110145

D-erythro-Sphingosine, N-Acetyl-

Biologically active, cell-permeable, non-physiological ceramide analog.

• Synonym(s): D-erythro-Sphingosine, N-Acetyl-, C₂ Ceramide
• Empirical Formula (Hill Notation): C₂₀H₃₉NO₃
• CAS Number: 3102-57-6
• Molecular Weight: 341.53
• UNSPSC Code: 12352211
• NACRES: NA.77

Properties

• Quality Level: 100
• assay: ≥98% (TLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: white to off-white
• solubility: DMSO: 25 mg/mL; ethanol: 5 mg/mL; methanol: 5 mg/mL
• shipped in: ambient
• storage temp.: −20°C
• InChI: 1S/C20H39NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20(24)19(17-22)21-18(2)23/h15-16,19-20,22,24H,3-14,17H2,1-2H3,(H,21,23)/b16-15+/t19-,20+/m0/s1
• InChI key: BLTCBVOJNNKFKC-QUDYQQOWSA-N

Description

General description

Biologically active, cell-permeable, non-physiological ceramide analog. Inhibits cell growth and induces apoptosis in HL-60 cells. Induces intranucleosomal DNA fragmentation. An activator of heterotrimeric protein phosphatase 2A (PP2A). Stimulates a cytosolic serine/threonine protein phosphatase in T9 cells at concentrations as low as 100 nM. Activates stress activated protein kinase (SAPK) in HL-60 human promyelocytic cells.

Biologically active, cell-permeable, non-physiological ceramide analog. Inhibits cell growth and induces apoptosis of HL-60 cells. Induces intranucleosomal DNA fragmentation. An activator of heterotrimeric protein phosphatase 2A. Stimulates a cytosolic serine/threonine protein phosphatase in T9 cells at concentrations as low as 100 nM. Activates stress-activated protein (SAP) kinase in HL-60 human promyelocytic cells.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
Inhibits cell growth and induces apoptosis in HL-60 cells

Product does not compete with ATP.

Reversible: no

Warning

Toxicity: Irritant (B)

Preparation Note

When diluting into aqueous solution, sonication may be necessary to achieve a uniform suspension.

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). DMSO stock solutions are stable for up to 1 month at -20°C. Alcohol stock solutions are stable for <1 week at -20°C.

Other Notes

Westwick, J.K., et al. 1995. J. Biol. Chem.270, 22689.
Cifone, M.G., et al. 1994. J. Exp. Med.180, 1547.
Hannun, Y.A. 1994. J. Biol. Chem. 269, 3125.
Bielawska, A., et al. 1993. J. Biol. Chem.268, 26226.
Obeid, L.M., et al. 1993. Science259, 1769.
Ballou, L.R., et al. 1992. J. Biol. Chem.267, 20044.
Dobrowsky, R.T., and Hannun, Y.A. 1992. J. Biol. Chem.267, 5048.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable