Oleoyl Serinol

Oleoyl serinol is an analog of ceramide and an agonist of the cannabinoid receptor GPR119 that has an EC50 value of 12 µM for stimulating secretion of GLP-1 in mouse endocrine GLUTag cells. It has been found in E. coli that express human microbiota N-acyl synthase (hmNAS) genes. It induces cell death of F-11 murine neuroblastoma and apoptosis in U-87 human astrocytoma cells when used at a concentration of 100 µM. Oleoyl serinol (80 µM) induces formation of a complex including PAR-4 and PKCzeta in embryoid body-derived cells, decreases the levels of the pluripotency marker Oct-4 and prostate apoptosis response-4 (PAR-4), which mediates ceramide-induced apoptosis in embryonic stem cells. It induces apoptosis selectively in rapidly dividing cells over differentiated cells as well as prevents teratoma formation and promotes neural differentiation in a neonatal mouse engraftment model of teratoma formation.Formal Name: N-[2-hydroxy-1-(hydroxymethyl)ethyl]-9Z-octadecenamide. CAS Number: 72809-08-6. Synonyms: N-Oleoyl Serinol, S-18. Molecular Formula: C21H41NO3. Formula Weight: 355.6. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: >30 mg/ml, DMSO: >15 mg/ml, Ethanol: >30 mg/ml, PBS (pH 7.2): >290 µg/ml. SMILES: O=C(NC(CO)CO)CCCCCCC/C=C\CCCCCCCC. InChi Code: InChI=1S/C21H41NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(25)22-20(18-23)19-24/h9-10,20,23-24H,2-8,11-19H2,1H3,(H,22,25)/b10-9-. InChi Key: LGDVTFHRZXBSJM-KTKRTIGZSA-N.