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

Description

SPHINGOSYLPHOSPHORYLCHOLINE, also known as Lyso SM (d18:1), is a bioactive lipid molecule belonging to the lysophospholipid class. It is naturally present in blood plasma, ascites, and various tissues, playing a crucial role in cell regulation and transmembrane signaling. As a putative lipid second messenger, it is connected via Protein Kinase C to the phosphatidylinositol-derived second messengers for signal transduction.

Uses

Used in Cell Regulation and Signal Transduction:
SPHINGOSYLPHOSPHORYLCHOLINE is used as a lipid second messenger for cell regulation and signal transduction, playing a vital role in connecting Protein Kinase C to the phosphatidylinositol-derived second messengers.
Used in Neurobiology Research:
In the field of neurobiology, SPHINGOSYLPHOSPHORYLCHOLINE is used to study its neurotrophic effects on cerebellar granule neurons of mice and PC-12 cells, contributing to the understanding of its role in neuronal development and function.
Used in Skeletal Muscle Research:
SPHINGOSYLPHOSPHORYLCHOLINE is used as a research tool 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 bilayers.
Used as an Inhibitor in Biochemical Studies:
In biochemical research, SPHINGOSYLPHOSPHORYLCHOLINE is used as an inhibitor of Ca2+ sensor calmodulin (CaM), helping researchers investigate the interactions between lipids and proteins.
Used in Spectroscopy Analysis:
As a standard in circular dichroism (CD) spectroscopy, SPHINGOSYLPHOSPHORYLCHOLINE is used to determine lipid selectivity of lipid-peptide interactions, providing valuable insights into the structural aspects of these molecular interactions.
Chemical Properties:
SPHINGOSYLPHOSPHORYLCHOLINE is a yellowish waxy solid, which is a characteristic feature of its chemical nature as a lysophospholipid.

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

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

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.