124753-97-5

Basic information

• Product Name: C6 CERAMIDE
• Synonyms: CAPROYL CERAMIDE;CERAMIDE C6;C6 CERAMIDE OF D-ERYTHRO-C8-SPHINGOSINE;C6 CERAMIDE;C6-D-ERYTHRO-CERAMIDE;C8 SPHINGOID BASE;D-ERYTHRO-SPHINGOSINE, N-HEXANOYL-;06:0 CERAMIDE
• CAS NO: 124753-97-5
• Molecular Formula: C24H47NO3
• Molecular Weight: 397.63
• Product Categories: Mixed Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols;Inhibitors;Protein Kinase Inhibitors and Activators
• Mol File: 124753-97-5.mol

Chemical Properties

• Melting Point: 76-77°C
• Boiling Point: 521.03°C (rough estimate)
• Flash Point: 301.4°C
• Appearance: White/Powder
• Density: 1.0077 (rough estimate)
• Vapor Pressure: 1.34E-15mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: −20°C
• Solubility: Soluble in 100% ethanol at 25mg/ml and also in DMSO at 50mg/ml.
• PKA: 13.53±0.20(Predicted)
• Stability: Freezer -20°C
• CAS DataBase Reference: C6 CERAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: C6 CERAMIDE(124753-97-5)
• EPA Substance Registry System: C6 CERAMIDE(124753-97-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 124753-97-5(Hazardous Substances Data)

Usage

Uses

Used in Cancer Research:
C6 Ceramide is used as a chemotherapeutic agent for testing its anti-tumor effects in breast cancer cells and ovarian cancer cell lines. It is also used to test chemo-sensitization effects in cancer cells, as it induces a dramatic arrest in the G0/G1 phase of the cell cycle and activates MAP kinase.
Used in Cellular Signaling Studies:
C6 Ceramide is used as a research tool to study cellular signaling pathways. It activates protein phosphatase 2A at concentrations as low as 10 nM and inhibits diacylglycerol accumulation and phospholipase D (PLD) activation in fibroblasts.
Used in Neurobiology Research:
C6 Ceramide is used in neurobiology research to study its effects on neuronal axons, where it acts to inhibit neurite growth.
Used in Cell Biology Applications:
C6 Ceramide is used in cell biology applications to induce apoptosis in MOLT-4 leukemia cells and to enhance the expression of COX-2 in rat granulosa cells. It also stimulates the growth of bovine aortic smooth muscle cells.

Biochem/physiol Actions

C6 Ceramide (d18:1/6:0) is involved in inhibiting proliferation and inducing apoptosis. When used in combination with acid ceramidase inhibitor DM102, [(2R,3Z)-N-(1-hydroxyoctadec-3-en-2-yl)pivaloylamide], it favors cell death in human breast cancer cells lines. C6 Ceramide may serve as an adjunct in chemotherapy. It elicits anti-tumor effects via AKT (serine/threonine-specific protein kinase) dephosphorylation and α-tubulin acetylation.

InChI:InChI=1/C24H47NO3/c1-3-5-7-8-9-10-11-12-13-14-15-16-18-19-23(27)22(21-26)25-24(28)20-17-6-4-2/h18-19,22-23,26-27H,3-17,20-21H2,1-2H3,(H,25,28)

Upstream product

• 142-61-0 Hexanoyl chloride 
• 6036-85-7 (2R,3R,4E)-2-amino-octadec-4-ene-1,3-diol 
• 6036-75-5 (2R,3S,4E)-2-aminooctadec-4-ene-1,3-diol 
• 25695-95-8 (2S,3S,4E)-L-threo sphingosine 
• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 

Relevant articles and documents

Synthesis and evaluation of novel phosphate ester analogs as neutral sphingomyelinase inhibitors

A novel sphingomyelin inhibitor RY221B-a, which contains a bipyridyl moiety as a metal coordination site was designed based upon the mechanism of phosphate ester hydrolysis. RY221B-a was synthesized from N-Boc-sphingosine in three steps via selective etherification using stannyl acetal. Synthesized RY221B-a exhibited relatively-strong inhibitory activity against Bc-SMase (IC 50 = 1.2 μM).

SPHINGOSINE COMPOUND, METHOD FOR PRODUCING THE SAME, AND SPHINGOMYELINASE INHIBITOR

An object of the invention is to provide a novel sphingosine compound with an inhibitory activity against sphingomyelinase, and a method for producing the sphingosine compound. The novel sphingosine compound or a salt thereof according to the invention is represented by Formula (1): wherein one of R1 and R2 is hydrogen, and the other is a group represented by Formula (G): wherein n is 0 or 1; and R3 is hydrogen, C1-23 alkyl, C3-8 cycloalkyl, C2-6 alkenyl, C1-6 alkoxy, C3-8 cycloalkyloxy, phenyl, or furil.

Inhibitory activity of a ceramide library on interleukin-4 production from activated T cells

Allergic diseases are hypersensitivity disorders associated with the production of specific immunoglobulin E (IgE) to environmental allergens. Interleukin (IL)-4, produced primarily by CD4+ T cells, is an important stimulus for the switch of th

The synthesis and biological characterization of a ceramide library

A facile synthesis of a combinatorial ceramide library and their activities in the NF-κB pathway and in apoptosis induction/prevention were demonstrated. A novel NF-κB activating molecule was discovered among ceramide containing β-galactose, and the structural requirements of ceramides for apoptosis induction was elucidated. Copyright