Uses
1,2-Dioctanoyl-sn-glycerol is a cell permeable analog of the PKC-activating second messenger DAG. 1,2-Dioctanoyl-sn-glycerol and 1,2-dioleoyl-sn-glycerol are nearly equipotent in induction of the acrosome reaction in human sperm.[Cayman Chemical]
Biological Activity
Cell permeable: yes', 'Primary Target
Protein kinase C', 'Reversible: no
Synthesis
Over ten minutes, octanoyl chloride (8.93 g, 54.87 mmol) was added dropwise to a solution of (R)-(+)-3-benzyloxy-1,2-propanediol (4.0 g, 21.95 mmol) in anhydrous pyridine (40 mL) followed by DMAP (267 mg, 2.19 mmol). The reaction mixture was stirred at 55C for 48 h. The reaction mixture was diluted with EtOAc (300 mL), washed sequentially with water (100 mL), 1NHCl (2x100 mL) and brine (100 mL), dried (Na2SO4) and concentrated. The residue was purified on a SiO2 column (3% EtOAc/hexane) to give 7.3 g (75%) of colorless slurry product. Yield 7.3 g (75%).
A solution of the above oil (6.8 g,15.66 mmol) dissolved in EtOH:EtOAc:AcOH (9:1:0.1) (30 mL) was hydrogenated in 10% Pd/C (900 mg, 10%) at 40 psi for 3 hours. The catalyst was filtered over a bed of diatomaceous earth and concentrated to give 1,2-octadecanoyl-SN-glycerol in (5.0,93%) yield.
