VOLATILE OILS: PART 2A (HYDROCARBONS- KETONE)

HYDROCARBONS

Linear/acyclic

myrcene

HYDROCARBONS

monocyclic

• limonene

• cymene

HYDROCARBONS

dicyclic

• pinene

• sabinene

• cadinene

• caryophyllene

Pinene:

2 fused rings: cyclohexene and cyclobutane; from Pinus palustris

Sabinene:

from Piper nigrum (spiciness) 

Caryophyllene:

bicyclic sesquiterpene from clove, Piper nigrum, hops, rosemary

HYDROCARBONS

• turpentine

• junipers

Turpentine

source

oleoresin of Pinus palustris

Turpentine

constituents

• alpha pinene

• beta pinene

• camphene

Turpentine

uses: internally

rarely given

Turpentine

externally

• counterirritant

• rubefacient

rectified turpentine oil

by distillation from NaOH

Turpentine

odor and taste

becomes stronger with age

Turpentine

family

pinaceae

Terpin hydrate

• due to action of nitric acid on rectified turpentine

• expectorant

Terebene

• preparaed from oil of turpentine by action of cold sulfuric acid (converts pinene to optically inactive limonene)

• expectorant and antiseptic

Junipers

• cade

• juniper

Cade

source

Juniperus oxycedrus

Cade

family

cupressaceae

Cade

constituent

• cadinene

• phenolic cmpds (guicol, ethylguiacol, cresol)

Cade

uses

• veterinary

• skin diseases

• Moroccan traditional medicine

Cade

distillate is alowed to __

stand for atleast 15-20 days, when a layer of cade oil may be separated

Cade

extraction

Dry distillation from the branches

Juniper

source

Juniperus communis

Juniper

family

cupressaceae

Juniper

uses

• diuretic

• carminative

• antirheumatic

Juniper

prolonged intake may cause

kidney damage due to high terpene HC content and low proportion of terpenen-4-ol

Juniper is key material for

production of gin

Terpinen-4-ol

anti- fungal, ascarizidal, candidiasis

ALCOHOLS

Linear

• geraniol

• linalool

• citronellol

ALCOHOLS

monocyclic

• menthol

• terpineol

ALCOHOLS

bicyclic/ dicyclic

borneol

ALCOHOLS

• peppermint

• rose

• neroli

• pine oil

• cardamom

• sandalwood

• coriander/ silantro

Neutral cellulase-assisted steam distillation (NCSD):

used to optimize the distillation of borneol

Borneol

obtained from Camphor (first discovered in Borneo)

Peppermint

source

Mentha piperita

Japanese peppermint

Mentha arvensis var. piperascens

Peppermint

constituents

• 44% free alcohols (menthol)

• 15-32% ketone (menthone)

Peppermint

uses

• flavor in chewing gums and mouthwash

• carminative

• stimulant

• counterirritant

• “Cooling” additive in cigarettes, cough medicines, antipyretics

Peppermint

family

lamiaceae

flavors of peppermint is due to

ketone and alcohol constituents

medicinal value of peppermint is due to

alcohol constituent

pulegone

• predominant terpene in young tissues

• hepatotoxic due to menthofuran (reduces GSH)

menthone

• older tissues; disappears while menthol accumuates and replaced by menthyl acetate

• ketone analog of menthol

ROSE

Source

Rosa gallica

ROSE

constituents

• citronellol (60%)

• geraniol

• nerol

ROSE

family

rosaceae

ROSE

uses

• astringent (due to tannins)

• frruits are rich in antioxidants like vit c and are generally deemed nutritious (anti-inflammatory for osteoarthritis)

ROSE

sulfur containing cmpds

no artificial mistures can reproduce

Citronellol

• Marketed as colorless oil liquid with fresh rosy odor & bitter taste; moderately soluble in water 

