| Identification | Back Directory | [Name]
C2 CERAMIDE | [CAS]
3102-57-6 | [Synonyms]
CERAMIDE
C2 CERAMIDE
CERAMIDE C2
TOC Ceramide
C2:0 CERAMIDE
ACETYL CERAMIDE
C14 SPHINGOID BASE
N-ACETYLSPHINGOSINE
C2-D-ERYTHRO-CERAMIDE
N-ACETYL-D-SPHINGOSINE
C2 Ceramide (d18:1/2:0)
N-Ethanoyl-D-sphingosine
N-ACETYLSPHINGOSINE, D-ERYTHRO
N-ACETYL-D-ERYTHRO-SPHINGOSINE
Acetyl ceramide, C2 ceramide
(D-erythro-N-Acetylsphingosine)
D-ERYTHRO-SPHINGOSINE, N-ACETYL-
N-ETHANOYL-D-ERYTHRO-SPHINGOSINE
D-erythro-Sphingoshine, N-Acetyl-
C2 CERAMIDE OF D-ERYTHRO-C14-SPHINGOSINE
N-Ethanoyl-D-erythro-sphingosine, synthetical
(2S,3R,4E)-2-(Acetylamino)-4-octadecene-1,3-diol
N-ETHANOYL-D-ERYTHRO-SPHINGOSINE SYNTHE TICAL 99+%
N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxyMethyl)-3-heptadecen-1-yl]acetaMide | [Molecular Formula]
C20H39NO3 | [MDL Number]
MFCD00153903 | [MOL File]
3102-57-6.mol | [Molecular Weight]
341.53 |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [Melting point ]
93-96 °C
| [Boiling point ]
477.13°C (rough estimate) | [density ]
1.0283 (rough estimate) | [refractive index ]
1.5614 (estimate) | [storage temp. ]
−20°C
| [solubility ]
DMSO: soluble
| [form ]
powder
| [pka]
13.50±0.20(Predicted) | [color ]
white
| [biological source]
semisynthetic | [Stability:]
Moisture Sensitive |
| Hazard Information | Back Directory | [Chemical Properties]
White Crystalline Solid | [Uses]
A biologically active, cell permeable, but nonphysiologic ceramide analog. It inhibits cell proliferation and induces monocytic differentiation of HL-60 cells and induces apoptosis. It stimulates protein phosphatase 2A and activates MAP Kinase2 | [Biological Activity]
A potent modulator of cell proliferation and differentiation. Activates protein phosphatase-1 (PP1) and -2A (PP2A), as well as ceramide-activated protein phosphatase (CAPP) in vitro . | [Description]
C2 ceramide is a cell-permeable analog of naturally occurring ceramides. It mediates many diverse biological activities, as do natural ceramides. These processes include differentiation of HL-60 cells, induction of apoptosis, activation of protein phosphatase 2A, and inhibition of the mitochondrial respiratory chain. C2 ceramide also enhances the expression of COX-2 in human dermal fibroblasts and stimulates the growth of bovine aortic smooth muscle cells. The ability of C2 ceramide to destabilize membranes may be responsible for its inhibition of platelet aggregation. | [Definition]
ChEBI: N-acetylsphingosine is a N-acylsphingosine that has an acetamido group at position 2. | [Biochem/physiol Actions]
Cell-permeable, biologically active ceramide. It induces differentiation and apoptosis in cells and has been shown to activate protein phosphatases. | [storage]
Desiccate at -20°C | [References]
1) Minano et al. (2008), C2-ceramide mediates cerebellar granule cells apoptosis by activation of caspases-2, -9, and -3; J. Neurosci. Res., 86 1734
2) Prinetti et al. (1997), Involvement of a ceramide activated protein phosphatase in the differentiation of neuroblastoma Neuro2a cells; FEBS Lett., 414 475
3) Zhang et al. (1997), Kinase suppressor of Ras is ceramide-activated protein kinase; Cell, 89 63
4) Matsuzaka et al. (2016) Characterization and Functional Analysis of Extracellular Vesicles and Muscle-Abundant miRNAs (miR-1, miR-133a, and miR-206) in C2C12 Myocytes and mdx Mice; PLoS One 11(12) e0167811 [Focus Biomolecules Citation]
5) Matsuzaka et al. (2016) Characterization and functional analysis of extracellular vesicles and muscle-abundant miRNA in C2C12 myocytes and Mdx mice; PLoS One 11(12) e0167811 [Focus Biomolecules Citation] |
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