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VOLATILE OILS
Prepared by-
Afia Nabila
Lecturer
Department of Pharmacy, USTC.
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Definition
• Volatile oils are the odorous and volatile products of various plant.
As they have a tendency to undergo evaporation on being exposed
to the air even at an ambient temperature, they are invariably
termed as volatile oils, essential oil or ethereal oils.
• Chemically, they are composed of hydrocarbons of the general
formula (C5H8) and their oxygenated, hydrogenated and
dehydrogenated derivatives.
• All the volatile oils are of vegetable origin.
• These volatile oils are usually formed by two modes namely; first,
by hydrolysis of some glycosides; and secondly, by the
protoplasm directly.
• In most instances, the volatile oil preexists in the plant
and is usually contained in some special secretory
tissuesas glandular hairs, parenchyma cells, vittae or oil
tubes, in mesophyll (Eucalyptus leaves), sub-epidermal
tissues of Lemon and Orange. in lysigenous or
schizogenous passages, in all tissues (Conifers), In
petals (Orange. Rose), in bark and leaves (Cinnamon),
in pericarp (Umbelliferous fruits), in glandular hairs of
the stems and leaves (Mint), and in rind (Orange).
• These represent essence of active constituents of the plant
and hence also known as essential oils.
Why they are called Essential Oil?
• They are evaporated at ordinary temperature
• Volatile oils are colourless liquids, but when exposed
to air and direct sunlight these become darker due to
oxidation.
To prevent this darkening, they should he stored in a cool,
dry place in tightly stoppered preferably amber glass
containers.
• They possess characteristic odors
• Characterized by high refractive indices
• Most of them are optically active [specific rotation
is often a valuable diagnostic properties]
Physical Properties
• Volatile oils are immiscible with water, but they are
sufficiently soluble to impart their odor to water
• Soluble in ether, alcohol, chloroform and most
organic solvents.
• Volatile oils neither leave permanent grease spot on
filter paper nor saponified with alkalis
• They are present in entire plants (Mint, Conifers) or
any part of the plant (Rose)
No Volatile oil Fixed oil
1.
Volatile oil can evaporate when placed
under room temperature
Fixed oils do not evaporate at room temperature
2.
Mixtures of cleoptenes & stearoptenes are
termed as volatile oils
Esters of higher fatty acids & glycerin are called
as fixed oils.
3
Their primary source is leaves, roots, in
petals and bark.
Their major source is seeds of the plant and
animal.
4. Possess high refractive index Possess low refractive index
5. These are optically active. These are optically inactive.
6.
There is no spot (no permanent stain) left
after evaporation
Some type of spot (permanent stain) left after
evaporation
7. They are unable to undergo saponification Fixed oils can be easily saponified.
8.
Essential oils do not go rancid, rather they
oxidize and lose their therapeutic benefit
Fixed oils can go rancid (stale) over time
9. Colorless Some possess colors (yellowish)
10. Have characteristic odor May or may not possess odor
11. Immiscible in water Soluble in water
12. Obtained by distillation Obtained by extraction
13. Low boiling point High boiling point
14. Soybean oil, castor oil Cinnamon oil, peppermint oil.
Chemical composition
• Many volatile oils consist largely of Terpenes. The term
‘terpene’ was given to the compounds isolated from
terpentine, a volatile liquid isolated from pine trees.
• But there is a tendency to use more general term ‘terpenoids’,
which includes hydrocarbons and their oxygenated
derivatives.
• Terpenoids are volatile substances which give plants and
flowers their fragrance
• ‘Terpenoids are the hydrocarbons of plant origin of the
general formula (C5H8)n as well as their oxygenated,
hydrogenated, and dehydrogenated derivatives.’
• Isoprene Rule
Isoprene rule states that the terpenoid
molecules are constructed from two or
more isoprene unit.
• Special Isoprene Rule
It states that the terpenoid molecules
are constructed of two or more
isoprene units joined in a ‘head to tail’
fashion.
• But this rule can only be used as
guiding principle and not as a fixed
rule
• Most natural terpenoid hydrocarbons have the general
formula (C5H8) n. They can be classified on the basis
of number of carbon atoms present in the structure.
1. Monoterpenoids, 2 isoprene units (C5H8) 2
2. Sesquiterpenoids, 3 isoprene units (C5H8) 3
3. Diterpenoids, 4 isoprene units (C5H8)4
4. Triterpenoids, 6 isoprene units (C5H8) 6
5. Tetraterpenoids, 8 isoprene units (C5H8) 8
6. Polyterpenoid with a larger number (>8) of
isoprene units (C5H8) >8
Classification of Terpinoids
limonene
Monoterpenes Sesquiterpenes
Triterpenes
Lanosterol
Polyterpene
Cinnamaldehyde
• Each class can be further subdivided into subclasses
according to the number of rings present in the
structure.
1. Acyclic Terpenoids:
They contain open structure.
2. Monocyclic Terpenoids:
They contain one ring in the structure.
3. Bicyclic Terpenoids:
They contain two rings in the structure.
4. Tricyclic Terpenoids:
They contain three rings in the structure.
5. Tetracyclic Terpenoids:
They contain four rings in the structure.
Acyclic
Limonene
Monocyclic Bicyclic
Tricyclic
Tetracyclic
Lanosterol
Sources of Volatile oil
• Dried ripe fruits: Coriandar
oil, Anise oil
• Fresh ripe fruit: Lemon oil
• Dried ripe fruit rind: Bitter
range oil
• Dried leaves and flowering
tops: Peppermint oil,
Spearmint oil.
• Fresh leaves: Eucalyptus oil
• Dried bark: Cinnamon oil
• Dried stigma and style tops:
Saffron oil
• Dried flower buds: Clove oil
• Dried ripe seed: Nutmeg oil,
Cardamom oil
• Dried peel rhizome:
Calamus oil
• Aerial part: Chenopodium
oil
• Dried roots rhizome:
Valerian oil
• Ripe bulb: Garlic oil
• Wood : Sandal wood oil
• Unripe fruit: Black pepper
oil.
