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860508P

Avanti

C8 Ceramide (d18:1/8:0)

Avanti Polar Lipids 860508P, powder

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Synonym(s):
N-octanoyl-D-erythro-sphingosine
Empirical Formula (Hill Notation):
C26H51NO3
CAS Number:
74713-59-0
Molecular Weight:
425.69
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 5 mg (860508P-5mg)

manufacturer/tradename

Avanti Polar Lipids 860508P

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

OC[C@]([H])(NC(CCCCCCC)=O)[C@]([H])(O)/C=C/CCCCCCCCCCCCC

InChI

1S/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

InChI key

APDLCSPGWPLYEQ-WRBRXSDHSA-N

General description

C8 Ceramide is a short chain ceramide and is cell permeable.

Application

C8 Ceramide (d18:1/8:0) has been used as an internal ceramide standard in electrospray ionization. It has also been used as a substrate for ceramide kinase activity assay. It is suitable for use as a substrate for galactocerebrosidase.

Biochem/physiol Actions

C8 Ceramide has anti-tumor functionality. Synthetic liposomal C8 ceramide inhibits hepatocellular carcinoma (HCC). Addition of exogenous C8 ceramide causes necrosis in hepatocytes by decreasing ATP levels and impairing mitochondrial functionality. C8 ceramide inhibition of serine palmitoyl transferase halts de novo sphingolipid biosynthesis. It also acts as chemotherapeutic agent by increasing the reactive oxygen species in lung cancer cells.

Packaging

5 mL Amber Glass Screw Cap Vial (860508P-5mg)

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Chronological ageing of human hair keratin fibres
Thibaut S, et al.
International Journal of Cosmetic Science, 32(6), 422-434 (2010)
Preclinical evaluation of liposomal C8 ceramide as a potent anti-hepatocellular carcinoma agent
Lv H, et al.
Testing, 11(1), e0145195-e0145195 (2016)
Ceramide induces hepatocyte cell death through disruption of mitochondrial function in the rat
Arora AS, et al.
Hepatology, 25(4), 958-963 (1997)
Exogenous C8-Ceramide Induces Apoptosis by Overproduction of ROS and the Switch of Superoxide Dismutases SOD1 to SOD2 in Human Lung Cancer Cells
Chang Y, et al.
International Journal of Molecular Sciences, 19(10), 3010-3010 (2018)
The ORMDL/Orm-serine palmitoyltransferase (SPT) complex is directly regulated by ceramide: Reconstitution of SPT regulation in isolated membranes
Davis DL, et al.
The Journal of Biological Chemistry, 294(13), 5146-5156 (2019)
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