1670-26-4

Basic information

• Product Name: SPHINGOSYLPHOSPHORYLCHOLINE
• Synonyms: LYSO-SPHINGOMYELIN;D-ERYTHRO-SPC;D-ERYTHRO-SPHINGOSYLPHOSPHORYLCHOLINE;SPHINGOSYLPHOSPHORYLCHOLINE;SPHINGOSYLPHOSPHORYLCHOLINE, D-ERYTHRO;SPC;2-[[[(2-amino-3-hydroxy-4-octadecenyl)oxy]hydroxy-phosphinyl]oxy]-n,n,n-trimethylethanaminium inner salt;spingosyl-phosphorylcholine
• CAS NO: 1670-26-4
• Molecular Formula: C₂₃H₄₉N₂O₅P
• Molecular Weight: 464.62
• Product Categories: Chemical Activators;Activators;Fatty Acid Derivatives & Lipids;Glycerols;Inhibitors;Protein Kinase Inhibitors and Activators
• Mol File: 1670-26-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 90-102°C
• Appearance: light yellow/powder
• Storage Temp.: −20°C
• Solubility: chloroform/methanol (2:1): complete10 mg/ml, clear to slightly h
• BRN: 7342520
• CAS DataBase Reference: SPHINGOSYLPHOSPHORYLCHOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: SPHINGOSYLPHOSPHORYLCHOLINE(1670-26-4)
• EPA Substance Registry System: SPHINGOSYLPHOSPHORYLCHOLINE(1670-26-4)

Safety Data

• WGK Germany: 3
• F: 1-8-10
• Hazardous Substances Data: 1670-26-4(Hazardous Substances Data)

Usage

Chemical Properties

Yellowish Waxy Solid

Uses

Different sources of media describe the Uses of 1670-26-4 differently. You can refer to the following data:
1. Involved in cell regulation, and transmembrane signaling. A putative lipid second messenger, connected via Protein Kinase C to the phosphatidylinositol-derived second messengers for signal transduction.
2. Neurotrophic effects of Sphingosylphosphorylcholine were studied in cerebellar granule neurons of mice and PC-12 cells.
3. Lyso SM (d18:1) has been used: to study its effect on the skeletal muscle ryanodine receptor (RyR1), in the presence and absence of calmodulin through single channel recordings in planar lipid bilayersas an inhibitor of Ca2+ sensor calmodulin (CaM)as a standard in circular dichroism (CD) spectroscopy to determine lipid selectivity of the lipid-peptide interactions

General Description

Lyso SM (d18:1), also known as sphingosylphosphorylcholine (SPC), is a bioactive lipid molecule. This lysophospholipid is present in normal blood plasma, ascites and various tissues.

Biochem/physiol Actions

Sphingosylphosphorylcholine (SPC) is a bioactive lipid that mediates intracellular and extracellular signaling. It mobilizes Ca2+ from intracellular stores via an IP3-independent pathway. It stimulates the production of CCL2 that may contribute to development of atherosclerosis. SPC is a ligand for endothelial differentiation gene receptor 3 (EDG3).

InChI:InChI=1/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

Upstream product

• 860021-45-0 (4S)-4-[(1R)-1-(tert-butyldiphenylsilyloxy)-hexadec-2-enyl]-2-chloro-2-oxo-[1,3,2]-oxazaphospholidine 
• 55357-38-5 choline tosylate 
• 916159-70-1 (2S,3R)-(E)-2-azido-1-(tert-butyldiphenylsilyloxy)octadec-4-en-3-ol 
• 103348-49-8 2-azido-sphingosine 
• 114275-40-0 (2R,3R)-trans-2-azide-1,3-O-benzylidene-1,3-octadec-4-enediol 
• 114275-39-7 (2R,3R,4E)-1,3-benzylidene-4-octadecene-1,2,3-triol 
• 3006-41-5 4,6-O-benzylidene-α,β-D-galactopyranose 
• 10257-28-0 D-Galactose 
• 103348-50-1 (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol 
• 168411-99-2 <(2S,3R,4E)-2-amino-3-(tert-butyldimethylsilyloxy)-4-octadecene-1-yl><2-(trimethylammonio)ethyl> phosphate 

Downstream Products

• 1211325-02-8 C₆₅H₈₉F₄N₅O₈P⁽¹⁺⁾ 
• 1211325-08-4 C₆₅H₈₈F₄N₅O₁₄PS₂ 
• 807617-46-5 N-perdeuteriopalmitoylsphingomyelin 
• 115-18-4 2-methyl-3-buten-2-ol 

Related news

Effect of direct albumin binding to SPHINGOSYLPHOSPHORYLCHOLINE (cas 1670-26-4) in Jurkat T cells09/30/2019

We investigated the effects of serum on lysophospholipid-induced cytotoxicity in Jurkat T cells. We found that sphingosylphosphorylcholine (SPC, also known as lysosphingomyelin) induced cytotoxicity and that albumin in serum could protect cells by binding directly to SPC. Furthermore, we also fo...detailed

SPHINGOSYLPHOSPHORYLCHOLINE (cas 1670-26-4) inhibits macrophage adhesion to vascular smooth muscle cells09/29/2019

Inflammation in de-endothelialised arteries contributes to the development of cardiovascular diseases. The process that initiates this inflammatory response is the adhesion of monocytes/macrophages to exposed vascular smooth muscle cells, typically stimulated by cytokines such as tumour necrosis...detailed

Novel effects of SPHINGOSYLPHOSPHORYLCHOLINE (cas 1670-26-4) on invasion of breast cancer: Involvement of matrix metalloproteinase-3 secretion leading to WNT activation09/27/2019

Sphingosylphosphorylcholine (SPC) participates in several cellular processes including metastasis. SPC induces keratin reorganization and regulates the viscoelasticity of metastatic cancer cells including PANC-1 cancer cells leading to enhanced migration and invasion. The role of SPC and the rel...detailed

SPHINGOSYLPHOSPHORYLCHOLINE (cas 1670-26-4) protects cardiomyocytes against ischemic apoptosis via lipid raft/PTEN/Akt1/mTOR mediated autophagy09/25/2019

Autophagy, evoked by diverse stresses including myocardial ischemia/reperfusion (I/R), profoundly affects the development of heart failure. However, the specific molecular basis of autophagy remains to be elucidated. Here we report that sphingosylphosphorylcholine (SPC), a bioactive sphingolipid...detailed

SPHINGOSYLPHOSPHORYLCHOLINE (cas 1670-26-4) regulates the Hippo signaling pathway in a dual manner09/24/2019

Sphingosylphosphorylcholine (SPC) is a bioactive sphingolipid which regulates many cancer-related processes, including cellular proliferation. The Hippo signaling pathway consists of a cascade of tumor suppressive kinases Mst1/2 and Lats1/2 and their downstream targets YAP and TAZ which are gene...detailed

Relevant articles and documents

An Improved, Versatile, and Easily Scalable Synthesis of Sphingomyelins: Application to Stable Isotope Labeling

With a view to make conveniently labeled mass spectrometry standards available, a set of deuterated sphingomyelins were prepared by a new expedient, flexible, robust, scalable, and high-yielding synthetic scheme starting from 2-azido-3- O -benzoylsphingos

Process for the preparation of cyclic 4-oxoamidines

The present invention relates to a process for the preparation of cyclic 4-oxoamidines. Such substances are precursors of active substances having biological action. The process according to the invention forms a further method of obtaining this class of compound. By reacting condensation products of aldehydes and aminonitriles or amino acid amides with oxidizing agents, the desired cyclic 4-oxoamidines are obtained according to the invention in good to very good yields.