74713-59-0

Basic information

• Product Name: C8 CERAMIDE
• Synonyms: N-OCTANOYLSPHINGOSINE, D-ERYTHRO;N-OCTANOYL-D-ERYTHRO-SPHINGOSINE;N-OCTANOYL-D-SPHINGOSINE;N-OCTANOYLSPHINGOSINE;08:0 CERAMIDE;C8 CERAMIDE;C8 CERAMINE, D-ERYTHRO;C8-D-ERYTHRO-CERAMIDE
• CAS NO: 74713-59-0
• Molecular Formula: C₂₆H₅₁NO₃
• Molecular Weight: 425.69
• Product Categories: Mixed Fatty Acids;Activators;Fatty Acid Derivatives & Lipids;Glycerols;Inhibitors;Protein Kinase Inhibitors and Activators
• Mol File: 74713-59-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 68-70°C
• Boiling Point: 541.37°C (rough estimate)
• Flash Point: 313.9°C
• Appearance: /waxy solid
• Density: 0.9974 (rough estimate)
• Vapor Pressure: 1.16E-16mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: −20°C
• Solubility: DMSO or ethanol: soluble
• Stability: Temperature Sensitive
• CAS DataBase Reference: C8 CERAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: C8 CERAMIDE(74713-59-0)
• EPA Substance Registry System: C8 CERAMIDE(74713-59-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 74713-59-0(Hazardous Substances Data)

Usage

Description

C8 Ceramide, also known as C8-ceramide, is a cell permeable ceramide analog with the chemical formula (74713-59-0). It is an off-white powder that possesses biological activity and is capable of inducing phosphorylation on Thr-669 in A-431 cells by stimulating ceramide-activated protein kinase. C8 Ceramide is known for its ability to stimulate IL-2 secretion, induce apoptosis, inhibit apoptosis, and gap junction intercellular communication (GJIC) in rat liver epithelial cells. Additionally, it has been reported to induce the secretion of brain-derived neurotrophic factor (BDNF) from microglia in vitro.

Uses

Used in Pharmaceutical Applications:
C8 Ceramide is used as a pharmaceutical agent for its ability to induce apoptosis, which is the process of programmed cell death. This property makes it a potential candidate for the development of treatments targeting various diseases, including cancer.
Used in Cellular Signaling Research:
C8 Ceramide is used as a research tool in the field of cellular signaling, particularly in studying the role of ceramide-activated protein kinase and its effects on cell signaling pathways.
Used in Neurobiology Research:
C8 Ceramide is used as a research tool in neurobiology, specifically for investigating the secretion of brain-derived neurotrophic factor (BDNF) from microglia, which is essential for neuronal growth, survival, and synaptic plasticity.
Used in Drug Delivery Systems:
C8 Ceramide can be employed in the development of novel drug delivery systems to enhance its applications and efficacy in various therapeutic areas, such as cancer treatment and neurodegenerative diseases.
Used in Cosmetics Industry:
C8 Ceramide may also be used in the cosmetics industry for its potential benefits in promoting skin health and maintaining the skin's natural barrier function.

References

1) Mathias?et al. (1991) Characterization of a ceramide-activated protein kinase: stimulation by tumor necrosis factor alpha; Proc. Natl. Acad. Sci. USA,?88?109 2) Jarvis?et al. (1993)?Induction of apoptotic DNA damage and cell death by activation of the sphingomyelin pathway; Proc. Natl. Acad. Sci. USA?91?73 3) Upham?et al. (2003),?Differential roles of 2,6 and 8 carbon ceramides on the modulation of gap junctional communication and apoptosis during carcinogenesis; Cancer Lett.,?191?27 4) Nakajima?et al. (2002),?Ceramide activates microglia to enhance the production/secretion of brain-derived neurotrophic factor (BDNF) without induction of deleterious factors in vitro; J. Neurochem.,?80?697

InChI:InChI=1/C26H51NO3/c1-3-5-7-9-10-11-12-13-14-15-16-18-19-21-25(29)24(23-28)27-26(30)22-20-17-8-6-4-2/h19,21,24-25,28-29H,3-18,20,22-23H2,1-2H3,(H,27,30)/b21-19+/t24-,25+/m0/s1

Upstream product

• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 1956-10-1 p-nitrophenyl-caprylate 
• 111-64-8 n-octanoic acid chloride 
• 2673-72-5 (2S,3R,E)-2-aminooctadec-4-ene-1,3-diol hydrochloride 

Downstream Products

• 158983-55-2 N-Octanoyl-1-O-benzoyl-3-O-tetrahydropyranyl-D-erythro-sphingosine 
• 158983-53-0 D-erythro-C8-ceramide-1-phosphate 
• 158983-54-1 N-Octanoyl-1-O-benzoyl-D-erythro-sphingosine 

Relevant articles and documents

Chiral combinatorial preparation and biological evaluation of unique ceramides for inhibition of sphingomyelin synthase

Enantiomers or diastereomers of chiral bioactive compounds often exhibit different biological and toxicological properties. Here, we report the efficient synthesis of four stereoisomers of sphingosine and derivatization of unique chiral ceramides through a combinatorial chemistry by solid-phase activated resin ester. In addition, to test the effectivity of stereochemistry of ceramide, we demonstrated a cell-based assay of sphingomyelin synthase inhibition in the presence ofchiral unique ceramides, which suggested that libraries of this sort will be a rich source of biologically active synthetic molecules.

Exploring Leishmania major Inositol Phosphorylceramide Synthase (LmjIPCS): Insights into the ceramide binding domain

The synthesis of set of ceramide analogues exploring hydrophobicity in the acyl chains and the degree and nature of hydroxylation is described. These have been assayed against the parasitic protozoan enzyme LmjIPCS. These studies showed that whilst the C-3 hydroxyl group was not essential for turnover it provided enhanced affinity. Reflecting the membrane bound nature of the enzyme a long (C13) hydrocarbon ceramide tail was necessary for both high affinity and turnover. Whilst the N-acyl chain also contributed to affinity, analogues lacking the amide linkage functioned as competitive inhibitors in both enzyme and cell-based assays. A model that accounts for this observation is proposed.

Synthesis of sphingomyelin and ceramide 1-phosphate from ceramide without protection of the allylic hydroxyl group

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