Synthesis and Antimicrobial Activity Evaluation of Ethyl Salicyl Fumarate and Ethyl Furfuryl Fumarate: Sintesis dan um khasiat anteviikrosa terhadap etil salisil fumarat dan etil furfuril fumarat
This research was conducted in order to synthesize and investigate the antimicrobial activity of ethyl salicyl fumarate and ethyl furfuryl fumarate. These two target molecules were chosen as the former is the derivative of C-9154 antibiotic containing phenolic hydroxyl group, whereas the latter is a...
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| Formato: | Artigo |
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[Yogyakarta] : Universitas Gadjah Mada
2002
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| _version_ | 1826032482594586624 |
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| author | Perpustakaan UGM, i-lib |
| author_facet | Perpustakaan UGM, i-lib |
| author_sort | Perpustakaan UGM, i-lib |
| collection | UGM |
| description | This research was conducted in order to synthesize and investigate the antimicrobial activity of ethyl salicyl fumarate and ethyl furfuryl fumarate. These two target molecules were chosen as the former is the derivative of C-9154 antibiotic containing phenolic hydroxyl group, whereas the latter is an example of C9154 antibiotic derivative bearing furan ring instead of benzene.
Ethyl salicyl fumarate was synthesized from methyl salicylate through reduction with LiAIH4, condensation of salicyl alcohol with maleic anhydride, and esterification of salicyl maleic acid with ethanol in the presence of benzenesulfonic acid as the catalyst. These reactions gave satisfactory yields (76-92 %) in all steps involved. Similar to this procedure, ethyl furfuryl fumarate was prepared from furfural through reduction with NaBH4 followed by condensation of the resulted furfuryl alcohol with maleic anhydride and esterification of furfuryl maleic acid with ethanol in the presence of benzenesulfonic acid. Although the reduction of furfural and the condensation of furfuryl alcohol with maleic anhydride could be performed smoothly, the esterification of furfuryl maleic acid with ethanol only gave 38 % yield of ethyl furfuryl fumarate.
The results of antimicrobial activity test showed that the value of minimum inhibition concentration (M1C) of salicyl maleic acid and ethyl salicyl fumarate towards Staphyllococcus aureus- were 500 and 100 tg/mL, whereas towards Eschericia coil were 2000 and 4000 ag/mL respectively. In contrast, the MIC values of furfuryl maleic acid and ethyl furfuryl fumarate towards Staphyllococcus aureus and Eschericia tali were 150 and 100 p.g/mL respectively.
Keywords: synthesis, activity, C-9154 antibiotic, fumarate.
ABSTRAK
Penelitian ini dilakukan dengan tujuan melakukan sintesis dan uji khasiat antimikroba terhadap etil salisil fumarat dan etil furfuryl fumarat. Kedua molekul target tersebut dipilih dengan pertimbangan bahwa etil salisil fumarat akan merupakan contoh turunan antibiotik C-9154 yang mengandung gugus fenol, sedangkan etil furfuryl fumarat akan menjadi contoh turunan antibiotik C-9154 yang mengikat cincin furan.
Etil salisil fumarat disintesis dari metil salisilat melalui reduksi dengan LiAIH4i kondensasi dari salisil alkohoi dengan anhidrida maleat, dan esterifikasi asam salisil maleat dengan etanol menggunakan katalis asam benzenasulfonat. Keseluruhan tahapan reaksi tersebut memberikan rendemen hasil yang
memuaskan (76-92 %). Serupa dengan itu, etil furfuril fiunarat disintesis dart furfural melalui reduksi menggunalcan NaBH4 diteruskan dengan kondensasi furfuril alkohol dengan anhidrida maleat dan esterifikasi asam furfuril maleat dengan etanol. Walaupun reduksi furfural dan kondensasi furfuril alkohol dengan anhidrida maleat dapat dilakukan dengan balk, esterifikasi asam furfuril maleat dengan etanol hanya menghasiikan 38 % etil furfuril fumarat.
