By: Jammy Cartoon Mind Marco F

Vanilla
Only edible fruit of 35,000 species in the family Orchidaceae.
Native to Central America, southeastern Mexico, the West Indies and
northern South America.
The major producing country of vanilla are Madagascar, Malagasy
Republic, Indonesia, Comoros and Uganda.
Vanilla is the most popular flavor in the world and second most expensive
spice next to saffron.
The commercial product of vanilla, are the source of the popular
flavoring substance called vanillin.

VANILLIN C8H8O2
4-Hydroxy-3-methoxybenzaldehyde

Functional groups of vanillin are aldehyde, ether and phenol.

The primary component of the extract of the vanilla bean.
It is also found in Leptotes bicolor, roasted coffee and the
Chinese red pine.

Application

Vanillin is component of
natural vanilla flavoring.
It used in foods and beverage
industry for centuries such as a
chocolate drink flavored with
vanilla as well as in perfumes and
pharmaceuticals.
Also used as an aromatic
additive for candles, incense,
potpourri, fragrances, perfumes,
and air fresheners.

Physical Properties
Molecular weight

152.15 g/mol

Color/Form

White crystalline
needles from water

Odor

Sweetish smell /
Pleasant aromatic
vanilla odor

taste

Pleasant vanilla
taste

Boiling point

285 deg C

Melting point

81-83 deg C

Density/specific
gravity

1.056 g/cm^3

Heat of combustion

914.1 kg cal at 20
deg C

Chemical Properties
Dissociation
constant

pKa = 7.4 at 25 deg

C

pH

Solutions are acid

to litmus

Solubilities

-In water,
1.102X10+4 mg/L at
25 deg C
-In water >2%; in
ethanol is 1:2
vanillin:ethanol.
Freely soluble in
chloroform, ether,
in solutions of fixed
alkali hydroxides;
solutions in glycerin
and hot water.
-Soluble in 125
parts water, 20

Chemical Properties
Reaction

React with Br2,

HClO4, potassiumtert-butoxide,
(tert-chlorobenzene + NaOH),
(formic acid + Tl
(NO3)3 (NTP, 1992).
Vanillin is
Aldehydes.
Aldehydes are
readily oxidized to
give carboxylic
acids.

Heating

Heating Vanillin
gives CO and CO2
and it is give also
antimicrobial
activity against
pathogenic

EUGENOL C10H12O2
4-Allyl-2-methoxyphenol

Because natural vanilla extract is expensive so synthetic vanillin can be use instead of
natural vanillin.
The first commercial synthesis of vanillin start with eugenol. Nowadays, artificial vanillin
is made from either guaiacol or from lignin.

Eugenol
Eugenol is an organic molecule consisting of a six carbon ring of alternating double-bonds;
two oxygen atoms are singly-bonded to carbons in the ring, one of the oxygen atoms is singlebonded to another carbon with three hydrogen atoms and the other is bonded only to hydrogen;
another carbon atom is singly-bonded to a remaining carbon in the ring, which is bonded to two
other carbons each of which are also bonded to hydrogen atoms.

Local anesthetic. It is widely used

Application

in dental products, being incorporated

into impression pastes, periodontal
dressings, cement, endodontic sealers,
fillings, and dressings for dry sockets.
Eugenol is also used as a flavoring
in foods and pharmaceuticals, and in
the manufacture of textiles. Other
forms include clove oil and clove
cigarettes.

Physical Properties
Molecular formula
IUPAC name

C10H12O2
4-Allyl-2methoxyphenol

Molecular weight

164.20108 g/mol

Color/Form

Clear colorless pale

yellow or ambercolored liquid.

Odor

Odor of cloves

taste

Spicy pungent
taste.

Boiling point

225 deg C

Melting point

-9.2 to -9.1 deg C

Density/specific
gravity

1.0652 g/cm^3 at
20 deg C

Vapor pressure

0.0221 mm Hg at 25

Chemical Properties
Dissociation
constant

pKa = 10.19 at 25
deg C

pH

Solutions are
slightly acid to
litmus

Solubilities

In water, 2460
mg/L at 25 deg C

Chemical Properties
Eugenol to vanillin

Eugenol isomerizes
to isoeugenol in
alkaline solution. It
can be oxidized (by
nitrobenzene) to
vanillin. Other
oxidizing agents
like acidified
potassium
dichromate can be
used, but then the
OH group has to be
protected by
acetylation prior to
oxidation. The
double bond was
isomerizes, and
then oxidized and
cleaved to form
vanillin. (As figure
below)

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