VOLATILE OILS

Chapter Outline
 Introduction and chemistry of volatile oils
 Significance of volatile oils
 Methods of obtaining volatile oils
 Classification of volatile oils
 Detailed study of;
• Hydrocarbon volatile oils: Cubeb oil, Turpentine oil
• Alcoholic volatile oils: Peppermint oil, Coriander oil, Cardamom oil
• Aldehydic volatile oils: Bitter orange peel oil, Sweet orange peel oil, Lemon oil, Cinnamon oil,
Bitter almond oil
• Ketonic volatile oils: Camphor, Spearmint, Caraway, Buchu
• Phenolic volatile oils: Clove, Thyme
• Phenolic ether volatile oils: Fennel, Anise, Myristica
• Oxide volatile oils: Eucalyptus, Chenopodium
• Ester volatile oils: Rosemary
• Miscellaneous volatile oils: Allium, Anethum

CH3
OH OH

Note: In this chapter, free ends of structural formulae are alkyl groups
CH2

H3 C CH3
Linalool Linalool

Introduction, Physical Properties and Chemistry

 Volatile oils are odorous principles found in various plant parts

 These evaporate when exposed to air at ordinary temperature, so are called volatile oils or ethereal oils
 Volatile oils represent the ‘essences’ or odoriferous constituents of plants, so are called essential oils
 Colorless, particularly when fresh
 With the passage of time, may become dark. So, should be stored in a cool, dry place in tightly stoppered,
preferably full (not half emptied), amber colored containers
Physical properties of volatile oils
 Possess characteristic odor
 Have high refractive index
 Most are optically active e.g. natural menthol is levorotatory, synthetic is racemic
 Immiscible with water, but aromatic waters (‫ عرقیات‬water saturated with volatile oil) can be prepared
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 Soluble in ether, alcohol and most organic solvents
 Colorless, particularly when fresh
Chemistry of volatile oils
 With the exception of oils derived from glycosides (e.g. bitter almond oil and mustard oil), volatile oils
are generally mixture of hydrocarbons (eleoptenes) and oxygenated hydrocarbons (stearoptenes)
• Stearoptenes: May be solid, present in low concentration, medically important, give particular odor
and taste
• Eleoptenes: generally liquid, present in high concentration
• Almost any type of organic compound may be found in volatile oils (hydrocarbons, alcohols, ketones,
aldehydes, ethers, oxides, esters and others). Only a few possess a single component in high percentage
e.g. clove oil contains not less than 85% of phenolic substances, chiefly eugenol
 Based on biosynthetic origin, chemical constituents of volatile oils may be divided into two broad classes;
A. Terpene derivatives (formed via the acetate-mevalonic acid pathway)
B. Phenylpropanoid derivatives (formed via the shikimic acid-phenylpropanoid route)
• Terpenes: Natural products whose structures may be divided into isoprene units
Monoterpenes Composed of 2 isoprene units (C10H16)
H3C
Sesquiterpenes Composed of 3 isoprene units (C15H24) C CH CH2
H2C
Diterpenes Composed of 4 isoprene units (C20H32)
Isoprene unit (C5H8)
Triterpenes Composed of 6 isoprene units (C30H48)
• In volatile oils, mostly monoterpenes are found, few are sesquiterpenes
• These monoterpenes can occur in acyclic, monocyclic and bicyclic forms

CHO

CH2 CH2 CH3 CH CH CHO

Geranial Limonene -pinene

(Acyclic monoterpene) (Monocyclic monoterpene) (Bicyclic monoterpene) Phenylpropanoid Cinnamaldehyde

Phenylpropanoids are the compounds which contain C6 phenyl ring with an attached C3 propane side chain,
e.g. cinnamaldehyde

