Untargeted synthesis leading to the formation of a significant product is a common practiceand has been successfully achieved after holistic characterization of the accidentally formed molecule ofthe trimer of pyrazolone. Its significance was further explored in the pharmaceutical field emphasizing theneed for the synthesis and validating the newly established pathways for its synthesis. It was known thatpyrazolone exhibit a plethora of applications ranging from catalysis, decolourisation of dyes and metallurgicalextractions. Paramount importance has been attributed to pyrazolones in recent years for theirbroad-spectrum biological activities manifested in their anti-inflammatory, analgesic, anticancer and antitubercularfunctions. In the ongoing research 4,4-Bis-(3-methyl-phenyl-pyrozolin-5-on-4-yl)-3-methyl-1-phenyl-pyrzolin-5-one was synthesized economically and efficiently via a novel one-step bio-catalyticpathway using laccase as a catalyst. To validate the utility of our accidental discovery, we have alsocalculated its antioxidant activity against ascorbic acid as a standard compound. DPPH and ABTS havebeen used to study the scavenging of free radicals in-vitro. This is the first report of the enzyme drivensynthesis of trimeric form of pyrazolone. These results will emphasise the utilization of pyrazolonetrimers as eco-friendly compounds which exhibit a promising natural antioxidant property in physiologicalenvironments.