NAME

SYNONYMS

HYDROCARBON VOLATILE OILS

Turpentine oil
Spirits of turpentine

SCIENTIFIC NAME AND

FAMILY

PART USED

Pinus palustris (pinaceae)

ACTIVE
CONSTITUENT

USE

OTHERS

65% -pinene, 30% pinene, and 5% other

terpenes

Counterirritant (vicks
vaporub, mentholatum
deep heating, sloans
liniment)

Distilled
Yield terpene oils exclusively
Largest volume of essential oil in commerce (little
is used by the pharmaceutic industry cause it is a
raw material)
Rectified by distillation from an aqueous solution of
NaOH.
Dispensed if internal use is required.
Action of nitric acid on rectified turpentine oil in the
presence of alcohol
Usual dose: 85mg

Rectified turpentine
oil
Terpin hydrate

expectorant

Terpinol, cis-pmenthane-1,8-diol
hydrate

ALCOHOL VOLATILE OILS

Peppermint
American peppermint
oil
Japanese peppermint
Peppermint oil
oil

Japanese peppermint
oil

Menthe arvensis oil

Menthol

Menthan-3-ol

American peppermint oil cointains:

50-78% of free (-)menthol
5-20% combined in various esters such as acetate
(+) and (-) menthone
Cineole
(+) isomenthone
(+) neomenthone
(+) menthofuran

Expectorant cause it is
a Stimulant to mucous
membranes
Menthe piperita (labiatae)
M. arvensis
M. piperascens

Leaf and
flowering
top
Overground
parts of the
flowering
plant

Volatile oil (1%), resin,

tannin
Not less than 5% of
esters (menthyl
acetate)
Not less than 50% of
total menthol (free
and as esters)

Distillate water may be aromatic

Pharmaceutic aid
(flavor), carminative,
stimulant,
counterirritant
Chief commercial
importance: flavor for
confections (chewing
gum)
Source of menthol

Distilled with steam, rectified by distillation and

neither partially nor wholly dementholized

Steam distillation
Higher in menthol content but inferior to flavor to
peppermint oil
Alcohol; Synthetic
May be levorotatory (-) menthol (natural/synthetic)
or racemic (+) menthol (synthetic)
Usually prepared by refrigeration (-22 C) ->
menthol crystallizes -> liquid is removed ->
menthol is pressed between filter papers ->
subsequently purified by recrystallization
Synthetic racemic menthol: produced by
hydrogenation of thymol
May also be prepared from pinene

An enzyme preparation frim menthe leaves has

also been shown to reduce the isopropylidene
double bond of pipertenone -> piperitone
Small amounts of menthone and menthol were
also formed with piperitenone as the substrate
(indicate the cyclohexene double bond of the
precursor was reduced)
Key step!! Dehydration of -terpineol ->
terpinolene and limonene
Leading to the formation of -terpineol +
mevalonic acid
Cardamom oil

Elettaria cardamomum
(zingiberaceae)

Dried, ripe
seed

Coriander oil

Coriandrum sativum
(umbelliferae)

Dried, ripe
fruit

Rosa gallica, R.
damascena, R. alba, R.
centifolia (rosaceae)
Citrus aurantium
(rutaceae)

Fresh
flowers

Juniper oil

Juniperus communis
(cupressaceae)

Dried, ripe
fruit

Pine oil

Pinus palustris (pinaceae)

Wood

ALDEHYDE VOLATILE OILS

Cinnamon
Saigon cinnamon
Ceylon cinnamon
Cassia cinnamon

Cinnamomum loureirii
c. zeylanicum
C. cassia (lauraceae)

Inner Bark

Rose oil

Otto of rose

Orange flower oil

Neroli oil

Fresh
flowers

26-40% cineole, 2834% - terpinyl

acetate, 2-14%
limonene, 3-5%
sabinene, 2-8% linalyl
acetate
60-70% (+) linalool,
limonene, -pinene,
- terpinene, pcymene, camphor
Geraniol, (-)
citronellol, nerol

Flavor, carminative

distilled

Flavor, carminative

Distilled with steam

Perfume

Distilled with steam

30% (-) linalool, (+) terpineol, geraniol,

geranyl acetate, pinene, 7% linalyl
acetate, limonene
70% -pinene, pinene,-terpineol,
borneol, geraniol
65% -terpineol, 10%
methyl chavicol and
related phenol ethers,
9% borneol, 8%
fenchol, 4% menthols

Perfume, flavor

Distilled

Flavor, diuretic in
odrinil (otc drug)

