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Merck

91553

Sigma-Aldrich

N-Palmitoyl-D-sphingomyelin

≥96.0% (TLC)

Synonym(e):

(2S,3R,4E)-2-(Palmitoylamino)-4-octadecen-3-hydroxy-1-phosphocholin, 16:0 SM (d18:1/16:0), N-(Hexadecanoyl)-sphing-4-enin-1-phosphocholin, N-Palmitoyl-D-erythro-sphingosin-1-phosphorsäure-cholinester, N-Palmitoyl-D-erythro-sphingosylphosphorylcholin, C16 Sphingomyelin

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About This Item

Empirische Formel (Hill-System):
C39H79N2O6P
CAS-Nummer:
Molekulargewicht:
703.03
Beilstein:
4833682
MDL-Nummer:
UNSPSC-Code:
12352211
PubChem Substanz-ID:
NACRES:
NA.85

Qualitätsniveau

Assay

≥96.0% (TLC)

Form

powder or crystals

Zusammensetzung

carbon content, 66.63%
hydrogen content, 11.33%
nitrogen content, 3.98%

Verunreinigungen

≤6.0 wt. % water

Lipid-Typ

sphingolipids

Versandbedingung

wet ice

Lagertemp.

−20°C

SMILES String

[H][C@](/C=C/CCCCCCCCCCCCC)(O)[C@@]([H])(NC(CCCCCCCCCCCCCCC)=O)COP([O-])(OCC[N+](C)(C)C)=O

InChI

1S/C39H79N2O6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-38(42)37(36-47-48(44,45)46-35-34-41(3,4)5)40-39(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h30,32,37-38,42H,6-29,31,33-36H2,1-5H3,(H-,40,43,44,45)/b32-30+/t37-,38+/m0/s1

InChIKey

RWKUXQNLWDTSLO-GWQJGLRPSA-N

Verpackung

Bottomless glass bottle. Contents are inside inserted fused cone.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


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Atsushi Hori et al.
Clinica chimica acta; international journal of clinical chemistry, 453, 95-99 (2015-11-21)
Sphingomyelin (SM) is a key component of extracellular membranes and lipoproteins, and plays roles in cell signaling and as a component of lipoproteins. SM species differ in terms of fatty acid (FA) composition. However, no simple, rapid, quantitative assay for
Simone Colombo et al.
Scientific reports, 8(1), 12365-12365 (2018-08-19)
Endothelial dysfunction has been widely associated with oxidative stress, glucotoxicity and lipotoxicity and underlies the development of cardiovascular diseases (CVDs), atherosclerosis and diabetes. In such pathological conditions, lipids are emerging as mediators of signalling pathways evoking key cellular responses as
Reza Siavashi et al.
Biophysical journal, 117(2), 296-306 (2019-07-08)
Sphingolipids constitute a significant fraction of cellular plasma membrane lipid content. Among sphingolipids, ceramide levels are usually very low. However, in some cell processes like apoptosis, cell membrane ceramide levels increase markedly because of the activation of enzymes like acid
Saskia Klutzny et al.
Cell death & disease, 8(3), e2709-e2709 (2017-03-31)
Owing to lagging or insufficient neo-angiogenesis, hypoxia is a feature of most solid tumors. Hypoxic tumor regions contribute to resistance against antiproliferative chemotherapeutics, radiotherapy and immunotherapy. Targeting cells in hypoxic tumor areas is therefore an important strategy for cancer treatment.
Ebru Afşar et al.
Redox biology, 30, 101430-101430 (2020-01-25)
We aimed to determine sphingolipid levels and examine apoptotic pathways in human retinal pigment epithelial cells (ARPE-19) undergoing endoplasmic reticulum (ER) stress. Cells were treated with tunicamycin (TM) to induce ER stress and tauroursodeoxycholic acid (TUDCA), an ER stress inhibitor

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