title: A novel biosurfactant, 2-acyloxyethylphosphonate, isolated from waterblooms of Aphanizomenon flos-aquae.
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.
authors.affiliation: Graduate School of Environmental Studies, Tohoku University, Aoba-ku, Sendai 980-8579, Japan. kaya@mail.kankyo.tohoku.ac.jp
authors.forename: Kunimitsu
authors.initials: K
authors.lastname: Kaya
authors.forename: Louise F
authors.initials: LF
authors.lastname: Morrison
authors.forename: Geoffrey A
authors.initials: GA
authors.lastname: Codd
authors.forename: James S
authors.initials: JS
authors.lastname: Metcalf
authors.forename: Tomoharu
authors.initials: T
authors.lastname: Sano
authors.forename: Hiroo
authors.initials: H
authors.lastname: Takagi
authors.forename: Takuya
authors.initials: T
authors.lastname: Kubo
mesh_terms: 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*
chemical_list: D005231:Fatty Acids, Unsaturated; D063065:Organophosphonates; D013501:Surface-Active Agents