PHCG 303: PHYTOCHEMISTRY OF NATURAL PRODUCTS - LIPIDS AND VOLATITLE OILS

Plant lipids are a diverse group of naturally occurring organic compounds found in plants
that are insoluble in water but soluble in organic solvents. They serve various structural,
energy storage, and signaling roles in plant biology.

Pharmaceutically useful oils are typically classified based on their origin, composition, and
functional properties.

Based on Source

a) Vegetable Oils (Plant-Based)

• Derived from seeds, nuts, or fruits of plants.

✓ Examples: Olive oil, Castor oil, Coconut oil, Soybean oil.

b) Animal Oils

• Less common in pharmaceuticals today due to ethical and allergenic concerns.

✓ Examples: Cod liver oil (rich in omega-3 fatty acids).

Based on Chemical Composition

a) Fixed Oils (Non-Volatile)

• Mainly triglycerides (glycerol + fatty acids).

✓ Do not evaporate at room temperature.

✓ Examples: Sunflower oil, Almond oil.

b) Essential Oils (Volatile)

• Contain volatile compounds like terpenes and phenols.

✓ Used more in aromatherapy, topical formulations, and antimicrobial agents.

✓ Examples: Peppermint oil, Eucalyptus oil.

Based on Pharmaceutical Use

a) Carrier Oils

• Used as bases for ointments, creams, or to dilute essential oils.

✓ Examples: Grapeseed oil, Jojoba oil.

b) Medicinal Oils

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 • Contain bioactive fatty acids or compounds with specific therapeutic actions.

Examples include:

✓ Castor oil – laxative.

✓ Evening primrose oil – hormonal balance, anti-inflammatory.

✓ Cod liver oil – vitamin D & A source, anti-inflammatory.

Based on Degree of Saturation

• Saturated Oils – Solid or semi-solid at room temperature (e.g., Coconut oil).

• Monounsaturated Oils – High in oleic acid (e.g., Olive oil).

• Polyunsaturated Oils – Rich in omega-3 and omega-6 (e.g., Flaxseed oil).

Based on its drying tendency

– Non-drying oils: (eg. Castor, olive, peanut, rapeseed oils)

– Semi-drying oils. (eg Corn, sesame, cottonseed oils)

– Drying oils: (Soybean, sunflower, linseed oils)

The more unsaturation in the oil, the more likely the “drying” process

GLYCERIDES

Glycerides are a type of lipid formed when fatty acids combine with glycerol (a 3-carbon
alcohol). They are also called acylglycerols, and they are the main components of fats and
oils in both plants and animals.

Basic Chemistry of Glycerides

• Glycerol has three hydroxyl (-OH) groups.

• Each -OH group can react with a fatty acid (via esterification) to form:

1. Monoglyceride → 1 fatty acid + 1 glycerol

2. Diglyceride → 2 fatty acids + 1 glycerol

3. Triglyceride → 3 fatty acids + 1 glycerol

The glycerides could be classified as

1. Simple glycerides (R1=R2=R3) e.g. tripalmitin

2. Mixed glycerides (R1≠R2≠R3) e.g. oleopalmiostearin, or oleodistearin

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Types of Fatty Acids in Glycerides

• Saturated (no double bonds) → solid fats (e.g., in coconut oil).

• Unsaturated (one or more double bonds) → liquid oils (e.g., in olive oil).

The nature of the fatty acids affects the physical and nutritional properties of the glyceride.

Pharmaceutical Relevance

• Triglycerides are used as:

o Carriers for fat-soluble drugs and vitamins.

o Nutraceuticals (e.g., omega-3-rich triglycerides).

o Base oils in topical preparations.

• Medium-Chain Triglycerides (MCTs) are used in special diets and drug delivery.

Physical Properties of Glycerides

✓ fats are solids /semi solids while oils are liquids

✓ melting points and boiling points are not usually sharp (most fats/oils are mixtures)

✓ when shaken with water, oils tend to emulsify

✓ pure fats and oils are colorless and odorless (color and odor is always a result of
contaminants) – i.e. butter (bacteria give flavor, carotene gives color).

Chemical Properties of Glycerides

• Hydrogenation

CH3(CH2)7 CH=CH(CH2)7COOH → CH3(CH2)16COOH

Oleic acid Stearic acid

• Hydrolysis – acid, alkali & enzymes

• Rancidity – hydrolytic & Oxidative

• Acrolein formation (Test for glycerides)

Fat+ KHSO4 → CH2=CH-CHO (unpleasant odour)

• Salt Formation: When triglycerides are heated with a strong alkali like sodium
hydroxide (NaOH) or potassium hydroxide (KOH), the ester bonds break.

Triglyceride + 3NaOH → Glycerol + 3 Sodium salts of fatty acids (soap)

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 C₃H₅(OOCR)₃ + 3NaOH → C₃H₅(OH)₃ + 3 RCOONa

Types of Soaps Formed

• Sodium salts (with NaOH) → hard soaps (used in bars).

• Potassium salts (with KOH) → soft soaps (used in liquids).

Lipid Peroxidation: Lipid peroxidation is a chemical degradation of lipids, especially

unsaturated fatty acids in glycerides, caused by oxidative stress. It involves the attack of free
radicals (like reactive oxygen species, ROS) on the double bonds of fatty acids in glycerides.

In other words, glycerides, particularly unsaturated triglycerides, have fatty acids with C=C
double bonds. These are vulnerable to oxidation.

Consequences of Lipid peroxidation

▪ In biological systems: Leads to cell membrane damage, inflammation, and oxidative

stress (linked to aging, cancer, and chronic diseases).
▪ In pharmaceuticals and food: Causes rancidity, loss of efficacy, and formation of
toxic byproducts.

