Recovery and purification of 10-oxo-trans-8-decenoic acid enzymatically produced using a crude homogenate of Agaricus bisporus

A two-step method was developed to recover 10-oxo-trans-8-decenoic acid (ODA) at 85% purity using GRAS solvents that may be used either at laboratory or industrial scale. ODA was recovered from an aqueous reaction broth via extraction with ethyl acetate followed by evaporation. The residue was dissolved in hot hexane and subsequently crystallized at 5°C. Optimal recovery of ODA from the reaction broth was optimized by determining the partition coefficient between phosphate buffer (range pH 2.0 to 7.5) and ethyl acetate. The intrinsic partition coefficients were 75.38 and 1.43 for the undissociated and dissociated forms, respectively. To obtain a good recovery, the optimal pH was determined to be 3.0. Purification was optimized by determining the solubility curve of ODA in hexane as a function of temperature. The solubility of ODA in hexane decreased from 0.7 mg/mL at 50°C to 0.05 mg/mL at 10°C. The solubility at intermediate temperatures followed a linear van't Hoff model, indicating an approximately constant enthalpy of solution. Even when the solubility of ODA in hexane is relatively low, the temperature-solubility profile was adequate to recrystallize ODA.