Eugenol

  1. SYNTHESIS OF ANALOG L-α-METIL-DOPA FROM EUGENOL. Synthesis of analog L-α-metil-Dopa from eugenol has been achieved through conversion of allyl group to ketone, followed by reaction with NH3 and KCN and by hydrolisis. The addition reaction of methyleugenol with formic acid yield methyleugenyl formate(60, 69%). The hydrolis of methyileugenylformate with KOH in aqaueous-ethanolic solution produced methyleugenyl alcohol (73, 68%). The oxidation of methyleugenyl alcohol with PCC yield methyleugenyl ketone (67, 71%). The reaction of methyleugenyl ketone with NH3 and KCN yield D, L-α-amino-α-(3, 4-dimetoxybenzyl) propionitril (84, 14%). The hydrolisis of D, L-α-amino-α-(3, 4-dimetoxybenzyl) propionitril with concentrated hydrochloric acid gave Analog L-α-metil-Dopa as a main target (91, 98%). The structure elucidation of these products were analyzed by FTIR, 1H-NMR, 13C-NMR and MS.
  1. Sintesis 3, 4-Dimetoksifenil-2-Propanon dari Metileugenol
  2. Sintesis 1-(3, 4-Metilendioksifenil)-2-Propanon dari Safrol dan Sintesis Analog L-DOPA dari Eugenol. Eugenol, 3-(4-hidroksi-3-metoksifenili) propena dan safrol, 3-(3, 4-metilen dioksifenilf) propena adalah dua komponen utama dari minyak kulit lawang. Dalam penelitian ini, telah dilakukan konversi eugenol menjadi metileugenol, metileugenil format, l-(3, 4-dimetoksifenil)-2-propanol, l-(3, 4-dimetoksifenil)-2-propanon dan analog DOPA. Safrol telah dapat dikonversi menjadi safril format, l-(3 _, 4-metilendioksifenil)-2-propanol dan 1-8, 4-metilendioksifenil)-2-propanon. Beberapa metode yang menyangkut konversi eugenol dan safrol telah dipelajari secara detail seperti oksimerkurasi-demerkurasi metileugenol menjadi l-(3, 4-dimetoksifenil)-2-propanol, oksidasi l-(3, 4-dimetoksifenil)-2-propanol menjadi l-(3, 4-dimetoksifenil)-2-propanon dan sintesis analog DOPA dari turunan eugenol, formilasi safrol menjadi safril format, oksimerkurasi demerkurasi safrol menjadi l-(3, 4-metilendioksifenil)-2-propanol dan oksidasi l-(3, 4-metilendioksifenil)-2-propanol menjadi 1-8, 4-metilendioksifenil)-2-propanon. Selain aspek-aspek pembuatan metileugenil format dari metileugenol, aspek spektroskopi (lH-NMR dan 13C-NMR) dari metileugenil format juga telah dipelajari. Interpretasi terhadap spektrum lH-NMR, 250 MHz dari metileugenil format yang diekspansi pada daerah metilen berhasil diungkapkan bahwa kedua atom H berbeda berdasarkan tetapan kopling dan daerah pergeseran kimia. Aplikasi metode baru antara lain; formilasi dan oksimerkurasi-demerkurasi safrol dan metileugenol menjadi alkohol sekunder telah juga dipelajari dan yang paling menarik adalah oksidasi alkohol sekunder menjadi keton dengan menggunakan PCC-AlgO3.
  1. Sintesis 1-fenil-4-(3’, 4’-dimetoksi fenil)-1-buten-3-on dari Eugenol. The synthesis of 1-phenyl-4-(3’, 4’-dimethoxy phenyl)-1-buten-3-one from eugenol has been done through four reaction steps. The metilation of eugenol with dimethyl sulphate yields 81.81% of methyl eugenol. Oxymercuration-demercuration of methyl eugenol with mercury acetate yields 67.27% of methyl eugenyl alcohol. Oxidation of methyl eugenyl alcohol with pyridinium chloro chromate (PCC) yields 45.31% of methyl eugenyl ketone. Aldol condensation reaction of methyl eugenyl ketone with benzaldehide catalyzed by potasium hydroxyde yields 7.38% of 1-phenyl4-(3’, 4’-dimethoxyphenyl)-1-buten-3-one. The purity of compounds was tested by GC and LC. The Elucidation of structure was analyzed by FTIR, GC-MS, LC-ESI-MS, and H-NMR.
  1. SYNTHESIS OF SECONDARY ALCOHOL COMPOUNDS FROM SAFROLE AND METHYLEUGENOL. Synthesis of secondary alcohols compound from safrole and methyleugenol has been achieved through conVersion of allyl group to alcohol. The reaction of safrole and methyleugenol with mercuric acetate in aqueous tetrahydrofuran, followed by in situ reduction of the mercurial intermediate by alkaline sodium borohydride produced secondary alcohol namely safryl alcohol (71.25%) and methyleugenil alcohol (65.56%). The structure elucidation of these products were analyzed by FTIR, 1H-NMR, 13C-NMR and MS.
  2. Pembuatan Vanilin dari Eugenol
  3. Synthesis Of 1-phenyl-4-(3’, 4’-dimethoxy phenyl)-1-Buten-3-on From Eugenol. The synthesis of 1-phenyl-4-(3’, 4’-dimethoxy phenyl)-1-buten-3-one from eugenol has been done through four reaction steps. The metilation of eugenol with dimethyl sulphate yields 81.81% of methyl eugenol. Oxymercuration-demercuration of methyl eugenol with mercury acetate yields 67.27% of methyl eugenyl alcohol. Oxidation of methyl eugenyl alcohol with pyridinium chloro chromate (PCC) yields 45.31% of methyl eugenyl ketone. Aldol condensation reaction of methyl eugenyl ketone with benzaldehide catalyzed by potasium hydroxyde yields 7.38% of 1-phenyl4-(3’,4’-dimethoxyphenyl)-1-buten-3-one. The purity of compounds was tested by GC and LC. The Elucidation of structure was analyzed by FTIR, GC-MS, LC-ESI-MS, and 1H-NMR.
  1. ISOLASI EUGENOL DARI BUNGA CENGKEH DAN SINTESIS EUGENIL ASETAT (2-METHOXY-4-(2-PROPEN-1-YL)-PHENYL ACETATE). Telah dilakukan isolasi eugenol dari minyak cengkeh dan sintesis eugenil asetat. Minyak cengkeh diekstrak dari bunga cengkeh menggunakan petrolium benzen dengan metode ekstraksi soxhlet diperoleh 33.82%. Isolasi eugenol menggunakan NaOH diperoleh 32, 07% dengan kemurnian 97, 47%. Reaksi esterifikasi eugenol dengan anhidrida asetat menggunakan natrium asetat anhidrat sebagai katalis diperoleh eugenil asetat 51, 67% dengan kemurnian 98, 38%. Elusidasi struktur menggunakan Spektrofotometer Infra Red (IR), Spektrofotometer Resonansi Magnetik Inti Proton (1H-NMR) dan Spektrofotometer Massa (MS) serta uji kemurnian dengan Kromatografi Gas (GC).