669011-08-9

Basic information

• Product Name: Tetradecanoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, phenylmethyl ester
• CAS NO: 669011-08-9
• Molecular Formula: C26H43NO4
• Molecular Weight: 433.632
• Mol File: 669011-08-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Tetradecanoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Tetradecanoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, phenylmethyl ester(669011-08-9)
• EPA Substance Registry System: Tetradecanoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, phenylmethyl ester(669011-08-9)

Safety Data

• Hazardous Substances Data: 669011-08-9(Hazardous Substances Data)

Upstream product

• 129850-62-0 2-(tert-butoxycarbonylamino)-D,L-tetradecanoic acid 
• 100-44-7 benzyl chloride 
• 143-15-7 1-dodecylbromide 
• 24424-99-5 di-tert-butyl dicarbonate 

Relevant articles and documents

Design, Synthesis, and Evaluation of a Liposaccharide Drug Delivery Agent: Application to the Gastrointestinal Absorption of Gentamicin

The design, synthesis, and evaluation of a liposaccharide (11) for use as an agent to enhance the gastrointestinal absorption of charged, hydrophilic drugs with poor membrane permeability is reported. 11 was designed to possess both surfactant and ion-pairing properties and was conveniently synthesized from D-glucuronic acid (2) and N-Boc-lipoamino acid (5) precursors in eight steps in good yield. Isothermal titration microcalorimetry was used to determine the critical micelle concentration of 11 (in PBS) to be 2.09 ± 0.01 mM with an enthalpy of demicellization of 4.91 ± 0.11 kJ/mol. The ability of 11 to enhance the gastrointestinal absorption of the aminoglycoside antibiotic gentamicin (1), a hydrophilic polycation with negligible oral bioavailability, was assessed in vivo using rats. Rats dosed orally with a mixture of 11 (100 mg/kg) and 1 (60 mg/kg) had a statistically significant (P ≤ 0.034) increase in Cmax, AUC120, and percent absolute bioavailability (F) compared to control 1 (60 mg/kg) alone. The highest bioavailability (F = 9.1 ± 2.0%) was achieved by dosing with the mixture 11 (100 mg/kg) and 1 (15 mg/kg). This represents a 6-fold increase in bioavailability compared to the control (F = 1.4 ± 0.3%). These results suggest that the molar ratio of 1:11 may be critical in optimizing the delivery system, a finding ascribed in part to the ion-pairing properties of 11. The effect of 11 on the gastrointestinal mucosa was assessed using light microscopy to examine tissue samples from rats used in the pharmacokinetic study. No morphological changes were found in either the esophagi or duodena of the rats examined. One rat dosed with 11 (100 mg/kg) and 1 (60 mg/kg) exhibited slight gastric erosion, which could be attributed to 11.