HYDROCARBONS AND

DERIVATIVES
PREPARED BY: ANA MARIE L. RUBENICIA, RPH, MS PHARM

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General Objectives:
 To identify the pharmacopoeial and related drugs of
biological origin with constituents that contains
hydrocarbons and its derivatives.
 To understand the chemistry of those constituents
and their significance in the pharmaceutical
industry.
References:
Trease and Evans Pharmacognosy 16th edition
Tyler, V. E., L.R. Brady and J. E. Robbers. Pharmacognosy.
9th ed.

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Outline:
Hydrocarbons and derivatives
Monobasic Acids
 C1–C6 Monocarboxylic acids
 Fatty acids
 Aromatic acids
Dibasic and Tribasic Acids
Alcohols
 Monohydric aliphatic alcohols, Monohydric terpene alcohols,
Monohydric aromatic alcohols, Dihydric alcohols, Trihydric
alcohols, Polyhydric aliphatic alcohols
Fats and Oils
Waxes
Prostaglandins
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Organic
Compounds
 Capsaicin, the compound
responsible for the
characteristic spiciness of hot
peppers, is the active
ingredient in several topical
creams for pain relief.
 Caffeine is the bitter-tasting
stimulant found in coffee, tea,
cola beverages, and chocolate.
---notice the elements that makes up the
molecules of capsaicin and caffeine.
What are the common features of these
organic compounds?
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What are the common features
of these organic compounds?

 All organic compounds contain carbon

atoms and most contain hydrogen atoms.
Carbon always forms four covalent
bonds, and hydrogen forms one covalent
bond.
 Carbon forms single, double, and triple
bonds to other carbon atoms.
 Some compounds have chains of atoms
and some compounds have rings.
 Organic compounds may also contain
elements other than carbon and
hydrogen. Any atom that is not carbon or
hydrogen is called a heteroatom.
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FUNCTIONAL GROUPS
In addition to strong C- C and C -H bonds, organic molecules may
have other structural. There are features as well. →structural
features, called functional groups

Ethanol (CH3CH2OH), for example, has two carbons and five hydrogens in its carbon
backbone, as well as an OH group, a functional group called a hydroxyl group. The hydroxyl
group determines the physical properties of ethanol as well as the type of reactions it
undergoes. Moreover, any organic molecule containing a hydroxyl group has properties
similar to ethanol. Compounds that contain a hydroxyl group are called alcohols.

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HYDROCARBONS
Hydrocarbons are compounds that contain only the elements of
carbon and hydrogen, as shown in

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HYDROCARBONS
Hydrocarbons are compounds that contain only the elements of
carbon and hydrogen, as shown in

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COMPOUNDS CONTAINING A SINGLE BOND TO A
HETEROATOM
Several types of functional groups contain a carbon atom singly
bonded to a heteroatom. Common examples include alkyl halides,
alcohols, ethers, and amines

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COMPOUNDS CONTAINING A
SINGLE BOND TO A Identify the functional
HETEROATOM
group.

Tetrahydrocannabinol
(THC), the active
component in
marijuana, is an ether
because it contains
an O atom bonded to
two carbon atoms. In
this case the O atom
is also part of a ring.

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COMPOUNDS CONTAINING A C=O GROUP
Many different kinds of compounds contain a carbon–oxygen double
bond (C O, carbonyl group). Carbonyl compounds include aldehydes,
ketones, carboxylic acids, esters, and amides.

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COMPOUNDS CONTAINING A C=O GROUP
Take special note of the condensed structures used to draw
aldehydes, carboxylic acids, and esters.

Hydrocarbon derivatives are compounds that are made primarily of

carbon and hydrogen atoms with specific groups of atoms attached.
These specific groups of atoms are called functional groups.
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IIdentify the ff compounds.

 HYDROCARBONS
DERIVATIVES

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 HC are found in Isoprene (C5H8),
HYDROCARBONS (HC) the unsaturated hydrocarbon
Some substances from natural moiety from which the terpenoids
sources where we find HCs: (isoprenoids) can be constructed.

HC are important in nature as

components of cuticular waxes.
Waxes - are odd-numbered long-
chain alkanes within the range C25–35
formed by decarboxylation of the
next higher, even-numbered, free Sesquiterpene Squalene
fatty acid.
A number of cyclic terpenoid
hydrocarbons including
limonene, pinene,
phellandrene and cadinene are
components of essential oils.
Rubber, gutta and the
carotenes are polyunsaturated
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MONOBASIC ACIDS
Important Monobasic
 Organic acids possess one or Acids:
more carboxyl groups and a
monobasic acid may be  C1–C6 Monocarboxylic
represented as RCOOH. acids
 Acids are found in all living
organisms and as derivatives  Fatty acids
of all the major metabolic
groups.  Aromatic acids
 Acids participate in essential
metabolism.
 Acid function in association
with coenzymes, and may
accumulate as simple salts,
esters and amides, or less
frequently in the free state.
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MONOBASIC ACIDS
Review on carboxylic acids
Carboxylic acids belongs to a family of organic molecules that
contain a carbonyl group (C= O) bonded to an element more
electronegative than carbon.
Carboxylic acids are organic
compounds containing a
carboxyl group (COOH).
 Although the structure of a
carboxylic acid is often
abbreviated as RCOOH or
RCO H, keep in mind that the
2

central carbon atom of the

functional group has a double
bond to one oxygen atom and a
single bond to another.

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 C1–C6 Monocarboxylic MONOBASIC ACIDS
acids
 these acids together with hydroxy- and keto-
derivatives are intermediates in the early
stages of the biosynthesis of fats, isoprenoid
compounds and various amino acids
 occur scattered throughout the plant kingdom
in the esterified form as a feature of some
volatile oils, resins, fats, coumarin derivatives
and alkaloids.

