pcog Flashcards
(254 cards)
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VOLATILE OILS
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Janne Paulyne Libunao
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RPh
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• odoriferous plant principles
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• insect repellant & insect attractant
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• composed of terpenoids - compounds having
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isoprene unit (5C) as building blocks
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– Thermal decomposition of terpenoids gives
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isoprene as one of the product.
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– Isoprene rule states that the terpenoid molecules
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are constructed from two or more isoprene unit.
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• aka: Ethereal oils or Essential Oils or Essences
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• Standard Storage Conditions: stored in a dark
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cool place preferably in a full amber glass
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container
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Reasons for Storage
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• Volatility
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• Autooxidation
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• Photosensitivity
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FAMILIES
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SECRETORY
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FAMILY
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STRUCTURES
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Lamiaceae
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Glandular Hairs
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(Labiatae)
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Piperaceae Modified Parenchyma Cells
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Apiaceae
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"Vittae" or oil tubes
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(Umbilliferae)
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Rutaceae/ Schizogenous/ Lysigenous
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Pinaceae ducts
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Physical Characteristics
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• Posses characteristic odor
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• High refractive index - refractometry
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• Optically active
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• Immiscible in water but they can be sufficiently soluble
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to impart their odor in water → aromatic waters
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Difference between V.O. and F.O.
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• V.O. can be distilled
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• V.O. don't saponify
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• V.O. don't leave a greasy spot on paper
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• V.O. don't have glycerol as backbone
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• V.O. don't become rancid
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Methods of Isolating
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Volatile Oil
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1. DISTILLATION
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• Water - vehicle; requires fresh sample or samples which are resistant to
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high-temp (Ex: Turpentine Oil)
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• H2O & Steam - no active boiling of the sample
can be done on fresh or
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dried samples (Ex: Cinnamon & Clove Oil)
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• Steam distillation
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– Peppermint & spearmint
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– For fresh samples only
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• No vehicle - Destructive Distillation
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– Disadvantage: formation of smoke-like/ burn-like odor (empyreumatic odor)
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– Empyreumetric oils (heat w/o air access)
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– Incineration: only Pinaceae & Cuppresiaceae
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2. EXPRESSION
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• Ecuelle - a process involving a machine/ mechanical
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device with spikes designed to puncture the oil glands
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– preferable for citrus samples
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• Enfleurage - involves the use of a fatty pomade which
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absorbs the oil from the sample → Ethanol extract
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3. EXTRACTION
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• involves the use of organic solvents
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• advantage: low BPs - the process can be done at a
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much lower temp. w/o compromising the quality of the
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oil
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• disadvantage: cost of solvents; some are toxic (e.g.
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benzene)
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4. ENZYMATIC HYDROLYSIS
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• Ex: Glycosidic volatile oils
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• Sinalbin/ Sinigrin (Myrosin) --> Glycosidic
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volatile oils
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Components of Volatile Oil
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• STEAROPTENE - solid portion
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• ELEOPTENE - liquid portion
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• Medicinal and Commercial Uses: Fabrication of perfumes
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1. Top notes - most volatile products; they leave skin readily
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2. Middle notes - intermediate tenacity and volatility
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3. Base note - low volatility and high tenacity
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• Aka: fixatives : staying power
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• Most oil-based perfume
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Sources:
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1. Musk
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– Dried secretion from the preputial follicles of the male musk deer of asia
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– Moschus spp.
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2. Civet
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– A glandular secretion appearing outwardly discharging pockets of Civet
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cats (Paradoxus hermaphroditus)
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3. Ambergris
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– Most valuable base note
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– Pathologic product formed in the stomach of sperm whale when it feeds
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on squid or cattle fish
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– Ambrein
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Constituents of Volatile oil
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• Terpenes/Terpenoids
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– Natural products whose structures are made up of
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isoprene units (C5)- building blocks
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– compounds isolated from terpentine
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– modern definition: ‘Terpenoids are the hydro-
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carbons of plant origin of the general formula
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(C5H8)n as well as their oxygenated
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hydrogenated
and dehydrogenated derivatives.’
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CLASSIFICATION OF TERPENOIDS
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CLASSIFICATION OF TERPENOIDS
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• Each class can be further subdivided into subclasses according
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to the number of rings present in the structure.
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1. Acyclic Terpenoids: They contain open structure.
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2. Monocyclic Terpenoids: They contain one ring in the structure.
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3. Bicyclic Terpenoids: They contain two rings in the structure.
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4. Tricyclic Terpenoids: They contain three rings in the structure.
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5. Tetracyclic Terpenoids: They contain four rings in the
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structure.
