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Phenylpropane-rich Volatile Oils

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)]

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Phenylpropane-rich Volatile Oils

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  1. Phenylpropane-rich Volatile Oils Some examples: • Cinnamon oil • Anise oil • Fennel oil • Clove oil • Nutmeg oil • Peru balsam • Tolu balsam

  2. 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)

  3. 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

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

  5. Fruits of Foeniculumvulgare, Apiaceae • 2-6% v.o • 50-60% anethole • 20% fenchone (bicyclic monoterpene) distinction odour from anise oil • Flavouring agent • Carminative

  6. 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 toothache C/I: anticoagulant

  7. 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) Amphetamine

  8. Monoterpene-rich volatile oils Some examples: • Peppermint oil • Lavender oil • Lemon oil • Camphor • Thyme oil • Turpentine oil • Rosemary oil

  9. Terpenoid Components of V.O Monoterpenes & sesquiterpenes Monopterpenes: • 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)

  10. 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

  11. 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

  12. 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

  13. SpearmintMentha spicata (Lamiaceae) Fresh leaves 1-2 % VO Mainly (-)Carvone 50-70% (-) Limonene 2-25% Aromatherapy Carminative Flavouring Chewing gum industry!

  14. 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

  15. 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 colds Oil induces irritation of mucous membrane Eucalyptol is not irritant to mucous membrane

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

  17. Chamomile VO Other sesquiterpenes representing 10-25% of VO

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