Molecules 2006, 11(7), 539-548; doi:10.3390/11070539
Article

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

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Received: 16 June 2006; in revised form: 18 July 2006 / Accepted: 18 July 2006 / Published: 22 July 2006
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: 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.
Keywords: biosurfactant; cyanobacterium; Aphanizomenon flos-aquae; fatty acids; 2-hydroxyethanephosphonate; 2-acyloxyethanephosphonate; C-P linkage; surface tension; toxicity; critical micelle concentration (CMC).
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MDPI and ACS Style

Kaya, K.; Morrison, L.F.; Codd, G.A.; Metcalf, J.S.; Sano, T.; Takagi, H.; Kubo, T. A Novel Biosurfactant, 2-Acyloxyethylphosphonate, Isolated from Waterblooms of Aphanizomenon flos-aquae. Molecules 2006, 11, 539-548.

AMA Style

Kaya K, Morrison LF, Codd GA, Metcalf JS, Sano T, Takagi H, Kubo T. A Novel Biosurfactant, 2-Acyloxyethylphosphonate, Isolated from Waterblooms of Aphanizomenon flos-aquae. Molecules. 2006; 11(7):539-548.

Chicago/Turabian Style

Kaya, Kunimitsu; Morrison, Louise F.; Codd, Geoffrey A.; Metcalf, James S.; Sano, Tomoharu; Takagi, Hiroo; Kubo, Takuya. 2006. "A Novel Biosurfactant, 2-Acyloxyethylphosphonate, Isolated from Waterblooms of Aphanizomenon flos-aquae." Molecules 11, no. 7: 539-548.

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