SINTESIS DAN AKTIVITAS ANTIOKSIDAN SENYAWA 2-METOKSI- 4,6-DI(PROP-1-ENIL) FENOL DARI EUGENOL

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-methoxybe...

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Main Authors: , Hernawan, , Drs. Bambang Purwono, M.Sc, Ph.D
Format: Thesis
Published: [Yogyakarta] : Universitas Gadjah Mada 2011
Subjects:
ETD
_version_ 1797032058920370176
author , Hernawan
, Drs. Bambang Purwono, M.Sc, Ph.D,
author_facet , Hernawan
, Drs. Bambang Purwono, M.Sc, Ph.D,
author_sort , Hernawan
collection UGM
description 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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spelling oai:generic.eprints.org:973912016-03-04T08:49:58Z https://repository.ugm.ac.id/97391/ SINTESIS DAN AKTIVITAS ANTIOKSIDAN SENYAWA 2-METOKSI- 4,6-DI(PROP-1-ENIL) FENOL DARI EUGENOL , Hernawan , Drs. Bambang Purwono, M.Sc, Ph.D, ETD 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. [Yogyakarta] : Universitas Gadjah Mada 2011 Thesis NonPeerReviewed , Hernawan and , Drs. Bambang Purwono, M.Sc, Ph.D, (2011) SINTESIS DAN AKTIVITAS ANTIOKSIDAN SENYAWA 2-METOKSI- 4,6-DI(PROP-1-ENIL) FENOL DARI EUGENOL. UNSPECIFIED thesis, UNSPECIFIED. http://etd.ugm.ac.id/index.php?mod=penelitian_detail&sub=PenelitianDetail&act=view&typ=html&buku_id=53986
spellingShingle ETD
, Hernawan
, Drs. Bambang Purwono, M.Sc, Ph.D,
SINTESIS DAN AKTIVITAS ANTIOKSIDAN SENYAWA 2-METOKSI- 4,6-DI(PROP-1-ENIL) FENOL DARI EUGENOL
title SINTESIS DAN AKTIVITAS ANTIOKSIDAN SENYAWA 2-METOKSI- 4,6-DI(PROP-1-ENIL) FENOL DARI EUGENOL
title_full SINTESIS DAN AKTIVITAS ANTIOKSIDAN SENYAWA 2-METOKSI- 4,6-DI(PROP-1-ENIL) FENOL DARI EUGENOL
title_fullStr SINTESIS DAN AKTIVITAS ANTIOKSIDAN SENYAWA 2-METOKSI- 4,6-DI(PROP-1-ENIL) FENOL DARI EUGENOL
title_full_unstemmed SINTESIS DAN AKTIVITAS ANTIOKSIDAN SENYAWA 2-METOKSI- 4,6-DI(PROP-1-ENIL) FENOL DARI EUGENOL
title_short SINTESIS DAN AKTIVITAS ANTIOKSIDAN SENYAWA 2-METOKSI- 4,6-DI(PROP-1-ENIL) FENOL DARI EUGENOL
title_sort sintesis dan aktivitas antioksidan senyawa 2 metoksi 4 6 di prop 1 enil fenol dari eugenol
topic ETD
work_keys_str_mv AT hernawan sintesisdanaktivitasantioksidansenyawa2metoksi46diprop1enilfenoldarieugenol
AT drsbambangpurwonomscphd sintesisdanaktivitasantioksidansenyawa2metoksi46diprop1enilfenoldarieugenol