(±)12(13)-DiHOME

(±)12(13)-DiHOME (CAS No.: 263399-35-5) is an endogenous lipid metabolite derived from linoleic acid via cytochrome P450-mediated epoxidation followed by hydrolysis through soluble epoxide hydrolase, and is widely recognized as a bioactive lipokine involved in the regulation of energy homeostasis and lipid metabolism. It functions as a thermogenic signaling molecule that activates brown adipose tissue, particularly under conditions such as cold exposure or exercise, by promoting the translocation of fatty acid transport proteins FATP1 and CD36 to the plasma membrane, thereby enhancing fatty acid uptake and fuel utilization. This mechanism contributes to increased thermogenesis, improved cold tolerance, and reductions in circulating triglyceride levels in preclinical models. In addition to its metabolic regulatory roles, (±)12(13)-DiHOME has been implicated in inflammatory and stress-related responses, with elevated levels observed in biological fluids following environmental exposure, allergic reactions, and tissue injury, and it has demonstrated cytotoxic effects in certain cellular systems expressing soluble epoxide hydrolase. As a result, this molecule is broadly utilized in studies of metabolic disorders, including obesity and diabetes, as well as in investigations of lipid signaling, mitochondrial function, and immune-metabolic interactions. In vitro and in vivo studies typically employ concentrations in the nanomolar to micromolar range, with specific dosing regimens varying depending on experimental design, making (±)12(13)-DiHOME a valuable tool for mechanistic research and therapeutic target exploration in metabolic disease contexts.