SINTESIS 2,5�bis(4��HIDROKSI�5��KLORO�3��METOKSIBENZILIDIN) SIKLOPENTANON DAN UJI AKTIVITASNYA SEBAGAI ANTIOKSIDAN
A study was performed to obtain a curcumin analogue compound which ha �Cl substituent in the aromatic ring i.e. 2,5�bis(5��chloro�4��hydroxy�3�� methoxybenzylidene)cyclopentanone. The synthesis of this compound was carried out by condensation of cyclopentanone with chlorinated va...
| Main Authors: | , |
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| Format: | Thesis |
| Published: |
[Yogyakarta] : Universitas Gadjah Mada
2013
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| _version_ | 1826046103201513472 |
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| author | , warsi , Dr. Sardjiman, M.S., Apt., |
| author_facet | , warsi , Dr. Sardjiman, M.S., Apt., |
| author_sort | , warsi |
| collection | UGM |
| description | A study was performed to obtain a curcumin analogue compound which
ha �Cl substituent in the aromatic ring i.e. 2,5�bis(5��chloro�4��hydroxy�3��
methoxybenzylidene)cyclopentanone. The synthesis of this compound was carried
out by condensation of cyclopentanone with chlorinated vanilin (5�chloro�4�
hydroxy�3�methoxybenzaldehyde). This compound has been identified. Its
activity as an antioxidant using DPPH (1,1�diphenyl�2�picrylhydrazyl) radical
scavenging and the �-carotene�linoleic acid methods have been investigated.
Th
Chlorination reaction of vanillin performed using Cl2 gas, which produced
by reaction of kaporit with concentrated hydrochloric acid. e reaction occured
at 35ºC for 30 minutes, with the AlCl3 as a catalyst and THF as the solvent. It
produced a yellow compound of 5�chloro�4�hydroxy�3�methoxybenzaldehyde.
The average yield was 40.54 % and the melting point was 163.3�164.8ºC. Then,
5�chloro�4�hydroxy�3�methoxybenzaldehyde was condensed with cyclopen-
tanone to form a green�yellow compound of 2,5�bis(5��chloro�4� Hydroxyl � 3��
methoxybenzylidene)cyclopentanone. This condensation reaction occured at room
temperature for 4 hours, under acidic conditions and THF as the solvent. The
reaction mixture was set aside for 6 days. The average yield is 49,77 % and the
melting point of 268.0�270.0ºC. The purity of the synthesized compounds were
determined by Thin Layer Chromatography and High Performance Liquid
Chromatography. The structure elucidation of this synthesized compounds have
been performed using spectroscopy techniques, including infrared, nuclear
magnetic resonance proton, nuclear magnetic resonance carbon and mass
spectrometry.
�
The antioxidant activity of synthesized product was determined by DPPH
radical scavenging method and the absorbance was measured by the UV Vis
spectrophotometer at �max of 517 nm. The synthesized compound showed the
activity of DPPH radical scavenging metode (IC50 184.23 �M). Its potency as an
antioxidant was lower than PGV�0 (IC50 26.76 �M) and curcumin (IC50 13.69
�M). The potency of antioxidant activity of synthesized product was also
determined based on inhibition of the �-carotene bleaching by the linoleic acid
radical and the absorbance was measured by the UV�Vis spectrophotometer at
�max of 450 nm. The result of this method obtained EC50 value of 23.04 �M. The
antioxidant potency of the sample was more potent than those curcumin (EC50
25.86 �M) and PGV�0 (EC50 32.15 �M). |
| first_indexed | 2024-03-13T22:47:58Z |
| format | Thesis |
| id | oai:generic.eprints.org:118885 |
| institution | Universiti Gadjah Mada |
| last_indexed | 2024-03-13T22:47:58Z |
| publishDate | 2013 |
| publisher | [Yogyakarta] : Universitas Gadjah Mada |
| record_format | dspace |
