Volatile Oil

By
Hany Nashaat Baraka , Ph.D

Definition of the Volatile

Volatile
oil are water immiscible
Oil

complex mixture of low molecular

weight, Volatile constituents of
different
classes
of
organic
compounds.
They
are
termed
ethereal or essential oils.
An essential oil is a concentrated,
hydrophobic
liquid
containing
volatile aroma compounds from
plants.
Fixed Oil: is non volatile glyceryl ester of
fatty acid.

water immiscible
complex

Volatilizati
on
Distillation

V.O

F.O

Glycero
Compositio Low
l+ fatty
n
M.W
acid
Saponificat
+
ion
+
Rancidity
+
+
Oxidation
Stain on
+
Filter

Different classes of organic compounds

Hydrocarbons
Alcohols
Phenols
Aldehydes
Ketones
Ester
Oxides
Peroxides
Nitrogenous
compounds
Sulfur
compounds

OH
OH

O
H3 CO

H3 CO

Aromatherapy
is a form of alternative medicine that uses volatile
liquid plant materials, known as essential oil, and
other aromatic compounds from plants for the
purpose of affecting a person's mood or health.
Scientific evidence is weak and preliminary but
mildly encouraging for a limited number of claims.
Essential oils differ in chemical composition from
other herbal products because the distillation
process only recovers the lighter phytomolecules.
For this reason essential oils are rich in
monoterpenes and sesquiterpenes, as well as other
VOC substances (esters, aromatic compounds, nonterpene hydrocarbons, some organic sulfides etc.).
Aromatherapy is a generic term that refers to any of
the various traditions that make use of essential oils
sometimes in combination with other alternative
medical practices and spiritual beliefs. Popular use
of these products include massaging products,
medicine,
or
any
topical
application
that
incorporates the use of essential oils to their
products. It has a particularly Western currency and
persuasion. Medical treatment involving aromatic
compounds may exist outside of the West, but may
or may not be included in the term 'aromatherapy'.

Why plants produce volatile oils?

Help pollination.
Prevent animal feeding and
parasites.
Varnish to decrease water loss.
Hydrogen donors in redox.
Detoxification products.
Help in sealing wounds.
Act as reserve food.

Where volatile oils are produced?

Oil cells as in cinnamon.

Glandular hairs as in mentha.
Shizogenous glands as in pine.
Schizolysogenous glands as in
clove, or even lysogenous oil
glands.
Vittae as in anise.

Use of volatile oils

Volatile oils possess a wide range of

pharmacological activities e.g.
smooth muscle relaxant, mucolytic,
stomachic,
antibacterial
and
antifungal..etc.
On the other hand volatile oils are
economically important since they
used in perfume and cosmetics

Plants chemotypes & Chemical polymorphism

Some Plants of the same species

may have different therapeutic
effects due to their unique
biochemical individuality (geog.,
climatic & agriculture. differences)
e.g. Thyme and Rosemary

Rosemary Chemotypes

France, Spain, yugoslavia

(Comphor, borneol)
(Stimulant).
Italy, Tunisia, Morocco
(Cineol)
(improves liver and kidneys)

Preparation Of Volatile
Oil

Preparation of Volatile Oil

Distillation

Water
Distillation

Steam
Distillation

Extraction

Mechanical

Water-Steam
Distillation
Expression , Sponge
Method

Cold Fat or Enfleurage

Method

Hot Fat, Maceration

Method

Scarification
Method

Solvent Extraction

Enzymatic

Distillation
Condensation:
Water
condensation

Volatile oil:
Lighter or heaver
Oil Recovery

Water:
Water of Cohabation

Plant material:
Fresh or dry
Dry in shade
Particle size reduction
Stored away from light,
moisture at low temp.

Heating Methods:
Fractional distillation
Boiling water
Steam
Water-steam

Plant Material
Plants could be fresh or dry
Drying should be in shade.
Size reduction reduces the thickness of
the tissue through which the oil and
water penetrate by increasing the
porosity and diffusion.
Stored materials should be away from
light, moisture and at low temperature.

