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Just how insoluble are monoterpenes?
Authors:Jeffrey D. Weidenhamer  Francisco A. Macias  Nikolaus H. Fischer  G. Bruce Williamson
Affiliation:(1) Department of Chemistry, Louisiana State University, 70803 Baton Rouge, Louisiana;(2) Department of Botany, Louisiana State University, 70803 Baton Rouge, Louisiana;(3) Present address: Departamento de Química Orgánica, Universidad de Cadiz, 11510 Puerto Real, Cadiz, Spain;(4) Present address: Department of Chemistry, Ashland University, 44805 Ashland, Ohio
Abstract:Prior generalizations about the ecological roles of monoterpenes may be misleading if based on the presumed insolubility of monoterpenes in water. We determined the aqueous solubility of 31 biologically active monoterpenes by gas chromatography. While hydrocarbons were of low solubility (< 35 ppm), oxygenated monoterpenes exhibited solubilities one or two orders of magnitude higher, with ranges of 155–6990 ppm for ketones and of 183–1360 ppm for alcohols. Many monoterpenes are phytotoxic in concentrations under 100 ppm, well below the saturated aqueous concentrations of oxygenated monoterpenes. Therefore, even dilute, unsaturated solutions of monoterpenes, occurring naturally in plant tissues and soil solutions, may act as potent biological inhibitors.
Keywords:Allelopathy  monoterpenes  Calamintha ashei  Conradina canescens  ursolic acid  borneol  camphor  juglone  solubility
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