On the basis of chemical composition of volatile oil-
• Alcohol volatile oils: Coriander oil, Cardamom oil,
Rose oil
• Aldehyde Volatile Oils: Cinnamon oil, Lemon oil,
Saffron oil
• Ketone Volatile oil: Camphor oil, Caraway oil,
Spearmint oil
• Phenol volatile oil: Clove oil, Thyme oil,
• Phenolic ether Volatile oil: Nutmeg oil, Anise oil
• Oxides volatile oil: Eucalyptus oil, Chenopodium oil
• Ester volatile oil: Lavender oil
Classification
Natural drugs containing volatile oils can be
tested by following chemical tests:
1. Thin section of drug on treatment with
alcoholic solution of Sudan III develops red
color in the presence of volatile oils.
2. Thin section of drug is treated with tincture
of alkana, which produces red color that
indicates the presence of volatile oils in natural
drugs.
CHEMICAL TESTS
Volatile oils are used as flavouring agent, perfuming agent in
pharmaceutical formulations, foods, beverages, and in
cosmetic industries. These are also used as important medicinal
agent for therapeutic purposes like:
1. Carminative (e.g. Umbilliferous fruits)
2. Anti-helminitic (e.g. Chenopodium oil)
3. Diuretics (e.g. Juniper)
4. Antiseptic (e.g. Eucalyptus)
5. Counter irritant (e.g. Oil of winter green)
6. Local anesthetic (e.g. Clove)
7. Sedative (e.g. Jatamansi)
8. Insect repellent (e.g. Citronella)
10. Source of vitamin A (e.g. Lemongrass)
PHARMACEUTICAL APPLICATIONS
Counter irritant:
An externally applied
substance that causes
irritation or mild
inflammation of the
skin for the purpose of
relieving pain in
muscles, joints and
viscera distal to the site
of application
PREPARATION OF VOLATILE OILS
Enzymatic
Hydrolysis
Distillation
Method
Expression/
Ecuelle Method
Extraction
Method
Destructive
Distillation
Water
Water +
Steam
Steam
Vacuum
CO2
Extraction
Enfleurage
• Volatile oils are usually obtained by distillation of the
plant part containing the oil
• The method depends on the condition of the plant
material.
DISTLLATION PROCESS
Steam Distillation
Water & Steam
Distillation
Water Distillation
Sample:
 Which are not destroyed or injured by boiling up to 100oC
 Dried plant sample
WATER DISTILLATION
A small piece of dried plant material is introduced into
the distilling chamber
Water is added
Heated up to 100oC
Vapor of volatile oil and water goes into the condenser
After being condensed, volatile oil is separated by
Florentine Flask
PROCEDURE
Florentine Flasks of the type FLW or FHW depending on whether the resulting oil is
lighter than water or heavier than water.
• The distillation flask is heated initially to start the
process of steam distillation. Once the distillation
commences the heat of the steam entering the flask
not only maintains the high-temperature required but
also in removing the volatile components to the water
condenser for ultimate collection in the respective
Florentine Flask.
• Excess heat must be avoided
• Process must be air tight
• Full amount of the water must be vaporized.
CAUTIONS
• Sample:
▫ Fresh material
▫ Materials which may be injured by direct boiling
▫ Materials which may be hydrolyzed
▫ Example: Peppermint Oil
STEAM DISTILLATION
NO
MECERATION
The plant sample taken into a metal distillation chamber over the
perforated tray
The steam is forced to the fresh sample from below
Then the vapor of the volatile oil and steam is passed through the
condenser
The volatile oil is finally separated through Florentine flask
PROCEDURE
• Samples:
▫ Both fresh and dried samples
▫ Materials which may be injured by direct boiling
▫ Example: Clove Oil, Cinnamon Oil
WATER AND STEAM DISTILLATION
MECERATION
BEFORE STEAM
DISTILLATION
The sample is put into a flask with water so that the
sample is well mecerated
Steam is generated else where to prevent the impairing
of drug due to direct heat is passed through the
mecerated mixture
The vapor of volatile oil and liquid pass through the
condenser
Two layer is formed – one is oleaginous layer and
another is aqueous layer
Finally the volatile oil is separated through Florentine
flask.
PROCEDURE
• Performed under reduced pressure
• This technique separates compounds based on
differences in boiling points
difficult to achieve or will cause the compound to
decompose
pressure boiling point of compounds
• Fresh plant parts
• Heat sensitive materials
• Prevent the oxidation of volatile oils.
VACUUM DISTILLATION
Sample with water is introduced into the distilling
chamber
Hg-pump is added to remove gas and create the vacuum
Heat is applied and the steam of oil and water are passed
through the condenser
Finally the volatile oil is separated through Florentine
flask
PROCEDURE
Hg-Pump
• There are some glycosides which contain volatile oil.
To separate these types of volatile oils, we need
Enzymatic Hydrolysis process.
ENZYMATIC HYDROLYSIS
Gylcosides
Glycone Aglycone (volatile oil)
Amygdalase,
Prunase
Myrosine
C6H11O5
1.
2.
3.
• Often referred to as “cold pressing.”
• The term expression refers to any physical process in which
the essential oil glands in the peel are crushed or broken to
release the oil.
• Sample: citrus essential oils, such as tangerine, lemon,
bergamot, sweet orange, and lime,
• This method involves the rind portion of the fruit, or the
outermost waxy layer of the fruit’s peel
• This method is most useful with plant materials that lose
their fragrance and beneficial properties when exposed to
the temperatures required for steam distillation
• Oil is forced from the material under high mechanical
pressure and generally produces a good quality oil
EXPRESSION
SPONGE EXTRACTION PROCESS
The fruit pulp was removed.
The remaining rind and pith were soaked in warm water to make
the rind more pliable, because the pith of the fruit absorbed the
water.
The operator takes a sponge in one hand and with the other presses
the softener peel against the sponge, so that the oil glands burst open
and the sponge absorbs the exuded oil
As the sponge became saturated with oil, it was squeezed and the
essential oil collected in a vessel and then decanted.
• The whole of the above process is carried out in cool,
darkened rooms to minimize the harmful effects of
heat and light on the oil
or
• In this process, the rinds are ruptured
mechanically using numerous pointed
projections with a rotary movement and
the oil is collected.
• Ecuelle a piquer is a specially designed
apparatus is nothing but a large bowl
meant for pricking the outer surface of
citrus fruits.
• It is more or less a large funnel made of
copper having its inner layer tinned
properly. The inner layer has numerous
pointed metal needles just long enough to
penetrate the epidermis.
• The lower stem of the apparatus serve two
purposes; first, as a receiver for the oil;
and secondly, as a handle.
ECUELLE EXTRACTION PROCESS
The fruit is placed in a device with spikes and rotated repeatedly on
the side puncturing the oil cells in the skin of the fruit.