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Examples of C1–C6
monocarboxylic acids.
(monobasic acids)
Formic acid
FORMIC ACID (HCOOH)
 Name derives from its first
isolation from the ant, Formica
rufa. Ant bite release formic
acid causing itchiness.
 A decomposition product of
many vegetable materials.
 Occurs free in the hairs of the
stinging nettle.
 combined in the
gitaloxigenin series of
cardioactive glycosides.
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Examples of C1–C6
monocarboxylic acids
(monobasic acids) Acetic acid
ACETIC ACID (MeCOOH)
 An essential primary
metabolite, particularly as
acetyl-CoA.
 Common in the esterified
form.
 Vinegar is no less than 4%
acetic acid by volume,
making acetic acid the main
component of vinegar apart
from water.

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Examples of C1–C6
monocarboxylic acids
(monobasic acids) Propionic acid
PROPIONIC ACID
(MeCH2COOH)
 Esterified as a tropane
alkaloid.
 Produced in the fatty acid
oxidative cycle when an
acyl-CoA with an odd
number of carbon atoms is
involved

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Examples of C1–C6
monocarboxylic acids
(monobasic acids) n- butyric acid
iso- BUTYRIC ACID
 Occurs in traces in many
fats
 Occurs free in carob beans
(Ceratonia siliqua) and as its
ethyl ester in croton oil.
 Component of resins of the
Convolvulaceae and minor
tropane alkaloids.
 Intermediate in the
metabolism of valine
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Examples of C1–C6
monocarboxylic acids
Crotonic acid
(monobasic acids)
(transbutenoic acid)
CROTONIC ACID
Constituent of croton oil-
strong cathartic effect

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Examples of C1–C6
monocarboxylic acids Angelic acid
(monobasic acids)

ANGELIC ACID
 Occurs in the rhizome of
Angelica.
 Esterifying acid of the
Schizanthus alkaloid
schizanthine X and of some
volatile oils, e.g. chamomile
oils.
 Component of the Cevadilla
seed alkaloid cevadine and
Symphytum alkaloids

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agent
Examples of C1–C6
monocarboxylic acids
Senecioic acid
(monobasic acids)

SENECIOIC ACID
 First isolated from a species
of Senecio (Compositae).
 Occurs as the esterifying
acid of some alkaloids of
Dioscorea and Schizanthus.
 Component of the
pyranocoumarin samidin

Senecio
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(emmenagogue)
Fatty acids MONOBASIC ACIDS

 Naturally occurring animal fats and vegetable oils are formed

from fatty acids.
 Fatty acids are carboxylic acids (RCOOH) with long carbon
chains of 12–20 carbon atoms.
 Because a fatty acid has many nonpolar C- C and C- H bonds and
few polar bonds, fatty acids are insoluble in water. There are two
types of fatty acids.

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MONOBASIC ACIDS
Fatty acids
 Fatty acids are carboxylic acids (RCOOH) with long carbon
chains of 12–20 carbon atoms.
 Because a fatty acid has many nonpolar C- C and C- H bonds and
few polar bonds, fatty acids are insoluble in water. There are two
types of fatty acids.

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MONOBASIC ACIDS

Fatty acids
Here are four important fatty acids containing 18 carbon atoms:
 Stearic acid is one of the two most common saturated fatty acids.
 Oleic and linoleic acids are the most common unsaturated ones. Linoleic
and linolenic acids are essential fatty acids, meaning they cannot be
synthesized in the human body and must therefore be obtained in the diet. A
common source of these essential fatty acids is whole milk.

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MONOBASIC ACIDS

Fatty acids
Generally, double bonds in naturally occurring fatty acids are cis.
The presence of cis double bonds ( ) affects the melting point of these
fatty acids greatly.
As the number of double bonds in the fatty acid increases, the
melting point decreases --- don’t forget

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MONOBASIC ACIDS

Fatty acids
Fats and oils are organic molecules synthesized in plant and animal
cells from fatty acids. Fats and oils have different physical properties.
 Fats are solids at room temperature. Fats are generally formed
from fatty acids having few double bonds.
 Oils are liquids at room temperature. Oils are generally formed
from fatty acids having a larger number of double bonds.
Saturated fats are typically obtained from animal sources, while
unsaturated oils are common in vegetable sources. Thus, butter and
lard are formed from saturated fatty acids, while olive oil and
safflower oil are formed from unsaturated fatty acids. An exception to
this generalization is coconut oil, which is composed largely of
saturated fatty acids.
>Considerable evidence suggests that an elevated cholesterol level is
linked to increased risk of heart disease. Saturated fats stimulate
cholesterol synthesis in the liver, resulting in an increase in cholesterol
concentration in the blood.
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MONOBASIC ACIDS

Fatty acids
 When an oil is partially hydrogenated, some double bonds react with H2, while some double
bonds remain in the product. Since the product has fewer double bonds, it has a higher
melting point. Thus, a liquid oil is converted to a semi-solid.
 Partial hydrogenation decreases the number of carbons bonded to double bonds, making
the molecule less easily oxidized, thereby increasing its shelf life.

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Fatty acids MONOBASIC ACIDS
 Fatty acids are usually obtained by hydrolysis of fats or oils.
 The materials are usually mixtures, and the composition can vary with th source. Some
acids are used in topical antifungal preparations; sodium morrhuate is a sclerosing
agent, and linoleic and linolenic acids are used as a dietary supplement.
---Below are common fatty acids. Take note that saturated fatty acids have higher melting
points than unsaturated fatty acids.

