COMPLETE REPORT ORGANIC CHEMISTRY 2

HERMIN HARDYANTI UTAMI (111 304 0202)

CHEMISTRY DEPARTMENT MATHEMATIC AND SCIENCE FACULTY STATE UNIVERSITY OF MAKASSAR 2012

RATIFICATION PAGE The complete report of Organic Chemistry II with the title of Isolation of Ethyl p-Metoxhy Cinnamic Galingale which made by : Name ID Group Class : Hermin Hardyanti Utami : 111 304 0202 : VII : ICP B

Have been checked by assistant and assistant coordinator. So, this report is accepted. Makkassar, December Assistant Coordinator Assistant 2012

Fandi Ahmad, S.Pd. Known By,

Muhammad Arsad, S.Si

Responsibility Lecturer

Dra. Hj. Ramdani, M.Si.

A. Tittle of Experiment Isolation of Ethyl p-Metoxhy Cinnamic Galingale B. Purposes At the last experiment, student can be understand about :
1. Principles of organic compounds of natural products isolation phenyl

propanoid.
2. Isolation techniques in natural materials by maceration, separation and

purification method. C. Background Galingale (Kaempferia galanga L.) is a traditional medicinal plant belonging to the spices and already known by the public. Galingale is known by the public with the term herb or rice galingale sleep, because this plant contains approximately 2-4% volatile oil. Ethyl para-methoxy cinnamic (EPMS) is a major component derived from cinnamic compounds contained in the rhizome galingale and are known to have activity as a sunscreen ingredient. EPMS levels in crude could reach 2.5%. High levels of lead galingale EPMS has a good prospect to be used as the basis of the synthesis of sunscreen compounds his higher power (Suyatno, journal of Synthetic). According to Barus (2009, thesis of EPMS) EPMS is contain in ester compound that contain in benzene ring and metoxhy group that chaining ethyl that has a polar character so in it extraction can be using the solvent that has a polarity varitation namely ethanol, ethyl acetic, methanol, water, and hexan. In extraction

of one compound that must be look is it polarity that the solvent with extract compound, both of them must be have same polarity of near of the same polarity. Maceration is the process of soaking the samples using

solvent. This process is very beneficial in insulating compound of natural materials, because for immersion plasmolisis event occurs that causes the cell wall breakdown occurs due to the difference in pressure inside and outside the cell, so compounds present in the cytoplasm be dissolved in an organic solvent and the extraction of compounds will be perfect as it can be set long immersion desired. Selection of solvents for maceration process will provide high effectiveness with respect to the solubility of the compound in a solvent such natural materials. Generally, the methanol solvent is a solvent widely used in the isolation of organic compounds of natural ingredients because it can dissolve most of the compound (Nurdiansyah, Maceration Journal). According to Tim Dosen (2012:30) one of compound of ethyl ester that in contain galingale is ethyl para metoxhy cinnamic that in phenyl propanoid group. The biosynthesis of it compound following the cinnamic way and used as analgecyc, antifungi, and soon. The structure of it compound is:

COOC2H5

OCH3

Cinnamic acid and its derivatives are known to have many biological activities, such as could compete competitively binding to tyrosinase. Bond of cinnamic acid and derivatives by tyrosinase inhibition causes the formation of melanin, so that these compounds can be used as a sunscreen active ingredient preparation and bleach. In addition, the structure of cinnamic acid and its derivatives are eligible to be developed as an anti-inflammatory analgesic compounds. Cinnamic derivatives of known as a form of active compound analgesic-anti-inflammatory function is para metoxhy cinnamic acid (Ekowat, Journal Vol.8 No.2, Oktober 2010). According to Fescenden (1982:82) one of aster carboxylic acid is one compound that contain the COOR gropu with R can be form alkyl or aryle. An ester can be formed with direct reaction between an carboxylic acid and alcohol one of reaction called with esterifitication reaction. Esterifitication catalization acidic and it is a reversible reaction. Some kind of differencial carboxylic acid compound can be obtained with way changing the hydroxyl group from carboxyl with many kind of the group (Rasyid, 2009:180). According to Kusumawati (International Journal of Pharmacy and Pharmaceutical Sciences) the PC complexes, either extract or EPMS were found to be irregular shaped in powdered form. The morphology of their surfaces was seen to be rough. However, its irregular shaped did not affect their flowability as the complex was found to be free flowing particles. The shape and surface morphology, however, might be affected by the type of phospholipids since they

are natural components in which their purity grades were determinant factors. As for the melting point of EPMS is 480-500C (Wordpress,2011) D. Chemical and Equipment 1. Chemical a. Aquadest (H2O) b. Ethanol (C2H5OH) 95% solution c. Whatmann filter paper d. Filter paper e. Aluminium foil f. Capillary tube g. Matches 2. Equipment a. Place of galingale b. Electronical scale c. Evaporator d. Stir bar e. Buchner funnel f. Beaker glass 800 ml g. Round flask 500 ml h. Erlenmeyer 800 ml and 250 ml i. Thiele equipment j. Bunsen burner k. Blender (1 piece) (1 piece) ( 1 set ) (1 piece) (1 piece) (1 piece) (1 piece) (1 piece) (1 piece) (1 piece) (1 piece)

l. Spray flask m. Soft cloth and rough cloth E. Work Procedure

(1 piece) (2 pieces)

1. 1 kg of galingale was balanced on the electronical scale with using beaker glass 800 ml. 2. It was cleaned and grinded until smooth with using blender. 3. It was dried and remained in untransparent place and was added by 1 L of ethanol. 4. The mixture then macerated until 48th hours. 5. The mixture then separates from it galingale with using Erlenmeyer. 6. The extract then was filtered by using Buchner funnel. 7. It was evaporated with using evaporator until ethanol separate with the extract. 8. It was evaporated in room temperature and filtered by using funnel. 9. It was let stand until 7th days in room temperature. 10. It was filtered with using filter paper and took the residue. 11. The residue (crystal) was dried until the crystal get dry EPMS. 12. It was balanced on the electronical balance. 13. It was filled in capillary tube and the melting point was determined with using Thiele equipment. F. Observation Result No. 1. Galingale Observation was balanced on Result 1 kg galingale

electronical balance. 2. It was cleaned and grinded by blender. 3. It was died by fan (sunlight undirect). 4. It was remained in untransparent place and added by ethanol 5. It was macerated until 48th hours. Yellow mixture 1 L of ethanol Dry galingale Smooth galingale

6.