SOURCES OF OILS

• Olive Oil is a fixed oil obtained by cold expression from the ripe fruits of Olea
europaea (family Oleaceae). It is a pale yellow to greenish-yellow liquid with a
characteristic odor and bland taste. The oil primarily contains oleic acid, linoleic
acid, and linolenic acid as its major constituents. It is widely used in
pharmaceuticals, cosmetics, soaps, and as a solvent for medicinal
preparations. Olive oil is sometimes adulterated with cottonseed, sesame, and
teaseed oils.
• Castor Oil is a fixed oil obtained by cold expression from the seeds of Ricinus
communis Linn. (family Euphorbiaceae), followed by purification by boiling with
water. It is a viscous, pale-yellow liquid with a faint odor and a slightly
nauseating taste. The main constituent is ricinoleic acid, a unique hydroxylated
fatty acid responsible for its purgative (laxative) action. Castor oil is used in
pharmaceutical preparations, cosmetics, lubricants, and as a vehicle for
intramuscular injections. Origin-Brazil, USSR, India, China Thailand and Sudan.
• Sesame Oil is a fixed oil obtained by expression from the seeds of Sesamum
indicum Linn. (family Pedaliaceae). It is a clear, pale-yellow oil with a mild,
pleasant odor and taste. The oil mainly contains oleic acid, linoleic acid, palmitic
acid, and small amounts of sesamin and sesamol, which contribute to its
oxidative stability. Sesame oil is used in the preparation of emulsions, liniments,
and plasters, and serves as a solvent and vehicle in pharmaceutical
formulations.
• Linseed Oil is a fixed oil obtained by cold expression from the seeds of Linum
usitatissimum Linn. (family Linaceae), commonly known as flaxseed. It is a

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 yellow to brownish-yellow viscous liquid with a characteristic odor and a
slightly bitter taste. The oil is rich in linolenic acid, along with linoleic and oleic
acids, making it highly unsaturated and prone to oxidation and polymerization.
Linseed oil is primarily used in the preparation of plasters, paints, soaps, and
occasionally as a vehicle in pharmaceutical formulations.

WAXES
• Waxes are lipid-like substances that are esters of long-chain fatty acids and long-
chain monohydric alcohols (alcohols with one -OH group). Unlike oils and fats (which
are usually triglycerides), waxes do not contain glycerol.
• They are generally solid at room temperature, insoluble in water, but soluble in
organic solvents like chloroform or ether. Waxes may be of animal origin (e.g.,
beeswax), plant origin (e.g., carnauba wax).
acid or base
• Fatty Acid (R–COOH) + Alcohol (R’–OH) Enzyme or Heat
Wax (R–COO–R’) + H2O

✓ R = long alkyl chain from the fatty acid

✓ R' = long alkyl chain from the alcohol

Physical and Chemical Properties of Waxes

Physical Properties

Property Description
State at Room
Solid, but melts at moderate temperatures (usually between 60–100°C)
Temp
Texture Smooth, pliable or brittle depending on the source
Color Ranges from white to yellow or brown (depending on origin and purity)
Mild or characteristic depending on the source (e.g., beeswax has a honey-
Odor
like scent)
Insoluble in water; soluble in organic solvents like chloroform, ether,
Solubility
benzene
Density Less than water (usually between 0.9 and 0.98 g/cm³)
Hydrophobicity Strongly hydrophobic – forms protective coatings that repel water
Plasticity Some natural waxes are plastic and moldable at body temperature

Chemical Properties

Property Description
Ester Structure Waxes are esters of long-chain fatty acids and long-chain alcohols
Under acidic or basic conditions, waxes hydrolyze to yield fatty
Hydrolysis
acids and alcohols

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Property Description
Waxes can be saponified (alkaline hydrolysis), although less easily
Saponification
than fats
Natural waxes (especially those with antioxidants like sesamol in
Resistance to Oxidation
sesame oil) resist oxidation better than unsaturated oils
Combustibility Waxes are flammable and burn with a bright flame
Polymerization (in Some waxes (like linseed oil wax) can polymerize and form hard
drying waxes) films on exposure to air

Typical Reaction – Hydrolysis of a Wax

acid or base
R–COO–R’+H2O R–COOH+R’–OH

Where:

• R–COO–R' = Wax (ester)

• R–COOH = Long-chain fatty acid
• R'–OH = Long-chain alcohol

TERPENES

Terpenes are natural products of which structure may be derived from isoprene units joined
in a head to tail manner giving rise to structures which may be divided into isopentane units.
They are simple lipids, but lack fatty acid component

Isoprene Isopentane

CLASSIFICATION OF TERPENES

On the basis of the number of isoprene unit per molecule, terpenes can be divided into :

• Hemiterpenes (C-5) or 1 isoprene unit

• monoterpenes (C-10) or 2 isoprene units

• sesquiterpenes (C-15) or 3 isoprene units

• diterpenes (C-20) or 4 isoprene units

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 • sesterterpenes (C-25) or 5 isoprene units

• triterpenes (C-30) or 6 isoprene units

• tetraterpenes (C-40) or 8 isoprene units

Terpenes with additional functional group such as oxygen-based groups are known as
“Terpenoids”

Hemiterpenes- C5 One Isoprene Unit

Isoamyl alcohol Angelic acid Isovaleric acid

γ,γ - Dimethylallyl alcohol

Monoterpenes - C10 -Two Isoprenes Sesquiterpenes – C15 -Three Isoprenes

Menthol Myrcene γ-Bisabolene

Diterpenes – C20 – Four Isoprenes

Sesterterpenes – C25 – Five Isoprenes

Ophiobolin-A
Primaric acid
Triterpenes – C30 – Six Isoprenes

Dammarenediol

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 Cholesterol and cholesterol esters

They are also collectively classified as cyclopentanoperhydrophenanthrene

Tetraterpenes – C40 – Eight Isoprenes

β-Carotene α -tocopherol

Hemiterpenes, monoterpenes and diterpenes are major constituents of volatile oils

(essential oils)

VOLATILE OILS

These are the odorous principles of plants. They are formed directly in the protoplasm by
decomposition of the resinogenous layer of the cell wall or by the hydrolysis of certain
glycosides

Why plants synthesize essential oils

Defense Against Herbivores and Pathogens

• Repellent: Essential oils often contain compounds that deter herbivores, insects,
and animals from feeding on them.

