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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

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

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)

C2-Ceramide-Induced Rb-Dominant Senescence-Like Phenotype Leads to Human Breast Cancer MCF-7 Escape from p53-Dependent Cell Death.

Wen-Tsan Chang et al.

International journal of molecular sciences, 20(17) (2019-09-05)

Ceramide is a sphingolipid which regulates a variety of signaling pathways in eukaryotic cells. Exogenous ceramide has been shown to induce cellular apoptosis. In this study, we observed that exogenous ceramide induced two distinct morphologies of cell fate following C2-ceramide

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Global Trade Item Number

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

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