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Fatty acids MONOBASIC ACIDS
Fatty acids include cyclic compounds such as hydnocarpic acid and the
prostaglandins. The latter are a group of physiologically active essential fatty acids
found in most body tissues and are involved in the platelet-aggregation and
inflammatory processes. They promote smooth muscle contraction making them of
clinical use as effective abortifacients and for inducing labour.
All the active natural prostaglandins are derivatives of prostanoic acidA rich source
of prostaglandin A2 (PGA2) is the soft coral Plexaura homomalla. (study the
structures below)

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Examples of Fatty Acids
(monobasic acids)

Stearic acid of Stearic Acid

pharmaceutic quality
contains not less than 40% of  Stearic acid is used as an
stearic acid and not less than emulsion adjunct and a tablet
40% of palmitic acid; the sum lubricant.
of these 2 acids is not less  Calcium stearate and
than 90%. magnesium stearate are used as
-These materials are hard, tablet lubricants, zinc stearate is
white or faintly yellow solids used in dusting powders,
or powders and are sodium stearate is used as an
practically insoluble in water. emulsifying and stiffening
agent, and aluminum
monostearate is used as a
suspending agent.
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 Examples of Fatty Acids
Oleic Acid
(monobasic acids)

Oleic acid is obtained from edible fats and

fixed oils. It is often obtained as a by product in  Oleic acid is used as an
the production of stearic acid.
emulsion adjunct.
Oleic acid consists chiefly of cis-9-
octadecenoic acid and is a colorless to pale  Ethyl oleate is used as a
yellow, oily liquid. pharmaceuticvehicle, and oleyl
It is practically insoluble in water but is alcohol is employed as an
miscible with alcohol. It gradually absorbs emollient and emulsifying
oxygen and darkens when exposed to air. agent.
 Ethyl oleate, compared with
fixed oil vehicles, is less viscous
and more rapidly absorbed by
body tissues,
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 Examples of Fatty Acids Linoleic and Linolenic
(monobasic acids) Acids

Linoleic and linolenic acids are

polyunsaturated octadecennic acids.
These fatty acids are essential for
human nutrition and have been
called vitamin F.
A mixture of essential unsaturated
fatty acids that contains primarily
linoleic and linolenic acids can be
obtained from soybean oil and other
suitable vegetable oils. This mixture
of acids is used as a dietary
supplement.

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Examples of Fatty Acids Undecylenic Acid
(monobasic acids)

Undecylenic acid is 10-undecenoic

acid. It is prepared by pyrolysis of Undecylcnic acid has antifungal
ricinoleic acid, which is obtained properties and is an ingredient,
from castor oil. often combined with zinc
undecylenate or other agents, in
Calcium undecylenate is used in ointments and powders for topical
powders for diaper rash and similar application to treat athlete's loot
skin irritations (Decylenes, Desenexa, Merlenate
®, Quinsana Plus ®, and
Undoguent®).

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 Examples of Fatty Acids Sodium Morrhuate
(monobasic acids)

Sodium morrhuate is the sodium

 The usual dose, administered
salts of the fatty acids of cod liver oil.
intravenously by special
 It is available as a sterile solution injection, is 1 ml of a 5% solution
and is used as a sclerosing agent to to a localized area.
obliterate varicose veins.
 Sodium morrhuate injection may
show a separation of solid
material on standing; it should
not be used if any such material
does not dissolve completely
when warmed.

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FATTY ACIDS
(monobasic acids)  Iodine values are useful
Iodine Value constants for acids, fixed
oils, fats and waxes, and
Iodine Value - a measure of help to indicate the
unsaturatedness where in composition of complex
iodine or its equivalent is mixtures as well as pure
taken up at these double substances.
bonds found in fatty acids.
The iodine value is the
number of parts of iodine
absorbed by 100 parts by
weight of the substance.

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 Aromatic Acids
MONOBASIC ACIDS

Common aromatic acids:

CINNAMIC ACID
→benzoic acid and cinnamic acid
 (unsaturated side-chain)
 widely distributed in nature and
often occur free and combined in BENZOIC ACID
considerable amounts in drugs such
as balsams.
 Truxillic acid, a polymer of
cinnamic acid, occurs in coca
leaves.
---notice the aromatic rings and
TRUXILIC ACID
carboxylic functional groups. Aromatic
refers to compounds that contain a
benzene ring.
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MONOBASIC ACIDS
Examples of Aromatic Acids
with alcohol group
Quinic acid-
(tetrahydroxyhexahydrobenzoic acid) QUINIC ACID
- an acids having an alcohol group;
occurs in cinchona bark.
Mandelic acid- occurs in combination
in cyanogenetic glycosides such as MANDELIC ACID
those of bitter almonds and other
species of Prunus.
Shikimic acid -important intermediate
metabolite. It is the starting material
for the semisynthesis of the antiviral
drug oseltamivir (Tamiflu®) for use
against bird flu infections in humansIts SHIKIMIC ACID
principal source has been star-anise
fruits.
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MONOBASIC ACIDS
Examples of Aromatic
Acids
Chlorogenic or caffeotannic acid is
a condensation product of caffeic
acid and quinic acid.
It occurs in maté, coffee, elder CHLOROGENIC
flowers, lime flowers, hops and nux ACID
vomica and is converted into a
green compound, which serves for
its detection, when an aqueous
extract is treated with ammonia and
exposed to air

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Next to monobasic acids…
DIBASIC AND TRIBASIC
ACIDS
Dibasic acids or dicarboxylic acids
series are:
 malonic acid
 succinic acid

Oxalic acid is the basic unit of the first

malonic acid
of a series of dicarboxylic acids.
Fumaric acid – unsaturated, closely
related to malonic acid
Malic acid - found in fruits such as
apples and tamarinds
Tartaric acid - occurs in tamarinds and
other fruits.
---notice the number of carboxylic acid
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tartaric acid
group present in the molecules
DIBASIC AND TRIBASIC
ACIDS

Tribasic acids or tricarboxylic

acids that are related:
 citric, isocitric and aconitic
Citric acid is abundant in fruit
juices. It forms part of the Krebs’
cycle and the glyoxalate cycle in
microorganisms.
Aconitic acid, which occurs in
Aconitum spp., is anhydrocitric acid.
---notice the number of carboxylic
acid group present in the molecules
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Next dibasic and tribasic acids..

