VOLATILE OILS Methods of obtaining Volatile Oils
✓ Volatile oils are also known as essences, ethereal
oils and essential oils. 1. Distillation (Turpentine Oil)
✓ Volatile oils are odorous principles found in ✓ Three Distillation Methods used by industrial
various plant parts. firms:
✓ Volatile oils evaporate when exposed to air at a) Water Distillation- for dry materials not
ordinary temperatures. subjected to injury by boiling.
✓ Volatile oils are colorless but on standing are b) Water & Steam Distillation- dry/fresh
oxidized and resinified thus darkening in color. materials that may be injured by boiling.
✓ Volatile oils must be stored in a cool, dry place; c) Direct Steam Distillation- for fresh drugs.
tightly stoppered; preferably in full in an amber
glass container. 2. Enzymatic hydrolysis (Volatile Mustard Oil)
Volatile oils occur in Specialized Secretory Structures as: 3. Expression (Lemon Oil & Orange Oil)
1. Glandular hairs (Lamiaceae/Labiatae) ● Ecuelle Method- general method for citrus
2. Modified Parenchymal Cells (Piperaceae) oils. It makes use of a trough lined with
3. Oil-tubes called vittae sharp projections.
(Umbelliferae/Apiaceae)
4. Lysigenous/Schizogenous passages 4. Enfleurage (Rose Oil)
(Rutaceae & Pinaceae) ● It makes use of a glass plate and an
odourless bland oil or fat.
Volatile oils may be formed by: ● Formerly used in the production of perfume
1. Directly by the protoplasm pomades.
2. From the decomposition of the resigenous layer
of the cell wall. 5. Extraction
3. Hydrolysis of certain glycosides. ● It makes use of volatile organic solvents as
petroleum ether, benzene etc.
Roles of Volatile oils in plants:
1. Insect repellants- prevent the destruction of ✓ Advantage of extraction over distillation:
flowers and leaves. ● Uniform temperatures can be maintained as
2. Insect attractants- aiding in the cross-fertilization a result
of flowers. ● Extracted oils have a more natural odor
● Distilled oils may have undergone altered
Volatile oils differ in chemical composition but have chemical constitution by the high
common physical properties which includes: temperatures
1. High refractive index
2. Most are optically active 6. Destructive Distillation (Empyreumatic Oils)
3. Immiscible with water but possess sufficient ● Wood or resin are used
solubility to impart their odor to water. ● Heated without air and decompose
4. Soluble in most organic solvent (ether & ● Volatile compounds are driven off leaving
alcohol) charcoal (carbon)
● The distillate separate into two layers:
Differences between Volatile oils and Fixed oils: a) Upper aqueous layer containing
1. Volatile oils can be distilled from their natural wood naptha (CH3OH),
sources. pyroligneous acid (crude acetic
2. Volatile oils do not consist of glyceryl esters of fatty acid)
acid. b) Lower layer of tarry liquid (as in
3. Volatile oils do not leave permanent grease on pine tar, juniper tar)
paper.
4. Volatile oils cannot be saponified by alkalies. Medicinal and Commercial Uses of Volatile Oils
5. Volatile oils do not become rancid but instead are
oxidized and resinify. 1. Crude drugs are used medicinally for their volatile
oils. (Ginger & Garlic)
Composition of Volatile oils 2. Volatile oils are used as drugs themselves.
1. Hydrocarbon (Wintergreen oil & Eucalyptus)
2. Alcohols 3. Employed as spices and condiments. (Anise &
3. Ketones Cinnamon)
4. Aldehydes 4. Fabrication for perfume and scents.
5. Ethers
6. Oxides ✓ Perfumes are judicious blends of odorants, each
7. Esters having its own particular odor but whose combined
odor is characteristically unique.
✓ Perfume formulation has been compared to a 2. Sesquiterpenes- 2 isoprene units (C15H24)
musical composition. 3. Diterpenes- 4 isoprene units (C20H32)
4. Triterpenes- 6 isoprene units (C30H48)
Various odorants can be classified as:
a) Top notes- most volatile ✓ Phenylpropanoids- contain the C6 phenyl ring
(Lemon Oil, Lavender Oil, Anise Oil) with attached C3 propane side chain.
b) Middle notes- with intermediate volatility and ✓ Many of the phenylpropanoids found in Volatile Oils
tenacity (Thyme Oil, Neroli Oil, Rose Oil) are phenols and phenol ethers.
c) Base notes- low volatility and tenacity and provides Ex: Cinnamaldehyde & Methyl Salicylate
the staying power for the perfume.
