Investigation of isoprenoid benzoates and naphthoates by reversed-phase liquid chromatography. Isocratic elution characteristics of benzoates and naphthoates of C5C20 terpenoid alcohols

Tsan Hsi Yang, Mark Zabriskie, C. Dale Poulter

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Conditions for derivatization of C5C20 isoprenoid alcohols and the reversedphase 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 an degree of saturation inthe 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.

Original languageEnglish (US)
Pages (from-to)121-132
Number of pages12
JournalJournal of Chromatography A
Volume312
Issue numberC
DOIs
StatePublished - 1984
Externally publishedYes

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Benzoates
Terpenes
Liquid chromatography
Reverse-Phase Chromatography
Esters
Alcohols
Fluorine
Hydrocarbons
Hydrogen
Carbon
Derivatives
Liquids
Chemical analysis

ASJC Scopus subject areas

  • Analytical Chemistry

Cite this

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title = "Investigation of isoprenoid benzoates and naphthoates by reversed-phase liquid chromatography. Isocratic elution characteristics of benzoates and naphthoates of C5C20 terpenoid alcohols",
abstract = "Conditions for derivatization of C5C20 isoprenoid alcohols and the reversedphase 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 an degree of saturation inthe 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.",
author = "Yang, {Tsan Hsi} and Mark Zabriskie and Poulter, {C. Dale}",
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TY - JOUR

T1 - Investigation of isoprenoid benzoates and naphthoates by reversed-phase liquid chromatography. Isocratic elution characteristics of benzoates and naphthoates of C5C20 terpenoid alcohols

AU - Yang, Tsan Hsi

AU - Zabriskie, Mark

AU - Poulter, C. Dale

PY - 1984

Y1 - 1984

N2 - Conditions for derivatization of C5C20 isoprenoid alcohols and the reversedphase 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 an degree of saturation inthe 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.

AB - Conditions for derivatization of C5C20 isoprenoid alcohols and the reversedphase 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 an degree of saturation inthe 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.

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