Significance of Volatile Oils

 Many crude drugs are used medicinally because of their volatile oil content; however, in numerous cases,
the volatile oils separated from drugs are used as drugs themselves
 Various crude drugs having volatile oils, are powdered and are employed as spices and condiments (anise,
clove, nutmeg)
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 The volatile oil drugs and the separated oils are most commonly used for flavoring purposes
 They possess a carminative , but a few (eucalyptus oil, wintergreen oil) possess additional therapeutic
properties
 In addition to their pharmaceutic use, the volatile oils are employed widely as flavors for food and
confections and in the spice, perfume and cosmetic trade
 The fabrication of perfumes is a multimillion industry
 Volatile oils are used not only directly as perfumes, but also in the manufacture of soaps, toiletries and
deodorizers and for providing odor to household cleaners, polishes and insecticides
 Many volatile oils possess antiseptic properties (antibacterial, antifungal)
 Because of preservative and fragrance qualities, volatile oils were mixed with foodstuffs in early historic
times

Methods of obtaining Volatile Oils

1. By using heat (Distillation)

A. Water distillation
B. Water and steam distillation
C. Steam distillation
D. Special techniques of distillation (vacuum distillation, fractional distillation)
2. Without using heat (Expression)
A. Ecuelle method
B. Enfleurage method
C. Glycoside enzymatic hydrolysis
Water distillation
 Applied for heat stable dry drugs/plant materials
 Plant material is placed in distilling flask containing water
 Heated (boiled) directly, till plant material is exhausted
 Examples: Turpentine oil is obtained by this method
Water and steam distillation
 Applied for dried substances (crude drugs) that may be injured by boiling
 Material/crude drug is crushed/ground and soaked in water in distillation flask
 Steam is passed through this macerated material
 In water distillation, drug is constantly in contact with heat; but in steam distillation drug is not constantly
in contact with heat, steam come and goes out
 Examples: Cinnamon oil, clove oil is obtained by this method

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 Thermometer

Water Distillation
Water outlet

Stand Condenser

Distillation flask

Water inlet

Water and Steam Flask for ‘oils heavier than water’

Distillation

Distillation flask Water outlet

Condenser

Steam generator Flask for ‘oils lighter than water’

Water inlet

Steam distillation
 Applicable to fresh plant drugs
 Fresh plant parts are spread over large trays having perforated bottoms
 Steam is passed from lower side
 No need to add water, because fresh plant parts contain water
 Example: Peppermint oil, spearmint oil is obtained by this method
Vacuum distillation
 Distillation done at reduced pressure Fractionating column

 By reducing external pressure, boiling point is reduced

 A vacuum pump is employed between condenser and receiving flask
 Use for heat sensitive drugs
Fractional distillation
 A fractionating column is used between distillation flask and condenser
 This process is used to separate mixture of volatile substances having close boiling points
Ecuelle method
 Lemon oil is obtained by this method
 The apparatus is like a pan having small sharp projections
 Lemons are rolled in this pan, the projections puncture the oil glands present in the peel
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 Volatile oil is obtained
 Water is sprayed to wash the oil from peel (increases oil removal)
 The resulting oil-water emulsion is separated by centrifugation
Enfleurage method
 This method is used to get volatile oils from petals (production of perfumes)
 An odorless bland fixed oil or fat is spread in a thin layer on glass plates
 Flower petals are placed on the fat layer for a few hours
 Volatile oil is absorbed by fat layer
 When the petals are exhausted, are replaced by fresh ones
 When fat layer is saturated, it is removed and replaced by fresh layer of fat
 Volatile oil is separated from fat by distillation
Glycoside enzymatic hydrolysis
 In this method, volatile oils are obtained by enzymatic hydrolysis of the glycosides
 Examples: Mustard oil is obtained by hydrolysis of sinigrin (a glycoside) by myrosin (enzyme)

C3H5 C S C6H11O5 + H O Myrosin

2 S C N C3H5 + KHSO4 + C6H12O6
N O SO3K
Allylisothiocyanate Pot. acid sulfate Glucose
Sinigrin
(Mustard oil)

Classification of volatile oils

1. Hydrocarbon volatile oils

 The volatile oils which contain hydrocarbons as constituent, are called hydrocarbon
volatile oils
 Example: Turpentine oil; contains α- and β-pinene -pinene -pinene
2. Alcoholic volatile oils
OH
 The volatile oils which contain alcohol as constituent, are called alcoholic volatile
oils CH CH CHO
OH
 Example: Peppermint oil; contains menthol
Coriander oil; contains linalool
Linalool Menthol
3. Aldehydic volatile oils Cinnamaldehyde
 The volatile oils which contain aldehyde as constituent, are called aldehydic volatile oils
 Example: Cinnamon oil; contains cinnamaldehyde
O
4. Ketonic volatile oils
 The volatile oils which contain ketone as constituent, are called ketonic volatile oils
 Example: Spearmint; contains (–)-carvone
Caraway; contains (+)-carvone Carvone

