UMBELLIFERYL ARACHIDONATE Chemical Properties

Boiling point:

584.7±50.0 °C(Predicted)

Density 

1.052±0.06 g/cm3(Predicted)

Flash point:

14 °C

storage temp. 

−20°C

solubility 

≤25mg/ml in DMSO;50mg/ml in dimethyl formamide

form 

ethanol solution

Safety Information

Hazard Codes 

F,Xi

Risk Statements 

11-36/37/38

Safety Statements 

7-16-26-36

RIDADR 

UN 1170 3/PG 2

WGK Germany 

1

MSDS

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UMBELLIFERYL ARACHIDONATE Usage And Synthesis

Uses

7-hydroxycoumarinyl Arachidonate is the arachidonic acid ester of 7-hydroxycoumarin (umbelliferone) and behaves as a substrate for cPLA2. Hydrolysis of 7-hydroxycoumarinyl arachidonate by phospholipase results in the release of the fluorescent compound 7-hydroxycoumarin which can be monitored spectrophotometrically (excitation at 335 nm, emission at 450 nm).

Uses

7-HC-arachidonate is a PLA2 fluorogenic substrate for use in assays with phospholipid and Ca2+. It is for use with purified enzymes, as this substrate is nonspecific. 7-HC-arachidonate is ideal for drug discovery, HTS, and similar applications.

Biological Activity

7-hydroxycoumarinyl-arachidonate (7-hca), a fluorogenic substrate for monoacylglycerol lipase (magl), can be used with magl as a novel fluorescence-based assay to screen small molecule inhibitors of magl.magl protein catalyzed the hydrolysis of 7-hca to generate arachidonic acid and the highly fluorescent 7-hydroxyl coumarin (7-hc). 7-hydroxycoumarin (7-hc) can be monitored spectrophotometrically (excitation at 335 nm, emission at 450 nm). release of 7-hc was measured using a fluorometer. magl protein catalyzed the hydrolysis of 7-hca with an apparent km of 9.8 μm and vmax of 1.7 mmol/min/mg of protein. the assay is specific for magl as assay buffer alone or heat-denatured magl protein showed no significant activity against 7-hca [1]. 7-hydroxycoumarinyl arachidonate is the arachidonic acid ester of 7-hydroxycoumarin (umbelliferone) and can be used as a substrate for cpla2. hydrolysis of 7-hydroxycoumarinyl arachidonate by phospholipase resulted in the release of the fluorescent compound [2,3].

References

[1]. wang y, chanda p, jones p g, et al. a fluorescence-based assay for monoacylglycerol lipase compatible with inhibitor screening[j]. assay and drug development technologies, 2008, 6(3): 387-393.
[2]. huang z, laliberte f, tremblay n m, et al. a continuous fluorescence-based assay for the human high-molecular-weight cytosolic phospholipase a2[j]. analytical biochemistry, 1994, 222(1): 110-115.
[3]. pickard r t, chiou x g, strifler b a, et al. identification of essential residues for the catalytic function of 85-kda cytosolic phospholipase a2 probing the role of histidine, aspartic acid, cysteine, and arginine[j]. journal of biological chemistry, 1996, 271(32): 19225-19231.

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