A potent LPA receptor agonist
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1-Oleoyl-2-hydroxy-sn-glycero-3-PA

Item No. 10010093

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-O-9Z-octadecenoyl-sn-glyceryl-3-phosphoric acid
CAS Number
65528-98-5
Synonyms
  • 18:1 LPA
  • LPA 18:1
  • 1-Octadecenoyl-2-hydroxy-sn-glycero-3-phosphate
  • 1-Oleoyl LPA
  • 1-Oleoyl Lysophosphatidic Acid
  • PA(18:1/0:0)
Molecular Formula
C21H41O7P
Formula Weight
436.5
Purity
≥95%
Formulation
A 10 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
Ethanol: Soluble: ≥10 mg/mlEthanol:PBS (pH 7.2) (1:9): Slightly soluble: 0.1-1 mg/ml
SMILES
CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)O
InChi Code
InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26)/b10-9-/t20-/m1/s1
InChi Key
WRGQSWVCFNIUNZ-GDCKJWNLSA-N
Side Chain Carbon Sum
18:1
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $33

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    5 mg

    $149

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    10 mg

    $264

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    25 mg

    $578

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    Product Description

    1-Oleoyl-2-hydroxy-sn-glycero-3-PA (1-Oleoyl LPA) is a species of lysophosphatidic acid (LPA) containing oleic acid at the sn-1 position. Phosphatidic acid is produced either directly through the action of phospholipase D (PLD) or through a two step process involving liberation of diacylglycerol (DAG) by phospholipase C (PLC) followed by phosphorylation of DAG by diglycerol kinase.1 Hydrolysis of the fatty acid at the sn-2 position by phospholipase A2 (PLA2) yields bioactive LPA. 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.2,1 1-Oleoyl lysophosphatidic acid is the most potent of the LPA analogs for calcium mobilization in A431 cells and for growth stimulation of a variety of cell lines.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Moolenaar, W.H. LPA: A novel lipid mediator with diverse biological actions. Trends Cell Biol. 4(6), 213-219 (1994).

    2. 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. The Journal of Biological Chemisty 278(28), 25600-25606 (2003).

    3. Jalink, K., Hengeveld, T., Mulder, S., et al. Lysophosphatidic acid-induced Ca2+ mobilization in human A4431 cells: Structure-activity analysis. Biochem. J. 307, 609-616 (1995).

    4. van Corven, E.J., van Rijswijk, A., Jalink, K., et al. Mitogenic action of lysophosphatidic acid and phosphatidic acid on fibroblasts. Dependence on acyl-chain length and inhibition by suramin. Biochem. J. 281, 163-169 (1992).