Oil Recovery
Florentine cohabation Flasks

The water should recycled to be used in the distillation

process because it is saturated with oil. (Cohabation)

Oil in water of cohabation can be separated by:

Salting out: NaCl
Extraction with organic solvent immiscible with water

Water
Distillation
Advantages:
Simple & Cheap
Disadvantages
Incomplete exhaustion
Esters hydrolysis
Aldehydes Polymerization
Not suites high B.P. comps.
Need more space

Steam Distillation

Advantages:
Complete
exhaustion
Disadvantages
Sharing of the plant
material

Water-Steam
Distillation

Water:
used to control the temperature

Generate more steam

Cold Fat or Enfleurage Method

It depend on the extraction of the oil using
cold fat lard for 24 h up to several months.
Defleurage: Oil recovered by extraction with
Alcohol which is distilled off. eg. Jasmine oil.

Hot Fat or Maceration Method:

It depends on the immersing the plant material
in hot melted fat.
Pomade: The fragrant fat saturated with the
plant perfumes.
It is faster than enfleurage

Extraction used for heat sensitive or low

volatile oil containing in plants.

Solvent Extraction

1- volatile
2- selective
3- possesses low boiling point.
4-inert.
5- water immiscible.
6- of low price

Disadvantage:
Low quality V.O. Darker in color due to
extraction of some plant pigments.

A) Expression sponge
The essential oils of citrus fruits such as Orange,
Method
Mandarin, Bergamot, and Lime are
Lemon,
extracted from their fruits using a method called
expression. This is a simple method in which
machines using a centrifugal force, squeeze the
rind which produces the essential oil.

B) Scarification:

For the ecuelle a piquer process the

apparatus is made of a cup-shaped funnel.
across. It is provided with a lip and short,
closed stem, which serves both as a handle
and as a reservoir for the exuded oil.
Projecting from the inner surface of the 'Cup
are numerous brass pins across which the
softened peel is drawn with a rotary
movement. The liquid exuding from the
ruptured oil glands collects in the stem,
whence it is transferred to a collecting vessel

Quantitative determination of the Volatile oil

Oil heaver than water

Oil lighter than water

Clevenger's cohobation apparatus

Judgment the quality of the oils

Volatile oil could be adulterated by:
Adding cheap organic solvent or mineral oil
Production of byproducts or artifacts.

V.O. could be judged based on:

1-Estimation of specific active constituent.
constituent
Determination of esters,
alcohols,
aldehydes,
ketones, phenols, oxides and peroxides etc..
2-Detection of adulteration.
Moisture content; organic solvents as
alcohol, chloroform and benzene, fixed oils and
fats; turpentine oil; mineral oil, resin and
balsams, carboxylic acids esters and heavy

3-Specific physical properties

1- Color:

colorless to pale yellow,

Chamomileand guaicum are blue
lavander blue-violet floresce

2- Odor
3- Nature

Oil of peppermint (Stearopetene, Oleopetene)

Oil of Anise complete solidified.

45678-

Optical rotation (d, l & dl)

Refractive index
Sp. gr.
Melting point
Congealing point:

It is the highest Temp. at which the oil congeals or

solidifies.

9- Volatility
10- Evaporation residue
11- Solubility

Chemistry of Essential oils

Volatile oil composed of a mixture of different

volatile constituents:
It may contain one major component as Clove oil
contain not less than 85% eugenol.
Or entirely composed of one constiuent as Bitter
almond oil (benzaldehyde), oil of wintergreen
(methyl
salicylate),
mustard
oil
(allyl
isothiocyanate) [~ 100%].
Voatile oil manly composed of mixture of
Hydrocarbon compound Terpene less V.O and
Oxygenated hydrocarbonsterpenoids.
Terpene is derived from the German word
Terpentine , a specific hydrocarbons C 10H16 called
true terpenes and present in low boiling point
fraction of the oil.
The term terpenes applied to all C 10 isoprenoid
compounds including those containing oxygen and
also called terpenoids. Hydrocarbon terpenes
always end with ene.
The building units of all terpenoids are the
isoprene units which is C5H8.

Chemistry of the volatile oil

Head
Tail
Isoprene Unit

p-Menthane

Pinane

Fenchane

Chemistry of the volatile oil

No. of
isoprene
unite

No. of
carbons

Formula

C 5H 8

Monoterpen
es

10

C10H16

Sesquiterpe
nes

15

C15H24

Diterpenes

20

C20H32

Sisterterpe
nes

25

C25H40

Triterpenes

30

C30H48

Polyterpene
s

5n

(C5H8)n

Hemiterpen
es

Terpeno
ids

OH

OCH33

OH
OH

HO

Determination of terpenoid structure

Analytical methods

1-Elementary analysis and MS.