| spelling | oai:generic.eprints.org:1188852016-03-04T08:45:05Z https://repository.ugm.ac.id/118885/ SINTESIS 2,5�bis(4��HIDROKSI�5��KLORO�3��METOKSIBENZILIDIN) SIKLOPENTANON DAN UJI AKTIVITASNYA SEBAGAI ANTIOKSIDAN , warsi , Dr. Sardjiman, M.S., Apt., ETD A study was performed to obtain a curcumin analogue compound which ha �Cl substituent in the aromatic ring i.e. 2,5�bis(5��chloro�4��hydroxy�3�� methoxybenzylidene)cyclopentanone. The synthesis of this compound was carried out by condensation of cyclopentanone with chlorinated vanilin (5�chloro�4� hydroxy�3�methoxybenzaldehyde). This compound has been identified. Its activity as an antioxidant using DPPH (1,1�diphenyl�2�picrylhydrazyl) radical scavenging and the �-carotene�linoleic acid methods have been investigated. Th Chlorination reaction of vanillin performed using Cl2 gas, which produced by reaction of kaporit with concentrated hydrochloric acid. e reaction occured at 35ºC for 30 minutes, with the AlCl3 as a catalyst and THF as the solvent. It produced a yellow compound of 5�chloro�4�hydroxy�3�methoxybenzaldehyde. The average yield was 40.54 % and the melting point was 163.3�164.8ºC. Then, 5�chloro�4�hydroxy�3�methoxybenzaldehyde was condensed with cyclopen- tanone to form a green�yellow compound of 2,5�bis(5��chloro�4� Hydroxyl � 3�� methoxybenzylidene)cyclopentanone. This condensation reaction occured at room temperature for 4 hours, under acidic conditions and THF as the solvent. The reaction mixture was set aside for 6 days. The average yield is 49,77 % and the melting point of 268.0�270.0ºC. The purity of the synthesized compounds were determined by Thin Layer Chromatography and High Performance Liquid Chromatography. The structure elucidation of this synthesized compounds have been performed using spectroscopy techniques, including infrared, nuclear magnetic resonance proton, nuclear magnetic resonance carbon and mass spectrometry. � The antioxidant activity of synthesized product was determined by DPPH radical scavenging method and the absorbance was measured by the UV Vis spectrophotometer at �max of 517 nm. The synthesized compound showed the activity of DPPH radical scavenging metode (IC50 184.23 �M). Its potency as an antioxidant was lower than PGV�0 (IC50 26.76 �M) and curcumin (IC50 13.69 �M). The potency of antioxidant activity of synthesized product was also determined based on inhibition of the �-carotene bleaching by the linoleic acid radical and the absorbance was measured by the UV�Vis spectrophotometer at �max of 450 nm. The result of this method obtained EC50 value of 23.04 �M. The antioxidant potency of the sample was more potent than those curcumin (EC50 25.86 �M) and PGV�0 (EC50 32.15 �M). [Yogyakarta] : Universitas Gadjah Mada 2013 Thesis NonPeerReviewed , warsi and , Dr. Sardjiman, M.S., Apt., (2013) SINTESIS 2,5�bis(4��HIDROKSI�5��KLORO�3��METOKSIBENZILIDIN) SIKLOPENTANON DAN UJI AKTIVITASNYA SEBAGAI ANTIOKSIDAN. UNSPECIFIED thesis, UNSPECIFIED. http://etd.ugm.ac.id/index.php?mod=penelitian_detail&sub=PenelitianDetail&act=view&typ=html&buku_id=58862 |
| spellingShingle | ETD , warsi , Dr. Sardjiman, M.S., Apt., SINTESIS 2,5�bis(4��HIDROKSI�5��KLORO�3��METOKSIBENZILIDIN) SIKLOPENTANON DAN UJI AKTIVITASNYA SEBAGAI ANTIOKSIDAN |
| title | SINTESIS 2,5�bis(4��HIDROKSI�5��KLORO�3��METOKSIBENZILIDIN)
SIKLOPENTANON DAN UJI AKTIVITASNYA
SEBAGAI ANTIOKSIDAN |
| title_full | SINTESIS 2,5�bis(4��HIDROKSI�5��KLORO�3��METOKSIBENZILIDIN)
SIKLOPENTANON DAN UJI AKTIVITASNYA
SEBAGAI ANTIOKSIDAN |
| title_fullStr | SINTESIS 2,5�bis(4��HIDROKSI�5��KLORO�3��METOKSIBENZILIDIN)
SIKLOPENTANON DAN UJI AKTIVITASNYA
SEBAGAI ANTIOKSIDAN |
| title_full_unstemmed | SINTESIS 2,5�bis(4��HIDROKSI�5��KLORO�3��METOKSIBENZILIDIN)
SIKLOPENTANON DAN UJI AKTIVITASNYA
SEBAGAI ANTIOKSIDAN |
| title_short | SINTESIS 2,5�bis(4��HIDROKSI�5��KLORO�3��METOKSIBENZILIDIN)
SIKLOPENTANON DAN UJI AKTIVITASNYA
SEBAGAI ANTIOKSIDAN |
| title_sort | sintesis 2 5a��bis 4a��a��hidroksia��5a��a��kloroa��3a��a��metoksibenzilidin siklopentanon dan uji aktivitasnya sebagai antioksidan |
| topic | ETD |
| work_keys_str_mv | AT warsi sintesis25abis4aahidroksia5aakloroa3aametoksibenzilidinsiklopentanondanujiaktivitasnyasebagaiantioksidan AT drsardjimanmsapt sintesis25abis4aahidroksia5aakloroa3aametoksibenzilidinsiklopentanondanujiaktivitasnyasebagaiantioksidan |