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5. Phenolic volatile oils CH2 CH CH2
 The volatile oils which contain phenol as constituent, are called phenolic volatile oils
 Example: Clove oil; contains eugenol
OCH3
6. Phenolic ether volatile oils
OH
 The volatile oils which contain phenolic ether group as constituent, are called phenolic
Eugenol
ether volatile oils CH CH CH3
 Example: Fennel oil and anise oil; both contain anethole
7. Oxide volatile oils O
 The volatile oils which contain oxide group as constituent, are called oxide
OCH3
volatile oils Cineole Anethole
 Example: Eucalyptus oil; contains cineole
8. Ester volatile oils COOCH3

 The volatile oils which contain esters as constituent, are called ester volatile oils
OH
 Example: Oil of Wintergreen; contains methyl salicylate
Methyl salicylate
9. Volatile oils derived from glycosides
 See “Methods of obtaining volatile oils…. Glycoside enzymatic hydrolysis”

Hydrocarbon Volatile Oils: Cubeb Oil, Turpentine Oil

Cubeb oil
 It is a volatile oil obtained from the full grown unripe fruit of Piper cubeba (Fam. Piperaceae)
Constituents
 (+)-sabinene, 1,4-cineole, (–)-cadinene, terpineol
Uses
 Antiseptic
 Expectorant
 Stimulant
Turpentine oil
 It is a volatile oil distilled from oleoresin (gum turpentine) obtained from Pinus palustris and from other
species of Pinus (Fam. Pinaceae)
Constituents
 α-pinene (65%), β-pinene (30%), Other terpenes (5%)
Uses -pinene -pinene
 Counter irritant (mostly used externally)
 Rectified turpentine oil is used internally
Rectified turpentine oil
 It is a turpentine oil rectified by distillation from an aqueous solution of NaOH
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 Used as expectorant

Alcoholic Volatile Oils: Peppermint Oil, Coriander Oil, Cardamom Oil

Peppermint oil (Peppermint ‫)پودینہ‬
 Peppermint oil/American peppermint oil is the volatile oil distilled with steam from the fresh overground
parts of the flowering plant of Mentha piperita (Fam. Labiatae), rectified by distillation and neither
partially nor wholly dementholized
 It yields not less than 5% of esters, calculated as menthyl acetate; and not less than 50% of total menthol
(free and as esters)
Properties
 Colorless or pale yellow liquid
 Has a strong penetrating odor of peppermint
 Pungent taste that is followed by a sensation of cold when air is drawn into the mouth
Constituents
 (–)-menthol (50-78%); in free form
 Menthol combined in various esters such as the acetate (5-20%)
 Other constituents: (+)-menthone, (–)-menthone, cineole, (–)-limonene, (+)-isomenthone, (+)-
neomenthone, (–)-β-caryophyllene
Uses of peppermint oil
 Peppermint oil is pharmaceutic aid (flavor)
OH O OCOCH3
 Carminative
 Stimulant
Menthol Menthone Menthyl acetate
 Counter irritant
 In chewing gums, tooth pastes
Flavoring agent in Phillips Milk of Magnesia®
Japanese peppermint oil
 Japanese peppermint oil is the volatile oil distilled with steam from the fresh over-ground parts of the
flowering plant of Mentha arvensis var. piperascens (Fam. Labiatae), rectified by distillation and neither
partially nor wholly dementholized.
 This oil is higher in menthol content than American peppermint oil
 It is inferior in flavor than American peppermint oil
 Therefore, it is solely employed as a source of menthol
Menthol/Menthan-3-ol
 It is an alcohol obtained from diverse mint oils or prepared synthetically
• From natural source: (–)-menthol
• From synthetic source: (±)-menthol