(Vanillin, Musk, Civet, Ambergris) Division of Volatile Oils & Volatile Oil-containing Drugs
Preparation Volatile Oils (RPS) 1. Hydrocarbon Volatile Oils
1. Distillation with steam ● Limonene
2. Distillation per se ● P-cymene
3. Expression ● Pinene
a) Sponge process ● Sabinene
b) Ecuelle method ● Myrcene
c) Machine process ● Cadinene
4. Extraction ● B-caryophyllene
Drug- Turpentine Oil (Chiefly Hydrocabon)
Components of Volatile Oils
2. Alcohol Volatile Oils
1. Eleoptene- the haydrocarbon portion of the oil Alcohols may be classified into:
which is liquid. a) Acyclic (Geraniol, Linalool, Citronellol)
2. Stearoptenes- the oxidized hydrocarbon portion of b) Monocyclic (Menthol, A-Terpineol)
the oil which are usually solid (with exceptions) c) Dicyclic (Borneol)
● Solid Stearoptenes- (menthol, thymol, d) Sesquiterpene Alcohol (Zingiberol)
anethole) Drugs:
● Liquid Stearoptenes- (eucalyptol, eugenol, 1. Peppermint Oil
menthy salicylate) 2. Cardamom Oil
3. Coriander Oil
Methods of Separating Components of Volatile Oils 4. Rose Oil
5. Orange Flower Oil
1. Low temparatures 6. Juniper Oil
2. Fractional Distillation 7. Pine Oil
3. Fractional crystallization (from poor solvents) 8. Japanese Peppermint Oil
4. By chromatography
5. By chemical reaction 3. Aldehyde Volatile Oils
● Using NaHCO3 to remove acidic groups May be divided into two groups:
● Using HCl to remove basic compounds a) Acyclic- (Citral 3:1 mixture of geranial to
● Using NaOH to remove phenols neral, Neral), Citronellal
● Using NaHSO3 to remove aldehydes b) Cyclic- (Cinnamaldehyde, Vanillin)
6. Using advance instrumentation Drugs:
● Using Gas Chromatography 1. Cinnamon Oil
● Using HPLC (High Partition Liquid 2. Orange Oil
Chromatography) 3. Lemon Peel Oil
4. Lemon Oil
Volatile oils components can be grouped into two: 5. Hamamelis Oil
(Based on their biosynthetic origin) 6. Citronella Oil
1. Terpenes- formed via the acetate-mevalonic acid
pathway. 4. Ketone Volatile Oils
2. Phenylpropanoids- formed via shikimic acid- May be divided into:
phenylpropanoid route a) Monocyclic Terpene Ketones- (Menthone,
Carvone, Piperitone, Pulegone, Diosphenol
✓ Terpenes are natural products whose structures (crystalline ketone in Buchu)
maybe divided into isoprene units. b) Dicyclic Ketones- (Camphor, Fenchone,
Thujone)
Classification of Terpenes Drugs:
(The number of units incorporated into a particular terpene 1. Camphor
serves as the basis for the classification of these compounds) 2. Spearmint Oil
1. Monoterpenes- 2 isoprene units (C10H16) 3. Caraway Oil
4. Fennel Oil Examples:
5. Wormwood Oil/Absinthe Oil ● Ergot alkaloids
6. Cedarleaf Oil ● Quinine alkaloids
● Cannabinoids
5. Phenol Volatile Oils- (Eugenol, Thymol, Carvacrol) ● Phylloquinones such as Vit. K & Tocopherols such as
Drugs: Vit. E.
1. Thyme Sources:
2. Clove ● Abundant in higher plants, also in fungi, marine
3. Myrcia organisms, insect pheromones & defense secretions.
4. Creasote Roles:
5. Pine Tar a) Phytoalexins
6. Juniper Tar b) Insect infeedants & repellants
c) Pollination attractants
6. Phenolic Ether Volatile Oils- (Anethole, Saffrole) d) Defense against herbivores
Drugs: e) Pheromones
1. Nutmeg f) Signal molecules
2. Fennel Oil
3. Saffron ❖ Monoterpenoids
4. Anise ● Characteristic features includes volatility intense
5. Myristica pungent odor
● Most common component in plants
7. Oxide Volatile Oils ● Responsible for odor and flavour
● Cineole/Eucalyptol-in eucalyptus Drugs:
● Cajuputol- in cajuput) 1. Camphor (Ketone Volatile Oil)
Drugs: 2. Cineole (Oxide Volatile Oil)
1. Eucalyptus 3. Menthol (Alcohol Volatile Oil)
4. Terpin hydrate
8. Ester Volatile Oils 5. Thymol
● Acetates of Terpineol, Borneol, Geraniol
● Allyl isothiocyanate (Mustard Oil) ❖ Sesquiterpenoids
● Methyl Salicylate (Wintergreen Oil) ● Has a wide spectrum of biological activities
Drugs: (antimicrobial & antitumor)
