Dioleoylglycerol, commonly known as 1,2-dioleoyl-sn-glycerol (DOG) or diolein, is a diacylglycerol (DAG) species featuring two oleic acid (C18:1 cis-9) chains esterified at the sn-1 and sn-2 positions of glycerol. This unsaturated DAG acts as a second messenger analog and lipid model compound, extending properties from saturated DPG and the broader DAG family in signaling and membrane studies.

Chemical Structure

DOG has the molecular formula C39H72O5 and a molecular weight of 621.0 g/mol. Its chiral sn-glycerol backbone with symmetric monounsaturated oleoyl chains creates a conical geometry (packing parameter <1), favoring inverted hexagonal and cubic phases due to unsaturation-induced fluidity, distinct from lamellar-prone DPG.

Physical Properties

Appearing as a colorless to pale yellow liquid at room temperature (melting point ~12°C, density 0.89-0.92 g/cm³ at 50°C), DOG exhibits high lipophilicity (XLogP3-AA ~13-14) and solubility in ethanol, chloroform, and DMSO but insolubility in water. It hydrolyzes via lipases to release oleic acid and glycerol, with stability enhanced under inert conditions.

Biological Functions

As a 1,2-DAG regioisomer, DOG activates protein kinase C (PKC) isoforms and recruits C1-domain proteins like chimaerins and protein kinase D, mimicking phospholipase C signals in lipid metabolism and vesicle trafficking. Its fluid chains promote membrane fusion and nonlamellar transitions, influencing adipose tissue structure and DAG lipase inhibition studies.