It was separated from it galingale.

500 ml galingale (contain ethanol) Yellow extract.

extract

7.

It was filtered by Buchner funnel.

8.

It was evaporated by evaporator.

Separate : Ethanol / transparent. Galingale / greenish yellow Pure EPMS Forming yellow crystal with long square form. Dry crystal (like sugar structure). 0.8 g 420-500C

9. 10. 11. 12. 13.

It was filtered by funnel. It was let stand until 7th days. It was filtered and dried it residue. It was balanced the crystal. It was filled in capillary tube and determined it melting point.

Note : the crystal form like sugar (rough structure) and it melting point is same with theory (480-500C).

G. Discussion In this experiment, had done the isolation of ethyl para metoxhy cinnamic from galingale. Ethyl para metoxhy cinnamic (EPMS) is one of ethyl ester compound that contain in the galingale dan it is the phenyl propanoid group. Isolation is separation of the organic material from the nature. In this experiment, galingale was balanced and grinded to easy in dissolving galingale from it solvent (ethanol). After grinded, galingale then dried but undirect sunlight so that the chemical structure (EPMS) in galingale is not damage. Galingale the nadded by it solvent in untransparent place until 48th hours. The purpose of maceration is occur the solving processes in the cell wall and membrane galingale and easy to dissolving the secondary metabolite (sitoplasm) galingale with it solvent. Ethanol used as is solvent because has the same polarity with galingale namely polar. So that it can be are able to dissolve. Saperation and filtration of extract after macerated had done so that the pulp mixture (galingale and ethanol) not mixed with the extract. Extract then evaporeated to separating the galingale extract with it solvent (ethanol). After obtained the EPMS in solution form, EPMS then was let stand until 7th days until forming the yellow square crystal and has rough structure like the sugar structure. Cristal that obtained then filtered of it solution and dried to getting the pure crytal weight at doing the balancing. As for the crystal weight is 0.8 gram with the melting point is 420-500C, so that the experiment that had been done is same with the theory about it structure and it melting point.

As for chemical structure of EPMS is :

COOC2H5

OCH3

H. Closing 1. Conclusion Based on the experiment that hade been done, so it may be conclude that : a. The principle of isolation organic compound (EPMS) of phenyl propanoid from galingale are maceration, separation, extraction, and purification. b. The isolation technique in galingale can be obtained with maceration way, separation, and purification. 2. Suggestion a. Student can be more careful in doing the experiment. b. Student can me more compact with friends group.

BIBLIOGRAPHY

Barus, Rosbina. 2009. Amidasi Etil Para Metoksi Sinamat yang Diisolasi dari Kencur. Tesis, Universitas Sumatra Utara. Ekowati, Juni, dkk. 2010. Pengaruh Katalis pada Sintesis Asam Orto Metoksisinamat dengan Materi Awal Arto Metoksi Benzaldehida dan Uji Aktivitas Analgesiknya. Jurnal, Majalah Farmasi Airlangga, Vol.8, No.2, Oktober 2010. Fessenden, Ralph J. dan Joan S. Fessenden. 1982. Kimia Organik Edisi Ketiga. Jakarta : Erlangga. Kusumawati Idha dan Helmi Yusuf. 2011. Phospolipid Complex As A Carrier Of Camempferia Galangal Rhizome Extract To Improve Its Analgecic Activity. International Journal Of Pharmacy And Pharmaceutical Sciences ISSN- 0975-1491 Vol 3, Suppl 1, 2011. Nurdiansyah dan Abdi Radha. Efek Lama Maserasi Bubuk Kopra Terhadap Rendemen, Densitas, dan Bilangan Asam Biodiesel yang Dihasilkan dengan Metode Transesterifikasi In Situ. Penelitian Poltek Negeri Pontianak. Rasyid, Muhaidah. 2009. Kimia Organik I. Makasar : Badan Penerbit UNM. Suyatno dan Emil Kurniati. Sintesis Senyawa Tabir Surya Eugenil Para Metoksi Sinamat Melalui Reaksi Esterifikasi. Penelititan Unversitas Negeri Surabaya. Tim Dosen. 2012. Penuntun Praktikum Kimia Organik II. Makassar :Jurusan Kimia FMIPA UNM.

Question Answer 1. EPMS compound classified as based on its structure of benzene group and alkyl which is the ester group derivate alkaloid to synthesis of amino acid and binds cinnamic acid pathway. 2. Isolation of EPMS be masked and dried to ethyl para metoxhy cinnamic compound contained in galingale can extracted well. In addition to the teaching process can absorb the desired copound and galingale must be dry to eliminate or reduce the water molecules contain in galingale. 3. Distillation temperature should be maintained arrounf to 800C because who want to spent on distillation process is solvent ethanol. Where ethanol boils at 700-800C. if temperature less than or more than it temperature will be forming or that out instead of ethanol but others compound.