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CN

860586P

Avanti

18:0 SM (d18:1/18:0)

Avanti Research™ - A Croda Brand

Synonym(s):

N-stearoyl-D-erythro-sphingosylphosphorylcholine

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About This Item

Empirical Formula (Hill Notation):
C41H83N2O6P
CAS Number:
58909-84-5
Molecular Weight:
731.08
MDL number:
MFCD02259130
UNSPSC Code:
12352211
NACRES:
NA.25

Key Documents

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Product Name

18:0 SM (d18:1/18:0), Avanti Research™ - A Croda Brand

form

powder

SMILES string

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

InChI

1S/C41H83N2O6P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-41(45)42-39(38-49-50(46,47)48-37-36-43(3,4)5)40(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h32,34,39-40,44H,6-31,33,35-38H2,1-5H3,(H-,42,45,46,47)/b34-32+/t39-,40+/m0/s1

InChI key

LKQLRGMMMAHREN-YJFXYUILSA-N

assay

>99% (TLC)

packaging

pkg of 1 × 10 mg (860586P-10mg)
pkg of 1 × 5 mg (860586P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

Application

N-stearoyl-D-erythro-sphingosylphosphorylcholine (18:0 SM (d18:1/18:0)) has been used:
  • in liposomes to measure ostreolysin A (OlyA) binding in order to interpret the effects of phosphatidylcholines (PCs) on sphingomyelin (SM)/cholesterol interactions
  • as a standard for the quantitation of sphingolipid metabolites
  • as a standard for the absolute quantification of epidermal lipids using liquid chromatography-tandem mass spectrometry (LC/MS/MS)

Packaging

5 mL Amber Glass Screw Cap Vial (860586P-10mg)
5 mL Amber Glass Screw Cap Vial (860586P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

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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
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
Marion Régnier et al.
Scientific reports, 10(1), 6489-6489 (2020-04-18)
Peroxisome proliferator activated receptor α (PPARα) acts as a fatty acid sensor to orchestrate the transcription of genes coding for rate-limiting enzymes required for lipid oxidation in hepatocytes. Mice only lacking Pparα in hepatocytes spontaneously develop steatosis without obesity in
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
Zhixing Wang et al.
The Journal of investigative dermatology, 133(3), 668-676 (2012-10-26)
The stratum corneum is composed of protein-enriched corneocytes embedded in an intercellular matrix of nonpolar lipids organized as lamellar layers and giving rise to epidermal permeability barrier (EPB). EPB defects have an important role in the pathophysiology of skin diseases
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