ESSENTIAL OILS

Prepared by: Engr. Benedict S. Marzan

DEFINITION

The International Organization for

Standardization (ISO) in their Vocabulary of
Natural Materials (ISO/D1S9235.2) defines an
essential oil as a product made by distillation
with either water or steam or by mechanical
processing of citrus rinds or by dry distillation
of natural materials. Following the distillation,
the essential oil is physically separated from
the water phase.
Essential Oils

Essential oils may be defined as volatile, odoriferous

oils of vegetable origin.
Essential oils are connected with metabolism,
fertilization, or protection from enemies. It is found in
buds, flowers, leaves, bark, stems, fruits, seeds, wood,
roots and rhizomes.
In some trees in oleoresinous exudates.
Essential oils are insoluble in water and soluble in
organic solvents, although enough of the oil may
dissolve in water to give an intense odor to the
solution, e.g., rose water or orange flavor water.
Compounds occurring on essential oils

1. Esters mainly of benzoic, salicylic, acetic and cinnamic acids

2. Alcohols Linalool, geraniol, citronellol, terpinol, menthol,
borneol
3. Aldehydes citral, citronellol, benzaldehyde,
cinnamaldehyde, vanillin
4. Acids benzoic, cinnamic, myristic, isovaleric in the free state
5. Phenols eugenol, thymol, carvacrol
6. Ketones carvone, menthone, pulegone, irone, camphor,
methyl nonyl ketone, methyl heptenine
7. Esters cineole, internal ether (eucalyptole), anethole, safrole
8. Lactones coumarin
9. Terpenes camphene, pinene, limonene, phellandrene,
cedrene
The Biological Role Of Essential Oils Within Plants
While essential oils are in the plant, they are constantly changing
their chemical composition, helping the plant to adapt to the ever-
changing internal and external environment. Recent scientific
research has shown that plants produce essential oils for a variety of
purposes including:
To attract pollinators and dispersal agents
To play a role in allelopathy, a type of plant-to-plant
competition
To serve as defense compounds against insects and other
animals
To protect the plant by their antifungal and antibacterial
nature
1. To attract pollinators and dispersal agents

Insects have been pollinating flowers for over 200 million years. Insects, like
humans, are attracted to specific plants for one of three possible reasons: its
aroma, its color, or its morphology or physical structure. Scent appears to be
more ancient than flower color as an attractant to insects.Various insects,
including bees, butterflies, and even beetles, are known to be attracted by
the aroma of a plant.
2. To play a role in allelopathy, a type of plant-to-
plant competition

Allelopathy occurs when a plant releases chemicals to prevent competing

vegetation from growing within its area or zone. An often-cited example is in
southern California, home to the dominant shrubsSalvia leucophylla(sage
bush) andArtemisia californica(a type of sage). Both species release
allelopathic terpenoids, eucalyptol and camphor, into the surrounding area,
which effectively prevents other plant species from growing around them.
This is allelopathy. Chemicals that deter competing growth (terpenes, for
example) are referred to asallelochemics.
3. To serve as defense compounds against
insects and other animals

Plants, like other living things, need to protect themselves from various types
of predators. Plants use terpenoid compounds to deter insects and other
animals from approaching them. Insects are very rarely found on peppermint
plants, and the presence of linalol in the peel of citrus fruits confers
resistance to attack by the Caribbean fruit fly.The Douglas fir tree releases a
complex mixture of volatile oils, or terpenes, from their needles to defend
against the spruce budworm. Even more fascinating is that the Douglas fir
trees will vary the composition and production of terpenes each year thus
decreasing the ability of the budworm to develop widespread immunity to
specific compounds.
4. To protect the plant by their antifungal and
antibacterial nature

