| Abstrak/Abstract |
The aim of this study was to synthesize C-4-allyloxy-3- methoxyphenylcalix[4]resorcinarene (AMPC) and test its antioxidant activity. This
compound was synthesized through two stages of reaction, i.e. allylation reaction of
4–hydroxy–3-methoxybenzaldehyde to produce 4–allyloxy–3-methoxybenzaldehyde,
followed by the synthesis of AMPC via condensation of 4–allyloxy–3- methoxybenzaldehyde with resorcinol in the presence of hydrochloride as an acid
catalyst. The allylation reaction to 4-hydroxy-3-methoxybenzaldehyde produced 4- allyloxy-3-methoxybenzaldehyde in the form of a light yellow liquid with 79% in yield,
then the condensation reaction of the 4-allyloxy-3-methoxybenzaldehyde with
resorcinol produced the AMPC as brown solid in 78% yield having m.p. of 176–177 °C
(dec.). The resulted AMPC was characterized by means of FTIR, 1H–NMR, and LC–MS
spectrometers. Antioxidant activity of AMPC was determined by scavenging effect on
2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals with quercetin as a control. The
presence of phenol groups caused the antioxidant activity of the AMPC became
different compared to that having no phenol groups. The ES50 value of AMPC was
105.877 µg/mL, while that of C-4-hydroxy-3-methoxyphenylcalix[4]resorcinarene
(HMPC) was 28.208 µg/mL. |
