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110145

D-erythro-Sphingosine, N-Acetyl-

Name: D-<i>erythro</i>-Sphingosine, N-Acetyl-
Brand: MM

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

Synonym(s):

D-erythro-Sphingosine, N-Acetyl-, C₂ Ceramide

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About This Item

Empirical Formula (Hill Notation):

C₂₀H₃₉NO₃

CAS Number:

3102-57-6

Molecular Weight:

341.53

UNSPSC Code:

12352211

NACRES:

NA.77

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

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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