Skip to Content
Merck
All Photos(1)

Key Documents

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

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C39H79N2O6P
CAS Number:
Molecular Weight:
703.03
Beilstein:
4833682
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.85

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 Code

11 - Combustible Solids

WGK

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service