MAX REVOLTA JOHN RUNTUWENE, 090415492 D (2010) SINTESIS TURUNAN KUMARIN DARI EUGENOL DAN UJI AKTIVITAS ANTIOKSIDAN MASING-MASING TURUNAN. Disertasi thesis, UNIVERSITAS AIRLANGGA.

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Abstract

Research on the synthesis of coumarin derivatives from eugenol isolated from oil of clove leaves and test of each derivatives was conducted. Coumarin derivatives possess varied biological activities, antioxidant activity being one of them. Eugenol is a main constituent of clove oil. Theoretically, coumarin derivatives are capable of synthesis by the use of eugenol as a starting material. The purpose of the present research was to synthesize several coumarin derivatives and to determine antioxidant activities of those coumarin derivatives successfully synthesized. Purification of isolates was carried out by pressure-diminution distillation. Tests of purity were performed by means of thin-layer chromatography and determination of physical properties such as refractive index and melting point. Structures were subsequently identified by infra-red spectrometer, magnetic resonance of nuclear 1H and 13C and mass spectroscopy. Results indicated (1) seven successfully synthesized coumarin derived-compounds of 1A (methyl 6-allyl-8-methoxy-6-coumarin carboxylate), 2A (ethyl 6-allyl-8-methoxy-6-coumarincarboxylate), 1B (methyl 8-methoxy-6-prophenyl-4-coumarincarboxylate), 2B (ethyl 8-methoxy-6-prophenyl-4-coumarincarboxylate), 1C (methyl 6-formyl-8-methoxy-4-coumarincarboxylate), 2C (ethyl 6-formyl-8-methoxy-4-coumarincarboxylate), 1D (methyl 8-methoxy-6-[(2-phenylhydrazono) methyl]-4-coumarincarboxylate). (2) Four coumarin-derived compounds of 1B, 2A, 2B, and 1D are novel compounds. (3) In overall, antioxidant activities of the coumarin derivatives successfully synthesized increased relative to the starting compounds. (4) Two compounds possessed an antioxidant activity higher than that of -tocopherol (positive control), namely, compound 1D and 1B. (5) Antioxidant activities of the seven coumarin-derived compounds were reported for the first time in this dissertation.

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