned above especially the essential ones (α, γ-Linolenic acids,
EPA and DHA) also we are supposed to know about their sources of
fixed oils that are rich in these fatty acids.
**Examples of these sources:- EPA and DHA  present in Cod liver oil.
- α-Linolenic acid  one of the rare essential fatty acids, available
in some vegetable oils (plant oils) such as: flaxseed oil (linseed oil).
- γ-Linolenic acid It is of high essential nutritional value. There
are 2 important oils that are considered worldwide the main sources
of γ-Linolenic acid which are: Borage oil and Evening primrose oil,
both are rich in γ-Linolenic acid.
Both α and γ-Linolenic acids (particularly α) are not highly
distributed in nature and only exceptional oils contain good
quantities of these essential fatty acids.
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**Note:Oils in general are obtained from seeds or beans and some
exceptional oils are obtained from fruits and the best example of
fruit-derived oils is olive oil via expression of olive fruits. Another
example of fruit-derived oils is Avogado oil. While the rest of the
other fixed oils(that we will talk about in table 3.2) the majority of
them are obtained from seeds.
**Uses of fixed oils in general :1) Nutritional value:
Oils are used as sources of energy.
2) Food value:
Majority of oils have this food value. They are food oils, cooking
oils, we use them in food industry, they are added to our foods and
deserts. Most of food products contain at least one type of fixed
oils (fats). So we must distinguish between these oils and appreciate
their nutritional value.
**Note:It is important to distinguish between oils that have a food value
and oils that are sources of essential fatty acids added to dietary
supplements. (All of fixed oils have a food value and are energy
sources, but not all of them have this high nutritional value of
containing essential fatty acids that leads to adding them to dietary
supplements).
Examples of oils that are sources of dietary supplements are:
borage oil, primrose oil, flaxseed oil and cod liver oil.
 An oil should contain one of the essential fatty acids to be
considered as a dietary supplement and the four main essential
fatty acids are: (α-Linolenic acid, γ-Linolenic acid, EPA and DHA).
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In addition to arachidonic acid which is less widespread and less
important (as mentioned earlier). So these 4 fatty acids (α, γ, EPA,
DHA) give the oil an additional nutritional value as a source of
essential fatty acids to be added to dietary supplements.
3) Cosmetic value:
Oils have a very high cosmetic value. They are used in detergent &
soap manufacturing. Also, oils are emollients, bases for ointments &
creams (ointments & creams are emulsions w/o and o/w,
respectively) and always the oily phase is a fixed oil.
4) Pharmaceutical value:
Oils are usedas bases for parenteral intramuscular injections where
we have an oily base. Some regenerated pyrogen-free fixed oils are
utilized for this purpose.
Also, in aromatherapy a lot of volatile oils that are indicated to
treat external problems of skin or sometimes internal problems are
prepared and dissolved in an oily base as a carrier (vehicle). (Oils
are used as carriers for aromatherapy).
5) Therapeutic value:
Some of fixed oils have some specific and characteristic
valueresulted from characteristic properties such as containing
distinctive fatty acids. This characteristic value may be a
therapeutic value. A lot of fixed oils are of therapeutic value.
**Examples of fixed oils having therapeutic values:
1) Castor oil:
It is commonly used as cathartic (strong laxative) to evacuate the
gut content to prepare it before gastric endoscopy. Usually in the
day before endoscopy, the doctor advises the patient to take
portions of castor oil.
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**Castor oil is obtained from Ricinuscommunisseeds, these castor
plant seeds are a very good source of castor oil which is cathartic
therapeutic agent and also at the same time they are very veryvery
toxic seeds, because they contain one of the most poisonous toxins
on the earth (a substance which is a glycoprotein (493 aminoacids
with some sugars) that is called "ricin", it is a very toxic
glycoprotein that damages the essential organs (liver, kidneys) and
causes circulatory collapse leading to quick death. In the past, this
toxin was used to assassinate Khaled Meshaal.
Ricin exists in castor seeds, and these seeds are the source of
castor oil, but the castor oil that is obtained by expression of the
seeds does not contain ricin, because ricin is a water soluble
glycoprotein presents in very trace levels in the castor seeds (and
even in trace levels it is very toxic actually), but it is not obtained
by expression and the castor oil (because it is oily) cannot dissolve
ricin efficiently.