ALCOHOLS

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 Next dibasic and tribasic acids..They can be classed according to the
number of hydroxyl groups present:
ALCOHOLS  monohydric alcohols-one
hydroxyl
Alcohols possess one or more  dihydric-two,
hydroxyl groups and exist naturally  trihydric-three
in either the free state or combined  polyhydric-four or more
as esters.
Others:
Like phenols they generally have
common names ending in ‘ol’ (e.g. Monohydric aliphatic alcohols,
ethanol, glycerol and mannitol). Monohydric terpene alcohols,
Monohydric aromatic alcohols, Dihydric
. alcohols, Trihydric alcohols, Polyhydric
aliphatic alcohols

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Monohydric aliphatic
alcohols ALCOHOLS

monohydric aliphatic alcohols

such as methanol, ethanol →
esterified to form methyl
salicylate in oil of wintergreen
and methyl and ethyl esters
responsible for some fruit
aromas.

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Monohydric aliphatic
alcohols ALCOHOLS
Examples are esterified long-chain
alcohols which includes:
 cetyl alcohol (C16H33OH)
 ceryl alcohol (C26H53OH)
myricyl alcohol
 myricyl alcohol (C30H61OH)
ester
Such alcohols also participate in the
formation of esters which are
constituents of leaf cuticular waxes;
an example is Carnauba Wax BP
which contains myricyl cerotate.
---notice the long aliphatic carbon chain
esterified myricyl
and the number of alcohol group.
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alcohol
Monohydric terpene
alcohols ALCOHOLS

Monohydric terpene alcohols are

particularly evident as constituents of
volatile oils namely:
(1) non-cyclic terpene alcohols occur in
many volatile oils—for example
 geraniol in otto of rose, have the isoprene
units
 nerol in oils of orange and
 bergamot and linalool - both free and
combined as linalyl acetate in oils of
lavender and rosemary
---notice the alcohol group as well as the isoprene
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units
C5: The branched-chain
C5 ‘isoprene’ unit is a
feature of compounds
formed from mevalonate.
The isoprene units are
found in terpenes.

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Monohydric terpene
alcohols ALCOHOLS

Monohydric terpene alcohols

are particularly evident as
constituents of volatile oils
namely:
(2) monocyclic terpene alcohols terpenyl acetate
are represented by terpineol terpineol
and its acetate in oil of neroli
and menthol and its acetate n
oil of peppermint;

have the isoprene

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Methyl acetate
Monohydric terpene
alcohols ALCOHOLS

Monohydric terpene alcohols

are particularly evident as
constituents of volatile oils
namely:
(3) dicyclic terpene alcohols are
particularly abundant in the sabinyl acetate
Coniferae (e.g. sabinol and its sabinol
acetate in Juniperus sabina).

have the isoprene

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Juniperus sabina
Monohydric aromatic
alcohols ALCOHOL

EXAMPLES
Benzyl alcohol, and
cinnamyl alcohol, occur
both free and as esters of
benzoic and cinnamic acids
in balsams such as Tolu and
Peru.
---notice the benzene ring and
alcohol group

cinnamyl acetate
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Monohydric aromatic
alcohols ALCOHOL
EXAMPLES
 Coniferyl alcohol, which
forms an important
component of the lignin
molecule.
Lignins are extremely
complex phenylpropane
polymers; they form an
important strengthening
material of plant cell walls
coniferyl alcohol
---notice the benzene ring and
alcohol group
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Dihydric alcohols ALCOHOLS

Dihydric alcohols or glycols

are compounds containing
two hydroxyl groups.
The dihydric alcohol
panaxadiol is a component
of some ginseng steroids, and
oenanthotoxin, the panaxadiol
poisonous constituent of the
hemlock water dropworts
(Oenanthe spp.), is a polyene
diol.
---notice the number of alcohol
group.
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Trihydric alcohols ALCOHOLS

An important example is
glycerol (propan-1,2,3-
triol), an essential component
of fixed oils and fats.
-with 3 hydroxyl groups
---notice the number of alcohol glycerol
group.

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Polyhydric aliphatic ALCOHOLS
alcohols
Polyhydric aliphatic alcohols
are alcohols with either four
or six hydroxyl groups.
Examples:
Erythritol - found in
seaweeds and certain lichens
both free and combined with Erythritol
lecanoric acid.
---notice the number of alcohol
group.

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Polyhydric aliphatic
alcohols ALCOHOLS

Polyhydric aliphatic alcohols are

alcohols with either four or six hydroxyl
groups. Examples:
sorbitol, mannitol and dulcitol -
hexahydric sugar alcohols
 sorbitol is abundant in many
rosaceous fruits mannitol
sorbitol
 mannitol - abundant in manna
 dulcitol abundant in species of
Euonymus.
dulcitol
---notice the number of alcohol group.
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Alcohols
 Ethanol: 92.3% by weight of ethanol, 94.9% by volume; 70 %
which is used as local anti- infective
 Diluted Alcohol: 48.4 % to 49.5% used as solvent
 Brandy: distillation from wine
 Whisky: fermented malted grain
 Rum: fermented molasses
 Wine: mild stimulant and tonic

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 LIPIDS
(ESTERS)
 Lipids contain a
large number of
nonpolar carbon–
carbon and
carbon–hydrogen
bonds.
 In addition, most
lipids have a few
polar bonds that
may be found in a
variety of
functional groups.

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 Most hydrolyzable lipids
contain an ester. In the
Lipids can be categorized as presence of acid, base, or an
hydrolyzable or enzyme, the C O bond of the
nonhydrolyzable. ester is cleaved, and a
carboxylic acid and an
1. Hydrolyzable lipids can alcohol are formed.
be converted into smaller
molecules by hydrolysis with
water.

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Lipids can be categorized as hydrolyzable or nonhydrolyzable.
2. Nonhydrolyzable lipids cannot be cleaved into smaller units
by aqueous hydrolysis. Nonhydrolyzable lipids tend to be more
varied in structure. We will examine three different types: steroids,
fat-soluble vitamins, and eicosanoids.

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 Lipids are biomolecules that
are soluble in organic solvents
and insoluble in water.
 Contain a large number of
nonpolar carbon–carbon and
carbon–hydrogen bonds
 Most lipids have a few polar
bonds that may be found in a
variety of functional groups.