Distilled with steam

Disinfectant,
deodorant

Extraction and fractionation/ by steam distillation

Carminatives and
flavors

Cinnamon from southern asia and adjacent islands

is superior
Usually used: young trees (less than 6 yrs old)
Saigon cinnamon 2-6% of volatile oil
Cassia cinnamon- 0.5-1.5%
Ceylon cinnamon 0.5 1%
Other constituents: mannitol (causes the
sweetness of the bark), tannin (abundant in cassia
cinnamon)

Cinnamon oil

Cassia oil

Cinnamaldehyde

Cinnamic aldehyde,
cinnamyl aldehyde

Leaves and
twigs

Orange oil

Citrus sinensis (rutaceae)

Citronella oil

Cymbopogon winterianus,
C. nardus (gramineae)

Hamamelis water

Lemon peel
Lemon oil

Distilled with hazel

extract

Fresh peel
of the ripe
fruit
Leaves

Hamamelis virginiana
(hamamelidaceae)

Twigs

Citrus limon (rutaceae)

Fruit
fruit

Cinnamic aldehyde,
terpenes (limonene,
p-cymene, (-) linalool
and - caryophylene),
others such as
eugenol

Flavoring agent,
carminative, pungent
aromatic, antiseptic
properties

Naturally from cassia oil or synthetically from a

mixture of benzaldehyde and acetaldehyde by the
action of NaOH
Stored: well filled, tight, light resistant containers
and protected from excessive heat
Expression

1-2% decanal, more

than 90% limonene

Flavor

5-55% (+)-citronellal,
25-40% geraniol, 1115% (+) citronellol
9.7% 2-hexen-1-al,
3.2% acetaldehyde,
3.5% - ionone, 1.0%
- ionone, 0.2%
safrole

Perfume, insect
repellant

Distilled with steam

Astringent in the OTC

hemorrhoid prep
(tucks, rantex,
mediconet, hazelbalm, gentzwipes)
Flavoring agent,
stimulant, stomachic
Flavoring agent,
stimulant, carminative,
stomachic property
Valuable commodity in
cosmetics and liquid
cleansers

Hydroalcoholic solution
Steam distillation

(+) limonene
Others: -pinene and
-terpinene
Contains:
13% citral (but a
range of 2-4% is
optimum for high
quality oil)
Primary esters: neryl
and geranyl acetates
(believed to be
important in providing
a full bodied lemon
flavor)

Turpentine oil

Distilled with steam, rectified by distillation

Formerly an adulterant

Removed by grating or paring

Expression without the aid of heat, with or without
the previous separation of the pulp and the peel
Six processes are utilized in the recovery of the oil
of lemon:

Grating

Rotated in a saucer shaped

container(Ecuelle a piquer) entire fruit

Sponge process

Oil is separated like that of ecuelle a piquer

but only the peel is subjected to this
(machine process)

Application of extremely high pressure and

rapid removal of the juice and oil (cold
press)

Distillation does not conform to

pharmaceutic standards
Neral and geranial most important contributors to
the lemon oil flavor
If it has a terebinthinate odor it shouldnt be used
or dispensed.
Indicates decomposed terpenes or added
turpentine oil
Replaced by terpenes obtained in the preparation
of terpeneless oils

Terpeneless oils

Terpenless lemon oil

with a citral content of
40-50% may be
prepared.

California type 2.2-3.8% total aldehydes

(principally citral)
Italian type 3.0 5.5%
Lemon oil & orange oil high terpene content
Develops a terebinthenate odor during
storage terpenes may be removed by
distillation under reduced pressure

Terpeneless orange oil,

95% of the terpenes
have been removed
KETONE VOLATILE OILS
Camphor

Cinnamomum camphora
(lauraceae)

Topical antipruritic,
rubefacient, anti
infective (1-3% in prep
for skin use), plastics

Caraway
Caraway oil

Carum carvi
(umbelliferae)

Dried, ripe
fruit

Buchu

Barosina betulium, B.
crenulata, B. serratifolia
(rutaceae)
Artemisia absinthium
(compositae)

Dried leaf

Wormwood oil

Absinthe oil

Cedar leaf oil

Spearmint

Spearmint oil

Common spearmint
Scotch spearmint

Thuja occidentalis
(cupressaceae)
Mentha spicata
M. cardiac
(labiatae)

Dried leaves
and
flowering
tops
Fresh leaves
Leaves,
flowering
tops
Fresh
overground

3-6% volatile oil

50-85% (+) carvone,
40-50% (+)limonene
Volatile oil containing
about 30% diosphenol
(+) thujone,
camphene,
phellandrene, caryophyllene
(+) thujone, (-)
fenchone, -pinene
Resin, tannin, and a
volatile oil (about
0.5%) that contains
carvone
Not less than 55% by
volume, carvone

Flavor
Flavor, carminative
Diuretic in OTC drug
for menstrual problems
(fluidex and odrinil)
Counterirritant in OTC
drug (absorbine Jr.)