Hasil uji khasiat antimikroba menunjukkan bahwa harga konsentrasi hambatan minimum (MIC) dad asam salisil maleat dan etil salisil fumarat terhadap Slaphyllococcus aureus masing-masing adalah 500 dan 100 ig/mL, sedangkan terhadap Eschericia coli adalah 2000 and 4000 p.g/mL. Sebaliknya, harga MIC dan asam furfuril maleat dan etil furfuril fumarat terhadap Slaphyllococcus aureus dan Eschericia coil masingmasing adalah 150 dan 100 ug/mL.
Kata kuaci: sinlesrs, aklivilas, anlibiolik C-9154, fumarat. |
| first_indexed | 2024-03-13T18:54:20Z |
| format | Article |
| id | oai:generic.eprints.org:24608 |
| institution | Universiti Gadjah Mada |
| last_indexed | 2024-03-13T18:54:20Z |
| publishDate | 2002 |
| publisher | [Yogyakarta] : Universitas Gadjah Mada |
| record_format | dspace |
| spelling | oai:generic.eprints.org:246082014-06-18T00:32:17Z https://repository.ugm.ac.id/24608/ Synthesis and Antimicrobial Activity Evaluation of Ethyl Salicyl Fumarate and Ethyl Furfuryl Fumarate: Sintesis dan um khasiat anteviikrosa terhadap etil salisil fumarat dan etil furfuril fumarat Perpustakaan UGM, i-lib Jurnal i-lib UGM This research was conducted in order to synthesize and investigate the antimicrobial activity of ethyl salicyl fumarate and ethyl furfuryl fumarate. These two target molecules were chosen as the former is the derivative of C-9154 antibiotic containing phenolic hydroxyl group, whereas the latter is an example of C9154 antibiotic derivative bearing furan ring instead of benzene. Ethyl salicyl fumarate was synthesized from methyl salicylate through reduction with LiAIH4, condensation of salicyl alcohol with maleic anhydride, and esterification of salicyl maleic acid with ethanol in the presence of benzenesulfonic acid as the catalyst. These reactions gave satisfactory yields (76-92 %) in all steps involved. Similar to this procedure, ethyl furfuryl fumarate was prepared from furfural through reduction with NaBH4 followed by condensation of the resulted furfuryl alcohol with maleic anhydride and esterification of furfuryl maleic acid with ethanol in the presence of benzenesulfonic acid. Although the reduction of furfural and the condensation of furfuryl alcohol with maleic anhydride could be performed smoothly, the esterification of furfuryl maleic acid with ethanol only gave 38 % yield of ethyl furfuryl fumarate. The results of antimicrobial activity test showed that the value of minimum inhibition concentration (M1C) of salicyl maleic acid and ethyl salicyl fumarate towards Staphyllococcus aureus- were 500 and 100 tg/mL, whereas towards Eschericia coil were 2000 and 4000 ag/mL respectively. In contrast, the MIC values of furfuryl maleic acid and ethyl furfuryl fumarate towards Staphyllococcus aureus and Eschericia tali were 150 and 100 p.g/mL respectively. Keywords: synthesis, activity, C-9154 antibiotic, fumarate. ABSTRAK Penelitian ini dilakukan dengan tujuan melakukan sintesis dan uji khasiat antimikroba terhadap etil salisil fumarat dan etil furfuryl fumarat. Kedua molekul target tersebut dipilih dengan pertimbangan bahwa etil salisil fumarat akan merupakan contoh turunan antibiotik C-9154 yang mengandung gugus fenol, sedangkan etil furfuryl fumarat akan menjadi contoh turunan antibiotik C-9154 yang mengikat cincin furan. Etil salisil fumarat disintesis dari metil salisilat melalui