SINTESIS SENYAWA C18H26O9 DARI HIPTOLIDA HASIL ISOLASI DAUN HYPTIS PECTINATA

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 86-87^oC 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 86-87^oC 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.