• Toxicity: Some components are toxic to microbes, fungi, or insects, helping to protect
the plant from infection or infestation.

Attraction of Pollinators

• Aromatic compounds in essential oils (like terpenes and esters) help attract
pollinators such as bees, butterflies, and birds.

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 • This enhances cross-pollination, vital for plant reproduction.

Allelopathy (Chemical Warfare with Other Plants)

• Some essential oils are released into the environment to inhibit the growth of
competing plant species nearby, helping the plant conserve resources like nutrients,
sunlight, and water.

Protection Against Abiotic Stress

• Essential oils can help plants cope with environmental stress, such as:

o UV radiation

o Drought or heat stress

• They may act as antioxidants to reduce oxidative damage in plant cells.

Healing and Sealing of Wounds

• When a plant is damaged, essential oils may help seal wounds, prevent microbial
invasion, and aid tissue repair.

Intra- and Inter-Plant Communication

• Volatile compounds may signal stress or attack to neighboring plants, prompting

them to activate their own defense mechanisms.

USES OF VOLATILE OILS

Essential oils have a wide range of pharmaceutical and therapeutic applications, thanks to
their bioactive constituents like terpenes, phenolics, aldehydes, ketones, and esters. Here are
the main uses of essential oils in Pharmacy

Antimicrobial Agents

• Many essential oils (e.g., tea tree, thyme, clove, cinnamon) have antibacterial,
antifungal, and antiviral properties.

• They are used in:

o Topical antiseptics and disinfectants

o Treatment of skin infections like acne, athlete’s foot, and wounds

Respiratory Therapy

• Eucalyptus, peppermint, and camphor oils are used as expectorants and

decongestants.

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 • Found in:

o Inhalers

o Cough syrups

o Steam inhalation products for colds, bronchitis, and sinusitis

Anti-inflammatory and Analgesic Applications

• Oils like lavender, chamomile, and rosemary reduce inflammation and relieve
pain.

• Used in:

o Topical gels for arthritis and muscle pain

o Massage oils for muscular relaxation

Aromatherapy and Mental Health

• Lavender, ylang-ylang, and bergamot are used for anxiety, depression, stress,
and insomnia.

• Delivered through:

o Diffusers

o Inhalation therapy

o Bath oils and candles

Dermatological Use

• Essential oils are incorporated into:

o Creams, ointments, and serums for eczema, psoriasis, and acne

o Anti-aging and skin-brightening formulations

Antioxidant Properties

• Essential oils neutralize free radicals, helping to prevent cell damage and oxidative
stress.

• Potential use in nutraceuticals and preventive medicine.

Gastrointestinal Relief

• Peppermint oil is used in treating:

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 o Irritable Bowel Syndrome (IBS)

o Indigestion and flatulence

• Found in capsules, drops, and teas

Oral and Dental Care

• Oils like clove (rich in eugenol) have analgesic and antiseptic properties.

• Used in:

o Toothache gels

o Mouthwashes

o Gum treatments

Insect Repellents

• Essential oils such as citronella, lemongrass, and eucalyptus are used in natural
insect repellents and mosquito sprays.

Pharmaceutical Formulation and Preservation

• Used as natural preservatives due to antimicrobial effects.

• Improve taste, odor, and shelf life of products.

Occurrence in Plant Kingdom

Essential oils occur in a wide variety of medicinal, aromatic, and culinary plants across
several families. They are mostly found in angiosperms (flowering plants), and rarely in
gymnosperms.

Common Plant Families Rich in Volatile Oils:

• Lamiaceae (Mint family) – e.g., Mentha, Ocimum, Rosmarinus

• Rutaceae (Citrus family) – e.g., Citrus, Zanthoxylum

• Apiaceae (Carrot family) – e.g., Foeniculum, Coriandrum

• Myrtaceae – e.g., Eucalyptus, Melaleuca

• Zingiberaceae (Ginger family) – e.g., Zingiber, Curcuma

• Asteraceae (Daisy family) – e.g., Matricaria, Artemisia

• Lauraceae – e.g., Cinnamomum, Laurus

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Distribution in Plant Parts

Volatile oils are localized in specific organs or tissues of plants and stored in specialized
structures. These include:

Flowers

• Found in: Rosa (rose), Lavandula (lavender), Jasminum (jasmine)

• Function: Attract pollinators

Leaves

• Found in: Eucalyptus, Mentha, Ocimum

• Function: Defense against herbivores and pathogens

Fruits and Seeds

• Found in: Coriandrum (coriander), Foeniculum (fennel), Carum (caraway)

• Function: Seed protection and dispersal

Bark and Wood

• Found in: Cinnamomum (cinnamon), Santalum (sandalwood)

• Function: Protection and antimicrobial properties

Roots and Rhizomes

• Found in: Zingiber (ginger), Valeriana, Curcuma (turmeric)

• Function: Storage and defense

Resins and Gums (Oleoresins, Oleo-gum resins)

• Found in: Boswellia (frankincense), Commiphora (myrrh)

• Function: Healing and sealing plant wounds

Secretory Structures

Volatile oils are stored in specialized glandular structures within the plant, which include:

• Glandular trichomes – on leaves/stems (e.g., mint)

• Oil ducts or canals – in stem and fruit (e.g., citrus, fennel)

• Secretory cells or cavities – within plant tissues (e.g., Eucalyptus)

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 • Resin ducts – in bark or wood (e.g., pine, cinnamon)

Ecological and Evolutionary Significance

The widespread but selective distribution of essential oils suggests they are crucial for:

• Plant defense mechanisms

• Reproductive success (pollination)

• Adaptation to environmental pressures

PHYSICAL PROPERTIES OF VOLATILE OILS

Volatility

• They are highly volatile, meaning they can evaporate easily when exposed to air, even
at room temperature.

