Synthesis of Linoleic Acid 13-Hydroperoxides from Safflower Oil Utilizing Lipoxygenase in a Coupled Enzyme System with In-Situ Oxygen Generation

Linoleic acid hydroperoxides are versatile intermediates for the production of green note aroma compounds and bifunctional ω-oxo-acids. An enzyme cascade consisting lipoxygenase, lipase catalase was developed one-pot synthesis 13-hydroperoxyoctadecadienoic starting from safflower oil. Reaction conditions were optimized hydroperoxidation using lipoxygenase 1 Glycine max (LOX-1) in a solvent-free system. The addition surfactant Triton CG-110 improved reaction more than two-fold yields >50% obtained at linoleic concentrations up to 100 mM. To combine oil hydrolysis, 12 lipases screened hydrolysis under LOX-1. Lipases Candida rugosa Pseudomonas fluorescens able hydrolyze >75% within 5 h pH 8.0. In contrast C. lipase, P. did not exhibit lag phase. Combination LOX-1 worked well upon dosage synergistic effect observed leading >80% hydroperoxides. Catalase Micrococcus lysodeikticus used in-situ oxygen with continuous H2O2 LOX-1/lipase Foam generation significantly reduced 3-enzyme comparison aerated Safflower concentration increased 300 mM equivalent 13-hydroperoxides could be produced yield 70 g/L regioselectivity 90% 7 h.