1-Octadecyl Lysophosphatidic Acid (sodium salt)

1-Octadecyl Lysophosphatidic Acid (sodium salt) Exclusive

Cayman Chemical Item Number 10010291

1-Octadecyl LPA

Description

1-Octadecyl lysophosphatidic acid (sodium salt) (1-Octadecyl LPA (sodium salt)) is a LPA analog containing stearyl alcohol at the sn-1 position. LPA binds to one of five different G protein-linked receptors to mediate a variety of biological responses including cell proliferation, smooth muscle contraction, platelet aggregation, neurite retraction, and cell motility.^1,2 Alkyl ether-linked LPA derivatives have a higher platelet aggregating activity than the acyl derivatives, most likely stemming from an alkyl-specific LPA receptor. For example, 1-octadecyl LPA has platelet aggregating activity with an EC₅₀ value of 9 nM versus an EC₅₀ value of 177 nM for 1-octadecanoyl LPA.³

1 Noguchi, K., Ishii, S., and 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).

2 Moolenaar, W.H. LPA: A novel lipid mediator with diverse biological actions. Trends Cell Biol 4 213-219 (1994).

3 Tokumura, A., Sinomiya, J., Kishimoto, S., et al. Human platelets respond differentially to lysophosphatidic acids having a highly unsaturated fatty acyl group and alkyl ether-linked lysophosphatidic acids. Biochem J 365 617-628 (2002).

Synonyms

1-Octadecyl LPA

Formal Name

1-O-octadecyl-2-hydroxy-sn-glycero-3-phosphate, monosodium salt

Molecular Formula

C₂₁H₄₄O₆P · Na

Formula Weight

446.5

Formulation

A crystalline solid

Purity

≥95%

Stability

2 years

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

Copy SMILES to clipboard

[Na].CCCCCCCCCCCCCCCCCCOC[C@@H](O)COP(=O)(O)O

Background Reading

Noguchi, K., Ishii, S., and 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).

Moolenaar, W.H. LPA: A novel lipid mediator with diverse biological actions. Trends Cell Biol 4 213-219 (1994).

Tokumura, A., Sinomiya, J., Kishimoto, S., et al. Human platelets respond differentially to lysophosphatidic acids having a highly unsaturated fatty acyl group and alkyl ether-linked lysophosphatidic acids. Biochem J 365 617-628 (2002).

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1-Octadecyl Lysophosphatidic Acid (sodium salt) Exclusive