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LIPIDS
(ESTERS)

Lipids are esters of long-

chain fatty acids and
alcohols, or of closely related
derivatives.

Includes: waxes

Fixed oils and fats - glycerol

combines with the fatty acids.
Waxes - the alcohol has a
higher molecular weight,
e.g., cetvl alcohol.
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 Hydrolyzable lipids can be  Nonhydrolyzable lipids
converted into smaller cannot be cleaved into
molecules by hydrolysis with smaller units by aqueous
water. hydrolysis.

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Hydrolyzable Lipids

 Most hydrolyzable lipids

contain an ester.
 In the presence of acid,
base, or an enzyme, the C
O bond of the ester is
cleaved, and a carboxylic
acid and an alcohol are
formed.

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Fatty Acids Palmitic Acid

Fatty acids are carboxylic acids

(RCOOH) with long carbon
chains of 12–20 carbon atoms.
They have many nonpolar C-C
and C-H bonds and few polar
bonds, fatty acids are lipids,
making them soluble in organic
solvents and insoluble in water.

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 Fatty Acids
 Naturally occurring fatty acids
have an even number of
carbon atoms. There are two
types of fatty acids.
Saturated fatty acids have no double bonds in their long
hydrocarbon chains.
Unsaturated fatty acids have one or more double bonds in their long
hydrocarbon chains.
Generally, double bonds in naturally occurring fatty acids are cis.

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WAXES
LIPIDS

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WAXES LIPIDS
For example, spermaceti wax, isolated from the heads of
sperm whales, is largely cetyl palmitate, an ester with the
structure CH3(CH2)14COO(CH2)15CH3. Cetyl palmitate is
formed from a 16-carbon fatty acid [CH3(CH2)14COOH]
and a 16-carbon alcohol [CH3(CH2)15OH].

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 Yellow Beeswax ,
WAXES White Beeswax
Yellow beeswax is prepared, after removal
Beeswax is obtained by of the honey, by melting the comb under
melting and purifying the water , straining, and allowing the wax to
honeycomb of Apis solidify in suitable moulds.
mellifica and other bees
White beeswax is prepared from the above
Constituent/s: Beeswax is by treatment with charcoal, potassium
a true wax, consisting of permanganate, chromic acid, chlorine,
about 80% of myricyl etc., or by the slow bleaching action of
light, air and moisture.
palmitate (myricin), with
possibly a little myricyl
stearate.
Use/s: preparation of
plasters, ointments and
polishes.
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 Carnauba Wax
WAXES
Carnauba wax, included in the
BP/EP (2000) and USP/NF (1995), is
derived from the leaves of
Copernicia cerifera
Constituent/s: myricyl cerotate
Use/s: a tablet-coating agent and
in other industries for the
manufacture of candles and
leather polish. Ithas been
suggested as a replacement for
beeswax in the preparation of
phytocosmetics.
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WAXES Spermaceti
Spermaceti, a waxy substance
obtained from the head of the sperm
whale (endangered), Physeter
macrocephalus
Constituent/s: mixture of hexadecyl
esters of fatty acids.
Use/s: a quality emollient and a
desirable ingredient in cold creams and
other cosmetics.
Synthetic spermaceti or cetyl esters wax is
a mixture consisting primarily of estersof
saturated fatty alcohols (C 14 to C18) and
saturated fatty acids (C14 to C18).
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WAXES Jojoba Oil
Jojoba oil is a liquid wax expressed
from seeds of Simmondsia chinensis
Constituent/s : 35% of eicosenoic acid
(a C20 unsaturated acid), 22% of
eicosenol (a C20 unsaturated alcohol),
and 21% of docosenol (a C22
unsaturated alcohol).
Use/s: useful emollients and agents of
pharmaceutic necessity.

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Fats and oils are triacylglycerols from
animal fats and vehgetable oils.
LIPIDS

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Fats and Oils are
triacylglycerols. LIPIDS

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
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Fats and Oils are
triacylglycerols. LIPIDS

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 LIPIDS Fixed Oils and Fats
The United States Pharmacopeia 2) Saponification value
includes several tests that indicates the number of
determine the identity, quality, milligrams of potassium
and purity of fixed oils. hydroxide required to
neutralize the free acids and
1) acid value or acid number saponify the esters contained
(the number of milligrams of in I g of the substance
potassium hydroxide required to
neutralize the free fatty acids in 1 3) Iodine number (the
g of the substance) indicates the number of grams of iodine
amount of free fatty acids absorbed, under prescribed
present in the oil conditions, by 100 g of the
substance) indicates he
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 LIPIDS Fixed Oils and Fats
Fixed oils and fats of vegetable Animal fats are separated
origin are obtained by from other tissues by
expression in hydraulic presses. rendering with steam, with or
without pressure. The heat
1) "virgin oil“ or a "cold- melts the fat, which rises to
pressed oil“ – oil obtained by the top and may be
expression is carried out in separated by decantation.
the cold.
Oils may be further clarified
2) "hot-pressed oil “ - oil by filtration and bleached
obtained by expression is with ozone. Stearins are often
carried out in heat. removed by chilling and
filtration,
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Pharmaceutical Fixed Oils
and Fats
Almond Oil
Almond Oil is a fixed oil
obtained by expression from
the seeds of Prunus dulcis
CN: sweet almond, bitter
almond
Constituent/s: glycoside
amygdalin (bitter almonds).
Use/s:
 vehicle for oily injections
 mild, laxative action
 flavouring agents
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Pharmaceutical Fixed Oils
and Fats Arachis Oil
Arachis oil (peanut oil) is
obtained by expression from
the seeds of Arachis
hypogaea.
CN: earth-nut, ground-nut,
peanut
Constituent/s: oleic, linoleic,
palmitic, arachidic, stearic,
lignoceric and other acids.
Use/s: an ingredient of
camphorated oil but is used
mainly in the production of
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margarine, cooking fats, etc.
Pharmaceutical Fixed Oils
and Fats Coconut Oil

