Skip to main content
Proceedings of the National Academy of Sciences of the United States of America logoLink to Proceedings of the National Academy of Sciences of the United States of America
. 1973 Feb;70(2):289–293. doi: 10.1073/pnas.70.2.289

Hydrophobicity of Long Chain n-Alkyl Carboxylic Acids, as Measured by Their Distribution Between Heptane and Aqueous Solutions

Ross Smith 1, Charles Tanford 1
PMCID: PMC433241  PMID: 16592052

Abstract

Previous data for the distribution of the n-alkyl carboxylic acids between aqueous buffers and heptane have suggested that the free energy of transfer between the two solvents does not increase with the length of the alkyl chain beyond palmitic acid, indicating a limit to the hydrophobicity of the alkyl chain at a length of about 15 carbon atoms. It is shown in this paper that previous measurements were influenced by unexpectedly strong pH-dependent association of the long-chain acids in the aqueous phase. Under conditions where such association becomes negligible, the free energy of transfer becomes a strictly linear function of alkyl chain length for all acids up to behenic acid (C21H43COOH).

Keywords: fatty acids, lipids, hydrogen bonds

Full text

PDF
289

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Arvidsson E. O., Green F. A., Laurell S. Branching and hydrophobic bonding. Partition equilibria and serum albumin binding of palmitic and phytanic acids. J Biol Chem. 1971 Sep 10;246(17):5373–5379. [PubMed] [Google Scholar]
  2. GARVIN J. E., KARNOVSKY M. L. The titration of some phosphatides and related compounds in a non-aqueous medium. J Biol Chem. 1956 Jul;221(1):211–222. [PubMed] [Google Scholar]
  3. Tanford C. Hydrophobic free energy, micelle formation and the association of proteins with amphiphiles. J Mol Biol. 1972 Jun 14;67(1):59–74. doi: 10.1016/0022-2836(72)90386-5. [DOI] [PubMed] [Google Scholar]

Articles from Proceedings of the National Academy of Sciences of the United States of America are provided here courtesy of National Academy of Sciences

RESOURCES