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Preparation of menthol
 Prepared from Japanese peppermint oil by refrigeration (-22 °C), during which the menthol crystallizes
 The liquid portion is poured off and the crystallized menthol is pressed between filter papers and
subsequently purified by recrystallization
 Synthetic racemic menthol is produced by hydrogenation of thymol
 Menthol may also be prepared from pinene
Properties of menthol
 Colorless hexagonal crystals that are usually needle like, as fused masses or as a crystalline powder
 It has a pleasant peppermint like odor
Uses of menthol
 Topical antipruritic
 Used on skin and mucous membrane as counter irritant, antiseptic and stimulant
 Internally, it has a depressant effect on heart
 In chewing gums, toothpastes, shampoos
Menthol is a constituent of Vicks Vaporub®
Coriander oil (Coriander ‫)دھنیہ‬
 Coriander oil is a volatile oil distilled from dried ripe fruit of Coriandrum sativum (Fam. Umbelliferae)
Constituents
OH
 (+)-linalool (coriandrol) (60-70%)
 Other minor constituents: Limonene, γ-terpinene, p-cymene, α-pinene
Uses
 Flavoring agent
Linalool
 Carminative
Cardamom oil (Cardamom ‫)االئچی‬
 It is a volatile oil distilled from the dried ripe seeds of Elettaria cardamomum (Fam. Zingiberaceae)
Constituents
 Cineole (26-40%)
 α-terpinyl acetate (28-34%)
 Limonene (2-14%) O

 Sabinene (3-5%)
 Linalyl acetate (2-8%) Cineole

Uses
 Flavoring agent
 Carminative

Aldehydic Volatile Oils: Bitter Orange Peel Oil, Sweet Orange Peel Oil, Lemon Oil,
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 Cinnamon Oil, Bitter Almond Oil

