ORGANALYSIS.Cinnamaldehyde formal

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 Cinnamon is a widely used spice in some dishes, flavorings in gums, candies and other sweet delicacies and sometimes also as an antimicrobial for the mouth. It is derived from the cinnamon tree’s inner bark, and is grinded into powder. The cinnamon bark powder contains cinnamaldehyde, the organic compound which gives the cinnamon bark powder its flavor and odor. It is a pale yellow and viscous liquid.

unsaturated aldehyde. It named through IUPAC nomenclature as 3-phenyl-2-Propenal. The experiment aimed to isolate cinnamon oil from cinnamon bark by steam distillation. From cinnamon oil, cinnamaldehyde could be extracted by multiple extractions using DCM as a solvent, through aqueous dispersion. In the experiment done, cinnemaldehyde was analyzed by subjecting it to Tollen’s test and Phenylhydrazone test, both of which test for the presence of aldehydes.

EXPERIMENTAL

Figure 1 Cinnamaldehyde structure

A common way of isolating cinnamon oil along with cinnamaldehyde from cinnamon bark, even in industrial scale, is through steam distillation. The cinnamon oil isolated through steam distillation contains roughly around 90% trans-cinnamaldehyde. Cinnamaldehyde contains a formyl group, and is therefore an aldehyde. Its structure has a phenyl group attached to an

a. COMPOUNDS TESTED Cinnamaldehyde extracted from 13.0g Cinnamon powder. b. PROCEDURE ISOLATION About 13.0g

of Cinnamon powder was introduced into an Erlenmeyer flask. Enough amount of distilled water was added to the Cinnamon powder to moisten it. The reflux set-up was put together. The cinnamon mixture was subjected to heating in the

reflux set-up for about an hour and a half. After heating, two layers were formed, the upper oily layer contained the cinnamaldehyde.

EXTRACTION

The mixture was cooled to room temperature. The upper oily layer was then decanted and placed into a separatory funnel. The isolated oily layer was subjected to single extraction. 25mL of dichloromethane was added. The separatory funnel was swirled for 3 minutes with occasional release of pressure, and then it was left to stand for 2 minutes. Two layers were observed, the lower organic layer was transferred to a clean evaporating dish. The evaporating dish containing the dichloromethane-cinnamaldehyde mixture was covered with a clean bond paper and was secured with a masking tape, small holes were pierced onto the bond paper cover. Spontaneous evaporation was performed. The crude cinnamaldehyde was weighed, and the percent yield was computed.

About 0.5 mL phenylhydrazine reagent was added to 10-15 mL ethanolic mixture. Direct heating was employed to the mixture. Conjugated carbonyl compound formed a phenylhydrazone derivative, a red-orange crystalline precipitate. Non-conjugated carbonyl compound yielded a yellow crystalline precipitate.

RESULTS AND DISCUSSION 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. Steam distillation works on the principle that immiscible objects when mixed together can lower the boiling point of each other, as explained by Dalton’s law of partial pressures.

PRODUCT

PHYSICAL PROPERTIES State at Room Temp Color Appearance ODOR

TOLLEN’S TEST Solubility

A small amount of the crude cinnamaldehyde was dissolved in enough absolute ethanol. 1mL of 10% AgNO3 and 1mL 10% NaOH was added to the mixture. Ag(OH)2, a white precipitate was formed and was oxidized to form of Ag2O, a brown precipitate. The precipitate was dissolved completely, to just amount of NH4OH. The mixture was heated in a water bath. A positive result was the formation of silver mirror of a black precipitate. PHENYLHYDRAZONE TEST

CINNAMON OIL SANDARD

SOLID

LIQUID

Light brown Amorphous Sweet cinnamon aroma Soluble in ethanol

Dark brown Clear Sweet cinnamon aroma Soluble in ethanol

CHEMICAL PROPERTIES Tollen’s test Phenyl Hydrazone test

Silver mirror Light yellow solution; white ppt.

Silver mirrow Red orange solution; white ppt.

Two kinds of tests were done in the experiment, both tests characterize an organic compound as an aldehyde. Tollen’s test is a chemical test most commonly used to determine whether a known carbonyl-containing compound is an 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. • •

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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