16725-43-2

Basic information

• Product Name: O-Octadecyl-1,2-acetone glycerin acetal
• Synonyms: 2,2-Dimethyl-4((octadecyloxy)methyl)-1,3-dioxolane;O-Octadecyl-1,2-acetone glycerin acetal
• CAS NO: 16725-43-2
• Molecular Formula: C₂₄H₄₈O₃
• Molecular Weight: 384.64
• Mol File: 16725-43-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 32-33 °C
• Boiling Point: 210-215 °C(Press: 1 Torr)
• Appearance: /
• Density: 0.886±0.06 g/cm3(Predicted)
• CAS DataBase Reference: O-Octadecyl-1,2-acetone glycerin acetal(CAS DataBase Reference)
• NIST Chemistry Reference: O-Octadecyl-1,2-acetone glycerin acetal(16725-43-2)
• EPA Substance Registry System: O-Octadecyl-1,2-acetone glycerin acetal(16725-43-2)

Safety Data

• Hazardous Substances Data: 16725-43-2(Hazardous Substances Data)

Upstream product

• 112-89-0 1-Bromooctadecane 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 112-92-5 1-octadecanol 
• 23737-51-1 solketal tosylate 
• 3386-32-1 n-octadecyl p-toluenesulfonate 
• 31081-59-1 1-octadecyl methanesulfonate 
• 629-93-6 n-iodooctadecane 

Downstream Products

• 72490-82-5 2-hydroxy-3-(octadecyloxy)propyl 2-(trimethylammonio)ethyl phosphate 
• 86008-21-1 2-(benzyloxy)-3-(octadecyloxy)-1-propanol 
• 105405-86-5 1-O-octadecyl-2-O-methyl-3-O-trityl-rac-glycerol 
• 84337-43-9 2-methoxy-3-octadecyloxy-1-propanol 
• 133415-56-2 4-Benzyloxymethyl-2-octadecyloxymethyl-[1,3]dioxolane 
• 133281-07-9 2-Benzyloxymethyl-4-octadecyloxymethyl-[1,3]dioxolane 
• 124133-84-2 Toluene-4-sulfonic acid 1-hydroxymethyl-2-octadecyloxy-ethyl ester 
• 108225-24-7 3-benzyloxy-2-hydroxypropyl octadecyl ether 
• 16245-97-9 octadecyl glycidyl ether 
• 63326-69-2 1-O-Octadecyl-2-O-p-toluenesulfonyl-3-O-trityl-glycerol 
• 86334-56-7 1-octadecyloxy-3-trityloxy-propan-2-ol 
• 122971-78-2 rac-2-O-hexadecanoyl-3-O-octadecylglyceryldiphenyl phosphate 
• 85712-13-6 1-O-octadecyl-3-acetylglycerol 
• 83526-75-4 (S)-1-O-octadecyl-3-acetylglycerol 

Relevant articles and documents

Kinetic resolution of 1-O-alkylglycerols by lipase

Pseudomonas sp. lipase was employed to resolve kinetically 1-O- alkylglycerols by a sequential diacylation process. Only low or moderate E- values were obtained, but at approximately 60% conversion enantiomerically pure monoacetates were obtained of the natural S-configuration for glyceryl ether lipids.

Design, synthesis and cytotoxicity of chimeric erlotinib-alkylphospholipid hybrids

Two series of erlotinib-alkylphospholipid hybrids were prepared and evaluated for their antiproliferative activities against a panel of four cell lines representing lung, breast, liver and skin cancers using erlotinib and miltefosine as reference standards. Amide analogs elicited more enhanced cytotoxic activity than analogous esters. Amide derivatives 8d and 8e exhibited promising broad-spectrum antiproliferative activity and higher efficacy than reference erlotinib and miltefosine. Their cellular GI50 values was in the ranges of 24.7–46.9 μM and 26.8–43.1 μM for 8e and 8d respectively. Assay results of the inhibitory activity of the prepared compounds on EGFR kinase reaction and Akt phosphorylation in conjugation with statistical correlation analysis indicated that other mechanisms might contribute to their elicited cytotoxicities. In addition, statistical correlation analysis revealed that mechanisms of elicited cytotoxicities for amide series might be different from ester series. In addition, correlation analysis indicated variations in the mechanisms according to the types of cell line.

Lipase-catalysed kinetic resolution of 1-O-alkylglycerols by sequential transesterification

The natural S-configured chimyl, batyl and selachyl alcohols of the 1-O-alkylglycerol type were prepared by enantioselective lipase-catalysed transesterification. Their racemates were synthesised in two steps by reacting racemic solketal with the bromides of the corresponding fatty alcohols and a subsequent conversion of the intermediates into the 1-O-alkylglycerols by deprotection under acidic aqueous conditions. The Pseudomonas fluorescens lipase was employed to kinetically resolve the racemic 1-O-alkylglycerols by a sequential diacetylation process to afford them virtually enantiomerically pure. Dramatic enantioselectivity increase was observed for the saturated chimyl (E = 17-32) and batyl (E = 14-38) alcohols at decreased temperature, whereas for the monounsaturated selachyl (E = 12-13) alcohol no such temperature effects were observed.