• This property is responsible for their fragrance and use in aromatherapy.

Odor

• Possess a distinctive and characteristic aroma, often used to identify plant species.

• The odor varies depending on the source plant and the constituents present.

Solubility

• Insoluble in water, but they may float or form emulsions.

• Soluble in organic solvents such as:

o Alcohol (especially 90% ethanol)

o Ether

o Chloroform

o Fixed oils

Density

• Most volatile oils have lower density than water and will float on it.

o Exception: Some oils like clove oil and cinnamon oil are denser than water
and may sink.

• Specific gravity usually ranges between 0.87 and 1.10.

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Boiling Point

• Volatile oils have relatively high boiling points (150°C – 300°C).

• However, due to their volatility, they evaporate before reaching boiling temperature
under normal conditions.

Refractive Index

• They have a high refractive index, typically between 1.45 and 1.60.

• This is often used as a quality control parameter.

Optical Activity

• Some volatile oils are optically active (rotate plane-polarized light).

o e.g., Limonene may exist in D- or L- forms.

• Measured using a polarimeter for identification and purity testing.

Color

• Usually colorless when freshly distilled.

• May develop yellow to brown coloration upon aging or oxidation due to:

o Exposure to light, air, or heat

o Formation of resinous substances

Taste and Irritancy

• Often have a pungent, spicy, or burning taste.

• Can be irritant to skin and mucous membranes in high concentrations.

Volatile with Steam

• Can be distilled with steam, which is the basis of steam distillation, the most common
extraction method.

Summary Table
Property Description

Volatility Evaporates easily

Odor Strong, characteristic

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 Property Description

Solubility Insoluble in water; soluble in alcohol, ether

Density Mostly less than water; some exceptions

Boiling Point High (150°C – 300°C)

Refractive Index High (1.45–1.60)

Optical Activity May rotate plane-polarized light

Color Colorless → yellowish/brown with age

Taste/Irritation Spicy, pungent, often irritating

Steam Distillable Yes

Chemical Properties of Volatile Oils (Essential Oils)

Volatile oils are complex mixtures of organic compounds primarily consisting of terpenes,
alcohols, aldehydes, ketones, phenols, esters, and oxides. Their chemical properties reflect
their reactivity, therapeutic action, and behavior during extraction, storage, and formulation.

Chemical Composition

Volatile oils are mainly composed of:

a. Terpenes

• Monoterpenes (C₁₀H₁₆) – e.g., limonene, pinene

• Sesquiterpenes (C₁₅H₂₄) – e.g., zingiberene, farnesene

b. Oxygenated Derivatives

• Alcohols – e.g., linalool, menthol

• Aldehydes – e.g., citral, cinnamaldehyde

• Ketones – e.g., carvone, thujone

• Phenols – e.g., eugenol, thymol

• Esters – e.g., linalyl acetate

• Oxides – e.g., cineole (eucalyptol)

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Oxidation

• Volatile oils are readily oxidized on exposure to air, light, and heat.

• Oxidation may lead to:

o Loss of activity

o Change in color

o Formation of peroxides and resins

• Hence, essential oils must be stored in airtight, amber-colored containers.

Polymerization and Resinification

• Upon prolonged exposure to air and light, some components polymerize or undergo
resinification, becoming:

o Viscous

o Sticky

o Non-volatile

• This leads to loss of therapeutic and aromatic quality.

Hydrolysis

• Esters in volatile oils may undergo hydrolysis in the presence of moisture, releasing:

o Corresponding alcohols and acids

o e.g., Linalyl acetate → Linalool + Acetic acid

Reaction with Chemical Reagents

Volatile oils respond to a variety of reagents, which are often used in identification and
characterization:

Reagent/Test Reaction/Result Purpose

Ferric chloride Blue/green color with

Detects phenols (e.g., eugenol)
(FeCl₃) phenolic oils

Tollen’s reagent Silver mirror with aldehydes Detects aldehyde group (e.g., citral)

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 Reagent/Test Reaction/Result Purpose

Formation of oximes with

Hydroxylamine test Detects ketones (e.g., carvone)
ketones

Sulfuric acid Tests aromaticity or presence of

May char or produce color
(H₂SO₄) double bonds

Isomerism and Optical Activity

• Many essential oil constituents exhibit geometrical and optical isomerism.

• e.g., (+)-menthol vs (−)-menthol – same formula, different sensory and therapeutic

effects.

• Optical rotation is used for:

o Purity check

o Identity verification

Combustibility

• Volatile oils are flammable due to their hydrocarbon content.

• Require careful handling, especially during distillation or heating.

Summary of Key Chemical Properties

Property Description

Easily oxidized Prone to degradation

Undergo resinification Form non-volatile resins

Hydrolysis of esters Releases alcohols and acids

Reactivity with reagents Used for identification

Isomerism and chirality Affects biological activity

Flammable Handle with care

Storage Considerations

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Due to their chemical reactivity, volatile oils must be stored:

• In tightly sealed containers

• In cool, dry places

• Away from direct sunlight

• Preferably in amber-colored glass bottles

PROCESSES OF VOLATILE OIL (ESSENTIAL OIL) EXTRACTION

Volatile oils are extracted from various plant parts such as leaves, flowers, bark, seeds, fruits,
and roots. The extraction method chosen depends on the nature of the oil, the plant material,
and the intended use.

Steam Distillation

Principle:

Volatile oils are distilled along with steam; their low boiling points allow them to vaporize
and condense before the plant material is damaged.

