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860584P

Avanti

16:0 SM (d18:1/16:0)

Avanti Polar Lipids, powder

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Synonym(s):
N-palmitoyl-D-erythro-sphingosylphosphorylcholine
Empirical Formula (Hill Notation):
C39H79N2O6P
CAS Number:
6254-89-3
Molecular Weight:
703.03
NACRES:
NA.25

Assay

>99% (TOF, LC/MS)

form

powder

packaging

pkg of 1 × 10 mg (860584P-10mg)
pkg of 1 × 25 mg (860584P-25mg)
pkg of 1 × 5 mg (860584P-5mg)

manufacturer/tradename

Avanti Polar Lipids

lipid type

sphingolipids

shipped in

dry 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

Application

N-palmitoyl-D-erythro-sphingosylphosphorylcholine (16:0 SM (d18:1/16:0)) has been used as a standard for the quantitation of sphingolipid metabolites. It has also been used for the quantification of lipids in green fluorescence protein (GFP) and fatty acid transport protein 4 (FATP4) cells using electrospray ionization tandem mass spectrometry (ESI-MS/MS). It may be used in liposomes to measure ostreolysin A (OlyA) binding to determine the effects of phosphatidylcholines (PCs) on sphingomyelin (SM)/cholesterol interactions.

Packaging

5 mL Amber Glass Screw Cap Vial (860584P-10mg)
5 mL Amber Glass Screw Cap Vial (860584P-25mg)
5 mL Amber Glass Screw Cap Vial (860584P-5mg)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Shreya Endapally et al.
Cell, 176(5), 1040-1053 (2019-02-05)
Sphingomyelin and cholesterol are essential lipids that are enriched in plasma membranes of animal cells, where they interact to regulate membrane properties and many intracellular signaling processes. Despite intense study, the interaction between these lipids in membranes is not well
Xingzhong Zhang et al.
Cell metabolism, 30(5), 937-951 (2019-11-02)
Obesity-induced adipose dysfunction is a major contributor to atherosclerosis. Cold exposure has been reported to affect atherosclerosis through regulation of adipose function, but the mechanism has not been well clarified. Here, adipocyte hypoxia-inducible factor 2α (HIF-2α) was upregulated after mild cold
Elisabetta Albi et al.
International journal of molecular sciences, 15(7), 11555-11565 (2014-07-01)
Proliferating thyroid cells are more sensitive to UV-C radiations than quiescent cells. The effect is mediated by nuclear phosphatidylcholine and sphingomyelin metabolism. It was demonstrated that proton beams arrest cell growth and stimulate apoptosis but until now there have been
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
Elisabeth Corcelle-Termeau et al.
Autophagy, 12(5), 833-849 (2016-04-14)
Sphingomyelin is an essential cellular lipid that traffics between plasma membrane and intracellular organelles until directed to lysosomes for SMPD1 (sphingomyelin phosphodiesterase 1)-mediated degradation. Inactivating mutations in the SMPD1 gene result in Niemann-Pick diseases type A and B characterized by
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