Volatile Oils

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 Contents
 Introduction
 Distribution
 Occurrence
 Properties
 Extraction
 Uses
 Herbs containing Volatile Oils

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 Introduction
• Definition
– Odoriferous principles of varying chemical
composition
– Easily evaporate when exposed to air at ordinary
temperature
– Are used for either their specific therapeutic
activity or their aroma
• Synonymous: Ethereal oils, Essential oils

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 Introduction Cont…
• Difference from fixed oils
– Are capable of volatilization (distilled from their
natural source)
– Are not glyceryl esters of long chain fatty acid
(they are terpenoids, polyphenols),hence:
Do not leave permanent grease spot on
paper
Can not be saponified with alkalis
– Do not become rancid like fixed oils but will
oxidize and resinify up on exposure to light and
O2 4
 Distribution
• In plants
– (>17,500 spp. Belonging to>90 families)
– Main families include: Myrtaceae, Lauraceae,
Rutaceae, Lamiaceae, Astraceae, Apiaceae.
Cupressaceae, Poaceae, Zingiberaceae and
Piperaceae.
– volatile oils normally pre-exist in the plant –
stored in a special secretory tissue (e.g. Citrus
peel oil cells).
– Exception: Oil of bitter almond – formed by
hydrolysis of the glycosides.
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 Distribution Cont…

– Different organs of same plant may have different

oils!!!
E.g. The volatile oil from Cinnamomun zeylanicum
(Lauraceae):
–bark is rich in Cinnamaldehyde
–leaves is rich in Euginol
–root is rich in Camphor

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 Distribution Cont…

• In animals
– Very few volatile oils
• Civet and Musk

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 Properties
Physical properties of volatile oils
– Possess characteristic odors and liquid at ambient
temperature
– Volatile (compared to fixed oils)
– Colourless liquids with the exception of chamomile
oil
May darken in color when exposed to light

– Their density is lower than water, with the exception

Clove or cinnamon heavier than water.
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 Properties Cont…

– Most of them rotate the plane polarized light.

– All volatile oils are freely soluble in ether and in

chloroform, and fairly soluble in alcohol; they are
slightly soluble in water, sufficient to give it their
characteristic odour and taste.

– Essential oils often have an odor and are therefore

used in food flavoring and perfumery.

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 Properties Cont…
Chemical properties of volatile oils
 Common physical but different chemical properties.
 Volatile oils are divided into 2 main classes based on
their biosynthetic origin

I. Terpene derivatives. E.g limonene, menthol,

borneol, Bisobolol, Chamezulene (Chamomile),
Farnesol

ii. Aromatic compounds. E.g. Vanillin

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 Properties Cont…
Terpene derivatives
• Terpenes, or terpenoids, are the largest group of
secondary products (metabolites).

• All terpenes are formed from 5-C

elements…..Isoprene is the basic structural element.

• Terpenoids contain only the most volatile terpenes

May occur as oxygenated derivatives, e.g. alcohols,
aldehydes, ketones, phenols, oxides & esters

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 Properties Cont…
 Terpenes are classified by the number of 5-C atoms
they contain
10-Carbon terpenes (contain 2 C-5 units) –
monoterpenes
15- Carbon terpenes (3 C-5 units) are called
sesquiterpenes

20-carbon terpenes (4 C-5 units) are diterpenes.

Larger terpenes
30 Carbons-called triterpenes (triterpenoids)
40 Carbons – called tetraterpenes and polyterpenoids
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 Properties Cont…

Monoterpenes

• Present in almost all essential oils.

• Are a class of terpenes that consist of two isoprene
units and all contain the functional group C10H16.
• Monoterpenes may be linear (acyclic) (Aliphatic ) or
contain rings (Alicyclic).

