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A7191

Sigma-Aldrich

N-Acetyl-D-sphingosine

≥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
MDL number:
MFCD00153903
UNSPSC Code:
12352211
PubChem Substance ID:
24891187
NACRES:
NA.77

biological source

semisynthetic

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
Silvia Balosso et al.
Brain : a journal of neurology, 131(Pt 12), 3256-3265 (2008-10-28)
Interleukin-1beta (IL-1beta) is overproduced in human and rodent epileptogenic tissue and it exacerbates seizures upon brain application in rodents. Moreover, pharmacological prevention of IL-1beta endogenous synthesis, or IL-1 receptor blockade, mediates powerful anticonvulsive actions indicating a significant role of this
Trevor S Tippetts et al.
BMC cardiovascular disorders, 14, 165-165 (2014-11-25)
Cigarette smoking is a common and lethal worldwide habit, with considerable mortality stemming from its deleterious effects on heart function. While current theories posit altered blood lipids and fibrinogen metabolism as likely mediators, none have explored the role of the
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