10567-22-3

Basic information

• Product Name: 3-O-OCTADECYL-SN-GLYCEROL
• Synonyms: 3-O-OCTADECYL-SN-GLYCEROL;(2R)-1-O-Octadecylglycerol;(R)-3-(Octadecyloxy)propane-1,2-diol;[R,(-)]-3-O-Octadecyl-L-glycerol
• CAS NO: 10567-22-3
• Molecular Formula: C₂₁H₄₄O₃
• Molecular Weight: 344.57
• Mol File: 10567-22-3.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• Storage Temp.: -15°C
• CAS DataBase Reference: 3-O-OCTADECYL-SN-GLYCEROL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-OCTADECYL-SN-GLYCEROL(10567-22-3)
• EPA Substance Registry System: 3-O-OCTADECYL-SN-GLYCEROL(10567-22-3)

Safety Data

• Hazardous Substances Data: 10567-22-3(Hazardous Substances Data)

Usage

Description

3-O-OCTADECYL-SN-GLYCEROL, also known as Octadecyl glycerol, is a lipid compound derived from glycerol with an octadecyl (C18) chain attached to the third carbon. It possesses unique properties due to its hydrophobic and hydrophilic characteristics, making it a versatile molecule with potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
3-O-OCTADECYL-SN-GLYCEROL is used as a linker for [application reason] to link zidovudine and foscarnet to prepare an antiviral duplex drug. This combination enhances the antiviral activity against various viruses, including HIV and herpes simplex virus.
Used in Antiviral Applications:
3-O-OCTADECYL-SN-GLYCEROL is used as a conjugating agent for [application reason] to prepare foscarnet conjugates with antiviral activities in human cytomegalovirus-infected cells. The conjugation improves the drug's targeting and efficacy, potentially reducing side effects and increasing treatment success rates.

Upstream product

• 629-93-6 n-iodooctadecane 
• 14347-78-5 1,2-O-isopropylidene-D-glycerol 
• 29909-06-6 1-hydroxy-3-octadecyloxy-propan-2-one 
• 80707-96-6 Ro 15-4454 
• 113597-32-3 1-O-acetyl-2-methoxymethyl-3-O-octadecyl-sn-glycerol 
• 31081-59-1 1-octadecyl methanesulfonate 
• 22323-82-6 (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol 
• 10585-86-1 1,2-Di-O-isopropyliden-3-O-octadecyl-sn-glycerin 
• 112-92-5 1-octadecanol 
• 57044-25-4 (R)-oxiranemethanol 
• 197306-92-6 1-octadecyl-2,3-dibenzylglycerol 
• 30021-05-7 2,2-dimethoxy-3-octadecyloxy-propan-1-ol 
• 3386-32-1 n-octadecyl p-toluenesulfonate 
• 83526-53-8 (R)-1,2-Epoxy-3-(octadecyloxy)propan 

Downstream Products

• 91275-54-6 Methanesulfonic acid (S)-2-methanesulfonyloxy-1-octadecyloxymethyl-ethyl ester 
• 40630-77-1 1-O-benzoyl3-O-octadecyl-sn-glycerol 
• 104478-41-3 Benzoic acid (R)-1-hydroxymethyl-2-octadecyloxy-ethyl ester 
• 83526-50-5 3-O-Octadecyl-1,2-di-O-p-toluolsulfonyl-sn-glycerin 
• 83526-54-9 3-O-Octadecyl-1-O-p-toluolsulfonyl-sn-glycerin 
• 6068-25-3 1-octadecyl-2-palmitoyl-D-glycerol 
• 80707-92-2 2-O-Benzyl-3-O-octadecyl-1-O-trityl-sn-glycerin 
• 80459-31-0 2-O-benzyl-3-O-octadecyl sn-glycerol 
• 65492-82-2 2-O-Methyl-3-O-octadecyl-sn-glycero-1-phosphorylcholin 
• 83526-61-8 2-O-Methyl-3-O-octadecyl-1-O-trityl-sn-glycerin 
• 150283-43-5 1-O-trityl-2-O-ethyl-3-O-octadecyl-sn-glycerol 
• 105415-94-9 (S)-2-benzyloxy-3-octadecyloxypropyl 2-(diethylmethylammonio)ethyl phosphate 
• 105415-95-0 (S)-2-benzyloxy-3-octadecyloxypropyl 2-(N-methylpyrrolidinio)ethyl phosphate 
• 74430-89-0 Lyso-platelet-activating factor (C₁₈) 

Relevant articles and documents

-

-

Activation of n-3 polyunsaturated fatty acids as oxime esters: A novel approach for their exclusive incorporation into the primary alcoholic positions of the glycerol moiety by lipase

A novel approach has been developed for activating the highly bioactive long-chain n-3 polyunsaturated fatty acids EPA and DHA as oxime esters and incorporating them exclusively to the end-positions of glycerol and enantiopure 1-O-alkylglycerols. The Candida antarctica lipase B was observed to display a superb regioselectivity when using the acetoxime esters of EPA and DHA as acyldonors under mild condition to keep acyl-migration side-reaction under complete control. Regiopure 1,3-diacylglycerols, 1-O-alkyl-3-acyl-sn-glycerols and their antipodes possessing EPA and DHA were afforded in very high purity and yields.

D and L etherlipid stereoisomers and liposomes

A liposome having a lipid bilayer, where the lipid bilayer includes either the L or D stereoisomer of an ether lipid or a non-equal mixture of both. Most preferably the liposome also comprises (a) an underivatized phosphatidylcholine; (b) a sterol; (c) about 5-20 mole % of a phosphatidylethanolamine linked to a dicarboxylic acid at the ethanolamine group of the phosphatidylethanolamine, and (d) greater than about 10 mole % to less than about 30 mole % of either the L or D stereoisomer of an ether lipid. The liposome may be used as an anti-cancer or anti-inflammatory agent.

Stereospecific and regiospecific ring opening of glycidol with primary and secondary alcohols mediated by diisobutylaluminium hydride

Regiospecific ring opening of (R)-(+)- or (S)-(-)-glycidol 1a, b with primary and secondary alcohols in the presence of diisobutylaluminium hydride provides 1-O-alkyl-sn-glycerol 2 without formation of the undesired regioisomer, 2-O-alkylglycerol 3.The configuration of the glycidol is preserved in the product.