This causes the oil cells to rupture and the essential oil, and pigment,
to run down to the collection area in the center.
The liquid is separated and the oil is removed from the water-based
parts of the mixture and decanted.
PROCESS
Or
• The plant material containing
the volatile oil is usually
extracted with a low boiling
volatile solvent, such as n-
hexane, benzene, petroleum
ether etc., either by adopting
the method of hot continuous
extraction (Soxhlet
extraction) or by percolation
• Process depends on the
nature of volatile oil
Extraction Method
Carbondioxide Extraction
CO2 gas at low temperature and high pressure
Turns into liquid
Rupture the plant material
This fluid enters into the cell
Volatile oil extracted into the media (liq CO2)
Volatile oil is collected by fractional distillation
Enfleurage method
Glass plates are covered with a thin layer of fixed oil or fat those are
securedly placed in a covered wooden frame
Each glass plate is liberally sprinkled with fresh flower petals to
cover its top surface only.
loaded plates are allowed to remain for 24hours
flowers are then removed and recharged with fresh lots
This very process is repeated religiously for several weeks till the
fatty layers appear to be fully saturated with the essential oils of the
flowers
The flowers are subsequently removed
the fat is separated carefully and stirred with absolute alcohol
alcohol will dissolve the volatile oil portion thereby leaving the fat
undissolved in alcohol
The alcoholic extract is reasonably chilled and filtered to get rid off
any traces of residual fat.
Three successive extraction procedures are repeated so as to affect
the complete recovery of volatile oil
the resulting solution is employed as such in the perfume industry
and is commonly termed as the ‘Tripple Extract’
The volatile oil may be recovered from the ‘Triple Extract’ by
anyone of the following methods, namely:
 first, fractional distillation under vacuum at 0oC;
 secondly, evaporation under vacuum at 0o
C;
 thirdly, the alcoholic extract is diluted with water and
saturated with NaCl, when the oil will seaparate with the
retention of fresh natural ordour
Destructive distillation
• Destructive distillation is the chemical process of the
decomposition of unprocessed material by heating it to
a high temperature
• Empyreumatic oils: being or having an odor of
burnt organic matter as a result of decomposition at
high temperatures
• Destructive distillation is a means of obtaining
Empyreumatic oils
The wood or resin of members of the Pinaceae or Cupressaceae is
heated without access of air,
decomposition takes place, and a number of volatile compounds are
driven off.
The resultant mass is charcoal.
The condensed volatile matter usually separates into 2 layers:
1. an aqueous layer containing wood naphtha (methyl alcohol)
and pyroligneous acid crude acetic),
2. a tarry liquid in the form of pine tar, juniper tar, or other
tars, depending on the wood introduced.
Plants containing
volatile oils
• Obtained from the dried flower buds of Syzygium
aromaticum (Eugenia caryophyllus)
• Family : Myrtaceae
• Obtained by Steam distillation process.
Clove oil
• Physical properties:
 Colorless or pale yellow liquid
 Spicy order and pungent taste
 It becomes darker and thicker on exposure to air and by
aging.
Clove oil
1. Eugenol (70-95%)
2. Eugenol acetate
(3%)
3. ß-caryophyllene
4. Methyl amyl ketone
5. Methyl furfural
6. Carbinol
7. Vanillin
8. Methyl-n-heptyl-
ketone
1. Methyl salicylate
2. Methyl benzoate
3. Methyl alcohol
4. Benzyl alcohol
5. Furfuryl alcohol
6. Furfural
7. Methyl furfuryl
alcohol
8. 2-heptanol
9. 2 nonalol
Trace
amount
Chemical structure
Methyl benzoate
Furfural alcohol 2-heptanol
1. Flavoring agent
2. Commercially producing vanillin
3. Antioxidant
4. In throat infection
5. Remove fatigue
6. Toothache remedy
7. Antiseptic
8. Counterirritant
9. Carminative
10. Mouthwash
11. Dental preperation (eugenol)
12. Antimicrobial (diarrhea, intestinal worms, and other
digestive ailments)
13. Eugenol is also used as local anaesthetic in small doses.
14. The oil stimulates peristalsis; it is a strong germicide, also
a stimulating expectorant in bronchial problems.
15. Antiemetic
Uses
85% volatile oil
Phenolic type
Eugenol
Cinnamon oil
• Obtained from the leaves and barks of Cinnamonum
cassia
• Family : Lauraceae
• Obtained by Steam distillation process.
• Also known as cassia oil
• Physical properties:
 Yellowish or brownish color
 Sweet in taste
 Spicy delicate fragrance.
Chemical constituents
1. Cinnamaldehyde (80-95%)
2. Cinnamyl acetate
3. Limonene
4. Linalool
5. Eugenol (4-10%)
6. Mannitol (sweet taste)
7. ß-Caryophyllene
8. p-cymene
Chemical structure
limoneneCinnamaldehyde Cinnamalacetate
Uses
1. Mild antiseptic
2. Carminative
3. Astringent
4. Flavoring agent
5. Anti-diarrhoeal
6. Increase the action of insulin
• Source: Peppermint consists of dried leaves and
flowering tops of Mentha pipenta
• Family : Labiatae.
• Distilled with steam from the fresh overground parts
Peppermint oil
• Physical properties:
 Colourless, pale yellow or greenish yellow liquid
 Strong agreeable odour and a powerful aromatic
taste, followed by a cooling sensation when air is
drawn into the mouth
1. Menthol (50-90%)
2. L-and d-menthone (10%)
3. Menthyl acetate,
4. Menthyl valerate,
5. Menthofuran,
6. Jasmone,
7. Phellandrene.
8. Pinene.
9. Cineole,
10.Limonene,
11.Terpinene,
12.Cadinene,
13.Amyl alcohol,
14.Acetic acid, isovaleric acid.
15.Acetaldehyde, isovalenc aldehyde
16.Piperitone
Chemical structure
Menthol Menthone Menthylacetate
Eucalyptol/ cineol Piperitone
Uses
1. Flavoring agent
2. Carminative
3. Stimulant
4. Counterirritant
5. Reducing gastralgia, nausea, flatulence and vomiting
6. Mild antiseptic and local anaesthetic properties
7. Externally in rheumatism, neuralgia, headache and
toothache.
