HERMIN HARDYANTI UTAMI (111 304 0202)

CHEMISTRY DEPARTMENT

MATHEMATIC AND SCIENCE FACULTY

STATE UNIVERSITY OF MAKASSAR

2012

ORGANIC CHEMISTRY 2

COMPLETE REPORT

RATIFICATION PAGE

The complete report of Organic Chemistry II with the title of “Isolation of

Ethyl p-Metoxhy Cinnamic Galingale

” which made by :

Name : Hermin Hardyanti Utami

ID : 111 304 0202

Group : VII

Class : ICP B

Have been checked by assistant and assistant coordinator. So, this report is

accepted.

Makkassar, December 2012

Assistant Coordinator

Fandi Ahmad, S.Pd.

Assistant

Muhammad Arsad, S.Si

Known By,

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 480-50

0C (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 (1 piece)

b. Electronical scale (1 piece)

c. Evaporator ( 1 set )

d. Stir bar (1 piece)

e. Buchner funnel (1 piece)

f. Beaker glass 800 ml (1 piece)

g. Round flask 500 ml (1 piece)

h. Erlenmeyer 800 ml and 250 ml (1 piece)

i. Thiele equipment (1 piece)

j. Bunsen burner (1 piece)

k. Blender (1 piece)

l. Spray flask (1 piece)

m. Soft cloth and rough cloth (2 pieces)

E. Work Procedure

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. Observation Result

1. Galingale was balanced on - 1 kg galingale

2.

3.

4.

5.

6.

7.

8.

9.

10.

11.

12.

13.

electronical balance.

It was cleaned and grinded by

blender.

It was died by fan (sunlight

undirect).

It was remained in untransparent

place and added by ethanol

It was macerated until 48th

hours.

It was separated from it galingale.

It was filtered by Buchner funnel.

It was evaporated by evaporator.

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.

- Smooth galingale

- Dry galingale

- 1 L of ethanol

- Yellow mixture

- 500 ml galingale extract

(contain ethanol)

- Yellow extract.

- Separate :

Ethanol / transparent.

Galingale / greenish yellow

- Pure EPMS

- Forming yellow crystal with

long square form.

- Dry crystal (like sugar

structure).

- 0.8 g

- 420-50

0C

Note : the crystal form like sugar (rough structure) and it melting point is same

with theory (480-50

0C).

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 420-50

0C, 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

700-80

0C. if temperature less than or more than it temperature will be forming

or that out instead of ethanol but others compound.