74430-89-0

Basic information

• Product Name: 1-O-OCTADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE
• Synonyms: 1-O-OCTADECYL-2-HYDROXY-SN-GLYCERO-3-PHOSPHOCHOLINE;1-O-OCTADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE;1-O-OCTADECYL-SN-GLYCERO-3-PHOSPHORYLCHOLINE;1-O-OCTADECYL-SN-GLYCERYL-3-PHOSPHORYLCHOLINE;1-O-STEARYL-SN-GLYCERO-3-PHOSPHOCHOLINE;LYSO-PAF (C18);LYSO-PLATELET ACTIVATING FACTOR-18;LYSO-PLATELET ACTIVATING FACTOR (C18)
• CAS NO: 74430-89-0
• Molecular Formula: C26H56NO6P
• Molecular Weight: 509.7
• Mol File: 74430-89-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C
• CAS DataBase Reference: 1-O-OCTADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-OCTADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE(74430-89-0)
• EPA Substance Registry System: 1-O-OCTADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE(74430-89-0)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 74430-89-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-O-OCTADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE is used as a lipid component in the formulation of lipid nanoparticles for the encapsulation and protection of mRNA and other nucleic acids. This application is crucial for the development of mRNA-based vaccines and therapeutics, as it ensures the stability and efficient delivery of the mRNA payload into cells, thereby improving the effectiveness and safety of these therapies.
Used in mRNA-based Vaccines and Therapeutics:
1-O-OCTADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE is used as a key ingredient in the development of mRNA-based vaccines and therapeutics. Its role in the encapsulation and protection of mRNA within lipid nanoparticles is essential for the stability and efficient delivery of the mRNA payload, which in turn contributes to the overall effectiveness and safety of these treatments.
Used in Drug Delivery Systems:
1-O-OCTADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE is used as a component in drug delivery systems, particularly in the formulation of lipid nanoparticles. Its cationic nature allows for the encapsulation of mRNA and other nucleic acids, enabling their efficient delivery into cells. This application is vital for the development of advanced drug delivery systems that can improve the bioavailability and therapeutic outcomes of mRNA-based therapies.

Upstream product

• 74389-69-8 1-O-octadecyl-2-acetyl-sn-glycero-3-phosphocholine 
• 129170-96-3 C₂₉H₅₇N₂O₇P 
• 645-84-1 choline phosphate 
• 111860-28-7 (2S,3S)-2,3-Bis-benzoyloxy-3-carboxy-propionate((R)-2-hydroxy-3-octadecyloxy-propyl)-dimethyl-sulfonium; 
• 16245-97-9 octadecyl glycidyl ether 
• 112-92-5 1-octadecanol 
• 83526-54-9 3-O-Octadecyl-1-O-p-toluolsulfonyl-sn-glycerin 
• 83526-52-7 3-O-Octadecyl-2-O-p-toluolsulfonyl-sn-glycerin 
• 83526-59-4 2-O-Acetyl-3-O-benzyl-1-O-octadecyl-sn-glycerin 
• 83526-60-7 2-O-Acetyl-1-O-benzyl-3-O-octadecyl-sn-glycerin 
• 80483-86-9 2-O-Benzyl-1-O-octadecyl-sn-glycero-3-phosphorylcholin 
• 83526-58-3 ((S)-1-(benzyloxy)-3-(octadecyloxy)propan-2-yl) 4-methylbenzenesulfonate 
• 83526-53-8 (R)-1,2-Epoxy-3-(octadecyloxy)propan 
• 6076-32-0 3-O-Octadecyl-1-O-trityl-sn-glycerin 

Downstream Products

• 1159279-53-4 1-O-octadecyl-2-(4-(4-(bis(2-chloroethyl)amino)phenyl)butanoyl)-sn-glycero-3-phosphocholine 
• 74389-69-8 1-O-octadecyl-2-acetyl-sn-glycero-3-phosphocholine 

Relevant articles and documents

Synthesis and biophysical characterization of chlorambucil anticancer ether lipid prodrugs

The synthesis and biophysical characterization of four prodrug ether phospholipid conjugates are described. The lipids are prepared from the anticancer drug chlorambucil and have C16 and C18 ether chains with phosphatidylcholine or phosphatidylglycerol he

Synthesis and biological activity of anticancer ether lipids that are specifically released by phospholipase A2 in tumor tissue

The clinical use of anticancer lipids is severely limited by their ability to cause lysis of red blood cells prohibiting intravenous injection. Novel delivery systems are therefore required in order to develop anticancer ether lipids (AELs) into clinicall

Formation of a Structural Isomer of Platelet Activating Factor on the Acetylation of 1-Alkyl-sn-Glycero-3-Phosphocholines

The key stage in the synthesis of the platelet activating factor (PAT) - the acetylation of 1-alkyl-sn-glycero-3-phosphocholines (lyso-PAT) with acetic anhydride - has been studied.The formation of a structural isomer of PAT - 1-alkyl-3-acetyl-sn-glycero-3-phosphocholines - as a by-product when the reaction is carried out in the presence of bases (triethylamine, 4-dimethylaminopyridine) has been shown.Acetylation under the conditions of acid catalysis gave the isomerically pure PAT.The mechanism of the reaction leading to the formation of the PAT isomer is discussed.

Optically active oxiranes. Synthesis of PAF (Platelet Aggregating Factor)

A number of epoxides bearing no function in the α-position have been converted into β-hydroxy sulfonium salts.Association with an otically active acid (dibenzoyltartaric) allowed the resolution.This method has been used to prepare the optically active glycidol octadecyl ether which was converted into (-) PAF. Key words: oxiranes / resolution / PAF synthesis

An efficient synthesis of Platelet-Activating Factor (PAF) via 1-o-alkyl-2-o-(3-isoxazolyl)-SN-glycero-3-phosphocholine, a new PAF agonist utilization of the 3-isoxazolyloxy group as a protected hydroxyl

Potent PAF agonists (R)-3a,b were synthesized and converted into PAF. Key steps include Mitsunobu reaction of a chiral secondary alcohol with 3-hydroxyisoxazole as the acidic component, and hydrogenolytic ring cleavage of the resulting 3-isoxazolyloxy gro

Method of use of 1-(alkyl for alkylcarbanoyl)-2-carbamoylglycerol derivatives

Glycerol derivatives, inclusive of salts thereof, of the formula STR1 wherein R1 is alkyl or alkylcarbamoyl containing 10 to 30 carbon atoms, R2 and R3 are independently hydrogen, C1-6 alkyl or, taken together w

RESOLUTION OF OXIRANES. APPLICATION TO THE SYNTHESIS OF THE PLATELET AGGREGATION FACTOR

Resolution of racemic oxiranes has been achieved through their conversion into hydroxy sulfonium salts of dibenzoyltartaric acid.Thus, resolution of n-octadecyl glycidyl ether followed by reaction with phosphorylcholine and acetylation led to C18-P.A.F.