8. Peppermint oil is used for flavoring in pharmaceuticals.
dental preparation, mouth washes, cough, drops, soaps,
chewing gums, candles, confectionery and alcoholic liquers
chewing gum 55%; toothpaste, mouthwash, and
pharmaceuticals 34%; confectionary products, 10%; and
other products 1%.
• Sources: dried, scythe-shaped the fresh leaves of various
species of Eucalyptus such as E. globulus Labill. E.
polybractea. E. smithii, E. vimino.lis, and E.
australlana.
• Family : Myrtaceae
• Obtained by Steam distillation.
Physical properties:
• The oil is a colorless or pale yellow liquid that has
a characteristic, aromatic, camphoraceous odor and a
pungent, spicy, cooling taste
Eucalyptus oil
Eucalyptus
oil
1. Cineol/eucalyptol (70-85%)
2. P- coumaric acid
3. Terpenes
4. Rutin
5. Dihydroflavinol
6. P-cymene,
7. α-pinene
8. Gallic acid
9. Eucalyptin
10.Eucalyptic acid
11.Resin
12.Tannic acid
13.Camphene,
14.Butyric aldehyde, valerenic
aldehyde, caproic aldehyde,
aromadendrene, cuminaldehyde,
15.Pinocarveol, and phellandrene
Chemical structure
Eucalyptol/ cineol P- coumaric acid
Dihydro flavinol
P-cymene α phellandrene cuminaldehyde Gallic acid
Uses
1. Stimulant,
2. Antiseptic,
3. Flavoring agent,
4. Aroma therapy,
5. Deodorant,
6. Expectorant,
7. Antimicrobial,
8. Febrifuge,
9. Diuretic,
10. Antispasmodic.
11. Used in the treatment of lung diseases, sore throat, cold
12. A vapour bath for asthma and various respiratory ailments and in bronchitis
13. Burns and as mosquito repellant.
14. Eucalyptus Increases the flow of saliva, gastric and intestinal juices and thus
increases appetite and digestion.
15. It increases the rate of heart beats, lowers the arterial tension and quickens
respiration.
16. Toxic doses it is a narcotic poison. It paralyses the respiratory center in the
medulla
It is taken internally in
the form of mixtures,
inhalations, lozenges
and
pastilles and applied
externally as ointments
and liniments.
• The star-anise oil is obtained from Illicium verum
• Family: Illiciaceae
• Chemical constituents:
Anise seed oil
Anise seed
oil
1. Anethole (87–94%)
2. Estragole (0.5–5.0%)
3. Anisaldehyde (0.1–0.5%)
4. Foeniculin (0.1–3.0%);
5. Anisic acid,
6. Anise ketone,
7. Β-caryophylline,
8. Linalool;
9. Polymers of anethole,
dianethole, and
photoanethole.
10. Coumarins
11. Flavonoid glycosides (rutin,
isovitexin and quercetin),
12. Phenylpropanoids.
Uses
1. Flavouring agents
2. Carminatives
3. Expectorant
4. Used in the treatment of bronchitis, asthma,
5. Antimicrobial
6. Antispasmodic.
7. Enhance the memory,
8. Increases lactation,
9. Relieves menopausal discomforts,
10. Whooping cough,
11. Externally in scabies,
12. Overcomes nausea, and as a digestive.
• Nutmeg is the kernel of the dried ripe seed of Myristica
fragrans
• Family : Myristicaceae.
• Obtained from distilled with steam
• The oil is a colorless or pale yellow liquid that has the
characteristic odor and taste of nutmeg.
Nutmeg oil
Nutmeg oil
1. α-pinene (15–26%),
2. β-pinene (13–18%),
3. sabinine (14–29%),
4. myristicin (5–12%),
5. limonene (2–7%),
6. γ-terpinene (2–6%),
7. terpinen-4-ol (2–6%),
8. car-3-ene (0.5–2%),
9. safrole (2.5% maximum).
1. Elemicin and
isoelemicin,
2. Eugenol,
Methyleugenol
Methoxyeugenol
Methylisoeugeol
Isoeugenol.
3. Clemicine,
4. Geraniol,
5. Borneol,
6. Camphene,
7. Dipentene.
8. Myristic acid
Major Minor
γ
1. Flavoring agent
2. Carminative,
3. Astringent,
4. Aphrodisiac,
5. Stomachic
6. Nausea and vomiting
7. Antibacterial activity.
8. Ingestion of large quantities causes drowsiness,
stupor and death.
9. It has narcotic action and peripherally it irritates
and produces anesthetics action, since it irritates
intestine and uterus it can cause abortion.
Uses
• Biological Source : Fennel oil is obtained from the
dried, ripe fruits of F'oeniculum vulgare.
• Family : Umbelliferae
• Chemical constituents:
Fennel seed oil
1. Anethole (55–75%)
2. Fenchone (12–25%)
3. Anisaldehyde (maximum
2.0%)
4. Anisic acid,
5. Estragole (methyl
chavicol) (maximum
5.0%).
6. Dipentene,
7. Limonene
8. Phelandrene
9. Β-pinene,
Fennel
1. Stomachic
2. Aromatic stimulant
3. Diuretic
4. Carminative
5. Diaphoretic
6. Digestive
7. Flavouring agent
8. Anethole may have estrogen-like activity and inhibit spasms
in smooth muscles.
9. Fennel can increase production of bile,
10. Used in the treatment of infant colic,
11. Reduce pain in dysmenorrhea,
12. Can increase lactation,
13. Act as antipyretic,
14. Emmenagogue
15. Antimicrobial and anti-inflammatory
16. Anethole is used in mouth and dental preparations.
17. Fennel is useful in diseases of the chest, spleen and kidney.
Uses
1. linalool (65-70%)
2. pinene.
3. geranlol,
4. boineol.
5. p-cymene,
6. dipentene,
7. phellandrene,
8. terpinolene,
9. hydrocarbons such 3-terpinne,
10.geraniol,
11.n-decylic aldehyde
12.camphor,
13.malic acid,
14.esters of acetic and decylic acids,
tannins, and mucilage are also present.
15.Other constituents isolated from the
fruits include flavonoids, coumarins,
isocoumarins, phthalides and phenolic
acids.
Coriander
oil
# Obtained from the
dried, nearly ripe fruit of
Coriandrum sativum
Family : Umbelliferae
P-cymene α phellandrene
Uses
1. Flavouring agent
2. Carminative.
3. Aromatic stimulant,
4. Antispasmodic,
5. Diaphoretic
6. Appetizer,
7. Diuretic,
8. Aphrodisiac,
9. Stomachic.
10. Antibiliou
11. Coriander oil can be applied externally for rheumatism
and painful joints.
