C2 CERAMIDE Chemical Properties

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

InChI

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

InChIKey

BLTCBVOJNNKFKC-QUDYQQOWSA-N

SMILES

C(N[C@@H](CO)[C@H](O)/C=C/CCCCCCCCCCCCC)(=O)C

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29241990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

C2 CERAMIDE Usage And Synthesis

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.

Chemical Properties

White Crystalline Solid

Uses

Inhibits cell proliferation and induces monocytic differentiation of HL-60 cells. Activates protein phosphatases

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

Definition

ChEBI: N-acetylsphingosine is a N-acylsphingosine that has an acetamido group at position 2.

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 .

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] ALFREDO MIÑANO. C2-ceramide mediates cerebellar granule cells apoptosis by activation of caspases-2, -9, and -3[J]. Journal of Neuroscience Research, 2008, 86 8: 1734-1747. DOI:10.1002/jnr.21633
[2] ALESSANDRO PRINETTI. Involvement of a ceramide activated protein phosphatase in the differentiation of neuroblastoma Neuro2a cells[J]. FEBS Letters, 1997, 414 2: Pages 475-479. DOI:10.1016/s0014-5793(97)00981-2
[3] Y ZHANG. Kinase suppressor of Ras is ceramide-activated protein kinase.[J]. Cell, 1997, 89 1: 63-72. DOI:10.1016/s0092-8674(00)80183-x
[4] Y. MATSUZAKA. Characterization and Functional Analysis of Extracellular Vesicles and Muscle-Abundant miRNAs (miR-1, miR-133a, and miR-206) in C2C12 Myocytes and mdx Mice[J]. PLoS ONE, 2016, 11 1. DOI:10.1371/journal.pone.0167811
[5] Y. MATSUZAKA. Characterization and Functional Analysis of Extracellular Vesicles and Muscle-Abundant miRNAs (miR-1, miR-133a, and miR-206) in C2C12 Myocytes and mdx Mice[J]. PLoS ONE, 2016, 11 1. DOI:10.1371/journal.pone.0167811

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