Phenylpropane-rich Volatile OilsSome examples:• Cinnamon oil • Anise oil• Fennel oil• Clove oil• Nutmeg oil• Peru balsam• Tolu balsam

Cinnamon oil

• Obtained from the dried bark of Cinnamonum zeylanicum, Lauraceae by steam distillation ;

• [Cinnamomum aromaticum (Chinese cinnamon)]• Cinnamaledhyde is main constituent (65-75%)• Flavouring agent • Carminative• C.I. 1st trimester (uterine stimulant)

CINNAMALDEHYDE

O

H

Anise Oil (Anisi aetheroleum)• V.O. from anise fruits (Anisi fructus) Pimpinella anisum L.,

Apiaceae 1-3% v.o. or star anise Illicium verum, Magnoliaceae 2.5-5% v.o.

• Egypt, Greece, South America & Europe• Solidifies @ 15°C (fresh oil)• Anethole 80-90%• Occurs with its isomer with estragole →• Flavouring agent (indigestion) • Expectorant in cough mixtures• Dianethole (polymerization product [light & O2]) estrogenic

properties

OCH3

ANETHOLE

CH3

H2C

OCH3

H3CCH2

OCH3

CHC

Dianethol

4

Bastard Star Anise• Dried ripe fruit of Illicium religiosum = I. anisatum• Myristicin, methyleugenol in small amounts• V.O. leads to convulsions (sesquiterpenes-induced)

Fruits of Foeniculum vulgare, Apiaceae

• 2-6% v.o• 50-60% anethole• 20% fenchone (bicyclic monoterpene)

distinction odour from anise oil • Flavouring agent • Carminative

CH3

CH2CH

Anethole

OCH3

O

Fenchone

Syzygium aromaticum (Eugenia caryophyllata) Myrtaceae

Dried flower buds “Clove oil”Eugenol 85-95% Dental practice as disinfectant, analgesic & anti-

inflammatory The only V.O sold in pharmacy as OTC product for

toothacheC/I: anticoagulant

OH

OCH3

Eugenol (4-Allyl-2-methoxyphenol)

Myristica fragrans, Myristicaceae • Dried, ripe seed kernel• Indonesia, Malaysia & Sri Lanka v.o., terpenes • Hallucinogenic if taken in large quantity 15gm• [Prison opium]:reddening of skin, palpitations,

decreased salivation• Terpenoid and C6-C3 V.O.(Pinenes, Limonene,

Terpinenes)

OCH3OO

MyristicinOCH3

H3COOCH3Elemicin

Amphetamine

Monoterpene-rich volatile oils

Some examples:• Peppermint oil• Lavender oil• Lemon oil• Camphor• Thyme oil• Turpentine oil• Rosemary oil

Terpenoid Components of V.O

Monoterpenes & sesquiterpenesMonopterpenes: • Most monoterpene-rich v.o are flavouring

agents • Some as rubefacients, sedatives & bitters,

insecticides • Monoterpenes classified by degree of

oxidation (hydrocarbons, alcohols, aldehydes, ketones, phenols & oxides)

Turpentine Oil• Oleoresin from Pinus palustris USA, P. pinaster France, Pinaceae• wounding tree• Solid resin after distillation is known as colophony (70%) • Grading depending on Pinus spp• Vol. oils: 15-30%; Alpha & Beta-pinenes are major

constituents • Only rectified turpentine oil is used internally (diuretic,

expectorant, anthelmintic)• Externally as rubefacient in liniments for rheumatic pain

(+)-alpha-Pinene (+)-beta-Pinene

Camphor

• Obtained from the distilled oil of Cinnamomum camphora (Lauraceae)

• Characteristic odor, pungent aromatic taste• Natural camphor is optically active, while synthetic

camphor is a racemate; prepared from pinene• Used externally as rubefacient; internally as mild

antiseptic and carminative (low doses)• SE: respiratory stimulant

(+)-alpha-Pinene

Volatile oil of Peppermint

• Fresh leaves of Mentha piperita (Lamiaceae)steam distillation

• Menthol 50% (pleasant taste)• Menthofuran (disagreeable odour & taste) young

and/or wet leaves• Cooling effect (mouth wash & tooth paste)• Carminative

Menthylacetate

OH

Menthol

O

(+)-Menthofuran

SpearmintMentha spicata (Lamiaceae)

• Fresh leaves 1-2 % VO• Mainly (-)Carvone 50-70% (-) Limonene 2-25%• Aromatherapy • Carminative • Flavouring •Chewing gum industry!

O

(-)-Carvone (-)-Limonene

Thymus vulgaris (Medicinal thyme)Origanum vulgare (Oregano; زعتر)

Thymol Carvacrol p-cymene

Thymol and its isomer carvacrol are bactericidal, antispasmodic, antifungal

Thymol: colorless crystals/white crystalline powder; microsublimed

Eucalyptus Oil• Steam distillation of Eucalyptus globulus, E.

polybractea leaves (Myrtaceae)• 70-85% Euclyptol=cineole• Australia, Europe & Southern USA• V.O. 0ºC ppt Eucalyptol

Liquid Solid

(Room Temp) (< 0ºC)Lozenges and inhalants to ease discomfort associated with coldsOil induces irritation of mucous membraneEucalyptol is not irritant to mucous membrane

O

Cineole

Matricaria chamomilla =Chamomilla recutica flower head German chamomile (Asteraceae); ChamazulenesAnthemis nobilis Roman chamomile; Nobilinsesquiterpene volatile oils; antispasmodic, antiphlogistic, carminative, diuretic, diaphoretic

Chamazulene

OAC

O

O

OH

Matricin

HO2CChamazulene Carboxylic Acid

- CO2

- HOAc- 2 H2O

Fresh Plant Steam Distillation

Chamomile VO

Other sesquiterpenes representing 10-25% of VO

OHO

OH

O

OHBisbalol oxide B

Bisbalol oxide A

(-)-ALPHA-Bisbalol