12. The infusion of decoction of dried fruit of cardamom is
useful for the treatment of sore-throat, indigestion,
vomiting, flatulence, and other intestinal disorders.

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Volatile oils

  • 1. VOLATILE OILS Prepared by- Afia Nabila Lecturer Department of Pharmacy, USTC. P H A R M A C O G N O S Y
  • 2. Definition • Volatile oils are the odorous and volatile products of various plant. As they have a tendency to undergo evaporation on being exposed to the air even at an ambient temperature, they are invariably termed as volatile oils, essential oil or ethereal oils. • Chemically, they are composed of hydrocarbons of the general formula (C5H8) and their oxygenated, hydrogenated and dehydrogenated derivatives. • All the volatile oils are of vegetable origin. • These volatile oils are usually formed by two modes namely; first, by hydrolysis of some glycosides; and secondly, by the protoplasm directly.
  • 3. • In most instances, the volatile oil preexists in the plant and is usually contained in some special secretory tissuesas glandular hairs, parenchyma cells, vittae or oil tubes, in mesophyll (Eucalyptus leaves), sub-epidermal tissues of Lemon and Orange. in lysigenous or schizogenous passages, in all tissues (Conifers), In petals (Orange. Rose), in bark and leaves (Cinnamon), in pericarp (Umbelliferous fruits), in glandular hairs of the stems and leaves (Mint), and in rind (Orange). • These represent essence of active constituents of the plant and hence also known as essential oils. Why they are called Essential Oil?
  • 4.
  • 5. • They are evaporated at ordinary temperature • Volatile oils are colourless liquids, but when exposed to air and direct sunlight these become darker due to oxidation. To prevent this darkening, they should he stored in a cool, dry place in tightly stoppered preferably amber glass containers. • They possess characteristic odors • Characterized by high refractive indices • Most of them are optically active [specific rotation is often a valuable diagnostic properties] Physical Properties
  • 6. • Volatile oils are immiscible with water, but they are sufficiently soluble to impart their odor to water • Soluble in ether, alcohol, chloroform and most organic solvents. • Volatile oils neither leave permanent grease spot on filter paper nor saponified with alkalis • They are present in entire plants (Mint, Conifers) or any part of the plant (Rose)
  • 7. No Volatile oil Fixed oil 1. Volatile oil can evaporate when placed under room temperature Fixed oils do not evaporate at room temperature 2. Mixtures of cleoptenes & stearoptenes are termed as volatile oils Esters of higher fatty acids & glycerin are called as fixed oils. 3 Their primary source is leaves, roots, in petals and bark. Their major source is seeds of the plant and animal. 4. Possess high refractive index Possess low refractive index 5. These are optically active. These are optically inactive. 6. There is no spot (no permanent stain) left after evaporation Some type of spot (permanent stain) left after evaporation 7. They are unable to undergo saponification Fixed oils can be easily saponified. 8. Essential oils do not go rancid, rather they oxidize and lose their therapeutic benefit Fixed oils can go rancid (stale) over time 9. Colorless Some possess colors (yellowish) 10. Have characteristic odor May or may not possess odor 11. Immiscible in water Soluble in water 12. Obtained by distillation Obtained by extraction 13. Low boiling point High boiling point 14. Soybean oil, castor oil Cinnamon oil, peppermint oil.
  • 8. Chemical composition • Many volatile oils consist largely of Terpenes. The term ‘terpene’ was given to the compounds isolated from terpentine, a volatile liquid isolated from pine trees. • But there is a tendency to use more general term ‘terpenoids’, which includes hydrocarbons and their oxygenated derivatives. • Terpenoids are volatile substances which give plants and flowers their fragrance • ‘Terpenoids are the hydrocarbons of plant origin of the general formula (C5H8)n as well as their oxygenated, hydrogenated, and dehydrogenated derivatives.’
  • 9. • Isoprene Rule Isoprene rule states that the terpenoid molecules are constructed from two or more isoprene unit. • Special Isoprene Rule It states that the terpenoid molecules are constructed of two or more isoprene units joined in a ‘head to tail’ fashion. • But this rule can only be used as guiding principle and not as a fixed rule
  • 10. • Most natural terpenoid hydrocarbons have the general formula (C5H8) n. They can be classified on the basis of number of carbon atoms present in the structure. 1. Monoterpenoids, 2 isoprene units (C5H8) 2 2. Sesquiterpenoids, 3 isoprene units (C5H8) 3 3. Diterpenoids, 4 isoprene units (C5H8)4 4. Triterpenoids, 6 isoprene units (C5H8) 6 5. Tetraterpenoids, 8 isoprene units (C5H8) 8 6. Polyterpenoid with a larger number (>8) of isoprene units (C5H8) >8 Classification of Terpinoids
  • 12. • Each class can be further subdivided into subclasses according to the number of rings present in the structure. 1. Acyclic Terpenoids: They contain open structure. 2. Monocyclic Terpenoids: They contain one ring in the structure. 3. Bicyclic Terpenoids: They contain two rings in the structure. 4. Tricyclic Terpenoids: They contain three rings in the structure. 5. Tetracyclic Terpenoids: They contain four rings in the structure.
  • 14. Sources of Volatile oil • Dried ripe fruits: Coriandar oil, Anise oil • Fresh ripe fruit: Lemon oil • Dried ripe fruit rind: Bitter range oil • Dried leaves and flowering tops: Peppermint oil, Spearmint oil. • Fresh leaves: Eucalyptus oil • Dried bark: Cinnamon oil • Dried stigma and style tops: Saffron oil • Dried flower buds: Clove oil • Dried ripe seed: Nutmeg oil, Cardamom oil • Dried peel rhizome: Calamus oil • Aerial part: Chenopodium oil • Dried roots rhizome: Valerian oil • Ripe bulb: Garlic oil • Wood : Sandal wood oil • Unripe fruit: Black pepper oil.
  • 15.
