A7191

N-Acetyl-D-sphingosine

≥97% (TLC), powder

• Synonym(s): (2S,3R,4E)-2-(Acetylamino)-4-octadecene-1,3-diol, N-Acetoyl-D-erythro-sphingosine, Acetyl ceramide, C2 Ceramide (d18:1/2:0), C₂ ceramide
• Empirical Formula (Hill Notation): C₂₀H₃₉NO₃
• Molecular Weight: 341.53
• MDL number: MFCD00153903
• UNSPSC Code: 12352211
• PubChem Substance ID: 24891187
• NACRES: NA.77

Properties

• biological source: semisynthetic
• assay: ≥97% (TLC)
• form: powder
• color: white
• solubility: DMSO: soluble; ethanol: soluble
• lipid type: sphingolipids
• storage temp.: −20°C
• SMILES string: CCCCCCCCCCCCC\C=C\[C@H](O)[C@@H](CO)NC(C)=O
• 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+/m1/s1
• InChI key: BLTCBVOJNNKFKC-HEQKZDDYSA-N

Description

Application

N-Acetyl-D-sphingosine is a cell-permeable and biologically active ceramide. N-Acetyl-D-sphingosine induces differentiation and apoptosis in cells. N-Acetyl-D-sphingosine produces concentration-dependent impairment of vasorelaxation in response to the endothelium-dependent agonist acetylcholine in nontransgenic mice.

Biochem/physiol Actions

Cell-permeable, biologically active ceramide. It induces differentiation and apoptosis in cells and has been shown to activate protein phosphatases.

Preparation Note

Prepared from D-sphingosine from bovine brain cerebrosides.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)