Due to rapid expansion of derivatization based separation techniques for the trace determination of biomedical analytes, the use of combination of separation techniques and pre and post-column derivatization procedures following by UV or fluorescence detection remains the most convenient and wide spread analytical approach. 3(2H)-Furanones are a type of biologically important five-membered heterocyclic compounds and has not yet been exploited for any analytical application. By taking advantage of this fact, a novel fluorescent dye (3-[5-(4 Dimethylamino-phenyl)-3-oxo-3H-furan-2-ylidenemethyl)-benzoic acid, DMAFB) based on 3(2H)-furanone skeleton was designed and synthesized. Despite recent developments, the determination of many drugs and naturally occurring compounds through their hydroxyl group and amino group remains challenging. In this compound we are considering carboxylic acid moiety as a trigger, which has the potential to be tagged with biomolecules through functional group conversion. Furthermore, photophysical properties of DMAFB were studied and interesting solvatochromic behaviour was observed. Due to the presence of proton acceptor, DMAFB displays pH-sensitive emission characteristics. The interaction of DMAFB with various micelles has been studied by steady state fluorescence. Moreover, the results obtained from the quantum chemical calculations supported the experimentally observed properties of the title compound. All the preliminary results that were obtained from this study prove that 3-furanone could be an interesting template for the design of novel organic fluorescent dyes, which are potentially applicable for bio-analytical purposes.