2-Degree of unsaturated, by acatalytic hydrogenation using
platinum oxide or palladium.
B- Double bonds can be estimated
using excess organic per-acid as
per-benzoic acid. The excess acid
is estimated iodometrically.
3-Estimation of specific groups as
methyl group where chromic acid
oxidation of C-methyl give one
molecule of acetic or formic acid
which can be estimated.
4-Isopropylidene group could be
estimated by ozonolysis, which
afford acetone to be measured
volumetrically.

Physicochemical methods

Uv, IR, X-ray,

carbon-13
and H1-NMR,
mass
spectrometry
& GC-Ms.

Chemical methods

1-Oxidative degradation
gives partial structure.
2-Unsaturation can be
determined by formation of
addition products with Br2,
HBr or NOCl.
3-Dehydrogenation is useful
to get the corresponding
unsaturated hydrocarbon.
4-Functional groups as
alcoholic, ketonic, acidic .
etc. could be determined by
specific reactions.
5-Ozonolysis is used for
cleavage of the ethylenic
linkages.

Determination of terpenoid structure

Determined
against stander
Alkali

HCOOH
CH3COOH

hydrogenation using
platinum oxide or
palladium

CrO3

Analytically

Di

ally Function group

c
i
m
e
Ch
determination

ct
re

(O)

HI

OH

Analytically

Chemically

I2

r
Un
ea
cte
d

per-benzoic
acid or perChromic acid

Br2, HBr
NoCl

ct
ally
c
i
t
aly
An

Ch

em
ic

ally

Oxidative
degradation

O3
Chemically

/S

ire
Ind

OH

O3
Volumetrically

Physicochemical methods
1

H-NMR

C-NMR

13

X-Ray
crystallography
Gas Chromatography

Classification of Volatile oil

constituents

Hydrocarbons
Oxygenated derivatives.
1- Alcohols
2- Phenols,
Phenol ether
3- Aldehydes.
4- Ketones.
5- Esters.
6- Oxides.
7- Peroxides.
Sulfur and nitrogenous compounds.

Hydrocarbons
Monoterpene
Acyclic

Isolation:-

Sesquiterpenes

Alicyclic

Monocyclic

Fractional distillation.
Formation of crystalline
adducts, with cl2, Br2, HX,
N2O3, N2O4, NOCl and
NOBr.
Counter-current
extraction.
Chromatography as GLC,
HPLC, and TLC.

Aromatic

Bicycle

Monocyclic

Acyclic

Alicyclic

Tricyclic

Bicyclic

Naphthalene
drivetive

Azulene

Monoterpene, Acyclic
Myrcene

Ocimene

10

10

Origin

Separation
KMnO4

Pb salts of
degraded

Humulus lupulus,
cannabinaceae
( Hops )

Ocimum basillicum
O. gratissimum & other
O.spp.

fractional distillation

fractional distillation

succinic acid and used in

organic synthesis.

Mixture of acids

needle shape

rhombic in shape

Aromatic Hydrocarbons
Origin:
oils as oil of lemon, thyme and
cinnamon.
Separation:
Fractional distillation flowed by addition
of KMnO4, to destroy other constituents.
P-Cymene

Monocyclic terpenes
7

Structural isomers
( shift of sub. gp. )

6
5

2
3

8 9
10
p-Menthane

m-Menthane

0-Menthane

Geometric isomers

Trans-f orm

Cis-form

1-Limonene

Monocyclic terpenes

Origin: Many oils as citrus oils. d, l or dl

Uses: 1- Flavoring Agents in cosmetics, soaps & pharmaceuticals.
2- Substitutes for preparation of orange oil.
3- Solvents in manufacture of resins.
4- Wetting & Dispersing agents.

Monocyclic Monoterpenes
2- Terpinolene
X X
/H H
-te
rp
in
e
n
eT

e
rp
in
o
le
n
e X

Origin: Coriander and orange oils

Use: scenting

3- Silvestrene

Carvestrene a

Carvestrene b

It occurs as an artifact during preparation of oils containing

car-3-ene or car-4-ene (car-3 or 4-ene).

Bicyclic Monoterpenes

Camphane
Carane

Fenchane

Pinane

Thujane

Bicyclic Monoterpenes
1-Sabinene:
1- Acid treatment open the second ring.
2- optically active.