Steps:

1. Plant material is placed in a still.

2. Steam is passed through the material.

3. The oil-laden steam is condensed into a liquid.

4. The oil separates from the water and is collected.

Suitable For:

• Most herbs, flowers, and woody materials

• E.g., eucalyptus, peppermint, clove

Advantages:

• Preserves delicate oils

• Common and cost-effective

Hydrodistillation

Principle:

Plant material is immersed in water and the mixture is boiled.

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 Steps:

1. Material is placed in boiling water.

2. Steam carries the volatile components.

3. Vapors are condensed, and the oil is separated.

Suitable For:

• Materials that might clump or degrade with direct steam.

• E.g., rose petals, some roots

Advantage:

• Simple method, used traditionally

Hydrosteam Distillation

A combination of steam distillation and hydrodistillation:

• Material is partially immersed in water while steam is passed.

• Reduces thermal degradation and helps free oil flow.

Cold Expression (Mechanical Expression/Pressing)

Principle:

Mechanical pressure is applied to express oil without heating.

Used For:

• Citrus fruits (e.g., orange, lemon, bergamot)

Steps:

1. Fruit peels are pierced or grated.

2. Mechanical pressure squeezes out oil.

3. Oil is separated from juice and other components.

Advantage:

• Retains full aromatic and therapeutic quality

Solvent Extraction

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 Principle:

Non-polar solvents (e.g., hexane, petroleum ether) are used to dissolve volatile oil from
plant material.

Steps:

1. Plant material is soaked in solvent.

2. The extract is filtered and concentrated to get a concrete (oil + waxes).

3. Alcohol is used to extract the absolute (pure essential oil).

Used For:

• Delicate flowers (e.g., jasmine, tuberose) that cannot tolerate heat.

Note:

• Residual solvent traces must be carefully removed for pharmaceutical use.

Supercritical Fluid Extraction (SFE)

Principle:

Uses supercritical CO₂ as a solvent, which behaves like both a gas and a liquid under high
pressure.

Steps:

1. CO₂ is compressed to supercritical state.

2. It extracts the volatile oils efficiently.

3. Pressure is released to recover oil and recycle CO₂.

Advantages:

• Highly selective, efficient, and solvent-free

• Preserves fragile compounds

Limitation:

• Requires expensive equipment

7. Enfleurage (Traditional method)

Principle:

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Used for delicate flowers; oil is absorbed onto fat and later extracted.

Steps:

1. Fresh flowers are placed on glass plates smeared with fat.

2. The fat absorbs the oil over time.

3. Alcohol is used to extract oil from the fat.

Rarely used now due to labor-intensive nature.

Summary Table

Method Best For Pros Limitations

Steam Distillation Herbs, roots, leaves Efficient, common Not for delicate flowers

Flowers, resinous Some thermal

Hydrodistillation Simple, traditional
material degradation possible

Cold Expression Citrus fruits No heat involved Only for citrus oils

Solvent Extraction Fragile flowers High yield, gentle Residual solvents

Supercritical CO₂ Premium oils, Clean, pure, high-

Expensive setup
Extraction pharma-grade quality extract

Fragile blossoms Preserves fragrance Time-consuming,

Enfleurage
(e.g., jasmine) well outdated

CHEMICAL NATURE OF VOLATILE OILS (ESSENTIAL OILS)

Composition

Volatile oils contain primarily hydrocarbons and their oxygenated derivatives. The major
classes include:

Terpenes

• Monoterpenes (C₁₀H₁₆)
→ e.g., limonene, α-pinene, myrcene
→ Provide fragrance and medicinal properties.

• Sesquiterpenes (C₁₅H₂₄)
→ e.g., farnesene, zingiberene
→ More stable, often found in roots and resins.

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 Oxygenated Derivatives of Terpenes

• Alcohols – e.g., menthol, linalool

• Aldehydes – e.g., citral, cinnamaldehyde

• Ketones – e.g., carvone, thujone

• Phenols – e.g., eugenol, thymol

• Esters – e.g., linalyl acetate, geranyl acetate

• Oxides – e.g., cineole (eucalyptol)

These functional groups influence the biological activity, aroma, solubility, and chemical
reactivity of the oils.

General Chemical Characteristics

Property Details

Organic nature Composed of carbon, hydrogen, and oxygen

Volatility Evaporate readily at room temperature

Insolubility in water Immiscible with water but soluble in alcohol and organic solvents

Optical activity Many constituents are optically active (e.g., d-menthol vs. l-menthol)

Reactivity Susceptible to oxidation, polymerization, and hydrolysis

Combustibility Highly flammable due to hydrocarbon content

3. Common Constituents and Their Roles

Constituent Example Function

Monoterpenes Limonene Fragrance, antimicrobial

Sesquiterpenes Zingiberene Anti-inflammatory, aromatic

Alcohols Linalool, Menthol Antiseptic, cooling

Aldehydes Citral Antimicrobial, lemon scent

Ketones Carvone Spasmolytic, aromatic

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Constituent Example Function

Phenols Eugenol, Thymol Strong antiseptic, irritant at high doses

Esters Linalyl acetate Calming, fragrant

Oxides Cineole Expectorant, used in respiratory conditions

Factors Affecting Chemical Nature

• Plant species and variety

• Part of the plant used (leaf, root, flower, etc.)