Ricin separation requires a complex method of extraction,
preparation and isolation of this ricin material, but crushing the
seeds to prepare tablets and then taking these tablets leads to
toxic effects.
So, as pharmacists, we should be aware of these toxic plants
(Ricinus communis plant that is classified under toxic &
hallucinogenic plants (ricin toxin) with therapeutic application
(castor oil as laxative)).
Its toxicity: 2-3 or 2-4 seeds of this plant are fatal for a child,
while 6-8 seeds are fatal for an adult. So it is a very toxic plant
with high mortality resulted from direct usage of the seeds which
contain ricin.
Also, these seeds contain an alkaloid (which is not toxic) that
presents in small amounts "ricinine".
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The procedure to be taken if someone is toxicated by ricinis to save
the vital organs (liver,kidneys). The patient is given high sugar
intake to decrease the damage on the liver, and also for the kidneys
to decrease the acidity of the urine that may lead to precipitation
of hemoglobin and damage of kidneys so alkalinizationof the urine is
applied to decrease the damage of kidneys. Also, the patient is
given an emetic agent such as "Ipecac" to get rid of any unabsorbed
components of ricin.
2) Honesty oil:
It contains a very important fatty acid that is implicated in the
multiple sclerosis (an auto immune disease with unknown sure
reasons, a multi-reason disease, but it is thought to be associated
with nervous tissue causing degeneration of the neuronal
transduction and communication resulted from degeneration of the
myelin tissue of neurons). This fatty acid is one of the important
fatty acids in the myelin tissue of the neuronal cells and it is called
"nervonic acid" (its name indicates that it is associated with the
nervous system). Nervonic acid exists in good quantities in only one
fixed oil which is honesty oil so it can be helpful in the treatment of
multiple sclerosis.
Also, honesty oil contains erucic acid (20 carbon monounsaturated
fatty acid). Erucic acid is used in paint industry, it is found in large
quantities in the rapeseed oil (50% erucic acid), in addition to
honesty oil but in smaller quantities.
**Note:As pharmacists, we should focus on the uses & applications of fixed
oils.
The properties, uses and applications of fixed oils are dependent on
the quality of the oil, and the quality is determined by the nature
and the quantities of the active principles.
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-What are the active principles of the oils ??
Triglycerides, in general, (glycerol esterified with 3 fatty acids).
So, the composition, the identity and the quality of any fixed oil is
determined by its content of fatty acids (their nature (identity)
and their relative percentages).
Also, we should know the botanical name of the plant source of the
oil, (eg. Ricinuscommunis) and the part of the plant that is used as a
source (In general, seeds with some exceptions that are obtained
from fruits).
**Comparison between fixed oils & volatile oils:-Sources: Fixed oils are available in nature in both plants and
animals, unlike volatile oils that are obtained only from plants (aerial
parts). Majority of oils that we have talked about are from plant
sources (mainly from the seeds). An example of a fixed oilfrom
animal source is : cod liver oil (obtained from the liver of whales).
-Chemistry: Fixed oils contain triglycerides, they are fatty acidcontaining lipids, while volatile oils contain terpenoids (particularly
the lower terpenoids, monoterpenes and sesquiterpenes, and these
are obtained from mevalonic acid pathway as we will take in
phytochemistry 2).
-Production: Volatile oils are produced mainly by hydrodistillation.
Other methods include Florasols extraction and hot extraction.
Carbon dioxide is the best to be used in supercritical fluid
extraction. But the best traditional technique for the extraction of
volatile oils is by distillation (we mix the herbal material with water
in a vessel then we heat it, this vessel is combined with a distiller
(condenser), and then there is a collecting flask, the water boils and
evaporates the volatile oil, the vapors are mixed with each other,
then the vapor condenses and separates into 2 phases, usually the
upper phase is the oil and the lower phase is water except if the oil
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is a chlorinated hydrocarbon (heavier than water) so it will be in the
lower phase, finally we separate the upper phase.
While fixed oils are obtained mainly by expression (mechanical or
hydraulic press) to express the oil from seeds (mainly) or fruits.