Origin: in oils of savin.

Isolation: Fractional Distillation.

2-Pinene
Origin: Its The main constituent of oil of turpentine.
Prop.:
1- Its optically active:
* l-form is the main component of French oil of Turpentine.
* d-form is the main component of American oil of
Turpentine.
2- Its liquid that easily polymerizes on exposure to air.

-Pinene

-Pinene

Isolation by fractional distillation followed by

the addition of NoCl ( nitroso-chloride,
Tildens reagent ) and recovered by the
addition of analine.
Use: -pinene is used as a starting ( raw ) material for semi-synthesis of
different compounds like camphor, borneol & terpineol.

 -Pinene
Cl

OH

KOH

Cl
H

HCl
Isomrization
Bornyl Chloride

Pinene HCl

-Pinene

Borneol

-10 C

HNO3

oxidation
Molecular rearrangement
O

Ring opening
Camphor

HCl

Sesquiterpenes
Acyclic hydrocarbons:
* Farnesene in oil of Hops
( sesquiterpenoid
analogue of myrcene ).
* Sesquicitronellene from
oil of Citronella.
Isolation of Sesquicitronellene from oil of citronella :
1- Fractional Distillation.
2- 60-70 % Alcohols ( To extract oxygenated
compounds which soluble in alc. )
3- Repeated fractional distillation over Na metal ( To
remove exx. Alc.
Monocylic:

Z
in
g
ib
e
re
n
e

/S

a
a
le
n
e
(N
a
p
h
tC
h
ld
e
n
d
riv
a
tiv
e
)

Main constituent
of ginger oil

Bicyclic hydrocarbons:
Naphthalene derivative

Cadalene

Source: In oil of cade &

savin.
Uses:
1- In perfuming soaps to
give a gin-like flavor
2- Oil of cade itself has
been used as antieczematic

Aromatic Hydrocarbons:

H2SO4 or H3PO4 form

adducts decomposed by
H2O
TNT,TNP or TNR form
crystalline derivative
decomposed by Alk.

Guaiazulene
Chamazulene

Tricycilic
sesquiterpene:

Oil of Sandal Wood

Hydrocarbons

Monoterpene

Acyclic
5

Aromatic

Alicycic

10

10

Sesquiterpene

2
9

Bicyclic

Monocyclic

-Pinene

Bicyclic

Monocyclic

Acyclic

Farnesene

S es quicitronellene

Naphthalene

S
a
n
t
a
le
n

g
llo
b
u
le
n
e
e
r
e
n
e
o
ilo
fS
a
n
t
a
lu
m
a
le
b
u
m
)(C
(
o
ilo
fE
u
c
a
y
p
t
u
s
g
lo
b
u
ls
)(
o
n
id
fe
o
u
s
o
ils
)
Tricyclic

Azulene

Bis abolene

Guaiazule ne
Chamazulene

Oxygenated Terpenoids

Terpenoid Alcohols

Separation:
1-fractional distillation
2-Counter current extraction
3-Chromatography
4-preparation of a crystalline derivatives as phosphate or
benzoate, borate or phthalate ester.

Detection and identification

1-GCMS, HPLC, NMR and IR.
2-Formation of a dehydration product (H2SO4, acid
anhydrides, phosphoric pentoxide, ZnCl2 and MgCl2).
3-CalCl2 addition product usually formed with most
primary alcohols.
4-Formation of esters ether by acid anhydride or RCOX.

Quantitative Determination of
terpene Alcohols
By HPLC
By specific methods
By estrification followed by
saponification. Citronellol (using formic
acid instead of acetic anhydride).
(N:B.
phenolic and other products
interference).
Tertiary alcohols estrification. (Acetic
unhydride, acetyl chloride, Dimethyl
analine)
Tertiary alc. could be dehydrated by
ZnCl2 or I2.

Terpenoid Alchols

Acyclic

Alicyclic

Aromatic

Monocyclic
Monoterpene

Bicyclic
Monoterpene

Sesquiterpene

1- Linalol:
OH
Conc. H2SO4
Linalool
H+

AcetylationHydrolysis

(O)

Dipentene -Terpinene

5%H2SO4

OH

OH
CHO

.H2O
OH

Geraniol

Citral

-Terpinene
+Geraniol
+Nerol

2- Geraniol and Nerol

OH

PPt
CaCl 2

HCl or H3PO4

1???

