84337-43-9

Usage

Uses

Used in Pharmaceutical Industry:
1-O-Octadecyl-2-O-methyl-rac-glycerol is used as a precursor for the synthesis of Edelfosine, a potent inducer of apoptosis in human leukemic cells. Edelfosine has garnered significant attention as a promising drug candidate in cancer treatment, particularly for hematological malignancies.
Additionally, 1-O-Octadecyl-2-O-methyl-rac-glycerol is utilized in the preparation of phospholipids containing nitrogen homologs, which exhibit antitumor activities. These phospholipids have potential applications in the development of novel therapeutic agents targeting cancer cells, further highlighting the versatility and importance of this glycerol derivative in the pharmaceutical sector.

InChI:InChI=1/C22H46O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25-21-22(20-23)24-2/h22-23H,3-21H2,1-2H3

Upstream product

• 105405-86-5 1-O-octadecyl-2-O-methyl-3-O-trityl-rac-glycerol 
• 761-06-8 2-methylglycerol 
• 112-89-0 1-Bromooctadecane 
• 13538-48-2 Octadecylsulfonsaeuremethylester 
• 544-62-7 batyl alcohol 
• 16725-43-2 4-(n-octadecyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 86334-56-7 1-octadecyloxy-3-trityloxy-propan-2-ol 
• 112-92-5 1-octadecanol 
• 108225-24-7 3-benzyloxy-2-hydroxypropyl octadecyl ether 
• 90940-90-2 1-O-benzyl-2-O-methyl-3-O-octadecyl-rac-glycerol 
• 31081-59-1 1-octadecyl methanesulfonate 

Downstream Products

• 70641-51-9 Edelfosine 

Relevant academic research and scientific papers

Synthese sowie Antitumorwirksamkeit und Vertraeglichkeit im Tierexperiment von elementhomologen Phospholipiden

Stichworte: Antitumormittel * Phospholipide

Synthesis of alkyl chain-modified ether lipids and evaluation of their in vitro cytotoxicity

A series of alkyl lysophospholipid (ALP) analogs of ET-18-OCH3 (1-O- octadecyl-2-O-methyl-rac-glycero-3-phosphocholine) containing modifications in the long C-1 chain has been synthesized and evaluated in human tumor cell line cytotoxicity assays. The compounds have also been evaluated in platelet activating factor (PAF) receptor agonism and hemolysis tests. Two modifications have been studied, introduction of a carbonyl group at different positions of the C-1 chain and branching of this chain, in some compounds with incorporation of a phenyl group. Several compounds showed a cytotoxic potency comparable to that of the reference compound ET-18-OCH3, associated with reduced proaggregating and hemolytic effects. The two enantiomers of 1-O-(7-oxooctadecyl)-2-O-methyl-rac-glycero-3-phosphocholine (2) showed the same level of cytotoxicity or antiproliferative activity, with the PAF-agonistic effect confined to R-2. The very low stereoselectivity found in the in vitro cytotoxicity confirms earlier results and indicates a lack of stereospecific interactions with a macromolecular target.

Synthesis of 1-O-alkyl-2-O-methyl-glycerophospholipids with potential antitumor activity

Some synthetic alkyl-lysophospholipid analogs have been described as a new class of immunopotentiating and antitumor agents. Among them, 1-O-octadecyl-2-O-methyl-rac-glycero-3-phosphocholine has been reported to possess the highest antitumor activity. A new method for the synthesis of this compound and of the ethanolamine- and serine-containing analog is reported. 1-Alkyl-2-methyl-rac-glycerol, prepared from 1,2-isopropylidene-glycerol, is phosphorylated and the intermediate is condensed either with N-t-BOC-protected ethanolamine or with N-t-BOC-protected serine benzhydryl ester. The choline-derivative is obtained by methylation with CH3I of the ethanolamine derivative. The same synthetic sequence has been used also for synthesizing compounds unsaturated at the fatty alkyl chain in position 1 of the glycerol moiety. Preliminary observation are reported on the selective cytolytic action of the compounds on a tumor cell line.