SINTESIS ANALOG BENZALASETON MENGGUNAKAN KATALIS NaOH/ZrO2-MONTMORILONIT DAN UJI AKTIVITASNYA SEBAGAI ANTIOKSIDAN

• Main Authors: , Sri Handayani, M.Si, , Prof. Dr. Sabirin Matsjeh
• Format: Theses and Dissertations NonPeerReviewed
• Published: [Yogyakarta] : Universitas Gadjah Mada 2013
• Subjects: ETD
• Online Access: https://repository.ugm.ac.id/118646/; http://etd.ugm.ac.id/index.php?mod=penelitian_detail&sub=PenelitianDetail&act=view&typ=html&buku_id=58620
• Institution: Universitas Gadjah Mada

The synthesis of analogue benzalacetone i.e.: benzalacetone, dibenzalacetone, and 1.5-dibenzalacetone compounds has been carried out using homogeneus and heterogeneus catalysts. The synthesis of dibenzalacetone group was performed using NaOH as base catalyst and HCl as acid catalyst. The synthesis of benzalacetone and 1,5-dibenzalacetone groups were performed using NaOH/ZrO2-montmorillonite as cooperative catalyst. Purity identification of the target products was carried out by thin layer chromatography, while the structure elucidation was analyzed by FTIR and NMR spectrometer. Antioxidant activity of resulting compounds were then tested using the inhibition of deoxyribose degradation method to determine the IC50 value. Qualitative structure-activity relationship study was carried out by determining the Bond Dissociation Entalphy (BDE) value of compounds that contain ArO· group and comparing the BDE to the obtained IC50 value. Methoxy and hydroxydibenzalacetone compounds could be synthesized through cross aldol condensation reaction using NaOH, instead of HCl as catalyst. Condensation reaction between acetone and 4-hydroxybenzaldehyde using HCl as catalyst produce a new hemiacetal compounds (78.94%). Efficiency of NaOH/ZrO2-montmorillonite as cooperatif catalyst in benzalacetone and 1,5- dibenzalacetone synthesis were better than NaOH. The yield of benzalacetone and 1,5-dibenzalacetone derivative have increased from 1,6-6,5 to 1,2-16,3 time respectively. The analogue benzalacetone compound that active as antioxidant is material that contain hydroxyl group on its aromatic ring. The antioxidant activity order from the most active based on the BDE values are as follows 2,2'- dihydroxydibenzalacetone, vanilylacetone, 2-hydroxybenzalacetone, 3-hydroxybenzalacetone, 4-(hydroxy(4-hydroxyphenyl)methoxy)benzaldehyde, 3,3'- dihydroxydibenzalacetone dan 3-hydroxydibenzalacetone, respectively. The order of antioxidant activity based on the IC50 value is similar to sequence, but 3- hydroxydibenzalacetone slightly more active than 3,3'-dihydroxydibenzalacetone