Sintesis Senyawa Turunan Zingeron dan Raspberry Keton serta Uji Potensi sebagai Atraktan Lalat Buah Hama

YURI PRADIKA, Dr. Deni Pranowo, S.Si., M.Si; Prof. Drs. Sabirin Mastjeh, Ph.D

2019 | Tesis | MAGISTER KIMIA

Sintesis senyawa 4-(5-bromo-4-hidroksi-3-metoksifenil)-3-buten-2-ol (A2), 4-(3,5-dibromo-4-hidroksifenil)-3-buten-2-ol (B2), dan 4-(5-bromo-4-hidroksi-3-metoksifenil)-2-butanon (A3), 4-(3,5-dibromo-4-hidroksifenil )-2-butanon (B3) dan uji potensi sebagai atraktan lalat buah telah dilakukan. Tujuan penelitian ini adalah untuk mendapatkan senyawa atraktan lalat buah hama yang baru selain metil eugenol dan cue lure. Sintesis senyawa turunan zingeron dan raspberry keton (A2, B2, A3, dan B3) tersebut dilakukan melalui tiga tahap, tahap pertama yaitu reaksi brominasi terhadap vanilin dan 4-hidroksibenzaldehida dengan menggunakan KBrO3 dan HBr dalam kondisi asam. Tahap kedua yaitu reaksi kondensasi aldol terhadap 5-bromovanilin dan 4-hidroksibenzaldehida dengan aseton menggunakan katalis NaOH 20%. Tahap ketiga yaitu sintesis senyawa turunan zingeron dan raspberry keton (A2 dan B2) melalui reaksi reduksi produk kondensasi aldol dengan NaBH4, sedangkan turunan zingeron dan raspberry keton (A3 dan B3) disintesis melalui reaksi reduksi produk kondensasi aldol dengan NaBH4 dan NiCl2.6H2O. Semua produk hasil reaksi dianalisis dengan FT-IR, GC-MS, 1H-NMR dan 13C-NMR. Hasil penelitian menunjukkan bahwa reaksi brominasi vanilin dan 4-hidroksibenzaldehida masing-masing menghasilkan 5-bromovanilin dan 3,5-dibromo-4-hidroksibenzaldehida berupa padatan berwarna putih dengan rendemen 82,28 dan 56,52%. Hasil reaksi kondensasi aldol berupa padatan berwarna kuning dengan rendemen masing-masing 93,33 dan 40,54%. Hasil sintesis turunan zingeron dan turunan raspberry keton (A2, B2, A3, dan B3) berupa cairan dengan rendemen masing-masing 48,77; 37,60; 68,18; dan 59,37%. Uji potensi sebagai atraktan lalat buah hama menunjukkan bahwa senyawa hasil sintesis (A2, B2, A3, dan B3) dapat memikat lalat buah (Bactrocera spp). Kata kunci : atraktan, raspberry keton, reduksi, zingereon

Synthesis of 4-(5-bromo-4-hydroxy-3-methoxyphenyl)-3-buten-2-ol (A2), 4-(3,5-dibromo-4-hydroxyphenyl)-3-buten-2-ol (B2), 4-(5-bromo-4-hydroxy-3-methoxyphenyl)-2-butanone (A3), and 4-(3,5-dibromo-4-hydroxyphenyl)-2-butan one (B3) and their potensial test as fruit flies attractant have been done. The aim of this research was to found new fruit flies attractant compounds beside methyl eugenol dan cue lure. Synthesis of zingerone and raspberry ketone derivatives (A2, B2, A3, and B3) were carried out in tree steps reaction. First, the bromination of vanillin and 4-hydroxybenzaldehyde were performed using KBrO3 and HBr in acidic condition. Second, aldol condensation of 5-bromovanillin and 3,5-dibromo-4-hydroxybenzaldehyde with acetone using base catalyst NaOH 20%. Third, the zingerone and raspberry ketone derivatives (A2 and B2) were synthesized by reacting the reduction reaction of aldol condensation products with NaBH4, while zingerone and raspberry ketone derivatives (A3 and B3) were synthesized by reacting the reduction reaction of aldol condensation products with NaBH4 and NiCl2.6H2O. All of products were analyzed by FT-IR GC-MS, 1H-NMR and 13C-NMR. The result showed that the bromination of vanillin and 4-hydroxy benzaldehyde produced 5-bromovanilin and 3,5-dibromo-4-hydroxybenzaldehyde as white powder with 82.28 and 56.52% yield. The result of aldol condensation reaction produced yellow powder in 93.33 and 40.54%. Synthesis of zingerone and raspberry ketone derivatives (A2, B2, A3, and B3) were yielded 48.77; 37.60; 68.18 and 59.37%, respectively as liquid. Potensial test as attractant of pest fruit flies showed that synthesized compounds (A2, B2, A3, and B3) could lure pest fruit flies (Bactrocera spp). Synthesis of 4-(5-bromo-4-hydroxy-3-methoxyphenyl)-3-buten-2-ol (A2), 4-(3,5-dibromo-4-hydroxyphenyl)-3-buten-2-ol (B2), 4-(5-bromo-4-hydroxy-3-methoxyphenyl)-2-butanone (A3), and 4-(3,5-dibromo-4-hydroxyphenyl)-2-butan one (B3) and their potensial test as fruit flies attractant have been done. The aim of this research was to found new fruit flies attractant compounds beside methyl eugenol dan cue lure. Synthesis of zingerone and raspberry ketone derivatives (A2, B2, A3, and B3) were carried out in tree steps reaction. First, the bromination of vanillin and 4-hydroxybenzaldehyde were performed using KBrO3 and HBr in acidic condition. Second, aldol condensation of 5-bromovanillin and 3,5-dibromo-4-hydroxybenzaldehyde with acetone using base catalyst NaOH 20%. Third, the zingerone and raspberry ketone derivatives (A2 and B2) were synthesized by reacting the reduction reaction of aldol condensation products with NaBH4, while zingerone and raspberry ketone derivatives (A3 and B3) were synthesized by reacting the reduction reaction of aldol condensation products with NaBH4 and NiCl2.6H2O. All of products were analyzed by FT-IR GC-MS, 1H-NMR and 13C-NMR. The result showed that the bromination of vanillin and 4-hydroxy benzaldehyde produced 5-bromovanilin and 3,5-dibromo-4-hydroxybenzaldehyde as white powder with 82.28 and 56.52% yield. The result of aldol condensation reaction produced yellow powder in 93.33 and 40.54%. Synthesis of zingerone and raspberry ketone derivatives (A2, B2, A3, and B3) were yielded 48.77; 37.60; 68.18 and 59.37%, respectively as liquid. Potensial test as attractant of pest fruit flies showed that synthesized compounds (A2, B2, A3, and B3) could lure pest fruit flies (Bactrocera spp). Keyword: attractant, raspberry ketone, reduction, zingerone

Kata Kunci : Atraktan, Raspberry Keton, Reduksi, Zingeron