Bitter and Sweet orange peel oil

 Bitter orange peel is the dried outer part of the pericarp of the ripe or nearly ripe fruit of bitter orang, Citrus
aurantium var. amara (Fam. Rutaceae)
 Sweet orange peel is the dried outer part of the pericarp of the ripe or nearly ripe fruit of sweet orange C.
aurantium var. sinensis (Fam. Rutaceae)
 Bitter orange is not as widely cultivated as sweet orange
Collection and preparation of orange peel
 The peel should be removed with as little of white 'zest' as possible
 The peel may be removed in four quarters or in a spiral band
 Fine slicing causes the rupture of a large number of oil glands and some loss in aroma
 Sweet orange peel is thinner than that of the bitter orange
 Taste of sweet orange peel; though pungent and aromatic, lacks the extreme bitterness
Constituents of orange peel
 Dried bitter orange peel contains;
• Volatile oil (not less than 2.5%)
• Vitamin C
• Flavonoid glycosides (hesperidin and neohesperidin)
• Neohesperidin gradually disappears on ripening [Present only in bitter orange]
Orange peel oil
 Bitter orange peel oil: It is the oil obtained by expression, without the aid of heat, from the peel of bitter
orang, C. aurantium var. amara (Fam. Rutaceae)
 Sweet orange peel oil: It is the oil obtained by expression, without the aid of heat, from the peel of sweet
orang, C. aurantium var. sinensis (Fam. Rutaceae)
Constituents of orange peel oil
 (+)-limonene O
O
 Citral
 Citronellal
Citronellal Citral Limonene
 Methyl anthranilate
Terpeneless orange peel oil
 95% of the terpenes are removed by vacuum distillation
 One part of the terpeneless oil is equivalent to about 15 parts of the sweet orange oil
Uses of orange peel oil
 In aromatherapy, the essential oil is applied to the skin and also inhaled as a painkiller
 In foods, used as a flavoring agent
 Antispasmodic
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 Sedative
 Tonic
 In manufacturing, used in pharmaceuticals, cosmetics and soaps
Lemon oil (Lemon ‫)لیموں‬
 Lemon oil is the volatile oil obtained by expression, without the aid of heat, from fresh fruit of Citrus
limon (Fam. Rutaceae), with or without the previous separation of the pulp and the peel
Preparation of lemon oil
 Six methods are utilized, out of which five methods yield an oil meeting pharmaceutic requirements
1. Canvas bag method
 Outer portion of the rind, which contains the volatile oils, is removed by grating
 Resultant rasping are placed in canvas bags and subjected to pressure
 The resultant turbid liquid is allowed to stand until the sediment separates
 After that the oil is decanted
2. Sponge method
 Lemon is peeled
 Pieces of peel are pressed flat so that they flex and rupture the oil cells
 The oil is absorbed by the sponge
 When the sponge is saturated, is squeezed out, and the process is repeated
3. Ecuelle method
 Discussed earlier
4. Machine process
 Method is same to that of ecuelle method
 Only the peel is subjected in this method
5. Cold pressed California oil
 Extremely high pressure is applied to the lemons, the juice and oil is removed rapidly
 The juice and oil mixture is then separated by a high speed centrifugal separation at the lowest feasible
temperature and in the shortest possible time
6. Distillation method
 This oil does not conform to the pharmaceutic standards
 This is usually used for the preparation of terpeneless oil of lemon CHO
Constituents of lemon oil
CHO
 (+)-limonene (70-80%)
 β-pinene (8-10%)
Limonene Neral Geranial
 γ-terpinene (8-10%)
 Citral (neral+geranial) (2-4%) [Citral is responsible for lemon oil flavor]
 Lemon oil having terebinthinate odor must not be used or dispensed
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 • Such an odor indicates decomposed terpenes or added turpentine oil
Uses
 Flavoring agent
 Stimulant
 Carminative
 Stomachic
 Aroma and flavor of lemon oil are widely accepted by consumers, so used in cosmetics, liquid cleaners,
food etc.
Terpeneless lemon oil
 High terpene content of lemon oil often causes development of terebinthinate odor during storage
 A considerable amount of these terpenes can be removed by distillation under reduced pressure
 Terpeneless lemon oil contains;
• Citral (40-50%)
• Terpenes (5%) [95% of terpenes have been removed]
 Terpeneless lemon oil is relatively costly
 Produces same organoleptic effect in relatively low quantities
Cinnamon oil (Cinnamon ‫)دارچینی‬
 Cinnamon oil is the volatile oil distilled with steam from the leaves and twigs of Cinnamomum cassia
(Fam. Lauraceae) and rectified by distillation
 It is also known as cassia oil
Properties
 Yellowish to brownish liquid
 Become darker and thicker by age or by exposure to air
 Possesses characteristic odor and taste of cassia cinnamon
Constituents
CH CH CHO
 Cinnamic aldehyde (80-95%)
(Cinnamic aldehyde is also called as cinnamaldehyde, cinnamyl aldehyde)
 Other constituents: Cineole, p-cymene, (–)-linalool, eugenol, β-caryophyllene
Cinnamaldehyde
Uses
 Flavoring agent
 Carminative
 Pungent aromatic
 Antiseptic

Bitter almond oil (Almond ‫)بادام‬

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 Bitter almond oil is a volatile oil obtained by enzymatic hydrolysis of glycosides present in seed kernels
of Prunus amygdalus var. amara (Fam. Rosaceae)
• Sweet almond oil: From Prunus amygdalus var. dulcis
• Bitter almond oil: From Prunus amygdalus var. amara
Constituents of almond
 Both varieties of almonds contain;
• Fixed oil (40-55%)
• Proteins (21%)
• Mucilage
• Emulsin
• Amygdalin (cyanophore glycoside) [Present only in bitter almond]
Preparation of bitter almond oil
Seeds (bitter and sweet almonds) are grinded Expressed in canvass bags between slightly heated iron
plates Oil is clarified by filtration (it is a fixed oil, called ‘almond oil’)
Cake of bitter almonds (left after expressing) Macerated with water for some hours
Hydrolysis of amygdalin occurs Benzaldehyde and HCN are formed (It is a volatile oil, called ‘bitter
almond oil’)
 Bitter almond oil contains benzaldehyde and HCN
 Purified bitter almond oil consists mainly of benzaldehyde (HCN removed)
Uses
 Flavoring agent

