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Phenylpropane-rich Volatile Oils. Some 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)] - PowerPoint PPT Presentation
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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
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