-Uses:Fixed oils  all of the uses that we talked about (in
pharmacy, therapy, cosmetic and food industry).
Volatile oils  high therapeutic applications, used in aromatherapy
(a type of therapy that is defined based on the use of volatile oils
externally& internally). Also, volatile oils are the odoriferous
principles in plants, and thus they are used in the manufacturing of
perfumes, and also they are used as flavor & fragrance substances
in pharmaceutical & food industries.
**Summary:
Sources
Chemistry
Production
State at R.T
Uses
Fixed oils
Plants + animals
(seeds mainly)
Triglycerides
(fatty acids)
Expression
Fixed (not volatile)
Pharmacy, therapy,
cosmetic and food
industries,…
Volatile oils
Plants only
(aerial parts)
Terpenoids
Hydrodistillation
Volatile
High therapeutic value,
Aromatherapy, flavor &
fragrance substances,…
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This slide indicates the biosynthetic process of essential fatty
acids in the different living organisms (plants, bacteria, fungus and
animals (humans or animals)).
In humans  stearic acid is converted into oleic acid.
In plants & fungi  linoleic acid is formed from oleic acid.
In humans  linoleic acid is converted into γ-linolenic acid.
So linolenic acid is formed in humans actually, but from the
precursor linoleic acid that is not formed in humans, and that's why
linoleic acid and the other fatty acids that are formed from it are
essential fatty acids (because they are from external sources).
Linoleic acid (diunsaturated 9,12) with further desaturation 
γ-linolenic acid (18C, triunsaturated 6,9,12) with chain elongation
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(adding of 2 carbons so it converts from 18C to 20C)dihomo-γlinolenic acid (20C) with further unsaturation arachidonic acid
(20C with 4 unsaturations 5,8,11,14) and in another pathway it gives
EPA (20C), but in this pathway it ends with arachidonic acid.
In plants & fungi  linoleic acid is converted into α-linolenic acid.
Note that γ-linolenic acid is formed in humans from linoleic acid but
α-linolenic acid is not, and it is formed in plants and fungi.
In animals  α-linolenic acid stearidonic acid with chain
elongationeicosatetraenoic acid eicosapentaenoic acid (EPA, an
essential fatty acid) with further chain elongation by 2 carbons 
docosahexaenoic acid (DHA (22C), another essential fatty acid).
As we mentioned before, both EPA & DHA present in the cod liver
oil. They are substances that are essential in animals, formed
especially in the liver of animals, rarely formed in humans (except
arachidonic acid that may be formed in humans from γ-linolenic acid
and lenoleic acid precursors).
**Note:Eicosanoids (20 carbon fatty acid containing biological autocoids or
biological factors (hormone-like substances) formed in our bodies,
3 groups :
Prostaglandins, leukotrienes and thromboxanes.
The most widely known 20 carbon fatty acid that exists in
phospholipids is arachidonic acid.
- Dihomo-γ-linolenic acid is converted in a biosynthetic pathway to
give prostaglandins 1-series
- Arachidonic acid gives prostaglandins 2-series.
- EPA gives prostaglandins 3-series.
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These three fatty acids differ in the number of double bonds they
contain (3,4,5 double bonds, respectively), and this difference leads
to the different series of prostaglandins that they produce (1,2,3
also respectively). But how ???
The first process that leads to the formation of prostaglandins is a
process of cyclization & oxidation via enzymes called
cyclooxygenases (COX).
These enzymes catalyse cyclization between C8 and C12 (812
cyclization) to form a single bond and thus forming a cyclopentane
head to which attached two tails (one of them is a 7-carbon tail
starts with carboxylate and the other is an 8-carbon tail ends by
methyl terminus). This is the prostanoic acid (the structure that
represents the backbone of prostaglandins in general).
**The idea is that prostaglandins are classified into 3 groups based
on the total number of double bonds on the tails (side chains). Each
cycle encloses two double bonds and a certain number of double
bonds remains on the tails.
1-series  1 double bond on the tails, derived from dihomo-γlinolenic acid (3 double bonds).
2-series  2 double bonds (each side chain has one double bond),
derived from arachidonic acid (4 double bonds).
3-series  3 double bonds (one on the carboxylate side chain and
two on the methyl terminus side chain), derived from EPA (5 double
bonds).
