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A7191

N-Acetyl-D-sphingosine

Name: <I>N</I>-Acetyl-D-sphingosine
Brand: SIGMA

≥97% (TLC), powder

Synonym(s):

(2S,3R,4E)-2-(Acetylamino)-4-octadecene-1,3-diol, N-Acetoyl-D-erythro-sphingosine, Acetyl ceramide, C2 Ceramide (d18:1/2:0), C₂ ceramide

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About This Item

Empirical Formula (Hill Notation):

C₂₀H₃₉NO₃

Molecular Weight:

341.53

NACRES:

NA.77

PubChem Substance ID:

24891187

UNSPSC Code:

12352211

MDL number:

MFCD00153903

Assay:

≥97% (TLC)

Form:

powder

Quality level:

200

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biological source

semisynthetic

Quality Level

200

assay

≥97% (TLC)

form

powder

color

white

solubility

DMSO: soluble, ethanol: soluble

lipid type

sphingolipids

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCC\C=C\[C@H](O)[C@@H](CO)NC(C)=O

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+/m1/s1

InChI key

BLTCBVOJNNKFKC-HEQKZDDYSA-N

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Application

N-Acetyl-D-sphingosine is a cell-permeable and biologically active ceramide. N-Acetyl-D-sphingosine induces differentiation and apoptosis in cells. N-Acetyl-D-sphingosine produces concentration-dependent impairment of vasorelaxation in response to the endothelium-dependent agonist acetylcholine in nontransgenic mice.

Biochem/physiol Actions

Cell-permeable, biologically active ceramide. It induces differentiation and apoptosis in cells and has been shown to activate protein phosphatases.

Preparation Note

Prepared from D-sphingosine from bovine brain cerebrosides.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

0000539305

0000515157

0000394967

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Sphingomyelinase dependent apoptosis following treatment of pancreatic beta-cells with amyloid peptides Abeta(1-42) or IAPP.

Ying Zhang et al.

Apoptosis : an international journal on programmed cell death, 14(7), 878-889 (2009-06-03)

Amyloid peptides interfere with survival of pancreatic beta-cells. In some cells apoptosis is paralleled by ceramide-dependent alterations of ion channel activity. The purpose of the present study was to elucidate the dependence of amyloid peptides Abeta(1-42) and islet amyloid polypeptide

The antiproliferative effect of C2-ceramide on lung cancer cells through apoptosis by inhibiting Akt and NFκB.

I-Ling Lin et al.

Cancer cell international, 14(1), 1-1 (2014-01-08)

The anticancer effects of ceramide have been reported in many types of cancers but less in lung cancer. In this study, we used C2-ceramide to further investigate its possible anticancer effects and mechanisms on non-small cell lung cancer (NSCLC) H1299

Methionine and Arginine Supply Alters Abundance of Amino Acid, Insulin Signaling, and Glutathione Metabolism-Related Proteins in Bovine Subcutaneous Adipose Explants Challenged with N-Acetyl-d-sphingosine.

Yusheng Liang et al.

Animals : an open access journal from MDPI, 11(7) (2021-08-08)

The objective was to perform a proof-of-principle study to evaluate the effects of methionine (Met) and arginine (Arg) supply on protein abundance of amino acid, insulin signaling, and glutathione metabolism-related proteins in subcutaneous adipose tissue (SAT) explants under ceramide (Ce)

Ceramide-induced impairment of endothelial function is prevented by CuZn superoxide dismutase overexpression.

Sean P Didion et al.

Arteriosclerosis, thrombosis, and vascular biology, 25(1), 90-95 (2004-11-06)

Ceramide is an important intracellular second messenger that may also increase superoxide. The goal of this study was to determine whether overexpression of CuZn superoxide dismutase (SOD) protects against ceramide-induced increases in vascular superoxide and endothelial dysfunction. Carotid arteries from

Mitochondrial fission mediates ceramide-induced metabolic disruption in skeletal muscle.

Melissa E Smith et al.

The Biochemical journal, 456(3), 427-439 (2013-10-01)

Ceramide is a sphingolipid that serves as an important second messenger in an increasing number of stress-induced pathways. Ceramide has long been known to affect the mitochondria, altering both morphology and physiology. We sought to assess the impact of ceramide

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Global Trade Item Number

SKU	GTIN
A7191-5MG	04061833383780
A7191-1MG	04061833383773

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