  • 16. On the basis of chemical composition of volatile oil- • Alcohol volatile oils: Coriander oil, Cardamom oil, Rose oil • Aldehyde Volatile Oils: Cinnamon oil, Lemon oil, Saffron oil • Ketone Volatile oil: Camphor oil, Caraway oil, Spearmint oil • Phenol volatile oil: Clove oil, Thyme oil, • Phenolic ether Volatile oil: Nutmeg oil, Anise oil • Oxides volatile oil: Eucalyptus oil, Chenopodium oil • Ester volatile oil: Lavender oil Classification
  • 17. Natural drugs containing volatile oils can be tested by following chemical tests: 1. Thin section of drug on treatment with alcoholic solution of Sudan III develops red color in the presence of volatile oils. 2. Thin section of drug is treated with tincture of alkana, which produces red color that indicates the presence of volatile oils in natural drugs. CHEMICAL TESTS
  • 18. Volatile oils are used as flavouring agent, perfuming agent in pharmaceutical formulations, foods, beverages, and in cosmetic industries. These are also used as important medicinal agent for therapeutic purposes like: 1. Carminative (e.g. Umbilliferous fruits) 2. Anti-helminitic (e.g. Chenopodium oil) 3. Diuretics (e.g. Juniper) 4. Antiseptic (e.g. Eucalyptus) 5. Counter irritant (e.g. Oil of winter green) 6. Local anesthetic (e.g. Clove) 7. Sedative (e.g. Jatamansi) 8. Insect repellent (e.g. Citronella) 10. Source of vitamin A (e.g. Lemongrass) PHARMACEUTICAL APPLICATIONS Counter irritant: An externally applied substance that causes irritation or mild inflammation of the skin for the purpose of relieving pain in muscles, joints and viscera distal to the site of application
  • 19. PREPARATION OF VOLATILE OILS Enzymatic Hydrolysis Distillation Method Expression/ Ecuelle Method Extraction Method Destructive Distillation Water Water + Steam Steam Vacuum CO2 Extraction Enfleurage
  • 20. • Volatile oils are usually obtained by distillation of the plant part containing the oil • The method depends on the condition of the plant material. DISTLLATION PROCESS Steam Distillation Water & Steam Distillation Water Distillation
  • 21. Sample:  Which are not destroyed or injured by boiling up to 100oC  Dried plant sample WATER DISTILLATION
  • 22. A small piece of dried plant material is introduced into the distilling chamber Water is added Heated up to 100oC Vapor of volatile oil and water goes into the condenser After being condensed, volatile oil is separated by Florentine Flask PROCEDURE Florentine Flasks of the type FLW or FHW depending on whether the resulting oil is lighter than water or heavier than water.
  • 23.
  • 24. • The distillation flask is heated initially to start the process of steam distillation. Once the distillation commences the heat of the steam entering the flask not only maintains the high-temperature required but also in removing the volatile components to the water condenser for ultimate collection in the respective Florentine Flask. • Excess heat must be avoided • Process must be air tight • Full amount of the water must be vaporized. CAUTIONS
  • 25. • Sample: ▫ Fresh material ▫ Materials which may be injured by direct boiling ▫ Materials which may be hydrolyzed ▫ Example: Peppermint Oil STEAM DISTILLATION NO MECERATION
  • 26.
  • 27.
  • 28. The plant sample taken into a metal distillation chamber over the perforated tray The steam is forced to the fresh sample from below Then the vapor of the volatile oil and steam is passed through the condenser The volatile oil is finally separated through Florentine flask PROCEDURE
  • 29. • Samples: ▫ Both fresh and dried samples ▫ Materials which may be injured by direct boiling ▫ Example: Clove Oil, Cinnamon Oil WATER AND STEAM DISTILLATION MECERATION BEFORE STEAM DISTILLATION
  • 30. The sample is put into a flask with water so that the sample is well mecerated Steam is generated else where to prevent the impairing of drug due to direct heat is passed through the mecerated mixture The vapor of volatile oil and liquid pass through the condenser Two layer is formed – one is oleaginous layer and another is aqueous layer Finally the volatile oil is separated through Florentine flask. PROCEDURE
  • 31. • Performed under reduced pressure • This technique separates compounds based on differences in boiling points difficult to achieve or will cause the compound to decompose pressure boiling point of compounds • Fresh plant parts • Heat sensitive materials • Prevent the oxidation of volatile oils. VACUUM DISTILLATION
  • 32. Sample with water is introduced into the distilling chamber Hg-pump is added to remove gas and create the vacuum Heat is applied and the steam of oil and water are passed through the condenser Finally the volatile oil is separated through Florentine flask PROCEDURE
  • 34. • There are some glycosides which contain volatile oil. To separate these types of volatile oils, we need Enzymatic Hydrolysis process. ENZYMATIC HYDROLYSIS Gylcosides Glycone Aglycone (volatile oil)
  • 36. 3.
  • 37. • Often referred to as “cold pressing.” • The term expression refers to any physical process in which the essential oil glands in the peel are crushed or broken to release the oil. • Sample: citrus essential oils, such as tangerine, lemon, bergamot, sweet orange, and lime, • This method involves the rind portion of the fruit, or the outermost waxy layer of the fruit’s peel • This method is most useful with plant materials that lose their fragrance and beneficial properties when exposed to the temperatures required for steam distillation • Oil is forced from the material under high mechanical pressure and generally produces a good quality oil EXPRESSION
  • 38. SPONGE EXTRACTION PROCESS The fruit pulp was removed. The remaining rind and pith were soaked in warm water to make the rind more pliable, because the pith of the fruit absorbed the water. The operator takes a sponge in one hand and with the other presses the softener peel against the sponge, so that the oil glands burst open and the sponge absorbs the exuded oil As the sponge became saturated with oil, it was squeezed and the essential oil collected in a vessel and then decanted.
