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860586P

Avanti

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

Avanti Polar Lipids 860586P, powder

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
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

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

manufacturer/tradename

Avanti Polar Lipids 860586P

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

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

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 Code

11 - Combustible Solids

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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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
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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