isolation etil para metoxy cinnamate from kaemfria galanga
DESCRIPTION
COMPLETE REPORT ORGANIC CHEMISTRY 2HERMIN HARDYANTI UTAMI (111 304 0202)CHEMISTRY DEPARTMENT MATHEMATIC AND SCIENCE FACULTY STATE UNIVERSITY OF MAKASSAR 2012RATIFICATION 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 BHave been checked by assistant and assistant coordinator. So, this report is accepted. Makkassar, December AssistaTRANSCRIPT
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.