A Novel Biosurfactant, 2-Acyloxyethylphosphonate, Isolated from Waterblooms of Aphanizomenon flos-aquae

Autor: Takuya Kubo, Hiroo Takagi, Tomoharu Sano, James S. Metcalf, Geoffrey A. Codd, Louise F. Morrison, Kunimitsu Kaya
Jazyk: angličtina
Rok vydání: 2006
Předmět:
Zdroj: Molecules, Vol 11, Iss 7, Pp 539-548 (2006)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/11070539
Popis: A novel biosurfactant, 2-acyloxyethylphosphonate, was isolated from waterblooms of Aphanizomenon flos-aquae. Its structure was elucidated by chemical degradation and HRFABMS, GC/EI-MS and 1D- and 2D-NMR spectral analyses. The surfactant contained one mole of 2-hydroxyethylphosphonate and one mole of fatty acid, with hexadecanoic acid accounting for 84.1% of the total fatty acid content. The structure was confirmed by synthesis of 2-oleoyloxyethylphosphonate from ethylene oxide, phosphorus acid and oleic acid chloride. Considering the isolated surfactant molecule as hexadecanoyloxyethylphosphonic acid (mw. 364), the critical micelle concentration (CMC) was about 22 mM.
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