SYNTHESIS OF 2-METHOXY-4,6-DI(PROP-1-ENYL)PHENOL FROM EUGENOL AND ITS ACTIVITY AS AN ANTIOXIDANT

https://doi.org/10.22146/ijc.21360

Hernawan Hernawan(1*), Bambang Purwono(2), Tutik Dwi Wahyuningsih(3)

(1) Technical Implementation Unit for Development of Chemical Engineering Processes, Indonesian Institute of Sciences, Gading, Playen, Gunungkidul, Yogyakarta 55861
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281
(*) Corresponding Author

Abstract


Synthesis and antioxidant activity of 2-methoxy-4,6-di(prop-1-enyl) phenol from eugenol have been investigated. Synthesis was conducted through three stages of reaction. The first step was CTAB micellar catalytic O-allylation reaction at room temperature, to give 4-allyl-1-(allyloxy)-2-methoxybenzene (2). Compound (2) was subsequently heated for Claisen rearrangement and produced 2,4-diallyl-6- methoxyphenol (3). The final steps was isomerization of compound (3) in alkaline conditions in ethylene glycol, to yield 2-methoxy-4,6-di(prop-1-enyl) phenol (4). Antioxidant activity test was conducted by TBARS and DPPH methods. TBARS test showed that the compound (4) at a concentration of 50 μM could inhibit the oxidation of linoleic acid shown by the increasing of time lag phase (96 ± 2.94 min), reducing the rate of propagation (± 54.54%) and reducing of malonal dialdehyde (MDA) formation (68.04 ± 0.84%). The DPPH test revealed that compound (4) indicated DPPH free radical scavenging activity with IC50 107.66 μM and comparable with IC50 for BHT 107.37 μM.

Keywords


Claisen rearrangement; DPPH; eugenol; isomerization; O-allylation

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DOI: https://doi.org/10.22146/ijc.21360

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