Synthesis of 4-Hydroxy-2-Methylchalcone from meta-Cresol Formilation Product and Its Activities as an Antibacteria

DOI: https://doi.org/10.14710/jksa.21.4.193-197

Creative Commons License
This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.

Article Metrics: (Click on the Metric tab below to see the detail)

Article Info
Published: 31-10-2018
Section: Research Articles
Fulltext PDF Tell your colleagues Email the author

Research on the synthesis of 4-hydroxy-2-methylchalcone from 4-hidroksi-2-metilbenzaldehida as formilated meta-cresol product and its antibacterial activity test has been conducted. As the first step, synthesis of 4-hydroxy-2-methylbenzaldehyde was carried out by treatment meta-cresol with chloroform through the Reimer-Tiemann formylation. Product is a brown solid with 23.94% yields. Furthermore, the 4-hydroxy-2-methylchalcone was synthesized using the 4-hydroxy-2-methylbenzaldehyde and acetophenone through the Claisen-Schmidt reaction. The product is a brownish yellow solid with 29.74% yields. Antibacterial test against Escherichia coli and Staphylococcus aureus bacteria was carried out by comparing the activity of 4-hydroxy-2-methylchalcone with 4-hydroxy-3-methoxychalcone, and chalcone compounds. The antibacterial activity test showed that the 4-hydroxy-2-methylchalcone compound, 4-hydroxy-3-methoxychalcone, and chalcone compounds gave a better antibacterial activity against Escherichia coli than the Staphylococcus aureus.

Keywords

Claisen-Schmidt; Chalcone; Reimer-Tiemann; Antibacterial

  1. Ismiyarto Ismiyarto  Scopus Sinta
    Chemistry Department, Faculty of Sciences and Mathematics, Diponegoro University Jl. Prof. Soedarto, SH., Tembalang, Semarang, Indonesia
  2. Suyanti Suyanti 
    Chemistry Department, Faculty of Sciences and Mathematics, Diponegoro University Jl. Prof. Soedarto, SH., Tembalang, Semarang, Indonesia
  3. Ngadiwiyana Ngadiwiyana  Scopus Sinta
    Chemistry Department, Faculty of Sciences and Mathematics, Diponegoro University Jl. Prof. Soedarto, SH., Tembalang, Semarang, Indonesia
  4. Purbowatiningrum Ria Sarjono  Orcid Scopus Sinta
    Chemistry Department, Faculty of Sciences and Mathematics, Diponegoro University Jl. Prof. Soedarto, SH., Tembalang, Semarang, Indonesia
  5. Nor Basid Adiwibawa Prasetya  Orcid Scopus Sinta
    Chemistry Department, Faculty of Sciences and Mathematics, Diponegoro University Jl. Prof. Soedarto, SH., Tembalang, Semarang, Indonesia
  1. M. Hapsari, Tri Windarti, Purbowatiningrum Ria Sarjono, Ngadiwiyana, Ismiyarto, Synthesis of 4-hydroxy-3-methylchalcone from Reimer-Tiemann reaction product and its antibacterial activity test, IOP Conference Series: Materials Science and Engineering, 349, 1, (2018) 012036 https://doi.org/10.1088/1757-899X/349/1/012036
  2. Rajat Ghosh, Abhijit Das, Synthesis and biological activities of chalcones and their heterocyclic derivatives: a review, World Journal of Pharmacy and Pharmaceutical Sciences, 3, 3, (2014) 578-595
  3. Kishor V Gaikwad, Sandip V Gaikwad, Satish B Jadhav, Shantilal D Rathod, Synthesis of some novel chalcones of phthalimidoester possessing good anti-inflammatory and antimicrobial activity, Indian Jurnal of Chemistry, 49B, (2010) 131-136
  4. B. B. Chavan, A. S. Gadekar, P. P. Mehta, P. K. Vawhal, A. K. Kolsure, A. R. Chabukswar, Synthesis and Medicinal Signifiance of Chalcones- A Review, Asian Journal of Biomedical and Pharmaceutical Sciences, 6, 56, (2016) 1-7
  5. Hery Suwito, Jumina, Mustofa, Alfinda Novi Kristanti, Ni Nyoman Tri Puspaningsih, Chalcones: Synthesis, structure diversity and pharmacological aspects, Journal of Chemical and Pharmaceutical Research, 6, 5, (2014) 1075-1088
  6. V. M. Kamble, G. D. Hatnapure, A. P. Keche, S. Birajdar, S. G. Patil, R. H. Tale, A. H. Rodge, S. S. Turkar, K. Gour, Synthesis and biological evaluation of a novel series of methoxylated chalcones as antioxidant and anti-microbial agents, Journal of Chemical and Pharmaceutical Research, 3, 6, (2011) 639-648
  7. E. P. Kohler, H. M. Chadwell, Organic Syntheses, in, 1941.
  8. Madiyono, Sintesis Senyawa 4-hidroksi-3-metoksikalkon dari Vanilin dan Asetofenon, Departemen Kimia, Universitas Diponegoro, Semarang