Kwame Nkrumah University of

Science & Technology, Kumasi, Ghana

COURS TITLE: Phytochemistry

COURSE CODE: Pharm 271

TOPIC: Volatile oils, Resins and Balsam

Prof. Gustav Komlaga

Department: Pharmacognosy
Faculty & College: Faculty of Pharmacy and Pharma
Sciences, College of Health Sciences
 Learning objectives

1. Understand what volatile/essential oils, resins

and balsams are.
2. State their physical and chemical characteristics
3. Describe their various uses
4. Describe the production of volatile oils

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 Volatile oils
• These are fragrant/ordoriferous
/ordorous substances (usually liquid).
• Also referred to as ethereal or
essential oil.
• Volatile at ordinary temperature
• are of plants and sometimes animal
origin (civet and musk deer oil)

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 Physical properties
1. Exist as liquids
2. They possess characteristic agreeable odours.
3. Frequently associated with other substances such as gums and resins
4. They are volatile at ordinary temperature.
5. they give a temporary translucent strain when smeared on paper
6. They have high refractive indices.
7. Most of them are optically active.
8. less dense than water (exceptions is sassafras, clove, or cinnamon oils).
9. are immiscible with water, but sufficiently soluble to impart their odour to
water.
i. The so called aromatic waters are dependent on this slight solubility.
10.They are soluble in alcohol and are dissolved in alcohol to produce tincture

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Physical characteristics cont’ed

• Are of vegetables or plants origin

• They tend to resinify on exposure to high
temperature, light and oxygen
• They differ entirely in both chemical and
physical properties from fixed oils.

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 Origin of natural volatile oils
• All official volatile oils are of vegetable origin.
• They occur in all part of the plant including
fruit, bark, root, flower leaf, seed, wood
• Are stored in special secretory tissues/cells in
the plant
– Oil cell
– Glandular trichomes
– Secretory cavities
– Secretory canals Secretory canals
• For animals in odorous sacs
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 Exceptions to preformed oils
• mustard and almond oils are produced by
the enzymatic hydrolysis of their glycosides.
Amygdalin (cyanogenetic glycoside)
emulsin (enzyme)

glucose + benzaldehyde + HCN

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 Uses of volatile oils
• As Flavoring agents (e.g. oil of
lemon)
– In pharmaceutical industry to mask the
unpleasant tastes of medicines
– In food industry as taste enhancers
(vanilla, lemon and strawberry essences)
– In Cosmetic industry as fragrance: body
creams, soaps, perfumes

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 Uses of volatile oils cont.

• as starting materials for the

synthesis of other compounds (e.g.
oil of turpentine).

• In veterinary:
• As anthelminthic or worm-
expellers/killers.
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 Uses of volatile oils cont.
• As insecticides:
– Limonene and menthol are used to make
insecticides
• Industrial deodorants
– to deodorize industrial products like rubber,
plastic, Toys and paint.
– In the textile industry: before and after dyeing.
– In paper manufacture, products such as
notebooks, toilet paper, and face wipes are
scented
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 Medicinal uses
• Anti-septic and preservative
High phenol content
• as gargles and mouthwashes
• eg thymol oil
• Anti-spasmodic
– Eg. Ginger, Lemon balm, Rosemary,
Peppermint, Chamomile, Fennel,
Caraway oils
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 Uses of volatile oils cont.
• As carminatives
– e.g. peppermint oil
• Anti-bronchitis and Mucolytic.
– Administered as inhalants (e.g.
eucalyptus oil)
• As counterirritants
• As antioxidants
• In aromatherapy
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Chemical composition of volatile
oils mixture
• A typical VO is a complex
containing hundreds of volatile organic
compounds, which reflect the
characteristics of the oil.
• These volatile compounds belong to
various chemical classes:
– alcohols, ethers or oxides, aldehydes, ketones,
esters, amines, amides, phenols, heterocycles,
and others.
• most are terpenes.
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Some components of
volatile oils
 Chemical composition of VOs cont.
• The chemical composition of VOs depends on
the place of origin, climatic conditions, and
plant species. 
• the overall characteristics of different oils vary.
• Individual components differ for different oils
• The individual composition in a mixture can be
separated by physical methods such as
dissolving or distilling
• The removal of particular compounds from
essential oils common in the cosmetics,
pharmaceutical and food industries
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 Composition effect on physical
characteristics
• The odour and taste is mainly determined by the
oxygenated constituents
• Every member of the mixture is essential to the
odor and flavor.
• The absence of even a minor component may
change the aroma and flavour.
• The oxygenated constituents are to some extent
soluble in water but more soluble in alcohol.