• Geographical origin and climate

• Extraction method (e.g., distillation, solvent extraction)

• Storage conditions

Classification of Volatile Oils

Based on Chemical Composition / Functional Groups

This is the most widely used and pharmacologically relevant method. Volatile oils are
grouped according to the dominant functional groups present in their constituents:

Class Main Components Examples Uses

Limonene (citrus), Fragrance, anti-

Hydrocarbons Monoterpenes, Sesquiterpenes
Pinene inflammatory

Monoterpenoid/Sesquiterpenoid Antiseptic,
Alcohols Linalool, Menthol
alcohols calming, cooling

Citral, Antifungal,
Aldehydes Aldehyde-containing terpenes
Cinnamaldehyde antimicrobial

Mucolytic,
Ketones Ketonic compounds Carvone, Thujone
stimulant

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Class Main Components Examples Uses

Strong antiseptic,
Phenols Phenolic terpenoids Eugenol, Thymol
antimicrobial

Linalyl acetate, Sedative, anti-

Esters Esters of alcohols & acids
Geranyl acetate inflammatory

Expectorant,
Cineole
Oxides Cyclic ethers respiratory
(Eucalyptol)
therapy

Based on Botanical Source / Plant Part

Volatile oils can also be classified based on the part of the plant from which they are
obtained:

Plant Part Examples

Flowers Rose (Rosa spp.), Lavender (Lavandula spp.)

Leaves Eucalyptus, Peppermint, Tea Tree

Bark Cinnamon (Cinnamomum spp.)

Wood Sandalwood, Cedarwood

Seeds Nutmeg, Coriander

Roots Ginger, Vetiver

Peels (Rind) Lemon, Orange, Bergamot

Resins Frankincense, Myrrh

Based on Therapeutic Activity

This classification focuses on the pharmacological or medicinal properties of the oil.

Activity Examples

Antiseptic Tea Tree, Thyme, Eucalyptus

Analgesic Peppermint, Clove

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Activity Examples

Sedative/Calming Lavender, Chamomile

Stimulant Rosemary, Black Pepper

Antispasmodic Basil, Marjoram

Expectorant Eucalyptus, Pine

Based on Volatility (Note Class)

In aromatherapy and perfumery, volatile oils are classified by their rate of evaporation,
which affects blending and therapeutic effect duration:

Note Evaporation Rate Examples

Top Note Evaporates quickly Lemon, Eucalyptus, Peppermint

Middle Note Moderate evaporation Lavender, Rosemary, Geranium

Base Note Evaporates slowly Sandalwood, Patchouli, Myrrh

Based on Origin or Extraction Method

Classification Description

Natural Extracted from plants using physical means

Synthetic Lab-synthesized, mimicking natural constituents

Isolated Natural Constituents Single compounds (e.g., eugenol) from volatile oils

Summary

Volatile oils can be classified according to:

• Chemical composition (functional groups)

• Botanical source (flower, bark, leaf, etc.)

• Therapeutic use (antiseptic, sedative, etc.)

• Volatility (notes) (top, middle, base)

• Origin (natural vs. synthetic)

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This classification aids in standardizing their use in pharmacy, perfumery, aromatherapy,
and food industries.

DESCRIPTIONS OF SOME TYPICAL VOLATILE OILS

1. Eucalyptus Oil

• Botanical Source: Eucalyptus globulus (Leaves)

• Major Constituents: 1,8-Cineole (Eucalyptol), α-pinene, limonene

• Properties: Colorless to pale yellow oil with a strong camphoraceous odor

• Uses:

o Expectorant in cough syrups

o Antiseptic in mouthwashes and inhalants

o Insect repellent

Peppermint Oil

• Botanical Source: Mentha × piperita (Leaves)

• Major Constituents: Menthol, menthone, isomenthone

• Properties: Clear, cool-smelling oil with a strong, fresh minty odor

• Uses:

o Flavoring agent in toothpaste and gums

o Carminative for indigestion

o Local analgesic and antispasmodic

Clove Oil

• Botanical Source: Syzygium aromaticum (Dried flower buds)

• Major Constituents: Eugenol, eugenyl acetate, caryophyllene

• Properties: Yellow to brownish oil with a warm, spicy scent

• Uses:

o Dental analgesic (toothache drops)

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 o Antimicrobial in oral hygiene products

o Aromatic stimulant

Lavender Oil

• Botanical Source: Lavandula angustifolia (Flowers)

• Major Constituents: Linalool, linalyl acetate, camphor

• Properties: Pale yellow oil with a sweet, floral fragrance

• Uses:

o Sedative and anti-anxiety in aromatherapy

o Antiseptic and healing agent in burns

o Perfume and cosmetic formulations

Lemon Oil

• Botanical Source: Citrus limon (Peel)

• Major Constituents: Limonene, citral, pinene

• Properties: Light yellow oil with a fresh, citrusy aroma

• Uses:

o Flavoring in food and beverages

o Antiseptic and cleansing in skincare

o Mood-enhancing in aromatherapy

Cinnamon Oil

• Botanical Source: Cinnamomum zeylanicum (Bark or leaves)

• Major Constituents: Cinnamaldehyde (bark oil), eugenol (leaf oil)

• Properties: Yellow to brown oil with a spicy, warm scent

• Uses:

o Antifungal and antibacterial

o Flavoring agent

o Circulatory stimulant

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Tea Tree Oil

• Botanical Source: Melaleuca alternifolia (Leaves)

• Major Constituents: Terpinen-4-ol, γ-terpinene, α-terpinene

• Properties: Pale yellow oil with a medicinal, camphor-like odor

• Uses:

o Strong antimicrobial and antifungal agent

o Used in acne treatment and dandruff shampoos

o Wound disinfectant

Rosemary Oil

• Botanical Source: Rosmarinus officinalis (Leaves and flowering tops)

• Major Constituents: Cineole, camphor, borneol

• Properties: Clear to pale yellow oil with a woody, herbal aroma

• Uses:

o Memory and concentration enhancer

o Hair growth stimulation

o Muscle pain relief

Summary
Volatile Oil Main Source Major Compound(s) Key Use(s)

