SINTESIS SENYAWA C18H26O9 DARI HIPTOLIDA HASIL ISOLASI DAUN HYPTIS PECTINATA

*Meiny Suzery -  Laboratorium Kimia Organik Jurusan Kimia MIPA Universitas Diponegoro Jl. Prof. Sudharto, Tembalang, Semarang 50275, Telp. 024-76480824, Indonesia
Ely Kusniawati -  Laboratorium Kimia Organik Jurusan Kimia MIPA Universitas Diponegoro Jl. Prof. Sudharto, Tembalang, Semarang 50275, Telp. 024-76480824, Indonesia
Dwi Hudiyanti -  Laboratorium Kimia Organik Jurusan Kimia MIPA Universitas Diponegoro Jl. Prof. Sudharto, Tembalang, Semarang 50275, Telp. 024-76480824, Indonesia
Bambang Cahyono -  Laboratorium Kimia Organik Jurusan Kimia MIPA Universitas Diponegoro Jl. Prof. Sudharto, Tembalang, Semarang 50275, Telp. 024-76480824, Indonesia
Published: 21 Apr 2012.
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Section: Research Article
Language: EN
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Abstract

SYNTHESIS OF C18H26O9 COMPOUNDS FROM HYPTOLIDE ISOLATED FROM HYPTIS PECTINATA LEAVES. Isolation of hyptolide has been done from Hyptis pectinata, and alkene group transformation through oxidation reactions using H3B: OEt2 to the isolated compound was also conducted. Product analyses were carried out using TLC, UV spectrometry, IR, and LC-MS. Pure crystal with melting point of 86-87oC was isolated. The yield was 1.75% (w/w). After analysing and compilating of spectroscopic data it was confirmed as hyptolide compound. Hydroboration of this compound (followed by hydrolysis using H2O2 under alkaline conditions) produce its alcohol derivatives, with 28.9% the percentage of transformation, it was demonstrated by LCMS data. IR spectrum at 3600cm-1, confirming the replacement of hydroxyl bond by alkene. Regioselectivity of addition reaction is proposed through simulation with Chem Office. The reaction product was suspected as 6-hydroxy-7-(6-oxo-3,6-dihydro-2H-pyran-2-yl) heptane-2,3,5-tryil triacetate. Extension of reaction time to 24 hours, has increase hydroboration product to 78.3%. This research has opened other studies of natural materials in accordance to the roadmap set.

 

 

Telah dilakukan isolasi hiptolida dari bahan alam Hyptis pectinata, dan transformasinya melalui reaksi oksidasi menggunakan H3B:OEt2 terhadap gugus alkena pada senyawa hasil isolasi. Analisis produk dilakukan menggunakan KLT, spektrometri UV, IR, dan LC-MS. Kristal murni dengan titik leleh 86-87oC berhasil diisolasi dengan rendemen 1,75 % (b/b), dirujuk sebagai senyawa hiptolida setelah melalui analisis dan kompilasi data-data spektroskopi. Hidroborasi terhadap senyawa hiptolida (yang diikuti hidrolisis menggunakan H2O2 dalam suasana basa) menghasilkan senyawa alkohol turunannya, dengan persentase transformasi sebesar 28,9%, dapat ditunjukkan melalui data LCMS. Data spectrum IR menunjukkan adanya puncak pada 3600cm-1, memperkuat dugaan  adanya ikatan hidroksil menggantikan gugus alkena. Regioselektivitas reaksi adisi diusulkan melalui simulasi dengan Chem Office, produk reaksi diduga mempunyai struktur  sebagai 6-hydroxy-7-(6-oxo-3,6-dihydro-2H-pyran-2-yl)heptane-2,3,5-tryil triacetate. Perpanjangan waktu reaksi selama 24 jam, telah dapat menaikkan produk hidroborasi menjadi 78,3%. Data penelitian ini telah membuka jalan bagi penelitian-penelitian bahan alam lain sesuai dengan roadmap penelitian yang telah ditetapkan.

Keywords
hidroborasi; hyptis pectinata; hiptolida

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