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OIL?????
VOLATILE OILS
All official volatile oils are
of vegetable origin.
Normally pre-exist in the
plant stored in a
special secretory tissue
(e.g. Citrus peel oil cells
or oil ducts in
umbelliferous fruits).
Uses in industry ??
Therapeutically (Oil of
Eucalyptus)
Flavouring (Oil of Lemon)
Perfumery (Oil of Rose)
Starting materials to
synthesize other compounds
(Oil of Turpentine)
Anti-septic due to high
phenols (Oil of Thyme). Also
as a preservative (oils interfere
with bacterial respiration)
Anti-spasmodic (Ginger,
Lemon balm, Rosemary,
Peppermint, Chamomile,
Fennel, Caraway)
Aromatherapy
Fx OF VOLATILE OILS
In most cases, the biological
function of the terpenoids
of essential oils remains
obscure it is thought
that they play an
ecological role
protection from predators
& attraction of pollinators.
CHEMICAL COMPOSITION
Volatile oils are divided into 2 main classes based
on their biosynthetic origin
i.
ii.
iii.
Miscellaneous Origin
CLASSIFICATION OF TERPENES
All terpenes are formed
from 5-C elements
Isoprene is the basic
structural element.
TERPENOIDS
Terpenoids contain only the
most volatile terpenes
(i.e. molecular weight is
not too high) mono
and sesquiterpenes
May occur as oxygenated
derivatives, e.g. alcohols,
aldehydes, ketones,
phenols, oxides & esters.
Classification of Terpenes
Class
Number of carbon atoms
Monoterpene
10
Sesquiterpene
15
Diterpene
20
Sesterpene
25
Triterpene
30
Tetraterpene
40
Terpenes
Terpenes are natural products that
are structurally related to isoprene.
CH3
H2C
CH
CH2
or
Isoprene
(2-methyl-1,3-butadiene)
joined "head-to-tail."
head
tail
tail head
Figure 26.6
Representative Monoterpenes
OH
O
H
-Phellandrene
Menthol
(eucalyptus)
(peppermint)
Citral
(lemon grass)
Figure 26.6
Representative Monoterpenes
OH
O
H
-Phellandrene
Menthol
(eucalyptus)
(peppermint)
Citral
(lemon grass)
Figure 26.6
Representative Monoterpenes
-Phellandrene
Menthol
(eucalyptus)
(peppermint)
Citral
(lemon grass)
Figure 26.6
Representative Sesquiterpenes
H
-Selinene
(celery)
Figure 26.6
Representative Sesquiterpenes
H
-Selinene
(celery)
Figure 26.6
Representative Sesquiterpenes
-Selinene
(celery)
Figure 26.6
Representative Diterpenes
OH
Vitamin A
Figure 26.6
Representative Diterpenes
OH
Vitamin A
Figure 26.6
Representative Diterpenes
Vitamin A
Figure 26.6
Representative Triterpene
Squalene
(shark liver oil)
Cloves
Chinese breath
sweetener
Used in many food,
drugs, cigarettes
Myrtaceae
Spice Islands
Dutch destroyed many
plantations to drive up
the price (1700s)
Unopened flower buds
CLOVE
DEFINITION: Cloves are
the dried flower buds of
Syzygium aromaticum
(Eugenia caryophyllus),
(Myrtaceaea).
Geographical Sources
Molucca or Clove Islands,
Zanzibar, Pemba,
Madagascar, Indonesia &
Brazil.
CONSTITUENTS
14-21% Volatile oils
Mainly eugenol & isoeugenol
Sitosterol
Stigmasterol
Campesterol
Tannins
Triterpene acids & esters
Glycosides
Pyrogallol tanin
Citronella Oils
Latin: Cymbopogan
nardus
Family: Graminaceae
Extraction: Steam
Distillation
Part distilled: Fresh grass
Odor: Fresh, crisp,
lemony
Chemical Class: alcohol
Major Constituents:
USES
LESSON TAKE-AWAY
Definitions of Volatile
Oils
The properties of
volatile oil
Methods of
Production of Volatile
Oils
Herbs containing
Volatile Oils
Common Names:
Jamaican ginger, Ginger
Jamaica
China
India Africa
HISTORY
Cultivated in India from the
earliest times. Used by
Greeks and Romans and
was a common article of
commerce in the European
Middle Ages.