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Chemical nature of the components of VOs
Volatile oil compounds are mostly
terpenoids formed from isoprene units
(are subject to isoprene rule). Others are
of aromatic origin
The terpenoid volatile compounds can be
• cyclic or aliphatic in structure
• Hydrocarbon (isoprenes), oxygenated
hydrocarbon or in few cases
heterocycle.

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 Biosynthesis of volatile oils
Biosynthetic origin of VOs
1. Biosynthesis of essential oils occurs through
two complex natural biochemical pathways
involving different enzymatic reactions.
• Terpene derivatives (terpenoids) formed via the
acetate-mevalonic acid pathway and derived from
isoprene units (C5) bonded in a chain.
• Aromatic compounds formed via the shikimic acid-
phenylpropanoid route

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 Terpenoid compounds
CH3 CH3 CH3

OH OH

H3C CH3 H3C CH2 H3C CH3

Menthol Carvone Thymol
(peppermint oil) (caraway oil) (thyme oil)

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 Aromatic compounds
OH OCH3

OCH3

CH2 CH3 CHO

Eugenol Anethole Cinnamaldehyde

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

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Preparation of volatile
oils

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• Water distillation. The plant material
is boiled with water and the vapour is
passed through a condenser, collected
and the oil separated from the water.
• Steam distillation. The plants are
placed on a perforated base or sieve
and steam generated elsewhere is
passed through it. The volatile
component volatilise and escape with
the water vapour, passed through a
condenser, collected and the oil
separated from the water.

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• Enfleurage: Flower petals containing the oils
are spread over a thin film of fat placed on a
glass plate. The essence passes into the fat
until saturated. The oil saturated fat may be
used as a pomade or the essential oil may
be extracted using 70% alcohol. (extraction
of oils used in perfumery)

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• Pneumatic method: warm air passed
through the flower and then through a spray
of melted fat
• Digestion method: flower gently heated in
melted fat until exhausted, strain and cool
the oil laden fat. oil may be extracted with
alcohol and sold as flower perfume or oil
recovered in the pure form.

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• Scarification (ecuelle a piquer ): used to extract oil
from orange fruits. The fruit is place in a specially
designed bowl with spikes. The orange is then
rotated/tossed in the bowl. The oil cells are punctured
by the spikes thereby allowing the oil to flow out.
• Expression (cold pressing): used to extract essential oils
from the rinds of citrus fruits. 
• The peels are soaked in warm water and the oil is
forced/pressed from the material using a clothing
material/sieve or under high mechanical pressure. 
• Extraction with solvents: the plant material is steeped
in organic solvent eg ethanol to extract the oil. the oil is
often separated by distillation.
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• Enzymatic hydrolysis (for glycosidic volatile oils e.g.
mustard oil).
1. Amygdaline(glycoside)/water/emulsin = glucose+
cyanide + volatile oil (benzaldehyde)

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 Changes in essential oils and possible
consequences
• Essential oil constituents may be enzymatically or
chemically transformed through
• Oxidation
• degradation
• polymerization
• isomerization,
• cyclization, or
• dehydrogenation

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 Effects of changes in oil
components.
• Chemical transformation affects the
composition of the oil and its
characteristics including its consistency

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 Effects of changes in oil
• Organolepticcomponents.
and viscosity/consistency
– development of unpleasant and pungent flavours,
– changes in colour of oils
– changes in consistency due to resinification
• Also changes in composition

