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860587P

Avanti

18:1 SM (d18:1/18:1(9Z))

Avanti Research™ - A Croda Brand

Synonym(s):

N-oleoyl-D-erythro-sphingosylphosphorylcholine

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About This Item

Empirical Formula (Hill Notation):
C41H81N2O6P
CAS Number:
108392-10-5
Molecular Weight:
729.07
MDL number:
MFCD28143646
UNSPSC Code:
12352211
NACRES:
NA.25

Key Documents

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Product Name

18:1 SM (d18:1/18:1(9Z)), Avanti Research™ - A Croda Brand

SMILES string

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

InChI

1S/C41H81N2O6P/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/h20-21,32,34,39-40,44H,6-19,22-31,33,35-38H2,1-5H3,(H-,42,45,46,47)/b21-20-,34-32+/t39-,40+/m0/s1

InChI key

NBEADXWAAWCCDG-QDDWGVBQSA-N

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 5 mg (860587P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

Application

18:1 SM (d18:1/18:1(9Z)) may be used:
  • in liposomes to measure ostreolysin A (OlyA) binding in order to infer the effects of phosphatidylcholines (PCs) on sphingomyelin (SM)/cholesterol interactions
  • as a standard for the ratiometric quantification of SM
  • to study its effects on C2-domain mutations by surface plasmon resonance (SPR)

General description

18:1 SM (d18:1/18:1(9Z)) is a version of sphingomyelin (SM) containing a C16 ceramide base and an amide-linked oleoyl (18:1) acyl chain.

Packaging

2 mL Amber Glass Sealed Ampule (860587P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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
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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