MACROSCOPICAL FEATURES
MICROSCOPICAL FEATURES
Camphene
Cineole
Citral
Borneol
Sesquiterpene HCs
Resins
Starch
Mucilage
Zingiber officinale
VARIETIES
ALLIED DRUGS
ADULTERANTS
Spent ginger
Vegetable adulterants (detected with
microscopical examination).
ACTIONS
Carminative
Stimulant
Anti-emetic
Anti-bacterial & Anti-fungal
Sesquiterpene lactones Anti-ulcer
Gingerol pungent component
Anti-inflammatory
Shogaols increases bile secretion
& enhanced GIT activity
USES
Motion Sickness
Morning Sickness
Elettaria cardamomum
GEOGRAPHICAL
SOURCES
Sri Lanka
India
Guatemala
HISTORY
Traditional Indian
ceremonies
cultivated plants
(propagated by seedlings
or vegetatively
[problematic due to virus
infection]).
Capsules on the same
plant ripen at different
times important to
collect them before they
split.
MACROSCOPICAL FEATURES
MICROSCOPICAL FEATURES
Oil cells
Predominant
Parenchyma
(yellow colour)
Cells containing
silica
Starch grains
ADULTERATION
Powdered drug adulterated with the fruit pericarp
(powdered).
ALLIED HERBS
Official variety E. cardamomum var miniscula
Other: E. cardamomum var major (more elongated &
sometimes 4 cm long with dark brown pericarps)
Amomum aromaticum (Bengal cardamom)
CHEMICAL CONSTITUENTS
2.8 6.2 % volatile oil
Abundant starch (up to 50%)
Fixed oil (1 10%)
Calcium
oxalate
Flavouring agent
(curries & biscuits)
Liqueur manufacture
CINNAMON: Cinnamomum
zeylanicum
DEFINITION: Cinnamon
is the dried bark of
Cinnamomum zeylanicum
(Lauraceae).
GEOGRAPHICAL
SOURCES
Cultivated in Sri Lanka,
South India, Seychelles,
Madagascar, Martinique,
Cayenne, Jamaica &
Brazil.
PREPARATION OF Cinnamomum
Individually scraped
barks are placed
inside each other.
Compound quills are
dried on wooden
frames in the open air
without exposure to
direct sunlight.
Sorted into grades.
MACROSCOPICAL FEATURES
Normally received in shorter lengths
known as cigar lengths.
Consists of a single or double
compound quill about 6-10 mm
diameter of varying length.
Thickness of the quill varies according
to grade (good quality: Not >
0.5mm), bark: 10-40mm.
External surface: is yellow-brown,
shining, wavy lines (pericycle fibres)
and occasional scars & holes
(leave/twig positions).
Inner surface: darker, longitudinally
striated.
Odour: fragrant
Taste: Warm, sweet & aromatic
MICROSCOPICAL FEATURES
Transverse:
Cinnamomum - CONSTITUENTS
CINNAMON OIL
ADULTERATION & ALLIED HERBS
Adulterants
Cinnamon Leaf Oil
Oil of Cassia
Allied Herbs
Cayenne Cinnamon C. zeylanicum grown in
Brazil not used in Britain
C. loureirii from Vietnam Closely resembles
C. cassia
Carminative
Germicide
LEMON PEEL
Definition: Dried lemon
(Limonis Cortex) peel is
obtained from the fruit of
Citrus limon (Rutaceae).
Botanical Description:
Small tree, growing to 3-5 m
in height.
Geographical Sources
Mediterranean Regions
Limonis Cortex
COLLECTION & PREPARATION
Lemons are collected in
January, August &
November, before the
green colour changes to
yellow.
The smaller fruit, which
would not be sold on the
produce market, are used
in the preparation of oil of
lemon - the peel is
removed with a sharp
knife in the form of a
spiral band.
Limonis Cortex
CHARACTERISTICS
Dried lemon peel occurs
in spiral bands (2 cm
wide; 2-3 mm thick).
The outer surface is
rough & yellow; the
inner surface is pulpy
& white (anatomically
similar to that of an
orange peel).