1. Gaultheria Oil ● Abscisic acid is a sesquiterpenoid that is an
2. Lavender Oil essential plant hormone that control growth and
3. Pine needle Oil development.
4. Mustard Oil Drugs:
1. Artemisin/Qinghaosu
✓ Terpenoids are natural products whose structure 2. Chamomile
maybe divided into isoprene units. 3. Feverfew
✓ Terpenoids are also called as isoprenoids. 4. Valerian
Classification is based on the number of isoprene units ❖ Diterpenoids
same into monoterpenoids to triterpenoids. ● Mainly of plant or fungal origin, also formed by
● Tetraterpenoids/Carotenoids have 8 some marine organism and insects
isoprene units (C40H64). ● Examples are Abietic acid, Gibberelins,
Prodolactones
Categorized as: Drugs:
a) Acyclic- open chain 1. Forskolin
b) Monocyclic- one ring 2. Ginkgo
c) Bicyclic- two rings 3. Taxol/Paclitaxel
d) Tricyclic- three rings
❖ Triterpenoids
Terpenoids are not only isoprene oligomers but also: Examples:
● Also saturated/partially saturated isomers a) Cucurbitacins and quassinoids (Bitter
● As well as oxygenated derivatives such as taste, defense against herbivores)
alcohols, aldehydes, ketones, phenols, ethers & b) Saponins (toxic to cold-blooded
ester animals)
c) Limonoids (insect infeedant)
✓ Meroterpenoids are natural products of mixed
biosynthetic origin. They are constructed from ❖ Tetraterpenoids
isoprene and nonisoprenoids. ● Responsible for the yellow, orange, red and purple
colors seen in living organisms
Examples: o Uses: Treatment in peripheral vascular
1. B-carotene (most common carotenoids in higher disease and other peripheral arterial
plants) circulatory disorders
2. Xanthophylls
✓ Taxol/Paclitaxel/Pacific Yew
✓ Artemisinin o SN: Taxus brevifolia
o SN: Artemisia annua o Family: Taxaceae
o Family: Asteraceae o Part Used: Bark
o Part Used: Leaves & Flowering tops o Uses: One of the most promising
o Constituents: Artemisinin, Artemether, antineoplastic agent, Treatment of
Sodium Artesuanate metastatic carcinoma of the ovary after
o Use: Traditionally been used in China for failure of the 1st and subsequent
the trx of malaria, Potent and Rapidly acting chemotherapy, Treatment of breast cancer
schizontocides, Active against Plasmodium
vivax and against chloroquine-sensitive P. ✓ Neem Tree
Falciparum o SN: Azadirachta indica
o Family: Meliaceae
✓ Chamomile (Ginseng of Europe) o Part Used: Leaves
o SN: Martricaria recutita (German o Contituents: Limonoids (responsible for
Chamomile), Chamaemelum nobile (Roman antifeedant property)
Chamomile) o Uses: One of the most potent insect
o Family: Asteraceae antifeedant
o Part Used: Dried flower heads
o Constituents: Bisabolol, Bisabolosides A &
B, Matricin (Prochamazulene)
o Uses: Carminative, Spasmolytic, Anti-
inflammatory, Used as tea
✓ Feverfew
o SN: Tanacetum parthenium
o Family: Asteraceae
o Part Used: Leaves
o Constituents: Parthenolide (acts as
serotonin antagonist)
o Uses: Used for centuries as
antipyretic/febrifuge. Effective in
prophylaxis of migraine
✓ Valerian
o SN: Valeriana officinalis
o Family: Valerianaceae
o Part Used: Dried roots & rhizomes
o Constituents: Valerenic acid, Valerenolic
acid
o Uses: Employed as antianxiety agent and
sleep aid
✓ Forskolin/Colforsin
o SN: Coleus forskohlii
o Family: Lamiaceae
o Part Used: Roots
o Uses: Therapeutic potential in the following
diseases: Congestive Cardiomyopathy,
Bronchial asthma, Glaucoma, Hypertension
✓ Ginkgo
o SN: Ginkgo biloba
o Family: Ginkgoaceae
o Part Used: Dried leaves
o Constituents: Ginkgolides A, B, C & M