78858-44-3

Usage

Uses

Used in Pharmaceutical Industry:
1-O-HEXADECYL-2-O-METHYL-SN-GLYCERYL-3-PHOSPHORYLCHOLINE is used as a potential therapeutic agent for various applications, including decreasing plasma membrane fluidity and inhibiting tumor cell invasiveness. Its C-18 analog has demonstrated these effects in embryonic chick heart, making it a promising candidate for further research and development in the pharmaceutical industry.
Used in Neuroscience Research:
1-O-HEXADECYL-2-O-METHYL-SN-GLYCERYL-3-PHOSPHORYLCHOLINE is used as a research tool in neuroscience to study the effects of its C-18 analog on the release of nitric oxide (NO) in rat astrocytes. This helps researchers understand the underlying mechanisms and pathways involved in NO production and its role in various neurological processes.

InChI:InChI=1/C25H54NO6P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-21-30-23-25(29-5)24-32-33(27,28)31-22-20-26(2,3)4/h25H,6-24H2,1-5H3/t25-/m1/s1

Upstream product

• 4167-02-6 2-bromoethylphosphoric acid dichloride 
• 96960-92-8 1-O-hexadecyl-2-O-methyl-sn-glycerol 
• 75-50-3 trimethylamine 
• 111248-00-1 2-(1-hexadecyl-2-methyl-sn-glycerol)-2-oxo-1,3,2-dioxaphospholane 
• 36653-82-4 1-Hexadecanol 
• 122822-34-8 1-O-hexadecyl-2-O-methyl-3-O-(tert-butyldiphenylsilyl)-sn-glycerol 
• 119879-76-4 3-O-Hexadecyl-sn-glycerol 1-(tert-butyldiphenylsilyl ether) 
• 122822-32-6 1-O-hexadecyl-2-O-methyl-3-O-(p-tolylsulfonyl)-sn-glycerol 
• 111247-99-5 1-hexadecyl-2-methyl-3-(triphenylmethyl)-sn-glycerol 
• 96960-90-6 1-O-hexadecyl-3,4-O-isopropylidene-2-O-methyl-D-threitol 
• 96960-89-3 1-O-hexadecyl-3,4-O-isopropylidene-D-threitol 
• 96960-91-7 1-O-hexadecyl-2-O-methyl-D-threitol 
• 84379-55-5 1-O-hexadecyl-2-O-benzyl-3,4-O-isopropylidene-D-threitol 
• 20779-14-0 methanesulfonic acid hexadecyl ester 

Relevant academic research and scientific papers

Antitumor phospholipids: A one-pot introduction of a phosphocholine moiety into lipid hydroxy acceptors

A high-yielding, 3-step, one-pot conversion of lipid hydroxy acceptors 2 into clinically useful alkylphosphocholines 1 is reported. Reaction of 2 with ethylene chlorophosphite gave phosphite 3, which underwent oxidation and ring opening with bromine in CH2Cl2 to give (2-bromoethyl)phosphate ester 4; hydrolysis of the P-Br bond and quaternization of 4 with aqueous trimethylamine generated 1.

Regiospecific Opening of Glycidyl Derivatives Mediated by Boron Trifluoride. Asymmetric Synthesis of Ether-Linked Phospholipids

A short, chiral synthesis of unnatural, cytotoxic ether-linked phospholipids is reported in which the key step is the very high regio- and stereospecific nucleophilic opening of the p-toluenesulfonate (1a, 1b) or tert-butyldiphenylsilyl ether (6a, 6b) derivatives of (R)- or (S)-glycidol with 1-hexadecanol using boron trifluoride etherate as catalyst.The enantiomeric excess of the ring-opened products was >94percent, as judged by 1H NMR and chiral HPLC analysis of the Mosher ester derivatives, indicating that ring opening of 1 and 6 proceeds without significant loss of optical purity.The synthetic strategy of using optically active glycidyl derivatives as the precursor of the glycerol backbone permits the desired enantiomers of 1(3)-O-2-O-methylphosphocholines (5a, 5b) to be generated in good yield and high optical purity from the ring-opened intermediates (2, 7) in three steps without the use of protecting groups.

Stereospecific Synthesis of Ether and Thioether Phospholipids. The Use of L-Glyceric Acid as a Chiral Phospholipid Precursor

A novel stereospecific synthesis of biologically active ether phospholipids is reported.The synthesis is based on (1) the use of L-glyceric acid as the chiral center for the construction of the optically active phospholipid molecule, (2) the introduction

A NEW APPROACH TO THE SYNTHESIS OF ETHER PHOSPHOLIPIDS. PREPARATION OF 1,2-DIALKYLGLYCEROPHOSPHORYLCHOLINES FROM L-GLYCERIC ACID

A novel stereospecific synthesis of antitumor active ether phospholipids is reported.