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74713-59-0

74713-59-0 Structure

74713-59-0 Structure
IdentificationMore
[Name]

C8 CERAMIDE
[CAS]

74713-59-0
[Synonyms]

08:0 CERAMIDE
C8 CERAMIDE
C8 CERAMINE, D-ERYTHRO
C8-D-ERYTHRO-CERAMIDE
CERAMIDE C8
D-ERYTHRO-SPHINGOSINE, N-OCTANOYL-
N-OCTANOYL-D-ERYTHRO-SPHINGOSINE
N-OCTANOYL-D-SPHINGOSINE
N-OCTANOYLSPHINGOSINE
N-OCTANOYLSPHINGOSINE, D-ERYTHRO
D-erythro-N-Octanoylsphingosine
N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]Octanamide
N-Octanoyl-C18-sphingosine
N-Octanoyl-D-erythr
Octanamide, N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-, [R-[R*,S*-(E)]]-
N-Octanoyl-D-erythro-sp
N-OCTANOYL-D-ERYTHRO-SPHINGOSINE, 99+%, SYNTHETICAL
N-Octanoyl-D-erythro-sphingosine, synthetical
[Molecular Formula]

C26H51NO3
[MDL Number]

MFCD00236496
[Molecular Weight]

425.69
[MOL File]

74713-59-0.mol
Chemical PropertiesBack Directory
[Appearance]

Off White Powder
[Melting point ]

68-70°C
[Boiling point ]

541.37°C (rough estimate)
[density ]

0.9974 (rough estimate)
[refractive index ]

1.6000 (estimate)
[storage temp. ]

−20°C
[solubility ]

DMSO or ethanol: soluble
[form ]

waxy solid
[color ]

White
[Usage]

A biologically active, cell permeable, but nonphysiologic ceramide analog. It induces phosphorylation on Thr-669 in A-431 cells by stimulation of ceramide-activated protein kinase. It stimulates IL-2 secretion and induces apoptosis
[Stability:]

Temperature Sensitive
[InChIKey]

APDLCSPGWPLYEQ-WRBRXSDHSA-N
[SMILES]

C(N[C@@H](CO)[C@H](O)/C=C/CCCCCCCCCCCCC)(=O)CCCCCCC
[CAS DataBase Reference]

74713-59-0(CAS DataBase Reference)
Safety DataBack Directory
[Safety Statements ]

S24/25:Avoid contact with skin and eyes .
[WGK Germany ]

3
[HS Code ]

29225000
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Description]

C8-ceramide (74713-59-0) is a cell permeable ceramide analog. Stimulates ceramide-activated protein kinase.1?Induces apoptosis.2?Reported to inhibit apoptosis and gap junction intercellular communication (GJIC) in rat liver epithelial cells.3?C8-ceramide induces the secretion of brain-derived neurotrophic factor (BDNF) from microglia?in vitro.4
[Chemical Properties]

Off White Powder
[Uses]

A biologically active, cell permeable, but nonphysiologic ceramide analog. It induces phosphorylation on Thr-669 in A-431 cells by stimulation of ceramide-activated protein kinase. It stimulates IL-2 secretion and induces apoptosis
[Uses]

C-8 Ceramide is a ceramide analog.
[Definition]

ChEBI: N-octanoylsphingosine is an N-acylsphingosine in which the ceramide N-acyl group is specified as octanoyl. It is functionally related to an octanoic acid.
[in vivo]

C8-ceramide (0.1 mg/kg; intranasal administration) induces more robust CD8+ and CD4+ T cell responses to viral infections in virus infected mice[3].

Animal Model:C57BL/6 mice, with lymphocytic choriomeningitis virus infected[3]
Dosage:0.1 mg/kg
Administration:Intranasal administration
Result:Increased the CD8+ T cell response to influenza in the lungs.
[IC 50]

PKC; apoptosis; autophagy
[storage]

Store at -20℃, stored under nitrogen
[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
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

N-Octanoyl-D-erythro-sphingosine, synthetical, 99+%(74713-59-0)
[Sigma Aldrich]

74713-59-0(sigmaaldrich)
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