Investigation of isoprenoid benzoates and naphthoates by reversed-phase liquid chromatography. Isocratic elution characteristics of benzoates and naphthoates of C5-C20 terpenoid alcohols.
Conditions for derivatization of C5-C20 isoprenoid alcohols and the reversed-phase liquid chromatographic properties of the corresponding benzoate and naphthoate esters are described. A non-linear response of log k' to changes in the composition of the mobile phase was observed on a Radial-Pak C18 column. In general, the capacity factors (k') increased with increases in carbon content and degree of saturation in the hydrocarbon chain, and decreased with increases in branching and Z double bond content. Replacement of a single hydrogen in the methyl group at C-3 of geranyl benzoate with fluorine had little effect on k', while the difluoro- and trifuoromethyl derivatives showed regular increases in k'. The large extinction coefficients of the aromatic ester moieties, especially the 2-naphthoates, provide high sensitivity for UV detection.
D000438:Alcohols / Q000032:analysis; D001565:Benzoates / Q000032:analysis*; D002853:Chromatography, Liquid / Q000379:methods; D009281:Naphthalenes / Q000032:analysis*; D013056:Spectrophotometry, Ultraviolet / Q000379:methods; D013729:Terpenes / Q000032:analysis*
D000438:Alcohols; D001565:Benzoates; D009281:Naphthalenes; D013729:Terpenes