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About This Item
Empirical Formula (Hill Notation):
C20H39NO3
CAS Number:
Molecular Weight:
341.53
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.25
Product Name
C2 Ceramide (d18:1/2:0), Avanti Research™ - A Croda Brand 860502P, powder
SMILES string
OC[C@]([H])(NC(C)=O)[C@]([H])(O)/C=C/CCCCCCCCCCCCC
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
InChI key
BLTCBVOJNNKFKC-QUDYQQOWSA-N
assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 5 mg (860502P-5mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand 860502P
lipid type
sphingolipids
shipped in
dry ice
storage temp.
−20°C
Application
C2 Ceramide (d18:1/2:0) has been used to treat protoplasts for reactive oxygen species generation and as an substrate for sphingomyelin synthase 2 enzyme. It is suitable for use as an exogenous supplement in hippocampal cell cultures for the production of 2-hydroxyeicosatetraenoic acid (12-(S)-HETE).
Biochem/physiol Actions
C2 ceramide inhibits the progression of human bronchocarcinoma by modulating the matrix metallopeptidases-2 levels. It also inhibits glioma invasion and induces apoptosis in HT-29 and HCT-116 human colon cancer cells. Treatment of myotubes with C2-ceramide leads to decrease in glucose uptake and glycogen synthesis. C2 along with C6 ceramides induces insulin resistance in myoblastic C2C12 cell line and L6 myotubes.
General description
C2 Ceramide (d18:1/2:0) is a short-chain ceramide. In general ceramides are synthesized by de novo pathway from palmitic acid via series of intermediates to ceramidein the presence of dihydroceramide Δ4-desaturase.
Packaging
5 mL Amber Glass Screw Cap Vial (860502P-5mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Storage Class
11 - Combustible Solids
wgk
WGK 3
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Ceramide elevates 12-hydroxyeicosatetraenoic acid levels and upregulates 12-lipoxygenase in rat primary hippocampal cell cultures containing predominantly astrocytes
Prasad VVTS, et al.
Neurochemistry International, 53(6-8), 220-229 (2008)
Induction of apoptosis by sphingosine, sphinganine, and C2-ceramide in human colon cancer cells, but not by C2-dihydroceramide
Ahn EH and Schroeder JJ
Anticancer research, 30(7), 2881-2884 (2010)
Ceramide and insulin resistance: how should the issue be approached?
Gorski J
Diabetes, 61(12), 3081-3083 (2012)
Sphingolipid Metabolism: New Insight into Ceramide-Induced Lipotoxicity in Muscle Cells
Bandet C, et al.
International Journal of Molecular Sciences, 20(3), 479-479 (2019)
Exogenous C2 ceramide suppresses matrix metalloproteinase gene expression by inhibiting ROS production and MAPK signaling pathways in PMA-stimulated human astroglioma cells
Jung JS, et al.
International Journal of Molecular Sciences, 17(4), 477-477 (2016)
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