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A7191

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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Pack SizeSKUAvailabilityPrice
5 mg
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$113.00

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

$113.00

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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

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.

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This Item
H652473914110145
N-Acetyl-D-sphingosine ≥97% (TLC), powder

Sigma-Aldrich

A7191

N-Acetyl-D-sphingosine

N-Hexanoyl-D-sphingosine ≥98% (TLC), synthetic

Sigma-Aldrich

H6524

N-Hexanoyl-D-sphingosine

Sphingosine 1-phosphate ≥98.0% (TLC)

Sigma-Aldrich

73914

Sphingosine 1-phosphate

D-erythro-Sphingosine, N-Acetyl- Biologically active, cell-permeable, non-physiological ceramide analog.

Sigma-Aldrich

110145

D-erythro-Sphingosine, N-Acetyl-

form

powder

form

-

form

powder

form

solid

assay

≥97% (TLC)

assay

≥98% (TLC)

assay

≥98.0% (TLC)

assay

≥98% (TLC)

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

solubility

DMSO: soluble, ethanol: soluble

solubility

-

solubility

-

solubility

DMSO: 25 mg/mL, ethanol: 5 mg/mL, methanol: 5 mg/mL

color

white

color

-

color

-

color

white to off-white

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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
0000550310
0000539305
0000539305
0000550310
0000515157

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Related Content

Product Information Sheet - A7191

Product Information Sheet

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)
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
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
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Global Trade Item Number

SKUGTIN
A7191-5MG04061833383780
A7191-1MG04061833383773

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