This paper aims at investigating the dissolved gas analysis (DGA) and long-term performance of Environtemp (FR3) and Jatropha Curcas oil (JAT). Thermal stress is applied to both oils in a sealed setup at 150°C for up to 2000 hours and samples are removed and tested at 500 hour intervals. It is observed that FR3 is more prone to stray gassing as compared to JAT. The alterations in the structure of the oils are studied by Fourier-transform infrared spectroscopy (FTIR) and 600 MHz nuclear magnetic resonance (NMR) spectroscopy analyses. The DGA interpretation is done using the Duval triangle, Dornenburg ratios, Rogers ratios and IEC methods. In the proposed study, a regression model for the two types of oils is developed to predict the total dissolved combustible gases with time. The findings show that JAT holds considerable properties of an insulating fluid and is a substitute for mineral insulating oils.