Ketone ; distilled with steam

Crude camphor: freed of oil by centrifugation and
pressing and finally resublimed and pressed into
the familiar cakes
Synthetic camphor from pinene ( principal
constituent of turpentine oil)
Methods in producing synthetic camphor:

Converting pinene into bornyl esters

Hydrolyzed to isoborneol

Finally oxidized to camphor

Specific rotation of natural camphor: +41 deg and
+43 deg
Synthetic camphor optically inactive racemic
form
Note: must be labeled if natural or synthetic
Distilled with steam

Distilled with steam

Counterirritant in OTC
drug (vicks vaporub)
Flavor, carminative

Distilled with steam

Flavor, carminative
Domestic use:

Distilled with steam

parts

PHENOL VOLATILE OILS

Thymol
Thyme oil
Horsemint oil
Ajowan oil

Thyme oil

Myrcia oil

Bay oil

Creosote

Beechwood creosote

Juniper tar

Cade oil

Pine tar

Clove

Clove oil

Cloves

46-60% of (-) carvone,

6-20% alcohols and 420% of esters and
terpenes
(-) limonene,
cineole

Thymus vulgaris
Monarda punctate
Carum copticum

50% toothpaste and

mouthwash
47% chewing gum
3% other

Antifungal,
antibacterial
Topically (0.1-1%)
lotions, creams, and
ointments
Used in feminine
hygiene products
In otic products
In external analgesics

Thymus vulgaris, T. zygis,

T. gracilis (labiatae)

Flowering
plant

Thymol, carvacol, pcymene, camphene,

limonene

Pimento racemosa
(myrtaceae)
Fagus grandiflora
(fagaceae)

Leaves
Wood

55-65% eugenol,
myrcene, chavicol
Guaiacol, creosol

Juniperus oxycedrus
(cupressaceae)
Pinus palustris (pinaceae)

Heartwood

Cadinene

Wood

10-20% aqueous
distillate, 10-15%
light oily distillate,
phenol, creosol,
naphthalene

Eugenia caryophyllus, E.
caryophallata
(myrtaceae)

Dried flower
bud

14-20% volatile oil

10-13% gallotannic
acid
Oleonolic acid,
vanillin, eugenin
(chromone
Not less than 85% of
total phenolic
substances
eugenol
Contains free eugenol

Antiseptic in the OTC

drugs (unguentine
cream, dewitts oil for
ear use)
Perfume

Can be prepared synthetically from m-cresol or pcymene

Treated in 2 ways to obtain thymol crystals:

Subjected to freezing temperatures (cause

crystallization)

Treated with NaOH soln, the aqueous soln

of sodium thymol being separated and
decomposed with acid (liberating the
thymol) which is subsequently purified
May be readily microsublimed
Distilled with steam

Distilled with steam

Disinfectant in the OTC

drug (dewitts
toothache drops)
expectorant in the OTC
drugs (creomulsin,
creo-terpin)
Local antieczematic in
the OTC drug (polytar)
Local antieczematic
and anti psoriasis drug
in (pachers pine tar,
poly tar)
Expectorant in pinex
cough syrup
Carminative, flavor

Mixture of phenols obtained from wood tar

produced by destructive distillation

Flavor, toothache
remedy (topically on
dental cavities)
Antiseptic,
counterirritant,

Distilled with steam

Methyl-n-amyl ketone
Produces the characteristic, fresh, fruity
note of clove oil

Empyreumatic volatile oil distilled

Empyreumatic product obtained by the destructive
distillation

Best cloves are from pemba

(70-95%), eugenol
acetate, caryophyllene
Eugenol

4-allyl-2methoxyphenol

PHENOLIC ETHER VOLATILE OILS

Nutmeg
Myristica

Myristica fragrans
(myristicaceae)

Dried ripe
seed

25-40% fixed oil (solid

@ RT)

8-15% volatile oil

Myristicin and
saffrole

Nutmeg oil

Myristica oil

Fennel oil

Anise

Aniseed

Chinese anise

Star anise

Anise oil

OXIDE VOLATILE OILS

Eucalyptus

Eucalyptus oil

Dried
kernels of
the ripe
seed

Foeniculum vulgare
(umbelliferae)

Dried ripe
fruit

Pimpinella anisum
(umbelliferae)
Illicium verum
(magnoliaceae)
Pimpinella anisum
(umbelliferae)
Illicium verum
(magnoliaceae)

