PCOG

• Volatile oils


  Also known as essences, ethereal oils or essential oils
• Volatile oils


  • Evaporate when exposed to air
  • Odorous principles found in various plant parts
  • Undergo auto-oxidation and resinification
• Storage of volatile oils

  • Stored in tight, light resistant containers (amber bottles) in a cool, dry place
  • Stored in amber bottles to prevent air exposure which causes oxidation and resinification
• Plant parts where volatile oils are stored

  • Glandular hairs/trichomes (Lamiaceae)
  • Modified parenchymal cells (Piperaceae)
  • Oil tubes (Apiaceae)
  • Lysogenous & schizogenous ducts (Pinaceae/Rutaceae)

  
• Sources of volatile oils

  • Conifers
  • Rose petals
  • Cinnamon bark & leaves
  • Umbelliferous fruits pericarp
  • Mint stems & leaves
• Formation of volatile oils

  1. Decomposition of resinous layer of cell wall

  2. Hydrolysis of certain glycosides

  
• Physical characteristics of volatile oils

  • Colorless
  • Possess characteristic odors (can be fragrant or not)
  • High refractive index
  • Optically active
  • Immiscible with water but sufficiently soluble to impart odor in water
• Importance of volatile oils in plants

  • Repellent to bad insects
  • Attractant to good insects for cross-pollination
• Differences between volatile oils and fixed oils

  • Volatile oils are made up of terpenes, fixed oils are made up of esters of glycerol and fatty acids
  • Volatile oils do not leave permanent grease on paper, fixed oils do
  • Volatile oils cannot be saponified, fixed oils can
  • Volatile oils can be distilled, fixed oils cannot
  • Volatile oils resinify on long standing, fixed oils become rancid
  • Volatile oils have high refractive index, fixed oils have low refractive index
  • Volatile oils are optically active, fixed oils are optically inactive
  • Primary source of volatile oils is leaves, roots, petals, bark, source of fixed oils is seeds/kernels
• Components of volatile oils

  • Stearoptene (solid oxidized hydrocarbon portion, e.g. menthol, anethol, thymol, camphor)
  • Eleoptene (liquid hydrocarbon portion, e.g. methyl salicylate, eugenol, eucalyptol)
• Methods of extraction of volatile oils

  • Wet distillation (water distillation, steam distillation, water and steam distillation)
  • Dry distillation (destructive distillation)
  • Solvent extraction
  • Expression (ecuelle a piquer, enfleurage)
  • Enzymatic hydrolysis
• Clevenger apparatus


  Used to distill volatile oils that are heavier than water and lighter than water

  
• Commercial uses of volatile oils

  • Perfumes
  • Condiments
  • Spices
  • Cosmetics
• Perfume categories


  • Top notes (most volatile, leave skin rapidly)
  • Middle notes (intermediate tenacity and volatility)
  • Base notes (low volatility, high tenacity, fixatives)
• Examples of base note fixatives

  • Musks (from male musk deer)
  • Civets (from civet cats)
  • Ambergris (from sperm whales)
• Chemical constituents of volatile oils

  • Aromatic compounds (obtained via shikimic acid - phenylpropanoid route)
  • Terpene derivatives (obtained via acetate - mevalonic acid pathway)
• Types of terpene derivatives

  • Monoterpenes (10 carbons, 2 isoprene units)
  • Sesquiterpenes (15 carbons, 3 isoprene units)
  • Diterpenes (20 carbons, 4 isoprene units)
  • Sesterpenes (25 carbons, 5 isoprene units)
  • Triterpenes (30 carbons, 6 isoprene units)
  • Tetraterpenes (40 carbons, 8 isoprene units)
• Top notes

  • Anise oil
  • Lavender oil
  • Lemon Oil
• Top notes

  Evaporate the skin rapidly
• Middle notes

  • Thyme
  • Rose
  • Neroli Oils (Orange Peel)
• Middle notes


  Intermediate Tenacity and Volatility, somehow stay pero masnagsstay si base note
• Base notes

  • MUSKS
  • CIVETS
  • AMBERGRIS
• Base notes


  Low volatility but have a high tenacity, Pinaka nagsstay sa body, AKA: Fixatives — high staying power
• MUSKS


  From male musk deer of asia, Pheromone
• CIVETS


  From civet cats, Produced when stressed
• AMBERGRIS


  Most valuable material, Physiological products from the stomach of sperm whales when it accidentally feeds on squid or cuttlefish
• Chemical constituents of volatile oils

  • Aromatic Compounds
  • Terpene Derivatives
• Aromatic Compounds


  Obtained via Shikimic Acid - Phenylpropanoid Route
• Terpene Derivatives

  Obtained via acetate - mevalonic acid pathway, Terpenes — Natural products whose structures may be divided into isoprene units
• Terpene derivatives by number of carbons

  • Monoterpene (10 carbons, 2 isoprene units)
  • Sesquiterpene (15 carbons, 3 isoprene units)
  • Diterpene (20 carbons, 4 isoprene units)
  • Sesterpenes (25 carbons, 5 isoprene units)
  • Triterpene (30 carbons, 6 isoprene units)
  • Tetraterpene (40 carbons, 8 isoprene units)
• Isoprene unit


  Branched chain that contains 5 carbon units with 2 unsaturated bonds
• During the formation of terpenes, the isoprene units are linked together in a head to tail manner</b>
• The number of units of isoprene that are incorporated in a particular terpene serves as the basis of classifications of these compounds
• Mevalonic acid pathway for terpene production

  1. Starting product is 2 Acetyl CoA, when joined together will become Acetoacetyl CoA

  2. HMG CoA reductase is inhibited by statins

  3. Produces Sesquiterpenes, Sterols, Diterpene, Monoterpene
• Phenylpropanoids


  Compounds that contain the C6 phenyl ring with attached C3 propane side chain, Examples: Cinnamaldehyde, Anethole, Eugenol, Methyl salicylate
• Shikimic acid pathway for phenylpropanoid production

  Starting products: E4P (erythrose-4-phosphate) & PEP (Phospophenol pyruvate), either can be converted into deoxy arabino heptolonic acid phosphate (DAAP) with the aid of water loss of phosphate occurs

  
• Classification of volatile oils

  • Hydrocarbon volatile oil
  • Alcohol volatile oil
  • Aldehyde volatile oil
  • Ketone volatile oil
  • Phenol volatile oil
  • Phenolic-ether volatile oil
  • Oxide volatile oil
  • Ester volatile oil
• Turpentine oil / Spirits of turpentine


  From pine (Pinus palustris) and from other species of Pinus line, Contains Pinene, The only example of an oil that only contains hydrocarbons, The largest volume in commerce but used little in essential oil and pharmaceutical industry because it's primarily a raw material for chemical manufacturing
• Types of turpentine oil

  • Rectified turpentine oil
  • Terpin hydrate / Turpinol / Cis-p-methane-1, 8-diol hydrate
• Rectified turpentine oil


  If turpentine oil was rectified by distillation from an aqueous solution of NaOH, Dispense when turpentine oil is required for internal use, Used as an expectorant