Resins and complex combinations of terpenes are released by some plants

and trees, such as evergreens, to act as antimicrobial, antifungal, and
antibacterial agents against a wide range of organisms that may threaten the
survival of the plants. Compounds such as sesquiterpene lactones found in
plants such as feverfew, yarrow, and blessed thistle, have been found to play
a strong antimicrobial role as well as a protective role from herbivores.
The Storage Of Essential Oil Within The Plant
Plants store essential oils either inexternal secretory
structures, which are found on the surface of the plant,
orinternal secretory structures, which are found inside the
plant material. Usually with plants having external secretory
structure, you just have to lightly touch them and you will notice
an aroma imparted to your skin. With plants having internal
secretory structures, you may need to break the leaf or seed in
order to get to the aroma/essential oil.
External Secretory Structures
Glandular trichomes
External secretory structures in plants are Click icon to add picture
calledglandular trichomes. They can be
found on the surface of the plant (such as
herbaceous leaves) and are thought to be
responsible for the production of chemicals that
deter or attract pests or pollinators. Glandular
trichomes are most commonly found in the
Lamiaceae (syn. Labiatae) family. The oil
storage capacity varies from species to species
and also between trichomes. Biochemical
experiments have shown that these volatile oils
are synthesized by highly refined enzyme
reactions taking place within the plant.
Common essential oils that have glandular
trichomes:Basil, Lavender, Marjoram, Melissa,
Oregano, Peppermint, Rosemary, and
Spearmint
Internal Secretory
Secretory cavities and ducts Structures
Secretory cavities and ducts consist of large,
intercellular spaces that are formed either by
Click icon to add picture
the separation of the walls of neighboring cells,
or by the disintegration of cells.Cavities occur
as spherical spaces and are most commonly
found in the Myrtaceae and Rutaceae families.
Ducts are more elongated spaces and are most
commonly seen in the Asteraceae (syn.
Compositae), Pinaceae, Apiaceae (syn.
Umbelliferae), and Coniferae families.
Common essential oils with secretory
cavities:
Citrus oils: Bergamot, Grapefruit, Lemon, Lime,
Orange, and Tangerine; Eucalyptus species;
Clove bud; and Resin trees: Benzoin,
Frankincense, and Myrrh
Common essential oils with secretory
ducts:Angelica, Caraway, Carrot seed, Dill,
Fennel, Fir, Cedar, Pine, Spruce, Juniper, and
Essential Oil cells

Essential oil cells are found within the plant tissue and
are unique from other cells in content and size. They
can often be found throughout the plant and are most
commonly seen in the Lauraceae, Piperaceae,
Gramineae, and Zingiberaceae families.
Common essential oils with cells:Bay Laurel, Black
pepper, Cardamom, Cinnamon, Citronella, Ginger,
Lemongrass, Nutmeg, Palmarosa, and Patchouli
What are fragrances?

Manufacturing of perfume, cologne and toilet water

are collectively known as fragrances.
Perfume takes its name from Latin word perfumare,
means to fill with smoke
Perfume is a mixture of fragrant essential oils and
aroma compounds, fixatives, and solvents used to
give the human body, objects, and living spaces a
pleasant smell.
Flavors and Fragrances
Extraction process

Expression
Distillation
Extraction with volatile solvents
Enfleurage
Maceration
Microwave extraction
Supercritical solvent extraction
Expression

Expression is useful for things like lemon and lime peels.

For most plants, the oils are contaminated with too many other
undesirable compounds to make the method practical.
The compounds are not changed by heat, however, and in some
instances are better quality than steam distilled or
fractionally distilled.
Raw material is compressed to obtain the oil.
The only fragrant oil from the peels of fruits is in the
citrus family extracted in this manner .
Citrus fruits. Click icon to add picture

CarolinaBiologicalSupplyCo.
Distillation
Dry/destructive distillation:

Click icon to add picture

The raw materials are
directly heated in a still.
Fragrant compounds that are
released from the raw material
by the high heat often undergo
anhydrous pyrolysis, which
results in the formation of
different fragrant compounds.
This method is used to
obtain fragrant compounds
from fossil amber and fragrant
woods.
Distillation
Fractionation: Click icon to add picture

Through the use of a

fractionation column, different
fractions can be selectively
excluded to modify the scent of
the final product. This is
sometimes performed to
remove unpleasant scents of a
material with certain purpose.
Oil ylang-ylang
(Cananga odorata,
Annonaceae) is
widely used in
perfumes and is
relatively
expensive.
Steam distilling ylang ylang,
Cananga odorata NationalGeographic
Essential oil from Acacia dealbata
Lavender
(Lavendula
officinalis or
L. vera)
(Lamiaceae or
Labiatae) also
important from
Provence.
 Lemon grass oil (Cymbopogon citratus,
Poaceae or Gramineae) is widely used as
a substitute for expressed lemon oil.
It is used in soaps, perfumes, food
products, and in mosquito repellents.
Citronella oil
(Cymbopogon
nardus),
Poaceae, used to
be widely used
as a mosquito
repellent in the
South.
Extraction
Maceration/Solvent extraction:
Click icon to add picture

Maceration is the most used and

economically important technique with raw
materials that is submerged in a solvent.
Maceration lasts anywhere from hours to
months. Fragrant compounds from woody
and fibrous plant materials are often
obtained in this manner. The technique can
also be used to extract odorants that are too
volatile for distillation or easily denatured by
heat. Commonly used solvents for
maceration/solvent extraction include
hexane, and dimethyl ether.
The product of this process is called a
"concrete".
 Supercritical fluid extraction:
Extraction
A technique for extracting fragrant
compounds from a raw material, which often
employs Supercritical CO2 with low heat of
process and the relatively nonreactiveClick icon to add picture
solvent
used in the extraction.
*Supercritical fluid a substance at a
temperature and pressure about its own
thermodynamic critical point that can diffuse
through solids like a gas and dissolve
materials like a liquid.

