| Summary: | Synthesis and antioxidant activity of 2-methoxy-4,6-di(prop-1-enyl) phenol from
eugenol have been investigated. Synthesis was conducted via three stages of
reaction. The first step reaction was CTAB micellar catalytic O-allylation reaction
at room temperature to give 4-allyl-1-(allyloxy)-2-methoxybenzene (2).
Compound (2) was subsequently heated under Claisen rearrangement to produce
2,4-diallyl-6-methoxyphenol (3). The last step 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 50 μM could inhibit the
oxidation of linoleic acid indicated by the increasing of time lag phase (96 + 2.94
minutes), reducing the rate of propagation (+ 54.54%) and reducing of malonal
dialdehide (MDA) formation (68.04 + 0.84%). In addition, DPPH test revealed
that compound (4) has an activity as anti-DPPH with IC50 101.23 μM comparable
with BHT IC5098.98 μM.
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