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Key Documents

860584P

Avanti

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

Avanti Research - A Croda Brand, powder

Synonym(s):

N-palmitoyl-D-erythro-sphingosylphosphorylcholine

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About This Item

Empirical Formula (Hill Notation):
C39H79N2O6P
CAS Number:
Molecular Weight:
703.03
UNSPSC Code:
12352211
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 Research - A Croda Brand

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)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

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’.

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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
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
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
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
Delphine Milhas et al.
FEBS letters, 584(9), 1887-1894 (2009-10-28)
The plasma membrane (PM) is a major resource for production of bioactive lipids and contains a large proportion of the cellular sphingomyelin (SM) content. Consequently, the regulation of SM levels at the PM by enzymes such as sphingomyelinase (SMase) and

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