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 Properties Cont…

Monoterpenes
Aliphatic

2-methyl-6-methylene
D 2:7 Myrcene
2,6 dimethyl
octadiene D1,5,7 octatriene
Ocimene

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 Properties Cont…
7

• Alicyclic 1

– Monocyclic
6 2
5 3
4
8
9 10
D1,8 (9) - p-menthadiene
Limonene
1-methyl-4-isopropyl-1-cyclohexene
– Bicyclic

Thujane type Pinane type Carene type Camphane type Fenchone type
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 Properties Cont…

Sesquiterpenes
• The largest group of terpenes known naturally in the
plant and animal kingdom

• Larger than monoterpenes and are very viscous (less

volatile)
• Contain C15H24 functional group, three isoprene units

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 Acyclic Monocyclic Bicyclic

Tricyclic

CH2 CH3

Farnesene Zingiberene Cadinene Chamazulene

Sesquicitronellene

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 Properties Cont…
Aromatic compounds

OH OCH3

OCH3

CH2 CH3 CHO

Eugenol Anethole Cinnamaldehyde

(clove oil) (anise oils) (cinnamon oil)
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 Uses

• Therapeutically
• Oil of eucalyptus: Bronchitis and Mucolytic.
• Flavouring (Oil of Lemon)
• Perfumery (Oil of Rose)
• Anti-septic – due to high phenols (Oil of Thyme).
Also as a preservative (oils interfere with bacterial
respiration)
• Anti-spasmodic (Ginger, Lemon balm, Rosemary,
Peppermint, Chamomile, Fennel, Caraway)
• Aromatherapy
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 Extraction Methods

 Distillation in water or steam

 Expression
 Extraction with solvents

 Enzymatic hydrolysis
 Enfleurage

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 Distillation
There are three basic types of essential oil distillation:
1. water or "hydro-distillation"
2. water and steam or "wet steam"
3. steam or "dry steam“

Hydro-distillation - in this method the plant material is

immersed totally in boiling water.

 The disadvantages are that the heat is difficult to control

and hence the rate of distillation is variable.

 Also there is a possibility for overheating and "burning"

which lead to a poorer quality oil. 21
Water and steam or "wet steam“ --the plant material is
placed on a grid which keeps the plant material above the
water level.
 The water is boiled below the grid and "wet" steam passes
through the plant material.

Steam Distillation -----direct steam provided from a separate

boiler.
 The still contains a grid plate under which an open steam
pipe is fitted.
 The advantage of "dry" steam distillation is that it is rapid,
therefore it is less likely to damage those oils.
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Steam Distillation 23
wet steam
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 Expression
• These are mechanical techniques carried at room
temperature.
• Used in preparation of heat sensitive oils.

• This method is used for the preparation of oil of lemon, oil

of orange, and oil of bergamot.

• The two principal methods of scarification are the

"sponge," and the ecuelle a piquer.

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 Expression

The Sponge method

• Plant materials (e.g. rind of an orange) is turned in

side out and squeezed …Secretion glands (sacs)
rapture & the oil is collected by means of sponge

• The sponge is periodically squeezed in a vessel

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 Expression

• The Scarification method--- The instrument used is

called Ecuell a’ piquer
• It consists of funnel made of copper tinned inside.
• The upper saucer like part bears in its inner surface
numerous strong metal pins just long enough to
penetrate the epidermis of the peels.
• By repeatedly rotating the instrument after placing
lemons in the bowl the oil glands are punctured
(scarified) and discharge their oil contents which
collect in the handle.
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Ecuell a’ piquer

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 C- E
Extraction with solvents
For preparation of delicate flowers oils which contain either
small amounts of oils or heat sensitive oils

Classified into:
I. Non-volatile solvent extraction.
II. Volatile solvent extraction.

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 C- E
Extraction with solvents

Extraction by volatile solvent:

• Plant material is extracted with the volatile solvent (low
boiling point) by percolation.
• Evaporation of the volatile solvent containing the volatile oils
in vacuum at low temperature resulted in the evaporation of
the solvent leaving the volatile oils as floral concrete.
• The advantage of this method is
– Low and uniform temperature can be maintained
– Oils has more natural odour than oils extracted by
distillation. This is feature is desired by the perfume
industry.
• The disadvantage is it is very expensive method. 30
 C- E
Extraction with solvents
Extraction by non-volatile solvent: The Enfleurage
method:
• A mixture of melted beef tallow and lard is thickly
smeared on both surfaces of each of the glass plates,
which are enclosed in a wooden frames.

• Each glass plate is sprinkled with flowers to cover its

top, under this condition each layer of the flowers
will be enclosed between the two layers of fat (24
hours). The process is repeated and fresh flowers are
used for the same plates. 31
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 C- E
Extraction with solvents
• The process is repeated and fresh flowers are used
for the same plates.