Coconut oil is expressed oil of

the dried solid part of the
endosperm of the coconut, Cocos
nucifera
CN: coconut palm
Constituent/s: myristic acid,
lauric acid and other saturated
fatty acids
Use/s: ingredients in a number of
combination products for oral
administration (e.g., Lorialac
Powder® and Osmolite Liquid ®).
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Pharmaceutical Fixed Oils
and Fats
Cottonseed Oil
Cottonseed oil is the refined,
fixed oil obtained from the seed of
cultivated plants of various
varieties of Gossypium hirsutum.
Constituent/s: linoleic (45%),
oleic (30c/o), palmitic (20%),
myristic (3%), stearic and
arachidic (1% ofeach).
Use/s: employed
pharmaceutically as a solvent for
a number of injections
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Pharmaceutical Fixed Oils
and Fats Linseed and Linseed
Oil
Linseed (flaxseed) is the dried
ripe seed of Linum usitatissimum
Constituent/s: fixed oil,
mucilage, traces of cyanogenic
glycosides
Use/s: demulcent, liniments,
antibacterial propeeties

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Pharmaceutical Fixed Oils
and Fats
Olive Oil
Olive oil (salad oil, sweet oil) is a fixed
oil which is expressed from the ripe
fruits of Olea europoea
CN: Olive
Constituent/s: oleic, linoleic acid
palmitic, stearic acid
Use/s:
 in the manufacture of parenteral preparations is
required to have a lower acid value and
peroxide value than that normally required, and
to be almost free of water
 a demulcent, an emollient, and a laxative.
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Pharmaceutical Fixed Oils Palm Oil and Palm
and Fats Kernel Oil
Palm oil is obtained by steaming
and expression of the mesocarp
of the fruits of Elaeis guineënsis
CN: Olive
Constituent/s: Lauric acid
Use/s: Base for semi-solid
preparation

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Pharmaceutical Fixed Oils
and Fats Rapeseed Oil
Refined Rapeseed Oil BP/EP is
obtained by mechanical
expression orby extraction from
the seeds of Brassica napus
Constituent/s: Oleic, linoleic and
linolenic acids
Use/s: as salad oil/dressing

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Pharmaceutical Fixed Oils
and Fats
Sesame Oil
Sesame oil (Gingelly oil, Teel oil )
is obtained by refining the
expressed or extracted oil from
the seeds of Sesamum indicum.
Constituent/s: oleic and linoleic
(about 43 1/v of each), palmitic
(9%), and stearic (4%).
Use/s: it solvent for intramuscular
injections. It has nutritive, laxative,
demulcent, and emollient
properties.
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Pharmaceutical Fixed Oils
and Fats Soyabean Oil
Soya oil is obtained from the ripe seeds of
Glycine soja
Constituent/s: Refined soya oil linoleic (48–
58%), oleic (17–30%), linolenic (5–11%) and
stearic (3–5%).
Use/s: Hypercholesterolemia, treatment of
osteoarthritis
 an ingredient in parenteral nutrients
(Intralipid®, Soyacal®, and Travamulsion ®)
and is a source of lecithin.
 Lecithin is an ingredient in a number of
proprietary products that are useful in
controlling deranged lipid and cholesterol
metabolisms.
 Stigmasterol, obtained from the lipid fraction
of soybeans,
amrubenicia2020 can be used as a precursor for
steroidal hormones
Pharmaceutical Fixed Oils
and Fats Sunflower Oil

Sunflower oil is obtained from

the seeds of Helianthus annuus
Constituent/s: linoleic acid (48–
74%), oleic acid (14–40%),
palmitic acid (4–9%) and stearic
acid (1–7%).
Use/s: alternative to corn oil and
safflower oil for culinary
purposes; and it is an ingredient
in a number of specialty dietary
supplements
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Pharmaceutical Fixed Oils
and Fats Theobroma Oil

Oil of theobroma or cocoa

butter may be obtained from the
ground of Theobroma cacao
(Sterculiaceae) by hot expression
Constituent/s: glycerides of
stearic, palmitic, arachidic, oleic
and other acids.
Use/s: Its melting point (31–34°)
makes it ideal for the preparation
of suppositories.

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Pharmaceutical Fixed Oils
and Fats Germ Oils
The refined and virgin wheat-germ oils
are described in the BP/EP and are
obtained by cold expression or by other
suitable mechanical means from the
germ of the wheat grain, Triticum
aestivum
Constituent/s: linoleic (52–59%),
palmitic (14–19%), oleic (12–23%) and
linolenic (3–10%) with limits for
ecosenoic ( 2.0%) and stearic ( 2.0%).
Use/s: natural source of vitamin E for
therapeutic purposes/parenteral
purposes.
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 Castor Oil (Virgin
Pharmaceutical Fixed Oils
and Fats castor oil)
Castor oil (cold-drawn castor oil) is a fixed
oil obtained from the seeds of Ricinus
communis
Constituent/s: ricinoleic acid
Use/s: domestic purgative, is now more
restricted to hospital use for administration
after food poisoning and as a preliminary to
intestinal examination. The usual dose is 15 to
60 ml.
Allied drugs: Croton seeds are obtained from Croton
tiglium; Physic nuts or Purging nuts are the seeds of
Jatropha curcas; Abrus seeds (prayer beads) are the
attractive red and black, but poisonous, seeds of Abrus
precatorius
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 Evening Primrose
Pharmaceutical Fixed Oils
and Fats Oil
Evening Primrose Oil obtained by
extraction and/or expression from the
seeds of Oenothera spp.
Constituent/s: esterified γ-linolenic
acid (GLA)
Use/s: precursor of the prostaglandins
for those individuals whose enzymic
conversion of linoleic acid to GLA is
deficient. The oil is now widely marketed
as a dietary supplement, for cosmetic
purposes, and more specifically for the
treatment of atopic eczema and
premenstrual syndrome (prostaglandin
E may be depleted in this condition).
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Pharmaceutical Fixed Oils Borage Oil
and Fats
Borage Oil is a refined fixed oil
expressed from the seeds of Borago
officinalis (starflower)
Constituent/s: esterified γ-linolenic
acid (GLA) also
Use/s:same medicinal purposes as
evening primrose oil except for atopic
eczema.
Other sources of GLA: other seed oils
contain appreciable quantities of GLA,
including those of Ribes nigrum and R.
rubrum (the black and red currant) and
Symphytum officinale (comfrey).
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Pharmaceutical Fixed Oils Corn Oil
and Fats
Corn oil is the refined oil obtained from
the embryo of Zea mays
Constituent/s: linoleic (50%), oleic
(37%), palmitic (10%), stearic (3%).
Use/s:
 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)

