18892-74-5

Usage

InChI:InChI=1/C46H84NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h14,16,20,22,25,27,31,33,44H,6-13,15,17-19,21,23-24,26,28-30,32,34-43H2,1-5H3/b16-14-,22-20-,27-25-,33-31-

Upstream product

• 638-08-4 stearic anhydride 
• 17364-19-1 1-stearoyl-sn-glycero-3-phosphocholine 
• 55726-28-8 arachidonic acid anhydride 
• 816-94-4 {2-[(2,3-bis-stearoyloxy-propoxy)-hydroxy-phosphoryloxy]-ethyl}-trimethyl-ammonium betaine 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 19420-57-6 1-stearoyl-sn-glycero-3-phosphocholine 

Relevant academic research and scientific papers

Threshold protective effect of deuterated polyunsaturated fatty acids on peroxidation of lipid bilayers

Autoxidation of polyunsaturated fatty acids (PUFAs) damages lipid membranes and generates numerous toxic by-products implicated in neurodegeneration, aging, and other pathologies. Abstraction of bis-allylic hydrogen atoms is the rate-limiting step of PUFA autoxidation, which is inhibited by replacing bis-allylic hydrogens with deuterium atoms (D-PUFAs). In cells, the presence of a relatively small fraction of D-PUFAs among natural PUFAs is sufficient to effectively inhibit lipid peroxidation (LPO). Here, we investigate the effect of various D-PUFAs on the stability of liposomes under oxidative stress conditions. The permeability of vesicle membranes to fluorescent dyes was measured as a proxy for bilayer integrity, and the formation of conjugated dienes was monitored as a proxy for LPO. Remarkably, both approaches reveal a similar threshold for the protective effect of D-PUFAs in liposomes. We show that protection rendered by D-PUFAs depends on the structure of the deuterated fatty acid. Our findings suggest that protection of PUFAs against autoxidation depends on the total level of deuterated bi-sallylic (CD2) groups present in the lipid bilayer. However, the phospholipid containing 6,6,9,9,12,12,15,15,18,18-d10-docosahexaenoic acid exerts a stronger protective effect than should be expected from its deuteration level. These findings further support the application of D-PUFAs as preventive/therapeutic agents in numerous pathologies that involve LPO.

DEUTERATED COMPOUNDS, COMPOSITIONS, AND USES

Deuterated polyunsaturated fatty acid ("PUFA") compounds, compositions, and uses of the compounds for reducing lipid autooxidation and the treatment of various diseases and conditions are provided.

Derivatives of glycerophosphocholine and glycerophosphoethanolamine, their preparation and their use

The invention relates to new triphenylmethyl derivatives of sn-glycero-3-phosphocholine and sn-glycero-3-phosphoethanolamine of the general formula STR1 in which T denotes a triphenylmethyl group which is unsubstituted or monosubstituted or polysubstitute

13C NMR Spectra of 1-Stearoyl-2-Linoleyl-sn-Glycero-3-Phosphorylcholine and 1-Stearoyl-2-Arachidonoyl-sn-Glycero-3-Phosphorylcholine in CDCl3 Solution and in Sonicated Dispersions in 2H2O

Two mixed-acid lecithins: 1-stearoyl-2-linoleyl-sn-glycero-3-phosphorylcholine (SLL) and 1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphorylcholine (SAL) have been synthesized by phospholipase A2 digestion of 1,2-distearoyl-sn-glycero-3-phosphorylcholine (DSL), followed by reacylation of the lysolecithin with the desired fatty acid anhydride. 13C (25.2 MHz) NMR spectra of SLL and SAL in CDCl3 solution and in sonicated dispersions in 2H2O have been obtained.Complete spectral assignments are reported for the two molecules in both systems. 13C nuclear spin-lattice relaxation times (T1) af SLL and SAL in sonicated aqueous dispersions have also been measured.Relaxation rate profiles as a function of the chain segment position are in general agreement with those recently obtained from 2H NMR for similar systems.