Nerol:

geometric isomer of geraniol

Geraniol

• Fragrance

• Cosmetics

• Pesticide: mosquito & tick repellant/mites

Citronellol

• Food flavorings

• Household cleaning products

• Cosmetics 

• Colognes

Neroli
source

distilled flowers of Citrus aurantium (bitter orange)

Neroli

family

rutaceae

Neroli

constituents

• - linalool

• terpineol

• geraniol

Neroli

uses

• perfume

• flavor

• cosmetics

Neroli

oil from leaves ad twigs is called

petitgrain

petitgrain

• little grains

• traditionally in perfumery and cosmetics; now in aromatherapy

Pine Oil

sources

wood of pinus palustris

Pine Oil

family

pinaceae

Pine Oil

constituents

• alpha terpineol

• methyl chavicol

• borneol

Pine Oil

uses

• disinfectant (not broad spectrum)

• deodorant

Pine Oil

steam distillation of the wood

Cardamom

source

Elettaria cardamomum

Cardamom

family

zingiberaceae

Cardamom

constituents

high proportion of

• terpinyl acetate

• cineole

Cardamom

uses

• flavor

• carminative

• antispasmodic

• relieves nausea, indigestion, flatulence

Cardamom essential oil

is steam distilled from the dried seeds. 

Cardamom essential oil

has a warm, spicy, fruity, and balsamic aroma, and a spirit of yellow color.

Sandalwood

source

santalum album

Sandalwood

family

santalaceae

Sandalwood

constituents

santalol

Sandalwood

uses

perfumery

Sandalwood

extraction

from hardwood via steam distillation

Sandalwood by itself is an

excellent, mild, long-lasting, and sweet perfume, which makes it useful in the perfume industry, soapmaking, candlemaking, incense, folk medicine, and religious or cultural purposes for centuries

Coriander / Silantro

source

Coriandum sativum

Coriander / Silantro

family

apiaceae

Coriander / Silantro

constituents

(+) linalool (65-70%)

Coriander / Silantro

uses

• curry

• carminative

• flavoring agt

Coriander / Silantro

unripe plant

has an unpleasant mousy odor due to the presence of aliphatic aldehydes (mainly C10-C16 aldehydes)

Coriander / Silantro

decoction and tincture of powdered seeds when ripe or in combination with other herbal agents, are recommended for:

• Dyspeptic complaints

• Loss of appetite

• Convulsions

• Insomnia

• Anxiety

Coriander / Silantro

Essential oil can be extracted from

• various parts of the plant. However, composition may vary depending on the extracted part.

• holds promise for use as antihyperglycemic agent

Coriander / Silantro

fully ripe seed

•  colorless or pale yellow with a characteristic odor (mild, sweet, warm, aromatic flavor)

ALDEHYDES

linear

• geranial

• neral

• citronellal

ALDEHYDES

cyclic

• cinnamaldehyde

• vanillin

Cinnamon

source

• Cinnamomum zeylanicum (ceylon)

• cinnamomum cassia (cassia)

• cinnamomum loureiroi/ loureirii(saigon)

Cinnamon

family

lauraceae

Cinnamon

constituents

• 60-75% trans- cinnamaldehyde

• 4-10% phenol

Cinnamon

uses

• flavoring

• carminative

• mild astringent

• germicide

• GI upset; stimulate appetite

oil of cinnamon

70-95% eugenol (clove like odor)

oil of cinnamon

• antiseptic

• anesthetic

oil of cinnamon

• obtained from the dried inner bark of the shoots of C. zeylanicum

• steam distillation

Lemon

sources

citrus limon

Lemon

family

rutaceae

Lemon

constituents

90% of terpenes (limonene)

Lemon

uses

• flavoring

• carminative

• stomachic

• stimulant

• odor of many liquid cleaners

Lemon

Citral

• mixture of geranial and neral (3:1)

• major contributos of flavor: neral

Lemon

Citral upon hydrolysis

forms p-cymene

terpenes in lemon

give a terebinthinate odor which is unpleasant / undesirable