Ethanol extraction:
Used to extract fragrant compounds directly
from dry raw materials, as well as the impure
oily compounds materials resulting
enfleurage.
Not used to extract fragrance from fresh plant
materials .
Enfleurage:
Extraction
Absorption of aroma materialsClick icon to add picture
into solid fat or wax and then
extracting the odorous oil with
ethyl alcohol. Extraction by
enfleurage was commonly used
when distillation was not possible
because some fragrant compounds
denature through high heat. This
technique is not commonly used in
the present day industry due to its
prohibitive cost and the existence of
more efficient and effective
extraction methods.
Top notes: Notes
Fragrance
Click icon to add picture
The scents that are perceived
immediately on application of a
perfume. Top notes consist of
small, light molecules that
evaporate quickly. They form a
person's initial impression of a
perfume and thus are very
important in the selling of a
perfume. Also called the head
notes.
Fragrance Notes
Click icon to add picture
Middle notes or Heart Notes :

The scent of a perfume that emerges just prior to when the

top notes dissipate. The middle note compounds form the
"heart" or main body of a perfume and act to mask the often
unpleasant initial impression of base notes, which become more
pleasant with time. They are also called the heart notes.
Base notes:
The scent of a perfume thatClick icon to add picture
appears close to the
departure of the middle notes.
The base and middle notes
together are the main theme
of a perfume. Base notes
bring depth and solidity to a
perfume. Compounds of this
class of scents are typically
rich and "deep" and are
usually not perceived until 30
minutes after application.
The scents in the top and middle
Fragrance Notes by the base
notes are influenced
notes, as well as the scents of the
Click icon to add picture
base notes will be altered by the
type of fragrance materials used
as middle notes.

Manufacturers of perfumes usually

publish perfume notes and
typically they present it as
fragrance pyramid, with the
components listed in imaginative
and abstract terms.
 Odorants give the perfumes characteristic
odor.
There are five types:
concretes
absolutes
distilled and fractionally distilled oils
expressed oils
tinctures.
Concretes

Many factors determine which method is

used. Among these are cost, quality of
essence, and use of the product.
Concretes are the purest of the natural
odorants. They are obtained by using a
hydrocarbon solvent to dissolve the
essential oils out of the plant.
The solvent is then removed under
vacuum by mild heating.
Absolute

Absolutes are extracted from the

non-volatile materials with
alcohol.
The alcohol is removed under vacuum
The alcohol is recovered and used
in colognes and lotions.
Enfleurage

Tray of lard with jasmine flowers used for enfleurage

Distilled Oils

Oil ylang-ylang
(Cananga odorata,
Annonaceae) is
widely used in
perfumes and is
relatively
expensive.
Steam distilling ylang ylang,
Cananga odorata
Expressed Oils

Citrus fruits.

CarolinaBiologicalSupplyCo.
Tinctures

Tinctures (or alcoholic extracts) are

widely used. They are cheap, but they
are sometimes contaminated with other
undesirable products as well.
References
1Sell, Charles. (2010). Chapter 5: The Chemistry of Essential Oils. (Can Baser K
H, and Buchbauer G. Editors) in the bookHandbook of essential oils : science,
technology, and applications, (pp. 121-150). Boca Raton, FL: CRC Press, Taylor
& Francis Group.
2Lawrence, B. (2000). Essential Oils: From Agriculture to Chemistry.NAHAs

World of Aromatherapy III Conference Proceedings, pp. 826.

3Shawe, K. (1996). The Biological Role of Essential Oils, Aromatherapy

Quarterly, 50, 23-27.

4IBID.

5Shawe, K. (1996). The Biological Role of Essential Oils, Aromatherapy

Quarterly, 50, 23-27.

6Buhner, S. (2002). The Lost Language of Plants. White River Junction,

Vermont: Chelsea Green Publishing.

7Svoboda, K. (1996). The Biology of Fragrance. Aromatherapy Quarterly, 49,

25-28.