807617-46-5

Basic information

• Product Name: N-palMitoyl-d31-D-erythro-sphingosylphosphorylcholine
• Synonyms: N-palMitoyl-d31-D-erythro-sphingosylphosphorylcholine;16:0-d31 SM;RWKUXQNLWDTSLO-XDEXOTOPSA-N
• CAS NO: 807617-46-5
• Molecular Formula: C39H79N2O6P
• Molecular Weight: 703.04
• Mol File: 807617-46-5.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-palMitoyl-d31-D-erythro-sphingosylphosphorylcholine(CAS DataBase Reference)
• NIST Chemistry Reference: N-palMitoyl-d31-D-erythro-sphingosylphosphorylcholine(807617-46-5)
• EPA Substance Registry System: N-palMitoyl-d31-D-erythro-sphingosylphosphorylcholine(807617-46-5)

Safety Data

• Hazardous Substances Data: 807617-46-5(Hazardous Substances Data)

Usage

General Description

N-palmitoyl-d31-D-erythro-sphingosylphosphorylcholine is a chemical compound that belongs to the class of sphingolipids, which are important components of cell membranes. This particular compound is a labeled form of palmitoyl-D-erythro-sphingosylphosphorylcholine, where the hydrogen atoms in the palmitoyl chain are replaced with deuterium atoms. It is often used as a stable isotope-labeled internal standard for quantification of sphingolipids in biological samples using mass spectrometry. Sphingolipids play a crucial role in cell signaling, cell recognition, and modulation of various cellular processes, making this compound significant in biochemical research and pharmaceutical development.

Upstream product

• 1670-26-4 sphingosylphosphorylcholine 

Relevant articles and documents

Raftlike mixtures of sphingomyelin and cholesterol investigated by solid-state 2H NMR spectroscopy

Sphingomyelin is a lipid that is abundant in the nervous systems of mammals, where it is associated with putative microdomains in cellular membranes and undergoes alterations due to aging or neurodegeneration. We investigated the effect of varying the concentration of cholesterol in binary and ternary mixtures with N-palmitoylsphingomyelin (PSM) and 1-palmitoyl-2-oleoyl-sn- glycero-3-phosphocholine (POPC) using deuterium nuclear magnetic resonance (2H NMR) spectroscopy in both macroscopically aligned and unoriented multilamellar dispersions. In our experiments, we used PSM and POPC perdeuterated on the N-acyl and sn-1 acyl chains, respectively. By measuring solid-state 2H NMR spectra of the two lipids separately in mixtures with the same compositions as a function of cholesterol mole fraction and temperature, we obtained clear evidence for the coexistence of two liquid-crystalline domains in distinct regions of the phase diagram. According to our analysis of the first moments M1 and the observed 2H NMR spectra, one of the domains appears to be a liquid-ordered phase. We applied a mean-torque potential model as an additional tool to calculate the average hydrocarbon thickness, the area per lipid, and structural parameters such as chain extension and thermal expansion coefficient in order to further define the two coexisting phases. Our data imply that phase separation takes place in raftlike ternary PSM/POPC/cholesterol mixtures over a broad temperature range but vanishes at cholesterol concentrations equal to or greater than a mole fraction of 0.33. Cholesterol interacts preferentially with sphingomyelin only at smaller mole fractions, above which a homogeneous liquid-ordered phase is present. The reasons for these phase separation phenomena seem to be differences in the effects of cholesterol on the configurational order of the palmitoyl chains in PSM-d31 and POPC-d31 and a difference in the affinity of cholesterol for sphingomyelin observed at low temperatures. Hydrophobic matching explains the occurrence of raftlike domains in cellular membranes at intermediate cholesterol concentrations but not saturating amounts of cholesterol.