Geraniol
(Trans-form)
H+
(O)

Dipentene

5%H2SO4
OH

OH
Nerol
(Cis-form)

2???CHO

3??? .H2O

OH
Citral

4???

OH
-Terpineol

Geraniol can be separated from the

crude oil or even in a mixture with nerol
since geraniol form a crystalline
derivative with unhydrous CaCl2 while
3- Citronellol
nerol is not.

OH

Citronellol

(O)

CHO

H
Citronellal

Monocyclic Monoterpene
Alchol
1-Menthol:

CH3

OH
H3C

CH3

5-Terpineols

OH

OH
-H2O

OH
Terpin

OH

OH
5% H2SO4

-Terpineol

---H3PO4

60%H2SO4

----

HCOOH

+
KHSO3

O
Cineol

Dipentene

-Pinene

Terpinene
+ Terpinolene

Terpinolene

Bicyclic Monoterpene Alcohols

1-Borneol Borno-comphor:
OH
H

-H2O

(O)

Zn Cl2

H
Borneol

H
OH

Camphor

Camphene

Isoborneol

- Santalol:

-S
a
n
ta
lo
lC

H
O
H
2
2

Aromatic alcohol:
Benzyl
Alcohol:

Occurs
As ester of benzoate or cinnamate
Isolated
by CaCl2 Methods
Oxidized
to benzoic acid
Use:
1- fixative in perfumes.
2- antimicrobial.
3- In perfumes & cosmetics to give
synthetic flowers odor such as
jasmine, gardenia & tuberose.

CH2OH

Phenols and Phenolic

Ethers
Isolation:
Fractional distillation
Fractional crystallization by cooling
GCMS and HPLC
Formation of Phenolates with Alkaly which is water soluble.
Phenolic ethers are neutral and do not react with alkalies but
generate phenols on heating with HCl.

Test for identities:

Phenolics gave a color reaction with FeCl3 and can be esterified
with acid anhydrides, benzoyl chloride or p.nitrobenzoyl
chloride. Esterification require the presence of an organic base as
pyridine. Phenolics form a
crystalline bromides with Br2 by substitution reaction.

Estimation:
1. Phenol form water soluble salts with
alkalies (using cassia flask).
2. Specific
Specific color reaction with specific
reaagents.
3. GC-MS and HPLC
Use:

1-Antiseptic effects
2- Anti-oxidant
3-free radical scavanger.
4- Hypocholesterolemic
5- Insect repellant

A- Phenols:
Chemical test

1-Thymol:
H2SO4: Yellow
OHC
OH

ONa

NaOH

CHO
ONa

Thymoyl sulfonate

H2SO4 +HNO3:Bluish green

CHCl3

yellow

Use:
Anaesthetic in
tooth ache.
Antibacterial.
Anthelimentic.

Reddish violet

FeCl3

..

2- Carvacrol:
OH

Colorless liquid

3- Eugenol:
Carvacrol

yellow liquid

OH

OH

OCH3

e
p
a
sh
e
l
ed
Ne stals
cry

KOH

KOH le
sca
micro

OCH3

Eugenol

Isoeugenol

B-Phenol ethers
1- Anethole
Crystalline
from cold

OCH 3

ht
g
i
L
Air

H3 CO

OCH3

OCH 3

OCH3

KMnO4

CHO

COOH

3- Safrole:

O
O

(O)

KO

Heliotropine

CHO

O
O

Isosafrole

4- Myristicin:
O
H3 CO

O
H3 CO

KOH
(O)

O
H3 CO

O
O

H3 CO

CHO

COOH

5- Apiole (Parsely camphor)::

O
H3 CO

OCH3

6- Dillapiole:
O
H3 CO

H 3CO

Oxide and Peroxide

1,8-Cineol: Eucalyptol
1,4-Cineol:

1,4-Cineol
GCMS

and
HPLC for
detection,
isolation and
quatitation

Isolation:
H3PO4-Cineol
50% resorcinol solution,(Cineol)2-resorcinol,
decomposed by hot water or alkali
By fraction distillation.
GCMS and HPLC for detection, isolation and
quatitation
Eucalyptol is expectorant, diuretic, antiseptic,
antispasmodic, stimulant and prevent calculus
formation in kidney or even help in dissolving the
already formed calculus either in kidney or gall
bladder.