Eucalyptus Leaves Cineole Respiratory aid, antiseptic

Peppermint Leaves Menthol Digestion, analgesic

Clove Flower buds Eugenol Dental pain relief, antiseptic

Lavender Flowers Linalool Calming, burn treatment

Lemon Peel Limonene Flavoring, mood enhancer

Cinnamon Bark/Leaves Cinnamaldehyde/Eugenol Antimicrobial, stimulant

Tea Tree Leaves Terpinen-4-ol Skin infections, acne

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Volatile Oil Main Source Major Compound(s) Key Use(s)

Rosemary Leaves Cineole, Camphor Hair tonic, mental stimulant

Common Volatile Oils in Commerce

Volatile Oil Botanical Source Major Constituents Primary Commercial Uses

Eucalyptus Eucalyptus Cough remedies, lozenges,

Cineole (Eucalyptol)
Oil globulus liniments, inhalants

Peppermint Toothpaste, mouthwash,

Mentha × piperita Menthol, Menthone
Oil ointments, digestive tonics

Syzygium Dental analgesics, perfumes,

Clove Oil Eugenol
aromaticum soaps, mouthwashes

Lavandula Linalool, Linalyl Perfumery, stress relief, bath

Lavender Oil
angustifolia acetate products

Flavouring in food and beverages,

Lemon Oil Citrus limon Limonene, Citral
perfumes, cleaning products

Cinnamon Cinnamomum Cinnamaldehyde, Spices, perfumes, medicinal

Oil zeylanicum Eugenol preparations

High-end perfumery, cosmetics,

Rose Oil Rosa damascena Geraniol, Citronellol
aromatherapy

Melaleuca Terpinen-4-ol, γ- Antiseptics, skin care, shampoos,

Tea Tree Oil
alternifolia Terpinene acne treatments

Pelargonium
Geranium Oil Citronellol, Geraniol Perfumery, skincare, massage oils
graveolens

Cinnamomum Liniments, ointments, cough

Camphor Oil Camphor, Safrole
camphora preparations

Cough syrups, flavouring,

Anise Oil Pimpinella anisum Anethole
carminative preparations

Antiseptic, mouthwashes,
Thyme Oil Thymus vulgaris Thymol, Carvacrol
expectorant formulations

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Volatile Oil Botanical Source Major Constituents Primary Commercial Uses

Methyl chavicol, Flavouring agent, aromatic herb

Basil Oil Ocimum basilicum
Linalool oil

Flavouring, fragrance, industrial

Orange Oil Citrus sinensis Limonene
cleaners

Fixative in perfumery, incense,

Patchouli Oil Pogostemon cablin Patchoulol
cosmetic products

Ylang-Ylang Linalool, Geranyl Luxury perfumes, skin lotions,

Cananga odorata
Oil acetate hair oils

Turpentine Pinus spp. (from

α-pinene, β-pinene Solvents, liniments, industrial uses
Oil resin)

Key Characteristics of Volatile Oils in Commerce

• High demand in flavour, fragrance, and pharmaceutical industries.

• Often standardized based on chemical marker content (e.g., % cineole in eucalyptus

oil).

• Frequently subject to adulteration, hence quality control is critical.

• Traded globally as essential oils in bulk or refined form.

PLANT RESINS

Plant resins are natural, sticky substances produced by certain plants, especially trees, in
response to injury or stress. These resins are exuded from specialized ducts or glands within
the plant and have a variety of biological functions such as protection against pests,
pathogens, and environmental factors.

Definition of Plant Resins

Plant resins are organic substances that are usually viscous and solidify when exposed to air.
They are composed of volatile oils, terpenes, phenolic compounds, and other organic
molecules. Unlike latex, which is milky and often elastic, resins are typically solid or semi-
solid at room temperature.

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Occurrence and Source

• Produced by certain plant species, particularly gymnosperms (e.g., conifers like pine,
spruce, fir) and some angiosperms (e.g., frankincense and myrrh trees).

• Resins are secreted from specialized structures like resin ducts, glandular cells, or
external wounds of plants.

• Trees like pine, fir, and cedar produce copious amounts of resin, which is often
harvested for commercial use.

Chemical Composition

• Terpenes: Major components of resins are monoterpenes and diterpenes.

• Phenolic compounds: Contribute to the antioxidant and antimicrobial properties of

the resin.

• Other organic compounds: Include resin acids, esters, and flavonoids.

Types of Plant Resins

• Oleoresins: Mixtures of volatile oils and resin acids. Common in conifers like pine
and fir.

• Gum resins: Contain a mix of gums (polysaccharides) and resins. Examples include
myrrh and frankincense.

• Balsams: Specialized resins that are often aromatic and contain benzoic acid or
cinnamic acid. Examples include benzoin and tolu balsam.

Functions of Resins in Plants

• Protection: Resins act as a defense mechanism against pathogens, herbivores, and

physical damage.

• Sealing Wounds: When a plant is injured, resins seal the wounds, preventing
infection and water loss.

• Antimicrobial Action: Many resins have antibacterial and antifungal properties,

which help protect the plant from microbial invasion.

Uses of Plant Resins

In Traditional Medicine

• Myrrh and frankincense are used in incense, medicines, and ointments.

• Resins have antiseptic, anti-inflammatory, and analgesic properties, making them

valuable in wound healing.

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In Industry

• Varnishes and lacquers: Some resins are used in wood finishes.

• Adhesives: Certain resins serve as glues and binding agents.

• Aromatics: Resins like benzoin are used in fragrances and incense.

In Modern Medicine

• Resinous compounds like rosin and colophony are used in pharmaceuticals as

binders in tablets and capsules.

• Resinous oils can be employed in topical ointments and balms for their anti-
inflammatory and healing effects.

Examples of Plant Resins

• Pine Resin (Colophony): Extracted from the pine tree, used in rosin for making
varnishes and adhesives.

• Frankincense: A resin from the Boswellia tree, traditionally used in incense and
medicinal preparations.