**Fixed oils are classified into 2 categories:1) Saturated oils:Those that are rich in saturated fatty acids
(stearic acid,palmitic acid, lauric acid). But they do not only contain
saturated fatty acids, they may contain some unsaturated ones.
- unhealthy (because they are rich in saturated fatty acids)
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- Examples: (Both are from palm family)
1) Coconut oil
2) Palm oil
Although both are rich in saturated fatty acids, they are highly
utilized in food industry because they give a kind of consistency
since they are solid at R.T and they reduce the degree of fluidity of
some dosage forms. But they are added in small amount so they will
not increase the LDL.
2) Unsaturated oils:Those that are rich in unsaturated fatty acids.
- healthy oils (increase HDL (good cholesterol) at the expense of
LDL (bad cholesterol)).
- they are further classified into :
A) Monounsaturated oils: Oils containing one given unsaturated
fatty acid predominated (major, presents in the highestproportion
(more than 50%) in the compound as it is the only component) but
they contain other minor fatty acids.
-This does not necessarily mean that these oils contain fatty acids
with one unsaturation (one double bond). But usually the single
predominated fatty acid is a monounsaturated fatty acid.
- If we are asked about the identity or composition of a
monounsaturated oil, it is enough to mention only its single major
fatty acid without the other minor ones.
- Examples of monounsaturated oils: (memorize them please)
1) Castor oil: Its main fatty acid is ricinoleic acid (more than 90%).
Ricinoleic acid is a combination of two names: the genus name in the
species Ricinuscommunis + oleic acid which is a monounsaturated
fatty acid (9-octadecenoic acid)). The name is based on oleic acid
because ricinoleic acid has the same structure as oleic acid with
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hydroxylation at C12 (ricinoleic acid is a 12-hydroxyoleic acid). So
we can synthesize ricinoleic acid by simple hydroxylation of oleic
acid.
Oleic acid is a monounsaturated stearic acid, and stearic acid is an
octadecanoic acid (an 18 hydrocarbon chain starts with
carboxylate).
2) Olive oil: More than 50% of its content is oleic acid
3) Peanut oil "arachis oil": More than 50% of its content is oleic acid
4) Rapeseed oil: More than 50% erucic acid (monounsaturated 20C
fatty acid)
**Note:
We have a lot of oil pairs that resemble each other:
1) Olive oil + peanut oil: Both contain oleic acid (more than 50%),
and that's why they are highly resembling each other and they are
comparable in properties, uses and applications.
2) Cod liver oil + halibut liver oil: These are fish oils obtained from
two species of whales. They are different oils from different
sources but they are similar in everything (composition, properties
and applications).
3) Evening primrose oil + borage oil: Both are rich in γ-linolenic acid.
Also they are similar in their properties, applications and
composition.
B) Polyunsaturated oils:
- Comparable percentages of more than one unsaturated fatty acid
- Examples include: cooking oils in general (sunflower oil, safflower
oil, corn oil,almond oil and soybean oil).
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All of these are food oils, some of them are dietary oils, others
contain lecithin which decrease the absorption of lipids (e.g.
soybean oil).
- If we are asked about the identity or composition of these
polyunsaturated oils we have to mention at least two fatty acids as
the major components.
**Note:
Fixed oils obtained from plant sources are healthy oils (i.e. they are
liquid at R.T, rich in unsaturated fatty acids) with some exceptions
that are saturated (e.g. palm oil, coconut oil). While most of the oils
obtained from animal sources e.g. margarine, butter are bad fats
because they are rich in saturated fatty acids, solid at R.T (with
some exceptions e.g. cod liver oil).
**Table 3.2: (very very important)
This table is very valuable, and we should refer to it as pharmacists
because it summarizes the main fixed oils.
Read the introduction above the table (fixed oils, their sources in
general and how can I make some of the fixed oils solid at R.T
instead of liquid because the pharmaceutical industry requires the
use of a lot of these fixed oils as lubricants (hydrogenated oils) for
example in tablet manufacturing to prevent adhesion of tablets to
tubes, funnels, dies, lower and upper pistons of the tableting
machine (rotary tablet machine or single punch machine) or as
stiffening/hardening materials (i.e. instead of having liquid
ointments & creams at R.T, we will have them in solid state. This
rigidification can be performed by hydrogenation to render many of
the fatty acids components as saturated fatty acids) e.g. waxes
(bees wax) that are used as bases in suppositories also they are
stiffening agents that prevent suppositories from melting at R.T
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and keep them consistent via increasing their melting points, also
hydrogenated oils may be used for this purpose).
