CA1 M2: PCOG VOLATILE OILS

Optically active, with high refractive index

Volatile Oils

Used as insect repellant and attractant

Volatile oils

Drying agent to purify essential oils

anhydrous calcium sulfate

Which is saponifiable? Fixed or Volatile oils

Fixed oils

Which has nutritive value? Fixed or volatile oils

Fixed oils

Volatile oil location: Rutaceae

Schizogenous or lysigenous ducts

Volatile oil location: Pinaceae

Schizogenous or lysigenous ducts

Volatile oil location: Apiaceae/Umbelliferae

Oil tubes (vittae)

Volatile oil location: Piperaceae

Modified parenchyma cells

Volatile oil location: Lamiaceae/Labiatae

Glandular trichomes

Volatile oil location: Rose

petals

Volatile oil location: Cinnamon

Bark

Uses Clavenger apparatus

Distillation

Principle of distillation

Difference in boiling points

For dried parts not injured by boiling

Water distillation

example of a plant that can undergo water distillation

Turpentine

For dried and fresh parts that may be injured by heat (with maceration)

Water and steam distillation

example of a plant that can undergo water and steam distillation

cinnamon, clove

example of a plant that can undergo direct steam distillation

Peppermint, spearmint

For fresh materials having their own moisture (not macerated)

Direct steam distillation

Method of obtaining volatile oil for glycosidic volatile oils

Enzymatic hydrolysis

Example of plant that can undergo enzymatic hydrolysis

Black mustard (Sinapis nigra):

sinigrin - (myrosin) -> allyl isothiocyanate

Best method for citrus volatile oils (aroma injured by heat)

Expression

Expression: plant part used is rind

Sponge process

Expression: whole fruit is used, passed through a pan with spikes, puncturing the oil glands

Ecuelle method

Uses both sponge process and Ecuelle method after centrifugation

Machine Process

Most important VO and type

Citral (aldehyde VO)

- becomes p-cymene (hydrocarbon VO)

Uses Soxhlet apparatus and volatile solvent systems (benzene, ether)

Extraction

Fast, preserves quality (controlled temp at 50C)

Extraction

Uses inodorous bland fat (pomade) / fixed oil

Maceration

Uses moderate heat like maceration

Digestion

Used in making perfumes and pomades

Enflourage

Used to extract small amts of VO from plant parts like petals

Enflourage

Enflourage and percolation: the resulting solution which is composed of alcohol, VO, plant waxes

Concrete

Enflourage: what is used to remove the plant waxes from the concrete

Dissolving VO in alcohol, then filtering the waxes

Tedious but extracts the best quality of VO

Enflourage

Resulting fatty products impregnated with the floral odor

Pomade

Percolation with volatile solvents uses what solvent

Highly purified petroleum benzene

What is used to remove the volatile solvent in percolation?

Vacuum distillation

What is used to remove the alcohol used to dissolve the VO and soluble waxes?

Chilling to 20C

Resulting product after removing the waxes and alcohol from concrete

Absolutes (purified VO)

Process of heating without air

Destructive distillation

Used to obtain empyreumatic or smoke-like odor

Destructive distillation

Example of substance obtained from destructive distillation

Tar

Note that is high in volatility

Top note

Examples of top note

Lavender, anise, lemon

Note that is intermediate in volatility and tenacity

Middle note

Examples of middle note

Thymol, neroli, rose oils

Note that is low in volatility and high in tenacity (fixatives)

Base note

Examples of base note

Vanillin, musk, civet, ambergris

Only fixative from plants

Vanillin

Two broad classifications of VO and the pathways from which they are derived

a. Terpenoids - Acetate-mevalonate

b. Phenylpropranoids/Aromatics - Shikimic acid

Most common VO found in plants

Monoterpenes

Largest class of terpenoids

Sesquiterpenes

Monoterpenes are derived from what VO?

Limonene

Occurs as glycosides in plants

Monoterpenes

Trans form; precursor of acyclic monoterpenes

Geranyl pyrophosphate

Cis form; precursor of cyclic monoterpenes

Neryl pyrophosphate

Precursor of phenylpropanoids

Cinnamic acid

Example of monoterpene

Limonene

Example of sesquiterpene

Quinghaosu (Artemisia annua) - antimalarial

Example of diterpene

Paclitaxel (antineoplastic)

Example of triterpene

Neem (Azadirachta indica) - insect repellant

Component of VO that contains hydrocarbons, liquid

Eleoptene

Component of VO that contains oxidized hydrocarbons, solid

Stearoptene

Examples of eleoptene

Eugenol, methyl salicylate, eucalyptol

Examples of stearoptene

Menthol, anethole, thymol

Pinus palustris

Turpentine oil/Pine Tree oil/Spirit of Turpentine

Cons of turpentile oil

a-pinene, B-pinene

Used as counterirritant in Vicks VapoRub

Turpentine oil

Components of Vicks VapoRub

Camphor, menthol, eucalyptus oil

Turpentine oil treated w NaOH, expectorant

Rectified turpentine oil

Rectified turpentine oil treated w HNO3 in alcohol (elixir), expectorant

Terpin hydrate / Terpinol

Juniperus oxycedrus

Cade

Cons of cade

Cadenine, guiacol, ethylguiacol, cresol

Precursor of guaifenesin

Guiacol

Used for veterinary purposes and skin diseases

Cade

Distilled is allowed to stand for 15-20 days when a layer of oil may be separated

Cade

Juniperus communis

Juniper

Cons of juniper

a-pinene, B-pinene

Used as diuretic and antiseptic

Junioer

Used as diuretic, carminative, antirheumatic

Oil of juniper

Prolonged use can cause kidney damage

Juniper

Key material in gin production

Juniper

Monocyclic alcohol VO

Menthol, terpineol

Dicyclic alcohol VO: borneol