Dried, ripe
fruit
Dried, ripe
fruit
Dried, ripe
fruit

Eucalyptus globulus
(myrtaceae)

Dried leaf

Fresh leaf

carminative
High eugenol =
commercial production
of vanillin
Dental analgesic

Flavor, condiment,
controlling diarrhea,
hallucinogenic agent

Safrole, myristicin
(methoxysafrole),
methoxyeugenol, (+)
camphene, terpineol,
& pinene,
myrcene, ()
limonene, sabinene
50-60% transanethole, (+)fenchone, (+)-pinene
1-3% volatile oil

Flavoring agent,
carminative

2.5-3% volatile oil

Flavor

80-90% transanethole estragole,

anisaldehyde

Flavor, carminative

Flavor, carminative

From clove oil by shaking with a 10% solution of

NaOH -> sodium eugenolate (steam distillation)
Washed with ether and decomposed with
sulfuric acid

Fixed oils that occurs in prismatic crystals ->

nutmeg butter
15g- intoxication
Produces flushing of the skin, tachycardia,
absence of salivation & other undesirable
side effects
Elemicin & myristicin believed to be involved in
the effects of the CNS
Distilled with steam
Must indicate whether the oil is of east indian/ west
indian origin

Distilled with steam

Flavor

3-6% volatile oil

Several resins (tannic
acid)

Distilled with steam

Requires much water, used to dry up the marsh

land
Flavor, antiseptic,
diaphoretic,
expectorant

Distilled with steam

Useful eucalyptus oil: not less than 70% cineole
Must be free from eucalyptus oils
containing large amounts of phellandrene
Medicinal use: 70-85% cineole + lesser amts of
volatile aldehydes, terpenes, sesquiterpenes,

Cineole

ESTER VOLATILE OILS

Gaultheria oil

Methyl salicylate

Eucalyptol

Gaultheria,
wintergreen, teaberry
or checkerberry
Gaultheria oil
Wintergreen oil
Betula oil
Sweet birch oil

Flavor
Has properties similar
to those of eucalyptus
oil

Gaultheria procumbens
(ericaceae)
Betula lenta (betulaceae)

Dried leaves

Aromatic and
astringent

bark
Methyl salicylate
(formed when the
glycoside, gaultherin,
is hydrolyzed by the
naturally occurring
enzyme, gaultherase,
in the presence of
water)

Pharmaceutic aid
(flavor) for aromatic
cascara sagrada
Local irritant,
antiseptic,
antirheumatic
Topical: (10-25% conc)
lotions and solutions
Large doses: toxic
Ingestion of 10 mL may
cause death for children
Symptoms: N&V,
pulmonary edema,
convulsions
Principal adulterant:
synthetic methyl
salicylate

Lavender oil

Lavandula angustifolia
(labiatae)

Pine needle oil

Dwarf pine needle oil

Pinus mugo, P. pumilio

(pinaceae)

Mustard oil

Allyl isothiocyanate

Brassica nigra, B. juncea

(brassicaceae)

aromatic aldehydes, and alcohols, and phenols

Many of the minor constituents have
irritant properties
Removed by redistillation of the oil
Industrial purposes: have piperitone and/or
phellandrene as the principal constituents
Used for perfumery: rich in geraniol and its
esters and citronellal
May be obtained:
1. From eucalyptus oils by fractional
distillation and subsequent freezing of the
distillate/ by treating eucalyptus oil with
phosphoric acid and subsequently
decomposing the cineole-phosphoric acid
with water
2. Terpin hydrate as a dehydration product on
treatment with acids

Fresh
flowering
tops
Fresh leaf

Dried ripe
seed

30-60% (-) linalyl

acetate, (-) linalool,
cineole, terpinen-4-ol
3-10% bornyl acetate,
-pinene, - pinene,
careen, camphene
Not less than 93%
allyl isothiocyanate

Produced synthetically; obtained by maceration

and subsequent distillation
MUST indicate whether it was made synthetically/
distilled from either of the plants mentioned
Purified by rectification with steam
Made synthetically by distilling a mixture of
salicylic acid and methyl alcohol
Synthetic oil from betula optically inactive
Oil from gaultheria slightly levorotatory
Contains an ester that splits into enanthic alcohol
and an acid.
Enanthic alcohol and its ester possess the
characteristic odor that distinguishes natural from
the synthetic methyl salicylate

Perfume

Distilled with steam

Perfume, flavor

Distilled with steam

Rubefacient in the OTC

drug (musterole)

Maceration with water

Subsequent steam distillation