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 Ethiodjzed Oil
Pharmaceutical Fixed Oils Injection
and Fats
Ethiodized oil is an iodine addition
product of the ethyl ester of the fatty
acids of poppy seed
Constituent/s: not less than 35.2%
and not more than 38.9% of organically
combined iodine.
Use/s: radiopaque and is used as a
diagnostic aid in
hysterosalpingography and
lymphography.

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Pharmaceutical Fixed Oils Saw Palmetto Fruit
and Fats
Saw palmetto fruit BP/EP, BHP is
obtained from the palm Serenoa
repens (Bartram)
Constituent/s: flavonoids such as
rutin, isoquercitrin; phytosterols—
sitosterol
Use/s: inhibition of 5α-reductase
thus impeding the conversion of
testosterone to
dehydrotestosterone. The principal
use of the drug is for the
symptomatic treatment of benign
prostatic hyperplasia.
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Pharmaceutical Fixed Oils Hydnocarpus oil
and Fats
Hydnocarpus oil is the fixed oil obtained by
cold expression from the fresh ripe seeds of
Hydnocarpus wightiana, H. anthelmintica, H.
heterophylla and other species of Hydnocarpus,
and also of Taraktogenos kurzii
Constituent/s: hydnocarpic acid (about 48%),
chaulmoogric acid (about 27%), gorlic and other
acids
Use/s:strongly bactericidal towards the leprosy
micrococcus, esterified oil of H. wightiana is
preferable to that of other species.

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 Hydrous Wool Fat or
Pharmaceutical Fixed Oils Lanolin
and Fats
Lanolin contains between 25 and 30% of
water and therefore is commonly called
hydrous wool fat.
Lanolin is the purified, fatlike
substance from the wool of the sheep,
Ovis aries
Constituent/s: cholesterol and
isocholesterol; esters of lanopalmitic,
lanoceric, carnauhic, oleic, m yristic,
and other fatty acids.
Use/s: a water-absorbable ointment
base. It is an ingredient in many skin
creams and cosmetics
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 Wool Fat or Anhydrous
Pharmaceutical Fixed Oils Lanolin
and Fats
Anhydrous lanolin is lanolin that
contains not more than 0.25% of
water.
Wool fat (anhydrous lanolin) is a
purified fat-like substance prepared
from the wool of the sheep, Ovis aries
- Hydrous wool fat or lanolin contains
25% water.
Constituent/s: cholesterol and
isocholesterol, unsaturated
monohydric alcohols
Use/s: emollient base for creams and
ointments.
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 All prostaglandins (PC) have
PROSTAGLANDINS a cyclopentane ring with 2
aliphatic side chains.
Subscripts indicate the
Prostaglandins are C20 lipid number of double bonds in
metabolites formed in the body the side chains and the
(mammalian tissue) from essential, stereochemistry of members
unsaturated fatty acids of the diet. of each group.
The major prostaglandins have been
grouped into 4 main classes
designated as prostaglandins A, B, E,
and F.
Prostaglandin materials are
synthesized from in Plexaura
homomalla (sea fan or sea whip),
which is a coral found in reefs and
otheramrubenicia2020
chemical synthesis,
 PROSTAGLANDINS
Prostaglandin F2α Side Effects: contractile effect of
PGF2α; the action may extend to
Prostaglandin F2α , PGF2α , or smooth muscle of the
dinoprost is available as the gastrointestinal tract, producing
tromethamine salt. vomiting and/or diarrhea, and to
smooth muscle of the vascular
Use/s: terminating second system, causing elevation in
trimester pregnancy. blood pressure.
Action:stimulates
contractions of the gravid
uterus that are similar to the
contractions of the term
uterus at labor.

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Prostaglandin F2α
1 5-Methylprostaglandin F2α PROSTAGLANDINS
Side Effects: contractile effect of
15-Methyiprostaglandin F, PGF2α; the action may extend to
smooth muscle of the
15-methyl PGF2α , or gastrointestinal tract, producing
carboprost is the 15-methyl vomiting and/or diarrhea, and to
analog of PGF2α . smooth muscle of the vascular
system, causing elevation in
Use/s: terminating second blood pressure.
trimester pregnancy.
Action:stimulates
contractions of the gravid
uterus that are similar to the
contractions of the term
uterus at labor.
(action similar to Prostaglandin
F2α , PGF2α )
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Prostaglandin E2 PROSTAGLANDINS
Side Effects: vomiting, pyrexia,
Prostaglandin E2, PGE2, or diarrhea, nausea, headache, and
chills.
dinoprostone
Use/s: another uterine
stimulant that has been
approved for termination of
second trimester pregnancy.
PGE2 differs from PGF2α only in Prostaglandin E2
that the 9-oxygen substitutent is
a keto group. PGE2 is available
as a vaginal suppository that
should be stored at a
temperature below —20° C.
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ALPROSTADIL (PGE1) MISOPROSTOL
ACTION: Produces ACTION: Inhibits gastric
vasodilation; inhibits platelet acid secretion; also produces
aggregation and stimulates uterine contractions that may
intestinal and uterine smooth endanger pregnancy by
muscle. causing abortion.