• The flowers are then removed and the saturated fat

is extracted with absolute alcohol.

• The alcoholic extract is carefully cooled and filtered

to remove any traces of fats which might remain in
solution or suspension.

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 Enzymatic hydrolysis

• Occasionally, the volatile oil is found in the plant in a

glucosidal combination.

• The odoriferous substance is set free only by hydrolysis of

certain odorless glycosides present in plant.

• For glycosidic volatile oils e.g. mustard oil.

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Herbs containing Volatile Oils

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 Ginger/Ginjibil: Zingiber officinale

• Definition: Ginger is the

peeled or unpeeled rhizome
of Zingiber officinale
(Zingiberaceae).

• Common Names: Jamaican

ginger, Ginger

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 Constituents
• Volatile oils (1 – 2%)
– Camphene, Cineole, Citral, Borneol
• Gingerol – pungent component
• Shogaols, Zingiberene & Zingiberol
• Resins
• Starch
• Mucilage

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 Uses & actions
Actions
• Carminative
• Stimulant
• Anti-emetic
• Anti-bacterial and Anti-fungal
• Gingerol – Anti-inflammatory
• Shogaols– increases bile
secretion and enhanced GIT
activity
Uses
• Motion Sickness
• Morning Sickness
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 Cinnamon/qarafa: Cinnamomum
zeylanicum
• DEFINITION: Cinnamon
is the dried bark of
Cinnamomum
zeylanicum (Lauraceae).

• GEOGRAPHICAL
SOURCES
Cultivated in Sri Lanka,
South India, Seychelles,
Madagascar,
Martinique, Cayenne,
Jamaica & Brazil.
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 Constituents

• Volatile oils (at least 1.2

%)---cinnamyl acetate,
and cinnamyl alcohol
• Mucilage
• Calcium Oxalate
• Starch

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 Uses

• Aromatic,
carminative,
stimulant, anti-
microbial, anti-funga

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 CARDAMOM/kororima

DEFINITION: Cardamom
consists of the dried, nearly
dried ripe fruits of Elettaria
cardamomum var miniscula
(Zingiberaceae).

PARTS USED: Seeds (should

be kept in the fruit until
ready to be used – Prevents
loss of volatile oils).
 Elettaria cardamomum
• GEOGRAPHICAL
SOURCES
– Sri Lanka
– India
– Guatemala
 PRODUCTION, COLLECTION &
PREPARATION
• Mainly obtained from
cultivated plants
(propagated by seedlings or
vegetatively)
• Capsules on the same plant
ripen at different times –
important to collect them
before they split.
 Constituents
• The major components: 1,8-cineole, linalool,
terpinyl acetate

• Other monoterpenes, such as camphene and

carvacrol, are present in less than 0.1% levels

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 Actions and uses
• Flavouring agent

• Liqueur manufacture

• Small amount is used for

pharmaceutical
manufacture (Compound
Tincture of Cardamom).
 Clove/Qurufund
Cloves are the dried
flower buds of Syzygium
aromaticum (Eugenia
caryophyllus),
(Myrtaceaea).

Geographical Sources
Molucca or Clove Islands,
Zanzibar, Pemba,
Madagascar, Indonesia
and Brazil. 47
 Constituents

14-21% Volatile oils

• Mainly eugenol & isoeugenol
• Sitosterol
• Stigmasterol
• Campesterol

Tannins
Triterpene acids & esters
Glycosides
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 Uses of clove

 Anti-septic
 Stimulant aromatic
 Spice
 Flavouring Agent
 potential anti-
carcinogenic
compounds
(Sesquiterpene)

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 LEMON PEEL
Definition: Dried lemon
(Limonis Cortex) peel is
obtained from the fruit
of Citrus limon
(Rutaceae).
Botanical Description:
Small tree, growing to 3-5
m in height.
Geographical Sources
Mediterranean Regions
 Limonis Cortex – CHARACTERISTICS
Dried lemon peel occurs in
spiral bands (2 cm wide;
2-3 mm thick).
The outer surface is rough
& yellow; the inner
surface is pulpy & white
(anatomically similar to
that of an orange peel).
Odour: Strong &
characteristic
Taste: aromatic & bitter
 CONSTITUENTS
Should contain at least 2.5% volatile oil—Limonene,
alpa-Pinene, terpinene, and linalool/linalyl acetate

Vitamin C
Hesperidin (Flavonoid)
Mucilage

USES
Flavouring purposes
 Eucalyptus leaf
DEFINTION: Eucalyptus leaf
consists of the whole or cut
dried leaves of the older
branches of Eucalyptus
globulus, (Myrtaceae).