CH2OH H CN H CN
O O CH2 C HO CH2 C
OH O O Amygdalase O O
HO OH OH
Prunasin
OH HO HO
-D-glucose
Amygdalin OH OH
Prunase -D-glucose

H2O
H CN
HCN + OHC C
HO
Hydrocyanic acid Benzaldehyde Mandelonitrile
(Benzaldehyde cyanohydrin)

Ketonic Volatile Oils: Camphor, Spearmint Oil, Caraway, Buchu

Camphor ‫کا فو ر‬

Page 12 of 20
 It is a ketone obtained from Cinnamomum camphora (Fam. Lauraceae) (natural camphor) or produced
synthetically (synthetic camphor)
 The specific rotation of natural camphor is between +41° and +43°
 Synthetic camphor is synthetically inactive racemic form
Preparation of camphor
 Natural camphor occurs as a crystalline product in the woody stems and roots and, to a greater extent,
dissolved in the volatile oil
 The wood is chipped and distilled with steam
(One pound of crude camphor is obtained from 20-40 pounds of chips) O

 The crude camphor is then freed of oil by centrifugation and pressing

 Finally resublimed to get in pure grade Camphor
 Synthetic camphor is made from pinene, the principal constituent of turpentine oil
Uses
 Topical antipruritic
 Rubefacient
 Anti-infective
 Commercially used in the manufacture of certain plastics

)5 ‫ آیت‬: ‫بیشک نیک لوگ ایسے جام سے مشروبات پیئں گے جس میں کافور کی آمیزش ہو گی (سورۃالدھر‬
Spearmint oil
 It is a volatile oil distilled with steam from the fresh, overground parts of the flowering plant of Mentha
spicata (common spearmint) or of M. cardiaca (Scotch spearmint) which belong to family Labiatae.
Properties
 Colorless, yellow or greenish yellow liquid
 Has the characteristic odor and taste of spearmint
Constituents O
 (–)-carvone (45-60%)
 (–)-limonene, cineole, (–)-pinene
Oil of caraway and oil of dill contain (+)-carvone
Uses Carvone

 Flavoring agent
 Carminative
 Used to a considerable extent in chewing industry, tooth paste and mouth washes

Caraway oil (Caraway ‫)زیرہ‬

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 It is a volatile oil distilled with steam from the dried ripe fruits of Carum carvi (Fam. Umbelliferae)
Constituents
 (+)-carvone (50-60%) O
 (+)-limonene (40-50%)
Uses
 Flavoring agent
Carvone
 Carminative
Buchu
 Buchu is the dried leaf of Barosma betulina (short or round Buchu), or of B. crenulata (oval Buchu), or
of B. serratifolia (long Buchu) (Fam. Rutaceae)
Constituents
 Volatile oil (30%)
• Constituents of volatile oil: Phenolic camphor, diosphenol, isomenthone, limonene OH

 Mucilage
O
 Resin
 Calcium oxalate
Diosphenol
Uses
 Urinary antiseptic
 Carminative

Phenolic Volatile Oils: Clove Oil, Thyme Oil

Clove oil (Clove ‫)لونگ‬

 Clove oil is the volatile oil distilled with steam from the dried flower bud of Eugenia caryophyllus (Fam.
Myrtaceae)
Properties
 Colorless or pale yellow liquid
 Becomes darker and thicker by age or exposure to air
 Has the characteristic odor and taste of clove
CH2 CH CH2 CH2 CH CH2 CHO
Constituents
 Eugenol (70-90%)
 Eugenol acetate, β-caryophyllene OCH3 OCH3 OCH3
Uses OH OCOCH3 OH

 Flavoring agent Eugenol Eugenol acetate Vanillin

 Toothache remedy (applied topically)

 Used in tooth pastes
 Antiseptic
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 Counter irritant
 Carminative
 Used in commercial production of vanillin
Eugenol (4-allyl-2-methoxyphenol)
 It is a phenol, obtained from clove oil and from other sources
 Usually prepared from clove oil
• Clove oil is shaken with a 10% solution of NaOH to form sodium eugenolate (ionic product, soluble
in water)
• Water layer is extracted/separated and washed with ether (only sodium eugenolate will remain in water
layer, other constituents will go in ether layer
• Sodium eugenolate (present in water layer) is then decomposed with sulfuric acid
• The eugenol is separated by steam distillation

