1-Arachidonoyl-2-hydroxy-sn-glycero-3-PA (ammonium salt)

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, Cay-62150). 1-Arachidonoyl-2-hydroxy-sn-glycero-3-PA binds to the LPA2/EDG4 receptor with an EC50 value of approximately 10 nM. It prevents TNF-alpha and IL-6 secretion in wild-type but not Lpa2-/- dendritic cells stimulated by LPS. It also decreases differentiation of HT-29 human colon carcinoma cells to goblet cells in the presence of sodium butyrate.Formal Name: (5Z,8Z,11Z,14Z)-eicosatetraenoic acid, (2R)-hydroxy-3-(phosphonooxy)propyl ester, monoammonium salt. CAS Number: 799268-65-8. 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 . NH4. Formula Weight: 475.6. Purity: >95%. Formulation: (Request formulation change), A solid. 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.[NH4+]. InChi Code: InChI=1S/C23H39O7P.H3N/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),1H3/b7-6-,10-9-,13-12-,16-15-,/t22-,/m1./s1. InChi Key: MQNJYFKSBIEJTA-PWZWHAFSSA-N. Side Chain Carbon Sum: 20:4.