Utilization of cinnamaldehyde for synthesis of nitrogen-containing 2-hydroxy-1,4-naphthoquinone derivatives as antioxidant agent

N. Nurhikmah, A. H. Cahyana, A. R. Liandi

Research output: Chapter in Book/Report/Conference proceedingConference contributionpeer-review

Abstract

Cinnamaldehyde is the main compound in the cinnamon (Cinnamomum burmanii) that mostly applied in the essence and aroma industries and can be used as a medicinal product because of its bioactivities. This study aims to modify the cinnamaldehyde compound to 2-hydroxy-1,4-naphthoquinone derivatives containing nitrogen and test their bioactivity as an antioxidant. The synthesis of 2-hydroxy-1,4-naphthoquinone derivatives compounds was conducted which involves the precursors aromatic aldehyde variations (benzaldehyde, cinnamaldehyde, and 4-hydroxy benzaldehyde), and lawsone using iodine catalyst. The products were confirmed by UV-Vis, FTIR, and GC-MS obtained three 2-hydroxy-1,4- naphthoquinone derivatives, namely 2-(hydrazino-phenyl-methyl)-3-hydroxy-2,3-dihydro-[1,4]naphthoquinone (compound 1), 2-(1-hydrazino-3-phenyl-allyl)-3-hydroxy-2,3-dihydro-[1,4]naphthoquinone (compound 2), and 2-[hydrazino-(4-hydroxy-phenyl)-methyl]-3-hydroxy-2,3-dihydro-[1,4]naphthoquinone (compound 3) with yield 91.04, 82.62 and 87.22, respectively. IC50 values of compounds 1 and 2 are 204.94 and 139.06, which indicates that compound 2 is more active in antioxidants than compound 1.

Original languageEnglish
Title of host publicationProceedings of the 5th International Symposium on Current Progress in Mathematics and Sciences, ISCPMS 2019
EditorsTerry Mart, Djoko Triyono, Tribidasari Anggraningrum Ivandini
PublisherAmerican Institute of Physics Inc.
ISBN (Electronic)9780735420014
DOIs
Publication statusPublished - 1 Jun 2020
Event5th International Symposium on Current Progress in Mathematics and Sciences, ISCPMS 2019 - Depok, Indonesia
Duration: 9 Jul 201910 Jul 2019

Publication series

NameAIP Conference Proceedings
Volume2242
ISSN (Print)0094-243X
ISSN (Electronic)1551-7616

Conference

Conference5th International Symposium on Current Progress in Mathematics and Sciences, ISCPMS 2019
Country/TerritoryIndonesia
CityDepok
Period9/07/1910/07/19

Keywords

  • 2-hydroxy-1
  • 4-naphthoquinone
  • antioxidant activity
  • iodine
  • Lawsonia inermis

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