H2SO4
CH2 CH CH2
Eugenol
+ Eugenol + Na2SO4 (Sodium sulfate)
NaOH
H2O OCH3
ONa
Sodium eugenolate

 It is a colorless or pale yellow thin liquid

 It has a strong aromatic odor of clove and a pungent spicy taste
 It is a dental analgesic applied topically to dental cavities
 It is incorporated in dental protective
Thyme oil
 It is a volatile oil distilled with steam from flowering plants of Thymus vulgaris (Fam. Labiatae)
Constituents
 Thymol OH
 Carvacrol
 (–)-α-pinene, p-cymene, (–)-linalool OH

Uses
p-Cymene Thymol Carvacrol
 Antiseptic in OTC drugs
Thymol
 Thymol is a phenol, obtained from thyme oil and from other sources
 It may be prepared synthetically from m-cresol or p-cymene
 Procedure of preparation from thyme oil is same as that for clove oil
 Other method of preparation is; subjecting the thyme oil to freezing temperature, causing the thymol to
crystallize out
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 Thymol occurs as large colorless crystals or as a white crystalline powder
 It has an aromatic thyme like odor and a pungent taste
 It is an antifungal and antibacterial agent
 It is employed topically in lotions, creams and ointments ranging from 0.1 to 1%

Phenolic Ether Volatile Oils: Fennel, Anise, Myristica

Fennel oil (Fennel ‫)سونف‬
 It is a volatile oil distilled with steam from the dried ripe fruit of Foeniculum vulgare (Fam. Umbelliferae)
Constituents
CH CH CH3
 Anethole (50-60%)
 (+)-fenchone
O
 (+)-α-pinene
Uses OCH3
 Flavoring agent Anethole Fenchone

 Carminative
Anise / Aniseed / Star anise
 It is the dried ripe fruit of Pimpinella anisum (Fam. Umbelliferae)
Constituents of anise
 Volatile oil (1-3%)
 Fixed oil (upto 30%)
 Proteins and sugars
Uses of anise
 Flavoring agent used in certain type of bakery products
 Carminative
Anise oil
 Anise oil is the volatile oil distilled with steam from the dried ripe fruit of Pimpinella anisum (Fam.
Umbelliferae) or from the dried ripe fruit of Illicium verum (Fam. Magnoliaceae)
 Chinese star anise oil: Obtained from Illicium verum (Fam. Magnoliaceae) CH CH CH3
Constituents of anise oil
 Anethole (80-90%)
 Methyl chavicol
OCH3
 (+)-α-pinene
Anethole
 Linalool
 Anisaldehyde
Uses of anise oil
 Flavoring agent

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 Carminative
Myristica / Nutmeg ‫جائفل‬
Myristica/Nutmeg
 It is the dried ripe seed of Myristica fragrans (Fam. Myristicaceae) deprived of its seed coat and arillode
and with or without a thin coating of lime
Constituents of myristica/nutmeg
 Fixed oil (25-40%)
Solid at ordinary temperature, sometimes occurs in prismatic crystals and is known as ‘nutmeg butter’
 Volatile oil (8-15%)
 Proteins (in considerable amounts)
 Starch
Uses of myristica/nutmeg
 Flavoring agent
 Condiment
 Useful agent for controlling diarrhea associated with certain carcinoma
 It also causes hallucinations at higher doses (elemicin and myristicin are considered to be responsible for
this effect)
Myristica oil/Nutmeg oil
 It is a volatile oil distilled with steam from the dried kernels of the ripe seeds of Myristica fragrans which
belongs to family Myristicaceae
Properties of myristica oil/nutmeg oil
 Colorless or pale yellow liquid
 Has characteristic odor and taste of nutmeg
O O
Constituents of myristica oil/nutmeg oil
O H3CO O
 Safrole
 Myristicin (methoxysafrole)
 Elemicin CH2 CH CH2 CH2 CH CH2
 Methoxyeugenol Safrole Myristicin
H3CO
 (+)-camphene
 β-terpineol H3CO CH2 CH CH2
 α- and β-pinene
H3CO
 Myrcene Elemicin

