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EXPERIMENT 6: ISOLATION, EXTRACTION, AND GENERAL TEST FOR

CHARACTERIZATION OF CINNAMALDEHYDE FROM CINNAMON

John Paul C. Recio, Rio Pauline S. Roque, Deza Lyn M. Santos, Donna Rose J. Santos, Gerald C.
Sevilla
Group 8, 2A-Biochemistry Organic Analysis Laboratory

ABSTRACT
Cinnamaldehyde is an organic compound found in Cinnamon. It is responsible for giving cinnamon its odor
and color. And about 90% of cinnamaldehyde is found in cinnamon. The primary objective of the experiment was to
isolate, extract, and perform general test for cinnamaldehyde form cinnamon. In the end of the experiment, the
percentage yield was computed. About 13 grams of cinnamon power was utilized from the isolation and extraction of
cinnamaldehyde. In the isolation process, since cinnamaldehyde boils at 251°C, a reflux distillation setup was used in
the experiment to minimize the evaporation of the mixture of immiscible liquids. Ultimately follows Dalton’s law. There
were two tests performed in the experiment namely Tollen’s Test and Phenyl Hydrazone Test. The two test where
utilized to characterized the isolated and extracted compound. Tollen’s test yielded a silver mirror result which states
that the compound contains wheter a carbonyl – group contains a ketone or aldenyde. Obviously it should contain an
aldehyde. On the other hand Phenyl Hydrazone test is a follow up test wheter the compound contains an aldehyde.
Positive result for this test was an orange solution with white precipitate. This report will try to explain the principles
behind isolation, extraction and the general test for characterization of the compoung cinnamaldehyde.

INTRODUCTION unsaturated aldehyde. It named through


IUPAC nomenclature as 3-phenyl-2-Propenal.
Cinnamon is a widely used spice in
some dishes, flavorings in gums, candies and The experiment aimed to isolate
other sweet delicacies and sometimes also cinnamon oil from cinnamon bark by steam
as an antimicrobial for the mouth. It is
distillation. From cinnamon oil,
derived from the cinnamon tree’s inner bark,
and is grinded into powder. cinnamaldehyde could be extracted by
multiple extractions using DCM as a solvent,
The cinnamon bark powder contains through aqueous dispersion. In the
cinnamaldehyde, the organic compound experiment done, cinnemaldehyde was
which gives the cinnamon bark powder its analyzed by subjecting it to Tollen’s test and
flavor and odor. It is a pale yellow and
Phenylhydrazone test, both of which test for
viscous liquid.
the presence of aldehydes.

EXPERIMENTAL

a. COMPOUNDS TESTED
Cinnamaldehyde extracted from 13.0g
Figure 1 Cinnamaldehyde structure Cinnamon powder.

A common way of isolating cinnamon b. PROCEDURE


oil along with cinnamaldehyde from
cinnamon bark, even in industrial scale, is
ISOLATION
through steam distillation. The cinnamon oil
isolated through steam distillation contains About 13.0g of Cinnamon powder was
roughly around 90% trans-cinnamaldehyde. introduced into an Erlenmeyer flask. Enough
amount of distilled water was added to the
Cinnamaldehyde contains a formyl Cinnamon powder to moisten it. The reflux
group, and is therefore an aldehyde. Its set-up was put together. The cinnamon
structure has a phenyl group attached to an mixture was subjected to heating in the
reflux set-up for about an hour and a half.
After heating, two layers were formed, the About 0.5 mL phenylhydrazine reagent
upper oily layer contained the was added to 10-15 mL ethanolic mixture.
cinnamaldehyde. Direct heating was employed to the mixture.
Conjugated carbonyl compound formed a
phenylhydrazone derivative, a red-orange
EXTRACTION crystalline precipitate. Non-conjugated
carbonyl compound yielded a yellow
crystalline precipitate.
The mixture was cooled to room
temperature. The upper oily layer was then RESULTS AND DISCUSSION
decanted and placed into a separatory
funnel. The isolated oily layer was subjected Since cinnamaldehyde boils at 251°C,
to single extraction. 25mL of a reflux distillation setup was used in the
dichloromethane was added. The separatory experiment to minimize the evaporation of
funnel was swirled for 3 minutes with the mixture of immiscible liquids. Steam
occasional release of pressure, and then it distillation works on the principle that
was left to stand for 2 minutes. Two layers immiscible objects when mixed together can
were observed, the lower organic layer was lower the boiling point of each other, as
transferred to a clean evaporating dish. The explained by Dalton’s law of partial
evaporating dish containing the pressures.
dichloromethane-cinnamaldehyde mixture
was covered with a clean bond paper and
was secured with a masking tape, small PRODUCT CINNAMON
holes were pierced onto the bond paper OIL
SANDARD
cover. Spontaneous evaporation was
PHYSICAL PROPERTIES
performed. The crude cinnamaldehyde was State at SOLID LIQUID
weighed, and the percent yield was Room Temp
computed. Color Light brown Dark brown
Appearance Amorphous Clear
ODOR Sweet Sweet
cinnamon cinnamon
TOLLEN’S TEST aroma aroma
Solubility Soluble in Soluble in
ethanol ethanol
CHEMICAL PROPERTIES
A small amount of the crude Tollen’s test Silver mirror Silver mirrow
cinnamaldehyde was dissolved in enough Phenyl Light yellow Red orange
absolute ethanol. 1mL of 10% AgNO3 and Hydrazone solution; white solution; white
1mL 10% NaOH was added to the mixture. test ppt. ppt.
Ag(OH)2, a white precipitate was formed and
Two kinds of tests were done in the
was oxidized to form of Ag2O, a brown
experiment, both tests characterize an
precipitate. The precipitate was dissolved
organic compound as an aldehyde.
completely, to just amount of NH4OH. The
mixture was heated in a water bath. A
Tollen’s test is a chemical test most
positive result was the formation of silver
commonly used to determine whether a
mirror of a black precipitate.
known carbonyl-containing compound is an
PHENYLHYDRAZONE TEST aldehyde or a ketone. A positive result with
Tollens' reagent is an elemental silver
precipitating out of solution, a characteristic
and memorable "silver mirror" on the inner
vessel surface.
Phenyl Hydrazone test was another test
done to test the presence of aldehyde.

• Weight of Cinnamon: 13. g


• Weight of product and
evaporating dish: 145 g
Weight of evaporating dish: 143 g
Weight of product: 2. g
• %Yield 15%
Computation:

REFERENCES:
http://www.chemistrydaily.com/chemi
stry/Cinnamaldehyde 02/27/11

http://www.chm.bris.ac.uk/motm/cinn
amaldehyde/cinnc.htm 02/25/11

http://sbrs.cm.utexas.edu/virtual.html
02/27/11

Organic Analysis Laboratory Syllabus

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