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Merck
CN

860656P

Avanti

Lyso SM (d17:1)

Avanti Research™ - A Croda Brand

Synonym(s):

Sphingosylphosphorylcholine (C17 base)

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About This Item

Empirical Formula (Hill Notation):
C22H47N2O5P
CAS Number:
118540-32-2
Molecular Weight:
450.59
MDL number:
MFCD22416606
UNSPSC Code:
12352211
NACRES:
NA.25

Key Documents

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Product Name

Lyso SM (d17:1), Avanti Research™ - A Croda Brand 860656P, powder

InChI

1S/C22H47N2O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-22(25)21(23)20-29-30(26,27)28-19-18-24(2,3)4/h16-17,21-22,25H,5-15,18-20,23H2,1-4H3/b17-16+/t21-,22+/m0/s1

InChI key

AAERQLSYRRXFMA-FYBNUODKSA-N

SMILES string

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

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 10 mg (860656P-10mg)
pkg of 1 × 5 mg (860656P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860656P

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

Biochem/physiol Actions

Lyso-sphingomyelin (Lyso SM) is a vital lipid mediator, with an ability to regulate cell proliferation, migration, differentiation, metabolism and apoptosis. It exhibits various functions in cardiovascular system, immune system, central nervous system and skin. Increased concentration of Lyso SM has been observed in few disease states such as atopic dermatitis, Niemann-Pick disease (NPD) and cancer.

General description

Lyso-sphingomyelin (Lyso SM) (d17:1), is an amphiphilic lysophospholipid with a long-chain sphingosine (C17 base) and a hydrophilic phosphorylcholine. Lyso SM, also known as sphingosylphosphorylcholine (SPC) is a de-acylated form of sphingomyelin, found in blood plasma.

Packaging

5 mL Amber Glass Screw Cap Vial (860656P-10mg)
5 mL Amber Glass Screw Cap Vial (860656P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

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Certificates of Analysis (COA)

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Di Ge et al.
Acta pharmacologica Sinica, 39(12), 1830-1836 (2018-07-28)
Sphingosylphosphorylcholine (SPC) is a bioactive sphingolipid in blood plasma that is metabolized from the hydrolysis of the membrane sphingolipid. SPC maintains low levels in the circulation under normal conditions, which makes studying its origin and action difficult. In recent years
Hong-Wei Yue et al.
International journal of clinical and experimental medicine, 8(8), 11913-11921 (2015-11-10)
Sphingosylphosphorylcholine (SPC) is a naturally occurring bioactive sphingolipid in blood plasma, metabolizing from the hydrolysis of the membrane sphingolipid. It has been shown to exert multifunctional role in cell physiological regulation either as an intracellular second messenger or as an
Wei-Lien Chuang et al.
Molecular genetics and metabolism, 111(2), 209-211 (2014-01-15)
Niemann-Pick disease type B (NPD-B) is caused by a partial deficiency of acid sphingomyelinase activity and results in the accumulation of lysosomal sphingomyelin (SPM) predominantly in macrophages. Notably, SPM is not significantly elevated in the plasma, whole blood, or urine

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