Degraded oils may sensitize the skin leading to a

hypersensitivity reaction or allergic contact
dermatitis.
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Determinants of volatile oil stability
• Light: UV and visible lights accelerate
auto/photo-oxidation
• Temperature: Ambient temperature
crucially influences essential oil stability in
several respects
– Generally, chemical reactions rates increase
temperature

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 Determinants of volatile oil stability
• Oxygen availability. This leads to air-
induced oxidation reactions
– main cause of essential oils spoilage .
– The reason oils must be closed with no space
above it.
• Metal contaminants: heavy metals from
metallic containers (copper and ferrous
ions) promote autoxidation, in particular if
peroxides are already present

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 Determinants of volatile oil stability

• Water content. Moisture has been considered

as a possible reason for essential oil spoilage

• Compound structure and chemical

composition. Susceptibility of essential oils to
degradation largely depends on molecular
structures of the constituent compound

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 STORAGE OF VOLATILE OILS
• Volatile oils are liable to oxidation on
storage in presence of air, moisture, and
light.
• The oxidation is followed by the change in
colour, increase in viscosity, and change in
odour.
• Hence, volatile oils must be stored in well-
closed completely filled containers and
away from light in cool places

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Plant resins and resins
combination

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 Resin,

• The term ‘resin’ is applied to a more or less

solid, amorphous products of complex
chemical nature.
• It is natural or synthetic organic
compound which may be non-crystalline
or viscous liquid substance.

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 Physical properties
• On heating they soften and finally
melt.
• Insoluble in water and petroleum
ether
• But soluble in alcohol, chloroform
and ether.
• Resins burn with a characteristic,
smoky flame.
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 Chemical composition
• Chemically, resins are complex mixtures
of resin acids, resin alcohols (resinols),
resin phenols (resinotannols), esters and
chemically inert compounds known as
resenes.

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 Classification

• May be
– Oleoresins associate with volatile oils
– gum-resins associate with gums
– oleo-gum-resins associate with oil and gum
• Glycosidic resins occur as glycosides

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 Classification cont.

 Resins are classified in three different ways:

1. Taxonomical classification, i.e. according to botanical
origin, e.g. Berberidaceae resins.
2. Classification according to predominating chemical
constituent; e.g. acid resins, resene resins, glycosidal
resins; etc.
3. Resins may be classified according to the associating
component e.g. resins, oleoresins, oleogumresins,
balsams.
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 Examples of resins and resins
combination

• Resins: colophony, cannabis.

• Oleoresins: copaiba, ginger.
• Oleo-gum-resins: asafoetida, myrrh.

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Balsams

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• Basalms are aromatic resinous substance
with medicinal properties
• They contain cinnamic acid, benzoic acid,
or/and their derivatives
• True balsams include Benzoins, Liquid Storaque
and the Balsams of Tolu and Peru.
• Many other aromatic exudates, such as Copaiba Oil
and Canada Balsam, are wrongly called balsam.
– These are more or less essential oils, resins and
oleoresins.

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 uses

• For therapy and healing properties

• in the perfume industry as fixatives
• in the cosmetics industry and in cookery as
preservatives and aromatizers.

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 References
• Treas and Evans Pharmacognosy
• Abdallah A. Shaltout, El‐Sayed S. Abdel‐Hameed, Fabjola Bilo, Laura Borgese and Laura
E. Depero, Direct analysis of essential oils by means of TXRF spectrometry, X-Ray
Spectrometry, 49, 2, (322-331), (2019).
• Evans, W. C. (2009) Trease And Evans Pharmacognosy. 16th Editi. Edinburgh, UK: W.B.
Saunders.
• Langenheim, J. H. (2003) Plant Resins: Chemistry, Evolution, Ecology, and Ethnobotany.
Portland, Cambridge: Timber Press.
• The Editors of Encyclopaedia Britannica. Resin, Chemical compound. Available at
URL:https://www.britannica.com/science/resin. Accessed: 09/04/2020
• Turek, C. and Stintzing, F. C. (2013) ‘Stability of Essential Oils: A Review’,
Comprehensive Reviews in Food Science and Food Safety. John Wiley & Sons, Ltd,
12(1), pp. 40–53. doi: 10.1111/1541-4337.12006.

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