A phospholipid
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1-Arachidonoyl-2-hydroxy-sn-glycero-3-PA (sodium salt)

Item No. 10019

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5Z,8Z,11Z,14Z)-eicosatetraenoic acid, (2R)-hydroxy-3-(phosphonooxy)propyl ester, monosodium salt
Synonyms
  • 1-Arachidonoyl LPA
  • 1-Arachidonoyl Lysophosphatidic Acid
  • 1-Eicosatetraenoyl-2-hydroxy-sn-glycero-3-phosphate
  • 20:4 LPA
  • LPA 20:4
  • PA(20:4/0:0)
Molecular Formula
C23H38O7P • Na
Formula Weight
480.5
Purity
≥95%
Formulation (Request formulation change)
A semi-solid
Solubility(Learn about Variance in Solubility)
Methanol: Sparingly soluble
SMILES
O[C@@H](COP([O-])(O)=O)COC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O.[Na+]
InChi Code
InChI=1S/C23H39O7P.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(25)29-20-22(24)21-30-31(26,27)28;/h6-7,9-10,12-13,15-16,22,24H,2-5,8,11,14,17-21H2,1H3,(H2,26,27,28);/q;+1/p-1/b7-6-,10-9-,13-12-,16-15-;/t22-;/m1./s1
InChi Key
UOFILYTVJUFTBJ-PWZWHAFSSA-M
Side Chain Carbon Sum
20:4
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    500 µg

    $53

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    1 mg

    $101

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    5 mg

    $423

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    10 mg

    $792

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    Product Description

    1-Arachidonoyl-2-hydroxy-sn-glycero-3-PA is a phospholipid containing arachidonic acid at the sn-1 position. It has been found in rat brain as 37% of the arachidonic acid-containing lysophosphatidic acid (LPA) species and is a precursor to 1-arachidonoyl glycerol (1-AG; Item No. 62150).1 1-Arachidonoyl-2-hydroxy-sn-glycero-3-PA binds to the LPA2/EDG4 receptor with an EC50 value of approximately 10 nM.2 It prevents TNF-α and IL-6 secretion in wild-type but not Lpa2-/- dendritic cells stimulated by LPS.3 It also decreases differentiation of HT-29 human colon carcinoma cells to goblet cells in the presence of sodium butyrate.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nakane, S., Oka, S., Arai, S., et al. 2-Arachidonoyl-sn-glycero-3-phosphate, an arachidonic acid-containing lysophosphatidic acid: occurrence and rapid enzymatic conversion to 2-arachidonoyl-sn-glycerol, a cannabinoid receptor ligand, in rat brain. Arch. Biochem. Biophys. 402(1), 51-58 (2002).

    2. 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).

    3. Emo, J., Meednu, N., Chapman, T.J., et al. Lpa2 is a negative regulator of both dendritic cell activation and murine models of allergic lung inflammation. J. Immunol. 188(8), 3784-3790 (2012).

    4. Hidaka, M., Nishihara, M., and Tokumura, A. Three lysophosphatidic acids with a distinct long chain moiety differently affect cell differentiation of human colon epithelial cells to goblet cells. Life Sci. 197, 73-79 (2018).