  • 39. • The whole of the above process is carried out in cool, darkened rooms to minimize the harmful effects of heat and light on the oil
  • 40. or
  • 41. • In this process, the rinds are ruptured mechanically using numerous pointed projections with a rotary movement and the oil is collected. • Ecuelle a piquer is a specially designed apparatus is nothing but a large bowl meant for pricking the outer surface of citrus fruits. • It is more or less a large funnel made of copper having its inner layer tinned properly. The inner layer has numerous pointed metal needles just long enough to penetrate the epidermis. • The lower stem of the apparatus serve two purposes; first, as a receiver for the oil; and secondly, as a handle. ECUELLE EXTRACTION PROCESS
  • 42. The fruit is placed in a device with spikes and rotated repeatedly on the side puncturing the oil cells in the skin of the fruit. This causes the oil cells to rupture and the essential oil, and pigment, to run down to the collection area in the center. The liquid is separated and the oil is removed from the water-based parts of the mixture and decanted. PROCESS
  • 43. Or
  • 44. • The plant material containing the volatile oil is usually extracted with a low boiling volatile solvent, such as n- hexane, benzene, petroleum ether etc., either by adopting the method of hot continuous extraction (Soxhlet extraction) or by percolation • Process depends on the nature of volatile oil Extraction Method
  • 45. Carbondioxide Extraction CO2 gas at low temperature and high pressure Turns into liquid Rupture the plant material This fluid enters into the cell Volatile oil extracted into the media (liq CO2) Volatile oil is collected by fractional distillation
  • 46. Enfleurage method Glass plates are covered with a thin layer of fixed oil or fat those are securedly placed in a covered wooden frame Each glass plate is liberally sprinkled with fresh flower petals to cover its top surface only. loaded plates are allowed to remain for 24hours flowers are then removed and recharged with fresh lots This very process is repeated religiously for several weeks till the fatty layers appear to be fully saturated with the essential oils of the flowers
  • 47. The flowers are subsequently removed the fat is separated carefully and stirred with absolute alcohol alcohol will dissolve the volatile oil portion thereby leaving the fat undissolved in alcohol The alcoholic extract is reasonably chilled and filtered to get rid off any traces of residual fat. Three successive extraction procedures are repeated so as to affect the complete recovery of volatile oil the resulting solution is employed as such in the perfume industry and is commonly termed as the ‘Tripple Extract’
  • 48. The volatile oil may be recovered from the ‘Triple Extract’ by anyone of the following methods, namely:  first, fractional distillation under vacuum at 0oC;  secondly, evaporation under vacuum at 0o C;  thirdly, the alcoholic extract is diluted with water and saturated with NaCl, when the oil will seaparate with the retention of fresh natural ordour
  • 49. Destructive distillation • Destructive distillation is the chemical process of the decomposition of unprocessed material by heating it to a high temperature • Empyreumatic oils: being or having an odor of burnt organic matter as a result of decomposition at high temperatures • Destructive distillation is a means of obtaining Empyreumatic oils
  • 50. The wood or resin of members of the Pinaceae or Cupressaceae is heated without access of air, decomposition takes place, and a number of volatile compounds are driven off. The resultant mass is charcoal. The condensed volatile matter usually separates into 2 layers: 1. an aqueous layer containing wood naphtha (methyl alcohol) and pyroligneous acid crude acetic), 2. a tarry liquid in the form of pine tar, juniper tar, or other tars, depending on the wood introduced.
  • 51.
  • 53. • Obtained from the dried flower buds of Syzygium aromaticum (Eugenia caryophyllus) • Family : Myrtaceae • Obtained by Steam distillation process. Clove oil • Physical properties:  Colorless or pale yellow liquid  Spicy order and pungent taste  It becomes darker and thicker on exposure to air and by aging.
  • 54. Clove oil 1. Eugenol (70-95%) 2. Eugenol acetate (3%) 3. ß-caryophyllene 4. Methyl amyl ketone 5. Methyl furfural 6. Carbinol 7. Vanillin 8. Methyl-n-heptyl- ketone 1. Methyl salicylate 2. Methyl benzoate 3. Methyl alcohol 4. Benzyl alcohol 5. Furfuryl alcohol 6. Furfural 7. Methyl furfuryl alcohol 8. 2-heptanol 9. 2 nonalol Trace amount
  • 56. 1. Flavoring agent 2. Commercially producing vanillin 3. Antioxidant 4. In throat infection 5. Remove fatigue 6. Toothache remedy 7. Antiseptic 8. Counterirritant 9. Carminative 10. Mouthwash 11. Dental preperation (eugenol) 12. Antimicrobial (diarrhea, intestinal worms, and other digestive ailments) 13. Eugenol is also used as local anaesthetic in small doses. 14. The oil stimulates peristalsis; it is a strong germicide, also a stimulating expectorant in bronchial problems. 15. Antiemetic Uses 85% volatile oil Phenolic type Eugenol
  • 57. Cinnamon oil • Obtained from the leaves and barks of Cinnamonum cassia • Family : Lauraceae • Obtained by Steam distillation process. • Also known as cassia oil • Physical properties:  Yellowish or brownish color  Sweet in taste  Spicy delicate fragrance.
  • 58. Chemical constituents 1. Cinnamaldehyde (80-95%) 2. Cinnamyl acetate 3. Limonene 4. Linalool 5. Eugenol (4-10%) 6. Mannitol (sweet taste) 7. ß-Caryophyllene 8. p-cymene
  • 60. Uses 1. Mild antiseptic 2. Carminative 3. Astringent 4. Flavoring agent 5. Anti-diarrhoeal 6. Increase the action of insulin
  • 61. • Source: Peppermint consists of dried leaves and flowering tops of Mentha pipenta • Family : Labiatae. • Distilled with steam from the fresh overground parts Peppermint oil • Physical properties:  Colourless, pale yellow or greenish yellow liquid  Strong agreeable odour and a powerful aromatic taste, followed by a cooling sensation when air is drawn into the mouth
  • 62. 1. Menthol (50-90%) 2. L-and d-menthone (10%) 3. Menthyl acetate, 4. Menthyl valerate, 5. Menthofuran, 6. Jasmone, 7. Phellandrene. 8. Pinene. 9. Cineole, 10.Limonene, 11.Terpinene, 12.Cadinene, 13.Amyl alcohol, 14.Acetic acid, isovaleric acid. 15.Acetaldehyde, isovalenc aldehyde 16.Piperitone
  • 63. Chemical structure Menthol Menthone Menthylacetate Eucalyptol/ cineol Piperitone
  • 64. Uses 1. Flavoring agent 2. Carminative 3. Stimulant 4. Counterirritant 5. Reducing gastralgia, nausea, flatulence and vomiting 6. Mild antiseptic and local anaesthetic properties 7. Externally in rheumatism, neuralgia, headache and toothache. 8. Peppermint oil is used for flavoring in pharmaceuticals. dental preparation, mouth washes, cough, drops, soaps, chewing gums, candles, confectionery and alcoholic liquers chewing gum 55%; toothpaste, mouthwash, and pharmaceuticals 34%; confectionary products, 10%; and other products 1%.