**How to study this table ??
Study the oil name, its source (botanical binomial name, don't study
the family name), the part used (the most used parts are seeds,
others are beans/fruits (olive oil)/liver of animal source (cod liver
oil).
Oil content (don’t memorize this column), it only indicates that is
around 50% of the dry weight of the seeds or the source organ is
oil which is a high percentage.
Typical fatty acid composition (important column)  for
monounsaturated oils memorize only the main fatty acid, while for
saturated & polyunsaturated oils memorize at least two or three of
the major fatty acids. Percentages are not included.
Uses (very important): The principal pharmaceutical knowledge.
We should know everything about the applications and uses
especially pharmaceutical, cosmetic and therapeutic applications
(can be included under pharmaceutical applications, i.e.
pharmaceutical = pharmaceutical aids in dosage form manufacturing
+ therapeutic drug uses, or we separate them as pharmaceutical
(physical concerns, pharmaceutical aids) and therapeutic drug
(active ingredients).
This column includes the same general uses of oils that we have
talked about earlier.
**Note:
Now I will mention all of the informations that the doctor had
explained about this table, but it's better for you to study
everything in this table (except the family name, oil content and the
percentages of fatty acids).
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*Almond oil
*Borage oil
*Castor oil
*Arachis oil "peanut oil": resembles olive oil
*Coconut oil:
- one of the saturated oils (43-53% lauric acid (12C), high
percentage ! + myristic acid (14C) + palmitic acid (16C)  rich in
saturated fatty acids)
*Cod liver oil:
- Source cod"Gadusmorrhua" (whales)
There is another species of whales which is "Hippoglossus vulgaris"
and this is the species of halibut.
So we have halibut + cod liver oils, they are highly resembling each
other in composition, properties and applications.
- Composition of cod liver oil: It contains oleic acid (24%) the same
as other oils (olive oil, peanut oil), but we use it not due to its
content of oleic acid (nutritional), we use it actually because it is
the only source that contains acceptable levels of DHA & EPA (even
if they are only 14%, 6%) which are essential fatty acids.
- Uses: Dietary supplement due to presence of EPA & DHA +
antioxidant vitamins + vitamins A & D (very important vitamins,
optical power increases their use).
It has a very high nutritional value. Soft gelatin capsules of cod
liver & halibut oils are very good sources of energy for our body.
*Cottonseed oil:
- Source "Gossypium hirsutum"
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- This species is the source of cellulose rich cotton fibers, and the
seeds are also the source of the oil.
- Composition: rich in linoleic acid (one of the essential fatty acids)
+ palmitic + oleic + stearic acids.
- Uses:
This oil is not utilized as dietary supplement because it doesn't
contain one of the four main essential fatty acids (α, γ, EPA and
DHA)
Gossypium its oil is used as a solvent for injections
(intramuscular), soaps
Cotton seed itself contains 1.1-1.3% gossypol (i.e. a dimeric
sesquiterpene, has an anti-fertility (sterility) effect  used as mail
contraceptive agent).
Cotton oil is used as vehicle.
*Evening primrose oil:
- Uses:
Dietary supplement for the presence of γ-linolenic acid.
In dietary supplements, either we add γ-linolenic acid directly as
active essential fatty acid or we add the oil that is rich in this type
of fatty acid (e.g. evening primrose or borage oil  high nutritional
value due to linoleic acid content which is also essential).
*Honesty oil:
- Source "Lunaria annua"
- Composition: The main oil is erucic acid (43%).
Unique characteristic It exceptionally contains nervonic acid
(25%)  this is very important to help treatment of multiple
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sclerosis (i.e. an autoimmune disease that is characterized by
deficiency in nervonic acid (one of the important fatty acid
components of the phospholipids of the myelin tissue in neurons).
