Tetradecyl Phosphonate CAS: 4671-75-4
MF: C14H31O3P
MW: 278.37
A pan-antagonist of EDG-2, EDG-4, and EDG-7.

Tetradecyl Phosphonate (CAS 4671-75-4)

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Alternate Names: n-Tetradecylphosphonic acid; 1-Tetradecanephosphonic acid
Application: Tetradecyl Phosphonate is a pan-antagonist of EDG-2, EDG-4, and EDG-7
CAS Number: 4671-75-4
Molecular Weight: 278.37
Molecular Formula: C14H31O3P
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data (including water content).

Tetradecyl Phosphonate is a pan-antagonist of EDG-2, EDG-4, and EDG-7 (EDG-2, EDG-4, and EDG-7 receptors) with IC50 values for inhibition of EDG-induced calcium mobilization of 10 μM, 5.5 μM, and 3.1 μM, respectively. Tetradecyl Phosphonate is an inhibitor of Autotaxin.


References

1 Tokumura, A., Majima, E., Kariya, Y., et al. Identification of human lysophospholipase D, a lysophosphatidic acid-producing enzyme, as autotaxin, a multifunctional phosphodiesterase. J Biol Chem 277(42) 39436-39442 (2002 Oct 18). 2 Chun, J., Goetzl, E.J., Hla, T., et al. International union of pharmacology. XXXIV. Lysophospholipid receptor nomenclature. Pharmacol Rev 54 265-269 (2002). 3 Noguchi, K., Ishii, S., Shimizu, T. Identification of p2y9/GPR23 as a novel G protein-coupled receptor for lysophosphatidic acid, structurally distant from the Edg family. J Biol Chem 278(28) 25600-25606 (2003). 4 McIntyre, T.M., Pontsler, A.V., Silva, A.R., et al. Identification of an intracellular receptor for lysophosphatidic acid (LPA): LPA is a transcellular PPARγ agonist. Proc Natl Acad Sci USA 100(1) 131-136 (2003). 5 Durgam, G.G., Virag, T., Walker, M.D., et al. Synthesis, structure-activity relationships, and biological evaluation of fatty alcohol phosphates as lysophosphatidic acid receptors ligands, activators of PPARγ, and inhibitors of autotaxin. J Med Chem 48 4919-4930 (2005).

Physical State :
Solid
Solubility :
Soluble in ethanol (~30 mg/ml), DMSO (~2 mg/ml), DMF (~5 mg/ml), aqueous buffers (sparingly), and water (0.25 mg/ml at 25° C).
Storage :
Store at -20° C
Melting Point :
99-101° C
Boiling Point :
~411.2° C at 760 mmHg (Predicted)
Density :
~1.0 g/cm3 (Predicted)
Refractive Index :
n20D 1.46 (Predicted)
IC50 :
Autotaxin: IC50 = ~3 µM; EDG-7: IC50 = 3.1 µM (human); EDG-4: IC50 = 5.5 µM (human); LPA-induced calcium transients: IC50 = 9.67 µM (PC-3 cells); EDG-2: IC50 = 10 µM
Ki Data :
EDG-7: Ki= 1.12 µM (human); EDG-4: Ki= 3.55 µM (human); Binding affinity for Lysophosphatidic acid receptor: Ki= 4.62 µM (PC-3 cells)
pK Values :
pKa: 2.65 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
2
PubChem CID :
78401
MDL Number :
MFCD00015834
EC Number :
225-118-1
Beilstein Registry :
1784271
SMILES :
CCCCCCCCCCCCCCP(=O)(O)O

Download SDS (MSDS)

Certificate of Analysis

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