1-Arachidonoyl-2-hydroxy-sn-glycero-3-PA  (Synonyms: 1-Arachidonoyl-sn-glycerol 3-phosphate; 1-Arachidonoyl LPA; LPA (20:4))

1-Arachidonoyl-2-hydroxy-sn-glycero-3-PA is a phospholipid containing arachidonic acid at the sn-1 position. It is a precursor to 1-arachidonoyl glycerol (1-Monoarachidin; HY-130567)^[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].

458.53

C₂₃H₃₉O₇P

65446-08-4

O=P(O)(O)OC[C@H](O)COC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O

Room temperature in continental US; may vary elsewhere.

Please store the product under the recommended conditions in the Certificate of Analysis.

• [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).  [Content Brief]

  [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).  [Content Brief]

  [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).  [Content Brief]

  [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).  [Content Brief]