*Linseed (flaxseed) oil:
- Source "Linum usitatissimum"
- Composition: high level of α-linolenic acid (one of the rare oils that
are rich in α-linolenic acid)
- Uses:
Dietary supplement for α-linolenic acid content.
*Corn oil:
- Uses:
Food oil (cooking oil), added to a lot of food products
Dietary supplement due to the presence of a high level of linoleic
acid, but its value as dietary supplement is not that high like the
other dietary supplements (e.g. evening primrose, borage and linseed
oils, these oils contain α,γ-linolenic acids which are more essential
and nutritional than corn oil).
It also has a nutritional value.
*Olive oil:
- Uses:
Emolient base, food oil
*Palm oil:
Rich in saturated fatty acids same as the coconut oil.
*Rapeseed oil:
- Source "Brassica napus"
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- Composition: rich in erucic acid (30-60%)
*Two oils that are rich in erucicacid : rapeseed oil + honesty oil
- Uses:
Food oil, using varieties producing lower levels of erucic acid where
the main components are now oleic, linoleic, α-linolenic and palmitic
acids,this increases the nutritional value of the oil to be good as a
food oil.
Erucic acid doesn't have a high nutritional value,its presence
renders the rapeseed oil to be used in industrial applications such
as: being used as drying oil in paint industry, also in fuel industry it
is used to reduce the release of toxic gases such as carbon
monoxide forming diesters.
*Sesame oil:
- Source "Sesamumindicum"
- Uses:
Food oil, soaps, solvent for injections, carrier in aromatherapy.
*Soya (soybean) oil:
- Uses:
Cooking food oil, dietary supplement (very high level of linoleic acid,
also it contains α-linolenic acid)
*Soya oil contains also a substantial amount of the sterols
(sitosterols especially β-sitosterol (one of its best applications is as
tissue regenerator and it is found in some natural products like
Mebo which has a very magic effect on burns), stigmasterol).
Sesame oil also shares these properties with soya oil, and it is found
as one of the components of Mebo.
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*Suet oil
*Sunflower oil:
- Source "Helianthus annuus"
- Composition: linoleic acid
- Uses: food oil, carrier oil in aromatherapy
*Theobroma oil "Cocoa oil":
- Source  "Theobroma cacao"
- After roasting of Theobroma cocoa seeds  expression of the
butter that is used as chocolate butter  bleaching/
darking/adding of vanilla  white or dark chocolates.
- Uses:
Chocolate butter in chocolate manufacturing
Very commonly used as suppository base (cocoa butter), because it
is solid at R.T.
*The main reason that gives the cocoa butter its characteristic
properties is that it is rich in a triglyceride with a peculiar
structure (almost equal portions one third quantities of 3 fatty
acids oleic acid (unsaturated), palmitic (saturated 16C) acid and
stearic acid (saturated 18C), this leads to the sharpness of its
melting point (30-35 degree C), its brittleness and fragility, and
also its non-greasiness.
*There is a slide that talks about evening primrose oil and borage oil
read it please.
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Fatty acids
Fats as important pharmaceutical materials include 3 topics (before
talking about eicosanoids, biological substances
(prostaglandins,thromboxanes and leukotrienes)) :
1) Fixed oils
2) Fatty acids
3) Waxes
- Earlier we were talking about fixed oils.
- Now we will talk about fatty acids themselves, one of their
common values is as essential fatty acids  nutritional dietary
supplements (α,γ-linolenic acids, EPA and DHA). Other fatty
acids that have pharmaceutical applications are:
A) Stearic acid: a source of many fatty acid derivatives, each
derivative has certain properties and uses,
emollient/stiffening/ hardening agent/dusting powder/ base/
lubricant  different uses resulted from different metals
associated with the stearic acid.
B)Oleic acid: used as adjunct emollient, adjunct added to
ointments and bases, nutritional fatty acid.
*Derivatives of oleic acid:
1) Ricinoleic acid the active ingredient in castor oil.
2) Undecenoic acid:
- 11C fatty acid with one double bond at C9 (the same position
as in oleic acid)
- also calledundecylenic acid
- a semi-synthetic fatty acid  derived from natural
precursor (one of 2 common fatty acids: oleic acid or
ricinoleic acid)
- fungistatic material (antifungal) added with zinc oxides as
powder or ointments or creams used for athletes foot.
