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860502P

Avanti

C2 Ceramide (d18:1/2:0)

Name: C2 Ceramide (d18:1/2:0)
Brand: AVANTI

Avanti Polar Lipids 860502P, powder

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Synonym(s):

N-acetoyl-D-erythro-sphingosine

Empirical Formula (Hill Notation):

C₂₀H₃₉NO₃

CAS Number:

195194-58-2

Molecular Weight:

341.53

form

powder

packaging

pkg of 1 × 5 mg (860502P-5mg)

manufacturer/tradename

Avanti Polar Lipids 860502P

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

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

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.

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.

Packaging

5 mL Amber Glass Screw Cap Vial (860502P-5mg)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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 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)

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)

Ceramide and insulin resistance: how should the issue be approached?

Gorski J

Diabetes, 61(12), 3081-3083 (2012)

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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