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91553

Sigma-Aldrich

N-Palmitoyl-D-sphingomyelin

≥96.0% (TLC)

Synonym(s):

SM(d18:1/16:0), (2S,3R,4E)-2-(Palmitoylamino)-4-octadecene-3-hydroxy-1-phosphocholine, 16:0 SM (d18:1/16:0), N-(Hexadecanoyl)-sphing-4-enine-1-phosphocholine, N-Palmitoyl-D-erythro-sphingosylphosphorylcholine, C16 Sphingomyelin

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About This Item

Empirical Formula (Hill Notation):
C39H79N2O6P
CAS Number:
6254-89-3
Molecular Weight:
703.03
Beilstein/REAXYS Number:
4833682
MDL number:
MFCD02259286
UNSPSC Code:
12352211
PubChem Substance ID:
329770051
NACRES:
NA.85

Quality Level

100

assay

≥96.0% (TLC)

form

powder or crystals

composition

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

impurities

≤6.0 wt. % water

lipid type

sphingolipids

shipped in

wet ice

storage temp.

−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

InChI key

RWKUXQNLWDTSLO-GWQJGLRPSA-N

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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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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