PMID: 41067Sep 1, 1979

Inter-relationships between solubilities, distribution coefficients and melting points of some substituted benzoic and phenylacetic acids

The Journal of Pharmacy and Pharmacology
N A ArmstrongC K Wong

Abstract

Ten 4-hydroxy and 4-alkoxy benzoic and phenylalkanoic acids have been investigated. Solubilities in aqueous buffer at pH 1.2 were determined, together with distribution coefficients between the buffer and either octanol or isopropyl myristate. When plotted against the total number of carbon atoms in the side chains, log octanol/water distribution coefficients gave two parallel straight lines, one for the substituted benzoic acids, and the other for the substituted phenylalkanoic acids. The slopes approximated to 0.5, the generally accepted value for methylene. Similar plots could be obtained with isopropyl myristate, provided the hydroxy acid results were ignored, and also when log aqueous solubilities were plotted against carbon number, although there was considerable scatter. The differences between the distribution coefficient results were explained in terms of solute-solvent interactions, and the scatter attributed to variations in the heats of fusion of the solutes. Yalkowsky's equation (1977), linking aqueous solubilities and melting points with distribution coefficients, was applied to the results, and found to be of limited predictive value.

References

Dec 1, 1976·The Journal of Pharmacy and Pharmacology·K C James
Mar 1, 1977·Journal of Pharmaceutical Sciences·D R Flanagan, S H Yalkowsky
Sep 1, 1968·The Journal of Pharmacy and Pharmacology·F Reynolds, A H Beckett
Sep 1, 1968·The Journal of Pharmacy and Pharmacology·K C James, M Roberts
Dec 1, 1969·The Journal of Pharmacy and Pharmacology·A H Beckett, A C Moffat

Citations

Apr 9, 2005·International Journal of Pharmaceutics·Michael H Abraham, William E Acree

Related Concepts

Benzoate
butyrate
Phenylacetic Acids
Propionic Acids

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