Odour: Strong &
characteristic
Taste: aromatic & bitter
Limonis Cortex
CONSTITUENTS & USES
CONSTITUENTS
Should contain at least
2.5% volatile oil
Vitamin C
Hesperidin (Flavonoid)
Mucilage
Calcium Oxalate
USES
Flavouring purposes
Distilled Oils
Although not official, some lemon oils are produced by distillation,
mainly from the residue of the expression processes. It is
much cheaper than hand-pressed or machine-made oil.
iii.
Oleum limonis
ADULTATION & USES
ADULTERATION
Oil of turpentine
Terpenes from terpeneless oil
of lemon
Distilled oil of lemon
Oil of lemon-grass
USES
Perfumery
Flavouring
Agathosma betulina
CONSTITUENS & USES
CONSTITUENTS
Volatile oils
Pulegone
Menthone & isomenthone
limonene
Diosmin
Mucilage
Resin
Calcium oxalates
Buchu camphor Responsible for the diuretic action
USES/ACTIONS
Diuretic
Urinary Tract Anti-Septic Used for UTIs
MACROSCOPICAL FEATURES
Nutmeg trees are
evergreen, growing up to
20 m in height.
Nutmegs are oval, 2-3 cm
long & 2 cm broad.
If not heavily limed, the
surface is a brown or grey
brown in colour.
Odour: Strong & aromatic
Taste: Pungent and slightly
bitter.
MICROSCOPICAL FEATURES
Potassium acid tartrate
crystals
Parenchym with thin
brown walls
Oval oil cells
Feathery crystals of fat
Few tannin cells
(containing tannin &
starch)
NUTMEG OIL
Nutmeg oil is distilled from the
kernels of Myristica fragrans.
CONSTITUENTS
Pinene
Sabinene
Camphene
Dipentene
Safrole
Eugenol & eugenol derivatives
Myristicin a benzene: toxic to
humans (large does of nutmeg
or nutmeg oil may cause
convulsions).
MACE
Common mace or Banda
mace consists of the
dried arillus or arillode of
M. fragrans.
Description: bright red
colour & lacks in aroma.
HISTORY OF CLOVE
Cloves were used in China as
early as 266 BC, and by the
4th century, they were known
in Europe, although very
expensive.
Same as with nutmeg, the
Dutch also destroyed all trees
from surrounding native
islands to secure a monopoly,
and cultivated them only in a
small group of islands.
In 1770, the French managed to
introduce clove trees to
Mauritius, and started
cultivating them there, as well
as in Zanzibar, Penang and
Sumatra.
MACROSCOPICAL FEATURES
Cloves are 10-17.5 mm
long.
The head consists of 4
slightly projecting calyx
teeth, 4 membranous
petals and numerous
incurved stamens around
a large style.
Odour: Spicy & Pungent
Taste: Aromatic
MICROSCOPICAL FEATURES
Heavy cuticularized epidermis
Numerous oil cells (shizolysigenous)
Calcium oxalates (cluster crystals & prisms)
Stomata (epidermis of sepals)
Starch (Fruit mother cloves)
Lignified sclereids
USES OF CLOVE
Stimulant aromatic
Spice
For the preparation of
volatile oil
Sesquiterpenes:
potential anticarcinogenic
compounds
CLOVE OIL
Oil distilled in Europe and
the US normally does
not need purification,
while oil distilled in
other areas (e.g.
Madagascar) does.
After purification the oil
is sold with varying
eugenol contents.
Oil of cloves is yellow or
colourless, is slightly
heavier than water.
EUCALYPTUS LEAF
DEFINTION: Eucalyptus
leaf consists of the whole
or cut dried leaves of the
older branches of
Eucalyptus globulus,
(Myrtaceae).
GEOGRAPHICAL
SOURCES
Portugal, SA, Spain, China,
Brazil, Australia, India &
Paraguay.
Eucalyptus - DESCRIPTION
MACROSCOPICAL
Older dried leaves are
grey-brown & have lateral
veins. Secretory oil cells
are visible in leaves held
to the light.
MICROSCOPIC
Epidermal cells have a
thick cuticle.
Anisocytic stomata
Mesophyll has
schizogenous oil glands
Calcium oxalate crystals:
Prisms & Cluster crystals
Eucalyptus - CONSTITUENTS
Volatile Oil (at least 2
%)
sesquiterpene - Antibacterial action
against oral
pathogens.