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CLASSIFICATION OF VOLATILE OILS
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I. HYDROCARBON
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VOLATILE OILS
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• Limonene
P-cymene
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found in plants)
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• Sabin & Myrcene
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1. Turpentine Oil
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• Contains pinene
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• Source: Pine Tree (Pinus palustris)
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• Forms/ Preparations:
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– Rectified Turpentine Oil: distillation with an aqueous solution
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of NaOH
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– Terpinhydrate: or Terpineol - formed by the reaction of RTO
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w/ HNO3 in the presence of alcohol
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Use: both preparations are used as stimulant expectorant
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II. ALCOHOL VOLATILE OILS
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• Acyclic: Geraniol
Linalool & Citronellol
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• Monocyclic: Menthol
α-terpineol
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• Dicyclic: Borneol
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• Sesquiterpene: Zingiberol
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1. Peppermint Oil
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• SN: Mentha piperita
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• Japanese peppermint - SN: M. arvensis
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• used as a source of menthol (by freezing the oil)
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– synthetic menthol (racemic mixture)
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– natural menthol (levo)
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2. Cardamom Oil
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• SN: Elettaria cardamom
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• Chief Const: Cineole
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3. Coriander Oil
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• SN: Coriandrum sativum
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• Const: Linalool
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• Use: Carminative
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4. Rose Oil
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• CN: Otto of Rose
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• SN: Rosa gallica
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• Const: Geraniol
Nerol
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5. Orange Flower Oil
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• CN: Neroli Oil
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• SN: Citrus aurantium
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• Const: Linalool
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6. Juniper Oil
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• SN: Juniperus communis
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• Const: Borneol
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• Use: OTC as diuretic (Odrinyl®)
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7. Pine Oil
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• Const: α-terpineol
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III. ALDEHYDE VOLATILE OILS
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• Acyclic - Citral
Citronellol
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• Aromatic - Cinnamaldehyde
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1. Cinnamon
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• Saigon - Cinnamomum laureini
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• Ceylon - C. zeylanicum
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• Cassia - C. cassia
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• Constituent: Cinnamaldehyde
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• Flavor
carminative
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2. Lemon
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• Const: Citral - combination of Neral & Geranial
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(responsible for the odor)
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• Common problem: Terebinthenate Odor (attributed to
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the terpene content)
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• High quality: Terpeneless Oil (95% of terpenes are
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removed)
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3. Orange Oil (Sweet Orange)
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• SN: Citrus sinensis
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• Const: Decanal
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• Chief const: Limonene (HC)
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4. Citronella Oil
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• SN: Cymbopogon nandus
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• CN: Tanglad
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• Const: Citronellal - mosquito repellant action
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5. Hamamelis
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• Const: 2-hexen-1-al
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• Use: OTC for hemorrhoids (astringent
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property)
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IV. KETONE
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• Monocyclic: Menthone
Carvone
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Pulegone
Diosphenol
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• Dicyclic: Camphor
Fenchone
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1. Camphor
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• SN: Cinnamomum camphora
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• Const: Camphor
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– Natural: Dextro
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– Synthetic: Racemic
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• Anti-pruritic
rubefacient
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• Camphor + menthol = eutectic mixture =
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lower m.p.
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2. Spearmint
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• SN: Mentha spicata
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• Const: (-) Carvone
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3. Caraway
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• SN: Carum carvi
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• Const: (+) Carvone
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4. Buchu
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• SN: Barosma betulina
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• Const: Diosphenol
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• Use: OTC for menstrual period
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5. Wormwood Oil
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• SN: Artemisia absinthum
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• Const: (+) Thujone
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• Use: Counterirritant
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6. Cedar Leaf Oil
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• SN: Thuja occidentalis
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• Const: (+) Thujone
(-) Fenchone
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• Use: Vicks Vaporub®
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IV. PHENOL
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• contains phenolic substances in their
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structures
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1. Thyme Oil
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• SN: Thymus vulgaris
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• Uses: Antifungal
Antibacterial
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2. Clove Oil
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• SN: Eugenia caryophilus (Fam. Myrtaceae)
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• Const: Eugenol - analgesic property
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• Use: common ingredient in dental
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preparations
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3. Myrcia Oil
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• CN: Bay Oil
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• SN: Pimenta racemosa
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• Const: Eugenol
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4. Creosote
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• CN: Beechwood creosote
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• SN: Fagus grandiflora
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• Const: Guaiacol cresol
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5. Juniper Tar
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• SN: Juniperus oxycedrus
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• CN: Cade Oil
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• Use: OTC for eczema and psoriasis (Polytar®)
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6. Pine Tar
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• Use: Anti-eczema and psoriasis
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• Const: Phenol & Cresol
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VI. PHENOLIC ETHER
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• Nutmeg - "butter of nutmeg
" myristica
– Const: Myristicin, Saffrole
– Uses: Flavoring agent, Carminative
– Hallucinogen: date-rape drugs
• Const: Trans-anethole
– Anise - Pimpinella anisum
– Fennel - Foeniculum vulgare
– Chinese Star Anise - Illicum verum
VII. OXIDATIVE VOLATILE OILS
• Eucalyptus
– SN: Eucalyptus globulus
– Const: Eucalyptol (Cineole, Cajuptol, Cajupot)
– Use: Counterirritant
VIII. ESTER VOLATILE OIL
• contains esters in their structure
1. Gaultheria Oil
• CN: Wintergreen, Teaberry, Chuckerberry
• SN: Gaultheria procumbens
• Const: Methyl salicylate
• Name of Oil: Gaultheria Oil, Wintergreen Oil, Betula Oil, Sweet
Birch Oil
2. Lavender Oil
• SN: Lavandula augustifolia
• Const: Linalyl acetate - from Linalool
3. Pine Needle Oil
• SN: Pinus mugo
• Const: Bornyl acetate - from borneol
4. Mustard Oil
• Allyl and acrinyl isothiocyanate