• Myrrh: A gum resin from the Commiphora tree, used in perfumes, incense, and
traditional healing.

• Benzoin: Extracted from the bark of Styrax trees, used in incense, and as an antiseptic
in ointments.

Extraction and Processing

• Tapping: The process of cutting into tree bark to exude the resin.

• Solvent Extraction: Solvents like ethanol or hexane are used to extract volatile
compounds from resins.

• Distillation: In some cases, resins can be distilled to obtain essential oils.

Resins in Commerce

Plant resins, especially those like rosin, turpentine, frankincense, and myrrh, are
commercially valuable due to their wide range of uses in the pharmaceutical, cosmetic, and
aromatic industries.

PLANT GUMS

Plant gums are water-soluble polysaccharides produced by certain plants as a protective or

healing mechanism in response to injury, stress, or infection. These gums are sticky, viscous
substances that are primarily composed of complex sugars. Unlike resins, which are typically

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more hydrophobic and viscous, gums are hydrophilic and dissolve in water to form a gel-like
consistency.

Definition of Plant Gums

Plant gums are natural, complex carbohydrates (polysaccharides) that are excreted by plants
in response to injury or environmental stress. They are often secreted from specialized
glands or ducts and serve as a protective barrier for the plant.

Occurrence and Source

• Produced by certain plant species, particularly angiosperms (flowering plants) and

some gymnosperms (non-flowering plants).

• Gums are often harvested from trees and plants that naturally exude them. These
include species like Acacia, Gum Arabic trees, and Gum Tragacanth.

Types of Plant Gums

There are several types of plant gums, which are classified based on their chemical
composition, structure, and source:

1. Exudate Gums

These are gums that are secreted by plants into their surroundings, often as a response to
injury.

• Gum Arabic: Harvested from the Acacia senegal and Acacia seyal trees; used
extensively in food processing, pharmaceuticals, and cosmetics.

• Gum Tragacanth: Sourced from the Astragalus species; used in food and
pharmaceuticals as a thickening agent.

• Gum Karaya: From the Sterculia urens tree; used in food and medicine, especially
as a bulk-forming laxative.

Seed Gums

These gums are obtained from seeds of certain plants and are used primarily as thickening
agents.

• Guar Gum: Derived from the Cyamopsis tetragonoloba seed, widely used in the food
industry (as a thickener) and in fracking.

• Locust Bean Gum: Obtained from the seeds of Ceratonia siliqua, used in food and
pharmaceuticals.

Gum Resins

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These are combinations of gums and resins, such as Gum Benzoin, which are often aromatic
and used in incense and cosmetics.

Chemical Composition

• Polysaccharides: The primary constituent of gums. They are long chains of sugar
molecules, including galactose, mannose, xylose, arabinoses, glucuronic acid, and
others.

• Water-Solubility: Plant gums are highly water-soluble and can dissolve to form gel-
like textures, which gives them their characteristic viscosity.

• Amino Acids: Some gums, like gum tragacanth, contain amino acids that contribute
to their gelling properties.

Functions of Gums in Plants

• Protection: Gums help seal wounds and prevent the plant from losing moisture or
getting infected.

• Healing: By forming a protective film, gums protect the plant from further injury and
microbial invasion.

• Defense Against Herbivores: Gums act as a deterrent to herbivores due to their

stickiness and harsh texture.

• Water Retention: Some gums also help the plant in retaining water, especially in
arid environments.

Uses of Plant Gums

In the Food Industry

• Thickeners: Gums like guar gum, xanthan gum, and gum Arabic are used in dairy
products, sauces, beverages, and baked goods to improve texture and viscosity.

• Stabilizers: Plant gums are added to ice cream, dressings, and emulsions to prevent
separation of ingredients.

In Pharmaceuticals

• Binders: Gums like gum Arabic and tragacanth are used as binding agents in tablet
formulations.

• Laxatives: Gum Karaya and psyllium are used as bulk-forming laxatives.

• Controlled Release: Some gums are used in drug delivery systems to control the
release of active ingredients.

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In Cosmetics and Personal Care

• Thickeners and Emulsifiers: Plant gums such as gum Arabic and gum tragacanth
are used in lotions, creams, and shampoos for texture enhancement.

• Moisturizers: Due to their hydrophilic nature, gums are used in moisturizing

formulations for their water-retaining properties.

In Industrial Applications

• Oil Industry: Guar gum is used in the oil industry for hydraulic fracturing (fracking)
as a viscosity modifier.

• Textiles: Some gums are used in the textile industry as sizing agents.

Extraction of Plant Gums

• Tapping: Gums are harvested by tapping trees and scraping off the exudates. For
instance, gum Arabic is tapped from the bark of Acacia trees.

• Water Extraction: Some gums, like guar gum, are extracted from seeds by soaking in
water and then mechanically separating the gum.

• Boiling: The collected gum may be boiled or mixed with solvents to extract the
soluble components.

Examples of Plant Gums

• Gum Arabic (Acacia gum): Sourced from Acacia senegal and Acacia seyal, widely
used in the food, pharmaceutical, and cosmetic industries.

• Gum Tragacanth: Obtained from Astragalus species, used in food products,

pharmaceuticals, and cosmetics.

• Guar Gum: Derived from Cyamopsis tetragonoloba seeds, used as a thickening agent
in food, pharmaceuticals, and fracking.

• Gum Karaya: Comes from the Sterculia urens tree, used in bulk-forming laxatives
and as a thickener in food.

Plant Gums in Commerce

• Food Industry: Plant gums like guar gum, xanthan gum, and gum Arabic are widely
traded and used in the production of processed foods.

• Pharmaceutical Industry: Gum Arabic is used as a binder and stabilizer in tablet and
syrup formulations.

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• Cosmetic and Personal Care: Gums are widely utilized as emulsifiers, stabilizers,
and thickeners in skincare products.

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