reduksi dengan LiAIH4i kondensasi dari salisil alkohoi dengan anhidrida maleat, dan esterifikasi asam salisil maleat dengan etanol menggunakan katalis asam benzenasulfonat. Keseluruhan tahapan reaksi tersebut memberikan rendemen hasil yang memuaskan (76-92 %). Serupa dengan itu, etil furfuril fiunarat disintesis dart furfural melalui reduksi menggunalcan NaBH4 diteruskan dengan kondensasi furfuril alkohol dengan anhidrida maleat dan esterifikasi asam furfuril maleat dengan etanol. Walaupun reduksi furfural dan kondensasi furfuril alkohol dengan anhidrida maleat dapat dilakukan dengan balk, esterifikasi asam furfuril maleat dengan etanol hanya menghasiikan 38 % etil furfuril fumarat. Hasil uji khasiat antimikroba menunjukkan bahwa harga konsentrasi hambatan minimum (MIC) dad asam salisil maleat dan etil salisil fumarat terhadap Slaphyllococcus aureus masing-masing adalah 500 dan 100 ig/mL, sedangkan terhadap Eschericia coli adalah 2000 and 4000 p.g/mL. Sebaliknya, harga MIC dan asam furfuril maleat dan etil furfuril fumarat terhadap Slaphyllococcus aureus dan Eschericia coil masingmasing adalah 150 dan 100 ug/mL. Kata kuaci: sinlesrs, aklivilas, anlibiolik C-9154, fumarat. [Yogyakarta] : Universitas Gadjah Mada 2002 Article NonPeerReviewed Perpustakaan UGM, i-lib (2002) Synthesis and Antimicrobial Activity Evaluation of Ethyl Salicyl Fumarate and Ethyl Furfuryl Fumarate: Sintesis dan um khasiat anteviikrosa terhadap etil salisil fumarat dan etil furfuril fumarat. Jurnal i-lib UGM. http://i-lib.ugm.ac.id/jurnal/download.php?dataId=7586 |
| spellingShingle | Jurnal i-lib UGM Perpustakaan UGM, i-lib Synthesis and Antimicrobial Activity Evaluation of Ethyl Salicyl Fumarate and Ethyl Furfuryl Fumarate: Sintesis dan um khasiat anteviikrosa terhadap etil salisil fumarat dan etil furfuril fumarat |
| title | Synthesis and Antimicrobial Activity Evaluation of Ethyl Salicyl Fumarate and Ethyl Furfuryl Fumarate: Sintesis dan um khasiat anteviikrosa terhadap etil salisil fumarat dan etil furfuril fumarat |
| title_full | Synthesis and Antimicrobial Activity Evaluation of Ethyl Salicyl Fumarate and Ethyl Furfuryl Fumarate: Sintesis dan um khasiat anteviikrosa terhadap etil salisil fumarat dan etil furfuril fumarat |
| title_fullStr | Synthesis and Antimicrobial Activity Evaluation of Ethyl Salicyl Fumarate and Ethyl Furfuryl Fumarate: Sintesis dan um khasiat anteviikrosa terhadap etil salisil fumarat dan etil furfuril fumarat |
| title_full_unstemmed | Synthesis and Antimicrobial Activity Evaluation of Ethyl Salicyl Fumarate and Ethyl Furfuryl Fumarate: Sintesis dan um khasiat anteviikrosa terhadap etil salisil fumarat dan etil furfuril fumarat |
| title_short | Synthesis and Antimicrobial Activity Evaluation of Ethyl Salicyl Fumarate and Ethyl Furfuryl Fumarate: Sintesis dan um khasiat anteviikrosa terhadap etil salisil fumarat dan etil furfuril fumarat |
| title_sort | synthesis and antimicrobial activity evaluation of ethyl salicyl fumarate and ethyl furfuryl fumarate sintesis dan um khasiat anteviikrosa terhadap etil salisil fumarat dan etil furfuril fumarat |
| topic | Jurnal i-lib UGM |
| work_keys_str_mv | AT perpustakaanugmilib synthesisandantimicrobialactivityevaluationofethylsalicylfumarateandethylfurfurylfumaratesintesisdanumkhasiatanteviikrosaterhadapetilsalisilfumaratdanetilfurfurilfumarat |