 Cineole
 (±)-limonene
Uses of myristica oil/nutmeg oil
 Flavoring agent
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 Carminative

Oxide Volatile Oils: Eucalyptus, Chenopodium

Eucalyptus ‫سفیدہ‬
 Eucalyptus is the dried, scythe-shaped leaf of Eucalyptus globulus or other species of Eucalyptus (Fam.
Myrtaceae)
Constituents of eucalyptus
 Volatile oil (3-6%)
 Several resins
 Tannic acid
Eucalyptus oil
 It is the volatile oil distilled with steam from the fresh leaf of Eucalyptus globulus or from other species
of Eucalyptus which belong to family Myrtaceae
Properties of eucalyptus oil
 Colorless or pale yellow liquid
 Has a characteristic, aromatic, somewhat camphoraceous odor
O
 Pungent, spicy, cooling taste
 Constituents of eucalyptus oil
Cineole
 Cineole (not less than 70%), also called eucalyptol
 Eucalyptus oil intended for medicinal sue contains about 70-85% cineole; lesser amounts of volatile
aldehydes, terpenes, sesquiterpenes, aromatic aldehydes and alcohols, and phenols. Many of these minor
constituents have irritant properties and are removed by re-distillation of oil.
Uses of eucalyptus oil
 Flavor
 Antiseptic
 Diaphoretic (sweat inducing)
 Expectorant
Chenopodium oil (Chenopodium ‫)باتھو‬
 It is a volatile oil collected by steam distillation of fresh aerial parts of Chenopodium ambrosinoides (Fam.
Chenopodiaceae)
Properties of chenopodium oil
 Light yellow in color
 Characteristic unpleasant odor
 Bitter burning taste
Constituents
 Ascaridol (70%)

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 • It explodes on heating or on treating with certain acid
 Other constituents: Limonene, myrcene, methyl salicylate, pinene, thymol, carvone, camphor etc.
Uses
 Anthelmintic
 Generally used in veterinary medicine

Ester Volatile Oils: Rosemary

Rosemary
Rosemary oil
 It is a volatile oil distilled from the flowering tops of leafy twigs of Rosmarinus officinalis (Fam. Labiatae)
Constituents
 Volatile oil (1-2%)
• 1,8-cincole
• Borneol
• Camphor
Uses of rosemary oil
 Its main use in the perfumery industry
 It is a component of soap Liniment
 Frequently used in aromatherapy

Miscellaneous Volatile Oils: Allium, Anethum

Allium / Garlic (‫)لہسن‬
 It is the ripe bulb of Allium sativum (Fam. Liliaceae)
Constituents
 Allicin
• A yellow liquid, responsible for the odor of garlic
• Miscible with alcohol, ether and benzene
 Other constituents: Alliin, volatile oil, fatty oil, mucilage, albumin
 Volatile oil (0.06-0.1%) contains allyl propyl disulphide, diallyl disulphide and allicin
Uses
 Carminative
 Expectorant
 Aphrodisiac
 Used in fevers, respiratory diseases such as chronic bronchitis, bronchial asthma, whooping cough and TB
 Also used in hypertension

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 In Germany, garlic is used as a complement in the diet of hyperlipidemic patients and for prophylaxis of
vascular changes induced by aging

Anethum / Dill fruit

 It is the dried ripe fruits of Anethum graveolens (Apiaceae)
 Indian Dill consists of the dried ripe fruits of Anethum sowa (Apiaceae)
Constituents
 Volatile oil (3-4%)
• Carvone (50-60%)
• Dihydrocarvone
• Limonene
 Myristicin
 Coumarins
 Flavonoids
 Phenolic acids
 Sterols
Uses
 Carminative
 Stomachic
 Diuretic
 Anthelmintic
 Flavor
 To cure gastric disturbances of children
 For preparation of dill water and gripe water
Read Book (not notes) if you want to be a Good Professional

Hafiz Abdul Khaliq ♦ hakhaliq@yahoo.com ♦ pharmacist.hak@gmail.com

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