EUCALYPTUS OIL
Oil of eucalyptus is distilled from the fresh leaves
of various species of Eucalyptus and rectified.
They are produced in the same countries which
produce the dry herb.
Only a certain amount of species produce oil
suitable for medicinal use the main criteria is a
high cineole content and low amounts of
phellandrene and aldehydes.
Suitable oils are obtained from E. polybractea, E.
smithii, E. globulus and E. australiana.
CHARACTERISTICS &
CONSTITUENTS
CHARACTERISTICS
Colourless or pale yellow
liquid
Aromatic & camphoraceous
in odour.
Pungent & camphoraceous
in taste, which is followed
by a sensation of cold.
CONSTITUENTS
At least 70 volatile oils
(mainly cineole).
FENNEL
DEFINITION: Fennel
consists of the dried ripe
fruits of Foeniculum
vulgare (Umbelliferae).
GEOGRAPHICAL
SOURCES
Europe, India, China &
Egypt. Mediterranean
origin.
ACTIVE CONSTITUENTS
1-4 % Volatile oil
trans-anethole
Antethole
Estragole
Fenchone
Flavonoids
Coumarins
Glycosides
USES
Flatulence
Dyspepsia
Chronic coughs & catarrh
Foeniculum vulgare
MACROSCOPICAL FEATURES
A biennial herb growing up
to 1 m in height.
Herb: Normally consists of
mericarps separated from
the pedicels. Fruits are
slightly curved, brown &
glabrous.
Size: 4-7 mm long, 1-3 mm
wide
Often the stigma & style are
still attached.
Characteristic aromatic
odour & taste
MICROSCOPICAL FEATURES
Pitted sclerenchyma
secretory canals
Dark, red-brown cells
containing a pale
yellow or colourless
oleoresin
Thick cellulose walls
Calcium oxalate crystals
ACTIVE CONSTITUENTS
1-7 % Volatile oils
Carvone
Limonene
Carveole
8-20 % Fixed oils
Proteins
Calcium oxalates
Colouring matter
Resin
MACROSCOPICAL FEATURES
Annual herb growing 0.7 m
in height with white or
pink flowers.
Drug: Normally consists of
whole cremocarps
straw yellow & 2-4 mm in
diameter when ripe.
Considerable variation
occurs (e.g. Indian variety
> oval).
Apex has 2 styles.
Fruits have an aromatic
odour & spicy taste.
Unripe plant: unpleasant
mousy odour same
odour oil has when made
from unripe fruit.
MICROSCOPICAL FEATURES
Outer pericarp: stomata
& calcium oxalte
prisms.
Thick sclerenchyma
Testa:= brown flattened
cells
Endosperm is curved &
consists of
parenchymous cells
containing fixed oils.
ACTIVE CONSTITUENTS
1.8 % Volatile oils
Linalool/coriandrol
Pinene
Terpinene
Limonene
Cymene
Non-linalool alchols & esters
Flavonoids
Coumarins
Phenolic acids
High fat content (16-28%)
Protein (11-17%)
PEPPERMINT
& PEPPERMINT OIL
DEFINITION:
Peppermint is the
dried leaves of
Mentha piperita
(Labiate). It should
contain at least 1.2 %
volatile oil.
GEOGRAPHICAL
SOURCES:
Europe & America
MACROSCOPICAL FEATURES
All mints have a square
stem & creeping rhizome.
Black mint, which is the
most commonly cultivated
variety in England, has
purple stems and dark
green petiolate leaves
tinged with purple. Leaf
blades are 3-9 cm long
with a grooved petiolate
up to 1 cm long.
Pinnate venation.
Glandular trichomes: bright
yellow points (hand lens)
Small purple flowers appear
in late summer.
MICROSCOPIC FEATURES
Diacytic stomata
Multicellular clothing
trichomes
2 types of glandular
trichomes (one with a
unicellar head; with a
multicellular head).
Calcium oxalate is
absent.
Oleum Menthae
Oil of peppermint is
obtained from Mentha
piperita via steam
distillation using the
flowering tops.
Oil should contain at
least 44 % menthol,
15-32 & menthone
and 4.5-10 % menthyl
acetate.