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- It is derived from ricinoleic acid by a process of pyrolysis
(separation between C11 and C12 that carries the hydroxyl
group). Even from oleic acid the synthesis process is not
obtained directly by pyrolysis of oleic acid, instead it is always
obtained by pyrolysis of ricinoleic acid, so either we do
pyrolysis of ricinoleic acid to give undecylenic acid directly, or
we do oxidation of oleic acid at C12 (to determine the position
of cutting upon pyrolysis)to produce 12-hydroxyoleic acid
(ricinoleic acid) then we do pyrolysis to the produced
ricinoleic acid to give undecylenic acid (indirect method).
C) Sodium morrhuate:
- Its name is derived from the species name "Gadusmorrhua"
of cod liver oil, because this fatty acid resulted from the
sodium salts of the cod liver oil fatty acids.
- It is a sclerosing agent for varicose veins, and thus
facilitates obliteration. Before the surgical process we have
to use ointments/ oils based on morrhuate.
Waxes
The common ingredient between triglycerides, oils, fats, fatty
acids and waxes is: fatty acids.
All are described via their fatty acid composition.
- Triglycerides, oils and fats  described only by their fatty
acid composition, because the other part is glycerol and it is
common to all of them. We determine the nature and identity
of fatty acids and the type of salts that may be formed to
know the properties and uses.
- Waxes  described by both parts, fatty acid and alcohol
parts, because waxes differ from each other in both parts.
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*Waxes : are esters of long chain fatty acid (hydrocarbon
chain starts with carboxylate) and long chain fatty alcohol
(hydrocarbon chain starts with hydroxyl group).
- Range of chains of fatty acid part or fatty alcohol part : 16,
18or 20C chains.
- Usually both chains are saturated, and that's why waxes are
solid at R.T (with the exception of jojoba oil which is liquid
because it is rich in 20 (eicosa), 22 (docosa) multi-enoic acids.
- Jojoba oil is a wax because it is long chain fatty acid + long
chain fatty alcohol not glycerol, but it is called oil because it
is liquid at R.T.  jojoba oil doesn't consist of triglycerides.
- Jojoba oil is used in lipsticks; it has lubricant and emollient
effects.
**Examples of fatty acid-containing waxes:
1) Bees wax:
- The most common
- One of the best waxes utilized in pharmacy as a
pharmaceutical adjunct, pharmaceutical stiffening/hardening
agent, as a base for suppositories.
*General pharmaceutical uses of waxes : stiffening/ hardening
agents in ointments and creams or in liquid preparations to
increase the rigidity of the external or oily phase. In addition
to their use as bases (vehicles) for suppositories.
2) White wax:
- derived from bees wax (which is prepared from beehive
"Apis mellifera" ).
**Beehive is rich in many products:honey (nutritional and
therapeutic value), royal jelly (therapeutic value), bees wax
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and propolis / bee gum (rich in phenolic acids, flavonoids,
produced by bees to seal the cracks in the hive).
**Sources of waxes : animal and plant sources.
-examples of waxes from plant sources: Carnauba wax,
Bayberry wax. (not very important examples).
- White wax is obtained from bees wax by bleaching (exposing
the bees wax to sunlight)
- It has the same uses as bees wax.
3) Spermaceti:
- Obtained from the heads of certain species of whales
- It has a nice odor
- Precious wax; because its source is very rare (scarcity of
the source).
- Its composition is simple (fatty acid (stearic acid, palmitic
acid) esters of cetylalcohol (16C) = palmityl alcohol =
hexadecyl alcohol or hexadecanol) cetyl stearate or cetyl
palmitate.
- Since they are simple esters, we can synthesize them to
produce synthetic spermaceti (but no matter that the
composition of synthetic spermaceti could be of the same
value, quality and properties like that of the natural
spermaceti).
4) Jojoba oil: we have talked about it.
**Animals and plants (especially plants) produce waxes as
protective materials (protect the dermal tissues of plant) +
they prevent dehydration or drying of the plants, because the
presence of waxes leads to retention of water and prevents
evaporation of water and this keeps the plant aerial parts
fresh and vegetative.
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