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Essential oil

Definition
Essential oils:
- Volatile principles of plant and animal source,
evaporate when exposed to air at ordinary
temperature, and hence known as volatile or etheral
oils.

- Have the characteristic odor or flavor of the plant.

- Water-immiscible liquid separated by distillation from

the plant material.

- High boiling point (>150 oC).

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Popular essential oils

Trade name Vietnamese Plant
Cajeput oil TD Tràm Melaleuca leucadendron

Cassia oil TD Quế TQ, VN Cinnamomum cassia

Cinnamon oil TD Quế Srilanka Cinnamomum zeylanicum

Citronella oil TD Sả Java Cymbopogon winterianus

Clove oil TD Đinh hương Syzygium aromaticum

Coriander oil TD Mùi Coriandrum sativum

Star anise oil TD Hồi Illicium verum

Turpentine oil TD Thông Pinus sp.

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Trade name Vietnamese Plant

Eucalyptus oil TD Bạch đàn Eucalyptus globulus

Eucalyptus TD Bạch đàn

Eucalyptus citriodora
citriodora oil chanh

Lemon oil TD Chanh Citrus limon

Lemongrass oil TD Sả C. flexuosus, C. citratus

Palmarosa oil TD Sả hoa hồng C. martinii var. motia

Rose oil TD Hoa hồng Rosa damascena

Cinnamomum parthenoxylon
Sassafras oil TD Xá xị
và một số loài Cinnamomum
Ocimum gratissimum oil TD Hương nhu trắng Ocimum gratissimum 4

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Essential oil vs Fixed oil

Property Essential oil Fixed oil
Volatilization at room
Volatile Non-volatile
temperature
Soluble in organic
Almost insoluble
Solubility solvents (ether, CHCl3,
in alcohol
alcohol)
Stain on filter paper Transient Permanent greasy
Complex mixtures of
Composition hydrocarbons & Triglycerides
oxygenated compounds
Saponification with KOH Negative Positive

Essential oils differ entirely from fixed oils in both

chemical & physical properties. 5

Phytochemistry of essential oils

1. Monoterpene compounds

2. Sesquiterpene compounds

3. Aromatic compounds

4. Organo-nitrogen, organo-sulfur compounds

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Terpenoids - Rule
tail
head

tail
head
Isoprene Isoprene unit Myrcene

monoterpene sesquiterpene 7

Classification of terpenoids
Class Number of carbon atoms
Terpene 10
Sesquiterpene 15
Diterpene 20
Triterpene 30
Tetraterpene 40

b-carotene
8
Oleanane skeleton

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Monoterpene
a. Acylic monoterpene

- Hydrocarbon

ocimene myrcene

-Oxygenated

Alcol (geraniol, nerol, linalol, citronellol…)

Palmarosa Citronella (Sri Lanka)

smells sweet and rose-like (+)-Citronellol
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-Oxygenated

Aldehyde (geranial=citral a, neral=citral b, citronellal…)

Lemongrass Leaves of lime

Citronella java Eucalyptus citriodora

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Monoterpene
b. Monocyclic

Limonene Phelandrene Carvone

(peel of lime)

a-terpinene β-terpinene γ-terpinene

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Monoterpene
b. Monocyclic

OH OH

OH

a-terpineol b-terpineol ɣ-terpineol

(Tea tree oil)
Malaleuca alternifolia

O O

pulegone piperitone
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Monoterpene
b. Monocyclic

O O
O
OH O

menthol menthone ascaridol 1,8-cineol

(mint) (Cajeput, Eucalyptus oil)

Melaleuca cajuputi
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Monoterpene
b. Bicyclic

OH O

a-pinen b-pinen borneol camphor Cinnamomum

(Pine oil) camphora

a- b- g- d-fenchen

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Sesquiterpene
a. Hydrocarbon

farnesene zingiberene curcumene

b. azulene
Me Me

iPr

Me iPr Me Et
Me

Lactarius indigo guajazulen vetivazulen chamazulen

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Sesquiterpene
c. Sesquiterpene lactone

O
O O
O O

saussurea lactone santonin

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Aromatic compound
OH

OH

p-cymene thymol carvacrol

(Thyme) (oregano poleo)

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Aromatic compound

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Aromatic compound

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Aromatic compound
OMe
COOMe

OH
CHO

anethole cinnamic aldehyde Methylsalicylate

(anise) (Cinnamon bark)

Cinnamon tree:
- Bark oil: cinnamaldehyde
- Leaf: eugenol
- Root: camphor
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Organo-nitrogen
Organo-sulfur

methyl antranilate

allicin
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Common physical characters

• Colorless (azulene: blue). Darken in color if exposed to
air and light (resinification).

• Liquid (menthol, camphor, vanillin: solid)

• Volatile at room temperature, steam distillable

monoterpen : bp ≈ 150 – 180 oC

sesquiterpen : bp > 250 oC
Aromatic : bp > 300 oC

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Common physical characters

• Immiscible with water, but sufficiently soluble to impart a
fragrance to water --> hydrosols = aromatic waters

• Soluble in alcohol and common organic solvent

• Mostly optically active

• High refractive index (1.450-1.550)

•Density: 0.85-0.95 (lighter than water, except for few

ones) 24

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Methods of preparation of essential oils

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Distillation methods
• Principle: when 2 immiscible liquids are heated
together, they will boil at a temperature below the
boiling point of either one.

• Application: preparation of thermostable oils, present in

large amounts and not rich in esters.

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Distillation methods

Clevenger apparatus

Aromatic water = hydrosols = distilled aqueous layer saturated with oil

Return of aromatic water to distillation chamber, in water distillation, in order to

recover the dissolved oil
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Distillation methods

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The distillation chamber made

of stainless steel, free from
any Fe3+ ions to avoid
degradation of the oil
constituents à darker oils
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Florentine receivers

Bad smelling or dark colored oils are purified by:

- Redistillation
- Dehydration by passing over anhydrous sodium sulfate

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Expression methods

Outer colored zone: waves, pigments,

oil glands

Inner white zone: pectin + cellulose

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Expression methods
1. Squeezing of the peel under a stream of water à emulsion
(volatile oil, pectin, cellulose, pigments, trace of waxes)

2. Centrifugation to remove water, pectin, cellulose

3. Strong cooling to remove waxes

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Solvent extraction methods

According to the nature of the solvent used, three types are
distinguished:
1. Volatile solvent extraction
2. Non-volatile solvent extraction
3. Supercritical fluid extraction

Preparation of delicate flower oils:

1. Present in very small amounts, not easily obtained by
distillation or expression
2. Oils formed of thermolabile constituents (easily decomposed
by heat)
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Solvent extraction methods

Preparation of floral concretes:
1. Solvents used: petroleum ether or hexane
2. Extraction (percolation or maceration…)
3. Solvent removal (distillation under vacuum)

Floral concretes: frangrant constituents, fats, waxes, pigments

Floral absolute: consists mostly of the oxygenated constituents of
the oil
1. Repeated extraction with absolute alcohol
2. Removed the impurities by strong cooling and filtration
3. Removes solvent by distillation
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Enfleurage method

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