A lysophosphatidic acid analog
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1-Octadecyl-2-hydroxy-sn-glycero-3-phosphate

Item No. 10010164

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-(octadecyloxy)-1-(dihydrogen phosphate)-1,2-propanediol
CAS Number
52977-29-4
Synonyms
  • LPA O-18:0
  • O-18:0 LPA
  • 1-Octadecyl-2-hydroxy-sn-glycero-3-PA
  • 1-Octadecyl LPA
  • 1-Octadecyl Lysophosphatidic Acid
  • 1-Oleyl LPA
  • 1-Oleyl Lysophosphatidic Acid
  • PA(O-18:0/0:0)
  • 1-Stearyl-2-hydroxy-sn-glycero-3-PA
Molecular Formula
C21H45O6P
Formula Weight
424.6
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 10 mg/mlEthanol:PBS (pH 7.2) ((1:1): 0.5 mg/ml
SMILES
CCCCCCCCCCCCCCCCCCOC[C@@H](O)COP(O)(O)=O
InChi Code
InChI=1S/C21H45O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-26-19-21(22)20-27-28(23,24)25/h21-22H,2-20H2,1H3,(H2,23,24,25)/t21-/m1/s1
InChi Key
HUUYDUFSUADEJQ-OAQYLSRUSA-N
Side Chain Carbon Sum
18:0
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $29

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    1 mg

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    5 mg

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    10 mg

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    Product Description

    1-Octadecyl-2-hydroxy-sn-glycero-3-phosphate (1-Octadecyl LPA) is a LPA analog containing stearic acid 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 a platelet aggregating EC50 value of 9 nM versus 1-octadecanoyl LPA which has an EC50 value of 177 nM.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

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

    2. Moolenaar, W.H. LPA: A novel lipid mediator with diverse biological actions. Trends Cell Biol. 4(6), 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(Pt 3), 617-628 (2002).