USE: Palliative therapy to USE: Used orally in patients

maintain temporarily that are at high risk for
neonates with patent ductus developing ulcers during
arteriosus and congenital NSAID activity.
heart defects that restrict the
pulmonary or systemic blood
flow.
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DRUGS CONTAINING
ACIDS, ALCOHOLS AND Roselle
ESTERS
Roselle is a drug from dried calyces
and epicalyces of Hibiscus sabdariffa
Constituent/s: free acids including
citric, tartaric and malic acids and the
lactone of hydroxycitric acid;
anthocyanin
Use/s:
 colourant and flavouring component
for herbal preparations.
 Traditionally, all parts of the plant
have been employed as an astringent
and cooling agent; it has a diuretic
action.
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DRUGS CONTAINING ACIDS, Tamarind pulp
ALCOHOLS AND ESTERS
Tamarind pulp consists of the
fruit of the tree Tamarindus
indica.
Constituent/s: free organic
acids (about 10% of tartaric,
citric and malic) and their
salts, little nicotinic acid and
about 30–40% of invert sugar.
Use/s: mild laxative and was
formerly used in Confection of
Senna

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DRUGS CONTAINING ACIDS, Manna
ALCOHOLS AND ESTERS
The only manna of
commercial importance
is ash manna, derived
from Fraxinus ornus
Constituent/s: 55% of
the hexahydric alcohol
mannitol.
Use/s: mild laxative

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DRUGS CONTAINING ACIDS,
ALCOHOLS AND ESTERS Sumatra Benzoin
Two commercial varieties of benzoin—Sumatra
benzoin and Siam benzoinus
Sumatra benzoin (Gum Benjamin) is a balsamic
resin obtained from the incised stem of Styrax
benzoin, and Styrax paralleloneurus.
Constituent/s: free balsamic acids (cinnamic and
benzoic) and esters derived from them.
Use/s:
 when taken internally, acts as an expectorant
and antiseptic.
 food, drinks, perfumery and toiletry industries;
it is a component of incense.
Allied drug. Palembang benzoin, an inferior
variety produced in Sumatra
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DRUGS CONTAINING ACIDS,
ALCOHOLS AND ESTERS Siam Benzoin
Siam benzoin BP/EP is obtained by
incision of the trunk of Styrax
tonkinensis.
Constituent/s: coniferyl benzoate
Use/s: (same with Sumatra benzoin)
 when taken internally, acts as an
expectorant and antiseptic.
 food, drinks, perfumery and toiletry
industries; it is a component of
incense.
\

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DRUGS CONTAINING ACIDS,
ALCOHOLS AND ESTERS Ash Leaf
Ash leaf BP/EP consists of the
dried leaves of Fraxinus
excelsior, the common ash, or
Fraxinus oxyphylla.
Constituent/s: coumarin
glycoside fraxin, various
hydroxycinnamic acid
derivatives, e.g. chlorogenic
acid
Use/s: mild laxative and
diuretic\

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DRUGS CONTAINING ACIDS,
ALCOHOLS AND ESTERS Artichoke Leaf
The leaves of the globe
artichoke, Cynara
scolymus .
Constituent/s: Phenolic
acids are important
constituents and include
chlorogenic acid, caffeic
acid and cynarin (1, 5-di-
O-caffeoylquinic acid)
Use/s: treatment of
indigestion and dyspepsia;
for its use as a hepatic
amrubenicia2020
DRUGS CONTAINING ACIDS,
ALCOHOLS AND ESTERS Nettle Leaf
Dried leaves from Urtica dioica,
the stinging nettle, and U. urens
, the small nettle.
Constituent/s: chlorogenic,
caffeoylmalic, caffeic,malic and
fumaric; flavonoids include
quercetin and its glycosides
isoquercitrin and rutin (
Use/s:
 diuretic
 employed in various rheumatic
conditions
 assist micturition in cases of
benign prostatic hyperplasia.
amrubenicia2020
DRUGS CONTAINING ACIDS,
ALCOHOLS AND ESTERS Echinacea SPP
Three species are currently
important. Roots of Echinacea
augustifolia, the narrow-leaved
coneflower, and E. pallida, the
pale cornflower,
Constituent/s: A caffeic acid
derivative, echinacoside
Use/s:
 immunostimulant
 Prevention and treatment of
the common cold and other
respiratory complaints
.
amrubenicia2020
DRUGS CONTAINING ACIDS,
ALCOHOLS AND ESTERS Pygeum Bark
Pygeum bark is obtained from
the stems and branches of
Prunus Africana syn. Pygeum
africanum .
Constituent/s: ferulic acid
esters, phytosterols, triterpenoid
pentacyclic acids and a lipid
fraction involving C12–C24 fatty
acids
Use/s: symptomatic treatment of
benign prostatic hyperplasia.
The activity appears to be
comparable to that of Serenoa
repens fruit extracts
.
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DRUGS CONTAINING ACIDS,
ALCOHOLS AND ESTERS Peru Balsam
Balsam of Peru is obtained
from the trunk of Myroxylon
balsamum
Constituent/s: chief balsamic
esters present are benzyl
cinnamate (cinnamein), benzyl
benzoate and cinamyl
cinnamate (styracin)
Use/s:
 antiseptic dressing for wounds
and as a parasiticide.
 taken internally it is used to
treat catarrh and diarrhoea

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DRUGS CONTAINING ACIDS,
ALCOHOLS AND ESTERS Prepared Storax
Prepared storax (aka Levant
storax) is a balsam obtained
from the wounded trunk of
Liquidambar orientalis
Constituent/s: Storax is very
rich in free and combined
cinnamic acid. After purification
it yields 30–47% of total
balsamic acids.
Use/s: preparation of friars’
balsam and benzoin inhalation.

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DRUGS CONTAINING ACIDS,
ALCOHOLS AND ESTERS Tolu Balsam
Tolu Balsam is obtained by
incision from the trunk of
Myroxylon balsamum
Constituent/s: free aromatic
acids and contains about 12–
15% of free cinnamic and about
8% of free benzoic acid
Use/s: antiseptic and flavouring
properties and is commonly
added to cough mixtures in the
form of a syrup of tincture.

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amr2020

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