Peroxide
Ascaridol
O
O

o
o

Ascaridol

OH

+ 2HI

+ I2
OH

Chenopodium oil (60-70%). Oily liquid with disagreeable odor.

Anthelmintic for round worms and hookworms.
Test:
Give blood red color with Fe+2 + ammonium thiocyanate.

Esters

A- Esters of Aliphatic acids:

e.g. geranyl, linalyl, menthyl acetate, etc.
B- Esters of Aromatic acids:
1- Benzyl Benzoate
O

H2
C O C

2- Methyl Salicylate:
COOCH3
OH

B- Nitrogenous ester
Methyl anthranilate
COOCH3
NH2

Aldehydes and Ketone

Estimation:-

1- R-CHO+NH2OH.HCl
RCH=NOH+HCl+H2O
2- (R2-C=O+NH2OH.HCl
(R)2-C=N-OH +HCl+H2O.
3- RCHO+Ph-NH-NH2 Ph-NH = CHR+H2O
4- R- CHO + NaHSO3 RCH(OH)SO3Na
5- R- CHO + Na2SO3 RCH(OH)SO3Na + 2NaOH

NaO3S
O
+ 2 Na2SO3 + 3H2O

O
SO3Na

Aliphatic terpene
Aldhydes
1- Citronellal:

Citral + citronellal mixture can be resolved based on sod.

sulfite reaction, where Citral react with dilute solution while
citronellal requires a concentrated solution.

C
H
OC
H
O
C
H
O
C
H
O
g
e
r
a
n
i
a
l
o
r
C
i
t
r
a
l
n
e
r
a
l
o
r
citl(trans) H
c
i
t
b
(
c
i
s
)
+
o
r
K
H
S
O
3
o
x
i
d
a
t
i
o
n
reduction
C
O
O
H
g
e
r
a
n
i
o
l
c
i
t
o
e
a
l
geranicacid p-cym
ene -nlo

2- Citral:

Crystalline citral-a sod.

bisulfite adduct is sparingly
soluble in H2O while that of
citral-b is soluble.

Citral-a form an addition

compound with alkaline
cyanoacetic acid, while
citral-b is not.
CHO
(CN)CH2COOH/NAOH

CH=C(CN)COONa

CH O + H2-CH-CO-CH3

CH=CH-CO-CH3
-ionone
O

O
-ionone
(Violet odor)

-ionone

CHOAc
Citral-enolacetate

H+

CHOAc

Aromatic Aldehydes

1- Benzaldehyde
OGluc-Gluc.
HC

CHO
CN

Purnase
+ H2O
Amygdalin

+ HCN
Benzaldehyde

+ 2 Glucose

5-Vanillin:
Syntheses:
1- Oxidation of lignin
2- From eugenol
A
cO
O
KC
O
HO
A
cO
HO
H
C
C
H
3O
C
H
3O
C
H
3O
3
a
lk
a
i3 O
O
H
(O
)H
A
c
V
a
n
i
l
i
n
E
u
g
e
n
o
l
C
H
OC
H
O

Monocyclic Terepen Ketones

1- Menthone
H

H
H+ or OH
O

Na/EtOH
OH

O
Menthol

2- Ionenes
O

H2SO4
-ionone

-ionone
Separation:
1- Sod. Bisulfite of a ppt by Na Cl

3- Carvone
NOH
+ H2O + HCl
+NH2OH. HCl

SO3Na
O

SO3Na

+2Na2SO3 + 2H2O
Carvone

+ H2S/NH4OH
2

H 2S

+ 2NaOH

4- Diosphenol buchu camphor

Crytalline on cooling
As phenol in acidic character
FeCl3
Reduce Fehling and amonical
AgNO3

Bicyclic terpene Ketone

1- Fenchone

O
Fenchone

OH

O
Diosphenol

2- Camphor

O
Camphor

KOH

HNO 3

Isomer.

Bornyl chloride

Borneol

Cl

CL

OH

Pinene HCl

Nitrogenous and Sulfur volatile Constituents

1- Skatole

CH3
N

Skatole

HCl
-Pinene

2- Allyl isothiocyanate
From Sinigrin:

glucose

C
N

OSO3K

H2O

Myrosin

+ KHSO4

From Allylchloride:

+ Glucose