A glycerophospholipid
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1-Linoleoyl-2-hydroxy-sn-glycero-3-PA (sodium salt)

Item No. 38309

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9Z,12Z-octadecadienoic acid, 2R-hydroxy-3-(phosphonooxy)propyl ester, sodium salt
CAS Number
72777-86-7
Synonyms
  • 1-Linoleoyl LPA
  • 1-Linoleoyl Lysophosphatidic Acid
  • LPA 18:2
  • 18:2 LPA
  • 1-Octadecadienoyl-2-hydroxy-sn-glycero-3-phosphate
  • PA(18:2/0:0)
Molecular Formula
C21H39O7P • XNa
Formula Weight
434.5
Purity
≥95% (9:1 mixture of 1-acyl and 2-acyl)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Methanol: Soluble
SMILES
O=C(CCCCCCC/C=C\C/C=C\CCCCC)OC[C@@H](O)COP(O)(O)=O.[Na]
InChi Code
InChI=1S/C21H39O7P.Na/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;/h6-7,9-10,20,22H,2-5,8,11-19H2,1H3,(H2,24,25,26);/b7-6-,10-9-;/t20-;/m1./s1
InChi Key
CLFDTXJHXXYCFR-OOCWZJBTSA-N
Side Chain Carbon Sum
18:2
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    1-Linoleoyl-2-hydroxy-sn-glycero-3-PA (sodium salt) (1-linoleoyl LPA) is an agonist of the LPA2 receptor and a glycerophospholipid containing linoleic acid (Item Nos. 90150 | 90150.1 | 21909) at the sn-1 position.1 It is the most abundant LPA in mouse and human plasma.2,3 1-Linoleoyl LPA selectively increases intracellular calcium levels in LPA2 receptor-expressing Sf9 cells (EC50 = ~10 nM) over LPA1 and LPA3 receptor-expressing Sf9 cells (EC50s = ~200 and ~80 nM, respectively).1 Serum levels of 1-linoleoyl LPA are increased in mice bearing NCTC clone 2472 tumors.4 Plasma 1-linoleoyl LPA levels are decreased in patients with primary progressive, but not relapsing-remitting, multiple sclerosis and are negatively correlated with neurological deficit severity.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bandoh, K., Aoki, J., Taira, A., et al. Lysophosphatidic acid (LPA) receptors of the EDG family are differentially activated by LPA species. Structure-activity relationship of cloned LPA receptors. FEBS Lett. 478(1-2), 159-165 (2000).

    2. Baker, D.L., Desiderio, D.M., Miller, D.D., et al. Direct quantitative analysis of lysophosphatidic acid molecular species by stable isotope dilution electrospray ionization liquid chromatography-mass spectrometry. Anal. Biochem. 292(2), 287-295 (2001).

    3. Kano, K., Matsumoto, H., Kono, N., et al. Suppressing postcollection lysophosphatidic acid metabolism improves the precision of plasma LPA quantification. J. Lipid Res. 62, 100029 (2021).

    4. Khasabova, I.A., Khasabov, S.G., Johns, M., et al. Exosome-associated lysophosphatidic acid signaling contributes to cancer pain. Pain 164(12), 2684-2695 (2023).

    5. Amatruda, M., Petracca, M., Wentling, M., et al. Retrospective unbiased plasma lipidomic of progressive multiple sclerosis patients-identifies lipids discriminating those with faster clinical deterioration. Sci. Rep. 10(1), 15644 (2020).