GEOGRAPHICAL SOURCES
Portugal, SA, Spain, China,
Brazil, Australia, India &
Paraguay.

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 Eucalyptus - Constituents
Volatile Oil (at least 2 %)
At least 70 volatile oils----The main chemical
components of eucalyptus oil are a-pinene, b-
pinene, a-phellandrene, 1,8-cineole, limonene

Sesquiterpene - Anti-bacterial action against

oral pathogens.

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 Eucalyptus oil - uses
 Alleviating the symptoms of
nasopharyngeal infections
 Treating coughs
 Decongestant

Official preparations
Mixtures, inhalations, lozenges
also applied externally as
ointments and liniments.
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 Jasmine
• Jasmine (Jasminum) (from Old French Jasmine which
is from the Persian yasmin, i.e. "gift from God", via
Arabic)

• is a genus of shrubs(Jasminum sambac) in the olive

family (Oleaceae), with about 200 species, native to
tropical and warm temperate regions of the World.

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Active constituents:
• Volatile oil contains :Methyl anthranilate, indol, benzyl
alcohol and linalol.
Uses:
• Jasminum sambac flowers are also used to make tea,
which often has a base of green tea.
• The French are known for their jasmine syrup, most
commonly made from an extract of jasmine flowers.
• Many species are used in the production
of perfumes and incense.

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 Thyme
• Thyme is a well known herb; in common usage the
name may refer to any or all members of the
plant genus Thymus,

• Common thyme, Thymus vulgaris, and some other

species that are used as culinary herbs or for
medicinal purposes
• The dried aerial parts of Thymus vulgaris and other
Thymus species of the family Labiatae.

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Active Constituents
• Over 1% volatile oil: thymol, carvecol.
Use and action
• Thymol is an antiseptic.
• Used for cough and bronchitis.
• Very effective against inflammation of the throat when
gargled 3 times a day.
• Other infections and wounds can be dripped with thyme
that has been boiled in water and cooled.
• Its oxytocin-like effect causes uterine contractions and
more rapid delivery of the placenta.

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 Fennel Fruit (Fructus Foeniculi)
• The dried ripe fruits of Foeniculum vulgare F.
Umbelliferae (Apiaceae) obtained from cultivated
plants
• Indigenous to Mediterranean countries, cultivated in
Europe
Active Constituents & Uses
– Volatile oil (4 – 5%) composed of anethole and
fenchone

– Used as a flavouring agent and carminative

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 Anise oil/Fructus Anisi (Aniseed)

• The dried ripe fruits of Pimpinella anisum of family

Umbelliferae (Apiaceae)
• Indigenous to Egypt, Turkey and Greece and
cultivated in Europe

Active Constituents and Uses

• Volatile---80-90 % anethole

• Used as a carminative and flavouring agent

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 Caraway Fruit (Fructus Carvi)

• The dried ripe fruits of Carum carvi of the family

Umbelliferae (Apiaceae)
• Cultivated mainly in Europe and Russia

Active Constituents and Uses:

• Volatile oil (5 -7 %)…….Contains carvone (50 – 60 %)
as main component of oil

• Used as carminative and flavouring agent

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65
 PEPPERMINT
& PEPPERMINT OIL
DEFINITION: Peppermint
is the dried leaves of
Mentha piperita
(Labiate).
 Oleum Menthae
Oil of peppermint is
obtained from Mentha
piperita via steam
distillation using the
flowering tops.
Oil should contain at least
44 % menthol, 15-32 &
menthone and 4.5-10 %
menthyl acetate.
 Oleum Menthae - CONSTITUENTS
Menthol
Menthone & isomenthone
Menthyl acetate
Limonene
Cineole
Menthofuran
Pulegone
Cineole

OIL COMPOSITION: greatly

influenced by genetic
factors & seasonal variation.
PEPPERMINT & PEPPERMINT OIL USES
OIL: anti-bacterial,
cooling, carminative