ISOLATION AND CHARACTERIZATION OF EUGENOL FROM CLOVES SCIENTIFIC PAPER

ISOLATION AND CHARACTERIZATION OF EUGENOL FROM CLOVES

Wendell A. Tulay De La Salle University – University – Dasmariñas Dasmariñas City, Cavite, Philippines

ABSTRACT

Natural Products are compounds that can be found or extracted in nature and usually produced by plants, animals, and/or fungi. Molecules originating in nature have long held in the importance in Chemistry and at the society at large. In this experiment we will isolate natural products from cloves which are usually euglenol . This experiment has a lot of processes including isolation of natural oils and distillation we will also use different chemicals to extract the oil. This requires an ample of time to do.

INTRODUCTION

The clove tree is usually tropic al evergreen that develops clusters of flowers. These flowers are dried and grinded to use for cooking. Euglenol is responsible for that distinct aroma and taste that the cloves have. Eugenol is a phenylpropene, an allyl chain-substituted guaiacol. Eugenol is a member of  the phenylpropanoids class of chemical compounds. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, basiland basiland bay leaf. It is slightly soluble in water and soluble in organic solvents. This experiment will teach you on how to extract or isolate euglenol out of cloves by the process of distillation. This process is also known as steam distillation. Both eugenol and neutral product are separated from water by acid-base extraction.

MATERIALS AND METHOD

 A 5g of grinded cloves were weighed on a watch glass and transferred onto a 250 m L distilling flask. 75mL of distilled water were added and mixed. The used distillation apparatus was assembled for  steam distillation and stirred motor below the heating Bunsen burner. Water supply was added into the distillation apparatus and every now and then temperature was recorded. A total of 50ml distillate was collected from the distillation process; the temperature was recorded very 5mL of collected liquid. The collected distillate then now transferred into a 250mL Erlenmayer flask. 3g of NaCl was supposed to be added but then this experiment needs ample of time so there are shorts cuts done. We went straight in

adding a 25mL hexane and were shook or 5 minutes with occasional venting. To separate the upper and lower meniscus we then used the separatory funnel, the aqueous layer was drain leaving the organic layer inside, 25ml of 10% NaOH was supposed to be added but then again there was a lack in time. RESULTS AND DISCUSSION:

There are lots of time wasted on the first trial of the group when the flame was too hot then it contaminated the distillate so the group started all over again causing to skip lot of process than the original and supposed to be procedure. But there were extracted eugenol though. Here is to show how much eugenol was extracted here are the data and a table:

A. YIELD OF EUGENOL AND CHEMICAL REACTIONS

Mass of Ground Cloves: 5.0478g Mass of Eugenol Obtained: 0.356g Mass of Paper: 0.5508g Mass of Beaker: 68.2358g % Yield: 7.05% Color reaction of Eugenol with 1% FeCl3: Deep blue green Color reaction of Eugenol with Bayer’s reagent: Brown precipitate

B. DISTILATION CURVE

Distillation Curve 120 100 80 60 40 20 0 5ml

10ml

15ml

20ml

25ml

30ml

35ml

40ml

45ml

50ml

PICTURES TAKEN WHILE TAKING THE EXPERIMENT:

GUIDE QUESTIONS AND APPLICATION:

1.) Draw the structures of eugenol, eugenol acetate, and caryopyllene and explain the basic of  separation of eugenol from the other components in clove oil? (5pts)

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eugenol

eugenol acetate

caryopyllene

-Eugenol is not soluble in all liquids, so depending on the % of e ugenol in your particular preparation, it

willseperate out of the solution over time.

2.) What us the temperature of volatilization of eugenol? Is this higher or lower than the actual boiling point of egenol and why? -

The volatilization of eugenol in our experiment is 100°C and the actual boiling point of eugenol is

254°C that means that it is lower than it, this maybe cause of the w ater and the other contents of the clove oil.

3.) What are the biological and the pharmacological properties of eugenol?

A tincture of cloves (15% in 70% alcohol) has been reported to be effective in treating ringworms such as athlete's foot. Clove oil has antihistaminic and spasmolytic (musculotropic) properties, the latter probably due to its content of eugenyl acetate (see balm). - Clove oil (due to its eugenol) has anodyne and mildly antiseptic properties, e xhibiting broad antimicrobial activities (against Gram-positive, Gram-negative, and acid-fast bacteria, and fungi), as well as anthelmintic and larvicidal properties. No data are available that correlate the pharmacological properties of noneugenol clove constituents such as eugenyl acetate, methyl eugenol (see sweet bay), and caryophyllene, which are often present in relatively large amounts in cloves and clove derivatives. Aqueous extracts of cloves, c love oil, eugenol, eugenyl acetate, and methyl eugenol all have trypsin-potentiating activity (see cinnamon). Eugeniin exhibited strong antiviral activity against herpes simplex virus.

4.) Illustrate the reaction between eugenol and FeCl3. What is the implication of this reaction

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The reaction produces a green solution with purple precipitate. Thi s t es t c on fi rm ed fo r t he presence of the phenol in the sample which is a characteristics of eugenol

5.) Illustrate the reaction between eugenol and Bayer’s reagent. What is the implication of this reaction?

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Bayer’s test using Bayer’s reagent or potassium permanganate (KMnO) is used to test unsaturation or the presence of alkyne structures or double bonds.

REFERENCES:

http://lh6.ggpht.com/-aCXSv_CwLzA/UFu52vHcgyI/AAAAAAAABxo/ofwx4ltpWyM/s1600h/clip_image004%25255B9%25255D.gif  http://www.google.com.ph/url?sa=t&rct=j&q=isolation%20and%20characterization%20of%20eugenol% 20from%20cloves&source=web&cd=1&cad=rja&ved=0CC0QFjAA&url=http%3A%2F%2Fciteseerx.ist.psu. edu%2Fviewdoc%2Fdownload%3Bjsessionid%3DAA45CBAA4F05219072372808692E0A32%3Fdoi%3D10. 1.1.133.9423%26rep%3Drep1%26type%3Dpdf&ei=xr_FUO7dOY7krAe6uoCQBg&usg=AFQjCNFjDOG3U1 hH0glIY_d8gEU7KSwM_w&bvm=bv.1354675689,d.bmk http://www.sphinxsai.com/2012/chem/CHEM/CT=17(105-108)JM12.pdf  http://greenanswers.com/q/272434/other/what-basis-separation-eugenol-other-components-cloveoil#ixzz2EjeOzjB1 http://www.answers.com/topic/pharmacology-biological-activities-of-cloves-1#ixzz2EjgTfq8l