Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

06738

Sigma-Aldrich

Sphingosylphosphorylcholine

≥98.0% (TLC)

Synonym(s):

(2S,3R,4E)-2-Amino-4-octadecene-3-hydroxy-1-phosphocholine, 2-[[[(2-Amino-3-hydroxy-4-octadecenyl)oxy]hydroxy-phosphinyl]oxy]-N,N,N-trimethylethanaminium inner salt, D-erythro-Sphingosine phosphocholine, Lyso SM (d18:1), Lysosphingomyelin

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C23H49N2O5P
CAS Number:
1670-26-4
Molecular Weight:
464.62
Beilstein:
7342520
MDL number:
MFCD02259287
UNSPSC Code:
12352211
PubChem Substance ID:
329748271
NACRES:
NA.85
Pricing and availability is not currently available.

Quality Level

100

Assay

≥98.0% (TLC)

composition

carbon content, 59.46%
hydrogen content, 10.63%
nitrogen content, 6.03%

lipid type

sphingolipids

storage temp.

−20°C

SMILES string

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

InChI

1S/C23H49N2O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)22(24)21-30-31(27,28)29-20-19-25(2,3)4/h17-18,22-23,26H,5-16,19-21,24H2,1-4H3/b18-17+/t22-,23+/m0/s1

InChI key

JLVSPVFPBBFMBE-HXSWCURESA-N

Looking for similar products? Visit Product Comparison Guide

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCBM7269V
BCBH6561V
BCBH6561

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Feng-Tao Huang et al.
Journal of lipid research, 56(9), 1836-1842 (2015-07-02)
Lyso-glycosphingolipids (lyso-GSLs), the N-deacylated forms of glycosphingolipids (GSLs), are important synthetic intermediates for the preparation of GSL analogs. Although lyso-GSLs can be produced by hydrolyzing natural GSLs using sphingolipid ceramide N-deacylase (SCDase), the yield for this reaction is usually low
Satoshi Shirao et al.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism, 35(5), 835-842 (2015-01-22)
Hyperlipidemia is a risk factor for abnormal cerebrovascular events. Rafts are cholesterol-enriched membrane microdomains that influence signal transduction. We previously showed that Rho-kinase-mediated Ca(2+) sensitization of vascular smooth muscle (VSM) induced by sphingosylphosphorylcholine (SPC) has a pivotal role in cerebral
Christiane Mühle et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 34(1), 71-81 (2014-07-01)
In vitro and in vivo studies have demonstrated the role of the acid sphingomyelinase (ASM) in pathophysiological processes and alterations in response to ethanol exposure. Cellular and plasmatic ASM activities are increased in male alcohol dependent patients and decrease during

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service