  • 65. • Sources: dried, scythe-shaped the fresh leaves of various species of Eucalyptus such as E. globulus Labill. E. polybractea. E. smithii, E. vimino.lis, and E. australlana. • Family : Myrtaceae • Obtained by Steam distillation. Physical properties: • The oil is a colorless or pale yellow liquid that has a characteristic, aromatic, camphoraceous odor and a pungent, spicy, cooling taste Eucalyptus oil
  • 66. Eucalyptus oil 1. Cineol/eucalyptol (70-85%) 2. P- coumaric acid 3. Terpenes 4. Rutin 5. Dihydroflavinol 6. P-cymene, 7. α-pinene 8. Gallic acid 9. Eucalyptin 10.Eucalyptic acid 11.Resin 12.Tannic acid 13.Camphene, 14.Butyric aldehyde, valerenic aldehyde, caproic aldehyde, aromadendrene, cuminaldehyde, 15.Pinocarveol, and phellandrene
  • 67. Chemical structure Eucalyptol/ cineol P- coumaric acid Dihydro flavinol P-cymene α phellandrene cuminaldehyde Gallic acid
  • 68. Uses 1. Stimulant, 2. Antiseptic, 3. Flavoring agent, 4. Aroma therapy, 5. Deodorant, 6. Expectorant, 7. Antimicrobial, 8. Febrifuge, 9. Diuretic, 10. Antispasmodic. 11. Used in the treatment of lung diseases, sore throat, cold 12. A vapour bath for asthma and various respiratory ailments and in bronchitis 13. Burns and as mosquito repellant. 14. Eucalyptus Increases the flow of saliva, gastric and intestinal juices and thus increases appetite and digestion. 15. It increases the rate of heart beats, lowers the arterial tension and quickens respiration. 16. Toxic doses it is a narcotic poison. It paralyses the respiratory center in the medulla It is taken internally in the form of mixtures, inhalations, lozenges and pastilles and applied externally as ointments and liniments.
  • 69. • The star-anise oil is obtained from Illicium verum • Family: Illiciaceae • Chemical constituents: Anise seed oil Anise seed oil 1. Anethole (87–94%) 2. Estragole (0.5–5.0%) 3. Anisaldehyde (0.1–0.5%) 4. Foeniculin (0.1–3.0%); 5. Anisic acid, 6. Anise ketone, 7. Β-caryophylline, 8. Linalool; 9. Polymers of anethole, dianethole, and photoanethole. 10. Coumarins 11. Flavonoid glycosides (rutin, isovitexin and quercetin), 12. Phenylpropanoids.
  • 70.
  • 71. Uses 1. Flavouring agents 2. Carminatives 3. Expectorant 4. Used in the treatment of bronchitis, asthma, 5. Antimicrobial 6. Antispasmodic. 7. Enhance the memory, 8. Increases lactation, 9. Relieves menopausal discomforts, 10. Whooping cough, 11. Externally in scabies, 12. Overcomes nausea, and as a digestive.
  • 72. • Nutmeg is the kernel of the dried ripe seed of Myristica fragrans • Family : Myristicaceae. • Obtained from distilled with steam • The oil is a colorless or pale yellow liquid that has the characteristic odor and taste of nutmeg. Nutmeg oil
  • 73. Nutmeg oil 1. α-pinene (15–26%), 2. β-pinene (13–18%), 3. sabinine (14–29%), 4. myristicin (5–12%), 5. limonene (2–7%), 6. γ-terpinene (2–6%), 7. terpinen-4-ol (2–6%), 8. car-3-ene (0.5–2%), 9. safrole (2.5% maximum). 1. Elemicin and isoelemicin, 2. Eugenol, Methyleugenol Methoxyeugenol Methylisoeugeol Isoeugenol. 3. Clemicine, 4. Geraniol, 5. Borneol, 6. Camphene, 7. Dipentene. 8. Myristic acid Major Minor
  • 74. γ
  • 75. 1. Flavoring agent 2. Carminative, 3. Astringent, 4. Aphrodisiac, 5. Stomachic 6. Nausea and vomiting 7. Antibacterial activity. 8. Ingestion of large quantities causes drowsiness, stupor and death. 9. It has narcotic action and peripherally it irritates and produces anesthetics action, since it irritates intestine and uterus it can cause abortion. Uses
  • 76. • Biological Source : Fennel oil is obtained from the dried, ripe fruits of F'oeniculum vulgare. • Family : Umbelliferae • Chemical constituents: Fennel seed oil 1. Anethole (55–75%) 2. Fenchone (12–25%) 3. Anisaldehyde (maximum 2.0%) 4. Anisic acid, 5. Estragole (methyl chavicol) (maximum 5.0%). 6. Dipentene, 7. Limonene 8. Phelandrene 9. Β-pinene, Fennel
  • 77.
  • 78. 1. Stomachic 2. Aromatic stimulant 3. Diuretic 4. Carminative 5. Diaphoretic 6. Digestive 7. Flavouring agent 8. Anethole may have estrogen-like activity and inhibit spasms in smooth muscles. 9. Fennel can increase production of bile, 10. Used in the treatment of infant colic, 11. Reduce pain in dysmenorrhea, 12. Can increase lactation, 13. Act as antipyretic, 14. Emmenagogue 15. Antimicrobial and anti-inflammatory 16. Anethole is used in mouth and dental preparations. 17. Fennel is useful in diseases of the chest, spleen and kidney. Uses
  • 79. 1. linalool (65-70%) 2. pinene. 3. geranlol, 4. boineol. 5. p-cymene, 6. dipentene, 7. phellandrene, 8. terpinolene, 9. hydrocarbons such 3-terpinne, 10.geraniol, 11.n-decylic aldehyde 12.camphor, 13.malic acid, 14.esters of acetic and decylic acids, tannins, and mucilage are also present. 15.Other constituents isolated from the fruits include flavonoids, coumarins, isocoumarins, phthalides and phenolic acids. Coriander oil # Obtained from the dried, nearly ripe fruit of Coriandrum sativum Family : Umbelliferae
  • 81. Uses 1. Flavouring agent 2. Carminative. 3. Aromatic stimulant, 4. Antispasmodic, 5. Diaphoretic 6. Appetizer, 7. Diuretic, 8. Aphrodisiac, 9. Stomachic. 10. Antibiliou 11. Coriander oil can be applied externally for rheumatism and painful joints. 12. The infusion of decoction of dried fruit of cardamom is useful for the treatment of sore-throat, indigestion, vomiting, flatulence, and other intestinal disorders.