A novel biosurfactant, 2-acyloxyethylphosphonate, isolated from waterblooms of Aphanizomenon flos-aquae.
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.
Kaya
Kunimitsu
K
Graduate School of Environmental Studies, Tohoku University, Aoba-ku, Sendai 980-8579, Japan. kaya@mail.kankyo.tohoku.ac.jp
Morrison
Louise F
LF
Codd
Geoffrey A
GA
Metcalf
James S
JS
Sano
Tomoharu
T
Takagi
Hiroo
H
Kubo
Takuya
T
D046890:Aphanizomenon / Q000737:chemistry* / Q000254:growth & development; D005068:Eutrophication; D005231:Fatty Acids, Unsaturated / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D063065:Organophosphonates / Q000737:chemistry*; D013500:Surface Tension; D013501:Surface-Active Agents / Q000737:chemistry*
D005231:Fatty Acids, Unsaturated; D063065:Organophosphonates; D013501:Surface-Active Agents