Synthesis of 4-hydroxy-3-methylchalcone from Reimer-Tiemann reaction product and its antibacterial activity test

12th Joint Conference on Chemistry

Hapsari, M.^1 ; Windarti, T.^1 ; Purbowatiningrum^1 ; Ngadiwiyana^1 ; Ismiyarto^1

Organic Chemistry Laboratorium, Chemistry Departement, Faculty of Sciences, Mathematics Diponegoro University, Indonesia^1

关键词: Acetophenones;    Anti-bacterial activity;    Chalcone derivatives;    Disc diffusion methods;    Gram-positive bacterium;    Solid forms;    Staphylococcus aureus;   

Others  :  https://iopscience.iop.org/article/10.1088/1757-899X/349/1/012036/pdf
DOI  :  10.1088/1757-899X/349/1/012036

来源: IOP

【 摘 要 】

A 4-hydroxy-3-methylchalcone has been synthesized from 4-hydroxy-3-methylbenzaldehyde as the Reimer-Tiemann reaction product. This research consists of three steps involve synthesize of 4-hydroxy-3-methylbenzaldehyde from ortho-cresol, synthesize of chalcone derivatives from 4-hydroxy-3-methylbenzaldehyde and 4-hydroxy-3-methoxybenzaldehyde or vanillin for the comparison, the last is antibacterial activity test of both chalcone derivatives against Escherichia coli (negative gram) and Staphylococcus aureus (positive gram) bacteria using disc diffusion method. Results of Reimer-Tiemann reaction is 4-hydroxy-3-methylbenzaldehyde compound in an orange colour solid form which has 43% yields and melting point 110-114°C. A 4-hydroxy-3-methylbenzaldehyde then reacted with acetophenone in a base condition and form 4-hydroxy-3-methylchalcone compound in a yellow colour solid form which has 40% yields and melting point 83-86°C. The antibacterial activity of the 4-hydroxy-3-methylchalcone against gram-positive bacteria Staphylococcus aureus is better than the 4-hydroxy-3-methoxychalcone.