676259-93-1

Basic information

• Product Name: 1,2-Piperidinedicarboxylic acid, 2-[2,6-bis(1-methylethyl)phenyl] 1-(1,1-dimethylethyl) ester
• CAS NO: 676259-93-1
• Molecular Formula: C23H35NO4
• Molecular Weight: 389.535
• Mol File: 676259-93-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,2-Piperidinedicarboxylic acid, 2-[2,6-bis(1-methylethyl)phenyl] 1-(1,1-dimethylethyl) ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Piperidinedicarboxylic acid, 2-[2,6-bis(1-methylethyl)phenyl] 1-(1,1-dimethylethyl) ester(676259-93-1)
• EPA Substance Registry System: 1,2-Piperidinedicarboxylic acid, 2-[2,6-bis(1-methylethyl)phenyl] 1-(1,1-dimethylethyl) ester(676259-93-1)

Safety Data

• Hazardous Substances Data: 676259-93-1(Hazardous Substances Data)

Upstream product

• 2078-54-8 2,6-diisopropylphenol 
• 98303-20-9 1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid 
• 4043-87-2 pipecolic Acid 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 

Relevant articles and documents

Highly water-soluble derivatives of the anesthetic agent propofol: In vitro and in vivo evaluation of cyclic amino acid esters

Cyclic amino acid esters of propofol were synthesized in an attempt to develop new water-soluble anesthetic agents. Their solubility and stability in aqueous solution, and their ability to release propofol in vitro under physiological conditions were determined. L-Proline (6a) and racemic nipecotic acid (6c) esters were found to be highly soluble in water. Sufficiently stable at physiological pH (half-lives >6 h), the α-amino acid esters, 6a and 6b, were found to be quantitatively hydrolyzed in plasma and liver esterase solutions within a few minutes, showing prodrug behavior. The in vitro activity of the esters, determined either by the [ 35S]tert-butylbicyclophosphorothionate ([35S]TBPS) binding assay or electrophysiological measurements of the action at cloned human receptors, proved to be a mechanism involving allosteric modulation of GABAA receptors. Indeed, L-proline (6a), and racemic pipecolinate (6b) and nipecotate (6c), like propofol, reduced [35S]TBPS binding, whereas isonipecotate (6d) showed bicuculline-like behavior, increasing [ 35S]TBPS binding. A nonlinear relation between GABAA receptor binding affinity and lipophilicity, as assessed by reversed-phase high-performance liquid chromatography, emerged as a trend. The in vivo anticonvulsant and anesthetic activities of prolinate 6a, intraperitoneally administered in water solution, showed that is a water-soluble propofol prodrug candidate for developing formulations useful for parenteral administration.